Pyrrolopyrimidine and pyrrolopyridine derivatives substituted with cyclic amino group

Abstract

An object of the present invention is to provide an antagonist against CRF receptors which is effective as a therapeutic or prophylactic agent for diseases in which CRF is considered to be involved, such as depression, anxiety, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorder, hypertension, gastric diseases, drug dependence, epilepsy, cerebral infarction, cerebral ischemia, cerebral edema, cephalic external wound, inflammation, immunity-related diseases, alopecia, irritable bowel syndrome, sleep disorders, epilepsy, dermatitides, schizophrenia, etc. [Solution] A pyrrolopyrimidine or pyrrolopyridine derivative substituted with a cyclic amino group represented by the following formula [I]: 1 has a high affinity for CRF receptors and is effective against diseases in which CRF is considered to be involved.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001] 1. Technical Field

[0002] The present invention relates to a therapeutic agent for diseases in which corticotropin releasing factor (CRF) is considered to be involved, such as depression, anxiety, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorder, hypertension, gastral diseases, drug dependence, cerebral infarction, cerebral ischemia, cerebral edema, cephalic external wound, inflammation immunity-related diseases, alpecia, irritable bowel syndrome, sleep disorders, epilepsy, dermatitides, schizophrenia, etc.

[0003] 2. Description of the Prior Art

[0004] CRF is a hormone comprising 41 amino acids (Science, 213, 1394-1397, 1981; and J. Neurosci., 7, 88-100, 1987), and it is suggested that CRF plays a core role in biological reactions against stresses (Cell. Mol. Neurobiol., 14, 579-588, 1994; Endocrinol., 132, 723-728, 1994; and Neuroendocrinol. 61, 445-452, 1995). For CRF, there are the following two paths: a path by which CRF acts on peripheral immune system or sympathetic nervous system through hypothalamus-pituitary-adrenal system, and a path by which CRF functions as a neurotransmitter in central nervous system (in Corticotropin Releasing Factor: Basic and Clinical Studies of a Neuropeptide, pp. 29-52, 1990). Intraventricular administration of CRF to hypophysectomized rats and normal rats causes an anxiety-like symptom in both types of rats (Pharmacol. Rev., 43, 425-473, 1991; and Brain Res. Rev., 15, 71-100, 1990). That is, there are suggested the participation of CRF in hypothalamus-pituitary-adrenal system and the pathway by which CRF functions as a neurotransmitter in central nervous system.

[0005] The review by Owens and Nemeroff in 1991 summarizes diseases in which CRF is involved (Pharmacol. Rev., 43, 425-474, 1991). That is, CRF is involved in depression, anxiety, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorder, hypertension, gastrointestinal diseases, drug dependence, inflammation, immunity-related diseases, etc. It has recently been reported that CRF is involved also in epilepsy, cerebral infarction, cerebral ischemia, cerebral edema, and cephalic external wound (Brain Res. 545, 339-342, 1991; Ann. Neurol. 31, 48-498, 1992; Dev. Brain Res. 91, 245-251, 1996; and Brain Res. 744, 166-170, 1997). Accordingly, antagonists against CRF receptors are useful as therapeutic agents for the diseases described above.

[0006] WO02/002549 and WO0/053604 disclose pyrrolopyridine and pyrrolopyrimidine derivatives respectively as CRF receptor antagonists. Bioorganic & Medicinal Chemistry 10 (2002) 175-183 also discloses pyrrolopyrimidine derivatives. However, none disclose the compounds provided in the present invention.

PROBLEM(S) TO BE SOLVED BY INVENTION

[0007] An object of the present invention is to provide an antagonist against CRF receptors which is effective as a therapeutic or prophylactic agent for diseases in which CRF is considered to be involved, such as depression, anxiety, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorder, hypertension, gastral diseases, drug dependence, epilepsy, cerebral infarction, cerebral ischemia, cerebral edema, cephalic external wound, inflammation, immunity-related diseases, alpecia, irritable bowel syndrome, sleep disorders, epilepsy, dermatitides, schizophrenia, etc.

MEANS FOR SOLVING PROBLEM

[0008] The present inventors earnestly investigated pyrrolopyrimidine and pyrrolopyridine derivatives substituted with a cyclic amino group that have a high affinity for CRF receptors, whereby the present invention has been accomplished.

[0009] The present invention is pyrrolopyrimidine and pyrrolopyridine derivatives substituted with a cyclic amino group explained below.

[0010] A pyrrolopyrimidine or pyrrolopyridine derivative substituted with a cyclic amino group represented by the following formula [I]: 2

[0011] (wherein the cyclic amino group is represented by the following formula [II]: 3

[0012] in which the cyclic amino group is a 3- to 8-membered saturated cyclic amine or a 3- to 8-membered saturated cyclic amine bridged with C.sub.1-5alkylene or C.sub.1-4alkylene- O--C.sub.1-4alkylene between any different two carbon atoms of the cyclic amine, which cyclic amine is substituted with a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.s- up.3).sub.n--X, R.sup.4 and R.sup.5 independently on the same or different carbon atoms of the cyclic amine;

[0013] X is cyano, hydroxy or --OR.sup.9;

[0014] Y is N or CR.sup.10;

[0015] R.sup.1 is hydrogen, hydroxy, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl;

[0016] R.sup.2 is hydrogen or C.sub.1-5alkyl;

[0017] R.sup.3 is hydrogen, cyano, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1- -5alkyl or hydroxy-C.sub.1-5alkyl;

[0018] m is an integer selected from 0, 1, 2, 3, 4 and 5;

[0019] n is 0 or 1;

[0020] with the proviso that when X is hydroxy or OR.sup.9, and n is 0, then m is an integer selected from 1, 2,3,4 and 5;

[0021] R.sup.4 is hydrogen, hydroxy, hydroxy-C.sub.1-5alkyl, cyano, cyano-C.sub.1-5alkyl or C.sub.1-5alkyl;

[0022] R.sup.5 is hydrogen or C.sub.1-5alkyl;

[0023] R.sup.6 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy or --N(R.sup.11)R.sup.12;

[0024] R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen, halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy, N(R.sup.11a)R.sup.12a, --CO.sub.2R.sup.13, cyano, nitro, C.sub.1-5alkylthio, trifluoromethyl or trifluoromethoxy; or R.sup.7 and R.sup.9 are taken together to form --CH.sub.2--CH.sub.2--CH.s- ub.2--CH.sub.2-- or --CH.dbd.CH--CH.dbd.CH--;

[0025] R.sup.9 is C.sub.1-24acyl, C.sub.1-10alkoxycarbonyl, aryl-C.sub.1-5alkyloxycarbonyl, --CO--O--CHR.sup.14--OCO--R.sup.15, --P(.dbd.O)(OR.sup.14a)OR.sup.15a, --CO--(CH.sub.2).sub.p--(CHR.sup.16).s- ub.q--NR.sup.17R.sup.18, arylcarbonyl or heteroarylcarbonyl, wherein each said acyl, aryl and heteroaryl is unsubstituted or substituted with C.sub.1-5alkoxy, and C.sub.1-24acyl optionally includes one to six double bonds;

[0026] R.sup.10 is hydrogen, C.sub.1-5alkyl, halogen, cyano or --CO.sub.2R.sup.19;

[0027] Ar is aryl or heteroaryl which aryl or heteroaryl is unsubstituted or substituted with 1 or more substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.2-5alkenyl, C.sub.2-5alkynyl, C.sub.1-5alkoxy, C.sub.1-5alkylthio, C.sub.1-5alkylsulfinyl, C.sub.1-5alkylsulfonyl, cyano, nitro, hydroxy, --CO.sub.2R.sup.19a, --C(.dbd.O)R.sup.19a, --CONR.sup.11bR.sup.12b, --OC(.dbd.O)R.sup.19a, --NR.sup.11bCO.sub.2R.sup- .19a, --S(O).sub.rNR.sup.11bR.sup.12b, hydroxy-C.sub.2-5alkylamino-C.sub.2- -5alkoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, fluoromethoxy, methylenedioxy, ethylenedioxy and --N(R.sup.20)R.sup.21; with the proviso that when X is hydroxy, Y is N, and the cyclic amino group is 5-membered ring, then Ar is aryl or heteroaryl which aryl or heteroaryl is substituted with at least one of substituents which are selected from halogen and trifluoromethyl;

[0028] R.sup.11 and R.sup.12 are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl;

[0029] R.sup.11a and R.sup.12a are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl;

[0030] R.sup.11b and R.sup.12b are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl;

[0031] R.sup.13 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, C.sub.1-5alkoxy- C.sub.1-5alkyl, C.sub.3-8cycloalkyloxy-C.sub.1-5alkyl or phenyl;

[0032] R.sup.14 and R.sup.15 are the same or different, and independently are hydrogen, C.sub.1-5alkyl or aryl-C.sub.1-5alkyl;

[0033] R.sup.14a and R.sup.15a are the same or different, and independently are hydrogen, C.sub.1-5alkyl or aryl-C.sub.1-5alkyl;

[0034] R.sup.16 is hydrogen, C.sub.1-5alkyl, aryl, heteroaryl, aryl-C.sub.1-5alkyl, heteroaryl-C.sub.1-5alkyl, hydroxy-C.sub.1-5alkyl, hydroxycarbonyl-C.sub.1-5alkyl, hydroxyphenyl-C.sub.1-5alkyl, C.sub.1-5alkoxy- C.sub.1-5alkyl, amino-C.sub.1-5alkyl, guanidino-C.sub.1-5alkyl, mercapto-C.sub.1-5alkyl, C.sub.1-5alkylthio- C.sub.1-5alkyl or aminocarbonyl-C.sub.1-5alkyl;

[0035] R.sup.17 and R.sup.18 are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, C.sub.1-10acyl, C.sub.1-10alkoxycarbonyl or aryl-C.sub.1-5alkyloxycarbonyl;

[0036] or R.sup.16 and R.sup.17 are taken together to form --CH.sub.2--, --CH.sub.2CH.sub.2--, --CH.sub.2CH.sub.2CH.sub.2-- or --CH.sub.2CH.sub.2CH.sub.2CH.sub.2--;

[0037] p is an integer selected from 0, 1, 2, 3, 4 and 5;

[0038] q is 0 or 1;

[0039] R.sup.19 is hydrogen or C.sub.1-5alkyl;

[0040] R.sup.19a is hydrogen or C.sub.1-5alkyl;

[0041] r is 1 or 2;

[0042] R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-5alkyl), individual isomers thereof, racemic or non-racemic mixtures of isomers thereof or N-oxide thereof, or pharmaceutically acceptable salts and hydrates thereof.

[0043] The terms used in the present specification have the following meanings.

[0044] The term "a 3- to 8-membered saturated cyclic amine" means aziridine, azetidine, pyrrolidine, piperidine, azepane or azocane.

[0045] The term "C.sub.1-5alkylene" means a straight or branched chain alkylene of 1 to 5 carbon atoms, such as methylene, ethylene, propylene, trimethylene, tetramethylene, pentamethylene or the like.

[0046] The term "a 3- to 8-membered saturated cyclic amine bridged with C.sub.1-5alkylene or C.sub.1-4alkylene-O--C.sub.1-4alkylene between any different two carbon atoms of the cyclic amine" includes, for example, 8-azabicyclo[3.2.1]oct-8-yl, 9-azabicyclo[3.3.1]non-9-yl, 7-azabicyclo[2.2.1]hept-7-yl, 3-oxa-7-azabicyclo[3.3.1]non-7-yl and 3-oxa-9-azabicyclo[3.3.1]non-9-yl.

[0047] The term "C.sub.1-5alkyl" means a straight chain or branched chain alkyl group of 1 to 5 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, sec- butyl, pentyl, isopentyl or the like.

[0048] The term "C.sub.1-5alkoxy" means a straight chain or branched chain alkoxy group of 1 to 5 carbon atoms, such as methoxy, ethoxy, propoxy, isopropyloxy, butoxy, isobutyloxy, pentyloxy, isopentyloxy or the like.

[0049] The term "C.sub.1-5alkoxy-C.sub.1-5alkyl" means a substituted C.sub.1-5alkyl group having the above-mentioned C.sub.1-5alkoxy group as the substituent, such as methoxymethyl, 2-methoxyethyl, 2-ethoxyethyl or the like.

[0050] The term "hydroxy-C.sub.1-5alkyl" means a substituted C.sub.1-5alkyl group having hydroxy group, such as hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 5-hydroxypentyl or the like.

[0051] The term "cyano-C.sub.1-5alkyl" means a substituted C.sub.1-5alkyl group having cyano group, such as cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 3-cyanopropyl, 4-cyanobutyl, 5-cyanopentyl or the like.

[0052] The term "C.sub.3-8cycloalkyl" means a cyclic alkyl group of 3 to 8 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or the like.

[0053] The term "C.sub.3-8cycloalkyl-C.sub.1-5alkyl" means a substituted C.sub.1-5alkyl group having the above-mentioned C.sub.3-8cycloalkyl as the substituent, such as cyclopropylmethyl, cyclopropylethyl, cyclopentylethyl or the like.

[0054] The term "C.sub.3-8cycloalkyloxy" means a cyclic alkoxy group of 3 to 8 carbon atoms, such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or the like.

[0055] The term "halogen" means fluorine, chlorine, bromine or iodine atom.

[0056] The term "C.sub.3-8cycloalkyloxy-C.sub.1-5alkyl" means a substituted C.sub.1-5alkyl group having the above mentioned C.sub.3-8cycloalkyloxy as the substituent, such as cyclopropyloxymethyl, 2-cyclopropyloxyethyl or the like.

[0057] The term "C.sub.1-5alkylthio" means a straight chain or branched chain alkylthio group of 1 to 5 carbon atoms, such as methylthio, ethylthio, propylthio or the like.

[0058] The term "C.sub.1-24acyl" means a straight chain or branched chain, and saturated or unsaturated acyl group of 1 to 24 carbon atoms, such as acetyl, propionyl, butyryl, pentanoyl, hexanoyl, heptanoyl, octanoyl, nonanoyl, decanoyl, isobutyryl, 2,2-dimethylpropionyl, octadeca-9,12-dienoyl, eicosa-5,8,11,14-tetraenoyl, docosa-4,7,10,13,16,19-hexaenoyl, eicosa-5,8,11,14,17-pentaenoyl or the like.

[0059] The term "C.sub.1-10alkoxycarbonyl" means a straight chain or branched chain alkoxycarbonyl group of 2 to 11 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, isopropoxycarbonyl, t-butoxycarbonyl or the like.

[0060] The term "aryl" means a monocyclic or bicyclic group of 6 to 12 ring carbon atoms having at least one aromatic ring, such as phenyl, naphthyl or the like.

[0061] The term "aryl-C.sub.1-5alkyloxycarbonyl" means a substituted C.sub.1-5alkyloxycarbonyl group having the above-mentioned aryl as the substituent, such as benzyloxycarbonyl, phenethyloxycarbonyl or the like.

[0062] The term "arylcarbonyl" means a substituted carbonyl group having the above- mentioned aryl as the substituent, such as benzoyl, naphthalene-1-carbonyl, naphthalene-2-carbonyl or the like.

[0063] The term "heteroaryl" means a monocyclic or bicyclic group of 5 to 12 ring atoms having at least one aromatic ring having in its ring 1 to 4 atoms which may be the same or different and are selected from nitrogen, oxygen and sulfur, such as pyridyl, pyrimidinyl, imidazolyl, quinolyl, indolyl, benzofuranyl, quinoxalinyl, benzo[1,2,5]thiadiazolyl, benzo[1,2,5]oxadiazolyl or the like.

[0064] The term "heteroarylcarbonyl" means a substituted carbonyl group having the above-mentioned heteroaryl as the substituent, such as pyridine-2-carbonyl, pyridine-3-carbonyl, pyridine-4-carbonyl, pyrimidine-2-carbonyl, pyrimidine-4-carbonyl, pyrimidine-5-carbonyl or the like.

[0065] The term "C.sub.2-5alkenyl" means a straight chain or branched chain alkenyl group of 2 to 5 carbon atoms, such as vinyl, isopropenyl, allyl or the like.

[0066] The term "C.sub.2-5alkynyl" means a straight chain or branched chain alkynyl group of 2 to 5 carbon atoms, such as ethynyl, prop-1-ynyl, prop-2-ynyl or the like.

[0067] The term "C.sub.1-5alkysulfinyl" means a straight chain or branched chain alkylsulfinyl group of 1 to 5 carbon atoms, such as methanesulfinyl, ethanesulfinyl or the like.

[0068] The term "C.sub.1-5alkysulfonyl" means a straight chain or branched chain alkylsulfonyl group of 1 to 5 carbon atoms, such as methanesulfonyl, ethanesulfonyl or the like.

[0069] The term "hydroxy-C.sub.2-5alkylamino-C.sub.2-5alkoxy" means a substituted C.sub.2-5alkoxy group having a hydroxy-C.sub.2-5alkylamino group as the substituent such as 2-(2-hydroxyethylamino)ethoxy or the like.

[0070] The term "aryl-C.sub.1-5alkyl" means a substituted C.sub.1-5alkyl group having the above-mentioned aryl as the substituent, such as benzyl, phenethyl, 3-phenylpropyl, naphthalen-1-ylmethyl, naphthalen-2-ylmethyl or the like.

[0071] The term "heteroaryl-C.sub.1-5alkyl" means a substituted C.sub.1-5alkyl group having the above-mentioned heteroaryl as the substituent, such as 1H-indol-3-ylmethyl, 1H- imidazol-4-ylmethyl or the like.

[0072] The term "hydroxycarbonyl-C.sub.1-5alkyl" means a substituted C.sub.1-5alkyl group having a hydroxycarbonyl group as the substituent, such as hydroxycarbonylmethyl, 2-hydroxycarbonylethyl, 3-hydroxycarbonylpropyl, 4-hydroxycarbonylbutyl or the like.

[0073] The term "hydroxyphenyl-C.sub.1-5alkyl" means a substituted C.sub.1-5alkyl group having a hydroxyphenyl group as the substituent, such as 4-hydroxybenzyl, 3-hydroxybenzyl 2-hydroxybenzyl, 2-(4-hydroxyphenyl)ethyl or the like.

[0074] The term "amino-C.sub.1-5alkyl" means a substituted C.sub.1-5alkyl group having a amino group as the substituent, such as aminomethyl, 1-aminoethyl, 2-aminoethyl, 3-aminopropyl, 4-aminobutyl, 5-aminopentyl or the like.

[0075] The term "guanidino-C.sub.1-5alkyl" means a substituted C.sub.1-5alkyl group having a guanidino group as the substituent, such as guanidinomethyl, 1-guanidinoethyl, 2-guanidinoethyl, 3-guanidinopropyl, 4-guanidinobutyl, 5-guanidinopentyl or the like.

[0076] The term "mercapto-C.sub.1-5alkyl" means a substituted C.sub.1-5alkyl group having a mercapto group as the substituent, such as mercaptomethyl, 1-mercaptoethyl, 2-mercaptoethyl, 3-mercaptopropyl, 4-mercaptobutyl, 5-mercaptopentyl or the like.

[0077] The term "C.sub.1-5alkylthio-C.sub.1-5akyl" means a substituted C.sub.1-5alkyl group having the above-mentioned C.sub.1-5alkylthio group as the substituent, such as methylthiomethyl, 1-methylthioethyl, 2-methylthioethyl, 3-methylthiopropyl, 4-methylthiobutyl, 5-methylthiopentyl or the like.

[0078] The term "aminocarbonyl-C.sub.1-5alkyl" means a substituted C.sub.1-5alkyl group having an aminocarbonyl group as the substituent, such as aminocarbonylmethyl, 2-aminocarbonylethyl, 3-aminocarbonylpropyl, 4-aminocarbonylbutyl or the like.

[0079] The phrase "aryl or heteroaryl which aryl or heteroaryl is unsubstituted or substituted with 1 or more substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.2-5alkenyl, C.sub.2-5alkynyl, C.sub.1-5alkoxy, C.sub.1-5alkylthio, C.sub.1-5alkylsulfinyl, C.sub.1-5alkylsulfonyl, cyano, nitro, hydroxy, --CO.sub.2R.sup.19a, --C(.dbd.O)R.sup.19a, --CONR.sup.11bR.sup.12b, --OC(.dbd.O)R.sup.19a, NR.sup.11bCO.sub.2R.sup.19a, --S(O).sub.rNR.sup.11bR.sup.12b, hydroxy-C.sub.2-5alkylamino-C.sub.2-5alkoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, fluoromethoxy, methylenedioxy, ethylenedioxy and --N(R.sup.20)R.sup.21" includes, for example, 2,4-dimethylphenyl, 2,6-dimethylphenyl, 2,4-dibromophenyl, 2-bromo-4-isoproylphenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 2-chloro-4-trifluoromethylphenyl, 4-methoxy-2-methylphenyl, 2-chloro-4-trifluoromethoxyphenyl, 4-isopropyl-2-methylthiophenyl, 2,4,6-trimethylphenyl, 4-bromo-2,6-dimethylphenyl, 4-bromo-2,6-diethylphenyl, 4-chloro-2,6-dimethylphenyl, 2,4,6-tribromophenyl, 2,4,5-tribromophenyl, 2,4,6-trichlorophenyl, 2,4,5-trichlorophenyl, 4-bromo-2,6-dichlorophenyl, 6-chloro-2,4-dibromophenyl, 2,4-dibromo-6-fluorophenyl, 2,4-dibromo-6-methylphenyl, 2,4-dibromo-6-methoxyphenyl, 2,4-dibromo-6-methylthiophenyl, 2,6-dibromo-4-isopropylphenyl, 2,6-dibromo-4-trifluoromethylphenyl, 2-bromo-4-trifluoromethylphenyl, 4-bromo-2-chlorophenyl, 2-bromo-4-chlorophenyl, 4-bromo-2-methylphenyl, 4-chloro-2-methylphenyl, 2,4-dimethoxyphenyl, 2,6-dimethyl-4-methoxypheny- l, 4-chloro-2,6-dibromophenyl, 4-bromo-2,6-difluorophenyl, 2,6-dichloro-4-trifluoromethylphenyl, 2,6-dichloro-4-trifluoromethoxyphen- yl, 2,6-dibromo-4-trifluoromethoxyphenyl, 2-chloro-4,6-dimethylphenyl, 2-bromo-4,6-dimethoxyphenyl, 2-bromo-4-isopropyl-6-methoxyphenyl, 2,4-dimethoxy-6-methylphenyl, 2,6-dimethyl-4-[2-(2-hydroxyethylamino)etho- xy]phenyl, 6-dimethylamino-4-methylpyridin-3-yl, 2-chloro-6-trifluoromethy- lpyridin-3-yl, 2-chloro-6-trifluoromethoxypyridin-3-yl, 2-chloro-6-methoxypyridin-3-yl, 6-methoxy-2-trifluoromethylpyridin-3-yl, 2-chloro-6-difluoromethylpyridin-3-yl, 6-methoxy-2-methylpyridin-3-yl, 2,6-dimethoxypyridin-3-yl, 4,6-dimethyl-2-trifluoromethylpyrimidin-5-yl, 2-dimethylamino-6-methylpyridin-3-yl, 6-dimethylamino-2-methylpyridin-3-y- l, 2,3-dihydrobenzo[1,4]dioxin-5-yl and benzo[1,3]dioxol-4-yl, 5,7-dimethylbenzo[1,2,5]thiadiazol-4-yl, 5,7-dimethylbenzo[1,2,5]oxadiazo- l-4-yl, 2-isopropoxy-6-trifluoromethylpyridin-3-yl, 2-methoxy-6-methylpyridin-3-yl, 2,6-dimethylpyridin-3-yl, 2-bromo-6-methoxypyridin-3-yl, 2-chloro-6-dimethylaminopyridin-3-yl, 2,6-dichloropyridin-3-yl, 2,4-dimethyl-6-dimethylaminopyridin-3-yl, 2,4,6-trimethylpyridin-3-yl, 2,4,6-trimethylpyrimidin-5-yl, 4,6-dimethyl-2-dimethylaminopyrimidin-5-yl, 5-iodo-3-methylpyridin-2-yl, 3-methyl-5- methylaminopyridin-2-yl, 3-dimethylamino-5-methylpyridin-2-yl- , 5-methyl-3-methylaminopyridin-2-yl, 3-chloro-5-methylpyridin-2-yl, 3-amino-5-methylpyridin-2-yl, 5-methyl-3-nitropyridin-2-yl, 5-diethylamino-3-methylpyridin-2-yl, 5-fluoro-3-methylpyridin-2-yl, 5-chloro-3-methylpyridin-2-yl, 5-dimethylamino-3-methylpyridin-2-yl, 5-amino-3-methylpyridin-2-yl, 3-methyl-5-nitropyridin-2-yl, 3-bromo-5-methylpyridin-2-yl, 4-chloro-2,5-dimethoxyphenyl, 4,5-dimethyl-2-methoxyphenyl, 5-fluoro-2,4-dimethylphenyl, 2,4-dimethoxy-5-methylphenyl, 2-chloro-4-methoxy-5-methylphenyl, 2-chloro-5-fluoro-4-methylphenyl, 2-bromo-4,5-dimethoxyphenyl, 2-bromo-5-fluoro-4-methoxyphenyl, 2-chloro-4,5-dimethoxyphenyl, 2.5-dichloro-4-methoxyphenyl, 2,4-dichloro-5-fluorophenyl, 2-chloro-5-fluoro-4-methoxyphenyl, 2,4,5-trichlorophenyl, 2-chloro-5-fluoro-4-methylphenyl, 5-fluoro-4-methoxy-2-methylphenyl, 4,5-dimethoxy-2-methylphenyl, 5-chloro-4-methoxy-2-methylphenyl, 2,4,5-trimethylphenyl, 6-methoxy-4-methylpyridin-3-yl, 4-methoxy-6-methylpyridin-3-yl, 4,6-dimethylpyridin-3-yl, 2-chloro-4-isopropylphenyl, 2-chloro-4-methylphenyl, 4-amino-2-chlorophenyl, 2-chloro-4-dimethylcarbamoylphenyl, 2-chloro-4-methylcarbamoylphenyl, 4-carbamoyl-2-chlorophenyl, 2-chloro-4-methylsulfonylphenyl, 4-carboxy-2-chlorophenyl, 2-chloro-4-iodophenyl, 2-bromo-4-methylthiophenyl, 2-bromo-4-methylsulfinylphenyl, 2-bromo-4-dimethylaminophenyl, 2-bromo-4-methylsulfonylphenyl, 2-bromo-4-cyclopentylphenyl, 2-bromo-4-tert- butylphenyl, 2-bromo-4-propylphenyl, 2-bromo-4-methylphenyl, 2-bromo-4-trifluoromethoxyphenyl, 2-bromo-4-methoxyphenyl, 2-bromo-4-ethoxyphenyl, 4-isopropyl-2-methylsulf- onylphenyl, 4-cyclopentyl-2-methylthiophenyl, 4-butyl-2-methylthiophenyl, 4-methoxy-2-methylthiophenyl, 2-methylthio-4-propylphenyl, 2-dimethylamino-4-isopropylphenyl, 2-iodo-4-isopropylphenyl, 2-fluoro-4-methylphenyl, 2,4-difluorophenyl, 2-chloro-4-methoxyphenyl, 2-chloro-4-hydroxyphenyl, 4-cyano-2-methoxyphenyl, 4-bromo-2-methoxyphenyl, 2-methoxy-4-methylphenyl, 4-chloro-2-methoxyphenyl, 2-hydroxy-4-methylphenyl, 4-fluoro-2-methoxyphenyl, 2-hydroxy-4methylphenyl, 4-cyano-2-methoxyphenyl, 2-chloro-4-methylthiophenyl, 2-methoxy-4-trifluoromethylphenyl, 4-isopropyl-2-methoxyphenyl, 2-chloro-4-cyanophenyl, 2-chloro-4-ethoxycarbonylphenyl, 2-chloro-4-methylaminophenyl, 4-cyano-2-trifluoromethylphenyl, 4-cyano-2-methylphenyl, 2-methyl-4-trifluoromethoxyphenyl, 2-cyano-4-trifluoromethylphenyl, 4-carboxyamino-2-trifluoromethylphenyl, 4-methoxy-2-trifluoromethylphenyl, 4-fluoro-2-methylphenyl, 4-hydroxy-2-methylphenyl, 4-methoxy-2-methoxycarbonylphenyl, 2-ethyl-4-methoxyphenyl, 2-formyl-4-methoxyphenyl, 4-chloro-2-trifluoromethylphenyl, 4-dimethylamino-2-trifluoromethylphenyl- , 4-difluoromethoxy-2-methylphenyl, 2-cyano-4-methoxyphenyl, 4-hydroxy-2-trifluoromethylphenyl, 4-isopropyl-2-trifluoromethylphenyl, 4-diethylamino-2-methylphenyl, 4-fluoro-2-trifluoromethylphenyl, 4-propoxy-2-trifluoromethylphenyl, 4-dimethylamino-2-methylthiophenyl, 4-isopropyl-2-isopropylthiophenyl, 2-ethylthio-4-isopropylphenyl, 4-methylamino-2-methylthiophenyl, 2-methylthio-4-propionylphenyl, 4-acetyl-2-methylthiophenyl, 4-cyano-2-methylthiophenyl, 4-methoxy-2-methylthiophenyl, 4-ethyl-2-methylthiophenyl, 4-bromo-2-methylthiophenyl, 4-isopropyl-2-methylsulfinylphenyl, 2,4-dimethylthiophenyl, 4,6-dimethyl-2-isopropylphenyl, 4,6-dimethyl-2-isopropenylphenyl, 2-acetyl-4,6-dimethylphenyl, 2,6-dimethyl-4-trifluoromethylphenyl, 2,6-dimethyl-4-isopropenylphenyl, 4-acetyl-2,6-dimethylphenyl, 2,4,6-triethylphenyl, 4,6-dimethyl-2-methylthiophenyl, 4,6-dimethyl-2-iodophenyl, 2-fluoromethoxy-4,6-dimethylphenyl, 4,6-dimethyl-2-isopropoxyphenyl, 4,6-dimethyl-2-ethoxyphenyl, 2,6-dichloro-4-ethoxyphenyl, 2-bromo-4,6-dimethoxyphenyl, 2-bromo-6-hydroxy-4-methoxyphenyl, 2,6-dibromo-4-ethoxyphenyl, 4-bromo-2-methoxy-6-methylphenyl, 2,6-dibromo-4-methoxyphenyl, 4,6-dibromo-2-trifluoromethoxyphenyl, 2,4-dibromo-6-trifluoromethylphenyl, 4-bromo-2-chloro-6-methylphenyl, 4-chloro-2,6-dimethoxyphenyl, 2,4-dichloro-6-methoxyphenyl, 4,6-dichloro-2-methylthiophenyl, 4,6-dichloro-2-trifluoromethylphenyl, 2,6-dimethoxy-4-ethylphenyl, 4,6-dimethyl-2-methoxyphenyl, 2,6-dimethoxy-4-methylphenyl, 2-chloro-6-methoxy-4-methylphenyl, 4,6-dimethyl-2-ethoxyphenyl, 6-hydroxy-2,4-dimethylphenyl, 4-cyano-2-methoxy-6-methylphenyl, 6-fluoro-2-methoxy-4-methylphenyl, 4-acetyl-2-methoxy-6-methylphenyl, 2-chloro-4,6-dimethoxyphenyl, 2,6-dimethoxy-4-ethoxyphenyl, 2,4,6-trimethoxyphenyl, 4,6-dibromo-2-trifluoromethoxyphenyl, 2-bromo-4-dimethylamino-6-methoxyph- enyl, 4-bromo-2-methoxy-6-methylphenyl, 4,6-dimethoxy-2-propoxyphenyl, 4,6-dichloro-2-propoxyphenyl, 2-bromo-6-hydroxy-4-methoxyphenyl, 2,4,6-trifluorophenyl, 2-bromo-6-fluoro-4-methylphenyl, 4-difluoromethoxy-2,6-dimethylphenyl, 2,6-dimethyl-4-ethoxyphenyl, 2,6-dimethyl-4-isopropoxyphenyl, 2,6-dimethyl-4-methylthiophenyl, 2,6-dimethyl-4-methylsulfonylophenyl, 2,6-dimethyl-4-methylsulfinylopheny- l, 2,3-dichlorophenyl, 4-methoxy-2,3-dimethylphenyl, 2-chloro-3-fluoro-4-methoxyphenyl, 2,3,4-trichlorophenyl and 4-methoxy-2,5-dimethylphenyl.

[0080] The "pharmaceutically acceptable salts" in the present invention include, for example, salts with an inorganic acid such as sulfuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid or the like; salts with an organic acid such as acetic acid, oxalic acid, lactic acid, tartaric acid, fumaric acid, maleic acid, citric acid, benzenesulfonic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, camphorsulfonic acid, ethanesulfonic acid, glucoheptonic acid, gluconic acid, glutamic acid, glycolic acid, malic acid, malonic acid, mandelic acid, galactaric acid, naphthalene-2-sulfonic acid or the like; salts with one or more metal ions such as lithium ion, sodium ion, potassium ion, calcium ion, magnesium ion, zinc ion, aluminium ion or the like; salts with amines such as ammonia, arginine, lysine, piperazine, choline, diethylamine, 4-phenylcyclohexylamine, 2-aminoethanol, benzathine or the like.

