Patent CA-2090743-A1 (CA)
Title: Pharmaceutical compounds
Inventor: BRUNAVS MICHAEL
IPC: A61P3/00
Filed: 1993-02-24
Abstract: ABSTRACT            Pharmaceutical compounds of the formula                       (I) in which R1 and R2 are each hydrogen, hydroxyl, halo, C1-4 alkyl, C1-4 alkoxy, acyloxy, -O-glucoside, optionally substituted phenyl or optionally substituted phenyl-C1-4 alkoxy;            R3 is -CO2H, -NR'SO2R'' where R' is hydrogen or C1-4 alkyl and R'' is hydroxyl, C1-4 alkyl or optionally substituted phenyl, -CONR'R'' where R' and R'' are each hydrogen, C1-4 alkyl, acyl or optionally substituted phenyl, -CONR'OR'' where R' is C1-4 alkyl or optionally substituted phenyl and R'' is C1-4 alkyl or benzyl, -CR'R''.CR'''(NHR'''')CO2H, where R' and R'' are each hydrogen, C1-4 alkyl or optionally substituted phenyl, R''' is hydrogen, -CO2H or -C1-4 alkylene-CO2H, and R'''' is hydrogen or acyl, -CR'R'' .CHR''' CO2H where R' and R'' are each hydrogen or C1-4 alkyl and R''' is optionally substituted phenyl, -CR'R''S(O)nR''' where R' and R'' are each hydrogen or C1-4 alkyl, R ''' is optionally substituted phenyl and n is 0,1 or 2, -P03R'R'' where R' and R'' are each hydrogen, C1-4 alkyl or optionally substituted phenyl, -CR'R''-PO3R'''R'''' where R', R'', R''' and R'''' are each hydrogen, C1-4 alkyl or optionally substituted phenyl, -CH=CH-PO3R'R'' where R' and R'' are each hydrogen, C1-4 alkyl or optionally substituted phenyl, -CH=C-PO3R'R'' \ PO3R'''R'''' where R', R'', R''' and R'''' are each hydrogen, C1-4 alkyl or optionally suhstituted phenyl, -CH2CH-PO3R'R'' \ PO3R'''R'''' where R', R'', R''' and R'''' are each hydrogen, C1-4 alkyl or optionally substituted phenyl, -CH=CHR' where R' is -CO2H, nitrile, tetrazolyl, optionally substituted benzimidazol-2-yl, optionally substituted N-C1-4 alkyl benzimidazol-2-yl, optionally substituted oxazol-5-yl, optionally substituted thiazol-5-yl, optionally substituted isoxazol-5-yl, optionally substituted isothiazol-5-yl or optionally substituted oxadiazol-2-yl, tetrazolyl, or pyridyl, optionally substituted benzimidazol-2-yl, optionally substituted N-C1-4 alkyl benzimidazol-2-yl, optionally substituted oxazol-5-yl, optionally substituted thiazol-5-yl, optionally substituted isoxazol-5-yl, optionally substituted isothiazol-5-yl or optionally substituted oxadiazol-2-yl; and R4 and R5 are each hydrogen, hydroxy, acyloxy, nitro, C1-4 alkyl, C1-4 alkoxy, halo, optionally substituted phenyl, -SO3H or -NR'R'' where R' and R'' are each hydrogen or C1-4 alkyl;     provided that when R3 is -CR'R''.CHR'''CO2H or tetrazolyl, R1 and R2 are each hydroxyl, halo, C1-4 alkyl, C1-4 alkoxy, acyloxy, -O-glucoside, optionally substituted phenyl or optionally substituted phenyl C1-4 alkoxy; and provided that when R3 is CO2H, the 9,10-dihydro-9,10-dioxoanthracene nucleus is substituted by (1) 1,4,5-trihydroxy,  (2) 1,4,5-triacetoxy, (3) 1,4,5,8-tetramethoxy,  (4) 1,4,5,8-tetrahydroxy, (5) 1,4,5,8-tetracetoxy,  (6) 1,4-dimethoxy, (7) 1-acetoxy-4-hydroxy, (8) 4,5-dihydroxy-8-fluoro,  (9) 4,5-dimethoxy-8-fluoro, (10) 4,5-dimethoxy-6-fluoro,  (11) 4,5-dihydroxy-6-fluoro, (12) 3,6-difluoro-4,5-dimethoxy,  (13) 1,4,5-trimethoxy, (14) 1,4-dihydroxy, (15) 1,4-diacetoxy and (16) 4,5-dimethoxy;   or a pharmaceutically acceptable salt or ester thereof.     G.1278 FF