U.S. patent application number 10/761070 was filed with the patent office on 2004-10-21 for novel 2,3,4,5-tetrahydro-1h-[1,4]diazepino[1,7-a]indole compounds.
Invention is credited to Ennis, Michael Dalton, Ghazal, Nabil B., Hoffman, Robert Louis, Olson, Rebecca M..
Application Number | 20040209870 10/761070 |
Document ID | / |
Family ID | 22695943 |
Filed Date | 2004-10-21 |
United States Patent
Application |
20040209870 |
Kind Code |
A1 |
Ennis, Michael Dalton ; et
al. |
October 21, 2004 |
Novel 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
compounds
Abstract
A compound of formula I: 1 where a is a single bond or double
bond, and where R1a, R1b, R2a and R2b are each independently (a) H,
Cl, Br, I, F, CN, CF.sub.3, OCF.sub.3, OR5, CONR5R6COR5, CO2R5,
Y(CH.sub.2).sub.mXR5 or YC(O)(CH.sub.2).sub.mXR5, where m=0-3,
Y=CH.sub.2, S, O, or NR6, X=CH.sub.2, S, O, NR6; (b) (CH2).sub.pAr
where p=0-3 and Ar is aryl or heteroaryl optionally substituted
with one or more of the following: H, halogen, CN, NO.sub.2, OR7,
CF.sub.3, OCF.sub.3, SR7, SO.sub.2R7, SO.sub.2NR7R8, NR7R8,
CONR7R8, NR7COR8, NR7CONR8R9, CO.sub.2R7, COR7, or R7; or (c)
linear or branched C.sub.1-C.sub.8 alkyl, linear or branched
C.sub.2-C.sub.8 alkenyl, linear or branched C.sub.2-C.sub.8
alkynyl, C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 cycloalkenyl,
or C.sub.3-C.sub.8 cycloalkynyl; wherein any of these groups may be
optionally substituted with one or more of the following: halogen,
CN, NO.sub.2, COR7, OR7, NR7R8, SR7, CO2R7, CONR7R8 or NR7COR8; and
where R3 is (a) H, Cl, Br, I, F, CN, CF.sub.3, OCF.sub.3, alkyl,
Ar, OR5, SR5, CHO, CONR5R6, COR5, CO2R5, (Y).sub.o(CH2).sub.nXR5,
C(O)C(O)XR5, (Y).sub.o(CH.sub.2).sub.nC(O)XR5, C(O)(CH2).sub.nXR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)R5,
(Y).sub.o(CH2).sub.nN(R6)S(O).sub.2R5,
(Y).sub.o(CH2).sub.nN(R6)C(O)OR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)NR5R6 where o=0 or 1, n=0-3,
X=CH.sub.2, S, O, or NR6 and Y=CH.sub.2, S, O or NR6, where Ar is
aryl or heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; or (b) linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups may be optionally substituted with one
or more of the following: halogen, CN, NO.sub.2, COR10, OR10,
NR10R8, SR10, CO2R10, CONR10R8 or NR10COR8; and where R4, R5 and R6
are each independently (a) H, linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups other than H may be optionally
substituted with one or more of the following: halogen, CN,
NO.sub.2, COR10, OR10, NR10R11, SR10, CO2R10, CONR10R11 or
NR10COR11; or where R5 and R6 are linked to form a 3 to 8 member
ring; or (b) (CH.sub.2).sub.pAr where p=0-3 and Ar is aryl or
heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; and where R7, R8, and R9 are each
independently (a) H, linear or branched C.sub.1-C.sub.8 alkyl,
linear or branched C.sub.2-C.sub.8 alkenyl, linear or branched
C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl
groups, wherein any of these groups other than H may be optionally
substituted with halogen, CN, NO.sub.2, COR10, OR10, NR10R11, SR10,
CO2R10, CONR10R11, NR10COR11, NR10CONR11R12, or where R7, R8, or R9
are linked to form a ring; or (b) (CH2).sub.pAr where p=0-3 and Ar
is aryl or heteroaryl optionally substituted with one or more of
the following: H, halogen, CN, NO.sub.2, OR10, CF.sub.3, OCF.sub.3,
SR10, SO.sub.2R10, SO.sub.2NR10R11, NR10R11, CONR10R11, NR10COR11,
NR10CONR11R12, CO.sub.2R10, COR10, or R10; and where R10, R11 and
R12 are each independently H, linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl; or a
stereoisomer or pharmaceutically acceptable salt thereof.
Inventors: |
Ennis, Michael Dalton;
(Chesterfield, MO) ; Hoffman, Robert Louis; (San
Marcos, CA) ; Ghazal, Nabil B.; (Grand Rapids,
MI) ; Olson, Rebecca M.; (Mattawan, MI) |
Correspondence
Address: |
PHARMACIA & UPJOHN
301 HENRIETTA ST
0228-32-LAW
KALAMAZOO
MI
49007
US
|
Family ID: |
22695943 |
Appl. No.: |
10/761070 |
Filed: |
January 20, 2004 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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10761070 |
Jan 20, 2004 |
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09803242 |
Mar 8, 2001 |
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6734301 |
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60189103 |
Mar 14, 2000 |
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Current U.S.
Class: |
514/220 ;
540/558 |
Current CPC
Class: |
A61P 1/08 20180101; A61P
25/18 20180101; A61P 15/08 20180101; A61P 25/04 20180101; A61P
25/24 20180101; A61P 15/10 20180101; A61P 9/12 20180101; A61P 21/00
20180101; A61P 37/04 20180101; A61P 25/06 20180101; A61P 39/02
20180101; C07D 487/04 20130101; A61P 43/00 20180101; A61P 25/22
20180101; A61P 25/14 20180101; A61P 25/02 20180101; A61P 25/30
20180101; A61P 25/28 20180101; A61P 25/00 20180101; C07D 209/18
20130101; A61P 3/04 20180101; A61P 25/20 20180101 |
Class at
Publication: |
514/220 ;
540/558 |
International
Class: |
A61K 031/551; C07D
487/12 |
Claims
What is claimed is:
1. A compound of formula I: 219where a is a single bond or double
bond, and where R1a, R1b, R2a and R2b are each independently (a) H,
Cl, Br, I, F, CN, CF.sub.3, OCF.sub.3, OR5, CONR5R6, COR5, CO2R5,
Y(CH.sub.2).sub.mXR5 or YC(O)(CH.sub.2).sub.mXR5, where m=0-3,
Y=CH.sub.2, S, O, or NR6, X=CH.sub.2, S, O, NR6; (b) (CH2).sub.pAr
where p=0-3 and Ar is aryl or heteroaryl optionally substituted
with one or more of the following: H, halogen, CN, NO.sub.2, OR7,
CF.sub.3, OCF.sub.3, SR7, SO.sub.2R7, SO.sub.2NR7R8, NR7R8,
CONR7R8, NR7COR8, NR7CONR8R9, CO.sub.2R7, COR7, or R7; or (c)
linear or branched C.sub.1-C.sub.8 alkyl, linear or branched
C.sub.2-C.sub.8 alkenyl, linear or branched C.sub.2-C.sub.8
alkynyl, C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 cycloalkenyl,
or C.sub.3-C.sub.8 cycloalkynyl; wherein any of these groups may be
optionally substituted with one or more of the following: halogen,
CN, NO.sub.2, COR7, OR7, NR7R8, SR7, CO2R7, CONR7R8 or NR7COR8; and
where R3 is (a) H, Cl, Br, I, F, CN, CF.sub.3, OCF.sub.3, alkyl,
Ar, OR5, SR5, CHO, CONR5R6, COR5, CO2R5, (Y).sub.o(CH2).sub.nXR5,
C(O)C(O)XR5, (Y).sub.o(CH.sub.2).sub.nC(O)XR5, C(O)(CH2).sub.nXR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)R5,
(Y).sub.o(CH2).sub.nN(R6)S(O).sub.2R5,
(Y).sub.o(CH2).sub.nN(R6)C(O)OR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)NR5R6 where o=0 or 1, n=0-3,
X=CH.sub.2, S, O, or NR6 Y=CH.sub.2, S, O or NR6, where Ar is aryl
or heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, R7; or (b) linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups may be optionally substituted with one
or more of the following: halogen, CN, NO.sub.2, COR10, OR10,
NR10R8, SR10, CO2R10, CONR10R8 or NR10COR8; and where R4, R5 and R6
are each independently (a) H, linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups other than H may be optionally
substituted with one or more of the following: halogen, CN,
NO.sub.2, COR10, OR10, NR10R11, SR10, CO2R10, CONR10R11or
NR10COR11; or where R5 and R6 are linked to form a 3 to 8 member
ring; or (b) (CH.sub.2).sub.pAr where p=0-3 and Ar is aryl or
heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; and where R7, R8, and R9 are each
independently (a) H, linear or branched C.sub.1-C.sub.8 alkyl,
linear or branched C.sub.2-C.sub.8 alkenyl, linear or branched
C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl
groups, wherein any of these groups other than H may be optionally
substituted with halogen, CN, NO.sub.2, COR10, OR10, NR10R11, SR10,
CO2R10, CONR10R11, NR10COR11, NR10CONR11R12, or where R7, R8, or R9
are linked to form a ring; or (b) (CH2).sub.pAr where p=0-3 and Ar
is aryl or heteroaryl optionally substituted with one or more of
the following: H, halogen, CN, NO.sub.2, OR10, CF.sub.3, OCF.sub.3,
SR10, SO.sub.2R10, SO.sub.2NR10R11, NR10R11, CONR10R11, NR10COR11,
NR10CONR11R12, CO.sub.2R10, COR10, or R10; and where R10, R11 and
R12 are each independently H, linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl; or a
stereoisomer or pharmaceutically acceptable salt thereof.
2. The compound of claim 1 wherein R1a, R1b, R2a, R2b and R4 are H
and R3 is selected from either H,--C(O)C(O)XAr, --CH.sub.2C(O)XAr
or --C(O)CH.sub.2XAr.
3. The compound of claim 1 which is selected from the group
consisting of: 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbaldehyde
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
2,2,2-trifluoro-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl-
)-1-ethanone
11-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
11-chloro-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbon- itrile
8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbal-
dehyde
1-(8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)--
2,2,2-trifluoro-1-ethanone
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo- le-11-carboxamide
1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-y-
l)-1-ethanone hydrochloride
3-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[- 1,7-a]indole
3-ethyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
10-methoxy-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride ethyl
2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indol-11-yl)-2-oxoacetate
3-propyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino [1,7-a]indole
hydrochloride 2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indol-11-yl)-1-ethanamine
2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indol-11-yl)-1-ethanol
3-benzyl-11-(2-phenoxyethyl)-2,3,4,5-tetrah-
ydro-1H-[1,4]diazepino[1,7-a]indole
11-(2-phenoxyethyl)-2,3,4,5-tetrahydro-
-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(2-methoxyphenoxy)ethyl]-2,-
3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(2-fluoroph-
enoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(8-quinolinyloxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-
-1-ethanol
3-benzyl-11-[2-(2-methoxy-4-methylphenoxy)ethyl]-2,3,4,5-tetrah-
ydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(2-fluoro-6-methoxyphen-
oxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
11-[2-(2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indole
11-[2-(2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole hydrochloride
11-[2-(2-fluorophenoxy)ethyl]-2,3,4,5-tetrahy-
dro-1H-[1,4]diazepino[1,7-a]indole
11-[2-(2-methoxy-4-methylphenoxy)ethyl]-
-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
11-[2-(2-fluoro-6-metho-
xyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(2-chlorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
3-benzyl-11-[2-(4-bromo-2-methoxyphenoxy)ethyl]-2,3,4,5-te-
trahydro-1H-[1,4]diazepino[1,7-a]indole
N-benzyl-2-(3-benzyl-2,3,4,5-tetra-
hydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanamine
11-[2-(2-chlorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indole
11-[2-(4-bromo-2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
2-phenoxy-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indol-11-yl)-1-ethanone
N-(4-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
4-methoxy-N-[2-(2,3,4,5-te-
trahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethyl]aniline
dihydrochloride
2-hydroxy-N-(4-methoxyphenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a]indol-11-yl)acetamide
2-(2-methoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,-
4]diazepino[1,7-a]indol-11-yl)-1-ethanone
2-(4-bromo-2-methoxyphenoxy)-1-(-
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanone
N-(4-methoxyphenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-1-
1-yl)acetamide
2-(4-methoxyanilino)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indol-11-yl)-1-ethanone dihydrochloride
N-(2,4-difluorophenyl)-2-o-
xo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
N-(3-chloro-4-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indol-11-yl)acetamide
2-oxo-N-phenyl-2-(2,3,4,5-tetrahydro-1H-[1,4-
]diazepino[1,7-a]indol-11-yl)acetamide
N-(2-naphthyl)-2-oxo-2-(2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
N-(2,4-difluorophenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)acetamide
8-phenyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo- le
8-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
8-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
8-(2,4-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
8-(2-chloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indole
8-(4-isopropylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaze-
pino[1,7-a]indole
8-(4-butylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
8-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
8-(4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4,5-trimethylphenyl)-2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-chlorophenyl)-2,3,4,-
5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-methylphenyl)-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chloro-2-methylphenyl)-2,3,4,5-
-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,5-dichlorophenyl)-2,3,4,5--
tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-isopropyl-2-methoxyphenyl)--
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,6-dichlorophenyl)-2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,6-difluorophenyl)-2,-
3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-methoxy-2-(trifluorom-
ethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indole
8-(4-pyridinyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-furyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzenethiol
8-(2,3-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-ethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-chloro-2-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
8-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitril-
e
8-[3-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indole
8-(2-naphthyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
1-[4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]ethano-
ne
N-[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]acet-
amide
8-(2,3-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
8-(5-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
8-(2-fluoro-5-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
8-(5-fluoro-2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indole
8-(3-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
8-(3-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole
8-(2-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
8-(2-chloro-3-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
8-(2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
8-(4-ethoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
8-(4-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indole
8-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4-
]diazepino[1,7-a]indole
8-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(trifluoromethyl)phenyl]-2,3,4-
,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(trifluoromethoxy)phenyl-
]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
8-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
8-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indole
8-[2-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
8-(2,4,6-trifluorophenyl)-2,3,4,5-tetrahydro-1H--
[1,4]diazepino[1,7-a]indole
8-(2,4,6-trichlorophenyl)-2,3,4,5-tetrahydro-1-
H-[1,4]diazepino[1,7-a]indole
8-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4-trifluorophenyl)-2,3,4,5-t-
etrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chloro-2,6-difluorophenyl)-2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4,6-tetrafluorophe-
nyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
8-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indole
8-[2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
8-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5--
tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-isopropoxy-2-(trifluorometh-
yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
8-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-ethoxyphenyl]-2,3,4,5-tetrahy-
dro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-isopropoxyphenyl]-2,3,4,5-
-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-ethyl-4-methoxyphenyl)-2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5-tetrah-
ydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzaldehyde
8-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
8-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indol-8-yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]methanol
8-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-8-yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-8-yl)phenyl]-1-propanone methyl
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-y-
l)phenyl]-2-propenoate methyl
3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-8-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5-t-
etrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-2-propen-1-ol
methyl
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-y-
l)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indol-8-yl)phenyl]-2-propen-1-ol
8-[4-methoxy-2-(2-methoxyeth-
yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-fluoro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
8-(2-chloro-4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a]indole
8-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-ylmethyl)phenol
8-(2-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-ylmethyl)phenol
methyl
2-methoxy-6-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl-
)benzoate
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzoni-
trile
3-methyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)be-
nzonitrile
2-methyl-3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8--
yl)benzonitrile
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)b-
enzonitrile
3-trifluoromethyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indol-8-yl)benzonitrile
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-8-yl)benzaldehyde
[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
-8-yl)phenyl]methanol
8-[3-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5-tetrahydro-1H-[1,4]diaze-
pino[1,7-a]indol-8-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
2-fluoro-5-(2,3,4,5-tetrahyd-
ro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzamide
8-phenyl-2,3,4,5,11,11a-he- xahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4-dichlorophenyl)-2,3,4,5,11,1-
1a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-fluorophenyl)-2,3,4,5,11,-
11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chlorophenyl)-2,3,4,5,11-
,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chlorophenyl)-2,3,4,5,1-
1,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-methoxyphenyl)-2,3,4,5-
,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-(trifluorom-
ethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
8-(2-chloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
8-(4-isopropylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
8-(4-butylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
8-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5,11,11a--
hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-methoxy-2-methylphenyl)-2,3,-
4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
8-(2,4,5-trimethylphenyl)-2,3,4,5,11,11a-hexahydro--
1H-[1,4]diazepino[1,7-a]indole
8-(3-chlorophenyl)-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indole
8-(4-methylphenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
8-(4-chloro-2-methylphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,5-dichlorophenyl)-2,3,4,5,-
11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-isopropyl-2-methoxyph-
enyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,6-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
8-(2,6-difluorophenyl)-2,3,4,5,11,1a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indole
8-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indole
8-[2-(trifluoromethyl)phenyl]-2,3,4,5,11,1-
1a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-pyridinyl)-2,3,4,5,11,11a-
-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-furyl)-2,3,4,5,11,11a-hexah-
ydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indol-8-yl)benzenethiol
8-(2,3-dichlorophenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-ethylphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4-dimethoxyphenyl)-2,3,4,5-
,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-chloro-2-fluoropheny-
l)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indo-
le
8-[4-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino-
[1,7-a]indole
4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8--
yl)benzonitrile
8-[3-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
8-(2-naphthyl)-2,3,4,5,11,11a-hexahydro-1H-[1,-
4]diazepino[1,7-a]indole
1-[4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[-
1,7-a]indol-8-yl)phenyl]ethanone
N-[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indol-8-yl)phenyl]acetamide
8-(2,3-dimethylphenyl)-2,3,4,5,1-
1,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(5-fluoro-2-methylphenyl)-
-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-fluoro-5-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
8-(5-fluoro-2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
8-(3-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
8-(3-nitrophenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
8-(2-nitrophenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
8-(2-chloro-3-methylphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-methoxylphenyl)-2,3,4,5,11-
,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-ethoxy-2-methylphenyl)--
2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
8-(2-chloro-6-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
8-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5,11,11a-
-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(trifluoromethyl)phenyl]-2,-
3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino-
[1,7-a]indole
8-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5,11,11a-hexahydro-1-
H-[1,4]diazepino[1,7-a]indole
8-(2-methylphenyl)-2,3,4,5,11,11a-hexahydro--
1H-[1,4]diazepino[1,7-a]indole
8-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,-
4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
8-(2,4,6-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indole
8-(2,4,6-trichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
8-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4-trifluorophenyl)-2,3,4-
,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chloro-2,6-difluor-
ophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4,6-tetrafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[-
1,7-a]indole
8-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[-
1,4]diazepino[1,7-a]indole
8-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-(trifluoromethoxy)phenyl]--
2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
8-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,-
11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-chloro-2-(trifluorome-
thyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
8-[2-chloro-4-ethoxyphenyl]-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-isopropoxyphenyl]-2,3,4,5,11-
,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-ethyl-4-methoxyphenyl)--
2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)-
benzaldehyde
8-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indole
8-[4-methoxy-2-(1-methoxyethyl)phenyl]-2-
,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8--
yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indol-8-yl)phenyl]methanol
8-[4-methoxy-2-(methoxymethyl)phenyl]-2-
,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8--
yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indol-8-yl)phenyl]-1-propanone methyl
(2Z)-3-[5-methoxy-2-(2,-
3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-2-propen-
oate methyl
3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indol-8-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahy-
dro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-2-propen-1-ol methyl
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-8-yl)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-2-propen-1-ol
8-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
8-(2-fluoro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
8-(2-chloro-4-fluorophenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-benzyl-2,3,4,5,11,11a-hexahyd- ro-1H-[1,4]diazepino[1,7-a]indole
8-(2-fluorobenzyl)-2,3,4,5,11,11a-hexahy-
dro-1H-[1,4]diazepino[1,7-a]indole
8-(3-fluorobenzyl)-2,3,4,5,11,11a-hexah-
ydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-fluorobenzyl)-2,3,4,5,11,11a-hexa-
hydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-methoxybenzyl)-2,3,4,5,11,11a-he-
xahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4-
]diazepino[1,7-a]indol-8-ylmethyl)phenol
8-(2-methoxybenzyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indol-8-ylmethyl)phenol methyl
2-methoxy-6-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)-
benzoate
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)be-
nzonitrile
3-methyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-8-yl)benzonitrile
2-methyl-3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepi-
no[1,7-a]indol-8-yl)benzonitrile
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indol-8-yl)benzonitrile
3-trifluoromethyl-4-(2,3,4,5,11,11a-hex-
ahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzaldehy-
de
[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-
methanol
8-[3-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indol-8-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
2-fluoro-5-(2,3,4,5,11,-
11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzamide
7-phenyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
7-(2,4-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
7-(2-chloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indole
7-(4-isopropylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaze-
pino[1,7-a]indole
7-(4-butylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
7-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
7-(4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4,5-trimethylphenyl)-2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-chlorophenyl)-2,3,4,-
5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-methylphenyl)-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chloro-2-methylphenyl)-2,3,4,5-
-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,5-dichlorophenyl)-2,3,4,5--
tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-isopropyl-2-methoxyphenyl)--
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,6-dichlorophenyl)-2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,6-difluorophenyl)-2,-
3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-methoxy-2-(trifluorom-
ethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indole
7-(4-pyridinyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-furyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzenethiol
7-(2,3-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-ethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-chloro-2-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
7-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitril-
e
7-[3-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indole
7-(2-naphthyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
1-[4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]ethano-
ne
N-[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]acet-
amide
7-(2,3-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
7-(5-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
7-(2-fluoro-5-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
7-(5-fluoro-2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indole
7-(3-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
7-(3-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole
7-(2-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
7-(2-chloro-3-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
7-(2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
7-(4-ethoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
7-(4-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indole
7-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4-
]diazepino[1,7-a]indole
7-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(trifluoromethyl)phenyl]-2,3,4-
,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(trifluoromethoxy)phenyl-
]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
7-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
7-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indole
7-[2-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
7-(2,4,6-trifluorophenyl)-2,3,4,5-tetrahydro-1H--
[1,4]diazepino[1,7-a]indole
7-(2,4,6-trichlorophenyl)-2,3,4,5-tetrahydro-1-
H-[1,4]diazepino[1,7-a]indole
7-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4-trifluorophenyl)-2,3,4,5-t-
etrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chloro-2,6-difluorophenyl)-2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4,6-tetrafluorophe-
nyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
7-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indole
7-[2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
7-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5--
tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-isopropoxy-2-(trifluorometh-
yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
7-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-ethoxyphenyl]-2,3,4,5-tetrahy-
dro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-isopropoxyphenyl]-2,3,4,5-
-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-ethyl-4-methoxyphenyl)-2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5-tetrah-
ydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzaldehyde
7-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
7-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indol-7-yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]methanol
7-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-7-yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-7-yl)phenyl]-1-propanone methyl
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-y-
l)phenyl]-2-propenoate methyl
3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-7-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5-t-
etrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propen-1-ol
methyl
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-y-
l)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indol-7-yl)phenyl]-2-propen-1-ol
7-[4-methoxy-2-(2-methoxyeth-
yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-fluoro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
7-(2-chloro-4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a]indole
7-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-ylmethyl)phenol
7-(2-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-ylmethyl)phenol
methyl
2-methoxy-6-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl-
)benzoate
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzoni-
trile
3-methyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)be-
nzonitrile
2-methyl-3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7--
yl)benzonitrile
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)b-
enzonitrile
3-trifluoromethyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indol-7-yl)benzonitrile
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-7-yl)benzaldehyde
[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
-7-yl)phenyl]methanol
7-[3-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5-tetrahydro-1H-[1,4]diaze-
pino[1,7-a]indol-7-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
2-fluoro-5-(2,3,4,5-tetrahyd-
ro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzamide
7-phenyl-2,3,4,5,11,11a-he- xahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dichlorophenyl)-2,3,4,5,11,1-
1a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-fluorophenyl)-2,3,4,5,11,-
11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chlorophenyl)-2,3,4,5,11-
,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-chlorophenyl)-2,3,4,5,1-
1,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-methoxyphenyl)-2,3,4,5-
,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-(trifluorom-
ethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
7-(2-chloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
7-(4-isopropylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
7-(4-butylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
7-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5,11,11a--
hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-methoxy-2-methylphenyl)-2,3,-
4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
7-(2,4,5-trimethylphenyl)-2,3,4,5,11,11a-hexahydro--
1H-[1,4]diazepino[1,7-a]indole
7-(3-chlorophenyl)-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indole
7-(4-methylphenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
7-(4-chloro-2-methylphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,5-dichlorophenyl)-2,3,4,5,-
11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-isopropyl-2-methoxyph-
enyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,6-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
7-(2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
7-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
7-[2-(trifluoromethyl)phenyl]-2,3,4,5,11,-
11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-pyridinyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-furyl)-2,3,4,5,11,11a-hexa-
hydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indol-7-yl)benzenethiol
7-(2,3-dichlorophenyl)-2,3,4,5,11,1-
1a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-ethylphenyl)-2,3,4,5,11,1-
1a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dimethoxyphenyl)-2,3,4,-
5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-chloro-2-fluorophen-
yl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indo-
le
7-[4-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino-
[1,7-a]indole
4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7--
yl)benzonitrile
7-[3-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
7-(2-naphthyl)-2,3,4,5,11,11a-hexahydro-1H-[1,-
4]diazepino[1,7-a]indole
1-[4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[-
1,7-a]indol-7-yl)phenyl]ethanone
N-[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indol-7-yl)phenyl]acetamide
7-(2,3-dimethylphenyl)-2,3,4,5,1-
1,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(5-fluoro-2-methylphenyl)-
-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-fluoro-5-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
7-(5-fluoro-2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
7-(3-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
7-(3-nitrophenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
7-(2-nitrophenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
7-(2-chloro-3-methylphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-methoxylphenyl)-2,3,4,5,11-
,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-ethoxy-2-methylphenyl)--
2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
7-(2-chloro-6-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
7-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5,11,11a-
-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(trifluoromethyl)phenyl]-2,-
3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino-
[1,7-a]indole
7-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5,11,11a-hexahydro-1-
H-[1,4]diazepino[1,7-a]indole
7-(2-methylphenyl)-2,3,4,5,11,11a-hexahydro--
1H-[1,4]diazepino[1,7-a]indole
7-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,-
4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
7-(2,4,6-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indole
7-(2,4,6-trichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
7-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4-trifluorophenyl)-2,3,4-
,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chloro-2,6-difluor-
ophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4,6-tetrafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[-
1,7-a]indole
7-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[-
1,4]diazepino[1,7-a]indole
7-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-(trifluoromethoxy)phenyl]--
2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
7-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,-
11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-chloro-2-(trifluorome-
thyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
7-[2-chloro-4-ethoxyphenyl]-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-isopropoxyphenyl]-2,3,4,5,11-
,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-ethyl-4-methoxyphenyl)--
2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)-
benzaldehyde
7-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indole
7-[4-methoxy-2-(1-methoxyethyl)phenyl]-2-
,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7--
yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indol-7-yl)phenyl]methanol
7-[4-methoxy-2-(methoxymethyl)phenyl]-2-
,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7--
yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indol-7-yl)phenyl]-1-propanone methyl
(2Z)-3-[5-methoxy-2-(2,-
3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propen-
oate methyl
3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indol-7-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahy-
dro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propen-1-ol methyl
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-7-yl)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propen-1-ol
7-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
7-(2-fluoro-4-methoxyphenyl)-2,4,5,11,11a-hexahydro--
1H-[1,4]diazepino[1,7-a]indole
7-(2-chloro-4-fluorophenyl)-2,3,4,5,11,11a--
hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-benzyl-2,3,4,5,11,11a-hexahydro- -1H-[1,4]diazepino[1,7-a]indole
7-(2-fluorobenzyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
7-(3-fluorobenzyl)-2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indole
7-(4-fluorobenzyl)-2,3,4,5,11,11a-hexahy-
dro-1H-[1,4]diazepino[1,7-a]indole
7-(3-methoxybenzyl)-2,3,4,5,11,11a-hexa-
hydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indol-7-ylmethyl)phenol
7-(2-methoxybenzyl)-2,3,4,5,11,11a--
hexahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H-[1-
,4]diazepino[1,7-a]indol-7-ylmethyl)phenol methyl
2-methoxy-6-(2,3,4,5,11,-
11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzoate
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitri-
le
3-methyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl-
)benzonitrile
2-methyl-3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indol-7-yl)benzonitrile
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indol-7-yl)benzonitrile
3-trifluoromethyl-4-(2,3,4,5,11,11a-hexahydro-1-
H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
3-(2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzaldehyde
[3-(2,3,4,5,11,11a-hexahy-
dro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]methanol
7-[3-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
N,N-dimethyl[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indol-7-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1-
,4]diazepino[1,7-a]indol-7-yl)benzonitrile
2-fluoro-5-(2,3,4,5,11,11a-hexa-
hydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzamide
9-phenyl-2,3,4,5,11,11a- -hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dichlorophenyl)-2,3,4,5-t-
etrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-fluorophenyl)-2,3,4,5-tetrah-
ydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-chlorophenyl)-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
9-(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
9-(2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
9-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5-tetra-
hydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dimethylphenyl)-2,3,4,5-tetrah-
ydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chloro-4-methoxyphenyl)-2,3,4,5-t-
etrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-isopropylphenyl)-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-butylphenyl)-2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indole
9-(5-fluoro-4-methoxy-2-methylphenyl)-2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-methoxy-2-methylphenyl-
)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole
9-(2,4,5-trimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indole
9-(3-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indole
9-(4-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
9-(4-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
9-(2,5-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
9-(4-isopropyl-2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indole
9-(2,6-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indole
9-(2,6-difluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaze-
pino[1,7-a]indole
9-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahyd-
ro-1H-[1,4]diazepino[1,7-a]indole
9-[2-(trifluoromethyl)phenyl]-2,3,4,5-te-
trahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-pyridinyl)-2,3,4,5-tetrahydro- -1H-[1,4]diazepino[1,7-a]indole
9-(2-furyl)-2,3,4,5-tetrahydro-1H-[1,4]dia- zepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9--
yl)benzenethiol
9-(2,3-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
9-(4-ethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
9-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
9-(3-chloro-2-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
9-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
9-[4-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indole
4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)ben-
zonitrile
9-[3-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
9-(2-naphthyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]- indole
1-[4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-
ethanone
N-[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)pheny-
l]acetamide
9-(2,3-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
9-(5-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
9-(2-fluoro-5-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indole
9-(5-fluoro-2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,-
4]diazepino[1,7-a]indole
9-(3-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indole
9-(3-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
9-(2-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole
9-(2-chloro-3-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indole
9-(2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaze-
pino[1,7-a]indole
9-(4-ethoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
9-(4-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
9-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1-
H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4-
,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-(trifluoromethyl)phenyl]-
-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-(trifluoromethoxy)-
phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
9-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
9-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indole
9-[2-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
9-(2,4,6-trifluorophenyl)-2,3,4,5-tetrahydro-1H--
[1,4]diazepino[1,7-a]indole
9-(2,4,6-trichlorophenyl)-2,3,4,5-tetrahydro-1-
H-[1,4]diazepino[1,7-a]indole
9-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4-trifluorophenyl)-2,3,4,5-t-
etrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-chloro-2,6-difluorophenyl)-2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4,6-tetrafluorophe-
nyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
9-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indole
9-[2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
9-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5--
tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-isopropoxy-2-(trifluorometh-
yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
9-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-ethoxyphenyl]-2,3,4,5-tetrahy-
dro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-isopropoxyphenyl]-2,3,4,5-
-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-ethyl-4-methoxyphenyl)-2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5-tetrah-
ydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzaldehyde
9-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
9-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indol-9-yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]methanol
9-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-9-yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-9-yl)phenyl]-1-propanone methyl
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-y-
l)phenyl]-2-propenoate methyl
3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-9-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5-t-
etrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propen-1-ol
methyl
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-y-
l)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indol-9-yl)phenyl]-2-propen-1-ol
9-[4-methoxy-2-(2-methoxyeth-
yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-fluoro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
9-(2-chloro-4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a ]indole
9-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-ylmethyl)phenol
9-(2-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-ylmethyl)phenol
methyl
2-methoxy-6-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl-
)benzoate
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzoni-
trile
3-methyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)be-
nzonitrile
2-methyl-3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9--
yl)benzonitrile
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)b-
enzonitrile
3-trifluoromethyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indol-9-yl)benzonitrile
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-9-yl)benzaldehyde
[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
-9-yl)phenyl]methanol
9-[3-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5-tetrahydro-1H-[1,4]diaze-
pino[1,7-a]indol-9-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
2-fluoro-5-(2,3,4,5-tetrahyd-
ro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzamide
9-phenyl-2,3,4,5,11,11a-he- xahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dichlorophenyl)-2,3,4,5,11,1-
1a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-fluorophenyl)-2,3,4,5,11,-
11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-chlorophenyl)-2,3,4,5,11-
,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chlorophenyl)-2,3,4,5,1-
1,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-methoxyphenyl)-2,3,4,5-
,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-(trifluorom-
ethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
9-(2-chloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
9-(4-isopropylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
9-(4-butylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
9-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5,11,11a--
hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-methoxy-2-methylphenyl)-2,3,-
4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
9-(2,4,5-trimethylphenyl)-2,3,4,5,11,11a-hexahydro--
1H-[1,4]diazepino[1,7-a]indole
9-(3-chlorophenyl)-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indole
9-(4-methylphenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
9-(4-chloro-2-methylphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,5-dichlorophenyl)-2,3,4,5,-
11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-isopropyl-2-methoxyph-
enyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,6-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
9-(2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
9-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
9-[2-(trifluoromethyl)phenyl]-2,3,4,5,11,-
11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-pyridinyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-furyl)-2,3,4,5,11,11a-hexa-
hydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indol-9-yl)benzenethiol
9-(2,3-dichlorophenyl)-2,3,4,5,11,1-
1a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-ethylphenyl)-2,3,4,5,11,1-
1a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dimethoxyphenyl)-2,3,4,-
5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-chloro-2-fluorophen-
yl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indo-
le
9-[4-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino-
[1,7-a]indole
4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9--
yl)benzonitrile
9-[3-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
9-(2-naphthyl)-2,3,4,5,11,11a-hexahydro-1H-[1,- 4]diazepino[1,7-a
]indole 1-[4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino-
[1,7-a]indol-9-yl)phenyl]ethanone
N-[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indol-9-yl)phenyl]acetamide
9-(2,3-dimethylphenyl)-2,3,4,5,-
11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(5-fluoro-2-methylphenyl-
)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-fluoro-5-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
9-(5-fluoro-2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
9-(3-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
9-(3-nitrophenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
9-(2-nitrophenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
9-(2-chloro-3-methylphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-methoxylphenyl)-2,3,4,5,11-
,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-ethoxy-2-methylphenyl)--
2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
9-(2-chloro-6-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
9-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5,11,11a-
-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-(trifluoromethyl)phenyl]-2,-
3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino-
[1,7-a]indole
9-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5,11,11a-hexahydro-1-
H-[1,4]diazepino[1,7-a]indole
9-(2-methylphenyl)-2,3,4,5,11,11a-hexahydro--
1H-[1,4]diazepino[1,7-a]indole
9-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,-
4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
9-(2,4,6-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indole
9-(2,4,6-trichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
9-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4-trifluorophenyl)-2,3,4-
,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-chloro-2,6-difluor-
ophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4,6-tetrafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[-
1,7-a]indole
9-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[-
1,4]diazepino[1,7-a]indole
9-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-(trifluoromethoxy)phenyl]--
2,3,4,5,11,111a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
9-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,-
11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-chloro-2-(trifluorome-
thyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
9-[2-chloro-4-ethoxyphenyl]-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-isopropoxyphenyl]-2,3,4,5,11-
,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-ethyl-4-methoxyphenyl)--
2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)-
benzaldehyde
9-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indole
9-[4-methoxy-2-(1-methoxyethyl)phenyl]-2-
,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9--
yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indol-9-yl)phenyl]methanol
9-[4-methoxy-2-(methoxymethyl)phenyl]-2-
,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9--
yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indol-9-yl)phenyl]-1-propanone methyl
(2Z)-3-[5-methoxy-2-(2,-
3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propen-
oate methyl
3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indol-9-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahy-
dro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propen-1-ol methyl
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-9-yl)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propen-1-ol
9-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
9-(2-fluoro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
9-(2-chloro-4-fluorophenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-benzyl-2,3,4,5,11,11a-hexahyd- ro-1H-[1,4]diazepino[1,7-a]indole
9-(2-fluorobenzyl)-2,3,4,5,11,11a-hexahy-
dro-1H-[1,4]diazepino[1,7-a]indole
9-(3-fluorobenzyl)-2,3,4,5,11,11a-hexah-
ydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-fluorobenzyl)-2,3,4,5,11,11a-hexa-
hydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-methoxybenzyl)-2,3,4,5,11,11a-he-
xahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4-
]diazepino[1,7-a]indol-9-ylmethyl)phenol
9-(2-methoxybenzyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indol-9-ylmethyl)phenol methyl
2-methoxy-6-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)-
benzoate
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)be-
nzonitrile
3-methyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-9-yl)benzonitrile
2-methyl-3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepi-
no[1,7-a]indol-9-yl)benzonitrile
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indol-9-yl)benzonitrile
3-trifluoromethyl-4-(2,3,4,5,11,11a-hex-
ahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzaldehy-
de
[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-
methanol
9-[3-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indol-9-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile, and
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)b-
enzamide.
4. The compound of claim 1 in native form, acid salt form or base
salt form.