[0081] A compound of the present invention includes any isomers such as diastereomers, enantiomers, geometricisomers and tautomeric forms. In a compound represented by formula [I], if the cyclic amino group has one or more chiral carbons and/or if there is an axial chirality between Ar and pyrrolopyrimidine (or pyrrolopyridine) ring, several stereoisomers (diastereomers or enantiomers) can exist. The compound of the present invention includes the individual isomers and the racemic and non-racemic mixtures of the isomers.

[0082] Preferable examples of the compound of the present invention are as follows.

[0083] That is, preferable are compounds represented by the following formula [III] 4

[0084] (wherein the cyclic amino group is represented by the following formula [IV]: 5

[0085] in which the cyclic amino group is a 3- to 8-membered saturated cyclic amine or a 3- to 8-membered saturated cyclic amine bridged with C.sub.1-5alkylene or C.sub.1-4alkylene- O--C.sub.1-4alkylene between any different two carbon atoms of the cyclic amine, which cyclic amine is substituted with a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.s- up.3).sub.n--CN, R.sup.4 and R.sup.5 independently on the same or different carbon atoms of the cyclic amine;

[0086] Y is N or CR.sup.10;

[0087] R.sup.1 is hydrogen, hydroxy, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl;

[0088] R.sup.2 is hydrogen or C.sub.1-5alkyl;

[0089] R.sup.3 is hydrogen, cyano, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1- -5alkyl or hydroxy-C.sub.1-5alkyl;

[0090] m is an integer selected from 0, 1, 2, 3, 4 and 5;

[0091] n is 0 or 1;

[0092] R.sup.4 is hydrogen, hydroxy, hydroxy-C.sub.1-5alkyl, cyano, cyano-C.sub.1-5alkyl or C.sub.1-5alkyl;

[0093] R.sup.5 is hydrogen or C.sub.1-5alkyl;

[0094] R.sup.6 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy or --N(R.sup.11)R.sup.12;

[0095] R.sup.7 and R.sup.9 are the same or different, and independently are hydrogen, halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy, --N(R.sup.11a)R.sup.12a, --CO.sub.2R.sup.13, cyano, nitro, C.sub.1-5alkylthio, trifluoromethyl or trifluoromethoxy; or R.sup.7 and R.sup.8 are taken together to form --CH.sub.2--CH.sub.2--CH.s- ub.2--CH.sub.2-- or --CH.dbd.CH--CH.dbd.CH--;

[0096] R.sup.10 is hydrogen, C.sub.1-5alkyl, halogen, cyano or --CO.sub.2R.sup.19;

[0097] Ar is aryl or heteroaryl which aryl or heteroaryl is unsubstituted or substituted with 1 or more substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.2-5alkenyl, C.sub.2-5alkynyl, C.sub.1-5alkoxy, C.sub.1-5alkylthio, C.sub.1-5alkylsulfinyl, C.sub.1-5alkylsulfonyl, cyano, nitro, hydroxy, --CO.sub.2R.sup.19a--C(.dbd.O)R.sup.19a, CONR.sup.11bR.sup.12b, --OC(.dbd.O)R.sup.19a, --NR.sup.11bCO.sub.2R.sup.1- 9a, --S(O).sub.rNR.sup.11bR.sup.12b, hydroxy-C.sub.2-5alkylamino-C.sub.2-5- alkoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, fluoromethoxy, methylenedioxy, ethylenedioxy and --N(R.sup.20)R.sup.21;

[0098] R.sup.11 and R.sup.12 are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl;

[0099] R.sup.11a and R.sup.12a are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl;

[0100] R.sup.11b and R.sup.12b are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl;

[0101] R.sup.13 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, C.sub.1-5alkoxy- C.sub.1-5alkyl, C.sub.3-8cycloalkyloxy-C.sub.1-5alkyl or phenyl;

[0102] R.sup.19 is hydrogen or C.sub.1-5alkyl;

[0103] R.sup.19a is hydrogen or C.sub.1-5alkyl;

[0104] r is 1 or 2;

[0105] R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-5alkyl). More preferable are compounds represented by the formula [III] in which Y is N. More preferable are compounds represented by the formula [III] in which Y is N; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen. More preferable are compounds represented by the formula [III] in which Y is N; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 0, 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl). More preferable are compounds represented by the formula [III] in which wherein Y is N; the cyclic amino group is a 6-membered saturated cyclic amine; m is 0 or 1; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino.

[0106] Other preferable are compounds represented by the formula [III] in which Y is CR.sup.10. More preferable are compounds represented by the formula [III] in which Y is CR.sup.10; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.10 is hydrogen or halogen. More preferable are compounds represented by the formula [III] in which Y is CR.sup.10; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 0, 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; R.sup.10 is hydrogen or halogen; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl. More preferable are compounds represented by the formula [III] in which Y is CR.sup.10; the cyclic amino group is a 6-membered saturated cyclic amine; m is 0 or 1; n is 0; R.sup.17, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; R.sup.10 is hydrogen; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino.

[0107] Other preferable are compounds represented by the following formula [V]: 6

[0108] (wherein the cyclic amino group is represented by the following formula [VI]: 7

[0109] in which the cyclic amino group is a 3- to 8-membered saturated cyclic amine or a 3- to 8-membered saturated cyclic amine bridged with C.sub.1-5alkylene or C.sub.1-4alkylene- O--C.sub.1-4alkylene between any different two carbon atoms of the cyclic amine, which cyclic amine is substituted with a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.s- up.3).sub.n--OH, R.sup.4 and R.sup.5 independently on the same or different carbon atoms of the cyclic amine;

[0110] Y is N or CR.sup.10;

[0111] R.sup.1 is hydrogen, hydroxy, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl;

[0112] R.sup.2 is hydrogen or C.sub.1-5alkyl;

[0113] R.sup.3 is hydrogen, cyano, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1- -5alkyl or hydroxy-C.sub.1-5alkyl;

[0114] m is an integer selected from 0, 1, 2, 3, 4 and 5;

[0115] n is 0 or 1; with the proviso that when n is 0, m is an integer selected from 1, 2, 3, 4 and 5;

[0116] R.sup.4 is hydrogen, hydroxy, hydroxy-C.sub.1-5alkyl, cyano, cyano-C.sub.1-5alkyl or C.sub.1-5alkyl;

[0117] R.sup.5 is hydrogen or C.sub.1-5alkyl;

[0118] R.sup.6 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy or --N(R.sup.11)R.sup.12;

[0119] R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen, halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy, --N(R.sup.11a)R.sup.12a, --CO.sub.2R.sup.13, cyano, nitro, C.sub.1-5alkylthio, trifluoromethyl or trifluoromethoxy; or R.sup.7 and R.sup.8 are taken together to form --CH.sub.2--CH.sub.2--CH.s- ub.2--CH.sub.2-- or ----CH.dbd.CH--CH.dbd.CH--;

[0120] R.sup.10 is hydrogen, C.sub.1-5alkyl, halogen, cyano or --CO.sub.2R.sup.19;

[0121] Ar is aryl or heteroaryl which aryl or heteroaryl is unsubstituted or substituted with 1 or more substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.2-5alkenyl, C.sub.2-5alkynyl, C.sub.1-5alkoxy, C.sub.1-5alkylthio, C.sub.1-5alkylsulfinyl, C.sub.1-5alkylsulfonyl, cyano, nitro, hydroxy, --CO.sub.2R.sup.19a, --C(.dbd.O)R.sup.19a, --CONR.sup.11bR.sup.12b, --OC(.dbd.O)R.sup.19a, --NR.sup.11bCO.sub.2R.sup- .19a, --S(O).sub.rNR.sup.11bR.sup.12b, hydroxy-C.sub.2-5alkylamino-C.sub.2- -5alkoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, fluoromethoxy, methylenedioxy, ethylenedioxy and --N(R.sup.20)R.sup.21; with the proviso that when Y is N, and the cyclic amino group is 5-membered ring, then Ar is aryl or heteroaryl which aryl or heteroaryl is substituted with at least one of substituents which are selected from halogen and trifluoromethyl;

[0122] R.sup.11 and R.sup.12 are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl;

[0123] R.sup.11a and R.sup.12a are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl;

[0124] R.sup.11b and R.sup.12b are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl;

[0125] R.sup.13 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, C.sub.1-5alkoxy- C.sub.1-5alkyl, C.sub.3-8cycloalkyloxy-C.sub.1-5alkyl or phenyl;

[0126] R.sup.19 is hydrogen or C.sub.1-5alkyl;

[0127] R.sup.19a is hydrogen or C.sub.1-5alkyl;

[0128] r is 1 or 2;

[0129] R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-5alkyl). More preferable are compounds represented by the formula [V] in which Y is N. More preferable are compounds represented by the formula [V] in which Y is N;

[0130] m is an integer selected from 1, 2, 3, 4 and 5; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen. More preferable are compounds represented by the formula [V] in which Y is N; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; Ar. is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl); with the proviso that when the cyclic amino group is 5-membered ring, Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with at least one of substituents which are selected from halogen and trifluoromethyl. More preferable are compounds represented by the formula [V] in which Y is N; the cyclic amino group is a 6-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino.

[0131] Other preferable are compounds represented by the formula [V] in which Y is N; m is 1; n is 0; R.sup.1 is C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2, R.sup.4 and R.sup.5 are hydrogen. More preferable are compounds represented by the formula [V] in which Y is N; m is 1; n is 0; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; R.sup.1 is C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl). More preferable are compounds represented by the formula [V] in which Y is N; m is 1; n is 0; the cyclic amino group is a 6-membered saturated cyclic amine; R.sup.1 is C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino.

[0132] Other preferable are compounds represented by the formula [V] in which Y is N; m is an integer selected from 1, 2, 3, 4 and 5; n is 0; R.sup.1, R.sup.2 and R.sup.5 are hydrogen; R.sup.4 is cyano, wherein a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.sup.3).sub.n--OH and R.sup.4 are substituted on the same carbon atom of the cyclic amine. More preferable are compounds represented by the formula [V] in which Y is N; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2 and R.sup.5 are hydrogen; R.sup.4 is cyano; R.sup.6 is methyl; R.sup.7 and R.sup.5 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl), wherein a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.sup.3).sub.n--OH and R.sup.4 are substituted on the same carbon atom of the cyclic amine. More preferable are compounds represented by the formula [V] in which Y is N; the cyclic amino group is a 6-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2 and R.sup.5 are hydrogen; R.sup.4 is cyano; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino, wherein a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.sup.3).sub.n--OH and R.sup.4 are substituted on the same carbon atom of the cyclic amine.

[0133] Other preferable are compounds represented by the formula [V] in which wherein Y is CR.sup.10. More preferable are compounds represented by the formula [V] in which Y is CR.sup.10; m is an integer selected from 1, 2, 3, 4 and 5; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.10 is hydrogen or halogen. More preferable are compounds represented by the formula [V] in which Y is CR.sup.10; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; R.sup.10 is hydrogen or halogen; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl). More preferable are compounds represented by the formula [V] in which Y is CR.sup.10; the cyclic amino group is a 6-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; R.sup.10 is hydrogen; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino.

[0134] Other preferable are compounds represented by the formula [V] in which Y is CR.sup.10; m is 1; n is 0; R.sup.1 is C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.10 is hydrogen or halogen. More preferable are compounds represented by the formula [V] in which Y is CR.sup.10; m is 1; n is 0; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; R.sup.1 is C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; R.sup.10 is hydrogen or halogen; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl). More preferable are compounds represented by the formula [V] in which Y is CR.sup.10; m is 1; n is 0; the cyclic amino group is a 6-membered saturated cyclic amine; R.sup.1 is C.sub.1-5alkyl or hydroxy- C.sub.1-5alkyl; R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; R.sup.10 is hydrogen; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino.

[0135] Other preferable are compounds represented by the formula [V] in which Y is CR.sup.10; m is an integer selected from 1, 2, 3, 4 and 5; n is 0; R.sup.1, R.sup.2 and R.sup.5 are hydrogen; R.sup.4 is cyano; R.sup.10 is hydrogen or halogen, wherein a group represented by --(CR.sup.1R.sup.2).sub.m (CHR.sup.3)--OH and R.sup.4 are substituted on the same carbon atom of the cyclic amine. More preferable are compounds represented by the formula [V] in which Y is CR.sup.10; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2 and R.sup.5 are hydrogen; R.sup.4 is cyano; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; R.sup.10 is hydrogen or halogen; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl), wherein a group represented by (CR.sup.1R.sup.2).sub.m--- (CHR.sup.3).sub.n--OH and R.sup.4 are substituted on the same carbon atom of the cyclic amine. More preferable are compounds represented by the formula [V] in which Y is CR.sup.10; the cyclic amino group is a 6-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2 and R.sup.5 are hydrogen; R.sup.4 is cyano; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; R.sup.10 is hydrogen; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino, wherein a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.sup.3).sub.n--OH and R.sup.4 are substituted on the same carbon atom of the cyclic amine.

[0136] Other preferable are compounds represented by the following formula [VII]: 8

[0137] (wherein the cyclic amino group is represented by the following formula [VIII]: 9

[0138] in which the cyclic amino group is a 3- to 8-membered saturated cyclic amine or a 3- to 8-membered saturated cyclic amine bridged with C.sub.1-5alkylene or C.sub.1-4alkylene- O--C.sub.1-4alkylene between any different two carbon atoms of the cyclic amine, which cyclic amine is substituted with a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.s- up.3).sub.n--OR.sup.9, R.sup.4 and R.sup.5 independently on the same or different carbon atoms of the cyclic amine;

[0139] Y is N or CR.sup.10;

[0140] R.sup.1 is hydrogen, hydroxy, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl;

[0141] R.sup.2 is hydrogen or C.sub.1-5alkyl;

[0142] R.sup.3 is hydrogen, cyano, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1- -5alkyl or hydroxy-C.sub.1-5alkyl;

[0143] m is an integer selected from 0, 1, 2, 3, 4 and 5;

[0144] n is 0 or 1;

[0145] with the proviso that when n is 0, m is an integer selected from 1, 2, 3, 4 and 5;

[0146] R.sup.4 is hydrogen, hydroxy, hydroxy-C.sub.1-5alkyl, cyano, cyano-C.sub.1-5alkyl or C.sub.1-5alkyl;

[0147] R.sup.5 is hydrogen or C.sub.1-5alkyl;

[0148] R.sup.6 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy or --N(R.sup.11)R.sup.12;

[0149] R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen, halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy, N(R.sup.11a)R.sup.12a, --CO.sub.2R.sup.13, cyano, nitro, C.sub.1-5alkylthio, trifluoromethyl or trifluoromethoxy; or R.sup.7 and R.sup.8 are taken together to form --CH.sub.2--CH.sub.2--CH.s- ub.2--CH.sub.2-- or --CH.dbd.CH--CH.dbd.CH--;

[0150] R.sup.9 is C.sub.1-24acyl, Cl.sub.1-10alkoxycarbonyl, aryl-C.sub.1-5alkyloxycarbonyl, --CO--O--CHR.sup.14O--CO--R.sup.15, --P(.dbd.O)(OR.sup.14a)OR.sup.15a, --CO--(CH.sub.2).sub.p--(CHR.sup.16).s- ub.q--NR.sup.17R.sup.18, arylcarbonyl or heteroarylcarbonyl, wherein each said acyl, aryl and heteroaryl is unsubstituted or substituted with C.sub.1-5alkoxy, and C.sub.1-24acyl optionally includes one to six double bonds;

[0151] R.sup.10 is hydrogen, C.sub.1-5alkyl, halogen, cyano or --CO.sub.2R.sup.19;

[0152] Ar is aryl or heteroaryl which aryl or heteroaryl is unsubstituted or substituted with 1 or more substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.2-5alkenyl, C.sub.2-5alkynyl, C.sub.1-5alkoxy, C.sub.1-5alkylthio, C.sub.1-5alkylsulfinyl, C.sub.1-5alkylsulfonyl, cyano, nitro, hydroxy, --CO.sub.2R.sup.19a, C(.dbd.O)R.sup.19a, CONR.sup.11bR.sup.12b, --OC(.dbd.O)R.sup.19a, --NR.sup.11bCO.sub.2R.sup.1- 9a, --S(O).sub.rNR.sup.11bR.sup.12b, hydroxy-C.sub.2-5alkylamino-C.sub.2-5- alkoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, fluoromethoxy, methylenedioxy, ethylenedioxy and --N(R.sup.20)R.sup.21;

[0153] R.sup.11 and R.sup.12 are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl;

[0154] R.sup.11a and R.sup.12a are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl;

[0155] R.sup.11b and R.sup.12b are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl;

[0156] R.sup.13 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, C.sub.1-5alkoxy- C.sub.1-5alkyl, C.sub.3-8cycloalkyloxy-C.sub.1-5alkyl or phenyl;

[0157] R.sup.14 and R.sup.15 are the same or different, and independently are hydrogen, C.sub.1-5alkyl or aryl-C.sub.1-5alkyl;

[0158] R.sup.14a and R.sup.15a are the same or different, and independently are hydrogen, C.sub.1-5alkyl or aryl-C.sub.1-5alkyl;

[0159] R.sup.16 is hydrogen, C.sub.1-5alkyl, aryl, heteroaryl, aryl-C.sub.1-5alkyl, heteroaryl-C.sub.1-5alkyl, hydroxy-C.sub.1-5alkyl, hydroxycarbonyl-C.sub.1-5alkyl, hydroxyphenyl-C.sub.1-5alkyl, C.sub.1-5alkoxy- C.sub.1-5alkyl, amino-C.sub.1-5alkyl, guanidino-C.sub.1-5alkyl, mercapto-C.sub.1-5alkyl, C.sub.1-5alkylthio- C.sub.1-5alkyl or aminocarbonyl-C.sub.1-5alkyl;

[0160] R.sup.17 and R.sup.18 are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, C.sub.1-10acyl, C.sub.1-10alkoxycarbonyl and aryl-C.sub.1-5alkyloxycarbonyl, or R.sup.16 and R.sup.17 are taken together to form --CH.sub.2--, --CH.sub.2CH.sub.2--, --CH.sub.2CH.sub.2CH.sub.2-- or --CH.sub.2CH.sub.2CH.sub.2CH.sub.2--;

[0161] p is an integer selected from 0, 1, 2, 3, 4 and 5;

[0162] q is 0 or 1;

[0163] R.sup.19 is hydrogen or C.sub.1-5alkyl;

[0164] R.sup.19a is hydrogen or C.sub.1-5alkyl;

[0165] r is 1 or 2;

[0166] R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-5alkyl). More preferable are compounds represented by the formula [VII] in which Y is N. More preferable are compounds represented by the formula [VII] in which Y is N; m is an integer selected from 1, 2, 3, 4 and 5; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen. More preferable are compounds represented by the formula [VII] in which the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 1, 2, 3, 4 and 5; n is 0; Y is N; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.3 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl). More preferable are compounds represented by the formula [VII] in which the cyclic amino group is a 6-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; Y is N; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino.

[0167] Other preferable are compounds represented by the formula [VII] in which Y is CR.sup.10. More preferable are compounds represented by the formula [VII] in which Y is CR.sup.10; m is an integer selected from 1, 2, 3, 4 and 5; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen. More preferable are compounds represented by the formula [VII] in which Y is CR.sup.10; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; R.sup.10 is hydrogen or halogen; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl). More preferable are compounds represented by the formula [VII] in which Y is CR.sup.10; the cyclic amino group is a 6-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; R.sup.10 is hydrogen; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino.

[0168] Especially preferable compounds of the present invention are: 2-{1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo- [2,3-d]pyrimidin-4-yl]-piperidin-2-yl}-ethanol, 10

[0169] 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidin-2-yl}-ethanol, 11

[0170] 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidin-2-yl}-ethanol, 12

[0171] 2-{1-[7-(4-bromo-2,6-diethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]- pyrimidin-4-yl]-piperidin-2-yl}-ethanol, 13

[0172] 2-{1-[2,5-dimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]pyrim- idin-4-yl]-piperidin-2-yl}-ethanol, 14

[0173] 3-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidin-2-yl}-propan-1-ol, 15

[0174] 3-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidin-2-yl}-propan-1-ol, 16

[0175] {1-[7-(2,4-dibromo-6-methoxy-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]- pyrimidin-4-yl]-piperidin-3-yl}-methanol, 17

[0176] {1-[7-(2,4-dibromo-6-methylsulfanyl-phenyl)-2,5-dimethyl-7H-pyrrolo- [2,3-d]pyrimidin-4-yl]-piperidin-3-yl}-methanol, 18

[0177] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-piperidin-3-yl}-methanol, 19

[0178] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-piperidin-3-yl}-methanol, 20

[0179] {1-[2,5-dimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]pyrimid- in-4-yl]-piperidin-3-yl}-methanol, 21

[0180] 2-{1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-p- yrrolo[2,3-d]pyrimidin-4-yl]-piperidin-3-yl}-ethanol, 22

[0181] 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidin-3-yl}-ethanol, 23

[0182] 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidin-3-yl}-ethanol, 24

[0183] 2-{1-[2,5-dimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]pyrim- idin-4-yl)- piperidin-3-yl}-ethanol, 25

[0184] {1-[2,5,6-trimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyr- imidin-4-yl]-piperidin-4-yl}-methanol, 26

[0185] {1-[2,5-dimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimi- din-4-yl]-piperidin-4-yl}-methanol, 27

[0186] {1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-pyr- rolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, 28

[0187] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, 29

[0188] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-piperidin-4-yl}-methanol, 30

[0189] {1-[2-methyl-9-(2,4,6-trimethyl-phenyl)-9H-1,3,9-triaza-fluoren-4-y- l]-piperidin-4-yl}-methanol, 31

[0190] {1-[7-(4-bromo-2,6-diethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidin-4-yl}-methanol, 32

[0191] {1-[7-(4-bromo-2,6-diethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]py- rimidin-4-yl]-piperidin-4-yl}-methanol, 33

[0192] {1-[2,5,6-trimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]pyri- midin-4-yl]-piperidin-4-yl}-methanol, 34

[0193] {1-[2,5-dimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]pyrimid- in-4-yl]-piperidin-4-yl}-methanol, 35

[0194] {1-[7-(4-bromo-2,6-dichloro-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, 36

[0195] {1-[7-(4-bromo-2,6-dichloro-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-piperidin-4-yl}-methanol, 37

[0196] {1-[7-(2,6-dibromo-4-isopropyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2- ,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, 38

[0197] {1-[7-(2,6-dibromo-4-isopropyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, 39

[0198] {1-[7-(4-chloro-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3- -d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, 40

[0199] {1-[7-(4-chloro-2,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piper- idin-4-yl}-methanol, 41

[0200] 2-{1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-p- yrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-ethanol, 42

[0201] 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidin-4-yl}-ethanol, 43

[0202] 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidin-4-yl}-ethanol, 44

[0203] 2-{1-[2,5,6-trimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]py- rimidin-4-yl]piperidin-4-yl}-ethanol, 45

[0204] 2-{1-[2,5-dimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]pyrim- idin-4-yl]-piperidin-4-yl}-ethanol, 46

[0205] 3-{1-[2,5,6-trimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-piperidin-4-yl}-propan-1-ol, 47

[0206] 3-{1-[2,5-dimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyri- midin-4-yl]-piperidin-4-yl}-propan-1-ol, 48

[0207] 3-{1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-p- yrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-propan-1-ol, 49

[0208] 3-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidin-4-yl}-propan-1-ol, 50

[0209] 3-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidin-4-yl}-propan-1-ol, 51

[0210] 3-{1-[2,5-dimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]pyrim- idin-4-yl]-piperidin-4-yl}-propan-1-ol, 52

[0211] 3-{1-[7-(4-bromo-2,6-dichloro-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidin-4-yl}-propan-1-ol, 53

[0212] 3-{1-[7-(4-bromo-2,6-dichloro-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidin-4-yl}-propan-1-ol, 54

[0213] {1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-pyr- rolo[2,3-d]pyrimidin-4-yl]-3-methyl-piperidin-3-yl}-methanol, 55

[0214] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-3-methyl-piperidin-3-yl}-methanol, 56

[0215] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-3-methyl-piperidin-3-yl}-methanol, 57

[0216] 1-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidin-4-yl}-ethane-1,2-diol, 58

[0217] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-pyrrolidin-2-yl}-methanol 59

[0218] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-pyrrolidin-2-yl}-methanol, 60

[0219] 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-pyrrolidin-3-yl}-ethanol, 61

[0220] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-azepan-4-yl}-methanol, 62

[0221] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-azepan-4-yl}-methanol, 63

[0222] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-piperidin-2-yl}-acetonitrile, 64

[0223] 1-[2,5,6-trimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyri- midin-4-yl]-piperidine-3-carbonitrile, 65

[0224] 1-[2,5-dimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimid- in-4-yl]-piperidine-3-carbonitrile, 66

[0225] 1-[7-(2,4-dibromo-6-methylsulfanyl-phenyl)-2,5-dimethyl-7H-pyrrolo[- 2,3-d]pyrimidin-4-yl]-piperidine-3-carbonitrile, 67

[0226] 1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-pyrr- olo[2,3-d]pyrimidin-4-yl]-piperidine-3-carbonitrile, 68

[0227] 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidine-3-carbonitrile, 69

[0228] 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]py- rimidin-4-yl]-piperidine-3-carbonitrile, 70

[0229] 1-[7-(4-isopropyl-2-methylsulfanyl-phenyl)-2,5,6-trimethyl-7H-pyrro- lo[2,3-d]pyrimidin-4-yl]-piperidine-3-carbonitrile, 71

[0230] 1-[7-(4-isopropyl-2-methylsulfanyl-phenyl)-2,5-dimethyl-7H-pyrrolo[- 2,3-d]pyrimidin-4-yl]-piperidine-3-carbonitrile, 72

[0231] 1-[7-(2-bromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[- 2,3-d]pyrimidin-4-yl]-piperidine-3-carbonitrile, 73

[0232] 1-[7-(4-bromo-2,6-diethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]- pyrimidin-4-yl]-piperidine-3-carbonitrile, 74

[0233] 1-[7-(4-bromo-2,6-diethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyr- imidin-4-yl]-piperidine-3-carbonitrile, 75

[0234] {1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-pyr- rolo[2,3-d]pyrimidin-4-yl]-piperidin-3-yl}-acetonitrile, 76

[0235] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-piperidin-3-yl}-acetonitrile, 77

[0236] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-piperidin-3-yl}-acetonitrile, 78

[0237] 3-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidin-3-yl}-propionitrile, 79

[0238] 3-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidin-3-yl}-propionitrile, 80

[0239] 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidine-4-carbonitrile, 81

[0240] 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]py- rimidin-4-yl]-piperidine-4-carbonitrile, 82

[0241] {1-[2,5,6-trimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyr- imidin-4-yl]-piperidin-4-yl}-acetonitrile, 83

[0242] {1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-pyr- rolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 84

[0243] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 85

[0244] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 86

[0245] {1-[7-(4-bromo-2,6-diethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 87

[0246] {1-[7-(4-bromo-2,6-diethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]py- rimidin-4-yl]-piperidin-4-yl}-acetonitrile, 88

[0247] {1-[2,5,6-trimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]pyri- midin-4-yl]-piperidin-4-yl}-acetonitrile, 89

[0248] {1-[2,5-dimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]pyrimid- in-4-yl]-piperidin-4-yl}-acetonitrile, 90

[0249] {1-[7-(4-bromo-2,6-dichloro-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 91

[0250] {1-[7-(4-bromo-2,6-dichloro-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 92

[0251] {1-[7-(2,6-dibromo-4-isopropyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2- ,3-d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 93

[0252] {1-[7-(2,6-dibromo-4-isopropyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 94

[0253] {1-[7-(4-methoxy-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 95

[0254] {1-[7-(4-methoxy-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 96

[0255] {1-[7-(4-chloro-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3- -d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 97

[0256] {1-[7-(4-chloro-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]- pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 98

[0257] 8-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-8-aza-bicyclo[3.2.1]octane-3-carbonitrile, 99

[0258] 8-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]py- rimidin-4-yl]-8-aza-bicyclo[3.2.1]octane-3-carbonitrile, 100

[0259] 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-pyrrolidine-3-carbonitrile, 101

[0260] 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]py- rimidin-4-yl]-pyrrolidine-3-carbonitrile, 102

[0261] 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-azepane-4-carbonitrile, 103

[0262] 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]py- rimidin-4-yl]-azepane-4-carbonitrile, 104

[0263] 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-3-hydroxymethyl-piperidine-3-carbonitrile, 105

[0264] {1-[7-(4-isopropyl-2-methylsulfanyl-phenyl)-2,5-dimethyl-7H-pyrrolo- [2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, 106

[0265] {1-[7-(2-bromo-4-isopropyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]py- rimidin-4-yl]-piperidin-4-yl}-methanol, 107

[0266] {1-[7-(2,4-dibromo-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-- 4-yl]-piperidin-4-yl}-methanol, 108

[0267] {1-[7-(2,6-dibromo-4-chloro-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-piperidin-4-yl}-methanol, 109

[0268] 2-{1-[7-(2,6-dibromo-4-chloro-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidin-4-yl}-ethanol, 110

[0269] 1-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidin-4-yl}-propane-1,3-diol, 111

[0270] {1-[7-(2,6-dibromo-4-chloro-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 112

[0271] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-pyrrolidin-3-yl}-acetonitrile, 113

[0272] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-pyrrolidin-3-yl}-acetonitrile, 114

[0273] {1-[2,5-dimethyl-7-(2,4,6-trichloro-phenyl)-7H-pyrrolo[2,3-d]pyrimi- din-4-yl]-piperidin-4-yl}-methanol, 115

[0274] {1-[7-(2,6-dichloro-4-trifluoromethyl-phenyl)-2,5-dimethyl-7H-pyrro- lo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, 116

[0275] 3-{1-[7-(4-chloro-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2- ,3-d]pyrimidin-4-yl]-piperidin-4-yl}-propan-1-ol, 117

[0276] 1-[7-(4-chloro-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-piperidine-4-carbonitrile, 118

[0277] {1-[7-(2,6-Dichloro-4-trifluoromethyl-phenyl)-2,5-dimethyl-7H-pyrro- lo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 119

[0278] 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-azetidine-3-carbonitrile, 120

[0279] 1-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidin-4-yl}-ethanol, 121

[0280] 1-{1-[7-(4-isopropyl-2-methylsulfanyl-phenyl)-2,5-dimethyl-7H-pyrro- lo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-ethanol, 122

[0281] 1-{1-[7-(4-chloro-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2- ,3-d]pyrimidin-4-yl]-piperidin-4-yl}-ethanol, 123

[0282] 1-{1-[7-(4-chloro-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-piperidin-4-yl}-ethanol, 124

[0283] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-3-methyl-piperidin-4-yl}-methanol, 125

[0284] {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-3-methyl-piperidin-4-yl}-methanol, 126

[0285] {8-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-8-aza-bicyclo[3.2.1]oct-3-yl}-methanol, 127

[0286] {8-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-8-aza-bicyclo [3.2.1]oct-3-yl}-methanol, 128

[0287] {8-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-8-aza-bicyclo [3.2.1]oct-3-yl}-acetonitrile, 129

[0288] {8-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-8-aza-bicyclo[3.2.1]oct-3-yl}-acetonitrile, 130

[0289] 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidin-4-yl}-malononitrile, 131

[0290] 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidin-4-yl}-malononitrile, 132

[0291] 2-{1-[1-(2,4-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyri- din-4-yl]-piperidin-3-yl}-ethanol, 133

[0292] 2-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dim ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-3-yl}-ethanol, 134

[0293] {1-[1-(2,4-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridi- n-4-yl]-piperidin-4-yl}-methanol, 135

[0294] {1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]p- yridin-4-yl]-piperidin-4-yl}-methanol, 136

[0295] 2{-[1-(2,4-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridi- n-4-yl]-piperidin-4-yl}-ethanol, 137

[0296] 2-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidin-4-yl}-ethanol, 138

[0297] 3-{1-[1-(2,4-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyri- din-4-yl]-piperidin-4-yl}-propan-1-ol, 139

[0298] 3-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 140

[0299] 1-[1-(2,4-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin- -4-yl]-piperidine-3-carbonitrile, 141

[0300] 1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidine-3-carbonitrile, 142

[0301] {1-[1-(2,4-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridi- n-4-yl]-piperidin-3-yl}-acetonitrile, 143

[0302] 1-[1-(2,4-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin- -4-yl]-piperidine-4-carbonitrile, 144

[0303] 1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidine-4-carbonitrile, 145

[0304] {1-[1-(2,4-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridi- n-4-yl]-piperidin-4-yl}-acetonitrile, 146

[0305] 2-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-3-yl}-ethanol, 147

[0306] {1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-- b]pyridin-4-yl]-piperidin-4-yl}-methanol, 148

[0307] {1-[1-(4-chloro-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3- -b]pyridin-4-yl]-piperidin-4-yl}-methanol, 149

[0308] {1-[1-(4-chloro-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]- pyridin-4-yl]-piperidin-4-yl}-methanol, 150

[0309] 2-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 151

[0310] 2-{1-[1-(4-chloro-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2- ,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 152

[0311] 2-{1-[1-(4-chloro-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-- b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 153

[0312] 3-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 154

[0313] 3-{1-[1-(4-chloro-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2- ,3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 155

