U.S. patent application number 13/820497 was filed with the patent office on 2014-10-02 for novel compounds and compositions for the inhibition of nampt.
The applicant listed for this patent is Kenneth W. Bair, Timm R. Baumeister, Alexandre J. Buckmelter, Karl H. Clodfelter, Peter Dragovich, Francis Gosselin, Bingsong Han, Jian Lin, Dominic J. Reynolds, Bruce Roth, Chase C. Smith, Zhongguo Wang, Po-Wai Yuen, Xiaozhang Zheng. Invention is credited to Kenneth W. Bair, Timm R. Baumeister, Alexandre J. Buckmelter, Karl H. Clodfelter, Peter Dragovich, Francis Gosselin, Bingsong Han, Jian Lin, Dominic J. Reynolds, Bruce Roth, Chase C. Smith, Zhongguo Wang, Po-Wai Yuen, Xiaozhang Zheng.
Application Number | 20140294805 13/820497 |
Document ID | / |
Family ID | 44651990 |
Filed Date | 2014-10-02 |
United States Patent
Application |
20140294805 |
Kind Code |
A1 |
Bair; Kenneth W. ; et
al. |
October 2, 2014 |
NOVEL COMPOUNDS AND COMPOSITIONS FOR THE INHIBITION OF NAMPT
Abstract
The present invention relates to compounds and compositions for
the inhibition of NAMPT, their synthesis, applications and
antidotes. An illustrative compound of the invention is shown
below: ##STR00001##
Inventors: |
Bair; Kenneth W.;
(Watertown, MA) ; Baumeister; Timm R.; (Watertown,
MA) ; Buckmelter; Alexandre J.; (Watertown, MA)
; Clodfelter; Karl H.; (Watertown, MA) ;
Dragovich; Peter; (South San Francisco, CA) ;
Gosselin; Francis; (South San Francisco, CA) ; Han;
Bingsong; (Watertown, MA) ; Lin; Jian;
(Watertown, MA) ; Reynolds; Dominic J.;
(Watertown, MA) ; Roth; Bruce; (South San
Francisco, CA) ; Smith; Chase C.; (Watertown, MA)
; Wang; Zhongguo; (Watertown, MA) ; Yuen;
Po-Wai; (Beijing, CN) ; Zheng; Xiaozhang;
(Watertown, MA) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Bair; Kenneth W.
Baumeister; Timm R.
Buckmelter; Alexandre J.
Clodfelter; Karl H.
Dragovich; Peter
Gosselin; Francis
Han; Bingsong
Lin; Jian
Reynolds; Dominic J.
Roth; Bruce
Smith; Chase C.
Wang; Zhongguo
Yuen; Po-Wai
Zheng; Xiaozhang |
Watertown
Watertown
Watertown
Watertown
South San Francisco
South San Francisco
Watertown
Watertown
Watertown
South San Francisco
Watertown
Watertown
Beijing
Watertown |
MA
MA
MA
MA
CA
CA
MA
MA
MA
CA
MA
MA
MA |
US
US
US
US
US
US
US
US
US
US
US
US
CN
US |
|
|
Family ID: |
44651990 |
Appl. No.: |
13/820497 |
Filed: |
September 2, 2011 |
PCT Filed: |
September 2, 2011 |
PCT NO: |
PCT/US2011/050321 |
371 Date: |
May 15, 2014 |
Related U.S. Patent Documents
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Application
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Filing Date |
Patent Number |
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61379789 |
Sep 3, 2010 |
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61379796 |
Sep 3, 2010 |
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61386028 |
Sep 24, 2010 |
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61386023 |
Sep 24, 2010 |
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61475813 |
Apr 15, 2011 |
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61483242 |
May 6, 2011 |
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Current U.S.
Class: |
424/133.1 ;
424/649; 514/171; 514/214.02; 514/233.2; 514/253.04; 514/255.05;
514/259.1; 514/300; 514/301; 514/302; 514/355; 514/356; 514/43;
540/579; 544/127; 544/281; 544/362; 544/405; 546/113; 546/114;
546/115 |
Current CPC
Class: |
A61P 17/00 20180101;
C07D 495/04 20130101; A61P 31/18 20180101; A61P 1/04 20180101; A61K
31/497 20130101; A61K 45/06 20130101; A61K 31/519 20130101; A61K
31/4365 20130101; A61K 31/437 20130101; A61K 31/5377 20130101; A61P
37/02 20180101; C07D 491/04 20130101; A61P 9/10 20180101; A61P 3/10
20180101; A61P 11/06 20180101; A61P 11/08 20180101; A61P 17/04
20180101; A61P 37/06 20180101; A61K 31/55 20130101; A61P 3/04
20180101; A61P 29/00 20180101; A61P 35/00 20180101; A61P 25/28
20180101; A61P 35/02 20180101; A61K 31/4355 20130101; A61P 17/06
20180101; A61P 31/12 20180101; A61P 19/10 20180101; A61K 31/496
20130101; A61P 1/00 20180101; A61P 43/00 20180101; C07D 471/04
20130101; C07D 491/048 20130101; A61P 37/08 20180101; A61P 11/00
20180101; A61P 3/00 20180101; A61P 19/02 20180101; A61P 31/22
20180101; A61P 9/00 20180101; A61P 25/00 20180101; C07D 487/04
20130101; A61P 13/12 20180101 |
Class at
Publication: |
424/133.1 ;
514/355; 514/43; 424/649; 514/171; 514/356; 514/300; 546/113;
544/281; 514/259.1; 514/255.05; 544/405; 546/115; 514/302; 514/301;
546/114; 544/362; 514/253.04; 514/233.2; 544/127; 540/579;
514/214.02 |
International
Class: |
C07D 495/04 20060101
C07D495/04; A61K 31/437 20060101 A61K031/437; C07D 471/04 20060101
C07D471/04; C07D 487/04 20060101 C07D487/04; A61K 31/519 20060101
A61K031/519; A61K 31/55 20060101 A61K031/55; C07D 491/048 20060101
C07D491/048; A61K 31/4355 20060101 A61K031/4355; A61K 31/4365
20060101 A61K031/4365; A61K 31/496 20060101 A61K031/496; A61K
31/5377 20060101 A61K031/5377; A61K 45/06 20060101 A61K045/06; A61K
31/497 20060101 A61K031/497 |
Claims
1. Compounds of formula IIB or pharmaceutically acceptable salts
thereof: ##STR00129## wherein: R is bicyclic heteroaryl comprising
1, 2, 3 or 4 heteroatom(s) independently selected from the group
consisting of N, S and O, wherein said heteroaryl may be
substituted by one or more substituents selected from the group
consisting of amino, oxo, and halo; and wherein said heteroaryl can
comprise one or more N-oxide(s) formed with a N atom member of said
heteroaryl; R.sup.1 is --NHR.sup.4 and R.sup.4 is cycloalkyl,
heterocycloalkyl, aryl or heteroaryl; cycloalkyl; aryl; or
heteroaryl; wherein: (i) each of said cycloalkyl, aryl, or
heteroaryl is unsubstituted or substituted with 1, 2, 3, 4 or 5
substituents which can be the same or different and are
independently selected from the group consisting of: deuterium,
halo, hydroxy, hydroxyalkyl, cyano,
--(CH.sub.2).sub.mNR.sup.aR.sup.b, oxo, alkyl, cyanoalkyl,
haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl-, alkenyl, alkynyl,
alkynylalkoxy, --CONH.sub.2, --S-alkyl, --C(O)NH(alkyl),
--C(O)N(alkyl).sub.2, --C(O)NH(cycloalkyl), --C(O)NH(aryl),
--C(O)N(aryl).sub.2, arylalkyl-, arylalkoxy-, aryloxy-, cycloalkyl,
heterocycloalkyl, aryl, (heterocycloalkyl)alkyl-,
(heterocycloalkyl)alkoxy-, --C(O)heterocycloalkyl, heteroaryl,
(heteroaryl)alkyl-, --S(O).sub.2-alkyl, --S(O).sub.2-aryl,
--S(O).sub.2--CH.sub.zF.sub.3-z, --C(O)alkyl,
--N(R.sup.5)--C(O)-alkyl, --N(R.sup.5)--C(O)-aryl,
--S(O.sub.2)NH.sub.2, --S(O.sub.2)NH(alkyl),
--S(O.sub.2)N(alkyl).sub.2, --N(H)(SO.sub.2)(alkyl), and
methylenedioxy, wherein each of said cycloalkyl, heterocycloalkyl,
aryl or heteroaryl may be substituted by one or more halo, cyano,
alkyl or alkoxy and; (ii) each of said cycloalkyl,
heterocycloalkyl, aryl, or heteroaryl may optionally additionally
be fused with independently selected aryl, heteroaryl,
heterocycloalkyl or cycloalkyl to from a bicyclic or tricyclic
group that may be substituted by one or more halo, cyano, alkyl or
alkoxy; R.sup.2 and R.sup.3 can be independently selected from the
group consisting of H and deuterium; R.sup.5 is H, alkyl or
arylalkyl-; R.sup.a and R.sup.b are independently selected from the
group consisting of H, alkyl, alkoxy, alkoxyalkyl and haloalkyl; m
is 0, 1, 2, 3, 4, 5 or 6; and z is 0, 1 or 2.
2. The compounds of claim 1, wherein R is selected from 9 to 10
membered bicyclic heteroaryl groups containing 1, 2, 3 or 4
heteroatoms independently selected from the group consisting of N,
S and O.
3. The compounds of claim 1, wherein R is selected from the group
consisting of: benzothiazole, dihydronaphthyridine,
dihydropyridopyrimidine, dihydropyrrolopyridine, furopyridine,
imidazopyrazine, imidazopyrazole imidazopyridine,
imidazopyrimidine, indazole, indole, isoquinoline, naphthyridine,
pyrazolopyridine, pyrrolopyridine, tetrazolopyridine,
tetrahydroimidazopyridine, tetrahydropyrazolopyridine,
thiazolopyridine and thienopyridine.
4. The compounds of claim 1, wherein R is selected from the group
consisting of: 1H-pyrazolo[3,4-b]pyridine;
1,4,6,7-Tetrahydro-pyrazolo[4,3-c]pyridine;
7,8-Dihydro-5H-pyrido[4,3-d]pyrimidine;
5,7-Dihydro-pyrrolo[3,4-b]pyridine;
7,8-Dihydro-5H-[1,6]naphthyridine;
1,4,6,7-Tetrahydro-imidazo[4,5-c]pyridine;
1,8a-dihydroimidazo[1,2-a]pyridine; thieno[3,2-c]pyridine;
1H-imidazo[1,2-b]pyrazole; 1H-pyrazolo[3,4-b]pyridine;
furo[2,3-c]pyridine; 1H-pyrazolo[3,4-b]pyridine;
1H-pyrrolo[3,2-c]pyridine; thieno[2,3-b]pyridine;
imidazo[1,2-a]pyrimidine; furo[2,3-c]pyridine; isoquinoline;
1H-indazole; imidazo[1,2-a]pyridine; thieno[2,3-c]pyridine;
furo[2,3-c]pyridine; 1H-pyrrolo[2,3-c]pyridine;
imidazo[1,2-a]pyrazine; 1,3-benzothiazole; benzo[d]thiazole;
1H-pyrrolo[2,3-b]pyridine; [1,3]thiazolo[5,4-c]pyridine;
[1,2,3,4]tetrazolo[1,5-a]pyridine; 1,5-naphthyridine; 1H-indole;
1H-imidazo[4,5-c]pyridine; and 1,6-naphthyridine.
5. The compounds of claim 1, wherein R is substituted at a position
adjacent to a nitrogen atom on its cycle.
6. The compounds of claim 1, wherein R is selected from the group
consisting of: ##STR00130##
7. The compounds of claim 1, wherein R.sup.1 is --NHR.sup.4, and
R.sup.4 is cycloalkyl, heterocycloalkyl, aryl or heteroaryl.
8. The compounds of claim 7, wherein R.sup.4 is unsubstituted or
substituted cycloalkyl.
9. The compounds of claim 7, wherein R.sup.4 is unsubstituted or
substituted heterocycloalkyl.
10. The compounds of claim 7, wherein R.sup.4 is unsubstituted or
substituted aryl.
11. The compounds of claim 7, wherein R.sup.4 is unsubstituted or
substituted heteroaryl.
12. The compounds of claim 1, wherein R.sup.1 is unsubstituted or
substituted C.sub.3-C.sub.10-cycloalkyl.
13. The compounds of claim 1, wherein R.sup.1 is unsubstituted or
substituted aryl.
14. The compounds of claim 1, wherein R.sup.1 is unsubstituted or
substituted 5 to 10 membered monocyclic or bicyclic heteroaryl
comprising 1, 2, 3 or 4 heteroatom(s) selected from the group
consisting of N, S and O.
15. The compounds of claim 7, wherein R.sup.1 or R.sup.4 is
selected from the group consisting of: 6-methoxypyridine;
2-ethoxy-4-fluorophenyl; 3,4-difluorophenyl; 3,4-dimethoxyphenyl;
3,4-dimethoxyphenyl; 3-chloro-5-fluorophenyl;
3-fluoro-4-methoxyphenyl; 4-chloro-2-methylphenyl;
4-fluoro-2-methoxyphenyl; 4-methoxy-2,5-dimethylphenyl;
4-methylphenyl; 5-chloro-2-ethoxyphenyl; 5-fluoro-2-methoxyphenyl;
1-(3-chlorophenyl)-1H-pyrazole; 1-(4-fluorophenyl)-1H-pyrazole;
1-(propan-2-yl)-1H-pyrazole; 1,3-thiazole;
1,4-dimethyl-1H-imidazole; 1,5-dimethyl-1H-imidazole;
1-benzothiophene; 1H-indole; 1-methyl-1H-1,3-benzodiazole;
1-methyl-1H-indazole; 1-methyl-1H-indole; 1-methyl-1H-pyrazole;
1-methyl-3-(trifluoromethyl)-1H-pyrazole;
1-methyl-5-(trifluoromethyl)-1H-pyrazole; 1-propyl-1H-pyrazole;
2-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)phenyl;
2-(3-fluorophenyl)-1,3-thiazole;
2-(benzyloxy)-5-(trifluoromethyl)phenyl; 2-(benzyloxy)phenyl;
2-(dimethylamino)pyrimidine; 2-(dimethylcarbamoyl)phenyl;
2-(ethoxymethyl)phenyl; 2-(methylsulfamoyl)phenyl;
2-(morpholin-4-yl)pyridine; 2-(morpholin-4-yl)pyridine;
2-(morpholin-4-ylmethyl)phenyl; 2-(pyrrolidin-1-yl)-1,3-thiazole;
2-(trifluoromethoxy)phenyl; 2-(trifluoromethoxy)phenyl];
2-(trifluoromethyl)imidazo[1,2-a]pyridine;
2-(trifluoromethyl)phenyl; 2-(trifluoromethyl)pyridine;
2,3,6-trimethoxyphenyl; 2,3-difluoro-6-methoxyphenyl;
2,3-difluorophenyl; 2,3-dihydro-1,4-benzodioxine;
2,3-dihydro-1-benzofuran; 2,3-dihydro-1-benzofuranphenyl;
2,3-dimethoxy-5-methylphenyl; 2,3-dimethoxyphenyl;
2,3-dimethylphenyl; 2,4,5-trimethylphenyl;
2,4-bis(trifluoromethyl)phenyl; 2,4-dichloro-3-methoxyphenyl;
2,4-difluorophenyl; 2,4-dimethoxyphenyl; 2,4-dimethylphenyl;
2,5-difluorophenyl; 2,5-dimethoxyphenyl; 2,5-dimethylphenyl;
2,6-dichloro-3-methylphenyl; 2,6-dichlorophenyl;
2,6-dimethoxy-4-methylphenyl; 2,6-dimethoxypyridine;
2,6-dimethylphenyl; 2-[ethyl(methyl)amino]-1,3-thiazole;
2-acetylphenyl; 2-butoxy-4-fluorophenyl; 2-butoxy-5-chlorophenyl;
2-butoxy-6-fluorophenyl; 2-chloro-3-(trifluoromethyl)phenyl;
2-chloro-3-fluorophenyl; 2-chloro-4-(trifluoromethyl)phenyl;
2-chloro-4-fluorophenyl; 2-chloro-4-methoxyphenyl;
2-chloro-4-methylphenyl; 2-chloro-5-(hydroxymethyl)phenyl;
2-chloro-5-(trifluoromethoxy)phenyl;
2-chloro-5-(trifluoromethyl)phenyl; 2-chloro-5-fluorophenyl;
2-chloro-5-methoxyphenyl; 2-chloro-5-methoxyphenyl;
2-chloro-5-methylphenyl; 2-chloro-6-fluorophenyl;
3-trifluoromethylphenyl; 2-chloro-6-methoxyphenyl; 2-chlorophenyl;
2-cyanophenyl; 2-ethoxy-4-fluorophenyl; 2-ethoxy-6-fluorophenyl;
2-ethoxyphenyl; 2-ethylphenyl; 2-fluoro-3-(propan-2-yloxy)phenyl;
2-fluoro-3-(trifluoromethoxy)phenyl; 2-fluoro-3-methoxyphenyl;
2-fluoro-3-methylphenyl; 2-fluoro-4-(1H-pyrazol-1-yl)phenyl;
2-fluoro-4-(trifluoromethyl)phenyl; 2-fluoro-4-methoxyphenyl;
2-fluoro-4-methylphenyl; 2-fluoro-5-methoxyphenyl;
2-fluoro-5-methylphenyl; 2-fluoro-6-methoxyphenyl;
2-fluoro-6-propoxyphenyl; 2-fluorophenyl; 2H-1,3-benzodioxole;
2-methanesulfonamidophenyl; 2-methanesulfonylphenyl;
2-methoxy-3-(trifluoromethyl)phenyl;
2-methoxy-4-(1H-pyrazol-1-yl)phenyl;
2-methoxy-4-(trifluoromethyl)phenyl;
2-methoxy-5-(propan-2-yl)phenyl;
2-methoxy-5-(trifluoromethoxy)phenyl; 2-methoxy-5-methylphenyl;
2-methoxy-6-(propan-2-yloxy)phenyl; 2-methoxyphenyl;
2-methyl-1,3-thiazole; 2-methyl-2H-indazole;
2-methyl-4-(1H-pyrazol-1-yl)phenyl;
2-methyl-4-(trifluoromethyl)phenyl; 2-methyl-4-propoxyphenyl;
2-methylphenyl; 2-methylpyridine; 2-phenoxyphenyl; 2-phenylethane;
3-(1H-pyrazol-1-yl)phenyl; 3-(2,2,2-trifluoroethoxy)phenyl;
3-(2-methylpropoxy)phenyl; 3-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl;
3-(4-fluorophenoxy)phenyl; 3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl;
3-(cyclopentylcarbamoyl)phenyl;
3-(diethylcarbamoyl)-5-fluorophenyl; 3-(difluoromethoxy)phenyl;
3-(dimethylsulfamoyl)phenyl; 3-(ethanesulfonyl)phenyl;
3-(ethylcarbamoyl)phenyl; 3-(methoxymethyl)phenyl,
3-(methylcarbamoyl)phenyl; 3-(morpholin-4-yl)phenyl;
3-(piperidin-1-yl)phenyl; 3-(piperidin-1-ylmethyl)phenyl;
3-(piperidin-1-ylphenyl; 3-(propan-2-yl)phenyl;
3-(propan-2-yloxy)phenyl; 3-(propane-1-sulfonamido)phenyl;
3-(pyrimidin-2-yl)phenyl; 3-(trifluoromethoxy)phenyl;
3-(trifluoromethyl)phenyl; 3,4-dichlorophenyl; 3,4-dimethoxyphenyl;
3,4-dimethylphenyl; 3,5-dichlorophenyl; 3,5-difluorophenyl;
3,5-dimethoxyphenyl; 3,5-dimethylphenyl;
3-[(2-methylpropyl)carbamoyl]phenyl;
3-[(dimethylamino)methylphenyl; 3-[(morpholin-4-yl)carbonyl]phenyl;
3-[(propan-2-yl)carbamoyl]phenyl; 3-[2-(dimethylamino)ethoxyphenyl;
3-[2-(dimethylamino)ethyl]phenyl;
3-[2-(morpholin-4-yl)ethoxy]phenyl; 3-acetylphenyl; 3-butoxyphenyl;
3-chloro-2-(morpholin-4-yl)pyridine; 3-chloro-2-fluorophenyl;
3-chloro-2-methoxyphenyl; 3-chloro-2-methylphenyl;
3-chloro-4-(trifluoromethyl)phenyl; 3-chloro-4-methoxyphenyl;
3-chloro-4-methylphenyl; 3-chloro-4-propoxyphenyl;
3-chloro-5-(diethylcarbamoyl)phenyl;
3-chloro-5-(hydroxymethyl)phenyl; 3-chloro-5-fluorophenyl;
3-chloro-5-methoxyphenyl; 3-chloro-5-methylphenyl; 3-chlorophenyl;
3-cyanophenyl; 3-ethoxy-2-fluorophenyl; 3-ethoxy-4-fluorophenyl;
3-ethoxyphenyl; 3-ethylphenyl; 3-fluoro-2-methoxyphenyl;
3-fluoro-2-methylphenyl; 3-fluoro-2-methylphenyl;
3-fluoro-4-(1H-pyrazol-1-yl)phenyl;
3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl;
3-fluoro-4-(methylsulfanyl)phenyl;
3-fluoro-4-(trifluoromethoxy)phenyl;
3-fluoro-4-(trifluoromethyl)phenyl; 3-fluoro-4-methoxyphenyl;
3-fluoro-4-methylphenyl; 3-fluoro-4-propoxyphenyl;
3-fluoro-5-(2,2,2-trifluoroethoxy)phenyl;
3-fluoro-5-(2-methylpropoxy)phenyl;
3-fluoro-5-(morpholin-4-yl)phenyl;
3-fluoro-5-(pyrrolidin-1-yl)phenyl;
3-fluoro-5-(trifluoromethyl)phenyl; 3-fluoro-5-methoxyphenyl;
3-fluoro-5-methylphenyl; 3-fluorophenyl; 3-hydroxyphenyl;
3-methanesulfonylphenyl; 3-methoxy-4-methylphenyl;
3-methoxy-5-methylphenyl; 3-methoxyphenyl; 3-methylphenyl;
3-phenylphenyl; 3-phenylpropane; 3-propoxyphenyl;
3-sulfamoylphenyl; 3-tert-butylphenyl;
4-(1-cyanocyclopentyl)phenyl; 4-(1H-imidazol-1-yl)phenyl;
4-(1H-imidazol-1-ylmethyl)phenyl; 4-(1H-pyrazol-1-yl)phenyl;
4-(2-methylpropoxy)phenyl; 4-(4-ethoxyphenyl)phenyl;
4-(4-methylpiperazin-1-yl)phenyl;
4-(difluoromethyl)-3-fluorophenyl; 4-(dimethylcarbamoyl)phenyl;
4-(ethoxymethyl)phenyl; 4-(ethylcarbamoyl)phenyl;
4-(hydroxymethyl)phenyl; 4-(morpholin-4-yl)phenyl;
4-(propan-2-yl)phenyl; 4-(propan-2-yloxy)phenyl;
4-(pyrrolidin-1-yl); 4-(pyrrolidin-1-yl)phenyl;
4-(trifluoromethoxy)phenyl; 4-(trifluoromethyl)phenyl;
4-(trifluoromethyl)pyridine; 3,5-difluorophenyl;
4,5-difluoro-2-methoxyphenyl; 4-[(1R)-1-hydroxybutylphenyl;
(dimethylamino)methylphenyl; 4-[(pyrrolidin-1-yl)carbonyl]phenyl;
4-[2-(dimethylamino)ethyl]phenyl;
4-[2-(pyrrolidin-1-yl)ethoxy]phenyl; 4-acetylphenyl;
4-butoxy-2-methylphenyl; 4-butoxy-3-chlorophenyl;
4-butoxy-3-fluorophenyl; 4-butoxyphenyl; 4-butylphenyl;
4-chloro-2-(trifluoromethyl)phenyl; 4-chloro-2-ethoxyphenyl;
4-chloro-2-methoxyphenyl; 4-chloro-2-methylphenyl;
4-chloro-3-(trifluoromethyl)phenyl; 4-chloro-3-fluorophenyl;
4-chloro-3-methoxyphenyl; 4-chlorophenyl; 4-cyanophenyl;
4-cyclohexylphenyl; 4-ethoxy-2-methylphenyl;
4-ethoxy-3-fluorophenyl; 4-ethoxyphenyl; 4-ethylphenyl;
4-fluoro-2-(propan-2-yloxy)phenyl; 4-fluoro-2,5-dimethylphenyl;
4-fluoro-2-methoxyphenyl; 4-fluoro-2-methylphenyl;
4-fluoro-3-(2,2,2-trifluoroethoxy)phenyl;
4-fluoro-3-(trifluoromethyl)phenyl;
4-fluoro-3-[(propan-2-yl)carbamoyl]phenyl;
4-fluoro-3-methoxyphenyl; 4-fluoro-3-methylphenyl; 4-fluorophenyl;
4-methanesulfonylphenyl; 4-methoxy-2-(trifluoromethyl)phenyl;
4-methoxy-2,5-dimethylphenyl; 4-methoxy-2-methylphenyl;
4-methoxy-3,5-dimethylphenyl; 4-methoxy-3-methylphenyl;
4-methoxyphenyl; 4-methylphenyl; 4-methylpyridine;
4-methylthiophene; 4-phenylbutane; 4-phenylphenyl; 4-phenyl-phenyl;
4-propoxyphenyl; 3,5-difluorophenyl;
5-(diethylcarbamoyl)-2-fluorophenyl; 5-(dimethylamino)pyrazine;
5-(pyrrolidin-1-yl)pyridine; 5-(trifluoromethyl)pyridine;
5-acetyl-2-methoxyphenyl; 5-chloro-2-(2,2,2-trifluoroethoxy)phenyl;
5-chloro-2-(2,2-difluoroethoxy)phenyl;
5-chloro-2-(prop-2-yn-1-yloxy)phenyl;
5-chloro-2-(propan-2-yloxy)phenyl; 5-chloro-2-ethoxyphenyl;
5-chloro-2-hydroxyphenyl; 5-chloro-2-methoxyphenyl;
5-chloro-2-methylphenyl; 5-chloro-2-propoxyphenyl;
5-chloropyridine; 5-cyano-2-methoxyphenyl;
5-fluoro-2-(hydroxymethyl)phenyl; 5-fluoro-2-methoxyphenyl;
5-fluoro-2-methylphenyl; 5-fluoro-6-methylpyridine;
5-fluoropyridine; 5H,6H,7H,8H,9H-imidazo[1,2-a]azepine;
5H,6H,7H,8H,9H-imidazo[1,2-a]azepinephenyl;
5-hydroxy-(4-phenylphenyl); 5-hydroxy-1-methyl-1H-indazole;
5-hydroxy-2-(trifluoromethoxy)phenyl;
5-hydroxy-3-(morpholin-4-yl)phenyl;
5-hydroxy-3-(piperidin-1-ylphenyl;
5-hydroxy-3-(pyrrolidin-1-ylphenyl; 5-methoxypyridine;
5-methylpyridine; 5-methylthiophene; 5-tert-butyl-2-methoxyphenyl;
6-(1H-pyrazol-1-yl)pyridine; 6-(3,4-difluorophenyl)pyridine;
6-(4-methylpiperazin-1-yl)pyridine; 6-(dimethylamino)pyridine;
6-(morpholin-4-yl)pyridine; 6-(trifluoromethyl)pyridine;
6-amino-(3,5-difluorophenyl); 6-chloro-2-fluoro-3-methylphenyl;
6-chloroimidazo[1,2-a]pyridine;
6-chloroimidazo[1,2-a]pyridinephenyl; 6-methoxynaphthalene;
6-methoxypyridine; 6-methylpyrazine; 6-methylpyridine;
8-thiatricyclo[7.4.0.0.sup.2,7]trideca-1(13),2,4,6,9,11-hexaene;
b6-chloroimidazo[1,2-a]pyridine; Cyclohexane;
dimethyl-1,3-thiazole; furan; isoquinoline; naphthalene;
naphthalenephenyl; phenoxathiine; phenyl; pyridine; and
quinoline.
16. The compounds of claim 1, wherein R.sup.1 is cycloalkyl, aryl
or heteroaryl, wherein each of said cycloalkyl, aryl, or heteroaryl
is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents
which can be the same or different and are independently selected
from the group consisting of: halo, hydroxy, hydroxyalkyl, cyano,
alkyl, alkynyl, alkynylalkoxy, alkoxyalkyl, alkoxy, haloalkyl,
haloalkoxy, --C(O)NH(alkyl), --C(O)NH(cycloalkyl),
--C(O)N(alkyl).sub.2, arylalkoxy-, aryloxy-, cycloalkyl,
heterocycloalkyl, aryl, (heterocycloalkyl)alkyl-,
(heterocycloalkyl)alkoxy-, --C(O)heterocycloalkyl, heteroaryl,
(heteroaryl)alkyl-, --S(O).sub.2-alkyl, --S-alkyl, --C(O)alkyl,
--S(O.sub.2)NH.sub.2, --S(O.sub.2)NH(alkyl),
--S(O.sub.2)N(alkyl).sub.2, and --N(H)(SO.sub.2)(alkyl), wherein
each of said cycloalkyl, heterocycloalkyl, aryl or heteroaryl may
be substituted by one or more halo, cyano, alkyl or alkoxy; and z
is 0, 1 or 2.
17. The compounds of claim 1, wherein R.sup.1 is cycloalkyl, aryl
or heteroaryl, wherein each of said cycloalkyl, aryl, or heteroaryl
is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents
which can be the same or different and are independently selected
from the group consisting of: halo, haloalkyl and haloalkoxy.
18. The compounds of claim 1, wherein haloalkyl is
--CH.sub.zF.sub.3-z or --CH.sub.2CH.sub.zF.sub.3-z, and z is 0, 1
or 2.
19. The compounds of claim 1, wherein haloalkoxy is
--OCH.sub.zF.sub.3-z, and z is 0, 1 or 2.
20. The compounds of claim 1, wherein halo is F.
21. The compounds of claim 1, wherein R is
1H-pyrazolo[3,4-b]pyridine.
22. The compounds of claim 1, wherein R is
1,8a-dihydroimidazo[1,2-a]pyridine.
23. A compound selected from the group consisting of:
N-[4-(piperidine-1-sulfonyl)phenyl]-3-(pyridin-3-yl)propanamide
N-[4-(piperidine-1-sulfonyl)phenyl]-2-(pyridin-3-yloxy)acetamide
N-[4-(piperidine-1-sulfonyl)phenyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxami-
de
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-2-
-carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}thieno[2,3-b]pyridine-2-carbox-
amide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1H-pyrrolo[2,3-c]pyridin-
e-2-carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1H-indazole-5-carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-5--
carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-carbo-
xamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1H-imidazo[1,2-b]pyrazo-
le-5-carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}thieno[3,2-c]pyridine-2-carbox-
amide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-[1,2,3,4]tetrazolo[1,5-a-
]pyridine-7-carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-7-carbo-
xamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1,6-naphthyridine-2-car-
boxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}pyridine-3-carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1H-1,3-benzodiazole-5-carboxa-
mide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1,3-benzothiazole-6-carbo-
xamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}furo[3,2-c]pyridine-2-ca-
rboxamide
N-{1-[4-(piperidine-1-sulfonyl)phenyl]ethyl}-1H-pyrrolo[3,2-c]py-
ridine-2-carboxamide
N-[(4-{8-oxa-3-azabicyclo[3.2.1]octane-3-sulfonyl}phenyl)methyl]thieno[2,-
3-c]pyridine-2-carboxamide
N-[(4-{8-oxa-3-azabicyclo[3.2.1]octane-3-sulfonyl}phenyl)methyl]-1H-pyrro-
lo[3,2-c]pyridine-2-carboxamide
N-[(4-{8-oxa-3-azabicyclo[3.2.1]octane-3-sulfonyl}phenyl)methyl]imidazo[1-
,2-a]pyridine-6-carboxamide N-({4-[(5-chloro-2-methoxyphenyl)
sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-acetylphenyl)
sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-chloro-2-methoxy-5-methylphenyl)sulfamoyl]phenyl}methyl)-1H-pyr-
rolo[3,2-c]pyridine-2-carboxamide N-({4-[(2-propoxyphenyl)
sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(5-fluoro-2-methoxyphenyl)sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(quinolin-8-yl)sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine--
2-carboxamide
N-[(4-{[2-(piperidin-1-yl)phenyl]sulfamoyl}phenyl)methyl]-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-[(4-{[2-(morpholin-4-yl)phenyl]sulfamoyl}phenyl)methyl]-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide N-({4-[(5-methoxy-2-methylphenyl)
sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(propan-2-yloxy)phenyl]sulfamoyl}phenyl)methyl]-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(2-phenoxyphenyl)sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridin-
e-2-carboxamide N-({4-[(3-methoxy-2-methylphenyl)
sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-2-methoxyphenyl)sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-[(4-{[2-(trifluoromethoxy)phenyl]sulfamoyl}phenyl)methyl]-1H-pyrrolo[3,-
2-c]pyridine-2-carboxamide
N-({4-[(5,6,7,8-tetrahydronaphthalen-1-yl)sulfamoyl]phenyl}methyl)-1H-pyr-
rolo[3,2-c]pyridine-2-carboxamide N-({4-[(2-methoxyphenyl)
sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-methoxy-6-methylphenyl)
sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-methoxy-2-methylphenyl)
sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2,3-dihydro-1,4-benzodioxin-6-yl)sulfamoyl]phenyl}methyl)-1H-pyrr-
olo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(2-hydroxyethoxy)phenyl]sulfamoyl}phenyl)methyl]-1H-pyrrolo[3,2-
-c]pyridine-2-carboxamide N-({4-[(4-ethoxy-2-fluorophenyl)
sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(hydroxymethyl)phenyl]sulfamoyl}phenyl)methyl]-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-({4-[(1-oxo-1H-isochromen-5-yl)sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-[(4-benzenesulfonamidophenyl)methyl]-1H-pyrrolo[3,2-c]pyridine-2-carbox-
amide
N-{[1-(benzenesulfonyl)piperidin-4-yl]methyl}-1H-pyrrolo[3,2-c]pyrid-
ine-2-carboxamide
N-[(4-benzamidophenyl)methyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(trifluoromethoxy)benzene]sulfonamido}phenyl)methyl]-1H-pyrrolo-
[3,2-c]pyridine-2-carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-carbox-
amide N-({4-[(2,5-dimethoxyphenyl)
sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-methoxy-5-(trifluoromethyl)phenyl]sulfamoyl}phenyl)methyl]-1H-p-
yrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-chloro-2-(trifluoromethoxy)phenyl]sulfamoyl}phenyl)methyl]-1H-p-
yrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(1H-indazol-6-yl)sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridin-
e-2-carboxamide 6-Amino-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid
4-(piperidine-1-sulfonyl)-benzylamide
1H-Pyrrolo[3,2-c]pyridine-2-carboxylic acid
4-(piperazine-1-sulfonyl)-benzylamide
1H-Pyrrolo[3,2-c]pyridine-2-carboxylic acid
4-(4-amino-cyclohexylsulfamoyl)-benzylamide
1H-Pyrrolo[3,2-c]pyridine-2-carboxylic acid
4-(3-amino-pyrrolidine-1-sulfonyl)-benzylamide
1H-Pyrrolo[3,2-c]pyridine-2-carboxylic acid
4-(3,8-diaza-bicyclo[3.2.1]octane-3-sulfonyl)-benzylamide
Imidazo[1,2-a]pyrimidine-6-carboxylic acid
4-(piperazine-1-sulfonyl)-benzylamide
Thieno[2,3-c]pyridine-2-carboxylic acid
4-(piperazine-1-sulfonyl)-benzylamide
1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid
4-(piperazine-1-sulfonyl)-benzylamide
Thieno[2,3-c]pyridine-2-carboxylic acid
4-(4-amino-cyclohexylsulfamoyl)-benzylamide
Furo[2,3-c]pyridine-2-carboxylic acid
4-(4-amino-cyclohexylsulfamoyl)-benzylamide
1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid
4-(4-amino-cyclohexylsulfamoyl)-benzylamide
Thieno[2,3-c]pyridine-2-carboxylic acid
4-(3-amino-pyrrolidine-1-sulfonyl)-benzylamide
Imidazo[1,2-a]pyridine-6-carboxylic acid
4-(3-amino-pyrrolidine-1-sulfonyl)-benzylamide
Furo[2,3-c]pyridine-2-carboxylic acid
4-(3-amino-pyrrolidine-1-sulfonyl)-benzylamide
1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid
4-(3-amino-pyrrolidine-1-sulfonyl)-benzylamide
Imidazo[1,2-a]pyridine-6-carboxylic acid
4-(piperazine-1-sulfonyl)-benzylamide
Furo[2,3-c]pyridine-2-carboxylic acid
4-(piperazine-1-sulfonyl)-benzylamide
Imidazo[1,2-a]pyrimidine-6-carboxylic acid
4-(3-amino-pyrrolidine-1-sulfonyl)-benzylamide
Imidazo[1,2-a]pyrimidine-6-carboxylic acid
4-(4-amino-cyclohexylsulfamoyl)-benzylamide
Imidazo[1,2-a]pyridine-6-carboxylic acid
4-(4-amino-cyclohexylsulfamoyl)-benzylamide
1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid
4-(4-cyano-piperidine-1-sulfonyl)-benzylamide
1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid
4-(4-cyanomethyl-piperidine-1-sulfonyl)-benzylamide
1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid
4-(4-methoxy-piperidine-1-sulfonyl)-benzylamide
1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid
4-(4-amino-piperidine-1-sulfonyl)-benzylamide
1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid
4-[4-(2,2,2-trifluoro-ethylamino)-piperidine-1-sulfonyl]-benzylamide
N-({4-[1-(3-chlorophenyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)-1H-pyrazo-
lo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-{[4-(dimethyl-1,3-thiazole-5-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]-
pyridine-5-carboxamide
N-[(4-{[2-fluoro-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-({4-[(2-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[(5-acetyl-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(2-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-[(4-{[3-fluoro-5-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-
imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[1-methyl-5-(trifluoromethyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)-
imidazo[1,2-a]pyrimidine-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl} isoquinoline-6-carboxamide
N-[(4-{[3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-[(4-{[3-(piperidin-1-ylmethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,-
2-a]pyridine-6-carboxamide
N-({4-[6-(trifluoromethyl)pyridine-3-sulfonyl]phenyl}methyl)thieno[2,3-c]-
pyridine-2-carboxamide
N-({4-[(4-butylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-ca-
rboxamide
N-{[4-(2-methylpyridine-3-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-
-c]pyridine-2-carboxamide
N-({4-[(4-methoxy-3,5-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]p-
yridine-2-carboxamide
N-({4-[(4-butoxy-3-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-{[4-(2-methyl-2H-indazole-6-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]p-
yridine-5-carboxamide
N-({4-[(2-methanesulfonylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-[(4-{[3-chloro-5-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[-
1,2-a]pyrimidine-6-carboxamide
N-[(4-{[3-(diethylcarbamoyl)-5-fluorobenzene]sulfonyl}phenyl)methyl]furo[-
2,3-c]pyridine-2-carboxamide
N-({4-[(2-chloro-6-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(3-chloro-4-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(2,3-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyri-
dine-2-carboxamide
N-[(4-{[3-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(4-acetylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
-carboxamide
N-{[4-({3-[(2-methylpropyl)carbamoyl]benzene}sulfonyl)phenyl]methyl}-1H-p-
yrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-chloro-6-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(3-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[6-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)furo[2,3-c]py-
ridine-2-carboxamide
N-{[4-({4-[2-(pyrrolidin-1-yl)ethoxy]benzene}sulfonyl)phenyl]methyl}-1H-p-
yrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(4-butoxy-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(4-fluoro-2,5-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a-
]pyrimidine-6-carboxamide
N-[(4-{[2-methyl-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-({4-[(3-ethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridine-
-5-carboxamide
N-({4-[(3-phenylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-c-
arboxamide
N-({4-[(2-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo-
[1,2-a]pyridine-6-carboxamide
N-({4-[(2-chloro-3-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-[(4-{[5-chloro-2-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-
imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[(4-butoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-c-
arboxamide
N-({4-[6-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)-1H-
-pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyri-
dine-2-carboxamide
N-({4-[(5-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-{[4-({3-[2-(morpholin-4-yl)ethoxy]benzene}sulfonyl)phenyl]methyl}thieno-
[2,3-c]pyridine-2-carboxamide
N-({4-[(3-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[(4-ethoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(4-chlorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carb-
oxamide
N-({4-[(4-ethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridin-
e-2-carboxamide
N-({4-[(4-ethoxy-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(3-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-[(4-{[4-(1-cyanocyclopentyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2--
a]pyrimidine-6-carboxamide
N-({4-[(3-propoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-c-
arboxamide
N-[(4-{[3-fluoro-4-(trifluoromethoxy)benzene]sulfonyl}phenyl)me-
thyl]imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[(4-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(3-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-[(4-{8-thiatricyclo[7.4.0.0.sup.2,7]trideca-1(13),2,4,6,9,11-hexaene-6--
sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-7-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine--
2-carboxamide
N-{[4-(5-chloro-3-methylpyridine-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-{[4-(isoquinoline-4-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-carb-
oxamide
N-({4-[(5-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
-c]pyridine-2-carboxamide
N-({4-[(3-fluoro-4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-[(4-{[3-chloro-5-(diethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imida-
zo[1,2-a]pyrimidine-6-carboxamide
N-({4-[(3,4-difluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2--
carboxamide
N-[(4-{[3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]py-
ridine-2-carboxamide
N-[(4-{[4-(4-methylpiperazin-1-yl)benzene]sulfonyl}phenyl)methyl]imidazo[-
1,2-a]pyridine-6-carboxamide
N-[(4-{[2-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-b-
]pyridine-5-carboxamide
N-({4-[6-(morpholin-4-yl)pyridine-3-sulfonyl]phenyl}methyl)-1H-pyrazolo[3-
,4-b]pyridine-5-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-pyrrolo[2,3-c]pyridine-3-carboxa-
mide
N-[(4-{[3-fluoro-4-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)met-
hyl]imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[(3-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(2-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-{[4-(quinoline-6-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-5-c-
arboxamide
N-{[4-(1-methyl-1H-indazole-5-sulfonyl)phenyl]methyl}imidazo[1,-
2-a]pyridine-6-carboxamide
N-({4-[(5-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-{[4-(1-propyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]p-
yridine-5-carboxamide
N-({4-[(3,4-dimethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
-2-carboxamide
N-({4-[(3-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(4-ethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carbo-
xamide
N-({4-[(2,4,5-trimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]-
pyridine-2-carboxamide
N-({4-[2-(trifluoromethyl)imidazo[1,2-a]pyridine-6-sulfonyl]phenyl}methyl-
)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[(4-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-[(4-{[2-fluoro-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-({4-[(2-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-({4-[(3-chloro-4-propoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-({4-[(2-fluoro-6-propoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-[(4-{[2-(morpholin-4-ylmethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
-c]pyridine-2-carboxamide
N-({4-[(5-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-[(4-{[2-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)benzene]sulfonyl}phe-
nyl)methyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-[(4-{6-chloroimidazo[1,2-a]pyridine-3-sulfonyl}phenyl)methyl]imidazo[1,-
2-a]pyrimidine-6-carboxamide
N-{2-[4-(benzenesulfonyl)phenyl]ethyl}-1H-pyrrolo[3,2-c]pyridine-2-carbox-
amide
N-[(4-{[3-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,-
3-c]pyridine-2-carboxamide
N-[(4-{[4-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-
-2-carboxamide
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-[(4-{[4-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
-c]pyridine-2-carboxamide
N-({4-[(3-ethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-car-
boxamide
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-b]-
pyridine-2-carboxamide
N-{[4-(6-methoxypyridine-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-c-
arboxamide
N-({4-[6-(dimethylamino)pyridine-3-sulfonyl]phenyl}methyl)-1H-p-
yrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-[(4-{[3-(methoxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(2-butoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(3-hydroxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6--
carboxamide
N-({4-[(3-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-[(4-{[2-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyri-
midine-6-carboxamide
N-{[4-(1-methyl-1H-indazole-4-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimi-
dine-6-carboxamide
N-({4-[(5-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(3-ethoxy-2-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(2-ethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine--
2-carboxamide
N-({4-[(4-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(4-ethoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-[(4-{[3-fluoro-5-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyr-
rolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-fluoro-6-propoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-[(4-{[2-methoxy-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imida-
zo[1,2-a]pyrimidine-6-carboxamide
N-{[4-(2-methylpyridine-3-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2--
carboxamide
N-[(4-{8-oxatricyclo[7.4.0.0.sup.2,7]trideca-1(13),2,4,6,9,11-hexaene-6-s-
ulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-({4-[(4-phenylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-({4-[(2-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
-c]pyridine-2-carboxamide
N-[(4-{[2-fluoro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-({4-[(5-chloro-2-propoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-{[4-(2H-1,3-benzodioxole-5-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]py-
ridine-5-carboxamide
N-{[4-({4-[(1R)-1-hydroxybutyl]benzene}sulfonyl)phenyl]methyl}imidazo[1,2-
-a]pyrimidine-6-carboxamide
N-{[4-(5-methylthiophene-2-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyrid-
ine-2-carboxamide
N-({4-[(3-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-car-
boxamide
N-{[4-({3-[2-(morpholin-4-yl)ethoxy]benzene}sulfonyl)phenyl]methy-
l}imidazo[1,2-a]pyridine-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}imidazo[1,2-a]pyrazine-2-carboxamide
N-({4-[(4-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-c-
arboxamide
N-{[4-(quinoline-8-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
-carboxamide
N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[(3,4-dichlorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2--
carboxamide
N-{[4-({4-fluoro-3-[(propan-2-yl)carbamoyl]benzene}sulfonyl)phenyl]methyl-
}imidazo[1,2-a]pyrimidine-6-carboxamide
N-[(4-{[2,4-bis(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,-
2-a]pyridine-6-carboxamide
N-{[4-(1-methyl-1H-indazole-6-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridin-
e-2-carboxamide
N-[(4-{[3-fluoro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2-
,3-c]pyridine-2-carboxamide
N-({4-[(2-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-[(4-{[2,4-bis(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrol-
o[3,2-c]pyridine-2-carboxamide
N-({4-[(2-methyl-4-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(3-phenylbenzene)sulfonyl]phenyl}methyl)-1,3-benzothiazole-6-carbo-
xamide
N-[(4-{[4-(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c-
]pyridine-2-carboxamide
N-({4-[(4-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine--
6-carboxamide
N-{[4-(1-methyl-1H-indazole-6-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridi-
ne-6-carboxamide
N-[(4-{[3-(cyclopentylcarbamoyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
-c]pyridine-2-carboxamide
N-({4-[(3-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(4,5-difluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2--
a]pyrimidine-6-carboxamide
N-[(4-{[3-(methoxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-[(4-{[3-fluoro-4-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-
thieno[2,3-c]pyridine-2-carboxamide
N-{[4-(2H-1,3-benzodioxole-4-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-
-2-carboxamide
N-[(4-{[5-chloro-2-(prop-2-yn-1-yloxy)benzene]sulfonyl}phenyl)methyl]imid-
azo[1,2-a]pyridine-6-carboxamide
N-({4-[(3-phenylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carb-
oxamide
N-({4-[(4-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3--
c]pyridine-2-carboxamide
N-[(4-{[3-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyrid-
ine-2-carboxamide
N-({4-[(3-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carb-
oxamide
N-({4-[6-(dimethylamino)pyridine-3-sulfonyl]phenyl}methyl)imidazo[-
1,2-a]pyrimidine-6-carboxamide
N-({4-[(5-chloro-2-propoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(4-methoxy-3,5-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2--
a]pyrimidine-6-carboxamide
N-({4-[(3-cyanobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carbo-
xamide
N-({4-[(3-fluoro-4-propoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c-
]pyridine-2-carboxamide
N-({4-[(2,6-dichloro-3-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]py-
ridine-2-carboxamide
N-[(4-{2-[ethyl(methyl)amino]-1,3-thiazole-5-sulfonyl}phenyl)methyl]thien-
o[2,3-c]pyridine-2-carboxamide
N-({4-[(3-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine--
6-carboxamide
N-({4-[(4-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-{[4-(1-propyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]py-
ridine-2-carboxamide
N-{[4-(2-methyl-2H-indazole-6-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridin-
e-2-carboxamide
N-({4-[(3-methanesulfonylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-[(4-{[4-chloro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-({4-[(3-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[(2-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(2-methanesulfonamidobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,-
2-c]pyridine-2-carboxamide
N-{[4-(2,3-dihydro-1,4-benzodioxine-6-sulfonyl)phenyl]methyl}imidazo[1,2--
a]pyrimidine-6-carboxamide
N-({4-[2-(dimethylamino)pyrimidine-5-sulfonyl]phenyl}methyl)-1H-pyrrolo[3-
,2-c]pyridine-2-carboxamide
N-({4-[(2-methyl-4-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(2-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(2,4-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyr-
idine-2-carboxamide
N-({4-[2-(dimethylamino)pyrimidine-5-sulfonyl]phenyl}methyl)-1H-pyrazolo[-
3,4-b]pyridine-5-carboxamide
N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[1-(4-fluorophenyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)thieno[2,3-
-c]pyridine-2-carboxamide
N-[(4-{[4-methoxy-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-p-
yrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-ethoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-{[4-(4-methylpyridine-3-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridi-
ne-2-carboxamide
N-{[4-({3-[2-(morpholin-4-yl)ethoxy]benzene}sulfonyl)phenyl]methyl}imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-({4-[(4-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-3-(pyridin-2-yl)-1H-pyrazole-5-carb-
oxamide
N-[(4-{[3-(5-methyl-1,2,4-oxadiazol-3-yl)benzene]sulfonyl}phenyl)m-
ethyl]thieno[2,3-c]pyridine-2-carboxamide
N-({4-[(3-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-{[4-(2-methyl-2H-indazole-5-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimi-
dine-6-carboxamide
N-{[4-(1,3-thiazole-2-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-carb-
oxamide
N-(4-(2-(trifluoromethoxy)phenylsulfonyl)benzyl)imidazo[1,2-a]pyri-
dine-6-carboxamide
N-{[4-(6-methylpyrazine-2-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2--
carboxamide
N-({4-[(3-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(4,5-difluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[-
3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(methylsulfamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-[(4-{[3-fluoro-4-(methylsulfanyl)benzene]sulfonyl}phenyl)methyl]thieno[-
2,3-c]pyridine-2-carboxamide
N-({4-[2-(3-fluorophenyl)-1,3-thiazole-4-sulfonyl]phenyl}methyl)furo[2,3--
c]pyridine-2-carboxamide
N-[(4-{[3-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]py-
ridine-2-carboxamide
N-({4-[5-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)thieno[2,3-c]-
pyridine-2-carboxamide
N-[(4-{[4-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yridine-6-carboxamide
N-({4-[(3-methoxy-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1-methyl-1H-pyrrolo[3,2-c]pyridine--
2-carboxamide
N-({4-[(3-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-{[4-(5-chloro-3-methylpyridine-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyri-
dine-2-carboxamide
N-({4-[6-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)thieno[2,3-c]-
pyridine-2-carboxamide
N-[(4-{[2-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-c]-
pyridine-2-carboxamide
N-({4-[1-(3-chlorophenyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)imidazo[1,-
2-a]pyridine-6-carboxamide
N-({4-[(3-methoxy-4-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-({4-[2-(3-fluorophenyl)-1,3-thiazole-4-sulfonyl]phenyl}methyl)imidazo[1-
,2-a]pyrimidine-6-carboxamide
N-[(4-{[3-(piperidin-1-ylmethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,-
2-a]pyrimidine-6-carboxamide
N-[(4-{[3-fluoro-5-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-({4-[5-(trifluoromethyl)pyridine-3-sulfonyl]phenyl}methyl)-1H-pyrazolo[-
3,4-b]pyridine-5-carboxamide
N-({4-[(4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridi-
ne-5-carboxamide
N-({4-[(3-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-[(4-{[2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]py-
ridine-2-carboxamide
N-{[4-(dimethyl-1,3-thiazole-5-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrim-
idine-6-carboxamide
N-({4-[(3-chloro-4-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(2,4-dichloro-3-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]p-
yridine-2-carboxamide
N-({4-[(2-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-(4-(phenylsulfonyl)benzyl)benzo[d]thiazole-5-carboxamide
N-{[4-(quinoline-3-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-carboxami-
de
N-({4-[(3,4-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine--
2-carboxamide
N-({4-[(3-fluoro-4-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-({4-[(4-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-({4-[(4-ethoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-[(4-{[3-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1-
,2-a]pyrimidine-6-carboxamide
N-{[4-(2H-1,3-benzodioxole-5-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimid-
ine-6-carboxamide
N-{[4-(2H-1,3-benzodioxole-4-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridin-
e-6-carboxamide
N-{[4-(6-methylpyridine-3-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyrid-
ine-5-carboxamide
N-({4-[(5-tert-butyl-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[-
3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(ethanesulfonyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyrid-
ine-2-carboxamide
N-({4-[(4-methoxy-3-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[5-(pyrrolidin-1-yl)pyridine-3-sulfonyl]phenyl}methyl)furo[2,3-c]py-
ridine-2-carboxamide
N-({4-[(3-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-({4-[(3-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-[(4-{[2-methoxy-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thien-
o[2,3-c]pyridine-2-carboxamide
N-({4-[5-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)imidazo[1,2-a-
]pyrimidine-6-carboxamide
N-[(4-{[3-(pyrimidin-2-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(6-chloro-2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)thieno[2-
,3-c]pyridine-2-carboxamide
N-({4-[(5-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(3-sulfamoylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
-carboxamide
N-({4-[(5-cyano-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-[(4-{[4-fluoro-3-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-
furo[2,3-c]pyridine-2-carboxamide
N-{[4-(1,3-thiazole-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-car-
boxamide
N-({4-[(3-cyanobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-car-
boxamide
N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)m-
ethyl]imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-({4-[(2,6-dichlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a-
]pyrimidine-6-carboxamide
N-[(4-{[2-fluoro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyridine-6-carboxamide
N-[(4-{[3-chloro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-({4-[(2-phenoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine--
6-carboxamide
N-{[4-(6-methylpyrazine-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-
-6-carboxamide
N-({4-[(2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-({4-[(2-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-[(4-{[2-methoxy-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]furo[-
2,3-c]pyridine-2-carboxamide
N-({4-[(4-ethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine--
2-carboxamide
N-{[4-(1-methyl-1H-indazole-7-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridi-
ne-6-carboxamide
N-[(4-{[3-(cyclopentylcarbamoyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c-
]pyridine-2-carboxamide
5-hydroxy-N-({4-[(4-phenylbenzene)sulfonyl]phenyl}methyl)-1H-indole-2-car-
boxamide
N-[(4-{[4-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
-c]pyridine-2-carboxamide
N-[(4-{[4-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyri-
midine-6-carboxamide
N-({4-[(3-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-[(4-{[4-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(4-ethoxy-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[(4-butoxy-3-chlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(4-methanesulfonylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-[(4-{8-oxatricyclo[7.4.0.0.sup.2,7]trideca-1(13),2,4,6,9,11-hexaene-6-s-
ulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-carboxamide
N-{[4-(1H-indole-7-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-carboxa-
mide
N-[(4-{[2-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyr-
idine-2-carboxamide
N-{[4-(naphthalene-1-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-ca-
rboxamide
N-{[4-(quinoline-3-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine--
2-carboxamide
N-({4-[(4-chloro-3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-{[4-(5-chloropyridine-3-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridi-
ne-2-carboxamide
N-({4-[(3-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[(4-butylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine--
2-carboxamide
N-({4-[(2,6-dichlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyr-
idine-5-carboxamide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(3-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-[(4-{[3-fluoro-4-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]thien-
o[2,3-c]pyridine-2-carboxamide
N-[(4-{[2-methoxy-5-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H--
pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-{[4-(phenoxathiine-4-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6--
carboxamide
N-[(4-{[3-(4-fluorophenoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yridine-6-carboxamide
N-{[4-(quinoline-3-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-5-c-
arboxamide
N-({4-[(5-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,-
3-c]pyridine-2-carboxamide
N-[(4-{[4-methoxy-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imida-
zo[1,2-a]pyrimidine-6-carboxamide
N-[(4-{[3-fluoro-4-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]furo[-
2,3-c]pyridine-2-carboxamide
N-[(4-{[3-(5-methyl-1,2,4-oxadiazol-3-yl)benzene]sulfonyl}phenyl)methyl]f-
uro[2,3-c]pyridine-2-carboxamide
N-({4-[(3-acetylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-({4-[(4-butoxy-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
-c]pyridine-2-carboxamide
N-({4-[(2-butoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-{[4-({3-[(propan-2-yl)carbamoyl]benzene}sulfonyl)phenyl]methyl}imidazo[-
1,2-a]pyrimidine-6-carboxamide
N-({4-[(4,5-difluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c-
]pyridine-2-carboxamide
N-({4-[(3,4-dichlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidi-
ne-6-carboxamide
N-({4-[6-(1H-pyrazol-1-yl)pyridine-3-sulfonyl]phenyl}methyl)imidazo[1,2-a-
]pyridine-6-carboxamide
N-({4-[(3-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-[(4-{[3-chloro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyridine-6-carboxamide
N-({4-[(4-ethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carb-
oxamide
N-({4-[(2,3-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-({4-[(3-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(2-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(4-propoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridin-
e-2-carboxamide
N-({4-[(2-fluoro-6-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[2-(3-fluorophenyl)-1,3-thiazole-4-sulfonyl]phenyl}methyl)-1H-pyrro-
lo[3,2-c]pyridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carboxa-
mide
N-{[4-(1-benzothiophene-7-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine--
2-carboxamide
N-({4-[(3-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridin-
e-2-carboxamide
N-({4-[(2-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-{[4-(6-methylpyrazine-2-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyrid-
ine-5-carboxamide
N-({4-[2-(morpholin-4-yl)pyridine-3-sulfonyl]phenyl}methyl)imidazo[1,2-a]-
pyrimidine-6-carboxamide
N-[(4-{[4-(1-cyanocyclopentyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]p-
yridine-2-carboxamide
N-({4-[(4,5-difluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]p-
yridine-2-carboxamide
N-[(4-{[4-(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
ridine-6-carboxamide
N-{[4-(isoquinoline-4-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-car-
boxamide
N-({4-[(3-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]-
pyridine-2-carboxamide
N-{[4-(1-methyl-1H-1,3-benzodiazole-6-sulfonyl)phenyl]methyl}imidazo[1,2--
a]pyrimidine-6-carboxamide
N-({4-[(2-ethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-car-
boxamide
N-({4-[(2-ethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridin-
e-2-carboxamide
N-({4-[(4-fluoro-2,5-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a-
]pyridine-6-carboxamide
N-({4-[5-(pyrrolidin-1-yl)pyridine-3-sulfonyl]phenyl}methyl)-1H-pyrrolo[3-
,2-c]pyridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-[1,2,4]triazolo[4,3-a]pyridine-6-ca-
rboxamide
N-[(4-{[3-(5-methyl-1,2,4-oxadiazol-3-yl)benzene]sulfonyl}phenyl-
)methyl]imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[4-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)thieno[2,3-c]-
pyridine-2-carboxamide
N-({4-[6-(3,4-difluorophenyl)pyridine-2-sulfonyl]phenyl}methyl)thieno[2,3-
-c]pyridine-2-carboxamide
N-({4-[(3-ethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carb-
oxamide
N-({4-[(2-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3--
c]pyridine-2-carboxamide
N-({4-[(2,3-dimethoxy-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[-
3,2-c]pyridine-2-carboxamide
N-[(4-{[3-fluoro-5-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyridine-6-carboxamide
N-({4-[(2,6-dimethoxy-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo-
[3,4-b]pyridine-5-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-carboxamide
N-[(4-{[4-(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-[(4-{[3-(methylcarbamoyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyri-
dine-2-carboxamide
N-{[4-(5-fluoro-6-methylpyridine-2-sulfonyl)phenyl]methyl}thieno[2,3-c]py-
ridine-2-carboxamide
N-({4-[(6-chloro-2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrr-
olo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-{[4-(2H-1,3-benzodioxole-4-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimid-
ine-6-carboxamide
N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yridine-6-carboxamide
N-[(4-{[4-fluoro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-{[4-(isoquinoline-4-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-c-
arboxamide
N-({4-[(2,4,5-trimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3--
c]pyridine-2-carboxamide
N-({4-[(2,4-dichloro-3-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2--
a]pyrimidine-6-carboxamide
(E)-2-cyano-3-({4-[(5-fluoro-2-methoxyphenyl)
sulfamoyl]phenyl}methyl)-1-(pyridin-4-yl)guanidine
N-[(4-{[2-fluoro-3-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]thieno[-
2,3-c]pyridine-2-carboxamide
N-({4-[(4-methoxy-3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[6-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)imidazo[1,2-a-
]pyrimidine-6-carboxamide
N-[(4-{[4-methoxy-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thien-
o[2,3-c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-6-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimi-
dine-6-carboxamide
N-({4-[2-(trifluoromethyl)imidazo[1,2-a]pyridine-6-sulfonyl]phenyl}methyl-
)thieno[2,3-c]pyridine-2-carboxamide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1,3-benzothiazo-
le-6-carboxamide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(4-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-[(4-{[3-fluoro-5-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-
-1H-pyrrolo[3,2-c]pyridine-2-carboxamide N-{[4-(phenylmethane)
sulfonylphenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-[(4-{[4-(1-cyanocyclopentyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[-
3,2-c]pyridine-2-carboxamide
N-({4-[(4-ethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-{[4-(2-methylpyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-[(4-{[4-fluoro-2-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]furo[2,-
3-c]pyridine-2-carboxamide
N-({4-[6-(3,4-difluorophenyl)pyridine-2-sulfonyl]phenyl}methyl)-1H-pyrazo-
lo[3,4-b]pyridine-5-carboxamide
N-[(4-{[2-fluoro-3-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]thien-
o[2,3-c]pyridine-2-carboxamide
N-[(4-{[2-methoxy-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-p-
yrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-propoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-car-
boxamide
N-({4-[(4-methoxy-2,5-dimethylbenzene)sulfonyl]phenyl}methyl)imid-
azo[1,2-a]pyrimidine-6-carboxamide
N-({4-[(5-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-[(4-{[2-methyl-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2-
,3-c]pyridine-2-carboxamide
N-[(4-{[4-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3-
,4-b]pyridine-5-carboxamide
N-({4-[(3,4-difluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyri-
dine-2-carboxamide
N-({4-[(3,5-dimethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
-2-carboxamide
N-[(4-{[4-chloro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-[1,3]thiazolo[5,4-c]pyridine-2-carb-
oxamide
N-({4-[5-(pyrrolidin-1-yl)pyridine-3-sulfonyl]phenyl}methyl)imidaz-
o[1,2-a]pyridine-6-carboxamide
N-[(4-{[2-methyl-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1-
H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-chloro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(3-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-{[4-(5-chloro-3-methylpyridine-2-sulfonyl)phenyl]methyl}thieno[2,3-c]py-
ridine-2-carboxamide
N-[(4-{[2-(dimethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]py-
ridine-2-carboxamide
N-[(4-{[4-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,-
4-b]pyridine-6-carboxamide
N-({4-[2-(pyrrolidin-1-yl)-1,3-thiazole-5-sulfonyl]phenyl}methyl)-1H-pyrr-
olo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(4-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-[(4-{[2-methoxy-5-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imid-
azo[1,2-a]pyrimidine-6-carboxamide
N-({4-[(4-methoxy-2,5-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]p-
yridine-2-carboxamide
N-[(4-{[3-fluoro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-[(4-{[3-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-{[4-({4-[(pyrrolidin-1-yl)carbonyl]benzene}sulfonyl)phenyl]methyl}thien-
o[2,3-c]pyridine-2-carboxamide
N-({4-[(2,4,6-trimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-
-2-carboxamide
N-({4-[(2-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-[(4-{[2-(benzyloxy)-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]i-
midazo[1,2-a]pyrimidine-6-carboxamide
N-{[4-(6-methoxypyridine-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidin-
e-6-carboxamide
N-[(4-{[2-methoxy-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-p-
yrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-b]-
pyridine-5-carboxamide
N-(1,3-benzothiazol-6-ylmethyl)-4-[(3-chlorobenzene)sulfonyl]benzamide
N-({4-[(2,4-dichloro-3-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c-
]pyridine-2-carboxamide
N-({4-[(4-ethoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[2-(trifluoromethyl)imidazo[1,2-a]pyridine-6-sulfonyl]phenyl}methyl-
)furo[2,3-c]pyridine-2-carboxamide
N-{[4-(phenoxathiine-4-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine--
2-carboxamide
N-({4-[1-(4-fluorophenyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)-1H-pyrrol-
o[3,2-c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]py-
ridine-2-carboxamide
N-[(4-{[2-methoxy-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-p-
yrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-[(4-{[3-(cyclopentylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,-
2-a]pyrimidine-6-carboxamide
N-{[4-({3-[2-(morpholin-4-yl)ethoxy]benzene}sulfonyl)phenyl]methyl}-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-fluoro-2-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]imidazo-
[1,2-a]pyridine-6-carboxamide
N-[(4-{[4-fluoro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-5-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine--
2-carboxamide
N-({4-[(2-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-{[4-({3-[(morpholin-4-yl)carbonyl]benzene}sulfonyl)phenyl]methyl}-1H-py-
razolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-(pyrimidin-2-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-[(4-{[4-fluoro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2,3-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2--
carboxamide
N-{[4-(1-methyl-1H-indazole-7-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimi-
dine-6-carboxamide
N-({4-[(3-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(2-chloro-6-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-({4-[(3,4-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimid-
ine-6-carboxamide
N-({4-[(3,5-difluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyr-
idine-5-carboxamide
N-[(4-{[3-fluoro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyridine-6-carboxamide
N-({4-[(4-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-({4-[(5-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-({4-[(2-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-5-(pyridin-3-yl)-1H-pyrazole-3-carb-
oxamide
N-({4-[(4-butylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimi-
dine-6-carboxamide
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
-carboxamide
N-[(4-{[3-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-
-2-carboxamide
N-[(4-{[3-(4-fluorophenoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]py-
ridine-2-carboxamide
N-[(4-{[5-chloro-2-(2,2-difluoroethoxy)benzene]sulfonyl}phenyl)methyl]-1H-
-pyrrolo[3,2-c]pyridine-2-carboxamide
N-{[4-(quinoline-6-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-carboxa-
mide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c-
]pyridine-2-carboxamide
N-({4-[(5-acetyl-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-[(4-{8-thiatricyclo[7.4.0.0.sup.2,7]trideca-1(13),2,4,6,9,11-hexaene-6--
sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[(4-butoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-({4-[5-(trifluoromethyl)pyridine-3-sulfonyl]phenyl}methyl)imid-
azo[1,2-a]pyridine-6-carboxamide
N-[(4-{[4-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyrid-
ine-2-carboxamide
N-{[4-(5-methoxypyridine-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-c-
arboxamide
N-({4-[(3-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo-
[1,2-a]pyrimidine-6-carboxamide
N-({4-[(2-acetylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-({4-[(4-acetylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(2-acetylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
-carboxamide
N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]im-
idazo[1,2-a]pyridine-6-carboxamide
N-({4-[(2-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-[(4-{[4-chloro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-({4-[(2-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(3-phenylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
-carboxamide
N-{[4-(6-methoxynaphthalene-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridi-
ne-6-carboxamide
N-[(4-{[4-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[1-(3-chlorophenyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)-1H-pyrrol-
o[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-chloro-5-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]thieno[2-
,3-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-({4-[(4-ethoxy-2-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-[(4-{[4-(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyr-
idine-2-carboxamide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(3-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-[(4-{[2-(dimethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3-
,2-c]pyridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-5-(pyridin-3-yl)-1,2,4-oxadiazole-3-
-carboxamide
5-hydroxy-N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-in-
dole-2-carboxamide
N-[(4-{[3-(dimethylsulfamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a-
]pyrimidine-6-carboxamide
N-{[4-(2,3-dihydro-1-benzofuran-7-sulfonyl)phenyl]methyl}imidazo[1,2-a]py-
ridine-6-carboxamide
N-{[4-(6-methylpyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-
-6-carboxamide
N-[(4-{[2-methoxy-5-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrro-
lo[3,2-c]pyridine-2-carboxamide
N-({4-[6-(dimethylamino)pyridine-3-sulfonyl]phenyl}methyl)furo[2,3-c]pyri-
dine-2-carboxamide
N-[(4-{[2-(trifluoromethoxy)benzene]sulfinyl}phenyl)methyl]-1H-pyrrolo[3,-
2-c]pyridine-2-carboxamide
N-({4-[(3,5-difluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine--
2-carboxamide
N-({4-[(4-chloro-3-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(2,4,5-trimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrim-
idine-6-carboxamide
N-({4-[(2,4-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2--
carboxamide
N-[(4-{[2-chloro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2-
,3-c]pyridine-2-carboxamide
N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1-
H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[(4-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[1-(propan-2-yl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)imidazo[1,2-a-
]pyridine-6-carboxamide
N-[(4-{[3-(difluoromethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyri-
dine-2-carboxamide
N-[(4-{[2-methoxy-6-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-chloro-3-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(2,3-dimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine--
2-carboxamide
N-({4-[(5-tert-butyl-2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]p-
yridine-2-carboxamide
N-({4-[(4-methoxy-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(2,5-dimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine--
2-carboxamide
N-({4-[(2-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-[(4-{[2-chloro-5-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrr-
olo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-2,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3-
,2-c]pyridine-2-carboxamide
N-({4-[(4-butoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[(2-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-[(4-{[2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyri-
dine-2-carboxamide
N-[(4-{[5-chloro-2-(2,2-difluoroethoxy)benzene]sulfonyl}phenyl)methyl]imi-
dazo[1,2-a]pyridine-6-carboxamide
N-({4-[(2-butoxy-5-chlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-[(4-{[2-chloro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-chloro-3-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]py-
ridine-2-carboxamide
N-[(4-{[3-fluoro-5-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyridine-6-carboxamide
N-({4-[(2-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(3-chloro-4-propoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-[(4-{[2,4-bis(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,-
2-a]pyrimidine-6-carboxamide
N-({4-[(4-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine--
6-carboxamide
N-({4-[(2-ethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-({4-[(3-phenylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-[(4-{[2-methoxy-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]imida-
zo[1,2-a]pyrimidine-6-carboxamide
N-[(4-{[2-methoxy-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thien-
o[2,3-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-({4-[(2-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-{[4-(isoquinoline-4-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-carbox-
amide
N-[(4-{[2-chloro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]f-
uro[2,3-c]pyridine-2-carboxamide
N-[(4-{[5-(diethylcarbamoyl)-2-fluorobenzene]sulfonyl}phenyl)methyl]-1H-p-
yrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-chloro-6-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-({4-[(3-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-({4-[2-(pyrrolidin-1-yl)-1,3-thiazole-5-sulfonyl]phenyl}methyl)imidazo[-
1,2-a]pyrimidine-6-carboxamide
N-[(4-{5H,6H,7H,8H,9H-imidazo[1,2-a]azepine-3-sulfonyl}phenyl)methyl]furo-
[2,3-c]pyridine-2-carboxamide
N-({4-[(4-butoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carb-
oxamide
N-({4-[(3,5-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-({4-[(5-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-[(4-{[3-fluoro-4-(methylsulfanyl)benzene]sulfonyl}phenyl)methyl]furo[2,-
3-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-({4-[(3-tert-butylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2--
carboxamide
N-[(4-{[3-fluoro-4-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imida-
zo[1,2-a]pyridine-6-carboxamide
N-({4-[(5-tert-butyl-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo-
[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-fluoro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyridine-6-carboxamide
N-({4-[(3-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(3-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(4-butoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-({4-[(3-methoxy-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[5-(pyrrolidin-1-yl)pyridine-3-sulfonyl]phenyl}methyl)-1,3-benzothi-
azole-6-carboxamide
N-{[4-(5-fluoro-6-methylpyridine-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyri-
dine-2-carboxamide
N-{[4-(phenoxathiine-4-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-carbo-
xamide
N-({4-[(3,4-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-[(4-{[2-methyl-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-[(4-{[2-(methylsulfamoyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
-c]pyridine-2-carboxamide
N-({4-[(4-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-({4-[(3-propoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridin-
e-2-carboxamide
N-[(4-{[2-(methylsulfamoyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyri-
dine-2-carboxamide
N-({4-[4-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)imidazo[1,2-a-
]pyrimidine-6-carboxamide
N-({4-[(4-ethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-({4-[(3-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-[(4-{[4-(1-cyanocyclopentyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2--
a]pyridine-6-carboxamide
N-[(4-{[2-methoxy-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-p-
yrrolo[3,2-c]pyridine-2-carboxamide
N-{[4-(dimethyl-1,3-thiazole-5-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridi-
ne-2-carboxamide
N-[(4-{[4-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[(4-cyclohexylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-
-6-carboxamide
N-[(4-{6-chloroimidazo[1,2-a]pyridine-3-sulfonyl}phenyl)methyl]-1H-pyrrol-
o[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
ridine-6-carboxamide
N-{[4-({4-[2-(dimethylamino)ethyl]benzene}sulfonyl)phenyl]methyl}imidazo[-
1,2-a]pyridine-6-carboxamide
N-({4-[(5-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}quinazoline-6-carboxamide
N-[(4-{[4-fluoro-3-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-
-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1,3-benzothiaz-
ole-6-carboxamide
N-({4-[(3,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyr-
idine-5-carboxamide
N-({4-[(3-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-[(4-{[4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,-
4-b]pyridine-5-carboxamide
N-({4-[(4-butoxy-3-chlorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[(4-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-{[4-({3-[(propan-2-yl)carbamoyl]benzene}sulfonyl)phenyl]methyl-
}imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[(2,4-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]py-
ridine-5-carboxamide
N-({4-[(2,3-dimethoxy-5-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c-
]pyridine-2-carboxamide
N-[(4-{[2-fluoro-3-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]imidazo-
[1,2-a]pyridine-6-carboxamide
N-({4-[6-(morpholin-4-yl)pyridine-3-sulfonyl]phenyl}methyl)thieno[2,3-c]p-
yridine-2-carboxamide
N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,-