5. A compound of formula I: 220where a is a single bond or double
bond, and where R1a, R1b, R2a and R2b are each independently (a) H,
Cl, Br, I, F, CN, CF.sub.3, OCF.sub.3, OR5, CONR5R6, COR5, CO2R5,
Y(CH.sub.2).sub.mXR5 or YC(O)(CH.sub.2).sub.mXR5, where m=0-3,
Y=CH.sub.2, S, O, or NR6, X=CH.sub.2, S, O, NR6; (b) (CH2).sub.pAr
where p=0-3 and Ar is aryl or heteroaryl optionally substituted
with one or more of the following: H, halogen, CN, NO.sub.2, OR7,
CF.sub.3, OCF.sub.3, SR7, SO.sub.2R7, SO.sub.2NR7R8, NR7R8,
CONR7R8, NR7COR8, NR7CONR8R9, CO.sub.2R7, COR7, or R7; or (c)
linear or branched C.sub.1-C.sub.8 alkyl, linear or branched
C.sub.2-C.sub.8 alkenyl, linear or branched C.sub.2-C.sub.8
alkynyl, C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 cycloalkenyl,
or C.sub.3-C.sub.8 cycloalkynyl; wherein any of these groups may be
optionally substituted with one or more of the following: halogen,
CN, NO.sub.2, COR7, OR7, NR7R8, SR7, CO2R7, CONR7R8 or NR7COR8; and
where R3 is (a) H, Cl, Br, I, F, CN, CF.sub.3, OCF.sub.3, alkyl,
Ar, OR5, SR5, CHO, CONR5R6, COR5, CO2R5, (Y).sub.o(CH2).sub.nXR5,
C(O)C(O)XR5, (Y).sub.o(CH.sub.2).sub.nC(O)XR5, C(O)(CH2).sub.nXR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)R5,
(Y).sub.o(CH2).sub.nN(R6)S(O).sub.2R5,
(Y).sub.o(CH2).sub.6)C(O)OR5, (Y).sub.o(CH2).sub.nN(R6)C(O)NR5R6
where o=0 or 1, n=0-3, X=CH.sub.2, S, O, or NR6 and Y=CH.sub.2, S,
O or NR6, where Ar is aryl or heteroaryl optionally substituted
with one or more of the following: H, halogen, CN, NO.sub.2, OR7,
CF.sub.3, OCF.sub.3, SR7, SO.sub.2R7, SO.sub.2NR7R8, NR7R8,
CONR7R8, NR7COR8, NR7CONR8R9, CO.sub.2R7, COR7, or R7; or (b)
linear or branched C.sub.1-C.sub.8 alkyl, linear or branched
C.sub.2-C.sub.8 alkenyl, linear or branched C.sub.2-C.sub.8
alkynyl, C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 cycloalkenyl,
or C.sub.3-C.sub.8 cycloalkynyl; wherein any of these groups may be
optionally substituted with one or more of the following: halogen,
CN, NO.sub.2, COR10, OR10, NR10R8, SR10, CO2R10, CONR10R8 or
NR10COR8; and where R4, R5 and R6 are each independently (a) H,
linear or branched C.sub.1-C.sub.8 alkyl, linear or branched
C.sub.2-C.sub.8 alkenyl, linear or branched C.sub.2-C.sub.8
alkynyl, C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 cycloalkenyl,
or C.sub.3-C.sub.8 cycloalkynyl; wherein any of these groups other
than H may be optionally substituted with one or more of the
following: halogen, CN, NO.sub.2, COR10, OR10, NR10R11, SR10,
CO2R10, CONR10R11 or NR10COR11; or where R5 and R6 are linked to
form a 3 to 8 member ring; or (b) (CH.sub.2).sub.pAr where p=0-3
and Ar is aryl or heteroaryl optionally substituted with one or
more of the following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3,
OCF.sub.3, SR7, SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8,
NR7CONR8R9, C.sub.2R7, COR7, or R7, and where R7, R8, and R9 are
each independently (a) H, linear or branched C.sub.1-C.sub.8 alkyl,
linear or branched C.sub.2-C.sub.8 alkenyl, linear or branched
C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl
groups, wherein any of these groups other than H may be optionally
substituted with halogen, CN, NO.sub.2, COR10, OR10, NR10R11, SR10,
CO2R10, CONR10R11, NR10COR11, NR10CONR11R12, or where R7, R8, or R9
are linked to form a ring; or (b) (CH2).sub.pAr where p=0-3 and Ar
is aryl or heteroaryl optionally substituted with one or more of
the following: H, halogen, CN, NO.sub.2, OR10, CF.sub.3, OCF.sub.3,
SR10, SO.sub.2R10, SO.sub.2NR10R11, NR10R11, CONR10R11, NR10COR11,
NR10CONR11R12, CO.sub.2R10, COR10, or R10; and where R10, R11 and
R12 are each independently H, linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl; or a
stereoisomer or pharmaceutically acceptable salt thereof.
6. The composition of claim 5 wherein R1a, R1b, R2a, R2b and R4 are
H and R3 is selected from either H,--C(O)C(O)XAr, --CH.sub.2C(O)XAr
or --C(O)CH.sub.2XAr.
7. The composition of claim 5 wherein the compound of formula I is
selected from the group consisting of:
2,3,4,5-tetrahydro-1H-[1,4]diazepi- no[1,7-a]indole hydrochloride
8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino- [1,7-a]indole
hydrochloride 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ole-11-carbaldehyde
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-1-yl)acetamide
2,2,2-trifluoro-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indol-11-yl)-1-ethanone
11-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazep- ino[1,7-a]indole
hydrochloride 11-chloro-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole hydrochloride
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]- indole-11-carbonitrile
8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indole-11-carbaldehyde
1-(8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a]indol-11-yl)-2,2,2-trifluoro-1-ethanone
2,3,4,5-tetrahydro-1H-[1,4]diaz- epino[1,7-a]indole-11-carboxamide
1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indol-11-yl)-1-ethanone hydrochloride
3-methyl-2,3,4,5-tetrahydro-1H- -[1,4]diazepino[1,7-a]indole
3-ethyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[- 1,7-a]indole
3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
10-methoxy-2,3,4,5-tetrahydro-1H-[1,4]diazepino [1,7-a]indole
hydrochloride ethyl
2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indol-11-yl)-2-oxoacetate
3-propyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[- 1,7-a]indole
hydrochloride 2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndol-11-yl)-1-ethanamine
2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indol-11-yl)-1-ethanol
3-benzyl-11-(2-phenoxyethyl)-2,3,4,5-tetrahyd-
ro-1H-[1,4]diazepino[1,7-a]indole
11-(2-phenoxyethyl)-2,3,4,5-tetrahydro-1-
H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(2-methoxyphenoxy)ethyl]-2,3,-
4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(2-fluorophen-
oxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(8-quinolinyloxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-
-1-ethanol
3-benzyl-11-[2-(2-methoxy-4-methylphenoxy)ethyl]-2,3,4,5-tetrah-
ydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(2-fluoro-6-methoxyphen-
oxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
11-[2-(2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indole
11-[2-(2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole hydrochloride
11-[2-(2-fluorophenoxy)ethyl]-2,3,4,5-tetrahy-
dro-1H-[1,4]diazepino[1,7-a]indole
11-[2-(2-methoxy-4-methylphenoxy)ethyl]-
-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
11-[2-(2-fluoro-6-metho-
xyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-benzyl-11-[2-(2-chlorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
3-benzyl-11-[2-(4-bromo-2-methoxyphenoxy)ethyl]-2,3,4,5-te-
trahydro-1H-[1,4]diazepino[1,7-a]indole
N-benzyl-2-(3-benzyl-2,3,4,5-tetra-
hydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanamine
11-[2-(2-chlorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indole
11-[2-(4-bromo-2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
2-phenoxy-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indol-11-yl)-1-ethanone
N-(4-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
4-methoxy-N-[2-(2,3,4,5-te-
trahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethyl]aniline
dihydrochloride
2-hydroxy-N-(4-methoxyphenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a]indol-11-yl)acetamide
2-(2-methoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,-
4]diazepino[1,7-a]indol-11-yl)-1-ethanone
2-(4-bromo-2-methoxyphenoxy)-1-(-
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanone
N-(4-methoxyphenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-1-
1-yl)acetamide
2-(4-methoxyanilino)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indol-11-yl)-1-ethanone dihydrochloride
N-(2,4-difluorophenyl)-2-o-
xo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
N-(3-chloro-4-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indol-1-yl)acetamide
2-oxo-N-phenyl-2-(2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indol-11-yl)acetamide
N-(2-naphthyl)-2-oxo-2-(2,3,4,5-tetr-
ahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
N-(2,4-difluorophenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)acetamide
8-phenyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo- le
8-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
8-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
8-(2,4-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
8-(2-chloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indole
8-(4-isopropylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaze-
pino[1,7-a]indole
8-(4-butylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
8-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
8-(4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4,5-trimethylphenyl)-2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-chlorophenyl)-2,3,4,-
5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-methylphenyl)-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chloro-2-methylphenyl)-2,3,4,5-
-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,5-dichlorophenyl)-2,3,4,5--
tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-isopropyl-2-methoxyphenyl)--
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,6-dichlorophenyl)-2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,6-difluorophenyl)-2,-
3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-methoxy-2-(trifluorom-
ethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indole
8-(4-pyridinyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-furyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino
[1,7-a]indol-8-yl)benzenethiol
8-(2,3-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-ethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-chloro-2-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
8-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitril-
e
8-[3-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indole
8-(2-naphthyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
1-[4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]ethano-
ne
N-[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]acet-
amide
8-(2,3-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
8-(5-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
8-(2-fluoro-5-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
8-(5-fluoro-2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indole
8-(3-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
8-(3-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole
8-(2-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
8-(2-chloro-3-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
8-(2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
8-(4-ethoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
8-(4-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indole
8-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4-
]diazepino[1,7-a]indole
8-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(trifluoromethyl)phenyl]-2,3,4-
,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(trifluoromethoxy)phenyl-
]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
8-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
8-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino [1,7-a]indole
8-[2-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[-
1,4]diazepino[1,7-a]indole
8-(2,4,6-trifluorophenyl)-2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indole
8-(2,4,6-trichlorophenyl)-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
8-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5-te-
trahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4-trifluorophenyl)-2,3,4,5--
tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chloro-2,6-difluorophenyl)--
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4,6-tetrafluoroph-
enyl)-2,34,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
8-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indole
8-[2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
8-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5--
tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-isopropoxy-2-(trifluorometh-
yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
8-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-ethoxyphenyl]-2,3,4,5-tetrahy-
dro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-isopropoxyphenyl]-2,3,4,5-
-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-ethyl-4-methoxyphenyl)-2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5-tetrah-
ydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzaldehyde
8-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
8-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indol-8-yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]methanol
8-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-8-yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-8-yl)phenyl]-1-propanone methyl
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-y-
l)phenyl]-2-propenoate methyl
3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-8-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5-t-
etrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-2-propen-1-ol
methyl (2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-b
1H-[1,4]diazepino[1,7-a]indol-8- -yl)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-8-yl)phenyl]-2-propen-1-ol
8-[4-methoxy-2-(2-methoxye-
thyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-fluoro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
8-(2-chloro-4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a]indole
8-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-ylmethyl)phenol
8-(2-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-ylmethyl)phenol
methyl
2-methoxy-6-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl-
)benzoate
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzoni-
trile
3-methyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)be-
nzonitrile
2-methyl-3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8--
yl)benzonitrile 2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino
[1,7-a]indol-8-yl)benzonitrile
3-trifluoromethyl-4-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
3-(2,3,4,5-tetrahydro-1H-[1,-
4]diazepino[1,7-a]indol-8-yl)benzaldehyde
[3-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-8-yl)phenyl]methanol
8-[3-(methoxymethyl)phenyl]-2,3,-
4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5-tetr-
ahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzoni-
trile
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)be-
nzamide
8-phenyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
8-(4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
8-(4-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
8-(2-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
8-(2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
8-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a
8-(2,4-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1-
H-[1,4]diazepino[1,7-a]indole
8-(2-chloro-4-methoxyphenyl)-2,3,4,5,11,11a--
hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-isopropylphenyl)-2,3,4,5,11,-
11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-butylphenyl)-2,3,4,5,11,-
11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(5-fluoro-4-methoxy-2-methy-
lphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-methoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
8-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4,5-trimethylphenyl)-2,3,4,5,11,11a-
-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-chlorophenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-methylphenyl)-2,3,4,5,11,1-
1a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(4-chloro-2-methylphenyl)-2,-
3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,5-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
8-(4-isopropyl-2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indole
8-(2,6-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,-
4]diazepino[1,7-a]indole
8-(2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1-
H-[1,4]diazepino[1,7-a]indole
8-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,-
4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[-
1,7-a]indole
8-(4-pyridinyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
8-(2-furyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dole
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzen-
ethiol
8-(2,3-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
8-(4-ethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
8-(2,4-dimethoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
8-(3-chloro-2-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
8-(4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1-
H-[1,4]diazepino[1,7-a]indole
8-[4-(methylsulfanyl)phenyl]-2,3,4,5,11,11a--
hexahydro-1H-[1,4]diazepino[1,7-a]indole
4-(2,3,4,5,11,11a-hexahydro-1H-[1-
,4]diazepino[1,7-a]indol-8-yl)benzonitrile
8-[3-(trifluoromethyl)phenyl]-2-
,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-naphthyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-
ethanone
N-[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl-
)phenyl]acetamide
8-(2,3-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
8-(5-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
8-(2-fluoro-5-methylphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(5-fluoro-2-methoxylphenyl)-2-
,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(3-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
8-(3-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
8-(2-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
8-(2-chloro-3-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
8-(2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4-
]diazepino[1,7-a]indole
8-(4-ethoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indole
8-(4-fluoro-2-methylphenyl)-2,3,4,5,11,1-
1a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chloro-6-fluorophenyl)-2,-
3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
8-[4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indole
8-[4-(trifluoromethoxy)phenyl]-2,3,4,5,1-
1,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(6-fluoro-2,4-dimethoxylp-
henyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-
e
8-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
8-[2-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4,6-trifluorophenyl)-2,3,4,5,11,11a-
-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,4,6-trichlorophenyl)-2,3,4,-
5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,6-dichloro-4-methox-
yphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
8-(4-chloro-2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
8-(2,3,4,6-tetrafluorophenyl)-2,3,4,5,11,11a-hexahy-
dro-1H-[1,4]diazepino[1,7-a]indole
8-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5-
,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2,6-di(trifluoromethyl-
)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino-
[1,7-a]indole
8-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexah-
ydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-isopropoxy-2-(trifluoromethyl)phe-
nyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
8-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-ethoxyphenyl]-2,3-
,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[2-chloro-4-isopropoxyphenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indole
8-(2-ethyl-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,-
4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indol-8-yl)benzaldehyde
8-[4-methoxy-2-(1-hydroxyethyl)phenyl-
]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indol-8-yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5,11,11a-hexah-
ydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]methanol
8-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indol-8-yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5,11,11a-h-
exahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-1-propanone
methyl
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-8-yl)phenyl]-2-propenoate methyl
3-[5-methoxy-2-(2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-8-yl)phenyl]-2-propen-1-ol methyl
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-h-
exahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-8-yl)phenyl]-2-propen-1-ol
8-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4-
,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-fluoro-4-methoxyph-
enyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
8-(2-chloro-4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
8-benzyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol- e
8-(2-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indo-
le
8-(3-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]ind-
ole
8-(4-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dole
8-(3-methoxybenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-ylmethy-
l)phenol
8-(2-methoxybenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-ylm-
ethyl)phenol methyl
2-methoxy-6-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indol-8-yl)benzoate
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[-
1,7-a]indol-8-yl)benzonitrile
3-methyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4-
]diazepino[1,7-a]indol-8-yl)benzonitrile
2-methyl-3-(2,3,4,5,11,11a-hexahy-
dro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitrile
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitri-
le
3-trifluoromethyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]i-
ndol-8-yl)benzonitrile
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indol-8-yl)benzaldehyde
[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indol-8-yl)phenyl]methanol
8-[3-(methoxymethyl)phenyl]-2,3,4,5,11,11a--
hexahydro-1H-[1,4]diazepino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5,11,11a-he-
xahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)b-
enzonitrile
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]i-
ndol-8-yl)benzamide
7-phenyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in- dole
7-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ole
7-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
7-(2,4-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
7-(2-chloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indole
7-(4-isopropylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaze-
pino[1,7-a]indole
7-(4-butylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
7-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
7-(4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4,5-trimethylphenyl)-2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-chlorophenyl)-2,3,4,-
5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-methylphenyl)-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chloro-2-methylphenyl)-2,3,4,5-
-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,5-dichlorophenyl)-2,3,4,5--
tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-isopropyl-2-methoxyphenyl)--
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,6-dichlorophenyl)-2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,6-difluorophenyl)-2,-
3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-methoxy-2-(trifluorom-
ethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indole
7-(4-pyridinyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-furyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzenethiol
7-(2,3-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-ethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-chloro-2-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
7-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitril-
e
7-[3-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indole
7-(2-naphthyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
1-[4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]ethano-
ne
N-[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]acet-
amide
7-(2,3-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
7-(5-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
7-(2-fluoro-5-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
7-(5-fluoro-2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indole
7-(3-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
7-(3-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole
7-(2-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
7-(2-chloro-3-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
7-(2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
7-(4-ethoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
7-(4-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indole
7-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4-
]diazepino[1,7-a]indole
7-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(trifluoromethyl)phenyl]-2,3,4-
,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(trifluoromethoxy)phenyl-
]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
7-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
7-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indole
7-[2-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
7-(2,4,6-trifluorophenyl)-2,3,4,5-tetrahydro-1H--
[1,4]diazepino[1,7-a]indole
7-(2,4,6-trichlorophenyl)-2,3,4,5-tetrahydro-1-
H-[1,4]diazepino[1,7-a]indole
7-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4-trifluorophenyl)-2,3,4,5-t-
etrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chloro-2,6-difluorophenyl)-2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4,6-tetrafluorophe-
nyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
7-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indole
7-[2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
7-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5--
tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-isopropoxy-2-(trifluorometh-
yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
7-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-ethoxyphenyl]-2,3,4,5-tetrahy- dro-1
H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-isopropoxyphenyl]-2,3,4,-
5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-ethyl-4-methoxyphenyl)-2,-
3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5-tetra-
hydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzaldehyde
7-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
7-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indol-7-yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]methanol
7-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-7-yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-7-yl)phenyl]-1-propanone methyl
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-y-
l)phenyl]-2-propenoate methyl
3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-7-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5-t-
etrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propen-1-ol
methyl
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-y-
l)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indol-7-yl)phenyl]-2-propen-1-ol
7-[4-methoxy-2-(2-methoxyeth-
yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-fluoro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
7-(2-chloro-4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a]indole
7-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-ylmethyl)phenol
7-(2-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-ylmethyl)phenol
methyl
2-methoxy-6-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl-
)benzoate
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzoni-
trile
3-methyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)be-
nzonitrile
2-methyl-3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7--
yl)benzonitrile
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)b-
enzonitrile
3-trifluoromethyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indol-7-yl)benzonitrile
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-7-yl)benzaldehyde
[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
-7-yl)phenyl]methanol
7-[3-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5-tetrahydro-1H-[1,4]diaze-
pino[1,7-a]indol-7-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
2-fluoro-5-(2,3,4,5-tetrahyd-
ro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzamide
7-phenyl-2,3,4,5,11,11a-he- xahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dichlorophenyl)-2,3,4,5,11,1-
1a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-fluorophenyl)-2,3,4,5,11,-
11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chlorophenyl)-2,3,4,5,11-
,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-chlorophenyl)-2,3,4,5,1-
1,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-methoxyphenyl)-2,3,4,5-
,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-(trifluorom-
ethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
7-(2-chloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
7-(4-isopropylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
7-(4-butylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
7-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5,11,11a--
hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-methoxy-2-methylphenyl)-2,3,-
4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
7-(2,4,5-trimethylphenyl)-2,3,4,5,11,11a-hexahydro--
1H-[1,4]diazepino[1,7-a]indole
7-(3-chlorophenyl)-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indole
7-(4-methylphenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
7-(4-chloro-2-methylphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,5-dichlorophenyl)-2,3,4,5,-
11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-isopropyl-2-methoxyph-
enyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,6-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
7-(2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
7-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
7-[2-(trifluoromethyl)phenyl]-2,3,4,5,11,-
11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-pyridinyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-furyl)-2,3,4,5,11,11a-hexa-
hydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indol-7-yl)benzenethiol
7-(2,3-dichlorophenyl)-2,3,4,5,11,1-
1a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-ethylphenyl)-2,3,4,5,11,1-
1a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,4-dimethoxyphenyl)-2,3,4,-
5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-chloro-2-fluorophen-
yl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indo-
le
7-[4-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino-
[1,7-a]indole
4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7--
yl)benzonitrile
7-[3-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
7-(2-naphthyl)-2,3,4,5,11,11a-hexahydro-1H-[1,-
4]diazepino[1,7-a]indole
1-[4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[-
1,7-a]indol-7-yl)phenyl]ethanone
N-[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indol-7-yl)phenyl]acetamide
7-(2,3-dimethylphenyl)-2,3,4,5,1-
1,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(5-fluoro-2-methylphenyl)-
-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-fluoro-5-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
7-(5-fluoro-2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
7-(3-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
7-(3-nitrophenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
7-(2-nitrophenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
7-(2-chloro-3-methylphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-methoxylphenyl)-2,3,4,5,11-
,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-ethoxy-2-methylphenyl)--
2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
7-(2-chloro-6-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
7-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5,11,11a-
-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(trifluoromethyl)phenyl]-2,-
3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino-
[1,7-a]indole
7-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5,11,11a-hexahydro-1-
H-[1,4]diazepino[1,7-a]indole
7-(2-methylphenyl)-2,3,4,5,11,11a-hexahydro--
1H-[1,4]diazepino[1,7-a]indole
7-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,-
4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
7-(2,4,6-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indole
7-(2,4,6-trichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
7-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4-trifluorophenyl)-2,3,4-
,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-chloro-2,6-difluor-
ophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2,3,4,6-tetrafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[-
1,7-a]indole
7-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[-
1,4]diazepino[1,7-a]indole
7-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[2-(trifluoromethoxy)phenyl]--
2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
7-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,-
11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-chloro-2-(trifluorome-
thyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
7-[2-chloro-4-ethoxyphenyl]-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indole
7-[2-chloro-4-isopropoxyphenyl]-2,3,4,5,11-
,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-(2-ethyl-4-methoxyphenyl)--
2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)-
benzaldehyde
7-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indole
7-[4-methoxy-2-(1-methoxyethyl)phenyl]-2-
,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7--
yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indol-7-yl)phenyl]methanol
7-[4-methoxy-2-(methoxymethyl)phenyl]-2-
,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7--
yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indol-7-yl)phenyl]-1-propanone methyl
(2Z)-3-[5-methoxy-2-(2,-
3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propen-
oate methyl
3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indol-7-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahy-
dro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propen-1-ol methyl
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1-H-[1,4]diazepino[1,7-a]in-
dol-7-yl)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-2-propen-1-ol
7-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
7-(2-fluoro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
7-(2-chloro-4-fluorophenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
7-benzyl-2,3,4,5,11,11a-hexahyd- ro-1H-[1,4]diazepino[1,7-a]indole
7-(2-fluorobenzyl)-2,3,4,5,11,11a-hexahy-
dro-1H-[1,4]diazepino[1,7-a]indole
7-(3-fluorobenzyl)-2,3,4,5,11,11a-hexah-
ydro-1H-[1,4]diazepino[1,7-a]indole
7-(4-fluorobenzyl)-2,3,4,5,11,11a-hexa-
hydro-1H-[1,4]diazepino[1,7-a]indole
7-(3-methoxybenzyl)-2,3,4,5,11,11a-he-
xahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4-
]diazepino[1,7-a]indol-7-ylmethyl)phenol
7-(2-methoxybenzyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indol-7-ylmethyl)phenol methyl
2-methoxy-6-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)-
benzoate
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)be-
nzonitrile
3-methyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-7-yl)benzonitrile
2-methyl-3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepi-
no[1,7-a]indol-7-yl)benzonitrile
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indol-7-yl)benzonitrile
3-trifluoromethyl-4-(2,3,4,5,11,11a-hex-
ahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzaldehy-
de
[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-
methanol
7-[3-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indol-7-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitrile
2-fluoro-5-(2,3,4,5,11,-
11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzamide
9-phenyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
9-(2,4-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
9-(2-chloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indole
9-(4-isopropylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaze-
pino[1,7-a]indole
9-(4-butylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
9-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
9-(4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4,5-trimethylphenyl)-2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-chlorophenyl)-2,3,4,-
5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-methylphenyl)-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-chloro-2-methylphenyl)-2,3,4,5-
-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,5-dichlorophenyl)-2,3,4,5--
tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-isopropyl-2-methoxyphenyl)--
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,6-dichlorophenyl)-2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2;6-difluorophenyl)-2,-
3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-methoxy-2-(trifluorom-
ethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino [1,7-a]indole
9-[2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indole
9-(4-pyridinyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-furyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzenethiol
9-(2,3-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-ethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-chloro-2-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
9-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitril-
e
9-[3-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indole
9-(2-naphthyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
1-[4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]ethano-
ne
N-[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]acet-
amide
9-(2,3-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
9-(5-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
9-(2-fluoro-5-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
9-(5-fluoro-2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indole
9-(3-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
9-(3-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole
9-(2-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
9-(2-chloro-3-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
9-(2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
9-(4-ethoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
9-(4-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indole
9-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4-
]diazepino[1,7-a]indole
9-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-(trifluoromethyl)phenyl]-2,3,4-
,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-(trifluoromethoxy)phenyl-
]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
9-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
9-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indole
9-[2-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
9-(2,4,6-trifluorophenyl)-2,3,4,5-tetrahydro-1H--
[1,4]diazepino[1,7-a]indole
9-(2,4,6-trichlorophenyl)-2,3,4,5-tetrahydro-1-
H-[1,4]diazepino[1,7-a]indole
9-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5-tet-
rahydro-1H-L[1,4]diazepino[1,7-a]indole
9-(2,3,4-trifluorophenyl)-2,3,4,5--
tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-chloro-2,6-difluorophenyl)--
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4,6-tetrafluoroph-
enyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
9-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indole
9-[2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
9-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5--
tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-isopropoxy-2-(trifluorometh-
yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
9-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-ethoxyphenyl]-2,3,4,5-tetrahy-
dro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-isopropoxyphenyl]-2,3,4,5-
-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-ethyl-4-methoxyphenyl)-2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5-tetrah-
ydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzaldehyde
9-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
9-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indol-9-yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]methanol
9-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-9-yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-9-yl)phenyl]-1-propanone methyl
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-y-
l)phenyl]-2-propenoate methyl
3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-9-yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5-t-
etrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propen-1-ol
methyl
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in
ol-9-yl)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[-
1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propen-1-ol
9-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
9-(2-fluoro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indole
9-(2-chloro-4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[[1-
,4]diazepino[1,7-a]indole
9-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino [1,7-a]indole
9-(2-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a]indole
9-(3-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
9-(4-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-ylmethyl)phenol
9-(2-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-ylmethyl)phenol
methyl
2-methoxy-6-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl-
)benzoate
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzoni-
trile
3-methyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)be-
nzonitrile
2-methyl-3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9--
yl)benzonitrile
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)b-
enzonitrile
3-trifluoromethyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indol-9-yl)benzonitrile 3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino
[1,7-a]indol-9-yl)benzaldehyde
[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino
[1,7-a]indol-9-yl)phenyl]methanol
9-[3-(methoxymethyl)phenyl]-2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzoni-
trile
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)be-
nzamide
9-phenyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
9-(4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
9-(4-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
9-(2-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
9-(2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
9-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indole
9-(2,4-dimethylphenyl)-2,3,4,5,11,11a-hexa-
hydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chloro-4-methoxyphenyl)-2,3,4,5,-
11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-isopropylphenyl)-2,3,-
4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-butylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
9-(4-methoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-(trifluoromethoxy)phenyl]-2,-
3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4,5-trimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
9-(3-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indole
9-(4-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
9-(4-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
9-(2,5-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1-
,4]diazepino[1,7-a]indole
9-(4-isopropyl-2-methoxyphenyl)-2,3,4,5,11,11a-h-
exahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,6-dichlorophenyl)-2,3,4,5,11,-
11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,6-difluorophenyl)-2,3,4,-
5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-methoxy-2-(trifluor-
omethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[-
1,7-a]indole
9-(4-pyridinyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
9-(2-furyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dole
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzen-
ethiol
9-(2,3-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
9-(4-ethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
9-(2,4-dimethoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
9-(3-chloro-2-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
9-(4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1-
H-[1,4]diazepino[1,7-a]indole
9-[4-(methylsulfanyl)phenyl]-2,3,4,5,11,11a--
hexahydro-1H-[1,4]diazepino[1,7-a]indole
4-(2,3,4,5,11,11a-hexahydro-1H-[1-
,4]diazepino[1,7-a]indol-9-yl)benzonitrile
9-[3-(trifluoromethyl)phenyl]-2-
,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-naphthyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
1-[4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-
ethanone
N-[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl-
)phenyl]acetamide
9-(2,3-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
9-(5-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
9-(2-fluoro-5-methylphenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(5-fluoro-2-methoxylphenyl)-2-
,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
9-(3-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
9-(2-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
9-(2-chloro-3-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
9-(2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4-
]diazepino[1,7-a]indole
9-(4-ethoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indole
9-(4-fluoro-2-methylphenyl)-2,3,4,5,11,1-
1a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-chloro-6-fluorophenyl)-2,-
3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
9-[4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indole
9-[4-(trifluoromethoxy)phenyl]-2,3,4,5,1-
1,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(6-fluoro-2,4-dimethoxylp-
henyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-
e
9-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
9-[2-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4,6-trifluorophenyl)-2,3,4,5,11,11a-
-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,4,6-trichlorophenyl)-2,3,4,-
5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,6-dichloro-4-methox-
yphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
9-(4-chloro-2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
9-(2,3,4,6-tetrafluorophenyl)-2,3,4,5,11,11a-hexahy-
dro-1H-[1,4]diazepino[1,7-a]indole
9-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5-
,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2,6-di(trifluoromethyl-
)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino-
[1,7-a]indole
9-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexah-
ydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-isopropoxy-2-(trifluoromethyl)phe-
nyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
9-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-ethoxyphenyl]-2,3-
,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[2-chloro-4-isopropoxyphenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indole
9-(2-ethyl-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,-
4]diazepino[1,7-a]indole
5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indol-9-yl)benzaldehyde
9-[4-methoxy-2-(1-hydroxyethyl)phenyl-
]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole 1-[5-methoxy-2-(2,3,4,5,11,11
a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]ethanone
[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl-
)phenyl]methanol
9-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexa-
hydro-1H-[1,4]diazepino[1,7-a]indole
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahy-
dro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-1-propanol
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9--
yl)phenyl]-1-propanone methyl
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propenoate methyl
3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9--
yl)phenyl]propanoate
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4-
]diazepino[1,7-a]indol-9-yl)phenyl]-2-propen-1-ol methyl
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-9-yl)phenyl]-2-propenoate
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-2-propen-1-ol
9-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
9-(2-fluoro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydr-
o-1H-[1,4]diazepino[1,7-a]indole
9-(2-chloro-4-fluorophenyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
9-benzyl-2,3,4,5,11,11a-hexahyd- ro-1H-[1,4]diazepino[1,7-a]indole
9-(2-fluorobenzyl)-2,3,4,5,11,11a-hexahy-
dro-1H-[1,4]diazepino[1,7-a]indole
9-(3-fluorobenzyl)-2,3,4,5,11,11a-hexah-
ydro-1H-[1,4]diazepino[1,7-a]indole
9-(4-fluorobenzyl)-2,3,4,5,11,11a-hexa-
hydro-1H-[1,4]diazepino[1,7-a]indole
9-(3-methoxybenzyl)-2,3,4,5,11,11a-he-
xahydro-1H-[1,4]diazepino[1,7-a]indole
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4-
]diazepino[1,7-a]indol-9-ylmethyl)phenol
9-(2-methoxybenzyl)-2,3,4,5,11,11-
a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
2-(2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indol-9-ylmethyl)phenol methyl
2-methoxy-6-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)-
benzoate
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)be-
nzonitrile
3-methyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-9-yl)benzonitrile
2-methyl-3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepi-
no[1,7-a]indol-9-yl)benzonitrile
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indol-9-yl)benzonitrile
3-trifluoromethyl-4-(2,3,4,5,11,11a-hex-
ahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzaldehy-
de
[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-
methanol
9-[3-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
N,N-dimethyl[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indol-9-yl)phenyl]methanamine
2-fluoro-5-(2,3,4,5,11,11a-hexahyd-
ro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitrile, and
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)b-
enzamide.
8. A method for treating a disease or disorder of the central
nervous system in a mammal comprising administering to said mammal
a pharmaceutically effective amount of A compound of formula I:
221where a is a single bond or double bond, and where R1a, R1b, R2a
and R2b are each independently (a) H, Cl, Br, I, F, CN, CF.sub.3,
OCF.sub.3, OR5, CONR5R6, COR5, CO2R5, Y(CH.sub.2).sub.mXR5 or
YC(O)(CH.sub.2).sub.mXR5, where m=0-3, Y=CH.sub.2, S, O, or NR6,
X=CH.sub.2, S, O, NR6; (b) (CH2).sub.pAr where p=0-3 and Ar is aryl
or heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, R7; or (c) linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups may be optionally substituted with one
or more of the following: halogen, CN, NO.sub.2, COR7, OR7, NR7R8,
SR7, CO2R7, CONR7R8 or NR7COR8; and where R3 is (a) H, Cl, Br, I,
F, CN, CF.sub.3, OCF.sub.3, alkyl, Ar, OR5, SR5, CHO, CONR5R6,
COR5, CO2R5, (Y).sub.o(CH2).sub.nXR5, C(O)C(O)XR5,
(Y).sub.o(CH.sub.2).sub.nC(O)XR5, C(O)(CH2).sub.nXR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)R5,
(Y).sub.o(CH2).sub.nN(R6)S(O).sub.2R5,
(Y).sub.o(CH2).sub.nN(R6)C(O)OR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)NR5R6 where o=0 or 1, n=0-3,
X=CH.sub.2, S, O, or NR6 and Y=CH.sub.2, S, O or NR6, where Ar is
aryl or heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; or (b) linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups may be optionally substituted with one
or more of the following: halogen, CN, NO.sub.2, COR10, OR10,
NR10R8, SR10, CO2R10, CONR10R8 or NR10COR8; and where R4, R5 and R6
are each independently (a) H, linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups other than H may be optionally
substituted with one or more of the following: halogen, CN,
NO.sub.2, COR10, OR10, NR10R11, SR10, CO2R10, CONR10R11 or
NR10COR11; or where R5 and R6 are linked to form a 3 to 8 member
ring; or (b) (CH.sub.2).sub.pAr where p=0-3 and Ar is aryl or
heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; and where R7, R8, and R9 are each
independently (a) H, linear or branched C.sub.1-C.sub.8 alkyl,
linear or branched C.sub.2-C.sub.8 alkenyl, linear or branched
C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl
groups, wherein any of these groups other than H may be optionally
substituted with halogen, CN, NO.sub.2, COR10, OR10, NR10R11, SR10,
CO2R10, CONR10R11, NR10COR11, NR10CONR11R12, or where R7, R8, or R9
are linked to form a ring; or (b) (CH2).sub.pAr where p=0-3 and Ar
is aryl or heteroaryl optionally substituted with one or more of
the following: H, halogen, CN, NO.sub.2, OR10, CF.sub.3, OCF.sub.3,
SR10, SO.sub.2R10, SO.sub.2NR10R11, NR10R11, CONR10R11, NR10COR11,
NR10CONR11R12, CO.sub.2R10, COR10, or R10; and where R10, R11 and
R12 are each independently H, linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl; or a
stereoisomer or pharmaceutically acceptable salt thereof.
9. The method of claim 8 wherein the mammal is a human, food
animal, companion animal or other type of animal.
10. The method of claim 9 wherein the mammal is a human.
11. The method of claim 8 wherein said disease or disorder is
selected from the group consisting of obesity, depression,
schizophrenia, a stress related disease, panic disorder, a phobia,
obsessive compulsive disorder, post-traumatic-stress syndrome,
immune system depression, incontinence, a stress induced problem
with the urinary, gastrointestinal or cardiovascular system,
neurodegenerative disorders, autism, chemotherapy-induced vomiting,
hypertension, migraine headaches, cluster headaches, sexual
dysfunction in a mammal, addictive disorder and withdrawal
syndrome, an adjustment disorder, an age-associated learning and
mental disorder, anorexia nervosa, apathy, an attention-deficit
disorder due to general medical conditions, attention-deficit
hyperactivity disorder, bipolar disorder, bulimia nervosa, chronic
fatigue syndrome, conduct disorder, cyclothymic disorder, dysthymic
disorder, fibromyalgia and other somatoform disorders, generalized
anxiety disorder, an inhalation disorder, an intoxication disorder,
a movement disorder, oppositional defiant disorder, a pain
disorder, peripheral neuropathy, post-traumatic stress disorder,
premenstrual dysphoric disorder, a psychotic disorder, seasonal
affective disorder, a sleep disorder, a specific developmental
disorder, and selective serotonin reuptake inhibition (SSRI) "poop
out" syndrome and combinations thereof.
12. The method of claim 11 wherein said compound is administered
rectally, topically, nasally, orally, sublingually, transdermally
or parenterally.
13. The method of claim 11 wherein said compound is administered in
an amount ranging from about 0.1 to about 50 mg/kg of body weight
of said mammal per day.
14. The method of claim 13 wherein said compound is administered in
an amount ranging from about 0.1 to about 10 mg/kg of body weight
of said mammal per day.
