Patent ID: 8486962
Filing Date: 2013-07-16
Classification: A61K,A61P

Abstract:
1. A compound which is an indolizinyl derivative of formula (I), or a pharmaceutically acceptable salt thereof: wherein: X is a bond, —NR8—, —O—, —S—, —SO—, or —SO X R1 represents an unsubstituted or substituted group selected from C6-C10 aryl, a 5- to 12-membered heterocyclyl group, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C6 cycloalkyl, -A1-L1-A2, -L2-A2, —COR′, and —Y—Z; R8 represents hydrogen, or an unsubstituted or substituted group selected from C6-C10 aryl, a 5- to 12-membered heterocyclyl group, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C6 cycloalkyl, -A1-L1-A2, -L2-A2, —COR′, and —Y—Z; or when X is NR8, R1 and R8 together with the nitrogen to which they are attached may form an unsubstituted or substituted, aromatic or non-aromatic 5- to 12-membered heterocyclyl group; A1 is an unsubstituted or substituted C6-C10 arylene group; L1 is a bond, —NR′—, —O—, —CO—, —OCO—, —OCONR′R″ or —CONR′R″—; L2 is a substituted or unsubstituted C1-C4 alkylene or C2-C4 alkenylene group; A2 is a substituted or unsubstituted C6-C10 aryl or 5- to 12-membered-heterocyclyl group; R2 is an unsubstituted or substituted group selected from C6-C10 aryl, a 5- to 12-membered heterocyclyl group, C1-C8 alkyl and C3-C6 cycloalkyl, or halogen; R3, R4, R5 and R6 independently represent C6-C10 aryl, a 5- to 12-membered heterocyclyl group, —(C1-C4 alkylene)-(C6-C10 aryl), —(C1-C4 alkylene)-(5- to 12-membered heterocyclyl), hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, —OR′, —CO R7 represents hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, —OR′, —CO Y is C1-C8 alkylene, C2-C8 alkenylene or C2-C8 alkynylene; Z is halogen, C3-C6 cycloalkyl, —OR′, —SR′, —SOR′, —SO R′ and R″ independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl, wherein the substituent(s) on any substituted alkyl, alkenyl or alkynyl group or moiety of R1 to R9, L2 or Y are selected from halogen, hydroxyl, amino, (C1-C4 alkyl)amino, di(C1-C4 alkyl)amino, C1-C4 alkoxy, CO the substituent(s) on any substituted cycloalkyl of R1, R2, R8 or Z are selected from C1-C8 alkyl, C2-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, Z and —Y—Z; the substituent(s) on any substituted aryl or heterocyclyl group or moiety of R1, A1, A2 or R2 to R6 are selected from C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, unsubstituted phenyl, Z and —Y—Z, wherein any C1-C4 alkyl or C1-C4 alkoxy substituent on an aryl or heterocyclyl group or moiety may be further substituted with one, two or three unsubstituted groups selected from halogen, hydroxyl, amino, (C1-C4 alkyl)amino, di(C1-C4 alkyl)amino, C1-C4 alkoxy, cyano, —COR excluding: 6-Hydroxy-alpha-oxo-2-phenyl-3-indolizineacetic acid ethyl ester, 5-Methyl-alpha-oxo-2-phenyl-3-indolizineacetic acid ethyl ester, ethyl 2-(2,5-dimethylindolizin-3-yl)-2-oxoacetate, N,N-dimethyl-2-oxo-2-(2-phenyl-indolizin-3-yl)-acetamide, alpha-Oxo-2-phenyl-N-(4,5,6,7-tetrahydro-2-benzothiazolyl)-3-indolizineacetamide, N-Cyclohexyl-alpha-oxo-2-phenyl-3-indolizineacetamide, N-(2,4-Dimethyl-5-nitrophenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-[3-[(Diethylamino)sulfonyl]phenyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, N-[2-[4-(Aminosulfonyl)phenyl]ethyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, 