4-b]pyridine-5-carboxamide
N-{[4-(5-methoxypyridine-2-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
-carboxamide
N-({4-[(3-chloro-2-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-[(4-{[5-hydroxy-2-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]furo-
[2,3-c]pyridine-2-carboxamide
N-({4-[(3,4-dimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine--
2-carboxamide
N-[(4-{[4-chloro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(2-butoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-({4-[(4-propoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-c-
arboxamide
N'-(4-tosylphenyl)imidazo[1,2-a]pyridine-6-carbohydrazide
N-({4-[(3,4-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyr-
idine-5-carboxamide
N-{[4-(isoquinoline-4-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine--
5-carboxamide
N-({4-[(2,6-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2--
carboxamide
N-({4-[(4-methoxy-3,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[-
3,2-c]pyridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-[1,2,3,4]tetrazolo[1,5-a]pyridine-6-
-carboxamide
N-({4-[(4-cyanobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-ca-
rboxamide
N-{[4-({3-[(propan-2-yl)carbamoyl]benzene}sulfonyl)phenyl]methyl-
}furo[2,3-c]pyridine-2-carboxamide
N-({4-[(2,4-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidi-
ne-6-carboxamide
N-({4-[(4-butoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-{[4-(4-methylpyridine-3-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2--
carboxamide
N-[(4-{[2-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,-
2-c]pyridine-2-carboxamide
N-({4-[(4-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
-carboxamide
N-[(4-{[4-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-({4-[(3-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-{[4-(1-methyl-1H-indazole-4-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridin-
e-2-carboxamide
N-({4-[(4-chloro-3-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(3-cyanobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine--
2-carboxamide
N-{[4-(2,3-dihydro-1-benzofuran-7-sulfonyl)phenyl]methyl}imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[6-(dimethylamino)pyridine-3-sulfonyl]phenyl}methyl)-1H-pyrazolo[3,-
4-b]pyridine-5-carboxamide
N-({4-[(3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
-carboxamide
N-({4-[(2-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(4-ethoxy-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-[(4-{[2-(benzyloxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-c]pyr-
idine-2-carboxamide
N-({4-[(5-acetyl-2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-({4-[1-(3-chlorophenyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)imidazo[1,-
2-a]pyrimidine-6-carboxamide
N-[(4-{[4-chloro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2-
,3-c]pyridine-2-carboxamide
N-({4-[(2-butoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-[(4-{[2-methoxy-5-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H--
pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{2-[ethyl(methyl)amino]-1,3-thiazole-5-sulfonyl}phenyl)methyl]imida-
zo[1,2-a]pyridine-6-carboxamide
N-({4-[(4-ethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6--
carboxamide
N-({4-[(4-chloro-3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(2-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[5-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)imidazo[1,2-a-
]pyridine-6-carboxamide
N-{[4-(5-fluoropyridine-3-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2--
carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}thieno[2,3-b]pyrazine-6-carboxamide
N-({4-[5-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)furo[2,3-c]py-
ridine-2-carboxamide
N-({4-[(2-butoxy-5-chlorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-[(4-{2-[ethyl(methyl)amino]-1,3-thiazole-5-sulfonyl}phenyl)methyl]imida-
zo[1,2-a]pyrimidine-6-carboxamide
N-[(4-{[2-chloro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-{[4-(quinoline-6-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-carb-
oxamide
N-({4-[(3-ethoxy-2-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrol-
o[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(morpholin-4-ylmethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrol-
o[3,2-c]pyridine-2-carboxamide
N-({4-[(4-methoxy-3-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(3-fluoro-4-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-{[4-(5-methylpyridine-3-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2--
carboxamide
N-{[4-(2,3-dihydro-1-benzofuran-7-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-[(4-{6-chloroimidazo[1,2-a]pyridine-3-sulfonyl}phenyl)methyl]furo[2,3-c-
]pyridine-2-carboxamide
N-[(4-{[3-(propane-1-sulfonamido)benzene]sulfonyl}phenyl)methyl]imidazo[1-
,2-a]pyrimidine-6-carboxamide
N-({4-[(3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridi-
ne-5-carboxamide
N-({4-[(3-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-({4-[(4-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carb-
oxamide
N-({4-[(4-chloro-3-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,-
3-c]pyridine-2-carboxamide
N-{[4-({3-[2-(dimethylamino)ethoxy]benzene}sulfonyl)phenyl]methyl}furo[2,-
3-c]pyridine-2-carboxamide
N-{[4-(2-methyl-2H-indazole-6-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]py-
ridine-2-carboxamide
N-[(4-{[3-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1-
,2-a]pyridine-6-carboxamide
N-[(4-{[3-(cyclopentylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,-
2-a]pyridine-6-carboxamide
N-[(4-{[4-fluoro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-cyanobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-ca-
rboxamide
N-({4-[(2,4-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3-
,2-c]pyridine-2-carboxamide
N-{[4-(5-methylpyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-
-carboxamide
N-[(4-{[2-chloro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-[(4-{[2-chloro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyri-
dine-2-carboxamide
N-[(4-{[3-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(2-acetylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-({4-[(4-chloro-3-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
5-hydroxy-N-{[4-(1-methyl-1H-indazole-4-sulfonyl)phenyl]methyl}-1H-indole-
-2-carboxamide
N-{[4-(2,6-dimethoxypyridine-3-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-
-2-carboxamide
N-({4-[(2-butoxy-6-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-({4-[(3-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-{[4-(naphthalene-1-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-carboxa-
mide
N-({4-[(3,5-difluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]-
pyridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1-methyl-1H-pyrazolo[3,4-b]pyridine-
-5-carboxamide
N-[(4-{8-thiatricyclo[7.4.0.0.sup.2,7]trideca-1(13),2,4,6,9,11-hexaene-6--
sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[1-methyl-5-(trifluoromethyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)-
-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-ethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-({4-[(3-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-c-
arboxamide
N-({4-[2-(dimethylamino)pyrimidine-5-sulfonyl]phenyl}methyl)thi-
eno[2,3-c]pyridine-2-carboxamide
N-{[4-(6-methylpyridine-3-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2--
carboxamide
N-[(4-{[3-chloro-5-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[-
1,2-a]pyridine-6-carboxamide
N-[(4-{6-chloroimidazo[1,2-a]pyridine-3-sulfonyl}phenyl)methyl]thieno[2,3-
-c]pyridine-2-carboxamide
N-({4-[1-(4-fluorophenyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)furo[2,3-c-
]pyridine-2-carboxamide
N-{[4-(quinoline-6-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-carboxami-
de
N-({4-[6-(3,4-difluorophenyl)pyridine-2-sulfonyl]phenyl}methyl)imidazo[-
1,2-a]pyridine-6-carboxamide
N-({4-[6-(morpholin-4-yl)pyridine-3-sulfonyl]phenyl}methyl)-1H-pyrrolo[3,-
2-c]pyridine-2-carboxamide
N-{[4-(1,5-dimethyl-1H-imidazole-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-[(4-{[2-(dimethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]-
pyridine-2-carboxamide
N-({4-[(4-chloro-3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-({4-[(3-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-[(4-{[4-fluoro-2-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]thieno[-
2,3-c]pyridine-2-carboxamide
N-({4-[(2,6-dichlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyri-
dine-2-carboxamide
N-({4-[(4-acetylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-({4-[(3,5-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridin-
e-6-carboxamide
N-{[4-({4-[(1R)-1-hydroxybutyl]benzene}sulfonyl)phenyl]methyl}furo[2,3-c]-
pyridine-2-carboxamide
N-({4-[(4-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-{[4-(1-methyl-1H-indazole-7-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridin-
e-2-carboxamide
N-{[4-({3-[2-(dimethylamino)ethyl]benzene}sulfonyl)phenyl]methyl}-1H-pyrr-
olo[3,2-c]pyridine-2-carboxamide
N-{[4-(2-methyl-2H-indazole-6-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimi-
dine-6-carboxamide
N-({4-[(2-ethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-({4-[(2-ethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6--
carboxamide
N-({4-[(3,4-dimethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
-carboxamide
N-{[4-(1,5-dimethyl-1H-imidazole-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyri-
dine-2-carboxamide
N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-5-
-hydroxy-1H-indole-2-carboxamide
N-({4-[(5-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(2,3-dimethoxy-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo-
[3,4-b]pyridine-5-carboxamide
N-({4-[(3-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-{[4-(isoquinoline-4-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-2-
-carboxamide
N-[(4-{[2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-({4-[6-(dimethylamino)pyridine-3-sulfonyl]phenyl}methyl)imidazo[1,2-a]p-
yridine-6-carboxamide
N-[(4-{[3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(2-butoxy-6-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-[(4-{[3-(ethanesulfonyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
ridine-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-3-(pyridin-3-yl)-1,2-oxazole-5-carb-
oxamide
N-[(4-{[2-methoxy-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methy-
l]thieno[2,3-c]pyridine-2-carboxamide
N-[(4-{[3-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yridine-6-carboxamide
N-({4-[(3-chloro-4-propoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(5-chloro-2-propoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-[(4-{[3-fluoro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(5-tert-butyl-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2--
a]pyrimidine-6-carboxamide
N-({4-[(3-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-({4-[6-(3,4-difluorophenyl)pyridine-2-sulfonyl]phenyl}methyl)-1H-pyrrol-
o[3,2-c]pyridine-2-carboxamide
N-({4-[2-(trifluoromethyl)imidazo[1,2-a]pyridine-6-sulfonyl]phenyl}methyl-
)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[(4-cyanobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carbo-
xamide
N-[(4-{[4-fluoro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[(4-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-c-
arboxamide
N-({4-[(3,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[-
3,2-c]pyridine-2-carboxamide
N-({4-[(4-acetylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-({4-[(5-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-[(4-{[3-fluoro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-({4-[(2,3-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyr-
idine-2-carboxamide
N-({4-[(3-acetylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-[(4-{[2,4-bis(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c-
]pyridine-2-carboxamide
N-[(4-{[4-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridin-
e-2-carboxamide
N-{[4-(5-chloropyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-
-carboxamide
N-({4-[(2-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-({4-[(3-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(4-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-[(4-{[2-methoxy-5-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3--
c]pyridine-2-carboxamide
N-[(4-{[3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1,3-benzothiaz-
ole-6-carboxamide
N-{[4-(4-methylpyridine-3-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyrid-
ine-5-carboxamide
N-{[4-(pyridine-3-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-carboxamid-
e
N-({4-[(3-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
-carboxamide
N-({4-[(2-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-({4-[(2,5-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2--
carboxamide
N-({4-[(2-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-[(4-{[3-fluoro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2-
,3-c]pyridine-2-carboxamide
N-({4-[(3,5-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2--
carboxamide
N-({4-[(2,3-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimid-
ine-6-carboxamide
N-({4-[(3-ethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6--
carboxamide
N-{[4-(2H-1,3-benzodioxole-5-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
-carboxamide
N-[(4-{[2-methyl-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-({4-[(3-sulfamoylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine--
6-carboxamide
N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-[(4-{[4-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]-
pyrimidine-6-carboxamide
N-{[4-({3-[(2-methylpropyl)carbamoyl]benzene}sulfonyl)phenyl]methyl}imida-
zo[1,2-a]pyrimidine-6-carboxamide
N-({4-[(2,3,6-trimethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyrid-
ine-2-carboxamide
N-({4-[(2-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-({4-[(3-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-4-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine--
2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[(2-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(4-butoxy-3-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-(6-(4-(morpholinomethyl)phenoxy)hexyl)-1H-pyrrolo[3,2-c]pyridine-2-carb-
oxamide
N-({4-[(3-ethoxy-2-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,-
2-a]pyridine-6-carboxamide
N-[(4-{[4-(4-methylpiperazin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrr-
olo[3,2-c]pyridine-2-carboxamide
N-{[4-(quinoline-8-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-carb-
oxamide
N-({4-[(4-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrro-
lo[3,2-c]pyridine-2-carboxamide
N-({4-[6-(dimethylamino)pyridine-3-sulfonyl]phenyl}methyl)thieno[2,3-c]py-
ridine-2-carboxamide
N-({4-[(5-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-[(4-{[3-fluoro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-{[4-(1,4-dimethyl-1H-imidazole-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyri-
dine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-carboxami-
de
N-({4-[(3-propoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-c-
arboxamide
N-{[4-(5-methylpyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]-
pyrimidine-6-carboxamide
N-({4-[4-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)-1H-pyrazolo[-
3,4-b]pyridine-5-carboxamide
N-{[4-(2H-1,3-benzodioxole-4-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyr-
idine-2-carboxamide
N-[(4-{[4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-[(4-{5H,6H,7H,8H,9H-imidazo[1,2-a]azepine-3-sulfonyl}phenyl)methyl]-1H--
pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-fluoro-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-{[4-(6-methoxynaphthalene-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine--
2-carboxamide
N-{[4-(2-methyl-2H-indazole-6-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridi-
ne-6-carboxamide
N-({4-[(2-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-{[4-(5-fluoropyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-({4-[(2,4-dichloro-3-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2--
a]pyridine-6-carboxamide
N-({4-[(5-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-{[4-(naphthalene-1-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-carbo-
xamide
N-{[4-({4-[2-(dimethylamino)ethyl]benzene}sulfonyl)phenyl]methyl}im-
idazo[1,2-a]pyrimidine-6-carboxamide
N-[(4-{[2-methyl-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2,3,6-trimethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridin-
e-2-carboxamide
N-({4-[(3-butoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-c-
arboxamide
N-({4-[(3,5-dimethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]-
pyridine-2-carboxamide
N-({4-[(3-chloro-2-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-{[4-(5-chloropyridine-3-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyrid-
ine-5-carboxamide
N-({4-[(3-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-[(4-{[4-(dimethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]-1H--
pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(3,4-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]py-
ridine-5-carboxamide
N-{[4-(1-methyl-1H-indazole-6-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine--
2-carboxamide
N-{[4-(2,3-dihydro-1-benzofuran-7-sulfonyl)phenyl]methyl}thieno[2,3-c]pyr-
idine-2-carboxamide
N-{[4-(1H-indole-7-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-5-c-
arboxamide
N-({4-[(3-tert-butylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2--
a]pyrimidine-6-carboxamide
N-[(4-{[4-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
rimidine-6-carboxamide
N-{[4-({3-[(propan-2-yl)carbamoyl]benzene}sulfonyl)phenyl]methyl}thieno[2-
,3-c]pyridine-2-carboxamide
N-({4-[(2,3-dimethoxy-5-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]p-
yridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1,5-naphthyridine-2-carboxamide
5-hydroxy-N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-i-
ndole-2-carboxamide
N-[(4-{[3-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(2-methyl-4-propoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-{[4-({3-[(dimethylamino)methyl]benzene}sulfonyl)phenyl]methyl}furo[2,3--
c]pyridine-2-carboxamide
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carb-
oxamide
N-{[4-(5-fluoropyridine-3-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-[(4-{[3-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,-
4-b]pyridine-5-carboxamide
N-{[4-(2,3-dihydro-1,4-benzodioxine-6-sulfonyl)phenyl]methyl}thieno[2,3-c-
]pyridine-2-carboxamide
N-({4-[(4-methoxy-3,5-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2--
a]pyridine-6-carboxamide
N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]th-
ieno[2,3-c]pyridine-2-carboxamide
N-({4-[(2,5-dimethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
-carboxamide
N-({4-[(2,4,6-trimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrim-
idine-6-carboxamide
N-[(4-{[4-(4-methylpiperazin-1-yl)benzene]sulfonyl}phenyl)methyl]thieno[2-
,3-c]pyridine-2-carboxamide
N-[(4-{[2-methoxy-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imida-
zo[1,2-a]pyrimidine-6-carboxamide
N-({4-[(4-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-[(4-{[3-(ethanesulfonyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
rimidine-6-carboxamide
N-{[4-({3-[2-(dimethylamino)ethyl]benzene}sulfonyl)phenyl]methyl}thieno[2-
,3-c]pyridine-2-carboxamide
N-({4-[(4-methoxy-3,5-dimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c-
]pyridine-2-carboxamide
N-({4-[(3,4-difluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidi-
ne-6-carboxamide
N-[(4-{[3-fluoro-4-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-
furo[2,3-c]pyridine-2-carboxamide
N-({4-[2-(dimethylamino)pyrimidine-5-sulfonyl]phenyl}methyl)furo[2,3-c]py-
ridine-2-carboxamide
N-({4-[(2-ethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-[(4-{[2-methoxy-5-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1-
,2-a]pyridine-6-carboxamide
N-({4-[(2,6-dichlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-
-6-carboxamide
N-({4-[(2-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(2-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(3-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-({4-[(3,5-difluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidi-
ne-6-carboxamide
N-({4-[(2-ethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carbo-
xamide
N-({4-[(4-phenylbenzene)sulfonyl]phenyl}methyl)-1,3-benzothiazole-6-
-carboxamide
N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1-
,3-benzothiazole-6-carboxamide
N-[(4-{[4-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-c]-
pyridine-2-carboxamide
N-({4-[5-(dimethylamino)pyrazine-2-sulfonyl]phenyl}methyl)imidazo[1,2-a]p-
yridine-6-carboxamide
N-({4-[(2-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-[(4-{[3-chloro-5-(diethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]thien-
o[2,3-c]pyridine-2-carboxamide
N-[(4-{[4-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]py-
ridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}quinoline-6-carboxamide
N-({4-[(3-butoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carb-
oxamide
N-({4-[(4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrim-
idine-6-carboxamide
N-({4-[(3-methanesulfonylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(2,6-dimethoxy-4-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c-
]pyridine-2-carboxamide
N-{[4-({4-fluoro-3-[(propan-2-yl)carbamoyl]benzene}sulfonyl)phenyl]methyl-
}thieno[2,3-c]pyridine-2-carboxamide
N-({4-[(5-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(3,5-dichlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyr-
idine-5-carboxamide
N-[(4-{[2-methoxy-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imida-
zo[1,2-a]pyridine-6-carboxamide
N-[(4-{[4-(4-methylpiperazin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyra-
zolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(4-chloro-3-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-[(4-{[2-fluoro-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]furo[2-
,3-c]pyridine-2-carboxamide
N-{[4-(5-methoxypyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidin-
e-6-carboxamide
N-({4-[2-(trifluoromethyl)pyridine-3-sulfonyl]phenyl}methyl)furo[2,3-c]py-
ridine-2-carboxamide
N-[(4-{[4-fluoro-3-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-
imidazo[1,2-a]pyrimidine-6-carboxamide
N-[(4-{[3-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,-
2-c]pyridine-2-carboxamide
N-({4-[(3-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[(2-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-{[4-({3-[(2-methylpropyl)carbamoyl]benzene}sulfonyl)phenyl]methyl}furo[-
2,3-c]pyridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-5-carbox-
amide
N-{[4-(pyridine-3-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine--
2-carboxamide
N-{[4-(2H-1,3-benzodioxole-5-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyr-
idine-2-carboxamide
N-({4-[(3,5-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]py-
ridine-5-carboxamide
N-[(4-{[2-(morpholin-4-ylmethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,-
2-a]pyrimidine-6-carboxamide
N-({4-[(2,6-dichloro-3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a-
]pyrimidine-6-carboxamide
N-({4-[(2-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[(3-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carb-
oxamide
N-[(4-{[5-fluoro-2-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]t-
hieno[2,3-c]pyridine-2-carboxamide
N-({4-[(3-methoxy-4-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(2-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-{[4-(6-methylpyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-
-carboxamide
N-[(4-{[2-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyr-
idine-2-carboxamide
N-{[4-(1,5-dimethyl-1H-imidazole-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]p-
yridine-6-carboxamide
N-[(4-{[3-chloro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-[(4-{[5-hydroxy-2-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H--
pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-(1H-imidazol-1-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]-
pyrimidine-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-3-carbox-
amide
N-({4-[(4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridin-
e-6-carboxamide
N-({4-[(3,4-difluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyr-
idine-5-carboxamide
N-({4-[(4-butoxy-3-chlorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-6-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]py-
ridine-2-carboxamide
N-({4-[(3-methanesulfonylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[3-chloro-2-(morpholin-4-yl)pyridine-4-sulfonyl]phenyl}methyl)thien-
o[2,3-c]pyridine-2-carboxamide
N-({4-[(3-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-{[4-(1,3-thiazole-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-carbox-
amide
N-({4-[(2-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2--
a]pyridine-6-carboxamide
N-[(4-{[4-chloro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyridine-6-carboxamide
N-({4-[(4-butoxy-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-{[4-(6-methoxynaphthalene-2-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]py-
ridine-2-carboxamide
N-[(4-{[3-(propane-1-sulfonamido)benzene]sulfonyl}phenyl)methyl]thieno[2,-
3-c]pyridine-2-carboxamide
N-[(4-{[4-chloro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-[(4-{[3-fluoro-5-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-[(4-{[2-methyl-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-py-
razolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[5-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)-1H-pyrazolo[-
3,4-b]pyridine-5-carboxamide
N-({4-[(3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
-carboxamide
N-{[4-(2-methylpyridine-3-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyrid-
ine-5-carboxamide
N-({4-[(2-cyanobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carbo-
xamide
N-{[4-(6-methylpyridine-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyridin-
e-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-2-carboxa-
mide
N-[(4-{[3-(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]p-
yridine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-5-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridin-
e-2-carboxamide
N-({4-[(3-acetylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carb-
oxamide
N-({4-[(2-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3--
c]pyridine-2-carboxamide
N-[(4-{[4-fluoro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2-
,3-c]pyridine-2-carboxamide
N-({4-[(4-butoxy-2-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(3-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
-carboxamide
N-({4-[(3-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[4-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)imidazo[1,2-a-
]pyridine-6-carboxamide
N-[(4-{[4-chloro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2-
,3-c]pyridine-2-carboxamide
N-({4-[(4-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-{[4-(2,3-dihydro-1-benzofuran-7-sulfonyl)phenyl]methyl}furo[2,3-c]pyrid-
ine-2-carboxamide
N-[(4-{[3-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]-
pyrimidine-6-carboxamide
N-({4-[4-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)furo[2,3-c]py-
ridine-2-carboxamide
N-[(4-{[5-chloro-2-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]furo[2,-
3-c]pyridine-2-carboxamide
N-({4-[(2-chloro-6-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-{[3-(benzenesulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-2-carboxa-
mide
N-[(4-{[4-fluoro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]im-
idazo[1,2-a]pyridine-6-carboxamide
N-({4-[(2-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
-carboxamide
N-[(4-{[2-methoxy-5-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,-
3-c]pyridine-2-carboxamide
N-[(4-{[2-methyl-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyridine-6-carboxamide
N-({4-[(2-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-c-
arboxamide
N-({4-[(2-phenoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(4-chlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
-carboxamide
N-({4-[(3-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-({4-[(3-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-[(4-{[3-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3-
,4-b]pyridine-5-carboxamide
N-({4-[(2-butoxy-5-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-({4-[(2-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[(2-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(3-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-[(4-{[3-(ethanesulfonyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(2-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carb-
oxamide
N-{[4-(4-methylpyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-({4-[(3,4-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyr-
idine-2-carboxamide
N-{[4-(1,4-dimethyl-1H-imidazole-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]p-
yridine-6-carboxamide
N-({4-[2-(dimethylamino)pyrimidine-5-sulfonyl]phenyl}methyl)imidazo[1,2-a-
]pyridine-6-carboxamide
N-{[4-(1-methyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimi-
dine-6-carboxamide
N-[(4-{[3-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yridine-6-carboxamide
N-[(4-{[2-chloro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-({4-[(3-butoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-({4-[(2,4-dimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]-
pyridine-2-carboxamide
N-({4-[(4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridin-
e-2-carboxamide
N-[(4-{[4-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridi-
ne-2-carboxamide
N-[(4-{[2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
-c]pyridine-2-carboxamide
N-({4-[(3-acetylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-({4-[(2-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-{[4-(5-chloro-3-methylpyridine-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]p-
yridine-6-carboxamide
N-({4-[2-(3-fluorophenyl)-1,3-thiazole-4-sulfonyl]phenyl}methyl)-1H-pyraz-
olo[3,4-b]pyridine-5-carboxamide
N-({4-[(3,5-dichlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyri-
dine-2-carboxamide
N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]fu-
ro[2,3-c]pyridine-2-carboxamide
N-{[4-(5-methoxypyridine-3-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
-carboxamide
N-[(4-{[2-fluoro-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-py-
razolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-chloro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-{[4-(2-methyl-2H-indazole-6-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine--
2-carboxamide
N-(4-(phenylsulfonyl)benzyl)-1H-imidazo[4,5-b]pyridine-6-carboxamide
N-[(4-{[4-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyr-
idine-2-carboxamide
N-{[4-(quinoline-3-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-2-ca-
rboxamide
N-({4-[(3-ethoxy-2-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[-
1,2-a]pyrimidine-6-carboxamide
N-({4-[(3-fluoro-4-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-{[4-(1-benzothiophene-7-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyrid-
ine-5-carboxamide
N-[(4-{[3-chloro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-({4-[(3,5-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyr-
idine-2-carboxamide
N-({4-[6-(morpholin-4-yl)pyridine-3-sulfonyl]phenyl}methyl)imidazo[1,2-a]-
pyridine-6-carboxamide
N-({4-[(2-chloro-4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-({4-[(3-acetylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
-carboxamide
N-{[4-(quinoline-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-carbox-
amide
N-[(4-{[3-fluoro-5-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]im-
idazo[1,2-a]pyridine-6-carboxamide
N-[(4-{[2-(morpholin-4-ylmethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazo-
lo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-(1H-imidazol-1-ylmethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
-c]pyridine-2-carboxamide
N-({4-[(4-methoxy-2,5-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2--
a]pyridine-6-carboxamide
N-[(4-{[4-fluoro-3-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-
thieno[2,3-c]pyridine-2-carboxamide
N-[(4-{[3-fluoro-5-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2,5-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyr-
idine-2-carboxamide
N-({4-[(2-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[5-(pyrrolidin-1-yl)pyridine-3-sulfonyl]phenyl}methyl)-1H-pyrazolo[-
3,4-b]pyridine-5-carboxamide
N-({4-[(3-phenylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-{[4-({4-(dimethylamino)methyl]benzene}sulfonyl)phenyl]methyl}imidazo[1,-
2-a]pyrimidine-6-carboxamide
N-[(4-{[3-(diethylcarbamoyl)-5-fluorobenzene]sulfonyl}phenyl)methyl]-1H-p-
yrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{2-[ethyl(methyl)amino]-1,3-thiazole-5-sulfonyl}phenyl)methyl]furo[-
2,3-c]pyridine-2-carboxamide
N-({4-[(5-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(5-chloro-2-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-[(4-{[4-(1H-imidazol-1-ylmethyl)benzene]sulfonyl}phenyl)methyl]thieno[2-
,3-c]pyridine-2-carboxamide
N-({4-[(4-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(3-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-[(4-{[4-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyri-
dine-2-carboxamide
N-[(4-{[4-fluoro-2-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]-1H-pyr-
rolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carb-
oxamide
N-[(4-{[3-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[-
3,2-c]pyridine-2-carboxamide
N-({4-[1-(3-chlorophenyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)furo[2,3-c-
]pyridine-2-carboxamide
N-[(4-{5H,6H,7H,8H,9H-imidazo[1,2-a]azepine-3-sulfonyl}phenyl)methyl]imid-
azo[1,2-a]pyrimidine-6-carboxamide
N-({4-[(3-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(3-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-{[4-(2-methyl-1,3-thiazole-4-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]-
pyridine-5-carboxamide
N-({4-[6-(4-methylpiperazin-1-yl)pyridine-3-sulfonyl]phenyl}methyl)-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-2,5-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]py-
ridine-2-carboxamide
N-{[4-(2-methyl-1,3-thiazole-4-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-
-2-carboxamide
N-({4-[(2,3-dimethoxy-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2--
a]pyrimidine-6-carboxamide
N-({4-[(2-methanesulfonylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-[(4-{[4-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrim-
idine-6-carboxamide
N-{[4-(quinoline-8-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-5-c-
arboxamide
N-{[4-(1-methyl-1H-indazole-4-sulfonyl)phenyl]methyl}-1H-pyrazo-
lo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-cyclohexylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine--
2-carboxamide
N-{[4-(1-propyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridi-
ne-6-carboxamide
N-({4-[(2-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-({4-[(2-butoxy-6-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-{[4-(5-fluoropyridine-3-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyrid-
ine-5-carboxamide
N-{[4-({3-[2-(dimethylamino)ethyl]benzene}sulfonyl)phenyl]methyl}imidazo[-
1,2-a]pyrimidine-6-carboxamide
N-({4-[(2,6-dimethoxy-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[-
3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyrid-
ine-2-carboxamide
N-[(4-{5H,6H,7H,8H,9H-imidazo[1,2-a]azepine-3-sulfonyl}phenyl)methyl]thie-
no[2,3-c]pyridine-2-carboxamide
N-({4-[(3-tert-butylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine--
2-carboxamide
N-[(4-{[3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,-
4-b]pyridine-5-carboxamide
N-[(4-{[3-fluoro-4-(methylsulfanyl)benzene]sulfonyl}phenyl)methyl]imidazo-
[1,2-a]pyridine-6-carboxamide
N-{[4-(2,3-dihydro-1,4-benzodioxine-6-sulfonyl)phenyl]methyl}furo[2,3-c]p-
yridine-2-carboxamide
N-({4-[(4-butylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carbo-
xamide
N-{[4-(1-methyl-1H-indole-2-sulfonyl)phenyl]methyl}thieno[2,3-c]pyr-
idine-2-carboxamide
N-[(4-{6-chloroimidazo[1,2-a]pyridine-3-sulfonyl}phenyl)methyl]-1H-pyrazo-
lo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-fluoro-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]furo[2-
,3-c]pyridine-2-carboxamide
N-({4-[(4-phenylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-({4-[(4-ethoxy-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-{[4-(5-chloro-3-methylpyridine-2-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,-
4-b]pyridine-5-carboxamide
N-{[4-(1-propyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridin-
e-2-carboxamide
N-[(4-{[4-(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
rimidine-6-carboxamide
N-{[4-(4-methylpyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-
-carboxamide
N-[(4-{[3-(methoxymethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(2-butoxy-5-chlorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[(3-fluoro-4-propoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(2-methyl-4-propoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-[(4-{[5-fluoro-2-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[-
1,2-a]pyrimidine-6-carboxamide
N-[(4-{[3-(methoxymethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridi-
ne-2-carboxamide
N-{[4-(5-methoxypyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine--
6-carboxamide
N-({4-[1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)-
imidazo[1,2-a]pyridine-6-carboxamide
N-[(4-{[4-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yridine-6-carboxamide
N-[(4-{[2-(benzyloxy)-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]--
1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-{[4-(cyclohexanesulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-2-car-
boxamide
N-[(4-{8-thiatricyclo[7.4.0.0.sup.2,7]trideca-1(13),2,4,6,9,11-he-
xaene-6-sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-carboxamide
N-({4-[(3,4-difluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine--
2-carboxamide N-{[4-(benzenesulfonyl)phenyl]methyl}
isoquinoline-7-carboxamide
N-[(4-{[3-fluoro-4-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-
imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[(2-butoxy-5-chlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-[(4-{[4-fluoro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-{[4-(5-methylthiophene-2-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
-carboxamide
N-({4-[(2,6-dichlorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine--
2-carboxamide
N-[(4-{[2-methyl-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]furo[2-
,3-c]pyridine-2-carboxamide
N-{[4-({4-[(pyrrolidin-1-yl)carbonyl]benzene}sulfonyl)phenyl]methyl}-1H-p-
yrazolo[3,4-b]pyridine-5-carboxamide
N-{[4-(quinoline-8-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-carboxa-
mide
N-({4-[6-(morpholin-4-yl)pyridine-3-sulfonyl]phenyl}methyl)furo[2,3-c-
]pyridine-2-carboxamide
N-({4-[(4-butoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(3-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-[(4-{[3-fluoro-5-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-({4-[(4-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-{[4-(6-methylpyrazine-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-ca-
rboxamide
N-{[4-(1-methyl-1H-indazole-4-sulfonyl)phenyl]methyl}-1,3-benzot-
hiazole-6-carboxamide
N-[(4-{[3-(difluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-({4-[(3-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-({4-[(5-acetyl-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(4-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6--
carboxamide
N-({4-[(2,3-dimethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
-carboxamide
N-[(4-{[5-fluoro-2-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[-
1,2-a]pyridine-6-carboxamide
N-({4-[(5-tert-butyl-2-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c-
]pyridine-2-carboxamide
N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
-c]pyridine-2-carboxamide
N-[(4-{[3-fluoro-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-py-
razolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-chloro-4-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[(2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-{[4-(2,6-dimethoxypyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrid-
ine-6-carboxamide
N-{[4-(2H-1,3-benzodioxole-4-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
-carboxamide
N-({4-[(2,3-difluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyr-
idine-5-carboxamide
N-[(4-{[3-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-[(4-{[3-fluoro-5-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyrimidine-6-carboxamide
N-({4-[(3-fluoro-4-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-[(4-{[4-(4-methylpiperazin-1-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
-c]pyridine-2-carboxamide
N-({4-[(3-ethoxy-2-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[(4-butylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-car-
boxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-3-bromo-1H-pyrrolo[3,2-c]py-
ridine-2-carboxamide
N-[(4-{6-chloroimidazo[1,2-a]pyridine-3-sulfonyl}phenyl)methyl]imidazo[1,-
2-a]pyridine-6-carboxamide
N-({4-[(2,6-dichlorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2--
carboxamide
N-{[4-({3-[(dimethylamino)methyl]benzene}sulfonyl)phenyl]methyl}imidazo[1-
,2-a]pyrimidine-6-carboxamide
N-({4-[(2-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-[(4-{[2-methoxy-5-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imid-
azo[1,2-a]pyridine-6-carboxamide
N-{[4-(2-methyl-1,3-thiazole-4-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrim-
idine-6-carboxamide
N-{[4-(phenoxathiine-4-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-car-
boxamide
N-[(4-{[3-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]furo[2,-
3-c]pyridine-2-carboxamide
N-({4-[(5-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridin-
e-2-carboxamide
N-{[4-(1-propyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine--
2-carboxamide
N-{[4-(dimethyl-1,3-thiazole-5-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrid-
ine-6-carboxamide
N-({4-[(2-methyl-4-propoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(3-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(4-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(2,3-dimethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
-2-carboxamide
N-({4-[(4-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(5-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-[(4-{[2-chloro-5-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imida-
zo[1,2-a]pyrimidine-6-carboxamide
N-({4-[(4-phenylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
-carboxamide
N-({4-[(2-butoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-{[4-(2H-1,3-benzodioxole-5-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-
-2-carboxamide
N-({4-[(2,5-difluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyr-
idine-5-carboxamide
N-[(4-{[4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(2,5-dimethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
-2-carboxamide
N-{[4-(5-methoxypyridine-3-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyri-
dine-5-carboxamide
N-{[4-(5-fluoropyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-
-carboxamide
N-[(4-{2-[ethyl(methyl)amino]-1,3-thiazole-5-sulfonyl}phenyl)methyl]-1H-p-
yrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(3-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[(3,5-dimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine--
2-carboxamide
N-[(4-{[4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
-c]pyridine-2-carboxamide
N-{[4-(2-methyl-2H-indazole-5-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridi-
ne-6-carboxamide
N-[(4-{[3-chloro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2-
,3-c]pyridine-2-carboxamide
N-{[4-(2-methyl-2H-indazole-5-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridin-
e-2-carboxamide
N-{[4-(quinoline-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-carb-
oxamide
N-[(4-{[3-(dimethylsulfamoyl)benzene]sulfonyl}phenyl)methyl]furo[2-
,3-c]pyridine-2-carboxamide
N-({4-[2-(3-fluorophenyl)-1,3-thiazole-4-sulfonyl]phenyl}methyl)thieno[2,-
3-c]pyridine-2-carboxamide
5-hydroxy-N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]-1H-in-
dole-2-carboxamide
N-({4-[(2-chlorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-{[4-(1-benzothiophene-7-sulfonyl)phenyl]methyl}thieno[2,3-c]py-
ridine-2-carboxamide
N-({4-[(3-tert-butylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-
-6-carboxamide
N-({4-[(3-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-[(4-{[3-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrim-
idine-6-carboxamide
N-({4-[(4-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(3-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-c-
arboxamide
N-({4-[(3-cyanobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-({4-[2-(benzenesulfonyl)ethyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine--
2-carboxamide
N-({4-[(3-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-[(4-{[5-fluoro-2-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrr-
olo[3,2-c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-4-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridi-
ne-6-carboxamide
N-({4-[(3-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(3,5-dichlorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine--
2-carboxamide
N-{[4-(4-methylthiophene-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine--
6-carboxamide
N-({4-[(2-fluoro-4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-carboxamide
N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[2-(3-fluorophenyl)-1,3-thiazole-4-sulfonyl]phenyl}methyl)imidazo[1-
,2-a]pyridine-6-carboxamide
N-({4-[(5-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-[(4-{[3-(methylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-{[4-(2,6-dimethoxypyridine-3-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]-
pyridine-5-carboxamide
N-[(4-{[4-methoxy-2-[(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo-
[2,3-c]pyridine-2-carboxamide
N-{[4-(pyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-carbo-
xamide
N-({4-[(4-cyclohexylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
rimidine-6-carboxamide
N-({4-[(4-butoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-({4-[2-(pyrrolidin-1-yl)-1,3-thiazole-5-sulfonyl]phenyl}methyl)thieno[2-
,3-c]pyridine-2-carboxamide
N-({4-[(4-phenylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-[(4-{[3-(diethylcarbamoyl)-5-fluorobenzene]sulfonyl}phenyl)methyl]imida-
zo[1,2-a]pyrimidine-6-carboxamide
N-{[4-(5-methoxypyridine-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine--
6-carboxamide
N-[(4-{[3-fluoro-5-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-
furo[2,3-c]pyridine-2-carboxamide
N-[(4-{[2-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)benzene]sulfonyl}phe-
nyl)methyl]imidazo[1,2-a]pyridine-6-carboxamide
N-[(4-{[3-chloro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-(4-ethoxyphenyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-({4-[(5-chloro-2-hydroxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(3-fluoro-4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(3-fluoro-4-propoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(4-methoxy-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-5-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimi-
dine-6-carboxamide
N-{[4-(6-methylpyridine-3-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridi-
ne-2-carboxamide
N-({4-[(2-phenoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-c-
arboxamide
N-[(4-{[3-fluoro-5-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phen-
yl)methyl]thieno[2,3-c]pyridine-2-carboxamide
N-({4-[(3-ethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-[(4-{[3-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-({4-[2-(pyrrolidin-1-yl)-1,3-thiazole-5-sulfonyl]phenyl}methyl)-1H-pyra-
zolo[3,4-b]pyridine-5-carboxamide
N-{[4-({3-[(2-methylpropyl)carbamoyl]benzene}sulfonyl)phenyl]methyl}thien-
o[2,3-c]pyridine-2-carboxamide
N-({4-[(4-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-car-
boxamide
N-[(4-{[5-chloro-2-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl-
]imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[(2,4-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyr-
idine-5-carboxamide
N-({4-[6-(morpholin-4-yl)pyridine-3-sulfonyl]phenyl}methyl)imidazo[1,2-a]-
pyrimidine-6-carboxamide
N-[(4-{[3-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-2,5-dimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]-
pyridine-2-carboxamide
N-[(4-{[2-chloro-5-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-p-
yrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-car-
boxamide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
-c]pyridine-2-carboxamide
N-({4-[(4-phenylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carb-
oxamide
N-({4-[(2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyri-
midine-6-carboxamide
N-({4-[(3-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-({4-[1-(3-chlorophenyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)thieno[2,3-
-c]pyridine-2-carboxamide
N-({4-[(2-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-({4-[(2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-{[4-(pyridine-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-carboxamid-
e
N-({4-[(3-butoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridin-
e-2-carboxamide
N-({4-[(3,4-dichlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyr-
idine-5-carboxamide
N-({4-[(2,4-dimethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
-2-carboxamide
N-[(4-{[2-fluoro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(dimethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a-
]pyridine-6-carboxamide
N-({4-[(2-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-{[4-(4-methylpyridine-3-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-ca-
rboxamide
N-({4-[(4-butoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2-
,3-c]pyridine-2-carboxamide
N-({4-[(3-ethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carbo-
xamide
N-[(4-{[3-fluoro-5-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]-
furo[2,3-c]pyridine-2-carboxamide
N-({4-[(3-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(3-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-[(4-{[2-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]-
pyrimidine-6-carboxamide
N-({4-[(2-ethoxy-6-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[(3,5-difluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-
-6-carboxamide
N-[(4-{[4-fluoro-2-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]imidazo-
[1,2-a]pyrimidine-6-carboxamide
N-({4-[2-(morpholin-4-yl)pyridine-3-sulfonyl]phenyl}methyl)furo[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(2-phenoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridin-
e-2-carboxamide
N-[(4-{[3-chloro-5-(diethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]furo[-
2,3-c]pyridine-2-carboxamide
N-({4-[(2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[(3-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-[(4-{[3-(ethanesulfonyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-{[4-(1,4-dimethyl-1H-imidazole-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]p-
yrimidine-6-carboxamide
N-[(4-{[4-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(3-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine--
6-carboxamide
N-({4-[(4-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-[(4-{[5-fluoro-2-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
-c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-indole-2-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyr-
idine-5-carboxamide
N-({4-[(4-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-({4-[(2,6-dichloro-3-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]-
pyridine-2-carboxamide
N-({4-[(2,5-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimid-
ine-6-carboxamide
N-({4-[(3-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-ca-
rboxamide
N-({4-[(4-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)thieno[-
2,3-c]pyridine-2-carboxamide
N-({4-[2-(pyrrolidin-1-yl)-1,3-thiazole-5-sulfonyl]phenyl}methyl)imidazo[-
1,2-a]pyridine-6-carboxamide
N-[(4-{[3-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3--
c]pyridine-2-carboxamide
N-{[4-(dimethyl-1,3-thiazole-5-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-
-2-carboxamide
N-{[4-(6-methoxypyridine-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine--
6-carboxamide
N-[(4-{[3-fluoro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
rrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2,4,6-trimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]p-
yridine-2-carboxamide
N-({4-[6-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)imidazo[1,2-a-
]pyridine-6-carboxamide
N-({4-[(4-chloro-3-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-({4-[(3-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-[(4-{[3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
-c]pyridine-2-carboxamide
N-({4-[(2-cyanobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-car-
boxamide
N-[(4-{[2-fluoro-3-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl-
]imidazo[1,2-a]pyrimidine-6-carboxamide
N-[(4-{[4-(difluoromethyl)-3-fluorobenzene]sulfonyl}phenyl)methyl]imidazo-
[1,2-a]pyrimidine-6-carboxamide
N-{[4-(1-methyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine--
2-carboxamide
N-{[4-(phenoxathiine-4-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-
-5-carboxamide
N-[(4-{[2-(dimethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a-
]pyrimidine-6-carboxamide
N-({4-[(3-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-({4-[(4-methoxy-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyrid-
ine-2-carboxamide
N-[4-(benzenesulfonyl)phenyl]pyridine-3-carboxamide
N-({4-[(2-methyl-4-propoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyr-
idine-2-carboxamide
N-({4-[(3-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridi-
ne-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-imidazo[4,5-c]pyridine-2-carboxa-
mide
N-[(4-{[2,4-bis(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-{[4-(6-methoxynaphthalene-2-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridin-
e-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-3-(pyridin-4-yl)-1H-pyrazole-5-carb-
oxamide
N-({4-[(2-acetylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-
-2-carboxamide
N-({4-[(4-methanesulfonylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-{[4-(4-methylpyridine-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-ca-
rboxamide
N-({4-[(3-fluoro-4-methoxybenzene)sulfonyl]phenyl}methyl)imidazo-
[1,2-a]pyrimidine-6-carboxamide
N-[(4-{[3-fluoro-4-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-p-
yrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-[(4-{[2-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]p-
yridine-2-carboxamide
N-({4-[(4-ethoxy-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
imidine-6-carboxamide
N-({4-[(6-chloro-2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
-c]pyridine-2-carboxamide
N-({4-[(5-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-{[4-(furan-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-carboxamid-
e
N-({4-[(2,6-dimethoxy-4-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]-
pyridine-2-carboxamide N-({4-[(2-phenylethane)
sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyri-
dine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-4-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]py-
ridine-2-carboxamide
N-[(4-{[3-fluoro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno-
[2,3-c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-6-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]p-
yridine-5-carboxamide
N-[(4-{[4-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyri-
dine-2-carboxamide
N-({4-[6-(3,4-difluorophenyl)pyridine-2-sulfonyl]phenyl}methyl)furo[2,3-c-
]pyridine-2-carboxamide
N-({4-[(3-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-({4-[(3-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(3,5-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimid-
ine-6-carboxamide
N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]-1,3-benzothiazo-
le-6-carboxamide
N-({4-[(3-ethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide
N-({4-[(3-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(4-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-{[4-({4-[(pyrrolidin-1-yl)carbonyl]benzene}sulfonyl)phenyl]methyl}furo[-
2,3-c]pyridine-2-carboxamide
N-[(4-{[3-(methoxymethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-c-
]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-7-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]py-
ridine-2-carboxamide
N-[(4-{[3-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
-c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-5-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]py-
ridine-2-carboxamide
N-({4-[(4-cyanobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine--
2-carboxamide
N-{[4-(2,3-dihydro-1-benzofuran-7-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2--
c]pyridine-2-carboxamide
N-({4-[(2-cyanobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine--
2-carboxamide
5-N-({4-[(3,5-difluorobenzene)sulfonyl]phenyl}methyl)pyridine-2,5-diamido
N-({4-[(4-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1,6-naphthyridine-2-carboxamide
N-({4-[(4-methoxy-3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(4-methanesulfonylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(2-cyanobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridine-
-5-carboxamide
N-({4-[(3-methoxy-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-[(4-{[3-fluoro-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyridine-6-carboxamide
N-{[4-(2H-1,3-benzodioxole-5-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridin-
e-6-carboxamide
N-({4-[(2-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-({4-[(4-fluoro-2,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[-
3,4-b]pyridine-5-carboxamide
N-({4-[(2,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyr-
idine-5-carboxamide
N-({4-[(5-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-[(4-{[2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]p-
yridine-6-carboxamide
N-({4-[(2-acetylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-[(4-{[2-methyl-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
razolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-fluoro-6-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-{[4-(quinoline-8-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-carbox-
amide
N-[(4-{[4-chloro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]--
1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2,5-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]py-
ridine-5-carboxamide
N-({4-[(4-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(2-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-c-
arboxamide
N-[(4-{[3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imida-
zo[1,2-a]pyridine-6-carboxamide
N-[(4-{8-oxatricyclo[7.4.0.0.sup.2,7]trideca-1(13),2,4,6,9,11-hexaene-6-s-
ulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
6-amino-N-({4-[(3,5-difluorobenzene)sulfonyl]phenyl}methyl)pyridine-3-car-
boxamide
N-({4-[(3-chloro-4-propoxybenzene)sulfonyl]phenyl}methyl)-1H-pyra-
zolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-methoxy-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-p-
yrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(4-methoxy-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(3-ethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-ca-
rboxamide
N-({4-[(4-ethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyri-
dine-6-carboxamide
N-[(4-{[4-chloro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyridine-6-carboxamide
N-[(4-{[4-fluoro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
razolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-(cyclopentylcarbamoyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazo-
lo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,-
4-b]pyridine-5-carboxamide
N-[(4-{[2-(morpholin-4-ylmethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,-
2-a]pyridine-6-carboxamide
N-({4-[(2-ethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridine-
-5-carboxamide
N-[(4-{[3-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrid-
ine-6-carboxamide
N-({4-[(5-tert-butyl-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2--
a]pyridine-6-carboxamide
N-({4-[(4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-c-
arboxamide
N-({4-[(3,4-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
-a]pyridine-6-carboxamide
N-({4-[(2-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-{[4-(phenoxathiine-4-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-ca-
rboxamide
N-({4-[(2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(2-phenoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6--
carboxamide
N-[(4-{[4-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(2-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(4-methoxy-2,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo-
[3,4-b]pyridine-5-carboxamide
N-[(4-{[2-chloro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
razolo[3,4-b]pyridine-5-carboxamide
N-{[4-(1-methyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]p-
yridine-5-carboxamide
N-({4-[(3-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[(4,5-difluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2--
a]pyridine-6-carboxamide
N-({4-[(2,4-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridin-
e-6-carboxamide
N-({4-[(2,4-difluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-
-6-carboxamide
N-{[4-(5-methylthiophene-2-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyri-
dine-5-carboxamide
N-[(4-{[5-fluoro-2-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyra-
zolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(4-methoxy-3,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo-
[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-fluoro-5-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]-1H-py-
razolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-propoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridi-
ne-5-carboxamide
N-({4-[(2,4,5-trimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]-
pyridine-5-carboxamide
N-({4-[(2-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(2,3,6-trimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b-
]pyridine-5-carboxamide
N-[(4-{[2-chloro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
razolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[(3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-c-
arboxamide
N-[(4-{[2-methoxy-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)me-
thyl]imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[(5-acetyl-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(4-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-[(4-{[3-chloro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
razolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-phenoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridi-
ne-5-carboxamide
N-({4-[(4-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-[(4-{[4-fluoro-3-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-
-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-fluoro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
razolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2,4,5-trimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrid-
ine-6-carboxamide
N-({4-[(2,3-difluoro-6-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[-
3,2-c]pyridine-2-carboxamide
N-{[4-(quinoline-6-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-carbox-
amide
N-[(4-{[3-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1-
,2-a]pyridine-6-carboxamide
N-({4-[(2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridi-
ne-5-carboxamide
N-({4-[(4-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-[(4-{[2,4-bis(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazo-
lo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-fluoro-4-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(2,3-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-
-6-carboxamide
N-({4-[(2-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-[(4-{[3-chloro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
razolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-chloro-3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(3,5-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-
-6-carboxamide
N-[(4-{[4-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,-
4-b]pyridine-5-carboxamide
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-c-
arboxamide
N-({4-[(2-fluoro-4-methoxybenzene)sulfonyl]phenyl}methyl)imidaz-
o[1,2-a]pyridine-6-carboxamide
N-({4-[(2,4-dichloro-3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo-
[3,4-b]pyridine-5-carboxamide
N-({4-[(2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6--
carboxamide
N-[(4-{[3-fluoro-4-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-
-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(5-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[(2,3-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridin-
e-6-carboxamide
N-({4-[(4-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6--
carboxamide
N-({4-[(2-butoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[(2,5-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridin-
e-6-carboxamide
N-({4-[(3,5-dichlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-
-6-carboxamide
N-({4-[(3-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6--
carboxamide
N-{[4-(1-methyl-1H-indazole-5-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]p-
yridine-5-carboxamide
N-({4-[(3-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-[(4-{[3-fluoro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-py-
razolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-c-
arboxamide
N-[(4-{[4-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyra-
zolo[3,4-b]pyridine-5-carboxamide N-({4-[(4-phenylbutane)
sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[(4-cyanobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridine-
-5-carboxamide
N-({4-[(3-sulfamoylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyri-
dine-5-carboxamide
N-[(4-{[2-(benzyloxy)-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]--
1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-{[4-(naphthalene-1-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-5-
-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-3-carboxa-
mide
N-{[4-(1-methyl-1H-indazole-7-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(5-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-{[4-(2H-1,3-benzodioxole-4-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]py-
ridine-5-carboxamide
N-({4-[(5-chloro-2-propoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(3-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(2-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-({4-[(4-butoxy-2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-[(4-{[4-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrid-
ine-6-carboxamide
N-({4-[(2,3-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]py-
ridine-5-carboxamide
N-({4-[(3-fluoro-4-propoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
-b]pyridine-5-carboxamide
N-[(4-{[2-(methylsulfamoyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,-
4-b]pyridine-5-carboxamide
N-[(4-{[2-methoxy-5-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]-1H-pyraz-
olo[3,4-b]pyridine-5-carboxamide
N-[(4-{[2-methyl-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyridine-6-carboxamide
N-[(4-{[2-fluoro-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]imidaz-
o[1,2-a]pyridine-6-carboxamide
N-({4-[(2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-({4-[(6-chloro-2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyra-
zolo[3,4-b]pyridine-5-carboxamide
N-{[4-({4-fluoro-3-[(propan-2-yl)carbamoyl]benzene}sulfonyl)phenyl]methyl-
}-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-butylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridine-
-5-carboxamide
N-({4-[(2-ethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-ca-
rboxamide
N-({4-[(2,4-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a-
]pyridine-6-carboxamide
N-[(4-{[3-(methoxymethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[(2,5-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-
-6-carboxamide
N-[(4-{[5-chloro-2-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]-1H-pyr-
azolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-butoxy-5-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[(4-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(3-butoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-({4-[(3-acetylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-c-
arboxamide N-({4-[(3-phenylpropane)
sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-butoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-({4-[(2,6-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyr-
idine-5-carboxamide
N-({4-[(2-chloro-6-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(4-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-[(4-{[3-fluoro-5-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-
-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-({4-[(3-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyr-
idine-6-carboxamide
N-({4-[(3,4-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-
-6-carboxamide
N-[(4-{[2-methoxy-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imida-
zo[1,2-a]pyridine-6-carboxamide
N-({4-[(2-chlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-c-
arboxamide
N-({4-[(3-cyanobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4--
b]pyridine-5-carboxamide
N-({4-[(2,4,6-trimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]-
pyridine-5-carboxamide
N-[(4-{[3-fluoro-4-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-p-
yrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(5-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]py-
ridine-6-carboxamide
N-(4-(3-(trifluoromethoxy)phenylsulfonyl)benzyl)-1H-pyrazolo[3,4-b]pyridi-
ne-5-carboxamide
N-(4-(3-(trifluoromethyl)phenylsulfonyl)benzyl)-1H-pyrazolo[3,4-b]pyridin-
e-5-carboxamide
N-(4-(3,5-difluorophenylsulfonyl)benzyl)-1,8a-dihydroimidazo[1,2-a]pyridi-
ne-6-carboxamide 7,8-Dihydro-5H-pyrido[3,4-b]pyrazine-6-carboxylic
acid 4-benzenesulfonyl-benzylamide
3,4-Dihydro-1H-[2,6]naphthyridine-2-carboxylic acid
4-benzenesulfonyl-benzylamide
3,4-Dihydro-1H-[2,7]naphthyridine-2-carboxylic acid
4-benzenesulfonyl-benzylamide
6,7-Dihydro-4H-isoxazolo[4,3-c]pyridine-5-carboxylic acid
4-benzenesulfonyl-benzylamide
5,8-Dihydro-6H-[1,7]naphthyridine-7-carboxylic acid
4-benzenesulfonyl-benzylamide
6,7-Dihydro-4H-isoxazolo[4,5-c]pyridine-5-carboxylic acid
4-benzenesulfonyl-benzylamide
1,3-Dihydro-pyrrolo[3,4-c]pyridine-2-carboxylic acid
4-benzenesulfonyl-benzylamide Imidazo[1,2-a]pyrazine-6-carboxylic
acid 4-benzenesulfonyl-benzylamide
Imidazo[1,5-a]pyridine-6-carboxylic acid
4-benzenesulfonyl-benzylamide
1H-Pyrazolo[3,4-c]pyridine-5-carboxylic acid
4-benzenesulfonyl-benzylamide Imidazo[1,2-a]pyridine-7-carboxylic
acid 4-(3,5-difluoro-benzenesulfonyl)-benzylamide
1H-Pyrazolo[4,3-b]pyridine-5-carboxylic acid
4-benzenesulfonyl-benzylamide Furo[3,2-b]pyridine-2-carboxylic acid
4-benzenesulfonyl-benzylamide
N-{[4-(benzenesulfonyl)phenyl]methyl}thieno[3,2-b]pyridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}imidazo[1,5-a]pyridine-6-carboxamide
N-{[5-(benzenesulfonyl)pyridin-2-yl]methyl}-1H-pyrrolo[3,2-c]pyridine-2-c-
arboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}imidazo[1,2-a]pyrazine-6-c-
arboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}furo[3,2-b]pyridine-2-carb-
oxamide
N-{[6-(benzenesulfonyl)pyridin-3-yl]methyl}-1H-pyrrolo[3,2-c]pyrid-
ine-2-carboxamide
N-{[4-(piperazine-1-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-carbox-
amide
N-{[4-(piperazine-1-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6--
carboxamide
N-{[4-(3-aminopyrrolidine-1-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine--
2-carboxamide hydrochloride
N-{[4-(3-aminopyrrolidine-1-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2--
carboxamide hydrochloride
N-({4-[(3,5-difluorobenzene)sulfinyl]phenyl}methyl)imidazo[1,2-a]pyridine-
-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-5,6,7,8-tetrahydro-1,6-naphthyridin-
e-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-5H,6H,7H-pyrrolo[3,4-b]pyridine-6-c-
arboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H,4H,5H,6H,7H-pyrazolo[4-
,3-c]pyridine-5-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine-
-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H,4H,5H,6H,7H-imidazo[4,5-c]pyridi-
ne-5-carboxamide; and
N-{[4-(benzenesulfonyl)phenyl]methyl}-4H,5H,6H,7H-[1,2]oxazolo[4,3-c]pyri-
dine-5-carboxamide and pharmacteutical acceptable salts
thereof.
24. A pharmaceutical composition comprising a compound of claim 1
and a pharmaceutically acceptable carrier.
25. The pharmaceutical composition of claim 24, further comprising
a chemotherapeutic agent.
26. The pharmaceutical composition of claim 25, wherein said
chemotherapeutic agent is a DNA damaging agent.
27. The pharmaceutical composition of claim 24, further comprising
a cell rescuing agent.
28. The pharmaceutical composition of claim 27, wherein said cell
rescuing agent is nicotinamide, nicotinic acid or nicotinamide
mononucleotide (NMN).