15. A method for modulating 5-HT receptor function, comprising
contacting the receptor with an effective inhibitory amount of a
compound of a compound of formula I: 222where a is a single bond or
double bond, and where R1a, R1b, R2a and R2b are each independently
(a) H, Cl, Br, I, F, CN, CF.sub.3, OCF.sub.3, OR5, CONR5R6, COR5,
CO2R5, Y(CH.sub.2).sub.mXR5 or YC(O)(CH.sub.2).sub.mXR5, where
m=0-3, Y=CH.sub.2, S, O, or NR6, X=CH.sub.2, S, O, NR6; (b)
(CH2).sub.pAr where p=0-3 and Ar is aryl or heteroaryl optionally
substituted with one or more of the following: H, halogen, CN,
NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7, SO.sub.2R7, SO.sub.2NR7R8,
NR7R8, CONR7R8, NR7COR8, NR7CONR8R9, CO.sub.2R7, COR7, or R7; or
(c) linear or branched C.sub.1-C.sub.8 alkyl, linear or branched
C.sub.2-C.sub.8 alkenyl, linear or branched C.sub.2-C.sub.8
alkynyl, C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 cycloalkenyl,
or C.sub.3-C.sub.8 cycloalkynyl; wherein any of these groups may be
optionally substituted with one or more of the following: halogen,
CN, NO.sub.2, COR7, OR7, NR7R8, SR7, CO2R7, CONR7R8 or NR7COR8; and
where R3 is (a) H, Cl, Br, I, F, CN, CF.sub.3, OCF.sub.3, alkyl,
Ar, OR5, SR5, CHO, CONR5R6, COR5, CO2R5, (Y).sub.o(CH2).sub.nXR5,
C(O)C(O)XR5, (Y).sub.o(CH.sub.2).sub.nC(O)XR5, C(O)(CH2).sub.nXR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)R5,
(Y).sub.o(CH2).sub.nN(R6)S(O).sub.2R5,
(Y).sub.o(CH2).sub.nN(R6)C(O)OR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)NR5R6 where o=0 or 1, n=0-3,
X=CH.sub.2, S, O, or NR6 and Y=CH.sub.2, S, O or NR6, where Ar is
aryl or heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; or (b) linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups may be optionally substituted with one
or more of the following: halogen, CN, NO.sub.2, COR10, OR10,
NR10R8, SR10, CO2R10, CONR10R8 or NR10COR8; and where R4, R5 and R6
are each independently (a) H, linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups other than H may be optionally
substituted with one or more of the following: halogen, CN,
NO.sub.2, COR10, OR10, NR10R11, SR10, CO2R10, CONR10R11or
NR10COR11; or where R5 and R6 are linked to form a 3 to 8 member
ring; or (b) (CH.sub.2).sub.pAr where p=0-3 and Ar is aryl or
heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; and where R7, R8, and R9 are each
independently (a) H, linear or branched C.sub.1-C.sub.8 alkyl,
linear or branched C.sub.2-C.sub.8 alkenyl, linear or branched
C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl
groups, wherein any of these groups other than H may be optionally
substituted with halogen, CN, NO.sub.2, COR10, OR10, NR10R11, SR10,
CO2R10, CONR10R11, NR10COR11, NR10CONR11R12, or where R7, R8, or R9
are linked to form a ring; or (b) (CH2).sub.pAr where p=0-3 and Ar
is aryl or heteroaryl optionally substituted with one or more of
the following: H, halogen, CN, NO.sub.2, OR10, CF.sub.3, OCF.sub.3,
SR10, SO.sub.2R10, SO.sub.2NR10R11, NR10R11, CONR10R11, NR10COR11,
NR10CONR11R12, CO.sub.2R10, COR10, or R10; and where R10, R11 and
R12 are each independently H, linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl; or a
stereoisomer or pharmaceutically acceptable salt thereof.
16. The use of a compound of formula I: 223where a is a single bond
or double bond, and where R1a, R1b, R2a and R2b are each
independently (a) H, Cl, Br, I, F, CN, CF.sub.3, OCF.sub.3, OR5,
CONR5R6, COR5, CO2R5, Y(CH.sub.2).sub.mXR5 or
YC(O)(CH.sub.2).sub.mXR5, where m=0-3, Y=CH.sub.2, S, O, or NR6,
X=CH.sub.2, S, O, NR6; (b) (CH2).sub.pAr where p=0-3 and Ar is aryl
or heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; or (c) linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups may be optionally substituted with one
or more of the following: halogen, CN, NO.sub.2, COR7, OR7, NR7R8,
SR7, CO2R7, CONR7R8 or NR7COR8; and where R3 is (a) H, Cl, Br, I,
F, CN, CF.sub.3, OCF.sub.3, alkyl, Ar, OR5, SR5, CHO, CONR5R6,
COR5, CO2R5, (Y).sub.o(CH2).sub.nXR5, C(O)C(O)XR5,
(Y).sub.o(CH.sub.2).sub.nC(O)XR5, C(O)(CH2).sub.nXR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)R5,
(Y).sub.o(CH2).sub.nN(R6)S(O).sub.2R5,
(Y).sub.o(CH2).sub.nN(R6)C(O)OR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)NR5R6 where o=0 or 1, n=0-3,
X=CH.sub.2, S, O, or NR6 and Y=CH.sub.2, S, O or NR6, where Ar is
aryl or heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; or (b) linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups may be optionally substituted with one
or more of the following: halogen, CN, NO.sub.2, COR10, OR10,
NR10R8, SR10, CO2R10, CONR10R8 or NR10COR8; and where R4, R5 and R6
are each independently (a) H, linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups other than H may be optionally
substituted with one or more of the following: halogen, CN,
NO.sub.2, COR10, OR10, NR10OR11, SR10, CO2R10, CONR10R11 or
NR10COR11; or where R5 and R6 are linked to form a 3 to 8 member
ring; or (b) (CH.sub.2).sub.pAr where p=0-3 and Ar is aryl or
heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; and where R7, R8, and R9 are each
independently (a) H, linear or branched C.sub.1-C.sub.8 alkyl,
linear or branched C.sub.2-C.sub.8 alkenyl, linear or branched
C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl
groups, wherein any of these groups other than H may be optionally
substituted with halogen, CN, NO.sub.2, COR10, OR10, NR10R11, SR10,
CO2R10, CONR10R11, NR10COR11, NR10CONR11R12, or where R7, R8, or R9
are linked to form a ring; or (b) (CH2).sub.pAr where p=0-3 and Ar
is aryl or heteroaryl optionally substituted with one or more of
the following: H, halogen, CN, NO.sub.2, OR10, CF.sub.3, OCF.sub.3,
SR10, SO.sub.2R10, SO.sub.2NR10R11, NR10R11, CONR10R11, NR10COR11,
NR10CONR11R12, CO.sub.2R10, COR10, or R10; and where R10, R11 and
R12 are each independently H, linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl; or a
stereoisomer or pharmaceutically acceptable salt thereof. to
prepare a medicament for treating or preventing diseases or
disorders of the central nervous system.
17. A substance or a compound of formula I: 224where a is a single
bond or double bond, and where R1a, R1b, R2a and R2b are each
independently (a) H, Cl, Br, I, F, CN, CF.sub.3, OCF.sub.3, OR5,
CONR5R6, COR5, CO2R5, Y(CH.sub.2).sub.mXR5 or
YC(O)(CH.sub.2).sub.mXR5, where m=0-3, Y=CH.sub.2, S, O, or NR6,
X=CH.sub.2, S, O, NR6; (b) (CH2).sub.pAr where p=0-3 and Ar is aryl
or heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; or (c) linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups may be optionally substituted with one
or more of the following: halogen, CN, NO.sub.2, COR7, OR7, NR7R8,
SR7, CO2R7, CONR7R8 or NR7COR8; and where R3 is (a) H, Cl, Br, I,
F, CN, CF.sub.3, OCF.sub.3, alkyl, Ar, OR5, SR5, CHO, CONR5R6,
COR5, CO2R5, (Y).sub.o(CH2).sub.nXR5, C(O)C(O)XR5,
(Y).sub.o(CH.sub.2).sub.nC(O)XR5, C(O)(CH2).sub.nXR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)R5,
(Y).sub.o(CH2).sub.nN(R6)S(O).sub.2R5,
(Y).sub.o(CH2).sub.nN(R6)C(O)OR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)NR5R6 where o=0 or 1, n=0-3,
X=CH.sub.2, S, O, or NR6 and Y=CH.sub.2, S, O or NR6, where Ar is
aryl or heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; or (b) linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups may be optionally substituted with one
or more of the following: halogen, CN, NO.sub.2, COR10, OR10,
NR10R8, SR10, CO2R10, CONR10R8 or NR10COR8; and where R4, R5 and R6
are each independently (a) H, linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups other than H may be optionally
substituted with one or more of the following: halogen, CN,
NO.sub.2, COR10, OR10, NR10R11, SR10CO2R10, CONR10R11 or NR10COR11;
or where R5 and R6 are linked to form a 3 to 8 member ring; or (b)
(CH.sub.2).sub.pAr where p=0-3 and Ar is aryl or heteroaryl
optionally substituted with one or more of the following: H,
halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7, SO.sub.2R7,
SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9, CO.sub.2R7,
COR7, or R7; and where R7, R8, and R9 are each independently (a) H,
linear or branched C.sub.1-C.sub.8 alkyl, linear or branched
C.sub.2-C.sub.8 alkenyl, linear or branched C.sub.2-C.sub.8
alkynyl, C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 cycloalkenyl,
or C.sub.3-C.sub.8 cycloalkynyl groups, wherein any of these groups
other than H may be optionally substituted with halogen, CN,
NO.sub.2, COR10, OR10, NR10R11, SR10, CO2R10, CONR10R11, NR10COR11,
NR10CONR11R12, or where R7, R8, or R9 are linked to form a ring; or
(b) (CH2).sub.pAr where p=0-3 and Ar is aryl or heteroaryl
optionally substituted with one or more of the following: H,
halogen, CN, NO.sub.2, OR10, CF.sub.3, OCF.sub.3, SR10,
SO.sub.2R10, SO.sub.2NR10R11, NR10R11, CONR10R11, NR10COR11,
NR10CONR11R12, CO.sub.2R10, COR10, or R10; and where R10, R11 and
R12 are each independently H, linear or branched C.sub.1-C.sub.8
alkyl, linear or branched C.sub.2-C.sub.8 alkenyl, linear or
branched C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl; or a
stereoisomer or pharmaceutically acceptable salt thereof. for use
as a medicament.
18. A compound of the following formula: 225where R1a, R1b, R2a and
R2b are each independently H, Cl, Br, I, F, CN, CF.sub.3,
OCF.sub.3, C.sub.1-C.sub.4 alkyl, OR5, CONR5R6, COR5, CO2R5,
Y(CH.sub.2).sub.mXR5 or YC(O)(CH.sub.2).sub.mXR5, where m=0-3,
Y=CH.sub.2, S, O, or NR6, X=CH.sub.2, S, O, or NR6; and R5 and R6
are each independently H, linear, branched or cyclic
C.sub.1-C.sub.8 alkyl, alkenyl, or alkynyl groups or
(CH.sub.2).sub.pAr where p=0-3 and Ar is aryl or heteroaryl, Ar
being optionally substituted with one or more of the following: H,
halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7, SO.sub.2R7,
NR7R8, CONR7R8, COR7, or R7 where R7 and R8 are each independently
H, linear, branched or cyclic C.sub.1-C8 alkyl, alkenyl, or alkynyl
groups, or (CH2).sub.pPh where p=0-3.
19. A compound of the following formula: 226where R1a, R1b, R2a and
R2b are each independently H, Cl, Br, I, F, CN, CF.sub.3,
OCF.sub.3, C.sub.1-C.sub.4 alkyl, OR5, CONR5R6, COR5, CO2R5,
Y(CH.sub.2).sub.mXR5 or YC(O)(CH.sub.2).sub.mXR5, where m=0-3,
Y=CH.sub.2, S, O, or NR6, X=CH.sub.2, S, O, or NR6; and R5 and R6
are each independently H, linear, branched or cyclic
C.sub.1-C.sub.8 alkyl, alkenyl, or alkynyl groups or
(CH.sub.2).sub.pAr where p=0-3 and Ar is aryl or heteroaryl, Ar
being optionally substituted with one or more of the following: H,
halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7, SO.sub.2R7,
NR7R8, CONR7R8, COR7, or R7 where R7 and R8 are each independently
H, linear, branched or cyclic C.sub.1-C.sub.8 alkyl, alkenyl, or
alkynyl groups, or (CH2).sub.pPh where p=0-3.
20. A compound of the following formula: 227where R1a, R1b, R2a and
R2b are each independently H, Cl, Br, I, F, CN, CF.sub.3,
OCF.sub.3, C.sub.1-C.sub.4 alkyl, OR5, CONR5R6, COR5, CO2R5,
Y(CH.sub.2).sub.mXR5 or YC(O)(CH.sub.2).sub.mXR5, where m=0-3,
Y=CH.sub.2, S, O, or NR6, X=CH.sub.2, S, O, or NR6, with the
proviso that both R1 and R2 cannot be H; and R5 and R6 are each
independently H, linear, branched or cyclic C.sub.1-C.sub.8 alkyl,
alkenyl, or alkynyl groups or (CH.sub.2).sub.pAr where p=0-3 and Ar
is aryl or heteroaryl, Ar being optionally substituted with one or
more of the following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3,
OCF.sub.3, SR7, SO.sub.2R7, NR7R8, CONR7R8, COR7, or R7 where R7
and R8 are each independently H, linear, branched or cyclic
C.sub.1-C.sub.8 alkyl, alkenyl, or alkynyl groups, or (CH2).sub.pPh
where p=0-3.
21. A compound selected from the group consisting of: tert-butyl
1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]-indole-3-carboxylate;
11-[(E)-2-nitroethyl]-2,3,4,5-tetrahydro-1,4[1,4]diazepino-[1,7-a]indole;
3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino-[1,7-1]indole;
and
2-bromo-1-1[3-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
71-a]indole-11-yl]ethanone; or a pharmaceutically effective salt
thereof.
22. A method for treating a disease or disorder of the central
nervous system is a mammal comprising administering to said mammal
a pharmaceutically effective amount of the compound of claim
21.
23. The use of a compound of claim 21 to prepare a medicament for
treating or preventing diseases or disorders of the central nervous
system.
24. A substance or compound of claim 21 for use as a
medicament.
25. A compound of the formula 228
26. A compound of the formula 229
27. A compound of the formula 230
Description
CROSS-REFERENCE TO RELATED APPLICATION
[0001] This application claims the benefit of U.S. Provisional
Application Serial No. 60/189103, filed Mar. 14, 2000, under 37 CFR
1.53(c).
BACKGROUND OF THE INVENTION
[0002] 1. Field of the Invention
[0003] The present invention provides novel diazepinoindole
compounds of Formula I. These compounds are 5-HT ligands and are
useful for treating diseases wherein modulation of 5-HT activity is
desired.
[0004] 2. Technology Description
[0005] Serotonin has been implicated in a number of diseases and
conditions that originate in the central nervous system. These
include diseases and conditions related to sleeping, eating,
perceiving pain, controlling body temperature, controlling blood
pressure, depression, anxiety, schizophrenia, and other bodily
states. Serotonin also plays an important role in peripheral
systems, such as the gastrointestinal system, where it has been
found to mediate a variety of contractile, secretory, and
electrophysiologic effects.
[0006] As a result of the broad distribution of serotonin within
the body, there is a tremendous interest in drugs that affect
serotonergic systems. In particular, agonists, partial agonists and
antagonists are of interest for the treatment of a wide range of
disorders, including anxiety, depression, hypertension, migraine,
obesity, compulsive disorders, schizophrenia, autism,
neurodegenerative disorders (e.g. Alzheimer's disease,
Parkinsonism, and Huntington's chorea), and chemotherapy-induced
vomiting.
[0007] The major classes of serotonin receptors (5-HT.sub.1-7)
contain fourteen to eighteen separate receptor subtypes that have
been formally classified. See Glennon, et al., Neuroscience and
Behavioral Reviews, 1990, 14, 35; and D. Hoyer, et al. Pharmacol.
Rev. 1994, 46, 157-203.
[0008] For example, the 5-HT.sub.2 family of receptors is comprised
of 5-HT.sub.2A, 5-HT.sub.2B, and 5-HT.sub.2C subtypes, which have
been grouped together on the basis of primary structure, secondary
messenger system, and operational profile. All three subtypes are
G-protein coupled, activate phospholipase C as a principal
transduction mechanism, and contain a seven-transmembrane domain
structure. There are distinct differences in the distribution of
the three 5-HT.sub.2 subtypes. The 5-HT.sub.2B and 5-HT.sub.2A
receptors are widely distributed in the periphery, while the
5-HT.sub.2C receptor has been found only in the central nervous
system, being highly expressed in many regions of the human brain.
See G. Baxter, et al. Trends in Pharmacol. Sci. 1995, 16,
105-110.
[0009] Subtype 5-HT.sub.2A has been associated with effects
including vasoconstriction, platelet aggregation, and
bronchoconstriction, while subtype 5-HT.sub.2C has been associated
with diseases that include depression, anxiety, obsessive
compulsive disorder, panic disorders, phobias, psychiatric
syndromes, and obesity. Very little is known about the
pharmocologic role of the 5-HT.sub.2B receptor. See F. Jenck, et
al., Exp. Opin. Invest. Drugs, 1998, 7, 1587-1599; M. Bos, et al.,
J. Med. Chem., 1997, 40, 2762-2769; J. R. Martin, et al., The
Journal of Pharmacology and Experimental Therapeutics, 1998, 286,
913-924; S. M. Bromidge, et al., J. Med. Chem., 1998, 41,
1598-1612; G. A. Kennett, Drugs, 1998, 1, 4, 456-470; and A.
Dekeyne, et al., Neuropharmacology, 1999, 38, 415-423.
[0010] The following references possibly suggest molecules
containing both indole groups and cyclic rings wherein the indolyl
nitrogen atom and an additional nitrogen atom form a part of the
cyclic ring: SU 460724 and U.S. Pat. No. 4,673,674. However, the
molecules described in the above-described references contain
additional substituents that the inventors of the instant invention
have discovered are not required, and potentially not desired. U.S.
Pat. No. 4,210,590 suggests the reduction of indole compounds to
indoline compounds to yield compounds having biological and/or
pharmacological properties. U.S. Pat. No. 3,689,503 and U.S. Pat.
No. 3,867,374 disclose 2,3,4,5-tetrahydro-1H-[1,4]-diazepino[1,-
2-a]indole compounds and their use in treating central nervous
system diseases or disorders.
[0011] Despite the above teachings, there is currently a need for
pharmaceutical agents that are useful in treating diseases and
conditions that are associated with 5-HT receptors.
BRIEF SUMMARY OF THE INVENTION
[0012] In accordance with the present invention novel compounds
which demonstrate useful biological activity, and particularly
activity as 5-HT receptor ligands are provided. More specifically,
the compounds are unsubstituted or substituted
2,3,4,5-tetrahydro-1H-[1,4]-diazepino[1,7-a]- indoles.
[0013] A first embodiment of the present invention provides
compounds of formula I:
[0014] A compound of formula I: 2
[0015] where a is a single bond or double bond, and where
[0016] R1a, R1b, R2a and R2b are each independently
[0017] (a) H, Cl, Br, I, F, CN, CF.sub.3, OCF.sub.3, OR5, CONR5R6,
COR5, CO2R5, Y(CH.sub.2).sub.mXR5 or YC(O)(CH.sub.2).sub.mXR5,
where m=0-3, Y=CH.sub.2, S, O, or NR6, X=CH.sub.2, S, O, NR6;
[0018] (b) (CH2).sub.pAr where p=0-3 and Ar is aryl or heteroaryl
optionally substituted with one or more of the following: H,
halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7, SO.sub.2R7,
SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9, CO.sub.2R7,
COR7, or R7; or
[0019] (c) linear or branched C.sub.1-C.sub.8 alkyl, linear or
branched C.sub.2-C.sub.8 alkenyl, linear or branched
C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups may be optionally substituted with one
or more of the following: halogen, CN, NO.sub.2, COR7, OR7, NR7R8,
SR7, CO2R7, CONR7R8 or NR7COR8; and where
[0020] R3 is
[0021] (a) H, Cl, Br, I, F, CN, CF.sub.3, OCF.sub.3, alkyl, Ar,
OR5, SR5, CHO, CONR5R6, COR5, CO2R5, (Y).sub.o(CH2).sub.nXR5,
C(O)C(O)XR5, (Y).sub.o(CH.sub.2).sub.nC(O)XR5, C(O)(CH2).sub.nXR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)R5,
(Y).sub.o(CH2).sub.nN(R6)S(O).sub.2R5,
(Y).sub.o(CH2).sub.nN(R6)C(O)OR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)NR5R6 where o=0 or 1, n=0-3,
X=CH.sub.2, S, O, or NR6 and Y=CH.sub.2, S, O or NR6, where Ar is
aryl or heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; or
[0022] (b) linear or branched C.sub.1-C.sub.8 alkyl, linear or
branched C.sub.2-C.sub.8 alkenyl, linear or branched
C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups may be optionally substituted with one
or more of the following: halogen, CN, NO.sub.2, COR10, OR10,
NR10R8, SR10, CO2R10, CONR10R8 or NR10COR8; and where
[0023] R4, R5 and R6 are each independently
[0024] (a) H, linear or branched C.sub.1-C.sub.8 alkyl, linear or
branched C.sub.2-C.sub.8 alkenyl, linear or branched
C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups other than H may be optionally
substituted with one or more of the following: halogen, CN,
NO.sub.2, COR10, OR10, NR10R11, SR10CO2R10, CONR10R11 or NR10COR11;
or where R5 and R6 are linked to form a 3 to 8 member ring; or
[0025] (b) (CH.sub.2).sub.pAr where p=0-3 and Ar is aryl or
heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; and where
[0026] R7, R8, and R9 are each independently
[0027] (a) H, linear or branched C.sub.1-C.sub.8 alkyl, linear or
branched C.sub.2-C.sub.8 alkenyl, linear or branched
C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl
groups, wherein any of these groups other than H may be optionally
substituted with halogen, CN, NO.sub.2, COR10, OR10, NR10R11, SR10,
CO2R10, CONR10R11, NR10COR11, NR10CONR11R12, or where R7, R8, or R9
are linked to form a ring; or
[0028] (b) (CH2).sub.pAr where p=0-3 and Ar is aryl or heteroaryl
optionally substituted with one or more of the following: H,
halogen, CN, NO.sub.2, OR10, CF.sub.3, OCF.sub.3, SR10,
SO.sub.2R10, SO.sub.2NR10R11, NR10R11, CONR10R11, NR10COR11,
NR10CONR11R12, CO.sub.2R10, COR10, or R10; and where
[0029] R10, R11 and R12 are each independently H, linear or
branched C.sub.1-C.sub.8 alkyl, linear or branched C.sub.2-C.sub.8
alkenyl, linear or branched C.sub.2-C.sub.8 alkynyl,
C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 cycloalkenyl, or
C.sub.3-C.sub.8 cycloalkynyl;
[0030] or a stereoisomer or pharmaceutically acceptable salt
thereof.
[0031] In particularly preferred embodiments, R1a, R1b, R2a, R2b
and R4 are H and R3 is selected from either H, --C(O)C(O)XAr,
--CH.sub.2C(O)XAr or --C(O)CH.sub.2XAr where X and Ar are as
defined above.
[0032] Another embodiment of the present invention provides a
pharmaceutical composition comprising a compound of formula I, or a
pharmaceutically acceptable salt thereof, and a pharmaceutically
acceptable carrier. In preferred embodiments, the composition
preferably comprises a therapeutically effective amount of the
compound or salt.
[0033] Still another embodiment of the present invention provides a
method for treating a disease or condition in a mammal (e.g. animal
or human) wherein a 5-HT receptor is implicated and modulation of a
5-HT function is desired comprising administering to the mammal a
therapeutically effective amount of a compound of formula I, or a
pharmaceutically acceptable salt thereof.
[0034] Yet another embodiment of the present invention provides a
method for treating or preventing diseases or disorders of the
central nervous system comprising administering a therapeutically
effective amount of a compound of formula I, or a pharmaceutically
acceptable salt thereof to the mammal. Specific diseases or
disorders for which the compound of formula I may have activity
include, but are not limited to the following: obesity, depression,
schizophrenia, a stress related disease, panic disorder, a phobia,
obsessive compulsive disorder, post-traumatic-stress syndrome,
immune system depression, incontinence, a stress induced problem
with the urinary, gastrointestinal or cardiovascular system,
neurodegenerative disorders, autism, chemotherapy-induced vomiting,
hypertension, migraine headaches, cluster headaches, sexual
dysfunction in a mammal, addictive disorder and withdrawal
syndrome, an adjustment disorder, an age-associated learning and
mental disorder, anorexia nervosa, apathy, an attention-deficit
disorder due to general medical conditions, attention-deficit
hyperactivity disorder, bipolar disorder, bulimia nervosa, chronic
fatigue syndrome, conduct disorder, cyclothymic disorder, dysthymic
disorder, fibromyalgia and other somatoform disorders, generalized
anxiety disorder, an inhalation disorder, an intoxication disorder,
a movement disorder, oppositional defiant disorder, a pain
disorder, peripheral neuropathy, post-traumatic stress disorder,
premenstrual dysphoric disorder, a psychotic disorder, seasonal
affective disorder, a sleep disorder, a specific developmental
disorder, and selective serotonin reuptake inhibition (SSRI) "poop
out" syndrome.
[0035] A further embodiment of the present invention comprises the
use of a compound of formula (I) or a pharmaceutically acceptable
salt thereof to prepare a medicament for treating or preventing
diseases or disorders of the central nervous system.
[0036] A final embodiment of the present invention comprises a
method for modulating 5-HT receptor function with an effective
amount of a compound of formula I, or a pharmaceutically acceptable
salt thereof.
[0037] An object of the present invention is to provide novel
compounds having biological activity.
[0038] Still another object of the present invention is to provide
a method for treating a disease or condition in a mammal wherein a
5-HT receptor is implicated and modulation of a 5-HT function is
desired by using the novel compounds of the present invention.
[0039] A further object of the present invention is to provide a
method for treating or preventing diseases of the central nervous
system by using the novel compounds of the present invention.
[0040] These, and other objects, will readily be apparent to those
skilled in the art as reference is made to the detailed description
of the preferred embodiment.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT
[0041] In describing the preferred embodiment, certain terminology
will be utilized for the sake of clarity. Such terminology is
intended to encompass the recited embodiment, as well as all
technical equivalents which operate in a similar manner for a
similar purpose to achieve a similar result.
1. Terminology Definitions
[0042] The following definitions are used, unless otherwise
described: halo is fluoro, chloro, bromo, or iodo. Alkyl, alkoxy,
etc. denote both straight and branched groups; but reference to an
individual group or moiety such as "propyl" embraces only the
straight chain group or moiety, a branched chain isomer such as
"isopropyl 38 being specifically referred to. When alkyl can be
partially unsaturated, the alkyl chain may comprise one or more
(e.g. 1, 2, 3, or 4) double or triple bonds in the chain.
[0043] Aryl denotes a phenyl group or moiety or an ortho-fused
bicyclic carbocyclic group optionally substituted with one or more
of the following; O, S, N, halogen, or C.sub.1-4alkyl or moiety
having about nine to ten ring atoms in which at least one ring is
aromatic. Heteroaryl denotes a group or moiety of a monocyclic or
polycyclic aromatic ring containing five or six ring atoms
consisting of carbon and 1, 2, 3, or 4 heteroatoms each selected
from the group consisting of non-peroxide oxygen, sulfur, and N(X)
wherein X is absent or is H, O, S, C.sub.1-4alkyl, phenyl or
benzyl.
[0044] It will be appreciated by those skilled in the art that
compounds of the invention having a chiral center may exist in and
be isolated in optically active and racemic forms. Some compounds
may exhibit polymorphism. It is to be understood that the present
invention encompasses any racemic, optically-active, polymorphic,
tautomeric, or stereoisomeric form, or mixture thereof, of a
compound of the invention, which possesses the useful properties
described herein, it being well known in the art how to prepare
optically active forms (for example, by resolution of the racemic
form by recrystallization techniques, by synthesis from
optically-active starting materials, by chiral synthesis, or by
chromatographic separation using a chiral stationary phase) and how
to determine activity using the standard tests described herein, or
using other similar tests which are well known in the art.
[0045] To the extent that any pharmaceutically active compound is
disclosed or claimed, it is expressly intended to include all
active metabolites produced in vivo.
[0046] The carbon atom content of various hydrocarbon-containing
moieties is indicated by a prefix designating the minimum and
maximum number of carbon atoms in the moiety, i.e., the prefix
C.sub.i-j indicates a moiety of the integer `i" to the integer "j"
carbon atoms, inclusive. Thus, for example, C.sub.1-7alkyl refers
to alkyl of one to seven carbon atoms, inclusive.
[0047] The compounds of the present invention are generally named
according to the IUPAC or CAS nomenclature system. Abbreviations
which are well known to one of ordinary skill in the art may be
used (e.g. "Ph" for phenyl, `Me" for methyl, "Et" for ethyl, "h"
for hour or hours and "rt" for room temperature).
[0048] To the extent that any numerical range is recited in
connection with any aspect of the inventive compounds (e.g.,
dosages, treatment regimens, etc.) it expressly includes all
numerals, integer and fractional, falling within the range.
[0049] Specific and preferred values listed below for groups or
moieties, substituents, and ranges, are for illustration only; they
do not exclude other defined values or other values within defined
ranges.
2. The Invention
[0050] The present invention comprises compounds of formula I:
[0051] A compound of formula I: 3
[0052] where a is a single bond or double bond, and where
[0053] R1a, R1b, R2a and R2b are each independently
[0054] (a) H, Cl, Br, I, F, CN, CF.sub.3, OCF.sub.3, OR5, CONR5R6,
COR5, CO2R5, Y(CH.sub.2).sub.mXR5 or YC(O)(CH.sub.2).sub.mXR5,
where m=0-3, Y=CH.sub.2, S, O, or NR6, X=CH.sub.2, S, O, NR6;
[0055] (b) (CH2).sub.pAr where p=0-3 and Ar is aryl or heteroaryl
optionally substituted with one or more of the following: H,
halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7, SO.sub.2R7,
SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9, CO.sub.2R7,
COR7, or R7; or
[0056] (c) linear or branched C.sub.1-C.sub.8 alkyl, linear or
branched C.sub.2-C.sub.8 alkenyl, linear or branched
C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups may be optionally substituted with one
or more of the following: halogen, CN, NO.sub.2, COR7, OR7, NR7R8,
SR7, CO2R7, CONR7R8 or NR7COR8; and where
[0057] R3 is
[0058] (a) H, Cl, Br, I, F, CN, CF.sub.3, OCF.sub.3, alkyl, Ar,
OR5, SR5, CHO, CONR5R6, COR5, CO2R5, (Y).sub.o(CH2).sub.nXR5,
C(O)C(O)XR5, (Y).sub.o(CH.sub.2).sub.nC(O)XR5, C(O)(CH2).sub.nXR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)R5,
(Y).sub.o(CH2).sub.nN(R6)S(O).sub.2R5,
(Y).sub.o(CH2).sub.nN(R6)C(O)OR5,
(Y).sub.o(CH2).sub.nN(R6)C(O)NR5R6 where o=0 or 1, n=0-3,
X=CH.sub.2, S, O, or NR6 and Y=CH.sub.2, S, O or NR6, where Ar is
aryl or heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; or
[0059] (b) linear or branched C.sub.1-C.sub.8 alkyl, linear or
branched C.sub.2-C.sub.8 alkenyl, linear or branched
C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups may be optionally substituted with one
or more of the following: halogen, CN, NO.sub.2, COR10, OR10,
NR10R8, SR10, CO2R10, CONR10R8 or NR10COR8; and where
[0060] R4, R5 and R6 are each independently
[0061] (a) H, linear or branched C.sub.1-C.sub.8 alkyl, linear or
branched C.sub.2-C.sub.8 alkenyl, linear or branched
C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl,
C.sub.3-C.sub.8 cycloalkenyl, or C.sub.3-C.sub.8 cycloalkynyl;
wherein any of these groups other than H may be optionally
substituted with one or more of the following: halogen, CN,
NO.sub.2, COR10, OR10, NR10R11, SR10, CO2R10, CONR10R11 or
NR10COR11; or where R5 and R6 are linked to form a 3 to 8 member
ring; or
[0062] (b) (CH.sub.2).sub.pAr where p=0-3 and Ar is aryl or
heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, SO.sub.2NR7R8, NR7R8, CONR7R8, NR7COR8, NR7CONR8R9,
CO.sub.2R7, COR7, or R7; and where
[0063] R7, R8, and R9 are each independently
[0064] (a) H, linear or branched C.sub.1-C.sub.8 alkyl, linear or
branched C.sub.2-C.sub.8alkenyl, linear or branched C.sub.2-C.sub.8
alkynyl, C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 cycloalkenyl,
or C.sub.3-C.sub.8 cycloalkynyl groups, wherein any of these groups
other than H may be optionally substituted with halogen, CN,
NO.sub.2, COR10, OR10, NR10R11, SR10, CO2R10, CONR10R11, NR10COR11,
NR10CONR11R12, or where R7, R8, or R9 are linked to form a ring;
or
[0065] (b) (CH2).sub.pAr where p=0-3 and Ar is aryl or heteroaryl
optionally substituted with one or more of the following: H,
halogen, CN, NO.sub.2, OR10, CF.sub.3, OCF.sub.3, SR10,
SO.sub.2R10, SO.sub.2NR10R11, NR10R11, CONR10R11, NR10COR11,
NR10CONR11R12, CO.sub.2R10, COR10, or R10; and where
[0066] R10, R11 and R12 are each independently H, linear or
branched C.sub.1-C.sub.8 alkyl, linear or branched C.sub.2-C.sub.8
alkenyl, linear or branched C.sub.2-C.sub.8 alkynyl,
C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 cycloalkenyl, or
C.sub.3-C.sub.8 cycloalkynyl;
[0067] or a stereoisomer or pharmaceutically acceptable salt
thereof.
[0068] Compounds of this formula are 5-HT receptor ligands, and as
such may be useful in treating animals (including humans, food
animals, companion animals and other animals) against diseases and
disorders of the central nervous system.
[0069] In particularly preferred embodiments, R1a, R1b, R2a, R2b
and R4 are H and R3 is selected from either H, --C(O)C(O)XAr,
--CH.sub.2C(O)XAr or --C(O)CH.sub.2XAr where X and Ar are as
defined above. Even more preferred embodiments comprise the above
definition where X is CH.sub.2, S, O, or NR6 and Ar is phenyl or
heteroaryl optionally substituted with one or more of the
following: H, halogen, CN, NO.sub.2, OR7, CF.sub.3, OCF.sub.3, SR7,
SO.sub.2R7, NR7R8, CONR7R8, COR7, or R7 where R7 and R8 are each
independently H, linear or branched C.sub.1-C.sub.8 alkyl, alkenyl,
or alkynyl groups, or (CH2).sub.pPh where p=0-3.
