Patent ID: 6440986
Filing Date: 2002-08-27
Classification: A61P,C07D

Abstract:
A compound of formula a N-oxide, a pharmaceutically acceptable addition salt or a stereochemically isomeric form thereof, whereinA is CH, CR4 or N; Q is hydrogen or â€”NR1R2; R1 and R2 are each independently selected from hydrogen, hydroxy, C1-12alkyl, C1-12alkyloxy, C1-12alkylcarbonyl, C1-12alkyloxycarbonyl, aryl, amino, mono- or di(C1-12alkyl)amino, mono- or di(C1-12alkyl)aminocarbonyl wherein each of the aforementioned C1-12alkyl groups may optionally and each individually be substituted with one or two substituents each independently selected from hydroxy, C1-6alkyloxy, hydroxyC1-6alkyloxy, carboxyl, C1-6alkyloxycarbonyl, cyano, amino, imino, aminocarbonyl, aminocarbonylamino, mono- or di(C1-6alkyl)amino, aryl and Het; or R1 and R2 taken together may form pyrrolidinyl, piperidinyl, morpholinyl, azido or mono- or di(C1-12alkyl)aminoC1-4alkylidene; R3 is hydrogen, aryl, C1-6alkylcarbonyl, C1-6alkyl, C1-6alkyloxycarbonyl, C1-6alkyl substituted with C1-6alkyloxycarbonyl; and each R4 independently is hydroxy, halo, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, nitro, amino, trihalomethyl, trihalomethyloxy or C1-6alkyl substituted with cyano or aminocarbonyl; R5 is hydrogen or C1-4alkyl; L is C1-10alkyl substituted with one or two substituents independently selected from C3-7cycloalkyl, indanyl, indolyl, and phenyl, wherein said phenyl, indanyl, and indolyl may be substituted with one, two, three, four, or where possible five substituents each independently selected from halo, hydroxy, C1-6alkyl, C1-6alkyloxy, cyano, aminocarbonyl, C1-6alkyloxycarbonyl, formyl, nitro, amino, trihalomethyl, trihalomethyloxy, and C1-6alkylcarbonyl; or L is â€”X1â€”R6 wherein X1 is â€”NR3â€”, or â€”Oâ€” and R6 is 2,4,6-trichlorophenyl, 2,4,6-trimethyl-phenyl, 2,4-dibromo-3,5-dichloro-phenyl, 2,4-dibromo-6-fluoro-phenyl, 2,4-dichloro-6-methyl-phenyl, 2,6-dibromo-4-isopropyl-phenyl, 2,6-dibromo-4-methylphenyl, 2,6-dibromo-4-prop-1-yl-phenyl, 2,6-dichloro-4-cyano-phenyl, 2,6-dichloro-4-trifluoromethoxy-phenyl, 2,6-dichloro-4-trifluoromethyl-phenyl, 2,6-dichloro-phenyl, 2,6-dimethyl-4-(1,1-dimethylethyl)-phenyl, 2,6-dimethyl-phenyl, 2-bromo-4-fluoro-6-methyl-phenyl, 2-bromo-6-chloro-4-fluoro-phenyl, 4-bromo-2,6-dimethyl-phenyl, 4-chloro-2,6-dimethyl-phenyl, 4-cyano-2,6-dimethyl-phenyl; or L is â€”X2â€”Alkâ€”R7 wherein R7 is phenyl or phenyl substituted with one, two, three, four, or five substituents each independently selected from halo, hydroxy, C1-6alkyl, C1-6alkyloxy, C1-6alkylcarbonyl, C1-6alkyloxycarbonyl, formyl, cyano, aminocarbonyl, nitro, amino, trihalomethyloxy, and trihalomethyl; and X2 is â€”NR3â€”, â€”NHâ€”NHâ€”, â€”N&boxH;Nâ€”, â€”Oâ€”, â€”Sâ€”, â€”S(&boxH;O)â€” or â€”S(&boxH;O)2â€”; Alk is C1-4alkanediyl; aryl is phenyl or phenyl substituted with one, two, three, four, or five substituents each independently selected from halo, C1-6alkyl, C1-6alkyloxy, cyano, nitro, and trifluoromethyl; Het is an aliphatic or aromatic heterocyclic radical, said aliphatic heterocyclic radical is selected from pyrrolidinyl, piperidinyl, homopiperidinyl, piperazinyl, morpholinyl, tetrahydrofuranyl, and tetrahydrothienyl wherein each of said aliphatic heterocyclic radical may optionally be substituted with an oxo group; and said aromatic heterocyclic radical is selected from pyrrolyl, furanyl, thienyl, pyridyl, pyrimidinyl, pyrazinyl, and pyridazinyl wherein each of said aromatic heterocyclic radical may optionally be substituted with hydroxy; and R4â€²is cyano, aminocarbonyl, or C1-6alkyl substituted with cyano or aminocarbonyl; nâ€²is 0, 1, 2 or 3; with the proviso that Q is other than anilino, 2,4,6-trinitro-anilino, 3-methoxy-anilino, 4-methoxy-anilino, 3,4-dimethoxy-anilino, 3-chloro-4-fluoro-anilino, 4-cyano-anilino, 2-(C1-6alkyl)-anilino, 4-(C1-6alkyl)-anilino, 3-chloro-anilino, 4-bromo-anilino, 4-nitro-anilino, and 4-chloro-anilino.