[0314] 3-{1-[1-(4-chloro-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-- b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 156

[0315] 1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidine-3-carbonitrile, 157

[0316] 1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidine-4-carbonitrile, 158

[0317] 1-[1-(4-chloro-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-- b]pyridin-4-yl]-piperidine-4-carbonitrile, 159

[0318] 1-[1-(4-chloro-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]p- yridin-4-yl]-piperidine-4-carbonitrile, 160

[0319] {1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-- b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile, 161

[0320] {1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]p- yridin-4-yl]-piperidin-4-yl}-acetonitrile, 162

[0321] {1-[1-(4-chloro-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]- pyridin-4-yl]-piperidin-4-yl}-acetonitrile, 163

[0322] {1-[1-(2,6-dibromo-4-isopropyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2- ,3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, 164

[0323] {1-[1-(2,6-dibromo-4-isopropyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-- b]pyridin-4-yl]-piperidin-4-yl}-methanol, 165

[0324] {1-[2,3,6-trimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyri- din-4-yl]-piperidin-4-yl}-methanol, 166

[0325] {1-[3,6-dimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyridin- -4-yl]-piperidin-4-yl}-methanol, 167

[0326] {1-[1-(4-bromo-2,6-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-- b]pyridin-4-yl]-piperidin-4-yl}-methanol, 168

[0327] {1-[1-(4-bromo-2,6-dichloro-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]p- yridin-4-yl]-piperidin-4-yl}-methanol, 169

[0328] {1-[2,3,6-trimethyl-1-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]pyr- idin-4-yl]-piperidin-4-yl}-methanol, 170

[0329] {1-[3,6-dimethyl-1-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]pyridi- n-4-yl]-piperidin-4-yl}-methanol, 171

[0330] {1-[1-(2,6-dibromo-4-chloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-- b]pyridin-4-yl]-piperidin-4-yl}-methanol, 172

[0331] {1-[1-(2,6-dibromo-4-chloro-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]p- yridin-4-yl]-piperidin-4-yl}-methanol, 173

[0332] {1-[1-(4-methoxy-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, 174

[0333] {1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidin-4-yl}-methanol, 175

[0334] {1-[1-(2-bromo-4-isopropyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidin-4-yl}-methanol, 176

[0335] {1-[1-(4-isopropyl-2-methylsulfanyl-phenyl)-3,6-dimethyl-1H-pyrrolo- [2,3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, 177

[0336] {1-[1-(2,4-dibromo-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-- yl]-piperidin-4-yl}-methanol, 178

[0337] {1-[1-(2-bromo-4-trifluoromethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, 179

[0338] {1-[2,3,6-trimethyl-1-(2,4,5-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyri- din-4-yl]-piperidin-4-yl}-methanol, 180

[0339] {1-[3,6-dimethyl-1-(2,4,5-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyridin- -4-yl]-piperidin-4-yl}-methanol, 181

[0340] 2-{1-[1-(2,6-dibromo-4-isopropyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo- [2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 182

[0341] 2-{1-[1-(2,6-dibromo-4-isopropyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 183

[0342] 2-{1-[2,3,6-trimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidin-4-yl-ethanol, 184

[0343] 2-{1-[3,6-dimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyrid- in-4-yl]-piperidin-4-yl]-ethanol, 185

[0344] 2-{1-[1-(4-bromo-2,6-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 186

[0345] 2-{1-[1-(4-bromo-2,6-dichloro-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidin-4-yl}-ethanol, 187

[0346] 2-{1-[2,3,6-trimethyl-1-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]p- yridin-4-yl]-piperidin-4-yl}-ethanol, 188

[0347] 2-{1-[3,6-dimethyl-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]pyridi- n-4-yl]-piperidin-4-yl}-ethanol, 189

[0348] 2-{1-[1-(2,6-dibromo-4-chloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 190

[0349] 2-{1-[1-(2,6-dibromo-4-chloro-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidin-4-yl}-ethanol, 191

[0350] 2-{1-[1-(4-methoxy-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[- 2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 192

[0351] 2-{1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3- -b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 193

[0352] 2-{1-[1-(2-bromo-4-isopropyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]- pyridin-4-yl]-piperidin-4-yl}-ethanol, 194

[0353] 2-{1-[1-(4-isopropyl-2-methylsulfanyl-phenyl)-3,6-dimethyl-1H-pyrro- lo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 195

[0354] 2-{1-[1-(2,4-dibromo-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-- 4-yl]-piperidin-4-yl}-ethanol, 196

[0355] 2-{1-[2,3,6-trimethyl-1-(2,4,5-tribromo-phenyl)-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidin-4-yl}-ethanol, 197

[0356] 2-{1-[3,6-dimethyl-1-(2,4,5-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyrid- in-4-yl]-piperidin-4-yl}-ethanol, 198

[0357] 2-{1-[5-bromo-1-(4-chloro-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrr- olo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 199

[0358] 3-{1-[1-(2,6-dibromo-4-isopropyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo- [2,3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 200

[0359] 3-{1-[1-(2,6-dibromo-4-isopropyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 201

[0360] 3-{1-[2,3,6-trimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidin-4-yl}-propan-1-ol, 202

[0361] 3-{1-[3,6-dimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyrid- in-4-yl]-piperidin-4-yl}-propan-1-ol, 203

[0362] 3-{1-[1-(4-bromo-2,6-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 204

[0363] 3-{1-[1-(4-bromo-2,6-dichloro-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 205

[0364] 3-{1-[2,3,6-trimethyl-1-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]p- yridin-4-yl]-piperidin-4-yl}-propan-1-ol, 206

[0365] 3-{1-[3,6-dimethyl-1-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]pyri- din-4-yl]-piperidin-4-yl}-propan-1-ol, 207

[0366] 3-{1-[1-(2,6-dibromo-4-chloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 208

[0367] 3-{1-[1-(2,6-dibromo-4-chloro-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 209

[0368] 3-{1-[1-(4-methoxy-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[- 2,3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 210

[0369] 3-{1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3- -b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 211

[0370] 3-{1-[1-(4-isopropyl-2-methylsulfanyl-phenyl)-3,6-dimethyl-1H-pyrro- lo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 212

[0371] 3-{1-[2,3,6-trimethyl-1-(2,4,5-tribromo-phenyl)-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidin-4-yl}-propan-1-ol, 213

[0372] 3-{1-[3,6-dimethyl-1-(2,4,5-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyrid- in-4-yl]-piperidin-4-yl}-propan-1-ol, 214

[0373] 1-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-4-yl}-ethane-1,2-diol, 215

[0374] 1-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidin-4-yl}-ethane-1,2-diol, 216

[0375] 1-1{1-[1-(4-bromo-2,6-dimethyl-phenyl)-23,6-trimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-4-yl}-propane-1,3-diol, 217

[0376] 1-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidin-4-yl}-propane-1,3-diol, 218

[0377] 1-[1-(2,6-dibromo-4-isopropyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidine-4-carbonitrile, 219

[0378] 1-[1-(2,6-dibromo-4-isopropyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidine-4-carbonitrile, 220

[0379] 1-[2,3,6-trimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyrid- in-4-yl]-piperidine-4-carbonitrile, 221

[0380] 1-[3,6-dimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyridin-- 4-yl]-piperidine-4-carbonitrile, 222

[0381] 1-[1-(4-bromo-2,6-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidine-4-carbonitrile, 223

[0382] 1-[1-(4-bromo-2,6-dichloro-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidine-4-carbonitrile, 224

[0383] 1-[2,3,6-trimethyl-1-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]pyri- din-4-yl]-piperidine-4-carbonitrile, 225

[0384] 1-[3,6-dimethyl-1-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]pyridin- -4-yl]-piperidine-4-carbonitrile, 226

[0385] 1-[1-(2,6-dibromo-4-chloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidine-4-carbonitrile, 227

[0386] 1-[1-(2,6-dibromo-4-chloro-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidine-4-carbonitrile, 228

[0387] 1-[1-(4-methoxy-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3- -b]pyridin-4-yl]-piperidine-4-carbonitrile, 229

[0388] 1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]- pyridin-4-yl]-piperidine-4-carbonitrile, 230

[0389] 1-[1-(2-bromo-4-isopropyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyr- idin-4-yl]-piperidine-4-carbonitrile, 231

[0390] 1-[1-(4-isopropyl-2-methylsulfanyl-phenyl)-3,6-dimethyl-1H-pyrrolo[- 2,3-b]pyridin-4-yl]-piperidine-4-carbonitrile, 232

[0391] 1-[1-(2,4-dibromo-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-y- l]-piperidine-4-carbonitrile, 233

[0392] 1-[1-(2-bromo-4-trifluoromethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3- -b]pyridin-4-yl]-piperidine-4-carbonitrile, 234

[0393] 1-[2,3,6-trimethyl-1-(2,4,5-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyrid- in-4-yl]-piperidine-4-carbonitrile, 235

[0394] 1-[3,6-dimethyl-1-(2,4,5-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyridin-- 4-yl]-piperidine-4-carbonitrile, 236

[0395] {1-[1-(4-chloro-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3- -b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile, 237

[0396] {1-[1-(2,6-dibromo-4-isopropyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2- ,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile, 238

[0397] {1-[1-(2,6-dibromo-4-isopropyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-- b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile, 239

[0398] {1-[2,3,6-trimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyri- din-4-yl]-piperidin-4-yl}-acetonitrile, 240

[0399] {1-[3,6-dimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyridin- -4-yl]-piperidin-4-yl}-acetonitrile, 241

[0400] {1-[1-(4-bromo-2,6-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-- b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile, 242

[0401] {1-[1-(4-bromo-2,6-dichloro-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]p- yridin-4-yl]-piperidin-4-yl}-acetonitrile, 243

[0402] {1-[2,3,6-trimethyl-1-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]pyr- idin-4-yl]-piperidin-4-yl}-acetonitrile, 244

[0403] {1-[3,6-dimethyl-1-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]pyridi- n-4-yl]-piperidin-4-yl}-acetonitrile, 245

[0404] {1-[1-(2,6-dibromo-4-chloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-- b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile, 246

[0405] {1-[1-(2,6-dibromo-4-chloro-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]p- yridin-4-yl]-piperidin-4-yl}-acetonitrile, 247

[0406] {1-[1-(4-methoxy-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile, 248

[0407] {1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidin-4-yl}-acetonitrile, 249

[0408] {1-[1-(2-bromo-4-isopropyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidin-4-yl}-acetonitrile, 250

[0409] {1-[1-(4-isopropyl-2-methylsulfanyl-phenyl)-3,6-dimethyl-1H-pyrrolo- [2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile, 251

[0410] {1-[1-(2,4-dibromo-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-- yl]-piperidin-4-yl}-acetonitrile, 252

[0411] {1-[1-(2-bromo-4-trifluoromethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,- 3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile, 253

[0412] {1-[3,6-dimethyl-1-(2,4,5-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyridin- -4-yl]-piperidin-4-yl}-acetonitrile, 254

[0413] carbonic acid 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-py- rrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmethyl ester ethyl ester, 255

[0414] pyridine-2-carboxylic acid 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-d- imethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmethyl ester, 256

[0415] methoxy-acetic acid 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl- -7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmethyl ester, 257

[0416] methoxy-acetic acid 1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl- -1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-ylmethyl ester, 258

[0417] carbonic acid benzyl ester 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-d- imethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmethyl ester, 259

[0418] decanoic acid 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-py- rrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmethyl ester, 260

[0419] 3-diethylamino-propionic acid 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,- 5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmethyl ester, 261

[0420] and phosphoric acid mono-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-di- methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmethyl}ester. 262

[0421] The compound represented by the formula [I] can be produced, for example, by the process shown in the following reaction scheme 1-4 [in the following reaction scheme, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, m, n, X, Y and Ar are as defined above; LG is chloro, bromo, iodo, methanesulfonyloxy, benzenesulfonyloxy, 4-toluenesulfonyloxy or trifluoromethanesulfonyloxy group; Z.sup.1 and Z.sup.2 are the same or different, and independently are chloride or bromide; R.sup.a and R.sup.b are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl; and X.sup.a is --(CHR.sup.3).sub.n--OH, --(CHR.sup.3).sub.n--CN or --CO.sub.2--(C.sub.1-5alkyl)]. 263

[0422] Step 1:

[0423] Compound (3), a compound of the present invention, can be obtained by reacting Compound (1) with Compound (2) in an inert solvent in the presence or absence of a base. Herein, the base includes, for example, amines such as triethylamine, N,N-diisopropylethylamine, pyridine and the like; inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium hydride and the like; metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like; metal amides such as sodium amide, lithium diisopropylamide and the like; and Grignard reagents such as methylmagnesium bromide and the like. The inert solvent includes, for example, alcohols such as methanol, ethanol, isopropyl alcohol, ethylene glycol and the like; ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like; hydrocarbons such as benzene, toluene, xylene and the like; amides such as N,N-dimethylformamide, N-methylpyrrolidone, N,N-dimethylacetamide and the like; acetonitrile; dimethyl sulfoxide; pyridine; water; and mixtures of solvents selected from these inert solvents.

[0424] The compound of the present invention can be converted to a salt in an inert solvent with an inorganic acid such as sulfuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid or the like, with an organic acid such as acetic acid, oxalic acid, lactic acid, tartaric acid, fumaric acid, maleic acid, citric acid, benzenesulfonic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, camphorsulfonic acid, ethanesulfonic acid, glucoheptonic acid, gluconic acid, glutamic acid, glycolic acid, malic acid, malonic acid, mandelic acid, galactaric acid, naphthalene-2-sulfonic acid or the like, with an inorganic base such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, zinc hydroxide, aluminum hydroxide or the like or with an organic base such as ammonia, arginine, lysine, piperazine, choline, diethylamine, 4-phenylcyclohexylamine, 2-aminoethanol, benzathine or the like. The inert solvent includes, for example, alcohols such as methanol, ethanol, isopropyl alcohol, ethylene glycol and the like; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like; hydrocarbons such as benzene, toluene and the like; esters such as ethyl acetate, ethyl formate and the like; ketones such as acetone, methylethylketone and the like; amides such as N,N-dimethylformamide, N-methylpyrrolidone, N,N-dimethylacetamide and the like; acetonitrile; dichloromethane; chloroform; dimethyl sulfoxide; pyridine; water; and mixtures of solvents selected from these inert solvents. 264

[0425] Step 2:

[0426] Compound (4) can be converted to Compound (6) by reacting Compound (4) with Compound (5) in an inert solvent in the presence or absence of a base. Herein, the base includes, for example, amines such as triethylamine, N,N-diisopropylethylamine, pyridine and the like; inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium hydride and the like; metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like; metal amides such as sodium amide, lithium diisopropylamide and the like; and Grignard reagents such as methyl magnesium bromide and the like. The inert solvent includes, for example, alcohols such as methanol, ethanol, isopropyl alcohol, ethylene glycol and the like; ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like; hydrocarbons such as benzene, toluene, xylene and the like; amides such as N,N-dimethylformamide, N-methylpyrrolidone, N,N-dimethylacetamide and the like; acetonitrile; dimethyl sulfoxide; pyridine; water; and mixtures of solvents selected from these inert solvents.

[0427] Step 3:

[0428] Compound (6) can be converted to Compound (7) by reacting Compound (6) with malononitrile in an inert solvent in the presence or absence of a base. Herein, the base includes, for example, amines such as triethylamine, N,N-diisopropylethylamine, pyridine and the like; inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium hydride, potassium hydride and the like; metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like; metal amides such as sodium amide, lithium diisopropylamide, lithium hexamethyldisilazamide, sodium hexamethyldisilazamide, potassium hexamethyldisilazamide and the like; alkyl lithiums such as methyl lithium, n-butyl lithium, sec-butyl lithium, tert-butyl lithium and phenyl lithium; and Grignard reagents such as methyl magnesium bromide and the like. The inert solvent includes, for example, alcohols such as methanol, ethanol, isopropyl alcohol, ethylene glycol and the like; ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like; hydrocarbons such as benzene, toluene and the like; amides such as N,N-dimethylformamide, N-methylpyrrolidone, N,N-dimethylacetamide and the like; acetonitrile; dimethyl sulfoxide; pyridine; water; and mixtures of solvents selected from these inert solvents.

[0429] Step 4:

[0430] Compound (7) can be converted to Compound (8) by acylation of amino group in Compound (7) and followed by formation of pyrimidine ring. The acylation and the formation of pyrimidine ring may occur continuously in one pot. The acylation can be achieved by reacting Compound (7) with an acylating reagent in an inert solvent in the presence or absence of a base or an acid. The following formation of pyrimidine ring can be carried out by heating the acylated compound in an inert solvent in the presence or absence of an acid. Herein, the acylating reagent includes, for example, halogenated acyls such as acetyl chloride, acetyl bromide, propionyl chloride, propionyl bromide, butyryl chloride, cyclopropanecarbonyl chloride, benzoyl chloride and the like; acid anhydride such as acetic anhydride, propionic anhydride, butyric anhydride, benzoic anhydride and the like. The base includes, for example, amines such as triethylamine, N,N-diisopropylethylamine, pyridine and the like; inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium hydride, potassium hydride and the like; metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like; metal amides such as sodium amide, lithium diisopropylamide, lithium hexamethyldisilazamide, sodium hexamethyldisilazamide, potassium hexamethyldisilazamide and the like; and Grignard reagents such as methyl magnesium bromide and the like. The acid includes, for example, organic acids such as formic acid, acetic acid, trifluoroacetic acid, benzenesulfonic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, trifluoromethanesulfonic acid and the like; inorganic acids such as sulfuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid, polyphosphoric acid, nitric acid or the like. The inert solvent includes, for example, alcohols such as methanol, ethanol, isopropyl alcohol, ethylene glycol and the like; ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like; hydrocarbons such as benzene, toluene, xylene and the like; amides such as N,N-dimethylformamide, N-methylpyrrolidone, N,N-dimethylacetamide and the like; acetonitrile; dimethyl sulfoxide; pyridine; acetic acid; water; and mixtures of solvents selected from these inert solvents.

[0431] Step 5

[0432] Compound (8) can be converted to Compound (9) by reacting (8) with a halogenating reagent or a sulfonating reagent in the presence or absence of a base in an inert solvent or without any solvent. Herein, the halogenating reagent includes, for example, phosphoryl chloride, phosphoryl bromide, phosphorous pentachloride, phosphorous trichloride, phosphorous pentabromide, phosphorous tribromide, thionyl chloride, thionyl bromide, oxalyl chloride, oxalyl bromide and the like. The sulfonating reagent includes, for example, p-toluenesulfonyl chloride, methanesulfonyl chloride, p-toluenesulfonic anhydride, methansulfonic anhydride, trifluoromethanesulfonic anhydride, N-phenylbis(trifluorometha- nesulfonimide) and the like. The base includes, for example, amines such as triethylamine, N,N-diisopropylethylamine, pyridine, N,N-dimethylaniline, N,N-diethylaniline and the like; inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium hydride and the like; metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like; metal amides such as sodium amide, lithium diisopropylamide and the like; and Grignard reagents such as methyl magnesium bromide and the like. The inert solvent includes, for example, alcohols such as methanol, ethanol, isopropyl alcohol, ethylene glycol and the like; ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like; hydrocarbons such as benzene, toluene and the like; amides such as N,N-dimethylformamide, N-methylpyrrolidone, N,N-dimethylacetamide and the like; dichloromethane; chloroform; acetonitrile; dimethyl sulfoxide; pyridine; water; and mixtures of solvents selected from these inert solvents.

[0433] Step 6

[0434] Compound (9) can be converted to Compound (11) by reacting Compound (9) with Compound (10) in the same method as step 1.

[0435] Step 7

[0436] Compound (11) can be converted to Compound (12) by reduction of Compound (11) with a conventional reducing agent in an inert solvent. Or if necessary, treatment with an acid in the presence or absence of inert solvent after the reduction can provide Compound (12). When X.sup.a is --CO.sub.2--(C.sub.1-5alkyl), the ester group can be converted to a hydroxymethyl group at the same time. Herein, the reducing agent includes, for example, lithium borohydride, sodium borohydride, calcium borohydride, lithium triethylborohydride, lithium tri-sec-butylborohydrid- e, potassium tri-sec-butylborohydride, zinc borohydride, borane, lithium trimethoxyborohydride, lithium triacetoxyborohydride, tetramethylammonium borohydride, lithium aluminum hydride, sodium aluminum hydride, sodium bis(2-methoxyethoxy)aluminum hydride, diisobutylaluminum hydride, trichlorosilane and the like. The reduction can be also carried out by hydrogenation using a catalyst including palladium, platinum dioxide, Raney nickel or the like. The acid includes, for example, organic acids such as acetic acid, trifluoroacetic acid, benzenesulfonic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid and the like; inorganic acids such as sulfuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid, polyphosphoric acid, nitric acid or the like. The inert solvent includes, for example, alcohols such as methanol, ethanol, isopropyl alcohol, ethylene glycol and the like; ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like; hydrocarbons such as benzene, toluene and the like; amides such as N,N-dimethylformamide, N-methylpyrrolidone, N,N-dimethylacetamide and the like; acetonitrile; dimethyl sulfoxide; pyridine; water; and mixtures of solvents selected from these inert solvents. 265

[0437] Step 8

[0438] Compoumd (7) can be converted to Compound (13) by reacting Compound (7) with ketones such as acetone and the like; vinyl ethers such as isopropenyl methyl ether and the like in an inert solvent in the presence or absence of an acid, and the following conversion from Compound (13) to Compound (14) can be carried out in the presence of base in an inert solvent. Herein, the acid includes, for example, organic acids such as acetic acid, trifluoroacetic acid, benzenesulfonic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid and the like. The base includes, for example, amines such as triethylamine, N,N-diisopropylethylamine, pyridine, 1,8-diazabicyclo[5.4.0]undec-7-ene and the like; inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium hydride and the like; metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like; metal amides such as sodium amide, lithium diisopropylamide, lithium hexamethyldisilazamide, sodium hexamethyldisilazamide, potassium hexamethyldisilazamide and the like; alkyl lithiums such as n-butyl lithium, sec-butyl lithium, tert-butyl lithium, methyl lithium and the like; and Grignard reagents such as methyl magnesium bromide and the like. The inert solvent includes, for example, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like; hydrocarbons such as benzene, toluene and the like; amides such as N,N-dimethylformamide, N-methylpyrrolidone, N,N-dimethylacetamide and the like; acetonitrile; dimethyl sulfoxide; pyridine; and mixtures of solvents selected from these inert solvents.

[0439] Step 9

[0440] Compound (14) can be converted to Compound (15) in the same manner as step 7.

[0441] Step 10

[0442] Compound (15) can be converted into Compound (16) via the corresponding diazonium compound. The conversion to the diazonium compound can be carried out using, for example, sodium nitrite, potassium nitrite, butylnitrite, tert-butylnitrite, iso-butylnitrite or the like in the presence or absence of an acid in an inert solvent. The acid includes, for example, inorganic acids such as sulfuric acid, hydrochloric acid, hydrobromic acid, nitric acid or the like. The inert solvent includes, for example, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like; hydrocarbons such as benzene, toluene and the like; amides such as N,N-dimethylformamide, N-methylpyrrolidone, N,N-dimethylacetamide and the like; acetonitrile; dimethyl sulfoxide; pyridine; water; and mixtures of solvents selected from these inert solvents.

[0443] Step 11

[0444] Compound (16) can be converted to Compound (17) in the same manner as step 5.

[0445] Step 12

[0446] When LG is chloride, bromide or iodide, Compound (17) can be obtained from Compound (15) directly by formation of the diazonium compound in the presence of one or more metal salts in an inert solvent. The formation of the diazonium compound can be carried out in the same manner as step 10. The metal salts include, for example, potassium iodide, potassium bromide, sodium iodide, sodium bromide, sodium chloride, copper (I) chloride, copper (II) chloride, copper (I) bromide, copper (II) bromide, copper (I) iodide and the like. The inert solvent includes, for example, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like; hydrocarbons such as benzene, toluene and the like; amides such as N,N-dimethylformamide, N-methylpyrrolidone, N,N-dimethylacetamide and the like; acetonitrile; dimethyl sulfoxide; pyridine; water; and mixtures of solvents selected from these inert solvents.

[0447] Step 13

[0448] Compound (17) can be converted to Compound (18) in the same manner as step 1.

[0449] Step 14

[0450] When X.sup.a is --CO.sub.2--(C.sub.1-5alkyl), the ester group can be converted to hydroxymethyl group in the same manner as step 7. 266

[0451] Step 15

[0452] Compound (20) can be converted to Compound (21) by a coupling of Compound (20) with the corresponding carboxylic acid using a conventional coupling reagent in the presence or absence of an additive or a base in an inert solvent or a coupling of Compound (20) with the corresponding acyl halide in the presence or absence of a base in an inert solvent. When R.sup.9 has protective groups of an amino group, a hydroxy group, a mercapto goup, a carboxy group, a guanidine group or a phosphoric acid group, those protective groups can be removed by conventional methods for deprotection (ref. Theodora W Greene and Peter G. M. Wuts "Protective Groups in Organic Synthesis"; Wiley-Interscience) after the above coupling. Herein, the coupling reagent includes, for example, N,N'-dicyclohexylcarbodiimide (DCC), 1-(3-dimethylaminopropyl)-3-ethylcar- bodiimide (EDC), 1,1'-carbonyldiimidazole (CDI), diphenylphosphorylazide (DPPA), diethyl cyanophosphate and the like. The additive includes, for example, 1-hydroxybenzotriazole (HOBt), N-hydroxysuccinimide, 4-dimethylaminopyridine and the like. The base includes amines such as triethylamine, N,N-diisopropylethylamine, pyridine, 1,8-diazabicyclo[5.4.0]undec-7-ene and the like; inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium hydride and the like; metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like; metal amides such as sodium amide, lithium diisopropylamide, lithium hexamethyldisilazamide, sodium hexamethyldisilazamide, potassium hexamethyldisilazamide and the like; alkyl lithiums such as n-butyl lithium, sec-butyl lithium, tert-butyl lithium, methyl lithium and the like; and Grignard reagents such as methyl magnesium bromide and the like. The inert solvent includes, for example, alcohols such as methanol, ethanol, isopropyl alcohol, ethylene glycol and the like; ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like; hydrocarbons such as benzene, toluene and the like; amides such as N,N-dimethylformamide, N-methylpyrrolidone, N,N-dimethylacetamide and the like; acetonitrile; dimethyl sulfoxide; pyridine; chloroform; dichloromethane; water; and mixtures of solvents selected from these inert solvents.

[0453] The compound of the present invention is useful as a therapeutic or prophylactic agent for diseases in which CRF is considered to be involved. For this purpose, the compound of the present invention can be formulated into tablets, pills, capsules, granules, powders, solutions, emulsions, suspensions, injections and the like by a conventional preparation technique by adding conventional fillers, binders, disintegrators, pH-adjusting agents, solvents, etc.

[0454] The compound of the present invention can be administered to an adult patient in a dose of 0.1 to 500 mg per day in one portion or several portions orally or parenterally. The dose can be properly increased or decreased depending on the kind of a disease and the age, body weight and symptom of a patient.

ENBODIMENTS OF THE INVENTION

[0455] The present invention is concretely explained with reference to the following examples and test example, but is not limited thereto.

Example 1

Synthesis of 2-{1-[7-(4-bromo-2,6-dimethylphenyl)-2,5-dimethyl-7H-pyrrolo[- 2,3-d]pyrimidin-4-yl]piperidin-4-yl}ethanol hydrochloride (compound 1-074)

[0456] 267

[0457] (1) A mixture of 7-(4-bromo-2,6-dimethylphenyl)-4-chloro-2,5-dimeth- yl-7H-pyrrolo[2,3-d]pyrimidine (6.0 g), 4-(2-hydroxyethyl)piperidine (3.2 g), N,N-diisopropylethylamine (3.2 g) in ethanol (15 mL) was heated at reflux for 5.5 hours. The reaction mixture was cooled to room temperature, poured into a saturated aqueous sodium hydrogencarbonate, and then extracted with ethyl acetate three times. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by a silica gel column chromatography (silica gel: Wako Gel (C200); eluent: hexane/ethyl acetate=2:1) to obtain 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)- -2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-ethanol as a white solid (6.41 g).

[0458] (2) To a suspension of 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-di- methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-ethanol (6.41 g) in ethanol (51 mL) was added 4 M HCl in ethyl acetate (4.2 mL) under ice-cooling. After removing the solvent, ethyl acetate (26 mL) was added to the residue. The mixture was stirred overnight to afford a white crystal. The crystal was collected by filtration to give the title compound (6.1 g).

[0459] m.p. 187-189.degree. C.

[0460] Table 1 and Table 2 list the compound obtained in Example 1 and compounds obtained by the similar procedure as in Example 1.

Example 2

Synthesis of optically active 1-[7-(2-bromo-4-trifluoromethylphenyl)-2,5,6- -trimethyl-7H-pyrrolo[2,3-d]pyrimidine-4-yl]piperidine-3-carbonitrile (compound 1-134, 1-135, 1-136 and 1-137)

[0461] 268

[0462] A mixture of 7-(2-bromo-4-trifluoromethylphenyl)-4-chloro-2,5,6-tri- methyl-7H-pyrrolo[2,3-d]pyrimidine (400 mg), piperidine-3-carbonitrile (290 mg), N,N-diisopropylethylamine (309 mg) in ethanol (2 mL) was heated at reflux for 6 days. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=5:1) to obtain two diastereoisomers (low polar diastereoisomer: 62 mg and high polar diastereoisomer: 36 mg) of 1-[7-(2-bromo-4-trifuoromethylphenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d- ]pyrimidine-4-yl]piperidine-3-carbonitrile.

[0463] Low Polar Diastereoisomer:

[0464] Rf value 0.64 (developing solvent: hexane/ethyl acetate=1:1, TLC plate Silica gel 60 F.sub.254 (Merck))

[0465] .sup.1H NMR (300 MHz) .delta. 1.68-1.83 (1H, m), 1.85-2.07 (3H, m), 2.08 (3H, s), 2.40 (3H, s), 2.51 (3H, s), 3.04-3.16 (1H, m), 3.26-3.62 (3H, m), 3.81-3.95 (1H, m), 7.43 (1H, d, J=8.2 Hz), 7.74 (1H, d, J=8.2 Hz), 8.02 (1H, s)

[0466] High Polar Diastereoisomer:

[0467] Rf value 0.56 (developing solvent: hexane/ethyl acetate=1:1, TLC plate Silica gel 60 F.sub.254 (Merck))

[0468] .sup.1H NMR (300 MHz) .delta. 1.65-1.83 (1H, m), 1.82-2.16 (6H, m), 2.40 (3H, s), 2.51 (3H, s), 3.04-3.17 (1H, m), 3.28-3.63 (3H, m), 3.85-3.98 (1H, m), 7.47 (1H, d, J=8.6 Hz), 7.74 (1H, d, J=8.6 Hz), 8.02 (1H, s)

[0469] The low polar diastereoisomer was optically resolved by high performance liquid chromatography to give each enantiomer.

[0470] Compound 1-134:

[0471] .sup.1H NMR (300 MHz) .delta. 1.68-1.83 (1H, m), 1.85-2.07 (3H, m), 2.08 (3H, s), 2.40 (3H, s), 2.51 (3H, s), 3.04-3.16 (1H, m), 3.26-3.62 (3H, m), 3.81-3.95 (1H, m), 7.43 (1H, d, J=8.2 Hz), 7.74 (1H, d, J=8.2 Hz), 8.02 (1H, s)

[0472] HPLC retention time: 20.0 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 2.0 cm I.D..times.25 cm, mobile phase: hexane-IPA=4:1, flow rate: 5.0 mL/min.)

[0473] Compound 1-135:

[0474] .sup.1H NMR (300 MHz) .delta. 1.68-1.83 (1H, m), 1.85-2.07 (3H, m), 2.08 (3H, s), 2.40 (3H, s), 2.51 (3H, s), 3.04-3.16 (1H, m), 3.26-3.62 (3H, m), 3.81-3.95 (1H, m), 7.43 (1H, d, J=8.2 Hz), 7.74 (1H, d, J=8.2 Hz), 8.02 (1H, s)

[0475] HPLC retention time: 23.0 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 2.0 cm I.D..times.25 cm, mobile phase: hexane-IPA=4:1, flow rate: 5.0 mL/min.)

[0476] The high polar diastereoisomer was also optically resolved by high performance liquid chromatography to give each enantiomer.

[0477] Compound 1-136:

[0478] .sup.1H NMR (300 MHz) .delta. 1.65-1.83 (1H, m), 1.82-2.16 (6H, m), 2.40 (3H, s), 2.51 (3H, s), 3.04-3.17 (1H, m), 3.28-3.63 (3H, m), 3.85-3.98 (1H, m), 7.47 (1H, d, J=8.6 Hz), 7.74 (1H, d, J=8.6 Hz), 8.02 (1H, s)

[0479] HPLC retention time: 21.4 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 2.0 cm I.D..times.25 cm, mobile phase: hexane-IPA=4:1, flow rate: 5.0 mL/min.)