[0070] The names of compounds falling within the scope of the
present invention include, but are not limited to the
following:
[0071] 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
[0072] 8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
[0073]
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbaldehyde
[0074]
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ace-
tamide
[0075]
2,2,2-trifluoro-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
-11-yl)-1-ethanone
[0076] 11-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
[0077] 11-chloro-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
[0078]
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbonitrile
[0079]
8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbal-
dehyde
[0080]
1-(8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)--
2,2,2-trifluoro-1-ethanone
[0081]
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carboxamide
[0082]
1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethano-
ne hydrochloride
[0083]
3-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0084]
3-ethyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0085]
3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0086] 10-methoxy-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
[0087] ethyl
2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol--
11-yl)-2-oxoacetate
[0088] 3-propyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
[0089]
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethana-
mine
[0090]
2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-
-1-ethanol
[0091]
3-benzyl-11-(2-phenoxyethyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0092]
11-(2-phenoxyethyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
le
[0093]
3-benzyl-11-[2-(2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0094]
3-benzyl-11-[2-(2-fluorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0095]
3-benzyl-11-[2-(8-quinolinyloxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0096]
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethano-
l
[0097]
3-benzyl-11-[2-(2-methoxy-4-methylphenoxy)ethyl]-2,3,4,5-tetrahydro-
-1H-[1,4]diazepino[1,7-a]indole
[0098]
3-benzyl-11-[2-(2-fluoro-6-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-
-1H-[1,4]diazepino[1,7-a]indole
[0099]
11-[2-(2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indole
[0100]
11-[2-(2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indole hydrochloride
[0101]
11-[2-(2-fluorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0102]
11-[2-(2-methoxy-4-methylphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0103]
11-[2-(2-fluoro-6-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0104]
3-benzyl-11-[2-(2-chlorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0105]
3-benzyl-11-[2-(4-bromo-2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indole
[0106]
N-benzyl-2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-11-yl)-1-ethanamine
[0107]
11-[2-(2-chlorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0108]
11-[2-(4-bromo-2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0109]
2-phenoxy-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl-
)-1-ethanone
[0110]
N-(4-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indol-11-yl)acetamide
[0111]
4-methoxy-N-[2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-
-yl)ethyl]aniline dihydrochloride
[0112]
2-hydroxy-N-(4-methoxyphenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indol-11-yl)acetamide
[0113]
2-(2-methoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-11-yl)-1-ethanone
[0114]
2-(4-bromo-2-methoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indol-11-yl)-1-ethanone
[0115]
N-(4-methoxyphenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndol-11-yl)acetamide
[0116]
2-(4-methoxyanilino)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-11-yl)-1-ethanone dihydrochloride
[0117]
N-(2,4-difluorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indol-11-yl)acetamide
[0118]
N-(3-chloro-4-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indol-11-yl)acetamide
[0119]
2-oxo-N-phenyl-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol--
11-yl)acetamide
[0120]
N-(2-naphthyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-11-yl)acetamide
[0121]
N-(2,4-difluorophenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indol-11-yl)acetamide
[0122]
8-phenyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0123]
8-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0124]
8-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0125]
8-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0126]
8-(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0127]
8-(2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
le
[0128]
8-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0129]
8-(2,4-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0130]
8-(2-chloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0131]
8-(4-isopropylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
[0132]
8-(4-butylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0133]
8-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0134]
8-(4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0135]
8-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0136]
8-(2,4,5-trimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
[0137]
8-(3-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0138]
8-(4-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0139]
8-(4-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0140]
8-(2,5-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0141]
8-(4-isopropyl-2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0142]
8-(2,6-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0143]
8-(2,6-difluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0144]
8-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0145]
8-[2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0146]
8-(4-pyridinyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0147]
8-(2-furyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0148]
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzenethi-
ol
[0149]
8-(2,3-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0150]
8-(4-ethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0151]
8-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0152]
8-(3-chloro-2-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0153]
8-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
le
[0154]
8-[4-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0155]
4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitri-
le
[0156]
8-[3-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0157]
8-(2-naphthyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0158]
1-[4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-
ethanone
[0159]
N-[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]-
acetamide
[0160]
8-(2,3-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0161]
8-(5-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0162]
8-(2-fluoro-5-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0163]
8-(5-fluoro-2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0164]
8-(3-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0165]
8-(3-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0166]
8-(2-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0167]
8-(2-chloro-3-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0168]
8-(2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ole
[0169]
8-(4-ethoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0170]
8-(4-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0171]
8-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0172]
8-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0173]
8-[4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0174]
8-[4-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indole
[0175]
8-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0176]
8-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0177]
8-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0178]
8-[2-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0179]
8-(2,4,6-trifluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
[0180]
8-(2,4,6-trichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
[0181]
8-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
[0182]
8-(2,3,4-trifluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
[0183]
8-(4-chloro-2,6-difluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0184]
8-(2,3,4,6-tetrafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0185]
8-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0186]
8-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0187]
8-[2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indole
[0188]
8-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0189]
8-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
[0190]
8-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0191]
8-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0192]
8-[2-chloro-4-ethoxyphenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0193]
8-[2-chloro-4-isopropoxyphenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0194]
8-(2-ethyl-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0195]
5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)-
benzaldehyde
[0196]
8-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0197]
8-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0198]
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8--
yl)phenyl]ethanone
[0199]
[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl-
)phenyl]methanol
[0200]
8-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0201]
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8--
yl)phenyl]-1-propanol
[0202]
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8--
yl)phenyl]-1-propanone
[0203] methyl
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indol-8-yl)phenyl]-2-propenoate
[0204] methyl
3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndol-8-yl)phenyl]propanoate
[0205]
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-8-yl)phenyl]-2-propen-1-ol
[0206] methyl
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indol-8-yl)phenyl]-2-propenoate
[0207]
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-8-yl)phenyl]-2-propen-1-ol
[0208]
8-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0209]
8-(2-fluoro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0210]
8-(2-chloro-4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0211]
8-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0212]
8-(2-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0213]
8-(3-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0214]
8-(4-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0215]
8-(3-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
le
[0216]
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-ylmethyl)phen-
ol
[0217]
8-(2-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
le
[0218]
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-ylmethyl)phen-
ol
[0219] methyl
2-methoxy-6-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-8-yl)benzoate
[0220]
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitri-
le
[0221]
3-methyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)b-
enzonitrile
[0222]
2-methyl-3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)b-
enzonitrile
[0223]
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzonitri-
le
[0224]
3-trifluoromethyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-8-yl)benzonitrile
[0225]
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benzaldehy-
de
[0226]
[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phenyl]me-
thanol
[0227]
8-[3-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0228]
N,N-dimethyl[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8--
yl)phenyl]methanamine
[0229]
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)b-
enzonitrile
[0230]
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)b-
enzamide
[0231]
8-phenyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
[0232]
8-(2,4-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0233]
8-(4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0234]
8-(4-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0235]
8-(2-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0236]
8-(2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
[0237]
8-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0238]
8-(2,4-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0239]
8-(2-chloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0240]
8-(4-isopropylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0241]
8-(4-butylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0242]
8-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[-
1,4]diazepino[1,7-a]indole
[0243]
8-(4-methoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0244]
8-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-
-[1,4]diazepino[1,7-a]indole
[0245]
8-(2,4,5-trimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0246]
8-(3-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0247]
8-(4-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0248]
8-(4-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0249]
8-(2,5-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0250]
8-(4-isopropyl-2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0251]
8-(2,6-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0252]
8-(2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0253]
8-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-
-[1,4]diazepino[1,7-a]indole
[0254]
8-[2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0255]
8-(4-pyridinyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dole
[0256]
8-(2-furyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
[0257]
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benz-
enethiol
[0258]
8-(2,3-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0259]
8-(4-ethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0260]
8-(2,4-dimethoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0261]
8-(3-chloro-2-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0262]
8-(4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
[0263]
8-[4-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0264]
4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benz-
onitrile
[0265]
8-[3-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0266]
8-(2-naphthyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]ind-
ole
[0267]
1-[4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)p-
henyl]ethanone
[0268]
N-[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)p-
henyl]acetamide
[0269]
8-(2,3-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0270]
8-(5-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0271]
8-(2-fluoro-5-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0272]
8-(5-fluoro-2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0273]
8-(3-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0274]
8-(3-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0275]
8-(2-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0276]
8-(2-chloro-3-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0277]
8-(2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indole
[0278]
8-(4-ethoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0279]
8-(4-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0280]
8-(2-chloro-6-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0281]
8-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0282]
8-[4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0283]
8-[4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indole
[0284]
8-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0285]
8-(2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0286]
8-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0287]
8-[2-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0288]
8-(2,4,6-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0289]
8-(2,4,6-trichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0290]
8-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0291]
8-(2,3,4-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0292]
8-(4-chloro-2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0293]
8-(2,3,4,6-tetrafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0294]
8-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0295]
8-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0296]
8-[2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indole
[0297]
8-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-
-[1,4]diazepino[1,7-a]indole
[0298]
8-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indole
[0299]
8-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0300]
8-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0301]
8-[2-chloro-4-ethoxyphenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0302]
8-[2-chloro-4-isopropoxyphenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0303]
8-(2-ethyl-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0304]
5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-
-8-yl)benzaldehyde
[0305]
8-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0306]
8-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0307]
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-8-yl)phenyl]ethanone
[0308]
[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indo-
l-8-yl)phenyl]methanol
[0309]
8-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[-
1,4]diazepino[1,7-a]indole
[0310]
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-8-yl)phenyl]-1-propanol
[0311]
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-8-yl)phenyl]-1-propanone
[0312] methyl
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indol-8-yl)phenyl]-2-propenoate
[0313] methyl
3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indol-8-yl)phenyl]propanoate
[0314]
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indol-8-yl)phenyl]-2-propen-1-ol
[0315] methyl
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indol-8-yl)phenyl]-2-propenoate
[0316]
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indol-8-yl)phenyl]-2-propen-1-ol
[0317]
8-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0318]
8-(2-fluoro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0319]
8-(2-chloro-4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0320]
8-benzyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
[0321]
8-(2-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0322]
8-(3-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0323]
8-(4-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0324]
8-(3-methoxybenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
[0325]
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-ylmethy-
l)phenol
[0326]
8-(2-methoxybenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
[0327]
2-(2,3,4,5,11,1a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-ylmethyl-
)phenol
[0328] methyl
2-methoxy-6-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indol-8-yl)benzoate
[0329]
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benz-
onitrile
[0330]
3-methyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol--
8-yl)benzonitrile
[0331]
2-methyl-3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol--
8-yl)benzonitrile
[0332]
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benz-
onitrile
[0333]
3-trifluoromethyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indol-8-yl)benzonitrile
[0334]
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)benz-
aldehyde
[0335]
[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-8-yl)phe-
nyl]methanol
[0336]
8-[3-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0337]
N,N-dimethyl[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-8-yl)phenyl]methanamine
[0338]
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol--
8-yl)benzonitrile
[0339]
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol--
8-yl)benzamide
[0340]
7-phenyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0341]
7-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0342]
7-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0343]
7-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0344]
7-(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0345]
7-(2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
le
[0346]
7-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0347]
7-(2,4-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0348]
7-(2-chloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0349]
7-(4-isopropylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
[0350]
7-(4-butylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0351]
7-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0352]
7-(4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0353]
7-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0354]
7-(2,4,5-trimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
[0355]
7-(3-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0356]
7-(4-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0357]
7-(4-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0358]
7-(2,5-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0359]
7-(4-isopropyl-2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0360]
7-(2,6-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0361]
7-(2,6-difluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0362]
7-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0363]
7-[2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0364]
7-(4-pyridinyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0365]
7-(2-furyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0366]
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzenethi-
ol
[0367]
7-(2,3-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0368]
7-(4-ethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0369]
7-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0370]
7-(3-chloro-2-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0371]
7-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
le
[0372]
7-[4-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0373]
4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitri-
le
[0374]
7-[3-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0375]
7-(2-naphthyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0376]
1-[4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-
ethanone
[0377]
N-[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]-
acetamide
[0378]
7-(2,3-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0379]
7-(5-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0380]
7-(2-fluoro-5-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0381]
7-(5-fluoro-2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0382]
7-(3-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0383]
7-(3-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0384]
7-(2-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0385]
7-(2-chloro-3-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0386]
7-(2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ole
[0387]
7-(4-ethoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0388]
7-(4-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0389]
7-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diaiepino[1,-
7-a]indole
[0390]
7-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0391]
7-[4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0392]
7-[4-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indole
[0393]
7-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0394]
7-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0395]
7-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0396]
7-[2-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0397]
7-(2,4,6-trifluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
[0398]
7-(2,4,6-trichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
[0399]
7-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
[0400]
7-(2,3,4-trifluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
[0401]
7-(4-chloro-2,6-difluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0402]
7-(2,3,4,6-tetrafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0403]
7-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0404]
7-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0405]
7-[2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indole
[0406]
7-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0407]
7-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
[0408]
7-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0409]
7-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0410]
7-[2-chloro-4-ethoxyphenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0411]
7-[2-chloro-4-isopropoxyphenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0412]
7-(2-ethyl-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0413]
5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)-
benzaldehyde
[0414]
7-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0415]
7-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0416]
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7--
yl)phenyl]ethanone
[0417]
[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl-
)phenyl]methanol
[0418]
7-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0419]
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7--
yl)phenyl]-1-propanol
[0420]
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7--
yl)phenyl]-1-propanone
[0421] methyl
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indol-7-yl)phenyl]-2-propenoate
[0422] methyl
3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndol-7-yl)phenyl]propanoate
[0423]
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-7-yl)phenyl]-2-propen-1-ol
[0424] methyl
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indol-7-yl)phenyl]-2-propenoate
[0425]
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-7-yl)phenyl]-2-propen-1-ol
[0426]
7-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0427]
7-(2-fluoro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0428]
7-(2-chloro-4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0429]
7-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0430]
7-(2-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0431]
7-(3-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0432]
7-(4-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0433]
7-(3-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
le
[0434]
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-ylmethyl)phen-
ol
[0435]
7-(2-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
le
[0436]
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-ylmethyl)phen-
ol
[0437] methyl
2-methoxy-6-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-7-yl)benzoate
[0438]
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitri-
le
[0439]
3-methyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)b-
enzonitrile
[0440]
2-methyl-3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)b-
enzonitrile
[0441]
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzonitri-
le
[0442]
3-trifluoromethyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-7-yl)benzonitrile
[0443]
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benzaldehy-
de
[0444]
[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phenyl]me-
thanol
[0445]
7-[3-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0446]
N,N-dimethyl[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7--
yl)phenyl]methanamine
[0447]
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)b-
enzonitrile
[0448]
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)b-
enzamide
[0449]
7-phenyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
[0450]
7-(2,4-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0451]
7-(4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0452]
7-(4-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0453]
7-(2-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0454]
7-(2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
[0455]
7-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0456]
7-(2,4-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0457]
7-(2-chloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0458]
7-(4-isopropylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0459]
7-(4-butylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0460]
7-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[-
1,4]diazepino[1,7-a]indole
[0461]
7-(4-methoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0462]
7-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-
-[1,4]diazepino[1,7-a]indole
[0463]
7-(2,4,5-trimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0464]
7-(3-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0465]
7-(4-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0466]
7-(4-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0467]
7-(2,5-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0468]
7-(4-isopropyl-2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0469]
7-(2,6-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0470]
7-(2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0471]
7-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-
-[1,4]diazepino[1,7-a]indole
[0472]
7-[2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0473]
7-(4-pyridinyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dole
[0474]
7-(2-furyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
[0475]
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benz-
enethiol
[0476]
7-(2,3-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0477]
7-(4-ethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0478]
7-(2,4-dimethoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0479]
7-(3-chloro-2-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0480]
7-(4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
[0481]
7-[4-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0482]
4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benz-
onitrile
[0483]
7-[3-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0484]
7-(2-naphthyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]ind-
ole
[0485]
1-[4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)p-
henyl]ethanone
[0486]
N-[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)p-
henyl]acetamide
[0487]
7-(2,3-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0488]
7-(5-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0489]
7-(2-fluoro-5-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0490]
7-(5-fluoro-2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0491]
7-(3-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0492]
7-(3-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0493]
7-(2-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0494]
7-(2-chloro-3-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0495]
7-(2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indole
[0496]
7-(4-ethoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0497]
7-(4-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0498]
7-(2-chloro-6-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0499]
7-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0500]
7-[4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0501]
7-[4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indole
[0502]
7-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0503]
7-(2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0504]
7-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0505]
7-[2-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0506]
7-(2,4,6-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0507]
7-(2,4,6-trichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0508]
7-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0509]
7-(2,3,4-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0510]
7-(4-chloro-2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0511]
7-(2,3,4,6-tetrafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0512]
7-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0513]
7-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0514]
7-[2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indole
[0515]
7-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-
-[1,4]diazepino[1,7-a]indole
[0516]
7-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indole
[0517]
7-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0518]
7-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0519]
7-[2-chloro-4-ethoxyphenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0520]
7-[2-chloro-4-isopropoxyphenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0521]
7-(2-ethyl-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0522]
5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-
-7-yl)benzaldehyde
[0523]
7-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0524]
7-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0525]
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-7-yl)phenyl]ethanone
[0526]
[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indo-
l-7-yl)phenyl]methanol
[0527]
7-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[-
1,4]diazepino[1,7-a]indole
[0528]
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-7-yl)phenyl]-1-propanol
[0529]
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-7-yl)phenyl]-1-propanone
[0530] methyl
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indol-7-yl)phenyl]-2-propenoate
[0531] methyl
3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indol-7-yl)phenyl]propanoate
[0532]
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indol-7-yl)phenyl]-2-propen-1-ol
[0533] methyl
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indol-7-yl)phenyl]-2-propenoate
[0534]
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indol-7-yl)phenyl]-2-propen-1-ol
[0535]
7-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0536]
7-(2-fluoro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0537]
7-(2-chloro-4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0538]
7-benzyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
[0539]
7-(2-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0540]
7-(3-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0541]
7-(4-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0542]
7-(3-methoxybenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
[0543]
3-(2,3,4,5,11,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-ylme-
thyl)phenol
[0544]
7-(2-methoxybenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
[0545]
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-ylmethy-
l)phenol
[0546] methyl
2-methoxy-6-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indol-7-yl)benzoate
[0547]
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benz-
onitrile
[0548]
3-methyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol--
7-yl)benzonitrile
[0549]
2-methyl-3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol--
7-yl)benzonitrile
[0550]
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benz-
onitrile
[0551]
3-trifluoromethyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indol-7-yl)benzonitrile
[0552]
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)benz-
aldehyde
[0553]
[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-7-yl)phe-
nyl]methanol
[0554]
7-[3-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0555]
N,N-dimethyl[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-7-yl)phenyl]methanamine
[0556]
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol--
7-yl)benzonitrile
[0557]
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol--
7-yl)benzamide
[0558]
9-phenyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
[0559]
9-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0560]
9-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0561]
9-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0562]
9-(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0563]
9-(2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
le
[0564]
9-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0565]
9-(2,4-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0566]
9-(2-chloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0567]
9-(4-isopropylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
[0568]
9-(4-butylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0569]
9-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0570]
9-(4-methoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0571]
9-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0572]
9-(2,4,5-trimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
[0573]
9-(3-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0574]
9-(4-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0575]
9-(4-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0576]
9-(2,5-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0577]
9-(4-isopropyl-2-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0578]
9-(2,6-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0579]
9-(2,6-difluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0580]
9-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0581]
9-[2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0582]
9-(4-pyridinyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0583]
9-(2-furyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0584]
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzenethi-
ol
[0585]
9-(2,3-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0586]
9-(4-ethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0587]
9-(2,4-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0588]
9-(3-chloro-2-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0589]
9-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
le
[0590]
9-[4-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0591]
4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitri-
le
[0592]
9-[3-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0593]
9-(2-naphthyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0594]
1-[4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-
ethanone
[0595]
N-[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]-
acetamide
[0596]
9-(2,3-dimethylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0597]
9-(5-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0598]
9-(2-fluoro-5-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0599]
9-(5-fluoro-2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0600]
9-(3-chloro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0601]
9-(3-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0602]
9-(2-nitrophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0603]
9-(2-chloro-3-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0604]
9-(2-methoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ole
[0605]
9-(4-ethoxy-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0606]
9-(4-fluoro-2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0607]
9-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepirio[1-
,7-a]indole
[0608]
9-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0609]
9-[4-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0610]
9-[4-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indole
[0611]
9-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0612]
9-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0613]
9-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0614]
9-[2-(methylsulfanyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0615]
9-(2,4,6-trifluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
[0616]
9-(2,4,6-trichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
[0617]
9-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
[0618]
9-(2,3,4-trifluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indole
[0619]
9-(4-chloro-2,6-difluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0620]
9-(2,3,4,6-tetrafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0621]
9-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0622]
9-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0623]
9-[2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indole
[0624]
9-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5-tetrahydro-1H-f[1,4-
]diazepino[1,7-a]indole
[0625]
9-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole
[0626]
9-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0627]
9-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0628]
9-[2-chloro-4-ethoxyphenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0629]
9-[2-chloro-4-isopropoxyphenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0630]
9-(2-ethyl-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0631]
5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)-
benzaldehyde
[0632]
9-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0633]
9-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0634]
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9--
yl)phenyl]ethanone
[0635]
[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl-
)phenyl]methanol
[0636]
9-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0637]
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9--
yl)phenyl]-1-propanol
[0638]
1-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9--
yl)phenyl]-1-propanone
[0639] methyl
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indol-9-yl)phenyl]-2-propenoate
[0640] methyl
3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndol-9-yl)phenyl]propanoate
[0641]
(2Z)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-9-yl)phenyl]-2-propen-1-ol
[0642] methyl
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indol-9-yl)phenyl]-2-propenoate
[0643]
(2E)-3-[5-methoxy-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-9-yl)phenyl]-2-propen-1-ol
[0644]
9-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0645]
9-(2-fluoro-4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0646]
9-(2-chloro-4-fluorophenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0647]
9-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0648]
9-(2-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0649]
9-(3-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0650]
9-(4-fluorobenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
e
[0651]
9-(3-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
le
[0652]
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-ylmethyl)phen-
ol
[0653]
9-(2-methoxybenzyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
le
[0654]
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-ylmethyl)phen-
ol
[0655] methyl
2-methoxy-6-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-9-yl)benzoate
[0656]
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitri-
le
[0657]
3-methyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)b-
enzonitrile
[0658]
2-methyl-3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)b-
enzonitrile
[0659]
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzonitri-
le
[0660]
3-trifluoromethyl-4-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-9-yl)benzonitrile
[0661]
3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benzaldehy-
de
[0662]
[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phenyl]me-
thanol
[0663]
9-[3-(methoxymethyl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0664] N,N-dimethyl
[3-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-
-yl)phenyl]methanamine
[0665]
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)b-
enzonitrile
[0666]
2-fluoro-5-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)b-
enzamide
[0667]
9-phenyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
[0668]
9-(2,4-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0669]
9-(4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0670]
9-(4-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0671]
9-(2-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0672]
9-(2-methoxyphenyl)-2,3,4,5,11,1a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0673]
9-[2-chloro-4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0674]
9-(2,4-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0675]
9-(2-chloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0676]
9-(4-isopropylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,-
7-a]indole
[0677]
9-(4-butylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0678]
9-(5-fluoro-4-methoxy-2-methylphenyl)-2,3,4,5,111,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0679]
9-(4-methoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0680]
9-[2-chloro-4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-
-[1,4]diazepino[1,7-a]indole
[0681]
9-(2,4,5-trimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0682]
9-(3-chlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0683]
9-(4-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0684]
9-(4-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
9-(2,5-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0685]
9-(4-isopropyl-2-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0686]
9-(2,6-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0687]
9-(2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0688]
9-[4-methoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-
-[1,4]diazepino[1,7-a]indole
[0689]
9-[2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0690]
9-(4-pyridinyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dole
[0691]
9-(2-furyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
[0692]
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benz-
enethiol
[0693]
9-(2,3-dichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0694]
9-(4-ethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0695]
9-(2,4-dimethoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[-
1,7-a]indole
[0696]
9-(3-chloro-2-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0697]
9-(4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
[0698]
9-[4-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0699]
4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benz-
onitrile
[0700]
9-[3-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0701]
9-(2-naphthyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]ind-
ole
[0702]
1-[4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)p-
henyl]ethanone
[0703]
N-[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)p-
henyl]acetamide
[0704]
9-(2,3-dimethylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indole
[0705]
9-(5-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0706]
9-(2-fluoro-5-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0707]
9-(5-fluoro-2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0708]
9-(3-chloro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0709]
9-(3-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0710]
9-(2-nitrophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0711]
9-(2-chloro-3-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0712]
9-(2-methoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indole
[0713]
9-(4-ethoxy-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0714]
9-(4-fluoro-2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0715]
9-(2-chloro-6-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0716]
9-[2-chloro-4-(difluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0717]
9-[4-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0718]
9-[4-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indole
[0719]
9-(6-fluoro-2,4-dimethoxylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0720]
9-(2-methylphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0721]
9-[6-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0722]
9-[2-(methylsulfanyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0723]
9-(2,4,6-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0724]
9-(2,4,6-trichlorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0725]
9-(2,6-dichloro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]d-
iazepino[1,7-a]indole
[0726]
9-(2,3,4-trifluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0727]
9-(4-chloro-2,6-difluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0728]
9-(2,3,4,6-tetrafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaz-
epino[1,7-a]indole
[0729]
9-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0730]
9-[2,6-di(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]-
diazepino[1,7-a]indole
[0731]
9-[2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]dia-
zepino[1,7-a]indole
[0732]
9-[4-ethoxy-2-(trifluoromethoxy)phenyl]-2,3,4,5,11,11a-hexahydro-1H-
-[1,4]diazepino[1,7-a]indole
[0733]
9-[4-isopropoxy-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-
-1H-[1,4]diazepino[1,7-a]indole
[0734]
9-[4-chloro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0735]
9-[4-fluoro-2-(trifluoromethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0736]
9-[2-chloro-4-ethoxyphenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0737]
9-[2-chloro-4-isopropoxyphenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]di-
azepino[1,7-a]indole
[0738]
9-(2-ethyl-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0739]
5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-
-9-yl)benzaldehyde
[0740]
9-[4-methoxy-2-(1-hydroxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0741]
9-[4-methoxy-2-(1-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0742]
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-9-yl)phenyl]ethanone
[0743]
[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indo-
l-9-yl)phenyl]methanol
[0744]
9-[4-methoxy-2-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[-
1,4]diazepino[1,7-a]indole
[0745]
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-9-yl)phenyl]-1-propanol
[0746]
1-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-9-yl)phenyl]-1-propanone
[0747] methyl
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indol-9-yl)phenyl]-2-propenoate
[0748] methyl
3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1-
,7-a]indol-9-yl)phenyl]propanoate
[0749]
(2Z)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indol-9-yl)phenyl]-2-propen-1-ol
[0750] methyl
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indol-9-yl)phenyl]-2-propenoate
[0751]
(2E)-3-[5-methoxy-2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indol-9-yl)phenyl]-2-propen-1-ol
[0752]
9-[4-methoxy-2-(2-methoxyethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H--
[1,4]diazepino[1,7-a]indole
[0753]
9-(2-fluoro-4-methoxyphenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diaze-
pino[1,7-a]indole
[0754]
9-(2-chloro-4-fluorophenyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0755]
9-benzyl-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
[0756]
9-(2-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0757]
9-(3-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0758]
9-(4-fluorobenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a-
]indole
[0759]
9-(3-methoxybenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
[0760]
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-ylmethy-
l)phenol
[0761]
9-(2-methoxybenzyl)-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indole
[0762]
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-ylmethy-
l)phenol
[0763] methyl
2-methoxy-6-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7--
a]indol-9-yl)benzoate
[0764]
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benz-
onitrile
[0765]
3-methyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol--
9-yl)benzonitrile
[0766]
2-methyl-3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol--
9-yl)benzonitrile
[0767]
2-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benz-
onitrile
[0768]
3-trifluoromethyl-4-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-
-a]indol-9-yl)benzonitrile
[0769]
3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)benz-
aldehyde
[0770]
[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol-9-yl)phe-
nyl]methanol
[0771]
9-[3-(methoxymethyl)phenyl]-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazep-
ino[1,7-a]indole
[0772]
N,N-dimethyl[3-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]in-
dol-9-yl)phenyl]methanamine
[0773]
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol--
9-yl)benzonitrile, and
[0774]
2-fluoro-5-(2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indol--
9-yl)benzamide.
[0775] Other compounds which technically are not within the scope
of formula I but are considered to be within the scope of the
instant invention include:
[0776] tert-butyl
1,2,4,5-tertrahydro-3H[1,4]diazepino[1,7-a]-indole-3-car-
boxylate;
[0777]
11[(E)-2-nitroethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino-[1,7-a]in-
dole;
[0778]
3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino-[1,7-a]ind-
ole; and
[0779]
2-bromo-1-[3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1-7-a]indole-11-yl]ethanone.
[0780] The following describe the preparation of compounds of the
present invention. All of the starting materials are prepared by
procedures described herein or by procedures that would be well
known to one of ordinary skill in organic chemistry.
[0781] Compounds of Formula I where R1a, R1b, R2a, R2b, R4, and
R3=H can be prepared by reactions outlined in Chart A1. Step 1
involves the reaction of a 2-nitrophenylacetic acid derivative with
carbonyl diimidazole followed by the addition of a magnesium salt
of ethylhydrogen malonate to provide compound 1. In Step 2,
treatment of the .beta.-ketoester with TiCl.sub.3 in the presence
of water and acetone reduces the nitro group followed by
spontaneous dehydrative cyclization with the ketone moiety to
provide 3-indoleacetic acid derivatives 2. This dehydrative
cyclization is also accomplished under heterogeneous palladium
catalyzed hydrogenylitic conditions. In Step 3, reduction of the
indole to the corresponding indoline 3 is achieved by the action of
NaCNBH.sub.3 in the presence of an acid such as acetic acid or
trifluoroacetic acid. In Step 4, the aniline moiety is alkylated
with 1,2-dibromoethane in the presence of base and a suitable
solvent such as CH.sub.3CN or N-methylpyrrolidinone to afford
trisubstituted amine derivatives 4. In Step 5, a second annulation
occurs by the reaction of 4 with a primary amine of formula R4NH2,
where R4 is as defined above, to provide azepinones 5. In Step 6,
the carbonyl group of compound 5 is reduced by reaction with a
reducing agent such as diisobutylaluminum hydride in a suitable
solvent such as tetrahydrofuran or toluene to yield azepines 6.
Finally, oxidation of indolines 6 to the corresponding indoles 7 is
achieved by the action of an oxidant such as
2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in the presence of
a suitable solvent such as dixoane (Examples 1-3).
[0782] Additionally, compounds of Formula I where R1a, R1b, R2a,
R2b, R3 and R4 are as defined above and bond a is a single or
double bond can be prepared by reactions outlined in Chart G. Step
1 involves the reaction of 20 (where X can be but is not limited to
I, Br, Cl, triflate, organotin, and organoboron) under various
catalytic transition metal coupling procedures. These procedures
can be performed by one skilled in the art of organic chemistry and
include, but are not limited to, the Suzuki coupling (for a review
see Snieckus, V.; Chem. Rev.; 90; 897; 1990), the Stille coupling
(for a review see Beletzkaya, I. P.; J. Organomet. Chem.; 250; 551;
1983), the Heck coupling (for a review see de Meijere, A. and
Meyer, F. E.; Angew. Chem. Int. Ed. Engl.; 33; 2379; 1994),
heteroatom carbon coupling reactions (for a review see Buchwald, S.
L. and Yang, B. H.; J. Organomet. Chem.; 576; 125; 1999), and
carbonylation reactions (for an example see Heck, R. F.;
Schoenberg, A.; Bartoletti, I.; J. Org. Chem.; 39; 3318; 1974).
[0783] The present invention also resides in the production of
compounds wherein R3 of Formula I is as defined above except for
hydrogen. To obtain compounds having specific R3 groups other than
hydrogen, 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole is
reacted with appropriate reactants using standard organic chemical
synthesis procedures as would be well understood in the art.
Examples of such standard procedures are shown in Charts B-E.
[0784] For example, Chart B illustrates the preparation of
compounds where R1a, R1b, R2a, R2b and R4 are H and R3 is
--C(O)C(O)XR5, where X and R5 are as defined above. In step 1, a
N-protected derivative 8 is reacted with oxalyl chloride in
dichloromethane at reduced temperatures to produce the
corresponding .alpha.-keto acid chloride. This uncharacterized
intermediate is reacted with various XR5 in the presence of a
tertiary amine base such as triethyl amine or diisopropylethyl
amine and an appropriate solvent such as dichloromethane or
toluene. Upon consumption of the .alpha.-keto acid chloride, the
protecting group is cleaved under standard deprotection conditions
such as trifluoroacetic acid for the tert-buyl carbamate group or
alkaline alcoholic conditions for the trifluoro acetamide group to
afford .alpha.-ketoamide products 9. This sequence can be carried
out with non-critical variations utilizing parallel synthetic
techniques and employing polymer supported reagents as reactants,
scavengers, and capture-release reagents to produce libraries of
final products.
[0785] Chart C illustrates the preparation of compounds where R1a,
R1b, R2a, R2b and R4 are H and R3 is --CH.sub.2C(O)XR5, where X and
R5 are as defined above. In step 1, products 9 (Chart B, step 1)
are reacted in an appropriate solvent such as 1,2-dichloroethane
with a reducing agent such as triethyl silane under acidic
conditions and elevated temperatures to afford the selectively
reduced products 10.
[0786] The production of compounds where R1a, R1b, R2a, R2b and R4
are H and R3 is --CH.sub.2CH.sub.2XR5, where X and R5 are as
defined above is depicted in Chart D. In step 1,
3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diaze- pino[1,7-a]indole is
reacted with oxalyl chloride in an appropriate solvent such as
diethyl ether or dichloromethane at reduced temperatures to give an
intermediate .alpha.-keto acid chloride that is reacted with
ethanol to afford compound 12. Reduction of the dicarbonyl moiety
is achieved in a two-step procedure involving initial reduction
with lithium aluminum hydride in an appropriate solvent such as
tetrahydrofuran to the corresponding diol followed by reduction of
the secondary alcohol by the action of triethyl silane under acidic
conditions in an appropriate solvent such as dichloromethane to
afford 13. In step 3, substitution with XR5 as defined above is
accomplished under Mitsunobu reaction conditions or by
functionalization of the terminal alcohol moiety of 13 to a
suitable leaving group such as mesylate followed by nucleophilic
displacement to give compounds 14. Finally, debenzylation of the
azepino nitrogen is accomplished by palladium catalyzed
hydrogenolysis in the presence of a hydrogen source such as
ammonium formate to afford compounds 15. Alternatively, conversion
of 14 to the corresponding trichloroethyl carbamate derivative
followed by cleavage of the newly installed protecting group by the
action of zinc in acetic acid affords compounds 15. This sequence
can be carried out with non-critical variations utilizing parallel
synthetic techniques and employing polymer supported reagents as
reactants, scavengers, and capture-release reagents to produce
libraries of final products.
[0787] Chart E illustrates the preparation of compounds where R1a,
R1b, R2a, R2b and R4 are H and R3 is --C(O)CH.sub.2XR5, where X and
R5 are as defined above. In step 1, protected intermediate 8 is
reacted with bromoacetyl bromide in the presence of a Lewis acid
such as aluminum trichloride and an appropriate solvent such as
dichloromethane to give 16. This .alpha.-bromo ketone is
substituted with XR5 as defined above by alkylation in the presence
of a suitable base such as potassium carbonate and solvent such as
acetonitrile. Upon consumption of the .alpha.-keto bromide, the
protecting group is cleaved under standard deprotection conditions
such as trifluoroacetic acid for the tert-buyl carbamate group or
alkaline alcoholic conditions for the trifluoro acetamide group to
afford products 17. This sequence can be carried out with
non-critical variations utilizing parallel synthetic techniques and
employing polymer supported reagents as reactants, scavengers, and
capture-release reagents to produce libraries of final
products.
[0788] The present invention also resides in the production of
compounds wherein bond a is a single bond of Formula I and where
R1a, R1b, R2a, R2b, R3, and R4 are as defined above. To obtain
compounds having bond a as a single bond, derivatives of
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7- -a] are reacted with
appropriate reactants using standard organic chemical synthesis
procedures as would be well understood in the art.
[0789] Chart F illustrates the preparation of compounds I where
bond a is a single bond and R1, R2, R3, and R4 are as defined
above. In step 1, the indole products 18 are reduced by the action
of a reducing reagent such as sodium cyanoborohydride or
triethylsilane in acidic conditions to afford the corresponding
indolines 19. Alternatively, reduction can be achieved by catalytic
hydrogenation under elevated pressures of hydrogen in the presence
of a metal catalyst such as palladium, platinum, rhodium, or
nickel. (for an overview of indole reductions to indolines see
Sundberg, R. J.; Indoles; Academic Press, 145; 1996).
[0790] The above compounds are useful in treating diseases or
disorders of the central nervous system occurring in animals,
preferably mammals. Typically, the mammal is a human being, but the
inventive compounds can be used to treat other animals such as food
animals (e.g., cows, pigs, sheep, goats, deer, poultry, etc.),
companion animals (e.g., dogs, cats, horses, birds and fish), or
other animals. The compounds may be administered in their native
form, or, more typically, with a pharmaceutically acceptable
excipient. The-compounds may also be administered in acid or basic
salt forms.
[0791] In cases where compounds are sufficiently basic or acidic to
form stable nontoxic acid or base salts, administration of the
compounds as salts may be appropriate. Examples of pharmaceutically
acceptable salts are organic acid addition salts formed with acids
which form a physiological acceptable anion, for example, tosylate,
methanesulfonate, acetate, citrate, malonate, tartarate, succinate,
benzoate, ascorbate, .alpha.-ketoglutarate, maleate, fumarate,
benzenesulfonate and .alpha.-glycerophosphate. Suitable inorganic
salts may also be formed, including hydrobromide, hydrochloride,
sulfate, nitrate, bicarbonate, and carbonate salts.
[0792] Pharmaceutically acceptable salts may be obtained using
standard procedures well known in the art, for example by reacting
a sufficiently basic compound such as an amine with a suitable acid
affording a physiologically acceptable anion. Alkali metal (for
example, sodium, potassium or lithium) or alkaline earth metal (for
example calcium) salts of carboxylic acids can also be made.
[0793] Compounds of the present invention can conveniently be
administered in a pharmaceutical composition containing the
compound in combination with a suitable excipient. Such
pharmaceutical compositions can be prepared by methods and contain
excipients which are well known in the art. A generally recognized
compendium of such methods and ingredients is Remington's
Pharmaceutical Sciences by E. W. Martin (Mark Publ. Co., 15th Ed.,
1975). To the extent necessary for completion, this reference is
hereby incorporated by reference. The compounds and compositions of
the present invention can be administered parenterally (for
example, by intravenous, intraperitoneal or intramuscular
injection), topically, nasally, orally, or rectally.
[0794] For oral therapeutic administration, the active compound may
be combined with one or more excipients and used in the form of
ingestible tablets, buccal tablets, troches, capsules, elixirs,
suspensions, syrups, wafers, and the like. Such compositions and
preparations should contain at least 0.1% of active compound. The
percentage of the compositions and preparations may, of course, be
varied and may conveniently be between about 2 to about 60% of the
weight of a given unit dosage form. The amount of active compound
in such therapeutically useful compositions is such that an
effective dosage level will be obtained.
[0795] The tablets, troches, pills, capsules, and the like may also
contain the following: binders such as gum tragacanth, acacia, corn
starch or gelatin; excipients such as dicalcium phosphate; a
disintegrating agent such as corn starch, potato starch, alginic
acid and the like; a lubricant such as magnesium stearate; and a
sweetening agent such as sucrose, fructose, lactose or aspartame or
a flavoring agent such as peppermint, oil of wintergreen, or cherry
flavoring. The above listing is merely representative and one
skilled in the art could envision other binders, excipients,
sweetening agents and the like. When the unit dosage form is a
capsule, it may contain, in addition to materials of the above
type, a liquid carrier, such as a vegetable oil or a polyethylene
glycol. Various other materials may be present as coatings or to
otherwise modify the physical form of the solid unit dosage form.
For instance, tablets, pills, or capsules may be coated with
gelatin, wax, shellac or sugar and the like. A syrup or elixir may
contain the active compound, sucrose or fructose as a sweetening
agent, methyl and propylparabens as preservatives, a dye and
flavoring such as cherry or orange flavor. Of course, any material
used in preparing any unit dosage form should be pharmaceutically
acceptable and substantially non-toxic in the amounts employed. In
addition, the active compound may be incorporated into
sustained-release preparations and devices including, but not
limited to, those relying on osmotic pressures to obtain a desired
release profile (e.g., the OROS drug delivery devices as designed
and developed by Alza Corporation).
[0796] The compounds or compositions can also be administered
intravenously or intraperitoneally by infusion or injection.
Solutions of the active compound or its salts can be prepared in
water, optionally mixed with a nontoxic surfactant. Dispersions can
also be prepared in glycerol, liquid polyethylene glycols,
triacetin, and mixtures thereof and in oils. Under ordinary
conditions of storage and use, these preparations contain a
preservative to prevent the growth of microorganisms.
[0797] Pharmaceutical dosage forms suitable for injection or
infusion can include sterile aqueous solutions or dispersions or
sterile powders comprising the active ingredient which are adapted
for the extemporaneous preparation of sterile injectable or
infusible solutions or dispersions, optionally encapsulated in
liposomes. In all cases, the ultimate dosage form should be
sterile, fluid and stable under the conditions of manufacture and
storage. The liquid carrier or vehicle can be a solvent or liquid
dispersion medium comprising, for example, water, ethanol, a polyol
(for example, glycerol, propylene glycol, liquid polyethylene
glycols, and the like), vegetable oils, nontoxic glyceryl esters,
and suitable mixtures thereof. The proper fluidity can be
maintained, for example, by the formation of liposomes, by the
maintenance of the required particle size in the case of
dispersions or by the use of surfactants. The prevention of the
action of microorganisms can be brought about by various
antibacterial and antifungal agents, for example, parabens,
chlorobutanol, phenol, sorbic acid, thimerosal, and the like. In
many cases, it will be preferable to include isotonic agents, for
example, sugars, buffers or sodium chloride. Prolonged absorption
of the injectable compositions can be brought about by the use in
the compositions of agents delaying absorption, for example,
aluminum monostearate and gelatin.