29. The pharmaceutical composition of claim 25, wherein said
chemotherapeutic agent is selected from the group consisting of:
cytotoxic agent, cisplatin, doxorubicin, taxotere, taxol,
etoposide, irinotecan, camptostar, topotecan, paclitaxel,
docetaxel, the epothilones, tamoxifen, 5-fluorouracil,
methoxtrexate, temozolomide, cyclophosphamide, SCH 66336,
tipifarnib (Zarnestra.RTM.), R115777, L778,123, BMS 214662,
Iressa.RTM., Tarceva.RTM., C225, GLEEVEC.RTM., Intron.RTM.,
Peg-Intron.RTM., aromatase combinations, ara-C, adriamycin,
cytoxan, gemcitabine, Uracil mustard, Chlormethine, Ifosfamide,
Melphalan, Chlorambucil, Pipobroman, Triethylenemelamine,
Triethylenethiophosphoramine, Busulfan, Carmustine, Lomustine,
Streptozocin, Dacarbazine, Floxuridine, Cytarabine,
6-Mercaptopurine, 6-Thioguanine, Fludarabine phosphate,
oxaliplatin, leucovirin, oxaliplatin (ELOXATIN.RTM.), Pentostatine,
Vinblastine, Vincristine, Vindesine, Bleomycin, Dactinomycin,
Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Mithramycin.TM.,
Deoxycoformycin, Mitomycin-C, L-Asparaginase, Teniposide
17.alpha.-Ethinylestradiol, Diethylstilbestrol, Testosterone,
Prednisone, Fluoxymesterone, Dromostanolone propionate,
Testolactone, Megestrol acetate, Methylprednisolone,
Methyltestosterone, Prednisolone, Triamcinolone, Chlorotrianisene,
Hydroxyprogesterone, Aminoglutethimide, Estramustine,
Medroxyprogesteroneacetate, Leuprolide, Flutamide, Toremifene,
goserelin, Carboplatin, Hydroxyurea, Amsacrine, Procarbazine,
Mitotane, Mitoxantrone, Levamisole, Navelbene, Anastrazole,
Letrazole, Capecitabine, Reloxafine, Droloxafine,
Hexamethylmelamine, Avastin, herceptin, Bexxar, Velcade, Zevalin,
Trisenox, Xeloda, Vinorelbine, Porfimer, Erbitux, Liposomal,
Thiotepa, Altretamine, Melphalan, Trastuzumab, Lerozole,
Fulvestrant, Exemestane, Ifosfomide, Rituximab, Campath,
leucovorin, dexamethasone, bicalutamide, carboplatin, chlorambucil,
letrozole, megestrol, valrubicin, and vinvlastin.
30. (canceled)
31. A method of inhibiting Nicotinamide phosphoribosyltransferase
("NAMPT") in a patient by administering to said patient a
therapeutically effective amount of at least one compound of claim
1.
32. (canceled)
33. A method of treating, preventing, inhibiting or eliminating a
disease or condition in a patient comprising administering to said
patient a therapeutically effective amount of at least one compound
of claim 1, wherein said disease or condition is selected from the
group consisting of cancer, ovarian cancer, breast cancer, uterine
cancer, colon cancer, cervical cancer, lung cancer, prostate
cancer, skin cancer, bladder cancer, pancreatic cancer, leukemia,
lymphoma, Hodgkin's disease, viral infections, Human
Immunodeficiency Virus, hepatitis virus, herpes virus, herpes
simplex, inflammatory disorders, irritable bowel syndrome,
inflammatory bowel disease, rheumatoid arthritis, asthma, chronic
obstructive pulmonary disease, osteoarthritis, osteoporosis,
dermatitis, atoptic dermatitis, psoriasis, systemic lupus
erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing
spodylitis, graft-versus-host disease, Alzheimer's disease,
cerebrovascular accident, atherosclerosis, diabetes,
glomerulonephiritis, metabolic syndrome, non-small cell lung
cancer, small cell lung cancer, multiple myeloma, leukemias,
lymphomas, squamous cell cancers, kidney cancer, uretral and
bladder cancers, cancers of head and neck, and cancers of the brain
and central nervous system.
34. The method of claim 33, wherein said disease is a cancer.
35. The method of claim 34, wherein said cancer is selected from
the group consisting of cancer is selected from leukemia, lymphoma,
ovarian cancer, breast cancer, uterine cancer, colon cancer,
cervical cancer, lung cancer, prostate cancer, skin cancer, CNS
cancer, bladder cancer, pancreatic cancer and Hodgkin's
disease.
36-39. (canceled)
Description
PRIORITY CLAIM
[0001] This application claims priority from U.S. provisional
application Ser. Nos. 61/379,789 and 61/379,796 filed Sep. 3, 2010,
U.S. provisional application Ser. Nos. 61/386,023 and 61/386,028
filed Sep. 24, 2010, U.S. provisional application Ser. No.
61/475,813 filed on Apr. 15, 2011, and U.S. provisional application
Ser. No. 61/483,242 filed on May 6, 2011, the contents of which are
fully incorporated herein by reference in their entirety.
FIELD OF THE INVENTION
[0002] The present invention relates to compounds and composition
for inhibition of Nicotinamide phosphoribosyltransferase ("NAMPT"),
their synthesis, applications and antidote.
BACKGROUND OF THE INVENTION
[0003] Nicotinamide adenine dinucleotide (NAD) plays fundamental
roles in both cellular energy metabolism and cellular signaling. In
energy metabolism, the chemistry of the pyridine ring allows NAD to
readily accept and donate electrons in hydride transfer reactions
catalyzed by numerous dehydrogenases.
[0004] The preparation of a class of compounds, comprising several
subclasses, which act as inhibitors of the formation of
nicotinamide adenyl nucleotide, and their use thereof as
anti-tumour agents, is already described in the patent applications
WO00/50399, WO97/48695, WO97/48696, WO97/48397, WO99/31063,
WO99/31060, WO99/31087, WO99/31064, WO00/50399, and WO03/80054.
[0005] One of these inhibitors,
(E)-N-[4-(1-benzoylpiperidin-4-yl)butyl]-3-(pyridine-3-yl)-acrylamide
also known as APO866, FK866, WK175, or WK22.175 and hereinafter
referred to as FK866 [International Non-proprietary Name], is
especially described in the literature as an anticancer agent.
FK866 may be used for treatment of diseases implicating deregulated
apoptosis such as cancer. It has been demonstrated in the prior art
that FK866 interferes with nicotinamide adenine dinucleotide (also
known and hereinafter referred to as NAD) biosynthesis and induces
apoptotic cell death without any DNA damaging effects.
[0006] Additionally, FK866 ((E)-N-[4-(1-benzoylpiperidin-4-yl)
butyl]-3-(pyridin-3-yl)acrylamide) induces apoptosis in HepG2 cells
without having primary effects on cellular energy metabolism.
(Hasmann M, Schemainda I. FK866, a Highly Specific Noncompetitive
Inhibitor of Nicotinamide Phosphoribosyltransferase, Represents a
Novel Mechanism for Induction of Tumor Cell Apoptosis. Cancer Res
2003; 63:7436-7442. [PubMed: 14612543]) Instead of causing
immediate cytotoxicity, it inhibits NAMPT and depletes the cells of
NAD, suggesting that FK866 could be a promising agent against
cancer cells that rely on nicotinamide to synthesize NAD. The
crystal structure of the NAMPT-FK866 complex reveals that the
compound binds at the nicotinamide-binding site of NAMPT to inhibit
its activity. FK866 has been tested in a murine renal cell
carcinoma model and shown to display anti-tumor, antimetastatic,
and anti-angiogenic activities (Drevs J, et al. Antiangiogenic
potency of FK866/K22.175, a new inhibitor of intracellular NAD
biosynthesis, in murine renal cell carcinoma. Anticancer Res 2003;
23:4853-4858. [PubMed:14981935]).
[0007] In a mouse mammary carcinoma model, FK866 also induces a
delay in tumor growth and an enhancement in tumor radiosensitivity
accompanied with dose-dependent decreases in NAD levels, pH, and
energy status. A chemosensitizing effect of FK866 has also been
observed on anti-neoplastic 1-methyl-3-nitro-1-nitrosoguanidinium
(MNNG)-induced cell death in THP-1 and K562 leukemia cell lines
(Pogrebniak A, et al. Chemopotentiating effects of a novel NAD
biosynthesis inhibitor, FK866, in combination with antineoplastic
agents. Eur J Med Res 2006; 11:313-321. [PubMed: 17052966]).
[0008] The efficacy of GMX1777 was evaluated in xenograft models
and the pharmacokinetic profile of GMX1778 and its effect on
nicotinamide adenine dinucleotide cellular levels was measured by
liquid chromatography/mass spectrometry. (Beauparlant P., et al.
Preclinical development of the nicotinamide phosphoribosyl
transferase inhibitor prodrug GMX1777. Anticancer Drugs. 2009 June;
20(5):346-54).
[0009] GMX1777 is a water-soluble intravenously administered
prodrug of GMX1778 that Gemin X in-licensed from LEO Pharma (LEO
numbers: EB1627 and CHS828, respectively). These compounds and
other substituted cyanoguanidines have the structures of Table 1.
None of the compounds of the present invention are
cyanoguanidines.
TABLE-US-00001 TABLE 1 ##STR00002## A ##STR00003## B1 ##STR00004##
B2 ##STR00005## C
Substituted Cyanoguanidines with Defined Pharmacological
Effects:
A Cytotoxic CHS 828;
[0010] B Potassium channel openers pinacidil (n) and 12 g of
compound as described in Perez-Medrano et al (B2); and C
Histamine-II receptor antagonist cimetidine. (from Lovborg et al.
BMC Research Notes 2009 2:114 doi:10.1186/1756-0500-2-114)
[0011] More recently, CHS-828 has been identified as a NAMPT
inhibitor (Olesen U H, et al. Anticancer agent CHS-828 inhibits
cellular synthesis of NAD. Biochem Biophys Res Commun 2008;
367:799-804. [PubMed: 18201551]). CHS-828 has been shown to
potently inhibit cell growth in a broad range of tumor cell lines,
although the detailed mechanism for this inhibitory effect of
CHS-828 remains undetermined (Ravaud A, et al. Phase I study and
guanidine kinetics of CHS-828, a guanidine-containing compound,
administered orally as a single dose every 3 weeks in solid tumors:
an ECSG/EORTC study. Eur J Cancer 2005; 41:702-707. [PubMed:
15763645]). Both FK866 and CHS-828 are currently in clinical trials
for cancer treatments.
[0012] There are numerous uses for drugs which inhibit NAMPT.
[0013] Lack of NAMPT expression strongly affects development of
both T and B lymphocytes. By using mutant forms of this protein and
a well-characterized pharmacological inhibitor (FK866), authors
demonstrated that the ability of the NAMPT to regulate cell
viability during genotoxic stress requires its enzymatic activity.
Collectively, these data demonstrate that NAMPT participates in
cellular resistance to genotoxic/oxidative stress, and it may
confer to cells of the immune system the ability to survive during
stressful situations such as inflammation. (Rongvaux, A., et al.
The Journal of Immunology, 2008, 181: 4685-4695).
[0014] NAMPT may also have effects on endothelium (EC) in relation
to high glucose levels, oxidative stress and on aging. It is also
believed that NAMPT may enable proliferating human EC to resist the
oxidative stress of aging and of high glucose, and to productively
use excess glucose to support replicative longevity and angiogenic
activity.
SUMMARY OF THE INVENTION
[0015] One aspect of this invention is the provision of compounds,
compositions, kits, and antidotes for the NAMPT pathway in mammals
having a compound of the Formula I:
##STR00006## [0016] wherein: [0017] R is an aryl, heteroaryl,
C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 cycloalkenyl,
heterocycloalkyl, arylalkyl-, (heteroaryl)alkyl-, (C.sub.3-C.sub.8
cycloalkyl)alkyl-, (C.sub.3-C.sub.8 cycloalkenyl)alkyl-,
(heterocycloalkyl)alkyl-, (aryloxy)alkyl-, (heteroaryloxy)alkyl-,
(C.sub.3-C.sub.8 cycloalkyloxy)alkyl-, (C.sub.3-C.sub.8
cycloalkenyloxy)alkyl- or (heterocycloalkyloxy)alkyl-, wherein the
heteroatom of each of said heteroaryl and heterocycloalkyl numbers
1, 2 or 3, and is independently selected from N, S or O, further
wherein each of said aryl, heteroaryl and heterocycloalkyl may
independently be either substituted or fused with an aryl or
heteroaryl, still further wherein any of said aryl, heteroaryl and
heterocycloalkyl is either unsubstituted or optionally
independently substituted with one or more substituents which can
be the same or different and are independently selected from the
group consisting of deuterium, halo, cyano, amino, aminoalkyl-,
(amino)alkoxy-, --CONH.sub.2, --C(O)NH(alkyl),
--C(O)N(alkyl).sub.2, --C(O)NH(aryl), --C(O)N(aryl).sub.2,
--CH.sub.zF.sub.3-z, --OCH.sub.zF.sub.3-z, -alkyl, -alkenyl,
-alkynyl, -alkoxy, hydroxyl, alkyl hydroxy, hydroxyl, alkyl
hydroxy, or (alkoxyalkyl)amino-, --N(R.sup.3)--C(O)-alkyl,
--N(R.sup.3)--C(O)-aryl, -cycloalkyl, -heterocycloalkyl, -aryl, and
heteroaryl, with the proviso that no two adjacent ring heteroatoms
are both S or both O; [0018] Ar is aryl, heteroaryl,
heterocycloalkyl or C.sub.3 to C.sub.8 cycloalkyl, with each of
said aryl, heteroaryl, heterocycloalkyl and cycloalkyl being either
unsubstituted or optionally independently substituted with 1, 2, 3
or 4 substituents which can be the same or different and are
independently selected from the group consisting of deuterium,
halo, cyano, amino, aminoalkyl-, (amino)alkoxy-, --CONH.sub.2,
--C(O)NH(alkyl), --C(O)N(alkyl).sub.2, --C(O)NH(aryl),
--C(O)N(aryl).sub.2, --CH.sub.zF.sub.3-z, --OCH.sub.zF.sub.3-z,
-alkyl, -alkenyl, -alkynyl, -alkoxy, hydroxyl, -alkyl hydroxyl,
aryloxy-, (alkoxyalkyl)amino-, --N(R.sup.3)--C(O)-alkyl,
--N(R.sup.3)--C(O)-aryl, -cycloalkyl, -heterocycloalkyl, -aryl, and
-heteroaryl; [0019] R.sup.4 is cycloalkyl, --CH.sub.zF.sub.3-z,
aryl, heterocycloalkyl, heteroaryl, alkyl, -alkenyl, -alkynyl,
(aryl)alkyl-, (heteroaryl)alkyl- or (heterocycloalkyl)alkyl-,
or
##STR00007##
[0019] wherein each of said cycloalkyl, aryl, heterocycloalkyl,
heteroaryl and alkyl is either unsubstituted or optionally
substituted with 1, 2, 3, 4 or 5 substituents which can be the same
or different and are independently selected from the group
consisting of deuterium, halo, cyano, amino, aminoalkyl-,
(amino)alkoxy-, --CONH.sub.2, --C(O)NH(alkyl),
--C(O)N(alkyl).sub.2, --C(O)NH(aryl), --C(O)N(aryl).sub.2,
--CH.sub.zF.sub.3-z, --OCH.sub.zF.sub.3-z, -alkyl, alkoxy-,
-alkenyl, -alkynyl, aryloxy-, (alkoxyalkyl)amino-, -cycloalkyl,
-heterocycloalkyl, (heterocycloalkyl)alkyl-, -aryl, (aryl)alkyl-,
-heteroaryl, (heteroaryl)alkyl-, --S(O).sub.2-alkyl,
--S(O).sub.2-aryl, --S(O).sub.2--CF.sub.3, --C(O)N(alkyl).sub.2,
--C(O)alkyl, --N(R.sup.3)--C(O)-alkyl, --N(R.sup.3)--C(O)-aryl,
--S(O.sub.2)NH.sub.2, --S(O.sub.2)NH(alkyl),
--S(O.sub.2)N(alkyl).sub.2, --N(H)S(O.sub.2)(alkyl),
--C(O)N(H)(alkyl), and methylenedioxy, (ii) further wherein each of
said cycloalkyl, aryl, heterocycloalkyl, and heteroaryl may
optionally additionally be fused with independently selected aryl,
heteroaryl, heterocycloalkyl or cycloalkyl; [0020] R.sup.3 is H,
alkyl or arylalkyl-; [0021] X is S, S(O), S(O).sub.2, O or C(O);
[0022] n is 1, 2, 3 or 4; [0023] m is 0, 1, 2, 3 or 4; [0024] q is
0 or 1; [0025] t is 0, 1 or 2; and [0026] z is 0, 1 or 2; [0027]
and pharmaceutically acceptable salts, solates, esters, prodrugs
and isomers thereof.
[0028] Another aspect of the invention are the compounds of Formula
I, where q=0, m=0, t=0, A=Ar, X=Q and R.sup.4 is
##STR00008##
and the formula is now Formula IB
##STR00009## [0029] where: [0030] R and R.sup.3 are as defined in
Formula I; [0031] R.sup.1 and R.sup.2 are the same or they are
different, and are independently selected from H, a straight or
branched C.sub.1 to C.sub.7 alkyl, straight or branched C.sub.1 to
C.sub.7 alkoxy, straight or branched C.sub.1 to C.sub.4
hydroxyalkyl, aryl, heteroaryl, heterocycloalkyl and cycloalkyl,
and wherein heteroatoms of said heteroaryl and heterocycloalkyl are
independently selected from one or more N, O and S, with the
proviso that no two adjacent ring heteroatoms are both S or both O,
further wherein R.sup.1 and R.sup.2 can be either unsubstituted or
optionally independently substituted with one or more substituents
which can be the same or different and are independently selected
from the group consisting of deuterium, halo, cyano, amino,
aminoalkyl-, (amino)alkoxy-, --CONH.sub.2, --C(O)NH(alkyl),
--C(O)N(alkyl).sub.2, --C(O)NH(aryl), --C(O)N(aryl).sub.2,
--CH.sub.zF.sub.3-z, --OCH.sub.zF.sub.3-z, -alkyl, -alkenyl,
-alkynyl, hydroxyalkyl-, -alkoxy, hydroxyl, alkyl hydroxy, carboxy,
(alkoxyalkyl)amino-, -alkylamine, aminocarbonyl-, --CHO,
--N(R.sup.3)--C(O)-alkyl, --N(R.sup.3)--C(O)-aryl, -cycloalkyl,
-heterocycloalkyl, -aryl, and heteroaryl; [0032] A is aryl,
heteroaryl, heterocycloalkyl or C.sub.3 to C.sub.8 cycloalkyl, with
each of said aryl, heteroaryl, heterocycloalkyl and cycloalkyl
being either unsubstituted or optionally independently substituted
with 1, 2, 3 or 4 substituents which can be the same or different
and are independently selected from the group consisting of
deuterium, halo, cyano, amino, aminoalkyl-, (amino)alkoxy-,
--CONH.sub.2, --C(O)NH(alkyl), --C(O)N(alkyl).sub.2,
--C(O)NH(aryl), --C(O)N(aryl).sub.2, --CH.sub.zF.sub.3-z,
--OCH.sub.zF.sub.3-z, -alkyl, -alkenyl, -alkynyl, -alkoxy,
hydroxyl, -alkyl hydroxyl, aryloxy-, (alkoxyalkyl)amino-,
--N(R.sup.3)--C(O)-alkyl, --N(R.sup.3)--C(O)-aryl, -cycloalkyl,
-heterocycloalkyl, -aryl, and -heteroaryl; [0033] Q is C(O), S(O),
S(O).sub.2, --N(H)--C(O)--, --S(O.sub.2)--NH--, or
--N(H)--S(O.sub.2)--; [0034] n is 0, 1, 2, 3 or 4; and [0035] z is
0, 1 or 2; [0036] and pharmaceutically acceptable salts, solvates,
esters, prodrugs or isomers thereof.
[0037] Another aspect of this invention is the provision of
compounds, compositions, kits, and antidotes for the NAMPT pathway
in mammals having a compound derived from Formula I where q=0, m=0
and t=0, whereby the formula becomes Formula II or pharmaceutically
acceptable salts thereof:
##STR00010##
where: [0038] R is heteroaryl comprising 1, 2, 3 or 4 heteroatom(s)
independently selected from N, S or O, wherein said heteroaryl may
be substituted by one or more substituents selected from the group
consisting of amino, oxo, and halo; and wherein said heteroaryl can
comprise one or more N-oxide(s) formed with a N atom member of said
heteroaryl; [0039] Ar is aryl or heteroaryl comprising 1, 2, 3 or 4
heteroatom(s) independently selected from N, S or O; [0040] X is
S(O).sub.2 or SO; [0041] R.sup.1 is --NHR.sup.4 where R.sup.4 is
cycloalkyl, heterocycloalkyl, aryl or heteroaryl; [0042]
cycloalkyl; [0043] aryl; [0044] heterocycloalkyl; or [0045]
heteroaryl; wherein: [0046] (i) each of said cycloalkyl, aryl, or
heteroaryl is unsubstituted or substituted with 1, 2, 3, 4 or 5
substituents which can be the same or different and are
independently selected from the group consisting of: [0047]
deuterium, halo, hydroxy, hydroxyalkyl, cyano,
--(CH.sub.2).sub.mNR.sup.aR.sup.b, oxo, alkyl, cyanoalkyl,
haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl-, alkenyl, alkynyl,
alkynylalkoxy, --CONH.sub.2, --S-alkyl, --C(O)NH(alkyl),
--C(O)N(alkyl).sub.2, --C(O)NH(cycloalkyl), --C(O)NH(aryl),
--C(O)N(aryl).sub.2, arylalkyl-, arylalkoxy-, aryloxy-, cycloalkyl,
heterocycloalkyl, aryl, (heterocycloalkyl)alkyl-,
(heterocycloalkyl)alkoxy-, --C(O)heterocycloalkyl, heteroaryl,
(heteroaryl)alkyl-, --S(O).sub.2-alkyl, --S(O).sub.2-aryl,
--S(O).sub.2--CH.sub.zF.sub.3-z, --C(O)alkyl,
--N(R.sup.5)--C(O)-alkyl, --N(R.sup.5)--C(O)-aryl,
--S(O.sub.2)NH.sub.2, --S(O.sub.2)NH(alkyl),
--S(O.sub.2)N(alkyl).sub.2, --N(H)(SO.sub.2)(alkyl), and
methylenedioxy, wherein each of said cycloalkyl, heterocycloalkyl,
aryl or heteroaryl may be substituted by one or more halo, cyano,
alkyl or alkoxy and; [0048] (ii) each of said cycloalkyl,
heterocycloalkyl, aryl, or heteroaryl may optionally additionally
be fused with independently selected aryl, heteroaryl,
heterocycloalkyl or cycloalkyl to from a bicyclic or tricyclic
group that may be substituted by one or more halo, cyano, alkyl or
alkoxy; [0049] R.sup.2 and R.sup.3 can be independently selected
from the group consisting of H and deuterium; [0050] R.sup.5 is H,
alkyl or arylalkyl-; [0051] R.sup.a and R.sup.b are independently
selected from the group consisting of H, alkyl, alkoxy, alkoxyalkyl
and haloalkyl; [0052] m is 0, 1, 2, 3, 4, 5 or 6; and [0053] n is 0
or 1.
[0054] Another aspect of this invention are compounds Formula II or
pharmaceutically acceptable salts thereof where X.dbd.SO.sub.2, and
the formula is:
##STR00011##
where: [0055] R is heteroaryl comprising 1, 2, 3 or 4 heteroatom(s)
independently selected from N, S or O, wherein said heteroaryl may
be substituted by one or more substituents selected from the group
consisting of amino, oxo, and halo; and wherein said heteroaryl can
comprise one or more N-oxide(s) formed with a N atom member of said
heteroaryl; [0056] Ar is aryl or 5 or 6 membered heteroaryl
comprising 1, 2, 3 or 4 heteroatom(s) independently selected from
N, S or O; [0057] R.sup.1 is --NHR.sup.4 and R.sup.4 is cycloalkyl,
heterocycloalkyl, aryl or heteroaryl; [0058] cycloalkyl; [0059]
aryl; or [0060] heteroaryl; wherein: [0061] each of said
cycloalkyl, aryl, or heteroaryl is unsubstituted or substituted
with 1, 2, 3, 4 or 5 substituents which can be the same or
different and are independently selected from the group consisting
of: [0062] deuterium, halo, hydroxy, hydroxyalkyl, cyano,
--(CH.sub.2).sub.mNR.sup.aR.sup.b, oxo, alkyl, cyanoalkyl,
haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl-, alkenyl, alkynyl,
alkynylalkoxy, --CONH.sub.2, --S-alkyl, --C(O)NH(alkyl),
--C(O)N(alkyl).sub.2, --C(O)NH(cycloalkyl), --C(O)NH(aryl),
--C(O)N(aryl).sub.2, arylalkyl-, arylalkoxy-, aryloxy-, cycloalkyl,
heterocycloalkyl, aryl, (heterocycloalkyl)alkyl-,
(heterocycloalkyl)alkoxy-, --C(O)heterocycloalkyl, heteroaryl,
(heteroaryl)alkyl-, --S(O).sub.2-alkyl, --S(O).sub.2-aryl,
--S(O).sub.2--CH.sub.zF.sub.3-z, --C(O)alkyl,
--N(R.sup.5)--C(O)-alkyl, --N(R.sup.5)--C(O)-aryl,
--S(O.sub.2)NH.sub.2, --S(O.sub.2)NH(alkyl),
--S(O.sub.2)N(alkyl).sub.2, --N(H)(SO.sub.2)(alkyl), and
methylenedioxy, wherein each of said cycloalkyl, heterocycloalkyl,
aryl or heteroaryl may be substituted by one or more halo, cyano,
alkyl or alkoxy and; [0063] each of said cycloalkyl,
heterocycloalkyl, aryl, or heteroaryl may optionally additionally
be fused with independently selected aryl, heteroaryl,
heterocycloalkyl or cycloalkyl to from a bicyclic or tricyclic
group that may be substituted by one or more halo, cyano, alkyl or
alkoxy; [0064] R.sup.2 and R.sup.3 can be independently selected
from the group consisting of H and deuterium; [0065] R.sup.5 is H,
alkyl or arylalkyl-; [0066] R.sup.a and R.sup.b are independently
selected from the group consisting of H, alkyl, alkoxy, alkoxyalkyl
and haloalkyl; and [0067] m is 0, 1, 2, 3, 4, 5 or 6.
[0068] Yet another aspect of the invention is compounds of Formula
II A, where Ar=phenyl, whereby the formula becomes Formula IIB: We
claim:
##STR00012##
where: [0069] R is bicyclic heteroaryl comprising 1, 2, 3 or 4
heteroatom(s) independently selected from N, S or O, wherein said
heteroaryl may be substituted by one or more substituents selected
from the group consisting of amino, oxo, and halo; and wherein said
heteroaryl can comprise one or more N-oxide(s) formed with a N atom
member of said heteroaryl; [0070] R.sup.1 is --NHR.sup.4 and
R.sup.4 is cycloalkyl, heterocycloalkyl, aryl or heteroaryl; [0071]
cycloalkyl; [0072] aryl; or [0073] heteroaryl; wherein: [0074] each
of said cycloalkyl, aryl, or heteroaryl is unsubstituted or
substituted with 1, 2, 3, 4 or 5 substituents which can be the same
or different and are independently selected from the group
consisting of: [0075] deuterium, halo, hydroxy, hydroxyalkyl,
cyano, (CH.sub.2).sub.mNR.sup.aR.sup.b, oxo, alkyl, cyanoalkyl,
haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl-, alkenyl, alkynyl,
alkynylalkoxy, --CONH.sub.2, --S-alkyl, --C(O)NH(alkyl),
--C(O)N(alkyl).sub.2, --C(O)NH(cycloalkyl), --C(O)NH(aryl),
--C(O)N(aryl).sub.2, arylalkyl-, arylalkoxy-, aryloxy-, cycloalkyl,
heterocycloalkyl, aryl, (heterocycloalkyl)alkyl-,
(heterocycloalkyl)alkoxy-, --C(O)heterocycloalkyl, heteroaryl,
(heteroaryl)alkyl-, --S(O).sub.2-alkyl, --S(O).sub.2-aryl,
--S(O).sub.2--CH.sub.zF.sub.3-z, --C(O)alkyl,
--N(R.sup.5)--C(O)-alkyl, --N(R.sup.5)--C(O)-aryl,
--S(O.sub.2)NH.sub.2, --S(O.sub.2)NH(alkyl),
--S(O.sub.2)N(alkyl).sub.2, --N(H)(SO.sub.2)(alkyl), and
methylenedioxy, wherein each of said cycloalkyl, heterocycloalkyl,
aryl or heteroaryl may be substituted by one or more halo, cyano,
alkyl or alkoxy and; [0076] each of said cycloalkyl,
heterocycloalkyl, aryl, or heteroaryl may optionally additionally
be fused with independently selected aryl, heteroaryl,
heterocycloalkyl or cycloalkyl to from a bicyclic or tricyclic
group that may be substituted by one or more halo, cyano, alkyl or
alkoxy; [0077] R.sup.2 and R.sup.3 can be independently selected
from the group consisting of H and deuterium; [0078] R.sup.5 is H,
alkyl or arylalkyl-; [0079] R.sup.a and R.sup.b are independently
selected from the group consisting of H, alkyl, alkoxy, alkoxyalkyl
and haloalkyl; [0080] m is 0, 1, 2, 3, 4, 5 or 6; [0081] z is 0, 1
or 2.
[0082] Another aspect of this invention is the provision of methods
of treating a disease via the inhibition of NAMPT in a subject
(e.g., a human) in need thereof by administering to the subject an
effective amount of the compound or the pharmaceutical formulation
of the present invention.
[0083] Still another aspect of this invention is to provide a
method for treating, preventing, inhibiting or eliminating a
disease or condition in a patient by inhibiting NAMPT in said
patient by administering a therapeutically effective amount of at
least one compound of this disclosure, wherein said disease or
condition is selected from the group consisting of cancer, ovarian
cancer, breast cancer, uterine cancer, colon cancer, cervical
cancer, lung cancer, prostate cancer, skin cancer, bladder cancer,
pancreatic cancer, leukemia, lymphoma, Hodgkin's disease, viral
infections, Human Immunodeficiency Virus, hepatitis virus, herpes
virus, herpes simplex, inflammatory disorders, irritable bowel
syndrome, inflammatory bowel disease, rheumatoid arthritis, asthma,
chronic obstructive pulmonary disease, osteoarthritis,
osteoporosis, dermatitis, atoptic dermatitis, psoriasis, systemic
lupus erythematosis, multiple sclerosis, psoriatic arthritis,
ankylosing spodylitis, graft-versus-host disease, Alzheimer's
disease, cerebrovascular accident, atherosclerosis, diabetes,
glomerulonephiritis, metabolic syndrome, non-small cell lung
cancer, small cell lung cancer, multiple myeloma, leukemias,
lymphomas, squamous cell cancers, kidney cancer, uretral and
bladder cancers, cancers of head and neck, cancers of the brain and
central nervous system.
[0084] Another preferred embodiment is a pharmaceutical formulation
comprising a pharmaceutically acceptable compound of the present
invention, which provides, upon administration to a human, a
decrease in tumor burden and/or metastases. The pharmaceutical
formulation can be administered by oral means or other suitable
means.
[0085] Yet another embodiment is a method of treating ovarian
cancer in a subject (e.g., a human) in need thereof by
administering to the subject an effective amount of the compound or
the pharmaceutical formulation of the present invention.
[0086] Yet another embodiment is a method of treating colon cancer
in a subject (e.g., a human) in need thereof by administering to
the subject an effective amount of the compound or the
pharmaceutical formulation of the present invention.
[0087] Yet another embodiment is a method of treating breast cancer
in a subject (e.g., a human) in need thereof by administering to
the subject an effective amount of the pharmaceutical formulation
of the present invention.
[0088] Yet another embodiment is a method of treating leukemia in a
subject (e.g., a human) in need thereof by administering to the
subject an effective amount of the compound or the pharmaceutical
formulation of the present invention.
[0089] Yet another embodiment is a method of treating colon cancer
before or after surgical resection and/or radiation therapy, in a
subject (e.g., a human) in need thereof by administering to the
subject an effective amount of the compound or the pharmaceutical
formulation of the present invention.
[0090] Yet another embodiment is a method of treating cancer before
or after surgical resection and/or radiation therapy, in a subject
(e.g., a human) in need thereof by administering to the subject an
effective amount of the compound or the pharmaceutical formulation
of the present invention, including adjunctive therapy to treat
nausea, with or without dexamethasone.
[0091] Yet another embodiment is a method of treating cancer before
or after surgical resection and or radiation therapy, in a subject
(e.g., a human) in need thereof by administering to the subject an
effective amount of the compound or the pharmaceutical formulation
of the present invention, including adjunctive therapy with one or
more additional therapeutic agents, or their pharmaceutically
acceptable salts. Non-limiting examples of such additional
therapeutic agents include cytotoxic agents (such as for example,
but not limited to, DNA interactive agents (such as cisplatin or
doxorubicin)); taxanes (e.g. taxotere, taxol); topoisomerase II
inhibitors (such as etoposide); topoisomerase I inhibitors (such as
irinotecan (or CPT-11), camptostar, or topotecan); tubulin
interacting agents (such as paclitaxel, docetaxel or the
epothilones); hormonal agents (such as tamoxifen); thymidilate
synthase inhibitors (such as 5-fluorouracil or 5-FU);
anti-metabolites (such as methoxtrexate); alkylating agents (such
as temozolomide, cyclophosphamide); Farnesyl protein transferase
inhibitors (such as, SARASAR.TM..
(4-[2-[4-[(11R)-3,10-dibromo-8-chloro-6,11-dihydro-5H-benzo[5,-6]cyclohep-
ta[1,2-b]pyridin-11-yl-]-1-piperidinyl]-2-oxoethyl]-1-piperidine-carboxami-
de, or SCH 66336), tipifarnib (Zarnestra.RTM. or R115777 from
Janssen Pharmaceuticals), L778,123 (a farnesyl protein transferase
inhibitor from Merck & Company, Whitehouse Station, N.J.), BMS
214662 (a farnesyl protein transferase inhibitor from Bristol-Myers
Squibb Pharmaceuticals, Princeton, N.J.); signal transduction
inhibitors (such as, Iressa.RTM. (from Astra Zeneca
Pharmaceuticals, England), Tarceva.RTM. (EGFR kinase inhibitors),
antibodies to EGFR (e.g., C225), GLEEVEC.RTM. (C-abl kinase
inhibitor from Novartis Pharmaceuticals, East Hanover, N.J.);
interferons such as, for example, Intron.RTM. (from Merck &
Company), Peg-Intron.RTM. (from Merck & Company); hormonal
therapy combinations; aromatase combinations; ara-C, adriamycin,
cytoxan, and gemcitabine.
[0092] Other anti-cancer (also known as anti-neoplastic) agents
include but are not limited to Uracil mustard, Chlormethine,
Ifosfamide, Melphalan, Chlorambucil, Pipobroman,
Triethylenemelamine, Triethylenethiophosphoramine, Busulfan,
Carmustine, Lomustine, Streptozocin, Dacarbazine, Floxuridine,
Cytarabine, 6-Mercaptopurine, 6-Thioguanine, Fludarabine phosphate,
oxaliplatin, leucovirin, oxaliplatin (ELOXATIN.RTM. from
Sanofi-Synthelabo Pharmaceuticals, France), Pentostatine,
Vinblastine, Vincristine, Vindesine, Bleomycin, Dactinomycin,
Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Mithramycin,
Deoxycoformycin, Mitomycin-C, L-Asparaginase, Teniposide
17.alpha.-Ethinylestradiol, Diethylstilbestrol, Testosterone,
Prednisone, Fluoxymesterone, Dromostanolone propionate,
Testolactone, Megestrolacetate, Methylprednisolone,
Methyltestosterone, Prednisolone, Triamcinolone, Chlorotrianisene,
Hydroxyprogesterone, Aminoglutethimide, Estramustine,
Medroxyprogesteroneacetate, Leuprolide, Flutamide, Toremifene,
goserelin, Cisplatin, Carboplatin, Hydroxyurea, Amsacrine,
Procarbazine, Mitotane, Mitoxantrone, Levamisole, Navelbene,
Anastrazole, Letrazole, Capecitabine, Reloxafine, Droloxafine,
Hexamethylmelamine, Avastin, herceptin, Bexxar, Velcade.RTM.,
Zevalin, Trisenox, Xeloda, Vinorelbine, Porfimer, Erbitux,
Liposomal, Thiotepa, Altretamine, Melphalan, Trastuzumab, Lerozole,
Fulvestrant, Exemestane, Ifosfomide, Rituximab, C225, and Campath,
5-fluorouracil and leucovorin, with or without a 5-HT.sub.3
receptor inhibitor (e.g., dolansetron, granisetron, ondansetron)
with or without dexamethasone.
[0093] If formulated as a fixed dose, such combination products
employ the compounds of this invention within the dosage range
described herein (or as known to those skilled in the art) and the
other pharmaceutically active agents or treatments within its
dosage range. For example, the CDC2 inhibitor olomucine has been
found to act synergistically with known cytotoxic agents in
inducing apoptosis (J. Cell Sci., (1995) 108, 2897). The compounds
of the invention may also be administered sequentially with known
anticancer or cytotoxic agents when a combination formulation is
inappropriate. In any combination treatment, the invention is not
limited in the sequence of administration; compounds of the
disclosed Formulas may be administered either prior to or after
administration of the known anticancer or cytotoxic agent. For
example, the cytotoxic activity of the cyclin-dependent kinase
inhibitor flavopiridol is affected by the sequence of
administration with anticancer agents. Cancer Research, (1997) 57,
3375. Such techniques are within the skills of persons skilled in
the art as well as attending physicians.
[0094] Any of the aforementioned methods may be augmented by
administration of fluids (such as water), loop diuretics, one or
more of a chemotherapeutic or antineoplastic agent, such as
leucovorin and fluorouracil, and an adjunctive chemotherapeutic
agent (such as filgrastim and erythropoietin), or any combination
of the foregoing.
[0095] Yet another embodiment is a method for administering a
compound of the instant invention to a subject (e.g., a human) in
need thereof by administering to the subject the pharmaceutical
formulation of the present invention.
[0096] Yet another embodiment is a method of preparing a
pharmaceutical formulation of the present invention by mixing at
least one pharmaceutically acceptable compound of the present
invention, and, optionally, one or more pharmaceutically acceptable
additives or excipients.
[0097] For preparing pharmaceutical compositions from the compounds
described by this invention, inert, pharmaceutically acceptable
carriers can be either solid or liquid. Solid form preparations
include powders, tablets, dispersible granules, capsules, cachets
and suppositories. The powders and tablets may be comprised of from
about 5 to about 95 percent active ingredient. Suitable solid
carriers are known in the art, e.g., magnesium carbonate, magnesium
stearate, talc, sugar or lactose. Tablets, powders, cachets and
capsules can be used as solid dosage forms suitable for oral
administration. Examples of pharmaceutically acceptable carriers
and methods of manufacture for various compositions may be found in
A. Gennaro (ed.), Remington's Pharmaceutical Sciences, 18th
Edition, (1990), Mack Publishing Co., Easton, Pa.
[0098] Liquid form preparations include solutions, suspensions and
emulsions. As an example may be mentioned water or water-propylene
glycol solutions for parenteral injection or addition of sweeteners
and opacifiers for oral solutions, suspensions and emulsions.
Liquid form preparations may also include solutions for intranasal
administration.
[0099] Aerosol preparations suitable for inhalation may include
solutions and solids in powder form, which may be in combination
with a pharmaceutically acceptable carrier, such as an inert
compressed gas, e.g. nitrogen.
[0100] Also included are solid form preparations that are intended
to be converted, shortly before use, to liquid form preparations
for either oral or parenteral administration. Such liquid forms
include solutions, suspensions and emulsions.
[0101] The compounds of the invention may also be deliverable
transdermally. The transdermal compositions can take the form of
creams, lotions, aerosols and/or emulsions and can be included in a
transdermal patch of the matrix or reservoir type as are
conventional in the art for this purpose.
[0102] The compounds of this invention may also be delivered
subcutaneously.
[0103] Preferably the compound is administered orally or
intravenously.
[0104] Preferably, the pharmaceutical preparation is in a unit
dosage form. In such form, the preparation is subdivided into
suitably sized unit doses containing appropriate quantities of the
active component, e.g., an effective amount to achieve the desired
purpose.
[0105] The quantity of active compound in a unit dose of
preparation may be varied or adjusted from about 1 mg to about 1000
mg, preferably from about 1 mg to about 500 mg, more preferably
from about 1 mg to about 250 mg, still more preferably from about 1
mg to about 25 mg, according to the particular application.
[0106] The actual dosage employed may be varied depending upon the
requirements of the patient and the severity of the condition being
treated. Determination of the proper dosage regimen for a
particular situation is within the skill of the art. For
convenience, the total daily dosage may be divided and administered
in portions during the day as required.
[0107] The amount and frequency of administration of the compounds
of the invention and/or the pharmaceutically acceptable salts
thereof will be regulated according to the judgment of the
attending clinician considering such factors as age, condition and
size of the patient as well as severity of the symptoms being
treated. A typical recommended daily dosage regimen for oral
administration can range from about 1 mg/day to about 500 mg/day,
preferably 1 mg/day to 200 mg/day, in two to four divided
doses.
DEFINITIONS
[0108] As used above, and throughout this disclosure, the following
terms, unless otherwise indicated, shall be understood to have the
following meanings. If a definition is missing, convention
definition as known to one skilled in the art controls.
[0109] "Patient" includes both human and animals.
[0110] "Mammal" means humans and other mammalian animals.
[0111] The term "inhibitor" refers to a molecule such as a
compound, a drug, an enzyme activator or a hormone that blocks or
otherwise interferes with a particular biologic activity.
[0112] The terms "effective amount" or "therapeutically effective
amount" refer to a sufficient amount of the agent to provide the
desired biological result. That result can be reduction and/or
alleviation of the signs, symptoms, or causes of a disease, or any
other desired alteration of a biological system. For example, an
"effective amount" for therapeutic use is the amount of the
composition comprising a compound as disclosed herein required to
provide a clinically significant decrease in a disease. An
appropriate "effective" amount in any individual case may be
determined by one of ordinary skill in the art using routine
experimentation. Thus, the expression "effective amount" generally
refers to the quantity for which the active substance has
therapeutic effects. In the present case the active substance is
the inhibitor of the formation of Nicotinamide
phosphoribosyltransferase (NAMPT).
[0113] As used herein, the terms "treat" or "treatment" are
synonymous with the term "prevent" and are meant to indicate a
postponement of development of diseases, preventing the development
of diseases, and/or reducing severity of such symptoms that will or
are expected to develop. Thus, these terms include ameliorating
existing disease symptoms, preventing additional symptoms,
ameliorating or preventing the underlying metabolic causes of
symptoms, inhibiting the disorder or disease, e.g., arresting the
development of the disorder or disease, relieving the disorder or
disease, causing regression of the disorder or disease, relieving a
condition caused by the disease or disorder, or stopping the
symptoms of the disease or disorder.
[0114] By "pharmaceutically acceptable" or "pharmacologically
acceptable" is meant a material which is not biologically or
otherwise substantially undesirable, i.e., the material may be
administered to an individual without causing any substantially
undesirable biological effects or interacting in a substantially
deleterious manner with any of the components of the composition in
which it is contained. Exemplary salts include, but are not
limited, to sulfate, citrate, acetate, oxalate, chloride, bromide,
iodide, nitrate, bisulfate, phosphate, acid phosphate,
isonicotinate, lactate, salicylate, acid citrate, tartrate, oleate,
tannate, pantothenate, bitartrate, ascorbate, succinate, maleate,
gentisinate, fumarate, gluconate, glucuronate, saccharate, formate,
benzoate, glutamate, methanesulfonate "mesylate", ethanesulfonate,
benzenesulfonate, p-toluenesulfonate, and pamoate (i.e.,
1,1'-methylene-bis(2-hydroxy-3-naphthoate)) salts. A
pharmaceutically acceptable salt may involve the inclusion of
another molecule such as an acetate ion, a succinate ion or other
counter ion. The counter ion may be any organic or inorganic moiety
that stabilizes the charge on the parent compound. Furthermore, a
pharmaceutically acceptable salt may have more than one charged
atom in its structure. Instances where multiple charged atoms are
part of the pharmaceutically acceptable salt can have multiple
counter ions. Hence, a pharmaceutically acceptable salt can have
one or more charged atoms and/or one or more counter ion.
[0115] "Carrier materials" or what are also referred to as
"excipients" include any commonly used excipients in pharmaceutics
and should be selected on the basis of compatibility and the
release profile properties of the desired dosage form. Exemplary
carrier materials include, e.g., binders, suspending agents,
disintegration agents, filling agents, surfactants, solubilizers,
stabilizers, lubricants, wetting agents, diluents, and the like.
"Pharmaceutically compatible carrier materials" may comprise, e.g.,
acacia, gelatin, colloidal silicon dioxide, calcium
glycerophosphate, calcium lactate, maltodextrin, glycerine,
magnesium silicate, sodium caseinate, soy lecithin, sodium
chloride, tricalcium phosphate, dipotassium phosphate, sodium
stearoyl lactylate, carrageenan, monoglyceride, diglyceride,
pregelatinized starch, and the like. See, e.g., Hoover, John E.,
Remington's Pharmaceutical Sciences, Mack Publishing Co., Easton,
Pa. 1975.
[0116] As used herein, the term "subject" encompasses mammals and
non-mammals. Examples of mammals include, but are not limited to,
any member of the Mammalian class: humans, non-human primates such
as chimpanzees, and other apes and monkey species; farm animals
such as cattle, horses, sheep, goats, swine; domestic animals such
as rabbits, dogs, and cats; laboratory animals including rodents,
such as rats, mice and guinea pigs, and the like. Examples of
non-mammals include, but are not limited to, birds, fish and the
like. In one embodiment of the present invention, the mammal is a
human.
[0117] As used herein, "alkyl" means a straight chain or branched
saturated chain having from 1 to 10 carbon atoms. Representative
saturated alkyl groups include, but are not limited to, methyl,
ethyl, n-propyl, isopropyl, 2-methyl-1-propyl, 2-methyl-2-propyl,
2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-3-butyl,
2,2-dimethyl-1-propyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl,
4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl,
4-methyl-2-pentyl, 2,2-dimethyl-1-butyl, 3,3-dimethyl-1-butyl,
2-ethyl-1-butyl, butyl, isobutyl, t-butyl, n-pentyl, isopentyl,
neopentyl, n-hexyl and the like, and longer alkyl groups, such as
heptyl, and octyl and the like. An alkyl group can be unsubstituted
or substituted. Alkyl groups containing three or more carbon atoms
may be straight, branched or cyclized. As used herein, "lower
alkyl" means an alkyl having from 1 to 6 carbon atoms.
[0118] As used herein, an "alkenyl group" includes an unbranched or
branched hydrocarbon chain having one or more double bonds therein.
The double bond of an alkenyl group can be unconjugated or
conjugated to another unsaturated group. Illustrative alkenyl
groups include, but are not limited to, (C.sub.2-C.sub.8) alkenyl
groups, such as ethylenyl, vinyl, allyl, butenyl, pentenyl,
hexenyl, butadienyl, pentadienyl, hexadienyl, 2-ethylhexenyl,
2-propyl-2-butenyl, 4-(2-methyl-3-butene)-pentenyl and the like. An
alkenyl group can be unsubstituted or substituted.
[0119] The term "hydroxyalkyl" denotes an alkyl group as defined
above wherein at least one of the hydrogen atoms of the alkyl group
is replaced by a hydroxy group. Examples of hydroxyalkyl include,
but are not limited to, methyl, ethyl, propyl, isopropyl, isobutyl,
sec-butyl, tert-butyl, pentyl or n-hexyl wherein one or more
hydrogen atoms are replaced by OH, as well as those hydroxyalkyl
groups specifically illustrated by the examples herein below.
[0120] The term "cyanoalkyl" denotes an alkyl group as defined
above wherein at least one of the hydrogen atoms of the alkyl group
is replaced by a cyano (--CN) group.
[0121] As used herein, "alkynyl group" includes an unbranched or
branched hydrocarbon chain having one or more triple bonds therein.
The triple bond of an alkynyl group can be unconjugated or
conjugated to another unsaturated group. Suitable alkynyl groups
include, but are not limited to, (C.sub.2-C.sub.6) alkynyl groups,
such as ethynyl, propynyl, butynyl, pentynyl, hexynyl,
methylpropynyl, 4-methyl-1-butynyl, 4-propyl-2-pentynyl,
4-butyl-2-hexynyl and the like. An alkynyl group can be
unsubstituted or substituted.
[0122] The term "haloalkyl" denotes an alkyl group as defined above
wherein at least one of the hydrogen atoms of the alkyl group is
replaced by a halogen atom, preferably fluoro or chloro, most
preferably fluoro. Examples of haloalkyl include, but are not
limited to, methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl,
tert-butyl, pentyl or n-hexyl wherein one or more hydrogen atoms
are replaced by Cl, F, Br or I atom(s), as well as those haloalkyl
groups specifically illustrated by the examples herein below. Among
the preferred haloalkyl groups are monofluoro-, difluoro- or
trifluoro-methyl, -ethyl or -propyl, for example
3,3,3-trifluoropropyl, 2-fluoroethyl, 2,2,2-trifluoroethyl,
fluoromethyl, trifluoromethyl.
[0123] The terms "trifluoromethyl," "sulfonyl," and "carboxyl"
include CF.sub.3, SO.sub.2, and CO.sub.2H, respectively.
[0124] The term "oxo" means .dbd.O-- group;
[0125] The term "hydroxy" means an OH group;
[0126] The term "alkoxy" as used herein includes --O-(alkyl),
wherein alkyl is defined above.
[0127] The term "aminoalkyl" as used herein means a group having
one or more nitrogen atoms and one or more alkyl groups as defined
above on the nitrogen.
[0128] "Aralkyl" or "arylalkyl" means an aryl-alkyl-group in which
the aryl and alkyl are as previously described. Preferred aralkyls
comprise a lower alkyl group. Non-limiting examples of suitable
aralkyl groups include benzyl, 2-phenethyl and naphthalenylmethyl.
The bond to the parent moiety is through the alkyl.
[0129] "Heteroarylalkyl" means a heteroaryl moiety as defined
herein linked via an alkyl moiety (defined above) to a parent core.
Non-limiting examples of suitable heteroaryls include
2-pyridinylmethyl, quinolinylmethyl and the like.
[0130] "Heterocyclylalkyl" means a heterocyclyl moiety as defined
herein linked via an alkyl moiety (defined above) to a parent core.
Non-limiting examples of suitable heterocyclylalkyls include
piperidinylmethyl, piperazinylmethyl and the like.
[0131] The term "bicyclic heteroaryl" means a structure having
atoms arranged in two rings fused together with at least two atoms
common to each ring, and at least one of the rings being a
heteroaryl ring. Non limiting examples of bicyclic heteroaryl
comprise bicyclic heteroaryl groups comprising 1, 2, 3 or 4
heteroatom(s) independently selected from N, S or O.
[0132] It should also be noted that any carbon as well as
heteroatom with unsatisfied valences in the text, schemes, examples
and Tables herein is assumed to have the sufficient number of
hydrogen atom(s) to satisfy the valences.
[0133] When any variable (e.g., aryl, heterocycle, R.sup.2, etc.)
occurs more than one time in any constituent or in the Formulas,
its definition on each occurrence is independent of its definition
at every other occurrence.
[0134] The term "N-oxide(s) formed with a N atom member of said
heteroaryl" denotes a heterorayl group containing a nitrogen atom
that forms a N-oxide. Illustrative and non limiting examples of
such N-oxides are:
##STR00013##
[0135] As used herein, the term "composition" is intended to
encompass a product comprising the specified ingredients in the
specified amounts, as well as any product which results, directly
or indirectly, from combination of the specified ingredients in the
specified amounts.
[0136] The term "deuterium" as used herein means a stable isotope
of hydrogen having odd numbers of protons and neutrons.
[0137] The term "halo" as used herein means a substituent having at
least one halogen selected from fluorine, chlorine, bromine, and
iodine.
[0138] The term "cyano" as used herein means a substituent having a
carbon atom joined to a nitrogen atom by a triple bond.
[0139] The term "amino" as used herein means a substituent
containing at least one nitrogen atom.
[0140] The term "(amino)alkoxy" as used herein means a substituent
having at least one amino group and at least one alkoxy group.
[0141] The term "aryloxy" as used herein means a substituent of the
form Ar--O-- where Ar is an aryl group as defined herein.
[0142] The term "methylenedioxy" as used herein means a functional
group with the structural formula --O--CH.sub.2--O-- which is
connected to the molecule by two chemical bonds via the
oxygens.
[0143] As used herein, "alkoxyalkyl" means -(alkyl)-O-(alkyl),
wherein each "alkyl" is independently an alkyl group defined
above.
[0144] The term "(alkoxyalkyl)amino" as used herein means a
substituent having at least one alkoxyalkyl group as defined above
and at least one amino group as defined above.
[0145] The term "spiroheterocycloalkyl" as used herein means a
spiro group (containing no heteroatom) linked in a spiro manner to
a heterocycloalkyl group. A non-limiting example would be the
moiety shown below:
##STR00014##
[0146] The term "heterospiroheterocycloalkyl" as used herein means
a spiro group (containing a hetero atom such O, N or S) linked in a
spiro manner to a heterocycloalkyl group. A non-limiting example
would be the moiety shown below:
##STR00015##
[0147] "Aryl" means a monovalent aromatic hydrocarbon radical of
6-20 carbon atoms (C.sub.6-C.sub.20) derived by the removal of one
hydrogen atom from a single carbon atom of a parent aromatic ring
system. Some aryl groups are represented in the exemplary
structures as "Ar". Aryl includes bicyclic radicals comprising an
aromatic ring fused to a saturated, partially unsaturated ring, or
aromatic carbocyclic ring. Typical aryl groups include, but are not
limited to, radicals derived from benzene (phenyl), substituted
benzenes, naphthalene, anthracene, biphenyl, indenyl, indanyl,
1,2-dihydronaphthalene, 1,2,3,4-tetrahydronaphthyl, and the like.
Aryl groups are optionally substituted independently with one or
more substituents described herein. Illustrative examples of aryl
groups include, but are not limited to phenyl, naphthalene and the
following moieties:
##STR00016##
and the like.
[0148] Illustrative substituted aryls include:
##STR00017## ##STR00018## ##STR00019## ##STR00020## ##STR00021##
##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026##
##STR00027##
and the like.
[0149] As used herein, the term "heteroaryl" refers to a
monocyclic, or fused polycyclic, aromatic heterocycle (ring
structure having ring atoms selected from carbon atoms as well as
nitrogen, oxygen, and/or sulfur atoms) having from 3 to 24 ring
atoms per ring. The term "heteroaryl" as used herein also includes
a monovalent aromatic radical of a 5-, 6-, or 7-membered ring and
includes fused ring systems (at least one of which is aromatic) of
5-10 atoms containing at least one heteroatom independently
selected from nitrogen, oxygen, and sulfur. Examples of heteroaryl
groups include, but are not limited to pyridinyl, imidazolyl,
imidazopyridinyl, pyrimidinyl, pyrazolyl, triazolyl, pyrazinyl,
tetrazolyl, furyl, thienyl, isoxazolyl, thiazolyl, oxazolyl,
isothiazolyl, pyrrolyl, quinolinyl, isoquinolinyl, indolyl,
benzimidazolyl, benzofuranyl, cinnolinyl, indazolyl, indolizinyl,
phthalazinyl, pyridazinyl, triazinyl, isoindolyl, pteridinyl,
purinyl, oxadiazolyl, triazolyl, thiadiazolyl, thiadiazolyl,
furazanyl, benzofurazanyl, benzothiophenyl, benzothiazolyl,
benzoxazolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, and
furopyridinyl. Spiro moieties are also included within the scope of
this definition. Heteroaryl groups may be optionally substituted
independently with one or more substituents described herein. 5 or
6 membered heteroaryl can be selected from the group consisting of
optionally substituted pyridinyl, pyrimidinyl, thiazolyl,
imidazolyl, oxazolyl, isoxazolyl, pyrazolyl, pyridinone and
benzimidazolyl. In a certain embodiment, heteroaryl is bicyclic
heteroaryl selected from benzothiazole, dihydronaphthyridine,
dihydropyridopyrimidine, dihydropyrrolopyridine, furopyridine,
imidazopyrazine, imidazopyrazole imidazopyridine,
imidazopyrimidine, indazole, indole, isoquinoline, naphthyridine,
pyrazolopyridine, pyrrolopyridine, tetrazolopyridine,
tetrahydroimidazopyridine, tetrahydropyrazolopyridine,
thiazolopyridine and thienopyridine. In a another embodiment,
heteroaryl is bicyclic heteroaryl selected from
1H-pyrazolo[3,4-b]pyridine;
1,4,6,7-Tetrahydro-pyrazolo[4,3-c]pyridine;
7,8-Dihydro-5H-pyrido[4,3-d]pyrimidine;
5,7-Dihydro-pyrrolo[3,4-b]pyridine;
7,8-Dihydro-5H-[1,6]naphthyridine;
1,4,6,7-Tetrahydro-imidazo[4,5-c]pyridine;
1,8a-dihydroimidazo[1,2-a]pyridine; thieno[3,2-c]pyridine;
1H-imidazo[1,2-b]pyrazole; 1H-pyrazolo[3,4-b]pyridine;
furo[2,3-c]pyridine; 1H-pyrazolo[3,4-b]pyridine;
1H-pyrrolo[3,2-c]pyridine; thieno[2,3-b]pyridine;
imidazo[1,2-a]pyrimidine; furo[2,3-c]pyridine; isoquinoline;
1H-indazole; imidazo[1,2-a]pyridine; thieno[2,3-c]pyridine;
furo[2,3-c]pyridine; 1H-pyrrolo[2,3-c]pyridine;
imidazo[1,2-a]pyrazine; 1,3-benzothiazole; benzo[d]thiazole;
1H-pyrrolo[2,3-b]pyridine; [1,3]thiazolo[5,4-c]pyridine;
[1,2,3,4]tetrazolo[1,5-a]pyridine; 1,5-naphthyridine; 1H-indole;
1H-imidazo[4,5-c]pyridine; and 1,6-naphthyridine.
By way of example and not limitation, carbon bonded heterocycles
and heteroaryls are bonded at position 2, 3, 4, 5, or 6 of a
pyridine, position 3, 4, 5, or 6 of a pyridazine, position 2, 4, 5,
or 6 of a pyrimidine, position 2, 3, 5, or 6 of a pyrazine,
position 2, 3, 4, or 5 of a furan, tetrahydrofuran, thiofuran,
thiophene, pyrrole or tetrahydropyrrole, position 2, 4, or 5 of an
oxazole, imidazole or thiazole, position 3, 4, or 5 of an
isoxazole, pyrazole, or isothiazole, position 2 or 3 of an
aziridine, position 2, 3, or 4 of an azetidine, position 2, 3, 4,
5, 6, 7, or 8 of a quinoline or position 1, 3, 4, 5, 6, 7, or 8 of
an isoquinoline. Further examples of carbon bonded heterocycles
include 2-pyridyl, 3-pyridyl, 4-pyridyl, 5-pyridyl, 6-pyridyl,
3-pyridazinyl, 4-pyridazinyl, 5-pyridazinyl, 6-pyridazinyl,
2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl,
2-pyrazinyl, 3-pyrazinyl, 5-pyrazinyl, 6-pyrazinyl, 2-thiazolyl,
4-thiazolyl, or 5-thiazolyl. By way of example and not limitation,
nitrogen bonded heterocycles and heteroaryls are bonded at position
1 of an aziridine, azetidine, pyrrole, pyrrolidine, 2-pyrroline,
3-pyrroline, imidazole, imidazolidine, 2-imidazoline,
3-imidazoline, pyrazole, pyrazoline, 2-pyrazoline, 3-pyrazoline,
piperidine, piperazine, indole, indoline, 1H-indazole, position 2
of an isoindole, or isoindoline, position 4 of a morpholine, and
position 9 of a carbazole, or .beta.-carboline. Still more
typically, nitrogen bonded heterocycles include 1-aziridyl,
1-azetedyl, 1-pyrrolyl, 1-imidazolyl, 1-pyrazolyl, and
1-piperidinyl.
[0150] The term "bicyclic heteroaryl" means a structure having
atoms arranged in two rings fused together with at least two atoms
common to each ring, and at least one of the rings being a
heteroaryl ring. Illustrative examples of bicyclic heteroaryls
include but are not limited to:
##STR00028## ##STR00029##
and the like.
[0151] Further examples of bicyclic heteroaryls include but are not
limited to:
##STR00030##
[0152] These bicyclic heteroaryl groups can be substituted as
defined for R herein.
[0153] As used herein, the terms "cycloalkyl" and "cycloalkenyl"
refers to a saturated or partially saturated, monocyclic or fused
or spiro polycyclic, carbocycle having from 3 to 24 ring atoms per
ring. Illustrative examples of cycloalkyl and "cycloalkenyl" groups
include, but are not limited to, the following moieties:
##STR00031##
and the like.
[0154] As used herein, the term "heterocycloalkyl" refers to a
monocyclic, or fused or spiro, polycyclic, ring structure that is
saturated or partially saturated and has from 3 to 24 ring atoms
per ring selected from C atoms and N, O, and/or S atoms.
Illustrative examples of heterocycloalkyl and substituted
heterocycloalkyl groups include, but are not limited to:
##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036##
##STR00037## ##STR00038## ##STR00039## ##STR00040##
##STR00041##
and the like.
[0155] Numerical ranges, as used herein, are intended to include
sequential whole numbers. For example, a range expressed as "from 0
to 4" would include 0, 1, 2, 3 and 4.
[0156] As used herein, the term "substituted" means that the
specified group or moiety bears one or more suitable
substituents.
[0157] As used herein, the term "unsubstituted" means that the
specified group bears no substituents.
[0158] As used herein, the term "optionally substituted" means that
the specified group is unsubstituted or substituted by one or more
substituents.
[0159] When a multifunctional moiety is shown, the point of
attachment to the core is indicated by a line. For e.g.
(cycloalkyloxy)alkyl- refers to alkyl being the point of attachment
to the core while cycloalkyl is attached to alkyl via the oxy
group.
[0160] The expression "adjunctive chemotherapeutic agent" generally
refers to agents which treat, alleviate, relieve, or ameliorate the
side effects of chemotherapeutic agents. Such agents include those
which modify blood cell growth and maturation. Examples of
adjunctive chemotherapeutic agents include, but are not limited to,
filgrastim and erythropoietin. Other such adjunctive
chemotherapeutic agents include those which inhibit nausea
associated with administration of the chemotherapeutic agents, such
as a 5-HT.sub.3 receptor inhibitor (e.g., dolansetron, granisetron,
or ondansetron), with or without dexamethasone.
[0161] The terms "chemotherapeutic agent" and "antineoplastic
agent" generally refer to agents which treat, prevent, cure, heal,
alleviate, relieve, alter, remedy, ameliorate, improve, or affect
malignancies and their metastasis. Examples of such agents (also
known as "antineoplastic agents") include, but are not limited to,
prednisone, fluorouracil (e.g., 5-fluorouracil (5-FU)),
anastrozole, bicalutamide, carboplatin, cisplatin, chlorambucil,
cisplatin, carboplatin, docetaxel, doxorubicin, flutamide,
interferon-alpha, letrozole, leuprolide, megestrol, mitomycin,
oxaliplatin, paclitaxel, plicamycin (Mithracin.TM.), tamoxifen,
thiotepa, topotecan, valrubicin, vinblastine, vincristine, and any
combination of any of the foregoing. Additional such agents are
described later.
[0162] "Nicotinamide phosphoribosyltransferase" also named NAMPT,
NMPRT, NMPRTase or NAmPRTase, (International nomenclature: E.C.
2.4.2.12) is a key enzyme in nicotinamide adenyl dinucleotide (NAD)
biosynthesis from the natural precursor nicotinamide.
[0163] It must be noted that, as used in the specification and the
appended claims, the singular forms "a," "an" and "the" include
plural referents unless the context clearly dictates otherwise.
[0164] When used as a therapeutic agent the inhibitors of the
formation of nicotinamide phosphoribosyltransferase (NAMPT)
described herein may be administered with one or more
physiologically acceptable excipients. A physiologically acceptable
carrier or excipient is a formulation to which the compound can be
added to dissolve it or otherwise facilitate its
administration.
[0165] The dosage forms of the present invention, may contain a
mixture of one or more compounds of this invention, and may include
additional materials known to those skilled in the art as
pharmaceutical excipients. Such pharmaceutical excipients include,
for example, the following: Stabilizing additives may be
incorporated into the delivery agent solution. With some drugs, the
presence of such additives promotes the stability and
dispersibility of the agent in solution. The stabilizing additives
may be employed at a concentration ranging from about 0.1 and 5%
(W/V), preferably about 0.5% (W/V). Suitable, but non-limiting,
examples of stabilizing additives include gum acacia, gelatin,
methyl cellulose, polyethylene glycol, carboxylic acids and salts
thereof, and polylysine. The preferred stabilizing additives are
gum acacia, gelatin and methyl cellulose.