[0480] Compound 1-137:

[0481] .sup.1H NMR (300 MHz) .delta. 1.65-1.83 (1H, m), 1.82-2.16 (6H, m), 2.40 (3H, s), 2.51 (3H, s), 3.04-3.17 (1H, m), 3.28-3.63 (3H, m), 3.85-3.98 (1H, m), 7.47 (1H, d, J=8.6 Hz), 7.74 (1H, d, J=8.6 Hz), 8.02 (1H, s)

[0482] HPLC retention time: 32.8 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 2.0 cm I.D..times.25 cm, mobile phase: hexane-IPA=4:1, flow rate: 5.0 mL/min.).

[0483] Table 1 lists the compounds obtained in Example 2.

Example 3

Synthesis of {1-[7-(4-bromo-2,6-dimethylphenyl)-2,5-dimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]piperidin-4-yl} methanol hydrochloride (1-054)

[0484] 269

[0485] (1) To a solution of 4-bromo-2,6-dimethylaniline (100.0 g) in tetrahydrofuran (400 mL) was added triethylamine (60.7 g) and 2-bromopropionyl bromide (129.5 g) under ice-cooling. The mixture was stirred at room temperature for 1 hour and cooled in an ice-cooling bath. To the reaction mixture was added a sodium hydrogencarbonate aqueous solution and the mixture was stirred at room temperature for 30 minutes. The precipitate was collected by filtration, washed with water and diethyl ether, and dried to give 2-bromo-N-(4-bromo-2,6-dimethylphenyl)pr- opionamide (151.2 g).

[0486] m.p. 187-189.degree. C. 270

[0487] (2) To a suspension of NaH (17.2 g) in tetrahydrofuran (500 mL) was added a solution of malononitrile (28.4 g) in tetrahydrofuran (100 mL) under ice-cooling and the mixture was stirred at room temperature for 1 hour. 2-Bromo-N-(4-bromo-2,6-dimethylphenyl)propionamide (120 g) was added and the mixture was heated at reflux for 1 hour. With ice-cooling, an ammonium chloride aqueous solution was added and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give a solid. The solid was washed with a mixture of diisopropylether and ethyl acetate and filtered, dried to give 2-amino-1-(4-bromo-2,6-dimethylphenyl)-4-methyl-5-oxo-4,5-dihydro-1H-pyrr- ole-3-carbonitrile (110.1 g).

[0488] m.p. 175-177.degree. C. 271

[0489] (3) To a suspension of 2-amino-1-(4-bromo-2,6-dimethylphenyl)-4-met- hyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carbonitrile (100 g) in acetic acid (100 mL) was added acetic anhydride (38.3 g) and the mixture was heated at reflux for 8 hours. After cooling to room temperature, the solvent was concentrated under reduced pressure, and water was added and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was crystallized from a mixture of ethyl acetate and diisopropylether to give 7-(4-bromo-2,6-dimethylphenyl)- -4-hydroxy-2,5-dimethyl-5,7-dihydropyrrolo[2,3-d]pyrimidin-6-one (56.6 g).

[0490] m.p. 271-273.degree. C. 272

[0491] (4) To a suspension of 7-(4-bromo-2,6-dimethylphenyl)-4-hydroxy-2,5- -dimethyl-5,7-dihydropyrrolo[2,3-d]pyrimidin-6-one (10.0 g) in phosphoryl chloride (25.7 mL) was added N,N-dimethylaniline (2.6 mL) and the mixture was heated at 120.degree. C. for 6 hours. After cooling to room temperature the mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with a sodium hydrogencarbonate aqueous solution and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give a solid. The solid was washed with diisopropylether to afford 7-(4-bromo-2,6-dimethylphenyl)-4-chloro-2,5-dimethyl-5,7-dihydropy- rrolo[2,3-d]pyrimidin-6-one (8.0 g)

[0492] m.p. 148-150.degree. C. 273

[0493] (5) A suspension of 7-(4-bromo-2,6-dimethylphenyl)-4-chloro-2,5-dim- ethyl-5,7-dihydropyrrolo[2,3-d]pyrimidin-6-one (7.5 g), ethyl isonipecotate (4.7 g), N,N-diisopropylethylamine (3.8 g) in ethanol (35 mL) was heated at reflux for 12 hours. The reaction mixture was stirred at room temperature to afford a solid. The solid was collected by filtration and washed with cold ethanol to give 1-[7-(4-bromo-2,6-dimethy- lphenyl)-2,5-dimethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]pi- peridine-4-carboxylic acid ethyl ester (7.7 g).

[0494] m.p. 159-161.degree. C. 274

[0495] (6) To a solution of lithium borohydride (2.61 g) in tetrahydrofuran (60 mL) was added a solution of 1-[7-(4-bromo-2,6-dimethy- lphenyl)-2,5-dimethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]pi- peridine-4-carboxylic acid ethyl ester (6.0 g) in a mixture of tetrahydrofuran (60 mL) and methanol (3 mL) dropwise over 10 minutes under ice-cooling. The reaction mixture was warmed up to room temperature and stirred for 3 hours. After cooling with an ice-bath, 6 M HCl aqueous solution (30 mL) was added and stirred at room temperature for 1 hour. The solution was made to alkaline (pH=9) with 6 M NaOH aqueous solution, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=1:1) to give {1-[7-(4-bromo-2,6-dimethylphenyl)-2,5-- dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl}methanol (4.6 g).

[0496] (7) To a suspension of {1-[7-(4-bromo-2,6-dimethylphenyl)-2,5-dimet- hyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl}methanol (0.71 g) in water (7 mL) was added concentrated HCl aqueous solution (0.15 mL) under ice-cooling. The mixture was stirred at room temperature for 5 minutes, cooled with an ice-bath again, and stirred for 15 minutes in an ice-cooling bath. The precipitate was collected by filtration, washed with water and dried to give the title compound (0.73 g).

Example 4

Synthesis of {1-[1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2- ,3-b]pyridin-4-yl]piperidin-4-yl}methanol hydrochloride (2-019)

[0497] 275

[0498] (1) To a solution of 2-amino-1-(4-chloro-2,6-dimethylphenyl)-4-meth- yl-5-oxo-4,5-dihydro-1H-pyrrole-3-carbonitrile (44.1 g), which was obtained in the same method as example 3, in tetrahydrofuran (220 mL) was added isopropenyl methyl ether (46.2 g) and p-toluenesulfonic acid (608 mg). The mixture was heated at reflux for 1 hour. After removing the solvent under reduced pressure, the residue was dissolved in tetrahydrofuran (500 mL) and cooled in an ice-NaCl bath. Lithium diisopropylamide in tetrahydrofuran solution (generated from 2.64M n-butyl lithium in hexane (127 mL), diisopropylamine (40.5 g) and tetrahydrofuran (300 mL)) was added dropwise over 30 minutes, and stirred at room temperature for 1 hour. To the reaction mixture a saturated NH.sub.4Cl aqueous solution was added and separated. The aqueous layer was extracted with CHCl.sub.3. The organic layer was washed with water, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=1:1) to give 4-amino-1-(4-chloro-2,6-dimethylphenyl)- -3,6-dimethyl-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (35.8 g) as an amorphous.

[0499] MS (ES, Pos.): 316 (M+1).sup.+, 318 (M+3).sup.+, 338 (M+Na).sup.+, 340 (M+Na+2).sup.+ 276

[0500] (2) To a suspension of lithium borohydride (11.6 g) in tetrahydrofuran (50 mL) was added a solution of 4-amino-1-(4-chloro-2,6-d- imethylphenyl)-3,6-dimethyl-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (33.7 g) in tetrahydrofuran (100 mL) was added. The mixture was stirred at reflux for 1 hour. After cooling with ice-cooling bath, a 6M HCl aqueous solution was added slowly. The solution was made to alkaline (pH=9) with 4 M NaOH aqueous solution, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=3:1) to give 1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-y- lamine (17.9 g) as a solid.

[0501] m.p. 190-192.degree. C. 277

[0502] (3) With ice-cooling, to a suspension of 1-(4-chloro-2,6-dimethylph- enyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-ylamine (17.9 g) in a mixure of 1,4-dioxane (45 mL) and water (45 mL) was added dropwise a mixture of concentrated H.sub.2SO.sub.4 (17.8 mL) and water (90 mL) and then a solution of NaNO.sub.2 (6.2 g) in water (62 mL). The mixture was stirred at room temperature for 20 minutes, and heated at 100.degree. C. for 1.5 hours. After cooling in an ice-cooling bath, the reaction mixture was poured into a cold saturated NaHCO.sub.3 aqueous solution and extracted with CHCl.sub.3. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give a solid. The solid was washed with a mixture of ethyl acetate and diisopropylether (1:5) to give 1-(4-chloro-2,6-dimethylphenyl- )-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-ol (14.4 g).

[0503] m.p. 260.degree. C. (decomp.) 278

[0504] (4) To a mixture of 1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H- -pyrrolo[2,3-b]pyridin-4-ol (14.4 g) and triethylamine (9.7 g) in CHCl.sub.3 (100 mL) was added trifluoromethansulfonic anhydride (9.7 mL) in an ice-cooling bath. After stirring for 10 miniutes, water was added and extracted with CHCl.sub.3. The organic layer was washed with water and brine successively, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give crude trifluoromethanesulfonic acid 1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethy- l-1H-pyrrolo[2,3-b]pyridin-4-yl ester (20.7 g).

[0505] A mixture of the crude trifluoromethanesulfonic acid 1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-y- l ester (20.5 g), ethyl isonipecotate (74.4 g) and N,N-diisopropylethylami- ne (12.2 g) was heated at 150-170.degree. C. for 1 hour. To the reaction mixture, water was added and extracted with ethyl acetate. The organic layer was washed with water, and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=5:1) to give 1-[1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-p- yrrolo[2,3-b]pyridin-4-yl]piperidine-4-carboxylic acid ethyl ester (16.6 g) as a pale yellow solid.

[0506] m.p. 140-142.degree. C. 279

[0507] (5) To a suspension of lithium borohydride (4.11 g) in tetrahydrofuran (50 mL) was added a solution of 1-[1-(4-chloro-2,6-dimeth- ylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carboxyl- ic acid ethyl ester (16.6 g) in a mixture of tertrahydrofuran (80 mL) and methanol (7.7 mL) in an ice-cooling bath. The mixture was stirred at room temperature for 2 hours. After cooling with an ice-cooling bath, water was added and the mixture was poured slowly into a 3M HCl aqueous solution. The solution was made to alkaline (pH=8) with 4 M NaOH aqueous solution to give a solid. The solid was collected by filtration and washed with water and diethylether. The solid was recrystallized from a mixture of ethanol and ethyl acetate to give {1-[1-(4-chloro-2,6-dimethyl- phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl}methanol (9.1 g).

[0508] (6) In the same method as example 1-(2), the title compound (8.0 g) was obtained from {1-[1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyr- rolo[2.3-b]pyridin-4-yl]piperidin-4-yl} methanol (9.1 g).

Example 5

Synthesis of carbonic acid 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl- -7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmethyl ester ethyl ester (3-001)

[0509] 280

[0510] {1-[7-(4-Bromo-2,6-dimethylphenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]py- rimidin-4-yl]piperidin-4-yl}methanol (1.15 g) synthesized in the similar manner as example 1 in tetrahydrofuran (25 mL) was stirred, then NaH (60% in paraffin, 0.10 g) was added and the mixture was heated at reflux for 3 hours. After cooling to 0.degree. C., ethyl chloroformate (0.28 g) in a small amount of tetrahydrofuran was added and the reaction mixture was allowed to reach room temperature and evaporated. The residue was purified over a silica gel on a glass filter (eluent: CH.sub.2Cl.sub.2/CH.sub.3CN=95:5 then 90:10) to give the title product (366 mg).

[0511] Table 3 lists the compound obtained in Example 5 and compounds obtained by the similar procedure as in Example 5.

Example 6

Synthesis of decanoic acid 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl- -7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmethyl ester (3-009)

[0512] 281

[0513] Under nitrogen atmosphere, {1-[7-(4-bromo-2,6-dimethylphenyl)-2,5-d- imethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl} methanol (1.15 g) synthesized in the similar manner as example 1 in tetrahydrofuran (25 mL) was stirred, then NaH (60% in paraffin, 0.10 g) was added and the mixture was heated at reflux overnight, giving mixture (I). Decanoic acid (0.45 g) in tetrahydrofuran (25 mL) was stirred, then 1,1'-carbonyldiimidazole (0.42 g) was added and the mixture was stirred overnight at room temperature, giving mixture (II). The mixture (II) was added dropwise to the mixture (I) at 0-5.degree. C. and the resulting reaction mixture was allowed to reach room temperature. The solvent was evaporated and the residue was purified over a silica gel on a glass filter (eluent: CH.sub.2Cl.sub.2/CH.sub.3CN=100:0, 95:5 then 90:10) to give the title product (888 mg).

[0514] Table 3 lists the compound obtained in Example 6 and compounds obtained by the similar procedure as in Example 6.

Example 7

Synthesis of eicosa-5,8,11,14-tetraenoic acid 1-[7-(4-bromo-2,6-dimethyl-p- henyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmethyl ester (3-020)

[0515] 282

[0516] Under nitrogen atmosphere, to a solution of 1-[7-(4-bromo-2,6-dimet- hylphenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl}met- hanol (606 mg) in CH.sub.2Cl.sub.2 (20 ml) was added arachidonic acid (500 mg), 4-dimethylaminopyridine (33 mg) and N,N'-dicyclohexylcarbodiimide (565 mg). The mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=7:1) to give the title compound (990 mg) as an oil.

[0517] Table 3 lists the compound obtained in Example 7 and compounds obtained by the similar procedure as in Example 7.

Example 8

Synthesis of (S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyr- imidin-4-yl]-piperidin-4-ylmethyl ester (3-014) and (S)-2-amino-3-(1H-indol-3-yl)-propionic acid 1-[7-(4-bromo-2,6-dimethyl-p- henyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmethyl ester (3-016)

[0518] 283

[0519] (1) A solution of N-(tert-butoxycarbonyl)-L-tryptophan (510 mg) and 1,1'-carbonyldiimidazole (330 mg) in acetonitrile (10 mL) was stirred at room temperature overnight. The solvent is evaporated and the residue is redissolved in toluene (5 mL). Sequentially {1-[7-(4-bromo-2,6-dimethylph- enyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl}methanol (594 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (40 .mu.L) were added and stirred at room temperature for 2 days. After evaporation of the solvent the residue was extracted with ethylacetate and dilute NaHCO.sub.3 solution. After the usual work-up the residue of the extract was purified over silica gel (eluent: CH.sub.2Cl.sub.2/MeOH=95:5) to give the title product 3-014 (578 mg). 284

[0520] (2) To a solution of 3-014 (1.16 g) in CH.sub.2Cl.sub.2 (200 mL) a 6M solution of HCl in isopropanol (2.7 mL) was added and stirred at room temperature for 2 days. After evaporation, the residue is purified by reversed-phase chromatography (BDS RP18, 8 .mu.m particle size, 200 g, ID 5 cm column, eluent: (0.5% NH.sub.4Ac/CH.sub.3CN: 9:1 (v/v))/CH.sub.3CN 85/15 to 1/9 gradient). After partial evaporation of the aqueous fractions a fine precipitate of pure compound is formed and recuperated, yielding the tiltle compound 3-016 (139 mg). The aqueous filtrate was extracted with CH.sub.2Cl.sub.2 and the organic extract was washed with dilute ammonia. After the usual work-up of the organic extract some more product 3-016 was recuperated (304 mg).

Example 9

Synthesis of phosphoric acid 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimeth- yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmethyl ester diethyl ester (3-017)

[0521] 285

[0522] Under nitrogen atmosphere, to a solution of {1-[7-(4-bromo-2,6-dime- thylphenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl}me- thanol (0.50 g) and 4-dimethylaminopyridine (0.55 g) in CH.sub.2Cl.sub.2 (50 mL) at 0.degree. C. diethyl chlorophosphate (0.38 g) was added dropwise and the reaction is slowly heated up to room temperature. The reaction mixture is poured on ice-water and extracted with CH.sub.2Cl.sub.2. After the usual work-up the residue is purified over silica gel on a glass filter (eluent: CH.sub.2Cl.sub.2/MeOH=98:2) yielding product 3-017 (0.31 g).

Example 10

Synthesis of phosphoric acid mono-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-- dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmethyl}ester (3-018)

[0523] 286

[0524] {1-[7-(4-bromo-2,6-dimethylphenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]py- rimidin-4-yl]piperidin-4-yl}methyl diphenoxyphosphate ester (1.8 g), which was produced in a similar way as in example 9, was dissolved in 50% NaOH (1 mL) and dioxane (50 mL) and stirred at 60.degree. C. for several hours until completion of the hydrolysis. The solution was treated with water (25 mL), acidified with HCl until pH=2 and extracted five times with portions CH.sub.2Cl.sub.2, using NaCl to improve the phase separation. After the usual work-up the residue is purified over silica gel on a glass filter (eluent: CH.sub.2Cl.sub.2/MeOH=9:1 to pure MeOH) yielding the title product 3-018 (0.38 g).

1TABLE 1*.sup.1 287 Com. No. Ex. No. 288 R.sup.6 R.sup.7 R.sup.8 --Ar melting point (.degree. C.) (solvent for crystallization) 1-001 1 289 CH.sub.3 CH.sub.3 CH.sub.3 290 142-144 (hexane) 1-002 1 291 CH.sub.3 CH.sub.3 H 292 124-126 (hexane) 1-003 1 293 CH.sub.3 CH.sub.3 CH.sub.3 294 amorphous 1-004 1 295 CH.sub.3 CH.sub.3 CH.sub.3 296 146-148*.sup.2(EtOAc/EtOH) 1-005 1 297 CH.sub.3 CH.sub.3 H 298 amorphous 1-006 1 299 CH.sub.3 CH.sub.3 CH.sub.3 300 144-146 (hexane) 1-007 1 301 CH.sub.3 CH.sub.3 H 302 121-122 (hexane) 1-008 1 303 CH.sub.3 CH.sub.3 H 304 141-143*.sup.2(EtOAc/EtOH) 1-009 1 305 CH.sub.3 CH.sub.3 CH.sub.3 306 134-136*.sup.2(EtOAc/EtOH) 1-010 1 307 CH.sub.3 CH.sub.3 H 308 157-159*.sup.2(EtOAc/EtOH) 1-011 1 309 CH.sub.3 CH.sub.3 CH.sub.3 310 amorphous 1-012 1 311 CH.sub.3 CH.sub.3 H 312 amorphous 1-013 1 313 CH.sub.3 CH.sub.3 H 314 amorphous*.sup.3 1-014 1 315 CH.sub.3 CH.sub.3 H 316 amorphous*.sup.3 1-015 1 317 CH.sub.3 CH.sub.3 CH.sub.3 318 amorphous 1-016 1 319 CH.sub.3 CH.sub.3 CH.sub.3 320 amorphous 1-017 1 321 CH.sub.3 CH.sub.3 CH.sub.3 322 144-146*.sup.2*.sup.4(EtOAc/Et- OH) 1-018 1 323 CH.sub.3 CH.sub.3 CH.sub.3 324 131-133*.sup.2*.sup.4(EtOAc/EtOH) 1-019 1 325 CH.sub.3 CH.sub.3 H 326 amorphous 1-020 1 327 CH.sub.3 CH.sub.3 H 328 152-154*.sup.2*.sup.4(EtOAc/EtOH) 1-021 1 329 CH.sub.3 CH.sub.3 H 330 145-147*.sup.2*.sup.4(EtOAc) 1-022 1 331 CH.sub.3 CH.sub.3 CH.sub.3 332 amorphous*.sup.3 1-023 1 333 CH.sub.3 CH.sub.3 H 334 amorphous 1-024 1 335 CH.sub.3 CH.sub.3 CH.sub.3 336 amorphous 1-025 1 337 CH.sub.3 CH.sub.3 H 338 amorphous 1-026 1 339 CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 340 amorphous 1-027 1 341 CH.sub.3 CH.sub.3 CH.sub.3 342 amorphous*.sup.3 1-028 1 343 CH.sub.3 --(CH.sub.2).sub.4-- 344 amorphous 1-029 1 345 CH.sub.3 --CH.dbd.CH--CH.dbd.CH-- 346 amorphous 1-030 1 347 CH.sub.3 CH.sub.3 CH.sub.3 348 amorphous 1-031 1 349 CH.sub.3 CH.sub.3 H 350 amorphous 1-032 1 351 CH.sub.3 CH.sub.3 H 352 159-161*.sup.2(EtOAc/Et- OH) 1-033 1 353 CH.sub.3 CH.sub.3 CH.sub.3 354 163-164*.sup.2(EtOAc/EtOH) 1-034 1 355 CH.sub.3 CH.sub.3 H 356 160-162*.sup.2(EtOAc/EtOH) 1-035 1 357 CH.sub.3 CH.sub.3 H 358 157-159*.sup.2(EtOAc/EtOH) 1-036 1 359 CH.sub.3 CH.sub.3 CH.sub.3 360 amorphous 1-037 1 361 CH.sub.3 CH.sub.3 H 362 amorphous 1-038 1 363 CH.sub.3 CH.sub.3 CH.sub.3 364 159-161 (IPE) 1-039 1 365 CH.sub.3 CH.sub.3 CH.sub.3 366 amorphous 1-040 1 367 CH.sub.3 CH.sub.3 H 368 amorphous 1-041 1 369 CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 370 amorphous 1-042 1 371 CH.sub.3 --(CH.sub.2).sub.4-- 372 134-136*.sup.5 1-043 1 373 CH.sub.3 --CH.dbd.CH--CH.dbd.CH-- 374 amorphous 1-044 1 375 CH.sub.3 CH.sub.3 CH.sub.3 376 amorphous 1-045 1 377 CH.sub.3 CH.sub.3 H 378 amorphous 1-046 1 379 CH.sub.3 CH.sub.3 H 380 172-174*.sup.2(EtOAc/Et- OH) 1-047 1 381 CH.sub.3 CH.sub.3 CH.sub.3 382 150-152*.sup.2(EtOAc/EtOH) 1-048 1 383 CH.sub.3 CH.sub.3 H 384 177-179*.sup.2(EtOAc/EtOH) 1-049 1 385 CH.sub.3 CH.sub.3 H 386 156-158*.sup.2(EtOAc/EtOH) 1-050 1 387 CH.sub.3 CH.sub.3 CH.sub.3 388 170-172 (hexane) 1-051 1 389 CH.sub.3 CH.sub.3 H 390 178-180 (hexane) 1-052 1 391 CH.sub.3 CH.sub.3 CH.sub.3 392 157-159 (IPE/hexane) 1-053 1 393 CH.sub.3 CH.sub.3 CH.sub.3 394 167-169*.sup.2(EtOAc) 1-054 1 395 CH.sub.3 CH.sub.3 H 396 173-175*.sup.2(EtOH) 1-055 1 397 CH.sub.3 --(CH.sub.2).sub.4-- 398 177-179 (IPE) 1-056 1 399 CH.sub.3 --CH.dbd.CH--CH.dbd.CH-- 400 amorphous 1-057 1 401 CH.sub.3 CH.sub.3 CH.sub.3 402 amorphous 1-058 1 403 CH.sub.3 CH.sub.3 H 404 166-168*.sup.2(EtOAc) 1-059 1 405 CH.sub.3 CH.sub.3 CH.sub.3 406 155-157*.sup.2(EtOAc) 1-060 1 407 CH.sub.3 CH.sub.3 H 408 176-178*.sup.2(EtOAc) 1-061 1 409 CH.sub.3 CH.sub.3 CH.sub.3 410 164-166*.sup.2(EtOAc) 1-062 1 411 CH.sub.3 CH.sub.3 H 412 170-172*.sup.2(EtOAc) 1-063 1 413 CH.sub.3 CH.sub.3 CH.sub.3 414 amorphous*.sup.2 1-064 1 415 CH.sub.3 CH.sub.3 H 416 164-166*.sup.2(EtOAc) 1-065 1 417 CH.sub.3 CH.sub.3 CH.sub.3 418 188-190*.sup.2(EtOAc) 1-066 1 419 CH.sub.3 CH.sub.3 H 420 184-186*.sup.2(EtOAc) 1-067 1 421 CH.sub.3 CH.sub.3 CH.sub.3 422 179-181*.sup.2(EtOAc) 1-068 1 423 CH.sub.3 CH.sub.3 H 424 178-180*.sup.2(EtOAc) 1-069 1 425 CH.sub.3 CH.sub.3 H 426 197-199*.sup.2(EtOAc/EtOH) 1-070 1 427 CH.sub.3 CH.sub.3 CH.sub.3 428 155-157*.sup.2(EtOAc) 1-071 1 429 CH.sub.3 CH.sub.3 H 430 167-169*.sup.2(EtOAc/EtOH) 1-072 1 431 CH.sub.3 CH.sub.3 CH.sub.3 432 220-222 (hexane) 1-073 1 433 CH.sub.3 CH.sub.3 CH.sub.3 434 212-214*.sup.2(EtOAc) 1-074 1 435 CH.sub.3 CH.sub.3 H 436 187-189*.sup.2(EtOAc) 1-075 1 437 CH.sub.3 CH.sub.3 CH.sub.3 438 180-182*.sup.2(hexane) 1-076 1 439 CH.sub.3 CH.sub.3 H 440 188-190*.sup.2(IPE) 1-077 1 441 CH.sub.3 CH.sub.3 CH.sub.3 442 179-181*.sup.2(EtOAc/EtOH) 1-078 1 443 CH.sub.3 CH.sub.3 H 444 194-196*.sup.2(EtOAc/EtOH- ) 1-079 1 445 CH.sub.3 CH.sub.3 CH.sub.3 446 199-201*.sup.2(EtOAc/EtOH) 1-080 1 447 CH.sub.3 CH.sub.3 H 448 193-195*.sup.2(EtOAc/EtOH) 1-081 1 449 CH.sub.3 CH.sub.3 CH.sub.3 450 164-166*.sup.2(EtOAc/EtOH) 1-082 1 451 CH.sub.3 CH.sub.3 H 452 177-179*.sup.2(EtOAc/EtOH) 1-083 1 453 CH.sub.3 CH.sub.3 CH.sub.3 454 170-172*.sup.2(EtOAc/EtOH) 1-084 1 455 CH.sub.3 CH.sub.3 H 456 162-164*.sup.2(EtOAc) 1-085 1 457 CH.sub.3 CH.sub.3 CH.sub.3 458 168-170*.sup.2(EtOAc) 1-086 1 459 CH.sub.3 CH.sub.3 H 460 187-189*.sup.2(EtOAc/EtOH) 1-087 1 461 CH.sub.3 CH.sub.3 CH.sub.3 462 183-184 (hexane) 1-088 1 463 CH.sub.3 CH.sub.3 H 464 165-167 (hexane) 1-089 1 465 CH.sub.3 CH.sub.3 CH.sub.3 466 191-193 (IPA) 1-090 1 467 CH.sub.3 CH.sub.3 CH.sub.3 468 189-191*.sup.2(THF/EtOAc) 1-091 1 469 CH.sub.3 CH.sub.3 H 470 202-204*.sup.2(EtOAc/EtOH) 1-092 1 471 CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 472 amorphous 1-093 1 473 CH.sub.3 --(CH.sub.2).sub.4-- 474 177-179 (IPE) 1-094 1 475 CH.sub.3 --CH.dbd.CH--CH.dbd.CH-- 476 amorphous 1-095 1 477 CH.sub.3 CH.sub.3 CH.sub.3 478 175-177*.sup.2(hexane) 1-096 1 479 CH.sub.3 CH.sub.3 H 480 174-176*.sup.2(EtOAc) 1-097 1 481 CH.sub.3 CH.sub.3 H 482 207-209*.sup.2(EtOAc/EtOH) 1-098 1 483 CH.sub.3 CH.sub.3 CH.sub.3 484 205-207*.sup.2(EtOAc/EtOH) 1-099 1 485 CH.sub.3 CH.sub.3 H 486 195-197*.sup.2(EtOAc/EtOH) 1-100 1 487 CH.sub.3 CH.sub.3 H 488 192-194*.sup.2(EtOAc/EtOH) 1-101 1 489 CH.sub.3 CH.sub.3 CH.sub.3 490 175-177*.sup.2(EtOAc) 1-102 1 491 CH.sub.3 CH.sub.3 H 492 158-160*.sup.2(EtOAc/EtOH) 1-103 1 493 CH.sub.3 CH.sub.3 CH.sub.3 494 amorphous 1-104 1 495 CH.sub.3 CH.sub.3 CH.sub.3 496 amorphous 1-105 1 497 CH.sub.3 CH.sub.3 H 498 amorphous 1-106 1 499 CH.sub.3 CH.sub.3 CH.sub.3 500 amorphous 1-107 1 501 CH.sub.3 CH.sub.3 H 502 amorphous 1-108 1 503 CH.sub.3 CH.sub.3 CH.sub.3 504 206-208 (IPE) 1-109 1 505 CH.sub.3 CH.sub.3 H 506 161-163 (IPE) 1-110 1 507 CH.sub.3 CH.sub.3 CH.sub.3 508 amorphous 1-111 1 509 CH.sub.3 CH.sub.3 H 510 141-143 (IPE) 1-112 1 511 CH.sub.3 CH.sub.3 CH.sub.3 512 184-186*.sup.2(EtOH) 1-113 1 513 CH.sub.3 CH.sub.3 H 514 181-182 (IPE) 1-114 1 515 CH.sub.3 CH.sub.3 CH.sub.3 516 amorphous 1-115 1 517 CH.sub.3 CH.sub.3 CH.sub.3 518 167-169*.sup.2*.sup.4(EtOAc) 1-116 1 519 CH.sub.3 CH.sub.3 H 520 amorphous*.sup.2*.sup.4 1-117 1 521 CH.sub.3 CH.sub.3 CH.sub.3 522 148-150*.sup.2*.sup.4(EtOA- c) 1-118 1 523 CH.sub.3 CH.sub.3 H 524 amorphous*.sup.2*.sup.4 1-119 1 525 CH.sub.3 CH.sub.3 CH.sub.3 526 214-216*.sup.2(EtOAc) 1-120 1 527 CH.sub.3 CH.sub.3 H 528 153-155*.sup.2(EtOH/EtOAc) 1-121 1 529 CH.sub.3 CH.sub.3 CH.sub.3 530 214-215*.sup.2(EtOAc) 1-122 1 531 CH.sub.3 CH.sub.3 H 532 148-150*.sup.2(EtOH/EtOAc) 1-123 1 533 CH.sub.3 CH.sub.3 CH.sub.3 534 170-172*.sup.2(EtOAc) 1-124 1 535 CH.sub.3 CH.sub.3 H 536 91-93*.sup.2(EtOH/EtOAc) 1-125 1 537 CH.sub.3 CH.sub.3 CH.sub.3 538 amorphous 1-126 1 539 CH.sub.3 CH.sub.3 H 540 amorphous 1-127 1 541 CH.sub.3 CH.sub.3 H 542 amorphous 1-128 1 543 CH.sub.3 CH.sub.3 H 544 amorphous 1-129 1 545 CH.sub.3 CH.sub.3 CH.sub.3 546 amorphous 1-130 1 547 CH.sub.3 CH.sub.3 CH.sub.3 548 amorphous 1-131 1 549 CH.sub.3 CH.sub.3 H 550 amorphous 1-132 1 551 CH.sub.3 CH.sub.3 CH.sub.3 552 amorphous*.sup.3 1-133 1 553 CH.sub.3 CH.sub.3 H 554 amorphous 1-134 1 555 CH.sub.3 CH.sub.3 CH.sub.3 556 amorphous*.sup.4 1-135 1 557 CH.sub.3 CH.sub.3 CH.sub.3 558 amorphous*.sup.4 1-136 1 559 CH.sub.3 CH.sub.3 CH.sub.3 560 amorphous*.sup.4 1-137 1 561 CH.sub.3 CH.sub.3 CH.sub.3 562 amorphous*.sup.4 1-138 1 563 CH.sub.3 CH.sub.3 H 564 amorphous 1-139 1 565 CH.sub.3 --(CH.sub.2).sub.4-- 566 173-175*.sup.5 1-140 1 567 CH.sub.3 --CH.dbd.CH--CH.dbd.CH-- 568 amorphous 1-141 1 569 CH.sub.3 CH.sub.3 CH.sub.3 570 amorphous 1-142 1 571 CH.sub.3 CH.sub.3 H 572 amorphous 1-143 1 573 CH.sub.3 CH.sub.3 CH.sub.3 574 amorphous 1-144 1 575 CH.sub.3 CH.sub.3 CH.sub.3 576 amorphous 1-145 1 577 CH.sub.3 CH.sub.3 H 578 147-149 (hexane) 1-146 1 579 CH.sub.3 CH.sub.3 CH.sub.3 580 amorphous 1-147 1 581 CH.sub.3 CH.sub.3 H 582 amorphous 1-148 1 583 CH.sub.3 CH.sub.3 CH.sub.3 584 195-197*.sup.2(EtOAc) 1-149 1 585 CH.sub.3 CH.sub.3 H 586 amorphous*.sup.2 1-150 1 587 CH.sub.3 CH.sub.3 CH.sub.3 588 164-166*.sup.2(EtOAc) 1-151 1 589 CH.sub.3 CH.sub.3 H 590 168-170*.sup.2(EtOAc) 1-152 1 591 CH.sub.3 CH.sub.3 CH.sub.3 592 145-147*.sup.2(EtOAc/IP- E) 1-153 1 593 CH.sub.3 CH.sub.3 CH.sub.3 594 182-184 (hexane) 1-154 1 595 CH.sub.3 CH.sub.3 CH.sub.3 596 166-168*.sup.2(IPE) 1-155 1 597 CH.sub.3 CH.sub.3 H 598 145-146*.sup.2(EtOAc) 1-156 1 599 CH.sub.3 CH.sub.3 CH.sub.3 600 164-166*.sup.2(EtOAc/IPE) 1-157 1 601 CH.sub.3 CH.sub.3 H 602 174-176*.sup.2(EtOAc/IPE) 1-158 1 603 CH.sub.3 CH.sub.3 CH.sub.3 604 194-196*.sup.2(EtOAc) 1-159 1 605 CH.sub.3 CH.sub.3 H 606 199-201*.sup.2(EtOAc) 1-160 1 607 CH.sub.3 CH.sub.3 CH.sub.3 608 162-164*.sup.2(EtOAc) 1-161 1 609 CH.sub.3 CH.sub.3 H 610 170-172*.sup.2(EtOAc) 1-162 1 611 CH.sub.3 CH.sub.3 CH.sub.3 612 164-166*.sup.2(EtOAc) 1-163 1 613 CH.sub.3 CH.sub.3 H 614 152-154*.sup.2(EtOAc) 1-164 1 615 CH.sub.3 CH.sub.3 CH.sub.3 616 158-160*.sup.2(EtOAc) 1-165 1 617 CH.sub.3 CH.sub.3 H 618 139-141*.sup.2(EtOAc/EtOH) 1-166 1 619 CH.sub.3 CH.sub.3 CH.sub.3 620 140-141*.sup.2(EtOAc) 1-167 1 621 CH.sub.3 CH.sub.3 H 622 137-139*.sup.2(EtOAc) 1-168 1 623 CH.sub.3 CH.sub.3 H 624 amorphous*.sup.2 1-169 1 625 CH.sub.3 CH.sub.3 CH.sub.3 626 219-221 (IPE) 1-170 1 627 CH.sub.3 CH.sub.3 H 628 179-181 (IPE) 1-171 1 629 CH.sub.3 CH.sub.3 CH.sub.3 630 amorphous 1-172 1 631 CH.sub.3 CH.sub.3 CH.sub.3 632 269-270 (IPE) 1-173 1 633 CH.sub.3 CH.sub.3 H 634 236-238 (IPE) 1-174 1 635 CH.sub.3 CH.sub.3 CH.sub.3 636 amorphous 1-175 1 637 CH.sub.3 CH.sub.3 H 638 196-198 (IPE) 1-176 1 639 CH.sub.3 CH.sub.3 CH.sub.3 640 153-155*.sup.2(EtOAc) 1-177 1 641 CH.sub.3 CH.sub.3 H 642 205-207*.sup.2(EtOAc/EtOH) 1-178 1 643 CH.sub.3 CH.sub.3 CH.sub.3 644 182-184*.sup.2(EtOAc) 1-179 1 645 CH.sub.3 CH.sub.3 H 646 amorphous*.sup.2 1-180 1 647 CH.sub.3 CH.sub.3 CH.sub.3 648 215-217 (hexane) 1-181 1 649 CH.sub.3 CH.sub.3 CH.sub.3 650 150-152*.sup.2(EtOAc/EtOH) 1-182 1 651 CH.sub.3 CH.sub.3 H 652 121-123*.sup.2(EtOAc/Et- OH) 1-183 1 653 CH.sub.3 CH.sub.3 H 654 125-127*.sup.2(EtOAc) 1-184 1 655 CH.sub.3 CH.sub.3 H 656 161-163*.sup.2(EtOAc/EtOH) 1-185 1 657 CH.sub.3 CH.sub.3 H 658 149-151*.sup.2(EtOAc/EtOH) 1-186 1 659 CH.sub.3 CH.sub.3 H 660 152-154*.sup.2(EtOAc/EtOH) 1-187 1 661 CH.sub.3 CH.sub.3 H 662 170-172*.sup.2(EtOAc/EtOH) 1-188 1 663 CH.sub.3 CH.sub.3 H 664 158-160*.sup.2(EtOAc) 1-189 1 665 CH.sub.3 CH.sub.3 H 666 173-175*.sup.2(EtOAc/EtOH) 1-190 1 667 CH.sub.3 CH.sub.3 H 668 155-157*.sup.2(EtOAc/EtOH) 1-191 1 669 CH.sub.3 CH.sub.3 H 670 146-148*.sup.2(EtOAc/EtOH) 1-192 1 671 CH.sub.3 CH.sub.3 H 672 150-152*.sup.2(EtOAc/EtOH) 1-193 1 673 CH.sub.3 CH.sub.3 H 674 158-160*.sup.2(EtOAc/EtOH) 1-194 1 675 CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 676 amorphous 1-195 1 677 CH.sub.3 CH.sub.3 H 678 177-179*.sup.2(EtOAc/EtOH) 1-196 1 679 CH.sub.3 CH.sub.3 H 680 154-156*.sup.2(EtOAc/EtOH) 1-197 1 681 CH.sub.3 CH.sub.3 H 682 153-155*.sup.2(EtOAc) 1-198 1 683 CH.sub.3 CH.sub.3 H 684 128-130*.sup.2(EtOAc/EtOH) 1-199 1 685 CH.sub.3 CH.sub.3 H 686 140-142*.sup.2(EtOAc) 1-200 1 687 CH.sub.3 CH.sub.3 H 688 149-151*.sup.2(EtOAc/EtOH) 1-201 1 689 CH.sub.3 CH.sub.3 H 690 168-170*.sup.2(EtOAc/EtOH) 1-202 1 691 CH.sub.3 CH.sub.3 H 692 152-154*.sup.2(EtOAc/EtOH) 1-203 1 693 CH.sub.3 CH.sub.3 H 694 153-155*.sup.2(EtOAc/EtOH) 1-204 1 695 CH.sub.3 CH.sub.3 H 696 157-159*.sup.2(EtOAc/EtOH) 1-205 1 697 CH.sub.3 CH.sub.3 H 698 179-181*.sup.2(EtOAc/EtOH) 1-206 1 699 CH.sub.3 CH.sub.3 H 700 170-172*.sup.2(EtOAc/EtOH) 1-207 1 701 CH.sub.3 CH.sub.3 H 702 184-186*.sup.2(EtOAc) 1-208 1 703 CH.sub.3 CH.sub.3 H 704 172-174*.sup.2(EtOAc/EtOH) 1-209 1 705 CH.sub.3 CH.sub.3 CH.sub.3 706 amorphous 1-210 1 707 CH.sub.3 CH.sub.3 H 708 amorphous 1-211 1 709 CH.sub.3 CH.sub.3 CH.sub.3 710 193-195*.sup.2(EtOAc) 1-212 1 711 CH.sub.3 CH.sub.3 H 712 164-166*.sup.2(EtOAc/EtOH) 1-213 1 713 CH.sub.3 CH.sub.3 CH.sub.3 714 163-165 (IPE) 1-214 1 715 CH.sub.3 CH.sub.3 H 716 182-184 (IPE) 1-215 1 717 CH.sub.3 CH.sub.3 CH.sub.3 718 180-182 (EtOAc/EtOH) 1-216 1 719 CH.sub.3 CH.sub.3 H 720 153-155 (IPE) 1-217 1 721 CH.sub.3 CH.sub.3 CH.sub.3 722 177-179*.sup.2(EtOAc) 1-218 1 723 CH.sub.3 CH.sub.3 H 724 162-164*.sup.2(EtOAc/EtOH) 1-219 1 725 CH.sub.3 CH.sub.3 H 726 151-153*.sup.2(EtOAc/EtOH- ) 1-220 1 727 CH.sub.3 CH.sub.3 CH.sub.3 728 138-140*.sup.2(EtOAc/EtOH) 1-221 1 729 CH.sub.3 CH.sub.3 H 730 164-166*.sup.2(EtOAc/EtOH) 1-222 1 731 CH.sub.3 CH.sub.2CH.sub.3 CH.sub.2CH.sub.3 732 amorphous 1-223 1 733 CH.sub.3 CH.sub.3 H 734 129-131*.sup.2(EtOAc/IPE) 1-224 1 735 CH.sub.3 CH.sub.3 H 736 138-140*.sup.2(EtOAc/EtOH) 1-225 1 737 CH.sub.3 CH.sub.3 H 738 131-133*.sup.2(EtOAc) 1-226 1 739 CH.sub.3 CH.sub.3 H 740 205-207*.sup.2(EtOAc) 1-227 1 741 CH.sub.3 CH.sub.3 H 742 180-182*.sup.2(EtOAc) 1-228 1 743 CH.sub.3 CH.sub.3 H 744 165-167*.sup.2(EtOAc/EtOH) 1-229 1 745 CH.sub.3 CH.sub.3 H 746 185-187*.sup.2(IPE) 1-230 1 747 CH.sub.3 CH.sub.3 H 748 130-132*.sup.2(EtOAc/EtOH) 1-231 1 749 CH.sub.3 CH.sub.3 H 750 131-133*.sup.2(EtOH) 1-232 1 751 CH.sub.3 CH.sub.3 H 752 146-148*.sup.2(EtOAc/EtOH-