[0798] Sterile injectable solutions can be prepared by
incorporating the active compound in the required amount in the
appropriate solvent with various of the other ingredients
enumerated above, as required, followed by filter sterilization. In
the case of sterile powders for the preparation of sterile
injectable solutions, the preferred methods of preparation are
vacuum drying and the freeze drying techniques, which yield a
powder of the active ingredient plus any additional desired
ingredient present in the previously sterile-filtered solutions.
Sterilization of the powders may also be accomplished through
irradiation and aseptic crystallization methods. The sterilization
method selected is the choice of the skilled artisan.
[0799] For topical administration, the present compounds may be
applied in pure form, i.e., when they are liquids. However, it will
generally be desirable to administer them to the skin as
compositions or formulations, in combination with a
dermatologically acceptable carrier, which may be a solid or a
liquid.
[0800] Useful solid carriers include finely divided solids such as
talc, clay, microcrystalline cellulose, silica, alumina and the
like. Useful liquid carriers include water, alcohols or glycols or
water-alcohol/glycol blends, in which the present compounds can be
dissolved or dispersed at effective levels, optionally with the aid
of non-toxic surfactants. Adjuvants such as fragrances and
additional antimicrobial agents can be added to optimize the
properties for a given use. The resultant liquid compositions can
be applied from absorbent pads, used to impregnate bandages and
other dressings, or sprayed onto the affected area using pump-type
or aerosol sprayers. Thickeners such as synthetic polymers, fatty
acids, fatty acid salts and esters, fatty alcohols, modified
celluloses or modified mineral materials can also be employed with
liquid carriers to form spreadable pastes, gels, ointments, soaps,
and the like, for application directly to the skin of the user. To
this extent, the present invention further contemplates the use of
the pharmaceutically active materials in personal care compositions
such as lotions, cleansers, powders, cosmetics and the like.
[0801] The compound is conveniently administered in unit dosage
form; for example, containing about 0.05 mg to about 500 mg,
conveniently about 0.1 mg to about 250 mg, most conveniently, about
1 mg to about 150 mg of active ingredient per unit dosage form. The
desired dose may conveniently be presented in a single dose or as
divided doses administered at appropriate intervals, for example,
as two, three, four or more sub-doses per day. The sub-dose itself
may be further divided, e.g., into a number of discrete loosely
spaced administrations.
[0802] The compositions can conveniently be administered orally,
sublingually, transdermally, or parenterally at dose levels of
about 0.01 to about 150 mg/kg, preferably about 0.1 to about 50
mg/kg, and more preferably about 0.1 to about 10 mg/kg of mammal
body weight.
[0803] For parenteral administration the compounds are presented in
aqueous solution in a concentration of from about 0.1 to about 10%,
more preferably about 0.1 to about 7%. The solution may contain
other ingredients, such as emulsifiers, antioxidants or
buffers.
[0804] The exact regimen for administration of the compounds and
compositions disclosed herein will necessarily be dependent upon
the needs of the individual subject being treated, the patient type
(i.e., human or animal), the type of treatment and, of course, the
judgment of the attending practitioner.
[0805] Generally, compounds of the invention are 5-HT ligands. The
ability of a compound of the invention to act as a 5-HT receptor
agonist, partial agonist or antagonist can also be determined using
in vitro and in vivo assays that are known in the art. The
invention provides compounds of formula I that act as either
agonists, partial agonists or as antagonists of one or more 5-HT
receptor subtypes.
[0806] The inventive compounds of the present invention may be
useful as modulators of 5-HT receptor function. Thus, the compounds
are useful for treating diseases or disorders where modulation of
5-HT receptor function is desired. This inventive composition is
used to treat any of the diseases or disorders of the central
nervous system. Such diseases and disorders are defined in The
Diagnostic and Statistical Manual of Mental Disorders-IV (DSM-IV)
(American Psychiatric Association (1995)). To the extent necessary
for completion, the contents of this reference and all of the
defined diseases or disorders are expressly incorporated by
reference. Representative diseases or disorders include, but are
not limited to the following: obesity, depression, schizophrenia, a
stress related disease (e.g. general anxiety disorder), panic
disorder, a phobia, obsessive compulsive disorder,
post-traumatic-stress syndrome, immune system depression,
incontinence, a stress induced problem with the urinary,
gastrointestinal or cardiovascular system (e.g., stress
incontinence), neurodegenerative disorders, autism,
chemotherapy-induced vomiting, hypertension, migraine headaches,
cluster headaches, sexual dysfunction in a mammal (e.g. a human),
addictive disorder and withdrawal syndrome, an adjustment disorder,
an age-associated learning and mental disorder, anorexia nervosa,
apathy, an attention-deficit disorder due to general medical
conditions, attention-deficit hyperactivity disorder, bipolar
disorder, bulimia nervosa, chronic fatigue syndrome, conduct
disorder, cyclothymic disorder, dysthymic disorder, fibromyalgia
and other somatoform disorders, generalized anxiety disorder, an
inhalation disorder, an intoxication disorder, a movement disorder
(e.g., Tourette's syndrome), oppositional defiant disorder, a pain
disorder, peripheral neuropathy, post-traumatic stress disorder,
premenstrual dysphoric disorder, a psychotic disorder, seasonal
affective disorder, a sleep disorder, a specific developmental
disorder, and selective serotonin reuptake inhibition (SSRI) "poop
out" syndrome. Treatment of the above diseases or disorders is
accomplished by delivering a therapeutically effective amount of
the inventive composition to a mammal. In most cases this will be a
human being, but treatment of food animals (e.g., livestock such as
cows, pigs, deer, sheep, goats and the like, and poultry) and
companion animals (e.g., dogs, cats, birds, fish and horses) is
expressly covered herein.
[0807] The invention is described in greater detail by the
following non-limiting examples.
EXAMPLE 1
2,3,4,5-Tetrahydro-1H-[1,4]diazepino[1,7-a]indole hydrochloride
[0808] 4
Method 1
[0809] (Chart A, Step 1): A solution of ethylhydrogen malonate
(19.82 g, 150 mmol) in 375 mL THF is treated with a single portion
of magnesium ethoxide (8.58 g, 75 mmol). The resulting light yellow
suspension is stirred for 1 hour at RT then concentrated under
reduced pressure to give a light golden foam. In a separate vessel,
a solution of 2-nitrophenylacetic acid in 750 mL of THF is treated
with 1,1-carbonyldiimidazole (26.75 g, 165 mmol). The resulting
clear light yellow solution is stirred until TLC indicates no
remaining starting acid (4 hours). At this time, the solution of
acylimidazole is transferred to the flask containing the crude
magnesium salt and is stirred at RT for 18 hours. At this time, the
volatiles are removed under reduced pressure with the resulting
residue diluted with 60 mL 0.5M hydrochloric acid and extracted
twice (600 mL) with dichloromethane. The combined organics are
washed once with brine (500 mL), dried over MgSO.sub.4, filtered,
and concentrated to give 35.44 g of a golden oil. This material is
purified by Prep 500 HPLC (250 g silica gel cartridge) eluting with
35% ethyl acetate/heptane to afford 29.48 g (78%) of ethyl
3-(2-nitrophenyl)-3-oxop- ropanoate as a ligh yellow oil. .sup.1H
NMR (300 MHz, CDCl.sub.3) .delta. 8.14 (dd, J=1, 9 Hz, 1H), 7.62
(dt, J=1, 7 Hz, 1H), 7.49 (dt, J=1, 8 Hz, 1H), 7.32 (dd, J=1, 8 Hz,
1H), 4.27 (s, 2H), 4.22 (qt, J=7 Hz, 2H), 3.64 (s, 2H), 1.31 (t,
J=7 Hz, 3H).
[0810] (Chart A, Step 2): A solution of ethyl
3-(2-nitrophenyl)-3-oxopropa- noate (29.45 g, 117 mmol) in 390 mL
acetone is diluted with 2.9 L of a 4 M solution of ammonium acetate
resulting in the dissolution of a small amount of the starting
P-ketoester. This pale yellow solution is treated with 900 mL of a
15% aqueous solution of titanium trichloride immediately turning an
emerald green color. Two additional portions of titanium
trichloride (670 mL & 100 mL) are required to completely
consume the starting .beta.-ketoester. Within 15 minutes of the
final treatment with titanium trichloride, the reaction mixture is
washed four times with water (700 mL), once with brine (700 mL),
dried over MgSO.sub.4, filtered, and concentrated to give a golden
oil. This material is purified by Prep 500 HPLC (250 g silica gel
cartridge) eluting with 20% ethyl acetate/heptane to afford 21.95 g
(92%) of ethyl 2-(1H-indol-2-yl)acetate as a golden oil. .sup.1H
NMR (300 MHz, CDCl.sub.3) .delta. 8.70 (bs, 1H), 7.57 (d, J=8 Hz,
1H), 7.35 (d, J=7 Hz, 1H), 7.13 (m, 2H), 6.37 (d, J=1 Hz, 1H), 4.23
(qrt, J=7 Hz, 2H), 3.83 (s, 2H), 1.31 (t, J=7 Hz, 3H); .sup.13C NMR
(75 MHz, CDCl.sub.3) .delta. 170.7, 136.8, 130.6, 128.3, 121.7,
120.2, 119.8, 110.9, 101.8, 61.4, 34.0, 14.2.
[0811] (Chart A, Step 3): A solution of ethyl
2-(1H-indol-2-yl)acetate (21.93 g, 108 mmol) in 490 mL acetic acid
is treated via solid addition funnel with sodium cyanoborohydride
(20.34 g, 324 mmol) with some foaming and a slight exotherm being
observed. The resulting clear light yellow solution is stirred 2
hours, quenched with 30 mL water, stirred an additional 30 minutes,
basified with saturated NaHCO.sub.3, and extracted three times with
ethyl acetate (600 mL). The combined organics are dried over
Na.sub.2SO.sub.4, filtered, and concentrated to give 27.03 g of a
yellow oil. This material is purified by Prep 500 HPLC (250 g
silica gel cartridge) eluting with 7% ethyl acetate/heptane to
afford 17.79 g (80%) of ethyl 2-(2,3-dihydro-1H-indol-2-yl)acetate
as a light yellow oil. .sup.1H NMR (300 MHz, CDCl.sub.3) .delta.
7.09 (d, J=7 Hz, 1H), 7.04 (t, J=8 Hz, 1H), 6.72 (t, J=7 Hz, 1H),
6.63 (d, J=8 Hz, 1H), 4.44 (bs, 1H), 4.23 (m, 3H), 3.21 (dd, J=9,
15 Hz, 1H), 2.71 (dd, J=8, 16 Hz, 1H), 2.64 (d, J=7 Hz, 2H),
1.30(t, J=7 Hz, 3H); .sup.13C NMR (75 MHz, CDCl.sub.3) .delta.
172.4, 150.6, 127.9, 127.5, 124.7, 118.7, 109.3, 60.6, 55.8, 40, 9,
35.8, 14.3.
[0812] (Chart A, Step 4): A solution of ethyl
2-(2,3-dihydro-1H-indol-2-yl- )acetate (11.00 g, 53.6 mmol) in 500
mL acetonitrile is charged with powdered potassium carbonate (22.2
g, 161 mmol). The resulting light yellow suspension is treated with
dibromoethane (92 mL, 1.07 mol, filtered through basic alumina)
followed by heating to reflux for 60 hours. The volatiles are
removed under reduced pressure, diluted with water (450 mL), and
extracted twice with dichloromethane (300 mL). The combined
organics are washed once with brine (300 mL), dried over
MgSO.sub.4, filtered, and concentrated to give 27.10 g of a golden
oil. This material is purified by Prep 500 HPLC (250 g silica gel
cartridge) eluting with 7% ethyl acetate/heptane to afford 13.20 g
(79%) of ethyl
2-[1-(2-bromoethyl)-2,3-dihydro-1H-indol-2-yl]acetate as a very
light lavender oil. .sup.1H NMR (300 MHz, CDCl.sub.3) .delta. 7.10
(m, 2H), 6.70 (t, J=7 Hz, 1H), 6.45 (d, J=8 Hz, 1H), 4.19 (dqr,
J=7, 1 Hz, 2H), 4.13 (m, 1H), 3.53 (m, 4H), 3.32 (dd, J=9, 16 Hz,
1H), 2.80 (m, 2H), 2.57 (dd, J=8, 15 Hz, 1H), 1.30 (t, J=7 Hz, 3H);
.sup.13C NMR (75 MHz, CDCl.sub.3) .delta. 171.4, 150.6, 128.0,
127.7, 124.6, 118.3, 106.3, 60.9, 60.8, 49.2, 39.7, 35.5, 28.9,
14.2.
[0813] (Chart A, Step 5): A solution of ethyl
2-[1-(2-bromoethyl)-2,3-dihy- dro-1H-indol-2-yl]acetate (13.18 g,
42.2 mmol) in ammonia saturated methanol (800 mL) is heated to
50.degree. C. in a thick walled sealed tube for 18 hours. The
volatiles are removed under reduced pressure, diluted with
dichloromethane (400 mL) and washed once with 1N sodium hydroxide
(200 mL), once with brine (200 mL), dried over MgSO.sub.4,
filtered, and concentrated to give 8.30 g of a white solid. This
material is purified by LC (230-400 silica gel) eluting with 5%
methanol/dichloromethane to afford 7.23 g (85%) of
4,5,11,11a-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-2(3H)-one as a
white solid, mp 186-188.degree. C. IR (drift) 3210, 3082, 3047,
2950, 1668, 1606, 1485, 1458, 1383, 1352, 1308, 1280, 1246, 881,
748 cm.sup.-1. .sup.1H NMR (300 MHz, CDCl.sub.3) .delta. 7.11 (m,
2H), 7.03 (bs, 1H), 6.74 (t, J=7 Hz, 1H), 6.49 (d, J=8 Hz, 1H),
3.60 (m, 3H), 3.35 (m, 1H), 3.07 (m, 2H), 2.87 (m, 1H), 2.71 (m,
2H); .sup.13C NMR (75 MHz, CDCl.sub.3) .delta. 176.6, 151.7, 128.3,
127.6, 124.5, 118.9, 106.7, 62.1, 48.6, 43.0, 42.6, 36.
[0814] (Chart A, Step 6): A solution of
4,5,11,11a-tetrahydro-1H-[1,4]diaz- epino[1,7-a]indol-2(3H)-one
(12.70 g, 63 mmol) in THF (630 mL) is drop-wise treated with borane
dimethylsulfide complex (126 mL, 2M THF) with effervescence. The
reaction is heated to reflux for 18 hours. At this time, the
reaction is quenched by the careful addition of approximately 450
mL ethanol and upon completion of hydrogen evolution the volatiles
are removed under reduced pressure. The resulting residue is
re-diluted with 650 mL ethanol and 400 mL 1M hydrochloric acid and
heated to reflux for 1 hour. The reaction is cooled, concentrated,
basified to pH 13, and extracted three times with dichloromethane
(500 mL). The combined organics are washed once with brine (200
mL), dried over MgSO.sub.4, filtered, and concentrated to give
12.74 g of a pale yellow oil. This material is purified by LC
(230-400 silica gel) eluting with 1:15:84
NH.sub.4OH/methanol/dichloromethane to afford 11.53 g (97%) of
2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole as a pale
yellow oil. IR (liq.) 2930, 2838, 1608, 1489, 1460, 1383, 1306,
1272, 1236, 1226, 1157, 1022, 745, 723, 708 cm.sup.-1; MS (FAB) m/z
189 (MH.sup.+).
[0815] (Chart A, Step 7): A solution of
2,3,4,5,11,11a-hexahydro-1H-[1,4]d- iazepino[1,7-a]indole (221 mg,
1.2 mmol) in 1,4 dioxane (6 mL) is treated with a single portion of
DDQ (266 mg, 1.2 mmol) instantly turning black. HPLC analysis after
15 min indicates 15% remaining indoline and the reaction mixture is
treated with additional DDQ (66 mg, 0.3 mmol). After an additional
15 min, the reaction mixture is poured into 2N sodium hydroxide (35
mL) and extracted three times with dichloromethane (30 mL). The
combined organics are washed once with brine (30 mL), dried over
MgSO.sub.4, filtered, and concentrated to give 185 mg of a golden
syrup. This material is purified by LC (230-400 silica gel) eluting
with 0.5:5:94.5 NH.sub.4OH/methanol/dichloromethane to afford 114
mg (52%) of a light golden solid. This material is dissolved in a
mixture of dichloromethane/diethyl ether and treated with a
solution of hydrochloric acid in methanol. The resulting salt is
recrystallized from methanol and ethyl acetate to afford 90 mg of
2,3,4,5-Tetrahydro-1H-[1,4]diazepino[1,7- -a]indole hydrochloride
as a tan solid, mp 280-283.degree. C. IR (drift) 2962, 2940, 2819,
2736, 2701, 2670, 2653, 2558, 2450, 1458, 1373, 1335, 795, 750, 740
cm.sup.-1.
Method 2
[0816] A solution of
4,5,11,11a-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-2- (3H)-one
(25.93 g, 128 mmol) in 1,4 dioxane (1.3 L) is heated to 60.degree.
C. and treated with a single portion of DDQ (32.02 g, 141 mmol)
instantly turning brown with the formation of a percipitate. After
45 min, the reaction mixture is cooled to RT (cooling bath),
diluted with ethyl acetate (1 L), and washed once with 5N sodium
hydroxide (1.5 L). The alkaline layer is extracted three time with
1:1 ethyl acetate/THF (900 mL) with the combined organics being
washed once with water (1 L), once with brine (1 L), dried over
MgSO.sub.4, filtered, and concentrated to give 24.4 g of an orange
solid. This material is purified by LC (biotage 90 g columns)
eluting with 3% methanol/dichloromethane to afford 21.27 g (83%) of
4,5-dihydro-1H-[1,4]diazepino[1,7-a]indol-2(3H)-one as an orange
solid. IR (drift) 3207, 3097, 1678, 1469, 1453, 1417, 1370, 1356,
1317, 1226, 1147, 796, 771, 757, 749 cm.sup.-1; MS (EI) m/z 200
(M.sup.+).
[0817] A solution of
4,5-dihydro-1H-[1,4]diazepino[1,7-a]indol-2(3H)-one (10.50 g, 52.4
mmol) in THF (520 mL) is cooled to -78.degree. C. and treated with
a 1M solution of diisobutylaluminum hydride (630 mL, 630 mmol). The
cooling bath is removed and the reaction is stirred at rt
overnight. After 18 hours, the reaction is cooled to 0.degree. C.
and quenched by the addition of methanol (104 mL). Upon completion
of gas evolution, the mixture is diluted with dichloromethane (1.2
mL) and saturated Na/K tartrate (1.2 L), and rapidly stirred for 30
min. The solution phases are separated and the aqueous phase is
extracted twice with dichloromethane (1 L). The combined organics
are washed once with brine (1.2 L), dried over MgSO.sub.4,
filtered, and concentrated to give 10.24 g of a golden oil. This
material is purified by LC (230-400 silica gel) eluting with
0.5:3.5:96 NH.sub.4OH/methanol/dichloromethane to afford 7.11 g
(73%) of 2,3,4,5-Tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a
golden solid. This material is disolved in mehtanol and treated
with a solution of hydrochloric acid in methanol to produce a white
solid. This salt is recrystallized from methanol/ethyl acetate to
afford a light tan solid, mp 280-283.degree. C. IR (mull) 2817,
2793, 2750, 2735, 2669, 2656, 2559, 2530, 2451, 1445, 1421, 1336,
797, 751, 742 cm.sup.-1; UV .lambda..sub.max 270 (7910, 95%
ethanol).
EXAMPLE 2
8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
[0818] 5
[0819] A 60% oil dispersion of sodium hydride (7.83 g, 196 mmol) is
washed three times with pentane, suspended in dimethylsulfoxide
(200 mL), and treated with neat dimethylmalonate (22.4 mL, 196
mmol) with gas evolution. The grey suspension is heated to
100.degree. C. for 30 min, cooled to rt, and treated with
2,5-dibromonitrobenzene (25.0 g, 89 mmol). The resulting red
solution is heated to 100.degree. C. for 1 hour followed by cooling
to rt. After 16 hr, the reaction is quenched with 700 mL saturated
NH.sub.4Cl and extracted once with 1:1 hexane/ethyl acetate. The
combined organics are washed once with saturated NH.sub.4Cl (300
mL), three times with water (300 mL), once with brine (300 mL),
dried over MgSO.sub.4, filtered, and concentrated to give 33.94 g
of a golden oil. This material crystallizes from ethyl
acetate/heptane to afford 23.02 g of dimethyl
2-(4-bromo-2-nitrophenyl)malonate as an off-white solid, mp
86-88.degree. C.
[0820] A solution of dimethyl 2-(4-bromo-2-nitrophenyl)malonate
(17.98 g, 54 mmol), lithium chloride (4.59 g, 108 mmol), and water
(0.97 mL, 54 mmol) in dimethylsulfoxide (360 mL) is heated to
90.degree. C. After 20 hrs, the reaction is cooled to rt, diluted
with ethyl acetate (700 mL), washed twice with brine (700 mL),
dried over MgSO.sub.4, filtered, and concentrated to give 15.21 g
of a golden syrup. This material is purified by Prep 500 HPLC (250
g silica gel cartridge) eluting with 7% ethyl acetate/heptane to
afford 10.07 g of methyl 2-(4-bromo-2-nitrophenyl)acet- ate as a
light yellow solid.
[0821] A solution of methyl 2-(4-bromo-2-nitrophenyl)acetate (11.40
g, 41.6 mmol) in methanol (42 mL) and THF (42 mL) is treated with
5M sodium hydroxide (42 mL, 208 mmol). After 20 hrs, the reaction
mixture is acidified with 1 M hydrochloric acid (300 mL) and
extracted twice with ethyl acetate (250 mL). The combined organics
are washed once with brine (200 mL), dried over MgSO.sub.4,
filtered, and concentrated to give 10.52 g of an orange solid. This
material is recrystallized from ethyl acetate/heptane to afford
9.21 g (85%) of 2-(4-bromo-2-nitrophenyl)acetic acid as a light
yellow solid, mp 166-168.degree. C. IR (drift) 3101, 3082, 3029,
2966, 2942, 2866, 1696, 1524, 1431, 1412, 1351, 1335, 1276, 1238,
885 cm.sup.-1.
[0822] (Chart A, Step 1): Following the general procedure of Step 1
of Example 1, and making non-critical variations but substituting
2-(4-bromo-2-nitrophenyl)acetic acid for 2-nitrophenylacetic acid,
gives 10.01 of a crude product. This material is purified by LC
(230-400 silica gel) eluting with 22% acetone/heptane to afford
9.16 g of ethyl 4-(4-bromo-2-nitrophenyl)-3-oxobutanoate as a white
solid, mp 78-80.degree. C. IR (drift) 1743, 1712, 1521, 1419, 1405,
1367, 1348, 1314, 1278, 1262, 1207, 1194, 1073, 1027, 882
cm.sup.-1.
[0823] (Chart A, Step 2): Following the general procedure of Step 2
of Example 1, and making non-critical variations but substituting
ethyl 4-(4-bromo-2-nitrophenyl)-3-oxobutanoate for ethyl
3-(2-nitrophenyl)-3-oxopropanoate, gives 8.39 g of a crude product.
This material is purified by LC (biotage 90 g column) eluting with
8% acetone/heptane to afford 6.88 g (97%) of ethyl
2-(6-bromo-1H-indol-2-yl)- acetate as a white solid, mp
67-69.degree. C. IR (drift) 3378, 2978, 1717, 1456, 1398, 1387,
1374, 1336, 1270, 1221, 1178, 1053, 910, 811, 650 cm.sup.-1.
[0824] (Chart A, Step 3): Following the general procedure of Step 3
of Example 1, and making non-critical variations but substituting
ethyl 2-(6-bromo-1H-indol-2-yl)acetate for ethyl
2-(1H-indol-2-yl)acetate and trifluoroacetic acid for acetic acid,
gives 6.86 g of a crude product. This material is purified by LC
(biotage 90 g column) eluting with 10% ethyl acetate/heptane to
afford 5.59 g of ethyl 2-(6-bromo-2,3-dihydro-1H-
-indol-2-yl)acetate as a pale yellow mobile oil. IR (liq.) 1726,
1606, 1483, 1443, 1398, 1386, 1372, 1318, 1299, 1259, 1232, 1188,
1054, 1027, 898 cm.sup.-1.
[0825] (Chart A, Step 4): Following the general procedure of Step 4
of Example 1, and making non-critical variations but substituting
ethyl 2-(6-bromo-2,3-dihydro-1H-indol-2-yl)acetate for ethyl
2-(2,3-dihydro-1H-indol-2-yl)acetate and 1-methyl-2-pyrrolidinone
for acetonitrile, gives 8.19 g of a crude product. This material is
purified by LC (230-400 silica gel) eluting 10% ethyl
acetate/heptane to afford 3.18 g (50%) of ethyl
2-[6-bromo-1-(2-bromoethyl)-2,3-dihydro-1H-indol-2-- yl]acetate as
a light yellow oil. IR (liq.) 1731, 1604, 1581, 1485, 1455, 1438,
1425, 1375, 1359, 1306, 1266, 1183, 1150, 1135, 1036 cm.sup.-1.
[0826] (Chart A, Step 5): Following the general procedure of Step 5
of Example 1, and making non-critical variations but substituting
ethyl 2-[6-bromo-1-(2-bromoethyl)-2,3-dihydro-1H-indol-2-yl]acetate
for ethyl 2-[1-(2-bromoethyl)-2,3-dihydro-1H-indol-2-yl]acetate,
gives 2.35 g of a crude product. This material is purified by LC
(biotage 90 g column) eluting with 45% ethyl
acetate/dichloromethane to afford 1.25 g (56%) of
8-bromo-4,5,11,11a-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-2(3H)-one
as a white solid. IR (drift) 3077, 2966, 1662, 1604, 1575, 1490,
1431, 1353, 1322, 1300, 1233, 905, 884, 814, 789 cm.sup.-1.
[0827] (Chart A, Step 6): Following the general procedure of Step 6
of Example 1, and making non-critical variations but substituting
8-bromo-4,5,11,1a-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-2(3H)-one
for 4,5,11,11a-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-2(3H)-one,
gives 1.10 g of a crude product. This material is purified by LC
(230-400 silica gel) eluting with 15% methanol/dichloromethane to
afford 989 mg of
8-bromo-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole as
a white solid. IR (drift) 2940, 2919, 2893, 2867, 2850, 2823, 1602,
1573, 1492, 1452, 1378, 1274, 1216, 787, 732 cm.sup.-1.
[0828] (Chart A, Step 7): Following the general procedure of Step 7
of Example 1, and making non-critical variations but substituting
8-bromo-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole for
2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole, gives 491
mg of a crude product. This material is purified by LC (230-400
silica gel) eluting with 10% methanol/dichloromethane to give a
yellow oil. This material is dissolved in a mixture of
methanol/ethyl acetate and treated with a solution of hydrochloric
acid in methanol. The resulting salt is recrystallized from
methanol/ethyl acetate to afford
8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride as a tan solid, mp 292-295.degree. C. IR (drift)
2959, 2850, 2818, 2806, 2773, 2742, 2708, 2670, 2655, 2628, 2564,
2446, 1456, 1371, 817 cm.sup.-1.
EXAMPLE 3
10-methoxy-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
[0829] 6
[0830] In a dry 25 mL flask 0.17 mg (1.0 mmol) of
2-methyl-3-nitroanisole is combined with 30 mg (0.97 mmol)
paraformaldehyde in 7 mL of dimethylsulfoxide (sure-seal). This
solution is treated with 1M Potassium t-butoxide/THF (0.20 ML) with
the reaction mixture becoming bright red in color. After 2 hours
the reaction mixture is diluted with water and ethyl acetate is
added. The layers are separated followed by two ethyl acetate
extractions. The organics are combined, washed with brine, dried
over MgSO.sub.4, filtered, and concentrated to give a crude yellow
oil that solidifies overnight. This material is purified by LC (45%
ethyl acetate/heptane) to yield 140 mg (71%) of
2-(2-methoxy-6-nitrophenyl)-1-e- thanol as a pale yellow solid.
.sup.1H NMR (300 MHz, DMSO-d.sub.6) .delta. 2.90 (t, J=7 Hz, 2H),
3.50 (q, J=7 Hz, 2H), 3.88 (s, 3H), 4.74 (t, J=5 Hz, 1H), 7.32 (dd,
J=2, 8 Hz, 1H), 7.46-7.36 (m, 2H); .sup.13C NMR (75 MHz,
CDCl.sub.3) .delta. 158.5, 127.8, 116.2, 114.2, 62.0, 56.3, 29.2;
IR (drift) 1536, 1469, 1458, 1352, 1279, 1266, 1217, 1065, 1040,
1031, 1014, 895, 806, 796, 740 cm.sup.-1.
[0831] A solution of 4.3 g of 2-(2-methoxy-6-nitrophenyl)-1-ethanol
acetone (117 mL) is slowly treated with a solution of Jones Reagent
(31 mL). The volatiles are removed under reduced pressure, diluted
with 5M sodium hydroxide, cooled to 0.degree. C., and treated
slowly with concentrated H.sub.2SO.sub.4. This solution is
extracted four times with ethyl acetate with the combine organics
washed with brine, dried over NaSO.sub.4, filtered, and
concentrated. The crude material is purified by LC (10%
MeOH/CH.sub.2Cl.sub.2) to give 3.5 g of 2-(2-methoxy-6-nitropheny-
l)acetic acid as a yellow/gold solid. .sup.1H NMR (300 MHz,
DMSO-d.sub.6) .delta. 3.84 (s, 3H), 3.87 (s, 2H), 7.42 (d, J=7 Hz,
1H), 7.52 (t, J=8 Hz, 1H), 7.59 (dd, J=1, 8 Hz, 1H); .sup.13C NMR
(75 MHz, CDCl.sub.3) .delta. 157.9, 150.7, 127.5, 120.1, 115.3,
114.8, 56.4, 11.1; IR (drift) 3020, 2983, 2945, 2888, 2840, 1710,
1531, 1471, 1434, 1353, 1274, 1256, 1229, 1058, 799 cm.sup.-1. HRMS
(FAB) calculated for C.sub.9H.sub.9NO.sub.5+H1 212.0559, found
212.0555.
[0832] (Chart A, Step 1): Following the general procedure of Step 1
of Example 1, and making non-critical variations but substituting
2-(2-methoxy-6-nitrophenyl)acetic acid for 2-nitrophenylacetic acid
gives a crude yellow oil. This material is purified by LC (230-400
silica gel) eluting with 35% ethyl acetate/heptane to afford 1.04 g
(74%) of ethyl 4-(2-methoxy-6-nitrophenyl)-3-oxobutanoate as yellow
solid. IR (drift) 1746, 1714, 1523, 1466, 1366, 1352, 1317, 1306,
1268, 1229, 1196, 1069, 1053, 1033, 736 cm.sup.-1; .sup.1H NMR (300
MHz, CDCl.sub.3) .delta. 1.32 (t, J=7 Hz, 3H), 3.62 (s, 2H), 3.89
(s, 3H), 4.25 (m, 4H), 7.17 (d, J=8 Hz, 1H), 7.42 (t, J=8 Hz, 1H),
7.64 (d, J=8 Hz, 1H); .sup.13C NMR (75 MHz, CDCl.sub.3) .delta.
198.2, 167.0, 158.4, 150.0, 128.7, 118.9, 116.8, 115.2, 61.5, 56.6,
49.3, 39.7, 14.
[0833] (Chart A, Step2): A solution of ethyl
4-(2-methoxy-6-nitrophenyl)-3- -oxobutanoate (10.6 g, 37.5 mmol) in
MeOH (350 mL) is purged with N.sub.2, and treated with 10% Pd/C
(1.10 g) turning the yellow solution black. The suspension is
treated with ammonium formate (27.4 g, 43.5 mmol) with a slight
exotherm and evolution of H.sub.2. After 15 minutes, the reaction
mixture is filtered through a pad of celite, and concentrated. The
residue is diluted with water and extracted 3 times with ethyl
acetate. The combined organics are washed with brine, dried over
NaSO.sub.4, filtered, and concentrated to give 9.4 g of crude
material which is combined with the crude material from a previous
1.5 mmol reaction. The crude material is purified by LC (25% ethyl
acetate/heptane) to give 8.08 g of substituting ethyl
2-(4-methoxy-1H-indol-2-yl)acetate as an oil that solidifies
overnight. IR (liq.) 3389, 1730, 1617, 1594, 1510, 1438, 1367,
1287, 1250, 1217, 1167, 1151, 1097, 1030, 767 cm.sup.-1.
[0834] (Chart A, Step 3): Following the general procedure of Step 3
of Example 1, and making non-critical variations but substituting
ethyl 2-(4-methoxy-1H-indol-2-yl)acetate for ethyl
2-(1H-indol-2-yl)acetate, gives 6.83 g of a crude product. This
material is purified by LC eluting with 10% ethyl acetate/heptane
to afford 4.82 g of ethyl
2-(4-methoxy-2,3-dihydro-1H-indol-2-yl)acetate as a yellow solid.
IR (drift) 1727, 1614, 1602, 1493, 1469, 1323, 1296, 1276, 1259,
1235, 1192, 1168, 1148, 1095, 1027 cm.sup.-1.
[0835] (Chart A, Step 4): Following the general procedure of Step 4
of Example 1, and making non-critical variations but substituting
ethyl 2-(4-methoxy-2,3-dihydro-1H-indol-2-yl)acetate for ethyl
2-(2,3-dihydro-1H-indol-2-yl)acetate, gives 8.68 g of a crude
product. This material is purified by LC to afford 6.95 g of ethyl
2-[1-(2-bromoethyl)-4-methoxy-2,3-dihydro-1H-indol-2-yl]acetate as
a light yellow solid. .sup.13C NMR (75 MHz, DMSO-d.sub.6) .delta.
171.0, 155.6, 152.1, 128.9, 113.1, 101.4, 100.3, 65.0, 60.0, 60.0,
54.9, 48.1, 32.0, 30.6, 14.0; IR (drift) 1726, 1712, 1617, 1596,
1477, 1357, 1269, 1255, 1214, 1157, 1080, 1071, 1027, 757, 704
cm.sup.-1.
[0836] (Chart A, Step 5): Following the general procedure of Step 5
of Example 1, and making non-critical variations but substituting
ethyl
2-[1-(2-bromoethyl)-4-methoxy-2,3-dihydro-1H-indol-2-yl]acetate for
ethyl 2-[1-(2-bromoethyl)-2,3-dihydro-1H-indol-2-yl]acetate and
isopropyl alcohol for methanol with a catalytic amount of sodium
iodide, gives 3.86 g of a crude product. This material is purified
by LC (biotage 90 g column) eluting with dichloromethane to 5%
methanol/dichloromethane to afford 3.6 g (82%) of
10-methoxy-4,5,11,11a-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indol-2(3H)-one as a white solid. IR (drift) 2953, 1666,
1608, 1487, 1473, 1445, 1353, 1305, 1261, 1237, 1223, 1097, 1076,
760, 709 cm.sup.-1.
[0837] (Chart A, Step 6): Following the general procedure of Step 6
of Example 1, and making non-critical variations but substituting
10-methoxy-4,5,11,11a-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-2(3H)-one
for 4,5,11,11a-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-2(3H)-one
gives 3.03 g of a crude product. This material is purified by LC
eluting with 0.5:9.5:90 NHOH.sub.4/methanol/dichloromethane to give
2.46 g of
10-methoxy-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
as a white solid. IR (drift) 2920, 2895, 2834, 2803, 1614, 1597,
1474, 1453, 1381, 1254, 1244, 1223, 1085, 762, 758 cm.sup.-1.
[0838] (Chart A, Step 7): Following the general procedure of Step 7
of Example 1, and making non-critical variations but substituting
10-methoxy-2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole
for 2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indole, gives
207 mg of a crude product. This material is purified by LC eluting
with 0.5:4.0:95.5 NH.sub.4OH/methanol/dichloromethane to afford 157
mg of an orange oil. This material is dissolved in ethyl acetate
and treated with a solution of 2M hydrochloric acid in methanol to
afford 167 mg of
10-methoxy-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride as a white solid. .sup.1H NMR (DMSO-d.sub.6) .delta.
3.27 (s, 6H), 3.85 (s, 3H), 4.55 (m, 2H), 6.34 (s, 1H), 6.52 (dd,
1H), 7.04 (m, 2H), 9.65 (br s, 2H); .sup.13C NMR (DMSO-d.sub.6)
.delta. 152.3, 138.0, 137.5, 121.7, 117.3, 102.8, 99.6, 97.6, 55.0,
46.7, 45.5, 40.7, 24.4; IR (drift) 2961, 2944, 2832, 2783, 2747,
2732, 2689, 2660, 1584, 1499, 1467, 1355, 1257, 762, 730
cm.sup.-1.
EXAMPLE 4
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbaldehyde
[0839] 7
[0840] A solution of DMF (10 mL) cooled to 0.degree. C. is treated
with phosphorus oxychloride (0.30 mL, 3.3 mmol) and stirred for 10
min. This clear colorless solution of the cloroiminium salt is
slowly treated with a solution of tert-butyl
1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indol- e-3-carboxylate
in DMF (9 mL) followed by warming to rt. After 18 hr, the reaction
is quenched with 5N sodium hydroxide (40 mL), stirred 5 min, and
extracted twice with dichloromethane (40 mL). The combined organics
are washed twice with water (25 mL), once with brine (25 mL), dried
over MgSO.sub.4, filtered, and concentrated to give 942 mg of a
crude yellow solid. This material is purified by LC (biotage 40 g
column) eluting with 35% ethyl acetate/heptane to afford 677 mg of
tert-butyl
11-formyl-1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indole-3-carboxylate
as a pale yellow solid, mp 167-168.degree. C. IR (drift) 1684,
1654, 1469, 1424, 1396, 1370, 1350, 1304, 1248, 1197, 1170, 1121,
762, 757, 752 cm.sup.-1.