2-Chloro-4-fluoro-benzoic acid 3-[[oxo-(2-phenyl-3-indolizinyl)acetyl]amino]propyl ester, N-[2-(1,1-Dimethylethyl)phenyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, N-(3-Bromophenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, 3,5-Dimethyl-1-[oxo(2-phenyl-3-indolizinyl)acetyl]-piperidine, N-(2-Hydroxyethyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-[2-[(4-Nitrobenzoyl)oxy]ethyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, 2-(4-Chlorophenyl)-alpha-oxo-3-Indolizineacetic acid (2-fluorophenyl)methyl ester, 4-Fluoro-benzoic acid 2-[[[2-(4-chlorophenyl)-3-indolizinyl]oxoacetyl]amino]ethyl ester, 1-[[2-(4-Chlorophenyl)-3-indolizinyl]oxoacetyl]hexahydro-1H-azepine, 2-(4-Chlorophenyl)-alpha-oxo-3-indolizineacetic acid cyclopentyl ester, 2-(4-Chlorophenyl)-N-(2-hydroxyethyl)-alpha-oxo-3-indolizineacetamide, 4-(1,1-Dimethylethyl)-benzoic acid 2-[[[2-(4-chlorophenyl)-3-indolizinyl]oxoacetyl]amino]ethyl ester, 1-[Oxo(2-phenyl-3-indolizinyl)acetyl]-4-phenyl-piperazine, 2,6-Dimethyl-4-[oxo(2-phenyl-3-indolizinyl)acetyl]-morpholine, N-1,3-Benzodioxol-5-yl-2-(4-chlorophenyl)-alpha-oxo-3-indolizineacetamide, N-(4-Ethoxyphenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-(2,4-Dimethylphenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-(3-Hydroxypropyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-Methyl-N-(1-methyl-4-piperidinyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-[3-[(Diethylamino)sulfonyl]-4-methylphenyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, N-(6-Methoxy-3-pyridinyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-(3-Methoxyphenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-[4-Methyl-3-(4-morpholinylsulfonyl)phenyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, alpha-Oxo-2-phenyl-N-[3-(1-piperidinylsulfonyl)phenyl]-3-indolizineacetamide, N-(4-Chloro-2-methoxy-5-methylphenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-(2-Chloro-3-pyridinyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-[2-[[(4-Chlorophenyl)amino]carbonyl]phenyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, N-[5-[(Diethylamino)sulfonyl]-2-(4-morpholinyl)phenyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, alpha-Oxo-N-(3-phenoxyphenyl)-2-phenyl-3-indolizineacetamide, alpha-Oxo-2-phenyl-N-[4-(trifluoromethyl)phenyl]-3-indolizineacetamide, alpha-Oxo-2-phenyl-N-[4-(1-piperidinyl)phenyl]-3-indolizineacetamide, 4-Chloro-2-nitro-benzoic acid 3-[[oxo(2-phenyl-3-indolizinyl)acetyl]amino]propyl ester, 3-[(2,6-Dimethyl-4-morpholinyl)sulfonyl]-benzoic acid 3-[[oxo(2-phenyl-3-indolizinyl)acetyl]amino]propyl ester, N-(2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-(3,5-Dimethoxyphenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-(3-Chloro-4-fluorophenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-[4-[(Diethylamino)sulfonyl]phenyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, N-(3,4-Dimethylphenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, alpha-Oxo-N-(2-phenoxyphenyl)-2-phenyl-3-indolizineacetamide, N-[5-(1,1-Dimethylethyl)-2-methoxyphenyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, alpha-Oxo-2-phenyl-N-[4-(1-piperidinylsulfonyl)phenyl]-3-indolizineacetamide, N-(2,3-Dimethylphenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-(4-Bromo-2-fluorophenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-2-Naphthalenyl-alpha-oxo-2-phenyl-3-indolizineacetamide, N-[2-Chloro-5-(4-morpholinylsulfonyl)phenyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, 