) 1-233 1 753 CH.sub.3 CH.sub.3 H 754 160-162*.sup.2(EtOAc/EtOH) 1-234 1 755 CH.sub.3 CH.sub.3 H 756 193-195*.sup.2(EtOAc/EtOH) 1-235 1 757 CH.sub.3 CH.sub.3 H 758 190-192*.sup.2(EtOAc/EtOH) 1-236 1 759 CH.sub.3 CH.sub.3 CH.sub.3 760 180-182*.sup.2(EtOAc/EtOH) 1-237 1 761 CH.sub.3 CH.sub.3 H 762 159-161*.sup.2(EtOAc/EtOH) 1-238 1 763 CH.sub.3 CH.sub.3 CH.sub.3 764 amorphous*.sup.4 1-239 1 765 CH.sub.3 CH.sub.3 CH.sub.3 766 amorphous*.sup.4 1-240 1 767 CH.sub.3 CH.sub.3 CH.sub.3 768 amorphous*.sup.4 1-241 1 769 CH.sub.3 CH.sub.3 CH.sub.3 770 amorphous*.sup.4 1-242 1 771 CH.sub.3 CH.sub.3 H 772 185-187*.sup.2(EtOH) 1-243 1 773 CH.sub.3 CH.sub.3 H 774 186-188*.sup.2(EtOAc/EtOH- ) 1-244 1 775 CH.sub.3 CH.sub.3 H 776 174-176*.sup.2(EtOAc/EtOH) 1-245 1 777 CH.sub.3 CH.sub.3 H 778 165-167*.sup.2(EtOAc/EtOH) 1-246 1 779 CH.sub.3 CH.sub.3 H 780 172-174*.sup.2(EtOAc/EtOH) 1-247 1 781 CH.sub.3 CH.sub.3 H 782 155-157*.sup.2(EtOAc/EtOH) 1-248 1 783 CH.sub.3 CH.sub.3 H 784 139-141*.sup.2(EtOAc/EtOH) 1-249 1 785 CH.sub.3 CH.sub.3 H 786 176-178*.sup.2(EtOAc/IPE) 1-250 1 787 CH.sub.3 CH.sub.3 H 788 147-149*.sup.2(EtOAc) 1-251 1 789 CH.sub.3 CH.sub.3 CH.sub.3 790 170-172*.sup.2(EtOAc) 1-252 1 791 CH.sub.3 CH.sub.3 CH.sub.3 792 193-195 (EtOAc/IPE) 1-253 1 793 CH.sub.3 CH.sub.3 H 794 200-202 (IPE) 1-254 1 795 CH.sub.3 CH.sub.3 CH.sub.3 796 155-157*.sup.2(EtOAc/EtOH) 1-255 1 797 CH.sub.3 CH.sub.3 CH.sub.3 798 222-224 (IPE) 1-256 1 799 CH.sub.3 CH.sub.3 H 800 193-195 (IPE) 1-257 1 801 CH.sub.3 CH.sub.3 CH.sub.3 802 199-201*.sup.2(EtOAc/EtOH) 1-258 1 803 CH.sub.3 CH.sub.3 H 804 166-168*.sup.2(EtOAc/EtOH) 1-259 1 805 CH.sub.3 CH.sub.3 H 806 165-167*.sup.2(EtOAc/EtOH) 1-260 1 807 CH.sub.3 CH.sub.3 H 808 167-169*.sup.2(EtOAc) 1-261 1 809 CH.sub.3 CH.sub.3 H 810 187-189*.sup.2(EtOAc/EtOH) 1-262 1 811 CH.sub.3 CH.sub.3 H 812 185-187*.sup.2(EtOAc/IPE) 1-263 1 813 CH.sub.3 CH.sub.3 H 814 141-143*.sup.2(EtOAc) 1-264 1 815 CH.sub.3 CH.sub.3 CH.sub.3 816 179-181 (IPE) 1-265 1 817 CH.sub.3 CH.sub.3 H 818 218-220*.sup.2(EtOAc/EtOH) 1-266 1 819 CH.sub.3 CH.sub.3 CH.sub.3 820 166-168*.sup.2(EtOAc/EtOH) 1-267 1 821 CH.sub.3 CH.sub.3 H 822 amorphous*.sup.2 1-268 1 823 CH.sub.3 CH.sub.3 CH.sub.3 824 158-160*.sup.2(EtOAc/EtOH) 1-269 1 825 CH.sub.3 CH.sub.3 H 826 160-162*.sup.2(EtOAc/EtOH) 1-270 1 827 CH.sub.3 CH.sub.3 H 828 162-164 (EtOAc/IPE) 1-271 1 829 CH.sub.3 CH.sub.3 H 830 133-136*.sup.2(EtOAc/EtOH) 1-272 1 831 CH.sub.3 CH.sub.3 CH.sub.3 832 229-231 (CH3CN) 1-273 1 833 CH.sub.3 CH.sub.3 H 834 208-210 (CH3CN) 1-274 1 835 CH.sub.3 CH.sub.3 OH 836 196-198 (EtOH) 1-275 1 837 CH.sub.3 CH.sub.3 H 838 129-131*.sup.2(EtOAc) 1-276 1 839 CH.sub.3 CH.sub.3 CH.sub.3 840 166-168*.sup.2*.sup.4(EtOAc/EtOH) 1-277 1 841 CH.sub.3 CH.sub.3 H 842 131-133*.sup.2*.sup.4(Et- OAc/EtOH) 1-278 1 843 CH.sub.3 CH.sub.3 CH.sub.3 844 158-160*.sup.2*.sup.4(EtOAc/EtOH) 1-279 1 845 CH.sub.3 CH.sub.3 H 846 129-131*.sup.2*.sup.4(EtOAc/EtOH) 1-280 1 847 CH.sub.3 CH.sub.3 H 848 144-146*.sup.2*.sup.4(EtOAc/EtOH) 1-281 1 849 CH.sub.3 CH.sub.3 H 850 170-173*.sup.2*.sup.4(EtOAc/EtOH) 1-282 1 851 CH.sub.3 CH.sub.3 H 852 152-155*.sup.2*.sup.4(EtOAc/EtOH) 1-283 1 853 CH.sub.3 CH.sub.3 CH.sub.3 854 184-185*.sup.2*.sup.4(EtOAc/EtOH) 1-284 1 855 CH.sub.3 CH.sub.3 H 856 122-124*.sup.2*.sup.4(EtOAc/EtOH) 1-285 1 857 CH.sub.3 CH.sub.3 CH.sub.3 858 150-152*.sup.2(EtOAc/EtOH) 1-286 1 859 CH.sub.3 CH.sub.3 H 860 165-167*.sup.2(EtOAc/EtOH) 1-287 1 861 CH.sub.3 CH.sub.3 CH.sub.3 862 182-184*.sup.2(EtOAc/EtOH) 1-288 1 863 CH.sub.3 CH.sub.3 H 864 172-174*.sup.2(EtOAc/EtOH) 1-289 1 865 CH.sub.3 CH.sub.3 CH.sub.3 866 162-165*.sup.2(EtOAc/EtOH) 1-290 1 867 CH.sub.3 CH.sub.3 H 868 149-151*.sup.2(EtOAc/EtOH- ) 1-291 1 869 CH.sub.3 CH.sub.3 CH.sub.3 870 232-234*.sup.2(EtOAc/EtOH) 1-292 1 871 CH.sub.3 CH.sub.3 H 872 164-166*.sup.2(EtOAc/EtOH) 1-293 1 873 CH.sub.3 CH.sub.3 CH.sub.3 874 192-194*.sup.2(EtOAc/EtOH) 1-294 1 875 CH.sub.3 CH.sub.3 H 876 153-155*.sup.2(EtOAc/EtOH) 1-295 1 877 CH.sub.3 CH.sub.3 CH.sub.3 878 162-164*.sup.2(EtOAc) 1-296 1 879 CH.sub.3 CH.sub.3 H 880 204-206*.sup.2(EtOAc/EtOH) 1-297 1 881 CH.sub.3 CH.sub.3 H 882 145-147 (EtOAc/IPE) 1-298 1 883 CH.sub.3 CH.sub.3 H 884 195-196 (EtOAc/IPE) 1-299 1 885 CH.sub.3 CH.sub.3 H 886 202-203 (EtOAc/IPE) 1-300 1 887 CH.sub.3 CH.sub.3 CH.sub.3 888 202-203 (EtOAc/IPE) 1-301 1 889 CH.sub.3 CH.sub.3 H 890 181-183 (EtOAc/IPE) 1-302 1 891 CH.sub.3 CH.sub.3 CH.sub.3 892 203-205*.sup.4(IPE) 1-303 1 893 CH.sub.3 CH.sub.3 H 894 156-158*.sup.4(IPE) 1-304 1 895 CH.sub.3 CH.sub.3 CH.sub.3 896 212-213*.sup.4(IPE) 1-305 1 897 CH.sub.3 CH.sub.3 H 898 164-166*.sup.4(IPE) 1-306 1 899 CH.sub.3 CH.sub.3 CH.sub.3 900 188-190 (IPE)*.sup.4 1-307 1 901 CH.sub.3 CH.sub.3 H 902 191-192 (IPE)*.sup.4 1-308 1 903 CH.sub.3 CH.sub.3 CH.sub.3 904 188-189 (IPE)*.sup.4 1-309 1 905 CH.sub.3 CH.sub.3 H 906 190-191 (IPE)*.sup.4 1-310 1 907 CH.sub.3 CH.sub.3 CH.sub.3 908 200-202 (IPE) 1-311 1 909 CH.sub.3 CH.sub.3 H 910 131-133 (IPE) 1-312 1 911 CH.sub.3 CH.sub.3 CH.sub.3 912 223-224 (IPE) 1-313 1 913 CH.sub.3 CH.sub.3 H 914 184-186 (IPE) 1-314 1 915 CH.sub.3 CH.sub.3 CH.sub.3 916 215-216 (IPE) 1-315 1 917 CH.sub.3 CH.sub.3 H 918 214-215 (IPE) 1-316 1 919 CH.sub.3 CH.sub.3 CH.sub.3 920 amorphous 1-317 1 921 CH.sub.3 CH.sub.3 CH.sub.3 922 151-153 (EtOAc) 1-318 1 923 CH.sub.3 CH.sub.3 H 924 149-151(IPE) 1-319 1 925 CH.sub.3 CH.sub.3 CH.sub.3 926 240-242*.sup.2(EtOAc/EtOH) 1-320 1 927 CH.sub.3 CH.sub.3 H 928 216-218*.sup.2(EtOAc/EtOH) 1-321 1 929 CH.sub.3 CH.sub.3 CH.sub.3 930 180-183*.sup.2(EtOAc/EtOH- ) 1-322 1 931 CH.sub.3 CH.sub.3 H 932 214-216*.sup.2(EtOAc/EtOH) 1-323 1 933 CH.sub.3 CH.sub.3 CH.sub.3 934 198-200*.sup.2(EtOAc/EtOH) 1-324 1 935 CH.sub.3 CH.sub.3 H 936 291-293*.sup.2(EtOAc/EtOH) 1-325 1 937 CH.sub.3 CH.sub.3 CH.sub.3 938 amorphous 1-326 1 939 CH.sub.3 CH.sub.3 CH.sub.3 940 183-186*.sup.2(EtOAc/EtOH) 1-327 1 941 CH.sub.3 CH.sub.3 H 942 154-156*.sup.2(EtOAc/EtOH) 1-328 1 943 CH.sub.3 CH.sub.3 CH.sub.3 944 192-194*.sup.2(No solvent) 1-329 1 945 CH.sub.3 H H 946 156-158*.sup.2*.sup.5 1-330 1 947 CH.sub.3 CH.sub.3 H 948 159-161*.sup.2(IPE) 1-331 1 949 CH.sub.3 CH.sub.3 OH 950 242-244*.sup.5 1-332 1 951 CH.sub.3 CH.sub.3 CH.sub.3 952 217-219*.sup.2(EtOAc/EtOH) 1-333 1 953 CH.sub.3 CH.sub.3 H 954 204-206*.sup.2(EtOAc/EtOH) 1-334 1 955 CH.sub.3 CH.sub.3 CH.sub.3 956 143-145*.sup.2(EtOAc/EtOH) 1-335 1 957 CH.sub.3 CH.sub.3 H 958 172-174*.sup.2(EtOAc/EtOH) 1-336 1 959 CH.sub.3 CH.sub.3 CH.sub.3 960 168-170 (IPE/hexane) 1-337 1 961 CH.sub.3 CH.sub.3 H 962 164-166 (IPE) 1-338 1 963 CH.sub.3 CH.sub.3 CH.sub.3 964 amorphous 1-339 1 965 CH.sub.3 CH.sub.3 H 966 amorphous 1-340 1 967 CH.sub.3 CH.sub.3 CH.sub.3 968 148-150 (IPE) 1-341 1 969 CH.sub.3 CH.sub.3 CH.sub.3 970 183-185 (IPE) 1-342 1 971 CH.sub.3 CH.sub.3 CH.sub.3 972 221-223 (EtOAc) 1-343 1 973 CH.sub.3 CH.sub.3 H 974 205-206 (EtOAc) 1-344 1 975 CH.sub.3 CH.sub.3 H 976 203-204 (EtOAc) 1-345 1 977 CH.sub.3 CH.sub.3 H 978 196-198 (EtOAc) 1-346 1 979 CH.sub.3 CH.sub.3 CH.sub.3 980 234-236 (EtOAc) 1-347 1 981 CH.sub.3 CH.sub.3 H 982 202-236 (EtOAc) 1-348 1 983 CH.sub.3 CH.sub.3 H 984 187-188 (EtOAc) 1-349 1 985 CH.sub.3 CH.sub.3 H 986 200-201 (EtOAc) *.sup.1: Com. No. = compound number, Ex. No. = example number, solvent for crystallization; EtOAc = ethyl acetate, EtOH = ethanol, IPE = diisopropylether, THF = tetrahydrofuran, IPA = isopropyl alcohol, ACE = acetone, CH3CN = acetonitrile

[0525] Analytical data of non-crystal compounds, diastereoisomers and optically active compounds are described below.

[0526] 1-003:

[0527] MS (ES, Pos.): 589 (M+1).sup.+, 591 (M+3).sup.+, 593 (M+5).sup.+, 611 (M+Na).sup.+, 613 (M+Na+2).sup.+, 615 (M+Na+4).sup.+; HPLC retention time: 4.84 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0528] 1-005:

[0529] MS (ES, Pos.): 457 (M+1).sup.+, 459 (M+3).sup.+, 479 (M+Na).sup.+, 481 (M+Na+2).sup.+; HPLC retention time: 9.47 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0530] 1-011:

[0531] MS (ES, Pos.): 393 (M+1).sup.+, 415 (M+Na).sup.+; HPLC retention time: 4.16 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0532] 1-012:

[0533] MS (ES, Pos.): 379 (M+1).sup.+, 401 (M+Na).sup.+; HPLC retention time: 3.8 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0534] 1-013:

[0535] MS (ES, Pos.): 523 (M+1).sup.+, 525 (M+3).sup.+, 527 (M+5).sup.+, 545 (M+Na).sup.+, 547 (M+Na+2).sup.+, 549 (M+Na+4).sup.+; HPLC retention time: 3.14 and 3.27 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0536] 1-014:

[0537] MS (ES, Pos.): 539 (M+1).sup.+, 541 (M+3).sup.+, 543 (M+5).sup.+, 561 (M+Na).sup.+, 563 (M+Na+2).sup.+, 565 (M+Na+4).sup.+; HPLC retention time: 3.57 and 3.69 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0538] 1-015:

[0539] MS (ES, Pos.): 575 (M+1).sup.+, 577 (M+3).sup.+, 579 (M+5).sup.+; HPLC retention time: 4.05 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0540] 1-016:

[0541] MS (ES, Pos.): 457 (M+1).sup.+, 459 (M+3).sup.+, 479 (M+Na).sup.+, 481 (M+Na+2).sup.+; HPLC retention time: 4.60 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0542] 1-017 (the Enantiomer of 1-018):

[0543] HPLC retention time: 10.0 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=20:1, flow rate: 1.0 mL/min.)

[0544] 1-018 (the Enantiomer of 1-017):

[0545] HPLC retention time: 11.4 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=20:1, flow rate: 1.0 mL/min.)

[0546] 1-019:

[0547] MS (ES, Pos.): 443 (M+1).sup.+, 466 (M+Na).sup.+; HPLC retention time: 4.27 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0548] 1-020 (the Enantiomer of 1-021):

[0549] HPLC retention time: 9.1 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=20:1, flow rate: 1.0 mL/min.)

[0550] 1-021 (the Enantiomer of 1-020):

[0551] HPLC retention time: 11.0 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=20:1, flow rate: 1.0 mL/min.)

[0552] 1-022:

[0553] MS (ES, Pos.): 439 (M+1).sup.+, 461 (M+Na).sup.+; HPLC retention time: 4.27 and 4.56 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0554] 1-023:

[0555] MS (ES, Pos.): 425 (M+1).sup.+, 447 (M+Na).sup.+; HPLC retention time: 4.16 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0556] 1-024:

[0557] MS (ES, Pos.): 497 (M+1).sup.+, 499 (M+3).sup.+, 519 (M+Na).sup.+, 521 (M+Na+2).sup.+; HPLC retention time: 3.72 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0558] 1-025:

[0559] MS (ES, Pos.): 483 (M+1).sup.+, 485 (M+3).sup.+, 505 (M+Na).sup.+, 507 (M+Na+2).sup.+; HPLC retention time: 3.66 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0560] 1-026:

[0561] MS (ES, Pos.): 421 (M+1).sup.+; HPLC retention time: 5.20 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0562] 1-027:

[0563] MS (ES, Pos.): 409 (M+1).sup.+, 431 (M+Na).sup.+; HPLC retention time: 2.70 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 m/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0564] 1-028:

[0565] MS (ES, Pos.): 419 (M+1).sup.+; HPLC retention time: 5.45 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0566] 1-029:

[0567] MS (ES, Pos.): 415 (M+1).sup.+; HPLC retention time: 5.27 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0568] 1-030:

[0569] MS (ES, Pos.): 485 (M+1).sup.+, 487 (M+3).sup.+, 507 (M+Na).sup.+, 509 (M+Na+2).sup.+; HPLC retention time: 8.57 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0570] 1-031:

[0571] MS (ES, Pos.): 471 (M+1).sup.+, 473 (M+3).sup.+, 493 (M+Na).sup.+, 495 (M+Na+2).sup.+; HPLC retention time: 7.71 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0572] 1-036:

[0573] MS (ES, Pos.): 407 (M+1).sup.+, 429 (M+Na).sup.+; HPLC retention time: 4.32 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 m/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0574] 1-037:

[0575] MS (ES, Pos.): 415 (M+Na).sup.+; HPLC retention time: 3.98 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0576] 1-039:

[0577] MS (ES, Pos.): 471 (M+1).sup.+, 473 (M+3).sup.+, 493 (M+Na).sup.+, 495 (M+Na+2).sup.+; HPLC retention time: 4.91 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0578] 1-040:

[0579] MS (ES, Pos.): 479 (M+Na).sup.+, 481 (M+Na+2).sup.+; HPLC retention time: 4.46 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0580] 1-041:

[0581] MS (ES, Pos.): 435 (M+1).sup.+; HPLC retention time: 5.56 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0582] 1-043:

[0583] MS (ES, Pos.): 429 (M+1).sup.+; HPLC retention time: 5.47 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0584] 1-044:

[0585] MS (ES, Pos.): 499 (M+1).sup.+, 501 (M+3).sup.+; HPLC retention time: 6.66 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0586] 1-045:

[0587] MS (ES, Pos.): 485 (M+1).sup.+, 487 (M+3).sup.+, 507 (M+Na).sup.+, 509 (M+Na+2).sup.+; HPLC retention time: 6.89 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0588] 1-056:

[0589] MS (ES, Pos.): 415 (M+1).sup.+; HPLC retention time: 4.45 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0590] 1-057:

[0591] MS (ES, Pos.): 485 (M+1).sup.+, 487 (M+3).sup.+; HPLC retention time: 7.54 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0592] 1-063:

[0593] MS (ES, Pos.): 571 (M+Na).sup.+, 573 (M+Na+2).sup.+, 575 (M+Na+4).sup.+; HPLC retention time: 5.20 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0594] 1-092:

[0595] MS (ES, Pos.): 449 (M+1).sup.+; HPLC retention time: 6.24 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0596] 1-094:

[0597] MS (ES, Pos.): 443 (M+1).sup.+; HPLC retention time: 6.22 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0598] 1-103:

[0599] MS (ES, Pos.): 589 (M+1).sup.+, 591 (M+3).sup.+, 593 (M+5), 611 (M+Na).sup.+, 613 (M+Na+2).sup.+, 615 (M+Na+4).sup.+; HPLC retention time: 5.01 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0600] 1-104:

[0601] MS (ES, Pos.): 471 (M+1).sup.+, 473 (M+3).sup.+, 493 (M+Na).sup.+, 495 (M+Na+2).sup.+; HPLC retention time: 6.69 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0602] 1-105:

[0603] MS (ES, Pos.): 457 (M+1).sup.+, 459 (M+3).sup.+, 479 (M+Na).sup.+, 481 (M+Na+2).sup.+; HPLC retention time: 6.01 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0604] 1-106:

[0605] MS (ES, Pos.): 499 (M+1).sup.+, 501 (M+3).sup.+, 521 (M+Na).sup.+, 523 (M+Na+2).sup.+; HPLC retention time: 8.06 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0606] 1-107:

[0607] MS (ES, Pos.): 485 (M+1).sup.+, 487 (M+3).sup.+, 507 (M+Na).sup.+, 509 (M+Na+2).sup.+; HPLC retention time: 10.24 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0608] 1-110:

[0609] MS (ES, Pos.): 501 (M+1).sup.+, 503 (M+3).sup.+, 523 (M+Na).sup.+, 525 (M+Na+2).sup.+; HPLC retention time: 4.61 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0610] 1-114:

[0611] MS (ES, Pos.): 613 (M+Na).sup.+, 615 (M+Na+2).sup.+, 617 (M+Na+4).sup.+; HPLC retention time: 2.57 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0612] 1-115:

[0613] HPLC retention time: 10.6 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=20:1, flow rate: 1.0 mL/min.)

[0614] 1-116:

[0615] MS (ES, Pos.): 451 (M+Na).sup.+, 453 (M+Na+2).sup.+; HPLC retention time: 11.5 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=20:1, flow rate: 1.0 mL/min.)

[0616] 1-117:

[0617] HPLC retention time: 9.3 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=20:1, flow rate: 1.0 mL/min.)

[0618] 1-118:

[0619] MS (ES, Pos.): 429 (M+1).sup.+, 431 (M+3).sup.+; HPLC retention time: 12.1 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=20:1, flow rate: 1.0 mL/min.)