[0841] A suspension of tert-butyl
11-formyl-1,2,4,5-tetrahydro-3H-[1,4]dia-
zepino[1,7-a]indole-3-carboxylate (225 mg, 0.72 mmol) in methanol
(5 mL) is cooled to 0.degree. C. and treated with a solution of
saturated hydrochloric acid in methanol (3 mL). After 15 min, the
yellow homogenous solution is treated with an additional portion of
the hydrochloric acid solution and warmed to rt. After 1 hr, the
reaction is concentrated under reduced pressure, diluted with 2M
sodium hydroxide (15 mL), and extracted twice with dichloromethane
(20 mL). The combined organics are washed once with brine (20 mL),
dried over MgSO.sub.4, filtered, and concentrated to give 165 mg of
a crude solid. This material is purified by LC (230-400) silica gel
eluting with 10% methanol/dichloromethane to afford 118 mg of
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbaldehyde
as an off-white solid. This material is recrystallized form ethyl
acetate/heptane to give a light yellow solid, mp 167-168.degree.
C.
[0842] IR (drift) 3307, 2941, 1636, 1464, 1429, 1391, 1367, 1350,
1269, 1205, 1124, 1052, 775, 750, 731 cm.sup.-1.
EXAMPLE 5
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
[0843] 8
[0844] A solution of tert-butyl
1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a- ]indole-3-carboxylate
(286 mg, 1 mmol) in dichloromethane (20 mL) is cooled to 0.degree.
C. and treated with oxalyl chloride (0.17 mL, 2.0 mmol) instantly
turning a golden color. After 1 hr, the reaction mixture is treated
with a 2M solution of ammonia in ethanol (4 mL) with the formation
of a white percipitate. After 30 min, the reaction mixture is
diluted with dichloromethane (15 mL) and washed once with saturated
sodium bicarbonate (25 mL), once with water (20 mL), once with
brine (20 mL), dried over MgSO.sub.4, filtered, and concentrated to
give 389 mg of a yellow solid. This material is purified by LC
(230-400) silica gel eluting with 60% ethyl acetate/heptane to
afford 294 mg of an off-white solid. This material is dissolved in
methanol (5 mL), cooled to 0.degree. C., and treated with a
saturated solution of hydrochloric acid in methanol (5 mL). After 3
hrs, the volatiles are removed under reduced pressure, diluted with
5M sodium hydroxide (15 mL), and extracted twice with a 1:1
solution of THF/ethyl acetate (20 mL). The combined organics are
dried over MgSO.sub.4, filtered, and concentrated to give a yellow
solid. This material is recrystallized from methanol/ethyl acetate
to afford 100 mg of
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)acetamide as a white solid, mp 214-215.degree. C. IR
(drift) 3363, 1680, 1619, 1588, 1512, 1465, 1407, 1356, 1347, 1335,
1186, 1077, 750, 672, 629 cm.sup.-1; MS (FAB) m/z 258
(MH.sup.+).
EXAMPLE 6
2,2,2-trifluoro-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-
-1-ethanone
[0845] 9
[0846] A solution of tert-butyl
11-formyl-1,2,4,5-tetrahydro-3H-[1,4]diaze-
pino[1,7-a]indole-3-carboxylate (286 mg, 1 mmol) in DMF (10 mL) is
treated with trifluoroacetic anhydride (0.17 mL, 1.2 mmol). After
24 hrs, a second portion of the anhydride is added with the
reaction becoming a darker color. After an additional 18 hrs, the
reaction is concentrated under reduced pressure, diluted with water
(15 mL), and extracted twice with dichloromethane (15 mL). The
combined organics are washed once with saturated sodium bicarbonate
(15 mL), once with water (15 mL), once with brine (20 mL), dried
over MgSO.sub.4, filtered, and concentrated to give 352 mg of a
crude solid. This material is purified by LC (230-400) silica gel
eluting with 25% ethyl acetate/heptane to afford 315 mg (82%) of a
rose colored solid. This material is dissolved in methanol (5 mL),
cooled to 0.degree. C., and treated with a saturated solution of
hydrochloric acid in methanol (3 mL). After 30 min, the volatiles
are removed under reduced pressure, diluted with ethyl acetate (30
mL), washed twice with saturated sodium bicarbonate, dried over
MgSO.sub.4, filtered, and concentrated to give 232 mg of a crude
solid. This material is purified by LC (230-400) silica gel eluting
with 10% methanol/dichloromethane to afford 202 mg (87%) of
2,2,2-trifluoro-1-(2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indol-11-yl)-1-ethanone as a light yellow solid, mp
131-133.degree. C. IR (drift) 1654, 1504, 1486, 1467, 1428, 1279,
1245, 1212, 1198, 1178, 1134, 1061, 936, 746, 739 cm.sup.-1.
EXAMPLE 7
11-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
[0847] 10
[0848] A solution of
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-- carbaldehyde
(208 mg, 0.97 mmol) in THF (5 mL) is treated with a 1M solution of
lithium aluminum hydride in THF (5 mL, 5 mmol) with instant gas
evolution. After 18 hrs at rt, the reaction is heated to reflux for
an additional hour, cooled to rt, and quenched by the successive
addition of water (0.19 mL), SM sodium hydroxide (0.17 mL), and
water (0.66 mL). The resulting gelatinous solution is diluted with
ethyl acetate (25 mL), filtered through a pad of celite, and
concentrated to give 185 mg of a yellow oil. This material is
purified by LC (230-400) silica gel eluting with 10%
methanol/dichloromethane to afford 92 mg of a pink solid. This
material is dissolved in a mixture of ethyl acetate/methanol and
treated with a solution of hydrochloric acid in methanol to produce
a pink solid. The resulting solid is triturated with diethyl
ether/ethyl acetate to give
11-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride as a light rose solid. IR (drift) 2974, 2954, 2864,
2825, 2749, 2680, 2656, 2444, 1581, 1469, 1425, 1378, 1331, 1186,
738 cm.sup.-1.
EXAMPLE 8
11-chloro-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
[0849] 11
[0850] A solution of tert-butyl
11-formyl-1,2,4,5-tetrahydro-3H-[1,4]diaze-
pino[1,7-a]indole-3-carboxylate (286 mg, 1 mmol) in THF (10 mL) is
cooled to 0.degree. C. and slowly treated with a solution of
N-chlorosuccinimide (134 mg, 1.0 mmol) in THF (10 mL). The
resulting florescent yellow solution is warmed to rt. After 18 hrs,
the now green reaction mixture is concentrated under reduced
pressure, diluted with water (20 mL) and brine (5 mL), and
extracted twice with ethyl acetate (20 mL). The combined organics
are washed once with brine (20 mL), dried over MgSO.sub.4,
filtered, and concentrated to give 361 mg of a crude oil. This
material is purified by LC (230-400) silica gel eluting with 10%
ethyl acetate/heptane to afford 277 mg of a white solid. This
material is dissolved in methanol (5 mL), cooled to 0.degree. C.,
and treated with a saturated solution of hydrochloric acid in
methanol (5 mL). After 15 min, the reaction mixture is warmed to rt
for an addition 1 hour, followed by removal of the volatiles under
reduced pressure to give a white solid. This material is
recrystallized from methanol/ethyl acetate to afford 135 mg of
11-chloro-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride as an off-white solid, mp >250.degree. C. IR
(drift) 2982, 2933, 2908, 2888, 2816, 2775, 2719, 2652, 2627, 2564,
2429, 1580, 1462, 1323, 744 cm.sup.-1.
EXAMPLE 9
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbonitrile
[0851] 12
[0852] A solution of tert-butyl
11-formyl-1,2,4,5-tetrahydro-3H-[1,4]diaze-
pino[1,7-a]indole-3-carboxylate in formic acid (1 mL) is treated
with hydroxylamine hydrochloride (90 mg, 1.3 mmol) and heated to
reflux. After 18 hrs, the reaction mixture is cooled to rt,
quenched with 1M sodium hydroxide (15 mL), and extracted twice with
ethyl acetate (20 mL). The combined organics are washed once with
brine (20 mL), dried over MgSO.sub.4, filtered, and concentrated to
give 224 mg of a crude solid. This material is purified by LC
(230-400) silica gel eluting with 5% methanol/dichloromethatne to
afford 123 mg of 2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indole-11-carbonitrile as a red solid, mp
161-164.degree. C. IR (drift) 3313, 2935, 2906, 2203, 1539, 1463,
1421, 1351, 1328, 1272, 1208, 1185, 822, 769, 752 cm.sup.-1.
EXAMPLE 10
8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbaldehyde
[0853] 13
[0854] A solution of
8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in- dole in
dichloromethane (6 mL) is successively treated with pyridine (0.13
mL, 1.6 mmol) and trifluoroacetic acid anhydride (0.23 mL, 1.6
mmol). After 3 hrs, the resulting black solution is diluted with
additional dichloromethane (20 mL) and washed twice with saturated
copper sulfate (10 mL), once with water (10 mL), once with brine
(10 mL), dried over MgSO.sub.4, filtered, and concentrated to give
374 mg of a crude solid. This material is purified by LC (230-400)
silica gel eluting with 15% ethyl acetate/heptane to afford 228 mg
of 1-(8-bromo-1,2,4,5-tetrahydro-3-
H-[1,4]diazepino[1,7-a]indol-3-yl)-2,2,2-trifluoro-1-ethanone as a
white solid and 109 mg of
1-[8-bromo-11-(2,2,2-trifluoroacetyl)-1,2,4,5-tetrahy-
dro-3H-[1,4]diazepino[1,7-a]indol-3-yl]-2,2,2-trifluoro-1-ethanone
as a white solid. Data for
1-(8-bromo-1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-
-a]indol-3-yl)-2,2,2-trifluoro-1-ethanone: .sup.1H NMR (300 MHz,
CDCl.sub.3) .delta. 7.42 (d, J=10 Hz, 2H), 7.22 (dd, J=2, 8 Hz,
1H), 6.34 (d, J=2 Hz, 1H), 4.29 (m, 2H), 3.90 (m, 4H), 3.15 (m,
2H). Data for
1-[8-bromo-11-(2,2,2-trifluoroacetyl)-1,2,4,5-tetrahydro-3H-[1,4]diazepin-
o[1,7-a]indol-3-yl]-2,2,2-trifluoro-1-ethanone: .sup.1H NMR (300
MHz, DMSO-d.sub.6) .delta. 8.06 (d, J=17 Hz, 1H), 7.79 (d, J=9 Hz,
1H), 7.49 (d, J=9 Hz, 1H), 4.72 (m, 2H), 3.87 (m, 4H), 3.73 (m,
2H).
[0855] Following the general procedure of Example 4, and making
non-critical variations but substituting
1-(8-bromo-1,2,4,5-tetrahydro-3H-
-[1,4]diazepino[1,7-a]indol-3-yl)-2,2,2-trifluoro-1-ethanone for
tert-butyl
1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indole-3-carboxylat- e,
gives 182 mg of a crude solid. This material is purified by LC
(230-400 silica gel) eluting with 7% methanol/dichloromethane to
afford 130 mg of a tan solid. This solid is recrystallized from
methanol/ethyl acetate to give 46 mg of
8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-1-
1-carbaldehyde as an off-white solid, mp 186-188.degree. C. IR
(drift) 1646, 1531, 1468, 1455, 1424, 1391, 1333, 1046, 1037, 954,
862, 837, 820, 753, 738 cm.sup.-1.
EXAMPLE 11
1-(8-bromo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-2,2,2-t-
rifluoro-1-ethanone
[0856] 14
[0857] A solution of
1-[8-bromo-11-(2,2,2-trifluoroacetyl)-1,2,4,5-tetrahy-
dro-3H-[1,4]diazepino[1,7-a]indol-3-yl]-2,2,2-trifluoro-1-ethanone
(105 mg, 0.23 mmol) in methanol (3 mL) is treated with 1M sodium
hydroxide (1 mL, 1 mmol). After 30 min, the reaction is diluted
with water (15 mL) and extracted twice with dichloromethane (20
mL). The combined organics are washed with brine (15 mL), dried
over MgSO.sub.4, filtered, and concentrated to give a crude solid.
This material is recrystallized from ethyl acetate/heptane to
afford 48 mg of a white solid. IR (drift) 1666, 1508, 1464, 1426,
1282, 1248, 1211, 1201, 1181, 1130, 1060, 1043, 956, 939, 757
cm.sup.-1.
EXAMPLE 12
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carboxamide
[0858] 15
[0859] A solution of
2,2,2-trifluoro-1-(1,2,4,5-tetrahydro-3H-[1,4]diazepi-
no[1,7-a]indol-3-yl)-1-ethanone (448 mg, 1.6 mmol) in
dichloromethane (20 mL) is treated with chlorosulfonyl isocyanate
(0.19 mL, 2.1 mmol). The resulting golden homogenous solution is
stirred for 1 hour and treated with methanol (10 mL) and a solution
of 25% sodium methoxide in methanol (2 mL, 8.8 mmol). The reaction
mixture quickly turns to a white suspension and after 30 min is
filtered to give a crude white solid. This material is triturated
with hot methanol, filtered through a pad of celite, and
concentrated to 184 mg of a white solid that is further purified by
LC (230-400 silica gel) eluting with 9:1:89
methanol/NH.sub.4OH/dichloromethane to afford 137 mg of
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carboxamide as
a white solid. IR (drift) 3353, 3341, 3173, 1641, 1602, 1549, 1463,
1432, 1418, 1322, 1314, 778, 740, 729, 654 cm.sup.-1.
EXAMPLE 13
1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanone
hydrochloride
[0860] 16
[0861] A solution of dimethylacetamide (0.12 mL, 1.3 mmol) in
chloroform (2 mL) is cooled to 0.degree. C. and treated with
phosphorus oxychloride (0.12 mL, 1.3 mmol) with no observable
change. The solution is warmed to rt over 10 min, treated with a
solution of 2,2,2-trifluoro-1-(1,2,4,5-tet-
rahydro-3H-[1,4]diazepino[1,7-a]indol-3-yl)-1-ethanone (120 mg,
0.43 mmol) in chloroform (2 mL), and heated to reflux. After 18
hrs, the reaction mixture is cooled to rt, quenched with 5N sodium
hydroxide (20 mL), methanol (10 mL), and reheated to 60.degree. C.
for 30 min. At this time, the reaction is cooled to rt, volatiles
removed under reduced pressure, and extracted twice with
dichloromethane (20 mL). The combined organics are washed with
brine (20 mL), dried over MgSO.sub.4, filtered, and concentrated to
give a crude solid. This material is purified by LC (230-400 silica
gel) eluting with 3:0.5:96.5 methanol:NH.sub.4OH:dichloro- methane
to afford 25 mg of an off-white solid. This solid is dissolved in
ethyl acetate (10 mL) and treated with 2M hydrochloric acid in
methanol (0.2 mL) to afford
1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-
-yl)-1-ethanone hydrochloride as a light golden solid. IR (drift)
2971, 2805, 2771, 2751, 2729, 2689, 1646, 1521, 1466, 1421, 1352,
1341, 1210, 966, 742 cm.sup.-1.
EXAMPLE 14
3-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0862] 17
[0863] A solution of
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole (372 mg, 2.0
mmol) in methanol (25 mL) is treated with a solution of 37% aqueous
formaldehyde (24 mmol, 2.0 mL). The resulting clear solution is
treated with a single portion of sodium cyanoborohydride (251 mg,
4.0 mmol) turning slightly a lighter yellow color. After 40 min,
the reaction is quenched with 1M hydrochloric acid (15 mL), stirred
over 10 min, basified to pH 13, volatiles removed under reduced
pressure, and extracted twice with ethyl acetate (25 mL). The
combined organics are washed with brine (20 mL), dried over
MgSO.sub.4, filtered, and concentrated to give a crude oil. This
material is purified by LC (230-400 silica gel) eluting with 70%
acetone/heptane to afford 234 mg (58%) of
3-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a
white solid, mp 59-60.degree. C. IR (drift) 2924, 2781, 2758, 2741,
1458, 1413, 1377, 1339, 1326, 1315, 1290, 1133, 1003, 799, 737
cm.sup.-1. MS (EI) m/z 200(M.sup.+).
EXAMPLE 15
3-ethyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0864] 18
[0865] A solution of
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole (280 mg, 1.5
mmol) in acetonitrile (15 mL) is treated with powdered potassium
carbonate (622 mg, 4.5 mmol) and bromoethane (0.12 mL, 1.65 mmol,
filtered through a pad of celite). The resulting milky suspenesion
is heated to 40.degree. C. After 22 hrs, the volatiles are removed
under reduced pressure, diluted with water (20 mL), and extracted
twice with ethyl acetate (20 mL). The combined organics are washed
with brine (20 mL), dried over MgSO.sub.4, filtered, and
concentrated to give a crude oil. This material is purified by LC
(230-400 silica gel) eluting with 5% methanol/dichloromethane to
afford 226 mg of 3-ethyl-2,3,4,5-tetrahydro-1-
H-[1,4]diazepino[1,7-a]indole as a white solid, mp 44-46.degree. C.
IR (drift) 2931, 2808, 1466, 1413, 1373, 1348, 1323, 1315, 1243,
1132, 1104, 776, 749, 732, 688 cm.sup.-1.
EXAMPLE 16
3-propyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
hydrochloride
[0866] 19
[0867] Following the general procedure of Example 15, and making
non-critical variations but substituting 1-iodopropane (0.18 mL,
1.8 mmol), gives 421 mg of a crude oil. This material is purified
by LC (230-400 silica gel) eluting with 14:1:85 acetone:triethyl
amine:heptane to afford 236 mg (69%) of a colorless oil. This
material is dissolved in ethyl acetate and treated with 2M
hydrochloric acid in methanol (0.75 mL) with immediate formation of
a white solid that is collected by filtration and dried to give
3-propyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind- ole
hydrochloride as a white solid, mp 257-259.degree. C. IR (drift)
2629, 2603, 2592, 2581, 2535, 2500, 2487, 1463, 1419, 1334, 1318,
920, 785, 749, 736 cm.sup.-1; MS (EI) m/z 228 (M.sup.+).
EXAMPLE 17
3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0868] 20
[0869] Following the general procedure of Example 15, and making
non-critical variations but substituting benzyl chloride (0.38 mL,
3.3 mmol), gives 850 mg of a crude oil. This material is purified
by LC (230-400 silica gel) eluting with 15% ethyl acetate/heptane
to afford 724 mg of
3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as an
ivory solid. IR (drift) 2932, 2807, 1460, 1451, 1408, 1365, 1349,
1325, 1317, 1197, 1138, 1027, 789, 736, 699 cm.sup.-1.
EXAMPLE 18
[0870] 21
[0871] A solution of
2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indol-11-yl)-1-ethanol (320 mg, 1.0 mmol) in dichloromethane (10
mL) is cooled to 0.degree. C., treated with methanesulfonyl
chloride (93 .mu.L, 1.2 mmol), and triethylamine (0.21 mL, 1.5
mmol). After 30 min, the yellow solution is diluted with additional
dichloromethane (15 mL) and washed once with water (15 mL), once
with brine (15 mL), dried over MgSO.sub.4, filtered, and
concentrated to give a yellow oil. This crude material is diluted
with acetonitrile (10 mL) and treated with benzylamine (0.33 mL,
3.0 mmol), and powdered potassium carbonate (415 mg, 3.0 mmol)
followed by heating to reflux. After 18 hrs, the yellow suspension
is cooled to rt, concentrated, diluted with water (15 mL), and
extracted twice with dichloromethane (20 mL). The combined organics
are washed with brine (20 mL), dried over MgSO.sub.4, filtered, and
concentrated to give a crude oil. This material is purified by LC
(230-400 silica gel) eluting with 4:0.5:95.5
methanol/NH.sub.4OH/dichloro- methane to afford 220 mg of
N-benzyl-2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,-
4]diazepino[1,7-a]indol-11-yl)-1-ethanamine as a yellow oil. IR
(liq.) 3025, 2913, 2811, 1494, 1478, 1469, 1453, 1427, 1372, 1363,
1347, 1324, 1120, 733, 698 cm.sup.-1; MS (EI) m/z 409
(M.sup.+).
EXAMPLE 19
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanamine
[0872] 22
Method 1
[0873] A solution of
N-benzyl-2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diaze-
pino[1,7-a]indol-11-yl)-1-ethanamine (195 mg, 0.48 mmol) in
methanol (10 mL) is treated with 10% palladium on carbon (40 mg)
and ammonium formate (210 mg, 3.3 mmol) followed by heating to
reflux. After 18 hrs, the reaction is cooled to rt, filtered
through celite, and concentrated to give a crude yellow oil. This
material is purified by LC (230-400 silica gel) eluting with
20:2.5:77.5 methanol/ammonuim hydroxide/dichloromethane to afford
51 mg (47%) of 2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)-1-ethanamine as a colorless oil that solidified, mp
77-80.degree. C. MS (EI) m/z 229 (M.sup.+); % Water (KF): 0.94;
Anal. Calculated for C.sub.14H.sub.19N.sub.3.0.94H.sub.2O: C,
72.64; H, 8.38; N, 18.15. Found: C, 72.66; H, 8.32; N, 18.03.
Method 2
[0874] A solution of
11-[(E)-2-nitroethenyl]-2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indole (236 mg, 0.92 mmol) in THF (9 mL) is cooled to
0.degree. C. and treated with lithium aluminum hydride (1M THF, 2.8
mL, 2.8 mmol) with gas evolution. The reaction is heated to reflux
for 4 hrs followed by cooling to rt for 16 hrs. At this time, the
reaction mixture is quenched by the successive addition of 0.11 mL
water, 0.10 mL 5N NaOH, and 0.37 mL water. The resulting thick
gelatinous suspension is diluted with dichloromethane (30 mL),
filtered through celite, and concentrated to give a crude oil. This
material is purified by LC (230-400 silica gel) eluting with
20:2.5:77.5 methanol/ammonuim hydroxide/dichloromethane to afford
92 mg of 2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl-
)-1-ethanamine as a yellow syrup. IR (liq.) 3353, 3307, 3087, 3048,
3025, 2935, 2844, 1469, 1426, 1373, 1340, 1324, 1181, 1015, 742
cm.sup.-1; MS (FAB) m/z 230 (MH.sup.+).
EXAMPLE 20
N-(4-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)acetamide
[0875] 23
[0876] (Chart B, Step 1): A solution
3-(trifluoroacetyl)-2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indole in dichloromethane (20 mL) is
cooled to 0.degree. C. and treated with oxalylchloride (0.17 mL,
2.0 mmol) instantly becoming a yellow color. After 40 min, the
reaction mixture is warmed to rt and volatiles are removed under
reduced pressure. The resulting solid is diluted with toluene (20
mL) and dichloromethane (5 mL) and treated with the 4-methoxy
aniline (160 mg, 1.3 mmol) and triethylamine (0.42 mL, 3.0 mmol)
with immediate smoke/haze forming. After 18 hrs, the reaction
mixture is concentrated, diluted with methanol (10 mL) and THF (10
mL) and treated with 1N sodium hydroxide (10 mL). After 15 min,
reaction mixture is concentrated, diluted with 1N sodium hydroxide
(20 mL), and extracted twice with dichloromethane (25 mL). The
combined organics are washed with brine (25 mL), dried over
MgSO.sub.4, filtered, and concentrated to give a crude solid. This
material is purified by LC (230-400 silica gel) eluting with 10%
methanol/dichloromethane to afford 359 mg of
N-(4-methoxyphenyl)-2-oxo-2--
(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
as a light yellow solid, mp 177-180.degree. C. IR (drift) 1670,
1621, 1559, 1507, 1465, 1416, 1333, 1264, 1242, 1221, 1211, 1073,
838, 789, 762 cm.sup.-1; OAMS supporting ions at: ESI+ 364.1.
EXAMPLE 21
N-(2,4-difluorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indol-11-yl)acetamide
[0877] 24
[0878] Following the general procedure of Example 20 (Chart B, Step
1), and making non-critical variations but substituting
2,4-difluoroaniline (327 mg, 2.5 mmol), gives 684 mg of a crude
solid. This material is recrystallized from methanol/ethyl acetate
to afford 597 mg of
N-(2,4-difluorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indol-11-yl)acetamide as a white solid, mp 184.5-185.5.degree. C.
IR (drift) 1674, 1618, 1566, 1507, 1459, 1423, 1331, 1205, 1099,
1065, 962, 849, 822, 762, 747 cm.sup.-1.
EXAMPLE 22
N-(3-chloro-4-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indol-11-yl)acetamide
[0879] 25
[0880] Following the general procedure of Example 20 (Chart B, Step
1), and making non-critical variations but substituting
3-chloro-p-anisidine (399 mg, 2.5 mmol), gives 846 mg of a crude
solid. This material is triturated with hot methanol/ethyl acetate
to afford 634 mg of
N-(3-chloro-4-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indol-11-yl)acetamide as a tan powder, mp 221-223.degree.
C. IR (drift) 1666, 1605, 1499, 1462, 1423, 1309, 1284, 1276, 1249,
1213, 1073, 1058, 837, 802, 753 cm.sup.-1.
EXAMPLE 23
2-oxo-N-phenyl-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)a-
cetamide
[0881] 26
[0882] Following the general procedure of Example 20 (Chart B, Step
1), and making non-critical variations but substituting aniline
(0.23 mL, 2.5 mmol), gives 684 mg of a crude solid. This material
is purified by LC (biotage 400 g column) eluting with 8%
methanol/dichloromethane to afford 603 mg of a yellow foam that is
recrystallized from ethyl acetate/heptane to afford
2-oxo-N-phenyl-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)acetamide as a light yellow solid, mp 157-160.degree. C.
IR (drift) 1675, 1620, 1611, 1600, 1559, 1509, 1463, 1444, 1420,
1325, 824, 770, 755, 743, 691 cm.sup.-1.
EXAMPLE 24
N-(2-naphthyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-1-
1-yl)acetamide
[0883] 27
[0884] Following the general procedure of Example 20 (Chart B, Step
1), and making non-critical variations but substituting
2-aminonaphthalene (341 mg, 2.4 mmol), gives 940 mg of a crude
solid. This material is recrystallized from ethyl acetate/heptane
to afford 647 mg of as an off-white powder. IR (drift) 1667, 1620,
1591, 1570, 1521, 1463, 1421, 1356, 1348, 1266, 1075, 856, 804,
758, 743 cm.sup.-1; OAMS supporting ions at: ESI+ 384.0.
EXAMPLE 25
N-(4-methoxyphenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-
-yl)acetamide
[0885] 28
[0886] (Chart C, Step 1): A solution of
N-(4-methoxyphenyl)-2-oxo-2-(2,3,4-
,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide (355
mg, 0.98 mmol) in 1,2-dichloroethane (20 mL) is treated with TFA
(2.5 mL) and triethylsilane (2.5 mL). The resulting clear golden
solution is heated to reflux. After 18 hrs, the reaction is cooled
to rt, washed twice with saturated sodium bicarbonate (50 mL), once
with brine (50 mL), dried over MgSO.sub.4, filtered, and
concentrated to give a golden oil. This material is purified by LC
(230-400 silica gel) eluting with 5:0.5:94.5
methanol/NH.sub.4OH/dichloromethane to afford 275 mg of
N-(4-methoxyphenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-1-
1-yl)acetamide as a white foam.
[0887] IR (drift) 1662, 1602, 1535, 1512, 1467, 1411, 1372, 1358,
1323, 1297, 1243, 1180, 1032, 830, 740 cm.sup.-1; OAMS supporting
ions at: ESI+ 350.2.
EXAMPLE 26
N-(2,4-difluorophenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
-11-yl)acetamide
[0888] 29
[0889] Following the general procedure of Example 25 (Chart C, Step
1), and making non-critical variations but substituting
N-(2,4-difluorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indol-11-yl)acetamide (374 mg, 1.0 mmol), gives a crude oil. This
material is purified by LC (230-400 silica gel) eluting with
5:0.5:94.5 methanol/NH.sub.4OH/dichloromethane to afford 326 mg of
N-(2,4-difluorophenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)acetamide as a white foam.
[0890] IR (drift) 1686, 1680, 1610, 1525, 1517, 1467, 1429, 1372,
1360, 1258, 1140, 1096, 969, 848, 741 cm.sup.-1; OAMS supporting
ions at: ESI+ 356.1; MS (FAB) m/z 356 (MH.sup.+); HRMS (FAB)
calculated for C.sub.20H.sub.19F.sub.2N.sub.3O+H.sub.1
356.1574.
EXAMPLE 27
N-phenyl-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetami-
de
[0891] 30
[0892] Following the general procedure of Example 25 (Chart C, Step
1), and making non-critical variations but substituting
2-oxo-N-phenyl-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-
acetamide (329 mg, 1.0 mmol), gives a crude oil. This material is
purified by LC (230-400 silica gel) eluting with 5:0.5:94.5
methanol/NH.sub.4OH/dichloromethane to afford 226 mg of
N-phenyl-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetam-
ide as a white foam. IR (drift) 1663, 1598, 1537, 1525, 1498, 1467,
1440, 1372, 1359, 1343, 1323, 1181, 754, 740, 694 cm.sup.-1; OAMS
supporting ions at: ESI+ 320.2.
EXAMPLE 28
4-methoxy-N-[2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)eth-
yl]aniline dihydrochloride
[0893] 31
[0894] A solution of 1M lithium aluminum hydride (7 mL, 7 mmol) and
THF (14 mL) is cooled to 0.degree. C. and portion-wise treated with
aluminum trichloride (317 mg, 2.4 mmol) with gas evolution. The
resulting colorless solution with a small amount of percipitate is
drop-wise treated with a solution of
N-(4-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide (433mg, 1.19 mmol)
in THF (10 mL) with additional gas evolution. The resulting yellow
suspension is warmed to rt for 20 hr followed by heating to
50.degree. C. for 8 hours. At this time, the reaction is quenched
by the successive addition of water (0.27 mL), 5M sodium hydroxide
(0.24 mL), and water (0.93 mL). The resulting gelatinous suspension
is diluted with dichloromethane, filtered through a pad of celite,
with the organics washed once with 1N sodium hydroxide (35 mL),
once with brine (35 mL), dried over MgSO.sub.4, filtered, and
concentrated to give a tan oil. This material is purified by LC
(230-400 silica gel) eluting with 5:0.75:94.25
methanol/NH.sub.4OH/dichloromethane to afford 330 mg of
4-methoxy-N-[2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)et-
hyl]aniline as a light golden oil. This material is dissolved in
ethyl acetate and treated with 2M hydrochloric acid in methanol
(1.1 mL) with immediate formation of a white solid that is
collected by filtration and recrystallized from methanol/ethyl
acetate to afford 343 mg of
4-methoxy-N-[2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)et-
hyl]aniline dihydrochloride as a white solid. IR (drift) 2818,
2803, 2746, 2726, 2694, 2669, 2642, 2585, 2552, 2449, 1514, 1471,
1255, 1244, 757 cm.sup.-1; OAMS supporting ions at: ESI+ 336.2.
EXAMPLE 29
Ethyl-2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)--
2-oxoacetate
[0895] 32
[0896] (Chart D, Step 1): A round bottom flask is charged with
3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole (1.17 g,
4.23 mmol) and ethyl ether (21 mL). The yellow homogeneous solution
is cooled with an ice bath for 10 minutes. Oxalyl chloride (0.37
mL, 4.23 mmol) is added drop-wise. A yellow precipitate is
observed, turning into a gel. After 10 minutes of stirring the
ether is removed under reduced pressure. Ethanol (21 mL) is quickly
added to the yellow residue and a nitrogen stream is established on
the surface of the reaction to remove excess HCl. Using a syringe,
triethylamine (1.30 mL, 9.31 mmol) is added dropwise forming HCl
gas which is carried away by the nitrogen stream. After the
triethylamine addition is complete, the flask is adapted with a
reflux condenser, and the reaction is heated to reflux for two
hours. The reaction is then cooled and concentrated to 2.79 g of a
yellow solid. The crude solid is purified on silica gel using a
gradient from 25% to 50% ethyl acetate/heptane as the eluent to
give 1.293 grams of ethyl
2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-2-oxo-
acetate as a yellow solid. Anal. Calculated for
C.sub.23H.sub.24N.sub.2O.s- ub.3: C, 73.38; H, 6.43; N, 7.44.
Found; C, 73.02; H, 6.55; N, 7.38.
EXAMPLE 30
2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-etha-
nol
[0897] 33
[0898] (Chart D, Step 2): A dry round bottom flask is charged with
THF (100 mL) and 1M LAH in THF (65.13 mL, 65.13 mmol). A solution
of ethyl
2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-2-oxo-
acetate (6.13 g, 16.28 mmol) in THF (75 mL) is slowly added to the
reaction via syringe. The addition is exothermic. The reaction
mixture is heated to reflux for 5 hours then reaction is quenched
with a very slow and sequential addition of a) 2.47 mL H.sub.2O, b)
2.22 mL of 5N aq. NaOH, and c) 8.64 mL H.sub.2O. The resulting
heterogeneous solution is stirred vigorously with excess ethyl
acetate for one hour and filtered through a pad of celite. The
filtrate is concentrated to give 9.23 g of
1-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1,2-e-
thanediol as a crude yellow solid. A 2 L round bottom is charged
with a solution of the crude diol in dichloromethane (541 mL). A
semi-dropwise addition of TFA (14.46 mL, 188 mmol) is followed by
the slow addition of triethylsilane (9.1 mL, 57 mmol) and the
mixture is first refluxed for two hours, then stirred at ambient
temperature for 18 hours. The resulting brown solution is
concentrated in vacuo, diluted with dichloromethane, basified with
sat. aq. Na.sub.2CO.sub.3 and vigorously stirred while cooling to
10.degree. C. The mixture is transferred to a round bottom,
volatiles are removed in vacuo at 50.degree. C. The residue is
partitioned between water and dichloromethane. The organics are
combined, dried with Na.sub.2SO.sub.4, filtered and concentrated to
give 5.57 g of an orange oil. Purification of the crude on silica
gel using a gradient of 35%-50% ethyl acetate/heptane as the eluent
gives 3.52 g of
2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-eth-
anol as a tan oil.
[0899] IR (liq.) 2933, 2873, 2816, 1469, 1453, 1427, 1376, 1364,
1347, 1325, 1185, 1046, 1015, 733, 699 cm.sup.-1.
EXAMPLE 31
3-benzyl-11-(2-phenoxyethyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dole
[0900] 34
[0901] (Chart D, Step 3): A dry round bottom flask is charged with
2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-eth-
anol (420 mg, 1.31 mmol), phenol (185.2 mg, 1.97 mmol),
triphenylphosphine (413 mg, 1.57 mmol), and THF (12 mL, freshly
distilled). After cooling the reaction to 0.degree. C.,
diethylazodicarboxylate (DEAD) (0.248 mL, 1.57 mmol) is added
dropwise via syringe. The ice bath is allowed to expire, and the
reaction is stirred at ambient temperature for 18 hours. The
reaction is quenched with 30% H.sub.2O.sub.2 (0.20 mL), diluted
with ethyl ether and washed twice with 10% aq. NaHSO.sub.3. The
organics are washed twice with aq. 1N NaOH, once with brine, dried
with Na.sub.2SO.sub.4, filtered and concentrated to 1.08 g of a
crude yellow solid. Purification of the crude using silica gel and
10% ethyl acetate in heptane as the eluent gives 392 mg (76%) of
3-benzyl-11-(2-phenoxyethy-
l)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a pale
yellow oil. HRMS (FAB) calculated for
C.sub.27H.sub.28N.sub.2O+H.sub.1 397.2280, found 397.2271.
EXAMPLE 32
11-(2-phenoxyethyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0902] 35
[0903] (Chart D, Step 4): A dry round bottom flask is charged with
3-benzyl-11-(2-phenoxyethyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole (317 mg, 0.80 mmol), ammonium formate (254 mg, 4.0 mmol),
methanol (18 mL) and dichloromethane (3.2 mL). After the addition
of 10% Pd/C (64 mg) the reaction is stirred at ambient temperature
for two days. The reaction mixture is filtered through a pad of
celite, and the catalyst is rinsed with methanol. The filtrates are
combined and concentrated to 380 mg of a crude solid. This material
is recrystallized from ethyl acetate/methanol/ethyl ether to afford
239 mg of 11-(2-phenoxyethyl)-2,3,-
4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a white solid. IR
(drift) 3026, 3015, 2998, 2983, 2948, 2910, 2869, 2806, 2781, 2752,
1468, 1451, 1245, 755, 746 cm.sup.-1.
EXAMPLE 33
3-benzyl-11-[2-(2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
[0904] 36
[0905] Following the general procedure of Example 31 (Chart D, Step
3), and making non-critical variations but substituting phenol with
2-methoxyphenol, gives 360 mg of a crude oil. This material is
purified by LC (230-400 silica gel) eluting with 10% ethyl acetate
in heptane to afford 149 mg of
3-benzyl-11-[2-(2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahyd-
ro-1H-[1,4]diazepino[1,7-a]indole as a pale yellow oil. HRMS (FAB)
calculated for C.sub.28H.sub.30N.sub.2O.sub.2+H.sub.1 427.2385,
found 427.2389.
EXAMPLE 34
3-benzyl-11-[2-(2-fluorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0906] 37
[0907] Following the general procedure of Example 31 (Chart D, Step
3) and making non-critical variations but substituting phenol with
2-fluorophenol, gives 326 mg of a yellow solid. This material is
purified by LC (230-400 silica gel) eluting with 10% ethyl acetate
in heptane to afford 176 mg of
3-benzyl-11-[2-(2-fluorophenoxy)ethyl]-2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indole as an ivory solid. HRMS (FAB)
calculated for C.sub.27H.sub.27FN.sub.2O+H.sub.1 415.2185, found
415.2180.
