Patent ID: 6414179
Filing Date: 2002-07-02
Classification: A61K,C07C,C07D

Abstract:
A compound of the formula whereinRa and Rb when taken together form an oxo (&boxH;O) group, or Ra and Rb are each independently hydrogen or OH; X is H, CF3, halogen, NR5R6, NH(CO)NR5R6, C(O)NR5R6, OH, OR7, SH, S(O)nR7, C(O)OR8, NH(CO)OR10, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl or C3-C7 cycloalkyl, said alkyl, alkenyl, alkynyl or cycloalkyl group being optionally substituted by COOR8, CN, C(O)NR5R6, PO3R8, SO3R8, heterocyclic, OH, OR7, SH, S(O)nR7, NR5R6, NH(CO)NR5R6, NH(CO)OR10, OC(O)OR10, aryl or heteroaryl, said aryl or heteroaryl being optionally substituted by one or two groups independently selected from COOR8, SO3R8, OCOR8, PO3R8 or heterocyclic; R1 and R2 are each independently H, OH, OR7, SH, S(O)nR7, substituted C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl or C3-C7 cycloalkyl, said alkyl, alkenyl, alkynyl or cycloalkyl group being substituted by COOR8, CN, C(O)NR5R6, PO3R8, SO3R8, heterocyclic, OH, OR7, SH, S(O)nR7, NR5R6, NH(CO)NR5R6, NH(CO)OR10, OC(O)OR10, aryl or heteroaryl, said aryl or heteroaryl group being optionally substituted by one or two groups independently selected from COOR8, SO3R8, PO3R8 or heterocyclic; R3 and R4 are each independently H, methylene, OH, OR7, SH, S(O)nR7, NHCOR7, COOR8, C(O)NR5R6, substituted C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl or C3-C7 cycloalkyl, said alkyl, alkenyl, alkynyl or cycloalkyl group being substituted by COOR8, CN, C(O)NR5R6, PO3R8, SO3R8, heterocyclic, OH, OR7, SH, S(O)nR7, NR5R6, NH(CO)NR5R6, NH(CO)OR10, OC(O)OR10, aryl or heteroaryl, said aryl or heteroaryl group being optionally substituted by one or two groups independently selected from COOR8, SO3R8, PO3R8 or heterocyclic; R5 and R6 are each independently H, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, C3-C7 cycloalkyl, heterocyclic, aryl or heteroaryl, said alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl or heteroaryl group being optionally substituted with COOR8, CN, OR8, NR8R9, SO3R8, PO3R8, halogen, aryl or heteroaryl, said aryl or heteroaryl substituent being optionally substituted with one or two groups independently selected from COOR8, SO3R8, PO3R8 or heterocyclic; R7 is C1-C7 alkyl or C3-C7 cycloalkyl, said alkyl or cycloalkyl group being optionally substituted by COOR8, CN, C(O)NR5R6, PO3R8, SO3R8, heterocyclic, OR5, SR5, S(O)nR10, NR5R6, NH(CO)NR5R6, NH(CO)OR10, C(O)2OR10, aryl or heteroaryl, said aryl or heteroaryl group being optionally substituted with one or two groups independently selected from COOR8, SO3R8, PO3R8 or heterocyclic; R8 and R9 are each independently H, C1-C7 alkyl or C3-C7 cycloalkyl; R10 is the same as R5 and R6 but is not H; Z is Yâ€”Z1 in which Y is â€”Oâ€”, â€”S(O)nâ€”, â€ƒor â€”CH2; n is 0, 1 or 2; Rc is H, â€”COCF3, â€”COC6H5, â€”COO(C1-C6)alkyl, â€ƒin which R19 and R20 are each independently H or (C1-C6)alkyl, (C1-C18)alkyl or (C1-C18)alkyl substituted by one or more of phenyl or phenyl substituted by 1-5 fluoro, 1-3 halo (other than fluoro), 1-3 (C1-C6)alkoxy, 1-3 (C1-C6)alkyl, 1-3 nitro, 1-3 cyano, 1-3 hydroxy, 1-3 trifluoromethyl, 1-3 (C1-C6)alkylthio, 1-3 amino, 1-3 (C1-C6)alkylamino, 1-3 di(C1-C6)alkylamino, 1-3 carboxyl, 1-3 â€”COO(C1-C6)alkyl, 1-3 â€”SO3H, 1-3 â€”SO2NHR21 in which R21 is hydrogen or (C1-C6)alkyl, or 1-3 â€ƒin which R19 and R20 are as defined above; and Z1 is â€ƒin which n1 is 0, 1 or 2 and R22 and R23 are phenyl or phenyl substituted by 1-5 fluoro, 1-3 halo (other than fluoro), 1-3 (C1-C6)alkoxy, 1-3 (C1-C6)alkyl, 1-3 nitro, 1-3 cyano, 1-3 hydroxy, 1-3 trifluoromethyl, 1-3 (C1-C6)alkylthio, 1-3 amino, 1-3 (C1-C6)alkylamino, 1-3 di(C1-C6)alkylamino, 1-3 carboxy, 1-3 â€”COO(C1-C6)alkyl, 1-3 â€”SO3H, 1-3 â€”SO2NHR21 in which R21 is hydrogen or (C1-C6)alkyl, or â€ƒin which R19 and R20 are as defined above; â€ƒin which n1 is 0, 1 or 2 and R22 and R23 are as defined above; â€ƒin which R22 and R23 are as defined above; â€ƒin which R22 and R23 are as defined above; â€ƒin which R22 and R23 are as defined above; or â€ƒin which R22 and R23 are as defined above; or a pharmaceutically acceptable salt thereof with the proviso that at least one of R1, R2, R3 and R4 is other than hydrogen.