[0166] Acidifying agents (acetic acid, glacial acetic acid, citric
acid, fumaric acid, hydrochloric acid, diluted hydrochloric acid,
malic acid, nitric acid, phosphoric acid, diluted phosphoric acid,
sulfuric acid, tartaric acid); Aerosol propellants (butane,
dichlorodifluoro-methane, dichlorotetrafluoroethane, isobutane,
propane, trichloromonofluoromethane); Air displacements (carbon
dioxide, nitrogen); Alcohol denaturants (denatonium benzoate,
methyl isobutyl ketone, sucrose octacetate); Alkalizing agents
(strong ammonia solution, ammonium carbonate, diethanolamine,
diisopropanolamine, potassium hydroxide, sodium bicarbonate, sodium
borate, sodium carbonate, sodium hydroxide, trolamine); Anticaking
agents (see glidant); Antifoaming agents (dimethicone,
simethicone); Antimicrobial preservatives (benzalkonium chloride,
benzalkonium chloride solution, benzelthonium chloride, benzoic
acid, benzyl alcohol, butylparaben, cetylpyridinium chloride,
chlorobutanol, chlorocresol, cresol, dehydroacetic acid,
ethylparaben, methylparaben, methylparaben sodium, phenol,
phenylethyl alcohol, phenylmercuric acetate, phenylmercuric
nitrate, potassium benzoate, potassium sorbate, propylparaben,
propylparaben sodium, sodium benzoate, sodium dehydroacetate,
sodium propionate, sorbic acid, thimerosal, thymol); Antioxidants
(ascorbic acid, acorbyl palmitate, butylated hydroxyanisole,
butylated hydroxytoluene, hypophosphorous acid, monothioglycerol,
propyl gallate, sodium formaldehyde sulfoxylate, sodium
metabisulfite, sodium thiosulfate, sulfur dioxide, tocopherol,
tocopherols excipient); Buffering agents (acetic acid, ammonium
carbonate, ammonium phosphate, boric acid, citric acid, lactic
acid, phosphoric acid, potassium citrate, potassium metaphosphate,
potassium phosphate monobasic, sodium acetate, sodium citrate,
sodium lactate solution, dibasic sodium phosphate, monobasic sodium
phosphate); Capsule lubricants (see tablet and capsule lubricant);
Chelating agents (edetate disodium, ethylenediaminetetraacetic acid
and salts, edetic acid); Coating agents (sodium
carboxymethylcellulose, cellulose acetate, cellulose acetate
phthalate, ethylcellulose, gelatin, pharmaceutical glaze,
hydroxypropyl cellulose, hydroxypropyl methylcellulose,
hydroxypropyl methylcellulose phthalate, methacrylic acid
copolymer, methylcellulose, polyethylene glycol, polyvinyl acetate
phthalate, shellac, sucrose, titanium dioxide, carnauba wax,
microcystalline wax, zein); Colorants (caramel, red, yellow, black
or blends, ferric oxide); Complexing agents
(ethylenediaminetetraacetic acid and salts (EDTA), edetic acid,
gentisic acid ethanolmaide, oxyquinoline sulfate); Desiccants
(calcium chloride, calcium sulfate, silicon dioxide); Emulsifying
and/or solubilizing agents (acacia, cholesterol, diethanolamine
(adjunct), glyceryl monostearate, lanolin alcohols, lecithin, mono-
and di-glycerides, monoethanolamine (adjunct), oleic acid
(adjunct), oleyl alcohol (stabilizer), poloxamer, polyoxyethylene
50 stearate, polyoxyl 35 caster oil, polyoxyl 40 hydrogenated
castor oil, polyoxyl 10 oleyl ether, polyoxyl 20 cetostearyl ether,
polyoxyl 40 stearate, polysorbate 20, polysorbate 40, polysorbate
60, polysorbate 80, propylene glycol diacetate, propylene glycol
monostearate, sodium lauryl sulfate, sodium stearate, sorbitan
monolaurate, soritan monooleate, sorbitan monopalmitate, sorbitan
monostearate, stearic acid, trolamine, emulsifying wax); Filtering
aids (powdered cellulose, purified siliceous earth); Flavors and
perfumes (anethole, benzaldehyde, ethyl vanillin, menthol, methyl
salicylate, monosodium glutamate, orange flower oil, peppermint,
peppermint oil, peppermint spirit, rose oil, stronger rose water,
thymol, tolu balsam tincture, vanilla, vanilla tincture, vanillin);
Glidants and/or anticaking agents (calcium silicate, magnesium
silicate, colloidal silicon dioxide, talc); Humectants (glycerin,
hexylene glycol, propylene glycol, sorbitol); Plasticizers (castor
oil, diacetylated monoglycerides, diethyl phthalate, glycerin,
mono- and di-acetylated monoglycerides, polyethylene glycol,
propylene glycol, triacetin, triethyl citrate); Polymers (e.g.,
cellulose acetate, alkyl celloloses, hydroxyalkylcelloloses,
acrylic polymers and copolymers); Solvents (acetone, alcohol,
diluted alcohol, amylene hydrate, benzyl benzoate, butyl alcohol,
carbon tetrachloride, chloroform, corn oil, cottonseed oil, ethyl
acetate, glycerin, hexylene glycol, isopropyl alcohol, methyl
alcohol, methylene chloride, methyl isobutyl ketone, mineral oil,
peanut oil, polyethylene glycol, propylene carbonate, propylene
glycol, sesame oil, water for injection, sterile water for
injection, sterile water for irrigation, purified water); Sorbents
(powdered cellulose, charcoal, purified siliceous earth); Carbon
dioxide sorbents (barium hydroxide lime, soda lime); Stiffening
agents (hydrogenated castor oil, cetostearyl alcohol, cetyl
alcohol, cetyl esters wax, hard fat, paraffin, polyethylene
excipient, stearyl alcohol, emulsifying wax, white wax, yellow
wax); Suspending and/or viscosity-increasing agents (acacia, agar,
alginic acid, aluminum monostearate, bentonite, purified bentonite,
magma bentonite, carbomer 934p, carboxymethylcellulose calcium,
carboxymethylcellulose sodium, carboxymethycellulose sodium 12,
carrageenan, microcrystalline and carboxymethylcellulose sodium
cellulose, dextrin, gelatin, guar gum, hydroxyethyl cellulose,
hydroxypropyl cellulose, hydroxypropyl methylcellulose, magnesium
aluminum silicate, methylcellulose, pectin, polyethylene oxide,
polyvinyl alcohol, povidone, propylene glycol alginate, silicon
dioxide, colloidal silicon dioxide, sodium alginate, tragacanth,
xanthan gum); Sweetening agents (aspartame, dextrates, dextrose,
excipient dextrose, fructose, mannitol, saccharin, calcium
saccharin, sodium saccharin, sorbitol, solution sorbitol, sucrose,
compressible sugar, confectioner's sugar, syrup); Tablet binders
(acacia, alginic acid, sodium carboxymethylcellulose,
microcrystalline cellulose, dextrin, ethylcellulose, gelatin,
liquid glucose, guar gum, hydroxypropyl methylcellulose,
methycellulose, polyethylene oxide, povidone, pregelatinized
starch, syrup); Tablet and/or capsule diluents (calcium carbonate,
dibasic calcium phosphate, tribasic calcium phosphate, calcium
sulfate, microcrystalline cellulose, powdered cellulose, dextrates,
dextrin, dextrose excipient, fructose, kaolin, lactose, mannitol,
sorbitol, starch, pregelatinized starch, sucrose, compressible
sugar, confectioner's sugar); Tablet disintegrants (alginic acid,
microcrystalline cellulose, croscarmellose sodium, corspovidone,
polacrilin potassium, sodium starch glycolate, starch,
pregelatinized starch); Tablet and/or capsule lubricants (calcium
stearate, glyceryl behenate, magnesium stearate, light mineral oil,
polyethylene glycol, sodium stearyl fumarate, stearic acid,
purified stearic acid, talc, hydrogenated vegetable oil, zinc
stearate); Tonicity agent (dextrose, glycerin, mannitol, potassium
chloride, sodium chloride); Vehicle: flavored and/or sweetened
(aromatic elixir, compound benzaldehyde elixir, iso-alcoholic
elixir, peppermint water, sorbitol solution, syrup, tolu balsam
syrup); Vehicle: oleaginous (almond oil, corn oil, cottonseed oil,
ethyl oleate, isopropyl myristate, isopropyl palmitate, mineral
oil, light mineral oil, myristyl alcohol, octyldodecanol, olive
oil, peanut oil, persic oil, sesame oil, soybean oil, squalane);
Vehicle: solid carrier (sugar spheres); Vehicle: sterile
(bacteriostatic water for injection, bacteriostatic sodium chloride
injection); Viscosity-increasing (see suspending agent); Water
repelling agent (cyclomethicone, dimethicone, simethicone); and
Wetting and/or solubilizing agent (benzalkonium chloride,
benzethonium chloride, cetylpyridinium chloride, docusate sodium,
nonoxynol 9, nonoxynol 10, octoxynol 9, poloxamer, polyoxyl 35
castor oil, polyoxyl 40, hydrogenated castor oil, polyoxyl 50
stearate, polyoxyl 10 oleyl ether, polyoxyl 20, cetostearyl ether,
polyoxyl 40 stearate, polysorbate 20, polysorbate 40, polysorbate
60, polysorbate 80, sodium lauryl sulfate, sorbitan monolaureate,
sorbitan monooleate, sorbitan monopalmitate, sorbitan monostearate,
tyloxapol). This list is not meant to be exclusive, but instead
merely representative of the classes of excipients and the
particular excipients which may be used in dosage forms of the
present invention.
[0167] The compounds of the disclosed Formulas can form salts which
are also within the scope of this invention. Reference to a
compound of the Formulas herein is understood to include reference
to salts thereof, unless otherwise indicated. The term "salt(s)",
as employed herein, denotes acidic salts formed with inorganic
and/or organic acids, as well as basic salts formed with inorganic
and/or organic bases. In addition, when a compound of the Formulas
contains both a basic moiety, such as, but not limited to a
pyridine or imidazole, and an acidic moiety, such as, but not
limited to a carboxylic acid, zwitterions ("inner salts") may be
formed and are included within the term "salt(s)" as used herein.
Pharmaceutically acceptable (i.e., non-toxic, physiologically
acceptable) salts are preferred, although other salts are also
useful. Salts of the compounds of the Formulas may be formed, for
example, by reacting a compound of Formulas with an amount of acid
or base, such as an equivalent amount, in a medium such as one in
which the salt precipitates or in an aqueous medium followed by
lyophilization.
[0168] Exemplary acid addition salts include acetates, ascorbates,
benzoates, benzenesulfonates, bisulfates, borates, butyrates,
citrates, camphorates, camphorsulfonates, fumarates,
hydrochlorides, hydrobromides, hydroiodides, lactates, maleates,
methanesulfonates, naphthalenesulfonates, nitrates, oxalates,
phosphates, propionates, salicylates, succinates, sulfates,
tartarates, thiocyanates, toluenesulfonates (also known as
tosylates,) and the like. Additionally, acids which are generally
considered suitable for the formation of pharmaceutically useful
salts from basic pharmaceutical compounds are discussed, for
example, by P. Stahl et al, Camille G. (eds.) Handbook of
Pharmaceutical Salts. Properties, Selection and Use. (2002) Zurich:
Wiley-VCH; S. Berge et al, Journal of Pharmaceutical Sciences
(1977) 66(1) 1-19; P. Gould, International J. of Pharmaceutics
(1986) 33 201-217; Anderson et al, The Practice of Medicinal
Chemistry (1996), Academic Press, New York; and in The Orange Book
(Food & Drug Administration, MD, on their website). These
disclosures are incorporated herein by reference thereto.
[0169] Exemplary basic salts include ammonium salts, alkali metal
salts such as sodium, lithium, and potassium salts, alkaline earth
metal salts such as calcium and magnesium salts, salts with organic
bases (for example, organic amines) such as dicyclohexylamines,
t-butyl amines, and salts with amino acids such as arginine, lysine
and the like. Basic nitrogen-containing groups may be quarternized
with agents such as lower alkyl halides (e.g. methyl, ethyl, and
butyl chlorides, bromides and iodides), dialkyl sulfates (e.g.
dimethyl, diethyl, and dibutyl sulfates), long chain halides (e.g.
decyl, lauryl, and stearyl chlorides, bromides and iodides),
aralkyl halides (e.g. benzyl and phenethyl bromides), and
others.
[0170] All such acid salts and base salts are intended to be
pharmaceutically acceptable salts within the scope of the invention
and all acid and base salts are considered equivalent to the free
forms of the corresponding compounds for purposes of the
invention.
[0171] Pharmaceutically acceptable esters of the compounds of the
invention are also considered to be part of the invention.
Pharmaceutically acceptable esters of the present compounds include
the following groups: (1) carboxylic acid esters obtained by
esterification of the hydroxy groups, in which the non-carbonyl
moiety of the carboxylic acid portion of the ester grouping is
selected from straight or branched chain alkyl (for example,
acetyl, n-propyl, t-butyl, or n-butyl), alkoxyalkyl (for example,
methoxymethyl), aralkyl (for example, benzyl), aryloxyalkyl (for
example, phenoxymethyl), aryl (for example, phenyl optionally
substituted with, for example, halogen, C.sub.1-4alkyl, or
C.sub.1-4alkoxy or amino); (2) sulfonate esters, such as alkyl- or
aralkylsulfonyl (for example, methanesulfonyl); (3) amino acid
esters (for example, L-valyl or L-isoleucyl); (4) phosphonate
esters and (5) mono-, di- or triphosphate esters. The phosphate
esters may be further esterified by, for example, a C.sub.1-20
alcohol or reactive derivative thereof, or by a
2,3-di(C.sub.6-24)acyl glycerol.
[0172] Prodrugs and solvates of the compounds of the invention are
also contemplated herein. A discussion of prodrugs is provided in
T. Higuchi and V. Stella, Pro-drugs as Novel Delivery Systems
(1987) 14 of the A.C.S. Symposium Series, and in Bioreversible
Carriers in Drug Design, (1987) Edward B. Roche, ed., American
Pharmaceutical Association and Pergamon Press. The term "prodrug"
means a compound (e.g, a drug precursor) that is transformed in
vivo to yield a compound of the instant Formulas or a
pharmaceutically acceptable salt, hydrate or solvate of the
compound. The transformation may occur by various mechanisms (e.g.,
by metabolic or chemical processes), such as, for example, through
hydrolysis in blood. A discussion of the use of prodrugs is
provided by T. Higuchi and W. Stella, "Pro-drugs as Novel Delivery
Systems," Vol. 14 of the A.C.S. Symposium Series, and in
Bioreversible Carriers in Drug Design, ed. Edward B. Roche,
American Pharmaceutical Association and Pergamon Press, 1987.
[0173] For example, if a compound of the instant Formulas or a
pharmaceutically acceptable salt, hydrate or solvate of the
compound contains a carboxylic acid functional group, a prodrug can
comprise an ester formed by the replacement of the hydrogen atom of
the acid group with a group such as, for example,
(C.sub.1-C.sub.8)alkyl, (C.sub.2-C.sub.12)alkanoyloxymethyl,
1-(alkanoyloxy)ethyl having from 4 to 9 carbon atoms,
1-methyl-1-(alkanoyloxy)-ethyl having from 5 to 10 carbon atoms,
alkoxycarbonyloxymethyl having from 3 to 6 carbon atoms,
1-(alkoxycarbonyloxy)ethyl having from 4 to 7 carbon atoms,
1-methyl-1-(alkoxycarbonyloxy)ethyl having from 5 to 8 carbon
atoms, N-(alkoxycarbonyl)aminomethyl having from 3 to 9 carbon
atoms, 1-(N-(alkoxycarbonyl)amino)ethyl having from 4 to 10 carbon
atoms, 3-phthalidyl, 4-crotonolactonyl, gamma-butyrolacton-4-yl,
di-N,N--(C.sub.1-C.sub.2)alkylamino(C.sub.2-C.sub.3)alkyl (such as
.beta.-dimethylaminoethyl), carbamoyl-(C.sub.1-C.sub.2)alkyl,
N,N-di(C.sub.1-C.sub.2)alkylcarbamoyl-(C.sub.1-C.sub.2)alkyl and
piperidino-, pyrrolidino- or morpholine (C.sub.2-C.sub.3)alkyl, and
the like.
[0174] Similarly, if a compound of the instant Formulas contains an
alcohol functional group, a prodrug can be formed by the
replacement of the hydrogen atom of the alcohol group with a group
such as, for example, (C.sub.1-C.sub.6)alkanoyloxymethyl,
1-((C.sub.1-C.sub.6)alkanoyloxy)ethyl,
1-methyl-1-((C.sub.1-C.sub.6)alkanoyloxy)ethyl,
(C.sub.1-C.sub.6)alkoxycarbonyloxymethyl,
N--(C.sub.1-C.sub.6)alkoxycarbonylaminomethyl, succinoyl,
(C.sub.1-C.sub.6)alkanoyl, .alpha.-amino(C.sub.1-C.sub.4)alkanyl,
arylacyl and .alpha.-aminoacyl, or
.alpha.-aminoacyl-.alpha.-aminoacyl, where each .alpha.-aminoacyl
group is independently selected from the naturally occurring
L-amino acids, P(O)(OH).sub.2,
--P(O)(O(C.sub.1-C.sub.6)alkyl).sub.2 or glycosyl (the radical
resulting from the removal of a hydroxyl group of the hemiacetal
form of a carbohydrate), and the like.
[0175] If a compound of the instant Formulas incorporates an amine
functional group, a prodrug can be formed by the replacement of a
hydrogen atom in the amine group with a group such as, for example,
R-carbonyl, RO-carbonyl, NRR'-carbonyl where R and R' are each
independently (C.sub.1-C.sub.10)alkyl, (C.sub.3-C.sub.7)
cycloalkyl, benzyl, or R-carbonyl is a natural .alpha.-aminoacyl or
natural .alpha.-aminoacyl, --C(OH)C(O)OY.sup.1 wherein Y.sup.1 is
H, (C.sub.1-C.sub.6)alkyl or benzyl, --C(OY.sup.2)Y.sup.3 wherein
Y.sup.2 is (C.sub.1-C.sub.4) alkyl and Y.sup.3 is
(C.sub.1-C.sub.6)alkyl, carboxy(C.sub.1-C.sub.6)alkyl,
amino(C.sub.1-C.sub.4)alkyl or mono-N-- or
di-N,N--(C.sub.1-C.sub.6)alkylaminoalkyl, --C(Y.sup.4)Y.sup.5
wherein Y.sup.4 is H or methyl and Y.sup.5 is mono-N-- or
di-N,N--(C.sub.1-C.sub.6)alkylamino morpholino, piperidin-1-yl or
pyrrolidin-1-yl, and the like.
[0176] One or more compounds of the invention may exist in
unsolvated as well as solvated forms with pharmaceutically
acceptable solvents such as water, ethanol, and the like, and it is
intended that the invention embrace both solvated and unsolvated
forms. "Solvate" means a physical association of a compound of this
invention with one or more solvent molecules. This physical
association involves varying degrees of ionic and covalent bonding,
including hydrogen bonding. In certain instances the solvate will
be capable of isolation, for example when one or more solvent
molecules are incorporated in the crystal lattice of the
crystalline solid. "Solvate" encompasses both solution-phase and
isolatable solvates. Non-limiting examples of suitable solvates
include ethanolates, methanolates, and the like. "Hydrate" is a
solvate wherein the solvent molecule is H.sub.2O.
[0177] One or more compounds of the invention may optionally be
converted to a solvate. Preparation of solvates is generally known.
Thus, for example, M. Caira et al, J. Pharmaceutical Sci., 93(3),
601-611 (2004) describe the preparation of the solvates of the
antifungal fluconazole in ethyl acetate as well as from water.
Similar preparations of solvates, hemisolvate, hydrates and the
like are described by E. C. van Tonder et al, AAPS PharmSciTech.,
5(1), article 12 (2004); and A. L. Bingham et al, Chem. Commun.,
603-604 (2001). A typical, non-limiting, process involves
dissolving the inventive compound in desired amounts of the desired
solvent (organic or water or mixtures thereof) at a higher than
ambient temperature, and cooling the solution at a rate sufficient
to form crystals which are then isolated by standard methods.
Analytical techniques such as, for example I. R. spectroscopy, show
the presence of the solvent (or water) in the crystals as a solvate
(or hydrate).
[0178] Compounds of the various Formulas, and salts, solvates,
esters and prodrugs thereof, may exist in their tautomeric form
(for example, as an amide or imino ether). All such tautomeric
forms are contemplated herein as part of the present invention.
[0179] The compounds of the various Formulas may contain asymmetric
or chiral centers, and, therefore, exist in different
stereoisomeric forms. It is intended that all stereoisomeric forms
of the compounds of the various Formulas as well as mixtures
thereof, including racemic mixtures, form part of the present
invention. In addition, the present invention embraces all
geometric and positional isomers. For example, if a compound of the
various Formulas incorporates a double bond or a fused ring, both
the cis- and trans-forms, as well as mixtures, are embraced within
the scope of the invention.
[0180] Diastereomeric mixtures can be separated into their
individual diastereomers on the basis of their physical chemical
differences by methods well known to those skilled in the art, such
as, for example, by chromatography and/or fractional
crystallization. Enantiomers can be separated by converting the
enantiomeric mixture into a diastereomeric mixture by reaction with
an appropriate optically active compound (e.g., chiral auxiliary
such as a chiral alcohol or Mosher's acid chloride), separating the
diastereomers and converting (e.g., hydrolyzing) the individual
diastereomers to the corresponding pure enantiomers. Also, some of
the compounds of the various Formulas may be atropisomers (e.g.,
substituted biaryls) and are considered as part of this invention.
Enantiomers can also be separated by use of chiral HPLC column.
[0181] It is also possible that the compounds of the various
Formulas may exist in different tautomeric forms, and all such
forms are embraced within the scope of the invention. Also, for
example, all keto-enol and imine-enamine forms of the compounds are
included in the invention.
[0182] All stereoisomers (for example, geometric isomers, optical
isomers and the like) of the present compounds (including those of
the salts, solvates, esters and prodrugs of the compounds as well
as the salts, solvates and esters of the prodrugs), such as those
which may exist due to asymmetric carbons on various substituents,
including enantiomeric forms (which may exist even in the absence
of asymmetric carbons), rotameric forms, atropisomers, and
diastereomeric forms, are contemplated within the scope of this
invention, as are positional isomers (such as, for example,
4-pyridyl and 3-pyridyl). (For example, if a compound of the
various Formulas incorporates a double bond or a fused ring, both
the cis- and trans-forms, as well as mixtures, are embraced within
the scope of the invention. Also, for example, all keto-enol and
imine-enamine forms of the compounds are included in the
invention.) Individual stereoisomers of the compounds of the
invention may, for example, be substantially free of other isomers,
or may be admixed, for example, as racemates or with all other, or
other selected, stereoisomers. The chiral centers of the present
invention can have the S or R configuration as defined by the IUPAC
1974 Recommendations. The use of the terms "salt", "solvate",
"ester", "prodrug" and the like, is intended to equally apply to
the salt, solvate, ester and prodrug of enantiomers, stereoisomers,
rotamers, tautomers, positional isomers, racemates or prodrugs of
the inventive compounds.
[0183] The present invention also embraces isotopically-labelled
compounds of the present invention which are identical to those
recited herein, but for the fact that one or more atoms are
replaced by an atom having an atomic mass or mass number different
from the atomic mass or mass number usually found in nature.
Examples of isotopes that can be incorporated into compounds of the
invention include isotopes of hydrogen, carbon, nitrogen, oxygen,
phosphorus, fluorine and chlorine, such as .sup.2H, .sup.3H,
.sup.13C, .sup.14C, .sup.15N, .sup.18O, .sup.17O, .sup.31P,
.sup.32P, .sup.35S, .sup.18F, and .sup.36Cl, respectively.
[0184] Certain isotopically-labelled compounds of the various
Formulas (e.g., those labelled with .sup.3H and .sup.14C) are
useful in compound and/or substrate tissue distribution assays.
Tritiated (i.e., .sup.3H) and carbon-14 (i.e., .sup.14C) isotopes
are particularly preferred for their ease of preparation and
detectability. Further, substitution with heavier isotopes such as
deuterium (i.e., .sup.2H) may afford certain therapeutic advantages
resulting from greater metabolic stability (e.g., increased in vivo
half-life or reduced dosage requirements) and hence may be
preferred in some circumstances. Isotopically labelled compounds of
the various Formulas can generally be prepared by following
procedures analogous to those disclosed in the Schemes and/or in
the Examples hereinbelow, by substituting an appropriate
isotopically labelled reagent for a non-isotopically labelled
reagent.
[0185] Polymorphic forms of the compounds of the various Formulas,
and of the salts, solvates, esters and prodrugs of the compounds of
the various Formulas, are intended to be included in the present
invention.
[0186] Benefits of the present invention include oral
administration of an optimal amount of a nicotinamide
phosphoribosyltransferase biosynthesis inhibitor.
[0187] Benefits of the present invention include intravenous
administration of an optimal amount of a nicotinamide
phosphoribosyltransferase biosynthesis inhibitor.
[0188] Benefits of the present invention include intraperitoneal
administration of an optimal amount of a nicotinamide
phosphoribosyltransferase biosynthesis inhibitor.
[0189] Benefits of the present invention include intramural
administration of an optimal amount of a nicotinamide
phosphoribosyltransferase biosynthesis inhibitor.
[0190] Benefits of the present invention include intramuscular
administration of an optimal amount of a nicotinamide
phosphoribosyltransferase biosynthesis inhibitor.
[0191] Benefits of the present invention include subcutaneous
administration of an optimal amount of a nicotinamide
phosphoribosyltransferase biosynthesis inhibitor.
[0192] Benefits of the present invention include intra-tumor
administration of an optimal amount of a nicotinamide
phosphoribosyltransferase biosynthesis inhibitor.
[0193] Benefits of the present invention include intrathecal
administration of an optimal amount of a nicotinamide
phosphoribosyltransferase biosynthesis inhibitor.
[0194] Benefits of the present invention include subdural
administration of an optimal amount of a nicotinamide
phosphoribosyltransferase biosynthesis inhibitor.
[0195] Benefits of the present invention include periorbital
administration of an optimal amount of a nicotinamide
phosphoribosyltransferase biosynthesis inhibitor.
[0196] Based on these results, the present invention has important
implications for the design of novel treatment strategies for
patients with cancer, including leukemias and solid tumors,
inflammatory diseases, osteoporosis, atherosclerosis; irritable
bowel syndrome and other conditions disclosed herein or that are
known to those skilled in the art.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0197] An aspect of the present invention concerns compounds
disclosed herein.
[0198] An aspect of the present invention concerns compounds which
are or can be inhibitors of the formation of nicotinamide
phosphoribosyltransferase.
[0199] An aspect of the present invention concerns the use of an
inhibitor of the formation of nicotinamide
phosphoribosyltransferase for the preparation of a medicament used
in the treatment, prevention, inhibition or elimination of
tumors.
[0200] An aspect of the present invention concerns the use of an
inhibitor of the formation of nicotinamide
phosphoribosyltransferase for the preparation of a medicament used
in the treatment, prevention, inhibition or elimination of
cancer.
[0201] An aspect of the present invention concerns the use of an
inhibitor of the formation of nicotinamide
phosphoribosyltransferase for the preparation of a medicament used
in the treatment, prevention, inhibition or elimination of cancer,
where the cancer is selected from leukemia, lymphoma, ovarian
cancer, breast cancer, uterine cancer, colon cancer, cervical
cancer, lung cancer, prostate cancer, skin cancer, CNS cancer,
bladder cancer, pancreatic cancer and Hodgkin's disease.
[0202] The present invention also describes one or more methods of
synthesizing the compounds of the present invention.
[0203] The invention also describes one or more uses of the
compounds of the present invention.
[0204] The invention also describes one or more uses of the
compounds of the present invention with an adjunctive agent such as
use with TNF, GCSF, or other chemotherapeutic agents
[0205] The invention also describes one or more uses of the
pharmaceutical compositions of the present invention.
[0206] An aspect of the present invention concerns the use as an
inhibitor of the formation of nicotinamide
phosphoribosyltransferase for the preparation of a medicament used
in the treatment of inflammatory diseases.
[0207] An aspect of the present invention concerns the use as an
inhibitor of the formation of nicotinamide
phosphoribosyltransferase for the preparation of a medicament used
in the treatment of inflammatory diseases, such as Irritable Bowel
Syndrome or Inflammatory Bowel Disease.
[0208] An aspect of the present invention concerns the use as an
inhibitor of the formation of nicotinamide
phosphoribosyltransferase for the preparation of a medicament used
in the treatment of disease of the bone such as osteoporosis.
[0209] An aspect of the present invention concerns the use as an
inhibitor of the formation of nicotinamide
phosphoribosyltransferase for the preparation of a medicament used
in the treatment of disease of the cardiovascular system, such as
atherosclerosis.
[0210] An aspect of the present invention concerns the use as an
inhibitor of the formation of nicotinamide
phosphoribosyltransferase for the preparation of a medicament used
in the treatment of disease or a condition caused by an elevated
level of NAMPT.
[0211] Such disease or condition is one or more selected from the
group consisting of cancer, ovarian cancer, breast cancer, uterine
cancer, colon cancer, cervical cancer, lung cancer, prostate
cancer, skin cancer, bladder cancer, pancreatic cancer, leukemia,
lymphoma, Hodgkin's disease, viral infections, Human
Immunodeficiency Virus, hepatitis virus, herpes virus, herpes
simplex, inflammatory disorders, irritable bowel syndrome,
inflammatory bowel disease, rheumatoid arthritis, asthma, chronic
obstructive pulmonary disease, osteoarthritis, osteoporosis,
dermatitis, atoptic dermatitis, psoriasis, systemic lupus
erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing
spodylitis, graft-versus-host disease, Alzheimer's disease,
cerebrovascular accident, atherosclerosis, diabetes,
glomerulonephiritis, metabolic syndrome, non-small cell lung
cancer, small cell lung cancer, multiple myeloma, leukemias,
lymphomas, squamous cell cancers, kidney cancer, uretral and
bladder cancers, cancers of head and neck, cancers of the brain and
central nervous system (CNS).
[0212] The inventive compounds can be useful in the therapy of
proliferative diseases such as, but not limited to cancer,
autoimmune diseases, viral diseases, fungal diseases,
neurological/neurodegenerative disorders, arthritis, inflammation,
anti-proliferative (e.g., ocular retinopathy), neuronal, alopecia
and cardiovascular disease.
[0213] More specifically, the compounds can be useful in the
treatment of a variety of cancers, including (but not limited to)
the following: carcinoma, including that of the bladder, breast,
colon, kidney, liver, lung, including small cell lung cancer,
non-small cell lung cancer, head and neck, esophagus, gall bladder,
ovary, pancreas, stomach, cervix, thyroid, prostate, and skin,
including squamous cell carcinoma; hematopoietic tumors of lymphoid
lineage, including leukemia, acute lymphocytic leukemia, acute
lymphoblastic leukemia, B-cell lymphoma, T-cell lymphoma, Hodgkins
lymphoma, non-Hodgkins lymphoma, hairy cell lymphoma, mantle cell
lymphoma, myeloma, and Burkett's lymphoma; hematopoietic tumors of
myeloid lineage, including acute and chronic myelogenous leukemias,
myelodysplastic syndrome and promyelocytic leukemia; tumors of
mesenchymal origin, including fibrosarcoma and rhabdomyosarcoma;
tumors of the central and peripheral nervous system, including
astrocytoma, neuroblastoma, glioma and schwannomas; and other
tumors, including melanoma, seminoma, teratocarcinoma,
osteosarcoma, xenoderoma pigmentosum, keratoctanthoma, thyroid
follicular cancer and Kaposi's sarcoma.
[0214] The compounds of the invention may induce or inhibit
apoptosis.
[0215] The compounds of the invention may also be useful in the
chemoprevention of cancer. Chemoprevention is defined as inhibiting
the development of invasive cancer by either blocking the
initiating mutagenic event or by blocking the progression of
pre-malignant cells that have already suffered an insult or
inhibiting tumor relapse.
[0216] A further aspect of the invention is a method of inhibiting
a NAMPT pathway in an animal, said method comprising administering
to said animal a pharmaceutically acceptable amount of a compound
of the invention to an animal in need thereof.
[0217] A further aspect of the invention is a pharmaceutical
formulation comprising a compound of the invention.
[0218] Another embodiment of the invention comprises a
pharmaceutical formulation of the invention, wherein the
pharmaceutical formulation, upon administration to a human, results
in a decrease in tumor burden.
[0219] Still another embodiment of the invention is a
pharmaceutical formulation, further comprising one or more of an
antineoplastic agent, a chemotherapeutic agent, or an adjunctive
chemotherapeutic agent.
[0220] The pharmaceutical formulations of the invention may further
comprise a therapeutic effective amount of an adjunctive
chemotherapeutic agent.
[0221] The adjunctive chemotherapeutic agent may be an agent which
modifies blood cell growth and maturation. Non-limiting examples of
adjunctive chemotherapeutic agent are filgrastim, pegfilgrastim and
erythropoietin.
[0222] The invention is also directed to a method of treating or
preventing a disorder associated with excessive rate of growth of
cells in a mammal comprising administering to the mammal an
effective amount of the pharmaceutical formulation of the
invention. Non-limiting examples of disorder include cancer or
metastasis from malignant tumors.
[0223] Another aspect of the invention is a method of inhibiting
tumor cell growth and rate of division in a mammal with cancer, or
other disorder associated with abnormally dividing cells comprising
administering to the mammal an effective amount of the
pharmaceutical formulation of this invention.
[0224] Another embodiment of the invention is a method of treating
bone pain due to excessive growth of a tumor or metastasis to bone
in a mammal in need thereof comprising administering to the mammal
an effective amount of the pharmaceutical formulation of this
invention.
[0225] Still another embodiment of the invention is a method for
administering a NAMPT-inhibitor-containing compound to a mammal in
need thereof comprising administering to the mammal the
pharmaceutical formulation of the invention. In one embodiment, the
mammal is a human.
[0226] A further embodiment of the invention is a method of
preparing a pharmaceutical formulation comprising mixing at least
one pharmaceutically acceptable compound of the present invention,
and, optionally, one or more pharmaceutically acceptable excipients
or additives.
[0227] The invention is also directed to methods of synthesizing
compounds of the present invention.
Compounds of the Invention
[0228] The invention is directed to compounds as described herein
and pharmaceutically acceptable salts, solvates, esters, prodrugs
or isomers thereof, and pharmaceutical compositions comprising one
or more compounds as described herein and pharmaceutically
acceptable salts or isomers thereof. The invention further relates
to molecules which are useful in inhibiting the enzyme nicotinamide
phosphoribosyltransferase (NAMPT) and pharmaceutically acceptable
salts, solvates, esters, prodrugs or isomers thereof.
[0229] An aspect of this invention is the provision of compounds,
compositions, kits, and antidotes for the NAMPT pathway in mammals
having a compound of the Formula I:
##STR00042## [0230] wherein R is an aryl, heteroaryl,
C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 cycloalkenyl,
heterocycloalkyl, arylalkyl-, (heteroaryl)alkyl-, (C.sub.3-C.sub.8
cycloalkyl)alkyl-, (C.sub.3-C.sub.8 cycloalkenyl)alkyl-,
(heterocycloalkyl)alkyl-, (aryloxy)alkyl-, (heteroaryloxy)alkyl-,
(C.sub.3-C.sub.8 cycloalkyloxy)alkyl-, (C.sub.3-C.sub.8
cycloalkenyloxy)alkyl- or (heterocycloalkyloxy)alkyl-, wherein the
heteroatom of each of said heteroaryl and heterocycloalkyl numbers
1, 2 or 3, and is independently selected from N, S or O, further
wherein each of said aryl, heteroaryl and heterocycloalkyl may
independently be either substituted or fused with an aryl or
heteroaryl, still further wherein any of said aryl, heteroaryl and
heterocycloalkyl is either unsubstituted or optionally
independently substituted with one or more substituents which can
be the same or different and are independently selected from the
group consisting of deuterium, halo, cyano, amino, aminoalkyl-,
(amino)alkoxy-, --CONH.sub.2, --C(O)NH(alkyl),
--C(O)N(alkyl).sub.2, --C(O)NH(aryl), --C(O)N(aryl).sub.2,
--CH.sub.zF.sub.3-z, --OCH.sub.zF.sub.3-z, -alkyl, -alkenyl,
-alkynyl, -alkoxy, hydroxyl, alkyl hydroxy, hydroxyl, alkyl
hydroxy, or (alkoxyalkyl)amino-, --N(R.sup.3)--C(O)-alkyl,
--N(R.sup.3)--C(O)-aryl, -cycloalkyl, -heterocycloalkyl, -aryl, and
heteroaryl, with the proviso that no two adjacent ring heteroatoms
are both S or both O; [0231] Ar is aryl, heteroaryl,
heterocycloalkyl or C.sub.3 to C.sub.8 cycloalkyl, with each of
said aryl, heteroaryl, heterocycloalkyl and cycloalkyl being either
unsubstituted or optionally independently substituted with 1, 2, 3
or 4 substituents which can be the same or different and are
independently selected from the group consisting of deuterium,
halo, cyano, amino, aminoalkyl-, (amino)alkoxy-, --CONH.sub.2,
--C(O)NH(alkyl), --C(O)N(alkyl).sub.2, --C(O)NH(aryl),
--C(O)N(aryl).sub.2, --CH.sub.zF.sub.3-z, --OCH.sub.zF.sub.3-z,
-alkyl, -alkenyl, -alkynyl, -alkoxy, hydroxyl, -alkyl hydroxyl,
aryloxy-, (alkoxyalkyl)amino-, --N(R.sup.3)--C(O)-alkyl,
--N(R.sup.3)--C(O)-aryl, -cycloalkyl, -heterocycloalkyl, -aryl, and
-heteroaryl; [0232] R.sup.4 is cycloalkyl, --CH.sub.zF.sub.3-z,
aryl, heterocycloalkyl, heteroaryl, alkyl, -alkenyl, -alkynyl,
(aryl)alkyl-, (heteroaryl)alkyl- or (heterocycloalkyl)alkyl-,
or
##STR00043##
[0232] wherein each of said cycloalkyl, aryl, heterocycloalkyl,
heteroaryl and alkyl is either unsubstituted or optionally
substituted with 1, 2, 3, 4 or 5 substituents which can be the same
or different and are independently selected from the group
consisting of deuterium, halo, cyano, amino, aminoalkyl-,
(amino)alkoxy-, --CONH.sub.2, --C(O)NH(alkyl),
--C(O)N(alkyl).sub.2, --C(O)NH(aryl), --C(O)N(aryl).sub.2,
--CH.sub.zF.sub.3-z, --OCH.sub.zF.sub.3-z, -alkyl, alkoxy-,
-alkenyl, -alkynyl, aryloxy-, (alkoxyalkyl)amino-, -cycloalkyl,
-heterocycloalkyl, (heterocycloalkyl)alkyl-, -aryl, (aryl)alkyl-,
-heteroaryl, (heteroaryl)alkyl-, --S(O).sub.2-alkyl,
--S(O).sub.2-aryl, --S(O).sub.2--CF.sub.3,
--C(O).sub.N(alkyl).sub.2, --C(O)alkyl, --N(R.sup.3)--C(O)-alkyl,
--N(R.sup.3)--C(O)-aryl, --S(O.sub.2)NH.sub.2,
--S(O.sub.2)NH(alkyl), --S(O.sub.2)N(alkyl).sub.2,
--N(H)S(O.sub.2)(alkyl), --C(O)N(H)(alkyl), and methylenedioxy,
(ii) further wherein each of said cycloalkyl, aryl,
heterocycloalkyl, and heteroaryl may optionally additionally be
fused with independently selected aryl, heteroaryl,
heterocycloalkyl or cycloalkyl; [0233] R.sup.3 is H, alkyl or
arylalkyl-; [0234] X is S, S(O), S(O).sub.2, O or C(O); [0235] n is
1, 2, 3 or 4; [0236] m is 0, 1, 2, 3 or 4; [0237] q is 0 or 1;
[0238] t is 0, 1 or 2; and [0239] z is 0, 1 or 2; [0240] and
pharmaceutically acceptable salts, solates, esters, prodrugs and
isomers thereof.
[0241] In the compounds of Formula I, the various moieties are
independently selected.
[0242] The following embodiments are directed to Formula I, as
applicable. For any moieties that are not specifically defined, the
previous definitions control. Further, the moieties aryl,
heteroaryl, and heterocycloalkyl in these embodiments can be
independently unsubstituted or optionally substituted or optionally
fused as described earlier. Any one or more of the embodiments
relating to Formula I below can be combined with one or more other
embodiments of Formula I.
[0243] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is aryl, and n, m, q, t, z, Ar, X, R.sup.4 and R.sup.3
are as defined.
[0244] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is heteroaryl, and n, m, q, t, z, Ar, X, R.sup.4 and
R.sup.3 are as defined.
[0245] An embodiment of the invention is the provision of a
compound of Formula I where the various moieties are independently
selected, Ar is aryl, and R, n, m, q, t, z, X, R.sup.4 and R.sup.3
are as defined.
[0246] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, Ar is heteroaryl, and R, n, m, q, t, z, X, R.sup.4 and
R.sup.3 are as defined.
[0247] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, Ar, R, n, m, q, t, z, R.sup.4 and R.sup.3 are as defined
and X is S.
[0248] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, Ar, R, n, m, q, t, z, R.sup.4 and R.sup.3 are as defined
and X is S(O).
[0249] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, Ar, R, n, m, q, t, z, R.sup.4 and R.sup.3 are as defined
and X is S(O.sub.2).
[0250] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, Ar, R, n, m, q, t, z, R.sup.4 and R.sup.3 are as defined
and X is O.
[0251] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, Ar, R, n, m, q, t, z, R.sup.4 and R.sup.3 are as defined
and X is C(O).
[0252] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, Ar, R, n, m, q, t, z, R.sup.4 and R.sup.3 are as defined
and X is C(O).
[0253] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, Ar, R, n, m, q, t, z, R.sup.4 and X are as defined and
R.sup.3 is H.
[0254] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, Ar, R, n, m, q, t, z, R.sup.4 and X are as defined and
R.sup.3 is alkyl.
[0255] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, Ar, R, n, m, q, t, z, R.sup.4 and X are as defined and
R.sup.3 is arylalkyl.
[0256] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, Ar, R, n, m, q, t, z, R.sup.3 and X are as defined and
R.sup.4 is aryl.
[0257] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, Ar, R, n, m, q, t, z, R.sup.3 and X are as defined and
R.sup.4 is heteroaryl.
[0258] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, Ar, R, n, m, q, t, z, R.sup.3 and X are as defined and
R.sup.4 is heterocycloalkyl.
[0259] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is aryl, R.sup.4 is heteroaryl, and n, m, q, t, z, Ar,
R.sup.3 and X are as defined.
[0260] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is aryl, R.sup.4 is aryl, and n, m, q, t, z, Ar,
R.sup.3 and X are as defined.
[0261] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is heteroaryl, R.sup.4 is heteroaryl, and n, m, q, t,
z, Ar, R.sup.3 and X are as defined.
[0262] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is heteroaryl, R.sup.4 is aryl, and n, m, q, t, z, Ar,
R.sup.3 and X are as defined.
[0263] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is phenyl, R.sup.1 is heteroaryl, and n, m, q, t, z,
Ar, R.sup.3 and X are as defined.
[0264] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is phenyl, R.sup.4 is aryl, and n, m, q, t, R.sup.1,
R.sup.3 z, and Ar are as defined.
[0265] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is heteroaryl, R.sup.4 is phenyl, and n, m, q, t, z,
Ar, R.sup.3 and X are as defined.
[0266] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is pyrrolopyridinyl, R.sup.4 is phenyl, and n, m, q, t,
Ar, z, R.sup.3 and X are as defined.
[0267] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is oxadiazolyl, R.sup.4 is phenyl, and n, m, q, t, Ar,
z, R.sup.3 and X are as defined.
[0268] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is oxadiazolyl (substituted with pyridinyl), R.sup.4 is
phenyl, and n, m, q, t, z, Ar, R.sup.3 and X are as defined.
[0269] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is pyrazolyl, R.sup.4 is phenyl, and n, m, q, t, z, Ar,
R.sup.3 and X are as defined.
[0270] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is pyrazolyl (substituted with pyridinyl), R.sup.4 is
phenyl, and n, m, q, t, z, Ar, R.sup.3 and X are as defined.
[0271] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is imidazolyl, R.sup.4 is phenyl, and n, m, q, t, Ar,
z, R.sup.3 and X are as defined.
[0272] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is triazolopyridinyl, R.sup.4 is phenyl, and n, m, q,
t, z, Ar, R.sup.3 and X are as defined.
[0273] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is naphthyridinyl, R.sup.4 is phenyl, and n, m, q, t,
z, Ar, R.sup.3 and X are as defined.
[0274] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is tetrazolopyridinyl, R.sup.4 is phenyl, and n, m, q,
t, z, Ar, R.sup.3 and X are as defined.
[0275] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is isoquinolinyl, R.sup.4 is phenyl, and n, m, q, t,
Ar, R.sup.3 z, and X are as defined.
[0276] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is quinolinyl, R.sup.4 is phenyl, and n, m, q, t, Ar,
z, R.sup.3 and X are as defined.
[0277] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is imidazopyrazinyl, R.sup.4 is phenyl, and n, m, q, t,
z, Ar, R.sup.3 and X are as defined.
[0278] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is quinazolinyl, R.sup.4 is phenyl, and n, m, q, t, z,
Ar, R.sup.3 and X are as defined.
[0279] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is benzothiazolyl, R.sup.4 is phenyl, and n, m, q, t,
z, Ar, R.sup.3 and X are as defined.
[0280] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is thienopyridinyl, R.sup.4 is phenyl, and n, m, q, t,
z, Ar, R.sup.3 and X are as defined.
[0281] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is pyrrolopyridinyl, R.sup.4 is thiophenyl, and n, m,
q, z, t, Ar, R.sup.3 and X are as defined.
[0282] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is oxadiazolyl, R.sup.4 is naphthalinyl, and n, m, q,
t, z, Ar, R.sup.3 and X are as defined.
[0283] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is oxadiazolyl (substituted with pyridinyl), R.sup.4 is
quinolinyl, and n, m, q, z, t, Ar, R.sup.3 and X are as
defined.
[0284] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is pyrazolyl, R.sup.4 is isoquinolinyl, and n, m, q, t,
z, Ar, R.sup.3 and X are as defined.
[0285] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is pyrazolyl (substituted with pyridinyl), R.sup.4 is
benzodioxinyl, and n, m, q, t, z, Ar, R.sup.3 and X are as
defined.
[0286] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is imidazolyl, R.sup.4 is phenoxathiinyl, and n, m, q,
t, z, Ar, R.sup.3 and X are as defined.
[0287] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is pyrrolopyridinyl, R.sup.4 is phenyl, Ar is phenyl,
and n, m, q, t, z, R.sup.3 and X are as defined.
[0288] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is oxadiazolyl, R.sup.4 is phenyl, Ar is phenyl, and n,
m, q, t, z, R.sup.3 and X are as defined.
[0289] An embodiment of the invention is the provision of a
compound of Formula I d, where the various moieties are
independently selected, R is oxadiazolyl (substituted with
pyridinyl), R.sup.4 is phenyl, Ar is phenyl, and n, m, z, q, t,
R.sup.3 and X are as defined.
[0290] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is pyrazolyl, R.sup.4 is phenyl, Ar is phenyl, and n,
m, q, t, z, R.sup.3 and X are as defined.
[0291] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is pyrazolyl (substituted with pyridinyl), R.sup.4 is
phenyl, Ar is phenyl, and n, m, q, z, t, R.sup.3 and X are as
defined.
[0292] An embodiment of the invention is the provision of a
compound, where the various moieties are independently selected, R
is imidazolyl, R.sup.4 is phenyl, Ar is phenyl, and n, m, q, t, z,
R.sup.3 and X are as defined.
[0293] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is triazolopyridinyl, R.sup.4 is phenyl, Ar is phenyl,
and n, m, q, t, z, R.sup.3 and X are as defined.
[0294] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is naphthyridinyl, R.sup.4 is phenyl, Ar is phenyl, and
n, m, q, t, z, R.sup.3 and X are as defined.
[0295] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is tetrazolopyridinyl, R.sup.4 is phenyl, Ar is phenyl,
and n, m, q, t, z, R.sup.3 and X are as defined.
[0296] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is isoquinolinyl, R.sup.4 is phenyl, Ar is phenyl, and
n, m, q, t, z, R.sup.3 and X are as defined.
[0297] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is quinolinyl, R.sup.4 is phenyl, Ar is phenyl, and n,
m, q, t, z, R.sup.3 and X are as defined.
[0298] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is imidazopyrazinyl, R.sup.4 is phenyl, Ar is phenyl,
and n, m, q, t, z, R.sup.3 and X are as defined.
[0299] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is quinazolinyl, R.sup.4 is phenyl, Ar is phenyl, and
n, m, q, t, z, R.sup.3 and X are as defined.
[0300] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is benzothiazolyl, R.sup.4 is phenyl, Ar is phenyl, and
n, m, q, t, z, R.sup.3 and X are as defined.
[0301] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is thienopyridinyl, R.sup.4 is phenyl, Ar is phenyl,
and n, m, q, t, z, R.sup.3 and X are as defined.
[0302] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is pyrrolopyridinyl, R.sup.4 is phenyl, Ar is phenyl, n
is 1, m is 1, q is 0, t is 0, z is 0, R.sup.3 and X are as
defined.
[0303] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is oxadiazolyl, R.sup.4 is phenyl, Ar is phenyl, n is
1, m is 1, q is 0, t is 0, z is 0, R.sup.3 and X are as
defined.
[0304] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is oxadiazolyl (substituted with pyridinyl), R.sup.4 is
phenyl, Ar is phenyl, n is 1, m is 1, q is 0, t is 0, z is 0,
R.sup.3 and X are as defined.
[0305] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is pyrazolyl, R.sup.4 is phenyl, Ar is phenyl, n is 1,
m is 1, q is 0, t is 0, z is 0, R.sup.3 and X are as defined.
[0306] An embodiment of the invention is the provision of a
compound of Formula I where the various moieties are independently
selected, R is pyrazolyl (substituted with pyridinyl), R.sup.4 is
phenyl, Ar is phenyl, n is 1, m is 1, q is 0, t is 0, z is 0,
R.sup.3 and X are as defined.
[0307] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is imidazolyl, R.sup.4 is phenyl, Ar is phenyl, n is 1,
m is 1, q is 0, t is 0, z is 0, R.sup.3 and X are as defined.
[0308] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is triazolopyridinyl, R.sup.4 is phenyl, Ar is phenyl,
n is 1, m is 1, q is 0, t is 0, z is 0, R.sup.3 and X are as
defined.
[0309] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is naphthyridinyl, R.sup.4 is phenyl, Ar is phenyl, n
is 1, m is 1, q is 0, t is 0, z is 0, R.sup.3 and X are as
defined.
[0310] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is tetrazolopyridinyl, R.sup.4 is phenyl, Ar is phenyl,
n is 1, m is 1, q is 0, t is 0, z is 0, R.sup.3 and X are as
defined.
[0311] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is isoquinolinyl, R.sup.4 is phenyl, Ar is phenyl, n is
1, m is 1, q is 0, t is 0, z is 0, R.sup.3 and X are as
defined.
[0312] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is quinolinyl, R.sup.4 is phenyl, Ar is phenyl, n is 1,
m is 1, q is 0, t is 0, z is 0, R.sup.3 and X are as defined.
[0313] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is imidazopyrazinyl, R.sup.4 is phenyl, Ar is phenyl, n
is 1, m is 1, q is 0, t is 0, z is 0, R.sup.3 and X are as
defined.
[0314] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is quinazolinyl, R.sup.4 is phenyl, Ar is phenyl, n is
1, m is 1, q is 0, t is 0, z is 0, R.sup.3 and X are as
defined.
[0315] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is benzothiazolyl, R.sup.4 is phenyl, Ar is phenyl, n
is 1, m is 1, q is 0, t is 0, z is 0, R.sup.3 and X are as
defined.
[0316] An embodiment of the invention is the provision of a
compound of Formula I, where the various moieties are independently
selected, R is thienopyridinyl, R.sup.4 is phenyl, Ar is phenyl, n
is 1, m is 1, q is 0, t is 0, z is 0, R.sup.3 and X are as
defined.
[0317] Another aspect of the invention are the compounds of Formula
I, where q=0, m=0, t=0, Ar=A, X=Q and R.sup.4 is
##STR00044##
and the formula is now Formula IB
##STR00045## [0318] wherein [0319] R and R.sup.3 are as defined in
Formula I; [0320] R.sup.1 and R.sup.2 are the same or they are
different, and are independently selected from H, a straight or
branched C.sub.1 to C.sub.7 alkyl, straight or branched C.sub.1 to
C.sub.7 alkoxy, straight or branched C.sub.1 to C.sub.4
hydroxyalkyl, aryl, heteroaryl, heterocycloalkyl and cycloalkyl,
and wherein heteroatoms of said heteroaryl and heterocycloalkyl are
independently selected from one or more N, O and S, with the
proviso that no two adjacent ring heteroatoms are both S or both O,
further wherein R.sup.1 and R.sup.2 can be either unsubstituted or
optionally independently substituted with one or more substituents
which can be the same or different and are independently selected
from the group consisting of deuterium, halo, cyano, amino,
aminoalkyl-, (amino)alkoxy-, --CONH.sub.2, --C(O)NH(alkyl),
--C(O)N(alkyl).sub.2, --C(O)NH(aryl), --C(O)N(aryl).sub.2,
--CH.sub.zF.sub.3-z, --OCH.sub.zF.sub.3-z, -alkyl, -alkenyl,
-alkynyl, hydroxyalkyl-, -alkoxy, hydroxyl, alkyl hydroxy, carboxy,
(alkoxyalkyl)amino-, -alkylamine, aminocarbonyl-, --CHO,
--N(R.sup.3)--C(O)-alkyl, --N(R.sup.3)--C(O)-aryl, -cycloalkyl,
-heterocycloalkyl, -aryl, and heteroaryl; [0321] A is aryl,
heteroaryl, heterocycloalkyl or C.sub.3 to C.sub.8 cycloalkyl, with
each of said aryl, heteroaryl, heterocycloalkyl and cycloalkyl
being either unsubstituted or optionally independently substituted
with 1, 2, 3 or 4 substituents which can be the same or different
and are independently selected from the group consisting of
deuterium, halo, cyano, amino, aminoalkyl-, (amino)alkoxy-,
CONH.sub.2, --C(O)NH(alkyl), --C(O)N(alkyl).sub.2, --C(O)NH(aryl),
--C(O)N(aryl).sub.2, --CH.sub.zF.sub.3-z, --OCH.sub.zF.sub.3-z,
-alkyl, -alkenyl, -alkynyl, -alkoxy, hydroxyl, -alkyl hydroxyl,
aryloxy-, (alkoxyalkyl)amino-, --N(R.sup.3)--C(O)-alkyl,
--N(R.sup.3)--C(O)-aryl, -cycloalkyl, -heterocycloalkyl, -aryl, and
-heteroaryl; [0322] Q is C(O), S(O), S(O).sub.2, --N(H)--C(O)--,
--S(O.sub.2)--NH--, or --N(H)--S(O.sub.2)--; [0323] n is 0, 1, 2, 3
or 4; and [0324] z is 0, 1 or 2; and pharmaceutically acceptable
salts, solvates, esters, prodrugs or isomers thereof.
[0325] Another embodiment of Formula IB are compounds of Formula
IC
##STR00046## [0326] wherein [0327] R, A, Q, R.sup.3, z and n are as
defined in Formula IB, and [0328] R.sup.1 and R.sup.2 are joined
together to form, along with the N they are shown attached to in
the formula, a C.sub.3-C.sub.8 heterocycloalkyl, a C.sub.3-C.sub.8
heterocycloalkenyl, a fused bicyclic heterocycloalkyl, a fused
tricyclic heterocycloalkyl, spiroheterocycloalkyl, or a
heterospiroheterocycloalkyl, wherein each of said heterocycloalkyl,
heterocycloalkenyl, spiroheterocycloalkyl, and
heterospiroheterocycloalkyl can optionally contain one or more
heteroatoms in addition to the N atom they are shown attached to in
the formula, said heteroatoms being selected from N, S and O, with
the proviso that no two adjacent ring heteroatoms are both S or
both O, further wherein each of said heterocycloalkyl and
heterocycloalkenyl can be either unsubstituted or optionally
independently substituted with one or more substituents which can
be the same or different and are independently selected from the
group consisting of deuterium, halo, cyano, amino, aminoalkyl-,
(amino)alkoxy-, --CONH.sub.2, --C(O)NH(alkyl),
--C(O)N(alkyl).sub.2, --C(O)NH(aryl), --C(O)N(aryl).sub.2,
--CH.sub.zF.sub.3-z, --OCH.sub.zF.sub.3-z, -alkyl, -alkenyl,
-alkynyl, hydroxyalkyl, -alkoxy, hydroxyl, -alkyl hydroxy, carboxy,
(alkoxyalkyl)amino-, -alkylamine, aminocarbonyl-, --CHO,
--N(R.sup.3)--C(O)-alkyl, --N(R.sup.3)--C(O)-aryl, -cycloalkyl,
-heterocycloalkyl, -aryl, and heteroaryl; and pharmaceutically
acceptable salts thereof.
[0329] In the compounds of Formulas IB and C the various moieties
are independently selected.
[0330] The following embodiments are directed to Formula IB and C,
as applicable. For any moieties that are not specifically defined,
the previous definitions control. Further, the moieties aryl,
heteroaryl, heterocycloalkyl, cycloalkyl, cycloalkenyl and
heterocycloalkenyl in these embodiments can be independently
unsubstituted or optionally substituted or optionally fused as
described earlier. Any one or more of the embodiments relating to
Formula IB and IC below can be combined with one or more other
embodiments for Formula IB and IC.
[0331] An embodiment of the invention is the provision of a
compound of Formulas IB and IC, where the various moieties are
independently selected, R is aryl, and n, A, Q and R.sup.1 and
R.sup.2 are as defined.
[0332] Another embodiment of the invention is the provision of a
compound of Formulas IB and IC where the various moieties are
independently selected, R is heteroaryl, and n, A, Q and R.sup.1
and R.sup.2 are as defined.
[0333] Another embodiment of the invention is the provision of a
compound of Formulas IB and IC, the various moieties are
independently selected, R is C.sub.3-C.sub.8 cycloalkyl, and n, A,
Q and R.sup.1 and R.sup.2 are as defined.
[0334] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is C.sub.3-C.sub.8 cycloalkenyl, and n,
A, Q and R.sup.1 and R.sup.2 are as defined.
[0335] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is heterocycloalkyl, and n, A, Q and
R.sup.1 and R.sup.2 are as defined.
[0336] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is arylalkyl, and n, A, Q and R.sup.1 and
R.sup.2 are as defined.
[0337] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is (heteroaryl)alkyl, and n, A, Q and
R.sup.1 and R.sup.2 are as defined.
[0338] Another embodiment of the invention is the provision of a
compound of Formula IB and IC where the various moieties are
independently selected, R is (C.sub.3-C.sub.8 cycloalkyl)alkyl, and
n, A, Q and R.sup.1 and R.sup.2 are as defined.
[0339] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is (C.sub.3-C.sub.8 cycloalkenyl)alkyl,
and n, A, Q and R.sup.1 and R.sup.2 are as defined.
[0340] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is (heterocycloalkyl)alkyl, and n, A, Q
and R.sup.1 and R.sup.2 are as defined.
[0341] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is (aryloxy)alkyl, and n, A, Q and
R.sup.1 and R.sup.2 are as defined.
[0342] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is (heteroaryloxy)alkyl, and n, A, Q and
R.sup.1 and R.sup.2 are as defined.
[0343] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is (C.sub.3-C.sub.8 cycloalkyloxy)alkyl,
and n, A, Q and R.sup.1 and R.sup.2 are as defined.
[0344] Another embodiment of the invention is the provision of a
compound of Formula IB, where the various moieties are
independently selected, R is (C.sub.3-C.sub.8
cycloalkenyloxy)alkyl, and n, A, Q and R.sup.1 and R.sup.2 are as
defined.
[0345] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is (heterocycloalkyloxy)alkyl, and n, A,
Q and R.sup.1 and R.sup.2 are as defined.
[0346] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, n, Q and R1 and R.sup.2 are as defined
and A is aryl.
[0347] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where he various moieties are
independently selected, R, n, Q and G are as defined and A is
heteroaryl.
[0348] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, n, Q and R1 and R.sup.2 are as defined
and A is heterocycloalkyl.
[0349] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, n, Q and R1 and R.sup.2 are as defined
and A is C.sub.3-C.sub.8 cycloalkyl.
[0350] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where he various moieties are
independently selected, R, A, Q and R1 and R.sup.2 are as defined
and n is 0.
[0351] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, A, Q and R1 and R.sup.2 are as defined
and n is 1.
[0352] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, A, Q and R1 and R.sup.2 are as defined
and n is 2.
[0353] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, A, Q and R1 and R.sup.2 are as defined
and n is 3.
[0354] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, A, Q and R1 and R.sup.2 are as defined
and n is 4.
[0355] Another embodiment of the invention is the provision of a
compound of Formula IB, where the various moieties are
independently selected, R, A, n and R1 and R.sup.2 are as defined
and Q is C(O).
[0356] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, A, n and R.sup.1 and R.sup.2 are as
defined and Q is S(O).
[0357] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, A, n and R.sup.1 and R.sup.2 are as
defined and Q is S(O.sub.2).
[0358] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, A, n and R.sup.1 and R.sup.2 are as
defined and Q is --N(H)--S(O.sub.2)--.
[0359] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, A, n and R.sup.1 and R.sup.2 are as
defined and Q is --S(O.sub.2)--N(H)--.
[0360] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, A, n and R.sup.1 and R.sup.2 are as
defined and Q is --N(H)--C(O)--.
[0361] An embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is phenyl, and n, A, Q and R.sup.1 and
R.sup.2 are as defined.
[0362] An embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is naphthyl, and n, A, Q and R.sup.1 and
R.sup.2 are as defined.
[0363] An embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is pyridyl, and n, A, Q and R.sup.1 and
R.sup.2 are as defined.
[0364] An embodiment of the invention is the provision of a
compound, where Formulas IB and IC the various moieties are
independently selected, R is a pyrrolopyridinyl group, and n, A, Q
and R.sup.1 and R.sup.2 are as defined.
[0365] An embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is a thienopyridinyl group, and n, A, Q
and R.sup.1 and R.sup.2 are as defined.
[0366] An embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is an indazolyl group, and n, A, Q and
R.sup.1 and R.sup.2 are as defined.
[0367] An embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is a pyrazolopyridinyl group, and n, A, Q
and R.sup.1 and R.sup.2 are as defined.
[0368] An embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is an imidazopyridinyl group, and n, A, Q
and R.sup.1 and R.sup.2 are as defined.
[0369] An embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is an imidazopyrazolyl group, and n, A, Q
and R.sup.1 and R.sup.2 are as defined.
[0370] An embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is a tetrazolopyridinyl group, and n, A,
Q and R.sup.1 and R.sup.2 are as defined.
[0371] An embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is a naphthyridinyl group, and n, A, Q
and R.sup.1 and R.sup.2 are as defined.
[0372] An embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is a benzodiazolyl group, and n, A, Q and
R.sup.1 and R.sup.2 are as defined.
[0373] An embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is a benzothiazolyl group, and n, A, Q
and R1 and R.sup.2 are as defined.
[0374] An embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is a furopyridinyl group, and n, A, Q and
R1 and R.sup.2 are as defined.
[0375] An embodiment of the invention is the provision of a
compound of Formula IB and I C, where the various moieties are
independently selected, R is a (pyridinyloxy)methyl group, and n,
A, Q and R.sup.1 and R.sup.2 are as defined.
[0376] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is (pyridinyl)alkyl, and n, A, Q and
R.sup.1 and R.sup.2 are as defined.
[0377] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is (pyridinyl)ethyl, and n, A, Q and
R.sup.1 and R.sup.2 are as defined.
[0378] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R is (pyrrolopyridinyl)methyl, and n, A, Q
and R1 and R.sup.2 are as defined.
[0379] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, n, Q and R1 and R.sup.2 are as defined
and A is phenyl.
[0380] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, n, Q and R1 and R.sup.2 are as defined
and A is piperidinyl.
[0381] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, R, A, n, R.sup.2, and Q are as defined, and
R.sup.1 is H.
[0382] Another embodiment of the invention is the provision of a
compound of Formula IB, where the various moieties are
independently selected, R, A, n, R.sup.1, and Q are as defined, and
--R.sup.2 is piperidinyl.
[0383] Another embodiment of the invention is the provision of a
compound of Formula IB, where the various moieties are
independently selected, R, A, n, R.sup.1, and Q are as defined, and
--R.sup.2 is quinolinyl.
[0384] Another embodiment of the invention is the provision of a
compound of Formula IB, where the various moieties are
independently selected, R, A, n, R.sup.1, and Q are as defined, R1
is H and --R.sup.2 is morpholinyl.
[0385] Another embodiment of the invention is the provision of a
compound of Formula IB, where the various moieties are
independently selected, R, A, n, R.sup.1, and Q are as defined,
R.sup.1 is H and --R.sup.2 is piperidinyl.
[0386] Another embodiment of the invention is the provision of a
compound of Formula IB, where the various moieties are
independently selected, R, A, n, R.sup.1, and Q are as defined, R1
is H and --R.sup.2 is quinolinyl.
[0387] Another embodiment of the invention is the provision of a
compound of Formula IB, where the various moieties are
independently selected, R, A, n, R.sup.1, and Q are as defined, and
--R.sup.2 is morpholinyl.
[0388] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, n, R.sup.1, R.sup.2, and Q are as defined,
both A and R are aryl.
[0389] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, n, R.sup.1, R.sup.2, and Q are as defined,
both A and R are heteroaryl.
[0390] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, n, R.sup.1, R.sup.2, and Q are as defined,
R is heteroaryl and A is aryl.
[0391] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, n, R.sup.1, R.sup.2, and Q are as defined,
R is (heteroaryl)alkyl and A is aryl.
[0392] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, n, R.sup.1, R.sup.2, and Q are as defined,
R is (heteroaryloxy)alkyl and A is aryl.
[0393] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, n, R.sup.1, R.sup.2, and Q are as defined,
R is aryl and A is heteroaryl.
[0394] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, n, R.sup.1, R.sup.2 are as defined, both A
and R are aryl and Q is S(O.sub.2).
[0395] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, n, R.sup.1, R.sup.2 are as defined, both A
and R are heteroaryl and Q is S(O.sub.2).
[0396] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, n, R.sup.1, R.sup.2 are as defined, A is
aryl, R is heteroaryl and Q is S(O.sub.2).