EXAMPLE 35
3-benzyl-11-[2-(8-quinolinyloxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0908] 38
[0909] Following the general procedure of Example 31 (Chart D, Step
3) and making non-critical variations but substituting phenol with
8-hydroxyquinoline, gives 312 mg of a crude yellow solid. This
material is purified by LC (230-400 silica gel) eluting with 25%
acetone in heptane to afford 69 mg
3-benzyl-11-[2-(8-quinolinyloxy)ethyl]-2,3,4,5-te-
trahydro-1H-[1,4]diazepino[1,7-a]indole as an oil. HRMS (FAB)
calculated for C.sub.30H.sub.29N.sub.3O+H.sub.1 448.2389, found
448.2383.
EXAMPLE 36
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanol
[0910] 39
[0911] Following the general procedure of Example 32 (Chart D, Step
4) and making non-critical variations but substituting with
2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-eth-
anol gives 128 mg of a crude oil. This material is purified by LC
(230-400 silica gel) eluting with 0.5% NH.sub.4OH and 10% methanol
in dichloromethane to afford 119 mg of
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indol-11-yl)-1-ethanol as a tan paste. HRMS (FAB)
calculated for C.sub.14H.sub.18N.sub.2O+H.sub.1 231.1497, found
231.1503.
EXAMPLE 37
3-benzyl-11-[2-(2-methoxy-4-methylphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,-
4]diazepino[1,7-a]indole
[0912] 40
[0913] Following the general procedure of Example 31 (Chart D, Step
3) and making non-critical variations but substituting phenol with
2-methoxy-4-methylphenol, gives 460 mg of a crude oil. This
material is purified by LC (230-400 silica gel) eluting with 10%
ethyl acetate in heptane to afford 158 mg of
3-benzyl-11-[2-(2-methoxy-4-methylphenoxy)eth-
yl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a pale
yellow oil. HRMS (FAB) calculated for
C.sub.29H.sub.32N.sub.2O.sub.2+H.sub.1 441.2542, found
441.2547.
EXAMPLE 38
3-benzyl-11-[2-(2-fluoro-6-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,-
4]diazepino[1,7-a]indole
[0914] 41
[0915] Following the general procedure of Example 31 (Chart D, Step
3) and making non-critical variations but substituting phenol with
2-fluoro-6-methoxyphenol, gives 430 mg of a crude oil. This
material is purified by LC (230-400 silica gel) eluting with 10%
ethyl acetate in heptane to afford 189 mg of
3-benzyl-11-[2-(2-fluoro-6-methoxyphenoxy)eth-
yl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a pale
yellow oil. HRMS (FAB) calculated for
C.sub.28H.sub.29FN.sub.2O.sub.2+H.sub.1 445.2291, found
445.2284.
EXAMPLE 39
11-[2-(2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indole
[0916] 42
[0917] Following the general procedure of Example 32 (Chart D, Step
4) and making non-critical variations but substituting
3-benzyl-11-[2-(2-methoxy-
phenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
with
3-benzyl-11-(2-phenoxyethyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole gives 146 mg of a crude white solid. This material is
purified by LC (230-400 silica gel) eluting with 0.25% NH.sub.4OH
and 2.5% methanol in dichloromethane to afford 137 mg of
11-[2-(2-methoxyphenoxy)ethyl]-2,3,4,-
5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a tan solid. IR
(liq.) 2936, 1591, 1505, 1469, 1455, 1373, 1340, 1326, 1252, 1227,
1179, 1124, 1027, 1015, 740 cm.sup.-1.
EXAMPLE 40
11-[2-(2-fluorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0918] 43
[0919] Following the general procedure of Example 32 (Chart D, Step
4) and making non-critical variations but substituting
3-benzyl-11-[2-(2-methoxy-
phenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
with
3-benzyl-11-[2-(2-fluorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole gives 179 mg of a crude yellow paste. This material
is purified by LC (230-400 silica gel) eluting with 0.25%
NH.sub.4OH and 2.5% methanol in dichloromethane to afford 141 mg of
11-[2-(2-fluorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indole as a white solid. IR (drift) 1502, 1466, 1342, 1319, 1307,
1283, 1264, 1255, 1203, 1181, 1106, 804, 772, 751, 742
cm.sup.-1.
EXAMPLE 41
11-[2-(2-methoxy-4-methylphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
[0920] 44
[0921] Following the general procedure of Example 32 (Chart D, Step
4) and making non-critical variations but substituting
3-benzyl-11-[2-(2-methoxy-
phenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
with
3-benzyl-11-[2-(2-methoxy-4-methylphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole gives 170 mg of a crude oil. This
material is purified by LC (230-400 silica gel) eluting with 0.25%
NH.sub.4OH and 2.5% methanol in dichloromethane to afford 107 mg of
11-[2-(2-methoxy-4-methylphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole as a pale yellow oil. IR (liq.) 2937, 2918, 1514,
1469, 1374, 1364, 1340, 1325, 1264, 1233, 1159, 1139, 1035, 1015,
741 cm.sup.-1.
EXAMPLE 42
11-[2-(2-fluoro-6-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indole
[0922] 45
[0923] Following the general procedure of Example 32 (Chart D, Step
4) and making non-critical variations but substituting
3-benzyl-11-[2-(2-methoxy-
phenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
with
3-benzyl-11-[2-(2-fluoro-6-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indole gives 279 mg of a crude solid. This
material is purified by LC (230-400 silica gel) eluting with 0.25%
NH.sub.4OH and 2.5% methanol in dichloromethane to afford 159 mg of
11-[2-(2-fluoro-6-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indole as a pale yellow oil. IR (liq.) 2940, 1608, 1497,
1476, 1470, 1440, 1374, 1304, 1283, 1247, 1230, 1086, 992, 775, 740
cm.sup.-1.
EXAMPLE 43
3-benzyl-11-[2-(2-chlorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0924] 46
[0925] Following the general procedure of Example 31 (Chart D, Step
3) and making non-critical variations but substituting phenol with
2-chlorophenol, gives 445 mg of a crude oil. This material is
purified by LC (230-400 silica gel) eluting with 10% ethyl acetate
in heptane to afford 192 mg of
3-benzyl-11-[2-(2-chlorophenoxy)ethyl]-2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indole as a pale yellow oil. HRMS (FAB)
calculated for C.sub.27H.sub.27CLN.sub.2O+H.sub.1 431.1890, found
431.1888.
EXAMPLE 44
3-benzyl-11-[2-(4-bromo-2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4-
]diazepino[1,7-a]indole
[0926] 47
[0927] Following the general procedure of Example 31 (Chart D, Step
3) and making non-critical variations but substituting phenol with
4-bromoguaiacol, gives 485 mg of a crude oil. This material is
purified by LC (230-400 silica gel) eluting with 10% ethyl acetate
in heptane to afford 224 mg of
3-benzyl-11-[2-(4-bromo-2-methoxyphenoxy)ethyl]-2,3,4,5--
tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a clear oil. HRMS
(FAB) calculated for C.sub.28H.sub.29BRN.sub.2O.sub.2+H.sub.1
505.1491, found 505.1486.
EXAMPLE 45
11-[2-(2-chlorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndole
[0928] 48
[0929] (Chart D, Step 4): A dry round bottom flask is charged with
a solution of
3-benzyl-11-[2-(2-chlorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H--
[1,4]diazepino[1,7-a]indole (176 mg, 0.41 mmol) in mehtylene
chloride (2 mL) and acetonitrile (5 mL). The addition of
2,2,2-trichloroformate (0.062 mL, 0.45 mmol) immediately turned the
solution to a fluorescent green color, which changes to purple
within 45 minutes. The reaction is concentrated in vacuo to give
247 mg of a crude purple oil. This material is purified by LC
(230-400 silica gel) eluting with 20% ethyl acetate in heptane to
afford 203 mg of 2,2,2-trichloroethyl 11-[2-(2-chlorophenoxy)e-
thyl]-1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indole-3-carboxylate
as a clear oil. The carboxylate is dissolved in glacial acetic acid
(3 mL). Zinc powder (300 mg) is added to the acidic solution,
changing the color from light to bright pink. After three hours of
stirring at ambient temperature, the reaction is filtered through
celite, and the zinc is thoroughly rinsed with water,
dichloromethane, 1N aq. NaOH, water and dichloromethane
sequentially. The filtrates are combined and neutralized with aq.
5N NaOH to pH 7 then diluted with aq. NaHCO.sub.3 and extracted
four times with dichloromethane. The extracts are combined, dried
over Na.sub.2SO.sub.4, filtered and concentrated to 151 mg of a
crude opaque oil. The crude is purified by LC (230-400 silica gel)
eluting with 1% NH.sub.4OH and 7% methanol in dichloromethane to
afford 92 mg (70%) of
11-[2-(2-chlorophenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indole as a an ivory solid. IR (drift) 1483, 1465, 1340, 1317,
1281, 1261, 1256, 1245, 1059, 1040, 913, 753, 749, 738, 688
cm.sup.-1.
EXAMPLE 46
11-[2-(4-bromo-2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indole
[0930] 49
[0931] Following the general procedure of Example 45 (Chart D, Step
4) and making non-critical variations but substituting with
3-benzyl-11-[2-(4-bromo-2-methoxyphenoxy)ethyl]-2,3,4,5-tetrahydro-1H-[1,-
4]diazepino[1,7-a]indole gives 153 mg of a crude opaque oil. This
material is purified by LC (230-400 silica gel) eluting with 5%
methanol in dichloromethane to afford 98 mg of
11-[2-(4-bromo-2-methoxyphenoxy)ethyl]-
-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as an ivory
foam. IR (drift) 2926, 1585, 1500, 1467, 1372, 1323, 1249, 1224,
1179, 1134, 1024, 1014, 838, 799, 739 cm.sup.-1.
EXAMPLE 47
2-phenoxy-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-eth-
anone
[0932] 50
[0933] (Chart E, Step 1): A dry round bottom flask is charged with
AlCl.sub.3 (66.7 mg, 0.5 mmol) and dichloromethane (4 mL) to make a
heterogeneous solution. Dropwise addition of bromo-acetylbromide
(0.044 mL, 0.5 mmol) turns the reaction into a homogeneous orange
solution. After 30 minutes of stirring at ambient temperature, a
solution of
2,2,2-trifluoro-1-(1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indol-3-yl)-
-1-ethanone (141.1 mg, 0.5 mmol) in dichloromethane (2 mL) is added
dropwise and stirred for three days. The reaction turns dark purple
within the first 4 hours of stirring. The reaction is poured in a
sat. aq. NaHCO.sub.3 solution and extracted three times with
dichloromethane. The combined organics are combined, dried with
MgSO.sub.4, filtered and concentrated to 192 mg of a purple foam.
The crude is purified by LC (230-400 silica gel) eluting with 10%
ethyl acetate and 20% dichloromethane in heptane to afford 120 mg
of 1-[11-(2-bromoacetyl)-1,2,-
4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indol-3-yl]-2,2,2-trifluoro-1-ethan-
one as a white foam.
[0934] (Chart E, Step 2): To a dry round bottom charged with a
heterogeneous mixture of K.sub.2CO.sub.3 (40.77 mg, 0.30 mmol) and
phenol (27.8 mg, 0.30 mmol) in DMF (1.5 mL) is added a solution of
1-[11-(2-bromoacetyl)-1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indol-3--
yl]-2,2,2-trifluoro-1-ethanone in DMF (1.5 mL). After stirring at
ambient temperature for 18 hours, aq. 1N NaOH (1 mL) is added at
once to deprotect the indole in situ. The mixture is stirred for an
hour then partitioned between water and ethyl acetate, the aqueous
layer is extracted two more times with ethyl acetate. The organics
are combined, dried with MgSO.sub.4, filtered and concentrated to
95 mg of a crude oil. The crude is purified by LC (230-400 silica
gel) eluting with 0.5% NH.sub.4OH and 3.5% methanol in
dichloromethane to afford 69 mg of
2-phenoxy-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-et-
hanone as a white solid. IR (drift) 1662, 1598, 1516, 1495, 1458,
1443, 1420, 1345, 1244, 1198, 1191, 1052, 975, 746, 688
cm.sup.-1.
EXAMPLE 48
2-(2-methoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-1-
1-yl)-1-ethanone
[0935] 51
[0936] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-methoxyphenol, gives 250 mg of a crude oil. This material is
purified by LC (230-400 silica gel) eluting with 0.5% NH.sub.4OH
and 3.5% methanol in dichloromethane to afford 172 mg of
2-(2-methoxyphenoxy)-1-(2,3,4,5-te-
trahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanone as an
ivory solid. IR (drift) 1662, 1515, 1505, 1456, 1442, 1422, 1345,
1253, 1225, 1190, 1130, 1032, 975, 758, 737 cm.sup.-1.
EXAMPLE 49
2-4-bromo-2-methoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-11-yl)-1-ethanone
[0937] 52
[0938] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
4-bromoguaicol, gives 300 mg of a crude oil. This material is
purified by LC (230-400 silica gel) eluting with 0.5% NH.sub.4OH
and 3.5% methanol in dichloromethane to afford 243 mg of
2-(4-bromo-2-methoxyphenoxy)-1-(2,3,4-
,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanone as an
ivory solid. IR (drift) 1659, 1514, 1501, 1465, 1422, 1343, 1250,
1222, 1189, 1137, 1031, 975, 836, 794, 736 cm.sup.-1.
EXAMPLE 50
2-(4-methoxyanilino)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-1-
1-yl)-1-ethanone dihydrochloride
[0939] 53
[0940] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
p-methoxyaniline, gives 350 mg of a crude oil. This material is
purified by LC (230-400 silica gel) eluting with 0.5% NH.sub.4OH
and 3.5% methanol in dichloromethane to afford 169 mg of
2-(4-methoxyanilino)-1-(2,3,4,5-te-
trahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanone as a
yellow oil. This material is dissolved in ethyl acetate (15 mL) and
treated with a 0.61 M hydrochloric acid solution in methanol (1 mL)
to afford 116 mg of
2-(4-methoxyanilino)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol--
11-yl)-1-ethanone dihydrochloride as a white solid. IR (drift)
2936, 2792, 2767, 2747, 2713, 2684, 2653, 2640, 2595, 2581; 1641,
1512, 1463, 1419, 1257 cm.sup.-1.
EXAMPLE 51
tert-butyl
1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indole-3-carboxylate
[0941] 54
[0942] A solution of
2,3,4,5-Tetrahydro-1H-[1,4]diazepino[1,7-a]indole (2.40 g, 12.9
mmol) in dichloromethane (64 mL) is treated with di-tertbutyl
dicarbonate (3.37 g, 15.5 mmol) quickly evolving carbon dioxide.
After 18 hrs, the reaction mixture is concentrated under reduced
pressure to give 4.54 g of a crude solid. This material is purified
by LC (biotage 90 g column) eluting with 10:10:80
dichloromethane/ethyl acetate/heptane to afford 3.79 g of
tert-butyl 1,2,4,5-tetrahydro-3H-[1,4-
]diazepino[1,7-a]indole-3-carboxylate as a white solid, mp
129-132.degree. C. IR (drift) 2971, 2934, 1686, 1458, 1406, 1366,
1333, 1255, 1242, 1221, 1195, 1179, 949, 798, 734 cm.sup.-1.
EXAMPLE 52
11-[(E)-2-nitroethenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0943] 55
[0944] A solution of tert-butyl
11-formyl-1,2,4,5-tetrahydro-3H-[1,4]diaze-
pino[1,7-a]indole-3-carboxylate (314 gm, 1.0 mmol) in nitromethane
(1 mL) is treated with ammonium acetate (23 mg, 0.3 mmol) and
heated to reflux. After 18 hrs, the resulting dark brown solution
is cooled to rt, diluted with water (15 mL), and extracted twice
with dichloromethane (20 mL). The combined organics are washed with
brine (15 mL), dried over MgSO.sub.4, filtered, and concentrated to
give a crude solid. This material is purified by LC (230-400 silica
gel) eluting with 10:40:50 ethyl acetate/dichloromethane/heptane to
afford 240 mg of tert-butyl
11-[(E)-2-nitroethenyl]-1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indole-
-3-carboxylate as a bright yellow solid, mp 227-230.degree. C. IR
(drift) 1692, 1621, 1493, 1472, 1419, 1323, 1310, 1302, 1291, 1277,
1259, 1248, 1198, 1164, 751 cm.sup.-1; MS (EI) m/z 357
(M.sup.+).
[0945] A solution of tert-butyl
11-[(E)-2-nitroethenyl]-1,2,4,5-tetrahydro-
-3H-[1,4]diazepino[1,7-a]indole-3-carboxylate (396 mg, 1.1 mmol) in
methanol (10 mL) is cooled to 0.degree. C. and treated with a
saturated solution of hydrochloric acid in methanol (5 mL). After 3
hrs, the volatiles are removed under reduced pressure, diluted with
5M sodium hydroxide (15 mL), and extracted twice with
dichloromethane (20 mL). The combined organics are washed once with
brine (15 mL), dried over MgSO.sub.4, filtered, and concentrated to
give a yellow solid. This material is recrystallized from
dichloromethane/ethyl acetate to afford 209 mg of
11-[(E)-2-nitroethenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indole as a light yellow solid, mp 225-226.degree. C. IR
(drift) 1603, 1488, 1469, 1318, 1301, 1281, 1257, 1251, 1206,1187,
1062, 976, 946, 763, 745 cm.sup.-1; OAMS supporting ions at: ESI+
258.1.
EXAMPLE 53
3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
[0946] 56
[0947] A solution of
2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole hydrochloride
(557 mg, 2.5 mmol) in dichloromethane (25 mL) is treated with
triethylamine (0.77 mL, 5.5 mmol) followed by cooling to 0.degree.
C. The clear golden solution is treated with the trifluoroacetic
acid anhydride (0.39 mL, 2.8 mmol) with a smoke/haze forming. After
15 min, the reaction mixture is diluted with additional
dichloromethane (25 mL), washed once with water (25 mL), once with
brine (25 mL), dried over MgSO.sub.4, filtered, and concentrated to
give a crude solid. This material is purified by LC (230-400 silica
gel) eluting with 25:5:70 dichloromethane/ethyl acetate/heptane to
afford 607 mg of
2,2,2-trifluoro-1-(1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indol-3-yl)-
-1-ethanone as a white solid. IR (drift) 1691, 1464, 1449, 1368,
1292, 1203, 1196, 1171, 1161, 1139, 970, 782, 749, 743, 651
cm.sup.-1; MS (EI) m/z 282 (M.sup.+).
EXAMPLE 54
2-bromo-1-[3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-11-yl]ethanone
[0948] 57
[0949] (Chart E, Step 1): A dry round bottom flask is charged with
AlCl.sub.3 (66.7 mg, 0.5 mmol) and dichloromethane (4 mL) to make a
heterogeneous solution. Dropwise addition of bromo-acetylbromide
(0.044 mL, 0.5 mmol) turns the reaction into a homogeneous orange
solution. After 30 minutes of stirring at ambient temperature, a
solution of
2,2,2-trifluoro-1-(1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indol-3-yl)-
-1-ethanone (141.1 mg, 0.5 mmol) in dichloromethane (2 mL) is added
dropwise and stirred for three days. The reaction turns dark purple
within the first 4 hours of stirring. The reaction is poured in a
sat. aq. NaHCO.sub.3 solution and extracted three times with
dichloromethane. The combined organics are combined, dried with
MgSO.sub.4, filtered and concentrated to 192 mg of a purple foam.
The crude is purified by LC (230-400 silica gel) eluting with 10%
ethyl acetate and 20% dichloromethane in heptane to afford 120 mg
of 1-[11-(2-bromoacetyl)-1,2,-
4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indol-3-yl]-2,2,2-trifluoro-1-ethan-
one as a white foam.
EXAMPLE 55
N-(1H-benzimidazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a]indol-11-yl)acetamide
[0950] 58
[0951] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 1H-benzimidazol-2-ylamine gives
N-(1H-benzimidazol-2-yl)-2-oxo-2-(2,3,4,5-
-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.21H.sub.19N.sub.5O.sub.2 m/z 373.9
(M+H).sup.+.
EXAMPLE 56
N-(4-methyl-1,3-thiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indol-11-yl)acetamide
[0952] 59
[0953] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-methyl-1,3-thiazol-2-amine gives
N-(4-methyl-1,3-thiazol-2-yl)-2-oxo-2--
(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide;
MS (ESI+) for C.sub.18H.sub.18N.sub.4O.sub.2S m/z 355.2
(M+H).sup.+.
EXAMPLE 57
N-[4-(4-morpholinyl)phenyl]-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indol-11-yl)acetamide
[0954] 60
[0955] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-(4-morpholinyl)phenylamine gives
N-[4-(4-morpholinyl)phenyl]-2-oxo-2-(2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.24H.sub.26N.sub.4O.sub.3 m/z 419.1
(M+H).sup.+.
EXAMPLE 58
2-oxo-N-phenyl-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)a-
cetamide
[0956] 61
[0957] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with aniline gives
2-oxo-N-phenyl-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol--
11-yl)acetamide; MS (ESI+) for C.sub.20H.sub.19N.sub.3O.sub.2 m/z
334.2 (M+H).sup.+.
EXAMPLE 59
N-(2-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)acetamide
[0958] 62
[0959] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 2-methoxyaniline gives
N-(2-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.21H.sub.21N.sub.3O.sub.3 m/z 364.1 (M+H).sup.+.
EXAMPLE 60
N-(4-methoxy-2-methylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indol-11-yl)acetamide
[0960] 63
[0961] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-methoxy-2-methylaniline gives
N-(4-methoxy-2-methylphenyl)-2-oxo-2-(2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.22H.sub.23N.sub.3O.sub.3 m/z 378.2
(M+H).sup.+.
EXAMPLE 61
N-(3-cyanophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)acetamide
[0962] 64
[0963] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-cyanophenylamine gives
N-(3-cyanophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.21H.sub.18N.sub.4O.sub.2 m/z 359.1 (M+H).sup.+.
EXAMPLE 62
N-(3,5-dimethylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indol-11-yl)acetamide
[0964] 65
[0965] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3,5-dimethylphenylamine gives
N-(3,5-dimethylphenyl)-2-oxo-2-(2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+)
for C.sub.22H.sub.23N.sub.3O.sub.2 m/z 362.2 (M+H).sup.+.
EXAMPLE 63
N-(4-chlorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-11-yl)acetamide
[0966] 66
[0967] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-chlorophenylamine gives
N-(4-chlorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.20H.sub.18ClN.sub.3O.sub.2 m/z 368.1 (M+H).sup.+.
EXAMPLE 64
N-(3-chlorophenyl)-N-methyl-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indol-11-yl)acetamide
[0968] 67
[0969] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-chlorophenylamine gives
N-(3-chlorophenyl)-N-methyl-2-oxo-2-(2,3,4,5-te-
trahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+)
for C.sub.21H.sub.20ClN.sub.3O.sub.2 m/z 382.1 (M+H).sup.+.
EXAMPLE 65
N-(6-chloro-2-pyrazinyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a]indol-11-yl)acetamide
[0970] 68
[0971] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 6-chloro-2-pyrazinylamine gives
N-(6-chloro-2-pyrazinyl)-2-oxo-2-(2,3,4,5-
-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.18H.sub.16ClN.sub.5O.sub.2 m/z 369.9
(M+H).sup.+.
EXAMPLE 66
N-mesityl-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-
acetamide
[0972] 69
[0973] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with mesitylamine gives
N-mesityl-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.23H.sub.25N.sub.3O.sub.- 2 m/z 376.2 (M+H).sup.+.
EXAMPLE 67
N-(2,4-difluorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indol-11-yl)acetamide
[0974] 70
[0975] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 2,4-difluorophenylamine gives
N-(2,4-difluorophenyl)-2-oxo-2-(2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+)
for C.sub.20H.sub.17F.sub.2N.sub.3O.sub.2 m/z 370.1
(M+H).sup.+.
EXAMPLE 68
N-methyl-2-oxo-N-phenyl-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)acetamide
[0976] 71
[0977] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with N-methylaniline gives
N-methyl-2-oxo-N-phenyl-2-(2,3,4,5-tetrahydro-1H-[1-
,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.21H.sub.21N.sub.3O.sub.2 m/z 348.2 (M+H).sup.+.
EXAMPLE 69
N-(2-ethylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)acetamide
[0978] 72
[0979] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 2-ethylphenylamine gives
N-(2-ethylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.22H.sub.23N.sub.3O.sub.2 m/z 362.1 (M+H).sup.+.
EXAMPLE 70
N-(4-chlorophenyl)-N-methyl-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indol-11-yl)acetamide
[0980] 73
[0981] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-chlorophenylamine gives
N-(4-chlorophenyl)-N-methyl-2-oxo-2-(2,3,4,5-te-
trahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+)
for C.sub.21H.sub.20ClN.sub.3O.sub.2 m/z 382.0 (M+H).sup.+.
EXAMPLE 71
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-N-(5,6,7,-
8-tetrahydro-1-naphthalenyl)acetamide
[0982] 74
[0983] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 5,6,7,8-tetrahydro-1-naphthalenylamine gives
2-oxo-2-(2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indol-11-yl)-N-(5,6,7,8-tetrahydro-1-naphthalenyl)-
acetamide; MS (ESI+) for C.sub.24H.sub.25N.sub.3O.sub.2 m/z 388.0
(M+H).sup.+.
EXAMPLE 72
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-N-(1,3,4--
thiadiazol-2-yl)acetamide
[0984] 75
[0985] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 1,3,4-thiadiazol-2-ylamine gives
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indol-11-yl)-N-(1,3,4-thiadiazol-2-yl)acetamide; MS
(ESI+) for C.sub.16H.sub.15N.sub.5O.sub.2S m/z 349.1
(M+H).sup.+.
EXAMPLE 73
2-oxo-N-(2-pyrazinyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol--
11-yl)acetamide
[0986] 76
[0987] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 2-pyrazinylamine gives
2-oxo-N-(2-pyrazinyl)-2-(2,3,4,5-tetrahydro-1H-[1,-
4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.18H.sub.17N.sub.5O.sub.2 m/z 336.0 (M+H).sup.+.
EXAMPLE 74
2-oxo-N-(2-pyridinyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol--
11-yl)acetamide
[0988] 77
[0989] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 2-pyridinylamine gives
2-oxo-N-(2-pyridinyl)-2-(2,3,4,5-tetrahydro-1H-[1,-
4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.19H.sub.18N.sub.4O.sub.2 m/z 335.0 (M+H).sup.+.
EXAMPLE 75
2-oxo-N-(3-pyridinyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol--
11-yl)acetamide
[0990] 78
[0991] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-pyridinylamine gives
2-oxo-N-(3-pyridinyl)-2-(2,3,4,5-tetrahydro-1H-[1,-
4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.19H.sub.18N.sub.4O.sub.2 m/z 335.0 (M+H).sup.+.
EXAMPLE 76
2-oxo-N-(4-pyridinyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol--
11-yl)acetamide
[0992] 79
[0993] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-pyridinylamine gives
2-oxo-N-(4-pyridinyl)-2-(2,3,4,5-tetrahydro-1H-[1,-
4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.19H.sub.18N.sub.4O.sub.2 m/z 335.0 (M+H).sup.+.
EXAMPLE 77
N-(2-cyanophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)acetamide
[0994] 80
[0995] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 2-cyanophenylamine gives
N-(2-cyanophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.21H.sub.18N.sub.4O.sub.2 m/z 358.9 (M+H).sup.+.
EXAMPLE 78
N-(2-fluoro-5-methylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indol-11-yl)acetamide
[0996] 81
[0997] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 2-fluoro-5-methylphenylamine gives
N-(2-fluoro-5-methylphenyl)-2-oxo-2-(2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.21H.sub.20FN.sub.3O.sub.2 m/z 366.0
(M+H).sup.+.
EXAMPLE 79
N-(2,3-dichlorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indol-11-yl)acetamide
[0998] 82
[0999] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 2,3-dichlorophenylamine gives
N-(2,3-dichlorophenyl)-2-oxo-2-(2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+)
for C.sub.20H.sub.17Cl.sub.2N.sub.3O.sub.2 m/z 401.8
(M+H).sup.+.
EXAMPLE 80
N-(2,6-dichlorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indol-11-yl)acetamide
[1000] 83
[1001] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 2,6-dichlorophenylamine gives
N-(2,6-dichlorophenyl)-2-oxo-2-(2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+)
for C.sub.20H.sub.17Cl.sub.2N.sub.3O.sub.2 m/z 401.8
(M+H).sup.+.
EXAMPLE 81
N-(2,3-dimethylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indol-11-yl)acetamide
[1002] 84
[1003] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 2,3-dimethylphenylamine gives
N-(2,3-dimethylphenyl)-2-oxo-2-(2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+)
for C.sub.22H.sub.23N.sub.3O.sub.2 m/z 362.0 (M+H).sup.+.
EXAMPLE 82
N-(2,6-dimethylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indol-11-yl)acetamide
[1004] 85
[1005] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 2,6-dimethylphenylamine gives
N-(2,6-dimethylphenyl)-2-oxo-2-(2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+)
for C.sub.22H.sub.23N.sub.3O.sub.2 m/z 362.0 (M+H).sup.+.
EXAMPLE 83
N-(3,5-difluorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indol-11-yl)acetamide
[1006] 86
[1007] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3,5-difluorophenylamine gives
N-(3,5-difluorophenyl)-2-oxo-2-(2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+)
for C.sub.20H.sub.17F.sub.2N.sub.3O.sub.2 m/z 370.0
(M+H).sup.+.
EXAMPLE 84
N-(3-chlorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-11-yl)acetamide
[1008] 87
[1009] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-chlorophenylamine gives
N-(3-chlorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.20H.sub.18ClN.sub.3O.sub.2 m/z 367.9 (M+H).sup.+.
EXAMPLE 85
N-(3-chloro-4-methylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indol-11-yl)acetamide
[1010] 88
[1011] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-chloro-4-methylphenylamine gives
N-(3-chloro-4-methylphenyl)-2-oxo-2-(2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.21H.sub.20ClN.sub.3O.sub.2 m/z 381.9
(M+H).sup.+.
EXAMPLE 86
N-(3-nitrophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)acetamide
[1012] 89
[1013] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-nitrophenylamine gives
N-(3-nitrophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.20H.sub.18N.sub.4O.sub.4 m/z 378.9 (M+H).sup.+.
EXAMPLE 87
N-(3-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)acetamide
[1014] 90
[1015] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-methoxyphenylamine gives
N-(3-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indol-1-yl)acetamide; MS (ESI+) for
C.sub.21H.sub.21N.sub.3O.sub.3 m/z 363.9 (M+H).sup.+.
EXAMPLE 88
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-N-[3-(tri-
fluoromethyl)phenyl]acetamide
[1016] 91
[1017] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-(trifluoromethyl)phenylamine gives
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indol-11-yl)-N-[3-(trifluoromethyl)phenyl]acetamide;
MS (ESI+) for C.sub.21H.sub.18F.sub.3N.sub.3O.sub.2 m/z 401.9
(M+H).sup.+.
EXAMPLE 89
N-(3-methylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-11-yl)acetamide
[1018] 92
[1019] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-methylphenylamine gives
N-(3-methylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.21H.sub.21N.sub.3O.sub.2 m/z 348.0 (M+H).sup.+.
EXAMPLE 90
N-(4-cyanophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)acetamide
[1020] 93
[1021] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-cyanophenylamine gives
N-(4-cyanophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.21H.sub.18N.sub.4O.sub.2 m/z 358.9 (M+H).sup.+.
EXAMPLE 91
N-(2-bromo-4-methylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indol-11-yl)acetamide
[1022] 94
[1023] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 2-bromo-4-methylphenylamine gives
N-(2-bromo-4-methylphenyl)-2-oxo-2-(2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.21H.sub.20BrN.sub.3O.sub.2 m/z 427.7
(M+H).sup.+.
EXAMPLE 92
N-(4-nitrophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)acetamide
[1024] 95
[1025] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-nitrophenylamine gives
N-(4-nitrophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.20H.sub.18N.sub.4O.sub.4 m/z 379.0 (M+H).sup.+.
EXAMPLE 93
2-oxo-N-(4-phenoxyphenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)acetamide
[1026] 96
[1027] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-phenoxyphenylamine gives
2-oxo-N-(4-phenoxyphenyl)-2-(2,3,4,5-tetrahydr-
o-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.26H.sub.23N.sub.3O.sub.3 m/z 425.9 (M+H).sup.+.
EXAMPLE 94
N-[1,1'-biphenyl]-4-yl-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indol-11-yl)acetamide
[1028] 97
[1029] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with [1,1'-biphenyl]-4-ylamine gives
N-[1,1'-biphenyl]-4-yl-2-oxo-2-(2,3,4,5-t-
etrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+)
for C.sub.26H.sub.23N.sub.3O.sub.2 m/z 409.9 (M+H).sup.+.
EXAMPLE 95
N-(4-isopropylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-1-yl)acetamide
[1030] 98
[1031] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-isopropylphenylamine gives
N-(4-isopropylphenyl)-2-oxo-2-(2,3,4,5-tetra-
hydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.23H.sub.25N.sub.3O.sub.2 m/z 376.0 (M+H).sup.+.
EXAMPLE 96
N-(4-chloro-2-fluorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indol-11-yl)acetamide
[1032] 99
[1033] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-chloro-2-fluorophenylamine gives
N-(4-chloro-2-fluorophenyl)-2-oxo-2-(2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.20H.sub.17ClFN.sub.3O.sub.2 m/z 385.9
(M+H).sup.+.
EXAMPLE 97
N-(2-cyano-3-fluorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indol-11-yl)acetamide
[1034] 100
[1035] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 2-cyano-3-fluorophenylamine gives
N-(2-cyano-3-fluorophenyl)-2-oxo-2-(2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.21H.sub.17FN.sub.4O.sub.2 m/z 376.9
(M+H).sup.+.
EXAMPLE 98
N-(4-chlorophenyl)-N-ethyl-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indol-11-yl)acetamide
[1036] 101
[1037] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with N-(4-chlorophenyl)-N-ethylamine gives
N-(4-chlorophenyl)-N-ethyl-2-oxo-2--
(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide;
MS (ESI+) for C.sub.22H.sub.22ClN.sub.3O.sub.2 m/z 395.9
(M+H).sup.+.
EXAMPLE 99
N-(4-bromo-2-chloro-6-methylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indol-11-yl)acetamide
[1038] 102
[1039] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-bromo-2-chloro-6-methylphenylamine gives
N-(4-bromo-2-chloro-6-methylph-
enyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acet-
amide; MS (ESI+) for C.sub.21H.sub.19BrClN.sub.3O.sub.2 m/z 461.7
(M+H).sup.+.
EXAMPLE 100
N-(3-chloro-4-iodophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indol-11-yl)acetamide
[1040] 103
[1041] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-chloro-4-iodophenylamine gives
N-(3-chloro-4-iodophenyl)-2-oxo-2-(2,3,4-
,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.20H.sub.17ClN.sub.3O.sub.2 m/z 493.8
(M+H).sup.+.
EXAMPLE 101
N-ethyl-N-(2-fluorophenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indol-11-yl)acetamide
[1042] 104
[1043] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with N-ethyl-N-(2-fluorophenyl)amine gives
N-ethyl-N-(2-fluorophenyl)-2-oxo-2--
(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide;
MS (ESI+) for C.sub.22H.sub.22FN.sub.3O.sub.2 m/z 380.0
(M+H).sup.+.
EXAMPLE 102
N-(3-benzylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-11-yl)acetamide
[1044] 105
[1045] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-benzylphenylamine gives
N-(3-benzylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.27H.sub.25N.sub.3O.sub.2 m/z 424.0 (M+H).sup.+.
EXAMPLE 103
N-(4-methylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-1-yl)acetamide
[1046] 106
[1047] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-methylphenylamine gives
N-(4-methylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.21H.sub.21N.sub.3O.sub.2 m/z 348.0 (M+H).sup.+.
EXAMPLE 104
N-(3-ethylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)acetamide
[1048] 107
[1049] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-ethylphenylamine gives
N-(3-ethylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.22H.sub.23N.sub.3O.sub.2 m/z 362.0 (M+H).sup.+.
EXAMPLE 105
N-(1-naphthyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-1-
1-yl)acetamide
[1050] 108
[1051] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 1-naphthylamine gives
N-(1-naphthyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indol-11-yl)acetamide; MS (ESI+) for
C.sub.24H.sub.21N.sub.3O.sub.2 m/z 384.0 (M+H).sup.+.
EXAMPLE 106
2-oxo-N-(8-quinolinyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
-11-yl)acetamide trifluoroacetate
[1052] 109
[1053] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 8-quinolinylamine gives
2-oxo-N-(8-quinolinyl)-2-(2,3,4,5-tetrahydro-1H-[-
1,4]diazepino[1,7-a]indol-11-yl)acetamide trifluoroacetate; MS
(ESI+) for C.sub.23H.sub.20N.sub.4O.sub.2 m/z 385.2
(M+H).sup.+.
EXAMPLE 107
N-(5-methyl-1,3-thiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indol-11-yl)acetamide
[1054] 110
[1055] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 5-methyl-1,3-thiazol-2-ylamine gives
N-(5-methyl-1,3-thiazol-2-yl)-2-oxo--
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide;
MS (ESI+) for C.sub.18H.sub.18N.sub.4O.sub.2S m/z 355.1
(M+H).sup.+.
EXAMPLE 108
N-(3-methyl-5-isothiazolyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indol-11-yl)acetamide trifluoroacetate
[1056] 111
[1057] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-methyl-5-isothiazolylamine gives
N-(3-methyl-5-isothiazolyl)-2-oxo-2-(2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide
trifluoroacetate; MS (ESI+) for C.sub.18H.sub.18N.sub.4O.sub.2S m/z
355.1 (M+H).sup.+.
EXAMPLE 109
N-(3-methyl-5-isoxazolyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indol-11-yl)acetamide
[1058] 112
[1059] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-methyl-5-isoxazolylamine gives
N-(3-methyl-5-isoxazolyl)-2-oxo-2-(2,3,4-
,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.18H.sub.18N.sub.4O.sub.3 m/z 339.1
(M+H).sup.+.
EXAMPLE 110
N-(1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indol-11-yl)acetamide
[1060] 113
[1061] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 1,3-benzothiazol-2-ylamine gives
N-(1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4-
,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.21H.sub.18N.sub.4O.sub.2S m/z 391.1
(M+H).sup.+.