[0620] 1-125:

[0621] MS (ES, Pos.): 388 (M+1).sup.+, 410 (M+Na).sup.+; HPLC retention time: 4.20 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0622] 1-126:

[0623] MS (ES, Pos.): 396 (M+Na).sup.+; HPLC retention time: 4.40 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0624] 1-127 (a Diastereoisomer of 1-128):

[0625] Rf value 0.55 (developing solvent: hexane/EtOAc=1:1, TLC plate Silica gel 60 F.sub.254 (Merck)); .sup.1H NMR (300 MHz, CDCl3) .delta. 1.64-1.82 (1H, m), 1.83-2.03 (2H, m), 2.05-2.18 (1H, m), 2.34 (3H, s), 2.46 (3H, m), 2.53 (3H, s), 2.99-3.12 (1H, m), 3.31-3.70 (3H, m), 3.90-4.02 (1H, m), 6.63 (1H, s), 7.30 (1H, d, J=2.0 Hz), 7.62 (1H, d, J=2.0 Hz); MS (ES, Pos.): 556 (M+Na).sup.+, 558 (M+Na+2), 560 (M+Na+4).sup.+

[0626] 1-128 (a Diastereoisomer of 1-127):

[0627] Rf value 0.48 (developing solvent: hexane/EtOAc=1:1, TLC plate Silica gel 60 F 254 (Merck)); .sup.1H NMR (300 MHz, CDCl.sub.3) .delta. 1.62-1.81 (1H, m), 1.89-2.03 (2H, m), 2.05-2.19 (1H, m), 2.35 (3H, s), 2.46 (3H, d, J=1.2 Hz), 2.53 (3H, s), 3.01-3.13 (1H, m), 3.34-3.70 (3H, m), 3.91-4.02 (1H, m), 6.63 (1H, s), 7.30 (1H, d, J=2.0 Hz), 7.62 (1H, d, J=2.0 Hz); MS (ES, Pos.): 534 (M+1).sup.+, 536 (M+3).sup.+, 538 (M+5).sup.+, 556 (M+Na).sup.+, 558 (M+Na+2), 560 (M+Na+4).sup.+

[0628] 1-129:

[0629] MS (ES, Pos.): 570 (M+1).sup.+, 572 (M+3).sup.+, 574 (M+5).sup.+; HPLC retention time: 4.46 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0630] 1-130:

[0631] MS (ES, Pos.): 452 (M+1).sup.+, 454 (M+3).sup.+, 474 (M+Na).sup.+, 476 (M+Na+2).sup.+; HPLC retention time: 5.36 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0632] 1-131:

[0633] MS (ES, Pos.): 460 (M+Na).sup.+, 462 (M+Na+2).sup.+; HPLC retention time: 4.87 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0634] 1-132:

[0635] MS (ES, Pos.): 456 (M+Na).sup.+; HPLC retention time: 5.12 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0636] 1-133:

[0637] MS (ES, Pos.): 442 (M+Na).sup.+; HPLC retention time: 4.64 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0638] 1-138:

[0639] MS (ES, Pos.): 500 (M+Na).sup.+, 502 (M+Na+2).sup.+; HPLC retention time: 4.05 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0640] 1-140:

[0641] MS (ES, Pos.): 410 (M+1).sup.+; HPLC retention time: 5.85 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0642] 1-141:

[0643] MS (ES, Pos.): 480 (M+1).sup.+, 482 (M+3).sup.+, 502 (M+Na).sup.+, 504 (M+Na+2).sup.+; HPLC retention time: 7.51 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0644] 1-142:

[0645] MS (ES, Pos.): 466 (M+1).sup.+, 468 (M+3).sup.+, 488 (M+Na).sup.+, 490 (M+Na+2).sup.+; HPLC retention time: 9.01 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0646] 1-143:

[0647] MS (ES, Pos.): 584 (M+1).sup.+, 586 (M+3).sup.+, 588 (M+5).sup.+, 606 (M+Na).sup.+, 608 (M+Na+2).sup.+, 610 (M+Na+4).sup.+; HPLC retention time: 4.48 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0648] 1-144:

[0649] MS (ES, Pos.): 466 (M+1).sup.+, 468 (M+3).sup.+, 488 (M+Na).sup.+, 490 (M+Na+2).sup.+; HPLC retention time: 5.92 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0650] 1-146:

[0651] MS (ES, Pos.): 516 (M+Na).sup.+, 518 (M+Na+2).sup.+; HPLC retention time: 8.63 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0652] 1-147:

[0653] MS (ES, Pos.): 480 (M+1).sup.+, 482 (M+3).sup.+, 502 (M+Na).sup.+, 504 (M+Na+2).sup.+; HPLC retention time: 3.44 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0654] 1-149:

[0655] MS (ES, Pos.): 466 (M+1).sup.+, 468 (M+3).sup.+, 488 (M+Na).sup.+, 490 (M+Na+2).sup.+

[0656] 1-168:

[0657] MS (ES, Pos.): 444 (M+1).sup.+, 466 (M+Na).sup.+; HPLC retention time: 4.11 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0658] 1-171:

[0659] MS (ES, Pos.): 596 (M+1).sup.+, 598 (M+3).sup.+, 600 (M+5).sup.+, 618 (M+Na).sup.+, 620 (M+Na+2).sup.+, 622 (M+Na+4).sup.+; HPLC retention time: 5.87 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0660] 1-174:

[0661] MS (ES, Pos.): 506 (M+1).sup.+, 508 (M+3).sup.+, 528 (M+Na).sup.+, 530 (M+Na+2).sup.+; HPLC retention time: 5.83 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0662] 1-179:

[0663] MS (ES, Pos.): 474 (M+Na).sup.+, 476 (M+Na+2).sup.+; HPLC retention time: 5.74 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0664] 1-194:

[0665] MS (ES, Pos.): 421 (M+1).sup.+; HPLC retention time: 5.08 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0666] 1-209:

[0667] MS (ES, Pos.): 496 (M+1).sup.+

[0668] 1-210:

[0669] MS (ES, Pos.): 482 (M+1).sup.+

[0670] 1-222:

[0671] MS (ES, Pos.): 421 (M+1).sup.+; HPLC retention time: 7.13 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0672] 1-238:

[0673] MS (ES, Pos.): 575 (M+1).sup.+, 577 (M+3).sup.+, 579 (M+5).sup.+

[0674] HPLC retention time: 8.6 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=20:1, flow rate: 1.0 mL/min.)

[0675] 1-239:

[0676] MS (ES, Pos.): 575 (M+1).sup.+, 577 (M+3).sup.+, 579 (M+5).sup.+

[0677] HPLC retention time: 9.6 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=20:1, flow rate: 1.0 mL/min.)

[0678] 1-240:

[0679] MS (ES, Pos.): 570 (M+1).sup.+, 572 (M+3).sup.+, 574 (M+5).sup.+

[0680] HPLC retention time: 13.0 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=100:1, flow rate: 1.0 mL/min.)

[0681] 1-241:

[0682] MS (ES, Pos.): 570 (M+1).sup.+, 572 (M+3).sup.+, 574 (M+5).sup.+

[0683] HPLC retention time: 11.9 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=100:1, flow rate: 1.0 mL/min.)

[0684] 1-267:

[0685] MS (ES, Pos.): 438 (M+1).sup.+, 440 (M+3).sup.+, 460 (M+Na).sup.+, 462 (M+Na+2).sup.+; HPLC retention time: 4.43 min. (Capcell Pak UG120, 4.6 mm.times.150 mm, Shiseido); Flow rate: 1.0 ml/min; Mobile phase: acetonitrile/0.05M ammonium acetate aqueous solution (80:20), pH of the solvent was adjusted to 7.4 with aqueous ammonia or acetic acid.

[0686] 1-276 (the Enantiomer of 1-278):

[0687] [.alpha.].sub.D.sup.29=+7.41 (c 1.00, CH.sub.3OH)

[0688] 1-277 (the Enantiomer of 1-279):

[0689] HPLC retention time: 6.0 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=8:1, flow rate: 1.0 mL/min.)

[0690] 1-278 (the enantiomer of 1-276):

[0691] [.alpha.].sub.D.sup.29=-5.90 (c 1.01, CH.sub.3OH)

[0692] 1-279 (the Enantiomer of 1-277):

[0693] HPLC retention time: 5.5 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=8:1, flow rate: 1.0 mL/min.)

[0694] 1-280:

[0695] [.alpha.].sub.D.sup.29=-9.30 (c 0.41, CH.sub.3OH)

[0696] 1-281:

[0697] [.alpha.].sub.D.sup.28=-11.2 (c 0.41, CH.sub.3OH)

[0698] 1-282:

[0699] [.alpha.].sub.D.sup.28=-18.0 (c 0.41, CH.sub.3OH)

[0700] 1-283:

[0701] [.alpha.].sub.D.sup.22=-6.6 (c 0.40, CH.sub.3OH)

[0702] 1-284:

[0703] [.alpha.].sub.D.sup.28=-5.5 (c 0.40, CH.sub.3OH)

[0704] 1-302 (the Enantiomer of 1-304):

[0705] HPLC retention time: 8.4 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=8:1, flow rate: 1.0 mL/min.)

[0706] 1-303 (the Enantiomer of 1-305):

[0707] HPLC retention time: 9.2 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=8:1, flow rate: 1.0 mL/min.)

[0708] 1-304 (the Enantiomer of 1-302):

[0709] HPLC retention time: 8.9 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=8:1, flow rate: 1.0 mL/min.)

[0710] 1-305 (the Enantiomer of 1-303):

[0711] HPLC retention time: 10.6 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), 0.46 cm I.D..times.25 cm, mobile phase: hexane/IPA=8:1, flow rate: 1.0 mL/min.)

[0712] 1-306 (the Enantiomer of 1-308):

[0713] [.alpha.].sub.D.sup.28=+5.38 (c 0.81, CH.sub.3OH)

[0714] 1-307 (the Enantiomer of 1-309):

[0715] HPLC retention time: 16.6 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), (0.46 cm I.D..times.25 cm).times.2, mobile phase: hexane/IPA=8:1, flow rate: 1.0 mL/min.)

[0716] 1-308 (the Enantiomer of 1-306):

[0717] [.alpha.].sub.D.sup.29=-7.69 (c 0.80, CH.sub.3OH)

[0718] 1-309 (the Enantiomer of 1-307):

[0719] HPLC retention time: 17.4 min. (CHIRAL PAK AD (DAICEL CHEMICAL INDUSTRIES, LTD), (0.46 cm I.D..times.25 cm).times.2, mobile phase: hexane/IPA=8:1, flow rate: 1.0 mL/min.)

[0720] 1-316:

[0721] MS (ES, Pos.): 451 (M+1).sup.+; HPLC retention time: 6.26 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0722] 1-325:

[0723] MS (ES, Pos.): 449 (M+1).sup.+; HPLC retention time: 5.78 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0724] 1-338:

[0725] MS (ES, Pos.): 360 (M+1).sup.+; HPLC retention time: 6.19 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0726] 1-339:

[0727] MS (ES, Pos.): 424 (M+1).sup.+, 426 (M+3).sup.+; HPLC retention time: 5.93 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0728] *2: HCl salt

[0729] *3: a mixture of diastereomers

[0730] *4: optically active compound

[0731] *5: Crystallized on standing from the compound purified (silica gel column chromatography) and dried.

2TABLE 2*.sup.1 987 Com. No. Ex. No. 988 R.sup.10 R.sup.6 R.sup.7 R.sup.8 --Ar melting point (.degree. C.) (solvent for crystallization) 2-001 1 989 H CH.sub.3 CH.sub.3 CH.sub.3 990 amorphous 2-002 1 991 H CH.sub.3 CH.sub.3 CH.sub.3 992 amorphous 2-003 1 993 H CH.sub.3 CH.sub.3 H 994 119-121*.sup.2(IPE) 2-004 1 995 H CH.sub.3 CH.sub.3 CH.sub.3 996 200-202*.sup.2(EtOAc) 2-005 1 997 H CH.sub.3 CH.sub.3 H 998 204-206*.sup.2(ACE) 2-006 1 999 H CH.sub.3 CH.sub.3 CH.sub.3 1000 228-230*.sup.2(EtOAc) 2-007 1 1001 H CH.sub.3 CH.sub.3 H 1002 218-220*.sup.2(ACE) 2-008 1 1003 H CH.sub.3 CH.sub.3 CH.sub.3 1004 179-181*.sup.2(EtOAc/EtOH) 2-009 1 1005 H CH.sub.3 CH.sub.3 H 1006 204-206*.sup.2(ACE) 2-010 1 1007 H CH.sub.3 CH.sub.3 CH.sub.3 1008 146-148*.sup.2(EtOAc/EtOH) 2-011 1 1009 H CH.sub.3 CH.sub.3 H 1010 108-110*.sup.2(IPE) 2-012 1 1011 H CH.sub.3 CH.sub.3 CH.sub.3 1012 amorphous 2-013 1 1013 H CH.sub.3 CH.sub.3 CH.sub.3 1014 163-165*.sup.2(EtOAc/EtOH) 2-014 1 1015 H CH.sub.3 CH.sub.3 H 1016 179-181*.sup.2(ACE) 2-015 1 1017 H CH.sub.3 CH.sub.3 CH.sub.3 1018 149-151*.sup.2(EtOAc) 2-016 1 1019 H CH.sub.3 CH.sub.3 CH.sub.3 1020 125-127*.sup.2(MeOH/IPE) 2-017 1 1021 H CH.sub.3 CH.sub.3 CH.sub.3 1022 172-174*.sup.2(ACE/IPE) 2-018 1 1023 H CH.sub.3 CH.sub.3 CH.sub.3 1024 133-135*.sup.2(MeOH) 2-019 1 1025 H CH.sub.3 CH.sub.3 H 1026 207-209*.sup.2(ACE) 2-020 1 1027 H CH.sub.3 CH.sub.3 CH.sub.3 1028 130-132*.sup.2(MeOH/IPE) 2-021 1 1029 H CH.sub.3 CH.sub.3 CH.sub.3 1030 124-126*.sup.2(MeOH) 2-022 1 1031 H CH.sub.3 CH.sub.3 H 1032 110-112*.sup.2(IPE) 2-023 1 1033 H CH.sub.3 CH.sub.3 CH.sub.3 1034 132-134*.sup.2(MeOH/IPE) 2-024 1 1035 H CH.sub.3 CH.sub.3 CH.sub.3 1036 130-132*.sup.2(MeOH) 2-025 1 1037 H CH.sub.3 CH.sub.3 H 1038 200-202*.sup.2(IPA) 2-026 1 1039 H CH.sub.3 CH.sub.3 CH.sub.3 1040 122-124*.sup.2(MeOH) 2-027 1 1041 H CH.sub.3 CH.sub.3 CH.sub.3 1042 198-200*.sup.2(MeOH/IPE) 2-028 1 1043 H CH.sub.3 CH.sub.3 CH.sub.3 1044 124-126*.sup.2(MeOH) 2-029 1 1045 H CH.sub.3 CH.sub.3 H 1046 184-186*.sup.2(Et2O) 2-030 1 1047 H CH.sub.3 CH.sub.3 CH.sub.3 1048 138-140*.sup.2(MeOH) 2-031 1 1049 H CH.sub.3 CH.sub.3 H 1050 157-159*.sup.2(ACE) 2-032 1 1051 H CH.sub.3 CH.sub.3 H 1052 154-156*.sup.2(EtOH) 2-033 1 1053 H CH.sub.3 CH.sub.3 CH.sub.3 1054 167-169*.sup.2(MeOH) 2-034 1 1055 H CH.sub.3 CH.sub.3 H 1056 amorphous*.sup.2 2-035 1 1057 H CH.sub.3 CH.sub.3 CH.sub.3 1058 223-225*.sup.2(ACE) 2-036 1 1059 H CH.sub.3 CH.sub.3 H 1060 236-238*.sup.2(CH3CN) 2-037 1 1061 H CH.sub.3 CH.sub.3 CH.sub.3 1062 228-230*.sup.2(ACE) 2-038 1 1063 H CH.sub.3 CH.sub.3 H 1064 230-232*.sup.2(CH3CN) 2-039 1 1065 H CH.sub.3 CH.sub.3 CH.sub.3 1066 218-220*.sup.2(ACE) 2-040 1 1067 H CH.sub.3 CH.sub.3 H 1068 232-234*.sup.2(ACE) 2-041 1 1069 H CH.sub.3 CH.sub.3 CH.sub.3 1070 amorphous*.sup.2 2-042 1 1071 H CH.sub.3 CH.sub.3 H 1072 241-243*.sup.2(CH3CN) 2-043 1 1073 H CH.sub.3 CH.sub.3 CH.sub.3 1074 218-220*.sup.2(ACE) 2-044 1 1075 H CH.sub.3 CH.sub.3 H 1076 182-184*.sup.2(CH3CN) 2-045 1 1077 H CH.sub.3 CH.sub.3 H 1078 amorphous*.sup.2 2-046 1 1079 H CH.sub.3 CH.sub.3 H 1080 amorphous*.sup.2 2-047 1 1081 H CH.sub.3 CH.sub.3 H 1082 198-200*.sup.2(CH3CN) 2-048 1 1083 H CH.sub.3 CH.sub.3 H 1084 amorphous*.sup.2 2-049 1 1085 H CH.sub.3 CH.sub.3 CH.sub.3 1086 amorphous*.sup.2 2-050 1 1087 H CH.sub.3 CH.sub.3 H 1088 amorphous*.sup.2 2-051 1 1089 CO.sub.2Et CH.sub.3 CH.sub.3 CH.sub.3 1090 169-171 (IPE) 2-052 1 1091 H CH.sub.3 CH.sub.3 CH.sub.3 1092 amorphous*.sup.2 2-053 1 1093 H CH.sub.3 CH.sub.3 H 1094 amorphous*.sup.2 2-054 1 1095 H CH.sub.3 CH.sub.3 CH.sub.3 1096 amorphous*.sup.2 2-055 1 1097 H CH.sub.3 CH.sub.3 H 1098 215-217*.sup.2(CH3CN) 2-056 1 1099 H CH.sub.3 CH.sub.3 CH.sub.3 1100 amorphous*.sup.2 2-057 1 1101 H CH.sub.3 CH.sub.3 H 1102 amorphous*.sup.2 2-058 1 1103 H CH.sub.3 CH.sub.3 CH.sub.3 1104 amorphous*.sup.2 2-059 1 1105 H CH.sub.3 CH.sub.3 H 1106 amorphous*.sup.2 2-060 1 1107 H CH.sub.3 CH.sub.3 CH.sub.3 1108 amorphous*.sup.2 2-061 1 1109 H CH.sub.3 CH.sub.3 H 1110 210-212*.sup.2(CH3CN) 2-062 1 1111 H CH.sub.3 CH.sub.3 CH.sub.3 1112 amorphous*.sup.2 2-063 1 1113 H CH.sub.3 CH.sub.3 H 1114 amorphous*.sup.2 2-064 1 1115 H CH.sub.3 CH.sub.3 H 1116 amorphous*.sup.2 2-065 1 1117 H CH.sub.3 CH.sub.3 H 1118 amorphous*.sup.2 2-066 1 1119 H CH.sub.3 CH.sub.3 H 1120 amorphous*.sup.2 2-067 1 1121 H CH.sub.3 CH.sub.3 H 1122 113-115*.sup.2(IPE) 2-068 1 1123 H CH.sub.3 CH.sub.3 CH.sub.3 1124 amorphous*.sup.2 2-069 1 1125 H CH.sub.3 CH.sub.3 H 1126 amorphous*.sup.2 2-070 1 1127 Br CH.sub.3 CH.sub.3 H 1128 216-218*.sup.2(EtOAc/EtOH) 2-071 1 1129 H CH.sub.3 CH.sub.3 CH.sub.3 1130 127-129*.sup.2(MeOH) 2-072 1 1131 H CH.sub.3 CH.sub.3 H 1132 amorphous*.sup.2 2-073 1 1133 H CH.sub.3 CH.sub.3 CH.sub.3 1134 amorphous*.sup.2 2-074 1 1135 H CH.sub.3 CH.sub.3 H 1136 215-217*.sup.2(CH3CN) 2-075 1 1137 H CH.sub.3 CH.sub.3 CH.sub.3 1138 202-204*.sup.2(ACE) 2-076 1 1139 H CH.sub.3 CH.sub.3 H 1140 197-199*.sup.2(CH3CN) 2-077 1 1141 H CH.sub.3 CH.sub.3 CH.sub.3 1142 amorphous*.sup.2 2-078 1 1143 H CH.sub.3 CH.sub.3 H 1144 amorphous*.sup.2 2-079 1 1145 H CH.sub.3 CH.sub.3 CH.sub.3 1146 amorphous*.sup.2 2-080 1 1147 H CH.sub.3 CH.sub.3 H 1148 212-214*.sup.2(CH3CN) 2-081 1 1149 H CH.sub.3 CH.sub.3 CH.sub.3 1150 amorphous*.sup.2 2-082 1 1151 H CH.sub.3 CH.sub.3 H 1152 178-180*.sup.2(CH3CN) 2-083 1 1153 H CH.sub.3 CH.sub.3 H 1154 amorphous*.sup.2 2-084 1 1155 H CH.sub.3 CH.sub.3 H 1156 amorphous*.sup.2 2-085 1 1157 H CH.sub.3 CH.sub.3 H 1158 201-203*.sup.2(CH3CN) 2-086 1 1159 H CH.sub.3 CH.sub.3 H 1160 192-194*.sup.2(IPE) 2-087 1 1161 H CH.sub.3 CH.sub.3 CH.sub.3 1162 amorphous*.sup.2 2-088 1 1163 H CH.sub.3 CH.sub.3 H 1164 amorphous*.sup.2 2-089 1 1165 H CH.sub.3 CH.sub.3 CH.sub.3 1166 153-155*.sup.2(Et2O) 2-090 1 1167 H CH.sub.3 CH.sub.3 H 1168 215-217*.sup.2(CH3CN) 2-091 1 1169 H CH.sub.3 CH.sub.3 CH.sub.3 1170 208-210*.sup.2(IPE) 2-092 1 1171 H CH.sub.3 CH.sub.3 H 1172 207-209*.sup.2(CH3CN) 2-093 1 1173 H CH.sub.3 CH.sub.3 CH.sub.3 1174 130-132*.sup.2(MeOH) 2-094 1 1175 H CH.sub.3 CH.sub.3 H 1176 amorphous*.sup.2 2-095 1 1177 H CH.sub.3 CH.sub.3 CH.sub.3 1178 236-238*.sup.2(ACE) 2-096 1 1179 H CH.sub.3 CH.sub.3 H 1180 226-238*.sup.2(Et2O) 2-097 1 1181 H CH.sub.3 CH.sub.3 CH.sub.3 1182 amorphous*.sup.2 2-098 1 1183 H CH.sub.3 CH.sub.3 H 1184 225-227*.sup.2(Et2O) 2-099 1 1185 H CH.sub.3 CH.sub.3 CH.sub.3 1186 amorphous 2-100 1 1187 H CH.sub.3 CH.sub.3 H 1188 amorphous*.sup.2 2-101 1 1189 H CH.sub.3 CH.sub.3 CH.sub.3 1190 amorphous*.sup.2 2-102 1 1191 H CH.sub.3 CH.sub.3 H 1192 amorphous*.sup.2 2-103 1 1193 H CH.sub.3 CH.sub.3 CH.sub.3 1194 amorphous*.sup.2 2-104 1 1195 H CH.sub.3 CH.sub.3 H 1196 amorphous*.sup.2 2-105 1 1197 H CH.sub.3 CH.sub.3 H 1198 amorphous*.sup.2 2-106 1 1199 H CH.sub.3 CH.sub.3 H 1200 amorphous*.sup.2 2-107 1 1201 H CH.sub.3 CH.sub.3 H 1202 amorphous*.sup.2 2-108 1 1203 H CH.sub.3 CH.sub.3 H 1204 amorphous*.sup.2 2-109 1 1205 H CH.sub.3 CH.sub.3 CH.sub.3 1206 amorphous*.sup.2 2-110 1 1207 H CH.sub.3 CH.sub.3 H 1208 amorphous*.sup.2 2-111 1 1209 H CH.sub.3 CH.sub.3 CH.sub.3 1210 amorphous*.sup.2 2-112 1 1211 H CH.sub.3 CH.sub.3 CH.sub.3 1212 amorphous*.sup.2 2-113 1 1213 H CH.sub.3 CH.sub.3 H 1214 amorphous*.sup.2 2-114 1 1215 H CH.sub.3 CH.sub.3 CH.sub.3 1216 amorphous*.sup.2 2-115 1 1217 H CH.sub.3 CH.sub.3 H 1218 217-219*.sup.2(ACE) 2-116 1 1219 H CH.sub.3 CH.sub.3 CH.sub.3 1220 amorphous*.sup.2 2-117 1 1221 H CH.sub.3 CH.sub.3 H 1222 amorphous*.sup.2 2-118 1 1223 H CH.sub.3 CH.sub.3 CH.sub.3 1224 amorphous*.sup.2 2-119 1 1225 H CH.sub.3 CH.sub.3 H 1226 amorphous*.sup.2 2-120 1 1227 H CH.sub.3 CH.sub.3 CH.sub.3 1228 amorphous*.sup.2 2-121 1 1229 H CH.sub.3 CH.sub.3 H 1230 amorphous*.sup.2 2-122 1 1231 H CH.sub.3 CH.sub.3 CH.sub.3 1232 amorphous*.sup.2 2-123 1 1233 H CH.sub.3 CH.sub.3 H 1234 amorphous*.sup.2 2-124 1 1235 H CH.sub.3 CH.sub.3 H 1236 amorphous*.sup.2 2-125 1 1237 H CH.sub.3 CH.sub.3 H 1238 amorphous*.sup.2 2-126 1 1239 H CH.sub.3 CH.sub.3 H 1240 amorphous*.sup.2 2-127 1 1241 H CH.sub.3 CH.sub.3 H 1242 212-214*.sup.2(IPE) 2-128 1 1243 H CH.sub.3 CH.sub.3 H 1244 amorphous*.sup.2 2-129 1 1245 CO.sub.2Et CH.sub.3 CH.sub.3 CH.sub.3 1246 176-178 (IPE) *.sup.1: Com. No. = compound number, Ex. No. = example number, solvent for crystallization; ACE = acetone, EtOAc = ethyl acetate, EtOH = ethanol, Et2O = diethylether, IPA = isopropyl alcohol, IPE = diisopropyl ether, MeOH = methanol, CH3CN = acetonitrile

[0732] Analytical data of non-crystal compounds are described below.

[0733] 2-001:

[0734] MS (ES, Pos.): 418 (M+1).sup.+, 420 (M+3).sup.+, 422 (M+5).sup.+

[0735] 2-002:

[0736] MS (ES, Pos.): 432 (M+1).sup.+, 434 (M+3).sup.+, 436 (M+5).sup.+

[0737] 2-012:

[0738] MS (ES, Pos.): 427 (M+1).sup.+

[0739] 2-034:

[0740] MS (ES, Pos.): 534 (M+1).sup.+, 536 (M+3).sup.+, 538 (M+5).sup.+; HPLC retention time: 6.55 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0741] 2-041:

[0742] MS (ES, Pos.): 540 (M+1).sup.+, 542 (M+3).sup.+, 544 (M+5).sup.+; HPLC retention time: 6.60 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acelonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0743] 2-045:

[0744] MS (ES, Pos.): 456 (M+1).sup.+, 458 (M+3).sup.+; HPLC retention time: 6.72 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0745] 2-046:

[0746] MS (ES, Pos.): 424 (M+1).sup.+; HPLC retention time: 6.61 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0747] 2-048:

[0748] MS (ES, Pos.): 482 (M+1).sup.+, 484 (M+3).sup.+; HPLC retention time: 5.67 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0749] 2-049:

[0750] MS (ES, Pos.): 584 (M+1).sup.+, 586 (M+3).sup.+, 588 (M+5).sup.+; HPLC retention time: 6.73 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0751] 2-050:

[0752] MS (ES, Pos.): 570 (M+1).sup.+, 572 (M+3).sup.+, 574 (M+5).sup.+; HPLC retention time: 6.90 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0753] 2-052:

[0754] MS (ES, Pos.): 562 (M+1).sup.+, 564 (M+3).sup.+, 562 (M+5).sup.+; HPLC retention time: 6.81 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0755] 2-053:

[0756] MS (ES, Pos.): 548 (M+1).sup.+, 550 (M+3).sup.+, 552 (M+5).sup.+; HPLC retention time: 6.72 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0757] 2-054:

[0758] MS (ES, Pos.): 598 (M+1).sup.+, 600 (M+3).sup.+, 602 (M+5).sup.+; HPLC retention time: 6.47 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0759] 2-056:

[0760] MS (ES, Pos.): 510 (M+1).sup.+, 512 (M+3).sup.+, 514 (M+5).sup.+; HPLC retention time: 6.42 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0761] 2-057:

[0762] MS (ES, Pos.): 496 (M+1).sup.+, 498 (M+3).sup.+, 500 (M+5).sup.+; HPLC retention time: 6.55 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0763] 2-058:

[0764] MS (ES, Pos.): 466 (M+1).sup.+, 468 (M+3).sup.+, 470 (M+5).sup.+; HPLC retention time: 6.82 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0765] 2-059:

[0766] MS (ES, Pos.): 452 (M+1).sup.+, 454 (M+3).sup.+, 456 (M+5).sup.+; HPLC retention time: 6.23 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0767] 2-060:

[0768] MS (ES, Pos.): 554 (M+1).sup.+, 556 (M+3).sup.+, 558 (M+5).sup.+; HPLC retention time: 6.43 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0769] 2-062:

[0770] MS (ES, Pos.): 422 (M+1).sup.+; HPLC retention time: 6.29 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0771] 2-063:

[0772] MS (ES, Pos.): 408 (M+1).sup.+; HPLC retention time: 5.94 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0773] 2-064:

[0774] MS (ES, Pos.): 470 (M+1).sup.+, 472 (M+3).sup.+, HPLC retention time: 6.92 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 m/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0775] 2-065:

[0776] MS (ES, Pos.): 438 (M+1).sup.+; HPLC retention time: 6.40 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0777] 2-066:

[0778] MS (ES, Pos.): 506 (M+1).sup.+, 508 (M+3).sup.+, 510 (M+5).sup.+; HPLC retention time: 6.31 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0779] 2-068:

[0780] MS (ES, Pos.): 598 (M+1).sup.+, 600 (M+3).sup.+, 602 (M+5).sup.+; HPLC retention time: 7.11 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0781] 2-069:

[0782] MS (ES, Pos.): 584 (M+1).sup.+, 586 (M+3).sup.+, 588 (M+5).sup.+; HPLC retention time: 7.11 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0783] 2-072:

[0784] MS (ES, Pos.): 562 (M+1).sup.+, 564 (M+3).sup.+, 566 (M+5).sup.+; HPLC retention time: 6.63 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0785] 2-073:

[0786] MS (ES, Pos.): 612 (M+1).sup.+, 614 (M+3).sup.+, 616 (M+5).sup.+; HPLC retention time: 6.61 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0787] 2-077:

[0788] MS (ES, Pos.): 480 (M+1).sup.+, 482 (M+3).sup.+, 484 (M+5).sup.+; HPLC retention time: 6.54 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0789] 2-078:

[0790] MS (ES, Pos.): 466 (M+1).sup.+, 468 (M+3).sup.+, 470 (M+5).sup.+; HPLC retention time: 5.95 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0791] 2-079:

[0792] MS (ES, Pos.): 568 (M+1).sup.+, 570 (M+3).sup.+, 572 (M+5).sup.+; HPLC retention time: 6.97 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0793] 2-081:

[0794] MS (ES, Pos.): 436 (M+1).sup.+; HPLC retention time: 6.49 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0795] 2-083:

[0796] MS (ES, Pos.): 484 (M+1).sup.+, 486 (M+3).sup.+; HPLC retention time: 7.09 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0797] 2-084:

[0798] MS (ES, Pos.): 452 (M+1).sup.+; HPLC retention time: 6.55 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0799] 2-087:

[0800] MS (ES, Pos.): 612 (M+1).sup.+, 614 (M+3).sup.+, 616 (M+5).sup.+; HPLC retention time: 7.24 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0801] 2-088:

[0802] MS (ES, Pos.): 598 (M+1).sup.+, 600 (M+3).sup.+, 602 (M+5).sup.+; HPLC retention time: 7.21 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0803] 2-094:

[0804] MS (ES, Pos.): 529 (M+1).sup.+, 531 (M+3).sup.+, 533 (M+5).sup.+; HPLC retention time: 6.40 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0805] 2-097:

[0806] MS (ES, Pos.): 491 (M+1).sup.+, 493 (M+3).sup.+, 495 (M+5).sup.+; HPLC retention time: 6.78 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 [un, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0807] 2-099:

[0808] MS (ES, Pos.): 447 (M+1).sup.+, 449 (M+3).sup.+, 451 (M+5).sup.+; HPLC retention time: 6.73 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0809] 2-100:

[0810] MS (ES, Pos.): 433 (M+1).sup.+, 435 (M+3).sup.+, 437 (M+5).sup.+; HPLC retention time: 5.70 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0811] 2-101:

[0812] MS (ES, Pos.): 535 (M+1).sup.+, 537 (M+3).sup.+, 539 (M+5).sup.+; HPLC retention time: 6.72 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0813] 2-102:

[0814] MS (ES, Pos.): 521 (M+1).sup.+, 523 (M+3).sup.+, 525 (M+5).sup.+; HPLC retention time: 6.27 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0815] 2-103:

[0816] MS (ES, Pos.): 403 (M+1); HPLC retention time: 6.24 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0817] 2-104:

[0818] MS (ES, Pos.): 389 (M+1).sup.+; HPLC retention time: 5.89 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% Ato 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0819] 2-105:

[0820] MS (ES, Pos.): 451 (M+1).sup.+, 453 (M+3).sup.+, HPLC retention time: 6.87 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 m/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0821] 2-106:

[0822] MS (ES, Pos.): 419 (M+1).sup.+; HPLC retention time: 6.33 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0823] 2-107:

[0824] MS (ES, Pos.): 487 (M+1).sup.+, 489 (M+3).sup.+, 491 (M+5).sup.+; HPLC retention time: 6.20 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0825] 2-108:

[0826] MS (ES, Pos.): 477 (M+1).sup.+, 479 (M+3).sup.+, 481 (M+5).sup.+; HPLC retention time: 6.21 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acelonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0827] 2-109:

[0828] MS (ES, Pos.): 579 (M+1).sup.+, 581 (M+3).sup.+, 583 (M+5).sup.+; HPLC retention time: 7.00 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0829] 2-110:

[0830] MS (ES, Pos.): 565 (M+1).sup.+, 567 (M+3).sup.+, 569 (M+5).sup.+; HPLC retention time: 7.00 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0831] 2-111:

[0832] MS (ES, Pos.): 421 (M+1).sup.+, 423 (M+3).sup.+; HPLC retention time: 6.84 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0833] 2-112:

[0834] MS (ES, Pos.): 557 (M+1).sup.+, 559 (M+3).sup.+, 561 (M+5).sup.+; HPLC retention time: 6.54 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0835] 2-113:

[0836] MS (ES, Pos.): 543 (M+1).sup.+, 545 (M+3).sup.+, 547 (M+5).sup.+; HPLC retention time: 6.69 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0837] 2-114:

[0838] MS (ES, Pos.): 593 (M+1).sup.+, 595 (M+3).sup.+, 597 (M+5).sup.+; HPLC retention time: 6.84 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0839] 2-116:

[0840] MS (ES, Pos.): 505 (M+1).sup.+, 507 (M+3).sup.+, 509 (M+5).sup.+; HPLC retention time: 6.37 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0841] 2-117:

[0842] MS (ES, Pos.): 491 (M+1).sup.+, 493 (M+3).sup.+, 495 (M+5).sup.+; HPLC retention time: 6.52 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0843] 2-118:

[0844] MS (ES, Pos.): 461 (M+1).sup.+, 463 (M+3).sup.+, 465 (M+5).sup.+; HPLC retention time: 6.34 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0845] 2-119:

[0846] MS (ES, Pos.): 447 (M+1).sup.+, 449 (M+3).sup.+, 451 (M+5).sup.+; HPLC retention time: 5.79 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0847] 2-120:

[0848] MS (ES, Pos.): 549 (M+1).sup.+, 551 (M+3).sup.+, 553 (M+5).sup.+; HPLC retention time: 6.77 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0849] 2-121:

[0850] MS (ES, Pos.): 535 (M+1).sup.+, 537 (M+3).sup.+, 539 (M+5).sup.+; HPLC retention time: 5.83 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 m/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0851] 2-122:

[0852] MS (ES, Pos.): 417 (M+1).sup.+; HPLC retention time: 6.49 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0853] 2-123:

[0854] MS (ES, Pos.): 403 (M+1).sup.+; HPLC retention time: 5.96 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0855] 2-124:

[0856] MS (ES, Pos.): 465 (M+1).sup.+, 467 (M+3).sup.+, HPLC retention time: 6.87 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0857] 2-125:

[0858] MS (ES, Pos.): 433 (M+1).sup.+; HPLC retention time: 6.38 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0859] 2-126:

[0860] MS (ES, Pos.): 501 (M+1).sup.+, 503 (M+3).sup.+, 505 (M+5).sup.+; HPLC retention time: 6.26 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0861] 2-128:

[0862] MS (ES, Pos.): 579 (M+1).sup.+, 581 (M+3).sup.+, 583 (M+5).sup.+; HPLC retention time: 6.10 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0863] *2: HCl salt

3TABLE 3*.sup.1 1247 Com. No. Ex. No. 1248 Y R.sup.6 R.sup.7 R.sup.8 --Ar melting point (.degree. C.) (solvent for crystallization) 3-001 5 1249 N CH.sub.3 CH.sub.3 H 1250 151-153 (No solvent) 3-002 5 1251 CH CH.sub.3 CH.sub.3 H 1252 amorphous 3-003 6 1253 N CH.sub.3 CH.sub.3 H 1254 142-144 (IPE) 3-004 6 1255 N CH.sub.3 CH.sub.3 H 1256 143-145 (IPE) 3-005 6 1257 CH CH.sub.3 CH.sub.3 H 1258 amorphous 3-006 6 1259 N CH.sub.3 CH.sub.3 H 1260 131-133 (hexane) 3-007 6 1261 CH CH.sub.3 CH.sub.3 H 1262 amorphous 3-008 5 1263 N CH.sub.3 CH.sub.3 H 1264 amorphous 3-009 6 1265 N CH.sub.3 CH.sub.3 H 1266 amorphous 3-010 6 1267 CH CH.sub.3 CH.sub.3 CH.sub.3 1268 oil 3-011 6 1269 CH CH.sub.3 CH.sub.3 H 1270 oil 3-012 5 1271 N CH.sub.3 CH.sub.3 H 1272 110-112 (No solvent) 3-013 5 1273 N CH.sub.3 CH.sub.3 CH.sub.3 1274 amorphous 3-014 8 1275 N CH.sub.3 CH.sub.3 H 1276 205-507*.sup.2(No solvent) 3-015 7 1277 N CH.sub.3 CH.sub.3 H 1278 amorphous 3-016 8 1279 N CH.sub.3 CH.sub.3 H 1280 amorphous*.sup.2 3-017 9 1281 N CH.sub.3 CH.sub.3 H 1282 94-96 (No solvent) 3-018 10 1283 N CH.sub.3 CH.sub.3 H 1284 215-217*.sup.3(No solvent) 3-019 7 1285 N CH.sub.3 CH.sub.3 H 1286 amorphous 3-020 7 1287 N CH.sub.3 CH.sub.3 H 1288 amorphous 3-021 7 1289 N CH.sub.3 CH.sub.3 H 1290 amorphous 3-022 7 1291 N CH.sub.3 CH.sub.3 H 1292 amorphous *.sup.1: Com. No. = compound number, Ex. No. = example number, solvent for crystallization; IPE = diisopropyl ether

[0864] Analytical data of non-crystal compounds are described below.

[0865] 3-002:

[0866] MS (ES, Pos.): 514 (M+1).sup.+, 516 (M+3).sup.+; HPLC Retention time: 6.77 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0867] 3-005:

[0868] MS (ES, Pos.): 547 (M+1).sup.+, 549 (M+3).sup.+; HPLC Retention time: 7.06 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0869] 3-007:

[0870] MS (ES, Pos.): 514 (M+1).sup.+, 516 (M+3).sup.+; HPLC Retention time: 7.01 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0871] 3-008:

[0872] MS (ES, Pos.): 577 (M+1).sup.+, 579 (M+3).sup.+; HPLC Retention time: 10.89 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.2 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 30% A, 50% B and 20% C to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0873] 3-009:

[0874] MS (ES, Pos.): 597 (M+1).sup.+, 599 (M+3).sup.+; HPLC Retention time: 13.94 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.2 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 30% A, 50% B and 20% C to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0875] 3-010:

[0876] MS No spectrum (decomposition in LC-MS); .sup.1H NMR (360 MHz, DMSO-D6) .delta. ppm 0.83 (3H, t, J=6.4 Hz), 1.24 (12H, br.s), 1.52 (4H, m), 1.79 (9H, m), 1.93 (3H, s), 2.29 (3H, s), 2.32 (2H, t, J=7.1 Hz), 2.39 (3H, s), 2.68 (2H, t, J=11.3 Hz), 3.46 (2H, d, J=11.7 Hz,), 4.00 (2H, d, J=5.9 Hz), 6.45 (1H, s), 7.47 (2H, s)

[0877] 3-011:

[0878] MS (ES, Pos.): 596 (M+1).sup.+, 598 (M+3).sup.+; HPLC Retention time: 6.45 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0879] 3-013:

[0880] MS (ES, Pos.): 617 (M+1).sup.+, 619 (M+3).sup.+, 621 (M+5).sup.+; HPLC Retention time: 6.65 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0881] 3-015:

[0882] MS (ES, Pos.): 570 (M+1).sup.+, 572 (M+3).sup.+; HPLC Retention time: 7.05 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 m/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0883] 3-016:

[0884] MS (ES, Pos.): 629 (M+1).sup.+, 631 (M+3).sup.+; HPLC Retention time: 6.86 min. (Xterra MS C18 (Waters, Milford, Mass.) 3.5 .mu.m, 4.6.times.100 mm); Flow rate 1.6 ml/min. Three mobile phases (mobile phase A 95% 25 mM ammonium acetate+5% acetonitrile; mobile phase B: acetonitrile; mobile phase C: methanol) were employed to run a gradient condition from 100% A to 50% B and 50% C in 6.5 min., to 100% B in 1 min, 100% B for 1 min. and reequilibrate with 100% A for 1.5 min)

[0885] 3-019:

[0886] MS (ES, Pos.): 705 (M+1).sup.+, 707 (M+3).sup.+; .sup.1H NMR (300 MHz, CDCl.sub.3) .delta. ppm 0.89 (3H, t, J=6.7 Hz), 1.17-1.40 (4H, m), 1.42-1.72 (4H, m), 1.81-1.93 (3H, m), 1.92 (6H, s), 2.00-2.07 (4H, m), 2.34 (2H, t, J=7.5 Hz), 2.44 (3H, d, J=1.1 Hz), 2.51 (3H, s), 2.74-2.81 (2H, m), 2.90-3.04 (2H, m), 4.03 (2H, d, J=6.4 Hz,), 4.10-4.19 (2H, m), 5.28-5.42 (4H, m), 6.57 (1H, m), 7.30 (2H, s)

[0887] 3-020:

[0888] MS (ES, Pos.): 729 (M+1).sup.+, 731 (M+3).sup.+; .sup.1H NMR (300 MHz, CDCl.sub.3) .delta. ppm 0.89 (3H, t, J=6.7 Hz), 1.20-1.40 (6H, m), 1.41-1.53 (2H, m), 1.65-1.80 (2H, m), 1.81-2.00 (3H, m), 1.92 (6H, s), 2.02-2.19 (4H, m), 2.36 (2H, t, J=7.5 Hz), 2.44 (3H, d, J=1.0 Hz), 2.51 (3H, s), 2.77-2.90 (6H, m), 2.92-3.05 (2H, m), 4.03 (2H, d, J=6.4 Hz,), 4.05-4.19 (2H, m), 5.28-5.47 (8H, m), 6.57 (1H, m), 7.30 (2H, s)

[0889] 3-021:

[0890] MS (ES, Pos.): 753 (M+1).sup.+, 754 (M+3).sup.+; .sup.1H NMR (500 MHz, CDCl.sub.3) .delta. ppm 0.97 (3H, t, J=7.3 Hz), 1.15-1.40 (1H, m), 1.45-1.55 (2H, m), 1.84-2.00 (3H, m), 1.92 (6H, s), 2.04-2.11 (2H, m), 2.38-2.44 (4H, m), 2.43 (3H, d, J=1.2 Hz), 2.50 (3H, s), 2.77-2.90 (10H, m), 2.94-3.02 (2H, m), 4.04 (2H, d, J=6.7 Hz,), 4.09-4.16 (2H, m), 5.27-5.46 (12H, m), 6.57 (1H, m), 7.30 (2H, s)

[0891] 3-022:

[0892] MS (ES, Pos.): 727 (M+1).sup.+, 729 (M+3).sup.+; .sup.1H NMR (500 MHz, CDCl.sub.3) .delta. ppm 0.97 (3H, t, J=7.3 Hz), 1.15-1.40 (1H, m), 1.45-1.55 (2H, m), 1.65-1.80 (2H, m), 1.84-1.98 (2H, m), 1.92 (6H, s), 2.03-2.17 (4H, m), 2.36 (2H, t, J=7.3 Hz), 2.43 (3H, d, J=1.2 Hz), 2.50 (3H, s), 2.77-2.91 (8H, m), 2.94-3.02 (2H, m), 4.04 (2H, d, J=6.7 Hz,), 4.09-4.16 (2H, m), 5.28-5.44 (10H, m), 6.57 (1H, m), 7.30 (2H, s)

[0893] *2: optically active compound

[0894] *3: 1 Na salt

Test Example

[CRF Receptor Binding Test]

[0895] Monkey amygdala membranes were used as a receptor preparation.

[0896] .sup.125I-CRF was used as .sup.125I-labeled ligand.

[0897] Binding reaction using the .sup.125I -labeled ligand was carried out by the following method described in The Journal of Neuroscience, 7, 88 (1987).

[0898] Preparation of Receptor Membranes:

[0899] Monkey amygdala was homogenized in 50 mM Tris-HCl buffer (pH 7.0) containing 10 mM MgCl.sub.2, 2 mM EDTA and centrifuged at 48,000.times.g for 20 min, and the precipitate was washed once with Tris-HCl buffer. The washed precipitate was suspended in 50 mM Tris-HCl buffer (pH 7.0) containing 10 mM MgCl.sub.2, 2 mM EDTA, 0.1% bovine serum albumin and 100 kallikrein units/ml aprotinin, to obtain a membrane preparation.

[0900] CRF Receptor Binding Test:

[0901] The membrane preparation (0.3 mg protein/ml), .sup.125I-CRF (0.2 nM) and a test drug were reacted at 25.degree. C. for 2 hours. After completion of the reaction, the reaction mixture was filtered by suction through a glass filter (GF/C) treated with 0.3% polyethylene imine, and the glass filter was washed three times with phosphate-buffered saline containing 0.01% Triton X-100. After the washing, the radioactivity of the filter paper was measured in a gamma counter.

[0902] The amount of .sup.125I-CRF bound when the reaction was carried out in the presence of 1 .mu.M CRF was taken as the degree of nonspecific binding of .sup.125I -CRF, and the difference between the total degree of .sup.125I -CRF binding and the degree of nonspecific .sup.125I -CRF binding was taken as the degree of specific .sup.125I -CRF binding. An inhibition curve was obtained by reacting a definite concentration (0.2 nM) of .sup.125I-CRF with various concentrations of each test drug under the conditions described above. A concentration of the test drug at which binding of .sup.125I -CRF is inhibited by 50% (IC.sub.50) was determined from the inhibition curve.

[0903] As a result, it was found that compounds 1-003, 1-004, 1-005, 1-007, 1-008, 1-009, 1-010, 1-013, 1-014, 1-016, 1-018, 1-019, 1-021, 1-032, 1-038, 1-039, 1-040, 1-046, 1-050, 1-051, 1-052, 1-053, 1-054, 1-056, 1-057, 1-058, 1-059, 1-060, 1-061, 1-062, 1-063, 1-064, 1-067, 1-068, 1-072, 1-073, 1-074, 1-077, 1-078, 1-087, 1-088, 1-089, 1-090, 1-091, 1-097, 1-098, 1-099, 1-103, 1-104, 1-105, 1-112, 1-117, 1-118, 1-120, 1-121, 1-122, 1-123, 1-125, 1-126, 1-127, 1-128, 1-129, 1-130, 1-131, 1-132, 1-133, 1-135, 1-141, 1-142, 1-143, 1-144, 1-145, 1-148, 1-149, 1-150, 1-151, 1-152, 1-153, 1-154, 1-155, 1-156, 1-157, 1-158, 1-159, 1-160, 1-161, 1-162, 1-163, 1-164, 1-165, 1-166, 1-167, 1-172, 1-173, 1-176, 1-177, 1-178, 1-179, 1-181, 1-183, 1-184, 1-188, 1-195, 1-208, 1-213, 1-235, 1-236, 1-237, 1-243, 1-245, 1-251, 1-257, 1-262, 1-264, 1-278, 1-280, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-302, 1-304, 1-306, 1-308, 1-319, 1-320, 1-332, 1-333, 1-336, 1-337, 2-002, 2-003, 2-004, 2-005, 2-006, 2-007, 2-008, 2-009, 2-010, 2-011, 2-012, 2-013, 2-014, 2-015, 2-016, 2-017, 2-018, 2-019, 2-020, 2-021, 2-022, 2-023, 2-024, 2-025, 2-026, 2-027, 2-028, 2-029, 2-030, 2-031, 2-032, 2-033, 2-034, 2-035, 2-036, 2-037, 2-038, 2-039, 2-040, 2-041, 2-042, 2-043, 2-044, 2-045, 2-046, 2-047, 2-048, 2-049, 2-050, 2-052, 2-053, 2-054, 2-055, 2-056, 2-057, 2-058, 2-059, 2-060, 2-061, 2-062, 2-063, 2-064, 2-065, 2-066, 2-068, 2-069, 2-070, 2-071, 2-072, 2-073, 2-074, 2-075, 2-076, 2-077, 2-078, 2-079, 2-080, 2-081, 2-082, 2-084, 2-087, 2-088, 2-089, 2-090, 2-091, 2-092, 2-093, 2-094, 2-095, 2-096, 2-097, 2-098, 2-099, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112, 2-113, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-122, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 3-001, 3-004, 3-006, 3-007, 3-008, 3-009, 3-015 and 3-018 can be exemplified as typical compounds having an IC.sub.50 value of 50 nM or less.

EFFECT OF THE INVENTION

[0904] According to the present invention, compounds having a high affinity for CRF receptors have been provided. These compounds are effective against diseases in which CRF is considered to be involved, such as depression, anxiety, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorder, hypertension, gastric diseases, drug dependence, epilepsy, cerebral infarction, cerebral ischemia, cerebral edema, cephalic external wound, inflammation, immunity-related diseases, alopecia, irritable bowel syndrome, sleep disorders, epilepsy, dermatitides, schizophrenia, etc.

Claims

1. A pyrrolopyrimidine or pyrrolopyridine derivative substituted with a cyclic amino group represented by the following formula [I]: 1293(wherein the cyclic amino group is represented by the following formula [II]: 1294in which the cyclic amino group is a 3- to 8-membered saturated cyclic amine or a 3- to 8-membered saturated cyclic amine bridged with C.sub.1-5alkylene or C.sub.1-4alkylene-O--C.sub.1-4alkylene between any different two carbon atoms of the cyclic amine, which cyclic amine is substituted with a group represented by --(CR.sup.1R.sup.2).sub.- m--(CHR.sup.3).sub.n--X, R.sup.4 and R.sup.5 independently on the same or different carbon atoms of the cyclic amine; X is cyano, hydroxy or --OR.sup.9; Y is N or CR.sup.10; R.sup.1 is hydrogen, hydroxy, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2 is hydrogen or C.sub.1-5alkyl; R.sup.3 is hydrogen, cyano, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; m is an integer selected from 0, 1, 2, 3, 4 and 5; n is 0 or 1; with the proviso that when X is hydroxy or OR.sup.9, and n is 0, then m is an integer selected from 1, 2, 3, 4 and 5; R.sup.4 is hydrogen, hydroxy, hydroxy-C.sub.1-5alkyl, cyano, cyano-C.sub.1-5alkyl or C.sub.1-5alkyl; R.sup.5 is hydrogen or C.sub.1-5alkyl; R.sup.6 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy or --N(R.sup.11)R.sup.12; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen, halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy, --N(R.sup.11a)R.sup.12a, --CO.sub.2R.sup.13, cyano, nitro, C.sub.1-5alkylthio, trifluoromethyl or trifluoromethoxy; or R.sup.7 and R.sup.8 are taken together to form --CH.sub.2--CH.sub.2--CH.s- ub.2--CH.sub.2-- or --CH.dbd.CH--CH.dbd.CH--; R.sup.9 is C.sub.1-24acyl, C.sub.1-10alkoxycarbonyl, aryl-C.sub.1-5alkyloxycarbonyl, --CO--O--CHR.sup.14--O--CO--R.sup.15, --P(.dbd.O)(OR.sup.14a)OR.sup.15a, --CO--(CH.sub.2).sub.p--(CHR.sup.16).sub.q--NR.sup.17R.sup.18, arylcarbonyl or heteroarylcarbonyl, wherein each said acyl, aryl and heteroaryl is unsubstituted or substituted with C.sub.1-5alkoxy, and C.sub.1-24acyl optionally includes one to six double bonds; R.sup.10 is hydrogen, C.sub.1-5alkyl, halogen, cyano or --CO.sub.2R.sup.19; Ar is aryl or heteroaryl which aryl or heteroaryl is unsubstituted or substituted with 1 or more substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.2-5alkenyl, C.sub.2-5alkynyl, C.sub.1-5alkoxy, C.sub.1-5alkylthio, C.sub.1-5alkylsulfinyl, C.sub.1-5alkylsulfonyl, cyano, nitro, hydroxy, --CO.sub.2R.sup.19a, C(.dbd.O)R.sup.19a, CONR.sup.11bR.sup.12b, --OC(.dbd.O)R.sup.19a, --NR.sup.11bCO.sub.2R.sup.1- 9b, --S(O).sub.rNR.sup.11bR.sup.12b, hydroxy-C.sub.2-5alkylamino-C.sub.2-5- alkoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, fluoromethoxy, methylenedioxy, ethylenedioxy and --N(R.sup.20)R.sup.21; with the proviso that when X is hydroxy, Y is N, and the cyclic amino group is 5-membered ring, then Ar is aryl or heteroaryl which aryl or heteroaryl is substituted with at least one of substituents which are selected from halogen and trifluoromethyl; R.sup.11 and R.sup.12 are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl; R.sup.11a and R.sup.12a are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl- ; R.sup.11b and R.sup.12b are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.su- b.1-5alkyl; R.sup.13 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl, C.sub.3-8cycloalkyloxy-C.sub.1-5alkyl or phenyl; R.sup.14 and R.sup.15 are the same or different, and independently are hydrogen, C.sub.1-5alkyl or aryl-C.sub.1-5alkyl; R.sup.14a and R.sup.15a are the same or different, and independently are hydrogen, C.sub.1-5alkyl or aryl-C.sub.1-5alkyl; R.sup.16 is hydrogen, C.sub.1-5alkyl, aryl, heteroaryl, aryl-C.sub.1-5alkyl, heteroaryl-C.sub.1-5alkyl, hydroxy-C.sub.1-5alkyl, hydroxycarbonyl-C.sub.1-5alkyl, hydroxyphenyl-C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl, amino-C.sub.1-5alkyl, guanidino-C.sub.1-5alkyl, mercapto-C.sub.1-5alkyl, C.sub.1-5alkylthio-C.sub.1-5alkyl or aminocarbonyl-C.sub.1-5alkyl; R.sup.17 and R.sup.18 are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.- 1-5alkyl, C.sub.1-10acyl, C.sub.1-10alkoxycarbonyl or aryl-C.sub.1-5alkyloxycarbonyl; or R.sup.16 and R.sup.17 are taken together to form --CH.sub.2--, --CH.sub.2CH.sub.2--, --CH.sub.2CH.sub.2CH.sub.2-- or --CH.sub.2CH.sub.2CH.sub.2CH.sub.2--; p is an integer selected from 0, 1, 2, 3, 4 and 5; q is 0 or 1; R.sup.19 is hydrogen or C.sub.1-5alkyl; R.sup.19a is hydrogen or C.sub.1-5alkyl; r is 1 or 2; R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-5alkyl), individual isomers thereof, racemic or non-racemic mixtures of isomers thereof or N-oxide thereof, or pharmaceutically acceptable salts and hydrates thereof.

2. The pyrrolopyrimidine or pyrrolopyridine derivative substituted with the cyclic amino group according to claim 1, which is a compound represented by the following formula [III]: 1295(wherein the cyclic amino group is represented by the following formula [IV]: 1296in which the cyclic amino group is a 3- to 8-membered saturated cyclic amine or a 3- to 8-membered saturated cyclic amine bridged with C.sub.1-5alkylene or C.sub.1-4alkylene-O--C.sub.1-4alkylene between any different two carbon atoms of the cyclic amine, which cyclic amine is substituted with a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.sup.3).sub.n--CN, R.sup.4 and R.sup.5 independently on the same or different carbon atoms of the cyclic amine; Y is N or CR.sup.10; R.sup.1 is hydrogen, hydroxy, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2 is hydrogen or C.sub.1-5alkyl; R.sup.3 is hydrogen, cyano, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; m is an integer selected from 0, 1, 2, 3, 4 and 5; n is 0 or 1; R.sup.4 is hydrogen, hydroxy, hydroxy-C.sub.1-5alkyl, cyano, cyano-C.sub.1-5alkyl or C.sub.1-5alkyl; R.sup.5 is hydrogen or C.sub.1-5alkyl; R.sup.6 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.- 1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy or --N(R.sup.11)R.sup.12; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen, halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy, --N(R.sup.11a)R.sup.12a, --CO.sub.2R.sup.13, cyano, nitro, C.sub.1-5alkylthio, trifluoromethyl or trifluoromethoxy; or R.sup.7 and R.sup.8 are taken together to form --CH.sub.2--CH.sub.2--CH.s- ub.2--CH.sub.2-- or --CH.dbd.CH--CH.dbd.CH--; R.sup.10 is hydrogen, C.sub.1-5alkyl, halogen, cyano or --CO.sub.2R.sup.19; Ar is aryl or heteroaryl which aryl or heteroaryl is unsubstituted or substituted with 1 or more substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.2-5alkenyl, C.sub.2-5alkynyl, C.sub.1-5alkoxy, C.sub.1-5alkylthio, C.sub.1-5alkylsulfinyl C.sub.1-5alkylsulfonyl, cyano, nitro, hydroxy, --CO.sub.2R.sup.19a, --C(.dbd.O)R.sup.19a, --CONR.sup.11bR.sup.12b, --OC(.dbd.O)R.sup.19a, --NR.sup.11bCO.sub.2R.sup.19a, S(O).sub.rNR.sup.11bR.sup.12b, hydroxy-C.sub.2-5alkylamino-C.sub.2-5alkox- y, trifluoromethyl, trifluoromethoxy, difluoromethoxy, fluoromethoxy, methylenedioxy, ethylenedioxy and --N(R.sup.20)R.sup.21; R.sup.11 and R.sup.12 are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl- ; R.sup.11 and R.sup.12 are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.su- b.1-5alkyl; R.sup.11b and R.sup.12b are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-15alkyl; R.sup.13 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl, C.sub.3-8cycloalkyloxy-C.sub.1-5alkyl or phenyl; R.sup.19 is hydrogen or C.sub.1-5alkyl; R.sup.19a is hydrogen or C.sub.1-5alkyl; r is 1 or 2; R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-5alkyl), individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

3. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 2 represented by formula [III], wherein Y is N; the cyclic amino group, m, n, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and Ar are as defined in claim 2; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

4. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 2 represented by formula [III], wherein Y is N; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; the cyclic amino group, m, R.sup.6, R.sup.7, R.sup.8 and Ar are as defined in claim 2; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

5. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 2 represented by formula [III], wherein Y is N; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 0, 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl); individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

6. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 2 represented by formula [III], wherein Y is N; the cyclic amino group is a 6-membered saturated cyclic amine; m is 0 or 1; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

7. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 2 represented by formula [III], wherein Y is CR.sup.10; the cyclic amino group, m, n, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 R.sup.8, R.sup.10 and Ar are as defined in claim 2; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

8. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 2 represented by formula [III], wherein Y is CR.sup.10; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.10 is hydrogen or halogen; the cyclic amino group, m, R.sup.6, R.sup.7, R.sup.8 and Ar are as defined in claim 2; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

9. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 2 represented by formula [III], wherein Y is CR.sup.10; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 0, 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; R.sup.10 is hydrogen or halogen; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl); individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

10. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 2 represented by formula [III], wherein Y is CR.sup.10; the cyclic amino group is a 6-membered saturated cyclic amine; m is 0 or 1; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; R.sup.10 is hydrogen; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

11. The pyrrolopyrimidine or pyrrolopyridine derivative substituted with the cyclic amino group according to claim 1, which is a compound represented by the following formula [V]: 1297(wherein the cyclic amino group is represented by the following formula [VI]: 1298in which the cyclic amino group is a 3- to 8-membered saturated cyclic amine or a 3- to 8-membered saturated cyclic amine bridged with C.sub.1-5alkylene or C.sub.1-4alkylene-O--C.sub.1-4alkylene between any different two carbon atoms of the cyclic amine, which cyclic amine is substituted with a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.sup.3).sub.n--OH, R.sup.4 and R.sup.5 independently on the same or different carbon atoms of the cyclic amine; Y is N or CR.sup.10; R.sup.1 is hydrogen, hydroxy, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2 is hydrogen or C.sub.1-5alkyl; R.sup.3 is hydrogen, cyano, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; m is an integer selected from 0, 1, 2, 3, 4 and 5; n is 0 or 1; with the proviso that when n is 0, m is an integer selected from 1, 2, 3, 4 and 5; R.sup.4 is hydrogen, hydroxy, hydroxy-C.sub.1-5alkyl, cyano, cyano-C.sub.1-5alkyl or C.sub.1-5alkyl; R.sup.5 is hydrogen or C.sub.1-5alkyl; R.sup.6 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy or --N(R.sup.11)R.sup.12; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen, halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy, --N(R.sup.11a)R.sup.12a- , --CO.sub.2R.sup.13, cyano, nitro, C.sub.1-5alkylthio, trifluoromethyl or trifluoromethoxy; or R.sup.7 and R.sup.8 are taken together to form --CH.sub.2--CH.sub.2--CH.sub.2--CH.sub.2-- or --CH.dbd.CH--CH.dbd.CH--; R.sup.10 is hydrogen, C.sub.1-5alkyl, halogen, cyano or --CO.sub.2R.sup.19; Ar is aryl or heteroaryl which aryl or heteroaryl is unsubstituted or substituted with 1 or more substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.2-5alkenyl, C.sub.2-5alkynyl, C.sub.1-5alkoxy, C.sub.1-5alkylthio, C.sub.1-5alkylsulfinyl, C.sub.1-5alkylsulfonyl, cyano, nitro, hydroxy, --CO.sub.2R.sup.19a, C(.dbd.O)R.sup.19a, CONR.sup.11bR.sup.12b --OC(.dbd.O)R.sup.19a, --NR.sup.11bCO.sub.2R.sup.19a, --S(O).sub.rNR.sup.11bR.sup.12b, hydroxy-C.sub.2-5alkylamino-C.sub.2-5alkoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, fluoromethoxy, methylenedioxy, ethylenedioxy and --N(R.sup.20)R.sup.21; with the proviso that when Y is N, and the cyclic amino group is 5-membered ring, then Ar is aryl or heteroaryl which aryl or heteroaryl is substituted with at least one of substituents which are selected from halogen and trifluoromethyl; R.sup.11 and R.sup.12 are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.su- b.1-5alkyl; R.sup.11a and R.sup.12a are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl; R.sup.11b and R.sup.12b are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl; R.sup.13 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.- 1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl, C.sub.3-8cycloalkyloxy-C.sub.1-5- alkyl or phenyl; R.sup.19 is hydrogen or C.sub.1-5alkyl; R.sup.19a is hydrogen or C.sub.1-5alkyl; r is 1 or 2; R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-5alkyl), individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

12. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is N; the cyclic amino group, m, n, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and Ar are as defined in claim 11; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

13. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is N; m is an integer selected from 1, 2, 3, 4 and 5; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; the cyclic amino group, R.sup.6, R.sup.7, R.sup.8 and Ar are as defined in claim 11; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

14. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is N; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20 R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl); with the proviso that when the cyclic amino group is 5-membered ring, Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with at least one of substituents which are selected from halogen and trifluoromethyl; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

15. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is N; the cyclic amino group is a 6-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

16. The pyrrolopyrimidine derivatives substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is N; m is 1; n is 0; R.sup.1 is C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2, R.sup.4 and R.sup.5 are hydrogen; the cyclic amino group, R.sup.6, R.sup.7, R.sup.8 and Ar are as defined in claim 11; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

17. The pyrrolopyrimidine derivatives substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is N; m is 1; n is 0; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; R.sup.1 is C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl); individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

18. The pyrrolopyrimidine derivatives substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is N; m is 1; n is 0; the cyclic amino group is a 6-membered saturated cyclic amine; R.sup.1 is C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and RB are the same or different, and independently are hydrogen or methyl; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

19. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is N; m is an integer selected from 1, 2, 3, 4 and 5; n is 0; R.sup.1, R.sup.2 and R.sup.5 are hydrogen; R.sup.4 is cyano; the cyclic amino group, R.sup.6, R.sup.7, R.sup.8 and Ar are as defined in claim 11, wherein a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.sup.3).sub.n--OH and R.sup.4 are substituted on the same carbon atom of the cyclic amine; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

20. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is N; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2 and R.sup.5 are hydrogen; R.sup.4 is cyano; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl), wherein a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.sup.3).sub.n--OH and R.sup.4 are substituted on the same carbon atom of the cyclic amine; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

21. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is N; the cyclic amino group is a 6-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2 and R.sup.5 are hydrogen; R.sup.4 is cyano; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino, wherein a group represented by --(CR.sup.1R.sup.2).sub.m, --(CHR.sup.3).sub.n--OH and R.sup.4 are substituted on the same carbon atom of the cyclic amine; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

22. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is CR.sup.10; the cyclic amino group, m, n, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.10 and Ar are as defined in claim 11; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

23. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is CR.sup.10; m is an integer selected from 1, 2, 3, 4 and 5; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.10 is hydrogen or halogen; the cyclic amino group, R.sup.6, R.sup.7, R.sup.9 and Ar are as defined in claim 11; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof or pharmaceutically acceptable salts and hydrates thereof.

24. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is CR.sup.10; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; R.sup.10 is hydrogen or halogen; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl); individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

25. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is CR.sup.10; the cyclic amino group is a 6-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; R.sup.10 is hydrogen; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

26. The pyrrolopyridine derivatives substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is CR.sup.10; m is 1; n is 0; R.sup.1 is C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.10 is hydrogen or halogen; the cyclic amino group, R.sup.6, R.sup.7, R.sup.8 and Ar are as defined in claim 11; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

27. The pyrrolopyridine derivatives substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is CR.sup.10; m is 1; n is 0; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; R.sup.1 is C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; R.sup.10 is hydrogen or halogen; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl); individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

28. The pyrrolopyridine derivatives substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is CR.sup.10; m is 1; n is 0; the cyclic amino group is a 6-membered saturated cyclic amine; R.sup.1 is C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; R.sup.10 is hydrogen; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

29. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is CR.sup.10; m is an integer selected from 1, 2, 3, 4 and 5; n is 0; R.sup.1, R.sup.2 and R.sup.5 are hydrogen; R.sup.4 is cyano; R.sup.10 is hydrogen or halogen; the cyclic amino group, R.sup.6, R.sup.7, R.sup.8 and Ar are as defined in claim 11, wherein a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.sup.3).sub.n--OH and R.sup.4 are substituted on the same carbon atom of the cyclic amine; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

30. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is CR.sup.10; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2 and R.sup.5 are hydrogen; R.sup.4 is cyano; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; R.sup.10 is hydrogen or halogen; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl), wherein a group represented by (CR.sup.1R.sup.2).sub.m--(CHR.sup.3).sub.n--OH and R.sup.4 are substituted on the same carbon atom of the cyclic amine; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

31. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 11 represented by formula [V], wherein Y is CR.sup.10; the cyclic amino group is a 6-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2 and R.sup.5 are hydrogen; R.sup.4 is cyano; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; R.sup.10 is hydrogen; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino, wherein a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.sup.3).sub- .n--OH and R.sup.4 are substituted on the same carbon atom of the cyclic amine; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

32. The pyrrolopyrimidine or pyrrolopyridine derivative substituted with the cyclic amino group according to claim 1, which is a compound represented by the following formula [VII]: 1299(wherein the cyclic amino group is represented by the following formula [VIII]: 1300in which the cyclic amino group is a 3- to 8-membered saturated cyclic amine or a 3- to 8-membered saturated cyclic amine bridged with C.sub.1-5alkylene or C.sub.1-4alkylene-O--C.sub.1-4alkylene between any different two carbon atoms of the cyclic amine, which cyclic amine is substituted with a group represented by --(CR.sup.1R.sup.2).sub.m--(CHR.sup.3).sub.n--OR.sup.9, R.sup.4 and R.sup.5 independently on the same or different carbon atoms of the cyclic amine; Y is N or CR.sup.10; R.sup.1 is hydrogen, hydroxy, C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; R.sup.2 is hydrogen or C.sub.1-5alkyl; R.sup.3 is hydrogen, cyano, C.sub.105alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl or hydroxy-C.sub.1-5alkyl; m is an integer selected from 0, 1, 2, 3, 4 and 5; n is 0 or 1; with the proviso that when n is 0, m is an integer selected from 1, 2, 3, 4 and 5; R.sup.4 is hydrogen, hydroxy, hydroxy-C.sub.1-5alkyl, cyano, cyano-C.sub.1-5alkyl or C.sub.1-5alkyl; R.sup.5 is hydrogen or C.sub.1-5alkyl; R.sup.6 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy or --N(R.sup.11)R.sup.12; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen, halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, hydroxy, C.sub.1-5alkoxy, C.sub.3-8cycloalkyloxy --N(R.sup.11a)R.sup.12a, --CO.sub.2R.sup.13, cyano, nitro, C.sub.1-5alkylthio, trifluoromethyl or trifluoromethoxy; or R.sup.7 and R.sup.8 are taken together to form --CH.sub.2--CH.sub.2--CH.sub.2--CH.sub.2-- or --CH.dbd.CH--CH.dbd.CH--; R.sup.9 is C.sub.1-24acyl, C.sub.1-10alkoxycarbonyl, aryl-C.sub.1-5alkyloxycarbonyl, --CO--O--CHR.sup.14--O--CO--R.sup.15, P(.dbd.O)(OR.sup.14a)OR.sup.15a, --CO--(CH.sub.2).sub.p--(CHR.sup.16).sub- .q--NR.sup.17R.sup.18, arylcarbonyl or heteroarylcarbonyl, wherein each said acyl, aryl and heteroaryl is unsubstituted or substituted with C.sub.1-5alkoxy, and C.sub.1-24acyl optionally includes one to six double bonds; R.sup.10 is hydrogen, C.sub.1-5alkyl, halogen, cyano or --CO.sub.2R.sup.19; Ar is aryl or heteroaryl which aryl or heteroaryl is unsubstituted or substituted with 1 or more substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.2-5alkenyl, C.sub.2-5alkynyl, C.sub.1-5alkoxy, C.sub.1-5alkylthio, C.sub.1-5alkylsulfinyl, C.sub.1-5alkylsulfonyl, cyano, nitro, hydroxy, --CO.sub.2R.sup.19a, --C(.dbd.O)R.sup.19a, --CONR.sup.11bR.sup.12b, --OC(.dbd.O)R.sup.19a, --NR.sup.11bCO.sub.2R.sup.19a, --S(O).sub.rNR.sup.11bR.sup.12b, hydroxy-C.sub.2-5alkylamino-C.sub.2-5alkoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, fluoromethoxy, methylenedioxy, ethylenedioxy and --N(R.sup.20)R.sup.21; R.sup.11 and R.sup.12 are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl; R.sup.11a and R.sup.12a are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.sub.1-5alkyl- ; R.sup.11b and R.sup.12b are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl or C.sub.3-8cycloalkyl-C.su- b.1-5alkyl; R.sup.13 is hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl, C.sub.3-8cycloalkyloxy-C.sub.1-5alkyl or phenyl; R.sup.14 and R.sup.15 are the same or different, and independently are hydrogen, C.sub.1-5alkyl or aryl-C.sub.1-5alkyl; R.sup.14a and R.sup.15a are the same or different, and independently are hydrogen, C.sub.1-5alkyl or aryl-C.sub.1-5alkyl; R.sup.16 is hydrogen, C.sub.1-5alkyl, aryl, heteroaryl, aryl-C.sub.1-5alkyl, heteroaryl-C.sub.1-5alkyl, hydroxy-C.sub.1-5alkyl, hydroxycarbonyl-C.sub.1-5alkyl, hydroxyphenyl-C.sub.1-5alkyl, C.sub.1-5alkoxy-C.sub.1-5alkyl, amino-C.sub.1-5alkyl, guanidino-C.sub.1-5alkyl, mercapto-C.sub.1-5alkyl, C.sub.1-5alkylthio-C.sub.1-5alkyl or aminocarbonyl-C.sub.1-5alkyl; R.sup.17 and R.sup.18 are the same or different, and independently are hydrogen, C.sub.1-5alkyl, C.sub.3-8cycloalkyl, C.sub.3-8cycloalkyl-C.sub.- 1-5alkyl, C.sub.1-10acyl, C.sub.1-10alkoxycarbonyl and aryl-C.sub.1-5alkyloxycarbonyl, or R.sup.16 and R.sup.17 are taken together to form --CH.sub.2--, --CH.sub.2CH.sub.2--, --CH.sub.2CH.sub.2CH.sub.2-- or --CH.sub.2CH.sub.2CH.sub.2CH.sub.2--; p is an integer selected from 0, 1, 2, 3, 4 and 5; q is 0 or 1; R.sup.19 is hydrogen or C.sub.1-5alkyl; R.sup.19a is hydrogen or C.sub.1-5alkyl; r is 1 or 2; R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-5alkyl), individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

33. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 32 represented by the formula [VII], wherein Y is N; the cyclic amino group, m, n, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and Ar are as defined in claim 32; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

34. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 32 represented by formula [VII], wherein Y is N; m is an integer selected from 1, 2, 3, 4 and 5; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; the cyclic amino group, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and Ar are as defined in claim 32; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

35. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 32 represented by the formula [VII], wherein the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 1, 2, 3, 4 and 5; n is 0; Y is N; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl); R.sup.9 is as defined in claim 32; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

36. The pyrrolopyrimidine derivative substituted with the cyclic amino group according to claim 32 represented by the formula [VII], wherein the cyclic amino group is a 6-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; Y is N; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or methyl; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino; R.sup.9 is as defined in claim 32; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

37. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 32 represented by formula [VII], wherein Y is CR.sup.10; the cyclic amino group, m, n, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10 and Ar are as defined in claim 32; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

38. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 32 represented by formula [VII], wherein Y is CR.sup.10; m is an integer selected from 1, 2, 3, 4 and 5; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; the cyclic amino group, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10 and Ar are as defined in claim 32; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

39. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 32 represented by formula [VII], wherein Y is CR.sup.10; the cyclic amino group is a 4- to 7-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.8 are the same or different, and independently are hydrogen or C.sub.1-5alkyl; R.sup.10 is hydrogen or halogen; Ar is phenyl or pyridyl which phenyl or pyridyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of halogen, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and --N(R.sup.20)R.sup.21 (wherein R.sup.20 and R.sup.21 are the same or different, and independently are hydrogen or C.sub.1-3alkyl); R.sup.9 is as defined in claim 32; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

40. The pyrrolopyridine derivative substituted with the cyclic amino group according to claim 32 represented by formula [VII], wherein Y is CR.sup.10; the cyclic amino group is a 6-membered saturated cyclic amine; m is an integer selected from 1, 2 and 3; n is 0; R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen; R.sup.6 is methyl; R.sup.7 and R.sup.9 are the same or different, and independently are hydrogen or methyl; R.sup.10 is hydrogen; Ar is phenyl which phenyl is substituted with two or three substituents, which are the same or different, selected from the group consisting of chloro, bromo, C.sub.1-3alkyl, C.sub.1-3alkoxy, C.sub.1-3alkylthio, trifluoromethyl, trifluoromethoxy and dimethylamino; R.sup.9 is as defined in claim 32; individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

41. Compounds represented by formula [I] according to claim 1, which compounds are selected from the group consisting of 2-{1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo- [2,3-d]pyrimidin-4-yl]-piperidin-2-yl}-ethanol, 2-{1-[7-(4-bromo-2,6-dimet- hyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-2-y- l}-ethanol, 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[- 2,3-d]pyrimidin-4-yl]-piperidin-2-yl}-ethanol, 2-{1-[7-(4-bromo-2,6-diethy- l-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-2-yl}-et- hanol, 2-{1-[2,5-dimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]pyrim- idin-4-yl]-piperidin-2-yl}-ethanol, 3-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-- 2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-2-yl}-pro pan-1-ol, 3-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2- ,3-d]pyrimidin-4-yl]-piperidin-2-yl}-propan-1-ol, {1-[7-(2,4-dibromo-6-met- hoxy-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-3-yl}- -methanol, {1-[7-(2,4-dibromo-6-methylsulfanyl-phenyl)-2,5-dimethyl-7H-pyr- rolo[2,3-d]pyrimidin-4-yl]-piperidin-3-yl}-methanol, {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyri- midin-4-yl]-piperidin-3-yl}-methanol, {1-[7-(4-bromo-2,6-dimethyl-phenyl)-- 2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-3-yl}-methanol, {1-[2,5-dimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-y- l]-piperidin-3-yl}-methanol, 2-{1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl- )-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-3-yl}-ethanol- , 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-piperidin-3-y}}-ethanol, 2-{1-[7-(4-bromo-2,6-dimethyl-phen- yl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-3-yl}-ethanol, 2-{1-[2,5-dimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo-2,3-d]pyrimidin-4- -yl]-piperidin-3-yl}-ethanol, {1-[2,5,6-trimethyl-7-(2,4,6-trimethyl-pheny- l)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, {1-[2,5-dimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-- yl]-piperidin-4-yl}-methanol, {1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl)- -2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol- , {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyr- imidin-4-yl]-piperidin-4-yl}-methanol, {1-[7-(4-bromo-2,6-dimethyl-phenyl)- -2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, {1-[2-methyl-9-(2,4,6-trimethyl-phenyl)-9H-1,3,9-triaza-fluoren-4-yl]-pip- eridin-4-yl}-methanol, {1-[7-(4-bromo-2,6-diethyl-phenyl)-2,5,6-trimethyl-- 7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, {1-[7-(4-bromo-2,6-diethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidi- n-4-yl]-piperidin-4-yl}-methanol, {1-[2,5,6-trimethyl-7-(2,4,6-tribromo-ph- enyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, {1-[2,5-dimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-y- l]-piperidin-4-yl}-methanol, {1-[7-(4-bromo-2,6-dichloro-phenyl)-2,5,6-tri- methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, {1-[7-(4-bromo-2,6-dichloro-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimid- in-4-yl]-piperidin-4-yl}-methanol, {1-[7-(2,6-dibromo-4-isopropyl-phenyl)-- 2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, {1-[7-(2,6-dibromo-4-isopropyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyri- midin-4-yl]-piperidin-4-yl}-methanol, {1-[7-(4-chloro-2,6-dimethyl-phenyl)- -2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol- , {1-[7-(4-chloro-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrim- idin-4-yl]-piperidin-4-yl}-methanol, 2-{1-[7-(2,6-dibromo-4-trifluoromethy- l-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}- -ethanol, 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo- [2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[7-(4-bromo-2,6-dimet- hyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-- ethanol, 2-{1-[2,5,6-trimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]- pyrimidin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[2,5-dimethyl-7-(2,4,6-tribr- omo-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-ethanol, 3-{1-[2,5,6-trimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimid- in-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[2,5-dimethyl-7-(2,4,6-trimethy- l-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo- [2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]py- rimidin-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[7-(4-bromo-2,6-dimethyl-p- henyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-propa- n-1-ol, 3-{1-[2,5-dimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]pyri- midin-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[7-(4-bromo-2,6-dichloro-phe- nyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-prop- an-1-ol, 3-{1-[7-(4-bromo-2,6-dichloro-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3- -d]pyrimidin-4-yl]-piperidin-4-yl}-propan-1-ol, {1-[7-(2,6-dibromo-4-trifl- uoromethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-3-meth- yl-piperidin-3-yl}-methanol, {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-tri- methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-3-methyl-piperidin-3-yl}-methanol, {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimid- in-4-yl]-3-methyl-piperidin-3-yl}-methanol, 1-{1-[7-(4-bromo-2,6-dimethyl-- phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-e- thane-1,2-diol, {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyr- rolo[2,3-d]pyrimidin-4-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimid- in-4-yl]-pyrrolidin-2-yl}-methanol, 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-- 2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyrrolidin-3-yl}-ethanol, {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyri- midin-4-yl]-azepan-4-yl}-methanol, {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5- -dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-azepan-4-yl}-methanol, {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyri- midin-4-yl]-piperidin-2-yl}-acetonitrile, 1-[2,5,6-trimethyl-7-(2,4,6-trim- ethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidine-3-carbonitrile, 1-[2,5-dimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-y- l]-piperidine-3-carbonitrile, 1-[7-(2,4-dibromo-6-methylsulfanyl-phenyl)-2- ,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidine-3-carbonitrile, 1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidine-3-carbonitrile, 1-[7-(4-bromo-2,6-dimethyl-- phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidine-3-carb- onitrile, 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidine-3-carbonitrile, 1-[7-(4-isopropyl-2-methylsulf- anyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidine-3- -carbonitrile, 1-[7-(4-isopropyl-2-methylsulfanyl-phenyl)-2,5-dimethyl-7H-- pyrrolo[2,3-d]pyrimidin-4-yl]-piperidine-3-carbonitrile, 1-[7-(2-bromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]- pyrimidin-4-yl]-piperidine-3-carbonitrile, 1-[7-(4-bromo-2,6-diethyl-pheny- l)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidine-3-carbonitr- ile, 1-[7-(4-bromo-2,6-diethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrim- idin-4-yl]-piperidine-3-carbonitrile, {1-[7-(2,6-dibromo-4-trifluoromethyl- -phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-3-yl}-- acetonitrile, {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrro- lo[2,3-d]pyrimidin-4-yl]-piperidin-3-yl}-acetonitrile, {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimid- in-4-yl]-piperidin-3-yl}-acetonitrile, 3-{1-[7-(4-bromo-2,6-dimethyl-pheny- l)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-3-yl}-propio- nitrile, 3-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3- -d]pyrimidin-4-yl]-piperidin-3-yl}-propionitrile, 1-[7-(4-bromo-2,6-dimeth- yl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidine-4-c- arbonitrile, 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidine-4-carbonitrile, {1-[2,5,6-trimethyl-7-(2,4,- 6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-aceto- nitrile, {1-[7-(2,6-dibromo-4-trifluoromethyl-phenyl)-2,5,6-trimethyl-7H-p- yrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyri- midin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[7-(4-bromo-2,6-dimethyl-phen- yl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-acetonit- rile, {1-[7-(4-bromo-2,6-diethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]- pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[7-(4-bromo-2,6-diethyl-p- henyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-aceto- nitrile, {1-[2,5,6-trimethyl-7-(2,4,6-tribromo-phenyl)-7H-pyrrolo[2,3-d]py- rimidin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[2,5-dimethyl-7-(2,4,6-trib- romo-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile- , {1-[7-(4-bromo-2,6-dichloro-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyr- imidin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[7-(4-bromo-2,6-dichloro-phe- nyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-acetoni- trile, {1-[7-(2,6-dibromo-4-isopropyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2- ,3-d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[7-(2,6-dibromo-4-is- opropyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-- yl}-acetonitrile, {1-[7-(4-methoxy-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H- -pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[7-(4-methoxy-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrim- idin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[7-(4-chloro-2,6-dimethyl-phen- yl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-aceto- nitrile, {1-[7-(4-chloro-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-- d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 8-[7-(4-bromo-2,6-dimethyl- -phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-8-aza-bicyclo[3.- 2.1]octane-3-carbonitrile, 8-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl- -7H-pyrrolo[2,3-d]pyrimidin-4-yl]-8-aza-bicyclo[3.2.1]octane-3-carbonitril- e, 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyr- imidin-4-yl]-pyrrolidine-3-carbonitrile, 1-[7-(4-bromo-2,6-dimethyl-phenyl- )-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyrrolidine-3-carbonitrile- , 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyri- midin-4-yl]-azepane-4-carbonitrile, 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5- -dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-azepane-4-carbonitrile, 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrim- idin-4-yl]-3-hydroxymethyl-piperidine-3-carbonitrile, {1-[7-(4-isopropyl-2-methylsulfanyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidin-4-yl}-methanol, {1-[7-(2-bromo-4-isopropyl-phen- yl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol- , {1-[7-(2,4-dibromo-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]- -piperidin-4-yl}-methanol, {1-[7-(2,6-dibromo-4-chloro-phenyl)-2,5-dimethy- l-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, 2-{1-[7-(2,6-dibromo-4-chloro-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrim- idin-4-yl]-piperidin-4-yl}-ethanol, 1-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-- 2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-propane-1- ,3-diol, {1-[7-(2,6-dibromo-4-chloro-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d- ]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[7-(4-bromo-2,6-dimethyl- -phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyrrolidin-3-yl}- -acetonitrile, {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo- [2,3-d]pyrimidin-4-yl]-pyrrolidin-3-yl}-acetonitrile, {1-[2,5-dimethyl-7-(2,4,6-trichloro-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-- yl]-piperidin-4-yl}-methanol, {1-[7-(2,6-dichloro-4-trifluoromethyl-phenyl- )-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol, 3-{1-[7-(4-chloro-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]p- yrimidin-4-yl]-piperidin-4-yl}-propan-1-ol, 1-[7-(4-chloro-2,6-dimethyl-ph- enyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidine-4-carbon- itrile, {1-[7-(2,6-Dichloro-4-trifluoromethyl-phenyl)-2,5-dimethyl-7H-pyrr- olo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-acetonitrile, 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrim- idin-4-yl]-azetidine-3-carbonitrile, 1-{1-[7-(4-bromo-2,6-dimethyl-phenyl)- -2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-ethanol, 1-{1-[7-(4-isopropyl-2-methylsulfanyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3- -d]pyrimidin-4-yl]-piperidin-4-yl}-ethanol, 1-{1-[7-(4-chloro-2,6-dimethyl- -phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-- ethanol, 1-{1-[7-(4-chloro-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,- 3-d]pyrimidin-4-yl]-piperidin-4-yl}-ethanol, {1-[7-(4-bromo-2,6-dimethyl-p- henyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-3-methyl-piperidin- -4-yl}-methanol, {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrro- lo[2,3-d]pyrimidin-4-yl]-3-methyl-piperidin-4-yl}-methanol, {8-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyri- midin-4-yl]-8-aza-bicyclo[3.2.1]oct-3-yl}-methanol, {8-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimid- in-4-yl]-8-aza-bicyclo[3.2.1]oct-3-yl}-methanol, {8-[7-(4-bromo-2,6-dimeth- yl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-8-aza-bicyclo[- 3.2.1]oct-3-yl}-acetonitrile, {8-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dime- thyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-8-aza-bicyclo[3.2.1]oct-3-yl}-aceton- itrile, 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2- ,3-d]pyrimidin-4-yl]-piperidin-4-yl}-malononitrile, 2-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrim- idin-4-yl]-piperidin-4-yl}-malononitrile, 2-{1-[1-(2,4-dichloro-phenyl)-2,- 3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-3-yl}-ethanol, 2-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyrid- in-4-yl]-piperidin-3-yl}-ethanol, {1-[1-(2,4-dichloro-phenyl)-2,3,6-trimet- hyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, {1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin- -4-yl]-piperidin-4-yl}-methanol, 2-{1-[1-(2,4-dichloro-phenyl)-2,3,6-trime- thyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyrid- in-4-yl]-piperidin-4-yl}-ethanol, 3-{1-[1-(2,4-dichloro-phenyl)-2,3,6-trim- ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyrid- in-4-yl]-piperidin-4-yl}-propan-1-ol, 1-[1-(2,4-dichloro-phenyl)-2,3,6-tri- methyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidine-3-carbonitrile, 1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-- 4-yl]-piperidine-3-carbonitrile, {1-[1-(2,4-dichloro-phenyl)-2,3,6-trimeth- yl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-3-yl}-acetonitrile, 1-[1-(2,4-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]- -piperidine-4-carbonitrile, 1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethy- l-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidine-4-carbonitrile, {1-[1-(2,4-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl- ]-piperidin-4-yl}-acetonitrile, 2-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,3,- 6-trimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-3-yl}-ethanol, {1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,3,6-trimethyl-H-pyrrolo[2,3-b]pyrid- in-4-yl]-piperidin-4-yl}-methanol, {1-[1-(4-chloro-2,6-dimethyl-phenyl)-2,- 3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, {1-[1-(4-chloro-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridi- n-4-yl]-piperidin-4-yl}-methanol, 2-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,- 3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[1-(4-chloro-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]p- yridin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[1-(4-chloro-2,6-dimethyl-pheny- l)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 3-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[1-(4-chloro-2,6-dimethyl-ph- enyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-propa- n-1-ol, 3-{1-[1-(4-chloro-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3- -b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 1-[1-(4-bromo-2,6-dimethyl-p- henyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidine-3-carboni- trile, 1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidine-4-carbonitrile, 1-[1-(4-chloro-2,6-dimethyl-phen- yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidine-4-carbonitri- le, 1-[1-(4-chloro-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyri- din-4-yl]-piperidine-4-carbonitrile, {1-[1-(4-bromo-2,6-dimethyl-phenyl)-2- ,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile- , {1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridi- n-4-yl]-piperidin-4-yl}-acetonitrile, {1-[1-(4-chloro-2,6-dimethyl-phenyl)- -3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[1-(2,6-dibromo-4-isopropyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]p- yridin-4-yl]-piperidin-4-yl}-methanol, {1-[1-(2,6-dibromo-4-isopropyl-phen- yl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, {1-[2,3,6-trimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyridin-4-- yl]-piperidin-4-yl}-methanol, {1-[3,6-dimethyl-1-(2,4,6-tribromo-phenyl)-1- H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, {1-[1-(4-bromo-2,6-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyri- din-4-yl]-piperidin-4-yl}-methanol, {1-[1-(4-bromo-2,6-dichloro-phenyl)-3,- 6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, {1-[2,3,6-trimethyl-1-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]pyridin-4-

-yl]-piperidin-4-yl}-methanol, {1-[3,6-dimethyl-1-(2,4,6-trichloro-phenyl)- -1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, {1-[1-(2,6-dibromo-4-chloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyri- din-4-yl]-piperidin-4-yl}-methanol, {1-[1-(2,6-dibromo-4-chloro-phenyl)-3,- 6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, {1-[1-(4-methoxy-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidin-4-yl}-methanol, {1-[1-(4-methoxy-2,6-dimethyl-phenyl- )-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, {1-[1-(2-bromo-4-isopropyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-- 4-yl]-piperidin-4-yl}-methanol, {1-[1-(4-isopropyl-2-methylsulfanyl-phenyl- )-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, {1-[1-(2,4-dibromo-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-pi- peridin-4-yl}-methanol, {1-[1-(2-bromo-4-trifluoromethyl-phenyl)-3,6-dimet- hyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, {1-[2,3,6-trimethyl-1-(2,4,5-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyridin-4-- yl]-piperidin-4-yl}-methanol, {1-[3,6-dimethyl-1-(2,4,5-tribromo-phenyl)-1- H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-methanol, 2-{1-[1-(2,6-dibromo-4-isopropyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[1-(2,6-dibromo-4-isopropyl-p- henyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol- , 2-{1-[2,3,6-trimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyridin- -4-yl]-piperidin-4-yl}-ethanol, 2-{1-[3,6-dimethyl-1-(2,4,6-tribromo-pheny- l)-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[1-(4-bromo-2,6-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[1-(4-bromo-2,6-dichloro-phenyl)- -3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[2,3,6-trimethyl-1-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]pyridin- -4-yl]-piperidin-4-yl}-ethanol, 2-{1-[3,6-dimethyl-(2,4,6-trichloro-phenyl- )-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[1-(2,6-dibromo-4-chloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[1-(2,6-dibromo-4-chloro-phenyl)- -3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[1-(4-methoxy-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]- pyridin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[1-(4-methoxy-2,6-dimethyl-phe- nyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[1-(2-bromo-4-isopropyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridi- n-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[1-(4-isopropyl-2-methylsulfanyl-phe- nyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[1-(2,4-dibromo-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-- piperidin-4-yl}-ethanol, 2-{1-[2,3,6-trimethyl-1-(2,4,5-tribromo-phenyl)-1- H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 2-{1-[3,6-dimethyl-1-(2,4,5-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyridin-4-y- l]-piperidin-4-yl}-ethanol, 2-{1-[5-bromo-1-(4-chloro-2,6-dimethyl-phenyl)- -3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethanol, 3-{1-[1-(2,6-dibromo-4-isopropyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[1-(2,6-dibromo-4-isoprop- yl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-pro- pan-1-ol, 3-{1-[2,3,6-trimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[3,6-dimethyl-1-(2,4,6-tr- ibromo-phenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[1-(4-bromo-2,6-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[1-(4-bromo-2,6-dichloro-phe- nyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-- ol, 3-{1-[2,3,6-trimethyl-1-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]pyri- din-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[3,6-dimethyl-1-(2,4,6-trichlo- ro-phenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[1-(2,6-dibromo-4-chloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[1-(2,6-dibromo-4-chloro-phe- nyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-- ol, 3-{1-[1-(4-methoxy-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3- -b]pyridin-4-yl]-piperidin-4-yl}-pro pan-1-ol, 3-{1-[1-(4-methoxy-2,6-dime- thyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-p- ropan-1-ol, 3-{1-[1-(4-isopropyl-2-methylsulfanyl-phenyl)-3,6-dimethyl-1H-- pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[2,3,6-trimethyl-1-(2,4,5-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyridin-- 4-yl]-piperidin-4-yl}-propan-1-ol, 3-{1-[3,6-dimethyl-1-(2,4,5-tribromo-ph- enyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-propan-1-ol, 1-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidin-4-yl}-ethane-1,2-diol, 1-{1-[1-(4-bromo-2,6-dimethyl- -phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ethan- e-1,2-diol, 1-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrro- lo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-propane-1,3-diol, 1-{1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyrid- in-4-yl]-piperidin-4-yl}-propane-1,3-diol, 1-[1-(2,6-dibromo-4-isopropyl-p- henyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidine-4-carboni- trile, 1-[1-(2,6-dibromo-4-isopropyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b- ]pyridin-4-yl]-piperidine-4-carbonitrile, 1-[2,3,6-trimethyl-1-(2,4,6-trib- romo-phenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidine-4-carbonitrile, 1-[3,6-dimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-- piperidine-4-carbonitrile, 1-[1-(4-bromo-2,6-dichloro-phenyl)-2,3,6-trimet- hyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidine-4-carbonitrile, 1-[1-(4-bromo-2,6-dichloro-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-- 4-yl]-piperidine-4-carbonitrile, 1-[2,3,6-trimethyl-1-(2,4,6-trichloro-phe- nyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidine-4-carbonitrile, 1-[3,6-dimethyl-1-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]- -piperidine-4-carbonitrile, 1-[1-(2,6-dibromo-4-chloro-phenyl)-2,3,6-trime- thyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidine-4-carbonitrile, 1-[1-(2,6-dibromo-4-chloro-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-- 4-yl]-piperidine-4-carbonitrile, 1-[1-(4-methoxy-2,6-dimethyl-phenyl)-2,3,- 6-trimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidine-4-carbonitrile, 1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridi- n-4-yl]-piperidine-4-carbonitrile, 1-[1-(2-bromo-4-isopropyl-phenyl)-3,6-d- imethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidine-4-carbonitrile, 1-[1-(4-isopropyl-2-methylsulfanyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]- pyridin-4-yl]-piperidine-4-carbonitrile, 1-[1-(2,4-dibromo-phenyl)-3,6-dim- ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidine-4-carbonitrile, 1-[1-(2-bromo-4-trifluoromethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyr- idin-4-yl]-piperidine-4-carbonitrile, 1-[2,3,6-trimethyl-1-(2,4,5-tribromo- -phenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidine-4-carbonitrile, 1-[3,6-dimethyl-1-(2,4,5-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-- piperidine-4-carbonitrile, {1-[1-(4-chloro-2,6-dimethyl-phenyl)-2,3,6-trim- ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[1-(2,6-dibromo-4-isopropyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]p- yridin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[1-(2,6-dibromo-4-isopropyl-- phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-aceton- itrile, {1-[2,3,6-trimethyl-1-(2,4,6-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyr- idin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[3,6-dimethyl-1-(2,4,6-tribrom- o-phenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[1-(4-bromo-2,6-dichloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyri- din-4-yl]-piperidin-4-yl}-acetonitrile, {1-[1-(4-bromo-2,6-dichloro-phenyl- )-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile- , {1-[2,3,6-trimethyl-1-(2,4,6-trichloro-phenyl)-1H-pyrrolo[2,3-b]pyridin-- 4-yl]-piperidin-4-yl}-acetonitrile, {1-[3,6-dimethyl-1-(2,4,6-trichloro-ph- enyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[1-(2,6-dibromo-4-chloro-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyri- din-4-yl]-piperidin-4-yl}-acetonitrile, {1-[1-(2,6-dibromo-4-chloro-phenyl- )-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile- , {1-[1-(4-methoxy-2,6-dimethyl-phenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]p- yridin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[1-(4-methoxy-2,6-dimethyl-p- henyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetoni- trile, {1-[1-(2-bromo-4-isopropyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]py- ridin-4-yl]-piperidin-4-yl}-acetonitrile, {1-[1-(4-isopropyl-2-methylsulfa- nyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-ac- etonitrile, {1-[1-(2,4-dibromo-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyrid- in-4-yl]-piperidin-4-yl}-acetonitrile, {1-[1-(2-bromo-4-trifluoromethyl-ph- enyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonit- rile, {1-[3,6-dimethyl-1-(2,4,5-tribromo-phenyl)-1H-pyrrolo[2,3-b]pyridin-- 4-yl]-piperidin-4-yl}-acetonitrile, carbonic acid 1-[7-(4-bromo-2,6-dimeth- yl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmet- hyl ester ethyl ester, pyridine-2-carboxylic acid 1-[7-(4-bromo-2,6-dimeth- yl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmet- hyl ester, methoxy-acetic acid 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dime- thyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-ylmethyl ester, methoxy-acetic acid 1-[1-(4-bromo-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-py- rrolo[2,3-b]pyridin-4-yl]-piperidin-4-ylmethyl ester, carbonic acid benzyl ester 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]py- rimidin-4-yl]-piperidin-4-ylmethyl ester, decanoic acid 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidi- n-4-yl]-piperidin-4-ylmethyl ester, 3-diethylamino-propionic acid 1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidi- n-4-yl]-piperidin-4-ylmethyl ester and phosphoric acid mono-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5-dimethyl-7H-pyrrolo[2,3-d]py- rimidin-4-yl]-piperidin-4-ylmethyl} ester, individual isomers thereof or racemic or non-racemic mixtures of isomers thereof, or pharmaceutically acceptable salts and hydrates thereof.

42. An antagonist for CRF receptors, comprising a pyrrolopyrimidine or pyrrolopyridine derivative substituted with a cyclic amino group, a pharmaceutically acceptable salt thereof or its hydrate according to any one of claims 1 to 41, as an active ingredient.

43. Use of a pyrrolopyrimidine or pyrrolopyridine derivative substituted with a cyclic amino group, a pharmaceutically acceptable salt thereof or its hydrate according to any one of claim 1 to 41, for the manufacture of an antagonist for CRF receptors.