[0397] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, n, R.sup.1, R.sup.2 are as defined, A is
aryl, R is (heteroaryl)alkyl and Q is S(O.sub.2).
[0398] Another embodiment of the invention is the provision of a
compound of Formula IB and IC, where the various moieties are
independently selected, n, R.sup.1, R.sup.2 are as defined, A is
aryl, R is (heteroaryloxy)alkyl and Q is S(O.sub.2).
[0399] Another aspect of the invention is compounds derived from
Formula I where q=0, m=0 and t=0, whereby the formula becomes
Formula II or pharmaceutically acceptable salts thereof:
##STR00047## [0400] wherein: [0401] R is heteroaryl comprising 1,
2, 3 or 4 heteroatom(s) independently selected from N, S or O,
wherein said heteroaryl may be substituted by one or more
substituents selected from the group consisting of amino, oxo, and
halo; and wherein said heteroaryl can comprise one or more
N-oxide(s) formed with a N atom member of said heteroaryl; [0402]
Ar is aryl or heteroaryl comprising 1, 2, 3 or 4 heteroatom(s)
independently selected from N, S or O; [0403] X is S(O).sub.2 or
S.dbd.O; [0404] R.sup.1 is --NHR.sup.4 and R.sup.4 is cycloalkyl,
heterocycloalkyl, aryl or heteroaryl; [0405] cycloalkyl; [0406]
aryl; [0407] heterocycloalkyl; or [0408] heteroaryl; wherein:
[0409] each of said cycloalkyl, aryl, or heteroaryl is
unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents
which can be the same or different and are independently selected
from the group consisting of: [0410] deuterium, halo, hydroxy,
hydroxyalkyl, cyano, --(CH.sub.2).sub.mNR.sup.aR.sup.b, oxo, alkyl,
cyanoalkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl-, alkenyl,
alkynyl, alkynylalkoxy, --CONH.sub.2, --S-alkyl, --C(O)NH(alkyl),
--C(O)N(alkyl).sub.2, --C(O)NH(cycloalkyl), --C(O)NH(aryl),
--C(O)N(aryl).sub.2, arylalkyl-, arylalkoxy-, aryloxy-, cycloalkyl,
heterocycloalkyl, aryl, (heterocycloalkyl)alkyl-,
(heterocycloalkyl)alkoxy-, --C(O)heterocycloalkyl, heteroaryl,
(heteroaryl)alkyl-, --S(O).sub.2-alkyl, --S(O).sub.2-aryl,
--S(O).sub.2--CH.sub.zF.sub.3-z, --C(O)alkyl,
--N(R.sup.5)--C(O)-alkyl, --N(R.sup.5)--C(O)-aryl,
--S(O.sub.2)NH.sub.2, --S(O.sub.2)NH(alkyl),
--S(O.sub.2)N(alkyl).sub.2, --N(H)(SO.sub.2)(alkyl), and
methylenedioxy, wherein each of said cycloalkyl, heterocycloalkyl,
aryl or heteroaryl may be substituted by one or more halo, cyano,
alkyl or alkoxy and; [0411] each of said cycloalkyl,
heterocycloalkyl, aryl, or heteroaryl may optionally additionally
be fused with independently selected aryl, heteroaryl,
heterocycloalkyl or cycloalkyl to from a bicyclic or tricyclic
group that may be substituted by one or more halo, cyano, alkyl or
alkoxy; [0412] R.sup.2 and R.sup.3 can be independently selected
from the group consisting of H and deuterium; [0413] R.sup.5 is H,
alkyl or arylalkyl-; [0414] R.sup.a and R.sup.b are independently
selected from the group consisting of H, alkyl, alkoxy, alkoxyalkyl
and haloalkyl; [0415] m is 0, 1, 2, 3, 4, 5 or 6; and [0416] n is 0
or 1;
[0417] An embodiment of Formula II of this invention is the
provision of compounds compositions, kits and antidotes for the
NAMPT pathway in mammals where X is S(O).sub.2 and n=1, the formula
now becoming the Formula II A:
##STR00048## [0418] wherein: [0419] R is heteroaryl comprising 1,
2, 3 or 4 heteroatom(s) independently selected from N, S or O,
wherein said heteroaryl may be substituted by one or more
substituents selected from the group consisting of amino, oxo, and
halo; and wherein said heteroaryl can comprise one or more
N-oxide(s) formed with a N atom member of said heteroaryl; [0420]
Ar is aryl or 5 or 6 membered heteroaryl comprising 1, 2, 3 or 4
heteroatom(s) independently selected from N, S or O; [0421] R.sup.1
is --NHR.sup.4 where R.sup.4 is cycloalkyl, heterocycloalkyl, aryl
or heteroaryl; [0422] cycloalkyl; [0423] aryl; or [0424]
heteroaryl; wherein: [0425] each of said cycloalkyl, aryl, or
heteroaryl is unsubstituted or substituted with 1, 2, 3, 4 or 5
substituents which can be the same or different and are
independently selected from the group consisting of: [0426]
deuterium, halo, hydroxy, hydroxyalkyl, cyano,
--(CH.sub.2).sub.mNR.sup.aR.sup.b, oxo, alkyl, cyanoalkyl,
haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl-, alkenyl, alkynyl,
alkynylalkoxy, --CONH.sub.2, --S-alkyl, --C(O)NH(alkyl),
--C(O)N(alkyl).sub.2, --C(O)NH(cycloalkyl), --C(O)NH(aryl),
--C(O)N(aryl).sub.2, arylalkyl-, arylalkoxy-, aryloxy-, cycloalkyl,
heterocycloalkyl, aryl, (heterocycloalkyl)alkyl-,
(heterocycloalkyl)alkoxy-, --C(O)heterocycloalkyl, heteroaryl,
(heteroaryl)alkyl-, --S(O).sub.2-alkyl, --S(O).sub.2-aryl,
--S(O).sub.2--CH.sub.zF.sub.3-z, --C(O)alkyl,
--N(R.sup.5)--C(O)-alkyl, --N(R.sup.5)--C(O)-aryl,
--S(O.sub.2)NH.sub.2, --S(O.sub.2)NH(alkyl),
--S(O.sub.2)N(alkyl).sub.2, --N(H)(SO.sub.2)(alkyl), and
methylenedioxy, wherein each of said cycloalkyl, heterocycloalkyl,
aryl or heteroaryl may be substituted by one or more halo, cyano,
alkyl or alkoxy and; [0427] each of said cycloalkyl,
heterocycloalkyl, aryl, or heteroaryl may optionally additionally
be fused with independently selected aryl, heteroaryl,
heterocycloalkyl or cycloalkyl to from a bicyclic or tricyclic
group that may be substituted by one or more halo, cyano, alkyl or
alkoxy; [0428] R.sup.2 and R.sup.3 can be independently selected
from the group consisting of H and deuterium; [0429] R.sup.5 is H,
alkyl or arylalkyl-; [0430] R.sup.a and R.sup.b are independently
selected from the group consisting of H, alkyl, alkoxy, alkoxyalkyl
and haloalkyl; and [0431] m is 0, 1, 2, 3, 4, 5 or 6.
[0432] In the compounds of Formulas II, and HA, the various
moieties are independently selected.
[0433] The following embodiments are directed to Formulas II, and
IIA as applicable. For any moieties that are not specifically
defined, the previous definitions control. Further, the moieties
aryl, heteroaryl, heterocycloalkyl, cycloalkyl, cycloalkenyl and
heterocycloalkenyl in these embodiments can be independently
unsubstituted or optionally substituted or optionally fused as
described earlier. Any one or more of the embodiments relating to
Formula II or IIA below can be combined with one or more other
embodiments for Formula II or IIA.
[0434] An embodiment of the invention is the provision of a
compound of Formula II or II A where the various moieties are
independently selected and Ar is aryl.
[0435] An embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and Ar is phenyl.
[0436] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and Ar has the formula of:
##STR00049##
[0437] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and Ar is 5 or 6 membered heteroaryl.
[0438] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and Ar is pyridine.
[0439] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and R is a bicyclic heteroaryl.
[0440] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and R is a 9 to 10 membered bicyclic
heteroaryl containing 1, 2, 3, or 4 heteroatoms independently
selected from N, S or O.
[0441] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and R is selected from benzothiazole,
dihydronaphthyridine, dihydropyridopyrimidine,
dihydropyrrolopyridine, furopyridine, imidazopyrazine,
imidazopyrazole imidazopyridine, imidazopyrimidine, indazole,
indole, isoquinoline, naphthyridine, pyrazolopyridine,
pyrrolopyridine, tetrazolopyridine, tetrahydroimidazopyridine,
tetrahydropyrazolopyridine, thiazolopyridine and
thienopyridine.
[0442] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and R is selected from
1H-pyrazolo[3,4-b]pyridine;
1,4,6,7-Tetrahydro-pyrazolo[4,3-c]pyridine;
7,8-Dihydro-5H-pyrido[4,3-d]pyrimidine;
5,7-Dihydro-pyrrolo[3,4-b]pyridine;
7,8-Dihydro-5H-[1,6]naphthyridine;
1,4,6,7-Tetrahydro-imidazo[4,5-c]pyridine;
1,8a-dihydroimidazo[1,2-a]pyridine; thieno[3,2-c]pyridine;
1H-imidazo[1,2-b]pyrazole; 1H-pyrazolo[3,4-b]pyridine;
furo[2,3-c]pyridine; 1H-pyrazolo[3,4-b]pyridine;
1H-pyrrolo[3,2-c]pyridine; thieno[2,3-b]pyridine;
imidazo[1,2-a]pyrimidine; furo[2,3-c]pyridine; isoquinoline;
1H-indazole; imidazo[1,2-a]pyridine; thieno[2,3-c]pyridine;
furo[2,3-c]pyridine; 1H-pyrrolo[2,3-c]pyridine;
imidazo[1,2-a]pyrazine; 1,3-benzothiazole; benzo[d]thiazole;
1H-pyrrolo[2,3-b]pyridine; [1,3]thiazolo[5,4-c]pyridine;
[1,2,3,4]tetrazolo[1,5-a]pyridine; 1,5-naphthyridine; 1H-indole;
1H-imidazo[4,5-c]pyridine; and 1,6-naphthyridine.
[0443] Another embodiment of the invention is the provision of
compounds of Formula II or IIA wherein R is selected from the group
consisting of:
##STR00050##
[0444] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is aryl and R is a 9 to 10 membered
bicyclic heteroaryl containing 1, 2, 3, or 4 heteroatoms
independently selected from N, S or O.
[0445] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is phenyl and R is a 9 to 10 membered
bicyclic heteroaryl containing 1, 2, 3, or 4 heteroatoms
independently selected from N, S or O.
[0446] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is phenyl and R is selected from
benzothiazole, dihydronaphthyridine, dihydropyridopyrimidine,
dihydropyrrolopyridine, furopyridine, imidazopyrazine,
imidazopyrazole imidazopyridine, imidazopyrimidine, indazole,
indole, isoquinoline, naphthyridine, pyrazolopyridine,
pyrrolopyridine, tetrazolopyridine, tetrahydroimidazopyridine,
tetrahydropyrazolopyridine, thiazolopyridine and
thienopyridine.
[0447] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and Ar is 5 or 6 membered heteroaryl and R
is a 9 to 10 membered bicyclic heteroaryl containing 1, 2, 3, or 4
heteroatoms independently selected from N, S or 0.
[0448] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is pyridine and R is a 9 to 10 membered
bicyclic heteroaryl containing 1, 2, 3, or 4 heteroatoms
independently selected from N, S or O.
[0449] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and R is substituted at a position adjacent
to a nitrogen atom on its cycle.
[0450] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is aryl and R is substituted at a
position adjacent to a nitrogen atom on its cycle.
[0451] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is phenyl and R is substituted at a
position adjacent to a nitrogen atom on its cycle.
[0452] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is 5 or 6 membered heteroaryl and R is
substituted at a position adjacent to a nitrogen atom on its
cycle.
[0453] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is pyridine and R is substituted at a
position adjacent to a nitrogen atom on its cycle.
[0454] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, R.sup.1 is --NHR.sup.4 and R.sup.4 is
cycloalkyl, heterocycloalkyl, aryl or heteroaryl.
[0455] Another embodiment of the invention is the provision of a
compound of Formula III or IIIA where the various moieties are
independently selected, Ar is aryl, R.sup.1 is --NHR.sup.4 and
R.sup.4 is cycloalkyl, heterocycloalkyl, aryl or heteroaryl.
[0456] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is phenyl, R.sup.1 is --NHR.sup.4 and
R.sup.4 is cycloalkyl, heterocycloalkyl, aryl or heteroaryl.
[0457] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is 5 or 6 membered heteroaryl, R.sup.1
is --NHR.sup.4 and R.sup.4 is cycloalkyl, heterocycloalkyl, aryl or
heteroaryl.
[0458] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is pyridine, R.sup.1 is --NHR.sup.4 and
R.sup.4 is cycloalkyl, heterocycloalkyl, aryl or heteroaryl.
[0459] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and R is a 9 to 10 membered bicyclic
heteroaryl containing 1,2,3, or 4 heteroatoms independently
selected from N, S or O, Ar is phenyl and R.sup.1 is --NHR.sup.4
and R.sup.4 is cycloalkyl, heterocycloalkyl, aryl or
heteroaryl.
[0460] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and R is a 9 to 10 membered bicyclic
heteroaryl containing 1,2,3, or 4 heteroatoms independently
selected from N, S or O, Ar is pyridine and R.sup.1 is --NHR.sup.4
and R.sup.4 is cycloalkyl, heterocycloalkyl, aryl or
heteroaryl.
[0461] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and R.sup.1 is unsubstituted or substituted
C.sub.3-C.sub.10 cycloalkyl.
[0462] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is aryl, and R.sup.1 is unsubstituted or
substituted C.sub.3-C.sub.10 cycloalkyl.
[0463] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is phenyl, and R.sup.1 is unsubstituted
or substituted C.sub.3-C.sub.10 cycloalkyl.
[0464] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is 5 or 6 membered heteroaryl, and
R.sup.1 is unsubstituted or substituted C.sub.3-C.sub.10
cycloalkyl.
[0465] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is pyridine, and R.sup.1 is
unsubstituted or substituted C.sub.3-C.sub.10 cycloalkyl.
[0466] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and R.sup.1 is unsubstituted or substituted
aryl.
[0467] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected and R.sup.1 is unsubstituted or substituted
5 to 11 membered monocyclic or bicyclic heterocycloalkyl comprising
1,2,3, or 4 heteroatom(s) selected from N, S or O.
[0468] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is aryl and R.sup.1 is unsubstituted or
substituted 5 to 11 membered monocyclic or bicyclic
heterocycloalkyl comprising 1, 2, 3, or 4 heteroatom(s) selected
from N, S or O.
[0469] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is phenyl and R.sup.1 is unsubstituted
or substituted 5 to 11 membered monocyclic or bicyclic
heterocycloalkyl comprising 1, 2, 3, or 4 heteroatom(s) selected
from N, S or O.
[0470] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is 5 or 6 membered heteroaryl and
R.sup.1 is unsubstituted or substituted 5 to 11 membered monocyclic
or bicyclic heterocycloalkyl comprising 1, 2, 3, or 4 heteroatom(s)
selected from N, S or O.
[0471] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is pyridine and R.sup.1 is unsubstituted
or substituted 5 to 11 membered monocyclic or bicyclic
heterocycloalkyl comprising 1, 2, 3, or 4 heteroatom(s) selected
from N, S or O.
[0472] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, R.sup.1 is unsubstituted or substituted 5
to 11 membered monocyclic or bicyclic heterocycloalkyl containing
at least one N-heteroatom from which the heterocycloalkyl is
attached to the rest of the compound of Formula II or IIA.
[0473] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is aryl and R.sup.1 is unsubstituted or
substituted 5 to 11 membered monocyclic or bicyclic
heterocycloalkyl containing at least one N-heteroatom from which
the heterocycloalkyl is attached to the rest of the compound of
Formula II or IIA.
[0474] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is phenyl and R.sup.1 is unsubstituted
or substituted 5 to 11 membered monocyclic or bicyclic
heterocycloalkyl containing at least one N-heteroatom from which
the heterocycloalkyl is attached to the rest of the compound of
Formula II or IIA.
[0475] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is 5 or 6 membered heterocyclic aryl and
R.sup.1 is unsubstituted or substituted 5 to 11 membered monocyclic
or bicyclic heterocycloalkyl containing at least one N-heteroatom
from which the heterocycloalkyl is attached to the rest of the
compound of Formula II or IIA.
[0476] Another embodiment of the invention is the provision of a
compound of Formula II or IIA where the various moieties are
independently selected, Ar is pyridine and R.sup.1 is unsubstituted
or substituted 5 to 11 membered monocyclic or bicyclic
heterocycloalkyl containing at least one N-heteroatom from which
the heterocycloalkyl is attached to the rest of the compound of
Formula II or IIA.
[0477] One embodiment of Formula IIA are compounds where Ar is
phenyl and the formula becomes Formula IIB
##STR00051## [0478] wherein: [0479] R is bicyclic heteroaryl
comprising 1, 2, 3 or 4 heteroatom(s) independently selected from
N, S or O, wherein said heteroaryl may be substituted by one or
more substituents selected from the group consisting of amino, oxo,
and halo; and wherein said heteroaryl can comprise one or more
N-oxide(s) formed with a N atom member of said heteroaryl; [0480]
R.sup.1 is --NHR.sup.4 and R.sup.4 is cycloalkyl, heterocycloalkyl,
aryl or heteroaryl; [0481] cycloalkyl; [0482] aryl; or [0483]
heteroaryl; wherein: [0484] each of said cycloalkyl, aryl, or
heteroaryl is unsubstituted or substituted with 1, 2, 3, 4 or 5
substituents which can be the same or different and are
independently selected from the group consisting of: [0485]
deuterium, halo, hydroxy, hydroxyalkyl, cyano,
--(CH.sub.2).sub.mNR.sup.aR.sup.b, oxo, alkyl, cyanoalkyl,
haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl-, alkenyl, alkynyl,
alkynylalkoxy, --CONH.sub.2, --S-alkyl, --C(O)NH(alkyl),
--C(O)N(alkyl).sub.2, --C(O)NH(cycloalkyl), --C(O)NH(aryl),
--C(O)N(aryl).sub.2, arylalkyl-, arylalkoxy-, aryloxy-, cycloalkyl,
heterocycloalkyl, aryl, (heterocycloalkyl)alkyl-,
(heterocycloalkyl)alkoxy-, --C(O)heterocycloalkyl, heteroaryl,
(heteroaryl)alkyl-, --S(O).sub.2-alkyl, --S(O).sub.2-aryl,
--S(O).sub.2--CH.sub.zF.sub.3-z, --C(O)alkyl,
--N(R.sup.5)--C(O)-alkyl, --N(R.sup.5)--C(O)-aryl,
--S(O.sub.2)NH.sub.2, --S(O.sub.2)NH(alkyl),
--S(O.sub.2)N(alkyl).sub.2, --N(H)(SO.sub.2)(alkyl), and
methylenedioxy, wherein each of said cycloalkyl, heterocycloalkyl,
aryl or heteroaryl may be substituted by one or more halo, cyano,
alkyl or alkoxy and; [0486] each of said cycloalkyl,
heterocycloalkyl, aryl, or heteroaryl may optionally additionally
be fused with independently selected aryl, heteroaryl,
heterocycloalkyl or cycloalkyl to from a bicyclic or tricyclic
group that may be substituted by one or more halo, cyano, alkyl or
alkoxy; [0487] R.sup.2 and R.sup.3 can be independently selected
from the group consisting of H and deuterium; [0488] R.sup.5 is H,
alkyl or arylalkyl-; [0489] R.sup.a and R.sup.b are independently
selected from the group consisting of H, alkyl, alkoxy, alkoxyalkyl
and haloalkyl; [0490] m is 0, 1, 2, 3, 4, 5 or 6; [0491] z is 0, 1
or 2.
[0492] An embodiment of the invention are compounds of Formula IIB
where R is selected from 9 to 10 membered bicyclic heteroaryl
groups containing 1,2, 3 or 4 heteroatoms independently selected
from N, S, and O.
[0493] Another embodiment of the invention are compounds of Formula
IIB, where R is selected from: benzothiazole, dihydronaphthyridine,
dihydropyridopyrimidine, dihydropyrrolopyridine, furopyridine,
imidazopyrazine, imidazopyrazole imidazopyridine,
imidazopyrimidine, indazole, indole, isoquinoline, naphthyridine,
pyrazolopyridine, pyrrolopyridine, tetrazolopyridine,
tetrahydroimidazopyridine, tetrahydropyrazolopyridine,
thiazolopyridine and thienopyridine.
[0494] Another embodiment of the invention are compounds of Formula
IIB, where R is selected from: 1H-pyrazolo[3,4-b]pyridine;
1,4,6,7-Tetrahydro-pyrazolo[4,3-c]pyridine;
7,8-Dihydro-5H-pyrido[4,3-d]pyrimidine;
5,7-Dihydro-pyrrolo[3,4-b]pyridine;
7,8-Dihydro-5H-[1,6]naphthyridine;
1,4,6,7-Tetrahydro-imidazo[4,5-c]pyridine;
1,8a-dihydroimidazo[1,2-a]pyridine; thieno[3,2-c]pyridine;
1H-imidazo[1,2-b]pyrazole; 1H-pyrazolo[3,4-b]pyridine;
furo[2,3-c]pyridine; 1H-pyrazolo[3,4-b]pyridine;
1H-pyrrolo[3,2-c]pyridine; thieno[2,3-b]pyridine;
imidazo[1,2-a]pyrimidine; furo[2,3-c]pyridine; isoquinoline;
1H-indazole; imidazo[1,2-a]pyridine; thieno[2,3-c]pyridine;
furo[2,3-c]pyridine; 1H-pyrrolo[2,3-c]pyridine;
imidazo[1,2-a]pyrazine; 1,3-benzothiazole; benzo[d]thiazole;
1H-pyrrolo[2,3-b]pyridine; [1,3]thiazolo[5,4-c]pyridine;
[1,2,3,4]tetrazolo[1,5-a]pyridine; 1,5-naphthyridine; 1H-indole;
1H-imidazo[4,5-c]pyridine; and 1,6-naphthyridine.
[0495] Another embodiment of the invention is compounds of Formula
IIB where R is substituted at a position adjacent to a nitrogen
atom on its cycle.
[0496] Another embodiment of the invention si compounds of Formula
IIB wherein R is selected from the group consisting of:
##STR00052##
[0497] Still another embodiment of the invention is compounds of
Formula IIB where R.sup.1 is --NHR.sup.4, R.sup.4 is cycloalkyl,
heterocycloalkyl, aryl or heteroaryl.
[0498] Yet another embodiment of the invention is compounds of
Formula IIB, where R.sup.4 is unsubstituted or substituted
cycloalkyl.
[0499] Another embodiment of the invention is compounds of Formula
IIB, where R.sup.4 is unsubstituted or substituted
heterocycloalkyl.
[0500] Another embodiment of the invention is compounds of Formula
IIB, where R.sup.4 is unsubstituted or substituted aryl.
[0501] Yet another embodiment of the invention is compounds of
Formula IIB, where R.sup.4 is unsubstituted or substituted
heteroaryl.
[0502] Still another embodiment of the invention is compounds of
Formula IIB, where R.sup.1 is unsubstituted or substituted
C.sub.3-C.sub.10-cycloalkyl.
[0503] Another embodiment of the invention is compounds of Formula
IIB, where R.sup.1 is unsubstituted or substituted aryl.
[0504] One embodiment of the invention is compounds of Formula IIB,
where R.sup.1 is unsubstituted or substituted 5 to 10 membered
monocyclic or bicyclic heteroaryl comprising 1, 2, 3 or 4
heteroatom(s) selected from N, S or O.
[0505] Another embodiment of the invention is compounds of Formula
IIB, where R.sup.1 or R.sup.4 is selected from the group consisting
of: 6-methoxypyridine; 2-ethoxy-4-fluorophenyl; 3,4-difluorophenyl;
3,4-dimethoxyphenyl; 3,4-dimethoxyphenyl; 3-chloro-5-fluorophenyl;
3-fluoro-4-methoxyphenyl; 4-chloro-2-methylphenyl;
4-fluoro-2-methoxyphenyl; 4-methoxy-2,5-dimethylphenyl;
4-methylphenyl; 5-chloro-2-ethoxyphenyl; 5-fluoro-2-methoxyphenyl;
1-(3-chlorophenyl)-1H-pyrazole; 1-(4-fluorophenyl)-1H-pyrazole;
1-(propan-2-yl)-1H-pyrazole; 1,3-thiazole;
1,4-dimethyl-1H-imidazole; 1,5-dimethyl-1H-imidazole;
1-benzothiophene; 1H-indole; 1-methyl-1H-1,3-benzodiazole;
1-methyl-1H-indazole; 1-methyl-1H-indole; 1-methyl-1H-pyrazole;
1-methyl-3-(trifluoromethyl)-1H-pyrazole;
1-methyl-5-(trifluoromethyl)-1H-pyrazole; 1-propyl-1H-pyrazole;
2-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)phenyl;
2-(3-fluorophenyl)-1,3-thiazole;
2-(benzyloxy)-5-(trifluoromethyl)phenyl; 2-(benzyloxy)phenyl;
2-(dimethylamino)pyrimidine; 2-(dimethylcarbamoyl)phenyl;
2-(ethoxymethyl)phenyl; 2-(methylsulfamoyl)phenyl;
2-(morpholin-4-yl)pyridine; 2-(morpholin-4-yl)pyridine;
2-(morpholin-4-ylmethyl)phenyl; 2-(pyrrolidin-1-yl)-1,3-thiazole;
2-(trifluoromethoxy)phenyl; 2-(trifluoromethoxy)phenyl];
2-(trifluoromethyl)imidazo[1,2-a]pyridine;
2-(trifluoromethyl)phenyl; 2-(trifluoromethyl)pyridine;
2,3,6-trimethoxyphenyl; 2,3-difluoro-6-methoxyphenyl;
2,3-difluorophenyl; 2,3-dihydro-1,4-benzodioxine;
2,3-dihydro-1-benzofuran; 2,3-dihydro-1-benzofuranphenyl;
2,3-dimethoxy-5-methylphenyl; 2,3-dimethoxyphenyl;
2,3-dimethylphenyl; 2,4,5-trimethylphenyl;
2,4-bis(trifluoromethyl)phenyl; 2,4-dichloro-3-methoxyphenyl;
2,4-difluorophenyl; 2,4-dimethoxyphenyl; 2,4-dimethylphenyl;
2,5-difluorophenyl; 2,5-dimethoxyphenyl; 2,5-dimethylphenyl;
2,6-dichloro-3-methylphenyl; 2,6-dichlorophenyl;
2,6-dimethoxy-4-methylphenyl; 2,6-dimethoxypyridine;
2,6-dimethylphenyl; 2-[ethyl(methyl)amino]-1,3-thiazole;
2-acetylphenyl; 2-butoxy-4-fluorophenyl; 2-butoxy-5-chlorophenyl;
2-butoxy-6-fluorophenyl; 2-chloro-3-(trifluoromethyl)phenyl;
2-chloro-3-fluorophenyl; 2-chloro-4-(trifluoromethyl)phenyl;
2-chloro-4-fluorophenyl; 2-chloro-4-methoxyphenyl;
2-chloro-4-methylphenyl; 2-chloro-5-(hydroxymethyl)phenyl;
2-chloro-5-(trifluoromethoxy)phenyl;
2-chloro-5-(trifluoromethyl)phenyl; 2-chloro-5-fluorophenyl;
2-chloro-5-methoxyphenyl; 2-chloro-5-methoxyphenyl;
2-chloro-5-methylphenyl; 2-chloro-6-fluorophenyl;
3-trifluoromethylphenyl; 2-chloro-6-methoxyphenyl; 2-chlorophenyl;
2-cyanophenyl; 2-ethoxy-4-fluorophenyl; 2-ethoxy-6-fluorophenyl;
2-ethoxyphenyl; 2-ethylphenyl; 2-fluoro-3-(propan-2-yloxy)phenyl;
2-fluoro-3-(trifluoromethoxy)phenyl; 2-fluoro-3-methoxyphenyl;
2-fluoro-3-methylphenyl; 2-fluoro-4-(1H-pyrazol-1-yl)phenyl;
2-fluoro-4-(trifluoromethyl)phenyl; 2-fluoro-4-methoxyphenyl;
2-fluoro-4-methylphenyl; 2-fluoro-5-methoxyphenyl;
2-fluoro-5-methylphenyl; 2-fluoro-6-methoxyphenyl;
2-fluoro-6-propoxyphenyl; 2-fluorophenyl; 2H-1,3-benzodioxole;
2-methanesulfonamidophenyl; 2-methanesulfonylphenyl;
2-methoxy-3-(trifluoromethyl)phenyl;
2-methoxy-4-(1H-pyrazol-1-yl)phenyl;
2-methoxy-4-(trifluoromethyl)phenyl;
2-methoxy-5-(propan-2-yl)phenyl;
2-methoxy-5-(trifluoromethoxy)phenyl; 2-methoxy-5-methylphenyl;
2-methoxy-6-(propan-2-yloxy)phenyl; 2-methoxyphenyl;
2-methyl-1,3-thiazole; 2-methyl-2H-indazole;
2-methyl-4-(1H-pyrazol-1-yl)phenyl;
2-methyl-4-(trifluoromethyl)phenyl; 2-methyl-4-propoxyphenyl;
2-methylphenyl; 2-methylpyridine; 2-phenoxyphenyl; 2-phenylethane;
3-(1H-pyrazol-1-yl)phenyl; 3-(2,2,2-trifluoroethoxy)phenyl;
3-(2-methylpropoxy)phenyl; 3-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl;
3-(4-fluorophenoxy)phenyl; 3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl;
3-(cyclopentylcarbamoyl)phenyl;
3-(diethylcarbamoyl)-5-fluorophenyl; 3-(difluoromethoxy)phenyl;
3-(dimethylsulfamoyl)phenyl; 3-(ethanesulfonyl)phenyl;
3-(ethylcarbamoyl)phenyl; 3-(methoxymethyl)phenyl,
3-(methylcarbamoyl)phenyl; 3-(morpholin-4-yl)phenyl;
3-(piperidin-1-yl)phenyl; 3-(piperidin-1-ylmethyl)phenyl;
3-(piperidin-1-ylphenyl; 3-(propan-2-yl)phenyl;
3-(propan-2-yloxy)phenyl; 3-(propane-1-sulfonamido)phenyl;
3-(pyrimidin-2-yl)phenyl; 3-(trifluoromethoxy)phenyl;
3-(trifluoromethyl)phenyl; 3,4-dichlorophenyl; 3,4-dimethoxyphenyl;
3,4-dimethylphenyl; 3,5-dichlorophenyl; 3,5-difluorophenyl;
3,5-dimethoxyphenyl; 3,5-dimethylphenyl;
3-[(2-methylpropyl)carbamoyl]phenyl;
3-[(dimethylamino)methylphenyl; 3-[(morpholin-4-yl)carbonyl]phenyl;
3-[(propan-2-yl)carbamoyl]phenyl; 3-[2-(dimethylamino)ethoxyphenyl;
3-[2-(dimethylamino)ethyl]phenyl;
3-[2-(morpholin-4-yl)ethoxy]phenyl; 3-acetylphenyl; 3-butoxyphenyl;
3-chloro-2-(morpholin-4-yl)pyridine; 3-chloro-2-fluorophenyl;
3-chloro-2-methoxyphenyl; 3-chloro-2-methylphenyl;
3-chloro-4-(trifluoromethyl)phenyl; 3-chloro-4-methoxyphenyl;
3-chloro-4-methylphenyl; 3-chloro-4-propoxyphenyl;
3-chloro-5-(diethylcarbamoyl)phenyl;
3-chloro-5-(hydroxymethyl)phenyl; 3-chloro-5-fluorophenyl;
3-chloro-5-methoxyphenyl; 3-chloro-5-methylphenyl; 3-chlorophenyl;
3-cyanophenyl; 3-ethoxy-2-fluorophenyl; 3-ethoxy-4-fluorophenyl;
3-ethoxyphenyl; 3-ethylphenyl; 3-fluoro-2-methoxyphenyl;
3-fluoro-2-methylphenyl; 3-fluoro-2-methylphenyl;
3-fluoro-4-(1H-pyrazol-1-yl)phenyl;
3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl;
3-fluoro-4-(methylsulfanyl)phenyl;
3-fluoro-4-(trifluoromethoxy)phenyl;
3-fluoro-4-(trifluoromethyl)phenyl; 3-fluoro-4-methoxyphenyl;
3-fluoro-4-methylphenyl; 3-fluoro-4-propoxyphenyl;
3-fluoro-5-(2,2,2-trifluoroethoxy)phenyl;
3-fluoro-5-(2-methylpropoxy)phenyl;
3-fluoro-5-(morpholin-4-yl)phenyl;
3-fluoro-5-(pyrrolidin-1-yl)phenyl;
3-fluoro-5-(trifluoromethyl)phenyl; 3-fluoro-5-methoxyphenyl;
3-fluoro-5-methylphenyl; 3-fluorophenyl; 3-hydroxyphenyl;
3-methanesulfonylphenyl; 3-methoxy-4-methylphenyl;
3-methoxy-5-methylphenyl; 3-methoxyphenyl; 3-methylphenyl;
3-phenylphenyl; 3-phenylpropane; 3-propoxyphenyl;
3-sulfamoylphenyl; 3-tert-butylphenyl;
4-(1-cyanocyclopentyl)phenyl; 4-(1H-imidazol-1-yl)phenyl;
4-(1H-imidazol-1-ylmethyl)phenyl; 4-(1H-pyrazol-1-yl)phenyl;
4-(2-methylpropoxy)phenyl; 4-(4-ethoxyphenyl)phenyl;
4-(4-methylpiperazin-1-yl)phenyl;
4-(difluoromethyl)-3-fluorophenyl; 4-(dimethylcarbamoyl)phenyl;
4-(ethoxymethyl)phenyl; 4-(ethylcarbamoyl)phenyl;
4-(hydroxymethyl)phenyl; 4-(morpholin-4-yl)phenyl;
4-(propan-2-yl)phenyl; 4-(propan-2-yloxy)phenyl;
4-(pyrrolidin-1-yl); 4-(pyrrolidin-1-yl)phenyl;
4-(trifluoromethoxy)phenyl; 4-(trifluoromethyl)phenyl;
4-(trifluoromethyl)pyridine; 3,5-difluorophenyl;
4,5-difluoro-2-methoxyphenyl; 4-[(1R)-1-hydroxybutylphenyl;
(dimethylamino)methylphenyl; 4-[(pyrrolidin-1-yl)carbonyl]phenyl;
4-[2-(dimethylamino)ethyl]phenyl;
4-[2-(pyrrolidin-1-yl)ethoxy]phenyl; 4-acetylphenyl;
4-butoxy-2-methylphenyl; 4-butoxy-3-chlorophenyl;
4-butoxy-3-fluorophenyl; 4-butoxyphenyl; 4-butylphenyl;
4-chloro-2-(trifluoromethyl)phenyl; 4-chloro-2-ethoxyphenyl;
4-chloro-2-methoxyphenyl; 4-chloro-2-methylphenyl;
4-chloro-3-(trifluoromethyl)phenyl; 4-chloro-3-fluorophenyl;
4-chloro-3-methoxyphenyl; 4-chlorophenyl; 4-cyanophenyl;
4-cyclohexylphenyl; 4-ethoxy-2-methylphenyl;
4-ethoxy-3-fluorophenyl; 4-ethoxyphenyl; 4-ethylphenyl;
4-fluoro-2-(propan-2-yloxy)phenyl; 4-fluoro-2,5-dimethylphenyl;
4-fluoro-2-methoxyphenyl; 4-fluoro-2-methylphenyl;
4-fluoro-3-(2,2,2-trifluoroethoxy)phenyl;
4-fluoro-3-(trifluoromethyl)phenyl;
4-fluoro-3-[(propan-2-yl)carbamoyl]phenyl;
4-fluoro-3-methoxyphenyl; 4-fluoro-3-methylphenyl; 4-fluorophenyl;
4-methanesulfonylphenyl; 4-methoxy-2-(trifluoromethyl)phenyl;
4-methoxy-2,5-dimethylphenyl; 4-methoxy-2-methylphenyl;
4-methoxy-3,5-dimethylphenyl; 4-methoxy-3-methylphenyl;
4-methoxyphenyl; 4-methylphenyl; 4-methylpyridine;
4-methylthiophene; 4-phenylbutane; 4-phenylphenyl; 4-phenyl-phenyl;
4-propoxyphenyl; 3,5-difluorophenyl;
5-(diethylcarbamoyl)-2-fluorophenyl; 5-(dimethylamino)pyrazine;
5-(pyrrolidin-1-yl)pyridine; 5-(trifluoromethyl)pyridine;
5-acetyl-2-methoxyphenyl; 5-chloro-2-(2,2,2-trifluoroethoxy)phenyl;
5-chloro-2-(2,2-difluoroethoxy)phenyl;
5-chloro-2-(prop-2-yn-1-yloxy)phenyl;
5-chloro-2-(propan-2-yloxy)phenyl; 5-chloro-2-ethoxyphenyl;
5-chloro-2-hydroxyphenyl; 5-chloro-2-methoxyphenyl;
5-chloro-2-methylphenyl; 5-chloro-2-propoxyphenyl;
5-chloropyridine; 5-cyano-2-methoxyphenyl;
5-fluoro-2-(hydroxymethyl)phenyl; 5-fluoro-2-methoxyphenyl;
5-fluoro-2-methylphenyl; 5-fluoro-6-methylpyridine;
5-fluoropyridine; 5H,6H,7H,8H,9H-imidazo[1,2-a]azepine;
5H,6H,7H,8H,9H-imidazo[1,2-a]azepinephenyl;
5-hydroxy-(4-phenylphenyl); 5-hydroxy-1-methyl-1H-indazole;
5-hydroxy-2-(trifluoromethoxy)phenyl;
5-hydroxy-3-(morpholin-4-yl)phenyl;
5-hydroxy-3-(piperidin-1-ylphenyl;
5-hydroxy-3-(pyrrolidin-1-ylphenyl; 5-methoxypyridine;
5-methylpyridine; 5-methylthiophene; 5-tert-butyl-2-methoxyphenyl;
6-(1H-pyrazol-1-yl)pyridine; 6-(3,4-difluorophenyl)pyridine;
6-(4-methylpiperazin-1-yl)pyridine; 6-(dimethylamino)pyridine;
6-(morpholin-4-yl)pyridine; 6-(trifluoromethyl)pyridine;
6-amino-(3,5-difluorophenyl); 6-chloro-2-fluoro-3-methylphenyl;
6-chloroimidazo[1,2-a]pyridine;
6-chloroimidazo[1,2-a]pyridinephenyl; 6-methoxynaphthalene;
6-methoxypyridine; 6-methylpyrazine; 6-methylpyridine;
8-thiatricyclo[7.4.0.0.sup.2,7]trideca-1(13),2,4,6,9,11-hexaene;
b6-chloroimidazo[1,2-a]pyridine; Cyclohexane;
dimethyl-1,3-thiazole; furan; isoquinoline; naphthalene;
naphthalenephenyl; phenoxathiine; phenyl; pyridine and
quinoline.
[0506] Another embodiment of the invention is compounds of Formula
IIB, where R.sup.1 is cycloalkyl, aryl or heteroaryl, wherein each
of said cycloalkyl, aryl, or heteroaryl is unsubstituted or
substituted with 1, 2, 3, 4 or 5 substituents which can be the same
or different and are independently selected from the group
consisting of: halo, hydroxy, hydroxyalkyl, cyano, alkyl, alkynyl,
alkynylalkoxy, alkoxyalkyl, alkoxy, haloalkyl, haloalkoxy,
--C(O)NH(alkyl), --C(O)NH(cycloalkyl), --C(O)N(alkyl).sub.2,
arylalkoxy-, aryloxy-, cycloalkyl, heterocycloalkyl, aryl,
(heterocycloalkyl)alkyl-, (heterocycloalkyl)alkoxy-,
--C(O)heterocycloalkyl, heteroaryl, (heteroaryl)alkyl-,
--S(O).sub.2-alkyl, --S-alkyl, --C(O)alkyl, --S(O.sub.2)NH.sub.2,
--S(O.sub.2)NH(alkyl), --S(O.sub.2)N(alkyl).sub.2,
--N(H)(SO.sub.2)(alkyl), wherein each of said cycloalkyl,
heterocycloalkyl, aryl or heteroaryl may be substituted by one or
more halo, cyano, alkyl or alkoxy; and z is 0, 1 or 2.
[0507] Still another embodiment of the invention is compounds of
Formula IIC, where R.sup.1 is cycloalkyl, aryl or heteroaryl,
wherein each of said cycloalkyl, aryl, or heteroaryl is
unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents
which can be the same or different and are independently selected
from the group consisting of: halo, haloalkyl and haloalkoxy.
[0508] Another embodiment of the invention is compounds of Formula
IIB, where haloalkyl is --CH.sub.zF.sub.3-z,
--CH.sub.2CH.sub.zF.sub.3-z, and z is 0, 1 or 2.
[0509] One embodiment of the invention is compounds of Formula IIB,
where haloalkoxy is --OCH.sub.zF.sub.3-z, and z is 0, 1 or 2.
[0510] Another embodiment of the invention is compounds of Formula
IIB, where halo is F.
[0511] Another embodiment of the invention is compounds of Formula
IIB, where R is 1H-pyrazolo[3,4-b]pyridine.
[0512] Another embodiment of the invention is compounds of Formula
IIB, where R is 1,8a-dihydroimidazo[1,2-a]pyridine.
[0513] Anyone or more embodiments of Formula IIB provided above may
be combined with one or more other embodiments of Formula IIB as
provided above.
[0514] In another embodiment, the invention is further illustrated
by the compounds shown in Table 2:
TABLE-US-00002 Lengthy table referenced here
US20140294805A1-20141002-T00001 Please refer to the end of the
specification for access instructions.
EXAMPLES
[0515] The following are illustrative, but non-limiting, examples
of certain embodiments of the present invention.
[0516] The invention is illustrated further by the following
examples, which are not to be construed as limiting the invention
in scope or spirit to the specific procedures described in them.
Those having skill in the art will recognize that the starting
materials may be varied and additional steps employed to produce
compounds encompassed by the present inventions, as demonstrated by
the following examples. In some cases, protection of certain
reactive functionalities may be necessary to achieve some of the
above transformations. In general, such need for protecting groups,
as well as the conditions necessary to attach and remove such
groups, will be apparent to those skilled in the art of organic
synthesis.
[0517] Compounds according to the invention may be synthesized by
synthetic routes that include processes analogous to those
well-known in the chemical arts, particularly in light of the
description contained herein, and those for other heterocycles
described in: Comprehensive Heterocyclic Chemistry II, Editors
Katritzky and Rees, Elsevier, 1997, e.g. Volume 3; Liebigs Annalen
der Chemie, (9):1910-16, (1985); Helvetica Chimica Acta,
41:1052-60, (1958); Arzneimittel-Forschung, 40(12):1328-31, (1990),
each of which are expressly incorporated by reference. Starting
materials are generally available from commercial sources such as
Aldrich Chemicals (Milwaukee, Wis.) or are readily prepared using
methods well known to those skilled in the art (e.g., prepared by
methods generally described in Louis F. Fieser and Mary Fieser,
Reagents for Organic Synthesis, v. 1-23, Wiley, N.Y. (1967-2006
ed.), or Beilsteins Handbuch der organischen Chemie, 4, Aufl. ed.
Springer-Verlag, Berlin, including supplements (also available via
the Beilstein online database).
[0518] Synthetic chemistry transformations and protecting group
methodologies (protection and deprotection) useful in synthesizing
compounds according to the invention and necessary reagents and
intermediates are known in the art and include, for example, those
described in R. Larock, Comprehensive Organic Transformations, VCH
Publishers (1989); T. W. Greene and P. G. M. Wuts, Protective
Groups in Organic Synthesis, 3rd Ed., John Wiley and Sons (1999);
and L. Paquette, ed., Encyclopedia of Reagents for Organic
Synthesis, John Wiley and Sons (1995) and subsequent editions
thereof.
[0519] Compounds according to the invention may be prepared singly
or as compound libraries comprising at least 2, for example 5 to
1,000 compounds, or 10 to 100 compounds. Libraries of compounds of
Formula I may be prepared by a combinatorial `split and mix`
approach or by multiple parallel syntheses using either solution
phase or solid phase chemistry, by procedures known to those
skilled in the art. Thus according to a further aspect of the
invention there is provided a compound library comprising at least
2 compounds, or pharmaceutically acceptable salts thereof.
[0520] The General Procedures and Examples provide exemplary
methods for preparing compounds according to the invention. Those
skilled in the art will appreciate that other synthetic routes may
be used to synthesize the compounds according to the invention.
Although specific starting materials and reagents are depicted and
discussed in the schemes, General Procedures, and Examples, other
starting materials and reagents can be easily substituted to
provide a variety of derivatives and/or reaction conditions. In
addition, many of the exemplary compounds prepared by the described
methods can be further modified in light of this disclosure using
conventional chemistry well known to those skilled in the art.
[0521] In preparing compounds according to the invention,
protection of remote functionality (e.g., primary or secondary
amine) of intermediates may be necessary. The need for such
protection will vary depending on the nature of the remote
functionality and the conditions of the preparation methods.
Suitable amino-protecting groups include acetyl, trifluoroacetyl,
t-butoxycarbonyl (BOC), benzyloxycarbonyl (CBz) and
9-fluorenylmethyleneoxycarbonyl (Fmoc). The need for such
protection is readily determined by one skilled in the art. For a
general description of protecting groups and their use, see T. W.
Greene, Protective Groups in Organic Synthesis, John Wiley &
Sons, New York, 1991.
[0522] In the methods of preparing compounds according to the
invention, it may be advantageous to separate reaction products
from one another and/or from starting materials. The desired
products of each step or series of steps is separated and/or
purified to the desired degree of homogeneity by the techniques
common in the art. Typically such separations involve multiphase
extraction, crystallization from a solvent or solvent mixture,
distillation, sublimation, or chromatography. Chromatography can
involve any number of methods including, for example: reverse-phase
and normal phase; size exclusion; ion exchange; high, medium and
low pressure liquid chromatography methods and apparatus; small
scale analytical; simulated moving bed (SMB) and preparative thin
or thick layer chromatography, as well as techniques of small scale
thin layer and flash chromatography.
[0523] Another class of separation methods involves treatment of a
mixture with a reagent selected to bind to or render otherwise
separable a desired product, unreacted starting material, reaction
by product, or the like. Such reagents include adsorbents or
absorbents such as activated carbon, molecular sieves, ion exchange
media, or the like. Alternatively, the reagents can be acids in the
case of a basic material, bases in the case of an acidic material,
binding reagents such as antibodies, binding proteins, selective
chelators such as crown ethers, liquid/liquid ion extraction
reagents (LIX), or the like. Selection of appropriate methods of
separation depends on the nature of the materials involved, such
as, boiling point and molecular weight in distillation and
sublimation, presence or absence of polar functional groups in
chromatography, stability of materials in acidic and basic media in
multiphase extraction, and the like.
[0524] Diastereomeric mixtures can be separated into their
individual diastereomers on the basis of their physical chemical
differences by methods well known to those skilled in the art, such
as by chromatography and/or fractional crystallization. Enantiomers
can be separated by converting the enantiomeric mixture into a
diastereomeric mixture by reaction with an appropriate optically
active compound (e.g., chiral auxiliary such as a chiral alcohol or
Mosher's acid chloride), separating the diastereomers and
converting (e.g., hydrolyzing) the individual diastereoisomers to
the corresponding pure enantiomers. Also, some of the compounds of
the present invention may be atropisomers (e.g., substituted
biaryls) and are considered as part of this invention. Enantiomers
can also be separated by use of a chiral HPLC column.
[0525] A single stereoisomer, e.g., an enantiomer, substantially
free of its stereoisomer may be obtained by resolution of the
racemic mixture using a method such as formation of diastereomers
using optically active resolving agents (Eliel, E. and Wilen, S.
"Stereochemistry of Organic Compounds," John Wiley & Sons,
Inc., New York, 1994; Lochmuller, C. H., (1975) J. Chromatogr.,
113(3):283-302). Racemic mixtures of chiral compounds of the
invention can be separated and isolated by any suitable method,
including: (1) formation of ionic, diastereomeric salts with chiral
compounds and separation by fractional crystallization or other
methods, (2) formation of diastereomeric compounds with chiral
derivatizing reagents, separation of the diastereomers, and
conversion to the pure stereoisomers, and (3) separation of the
substantially pure or enriched stereoisomers directly under chiral
conditions. See: "Drug Stereochemistry, Analytical Methods and
Pharmacology," Irving W. Wainer, Ed., Marcel Dekker, Inc., New York
(1993).
[0526] Under method (1), diastereomeric salts can be formed by
reaction of enantiomerically pure chiral bases such as brucine,
quinine, ephedrine, strychnine, a-methyl-b-phenylethylamine
(amphetamine), and the like with asymmetric compounds bearing
acidic functionality, such as carboxylic acid and sulfonic acid.
The diastereomeric salts may be induced to separate by fractional
crystallization or ionic chromatography. For separation of the
optical isomers of amino compounds, addition of chiral carboxylic
or sulfonic acids, such as camphorsulfonic acid, tartaric acid,
mandelic acid, or lactic acid can result in formation of the
diastereomeric salts.
[0527] Alternatively, by method (2), the substrate to be resolved
is reacted with one enantiomer of a chiral compound to form a
diastereomeric pair (E. and Wilen, S. "Stereochemistry of Organic
Compounds", John Wiley & Sons, Inc., 1994, p. 322).
Diastereomeric compounds can be formed by reacting asymmetric
compounds with enantiomerically pure chiral derivatizing reagents,
such as menthyl derivatives, followed by separation of the
diastereomers and hydrolysis to yield the pure or enriched
enantiomer. A method of determining optical purity involves making
chiral esters, such as a menthyl ester, e.g., (-) menthyl
chloroformate in the presence of base, or Mosher ester,
a-methoxy-a-(trifluoromethyl)phenyl acetate of the racemic mixture
and analyzing the .sup.1H NMR spectrum for the presence of the two
atropisomeric enantiomers or diastereomers (Jacob III. J. Org.
Chem. (1982) 47:4165). Stable diastereomers of atropisomeric
compounds can be separated and isolated by normal- and
reverse-phase chromatography following methods for separation of
atropisomeric naphthyl-isoquinolines (WO 96/15111). By method (3),
a racemic mixture of two enantiomers can be separated by
chromatography using a chiral stationary phase ("Chiral Liquid
Chromatography" (1989) W. J. Lough, Ed., Chapman and Hall, New
York; Okamoto, J. Chromatogr., (1990) 513:375-378). Enriched or
purified enantiomers can be distinguished by methods used to
distinguish other chiral molecules with asymmetric carbon atoms,
such as optical rotation and circular dichroism.
Definitions used in the following Schemes and elsewhere herein are:
[0528] BOP ammonium 4-(3-(pyridin-3-methyl)ureido)benzenesulfinate
[0529] CDCl.sub.3 deuterated chloroform [0530] .delta. chemical
shift (ppm) [0531] DCM dichloromethane or methylene chloride [0532]
DIEA N,N-diisopropylethylamine [0533] DMA N,N-dimethylacetamide
[0534] DMF N,N-dimethylformamide [0535] DMSO dimethylsulfoxide
[0536] DMSO-d.sub.6 deuterated dimethylsulfoxide [0537] EDCI
N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine
hydrochloride [0538] EtOAc ethyl acetate [0539] EtOH ethanol [0540]
GF/F glass microfiber filter [0541] .sup.1H NMR proton nuclear
magnetic resonance [0542] HOAc acetic acid [0543] HATU
2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium
hexafluorophosphate [0544] HOBT 1H-benzo[d][1,2,3]triazol-1-ol
hydrate [0545] HPLC high pressure liquid chromatography [0546] MHz
megahertz [0547] KOAc potassium acetate [0548] i-PrOH isopropanol
[0549] LC-MS liquid chromatography/mass spectrometry [0550] (M+1)
mass+1 [0551] m-CPBA m-chloroperbenzoic acid [0552] MeOH methanol
[0553] N.sub.2 nitrogen [0554] NaHCO.sub.3 sodium bicarbonate
[0555] MgSO.sub.4 magnesium sulfate [0556] PTLC preparative thin
layer chromatography [0557] TEA triethylamine [0558] THF
tetrahydrofuran [0559] TLC thin layer chromatography
Amide-Sulfonamide:
##STR00053##
[0561] In Scheme 1, compound III can be obtained by treating II
with I (G=OH) in the presence of a coupling reagent such as EDCI,
HATU, or HOBt, and a base (e.g.: K.sub.2CO.sub.3, Cs.sub.2CO.sub.3,
NR.sub.1R.sub.2R.sub.3, NaOR, KOR) in an inert solvent such as
dichloromethane, N,N-dialkylformamide, N,N-dialkylacetamide,
dialkylethers, cyclic ethers, DMSO, N-methyl-2-pyrrolidinone at
temperatures ranging from -78.degree. C. to 200.degree. C.
Alternatively, compound I can be treated with I (G=OR) in the
presence of trimethylaluminum in an inert solvent (such as toluene)
at temperatures ranging from -78.degree. C. to 200.degree. C.
[0562] Those having skill in the art will recognize that the
starting materials may be varied and additional steps employed to
produce compounds encompassed by the present inventions, as
demonstrated by the following examples. Unless otherwise specified,
all reagents and solvents were of standard commercial grade and
were used without further purification.
[0563] Amide Sulfone:
##STR00054##
Compound III of scheme 2 can be obtained by treating II with I
(G=OH) in the presence of a coupling reagent such as EDCI, HATU,
BOP, or HOBt, and a base (eg: K.sub.2CO.sub.3, Cs.sub.2CO.sub.3,
NR.sub.1R.sub.2R.sub.3, NaOR, KOR) in an inert solvent such as
dichloromethane, N,N-dialkylformamide, N,N-dialkylacetamide,
dialkylethers, DMSO, or N-methyl-2-pyrrolidinone at temperatures
ranging from -78.degree. C. to 200.degree. C. Alternatively,
compound III can be obtained by treating I (G=OR) with I and
trimethylaluminum in an inert solvent (such as toluene) at
temperatures ranging from -78.degree. C. to 200.degree. C.
[0564] Those having skill in the art will recognize that the
starting materials may be varied and additional steps employed to
produce compounds encompassed by the present inventions, as
demonstrated by the following examples. Unless otherwise specified
all reagents and solvent are of standard commercial grade and are
used without further purification.
##STR00055##
[0565] In Scheme 3, the compound of III present invention can also
be synthesized by following the steps outlined in Scheme IV.
Treating II with IV in the presence of a coupling reagent such as
EDCI, HATU, BOP, or HOBt, and a base (eg: K.sub.2CO.sub.3,
Cs.sub.2CO.sub.3, NR.sub.1R.sub.2R.sub.3, NaOR, KOR) in an inert
solvent such as dichloromethane, N,N-dialkylformamide,
N,N-dialkylacetamide, dialkylethers, DMSO, or
N-methyl-2-pyrrolidinone at temperatures ranging from -78.degree.
C. to 200.degree. C. gives compound V. Compound V can be treated
with a base such as sodium ethoxide in the present of a protonated
solvent such as ethanol to afford compound VI. Treating compound VI
with arylboronic acid or aryl halogens facilitated by palladium or
copper to obtain the target compound III.
Example 1
Preparation of Representative Amide-Sulfonamide Analogues
[0566] These examples illustrate the preparation of representative
substituted amide-sulfonamide analogues.
Example 1A
N-(4-(N-(2-(trifluoromethoxy)phenyl)sulfamoyl)benzyl)-1H-pyrrolo[3,2-c]pyr-
idine-2-carboxamide
##STR00056##
[0567] A:
4-cyano-N-(2-(trifluoromethoxy)phenyl)benzenesulfonamide
##STR00057##
[0569] 2-(Trifluoromethoxy)aniline (10.902 g, 58.5 mmol) was
dissolved in pyridine (100 mL) and cooled to 0.degree. C. A
solution of 4-cyanobenzene-1-sulfonyl chloride (11.573 g, 55.7
mmol) was added in pyridine (100 mL) over 10 minutes via addition
funnel. The mixture was heated to 85.degree. C. for 16 hours and
the pyridine was removed under reduced pressure. The residue was
diluted with DCM and washed with 1M HCl (.times.2), water
(.times.1), brine (.times.1), and saturated NaHCO.sub.3 (.times.1).
The organic layer was dried over anhydrous MgSO.sub.4, filtered,
concentrated, and purified by Biotage SP1 (hexanes/DCM) to afford
the title compound as a white solid.
[0570] .sup.1H NMR (300 HMz; DMSO-d.sub.6): .delta. 10.58 (s, 1H),
8.06 (d, 2H), 7.89 (d, 2H), 7.30 (s, 4H).
B:
4-(aminomethyl)-N-(2-(trifluoromethoxy)phenyl)benzenesulfonamide
##STR00058##
[0572] 4-Cyano-N-(2-(trifluoromethoxy)phenyl)benzenesulfonamide
(2.0 g, 5.84 mmol) was dissolved in THF (30 mL) and borane
tetrahydrofuran complex (14.61 mL of a 1M solution in THF) was
added. The mixture was heated to 70.degree. C. for 2 hours, then
cooled to room temperature followed by the addition of MeOH (10
mL). The mixture was briefly warmed to 70.degree. C. for 15
minutes, then the volatiles removed under reduced pressure and
EtOAc (100 mL) and 1N NaOH (50 mL) were added to the residue. The
layers were separated, and the organic layer washed with water and
brine. The combined aqueous washes were extracted with EtOAc,
combined with the previous organic extracts, and dried over
MgSO.sub.4. The residue was purified by Biotage SP1
(MeOH/DCM/NH.sub.3 gradient) to afford the title compound as a pale
yellow solid.
[0573] .sup.1H NMR (300 HMz; DMSO-d.sub.6): .delta. 7.70 (d, 2H),
7.41 (d, 2H), 7.19 (d, 1H), 7.00 (d, 1H), 6.89 (t, 1H), 6.58 (t,
1H), 3.84 (s, 2H).
C:
N-(4-(N-(2-(trifluoromethoxy)phenyl)sulfamoyl)benzyl)-1H-pyrrolo[3,2-c]-
pyridine-2-carboxamide
##STR00059##
[0575] A mixture of 1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid
(478 mg, 2.95 mmol),
4-(aminomethyl)-N-(2-(trifluoromethoxy)phenyl)benzenesulfonamide
(973 mg, 2.81 mmol), HATU (1.122 g, 2.95 mmol), DIEA (1.082 mL,
6.20 mmol), and DMF (15 mL) at 25.degree. C. were stirred for 16
hours at ambient temperature. The mixture was diluted with EtOAc
and washed successively with saturated NaHCO.sub.3 and brine. The
organic extracts were separated and dried over MgSO.sub.4,
filtered, concentrated, and purified by Biotage SP1 (DCM/MeOH
gradient). The combined fractions were triturated with Et.sub.2O to
afford the product as a white solid.
[0576] .sup.1H NMR (300 HMz; DMSO-d.sub.6): .delta. 12.10 (br s,
1H), 9.23 (t, 1H), 8.98 (s, 1H), 8.21 (d, 1H), 7.78 (d, 2H), 7.47
(d, 2H), 7.38 (d, 1H), 7.31-7.19 (m, 6H), 4.58 (d, 2H). LC-MS:
491.11 (M+1).
Example 1B
N-(4-(piperidin-1-ylsulfonyl)benzyl)thieno[3,2-c]pyridine-2-carboxamide
##STR00060##
[0578] (4-(Piperidin-1-ylsulfonyl)phenyl)methanamine (155 mg, 0.609
mmol) and trimethylaluminum (0.30 mL, 0.600 mmol) were combined in
toluene (2 mL) and stirred for 30 minutes at ambient temperature. A
solution of methyl thieno[3,2-c]pyridine-2-carboxylate (100 mg,
0.518 mmol, prepared according to WO 2004/064836) in toluene (2 mL)
was then added and the mixture heated to 110.degree. C. for 16
hours. Upon cooling, a saturated solution of potassium sodium
tartrate and EtOAc were added and the mixture stirred vigorously
for 30 minutes and then filtered. The layers were separated, the
organics dried over MgSO.sub.4, and purified by Biotage SP1 (100%
EtOAc) to afford the title compound as white foam.
[0579] .sup.1H NMR (300 HMz; CDCl.sub.3): .delta. 9.13 (s, 1H),
8.50 (d, 1H), 7.93 (s, 1H), 7.79 (t, 1H), 7.67 (d, 1H), 7.48 (d,
2H), 7.36 (d, 2H), 4.69 (d, 2H), 2.89 (t, 4H), 1.63-1.55 (m, 4H),
1.42-1.34 (m, 2H) LC-MS: 416.11 (M+1).
Example IC
N-(4-(N-(2,5-dimethoxyphenyl)sulfamoyl)benzyl)-1H-pyrrolo[3,2-c]pyridine-2-
-carboxamide
##STR00061##
[0580] A:
N-(4-(N-(2,5-dimethoxyphenyl)sulfamoyl)benzyl)acetamide
##STR00062##
[0582] A mixture of 4-(acetamidomethyl)benzene-1-sulfonyl chloride
(25 mg, 0.1 mmol), 2,5-dimethoxyaniline (15.3 mg, 0.1 mmol), and
pyridine (0.25 mL) in DMA (1 mL) were heated at 50.degree. C. for
16 hours before being concentrated under reduced pressure. The
residue was purified by PTLC (100% EtOAc) to afford the title
compound as white solid.
[0583] .sup.1H NMR (400 HMz; CDCl.sub.3): .delta. 7.73 (d, J=8 Hz,
2H), 7.30 (d, J=8 Hz, 2H), 7.14 (d, J=3.2 Hz, 1H), 7.05 (s, 1H),
6.66 (d, J=8.8 Hz, 1H), 6.54 (dd, J=8.8 Hz, J'=3.2 Hz, 1H), 5.95
(br s, 1H), 4.46 (d, J=6 Hz, 2H), 3.74 (s, 3H), 3.61 (s, 3H), 2.07
(s, 3H). LC-MS: 364.99 (M+1).
B: (4-(N-(2,5-dimethoxyphenyl)sulfamoyl)phenyl)methanaminium
chloride
##STR00063##
[0585] A mixture of
N-(4-(N-(2,5-dimethoxyphenyl)sulfamoyl)benzyl)acetamide (28 mg,
0.077 mmol) and 3N HCl (0.5 mL, 1.5 mmol) in 70% i-PrOH (0.5 mL)
was heated at 100.degree. C. for 5 hours. The mixture was
concentrated to dryness in vacuo to afford the title compound as
off-white solid.
[0586] .sup.1H NMR (400 HMz; CDCl.sub.3): .delta. 7.84 (d, J=8.4
Hz, 2H), 7.56 (d, J=8.8 Hz, 2H), 7.04 (d, J=2.8 Hz, 1H), 6.74 (d,
J=9.2 Hz, 1H), 6.60 (dd, J=9.2 Hz, J'=3.2 Hz, 1H), 5.95 (br s, 1H),
4.16 (s, 2H), 3.70 (s, 3H), 3.54 (s, 3H). LC-MS: 323.03 (M+1)
C:
N-(4-(N-(2,5-dimethoxyphenyl)sulfamoyl)benzyl)-1H-pyrrolo[3,2-c]pyridin-
e-2-carboxamide
##STR00064##
[0588] The title compound was prepared following Example 1C,
substituting BOP in place of HATU, and
4-(aminomethyl)-N-(2,5-dimethoxyphenyl)benzenesulfonamide in place
of
4-(aminomethyl)-N-(2-(trifluoromethoxy)phenyl)benzenesulfonamide.
The product was purified by PTLC.
[0589] .sup.1H NMR (400 HMz; CD.sub.3OD): .delta. 8.90 (d, J=0.8
Hz, 1H), 8.22 (d, J=5.6 Hz, 1H), 7.71 (d, J=8.4 Hz, 2H), 7.51 (d,
J=6 Hz, 1H), 7.45 (d, J=8.8 Hz, 2H), 7.28 (d, J=0.8 Hz, 1H), 7.02
(d, J=3.2 Hz, 1H), 6.70 (d, J=9.2 Hz, 1H), 6.59 (dd, J=8.8 Hz,
J'=3.2 Hz, 1H), 4.62 (s, 2H), 3.69 (s, 3H), 3.46 (s, 3H). LC-MS:
466.98 (M+1).
Example 2
Preparation of Representative Amide-Sulfone Analogues
[0590] These examples illustrate the preparation of representative
substituted amide-sulfonamide analogues.
Example 2A
N-(4-(phenylsulfonyl)benzyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
##STR00065##
[0591] a: 4-(phenylsulfonyl)benzonitrile
##STR00066##
[0593] A mixture of 4-fluorobenzonitrile (5 g, 41.3 mmol) and
sodium benzenesulfinate (7.45 g, 45.4 mmol) in DMSO (30 mL) was
heated at 130.degree. C. for 16 hours. The mixture was cooled to
room temperature and poured onto 300 g of ice. The precipitate was
collected, washed with water, and dried to afford the title
compound.
[0594] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 8.03-8.07 (m,
2H), 7.93-7.97 (m, 2H), 7.78-7.82 (m, 2H), 7.60 (m 7.65, 1H),
7.26-7.58 (m, 2H)
b: (4-[phenylsulfonyl]phenyl)methanamine
##STR00067##
[0596] A mixture of 4-(phenylsulfonyl)benzonitrile (9.4 g, 38.64
mmol) and Raney Ni (500 mg) in 2N NH.sub.3-MeOH (150 mL) was
hydrogenated for 16 hours at 50 psi. Nitrogen gas was bubbled
through the mixture, which was then filtered through a short Celite
pad, and washed with methanol. The filtrate was concentrated and
triturated with ether to afford the title compound.