EXAMPLE 111
N-(3-chloro-2-methylphenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-11-yl)acetamide
[1062] 114
[1063] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-chloro-2-methylphenylamine gives
N-(3-chloro-2-methylphenyl)-2-(2,3,4,5-
-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.21H.sub.22ClN.sub.3O m/z 368.2 (M+H).sup.+.
EXAMPLE 112
N-(3-chloro-2-methylphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indol-11-yl)acetamide
[1064] 115
[1065] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 3-chloro-2-methylphenylamine gives
N-(3-chloro-2-methylphenyl)-2-oxo-2-(2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.21 H.sub.20 Cl N.sub.3O.sub.2 m/z 382.1
(M+H).sup.+.
EXAMPLE 113
N-[2-methyl-3-(trifluoromethyl)phenyl]-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4-
]diazepino[1,7-a]indol-11-yl)acetamide
[1066] 116
[1067] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 2-methyl-3-(trifluoromethyl)phenylamine gives
N-[2-methyl-3-(trifluoromet-
hyl)phenyl]-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-y-
l)acetamide; MS (ESI+) for C.sub.22H.sub.20F.sub.3N.sub.3O.sub.2
m/z 416.0 (M+H).sup.+.
EXAMPLE 114
N-(4-bromo-2-chloro-6-methylphenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indol-11-yl)acetamide
[1068] 117
[1069] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-bromo-2-chloro-6-methylphenylamine gives
N-(4-bromo-2-chloro-6-methylph-
enyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide;
MS (ESI+) for C.sub.21H.sub.21BrClN.sub.3O m/z 447.8
(M+H).sup.+.
EXAMPLE 115
N-(1-ethyl-1H-pyrazol-5-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indol-11-yl)acetamide
[1070] 118
[1071] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 1-ethyl-1H-pyrazol-5-ylamine gives
N-(1-ethyl-1H-pyrazol-5-yl)-2-oxo-2-(2-
,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.19H.sub.21N.sub.5O.sub.2 nm/z 352.2
(M+H).sup.+.
EXAMPLE 116
2-oxo-N-(4-phenyl-1,3-thiazol-2-yl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepin-
o[1,7-a]indol-11-yl)acetamide
[1072] 119
[1073] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-phenyl-1,3-thiazol-2-ylamine gives
2-oxo-N-(4-phenyl-1,3-thiazol-2-yl)--
2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide;
MS (ESI+) for C.sub.23H.sub.20N.sub.4O.sub.2S m/z 417.0
(M+H).sup.+.
EXAMPLE 117
N-(5-methyl-3-isoxazolyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,-
7-a]indol-11-yl)acetamide
[1074] 120
[1075] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 5-methyl-3-isoxazolylamine gives
N-(5-methyl-3-isoxazolyl)-2-oxo-2-(2,3,4-
,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide; MS
(ESI+) for C.sub.18H.sub.18N.sub.4O.sub.3 m/z 339.1
(M+H).sup.+.
EXAMPLE 118
1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-2-(5,6,7,8-tetr-
ahydro-1-naphthalenyloxy)ethanone
[1076] 121
[1077] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
5,6,7,8-tetrahydro-1-naphthalenol gives
1-(2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indol-11-yl)-2-(5,6,7,8-tetrahydro-1-naphthalenyloxy)ethanone-
; MS (ESI+) for C.sub.24H.sub.26N.sub.2O.sub.2 m/z 375.1
(M+H).sup.+.
EXAMPLE 119
2-(2-bromophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11--
yl)ethanone
[1078] 122
[1079] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-bromophenol gives
2-(2-bromophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)ethanone; MS (ESI+) for C.sub.20H.sub.19BrN.sub.2O.sub.2
m/z 400.9 (M+H).sup.+.
EXAMPLE 120
2-(2-isopropylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
-11-yl)ethanone
[1080] 123
[1081] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-isopropylphenol gives
2-(2-isopropylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[-
1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.23H.sub.26N.sub.2O.sub.2 m/z 363.1 (M+H).sup.+.
EXAMPLE 121
2-(2-ethylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11--
yl)ethanone
[1082] 124
[1083] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-ethylphenol gives
2-(2-ethylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)ethanone; MS (ESI+) for C.sub.22H.sub.24N.sub.2O.sub.2
m/z 349.1 (M+H).sup.+.
EXAMPLE 122
2-(3-bromophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11--
yl)ethanone
[1084] 125
[1085] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
3-bromophenol gives
2-(3-bromophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)ethanone; MS (ESI+) for C.sub.20H.sub.19BrN.sub.2O.sub.2
m/z 400.9 (M+H).sup.+.
EXAMPLE 123
2-(3-fluorophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-
-yl)ethanone
[1086] 126
[1087] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
3-fluorophenol gives
2-(3-fluorophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.20H.sub.19FN.sub.2- O.sub.2 m/z 339.1 (M+H).sup.+.
EXAMPLE 124
2-(3-methoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-1-
1-yl)ethanone
[1088] 127
[1089] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
3-methoxyphenol gives
2-(3-methoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.21H.sub.22N.sub.2O.sub.3 m/z 351.1 (M+H).sup.+.
EXAMPLE 125
1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-2-[3-(trifluoro-
methyl)phenoxy]ethanone
[1090] 128
[1091] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
3-(trifluoromethyl)phenol gives
1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1-
,7-a]indol-11-yl)-2-[3-(trifluoromethyl)phenoxy]ethanone; MS (ESI+)
for C.sub.21H.sub.19F.sub.3N.sub.2O.sub.2 m/z 389.0
(M+H).sup.+.
EXAMPLE 126
2-(3-isopropylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
-11-yl)ethanone
[1092] 129
[1093] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
3-isopropylphenol gives
2-(3-isopropylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[-
1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.23H.sub.26N.sub.2O.sub.2 m/z 363.1 (M+H).sup.+.
EXAMPLE 127
2-(3-ethylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11--
yl)ethanone
[1094] 130
[1095] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
3-ethylphenol gives
2-(3-ethylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)ethanone; MS (ESI+) for C.sub.22H.sub.24N.sub.2O.sub.2
m/z 349.2 (M+H).sup.+.
EXAMPLE 128
2-(4-fluorophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-
-yl)ethanone
[1096] 131
[1097] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
4-fluorophenol gives
2-(4-fluorophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.20H.sub.19FN.sub.2- O.sub.2 m/z 339.1 (M+H).sup.+.
EXAMPLE 129
2-(4-iodophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-y-
l)ethanone
[1098] 132
[1099] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
4-iodophenol gives
2-(4-iodophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-11-yl)ethanone; MS (ESI+) for C.sub.20H.sub.19IN.sub.2O.sub.2
m/z 446.8 (M+H).sup.+.
EXAMPLE 130
2-[4-(benzyloxy)phenoxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-11-yl)ethanone
[1100] 133
[1101] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
4-(benzyloxy)phenol gives
2-[4-(benzyloxy)phenoxy]-1-(2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.27H.sub.26N.sub.2O.sub.3 m/z 427.0 (M+H).sup.+.
EXAMPLE 131
2-(4-butoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-
-yl)ethanone
[1102] 134
[1103] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
4-butoxyphenol gives
2-(4-butoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.24H.sub.28N.sub.2O- .sub.3 m/z 393.0 (M+H).sup.+.
EXAMPLE 132
2-(3-tert-butylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)ethanone
[1104] 135
[1105] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
3-tert-butylphenol gives
2-(3-tert-butylphenoxy)-1-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.24H.sub.28N.sub.2O.sub.2 m/z 377.0 (M+H).sup.+.
EXAMPLE 133
2-(4-ethylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11--
yl)ethanone
[1106] 136
[1107] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
4-ethylphenol gives
2-(4-ethylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)ethanone; MS (ESI+) for C.sub.22H.sub.24N.sub.2O.sub.2
m/z 349.1 (M+H).sup.+.
EXAMPLE 134
2-(1-naphthyloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-y-
l)ethanone
[1108] 137
[1109] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
1-naphthol gives
2-(1-naphthyloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-11-yl)ethanone; MS (ESI+) for C.sub.24H.sub.22N.sub.2O.sub.2 m/z
371.0 (M+H).sup.+.
EXAMPLE 135
2-[(4-chloro-1-naphthyl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a-
]indol-11-yl)ethanone
[1110] 138
[1111] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
4-chloro-1-naphthol gives
2-[(4-chloro-1-naphthyl)oxy]-1-(2,3,4,5-tetrahy-
dro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.24H.sub.21ClN.sub.2O.sub.2 m/z 405.0 (M+H).sup.+.
EXAMPLE 136
2-(2-naphthyloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-y-
l)ethanone
[1112] 139
[1113] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-naphthol gives
2-(2-naphthyloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-11-yl)ethanone; MS (ESI+) for C.sub.24H.sub.22N.sub.2O.sub.2 m/z
371.1 (M+H).sup.+.
EXAMPLE 137
2-(1,3-benzodioxol-5-yloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-11-yl)ethanone
[1114] 140
[1115] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
1,3-benzodioxol-5-ol gives
2-(1,3-benzodioxol-5-yloxy)-1-(2,3,4,5-tetrahy-
dro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.21H.sub.20N.sub.2O.sub.4 m/z 365.1 (M+H).sup.+.
EXAMPLE 138
2-(4-quinolinyloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-
-yl)ethanone
[1116] 141
[1117] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
4-quinolinol gives
2-(4-quinolinyloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndol-11-yl)ethanone; MS (ESI+) for C.sub.23H.sub.21N.sub.3O.sub.2
m/z 372.2 (M+H).sup.+.
EXAMPLE 139
2-(8-quinolinyloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-
-yl)ethanone
[1118] 142
[1119] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
8-quinolinol gives
2-(8-quinolinyloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]i-
ndol-11-yl)ethanone; MS (ESI+) for C.sub.23H.sub.21N.sub.3O.sub.2
m/z 372.2 (M+H).sup.+.
EXAMPLE 140
2-(5-isoquinolinyloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
-11-yl)ethanone
[1120] 143
[1121] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
5-isoquinolinol gives
2-(5-isoquinolinyloxy)-1-(2,3,4,5-tetrahydro-1H-[1,-
4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.23H.sub.21N.sub.3O.sub.2 m/z 372.3 (M+H).sup.+.
EXAMPLE 141
1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-2-(2,3,6,7-tetr-
ahydro-1H,5H-pyrido[3,2,1-ij]quinolin-8-yloxy)ethanone
[1122] 144
[1123] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-8-ol gives
1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-2-(2,3,6,7-tet-
rahydro-1H,5H-pyrido[3,2,1-ij]quinolin-8-yloxy)ethanone; MS (ESI+)
for C.sub.26H.sub.29N.sub.3O.sub.2 m/z 416.4 (M+H).sup.+.
EXAMPLE 142
2-(4-nitrophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11--
yl)ethanone
[1124] 145
[1125] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
4-nitrophenol gives
2-(4-nitrophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)ethanone; MS (ESI+) for C.sub.20H.sub.19N.sub.3O.sub.4
m/z 366.0 (M+H).sup.+.
EXAMPLE 143
2-(2-iodophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-y-
l)ethanone
[1126] 146
[1127] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-iodophenol gives
2-(2-iodophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-11-yl)ethanone; MS (ESI+) for C.sub.20H.sub.19IN.sub.2O.sub.2
m/z 446.9 (M+H).sup.+.
EXAMPLE 144
2-[(4'-bromo[1,1'-biphenyl]-4-yl)oxy]-1
-(2,3,4,5-tetrahydro-1H-[1,4]diaze-
pino[1,7-a]indol-11-yl)ethanone
[1128] 147
[1129] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
4'-bromo[1,1'-biphenyl]-4-ol gives
2-[(4'-bromo[1,1'-biphenyl]-4-yl)oxy]--
1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone;
MS (ESI+) for C.sub.26H.sub.23BrN.sub.2O.sub.2 m/z 476.8
(M+H).sup.+.
EXAMPLE 145
5-methoxy-6-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11--
yl)ethoxy]-1-indanone
[1130] 148
[1131] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
6-hydroxy-5-methoxy-1-indanone gives
5-methoxy-6-[2-oxo-2-(2,3,4,5-tetrah-
ydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethoxy]-1-indanone; MS
(ESI+) for C.sub.24H.sub.24N.sub.2O.sub.4 m/z 405.0
(M+H).sup.+.
EXAMPLE 146
7-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethoxy]-
-1-indanone
[1132] 149
[1133] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
7-hydroxy-1-indanone gives
7-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indol-11-yl)ethoxy]-1-indanone; MS (ESI+) for
C.sub.23H.sub.22N.sub.2O.sub.3 m/z 375.1 (M+H).sup.+.
EXAMPLE 147
5-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethoxy]-
-1-indanone
[1134] 150
[1135] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
5-hydroxy-1-indanone gives
5-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indol-11-yl)ethoxy]-1-indanone; MS (ESI+) for
C.sub.23H.sub.22N.sub.2O.sub.3 m/z 375.0 (M+H).sup.+.
EXAMPLE 148
2-[(2-acetyl-1,2,3,4-tetrahydro-5-isoquinolinyl)oxy]-1-(2,3,4,5-tetrahydro-
-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone
[1136] 151
[1137] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-acetyl-1,2,3,4-tetrahydro-5-isoquinolinol gives
2-[(2-acetyl-1,2,3,4-te-
trahydro-5-isoquinolinyl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.25H.sub.27N.sub.3O.sub.3 m/z 418.1 (M+H).sup.+.
EXAMPLE 149
2-([1,1'-biphenyl]-2-yloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-11-yl)ethanone
[1138] 152
[1139] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
[1,1'-biphenyl]-2-ol gives
2-([1,1'-biphenyl]-2-yloxy)-1-(2,3,4,5-tetrahy-
dro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.26H.sub.24N.sub.2O.sub.2 m/z 397.1 (M+H).sup.+.
EXAMPLE 150
2-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethoxy]-
-N-phenylbenzamide
[1140] 153
[1141] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-hydroxy-N-phenylbenzamide gives
2-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indol-11-yl)ethoxy]-N-phenylbenzamide; MS (ESI+)
for C.sub.27H.sub.25N.sub.3O.sub.3 m/z 440.0 (M+H).sup.+.
EXAMPLE 151
2-[2-(4-morpholinylcarbonyl)phenoxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indol-11-yl)ethanone
[1142] 154
[1143] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-(4-morpholinylcarbonyl)phenol gives
2-[2-(4-morpholinylcarbonyl)phenoxy-
]1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone;
MS (ESI+) for C.sub.25H.sub.27N.sub.3O.sub.4 m/z 434.0
(M+H).sup.+.
EXAMPLE 152
2-[2-methoxy-5-(1-pyrrolidinylmethyl)phenoxy]-1-(2,3,4,5-tetrahydro-1H-[1,-
4]diazepino[1,7-a]indol-11-yl)ethanone
[1144] 155
[1145] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-methoxy-5-(1-pyrrolidinylmethyl)phenol gives
2-[2-methoxy-5-(1-pyrrolid-
inylmethyl)phenoxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-
-yl)ethanone; MS (ESI+) for C.sub.26H.sub.31N.sub.3O.sub.3 m/z
434.0 (M+H).sup.+.
EXAMPLE 153
2-[(5-chloro-8-quinolinyl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a]indol-11-yl)ethanone
[1146] 156
[1147] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
5-chloro-8-quinolinol gives
2-[(5-chloro-8-quinolinyl)oxy]-1-(2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.23H.sub.20ClN.sub.3O.sub.2 m/z 406.0 (M+H).sup.+.
EXAMPLE 154
N-{4-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)etho-
xy]phenyl}urea
[1148] 157
[1149] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
N-(4-hydroxyphenyl)urea gives
N-{4-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-1-yl)ethoxy]phenyl}urea; MS (ESI+) for
C.sub.21H.sub.22N.sub.4O.sub.3 m/z 379.1 (M+H).sup.+.
EXAMPLE 155
N-{2-methyl-3-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-1-
1-yl)ethoxy]phenyl}acetamide
[1150] 158
[1151] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
N-(3-hydroxy-2-methylphenyl)acetamide gives
N-{2-methyl-3-[2-oxo-2-(2,3,4-
,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethoxy]phenyl}acetamide;
MS (ESI+) for C.sub.23H.sub.25N.sub.3O.sub.3 m/z 392.1
(M+H).sup.+.
EXAMPLE 156
2-phenoxy-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethano-
ne
[1152] 159
[1153] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations and without substituting for
phenol gives
2-phenoxy-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-1-yl)ethano-
ne; MS (ESI+) for C.sub.20H.sub.20N.sub.2O.sub.2 m/z 321.2
(M+H).sup.+.
EXAMPLE 157
2-(2,6-dimethylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)ethanone
[1154] 160
[1155] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2,6-dimethylphenol gives
2-(2,6-dimethylphenoxy)-1-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.22H.sub.24N.sub.2O.sub.2 m/z 349.3 (M+H).sup.+.
EXAMPLE 158
2-(4-methoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-1-
1-yl)ethanone
[1156] 161
[1157] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
4-methoxyphenol gives
2-(4-methoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.21H.sub.22N.sub.2O.sub.3 m/z 351.2 (M+H).sup.+.
EXAMPLE 159
2-(2,4-difluorophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)ethanone
[1158] 162
[1159] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2,4-difluorophenol gives
2-(2,4-difluorophenoxy)-1-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.20H18F.sub.2N.sub.2O.sub.2 m/z 357.2 (M+H).sup.+.
EXAMPLE 160
2-(2,4-dibromophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
-11-yl)ethanone
[1160] 163
[1161] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2,4-dibromophenol gives
2-(2,4-dibromophenoxy)-1-(2,3,4,5-tetrahydro-1H-[-
1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.20H.sub.18Br.sub.2N.sub.2O.sub.2 m/z 478.9 (M+H).sup.+.
EXAMPLE 161
2-(4-methylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-
-yl)ethanone
[1162] 164
[1163] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
4-methylphenol gives
2-(4-methylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.21H.sub.22N.sub.2O- .sub.2 m/z 335.3 (M+H).sup.+.
EXAMPLE 162
2-(2-chlorophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-
-yl)ethanone
[1164] 165
[1165] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-chlorophenol gives
2-(2-chlorophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.20H.sub.19ClN.sub.- 2O.sub.2 m/Z 355.1 (M+H).sup.+.
EXAMPLE 163
2-(2,4-dichlorophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)ethanone
[1166] 166
[1167] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2,4-dichlorophenol gives
2-(2,4-dichlorophenoxy)-1-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-1-yl)ethanone; MS (ESI+) for
C.sub.20H.sub.18Cl.sub.2N.sub.2O.sub.2 m/z 389.0 (M+H).sup.+.
EXAMPLE 164
2-(mesityloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-
11-yl)ethanone
[1168] 167
[1169] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2,4,6-trimethylphenol gives
2-(mesityloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.23H.sub.26N.sub.2O.sub.2 m/z 363.1 (M+H).sup.+.
EXAMPLE 165
2-(3-nitrophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11--
yl)ethanone
[1170] 168
[1171] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
3-nitrophenol gives
2-(3-nitrophenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)ethanone; MS (ESI+) for C.sub.20H.sub.19N.sub.3O.sub.4
m/z 366.1 (M+H).sup.+.
EXAMPLE 166
5-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethoxy]-
-3,4-dihydro-1(2H)-naphthalenone
[1172] 169
[1173] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
5-hydroxy-3,4-dihydro-1(2H)-naphthalenone gives
5-[2-oxo-2-(2,3,4,5-tetra-
hydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethoxy]-3,4-dihydro-1(2H)-naphth-
alenone; MS (ESI+) for C.sub.24H.sub.24N.sub.2O.sub.3 m/z 389.0
(M+H).sup.+.
EXAMPLE 167
2-(2,3-dimethylphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indo-
l-11-yl)ethanone
[1174] 170
[1175] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2,3-dimethylphenol gives
2-(2,3-dimethylphenoxy)-1-(2,3,4,5-tetrahydro-1H-
-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.22H.sub.24N.sub.2O.sub.2 m/z 349.1 (M+H).sup.+.
EXAMPLE 168
2-[(2-methyl-8-quinolinyl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a]indol-11-yl)ethanone
[1176] 171
[1177] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-methyl-8-quinolinol gives
2-[(2-methyl-8-quinolinyl)oxy]-1-(2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.24H.sub.23N.sub.3O.sub.2 m/z 386.0 (M+H).sup.+.
EXAMPLE 169
2-[(5,7-dibromo-8-quinolinyl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[-
1,7-a]indol-11-yl)ethanone
[1178] 172
[1179] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
5,7-dibromo-8-quinolinol gives
2-[(5,7-dibromo-8-quinolinyl)oxy]-1-(2,3,4-
,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS
(ESI+) for C.sub.23H.sub.19Br.sub.2N.sub.3O.sub.2 m/z 529.7
(M+H).sup.+.
EXAMPLE 170
2-[(5,7-dichloro-8-quinolinyl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indol-11-yl)ethanone
[1180] 173
[1181] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
5,7-dichloro-8-quinolinol gives
2-[(5,7-dichloro-8-quinolinyl)oxy]-1-(2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS
(ESI+) for C.sub.23H.sub.19Cl.sub.2N.sub.3O.sub.2 m/z 439.8
(M+H).sup.+.
EXAMPLE 171
2-(2,3-dimethoxyphenoxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-11-yl)ethanone
[1182] 174
[1183] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2,3-dimethoxyphenol gives
2-(2,3-dimethoxyphenoxy)-1-(2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone, MS (ESI+) for
C.sub.22H.sub.24N.sub.2O.sub.4 m/z 381.0 (M+H).sup.+.
EXAMPLE 172
2-[(5,7-dibromo-2-methyl-8-quinolinyl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-11-yl)ethanone
[1184] 175
[1185] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
5,7-dibromo-2-methyl-8-quinolinol gives
2-[(5,7-dibromo-2-methyl-8-quinol-
inyl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethano-
ne; MS (ESI+) for C.sub.24H.sub.21Br.sub.2N.sub.3O.sub.2 m/z 543.6
(M+H).sup.+.
EXAMPLE 173
2-[(5,7-dichloro-2-methyl-8-quinolinyl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]-
diazepino[1,7-a]indol-11-yl)ethanone
[1186] 176
[1187] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
5,7-dichloro-2-methyl-8-quinolinol gives
2-[(5,7-dichloro-2-methyl-8-quin-
olinyl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)etha-
none; MS (ESI+) for C.sub.24H.sub.21Cl.sub.2N.sub.3O.sub.2m/z 453.8
(M+H).sup.+.
EXAMPLE 174
2-[(5-fluoro-8-quinolinyl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a]indol-11-yl)ethanone
[1188] 177
[1189] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
5-fluoro-8-quinolinol gives
2-[(5-fluoro-8-quinolinyl)oxy]-1-(2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.23H.sub.20FN.sub.3O.sub.2 m/z 389.9 (M+H).sup.+.
EXAMPLE 175
2-[(7-propyl-8-quinolinyl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-
-a]indol-11-yl)ethanone
[1190] 178
[1191] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
7-propyl-8-quinolinol gives
2-[(7-propyl-8-quinolinyl)oxy]-1-(2,3,4,5-tet-
rahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.26H.sub.27N.sub.3O.sub.2 m/z 414.0 (M+H).sup.+.
EXAMPLE 176
2-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]-1-(2,3,4,5-tetrahydro--
1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone
[1192] 179
[1193] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2,2-dimethyl-2,3-dihydro-1-benzofuran-7-ol gives
2-[(2,2-dimethyl-2,3-dih-
ydro-1-benzofuran-7-yl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-11-yl)ethanone; MS (ESI+) for C.sub.24H.sub.26N.sub.2O.sub.3
m/z 391.0 (M+H).sup.+.
EXAMPLE 177
2-[2-fluoro-3-(trifluoromethyl)phenoxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indol-11-yl)ethanone
[1194] 180
[1195] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-fluoro-3-(trifluoromethyl)phenol gives
2-[2-fluoro-3-(trifluoromethyl)p-
henoxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone-
; MS (ESI+) for C.sub.21H.sub.18F.sub.4N.sub.2O.sub.2 m/z 406.9
(M+H).sup.+.
EXAMPLE 178
4-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethoxy]-
-1-indanone
[1196] 181
[1197] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
4-hydroxy-1-indanone gives
4-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepi-
no[1,7-a]indol-11-yl)ethoxy]-1-indanone; MS (ESI+) for
C.sub.23H.sub.22N.sub.2O.sub.3 m/z 375.0 (M+H).sup.+.
EXAMPLE 179
3-methyl-7-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-y-
l)ethoxy]-2-benzofuran-1(3H)-one
[1198] 182
[1199] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
7-hydroxy-3-methyl-2-benzofuran-1(3H)-one gives
3-methyl-7-[2-oxo-2-(2,3,-
4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethoxy]-2-benzofuran-1(-
3H)-one; MS (ESI+) for C.sub.23H.sub.22N.sub.2O.sub.4 m/z 390.9
(M+H).sup.+.
EXAMPLE 180
2-[(5,7-dimethyl-8-quinolinyl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino-
[1,7-a]indol-11-yl)ethanone
[1200] 183
[1201] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
5,7-dimethyl-8-quinolinol gives
2-[(5,7-dimethyl-8-quinolinyl)oxy]-1-(2,3-
,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS
(ESI+) for C.sub.25H.sub.25N.sub.3O.sub.2 m/z 400.0
(M+H).sup.+.
EXAMPLE 181
2-[(5,5-dimethyl-5,6,7,8-tetrahydro-1-naphthalenyl)oxy]-1-(2,3,4,5-tetrahy-
dro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone
[1202] 184
[1203] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
5,5-dimethyl-5,6,7,8-tetrahydro-1-naphthalenol gives
2-[(5,5-dimethyl-5,6,7,8-tetrahydro-1-naphthalenyl)oxy]-1-(2,3,4,5-tetrah-
ydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.26H.sub.30N.sub.2O.sub.2 m/z 403.0 (M+H).sup.+.
EXAMPLE 182
2-[(2-chloro-3-pyridinyl)oxy]-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7--
a]indol-11-yl)ethanone
[1204] 185
[1205] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-chloro-3-pyridinol gives
2-[(2-chloro-3-pyridinyl)oxy]-1-(2,3,4,5-tetra-
hydro-1H-[1,4]diazepino[1,7-a]indol-1-yl)ethanone; MS (ESI+) for
C.sub.19H.sub.18ClN.sub.3O.sub.2 m/z 356.0 (M+H).sup.+.
EXAMPLE 183
3-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethoxy]-
benzonitrile
[1206] 186
[1207] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
3-hydroxybenzonitrile gives
3-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazep-
ino[1,7-a]indol-11-yl)ethoxy]benzonitrile; MS (ESI+) for
C.sub.21H.sub.19N.sub.3O.sub.2m/z 346.1 (M+H).sup.+.
EXAMPLE 184
7-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethoxy]-
-2H-chromen-2-one
[1208] 187
[1209] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
7-hydroxy-2H-chromen-2-one gives
7-[2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]d-
iazepino[1,7-a]indol-11-yl)ethoxy]-2H-chromen-2-one; MS (ESI+) for
C.sub.23H.sub.20N.sub.2O.sub.4 m/z 389.0 (M+H).sup.+.
EXAMPLE 185
2-(phenylsulfanyl)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11--
yl)ethanone
[1210] 188
[1211] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
benzenethiol gives
2-(phenylsulfanyl)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)ethanone; MS (ESI+) for C.sub.20H.sub.20N.sub.2OS m/z
337.2 (M+H).sup.+.
EXAMPLE 186
2-(2,3-dihydro-1,4-benzodioxin-5-yloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indol-11-yl)ethanone
[1212] 189
[1213] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2,3-dihydro-1,4-benzodioxin-5-ol gives
2-(2,3-dihydro-1,4-benzodioxin-5-y-
loxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone;
MS (ESI+) for C.sub.22H.sub.22N.sub.2O.sub.4 m/z 379.1
(M+H).sup.+.
EXAMPLE 187
2-[(8,8-dimethyl-5,6,7,8-tetrahydro-2-naphthalenyl)oxy]-1-(2,3,4,5-tetrahy-
dro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone
[1214] 190
[1215] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
8,8-dimethyl-5,6,7,8-tetrahydro-2-naphthalenol gives
2-[(8,8-dimethyl-5,6,7,8-tetrahydro-2-naphthalenyl)oxy]-1-(2,3,4,5-tetrah-
ydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.26H.sub.30N.sub.2O.sub.2 m/z 403.2 (M+H).sup.+.
EXAMPLE 188
2-(4-pyridinyloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11--
yl)ethanone
[1216] 191
[1217] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
4-pyridinol gives
2-(4-pyridinyloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)ethanone; MS (ESI+) for
C.sub.19H.sub.19N.sub.3O.sub.2nm/z 322.1 (M+H).sup.+.
EXAMPLE 189
2-(2-pyrimidinyloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-1-
1-yl)ethanone
[1218] 192
[1219] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
2-pyrimidinol gives
2-(2-pyrimidinyloxy)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]-
indol-11-yl)ethanone; MS (ESI+) for
C.sub.18H.sub.18N.sub.4O.sub.2m/z 323.2 (M+H).sup.+.
EXAMPLE 190
2-(8-quinolinylsulfanyl)-1-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]ind-
ol-11-yl)ethanone
[1220] 193
[1221] Following the general procedure of Example 47 (Chart E, Step
2) and making non-critical variations but substituting phenol with
8-quinolinethiol gives
2-(8-quinolinylsulfanyl)-1-(2,3,4,5-tetrahydro-1H--
[1,4]diazepino[1,7-a]indol-11-yl)ethanone; MS (ESI+) for
C.sub.23H.sub.21N.sub.3OS m/z 388.2 (M+H).sup.+.
EXAMPLE 191
N-(6-methoxy-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indol-11-yl)acetamide
[1222] 194
[1223] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 6-methoxy-1,3-benzothiazol-2-ylamine gives
N-(6-methoxy-1,3-benzothiazol--
2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acet-
amide, MS (ESI+) for C.sub.22H.sub.20N.sub.4O.sub.3S m/z 421.2
(M+H).sup.+.
EXAMPLE 192
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-N-[6-(tri-
fluoromethoxy)-1,3-benzothiazol-2-yl]acetamide
[1224] 195
[1225] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 6-(trifluoromethoxy)-1,3-benzothiazol-2-ylamine gives
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-N-[6-(tr-
ifluoromethoxy)-1,3-benzothiazol-2-yl]acetamide, MS (ESI+) for
C.sub.22H.sub.17F.sub.3N.sub.4O.sub.3S m/z 475.0 (M+H).sup.+.
EXAMPLE 193
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-N-[6-(tri-
fluoromethyl)-1,3-benzothiazol-2-yl]acetamide
[1226] 196
[1227] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 6-(trifluoromethyl)-1,3-benzothiazol-2-ylamine gives
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-N-[6-(tr-
ifluoromethyl)-1,3-benzothiazol-2-yl]acetamide, MS (ESI+) for
C.sub.22H.sub.17F.sub.3N.sub.4O.sub.2S m/z 459.1 (M+H).sup.+.
EXAMPLE 194
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-N-{6-[(tr-
ifluoromethyl)sulfanyl]-1,3-benzothiazol-2-yl}acetamide
[1228] 197
[1229] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 6-[(trifluoromethyl)sulfanyl]-1,3-benzothiazol-2-ylamine gives
2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-N-{6-[(t-
rifluoromethyl)sulfanyl]-1,3-benzothiazol-2-yl}acetamide, MS (ESI+)
for C.sub.22H.sub.17F.sub.3N.sub.4O.sub.2S.sub.2 m/z 491.1
(M+H).sup.+.
EXAMPLE 195
N-(6-ethoxy-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indol-11-yl)acetamide
[1230] 198
[1231] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 6-ethoxy-1,3-benzothiazol-2-ylamine gives
N-(6-ethoxy-1,3-benzothiazol-2--
yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetam-
ide, MS (ESI+) for C.sub.23H.sub.22N.sub.4O.sub.3S m/z 435.2
(M+H).sup.+.
EXAMPLE 196
N-(6-fluoro-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indol-11-yl)acetamide
[1232] 199
[1233] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 6-fluoro-1,3-benzothiazol-2-ylamine gives
N-(6-fluoro-1,3-benzothiazol-2--
yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetam-
ide, MS (ESI+) for C.sub.21H.sub.17FN.sub.4O.sub.2S m/z 409.1
(M+H).sup.+.
EXAMPLE 197
N-(6-chloro-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indol-11-yl)acetamide
[1234] 200
[1235] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 6-chloro-1,3-benzothiazol-2-ylamine gives
N-(6-chloro-1,3-benzothiazol-2--
yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetam-
ide, MS (ESI+) for C.sub.21H.sub.17ClN.sub.4O.sub.2S m/z 425.1
(M+H).sup.+.
EXAMPLE 198
N-(6-methyl-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indol-11-yl)acetamide
[1236] 201
[1237] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 6-methyl-1,3-benzothiazol-2-ylamine gives
N-(6-methyl-1,3-benzothiazol-2--
yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetam-
ide, MS (ESI+) for C.sub.22H.sub.20N.sub.4O.sub.2S m/z 405.2
(M+H).sup.+.
EXAMPLE 199
N-(4-chloro-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indol-11-yl)acetamide
[1238] 202
[1239] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-chloro-1,3-benzothiazol-2-ylamine gives
N-(4-chloro-1,3-benzothiazol-2--
yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-1
I-yl)acetamide, MS (ESI+) for C.sub.21H.sub.17ClN.sub.4O.sub.2S m/z
425.2 (M+H).sup.+.
EXAMPLE 200
N-(4-methoxy-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]di-
azepino[1,7-a]indol-11-yl)acetamide
[1240] 203
[1241] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-methoxy-1,3-benzothiazol-2-ylamine gives
N-(4-methoxy-1,3-benzothiazol--
2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acet-
amide, MS (ESI+) for C.sub.22H.sub.20N.sub.4O.sub.3S m/z 421.2
(M+H).sup.+.
EXAMPLE 201
N-(4-methyl-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]dia-
zepino[1,7-a]indol-11-yl)acetamide
[1242] 204
[1243] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4-methyl-1,3-benzothiazol-2-ylamine gives
N-(4-methyl-1,3-benzothiazol-2--
yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetam-
ide, MS (ESI+) for C.sub.22H.sub.20N.sub.4O.sub.2S m/z 405.2
(M+H).sup.+.
EXAMPLE 202
N-(5,6-dichloro-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4-
]diazepino[1,7-a]indol-11-yl)acetamide
[1244] 205
[1245] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 5,6-dichloro-1,3-benzothiazol-2-ylamine gives
N-(5,6-dichloro-1,3-benzoth-
iazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-y-
l)acetamide, MS (ESI+) for C.sub.21H.sub.16Cl.sub.2N.sub.4O.sub.2S
m/z 459.1 (M+H).sup.+.
EXAMPLE 203
N-(5,6-dimethyl-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4-
]diazepino[1,7-a]indol-11-yl)acetamide
[1246] 206
[1247] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 5,6-dimethyl-1,3-benzothiazol-2-ylamine gives
N-(5,6-dimethyl-1,3-benzoth-
iazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-y-
l)acetamide, MS (ESI+) for C.sub.23H.sub.22N.sub.4O.sub.2S m/z
419.2 (M+H).sup.+.
EXAMPLE 204
N-(7-bromo-6-fluoro-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H--
[1,4]diazepino[1,7-a]indol-11-yl)acetamide
[1248] 207
[1249] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 7-bromo-6-fluoro-1,3-benzothiazol-2-ylamine gives
N-(7-bromo-6-fluoro-1,3-
-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]in-
dol-11-yl)acetamide, MS (ESI+) for
C.sub.21H.sub.16BrFN.sub.4O.sub.2S m/z 489.1 (M+H).sup.+.
EXAMPLE 205
N-(4,6-dichloro-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4-
]diazepino[1,7-a]indol-11-yl)acetamide
[1250] 208
[1251] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4,6-dichloro-1,3-benzothiazol-2-ylamine gives
N-(4,6-dichloro-1,3-benzoth-
iazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-y-
l)acetamide, MS (ESI+) for C.sub.21H.sub.16Cl.sub.2N.sub.4O.sub.2S
m/z 459.1 (M+H).sup.+.
EXAMPLE 206
N-(4,6-dimethyl-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4-
]diazepino[1,7-a]indol-11-yl)acetamide
[1252] 209
[1253] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4,6-dimethyl-1,3-benzothiazol-2-ylamine gives
N-(4,6-dimethyl-1,3-benzoth-
iazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-y-
l)acetamide, MS (ESI+) for C.sub.23H.sub.22N.sub.4O.sub.2S m/z
419.2 (M+H).sup.+.
EXAMPLE 208
N-(4,6-difluoro-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4-
]diazepino[1,7-a]indol-11-yl)acetamide
[1254] 210
[1255] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 4,6-difluoro-1,3-benzothiazol-2-ylamine gives
N-(4,6-difluoro-1,3-benzoth-
iazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-y-
l)acetamide, MS (ESI+) for C.sub.21H.sub.16F.sub.2N.sub.4O.sub.2S
m/z 427.1 (M+H).sup.+.
EXAMPLE 209
N-(6-nitro-1,3-benzothiazol-2-yl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diaz-
epino[1,7-a]indol-11-yl)acetamide
[1256] 211
[1257] Following the general procedure of Example 20 (Chart B) and
making non-critical variations but substituting 4-methoxyaniline
with 6-nitro-1,3-benzothiazol-2-ylamine gives
N-(6-nitro-1,3-benzothiazol-2-yl-
)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamid-
e, MS (ESI+) for C.sub.21H.sub.17N.sub.5O.sub.4S m/z 436.2
(M+H).sup.+.
Efficacy Data
[1258] All of the Example compounds provided above are believed to
be 5-HT ligands, with the ability to displace >50% of a
radiolabeled test ligand from one or more 5-HT receptor subtypes at
a concentration of 1 .mu.M. The procedures used for testing such
displacement are well known and would be readily available to one
skilled in the art. 212 213 214 215 216 217 218
[1259] Having described the invention in detail and by reference to
the preferred embodiments thereof, it will be apparent that
modifications and variations are possible without departing from
the scope of the appended claims.
* * * * *