Patent ID: 6479527
Filing Date: 2002-11-12
Classification: A61P,C07D

Abstract:
A compound of formula (I): or a pharmaceutically acceptable salt, ester or amide thereof, which is an inhibitor of monocyte chemoattractant protein-1 and wherein A and B together form an optionally substituted 5 membered aromatic ring which includes at least one heteroatom; X is CH2 or SO2; R1 is an optionally substituted aryl or heteroaryl ring; R2 is carboxy, cyano, â€”C(O)CH2OH, â€”CONHR4, â€”SO2NHR5, tetrazol-5-yl, SO3H, or a group of formula (VI): â€ƒwhere R4 is selected from the group consisting of hydrogen, alkyl, aryl, cyano, hydroxy, â€”SO2R9 where R9 is alkyl, aryl, heteroaryl, or haloalkyl, and a group-(CHR10)râ€”COOH where r is an integer of 1-3 and each R10 group is independently hydrogen and alkyl; R5 is alkyl, optionally substituted aryl or optionally substituted heteroaryl or a group COR6 where R6 is hydrogen, alkyl, aryl, heteroaryl or haloalkyl; R7 and R8 are independently hydrogen and alkyl; and R3 is hydrogen or a functional group selected from the group consisting of halo, cyano, nitro, oxo, C(O)nR11, OR11, S(O)mR11, NR12R12â€², C(O)NR12R12â€², OC(O)NR12R12â€², â€”CH&boxH;NOR11, â€”NR12C(O)nR11, â€”NR11CONR12R12â€², â€”N&boxH;CR12R12â€², S(O)mNR12R12â€² and â€”NR12S(O)mR11 where R11, R12 and R12â€² are independently hydrogen or optionally substituted hydrocarbyl, or R12 and R12â€² together form an optionally substituted ring which optionally contains further heteroatoms, n is an integer of 1 or 2, m is 0 or an integer of 1-3, and wherein optional substituents for hydrocarbyl groups R11, R12 and R12â€² are selected from the group consisting of halo, perhaloalkyl, mercapto, hydroxy, alkoxy, oxo, heteroaryloxy, alkenyloxy, alkynyloxy, alkoxyalkoxy, cyano, nitro, amino, mono- or di-alkyl amino, alkylamido, and oximino, and aryloxy where the aryl group may be substituted by halo, nitro, or hydroxy; or R3 is an optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted alkoxy, optionally substituted aralkyl, optionally substituted aralkyloxy or optionally substituted cycloalkyl; subject to the following provisos: a) that where Aâ€”B forms a group of sub-formula (i) or (iv): â€ƒwhere R13, R14 and R15 are independently hydrogen and a substituent group selected from functional groups as defined in respect to R3, R1 is other than phenyl, amino phenyl or nitrophenyl; and b) that where Aâ€”B forms a group of sub-formula (iii): â€ƒwhere R13 is hydrogen, R14 is not CHO; c) that where Aâ€”B a group of sub-formula (v): where R13 and R14 are as defined above in a), and X is SO2, R1 is other than unsubstituted phenyl.