[0597] .sup.1H NMR (300 MHz, DMSO-d.sub.6): .delta. 7.85-7.95 (m,
4H), 7.53-7.68 (m, 5H), 3.74 (s, 2H), 1.83 (br s, 2H)
c:
N-(4-(phenylsulfonyl)benzyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
##STR00068##
[0599] A mixture of 1H-pyrrolo[3,2-2]pyridine-2-carboxylic acid
(1.0 g, 6.17 mmol), HATU (3.52 g, 9.25 mmol), diisopropylethylamine
(2.69 mL, 15.42 mmol), and (4-(phenylsulfonyl)phenyl)methanamine
(1.754 g, 7.09 mmol) in DMF (70 mL) was stirred at room temperature
for 16 hours. The solvent was removed under reduced pressure, water
(200 mL) was added, and the mixture was extracted with EtOAc
(3.times.300 mL). The combined organic layers were successively
washed with water, saturated sodium bicarbonate, and brine. The
extracts were dried with sodium sulfate, concentrated in vacuo, and
purified by Biotage with MeOH/DCM (0%-10%) to afford the title
compound.
[0600] .sup.1H NMR (300 MHz, DMSO-d.sub.6) .delta. 4.56 (d, J=5.57
Hz, 2H), 7.29 (s, 1H), 7.34 (d, J=5.57 Hz, 1H), 7.56-7.66 (m, 5H),
7.91-7.94 (m, 4H), 8.20 (d, J=5.87 Hz, 1H), 8.91 (s, 1H),
9.245-9.28 (m, 1H). 12.03 (s, 1H) LC-MS: 392.13 (M+1).
Example 2B
3-bromo-N-(4-(phenylsulfonyl)benzyl)-!H-Pyrrolo[3,2-c]pyridine-2-carboxami-
de
##STR00069##
[0602] A mixture of
N-(4-(phenylsulfonyl)benzyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
(from Example 1; 200 mg, 0.511 mmol) and
1-bromopyrrolidine-2,5-dione (91 mg, 0.511 mmol) in DMF (10 mL) was
stirred at room temperature for 16 hours. EtOAc (100 mL) was added
to the mixture. The organic layer was washed with water and brine,
dried with sodium sulfate, and concentrated in vacuo. The crude was
purified by Biotage with MeOH/DCM (0%-10%) to afford the title
compound.
[0603] .sup.1H NMR (300 MHz, DMSO-d.sub.6): .delta. 12.42 (br s,
1H), 8.78 (m, 2H), 8.30 (d, 1H), 7.93 (d, 4H), 7.59-7.69 (m, 5H),
7.38 (dd, 1H), 4.59 (d, 2H) LC-MS: 470.06 (M+1).
Example 2C
N-({4-[(4-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-car-
boxamide
##STR00070##
[0604] a: 4-(4-fluorophenylsulfonyl)benzonitrile
##STR00071##
[0606] The title compound was prepared following Example 1A,
substituting sodium 4-fluorobenzenesulfinate for sodium
benzenesulfinate.
[0607] .sup.1H NMR (300 MHz, DMSO-D.sub.6) .delta.: 8.10-8.18 (m,
6H), 7.42-7.12 (t, 2H).
b: (4-[4-fluorophenylsulfonyl]phenyl)methanamine
##STR00072##
[0609] The title compound was prepared following Example 1B,
substituting 4-(4-fluorophenylsulfonyl)benzonitrile for
4-(phenylsulfonyl)benzonitrile.
[0610] .sup.1H NMR (300 MHz, (DMSO-d.sub.6): .delta. 7.8-7.96 (m,
4H), 3.74 (s, 2H), 7.42-7.64 (m, 4H), 3.64 (m, 2H).
c:
N-({4-[(4-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2--
carboxamide
##STR00073##
[0612] (4-(4-Fluorophenylsulfonyl)phenyl)methanamine hydrochloride
(1409 mg, 4.67 mmol) was mixed with toluene (20 mL) and cooled to
0.degree. C. Trimethylaluminum (7.00 mL of a 2M solution in
toluene) was added and the mixture was stirred for 40 minutes at
ambient temperature. A solution of methyl
thieno[2,3-c]pyridine-2-carboxylate (820 mg, 4.24 mmol, prepared
according to WO 2004/064836) in toluene (10 mL) was added via
syringe, and the mixture was heated to 80.degree. C. for 4 hours.
The mixture was diluted with saturated potassium sodium tartrate
(25 mL) and EtOAc (25 mL), stirred vigorously for 1 hour, and then
filtered through GF/F paper. The organic layer was separated, dried
over MgSO.sub.4, filtered, and concentrated to a yellow solid. The
residue was triturated with DCM and the title compound was
collected by vacuum filtration.
[0613] .sup.1H NMR (300 MHz, DMSO-d.sub.6) .delta. 9.59 (t, 1H),
9.30 (s, 1H), 9.50 (d, 1H), 8.15 (s, 1H), 8.04-7.98 (m, 2H),
7.96-7.90 (m, 3H), 7.56 (d, 2H), 7.47-7.40 (m, 2H), 4.55 (d,
2H)
[0614] LC-MS: 427.03 (M+1).
Example 2D
N-(4-(phenylsulfonyl)benzyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
##STR00074##
[0615] a: sodium 4-(acetamidomethyl)benzenesulfinate
##STR00075##
[0617] 4-(Acetamidomethyl)benzene-1-sulfonyl chloride (1.24 g, 5
mmol) was added to a water-cooled solution of Na.sub.2SO.sub.3
(1.89 g, 15 mmol) in water (3.75 mL) then solid NaHCO.sub.3 (850
mg, 10 mmol) was added in several small portions to keep the pH
slightly basic. The mixture was stirred at ambient temperature for
2 hours, affording a thick white suspension. Brine (2 ml) was added
and the mixture was stirred at ambient temperature for 15 minutes.
The precipitate was collected by filtration and dried overnight
under vacuum. The solid was ground up and stirred with 125 ml of
MeOH for 30 min then the solid was filtered off, washing with MeOH
(20 mL). The filtrate was concentrated to give the title compound
as a white solid.
[0618] .sup.1H NMR (400 MHz, CD.sub.3OD): .delta. 7.61 (d, J=8.4
Hz, 2H), 7.34 (d, J=8.4 Hz, 2H), 4.38 (s, 2H), 1.98 (s, 3H).
b: N-(4-(benzo[d][1,3]-dioxol-5-ylsulfonyl)benzyl)acetamide
##STR00076##
[0620] A mixture of sodium 4-(acetamidomethyl)benzenesulfinate
(23.5 mg, 0.1 mmol), benzo[d][1,3]dioxol-5-ylboronic acid (20.7 mg,
0.125 mmol), copper(II) acetate (22.7 mg, 0.125 mmol), and TEA
(0.063 mL, 0.45 mmol) in DMSO (1.5 mL) was heated at 60.degree. C.
for 16 hours. The mixture was cooled to room temperature and
partitioned between EtOAc-brine. The organic layer was separated
and concentrated in vacuo. The crude was purified by PTLC (100%
EtOAc) to afford the title compound as white solid.
[0621] .sup.1H NMR (400 MHz, CDCl.sub.3): .delta. 7.85 (d, J=8 Hz,
2H), 7.52 (dd, J=8 Hz, J'=1.6 Hz, 1H), 7.39 (d, J=8.4 Hz, 2H), 7.29
(d, J=2 Hz, 1H), 6.87 (d, J=8 Hz, 1H), 6.05 (s, 2H), 5.87 (br s,
1H), 4.47 (d, J=6.4 Hz, 2H), 2.04 (s, 3H).
[0622] LC-MS: 333.97 (M+1)
c: (4-(benzo[d][1,3]dioxol-5-ylsulfonyl)phenyl)methanamine
hydrochloride
##STR00077##
[0624] A mixture of
N-(4-(benzo[d][1,3]dioxol-5-ylsulfonyl)benzyl)acetamide (10 mg,
0.03 mmol) and 3N HCl (0.36 mL, 1.08 mmol) in 70% i-PrOH (0.2 mL)
was heated at 100.degree. C. for 5 hours. The mixture was
concentrated to dryness to afford the title compound as off-white
solid.
[0625] .sup.1H NMR (400 MHz, CD.sub.3OD): .delta. 8.00 (d, J=8.4
Hz, 2H), 7.64 (d, J=8.4 Hz, 2H), 7.55 (dd, J=8.4 Hz, J'=2 Hz, 1H),
7.34 (d, J=2.4 Hz, 1H), 6.98 (d, J=8 Hz, 1H), 6.08 (s, 2H), 4.19
(s, 2H).
[0626] LC-MS: 219.99 (M+1)
d:
N-(4-(phenylsulfonyl)benzyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
##STR00078##
[0628] The title compound was prepared following Example 1C,
substituting
(4-(benzo[d][1,3]dioxol-5-ylsulfonyl)phenyl)methanamine
hydrochloride for (4-(phenylsulfonyl)phenyl)methanamine, and
substituting BOP instead of HATU. The title compound was purified
by PTLC.
[0629] .sup.1H NMR (400 MHz, CD.sub.3OD): .delta. 9.05 (s, 1H),
8.29 (d, J=6 Hz, 1H), 7.90 (d, J=8.4 Hz, 2H), 7.68 (d, J=6 Hz, 1H),
7.57 (d, J=8 Hz, 2H), 7.52 (dd, J=8 Hz, J'=2 Hz, 1H), 7.42 (s, 1H),
7.31 (d, J=2 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 6.06 (s, 2H), 4.66
(s, 2H) LC-MS: 435.97 (M+1).
Example 2E
1-methyl-N-(4-(phenylsulfonyl)benzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxa-
mide
##STR00079##
[0631] Iodomethane (33.5 .mu.l, 0.535 mmol) was added to a mixture
of
N-(4-(phenylsulfonyl)benzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
(Example 12; 100 mg, 0.255 mmol) and potassium carbonate (106 mg,
0.764 mmol) in DMF (1 mL) at room temperature. The reaction mixture
was heated to 60.degree. C. for 16 hours, whereupon the mixture was
diluted with EtOAc and washed with brine (.times.3). The organic
layer was dried over Na.sub.2SO.sub.4 and concentrated in vacuo.
The residue was dissolved in DMSO (2 mL) and purified via HPLC to
afford the title compound.
[0632] .sup.1H NMR (DMSO-d.sub.6): .delta. 9.31 (t, 1H), 9.02 (d,
1H), 8.72 (d, 1H), 8.28 (s, 1H), 7.94-7.90 (m, 4H), 7.66-7.55 (m,
5H), 4.56 (d, 2H), 4.07 (s, 3H). LC-MS: 407.07 (M+1).
Example 2F
1-methyl-N-(4-(phenylsulfonyl)benzyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxam-
ide
##STR00080##
[0633] a: methyl
1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylate
##STR00081##
[0635] Sodium hydride (48 mg (60%), 1.226 mmol) was added to a
ice-cold solution of 1H-pyrrolo[3,2-c]pyridine-2-carboxylate 9180
mg, 1.022 mmol) in THF (3 mL). The mixture was then warmed to room
temperature over 10 minutes. Iodomethane (0.070 mL, 1.124 mmol) was
added and the mixture stirred for 16 hours. The mixture was
partitioned between EtOAc and water. The combined organic layers
were dried over MgSO.sub.4, filtered, and concentrated to dryness.
The residue was purified by Biotage to afford the title
compound.
[0636] .sup.1H NMR (CDCl.sub.3): .delta. 8.90 (s, 1H), 8.35 (d,
1H), 7.92 (s, 1H), 7.20 (d, 1H), 3.95 (s, 3H), 3.82 (s, 3H).
b:
1-methyl-N-(4-(phenylsulfonyl)benzyl)-1H-pyrrolo[3,2-c]pyridine-2-carbo-
xamide
##STR00082##
[0638] The title compound was prepared following Example 3C,
substituting methyl
1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylate and
(4-(phenylsulfonyl)phenyl)methanamine for methyl
thieno[2,3-c]pyridine-2-carboxylate and
(4-(4-fluorophenylsulfonyl)phenyl)methanamine, respectively. The
title compound was purified by PTLC.
[0639] .sup.1H NMR (DMSO-D.sub.6): .delta. 9.27 (t, 1H), 8.91 (s,
1H), 8.28 (d, 1H), 7.92-7.95 (m, 4H). 7.53-7.67 (m, 6H), 7.27 (s,
1H), 4.52 (d, 2H), 3.95 (s, 3H). LC-MS: 406.01 (M+1).
Example 2G
N-(4-(phenylsulfonyl)benzyl)-1H-imidazo[4,5-c]pyridine-2-carboxamide
##STR00083##
[0640] a: methyl 1H-imidazo[4,5-c]pyridine-2-carboxylate
##STR00084##
[0642] Methyl 2,2-dichloro-2-methoxyacetate (1.585 g, 9.16 mmol)
was added to a solution of pyridine-3,4-diamine (0.5 g, 4.58 mmol)
and DIEA (4.80 mL, 27.5 mmol) in DCM (20 mL). The mixture was
stirred at room temperature for 16 hours, whereupon EtOAc was added
and the mixture washed with saturated sodium bicarbonate and brine.
The organic layer was dried over MgSO.sub.4, filtered,
concentrated, and purified by Biotage to afford the title
compound.
[0643] .sup.1H NMR (CD.sub.3OD): .delta. 8.71 (s, 1H), 8.32 (d,
1H), 7.22 (d, 1H), 4.09 (s, 3H).
b:
N-(4-(phenylsulfonyl)benzyl)-1H-imidazo[4,5-c]pyridine-2-carboxamide
##STR00085##
[0644] The title compound was prepared following Example 3C,
substituting methyl 1H-imidazo[4,5-c]pyridine-2-carboxylate and
(4-(phenylsulfonyl)phenyl)methanamine for methyl
thieno[2,3-c]pyridine-2-carboxylate and
(4-(4-fluorophenylsulfonyl)phenyl)methanamine, respectively. The
title compound was purified by PTLC. .sup.1H NMR (CD.sub.3OD):
.delta. 8.32 (s, 1H), 8.16 (d, 1H), 7.89-7.93 (m, 4H), 7.51-7.64
(m, 5H), 7.30 (d, 1H), 4.81 (s, 2H).
[0645] LC-MS: 393.02 (M+1).
Example 2H
N-(4-((3-chloro-5-fluorophenyl)sulfonyl)benzyl)furo[2,3-c]pyridine-2-carbo-
xamide
##STR00086##
[0646] a: ethyl furo[2,3-c]pyridine-2-carboxylate
##STR00087##
[0647] To a solution of ethyl
3-(trifluoromethylsulfonyloxy)furo[2,3-c]pyridine-2-carboxylate
(524 mg, 1.545 mmol, prepared according to US 20070049603) in
ethanol (15 mL) was added 10% Pd/C (50 mg) and triethylamine (0.5
mL, 3.59 mmol). The mixture was placed under an atmosphere of
hydrogen (balloon) and stirred for 16 hours. The mixture was
filtered, concentrated, and purified by silica gel chromatography
to afford the title compound as an off-white solid (278 mg,
94%).
[0648] .sup.1H NMR (CDCl.sub.3): .delta. 9.03 (s, 1H), 8.51 (d,
1H), 7.63 (dd, 1H), 7.52 (d, 1H), 4.48 (q, 2H), 1.45 (t, 3H).
[0649] MS (ESI): 192.01 (M+H).
b: furo[2,3-c]pyridine-2-carboxylic acid
##STR00088##
[0650] To a solution of ethyl furo[2,3-c]pyridine-2-carboxylate
(3.82 g, 19.98 mmol) in water:THF:MeOH (1:1:1, 60 mL) was added
potassium hydroxide (3.36 g, 59.9 mmol) and the resulting mixture
was stirred at ambient temperature for 16 hours. The solvent volume
was then reduced to .about.20 mL and acetic acid was added until pH
.about.4. The solids were collected by vacuum filtration, washed
twice with water, and dried in a vacuum oven overnight to afford
the title compound (2.90 g, 89%).
[0651] .sup.1H NMR (DMSO-d.sub.6): .delta. 9.09 (s, 1H), 8.47 (d,
1H), 7.81 (dd, 1H), 7.71 (d, 1H), 3.36 (br s, 1H).
c:
N-(4-((3-chloro-5-fluorophenyl)sulfonyl)benzyl)furo[2,3-c]pyridine-2-ca-
rboxamide
##STR00089##
[0652] To a mixture of furo[2,3-c]pyridine-2-carboxylic acid (243
mg, 1.487 mmol),
(4-(3-chloro-5-fluorophenylsulfonyl)phenyl)methanamine
hydrochloride (500 mg, 1.487 mmol), and
(benzotriazol-1-yloxy)tris(dimethylamino)phosphonium
hexafluorophosphate (724 mg, 1.636 mmol) in DMF (8 mL) was added
N,N-diisopropylethylamine (0.571 mL, 3.27 mmol). The homogeneous
reaction mixture was stirred for 16 hours at ambient temperature,
then the DMF was removed under reduced pressure. The residue was
treated with EtOAc (10 mL) and 1N NaOH (5 mL) and the mixture was
stirred vigorously until a precipitate emerged. The solids were
collected by vacuum filtration, rinsing with water and EtOAc, to
afford the title compound (440 mg, 67%).
[0653] .sup.1H NMR (DMSO-d.sub.6): .delta. 9.62 (t, 1H), 9.03 (s,
1H), 8.46 (d, 1H), 8.02 (dt, 2H), 7.87-7.80 (m, 4H), 7.62 (d, 1H),
7.58 (d, 2H), 4.56 (d, 2H).
[0654] MS (ESI): 444.82 (M+H).
Example 2I
N-(4-(4-(ethylcarbamoyl)phenylsulfonyl)benzyl)imidazo[1,2-a]pyridine-6-car-
boxamide
##STR00090##
[0655] a. 4-((4-cyanophenylthio)benzoic acid
##STR00091##
[0656] In a 250 mL round-bottomed flask was added
4-fluorobenzonitrile (2.121 g, 17.51 mmol), 4-mercaptobenzoic acid
(3 g, 17.51 mmol), and potassium carbonate (7.26 g, 52.5 mmol) in
DMF (Volume: 50 mL). The reaction was heated to 100.degree. C.
overnight and monitored by LCMS. When complete, the slurry was
treated with 100 mL of water to give a clear solution. The solution
was then treated with 6M aq. HCl slowly until pH<4 upon which a
precipitate formed. The slurry was filtered and washed with water
to give 14.8 g of crude product after drying briefly on filter. NMR
showed product, an impurity and water. Dried in vacuum oven
overnight to give 4.41 g of material which was adsorbed onto 50 g
of silica gel and then plug filtered with 10% MeOH/CH.sub.2Cl.sub.2
to give 3.45 g of material which was used without further
purification.
[0657] .sup.1H NMR (300 MHz, DMSO-d6): .delta. 13.18 (br s, 1H),
7.96 (d, 2H), 7.80 (d, 2H), 7.52 (d, 2H), 7.42 (d, 2H).
b. 4-(4-cyanophenylthio)-N-ethylbenzamide
##STR00092##
[0658] In a 500 mL round-bottomed flask was added
4-(4-cyanophenylthio)benzoic acid (3.45 g, 13.51 mmol), HBTU (5.13
g, 13.51 mmol) and HOBT (2.070 g, 13.51 mmol) in DMF (Volume: 100
mL) followed by ethanamine (2M in THF, 20.27 mL, 40.5 mmol). The
reaction was stirred overnight and then concentrated under reduced
pressure. The residue was dissolved in ethyl acetate and washed
with 2M aq. NaOH, water and brine. The organic layer was separated,
dried with anhydrous sodium sulfate, filtered and concentrated to
give 2.81 g of product. Material used without further
purification.
[0659] .sup.1H NMR (300 MHz, DMSO-d6): .delta. 8.57 (t, 1H), 7.89
(d, 2H), 7.75 (d, 2H), 7.55 (d, 2H), 7.31 (d, 2H), 3.30 (m, 2H),
1.10 (t, 3H).
c. 4-(4-cyanophenylsulfonyl)-N-ethylbenzamide
##STR00093##
[0660] In a 500 mL round-bottomed flask was added
4-(4-cyanophenylthio)-N-ethylbenzamide (2.81 g, 9.95 mmol) in
chloroform (Volume: 50 mL) which was cooled to 0.degree. C.
followed by the addition of mCPBA (6.87 g, 29.9 mmol). The reaction
was stirred for 1 hour at 0.degree. C. and then warmed to room
temperature overnight. The reaction was diluted with chloroform and
poured into a separatory funnel. The organic layer was washed with
10% aqueous sodium thiolsulfate, 2M NaOH, and saturated, aqueous
sodium chloride. The bottom was separated, dried with anhydrous
sodium sulfate, filtered and concentrated under reduced pressure to
give 2.79 g of crude product. Material purified on Biotage to give
2.42 g of pure product (70% yield).
[0661] .sup.1H NMR (300 MHz, DMSO-d6): .delta. 8.68 (t, 1H), 8.15
(d, 2H), 8.09 (m, 4H), 7.95 (d, 2H), 3.28 (m, 2H), 1.02 (t,
3H).
[0662] LC-MS (ESI): 314.92 (M+1).
d. 4-(4-(aminomethyl)phenylsulfonyl)-N-ethylbenzamide
##STR00094##
[0663] A slurry of Raney Nickel (0.660 g, 7.70 mmol) was added to a
Paar flask and washed with methanol. The MeOH was removed by
pipette and the process repeated twice more.
4-(4-cyanophenylsulfonyl)-N-ethylbenzamide (2.42 g, 7.70 mmol) in
MeOH (Volume: 50 mL)) was then added followed by potassium
hydroxide (0.043 g, 0.770 mmol) and ammonia (7M, 11.00 mL, 77 mmol)
in MeOH. The slurry was placed on the Paar shaker and hydrogenated
at 35 psi overnight. Reaction monitored by LCMS. The solution was
then filtered through celite and washed with MeOH. The solution was
then concentrated under reduced pressure to give 2.56 g of product.
Material purified on Biotage to give 2.03 g of product (83%
yield).
[0664] .sup.1H NMR (300 MHz, DMSO-d6): .delta. 8.65 (t, 1H), 7.98
(m, 4H), 7.88 (d, 2H), 7.55 (d, 2H), 3.76 (d, 2H), 3.24 (m, 2H),
2.10 (br s, 2H), 1.15 (t, 3H).
[0665] LC-MS (ESI): 318.95 (M+1).
e.
N-(4-(4-(ethylcarbamoyl)phenylsulfonyl)benzyl)imidazo[1,2-a]pyridine-6--
carboxamide
##STR00095##
[0666] In a 250 mL round-bottomed flask was added
4-(4-(aminomethyl)phenylsulfonyl)-N-ethylbenzamide (1 g, 3.14
mmol), imidazo[1,2-a]pyridine-6-carboxylic acid (0.509 g, 3.14
mmol) and HATU (1.314 g, 3.45 mmol) in DMF (Volume: 50 mL) followed
by DIEA (1.207 mL, 6.91 mmol). The reaction was stirred overnight
and then concentrated under reduced pressure. The reaction was
diluted with methylene chloride and poured into a separatory
funnel. The organic layer was washed with 1M NaOH and water. The
bottom was separated and concentrated and purified directly on the
Biotage to give 514 mg of clean product (35% yield).
[0667] .sup.1H NMR (300 MHz, DMSO-d6): .delta. 9.19 (t, 1H), 9.11
(t, 1H), 8.64 (t, 1H), 8.04-9.92 (m, 7H), 6.63 (m, 3H), 7.55 (d,
2H), 4.53 (d, 2H), 3.25 (m, 2H), 1.08 (t, 3H).
[0668] LC-MS (ESI): 463.05 (M+1).
Example 2J
N-(4-((3-methoxyphenyl)sulfonyl)benzyl)imidazo[1,2-a]pyrimidine-6-carboxam-
ide
##STR00096##
[0670] The title compound was prepared with 80% yield by following
Example 4D. .sup.1H NMR 6 (d.sub.6-dmso) 9.47 (1H, d); 9.34 (1H,
t); 8.92 (1H, d); 8.01 (1H, d); 7.95 (2H, d); 7.80 (1H, d); 7.58
(2H, d); 7.54-7.47 (2H, m); 7.42-7.41 (1H, m); 7.23 (1H, dt); 4.57
(2H, d and 3.81 (3H, s).
[0671] LC-MS (ESI): 422.9 (M+1).
Example 2K
N-(4-(1-isopropyl-1H-pyrazol-4-ylsulfonyl)benzyl)
imidazo[1,2-a]pyridine-6-carboxamide
##STR00097##
[0672] a. N-(4-((1-isopropyl-1H-Pyrazol-4-yl)
sulfonyl)benzyl)acetamide
##STR00098##
[0673] In a 1 L round-bottomed flask were added sodium
4-(acetamidomethyl)benzenesulfinate (3.97 g, 16.89 mmol, 1.3 eq.),
1-isoproyl 1H-pyrazol-4-ylboronic acid (2 g, 12.99 mmol)] and
COPPER (II) ACETATE (2.6 g, 14.29 mmol)), POTASSIUM CARBONATE (3.95
g, 28.6 mmol) in DMSO (50 ml) followed by 10 g of 4 .ANG. molecular
sieves. The reaction was stirred overnight. Added water and EtOAc,
filtered through a short celite pad, added EtOAc, washed with water
twice, dried and concentrated. The biotage column purification
afforded 1.9 g of N-(4-((1-isopropyl-1H-Pyrazol-4-yl)
sulfonyl)benzyl)acetamide (45%).
[0674] .sup.1HNMR (DMSO-D.sub.6): .delta. 8.50 (s, 1H). 8.42 (t,
1H), 7.91 (s, 1H), 7.86 (d, 2H), 7.43 (d, 2H), 4.52 (m, 1H), 4.28
(d, 2H), 1.36 (d, 6H)
b. (4-(1-isopropyl-1H-pyrazol-4-ylsulfonyl)phenyl)methanamine
HCl
##STR00099##
[0675] The mixture of a 3M HCl solution (80 ml) and,
N-(4-(1-isopropyl-1H-pyrazol-4-ylsulfonyl)benzyl)acetamide (1.9 g,
5.91 mmol) in 2-Propanol (100 ml) was refluxed for over weekend,
removed solvent, added ether, filtered and dried to afford 1.4 g of
(4-(1-isopropyl-1H-pyrazol-4-ylsulfonyl)phenyl)methanamine HCl
salt(75%)
[0676] .sup.1HNMR (DMSO-d.sub.6): .delta. 8.50 (s, 1H), 7.94-7.98
(m, 3H), 7.85 (dd, 1H), 7.69 (d, 2H), 4.52 (m, 1H), 4.08 (d, 2H),
1.37 (d, 6H).
c.
N-(4-(1-isopropyl-1H-pyrazol-4-ylsulfonyl)benzyl)imidazo[1,2-a]pyridine-
-6-carboxamide
##STR00100##
[0677] In a 250 mL round-bottomed flask were added
imidazo[1,2-a]pyridine-6-carboxylic acid (0.719 g, 4.43 mmol),
(4-(1-isopropyl-1H-pyrazol-4-ylsulfonyl)phenyl)methanamine, HCl
(1.4 g, 4.43 mmol) and HBTU (1.849 g, 4.88 mmol), HOBT (0.747 g,
4.88 mmol) and DIEA (3.87 mL, 22.16 mmol) in DMF (Volume: 50 mL).
The reaction was stirred overnight and then concentrated under
reduced pressure. The residue was diluted with methylene chloride
and washed with 1M aq. NaOH. The organic layer was separated and
concentrated and directly purified in the Biotage to give 1.24 g of
N-(4-(1-isopropyl-1H-pyrazol-4-ylsulfonyl)benzyl)
imidazo[1,2-a]pyridine-6-carboxamide. .sup.1HNMR (DMSO-D.sub.6):
.delta. 9.20 (t, 1H), 9.13 (s, 2H), 8.51 (s, 1H), 8.05 (s, 1H),
7.88-7.91 (m, 3H), 7.53-7.67 (m, 4H), 4.42-4.55 (m, 3H), 1.37 (d,
6H).
[0678] LC-MS: 424.01 (M+1)
Example 2L
N-(4-(phenylsulfonyl)benzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
##STR00101##
[0679] The mixture of 1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid
(0.8 g, 4.90 mmol), HATU (1.87 g, 4.90 mmol), diisopropylethylamine
(1.2 mL, 6.69 mmol), and (4-(phenylsulfonyl)phenyl)methanamine
(1.10 g, 4.46 mmol) in DMF (50 mL) was stirred at room temperature
for 16 h. The DMF was removed under reduced pressure. 150 mL of
water was added to the residue and extracted with EtOAc
(3.times.100 mL). The combined organic layers was washed with
water, saturated sodium bicarbonate, brine, dried with sodium
sulfate, and concentrated in vacuo. The crude was purified by
Biotage with MeOH/DCM (0%-10%) to yield the title compound.
[0680] .sup.1H NMR (DMSO-d6): .delta. 9.27 (t, 1H), 8.98 (d, 1H),
8.72 (d, 1H), 8.27 (s, 1H), 7.94-7.90 (m, 4H), 7.66-7.55 (m, 5H),
4.56 (d, 2H).
[0681] LC-MS: 393.01 (M+1).
Example 2M
N-(4-(2,4-dimethylthiazol-5-ylsulfonyl)benzyl)imidazo[1,2-a]pyridine-6-car-
boxamide
##STR00102##
[0682] A mixture of copper iodide (0.2 M DMSO, 100 .mu.L, 20
.mu.mol), cesium (S)-pyrrolidine-2-carboxylate (0.2 M DMSO w/14%
MeOH (v/v), 200 .mu.L, 40 mmol), sodium
4-(acetamidomethyl)benzenesulfinate (0.2 M DMSO, 200 .mu.L, 40
mmol) and 5-bromo-2,4-dimethylthiazole (0.2 M DMSO, 240 .mu.L, 48
mmol) was heated at 90.degree. C. with shaking over night. The
reaction was treated with aqueous ammonia and extracted with EtOAc
and the organic extract was concentrated to dryness and the
resulting residue was dissolved in 70% i-PrOH (0.35 mL) and 3N HCl
(0.35 mL, 1.05 mmol) and was heated at 90.degree. C. for 4 hours
then concentrated to dryness. The residue was treated with
triethylamine (5% in ACN (v/v), 200 uL) and
imidazo[1,2-a]pyridine-6-carboxylic acid (0.2 M in DMA w/10% TEA
(v/v), 240 uL, 48 umol) and BOP (0.2 M DCE, 260 uL, 52 umol). The
solution was heated to 40.degree. C. for 4 h then cooled to room
temperature and partitioned between NaOH and EtOAc. The organic
layer was separated and concentrated in vacuo. The crude was
purified by LC/MS to afford the title compound as white solid.
[0683] .sup.1H NMR (400 MHz, CDCl.sub.3): .delta. 8.87 (dd, J=1.6
Hz, J'=0.8 Hz 1H), 7.89 (dt, J=8.4 Hz, J'=2 Hz, 2H), 7.71 (d, J=1.6
Hz, 1H), 7.67 (s, 1H), 7.60 (d, J=9.2 Hz, 1H), 7.50 (d, J=8.4 Hz
2H), 7.43 (dd, J=9.2 Hz, J'=2 Hz, 1H), 6.84 (bs, 1H), 4.73 (d, J=6
Hz, 2H), 2.65 (s, 3H), 2.57 (s, 3H).
[0684] LC-MS: 427.10 (M+1)
Example 2N
N-(3-(naphthalen-2-ylsulfonyl)benzyl)imidazo[1,2-a]pyridine-6-carboxamide
##STR00103##
[0685] To a mixture of sodium 4-(acetamidomethyl)benzenesulfinate
(0.2 M MeOH, 100 .mu.L, 20 mmol) and zinc chloride (0.5 M THF, 40
.mu.L, 20 .mu.mol), cesium carbonate (1.43 M MeOH, 25 .mu.L, 35
.mu.mol) then 2-bromonapthelene (0.2 M Toluene, 110 .mu.L, 22
.mu.mol) were added. A toluene solution of XantPhos and Pd.sub.2
dba.sub.3 (0.01 M XantPhos/0.005 M Pd.sub.2 dba.sub.3, 50 .mu.L,
2.5 mol %) was added and the reaction was heated for 4 h at
95.degree. C. under nitrogen. The reaction was cooled to room
temperature and 70% i-PrOH (0.35 mL) and 3N HCl (0.35 mL, 1.05
mmol) were added and was heated at 95.degree. C. for 4 hours then
concentrated to dryness. The residue was treated with triethylamine
(5% in ACN (v/v), 100 .mu.L) and
imidazo[1,2-a]pyridine-6-carboxylic acid (0.2 M in DMA w/10% TEA
(v/v), 120 .mu.L, 24 .mu.mol) and BOP (0.2 M DCE, 130 .mu.L, 26
.mu.mol). The solution was heated to 40.degree. C. for 4 h then
cooled to room temperature and partitioned between NaOH and EtOAc.
The organic layer was separated and deposited on a SCX-SPE
cartridge which was eluted to two fractions: the 1.sup.st with 25%
MeOH/EtOAc (v/v), the 2.sup.nd with Et3N/MeOH/EtOAc (1:1:10 v/v/v).
The second fraction was concentrated to dryness and was purified by
LC/MS to afford the title compound as white solid.
[0686] .sup.1H NMR (400 MHz, CDCl.sub.3): .delta. 8.85 (s, 1H),
8.55 (s, 1H), 7.93 (m, 4H), 7.87 (d, J=8 Hz, 1H), 7.81 (dd, J=8.8
Hz, J'=1.6 Hz, 1H), 7.63 (m, 5H), 7.47 (d, J=8.4 Hz, 2H), 7.34 (m,
1H), 6.81 (m, 1H), 4.70 (d, J=5.6 Hz, 2H).
[0687] LC-MS: 442.13 (M+1)
Example 2O
N-(4-(naphthalen-2-ylsulfonyl)benzyl)furo[2,3-c]pyridine-2-carboxamide
##STR00104##
[0688] a. tert-butyl 4-bromobenzylcarbamate
##STR00105##
[0689] A 200-mL RBF equipped with a magnetic stir bar was charged
with (4-bromophenyl)methanamine hydrochloride (5.23 g, 23.50 mmol),
K.sub.2CO.sub.3 (3.90 g, 28.2 mmol), MeTHF (Ratio: 4.00, Volume: 50
ml), and Water (Ratio: 1.000, Volume: 12.5 ml). To the resulting
mixture was added BOC.sub.2O (6.00 ml, 25.9 mmol) in one portion at
rt with stirring. LCMS after 1 h suggested clean, complete
conversion. The mixture was diluted with additional MeTHF (50 mL)
and water (10 mL), and the layers separated. The organic layer was
washed with half-saturated brine (2.times.25 mL) and then
concentrated under reduced pressure to 7.2 g of a white solid. The
crude product was used without further purification in the next
step.
[0690] .sup.1H NMR (400 MHz, CDCl.sub.3): .delta. 7.44 (d, J=8.4
Hz, 2H), 7.15 (d, J=8.3 Hz, 2H), 4.85 (br s, 1H), 4.26 (d, J=5.8
Hz, 2H), 1.45 (s, 9H) ppm.
b. methyl
3-(4-((tert-butoxycarbonylamino)methyl)phenylthio)propanoate
##STR00106##
[0691] A 200-mL RBF equipped with a magnetic stir bar and
containing tert-butyl 4-bromobenzylcarbamate, crude (6.72 g, 23.5
mmol) was charged with Toluene (Volume: 50 ml), Hunig'sBase (8.21
ml, 47.0 mmol), XANTPHOS (0.680 g, 1.175 mmol), Pd.sub.2(dba).sub.3
(0.538 g, 0.588 mmol), and finally methyl 3-mercaptopropanoate
(2.60 ml, 23.50 mmol). The mixture was then heated to 100.degree.
C. LCMS after 1 h suggested significant conversion, although
starting bromide was still evident by 220 nm. LCMS after 2 h a
little better. After 2.5 h, heating was discontinued. After
cooling, the mixture was loaded directly on a short silica gel
column. Elution with 5:1 hexanes-EtOAc, 4:1 hexanes-EtOAc, and
finally 3:1 hexanes-EtOAc afforded methyl
3-(4-((tert-butoxycarbonylamino)methyl)phenylthio)propanoate (7.19
g, 22.09 mmol, 94% yield) as a nearly colorless oil.
[0692] .sup.1H NMR (400 MHz, CDCl.sub.3): .delta. 7.32 (d, J=8.3
Hz, 2H), 7.21 (d, J=8.2 Hz, 2H), 4.84 (br s, 1H), 4.28 (d, J=5.8
Hz, 2H), 3.67 (s, 3H), 3.14 (t, J=7.4 Hz, 2H), 2.61 (t, J=7.5 Hz,
2H), 1.45 (s, 9H) ppm.
[0693] ESMS: 348.15 (M+Na)
c. methyl
3-(4-((tert-butoxycarbonylamino)methyl)phenylsulfonybpropanoate
##STR00107##
[0694] A 500-mL RBF equipped with a magnetic stir bar was charged
with OXONE (23.61 g, 38.4 mmol) and Water (Ratio: 1.822, Volume: 82
ml). The mixture was stirred at rt for 5 min in order to dissolve
the Oxone. Next, a solution of methyl
3-(4-((tert-butoxycarbonylamino)methyl)phenylthio)propanoate (5.0
g, 15.36 mmol) in Acetonitrile (Ratio: 1.000, Volume: 45 ml) was
added at rt with rapid stirring. The mixture was stirred at rt.
After 2.5 h, an aliquot was removed, worked up, and analyzed by
.sup.1H NMR, which confirmed complete conversion to sulfone. LCMS
also looked good. The reaction mixture was then extracted with
EtOAc (100 mL). This extract was concentrated under reduced
pressure. The aqueous layer was re-extracted once with fresh EtOAc.
This extract was combined with the first, concentrated extract. The
combined solution was washed twice with half-saturated brine
(2.times.50 mL) and concentrated under reduced pressure to afford
methyl
3-(4-((tert-butoxycarbonylamino)methyl)phenylsulfonyl)propanoate
(5.17 g, 14.46 mmol, 94% yield) as a white solid.
[0695] .sup.1H NMR (400 MHz, CDCl.sub.3): .delta. 7.86 (d, J=8.4
Hz, 2H), 7.48 (d, J=8.6 Hz, 2H), 5.03 (br s, 1H), 4.41 (d, J=6.2
Hz, 2H), 3.64 (s, 3H), 3.41 (t, J=7.7 Hz, 2H), 2.74 (t, J=7.8 Hz,
2H), 1.46 (s, 9H) ppm.
[0696] ESMS: 380.07 (M+Na)
d. methyl 3-(4-(aminomethyl)phenylsulfonyl)propanoate
hydrochlorid
##STR00108##
[0697] A 200-mL RBF equipped with a magnetic stir bar and
containing methyl
3-(4-((tert-butoxycarbonylamino)methyl)phenylsulfonyl)propanoate
(5.16 g, 14.44 mmol) was charged with MeOH (Volume: 50 ml) followed
by HYDROCHLORIC ACID, conc (1.323 ml, 15.88 mmol). The solution was
then heated to 50.degree. C. LCMS after overnight indicated
complete conversion. Heating was discontinued. After cooling, the
slurry was concentrated partially under reduced pressure, removing
32 mL of MeOH. The resulting concentrated slurry was diluted with
MTBE (50 mL). The slurry was stirred at rt for 30 min, then
filtered on a glass, medium frit, 60-mL Buchner funnel. The filter
cake was washed with MTBE and dried under suction and a positive
pressure of nitrogen to afford methyl
3-(4-(aminomethyl)phenylsulfonyl)propanoate hydrochloride (4.10 g,
13.96 mmol, 97% yield) as a snow-white, crystalline, free-flowing
solid.
[0698] .sup.1H NMR (400 MHz, DMSO-d.sub.6): .delta. 8.62 (br s,
2H), 7.92 (d, J=8.5 Hz, 2H), 7.77 (d, J=8.4 Hz, 2H), 4.14 (s, 2H),
3.58 (t, J=7.3 Hz, 2H), 3.52 (s, 3H), 2.59 (t, J=7.3 Hz, 2H)
ppm.
[0699] ESMS: 258.10 (M+1).
e. methyl
3-(4-((furo[2,3-c]pyridine-2-carboxamido)methyl)phenylsulfonybpr-
opanoate
##STR00109##
[0700] A 25-mL RBF equipped with a magnetic stir bar was charged
with furo[2,3-c]pyridine-2-carboxylic acid (135 mg, 0.828 mmol),
methyl 3-(4-(aminomethyl)phenylsulfonyl)propanoate hydrochloride
(243 mg, 0.828 mmol), EtOH (Volume: 2.7 ml), N-METHYLMORPHOLINE
(0.218 ml, 1.986 mmol), and finally EDC (190 mg, 0.993 mmol). The
reaction mixture was stirred at rt. LCMS after 75 min shows some
conversion, with longer-retaining by-product also forming. LCMS
after 3 h shows some more conversion, but not significant. After
3.5 h, HOBT (6.34 mg, 0.041 mmol) was added. LCMS, 75 min after
HOBT addition, not much different. LCMS after overnight not much
different. The reaction mixture was slowly diluted with water (8.1
mL). The resulting slurry was stirred at rt for 1 h, then filtered
on a 30-mL, medium frit, glass Buchner funnel. The solid was washed
with water and dried under suction and a positive pressure of
nitrogen to yield methyl
3-(4-((furo[2,3-c]pyridine-2-carboxamido)methyl)phenylsulfonyl)pro-
panoate (0.12 g, 0.298 mmol, 36.0% yield) as a slightly off-white
fluffy powder.
[0701] .sup.1H NMR (400 MHz, DMSO-d.sub.6): .delta. 9.67 (t, J=6.1
Hz, 1H), 9.05 (s, 1H), 8.47 (d, J=5.2 Hz, 1H), 7.85 (d, J=8.4 Hz,
2H), 7.82 (dd, J=5.3, 1.1 Hz, 1H), 7.65 (d, J=0.8 Hz, 1H), 7.60 (d,
J=8.4 Hz, 2H), 4.59 (d, J=6.1 Hz, 2H), 3.53 (t, J=7.2 Hz, 2H), 3.49
(s, 3H), 2.59 (t, J=7.2 Hz, 2H) ppm.
[0702] ESMS: 403.03 (M+1)
f. sodium
4-((furo[2,3-c]pyridine-2-carboxamido)methyl)benzenesulfinate
##STR00110##
[0703] A 25-mL RBF equipped with a magnetic stir bar was charged
with methyl 3-(4-((furo[2,3-c]pyridine-2-carboxamido)methyl)phenyl
sulfonyl)propanoate (113 mg, 0.281 mmol) followed by a solution of
SODIUM ETHOXIDE (21 wt % in EtOH) (91 mg, 0.281 mmol) dissolved in
MeOH (Volume: 2 ml). The mixture was stirred at rt. Over time, the
solid dissolved. LCMS after 30 min shows ca 80-85% conversion. LCMS
after 1 h shows essentially complete conversion. Note: no transient
intermediate/by-product isomeric with the SM was observed as in the
case with the analogous azaindole experiments. LCMS after 2 h shows
complete, clean conversion. After 2.5 h, the solution was
concentrated under a gentle stream of nitrogen overnight to afford
sodium
4-((furo[2,3-c]pyridine-2-carboxamido)methyl)benzenesulfinate
(0.102 g, 0.301 mmol, 107% yield) as an off-white/light tan
solid.
[0704] .sup.1H NMR (400 MHz, DMSO-d.sub.6): .delta. 8.99 (s, 1H),
8.42 (d, J=5.2 Hz, 1H), 7.76 (dd, J=5.2, 1.1 Hz, 1H), 7.55 (d,
J=0.6 Hz, 1H), 7.38 (d, J=8.0 Hz, 2H), 7.25 (d, J=8.1 Hz, 2H), 4.44
(s, 2H) ppm.
[0705] ESMS: 317.04 (M+1)
g.
N-(4-(naphthalen-2-ylsulfonyl)benzyl)furo[2,3-c]pyridine-2-carboxamide
##STR00111##
[0706] To a mixture of naphthylen-2-boronic acid (0.2 M dioxane,
150 .mu.L, 30 .mu.mol) and diacetoxycopper (0.2 M DMSO, 150 .mu.L,
30 .mu.mol) and triethylamine (Neat, 9.3 .mu.L, 67 .mu.mol), sodium
4-((furo[2,3-c]pyridine-2-carboxamido)methyl)benzene sulfinate (0.2
M DMSO, 50 .mu.L, 10 .mu.mol) was added and the reaction was heated
at 40.degree. C. over night. The reaction was cooled to room
temperature and partitioned between aqueous ammonia and EtOAc. The
organic layer was separated and deposited on a SCX-SPE cartridge
which was eluted to two fractions: the 1.sup.st with 25% MeOH/EtOAc
(v/v), the 2.sup.nd with ammonia in methanol (2 N). The second
fraction was concentrated to dryness and was purified by LC/MS to
afford the title compound as white solid.
[0707] .sup.1H NMR (400 MHz, CDCl.sub.3): .delta. 8.89 (s, 1H),
8.56 (d, J=2 Hz, 1H), 8.50 (d, J=5.2 Hz, 1H), 7.99 (m, 3H), 7.92
(d, J=8.8 Hz, 1H), 7.87 (m, 2H), 7.62 (m, 3H), 7.51 (m, 3H), 7.08
(m, 1H), 4.72 (d, J=6.4 Hz, 2H).
[0708] LC-MS: 443.22 (M+1)
Example 2P
N-(4-(5-(dimethylamino)pyrazin-2-ylsulfonyl)benzyl)imidazo[1,2-a]pyridine--
6-carboxamide
##STR00112##
[0709] a.
N-(4-(5-(dimethylamino)pyrazin-2-ylsulfonyl)benzyl)acetamide
##STR00113##
[0710] The mixture of XANTPHOS (0.573 g, 0.990 mmol), Cs2CO3 (6.45
g, 19.80 mmol), Pd2(dba)3 (0.453 g, 0.495
mmol),4-(acetamidomethyl)benzenesulfinic acid, sodium salt (3.51 g,
14.85 mmol), 5-bromo-N,N-dimethylpyrazin-2-amine (2 g, 9.90 mmol)
in Toluene (50 ml) was degassed and heated to 120.degree. C. for
overnight. Cooled to RT, added EtOAc, washed with water, dried and
concentrated, The Biotage purification afforded 1.6 g of the target
compound (48%).
[0711] .sup.1HNMR (CDCl.sub.3): .delta. 8.75 (s, 1H). 8.03 (s, 1H),
7.87 (d, 2H), 7.38 (d, 2H), 6.11 (b, 1H), 4.45 (d, 2H), 3.21 (s,
6H), 2.16 (s, 3H).
b. 5-((4-(aminomethyl)phenyl)sulfonyl)-N,N-dimethylpyrazin-2-amine
hydrochloride
##STR00114##
[0712] The mixture of a 3M HCl solution (80 ml) and,
N-(4-(5-(dimethylamino)pyrazin-2-ylsulfonyl)benzyl)acetamide (1.6
g) in 2-Propanol (100 ml) was refluxed for over weekend, removed
solvent, added ether, filtered and dried to afford 1.2 g of the
target compound as a hydrochloride (76%).
[0713] .sup.1HNMR (DMSO-D.sub.6): .delta. 8.71 (s, 1H), 8.14 (s,
1H), 7.92 (d, 2H), 7.45 (d, 2H), 4.08 (d, 2H), 3.13 (s, 6H).
c. N-(4-(5-(dimethylamino) pyrazin-2-ylsulfonyl)benzyl)
imidazo[1,2-a]pyridine-6-carboxamide
##STR00115##
[0714] In a 250 mL round-bottomed flask was added
imidazo[1,2-a]pyridine-6-carboxylic acid (0.592 g, 3.65 mmol),
5-(4-(aminomethyl)phenylsulfonyl)-N,N-dimethylpyrazin-2-amine, HCl
(1.2 g, 3.65 mmol) and HBTU (1.522 g, 4.01 mmol), HOBT (0.615 g,
4.01 mmol) and DIEA (3.19 mL, 18.25 mmol) in DMF (50 mL). The
reaction was stirred overnight and then concentrated under reduced
pressure. The residue was diluted with methylene chloride and
washed with 1M aq. NaOH. The organic layer was separated and
concentrated and directly purified in the Biotage to give 235 mg of
N-(4-(5-(dimethylamino) pyrazin-2-ylsulfonyl)benzyl)
imidazo[1,2-a]pyridine-6-carboxamide (15%).
[0715] .sup.1HNMR (DMSO-d.sub.6): .delta. 9.21 (t, 1H), 9.13 (s,
1H), 8.67 (s, 1H), 8.12 (s, 1H), 8.95 (s, 1H), 7.86 (d, 2H), 7.63
(d, 2H), 7.54 (d, 2H), 4.53 (d, 2H), 3.11 (s, 6H).
[0716] LC-MS: 437.0 (M+1)
Example 2Q
N-(4-((3-(trifluoromethoxy)phenyl)sulfonyl)benzyl)imidazo[1,2-a]pyrimidine-
-6-carboxamide
##STR00116##
[0717] a: 4-((3-(trifluoromethoxy)phenyl)thio)benzonitrile
##STR00117##
[0718] To a colorless solution of 3-(trifluoromethoxy)benzenethiol
(5.0 g, 25.8 mmol) in DMF (80 mL) was added K.sub.2CO.sub.3 (4.21
g, 30.4 mmol) forming a yellow mixture. To this mixture was added
4-fluorobenzonitrile (2.84 g, 23.4 mmol). The mixture was heated to
120.degree. C. for 16 h, cooled to room temperature, and diluted
with 1N NaOH and Et2O. The layers were separated. The organic layer
was washed sequentially with 1N NaOH and brine, dried over
Na.sub.2SO.sub.4, and concentrated in vacuo. The residue was
purified by Biotage SP1 to afford the desired product as colorless
oil (6.09 g, 88% yield).
[0719] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 8.8-8.06 (m, 2H),
7.89-7.80 (m, 2H), 7.78-7.82 (m, 2H), 7.61 (t, 1H), 7.47 (d,
2H).
[0720] LC-MS: 295.93 (M+H).
b: 4-((3-(trifluoromethoxy)phenyl)sulfonyl)benzonitrile
##STR00118##
[0721] To a solution of
4-(3-(trifluoromethoxy)phenylthio)benzonitrile (6.09 g, 20.6 mmol)
in CHCl.sub.3 (110 mL) at 0.degree. C. was added mCPBA (20.88 g,
91.0 mmol). The mixture was stirred and warmed to room temperature
slowly overnight. The solids were removed by vacuum filtration,
rinsed with CHCl.sub.3. The filtrate was washed with 1N NaOH
(.times.2). The separated organic layer was washed with water and
brine, dried over Na.sub.2SO.sub.4, filtered, concentrated to
afford the product without further purification for next step (6.00
g, 89%).
[0722] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 8.08 (d, 1H),
8.06 (d, 1H), 7.89-7.80 (m, 4H), 7.61 (t, 1H), 7.49-7.43 (m,
1H).
[0723] LC-MS: 349.90 (M+Na).
c: (4-((3-(trifluoromethoxy)phenyl)sulfonyl)phenyl)methanamine
##STR00119##
[0724] To a small flask was added 3 pipette-full slurry of Raney Ni
in water and then added methanol (2 mL). The wash solvent (MeOH)
was removed via pipette. The wash was repeated twice more,
affording about 7 equivalents of nickel. To a 500 mL Parr reaction
cylinder was added
4-(3-(trifluoromethoxy)phenylsulfonyl)benzonitrile (6.00 g, 18.3
mmol) in MeOH (120 ml), followed by addition of the prewashed
nickel, 7N ammonia (37.2 ml, 26.0 mmol) in MeOH and potassium
hydroxide (0.329 g, 5.9 mmol). The mixture was vacuumed and purged
with H.sub.2 three times, then hydrogenated at 50 psi overnight.
LC-MS analysis indicated the completion of the hydrogenation of
nitrile. The mixture was filtered through celite. The filtrate was
concentrated and purified by Biotage SP1 affording the product as
light yellow oil (4.20 g, 93% yield).
[0725] .sup.1H NMR (300 MHz, DMSO-d.sub.6): .delta. 7.99-7.91 (m,
4H), 7.75-7.73 (m, 3H), 7.58 (d, 2H), 3.76 (s, 2H).
[0726] LC-MS: 331.97 (M+H).
d:
N-(4-((3-(trifluoromethoxy)phenyl)sulfonyl)benzyl)imidazo[1,2-a]pyrimid-
ine-6-carboxamide
##STR00120##
[0727] A mixture of imidazo[1,2-a]pyrimidine-6-carboxylic acid
(0.739 g, 4.53 mmol),
(4-(3-(trifluoromethoxy)phenylsulfonyl)phenyl)methanamine (1.5 g,
4.53 mmol), BOP (2.203 g, 4.98 mmol) and DIEA (0.949 mL, 5.43 mmol)
in DMF (25 mL) was stirred at room temperature overnight. The
reaction mixture was concentrated in vacuo to remove the DMF. The
residue was diluted with EtOAc and then washed with 1N NaOH. The
separated aqueous layer was back-extracted with EtOAc. The combined
organic extracts were washed with 5% AcOH, water, brine and dried
(Na.sub.2SO.sub.4), filtered and concentrated. Purification by
Biotage SP1 of the crude afforded the title compound as off-white
solids (980 mg, 45% yield).
[0728] .sup.1H NMR (300 MHz, DMSO-d.sub.6): .delta. 9.47 (d, 1H),
9.35 (t, 1H), 9.23 (d, 1H), 8.01-7.98 (m, 5H), 7.80-7.31 (m, 3H),
7.60 (d, 2H), 4.57 (d, 2H).
[0729] LC-MS: 476.87 (M+1).
Example 2R
N-(4-(benzylsulfonyl)benzyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
##STR00121##
[0730] a: N-(4-(benzylsulfonyl)benzyl)acetamide
##STR00122##
[0731] To a solution of sodium 4-(acetamidomethyl)benzenesulfinate
(1 g, 4.25 mmol) in water (12 mL) were added TBAI (0.157 g, 0.425
mmol) and (bromomethyl)benzene (0.742 g, 4.34 mmol) under N.sub.2
flow. The reaction mixture was heated to 70.degree. C. for 2 h. The
white solids were precipitated out. LC-MS analysis showed that the
major peak was the desired product. The white solids were filtered
and washed with water and ether to remove TBAI, then dried under
reduced pressure to give 696 mg of desired product with 90% HPLC
purity. The collected solids were used for next step without
further purification.
[0732] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 7.55 (d, 2H),
7.33-7.23 (m, 5H), 7.08 (d, 2H), 5.94 (brs, 1H), 4.50 (d, 2H), 4.29
(s, 2H), 2.07 (s, 3H).
[0733] LC-MS: 304.12 (M+H).
b: (4-(benzylsulfonyl)phenyl)methanamine hydrochloride
##STR00123##
[0734] A mixture of N-(4-(benzylsulfonyl)benzyl)acetamide (300 mg,
0.989 mmol) and 3N HCl (11.87 ml, 35.6 mmol) in .sup.iPrOH (11 mL)
was heated to 100.degree. C. The cloudy mixture turned to a clear
solution as temperature rose. The reaction mixture was stirred for
16 h at 100.degree. C. LC-MS analysis indicated completion of
hydrolysis. The reaction mixture was allowed to cool to room
temperature. The white crystals were precipitated and filtered,
rinsed with cold mixture of .sup.iPrOH/ether to afford
hydrochloride salt of the desired product (235 mg, 80% yield).
[0735] .sup.1H NMR (300 MHz, DMSO-d.sub.6): .delta. 8.44 (brs, 3H),
7.75, 7.65 (dd, 4H), 7.29-7.27 (m, 3H), 7.16-7.13 (m, 2H), 4.69 (s,
2H), 4.12 (s, 2H).
[0736] LC-MS: 262.11 (M+H).
c:
N-(4-(benzylsulfonyl)benzyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
##STR00124##
[0737] 1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (57.2 mg, 0.353
mmol), 1H-benzo[d][1,2,3]triazol-1-ol (59.0 mg, 0.437 mmol) and EDC
(86 mg, 0.450 mmol) were dissolved in anhydrous THF (4 mL),
followed by addition of Hunig's base (0.12 mL, 0.7 mmol). The
mixture formed a slurry solution. DMF (1 mL) was added. After
stirring for 15 min., (4-(benzylsulfonyl)phenyl)methanamine
hydrochloride (100 mg, 0.336 mmol) and Hunig's base (0.12 mL, 0.7
mmol) in THF (1 mL) was added. The reaction mixture was heated and
stirred at 65.degree. C. overnight, then diluted with ethyl acetate
(.times.2). The combined organic layers were washed sequentially
with 5% aqueous acetic acid (.times.1), saturated aqueous sodium
bicarbonate (.times.2), and brine (.times.1). The organic layer was
dried over anhydrous sodium sulfate, filtered and concentrated in
vacuo to yield a crude product (65 mg). The crude was dissolved in
DCM and a few drops of MeOH, and purified by Biotage to give the
desired product (34 mg, 25% yield).
[0738] .sup.1H NMR (300 MHz, DMSO-d.sub.6): .delta. 12.05 (s, 1H),
9.31 (t, 1H), 8.93 (s, 1H), 8.21 (d, 1H), 7.68 (d, 2H), 7.51 (d,
2H), 7.36-7.26 (m, 5H), 7.16-7.13 (m, 2H), 4.63 (s, 2H), 4.59 (d,
2H).
[0739] LC-MS: 406.11 (M+H).
Example 2S
N-(4-(cyclohexylsulfonyl)benzyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
##STR00125##
[0740] a: N-(4-(cyclohexylsulfonyl)benzyl)acetamide
##STR00126##
[0741] To a solution of sodium 4-(acetamidomethyl)benzenesulfinate
(500 mg, 2.126 mmol) in DMSO (8 mL) was added iodocyclohexane (670
mg, 3.19 mmol). The reaction was heated up to 100.degree. C. for 48
h. The reaction mixture was diluted with EtOAc, and washed with
water (.times.1) and brine (.times.2). The organic was dried over
Na.sub.2SO.sub.4 and concentrated. The crude was purified by
Biotage to yield the desired product (52 mg, 8% yield).
[0742] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 7.66 (d, 2H),
7.36 (d, 2H), 6.72 (m, 1H), 4.46 (d, 2H), 2.83 (tt, 1H), 2.04 (s,
3H), 2.01-2.00 (m, 2H), 1.83-1.76 (m, 3H), 1.65 (d, 1H), 1.93-1.12
(m, 4H).
[0743] LC-MS: 296.06 (M+H).
b: (4-(cyclohexylsulfonyl)phenyl)methanamine
##STR00127##
[0744] A mixture of N-(4-(cyclohexylsulfonyl)benzyl)acetamide (52
mg, 0.176 mmol) and 3N HCl (2.11 mL, 6.34 mmol) in .sup.iPrOH (2.5
mL) was heated to 100.degree. C. The cloudy mixture turned to a
clear solution as temperature rose. The reaction mixture was
stirred and refluxed for 16 h at 100.degree. C. LC-MS analysis
indicated that no starting material was present and some other
by-product was formed (the desired product showed as 22% in HPLC).
The mixture was cooled to RT and the solvent was concentrated. The
resulting slurry was treated with 1N NaOH and EtOAc. The combined
organic extracts were washed with brine, dried and concentrated to
yield a crude product (120 mg). The crude was purified by Biotage
to yield the free amine (25 mg, 56% yield).
[0745] LC-MS: 254.08 (M+H).
c:
N-(4-(cyclohexylsulfonyl)benzyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamid-
e
##STR00128##
[0746] 1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (16.80 mg, 0.104
mmol), 1H-benzo[d][1,2,3]triazol-1-ol (17.33 mg, 0.128 mmol) and
EDC (25.3 mg, 0.132 mmol) were dissolved in anhydrous THF (3 mL),
followed by addition of Hunig's base (0.7 mL, 0.7 mmol). The
mixture formed a slurry solution. DMF (0.5 mL) was added. After
stirring for 15 min at 65.degree. C.,
(4-(cyclohexylsulfonyl)phenyl)methanamine (25 mg, 0.099 mmol) in
THF/DMF (1.0/0.3 mL) was added. The reaction mixture was stirred at
65.degree. C. overnight, then diluted with ethyl acetate. The
organic layer was washed sequentially with 5% aqueous acetic acid
(.times.2), saturated aqueous sodium bicarbonate (.times.2), and
brine (.times.1). The organic layer was dried over anhydrous sodium
sulfate, filtered and concentrated in vacuo to yield a crude
product (40 mg). The crude was dissolved in DMSO and purified by
reverse phase preparative HPLC to give the title compound (12.4 mg,
32% yield).
[0747] .sup.1H NMR (300 MHz, DMSO-d.sub.6): .delta. 12.05 (brs,
1H), 9.30 (t, 1H), 8.88 (s, 1H), 8.16 (d, 1H), 7.76 (d, 2H), 7.54
(d, 2H), 7.32 (d, 1H), 7.27 (s, 1H), 4.57 (d, 2H), 3.08 (m, 1H),
1.78-1.66 (m, 4H), 1.51 (d, 1H), 1.20-0.96 (m, 5H).
[0748] LC-MS: 398.0 (M+H).
It is understood that the person skilled in the art will be able to
prepare the compounds of the present invention using methods known
in the art along with the general method of synthesis described
herein.
Assays
Assay Example 1
Biochemical Inhibition Assay
NAMPT Protein Purification
[0749] Recombinant His-tagged NAMPT was produced in E. coli cells,
purified over a Ni column, and further purified over a
size-exclusion column by XTAL Biostructures.
The NAMPT Enzymatic Reaction
[0750] The NAMPT enzymatic reactions were carried out in Buffer A
(50 mM Hepes pH 7.5, 50 mM NaCl, 5 mM MgCl.sub.2, and 1 mM THP) in
96-well V-bottom plates. The compound titrations were performed in
a separate dilution plate by serially diluting the compounds in
DMSO to make a 100.times. stock. Buffer A (89 .mu.L) containing 33
nM of NAMPT protein was added to 1 .mu.L of 100.times. compound
plate containing controls (e.g. DMSO or blank). The compound and
enzyme mix was incubated for 15 minutes at room temperature, then
10 .mu.L of 10.times. substrate and co-factors in Buffer A were
added to the test well to make a final concentration of 1 .mu.M
NAM, 100 .mu.M 5-Phospho-D-ribose 1-diphosphate (PRPP), and 2.5 mM
Adenosine 5'-triphosphate (ATP). The reaction was allowed to
proceed for 30 minutes at room temperature, then was quenched with
the addition of 11 .mu.l of a solution of formic acid and
L-Cystathionine to make a final concentration of 1% formic acid and
10 .mu.M L-Cystathionine. Background and signal strength was
determined by addition (or non-addition) of a serial dilution of
NMN to a pre-quenched enzyme and cofactor mix.
Quantification of NMN
[0751] A mass spectrometry-based assay was used to measure the
NAMPT reaction product (NMN) and the internal control
(L-Cystathionine). NMN and L-Cystathionine were detected using the
services of Biocius Lifesciences with the RapidFire system. In
short, the NMN and L-Cystathionine are bound to a graphitic carbon
cartridge in 0.1% formic acid, eluted in 30% acetonitrile buffer,
and injected into a Sciex 4000 mass spectrometer. The components of
the sample were ionized with electrospray ionization and the
positive ions were detected. The Q1 (parent ion) and Q3 (fragment
ion) masses of NMN were 334.2 and 123.2, respectively. The Q1 and
Q3 for L-Cystathionine were 223.1 and 134.1, respectively. The
fragments are quantified and the analyzed by the following
method.
[0752] % Inhibitions are Determined Using this Method.
[0753] First the NMN signal is normalized to the L-Cystathionine
signal by dividing the NMN signal by the L-Cystathionine signal for
each well. The signal from the background wells are averaged and
subtracted from the test plates. The compound treated cells re then
assayed for % inhibition by using this formula.
%Inh=100-100*x/y
wherein x denotes the average signal of the compound treated wells
and y denotes the average signal of the DMSO treated wells. IC50s
are Determined Using Excel and this Formula.
IC50=10 (LOG 10(X)+(((50-%Inh at Cmpd Concentration 1)/(XX-YY)*(LOG
10(X)-LOG 10(Y))))
wherein X denotes the compound concentration 1, Y denotes the
compound concentration 2, XX denotes the % inhibition at compound
concentration 1 (X), and YY denotes the % inhibition at compound
concentration 2 (Y). The NAMPT-inhibitor compounds of this
invention have IC50 values that are preferably under 1 .mu.M, more
preferably under 0.1 .mu.M, and most preferably under 0.01 .mu.M.
Results for the compounds are provided in Table 3.
Assay Example 2
In-Vitro Cell Proliferation Assay
[0754] A2780 cells were seeded in 96-well plates at
1.times.10.sup.3 cells/well in 180 .mu.l of culture medium (10%
FBS, 1% Pen/Strep Amphotecricin B, RPMI-1640) with and without the
addition of either .beta.-nicotinamide mononucleotide (NMN) or
nicotinamide (NAM). After overnight incubation at 37.degree. C. and
5% CO.sub.2, the compound titrations were performed in a separate
dilution plate by serially diluting the compounds in DMSO to make a
1000.times. stock. The compounds were then further diluted to
10.times. final concentration in culture media, whereupon 20 .mu.l
of each dilution was added to the plated cells with controls (e.g.
DMSO and blank) to make a final volume of 200 .mu.L. The final DMSO
concentration in each well was 0.1%. The plates were then incubated
for 72 hours at 37.degree. C. in a 5% CO.sub.2 incubator. The
number of viable cells was then assessed using sulforhodamine B
(SRB) assay. Cells were fixed at 4.degree. C. for 1 hour with the
addition of 50 .mu.l 30% trichloroacetic acid (TCA) to make a final
concentration of 6% TCA. The plates were washed four times with
H.sub.2O and allowed to dry for at least 1 hour, whereupon 100
.mu.L of a 4% SRB in 1% acetic acid solution was added to each well
and incubated at room temperature for at least 30 minutes. The
plates were then washed three times with 1% acetic acid, dried, and
treated with 100 .mu.L of 10 mM Tris-Base solution. The plates were
then read in a microplate reader at an absorbance of 570 nm.
Background was generated on a separate plate with media only.
[0755] Method for Determining % Inhibition
[0756] First, the signals from the background plate are averaged,
then the background was subtracted from the test plates. The
compound-treated cells were then assayed for % inhibition by using
the following formula:
%Inh=100-100*x/y
wherein x denotes the average signal of the compound-treated cells
and y denotes the average signal of the DMSO-treated cells.