2,3-Dichloro-benzoic acid 3-[[oxo(2-phenyl-3-indolizinyl)acetyl]amino]propyl ester, 3,4-Dichloro-benzoic acid 3-[[oxo(2-phenyl-3-indolizinyl)acetyl]amino]propyl ester, N-(2,4-Dimethoxyphenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, 2-(4-Chlorophenyl)-alpha-oxo-N-phenyl-3-indolizineacetamide, 4-[[2-(4-Chlorophenyl)-3-indolizinyl]oxoacetyl]-morpholine, N-Ethyl-alpha-oxo-2-phenyl-3-indolizineacetamide, alpha-Oxo-2-phenyl-N-[3-(trifluoromethyl)phenyl]-3-indolizineacetamide, 4-[[Oxo(2-phenyl-3-indolizinyl)acetyl]amino]-benzoic acid methyl ester, N,N-Diethyl-alpha-oxo-2-phenyl-3-indolizineacetamide, N-[2-(Dimethylamino)ethyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, 2-Methyl-alpha-oxo-3-indolizineacetic acid, N-(2-Methoxyphenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-1-Naphthalenyl-alpha-oxo-2-phenyl-3-indolizineacetamide, 1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[oxo(2-phenyl-3-indolizinyl)acetyl]-isoquinoline, N-(1-Cyano-1-methylethyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, alpha-Oxo-2-phenyl-N-(2-phenylethyl)-3-indolizineacetamide, Hexahydro-1-[oxo(2-phenyl-3-indolizinyl)acetyl]-1H-azepine, alpha-Oxo-2-phenyl-N-4H-1,2,4-triazol-4-yl-3-indolizineacetamide, 1,2,3,4-Tetrahydro-1-[oxo(2-phenyl-3-indolizinyl)acetyl]-quinoline, N-(6-Methoxy-2-benzothiazolyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, alpha-Oxo-2-phenyl-N-2-thiazolyl-3-indolizineacetamide, N-[(4-Methoxyphenyl)methyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, N-[(4-Bromophenyl)methyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, N-(1,1-Dimethylethyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, N-Butyl-alpha-oxo-2-phenyl-3-indolizineacetamide, alpha-Oxo-N-[(3-phenoxyphenyl)methyl]-2-phenyl-3-indolizineacetamide, N-Ethyl-alpha-oxo-N,2-diphenyl-3-indolizineacetamide, alpha-Oxo-N,2-diphenyl-3-indolizineacetamide, N-[2-(3,4-Dimethoxyphenyl)ethyl]-alpha-oxo-2-phenyl-3-indolizineacetamide, alpha-Oxo-2-phenyl-N-(phenylmethyl)-3-indolizineacetamide, 4-[Oxo(2-phenyl-3-indolizinyl)acetyl]-morpholine, N-(4-Methylphenyl)-alpha-oxo-2-phenyl-3-indolizineacetamide, 2-Methyl-alpha-oxo-3-indolizineacetic acid ethyl ester, N,N-Dimethyl-2-phenyl-3-indolizineglyoxylamide, 2-Oxo-2-(2-phenyl-indolizin-3-yl)-N-(4-trifluoromethyl-phenyl)-acetamide, N-(2,4-Dichloro-phenyl)-2-oxo-2-(2-phenyl-indolizin-3-yl)-acetamide, 2-Oxo-2-(2-phenyl-indolizin-3-yl)-N-(3-trifluoromethyl-phenyl)-acetamide, 2-Oxo-2-(2-phenyl-indolizin-3-yl)-N-(4-piperidin-1-yl-phenyl)-acetamide 1-(5-methyl-2-phenyl-indolizin-3-yl)propane-1,2-dione 1-(5-methyl-2-phenyl-indolizin-3-yl)-propane-1,2-dione 1-oxime 1-(2,5-dimethyl-indolizin-3-yl)-2-phenyl-ethane-1,2-dione 1-oxime 1-(5-methyl-2-phenyl-indolizin-3-yl)-2-phenyl-ethane-1,2-dione 1-oxime 1-(2,5-dimethyl-indolizin-3-yl)-propane-1,2-dione 1-oxime 2-oxo-2-(2-phenylindolizin-3-yl)acetamide and their pharmaceutically or agriculturally acceptable salts thereof.