Formula for Determining IC.sub.50 Values:
[0757] IC50=10 (LOG 10(X)+(((50-%Inh at Cmpd Concentration
1)/(XX-YY)*(LOG 10(X)-LOG 10(Y))))
[0758] wherein X denotes the compound concentration 1, Y denotes
the compound concentration 2, XX denotes the % inhibition at
compound concentration 1 (X), and YY denotes the % inhibition at
compound concentration 2 (Y).
[0759] Specificity of Cytotoxicity.
[0760] Inhibition of NAMPT could be reversed by the addition of NAM
or NMN. The specificity of the compounds were determined via cell
viability assay in the presence of the compound and either NAM or
NMN. Percent inhibitions were determined using the method given
above.
[0761] The NAMPT-inhibitor compounds of this invention have IC50
values that are preferably under 1 .mu.M, more preferably under 0.1
.mu.M, and most preferably under 0.01 .mu.M. Most preferable
compounds of this invention are compounds that have both the
enzymatic IC50-value and the A2780 IC 50-value under 1 .mu.M, more
preferably both of the values are under 0.1 .mu.M, and most
preferably both of the values are under 0.01 .mu.M. Results for the
compounds are provided in Table 3.
TABLE-US-00003 TABLE 3 Biochem A2780 IUPAC Name IC50 uM IC50 uM
(E)-2-cyano-3-({4-[(5-fluoro-2- 0.0011 0.0030
methoxyphenyl)sulfamoyl]phenyl}methyl)-1-(pyridin-4-yl)guanidine
5-hydroxy-N-({4-[(4-phenylbenzene)sulfonyl]phenyl}methyl)-1H- 0.1-1
1-10 indole-2-carboxamide
5-hydroxy-N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]-
0.1-1 1-10 1H-indole-2-carboxamide
5-hydroxy-N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]-
0.1-1 1-10 1H-indole-2-carboxamide
5-hydroxy-N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]-
0.1442 0.1-1 1H-indole-2-carboxamide
5-hydroxy-N-{[4-(1-methyl-1H-indazole-4-sulfonyl)phenyl]methyl}-1H-
0.1-1 >1.0 indole-2-carboxamide
5-N-({4-[(3,5-difluorobenzene)sulfonyl]phenyl}methyl)pyridine-2,5-
1-10 0.661 diamido
6-amino-N-({4-[(3,5-difluorobenzene)sulfonyl]phenyl}methyl)pyridine-
0.0142 0.275 3-carboxamide
N-({4-[(2,3,6-trimethoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.0797
0.0663 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2,3,6-trimethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0399 0.0667 c]pyridine-2-carboxamide
N-({4-[(2,3-difluoro-6-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.204 0.0849 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2,3-difluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0820 0.2786 b]pyridine-5-carboxamide
N-({4-[(2,3-dimethoxy-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-
0.1462 0.0586 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2,3-dimethoxy-5- 0.0152 0.007
methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
carboxamide N-({4-[(2,3-dimethoxy-5- 0.0042 0.0156
methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(2,3-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.123
0.0833 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2,3-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0117 0.0049 c]pyridine-2-carboxamide
N-({4-[(2,3-dimethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0093 0.0136 c]pyridine-2-carboxamide
N-({4-[(2,3-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0687 0.0249 a]pyridine-6-carboxamide
N-({4-[(2,3-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0176 0.0776 a]pyrimidine-6-carboxamide
N-({4-[(2,3-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3- 0.0516
0.008 c]pyridine-2-carboxamide
N-({4-[(2,3-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0433 0.00985 a]pyridine-6-carboxamide
N-({4-[(2,3-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0041 0.0469 a]pyrimidine-6-carboxamide
N-({4-[(2,4,5-trimethylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0313
0.0193 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2,4,5-trimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0091 0.0141 c]pyridine-2-carboxamide
N-({4-[(2,4,5-trimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.00934 0.0141 a]pyridine-6-carboxamide
N-({4-[(2,4,5-trimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0069 0.0240 a]pyrimidine-6-carboxamide
N-({4-[(2,4,6-trimethylbenzene)sulfonyl]phenyl}methyl)-1H- 0.136
0.1-1 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2,4,6-trimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0592 0.1-1 c]pyridine-2-carboxamide
N-({4-[(2,4,6-trimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0288 0.1-1 a]pyrimidine-6-carboxamide
N-({4-[(2,4-dichloro-3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.02 0.0147 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2,4-dichloro-3- 0.0177 0.0162
methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
carboxamide N-({4-[(2,4-dichloro-3- 0.0311 0.013
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(2,4-dichloro-3- 0.0066 0.0255
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide N-({4-[(2,4-dichloro-3- 0.0051 0.0067
methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(2,4-difluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0283 0.0281 a]pyridine-6-carboxamide
N-({4-[(2,4-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.1744
0.0447 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2,4-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0582 0.0151 a]pyridine-6-carboxamide
N-({4-[(2,4-dimethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0045 0.0016 c]pyridine-2-carboxamide
N-({4-[(2,4-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0612 0.0716 b]pyridine-5-carboxamide
N-({4-[(2,4-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3- 0.0218
0.024 c]pyridine-2-carboxamide
N-({4-[(2,4-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0216 0.0321 a]pyridine-6-carboxamide
N-({4-[(2,4-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0021 0.0492 a]pyrimidine-6-carboxamide
N-({4-[(2,5-difluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.1-1 0.3921 b]pyridine-5-carboxamide
N-({4-[(2,5-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.0398
0.0248 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2,5-dimethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0114 0.0063 c]pyridine-2-carboxamide
N-({4-[(2,5-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0202 0.0128 a]pyridine-6-carboxamide
N-({4-[(2,5-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0069 0.0457 a]pyrimidine-6-carboxamide
N-({4-[(2,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0209 0.0172 b]pyridine-5-carboxamide
N-({4-[(2,5-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3- 0.0181
0.0239 c]pyridine-2-carboxamide
N-({4-[(2,5-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0293 0.0154 a]pyridine-6-carboxamide
N-({4-[(2,6-dichloro-3-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0108 0.0162 c]pyridine-2-carboxamide N-({4-[(2,6-dichloro-3-
0.0073 0.0560
methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide N-({4-[(2,6-dichloro-3- 0.0044 0.0082
methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(2,6-dichlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.1795 1-10 b]pyridine-5-carboxamide
N-({4-[(2,6-dichlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0447 0.0135 c]pyridine-2-carboxamide
N-({4-[(2,6-dichlorobenzene)sulfonyl]phenyl}methyl)furo[2,3- 0.0124
0.0601 c]pyridine-2-carboxamide
N-({4-[(2,6-dichlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0012 0.0188 a]pyridine-6-carboxamide
N-({4-[(2,6-dichlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0134 0.1-1 a]pyrimidine-6-carboxamide
N-({4-[(2,6-dichlorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0076 0.0182 c]pyridine-2-carboxamide
N-({4-[(2,6-dimethoxy-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-
0.1-1 0.1-1 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2,6-dimethoxy-4- 0.0050 0.0230
methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
carboxamide
N-({4-[(2,6-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.159 0.1-1 b]pyridine-5-carboxamide
N-({4-[(2,6-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3- 0.0323
0.1-1 c]pyridine-2-carboxamide
N-({4-[(2-acetylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0036 0.0114 b]pyridine-5-carboxamide
N-({4-[(2-acetylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0057 0.0065 carboxamide
N-({4-[(2-acetylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0025
0.0082 a]pyrimidine-6-carboxamide
N-({4-[(2-butoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.176
0.1-1 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-butoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0311
0.0055 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-butoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0335 0.0665 c]pyridine-2-carboxamide
N-({4-[(2-butoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0512 0.0062 a]pyridine-6-carboxamide
N-({4-[(2-butoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0073 0.0738 a]pyrimidine-6-carboxamide
N-({4-[(2-butoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0070 0.0063 c]pyridine-2-carboxamide
N-({4-[(2-butoxy-5-chlorobenzene)sulfonyl]phenyl}methyl)-1H- 0.117
0.0737 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-butoxy-5-chlorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0156
0.0083 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-butoxy-5-chlorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0243 0.0663 c]pyridine-2-carboxamide
N-({4-[(2-butoxy-5-chlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0110 0.0080 a]pyridine-6-carboxamide
N-({4-[(2-butoxy-5-chlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0037 0.0628 a]pyrimidine-6-carboxamide
N-({4-[(2-butoxy-5-chlorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0073 0.0100 c]pyridine-2-carboxamide
N-({4-[(2-butoxy-6-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0088
0.0056 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-butoxy-6-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0256 0.0698 c]pyridine-2-carboxamide
N-({4-[(2-butoxy-6-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0053 0.0069 a]pyridine-6-carboxamide
N-({4-[(2-chloro-3-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0736
0.1-1 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-chloro-3-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0170 0.0611 c]pyridine-2-carboxamide
N-({4-[(2-chloro-4-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0178 0.0634 c]pyridine-2-carboxamide
N-({4-[(2-chloro-4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0144 0.1-1 a]pyrimidine-6-carboxamide
N-({4-[(2-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0516 0.0877 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0093 0.0145 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-chloro-4- 0.0167 0.0114
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(2-chloro-4- 0.0065 0.0669
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide N-({4-[(2-chloro-4- 0.0027 0.0055
methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(2-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.005
0.00278 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0080
0.0027 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0141 0.0142 c]pyridine-2-carboxamide
N-({4-[(2-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0011 0.0009 a]pyridine-6-carboxamide
N-({4-[(2-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0015 0.0007 a]pyrimidine-6-carboxamide
N-({4-[(2-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0249 0.0016 c]pyridine-2-carboxamide
N-({4-[(2-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0281
0.0121 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0163 0.0248 c]pyridine-2-carboxamide
N-({4-[(2-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0210 0.0063 a]pyridine-6-carboxamide
N-({4-[(2-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0105 0.0530 a]pyrimidine-6-carboxamide
N-({4-[(2-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0042 0.0057 c]pyridine-2-carboxamide
N-({4-[(2-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0247 0.0668 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0110 0.0097 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0026 0.0206 c]pyridine-2-carboxamide N-({4-[(2-chloro-5- 0.0056
0.0027
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(2-chloro-5- 0.0061 0.0515
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide N-({4-[(2-chloro-5- 0.0049 0.0053
methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(2-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0602
0.0659 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0188
0.0091 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0178 0.0149 c]pyridine-2-carboxamide
N-({4-[(2-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0056 0.0046 a]pyridine-6-carboxamide
N-({4-[(2-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0057 0.0225 a]pyrimidine-6-carboxamide
N-({4-[(2-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0022 0.0049 c]pyridine-2-carboxamide
N-({4-[(2-chloro-6-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.1142
0.0371 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-chloro-6-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.1722 0.0766 a]pyridine-6-carboxamide
N-({4-[(2-chloro-6-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0167 0.0214 c]pyridine-2-carboxamide N-({4-[(2-chloro-6- 0.0202
0.0258
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(2-chloro-6- 0.0027 0.0029
methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(2-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0925 1-0.1 b]pyridine-5-carboxamide
N-({4-[(2-chlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0241
0.0567 a]pyridine-6-carboxamide
N-({4-[(2-chlorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.0024 0.0066 2-carboxamide
N-({4-[(2-cyanobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.131 0.1-1 b]pyridine-5-carboxamide
N-({4-[(2-cyanobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0253 0.0629 c]pyridine-2-carboxamide
N-({4-[(2-cyanobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0246 0.0635 carboxamide
N-({4-[(2-cyanobenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0156
0.0613 a]pyridine-6-carboxamide
N-({4-[(2-cyanobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.0146 0.0676 2-carboxamide
N-({4-[(2-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0863
0.0670 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0034
0.0018 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0077 0.0069 c]pyridine-2-carboxamide
N-({4-[(2-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0314 0.0015 a]pyridine-6-carboxamide
N-({4-[(2-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0071 0.0143 a]pyrimidine-6-carboxamide
N-({4-[(2-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0038 0.0009 c]pyridine-2-carboxamide
N-({4-[(2-ethoxy-6-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0170 0.0283 c]pyridine-2-carboxamide
N-({4-[(2-ethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0493 0.0269 b]pyridine-5-carboxamide
N-({4-[(2-ethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0659 0.006 carboxamide
N-({4-[(2-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0203
0.00339 a]pyridine-6-carboxamide
N-({4-[(2-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0010
0.0071 a]pyrimidine-6-carboxamide
N-({4-[(2-ethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0084 0.013 b]pyridine-5-carboxamide
N-({4-[(2-ethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0054 0.0129 carboxamide
N-({4-[(2-ethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-
0.0302 0.0129 6-carboxamide
N-({4-[(2-ethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0025
0.0249 a]pyrimidine-6-carboxamide
N-({4-[(2-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0086 0.0563 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-fluoro-3- 0.033 0.0135
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide
N-({4-[(2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0197
0.0239 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0758
0.0070 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0063 0.0079 c]pyridine-2-carboxamide
N-({4-[(2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0075 0.0033 a]pyridine-6-carboxamide
N-({4-[(2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0032 0.0215 a]pyrimidine-6-carboxamide
N-({4-[(2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0107 0.0033 c]pyridine-2-carboxamide
N-({4-[(2-fluoro-4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.1203 0.2067 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-fluoro-4- 0.0413 0.0229
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide
N-({4-[(2-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0123 0.0253 c]pyridine-2-carboxamide
N-({4-[(2-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0214 0.0247 a]pyridine-6-carboxamide
N-({4-[(2-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0063 0.0614 a]pyrimidine-6-carboxamide
N-({4-[(2-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.139
0.1-1 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0778 0.0144 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0268 0.0637 c]pyridine-2-carboxamide N-({4-[(2-fluoro-5- 0.0047
0.0128
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(2-fluoro-5- 0.0104 0.0629
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(2-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0023 0.0128 c]pyridine-2-carboxamide
N-({4-[(2-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0241
0.0716 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0059 0.0134 c]pyridine-2-carboxamide
N-({4-[(2-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0068 0.0275 a]pyrimidine-6-carboxamide N-({4-[(2-fluoro-6- 0.0481
0.0264
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide
N-({4-[(2-fluoro-6-propoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0133 0.0142 c]pyridine-2-carboxamide N-({4-[(2-fluoro-6- 0.0914
0.0010
propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide
N-({4-[(2-fluoro-6-propoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0115 0.0293 c]pyridine-2-carboxamide
N-({4-[(2-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0418 0.1-1 carboxamide
N-({4-[(2-methanesulfonylbenzene)sulfonyl]phenyl}methyl)-1H- 0.2022
0.1-1 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-methanesulfonylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0542 0.1-1 c]pyridine-2-carboxamide
N-({4-[(2-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-
0.0563 0.0244
pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0133 0.0068 c]pyridine-2-carboxamide N-({4-[(2-methoxy-5- 0.0431
0.0117
methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(2-methoxy-5- 0.0039 0.0072
methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0683 0.0618 b]pyridine-5-carboxamide
N-({4-[(2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-
0.0189 0.0265 2-carboxamide
N-({4-[(2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0265
0.0153 a]pyridine-6-carboxamide
N-({4-[(2-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0039
0.0747 a]pyrimidine-6-carboxamide
N-({4-[(2-methyl-4-propoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0644 0.0794 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(2-methyl-4-propoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0305 0.0221 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-methyl-4-propoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0225 0.0596 c]pyridine-2-carboxamide N-({4-[(2-methyl-4- 0.0092
0.0133
propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(2-methyl-4- 0.0100 0.0518
propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide N-({4-[(2-methyl-4- 0.0129 0.0017
propoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0926 1-0.1 b]pyridine-5-carboxamide
N-({4-[(2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0152 0.0433 carboxamide
N-({4-[(2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0669
0.0912 a]pyridine-6-carboxamide
N-({4-[(2-phenoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.1-1 0.1-1 b]pyridine-5-carboxamide
N-({4-[(2-phenoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-
0.0204 1-10 2-carboxamide
N-({4-[(2-phenoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0636
0.0607 a]pyridine-6-carboxamide
N-({4-[(2-phenoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0085
0.1-1 a]pyrimidine-6-carboxamide
N-({4-[(3,4-dichlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0067 0.0055 b]pyridine-5-carboxamide
N-({4-[(3,4-dichlorobenzene)sulfonyl]phenyl}methyl)furo[2,3- 0.0104
0.0048 c]pyridine-2-carboxamide
N-({4-[(3,4-dichlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0015 0.0017 a]pyrimidine-6-carboxamide
N-({4-[(3,4-difluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0542 0.0289 b]pyridine-5-carboxamide
N-({4-[(3,4-difluorobenzene)sulfonyl]phenyl}methyl)furo[2,3- 0.0168
0.013 c]pyridine-2-carboxamide
N-({4-[(3,4-difluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0041 0.0363 a]pyrimidine-6-carboxamide
N-({4-[(3,4-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.0206
0.0056 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3,4-dimethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0062 0.0038 c]pyridine-2-carboxamide
N-({4-[(3,4-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.012 0.00251 a]pyridine-6-carboxamide
N-({4-[(3,4-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0029 0.0073 a]pyrimidine-6-carboxamide
N-({4-[(3,4-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0051 0.0034 b]pyridine-5-carboxamide
N-({4-[(3,4-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3- 0.0150
0.003 c]pyridine-2-carboxamide
N-({4-[(3,4-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0111 0.00297 a]pyridine-6-carboxamide
N-({4-[(3,4-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0011 0.0016 a]pyrimidine-6-carboxamide
N-({4-[(3,5-dichlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0067 0.0021 b]pyridine-5-carboxamide
N-({4-[(3,5-dichlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.001 0.0004 c]pyridine-2-carboxamide
N-({4-[(3,5-dichlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.00549 0.00128 a]pyridine-6-carboxamide
N-({4-[(3,5-difluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.008 0.007 b]pyridine-5-carboxamide
N-({4-[(3,5-difluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.006 0.0015 a]pyridine-6-carboxamide
N-({4-[(3,5-difluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.002 0.003 a]pyrimidine-6-carboxamide
N-({4-[(3,5-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.0026
0.0022 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3,5-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0044 0.0015 c]pyridine-2-carboxamide
N-({4-[(3,5-dimethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0027 0.0017 c]pyridine-2-carboxamide
N-({4-[(3,5-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0032 0.0015 a]pyridine-6-carboxamide
N-({4-[(3,5-dimethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0024 0.0016 a]pyrimidine-6-carboxamide
N-({4-[(3,5-dimethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0013 0.0009 c]pyridine-2-carboxamide
N-({4-[(3,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0104 0.0061 b]pyridine-5-carboxamide
N-({4-[(3,5-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3- 0.0167
0.0028 c]pyridine-2-carboxamide
N-({4-[(3,5-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.00676 0.00317 a]pyridine-6-carboxamide
N-({4-[(3,5-dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0017 0.0020 a]pyrimidine-6-carboxamide
N-({4-[(3-acetylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0100 0.0129 b]pyridine-5-carboxamide
N-({4-[(3-acetylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0176 0.008 carboxamide
N-({4-[(3-acetylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0125
0.00637 a]pyridine-6-carboxamide
N-({4-[(3-acetylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0018
0.0105 a]pyrimidine-6-carboxamide
N-({4-[(3-butoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0384 0.0675 b]pyridine-5-carboxamide
N-({4-[(3-butoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0115 0.0216 c]pyridine-2-carboxamide
N-({4-[(3-butoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0123 0.0695 carboxamide
N-({4-[(3-butoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0047
0.0180 a]pyridine-6-carboxamide
N-({4-[(3-butoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3- 0.0033
0.0387 c]pyridine-2-carboxamide
N-({4-[(3-chloro-2-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0109 0.0128 c]pyridine-2-carboxamide
N-({4-[(3-chloro-2-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0024 0.0176 a]pyrimidine-6-carboxamide
N-({4-[(3-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0192 0.0623 c]pyridine-2-carboxamide
N-({4-[(3-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0369
0.0161 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0625
0.0120 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0026 0.0016 c]pyridine-2-carboxamide
N-({4-[(3-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0257 0.0050 a]pyridine-6-carboxamide
N-({4-[(3-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0043 0.0265 a]pyrimidine-6-carboxamide
N-({4-[(3-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0572 0.0071 c]pyridine-2-carboxamide
N-({4-[(3-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0040 0.0036 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0107 0.0021 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-chloro-4-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0073 0.0018 c]pyridine-2-carboxamide N-({4-[(3-chloro-4- 0.0018
0.0018
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide N-({4-[(3-chloro-4- 0.0050 0.0016
methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(3-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0061
0.0019 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0083
0.0025 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0528 0.0017 c]pyridine-2-carboxamide
N-({4-[(3-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0018 0.0012 a]pyrimidine-6-carboxamide
N-({4-[(3-chloro-4-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0051 0.0010 c]pyridine-2-carboxamide
N-({4-[(3-chloro-4-propoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0079 0.00958 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-chloro-4-propoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0740 0.0078 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-chloro-4-propoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0049 0.0119 c]pyridine-2-carboxamide N-({4-[(3-chloro-4- 0.0065
0.0060
propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(3-chloro-4- 0.0039 0.0024
propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(3-chloro-4-propoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0151 0.0174 c]pyridine-2-carboxamide
N-({4-[(3-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0133
0.0060 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0099
0.0014 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0178
0.0031 c]pyridine-2-carboxamide
N-({4-[(3-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0039 0.0003 a]pyridine-6-carboxamide
N-({4-[(3-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0024 0.0029 a]pyrimidine-6-carboxamide
N-({4-[(3-chloro-5-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0014 0.0006 c]pyridine-2-carboxamide
N-({4-[(3-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0093 0.0025 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0170 0.0025 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-chloro-5-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0265 0.0015 c]pyridine-2-carboxamide N-({4-[(3-chloro-5- 0.0092
0.0015
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(3-chloro-5- 0.0013 0.0008
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide N-({4-[(3-chloro-5- 0.0041 0.0011
methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(3-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0062
0.0026 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0269 0.0018 c]pyridine-2-carboxamide
N-({4-[(3-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0013 0.0008 c]pyridine-2-carboxamide
N-({4-[(3-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0064 0.002 a]pyridine-6-carboxamide
N-({4-[(3-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0048 0.0023 a]pyrimidine-6-carboxamide
N-({4-[(3-chloro-5-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0045 0.0016 c]pyridine-2-carboxamide
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.007 0.006 b]pyridine-5-carboxamide
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0039 0.013 b]pyridine-2-carboxamide
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0060 0.0033 carboxamide
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.00908
0.00307 a]pyridine-6-carboxamide
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0013
0.0012 a]pyrimidine-6-carboxamide
N-({4-[(3-cyanobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0185 0.00954 b]pyridine-5-carboxamide
N-({4-[(3-cyanobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0121 0.0113 c]pyridine-2-carboxamide
N-({4-[(3-cyanobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0154 0.0126 carboxamide
N-({4-[(3-cyanobenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0059
0.0192 a]pyrimidine-6-carboxamide
N-({4-[(3-cyanobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.0035 0.0056 2-carboxamide
N-({4-[(3-ethoxy-2-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0312
0.0116 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-ethoxy-2-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0175 0.0227 c]pyridine-2-carboxamide
N-({4-[(3-ethoxy-2-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0050 0.0062 a]pyridine-6-carboxamide
N-({4-[(3-ethoxy-2-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0040 0.0197 a]pyrimidine-6-carboxamide
N-({4-[(3-ethoxy-2-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0037 0.0129 c]pyridine-2-carboxamide
N-({4-[(3-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0261
0.012 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0824
0.0044 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0110 0.0072 c]pyridine-2-carboxamide
N-({4-[(3-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0170 0.006 a]pyridine-6-carboxamide
N-({4-[(3-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0003 0.0078 a]pyrimidine-6-carboxamide
N-({4-[(3-ethoxy-4-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0033 0.0031 c]pyridine-2-carboxamide
N-({4-[(3-ethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0146 0.0190 b]pyridine-5-carboxamide
N-({4-[(3-ethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0077 0.0035 c]pyridine-2-carboxamide
N-({4-[(3-ethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0068 0.0110 carboxamide
N-({4-[(3-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0050
0.0031 a]pyridine-6-carboxamide
N-({4-[(3-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0021
0.0067 a]pyrimidine-6-carboxamide
N-({4-[(3-ethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3- 0.0032
0.0029 c]pyridine-2-carboxamide
N-({4-[(3-ethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0070 0.0071 b]pyridine-5-carboxamide
N-({4-[(3-ethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0087 0.0065 carboxamide
N-({4-[(3-ethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-
0.00483 0.00323 6-carboxamide
N-({4-[(3-ethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0038
0.0041 a]pyrimidine-6-carboxamide
N-({4-[(3-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.121
0.1-1 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0324 0.0063 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0166 0.0309 c]pyridine-2-carboxamide N-({4-[(3-fluoro-2- 0.0769
0.0650
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(3-fluoro-2- 0.0289 0.1-1
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(3-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0133 0.0125 c]pyridine-2-carboxamide
N-({4-[(3-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0469
0.0718 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0576
0.0132 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0132 0.0307 c]pyridine-2-carboxamide
N-({4-[(3-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0469 0.0132 a]pyridine-6-carboxamide
N-({4-[(3-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0081 0.0656 a]pyrimidine-6-carboxamide
N-({4-[(3-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0071 0.0214 c]pyridine-2-carboxamide
N-({4-[(3-fluoro-4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0430 0.0060 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-fluoro-4-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0022 0.0068 c]pyridine-2-carboxamide N-({4-[(3-fluoro-4- 0.00595
0.00289
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(3-fluoro-4- 0.0017 0.0083
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(3-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0117
0.0056 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0140 0.0033 c]pyridine-2-carboxamide
N-({4-[(3-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0133 0.00378 a]pyridine-6-carboxamide
N-({4-[(3-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0023 0.0063 a]pyrimidine-6-carboxamide
N-({4-[(3-fluoro-4-propoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0116 0.0065 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-fluoro-4-propoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0309 0.0104 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-fluoro-4-propoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0068 0.0118 c]pyridine-2-carboxamide N-({4-[(3-fluoro-4- 0.0221
0.0044
propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(3-fluoro-4- 0.0027 0.0033
propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(3-fluoro-4-propoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0037 0.0081 c]pyridine-2-carboxamide
N-({4-[(3-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0044 0.0063 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-fluoro-5-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0174 0.0033 c]pyridine-2-carboxamide N-({4-[(3-fluoro-5- 0.0016
0.0033
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(3-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0095
0.0056 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0083
0.0018 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0034 0.0032 c]pyridine-2-carboxamide
N-({4-[(3-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0027 0.0006 a]pyridine-6-carboxamide
N-({4-[(3-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0015 0.0054 a]pyrimidine-6-carboxamide
N-({4-[(3-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0010 0.0006 c]pyridine-2-carboxamide
N-({4-[(3-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0339 0.0253 b]pyridine-5-carboxamide
N-({4-[(3-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0058 0.0145 carboxamide
N-({4-[(3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0221
0.0122 a]pyridine-6-carboxamide
N-({4-[(3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0019
0.0221 a]pyrimidine-6-carboxamide
N-({4-[(3-hydroxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.005
0.0070 a]pyridine-6-carboxamide
N-({4-[(3-methanesulfonylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0060 0.0068
c]pyridine-2-carboxamide N-({4-[(3- 0.0256 0.016
methanesulfonylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
a]pyridine-6-carboxamide
N-({4-[(3-methanesulfonylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0017 0.0035 c]pyridine-2-carboxamide
N-({4-[(3-methoxy-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-
0.0036 0.0034 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(3-methoxy-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-
0.0079 0.0030 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-methoxy-4-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0046 0.0031 c]pyridine-2-carboxamide N-({4-[(3-methoxy-4- 0.0013
0.0017
methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide N-({4-[(3-methoxy-4- 0.0027 0.0015
methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(3-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-
0.0096 0.0028 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0022 0.0016 c]pyridine-2-carboxamide N-({4-[(3-methoxy-5- 0.0053
0.0016
methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(3-methoxy-5- 0.0016 0.0013
methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide N-({4-[(3-methoxy-5- 0.0024 0.0008
methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0209 0.0100 b]pyridine-5-carboxamide
N-({4-[(3-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-
0.0035 0.0069 2-carboxamide
N-({4-[(3-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.00497 0.00245 a]pyridine-6-carboxamide
N-({4-[(3-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0020
0.0124 a]pyrimidine-6-carboxamide
N-({4-[(3-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0023 0.0053 carboxamide
N-({4-[(3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.00812
0.00639 a]pyridine-6-carboxamide
N-({4-[(3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0019
0.0091 a]pyrimidine-6-carboxamide
N-({4-[(3-phenylbenzene)sulfonyl]phenyl}methyl)-1,3-benzothiazole-6-
0.0185 1-10 carboxamide
N-({4-[(3-phenylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0023 0.0119 c]pyridine-2-carboxamide
N-({4-[(3-phenylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0137 0.0234 carboxamide
N-({4-[(3-phenylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0122
0.0068 a]pyridine-6-carboxamide
N-({4-[(3-phenylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0009
0.0033 a]pyrimidine-6-carboxamide
N-({4-[(3-phenylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.0045 0.0100 2-carboxamide
N-({4-[(3-phenylpropane)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.014 0.078 c]pyridine-2-carboxamide
N-({4-[(3-propoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0304 0.041 b]pyridine-5-carboxamide
N-({4-[(3-propoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0102 0.0122 c]pyridine-2-carboxamide
N-({4-[(3-propoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-
0.0101 0.0252 2-carboxamide
N-({4-[(3-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0042
0.0063 a]pyridine-6-carboxamide
N-({4-[(3-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0048
0.0075 a]pyrimidine-6-carboxamide
N-({4-[(3-propoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3- 0.0040
0.0122 c]pyridine-2-carboxamide
N-({4-[(3-sulfamoylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0301 0.1-1 b]pyridine-5-carboxamide
N-({4-[(3-sulfamoylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0103 0.0546 a]pyridine-6-carboxamide
N-({4-[(3-sulfamoylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0020 0.0121 c]pyridine-2-carboxamide
N-({4-[(3-tert-butylbenzene)sulfonyl]phenyl}methyl)furo[2,3- 0.0093
0.0070 c]pyridine-2-carboxamide
N-({4-[(3-tert-butylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0097 0.0032 a]pyridine-6-carboxamide
N-({4-[(3-tert-butylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
<0.00065 0.0012 a]pyrimidine-6-carboxamide
N-({4-[(3-tert-butylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0105 0.0091 c]pyridine-2-carboxamide N-({4-[(4,5-difluoro-2-
0.0281 0.0259
methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
carboxamide N-({4-[(4,5-difluoro-2- 0.0281 0.0068
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(4,5-difluoro-2- 0.0119 0.0249
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(4-acetylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0289 0.0037 b]pyridine-5-carboxamide
N-({4-[(4-acetylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0052
0.0065 a]pyrimidine-6-carboxamide
N-({4-[(4-butoxy-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0709
0.0688 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-butoxy-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0800
0.0625 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-butoxy-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0160 0.0648 c]pyridine-2-carboxamide N-({4-[(4-butoxy-2- 0.0100
0.0224
methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide
N-({4-[(4-butoxy-2-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0033 1.0-0.1 c]pyridine-2-carboxamide
N-({4-[(4-butoxy-3-chlorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0045
0.0111 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-butoxy-3-chlorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0178
0.0124 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-butoxy-3-chlorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0047 0.0100 c]pyridine-2-carboxamide
N-({4-[(4-butoxy-3-chlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0041 0.0076 a]pyridine-6-carboxamide
N-({4-[(4-butoxy-3-chlorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0048 0.0125 c]pyridine-2-carboxamide
N-({4-[(4-butoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0536
0.0134 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-butoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0123 0.0139 c]pyridine-2-carboxamide
N-({4-[(4-butoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0062 0.0031 a]pyridine-6-carboxamide
N-({4-[(4-butoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0012 0.0031 a]pyrimidine-6-carboxamide
N-({4-[(4-butoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0047 0.0126 c]pyridine-2-carboxamide
N-({4-[(4-butoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0275 0.0225 b]pyridine-5-carboxamide
N-({4-[(4-butoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0084 0.0171 c]pyridine-2-carboxamide
N-({4-[(4-butoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0062 0.0130 carboxamide
N-({4-[(4-butoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0038
0.0028 a]pyridine-6-carboxamide
N-({4-[(4-butoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3- 0.0036
0.0103 c]pyridine-2-carboxamide
N-({4-[(4-butylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0712 0.0684 b]pyridine-5-carboxamide
N-({4-[(4-butylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0146 0.0358 c]pyridine-2-carboxamide
N-({4-[(4-butylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0181 0.0265 carboxamide
N-({4-[(4-butylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-
0.0057 0.0076 6-carboxamide
N-({4-[(4-butylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0053
0.0107 a]pyrimidine-6-carboxamide
N-({4-[(4-butylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.0029 0.0260 2-carboxamide
N-({4-[(4-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.0112
0.0004 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0072 0.0051 c]pyridine-2-carboxamide
N-({4-[(4-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0041 0.0007 a]pyridine-6-carboxamide
N-({4-[(4-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0020 0.0045 a]pyrimidine-6-carboxamide
N-({4-[(4-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0024 <0.0004 c]pyridine-2-carboxamide
N-({4-[(4-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0085 0.0248 c]pyridine-2-carboxamide N-({4-[(4-chloro-2- 0.0187
0.0126
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(4-chloro-2- 0.0033 0.0247
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(4-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0775
0.0587 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0249 0.0647 c]pyridine-2-carboxamide
N-({4-[(4-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0066 0.0539 a]pyrimidine-6-carboxamide
N-({4-[(4-chloro-3-fluorobenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0185 0.0065 c]pyridine-2-carboxamide
N-({4-[(4-chloro-3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.00722 0.00724 a]pyridine-6-carboxamide
N-({4-[(4-chloro-3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0019 0.0089 a]pyrimidine-6-carboxamide
N-({4-[(4-chloro-3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0127 0.0130 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-chloro-3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0055 0.0036 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-chloro-3-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0059 0.0060 c]pyridine-2-carboxamide N-({4-[(4-chloro-3- 0.0135
0.006
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(4-chloro-3- 0.0027 0.0052
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide N-({4-[(4-chloro-3- 0.0026 0.0023
methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(4-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0288 0.022 b]pyridine-5-carboxamide
N-({4-[(4-chlorobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0049 0.0142 carboxamide
N-({4-[(4-chlorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0025
0.0236 a]pyrimidine-6-carboxamide
N-({4-[(4-cyanobenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0284 0.0208 b]pyridine-5-carboxamide
N-({4-[(4-cyanobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0111 0.0251 c]pyridine-2-carboxamide
N-({4-[(4-cyanobenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0053 0.0309 carboxamide
N-({4-[(4-cyanobenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0160
0.0141 a]pyridine-6-carboxamide
N-({4-[(4-cyclohexylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0178 0.0117 a]pyridine-6-carboxamide
N-({4-[(4-cyclohexylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0058 0.0077 a]pyrimidine-6-carboxamide
N-({4-[(4-cyclohexylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0034 0.0129 c]pyridine-2-carboxamide
N-({4-[(4-ethoxy-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.1083
0.0667 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-ethoxy-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0092
0.0126 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-ethoxy-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0216 0.0274 c]pyridine-2-carboxamide N-({4-[(4-ethoxy-2- 0.0066
0.0111
methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(4-ethoxy-2- 0.0117 0.0607
methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(4-ethoxy-2-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0012 0.0132 c]pyridine-2-carboxamide
N-({4-[(4-ethoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0095
0.0052 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-ethoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.0205
0.0054 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-ethoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0127 0.0018 a]pyridine-6-carboxamide
N-({4-[(4-ethoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0009 0.0031 a]pyrimidine-6-carboxamide
N-({4-[(4-ethoxy-3-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0089 0.0036 c]pyridine-2-carboxamide
N-({4-[(4-ethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0151 0.0084 b]pyridine-5-carboxamide
N-({4-[(4-ethoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0025 0.0071 carboxamide
N-({4-[(4-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0045
0.0029 a]pyridine-6-carboxamide
N-({4-[(4-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0020
0.0061 a]pyrimidine-6-carboxamide
N-({4-[(4-ethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3- 0.0021
0.0040 c]pyridine-2-carboxamide
N-({4-[(4-ethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0050 0.007 carboxamide
N-({4-[(4-ethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-
0.0165 0.00736 6-carboxamide
N-({4-[(4-ethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0012
0.0062 a]pyrimidine-6-carboxamide
N-({4-[(4-fluoro-2,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-
0.0373 0.0459 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-fluoro-2,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-
0.0514 0.0128 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-2,5-dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0176 0.0242 c]pyridine-2-carboxamide N-({4-[(4-fluoro-2,5- 0.0440
0.011
dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(4-fluoro-2,5- 0.0058 0.0294
dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide N-({4-[(4-fluoro-2,5- 0.0042 0.0136
dimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(4-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.159
0.0742 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0127 0.0160 c]pyridine-2-carboxamide N-({4-[(4-fluoro-2- 0.0193
0.00705
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(4-fluoro-2- 0.0191 0.0736
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(4-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0788
0.0983 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0187 0.0651 c]pyridine-2-carboxamide
N-({4-[(4-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0130 0.1-1 a]pyrimidine-6-carboxamide
N-({4-[(4-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0239 0.0115 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0278 0.0054 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0078 0.0070 c]pyridine-2-carboxamide N-({4-[(4-fluoro-3- 0.0197
0.0067
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(4-fluoro-3- 0.0049 0.0108
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(4-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0090 0.0031 c]pyridine-2-carboxamide
N-({4-[(4-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0050
0.0083 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0132 0.006 c]pyridine-2-carboxamide
N-({4-[(4-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0235 0.00714 a]pyridine-6-carboxamide
N-({4-[(4-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0022 0.0096 a]pyrimidine-6-carboxamide
N-({4-[(4-methanesulfonylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0293
0.0238 pyrazolo[3,4-b]pyridine-5-carboxamide N-({4-[(4- 0.105
0.0247 methanesulfonylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
a]pyridine-6-carboxamide
N-({4-[(4-methoxy-2,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-
0.0368 0.0236 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-methoxy-2,5- 0.0123 0.0128
dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
carboxamide N-({4-[(4-methoxy-2,5- 0.0281 0.006
dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(4-methoxy-2,5- 0.0052 0.0130
dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(4-methoxy-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.029
0.0555 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-methoxy-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0216 0.0351 c]pyridine-2-carboxamide N-({4-[(4-methoxy-2- 0.0024
0.0679
methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(4-methoxy-3,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-
0.005 0.00185 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(4-methoxy-3,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-
0.0516 0.0017 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-methoxy-3,5- 0.0056 0.0018
dimethylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
carboxamide N-({4-[(4-methoxy-3,5- 0.0146 0.0014
dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(4-methoxy-3,5- 0.0027 0.0013
dimethylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide N-({4-[(4-methoxy-3,5- 0.0098 0.0009
dimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide N-({4-[(4-methoxy-3- 0.0141 0.00532
methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(4-methoxy-3- 0.0022 0.0055
methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0209 0.0143 b]pyridine-5-carboxamide
N-({4-[(4-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-
0.0055 0.006 2-carboxamide
N-({4-[(4-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.00974 0.00866 a]pyridine-6-carboxamide
N-({4-[(4-methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0027
0.0207 a]pyrimidine-6-carboxamide
N-({4-[(4-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.1208 0.006 carboxamide
N-({4-[(4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0176
0.012 a]pyridine-6-carboxamide
N-({4-[(4-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0043
0.0194 a]pyrimidine-6-carboxamide
N-({4-[(4-phenylbenzene)sulfonyl]phenyl}methyl)-1,3-benzothiazole-6-
0.0207 0.1-1 carboxamide
N-({4-[(4-phenylbenzene)sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-
0.0320 0.0117 b]pyridine-5-carboxamide
N-({4-[(4-phenylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0310 0.0133 c]pyridine-2-carboxamide
N-({4-[(4-phenylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
0.0037 0.0069 carboxamide
N-({4-[(4-phenylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0032
0.0076 a]pyrimidine-6-carboxamide
N-({4-[(4-phenylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.0030 0.0106 2-carboxamide
N-({4-[(4-phenylbutane)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.216 0.0715
c]pyridine-2-carboxamide
N-({4-[(4-propoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.0053 0.0067 c]pyridine-2-carboxamide
N-({4-[(4-propoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-
0.0495 0.012 2-carboxamide
N-({4-[(4-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0061
0.0019 a]pyridine-6-carboxamide
N-({4-[(4-propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.0022
0.0061 a]pyrimidine-6-carboxamide
N-({4-[(4-propoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3- 0.0043
0.0081 c]pyridine-2-carboxamide
N-({4-[(5-acetyl-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0277 0.0275 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(5-acetyl-2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0072 0.0038 c]pyridine-2-carboxamide N-({4-[(5-acetyl-2- 0.0379
0.0127
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(5-acetyl-2- 0.0172 0.0548
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(5-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0022 0.0005 a]pyridine-6-carboxamide
N-({4-[(5-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0019 0.0033 a]pyrimidine-6-carboxamide
N-({4-[(5-chloro-2-ethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0027 0.0005 c]pyridine-2-carboxamide N-({4-[(5-chloro-2- 0.014
0.1682
hydroxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide
N-({4-[(5-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0492 0.0081 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(5-chloro-2- 0.0191 0.0032
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(5-chloro-2- 0.0055 0.0061
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(5-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0227
0.0139 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(5-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0058 0.0078 c]pyridine-2-carboxamide
N-({4-[(5-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0019 0.0037 a]pyridine-6-carboxamide
N-({4-[(5-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0031 0.0043 a]pyrimidine-6-carboxamide
N-({4-[(5-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0048 0.0066 c]pyridine-2-carboxamide
N-({4-[(5-chloro-2-propoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0492 0.0251 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(5-chloro-2-propoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0075 0.0012 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(5-chloro-2-propoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0080 0.0093 c]pyridine-2-carboxamide N-({4-[(5-chloro-2- 0.0080
0.0032
propoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide
N-({4-[(5-chloro-2-propoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0057 0.0012 c]pyridine-2-carboxamide N-({4-[(5-cyano-2- 0.0146
0.0119
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide
N-({4-[(5-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0390 0.0151 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(5-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0022 0.0124 c]pyridine-2-carboxamide N-({4-[(5-fluoro-2- 0.022
0.00665
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(5-fluoro-2- 0.0073 0.0261
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(5-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.0020 0.0008 c]pyridine-2-carboxamide
N-({4-[(5-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.0204
0.0597 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(5-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-
0.0143 0.0249 c]pyridine-2-carboxamide
N-({4-[(5-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0126 0.0229 a]pyridine-6-carboxamide
N-({4-[(5-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)imidazo[1,2-
0.0027 0.0351 a]pyrimidine-6-carboxamide
N-({4-[(5-tert-butyl-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.0456 0.0216 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(5-tert-butyl-2- 0.0218 0.0101
methoxybenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
carboxamide N-({4-[(5-tert-butyl-2- 0.029 0.00677
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-
carboxamide N-({4-[(5-tert-butyl-2- 0.0098 0.0077
methoxybenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-
carboxamide
N-({4-[(6-chloro-2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)-
0.112 0.1-1 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[(6-chloro-2-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)-
0.0065 0.0071 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(6-chloro-2-fluoro-3- 0.0219 0.0293
methylbenzene)sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-
carboxamide N-({4-[(6-chloro-2-fluoro-3- 0.0077 0.0068
methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[1-(3-chlorophenyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)-1H-
0.0282 0.0556 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[1-(3-chlorophenyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)-1H-
0.0169 0.0131 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[1-(3-chlorophenyl)-1H-pyrazole-4- 0.0116 0.0140
sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carboxamide
N-({4-[1-(3-chlorophenyl)-1H-pyrazole-4- 0.0140 0.0064
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[1-(3-chlorophenyl)-1H-pyrazole-4- 0.0022 0.0115
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[1-(3-chlorophenyl)-1H-pyrazole-4- 0.0041 0.0139
sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-carboxamide
N-({4-[1-(4-fluorophenyl)-1H-pyrazole-4-sulfonyl]phenyl}methyl)-1H-
0.0184 0.0066 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[1-(4-fluorophenyl)-1H-pyrazole-4- 0.0069 0.0074
sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carboxamide
N-({4-[1-(4-fluorophenyl)-1H-pyrazole-4- 0.0045 0.0062
sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-carboxamide
N-({4-[1-(propan-2-yl)-1H-pyrazole-4- 0.008 0.0027
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[1-methyl-3-(trifluoromethyl)-1H-pyrazole-4- 0.0299 0.0278
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[1-methyl-5-(trifluoromethyl)-1H-pyrazole-4- 0.0534 0.0434
sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[1-methyl-5-(trifluoromethyl)-1H-pyrazole-4- 0.0040 0.0679
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[2-(3-fluorophenyl)-1,3-thiazole-4-sulfonyl]phenyl}methyl)-1H-
0.0271 0.0609 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[2-(3-fluorophenyl)-1,3-thiazole-4-sulfonyl]phenyl}methyl)-1H-
0.0192 0.0232 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[2-(3-fluorophenyl)-1,3-thiazole-4- 0.0119 0.0504
sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carboxamide
N-({4-[2-(3-fluorophenyl)-1,3-thiazole-4- 0.0229 0.0128
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[2-(3-fluorophenyl)-1,3-thiazole-4- 0.0010 0.0069
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[2-(3-fluorophenyl)-1,3-thiazole-4- 0.0066 0.0244
sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-carboxamide
N-({4-[2-(benzenesulfonyl)ethyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.023 0.166 c]pyridine-2-carboxamide
N-({4-[2-(dimethylamino)pyrimidine-5-sulfonyl]phenyl}methyl)-1H-
0.0079 0.0059 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[2-(dimethylamino)pyrimidine-5-sulfonyl]phenyl}methyl)-1H-
0.0190 0.0035 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[2-(dimethylamino)pyrimidine-5- 0.0258 0.012
sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carboxamide
N-({4-[2-(dimethylamino)pyrimidine-5- 0.0229 0.0036
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[2-(dimethylamino)pyrimidine-5- 0.0080 0.0017
sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-carboxamide
N-({4-[2-(morpholin-4-yl)pyridine-3-sulfonyl]phenyl}methyl)furo[2,3-
0.0325 0.0605 c]pyridine-2-carboxamide
N-({4-[2-(morpholin-4-yl)pyridine-3- 0.0312 0.1-1
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[2-(pyrrolidin-1-yl)-1,3-thiazole-5-sulfonyl]phenyl}methyl)-1H-
0.0028 0.0009 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[2-(pyrrolidin-1-yl)-1,3-thiazole-5-sulfonyl]phenyl}methyl)-1H-
0.0060 0.0005 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[2-(pyrrolidin-1-yl)-1,3-thiazole-5- 0.0024 0.0004
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[2-(pyrrolidin-1-yl)-1,3-thiazole-5- 0.0029 0.0009
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[2-(pyrrolidin-1-yl)-1,3-thiazole-5- 0.0015 0.0007
sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-carboxamide
N-({4-[2-(trifluoromethyl)imidazo[1,2-a]pyridine-6- 0.0497 0.0330
sulfonyl]phenyl}methyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[2-(trifluoromethyl)imidazo[1,2-a]pyridine-6- 0.0212 0.0119
sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carboxamide
N-({4-[2-(trifluoromethyl)imidazo[1,2-a]pyridine-6- 0.0362 0.0070
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[2-(trifluoromethyl)imidazo[1,2-a]pyridine-6- 0.0031 0.0039
sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-carboxamide
N-({4-[2-(trifluoromethyl)pyridine-3-sulfonyl]phenyl}methyl)furo[2,3-
0.0304 0.0279 c]pyridine-2-carboxamide
N-({4-[3-chloro-2-(morpholin-4-yl)pyridine-4- 0.0085 0.0018
sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-carboxamide
N-({4-[4-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)-1H-
0.0283 0.0118 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[4-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)furo[2,3-
0.0139 0.0061 c]pyridine-2-carboxamide
N-({4-[4-(trifluoromethyl)pyridine-2- 0.0197 0.0032
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[4-(trifluoromethyl)pyridine-2- 0.0087 0.0130
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[4-(trifluoromethyl)pyridine-2- 0.0036 0.0030
sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-carboxamide
N-({4-[5-(dimethylamino)pyrazine-2- 0.016 0.0036
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[5-(pyrrolidin-1-yl)pyridine-3-sulfonyl]phenyl}methyl)-1,3-
0.0092 0.1-1 benzothiazole-6-carboxamide
N-({4-[5-(pyrrolidin-1-yl)pyridine-3-sulfonyl]phenyl}methyl)-1H-
0.0179 0.0040 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[5-(pyrrolidin-1-yl)pyridine-3-sulfonyl]phenyl}methyl)-1H-
0.0139 0.0020 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[5-(pyrrolidin-1-yl)pyridine-3-sulfonyl]phenyl}methyl)furo[2,3-
0.0228 0.0049 c]pyridine-2-carboxamide
N-({4-[5-(pyrrolidin-1-yl)pyridine-3- 0.004 0.0005
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[5-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)-1H-
0.1-1 0.1-1 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[5-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)furo[2,3-
0.0370 0.1-1 c]pyridine-2-carboxamide
N-({4-[5-(trifluoromethyl)pyridine-2- 0.0463 0.0326
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[5-(trifluoromethyl)pyridine-2- 0.0059 0.0708
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[5-(trifluoromethyl)pyridine-2- 0.0235 0.1-1
sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-carboxamide
N-({4-[5-(trifluoromethyl)pyridine-3-sulfonyl]phenyl}methyl)-1H-
0.011 0.004 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[5-(trifluoromethyl)pyridine-3- 0.009 0.0013
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[6-(1H-pyrazol-1-yl)pyridine-3- 0.004 0.0019
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[6-(3,4-difluorophenyl)pyridine-2-sulfonyl]phenyl}methyl)-1H-
0.0178 0.0410 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[6-(3,4-difluorophenyl)pyridine-2-sulfonyl]phenyl}methyl)-1H-
0.0160 0.0127 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[6-(3,4-difluorophenyl)pyridine-2- 0.0050 0.0427
sulfonyl]phenyl}methyl)furo[2,3-c]pyridine-2-carboxamide
N-({4-[6-(3,4-difluorophenyl)pyridine-2- 0.0043 0.0057
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[6-(3,4-difluorophenyl)pyridine-2- 0.0022 0.0132
sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-carboxamide
N-({4-[6-(4-methylpiperazin-1-yl)pyridine-3-sulfonyl]phenyl}methyl)-
0.006 0.0006 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[6-(dimethylamino)pyridine-3-sulfonyl]phenyl}methyl)-1H-
0.0305 0.0033 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[6-(dimethylamino)pyridine-3-sulfonyl]phenyl}methyl)-1H-
0.0209 0.0034 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[6-(dimethylamino)pyridine-3-sulfonyl]phenyl}methyl)furo[2,3-
0.003 0.0018 c]pyridine-2-carboxamide
N-({4-[6-(dimethylamino)pyridine-3- 0.0449 0.0027
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[6-(dimethylamino)pyridine-3- 0.0027 0.0059
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[6-(dimethylamino)pyridine-3- 0.001 0.0006
sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-carboxamide
N-({4-[6-(morpholin-4-yl)pyridine-3-sulfonyl]phenyl}methyl)-1H-
0.0057 0.0032 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[6-(morpholin-4-yl)pyridine-3-sulfonyl]phenyl}methyl)-1H-
0.0096 0.0015 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[6-(morpholin-4-yl)pyridine-3-sulfonyl]phenyl}methyl)furo[2,3-
0.002 0.0009 c]pyridine-2-carboxamide
N-({4-[6-(morpholin-4-yl)pyridine-3- 0.0090 0.0015
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[6-(morpholin-4-yl)pyridine-3- 0.0011 0.0033
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[6-(morpholin-4-yl)pyridine-3-sulfonyl]phenyl}methyl)thieno[2,3-
0.0041 0.0007 c]pyridine-2-carboxamide
N-({4-[6-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)-1H-
0.0242 0.0111 pyrazolo[3,4-b]pyridine-5-carboxamide
N-({4-[6-(trifluoromethyl)pyridine-2-sulfonyl]phenyl}methyl)furo[2,3-
0.0050 0.0031 c]pyridine-2-carboxamide
N-({4-[6-(trifluoromethyl)pyridine-2- 0.0087 0.0015
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-carboxamide
N-({4-[6-(trifluoromethyl)pyridine-2- 0.0114 0.0204
sulfonyl]phenyl}methyl)imidazo[1,2-a]pyrimidine-6-carboxamide
N-({4-[6-(trifluoromethyl)pyridine-2- 0.0021 0.0022
sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-carboxamide
N-({4-[6-(trifluoromethyl)pyridine-3- 0.0076 0.0067
sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-carboxamide
N-(1,3-benzothiazol-6-ylmethyl)-4-[(3- 0.0100 >10
chlorobenzene)sulfonyl]benzamide
N-[(4-{[2-(2,2,2-trifluoroethoxy)-4- 0.009 0.0010
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
c]pyridine-2-carboxamide N-[(4-{[2-(2,2,2-trifluoroethoxy)-4- 0.007
0.0012 (trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[2-(benzyloxy)-5- 0.1-1 0.1-1
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-
b]pyridine-5-carboxamide N-[(4-{[2-(benzyloxy)-5- 0.1303 0.0259
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
c]pyridine-2-carboxamide N-[(4-{[2-(benzyloxy)-5- 0.0332 0.1-1
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[2-(dimethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.1-1 0.1-1 pyrrolo[3,2-c]pyridine-2-carboxamide N-[(4-{[2- 0.1-1
1-10 (dimethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
c]pyridine-2-carboxamide N-[(4-{[2- >0.1667 0.1-1
(dimethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[2- 0.1-1 1-10
(dimethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[2- 0.1-1 0.1-1
(dimethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide
N-[(4-{[2-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]-1H- 0.0520
0.0612 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[2-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]-1H- 0.0185
0.0067 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0133 0.0260 c]pyridine-2-carboxamide
N-[(4-{[2-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
0.0037 0.0396 a]pyrimidine-6-carboxamide
N-[(4-{[2-(methylsulfamoyl)benzene]sulfonyl}phenyl)methyl]-1H-
>0.167 >10 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[2-(methylsulfamoyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0513 0.0740 c]pyridine-2-carboxamide N-[(4-{[2- 0.0304 1-10
(methylsulfamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[2-(morpholin-4-ylmethyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0694 0.0465 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[2-(morpholin-4- 0.136 0.0342
ylmethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide N-[(4-{[2-(morpholin-4- 0.0145 0.1-1
ylmethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide
N-[(4-{[2-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0086 0.0146 c]pyridine-2-carboxamide N-[(4-{[2- 0.0024 0.0115
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0194 0.0593 c]pyridine-2-carboxamide N-[(4-{[2- 0.0341 0.0579
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[2- 0.0100 0.1-1
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[2,4-bis(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0816 0.0562 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[2,4-bis(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0401 0.0140 pyrrolo[3,2-c]pyridine-2-carboxamide N-[(4-{[2,4-
0.0530 0.0637
bis(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
c]pyridine-2-carboxamide N-[(4-{[2,4- 0.2202 0.0532
bis(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[2,4- 0.0188 0.0964
bis(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[2,4-bis(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.0215 0.0043 c]pyridine-2-carboxamide
N-[(4-{[2-chloro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0365 0.0384 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[2-chloro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0364 0.0088 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-chloro-3- 0.0184 0.0279
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-
2-carboxamide N-[(4-{[2-chloro-3- 0.0024 0.0246
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[2-chloro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.114 0.0869 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[2-chloro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.1269 0.0254 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-chloro-4- 0.0184 0.0644
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[2-chloro-5-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]-
0.0083 0.0262 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-chloro-5-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-
0.0531 0.0120 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-chloro-5- 0.0080 0.0125
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[2-chloro-5- 0.0139 0.0141
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-
2-carboxamide N-[(4-{[2-chloro-5- 0.0070 0.0141
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[2-fluoro-3-(propan-2- 0.0078
0.0040
yloxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide N-[(4-{[2-fluoro-3-(propan-2- 0.0018 0.0070
yloxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide N-[(4-{[2-fluoro-3-(propan-2- 0.0047 0.0066
yloxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-
carboxamide N-[(4-{[2-fluoro-3- 0.0098 0.0133
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide
N-[(4-{[2-fluoro-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-
0.0389 0.0344 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[2-fluoro-4-(1H-pyrazol-1- 0.0184 0.008
yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-[(4-{[2-fluoro-4-(1H-pyrazol-1- 0.00844 0.0128
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide N-[(4-{[2-fluoro-4-(1H-pyrazol-1- 0.0022 0.0190
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide
N-[(4-{[2-fluoro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0802 0.0281 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-fluoro-4- 0.0156 0.0157
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[2-fluoro-4- 0.0202 0.0423
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide N-[(4-{[2-methoxy-3- 0.0219 0.0148
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[2-methoxy-3- 0.0094 0.0128
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide N-[(4-{[2-methoxy-4-(1H-pyrazol-1- 0.0242
0.0094
yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-b]pyridine-5-
carboxamide N-[(4-{[2-methoxy-4-(1H-pyrazol-1- 0.0065 0.006
yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-[(4-{[2-methoxy-4-(1H-pyrazol-1- 0.021 0.00359
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide
N-[(4-{[2-methoxy-4-(1H-pyrazol-1- 0.0032 0.0087
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide N-[(4-{[2-methoxy-4- 0.1200 0.0281
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-
b]pyridine-5-carboxamide N-[(4-{[2-methoxy-4- 0.0264 0.00984
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[2-methoxy-4- 0.0044 0.0224
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[2-methoxy-4- 0.01 0.0022
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide
N-[(4-{[2-methoxy-5-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]-
0.0892 0.0294 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[2-methoxy-5-(propan-2- 0.0154 0.0124
yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-[(4-{[2-methoxy-5-(propan-2- 0.0352 0.0064
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide N-[(4-{[2-methoxy-5- 0.0926 0.0246
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-
b]pyridine-5-carboxamide N-[(4-{[2-methoxy-5- 0.0481 0.0066
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
c]pyridine-2-carboxamide N-[(4-{[2-methoxy-5- 0.0677 0.0144
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[2-methoxy-5- <0.00065 0.0058
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[2-methoxy-5- 0.0068 0.0036
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[2-methyl-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-
0.0271 0.0235 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[2-methyl-4-(1H-pyrazol-1- 0.0062 0.006
yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-[(4-{[2-methyl-4-(1H-pyrazol-1- 0.00799 0.0036
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide N-[(4-{[2-methyl-4-(1H-pyrazol-1- 0.0015 0.0031
yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-
carboxamide
N-[(4-{[2-methyl-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.1-1 0.0746 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[2-methyl-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0305 0.0253 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-methyl-4- 0.0345 0.0631
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-
2-carboxamide N-[(4-{[2-methyl-4- 0.0247 0.0166
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[2-methyl-4- 0.0071 0.0511
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[2-methyl-4- 0.0103 0.0242
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide
N-[(4-{[3-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0097 0.0074 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0075 0.0091 c]pyridine-2-carboxamide N-[(4-{[3-(1H-pyrazol-1-
0.0048 0.0062
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide
N-[(4-{[3-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.0015 0.0001 c]pyridine-2-carboxamide N-[(4-{[3-(2,2,2- 0.0072
0.0120
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-
carboxamide N-[(4-{[3-(2,2,2- 0.0150 0.0059
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3-(2,2,2- 0.0055 0.0114
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[3-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]-1H-
0.0285 0.0342 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]-1H-
0.0322 0.0143 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0148 0.0677 c]pyridine-2-carboxamide N-[(4-{[3-(2- 0.0157 0.0106
methylpropoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3-(2- 0.0039 0.0132
methylpropoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[3-(2- 0.0032 0.0252
methylpropoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-
2-carboxamide N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1- 0.0179 0.1-1
yl)benzene]sulfonyl}phenyl)methyl]-1,3-benzothiazole-6-carboxamide
N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1- 0.0253 0.0053
yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-b]pyridine-5-
carboxamide N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1- 0.0132 0.0016
yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-c]pyridine-2-
carboxamide N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1- 0.1-1 0.1-1
yl)benzene]sulfonyl}phenyl)methyl]-5-hydroxy-1H-indole-2-
carboxamide N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1- 0.0071 0.0035
yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1- 0.0072 0.0008
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1- 0.0018 0.0041
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide N-[(4-{[3-(3,5-dimethyl-1H-pyrazol-1- 0.0031 0.0015
yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-
carboxamide N-[(4-{[3-(4- 0.0151 0.0340
fluorophenoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3-(4- 0.0026 0.0656
fluorophenoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-
2-carboxamide N-[(4-{[3-(5-methyl-1,2,4-oxadiazol-3- 0.0079 0.0032
yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-[(4-{[3-(5-methyl-1,2,4-oxadiazol-3- 0.0028 0.0023
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide N-[(4-{[3-(5-methyl-1,2,4-oxadiazol-3- 0.0033 0.0010
yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-
carboxamide
N-[(4-{[3-(cyclopentylcarbamoyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0333 0.033 pyrazolo[3,4-b]pyridine-5-carboxamide N-[(4-{[3-
0.0066 0.0226
(cyclopentylcarbamoyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
c]pyridine-2-carboxamide N-[(4-{[3- 0.0103 0.0162
(cyclopentylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3- 0.0047 0.0483
(cyclopentylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[3- 0.0048 0.0138
(cyclopentylcarbamoyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide
N-[(4-{[3-(diethylcarbamoyl)-5-fluorobenzene]sulfonyl}phenyl)methyl]-
0.0093 0.0033 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(diethylcarbamoyl)-5- 0.0103 0.0038
fluorobenzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-
carboxamide N-[(4-{[3-(diethylcarbamoyl)-5- 0.0047 0.0168
fluorobenzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide
N-[(4-{[3-(difluoromethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0028 0.0030 c]pyridine-2-carboxamide N-[(4-{[3- 0.0021 0.0050
(difluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[3- 0.0020 0.0032
(dimethylsulfamoyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
c]pyridine-2-carboxamide N-[(4-{[3- 0.0020 0.0112
(dimethylsulfamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[3-(ethanesulfonyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0170 0.0155 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(ethanesulfonyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0027 0.0032 c]pyridine-2-carboxamide N-[(4-{[3- 0.0135 0.0060
(ethanesulfonyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3- 0.0027 0.0645
(ethanesulfonyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[3-(ethanesulfonyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.0028 0.0054 c]pyridine-2-carboxamide
N-[(4-{[3-(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0060 0.0064 c]pyridine-2-carboxamide N-[(4-{[3- 0.0031 0.0655
(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[3-(methoxymethyl)benzene]sulfonyl}phenyl)methyl]-1H- 0.0387
0.0394 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-(methoxymethyl)benzene]sulfonyl}phenyl)methyl]-1H- 0.0202
0.0128 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(methoxymethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0185 0.0134 c]pyridine-2-carboxamide N-[(4-{[3- 0.0067 0.0068
(methoxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3- 0.0032 0.0138
(methoxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[3-(methoxymethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.0026 0.0067 c]pyridine-2-carboxamide
N-[(4-{[3-(methylcarbamoyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0081 0.0143 c]pyridine-2-carboxamide N-[(4-{[3- 0.0037 0.1-1
(methylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]-1,3-
0.0401 1-10 benzothiazole-6-carboxamide
N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0167 0.0130 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0207 0.0106 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0084 0.0017 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0050 0.0056 c]pyridine-2-carboxamide N-[(4-{[3-(morpholin-4-
0.0077 0.0033
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide N-[(4-{[3-(morpholin-4- 0.0027 0.0135
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide
N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.0040 0.0019 c]pyridine-2-carboxamide
N-[(4-{[3-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.0036 0.0032 c]pyridine-2-carboxamide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1,3-
0.0210
0.1-1 benzothiazole-6-carboxamide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0536 0.0140 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0144 0.0033 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0113 0.0127 c]pyridine-2-carboxamide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
0.0114 0.0034 a]pyridine-6-carboxamide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
0.0051 0.0114 a]pyrimidine-6-carboxamide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
0.0012 0.0057 a]pyrimidine-6-carboxamide
N-[(4-{[3-(piperidin-1-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.0167 0.0136 c]pyridine-2-carboxamide N-[(4-{[3-(piperidin-1-
0.0091 0.0035
ylmethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide N-[(4-{[3-(piperidin-1- 0.0019 0.0306
ylmethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide
N-[(4-{[3-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]-1H- 0.0139
0.0063 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0045 0.007 c]pyridine-2-carboxamide
N-[(4-{[3-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
0.0124 0.00349 a]pyridine-6-carboxamide
N-[(4-{[3-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
0.0029 0.0053 a]pyrimidine-6-carboxamide
N-[(4-{[3-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]-1H-
0.0461 0.0245 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0126 0.0144 c]pyridine-2-carboxamide N-[(4-{[3-(propan-2- 0.0023
0.0105
yloxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide N-[(4-{[3-(propane-1- 0.0023 0.0862
sulfonamido)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[3-(propane-1- 0.0015 0.0032
sulfonamido)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-
carboxamide
N-[(4-{[3-(pyrimidin-2-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
0.0219 0.0038 a]pyridine-6-carboxamide
N-[(4-{[3-(pyrimidin-2-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
0.0032 0.0130 a]pyrimidine-6-carboxamide
N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1,3-
0.0088 1-10 benzothiazole-6-carboxamide
N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0171 0.0128 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0134 0.0028 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0082 0.0074 c]pyridine-2-carboxamide
N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
0.0136 0.0016 a]pyridine-6-carboxamide
N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
0.0025 0.0041 a]pyrimidine-6-carboxamide
N-[(4-{[3-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.0019 0.0025 c]pyridine-2-carboxamide
N-[(4-{[3-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-
0.0204 0.0071 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0034 0.0067 c]pyridine-2-carboxamide N-[(4-{[3- 0.00873 0.00318
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3- 0.0025 0.0027
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1,3-
0.006 0.5481 benzothiazole-6-carboxamide
N-[(4-{[3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0607 0.0104 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0054 0.0048 c]pyridine-2-carboxamide N-[(4-{[3- 0.00842 0.00172
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3- 0.0027 0.0030
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[3-chloro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0843 0.0264 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-chloro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0133 0.0077 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-chloro-4- 0.0079 0.0062
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-
2-carboxamide N-[(4-{[3-chloro-4- 0.0029 0.0012
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3-chloro-4- 0.0028 0.0018
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[3-chloro-4- 0.0030 0.0023
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide N-[(4-{[3-chloro-5- 0.0084 0.0017
(diethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
c]pyridine-2-carboxamide N-[(4-{[3-chloro-5- 0.0009 0.0012
(diethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[3-chloro-5- 0.0023 0.0008
(diethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide N-[(4-{[3-chloro-5- 0.0058 0.0014
(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3-chloro-5- 0.0034 0.0114
(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[3-chloro-5- 0.0033 0.0008
(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide
N-[(4-{[3-chloro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0078 0.00273 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-chloro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0199 0.0027 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-chloro-5- 0.0044 0.0004
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[3-fluoro-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-
0.0131 0.0033 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-fluoro-4-(1H-pyrazol-1- 0.0173 0.005
yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-[(4-{[3-fluoro-4-(1H-pyrazol-1- 0.00537 0.00341
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide N-[(4-{[3-fluoro-4-(2,2,2- 0.0103 0.0223
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-
b]pyridine-5-carboxamide N-[(4-{[3-fluoro-4-(2,2,2- 0.0069 0.0238
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-
carboxamide N-[(4-{[3-fluoro-4-(2,2,2- 0.0150 0.008
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3-fluoro-4-(2,2,2- 0.0044 0.0073
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[3-fluoro-4-(2,2,2- 0.0046 0.0235
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-
2-carboxamide N-[(4-{[3-fluoro-4- 0.0123 0.0112
(methylsulfanyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-
carboxamide N-[(4-{[3-fluoro-4- 0.0056 0.0027
(methylsulfanyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3-fluoro-4- 0.0022 0.0020
(methylsulfanyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide
N-[(4-{[3-fluoro-4-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-
0.0174 0.0137 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-fluoro-4-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-
0.0262 0.0205 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-fluoro-4- 0.0100 0.0156
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-
c]pyridine-2-carboxamide N-[(4-{[3-fluoro-4- 0.0084 0.0063
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3-fluoro-4- 0.0040 0.0118
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[3-fluoro-4- 0.0115 0.0115
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide
N-[(4-{[3-fluoro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0103 0.0130 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-fluoro-4- 0.0092 0.0137
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-
2-carboxamide N-[(4-{[3-fluoro-4- 0.0402 0.0044
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3-fluoro-4- 0.0041 0.0069
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[3-fluoro-4- 0.0088 0.0072
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide N-[(4-{[3-fluoro-5-(2,2,2- 0.008 0.00482
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-
b]pyridine-5-carboxamide N-[(4-{[3-fluoro-5-(2,2,2- 0.0056 0.0019
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
c]pyridine-2-carboxamide N-[(4-{[3-fluoro-5-(2,2,2- 0.0074 0.0061
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-
carboxamide N-[(4-{[3-fluoro-5-(2,2,2- 0.0019 0.0015
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[3-fluoro-5-(2,2,2- 0.0029 0.0035
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-
2-carboxamide
N-[(4-{[3-fluoro-5-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]-
0.0112 0.00949 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-fluoro-5-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]-
0.0132 0.0070 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-fluoro-5-(2- 0.0103 0.0129
methylpropoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-
carboxamide N-[(4-{[3-fluoro-5-(2- 0.0113 0.003
methylpropoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[3-fluoro-5-(2- 0.0031 0.0034
methylpropoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[3-fluoro-5-(2- 0.0048 0.0075
methylpropoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-
2-carboxamide
N-[(4-{[3-fluoro-5-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]-
0.004 0.0008 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-fluoro-5-(morpholin-4- 0.003 0.0006
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide N-[(4-{[3-fluoro-5-(pyrrolidin-1- 0.0039 0.0022
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide N-[(4-{[3-fluoro-5-(pyrrolidin-1- 0.0031 0.0020
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide N-[(4-{[3-fluoro-5-(pyrrolidin-1- 0.0012 0.0027
yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-
carboxamide
N-[(4-{[3-fluoro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0112 0.00345 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[3-fluoro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0262 0.0036 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-fluoro-5- 0.0074 0.0050
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-
2-carboxamide N-[(4-{[3-fluoro-5- 0.0059 0.0011
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[3-fluoro-5- 0.0102 0.0031
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide
N-[(4-{[4-(1-cyanocyclopentyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0601 0.0189 pyrrolo[3,2-c]pyridine-2-carboxamide N-[(4-{[4-(1-
0.0080 0.0060
cyanocyclopentyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-
2-carboxamide N-[(4-{[4-(1- 0.0107 0.0030
cyanocyclopentyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[4-(1- 0.0032 0.0047
cyanocyclopentyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[4-(1H-imidazol-1- <0.00065
0.0122
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide N-[(4-{[4-(1H-imidazol-1- 0.0190 0.0137
ylmethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-
carboxamide N-[(4-{[4-(1H-imidazol-1- 0.0053 0.0122
ylmethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-
carboxamide
N-[(4-{[4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0123 0.0075 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0041 0.0073 c]pyridine-2-carboxamide
N-[(4-{[4-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]-1H-
0.0263 0.0162 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]-1H-
0.0127 0.0094 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-(2-methylpropoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0094 0.0116 c]pyridine-2-carboxamide N-[(4-{[4-(2- 0.0022 0.0027
methylpropoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[4-(2- 0.0055 0.0052
methylpropoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[4-(2- 0.0040 0.0103
methylpropoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-
2-carboxamide
N-[(4-{[4-(4-ethoxyphenyl)benzene]sulfonyl}phenyl)methyl]-1H- 0.009
0.0090 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-(4-methylpiperazin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-
0.004 0.0013 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-(4-methylpiperazin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-
0.003 0.0008 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-(4-methylpiperazin-1- 0.001 0.0005
yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-[(4-{[4-(4-methylpiperazin-1- 0.001 0.0002
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide N-[(4-{[4-(4-methylpiperazin-1- 0.001 0.0003
yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-
carboxamide N-[(4-{[4-(difluoromethyl)-3- 0.0082 0.0279
fluorobenzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide
N-[(4-{[4-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]-1H- 0.0266
0.0128 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]-1H- 0.0225
0.0068 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0049 0.0066 c]pyridine-2-carboxamide
N-[(4-{[4-(ethoxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
0.0027 0.0052 a]pyrimidine-6-carboxamide
N-[(4-{[4-(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]-1H- 0.103
0.0968 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0145 0.0141 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0045 0.0067 c]pyridine-2-carboxamide N-[(4-{[4- 0.0120 0.0063
(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[4- 0.0226 0.0878
(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[4-(ethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.0015 0.0033 c]pyridine-2-carboxamide
N-[(4-{[4-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0049 0.0062 c]pyridine-2-carboxamide N-[(4-{[4- 0.0142 0.0129
(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide
N-[(4-{[4-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.0038 0.0066 c]pyridine-2-carboxamide
N-[(4-{[4-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]-1H-
0.00445 0.00247 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0046 0.0025 c]pyridine-2-carboxamide N-[(4-{[4-(morpholin-4-
0.0035 0.0009
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide N-[(4-{[4-(morpholin-4- 0.0017 0.0040
yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide
N-[(4-{[4-(morpholin-4-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.0016 0.0015 c]pyridine-2-carboxamide
N-[(4-{[4-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0119 0.0080 c]pyridine-2-carboxamide
N-[(4-{[4-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
0.0146 0.00666 a]pyridine-6-carboxamide
N-[(4-{[4-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
0.0017 0.0081 a]pyrimidine-6-carboxamide
N-[(4-{[4-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]-1H-
0.0080 0.0066 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0068 0.0057 c]pyridine-2-carboxamide N-[(4-{[4-(propan-2- 0.0043
0.0032
yloxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide
N-[(4-{[4-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-
0.006 0.0045 pyrazolo[3,4-b]pyridine-6-carboxamide
N-[(4-{[4-(pyrrolidin-1-yl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
0.003 0.0014 a]pyridine-6-carboxamide
N-[(4-{[4-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-
0.0346 0.0223 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0094 0.0277 c]pyridine-2-carboxamide N-[(4-{[4- 0.0050 0.0176
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.0199 0.0194 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-
0.0087 0.0198 c]pyridine-2-carboxamide N-[(4-{[4- 0.0060 0.0235
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[4-chloro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.147 0.0783 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-chloro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0422 0.0174 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-chloro-2- 0.0098 0.0254
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-
2-carboxamide N-[(4-{[4-chloro-2- 0.0198 0.0085
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[4-chloro-2- 0.0079 0.0684
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[4-chloro-2- 0.0070 0.0096
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide N-[(4-{[4-chloro-3- 0.0060 0.0069
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-
2-carboxamide N-[(4-{[4-chloro-3- 0.00984 0.00357
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[4-chloro-3- 0.0028 0.0043
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[4-fluoro-2-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]-
0.0254 0.0033 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-fluoro-2-(propan-2- 0.0156 0.0139
yloxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-
carboxamide N-[(4-{[4-fluoro-2-(propan-2- 0.0222 0.0021
yloxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide N-[(4-{[4-fluoro-2-(propan-2- 0.0035 0.0150
yloxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide N-[(4-{[4-fluoro-2-(propan-2- 0.0050 0.0016
yloxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-
carboxamide
N-[(4-{[4-fluoro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.112 0.109 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-fluoro-2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0270 0.0141 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-fluoro-2- 0.0040 0.0150
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[4-fluoro-2- 0.0187 0.1-1
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[4-fluoro-2- 0.0064 0.0143
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide N-[(4-{[4-fluoro-3-(2,2,2- 0.01 0.0147
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-
b]pyridine-5-carboxamide N-[(4-{[4-fluoro-3-(2,2,2- 0.0103
0.0065
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
c]pyridine-2-carboxamide N-[(4-{[4-fluoro-3-(2,2,2- 0.0087 0.0255
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-
carboxamide N-[(4-{[4-fluoro-3-(2,2,2- 0.0024 0.0065
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[4-fluoro-3-(2,2,2- 0.0033 0.0118
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-
2-carboxamide
N-[(4-{[4-fluoro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0394 0.0138 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[4-fluoro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.0164 0.0043 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-fluoro-3- 0.0082 0.0072
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-
2-carboxamide N-[(4-{[4-fluoro-3- 0.0040 0.0017
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[4-fluoro-3- 0.0080 0.0032
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[4-fluoro-3- 0.0040 0.0028
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide N-[(4-{[4-methoxy-2- 0.0868 0.0628
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-
b]pyridine-5-carboxamide N-[(4-{[4-methoxy-2- 0.0804 0.0130
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
c]pyridine-2-carboxamide N-[(4-{[4-methoxy-2- 0.0146 0.0152
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-
2-carboxamide N-[(4-{[4-methoxy-2- 0.0070 0.0657
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide N-[(4-{[4-methoxy-2- 0.0217 0.0130
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide
N-[(4-{[5-(diethylcarbamoyl)-2-fluorobenzene]sulfonyl}phenyl)methyl]-
0.0384 0.0262 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[5-chloro-2-(2,2,2- 0.001 0.0003
trifluoroethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[5-chloro-2-(2,2- 0.005 0.0005
difluoroethoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
c]pyridine-2-carboxamide N-[(4-{[5-chloro-2-(2,2- 0.002 0.0003
difluoroethoxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[5-chloro-2-(prop-2-yn-1- 0.007
0.0014
yloxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-
carboxamide
N-[(4-{[5-chloro-2-(propan-2-yloxy)benzene]sulfonyl}phenyl)methyl]-
0.0678 0.0271 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[5-chloro-2-(propan-2- 0.0091 0.0121
yloxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-
carboxamide N-[(4-{[5-chloro-2-(propan-2- 0.0047 0.0146
yloxy)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-
carboxamide
N-[(4-{[5-fluoro-2-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]-
0.109 0.1-1 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{[5-fluoro-2-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]-
0.0169 0.0675 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[5-fluoro-2- 0.0229 0.0670
(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-
2-carboxamide N-[(4-{[5-fluoro-2- 0.0104 0.0650
(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyridine-6-carboxamide N-[(4-{[5-fluoro-2- 0.0129 0.1-1
(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]imidazo[1,2-
a]pyrimidine-6-carboxamide
N-[(4-{[5-fluoro-2-(hydroxymethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,-
3- 0.0077 0.0249 c]pyridine-2-carboxamide N-[(4-{[5-hydroxy-2-
0.0219 0.0679
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-
b]pyridine-5-carboxamide N-[(4-{[5-hydroxy-2- 0.0064 0.0115
(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]furo[2,3-
c]pyridine-2-carboxamide
N-[(4-{2-[ethyl(methyl)amino]-1,3-thiazole-5-sulfonyl}phenyl)methyl]-
0.0036 0.0015 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{2-[ethyl(methyl)amino]-1,3-thiazole-5- 0.0048 0.0009
sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-[(4-{2-[ethyl(methyl)amino]-1,3-thiazole-5- 0.0033 0.0004
sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-carboxamide
N-[(4-{2-[ethyl(methyl)amino]-1,3-thiazole-5- 0.0018 0.0009
sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-carboxamide
N-[(4-{2-[ethyl(methyl)amino]-1,3-thiazole-5- 0.0029 0.0012
sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-carboxamide
N-[(4-{5H,6H,7H,8H,9H-imidazo[1,2-a]azepine-3- 0.0316 0.0123
sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{5H,6H,7H,8H,9H-imidazo[1,2-a]azepine-3- 0.0060 0.0057
sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-[(4-{5H,6H,7H,8H,9H-imidazo[1,2-a]azepine-3- 0.0011 0.0287
sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-carboxamide
N-[(4-{5H,6H,7H,8H,9H-imidazo[1,2-a]azepine-3- 0.0030 0.0008
sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-carboxamide
N-[(4-{6-chloroimidazo[1,2-a]pyridine-3-sulfonyl}phenyl)methyl]-1H-
0.0033 0.0008 pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{6-chloroimidazo[1,2-a]pyridine-3-sulfonyl}phenyl)methyl]-1H-
0.0132 0.0014 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{6-chloroimidazo[1,2-a]pyridine-3- 0.0012 0.0004
sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-[(4-{6-chloroimidazo[1,2-a]pyridine-3- 0.0053 0.0004
sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-carboxamide
N-[(4-{6-chloroimidazo[1,2-a]pyridine-3- 0.0016 0.0004
sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-carboxamide
N-[(4-{6-chloroimidazo[1,2-a]pyridine-3- 0.0012 0.0004
sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-carboxamide
N-[(4-{8-oxatricyclo[7.4.0.0.sup.2,.sup.7]trideca-1(13),2,4,6,9,11-hexaene-
-6- 0.021 0.00752
sulfonyl}phenyl)methyl]-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-[(4-{8-oxatricyclo[7.4.0.0.sup.2,.sup.7]trideca-1(13),2,4,6,9,11-hexaene-
-6- 0.0124 0.0128
sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-[(4-{8-oxatricyclo[7.4.0.0.sup.2,.sup.7]trideca-1(13),2,4,6,9,11-hexaene-
-6- 0.0017 0.0029
sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-carboxamide
N-[(4-{8-thiatricyclo[7.4.0.0.sup.2,.sup.7]trideca-1(13),2,4,6,9,11-hexaen-
e-6- 0.0035 0.0032
sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{8-thiatricyclo[7.4.0.0.sup.2,.sup.7]trideca-1(13),2,4,6,9,11-hexaen-
e-6- 0.0087 0.012
sulfonyl}phenyl)methyl]furo[2,3-c]pyridine-2-carboxamide
N-[(4-{8-thiatricyclo[7.4.0.0.sup.2,.sup.7]trideca-1(13),2,4,6,9,11-hexaen-
e-6- 0.0018 0.0020
sulfonyl}phenyl)methyl]imidazo[1,2-a]pyrimidine-6-carboxamide
N-[(4-{8-thiatricyclo[7.4.0.0.sup.2,.sup.7]trideca-1(13),2,4,6,9,11-hexaen-
e-6- 0.0014 0.0043
sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-carboxamide
N-{[4-({3-[(2- 0.0193 0.0458
methylpropyl)carbamoyl]benzene}sulfonyl)phenyl]methyl}-1H-
pyrrolo[3,2-c]pyridine-2-carboxamide N-{[4-({3-[(2- 0.0169 0.0263
methylpropyl)carbamoyl]benzene}sulfonyl)phenyl]methyl}furo[2,3-
c]pyridine-2-carboxamide N-{[4-({3-[(2- 0.0070 0.0456
methylpropyl)carbamoyl]benzene}sulfonyl)phenyl]methyl}imidazo[1,2-
a]pyrimidine-6-carboxamide N-{[4-({3-[(2- 0.0052 0.0145
methylpropyl)carbamoyl]benzene}sulfonyl)phenyl]methyl}thieno[2,3-
c]pyridine-2-carboxamide N-{[4-({3- 0.0047 0.0062
[(dimethylamino)methyl]benzene}sulfonyl)phenyl]methyl}furo[2,3-
c]pyridine-2-carboxamide N-{[4-({3- 0.0044 0.0660
[(dimethylamino)methyl]benzene}sulfonyl)phenyl]methyl}imidazo[1,2-
a]pyrimidine-6-carboxamide
N-{[4-({3-[(morpholin-4-yl)carbonyl]benzene}sulfonyl)phenyl]methyl}-
0.1235 0.1-1 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-{[4-({3-[(propan-2- 0.0151 0.0157
yl)carbamoyl]benzene}sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
carboxamide N-{[4-({3-[(propan-2- 0.0222 0.0504
yl)carbamoyl]benzene}sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-
6-carboxamide N-{[4-({3-[(propan-2- 0.0070 0.0658
yl)carbamoyl]benzene}sulfonyl)phenyl]methyl}imidazo[1,2-
a]pyrimidine-6-carboxamide N-{[4-({3-[(propan-2- 0.0027 0.0067
yl)carbamoyl]benzene}sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
carboxamide N-{[4-({3-[2- 0.0118 0.0058
(dimethylamino)ethoxy]benzene}sulfonyl)phenyl]methyl}furo[2,3-
c]pyridine-2-carboxamide
N-{[4-({3-[2-(dimethylamino)ethyl]benzene}sulfonyl)phenyl]methyl}-
0.0292 0.0223 1H-pyrrolo[3,2-c]pyridine-2-carboxamide N-{[4-({3-[2-
0.0035 0.1-1
(dimethylamino)ethyl]benzene}sulfonyl)phenyl]methyl}imidazo[1,2-
a]pyrimidine-6-carboxamide N-{[4-({3-[2- 0.0025 0.0016
(dimethylamino)ethyl]benzene}sulfonyl)phenyl]methyl}thieno[2,3-
c]pyridine-2-carboxamide
N-{[4-({3-[2-(morpholin-4-yl)ethoxy]benzene}sulfonyl)phenyl]methyl}-
0.0649 0.0126 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-{[4-({3-[2-(morpholin-4- 0.0068 0.0034
yl)ethoxy]benzene}sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-
carboxamide N-{[4-({3-[2-(morpholin-4- 0.0031 0.0247
yl)ethoxy]benzene}sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-
6-carboxamide N-{[4-({3-[2-(morpholin-4- 0.0030 0.0015
yl)ethoxy]benzene}sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
carboxamide N-{[4-({4-[(1R)-1- 0.0285 0.0122
hydroxybutyl]benzene}sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
carboxamide N-{[4-({4-[(1R)-1- 0.0048 0.0142
hydroxybutyl]benzene}sulfonyl)phenyl]methyl}imidazo[1,2-
a]pyrimidine-6-carboxamide N-{[4-({4- 0.0033 0.0246
[(dimethylamino)methyl]benzene}sulfonyl)phenyl]methyl}imidazo[1,2-
a]pyrimidine-6-carboxamide
N-{[4-({4-[(pyrrolidin-1-yl)carbonyl]benzene}sulfonyl)phenyl]methyl}-
0.0158 0.0093 1H-pyrazolo[3,4-b]pyridine-5-carboxamide
N-{[4-({4-[(pyrrolidin-1- 0.0015 0.0014
yl)carbonyl]benzene}sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
carboxamide N-{[4-({4-[(pyrrolidin-1- 0.0037 0.0017
yl)carbonyl]benzene}sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
carboxamide N-{[4-({4-[2- 0.0021 0.0008
(dimethylamino)ethyl]benzene}sulfonyl)phenyl]methyl}imidazo[1,2-
a]pyridine-6-carboxamide N-{[4-({4-[2- 0.0020 0.0181
(dimethylamino)ethyl]benzene}sulfonyl)phenyl]methyl}imidazo[1,2-
a]pyrimidine-6-carboxamide
N-{[4-({4-[2-(pyrrolidin-1-yl)ethoxy]benzene}sulfonyl)phenyl]methyl}-
0.003 0.0023 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-{[4-({4-fluoro-3-[(propan-2- 0.0852 0.0631
yl)carbamoyl]benzene}sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-
b]pyridine-5-carboxamide N-{[4-({4-fluoro-3-[(propan-2- 0.0077
0.0854 yl)carbamoyl]benzene}sulfonyl)phenyl]methyl}imidazo[1,2-
a]pyrimidine-6-carboxamide N-{[4-({4-fluoro-3-[(propan-2- 0.0213
0.0068
yl)carbamoyl]benzene}sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
carboxamide
N-{[4-(1,3-thiazole-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
0.0198 0.0786 carboxamide
N-{[4-(1,3-thiazole-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-
0.021 0.0994 carboxamide
N-{[4-(1,3-thiazole-2-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
0.0144 0.0751 carboxamide
N-{[4-(1,4-dimethyl-1H-imidazole-2-sulfonyl)phenyl]methyl}furo[2,3-
0.0607 0.1-1 c]pyridine-2-carboxamide
N-{[4-(1,4-dimethyl-1H-imidazole-2- 0.1-1 0.0954
sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-carboxamide
N-{[4-(1,4-dimethyl-1H-imidazole-2- 0.0316 1-10
sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-carboxamide
N-{[4-(1,5-dimethyl-1H-imidazole-2-sulfonyl)phenyl]methyl}furo[2,3-
0.0574 0.0659 c]pyridine-2-carboxamide
N-{[4-(1,5-dimethyl-1H-imidazole-2- 0.0309 0.0731
sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-carboxamide
N-{[4-(1,5-dimethyl-1H-imidazole-2- 0.0329 1-10
sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-carboxamide
N-{[4-(1-benzothiophene-7-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-
0.0099 0.0128 b]pyridine-5-carboxamide
N-{[4-(1-benzothiophene-7-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-
0.0049 0.0139 2-carboxamide
N-{[4-(1-benzothiophene-7-sulfonyl)phenyl]methyl}thieno[2,3- 0.0015
0.0015 c]pyridine-2-carboxamide
N-{[4-(1H-indole-7-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4- 0.0147
0.0432 b]pyridine-5-carboxamide
N-{[4-(1-methyl-1H-indazole-6-sulfonyl)phenyl]methyl}thieno[2,3-
0.0023 0.0011 c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-7-sulfonyl)phenyl]methyl}-1H- 0.0918
0.0869 pyrazolo[3,4-b]pyridine-5-carboxamide
N-{[4-(1-methyl-1H-indazole-7-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-
0.0371 0.0111 c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-7-sulfonyl)phenyl]methyl}furo[2,3-
0.0115 0.0275 c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-indazole-7-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0287 0.0275 a]pyridine-6-carboxamide
N-{[4-(1-methyl-1H-indazole-7-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0233 0.1-1 a]pyrimidine-6-carboxamide
N-{[4-(1-methyl-1H-indazole-7-sulfonyl)phenyl]methyl}thieno[2,3-
0.0045 0.0104 c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-indole-2-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-
0.0140 0.0132 b]pyridine-5-carboxamide
N-{[4-(1-methyl-1H-indole-2-sulfonyl)phenyl]methyl}thieno[2,3-
0.0052 0.0034 c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}-1H- 0.182
0.1-1 pyrazolo[3,4-b]pyridine-5-carboxamide
N-{[4-(1-methyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}furo[2,3-
0.0168 0.0654 c]pyridine-2-carboxamide
N-{[4-(1-methyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0082 0.1-1 a]pyrimidine-6-carboxamide
N-{[4-(1-propyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}-1H- 0.008
0.0070 pyrazolo[3,4-b]pyridine-5-carboxamide
N-{[4-(1-propyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-
0.0149 0.0059 c]pyridine-2-carboxamide
N-{[4-(1-propyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}furo[2,3-
0.0057 0.0064 c]pyridine-2-carboxamide
N-{[4-(1-propyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0049 0.0052 a]pyridine-6-carboxamide
N-{[4-(1-propyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}thieno[2,3-
0.0019 0.0016 c]pyridine-2-carboxamide
N-{[4-(2,3-dihydro-1,4-benzodioxine-6- 0.0055 0.0062
sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-carboxamide
N-{[4-(2,3-dihydro-1,4-benzodioxine-6- 0.0002 0.0005
sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-carboxamide
N-{[4-(2,3-dihydro-1-benzofuran-7-sulfonyl)phenyl]methyl}-1H-
0.0248 0.0147 pyrazolo[3,4-b]pyridine-5-carboxamide
N-{[4-(2,3-dihydro-1-benzofuran-7-sulfonyl)phenyl]methyl}-1H-
0.0140 0.0038 pyrrolo[3,2-c]pyridine-2-carboxamide
N-{[4-(2,3-dihydro-1-benzofuran-7-sulfonyl)phenyl]methyl}furo[2,3-
0.0060 0.0071 c]pyridine-2-carboxamide
N-{[4-(2,3-dihydro-1-benzofuran-7- 0.0125 0.0064
sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-carboxamide
N-{[4-(2,3-dihydro-1-benzofuran-7- 0.0021 0.0258
sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-carboxamide
N-{[4-(2,3-dihydro-1-benzofuran-7-sulfonyl)phenyl]methyl}thieno[2,3-
0.0022 0.0030 c]pyridine-2-carboxamide
N-{[4-(2,6-dimethoxypyridine-3-sulfonyl)phenyl]methyl}-1H- 0.0307
0.0020 pyrazolo[3,4-b]pyridine-5-carboxamide
N-{[4-(2,6-dimethoxypyridine-3-sulfonyl)phenyl]methyl}furo[2,3-
0.0066 0.011 c]pyridine-2-carboxamide
N-{[4-(2,6-dimethoxypyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0433 0.0092 a]pyridine-6-carboxamide
N-{[4-(2H-1,3-benzodioxole-4-sulfonyl)phenyl]methyl}-1H- 0.047
0.0884 pyrazolo[3,4-b]pyridine-5-carboxamide
N-{[4-(2H-1,3-benzodioxole-4-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-
0.0205 0.0118 c]pyridine-2-carboxamide
N-{[4-(2H-1,3-benzodioxole-4-sulfonyl)phenyl]methyl}furo[2,3-
0.0258 0.0266 c]pyridine-2-carboxamide
N-{[4-(2H-1,3-benzodioxole-4-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0071 0.0130 a]pyridine-6-carboxamide
N-{[4-(2H-1,3-benzodioxole-4-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0029 0.0933 a]pyrimidine-6-carboxamide
N-{[4-(2H-1,3-benzodioxole-4-sulfonyl)phenyl]methyl}thieno[2,3-
0.0033 0.0072 c]pyridine-2-carboxamide
N-{[4-(2H-1,3-benzodioxole-5-sulfonyl)phenyl]methyl}-1H- 0.0482
0.0074 pyrazolo[3,4-b]pyridine-5-carboxamide
N-{[4-(2H-1,3-benzodioxole-5-sulfonyl)phenyl]methyl}furo[2,3-
0.0053 0.0087 c]pyridine-2-carboxamide
N-{[4-(2H-1,3-benzodioxole-5-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0107 0.00533 a]pyridine-6-carboxamide
N-{[4-(2H-1,3-benzodioxole-5-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0030 0.0117 a]pyrimidine-6-carboxamide
N-{[4-(2-methyl-1,3-thiazole-4-sulfonyl)phenyl]methyl}-1H- 0.0828
0.0207 pyrazolo[3,4-b]pyridine-5-carboxamide
N-{[4-(2-methyl-1,3-thiazole-4-sulfonyl)phenyl]methyl}furo[2,3-
0.0367 0.0690 c]pyridine-2-carboxamide
N-{[4-(2-methyl-1,3-thiazole-4-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0286 1-10 a]pyrimidine-6-carboxamide
N-{[4-(2-methyl-2H-indazole-5-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0133 0.0058 a]pyridine-6-carboxamide
N-{[4-(2-methyl-2H-indazole-5-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0012 0.0082 a]pyrimidine-6-carboxamide
N-{[4-(2-methyl-2H-indazole-5-sulfonyl)phenyl]methyl}thieno[2,3-
0.0055 0.0033 c]pyridine-2-carboxamide
N-{[4-(2-methyl-2H-indazole-6-sulfonyl)phenyl]methyl}-1H- 0.0147
0.0070 pyrazolo[3,4-b]pyridine-5-carboxamide
N-{[4-(2-methyl-2H-indazole-6-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-
0.0025 0.0032 c]pyridine-2-carboxamide
N-{[4-(2-methyl-2H-indazole-6-sulfonyl)phenyl]methyl}furo[2,3-
0.0034 0.0028 c]pyridine-2-carboxamide
N-{[4-(2-methyl-2H-indazole-6-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0019 0.0017 a]pyridine-6-carboxamide
N-{[4-(2-methyl-2H-indazole-6-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0012 0.0061 a]pyrimidine-6-carboxamide
N-{[4-(2-methyl-2H-indazole-6-sulfonyl)phenyl]methyl}thieno[2,3-
0.0014 0.0015 c]pyridine-2-carboxamide
N-{[4-(2-methylpyridine-3-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-
0.1045 0.1356 b]pyridine-5-carboxamide
N-{[4-(2-methylpyridine-3-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-
0.1803 0.0240 c]pyridine-2-carboxamide
N-{[4-(2-methylpyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0208 0.1-1 a]pyrimidine-6-carboxamide
N-{[4-(2-methylpyridine-3-sulfonyl)phenyl]methyl}thieno[2,3- 0.0154
0.0119 c]pyridine-2-carboxamide
N-{[4-(4-methylpyridine-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-
0.0192 0.0114 2-carboxamide
N-{[4-(4-methylpyridine-3-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-
0.1-1 0.2714 b]pyridine-5-carboxamide
N-{[4-(4-methylpyridine-3-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-
0.2599 0.0258 c]pyridine-2-carboxamide
N-{[4-(4-methylpyridine-3-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-
0.0252 0.062 2-carboxamide
N-{[4-(4-methylpyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0665 0.0658 a]pyridine-6-carboxamide
N-{[4-(4-methylpyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0191 0.1-1 a]pyrimidine-6-carboxamide
N-{[4-(5-methoxypyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0090 0.0034 a]pyridine-6-carboxamide
N-{[4-(5-methoxypyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0016 0.0258 a]pyrimidine-6-carboxamide
N-{[4-(5-methoxypyridine-3-sulfonyl)phenyl]methyl}thieno[2,3-
0.0090 0.0016 c]pyridine-2-carboxamide
N-{[4-(5-methylpyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0368 0.0071 a]pyridine-6-carboxamide
N-{[4-(5-methylpyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0022 0.0124 a]pyrimidine-6-carboxamide
N-{[4-(5-methylpyridine-3-sulfonyl)phenyl]methyl}thieno[2,3- 0.0060
0.0025 c]pyridine-2-carboxamide
N-{[4-(5-methylthiophene-2-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-
0.0223 0.0347 b]pyridine-5-carboxamide
N-{[4-(6-methoxynaphthalene-2-sulfonyl)phenyl]methyl}-1H- 0.0099
0.0051 pyrrolo[3,2-c]pyridine-2-carboxamide
N-{[4-(6-methoxynaphthalene-2-sulfonyl)phenyl]methyl}furo[2,3-
0.0030 0.0036 c]pyridine-2-carboxamide
N-{[4-(6-methoxynaphthalene-2-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0027 0.0018 a]pyridine-6-carboxamide
N-{[4-(6-methoxynaphthalene-2-sulfonyl)phenyl]methyl}thieno[2,3-
0.0015 0.0033 c]pyridine-2-carboxamide
N-{[4-(6-methoxypyridine-2-sulfonyl)phenyl]methyl}furo[2,3- 0.0025
0.0032 c]pyridine-2-carboxamide
N-{[4-(6-methoxypyridine-2-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0052 0.0013 a]pyridine-6-carboxamide
N-{[4-(6-methoxypyridine-2-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0022 0.0059 a]pyrimidine-6-carboxamide
N-{[4-(6-methylpyrazine-2-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-
0.0349 0.0312 b]pyridine-5-carboxamide
N-{[4-(6-methylpyrazine-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-
0.0209 0.0097 2-carboxamide
N-{[4-(6-methylpyrazine-2-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0010 0.0525 a]pyrimidine-6-carboxamide
N-{[4-(6-methylpyrazine-2-sulfonyl)phenyl]methyl}thieno[2,3- 0.0048
0.0051 c]pyridine-2-carboxamide
N-{[4-(6-methylpyridine-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-
0.0128 0.0125 2-carboxamide
N-{[4-(6-methylpyridine-3-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-
0.0241 0.0213 b]pyridine-5-carboxamide
N-{[4-(6-methylpyridine-3-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-
0.0557 0.0130 c]pyridine-2-carboxamide
N-{[4-(6-methylpyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0215 0.0139 a]pyridine-6-carboxamide
N-{[4-(6-methylpyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0059 0.0555 a]pyrimidine-6-carboxamide
N-{[4-(6-methylpyridine-3-sulfonyl)phenyl]methyl}thieno[2,3- 0.0220
0.0063 c]pyridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-[1,3]thiazolo[5,4-c]pyridine-2-
0.220 >10 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1,6-naphthyridine-2- 2.85
>10 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-3-
1.91 2.06 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2- 0.007
0.0088 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-
0.002 0.057 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}quinoline-6-carboxamide 0.108
>10
N-{[4-(cyclohexanesulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-
0.005 0.0176 2-carboxamide
N-{[4-(dimethyl-1,3-thiazole-5-sulfonyl)phenyl]methyl}-1H- 0.0386
0.0164 pyrazolo[3,4-b]pyridine-5-carboxamide
N-{[4-(dimethyl-1,3-thiazole-5-sulfonyl)phenyl]methyl}furo[2,3-
0.0083 0.0103 c]pyridine-2-carboxamide
N-{[4-(dimethyl-1,3-thiazole-5-sulfonyl)phenyl]methyl}imidazo[1,2-
0.009 0.0037 a]pyridine-6-carboxamide
N-{[4-(dimethyl-1,3-thiazole-5-sulfonyl)phenyl]methyl}imidazo[1,2-
0.0037 0.0495 a]pyrimidine-6-carboxamide
N-{[4-(dimethyl-1,3-thiazole-5-sulfonyl)phenyl]methyl}thieno[2,3-
0.0013 0.0030 c]pyridine-2-carboxamide
N-{[4-(furan-2-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-
0.0762 0.1-1 carboxamide
N-{[4-(isoquinoline-4-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-
0.0037 0.0025 b]pyridine-5-carboxamide
N-{[4-(isoquinoline-4-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-
0.0109 0.0016 c]pyridine-2-carboxamide
N-{[4-(isoquinoline-4-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
0.0190 0.003 carboxamide
N-{[4-(isoquinoline-4-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-
0.0224 0.0041 carboxamide
N-{[4-(isoquinoline-4-sulfonyl)phenyl]methyl}imidazo[1,2- 0.0016
0.0032 a]pyrimidine-6-carboxamide
N-{[4-(isoquinoline-4-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
0.0067 0.0008 carboxamide
N-{[4-(naphthalene-1-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-
0.0091 0.00368 b]pyridine-5-carboxamide
N-{[4-(naphthalene-1-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
0.0049 0.0031 carboxamide
N-{[4-(naphthalene-1-sulfonyl)phenyl]methyl}imidazo[1,2- 0.0029
0.0036 a]pyrimidine-6-carboxamide
N-{[4-(phenoxathiine-4-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-
0.0148 0.0204 b]pyridine-5-carboxamide
N-{[4-(phenoxathiine-4-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
0.0056 0.0131 carboxamide
N-{[4-(phenoxathiine-4-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-
0.00215 0.00218 6-carboxamide
N-{[4-(phenoxathiine-4-sulfonyl)phenyl]methyl}imidazo[1,2- 0.0021
0.0042 a]pyrimidine-6-carboxamide
N-{[4-(pyridine-2-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
0.0551 0.0870 carboxamide
N-{[4-(pyridine-3-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
0.0090 0.0664 carboxamide
N-{[4-(pyridine-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-
0.0059 0.1-1 carboxamide
N-{[4-(quinoline-3-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-
0.0052 0.0044 5-carboxamide
N-{[4-(quinoline-3-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-
0.0163 0.0029 2-carboxamide
N-{[4-(quinoline-3-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
0.0042 0.0032 carboxamide
N-{[4-(quinoline-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-
0.014 0.001 carboxamide
N-{[4-(quinoline-3-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-
0.0025 0.0036 carboxamide
N-{[4-(quinoline-3-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
0.0044 0.0009 carboxamide
N-{[4-(quinoline-6-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-
0.0101 0.0041 5-carboxamide
N-{[4-(quinoline-6-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
0.0073 0.005 carboxamide
N-{[4-(quinoline-6-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-
0.00516 0.00083 carboxamide
N-{[4-(quinoline-6-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-
0.0033 0.0056 carboxamide
N-{[4-(quinoline-8-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-
0.0455 0.0236 5-carboxamide
N-{[4-(quinoline-8-sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-
0.0076 0.0060 carboxamide
N-{[4-(quinoline-8-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-
0.0098 0.0055 carboxamide
N-{[4-(quinoline-8-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyrimidine-6-
0.0030 0.0277 carboxamide
N-({4-[(2,4-dimethoxyphenyl)sulfamoyl]phenyl}methyl)-1H- 0.0058
0.0069 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(2-hydroxyethyl)phenyl]sulfamoyl}phenyl)methyl]-1H-
0.0188 0.0199 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(5-fluoro-2-methoxyphenyl)sulfamoyl]phenyl}methyl)quinoline-
0.0660 1-10 6-carboxamide
N-({4-[(2,3,6-trimethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.012 0.0055 c]pyridine-2-carboxamide
N-({4-[(2,3-dimethoxy-5-methylbenzene)sulfonyl]phenyl}methyl)-1H-
0.010 0.002 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2,3-dimethoxy-5- 0.006 0.0027
methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(2,3-dimethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.009 0.0034 c]pyridine-2-carboxamide
N-({4-[(2,3-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.014 0.007 c]pyridine-2-carboxamide
N-({4-[(2,3-dimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.011 0.0044 c]pyridine-2-carboxamide
N-({4-[(2,4,5-trimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.008 0.0081 c]pyridine-2-carboxamide
N-({4-[(2,4,6-trimethylbenzene)sulfonyl]phenyl}methyl)-1H- 0.076
0.046 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2,4-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.027 0.007 c]pyridine-2-carboxamide
N-({4-[(2,4-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.021 0.012 c]pyridine-2-carboxamide
N-({4-[(2,4-dimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.012 0.0222 c]pyridine-2-carboxamide
N-({4-[(2,5-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.017 0.006 c]pyridine-2-carboxamide
N-({4-[(2,5-dimethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.004 0.0023 c]pyridine-2-carboxamide
N-({4-[(2,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.011 0.014 c]pyridine-2-carboxamide
N-({4-[(2,5-dimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.011 0.0086 c]pyridine-2-carboxamide
N-({4-[(2,6-dimethoxy-4-methylbenzene)sulfonyl]phenyl}methyl)-1H-
0.016 0.010 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2,6-dimethoxy-4- 0.007 0.0030
methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(2-acetylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.006 0.004 c]pyridine-2-carboxamide
N-({4-[(2-acetylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.001 0.0010 2-carboxamide
N-({4-[(2-chloro-6-methoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.013
0.003 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.006 0.117 c]pyridine-2-carboxamide
N-({4-[(2-ethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.011 0.002 c]pyridine-2-carboxamide
N-({4-[(2-ethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3- 0.002
0.0008 c]pyridine-2-carboxamide
N-({4-[(2-ethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.005 0.003 c]pyridine-2-carboxamide
N-({4-[(2-ethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.005 0.0029 2-carboxamide
N-({4-[(2-fluoro-3-methoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.010
0.007 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.011
0.021 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.008 0.0207 c]pyridine-2-carboxamide
N-({4-[(2-fluoro-5-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.025
0.024 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-methanesulfonamidobenzene)sulfonyl]phenyl}methyl)-1H-
0.284 >1 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-methoxy-5-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.012
0.003 pyrrolo[3,2-c]pyridine-2-carboxamide N-({4-[(2-methoxy-5-
0.006 0.0025
methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.009 0.007 c]pyridine-2-carboxamide
N-({4-[(2-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3- 0.007
0.0053 c]pyridine-2-carboxamide
N-({4-[(2-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.014 0.013 c]pyridine-2-carboxamide
N-({4-[(2-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3- 0.010
0.0222 c]pyridine-2-carboxamide
N-({4-[(2-phenoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.011 0.007 c]pyridine-2-carboxamide
N-({4-[(2-phenoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3- 0.011
0.0697 c]pyridine-2-carboxamide
N-({4-[(2-phenylethane)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.011 0.022 c]pyridine-2-carboxamide
N-({4-[(3,4-difluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.013 0.014 c]pyridine-2-carboxamide
N-({4-[(3,4-difluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.009 0.0081 c]pyridine-2-carboxamide
N-({4-[(3,4-dimethoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.014 0.003 c]pyridine-2-carboxamide
N-({4-[(3,4-dimethoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.003 0.0009 c]pyridine-2-carboxamide
N-({4-[(3,4-dimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.006 0.0023 c]pyridine-2-carboxamide
N-({4-[(3,5-dichlorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.006 0.0007 c]pyridine-2-carboxamide
N-({4-[(3,5-difluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.011 0.007 c]pyridine-2-carboxamide
N-({4-[(3,5-difluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.004 0.0027 c]pyridine-2-carboxamide
N-({4-[(3,5-dimethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.009 0.002 c]pyridine-2-carboxamide
N-({4-[(3,5-dimethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.005 0.0018 c]pyridine-2-carboxamide
N-({4-[(3-acetylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.012 0.006 c]pyridine-2-carboxamide
N-({4-[(3-acetylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.004 0.0026 2-carboxamide
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.005 0.003 c]pyridine-2-carboxamide
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.005 0.003 2-carboxamide
N-({4-[(3-ethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.006 0.0027 2-carboxamide
N-({4-[(3-fluoro-4-methoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.005
0.004 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-fluoro-4-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.005 0.0025 c]pyridine-2-carboxamide
N-({4-[(3-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.008
0.006 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(3-fluoro-4-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.003 0.0028 c]pyridine-2-carboxamide
N-({4-[(3-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.009 0.01 c]pyridine-2-carboxamide
N-({4-[(3-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.003 0.0033 2-carboxamide
N-({4-[(3-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.007 0.004 c]pyridine-2-carboxamide
N-({4-[(3-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3- 0.005
0.0026 c]pyridine-2-carboxamide
N-({4-[(3-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.009 0.004 c]pyridine-2-carboxamide
N-({4-[(3-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3- 0.004
0.0023 c]pyridine-2-carboxamide
N-({4-[(4,5-difluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.014 0.006 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4,5-difluoro-2- 0.005 0.0029
methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(4-acetylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.007 0.003 c]pyridine-2-carboxamide
N-({4-[(4-acetylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.004 0.0025 2-carboxamide
N-({4-[(4-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.022
0.003 pyrrolo[3,2-c]pyridine-2-carboxamide N-({4-[(4-chloro-2-
0.010 0.0038
methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(4-chloro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.027
0.025 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-chloro-3-fluorobenzene)sulfonyl]phenyl}methyl)-1H- 0.008
0.013 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-chloro-3-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.003 0.0071 c]pyridine-2-carboxamide
N-({4-[(4-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.009 0.025 c]pyridine-2-carboxamide
N-({4-[(4-ethylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.008 0.012 c]pyridine-2-carboxamide
N-({4-[(4-ethylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.006 0.0078 2-carboxamide
N-({4-[(4-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.031
0.007 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.009 0.0065 c]pyridine-2-carboxamide
N-({4-[(4-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.019
0.027 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.009
0.007 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-3-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.007 0.0029 c]pyridine-2-carboxamide
N-({4-[(4-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.038 0.008 c]pyridine-2-carboxamide
N-({4-[(4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2- 0.023
0.011 a]pyridine-6-carboxamide
N-({4-[(4-fluorobenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-
0.003 0.010 2-carboxamide
N-({4-[(4-methanesulfonylbenzene)sulfonyl]phenyl}methyl)-1H- 0.024
0.012 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-methoxy-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.024
0.024 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-methoxy-3-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.01
0.002 pyrrolo[3,2-c]pyridine-2-carboxamide N-({4-[(4-methoxy-3-
0.003 0.0024
methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(4-methoxybenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.011 0.009 c]pyridine-2-carboxamide
N-({4-[(4-methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3- 0.005
0.0027 c]pyridine-2-carboxamide
N-({4-[(4-methylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.006 0.009 c]pyridine-2-carboxamide
N-({4-[(4-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3- 0.005
0.0050 c]pyridine-2-carboxamide
N-({4-[(5-acetyl-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.02
0.006 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(5-chloro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.006
0.002 pyrrolo[3,2-c]pyridine-2-carboxamide N-({4-[(5-chloro-2-
0.004 0.0013
methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-({4-[(5-fluoro-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H- 0.005
0.003 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(5-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)-1H- 0.011
0.007 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(5-fluoro-2-methylbenzene)sulfonyl]phenyl}methyl)thieno[2,3-
0.003 0.0094 c]pyridine-2-carboxamide
N-({4-[(5-tert-butyl-2-methoxybenzene)sulfonyl]phenyl}methyl)-1H-
0.647 0.006 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(5-tert-butyl-2- 0.015 0.0046
methoxybenzene)sulfonyl]phenyl}methyl)thieno[2,3-c]pyridine-2-
carboxamide
N-(4-(2-(trifluoromethoxy)phenylsulfonyl)benzyl)imidazo[1,2- 0.008
a]pyridine-6-carboxamide
N-(4-(phenylsulfonyl)benzyl)-1H-imidazo[4,5-b]pyridine-6-carboxamide
5.780 >10
N-(4-(phenylsulfonyl)benzyl)benzo[d]thiazole-5-carboxamide 0.047
3.872
N-[(4-{[2-(benzyloxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
0.018 0.033 c]pyridine-2-carboxamide
N-[(4-{[2-(dimethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.951 0.484 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(methylsulfamoyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.076 0.202 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(morpholin-4-ylmethyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.034 0.006 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(morpholin-4- 0.013 0.0036
ylmethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-
carboxamide
N-[(4-{[2-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-
0.016 0.003 pyrrolo[3,2-c]pyridine-2-carboxamide N-[(4-{[2- 0.004
0.0028 (trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide
N-[(4-{[2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.022 0.025 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.013 0.0260 c]pyridine-2-carboxamide
N-[(4-{[2-fluoro-4-(1H-pyrazol-1- 0.006 0.0080
yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-
carboxamide N-[(4-{[2-methoxy-4-(1H-pyrazol-1- 0.016 0.002
yl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-c]pyridine-2-
carboxamide N-[(4-{[2-methoxy-4-(1H-pyrazol-1- 0.005 0.0026
yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-
carboxamide N-[(4-{[2-methoxy-4- 0.022 0.005
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-
c]pyridine-2-carboxamide N-[(4-{[2-methoxy-4- 0.009 0.0075
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide
N-[(4-{[2-methoxy-5-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]-
0.061 0.012 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-methoxy-5-(propan-2- 0.009 0.0062
yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-
carboxamide N-[(4-{[2-methoxy-6-(propan-2- 0.036 0.022
yloxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,2-c]pyridine-2-
carboxamide
N-[(4-{[2-methyl-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-
0.004 0.004 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]-1H- 0.006
0.004 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.009 0.0026 c]pyridine-2-carboxamide
N-[(4-{[3-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-
0.005 0.003 pyrrolo[3,2-c]pyridine-2-carboxamide N-[(4-{[3- 0.002
0.0024 (trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide
N-[(4-{[3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.009 0.003 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.003 0.0010 c]pyridine-2-carboxamide
N-[(4-{[3-fluoro-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-
0.011 0.004 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-(dimethylcarbamoyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.027 0.014 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-(propan-2-yl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
0.006 0.0071 c]pyridine-2-carboxamide
N-[(4-{[4-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-1H-
0.024 0.026 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-chloro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]-
0.008 0.005 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[4-chloro-3- 0.010 0.0034
(trifluoromethyl)benzene]sulfonyl}phenyl)methyl]thieno[2,3-
c]pyridine-2-carboxamide
N-[4-(benzenesulfonyl)phenyl]pyridine-3-carboxamide 12.038 >30
N-{[3-(benzenesulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-2-
>30 >30 carboxamide
N-{[4-(1H-indole-7-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
0.003 0.0027 carboxamide
N-{[4-(1-methyl-1H-pyrazole-4-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-
0.048 0.123 c]pyridine-2-carboxamide
N-{[4-(2,3-dihydro-1,4-benzodioxine-6- 0.004 0.0027
sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-carboxamide
N-{[4-(2H-1,3-benzodioxole-5-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-
0.008 0.007 c]pyridine-2-carboxamide
N-{[4-(2H-1,3-benzodioxole-5-sulfonyl)phenyl]methyl}thieno[2,3-
0.003 0.0025 c]pyridine-2-carboxamide
N-{[4-(5-methylthiophene-2-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-
0.007 0.013 c]pyridine-2-carboxamide
N-{[4-(5-methylthiophene-2-sulfonyl)phenyl]methyl}thieno[2,3- 0.005
0.0077 c]pyridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-[1,2,3,4]tetrazolo[1,5- 0.447
>30 a]pyridine-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-[1,2,4]triazolo[4,3-a]pyridine-
0.301 >10 6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1,5-naphthyridine-2- 0.875
>10 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-imidazo[4,5-c]pyridine-2-
7.062 5.37 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-3-
1.271 >10 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-5-
0.070 0.051 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-pyrrolo[2,3-b]pyridine-5-
1.906 >30 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-pyrrolo[2,3-c]pyridine-3-
>10 >10 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1-methyl-1H-pyrazolo[3,4-
1.725 >30 b]pyridine-5-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1-methyl-1H-pyrrolo[3,2-
>10 >30 c]pyridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-3-(pyridin-2-yl)-1H-pyrazole-5-
7.429 23.371 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-3-(pyridin-3-yl)-1,2-oxazole-5-
0.033 >30 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-3-(pyridin-4-yl)-1H-pyrazole-5-
3.176 21.554 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-3-bromo-1H-pyrrolo[3,2- 0.306
7.390 c]pyridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-5-(pyridin-3-yl)-1,2,4- 0.312
>30 oxadiazole-3-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-5-(pyridin-3-yl)-1H-pyrazole-3-
0.023 11.825 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}imidazo[1,2-a]pyrazine-2-
1.491 >30 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-
0.021 0.011 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}isoquinoline-6-carboxamide
16.082 21.303
N-{[4-(benzenesulfonyl)phenyl]methyl}isoquinoline-7-carboxamide
0.219 24.000
N-{[4-(benzenesulfonyl)phenyl]methyl}quinazoline-6-carboxamide
16.082 21.303
N-{[4-(benzenesulfonyl)phenyl]methyl}thieno[2,3-b]pyrazine-6- 0.052
>30 carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2- 0.011
0.012 carboxamide
N-{[4-(isoquinoline-4-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
0.003 0.0007 carboxamide
N-{[4-(naphthalene-1-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
0.002 0.0005 carboxamide
N-{[4-(phenoxathiine-4-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-
0.005 0.0009 c]pyridine-2-carboxamide
N-{[4-(phenoxathiine-4-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-
0.004 0.0017 2-carboxamide
N-{[4-(phenylmethane)sulfonylphenyl]methyl}-1H-pyrrolo[3,2- 0.029
0.3015 c]pyridine-2-carboxamide
N-{[4-(pyridine-3-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-2-
0.021 0.048 carboxamide
N-{[4-(quinoline-3-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
0.003 0.0008 carboxamide
N-{[4-(quinoline-6-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
0.003 0.0009 carboxamide
N-{[4-(quinoline-8-sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-
0.006 0.0025 carboxamide
N-{2-[4-(benzenesulfonyl)phenyl]ethyl}-1H-pyrrolo[3,2-c]pyridine-2-
0.410 9.1 carboxamide
N-({4-[(1H-indazol-6-yl)sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.135 5.44 c]pyridine-2-carboxamide
N-({4-[(1-oxo-1H-isochromen-5-yl)sulfamoyl]phenyl}methyl)-1H- 0.008
2.27 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2,3-dihydro-1,4-benzodioxin-6-yl)sulfamoyl]phenyl}methyl)-1H-
>10 >10 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-acetylphenyl)sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.005 0.005 c]pyridine-2-carboxamide
N-({4-[(2-methoxy-6-methylphenyl)sulfamoyl]phenyl}methyl)-1H- 0.006
12.4 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(2-methoxyphenyl)sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.089 2.150 c]pyridine-2-carboxamide
N-({4-[(2-phenoxyphenyl)sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-
4.019 12.000 c]pyridine-2-carboxamide
N-({4-[(2-propoxyphenyl)sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.052 0.100 c]pyridine-2-carboxamide
N-({4-[(3-methoxy-2-methylphenyl)sulfamoyl]phenyl}methyl)-1H- 0.030
0.006 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-chloro-2-methoxy-5-methylphenyl)sulfamoyl]phenyl}methyl)-
7.835 18.322 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-ethoxy-2-fluorophenyl)sulfamoyl]phenyl}methyl)-1H- 0.154
1.600 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-fluoro-2-methoxyphenyl)sulfamoyl]phenyl}methyl)-1H- 3.138
>30 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(4-methoxy-2-methylphenyl)sulfamoyl]phenyl}methyl)-1H- 1.451
>30 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(5,6,7,8-tetrahydronaphthalen-1-yl)sulfamoyl]phenyl}methyl)-
>30 >30 1H-pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(5-chloro-2-methoxyphenyl)sulfamoyl]phenyl}methyl)-1H- 0.197
17.984 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(5-fluoro-2-methoxyphenyl)sulfamoyl]phenyl}methyl)-1H- 0.232
>30 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(5-methoxy-2-methylphenyl)sulfamoyl]phenyl}methyl)-1H- 0.051
13.018 pyrrolo[3,2-c]pyridine-2-carboxamide
N-({4-[(quinolin-8-yl)sulfamoyl]phenyl}methyl)-1H-pyrrolo[3,2-
0.075 1.478 c]pyridine-2-carboxamide
N-[(4-{[2-(2-hydroxyethoxy)phenyl]sulfamoyl}phenyl)methyl]-1H-
19.611 23.854 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(hydroxymethyl)phenyl]sulfamoyl}phenyl)methyl]-1H- 0.030
0.006 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(morpholin-4-yl)phenyl]sulfamoyl}phenyl)methyl]-1H- 0.019
0.017 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(piperidin-1-yl)phenyl]sulfamoyl}phenyl)methyl]-1H- 0.072
0.008 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(propan-2-yloxy)phenyl]sulfamoyl}phenyl)methyl]-1H- 0.003
0.001 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(trifluoromethoxy)benzene]sulfonamido}phenyl)methyl]-1H-
0.003 0.001 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-(trifluoromethoxy)phenyl]sulfamoyl}phenyl)methyl]-1H-
0.006 0.001 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{[2-methoxy-5- 0.0005 0.0016
(trifluoromethyl)phenyl]sulfamoyl}phenyl)methyl]-1H-pyrrolo[3,2-
c]pyridine-2-carboxamide N-[(4-{[4-chloro-2- 0.002 0.002
(trifluoromethoxy)phenyl]sulfamoyl}phenyl)methyl]-1H-pyrrolo[3,2-
c]pyridine-2-carboxamide
N-[(4-{8-oxa-3-azabicyclo[3.2.1]octane-3-sulfonyl}phenyl)methyl]-1H-
0.008 0.003 pyrrolo[3,2-c]pyridine-2-carboxamide
N-[(4-{8-oxa-3-azabicyclo[3.2.1]octane-3- 0.004 0.003
sulfonyl}phenyl)methyl]imidazo[1,2-a]pyridine-6-carboxamide
N-[(4-{8-oxa-3-azabicyclo[3.2.1]octane-3- 0.015 0.003
sulfonyl}phenyl)methyl]thieno[2,3-c]pyridine-2-carboxamide
N-[(4-benzamidophenyl)methyl]-1H-pyrrolo[3,2-c]pyridine-2- 0.019
0.004 carboxamide
N-[(4-benzenesulfonamidophenyl)methyl]-1H-pyrrolo[3,2-c]pyridine-2-
0.011 0.005 carboxamide
N-[4-(piperidine-1-sulfonyl)phenyl]-1H-pyrrolo[3,2-c]pyridine-2-
0.008 0.006 carboxamide
N-[4-(piperidine-1-sulfonyl)phenyl]-2-(pyridin-3-yloxy)acetamide
0.0011 0.0066
N-[4-(piperidine-1-sulfonyl)phenyl]-3-(pyridin-3-yl)propanamide
0.003 0.007
N-{[1-(benzenesulfonyl)piperidin-4-yl]methyl}-1H-pyrrolo[3,2- 0.015
0.009 c]pyridine-2-carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-[1,2,3,4]tetrazolo[1,5-
0.003 0.009 a]pyridine-7-carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1,3-benzothiazole-6-
0.009 0.010 carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1,6-naphthyridine-2-
0.012 0.010 carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1H-1,3-benzodiazole-5-
0.021 0.010 carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1H-imidazo[1,2- 0.0008
0.0110 b]pyrazole-5-carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1H-indazole-5- 0.018
0.016 carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4- 0.017
0.033 b]pyridine-5-carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1H-pyrrolo[2,3-c]pyridine-
0.004 0.054 2-carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-
0.023 0.200 2-carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}furo[3,2-c]pyridine-2-
0.017 0.286 carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-
0.018 1.160 carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-7-
>0.1 >0.5 carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}pyridine-3-carboxamide
0.039 0.64
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}thieno[2,3-b]pyridine-2-
6.146 14.000 carboxamide
N-{[4-(piperidine-1-sulfonyl)phenyl]methyl}thieno[3,2-c]pyridine-2-
0.886 10 carboxamide
N-{1-[4-(piperidine-1-sulfonyl)phenyl]ethyl}-1H-pyrrolo[3,2-c]pyridine-
0.020 0.007 2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-5,6,7,8-tetrahydro-1,6- 0.544
>2 naphthyridine-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-5H,6H,7H-pyrrolo[3,4- 0.020
>2 b]pyridine-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H,4H,5H,6H,7H-pyrazolo[4,3-
>2 >2 c]pyridine-5-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-5H,6H,7H,8H-pyrido[4,3- >2
>2 d]pyrimidine-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H,4H,5H,6H,7H-imidazo[4,5-
>2 >2 c]pyridine-5-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}-4H,5H,6H,7H-[1,2]oxazolo[4,3-
>2 >2 c]pyridine-5-carboxamide
Assay Example 3
In-Vitro Cell Proliferation Assay
[0762] U251 cells were seeded in 96-well plates at 1.25.times.103
cells/well in 180 .mu.L of culture medium (10% FBS, 1% Pen/Strep
Amphotecricin B, RPMI-5 1640) with and without the addition of
either _-nicotinamide mononucleotide (NMN) or nicotinamide (NAM).
After overnight incubation at 37.degree. C. and 5% CO2, the
compound titrations were performed in a separate dilution plate by
serially diluting the compounds in DMSO to make a 1000.times.
stock. The compounds were then further diluted to 10.times. final
concentration in culture media, whereupon 20 .mu.L of each dilution
was added to the plated cells with controls (e.g. DMSO and blank)
to make a final volume of 5 200 .mu.L. The final DMSO concentration
in each well was 0.1%. The plates were then incubated for 72 hours
at 37.degree. C. in a 5% CO2 incubator. The number of viable cells
was then assessed using sulforhodamine B (SRB) assay. Cells were
fixed at 4.degree. C. for 1 hour with the addition of 50 .mu.L 30%
trichloroacetic acid (TCA) to make a final concentration of 6% 10
TCA. The plates were washed four times with H2O and allowed to dry
for at least 1 hour, whereupon 100 L of a 4% SRB in 1% acetic acid
solution was added to each well and incubated at room temperature
for at least 30 minutes. The plates were then washed three times
with 1% acetic acid, dried, and treated with 100 .mu.L of 10 mM
Tris-Base solution. The plates were then read in a microplate
reader at an absorbance of 570 nm. 15 Background was generated on a
separate plate with media only.
Method for Determining % Inhibition
[0763] First, the signals from the background plate are averaged,
then the background was subtracted from the test plates. The
compound-treated cells were then assayed for % 20 inhibition by
using the following formula:
%Inh=100-100*x/y
wherein x denotes the average signal of the compound-treated cells
and y denotes the average signal of the DMSO-treated cells.
[0764] 25 Formula for Determining 1050 Values:
IC50=10 (LOG 10(X)+(((50-%Inh at Cmpd Concentration 1)/(XXYY)*(LOG
10(X)-LOG 10(Y))))
wherein X denotes the compound concentration 1, Y denotes the
compound concentration 2, XX denotes the % inhibition at compound
concentration 1 (X), and YY 30 denotes the % inhibition at compound
concentration 2 (Y). Table 4 below shows U251-values for some
compounds.
TABLE-US-00004 U251 Chemical name IC50 (uM)
N-{[4-(benzenesulfonyl)phenyl]methyl}thieno[3,2- >2
b]pyridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}imidazo[1,5- >2
a]pyridine-6-carboxamide N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-
0.040 pyrrolo[3,2-c]pyridine-2-carboxamide
N-{[5-(benzenesulfonyl)pyridin-2-yl]methyl}-1H- 0.035
pyrrolo[3,2-c]pyridine-2-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}imidazo[1,2- >2
a]pyrazine-6-carboxamide
N-{[4-(benzenesulfonyl)phenyl]methyl}furo[3,2- 0.545
b]pyridine-2-carboxamide
N-{[6-(benzenesulfonyl)pyridin-3-yl]methyl}-1H- >2
pyrrolo[3,2-c]pyridine-2-carboxamide
N-{[4-(piperazine-1-sulfonyl)phenyl]methyl}thieno[2,3- 0.405
c]pyridine-2-carboxamide N-{[4-(piperazine-1-
sulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6- 0.556 carboxamide
N-{[4-(3-aminopyrrolidine-1- 0.31
sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2- carboxamide
hydrochloride N-{[4-(3-aminopyrrolidine-1- 1.85
sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2- carboxamide
hydrochloride N-({4-[(3,5- 0.0066
difluorobenzene)sulfinyl]phenyl}methyl)imidazo[1,2-
a]pyridine-6-carboxamide
Xenograft Studies:
[0765] C.B-17-Igh-1b-Prkdc.sup.scid mice (female) were injected
s.c. with 5.times.10.sup.6 A2780 cells (NCI) in the left flank.
10-12 days later when tumors reached 100-200 mm3 in size, mice were
randomized into treatment groups of 8 mice per group including
vehicle control and reference standard groups. The compounds were
formulated in 60:30:10 PEG-400:D5W: Ethanol and administered p.o.,
at the dose volume of 10 ml/kg BID for a duration of 5 or 10 days.
The dose used for efficacy was selected from the MTD (Maximum
Tolerated Dose) study. Mice were weighed and tumors measured using
vernier calipers every alternate day. Tumor volume was calculated
according to the formula (length.times.width)/2. All animal work
was approved by the Institutional Animal Care and Use Committee of
Biological Resource Centre, Singapore.
[0766] The compound
N-[(4-{[2-(trifluoromethoxy)phenyl]sulfamoyl}phenyl)methyl]-1H-pyrrolo[3,-
2-c]pyridine-2-carboxamide produced tumor stasis.
The following compounds produced tumor regression: [0767]
N-{[4-(benzenesulfonyl)phenyl]methyl}imidazo[1,2-a]pyridine-6-carboxamide-
; [0768]
N-{[4-(benzenesulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-carb-
oxamide; [0769]
N-{[4-(benzenesulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-2-carboxa-
mide [0770]
N-({4-[(4-fluorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide; [0771]
N-({4-[(4-fluorobenzene)sulfonyl]phenyl}methyl)imidazo[1,2-a]pyridine-6-c-
arboxamide; [0772]
N-({4-[(4-acetylbenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide; [0773]
N-[(4-{[2-(trifluoromethoxy)benzene]sulfonyl}phenyl)methyl]-1H-pyrrolo[3,-
2-c]pyridine-2-carboxamide; [0774]
N-({4-[(3-chlorobenzene)sulfonyl]phenyl}methyl)-1H-pyrrolo[3,2-c]pyridine-
-2-carboxamide.
[0775] The following compounds delayed tumor growth; [0776]
N-{[4-(pyridine-3-sulfonyl)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-2-car-
boxamide. [0777]
N-[(4-{[2-methoxy-4-(1H-pyrazol-1-yl)benzene]sulfonyl}phenyl)methyl]-1H-p-
yrrolo[3,2-c]pyridine-2-carboxamide
[0778] While the present invention has been described in
conjunction with the specific embodiments set forth above, many
alternatives, modifications and other variations thereof will be
apparent to those of ordinary skill in the art. All such
alternatives, modifications and variations are intended to fall
within the spirit and scope of the present invention.
TABLE-US-LTS-00001 LENGTHY TABLES The patent application contains a
lengthy table section. A copy of the table is available in
electronic form from the USPTO web site
(http://seqdata.uspto.gov/?pageRequest=docDetail&DocID=US20140294805A1).
An electronic copy of the table will also be available from the
USPTO upon request and payment of the fee set forth in 37 CFR
1.19(b)(3).
* * * * *
References