Patent GB-1285398-A (GB)
Title: Hydroxy-substituted tricyclic carboxylic acids and derivatives and pharmaceutical compositions containing them
Inventor: SHEN TSUNG-YING
IPC: C07D333/76
Filed: 1970-06-18
Abstract: 1285398 Hydroxy-tricyclic carboxylic acids MERCK & CO Inc 18 June 1970 [25 June 1969 20 April 1970] 29536/70 Heading C2C Novel compounds of the Formula (I) wherein X denotes hydrogen, alkyl, hydroxy, alkoxy, acyloxy, halogen, haloalkyl, nitro, amino, alkylamino, dialkylamino, acylamino, mercapto, alkylmercapto, alkylsulphinyl, alkylsulphonyl, sulphamoyl, aminosulphinyl, aminoalkyl, alkylaminoalkyl, hydroxyalkyl, alkoxyalkyl, mercaptoalkyl, alkylthioalkyl, cyano, carboxy, alkoxycarbonyl, carbamoyl, aryl, aralkyl, aryloxy, aralkoxy and acyl; Y is oxy, thio, sulphinyl, sulphonyl, imino, and alkylimino; R is hydroxy, amino, alkoxy, alkylamino,  dialkylaminoalkoxy, hydroxyalkoxy, polyhydroxyalkoxy, alkoxyalkoxy, arylalkoxy, phenoxy, substituted phenoxy, carboxy and alkoxy carbonyl, alkanoylaminoalkoxy, hydrazino, N - morpholino, and hydroxyalkylamino; N - (4 - alkyl)piperidino or N - (4- hydroxyalkyl piperidino) or an N-attached residue derived from an amino acid and R 2  is hydrogen, acyl, alkyl, or alkoxycarbonyl; provided that the 0R 2  group is always ortho to the COR group; and that when Y is imino or oxy at least one X is other than H, alkyl and hydroxy, may be obtained by reacting a compound of the Formula (II) with C0 2  at elevated temperatures and pressures. The corresponding esters, amides, anhydrides and salts of the resulting acid may be obtained by conventional procedures. The preparation of the following intermediates is also described: 7-fluoro-3-nitro-dibenzofuran, 7 - fluoro - 2 - nitrodibenzofuran, 8 - fluoro - 2- nitrodibenzofuran; 7 - fluoro - 3 - dibenzofuranamine, and other fluoro-, carboxy-, bromo-, and chloro-2- and 3-dibenzofuranamines; 7- fluoro - 3 - dibenzo - furanol and other carboxy-, methoxy-, nitro- or bromo- 3-dibenzofuranols; 4<SP>1 </SP>- fluoro-, 4<SP>1 </SP>- chloro-, 4<SP>1 </SP>- methoxy-, 41 - methyl- or 4<SP>1</SP> - trifluoromethyl - 2 - amino- 4 - nitrodiphenyl sulphide; 4<SP>1</SP> - fluoro-, 41- bromo-, 41 - chloro-, 41 - methyl, 41 - methoxy or 4<SP>1</SP>- trifluoromethyl 2 - amino - 5 - nitrodiphenylsulphide; 8 - fluoro - 2 - nitro - dibenzothiophene and similar 8-bromo, chloro, iodo-, methyl, methoxy or trifluoromethyl compounds; 7 - fluoro - 3 - nitrodibenzothiophene and corresponding 7-chloro, bromo and iodo compounds; and 5,5-dioxides corresponding to these dibenzothiophenes; 2-ammo-8-fluorodibenzothiophene and other 8-substituted-2- and 3-aminodibenzothiophenes and their 5,5-dioxides; 8- fluoro- and other 8-substituted 2- and 3- hydroxydibenzothiophenes and their 5,5-dioxides; 2 - (51 - fluoro - 21 - nitrophenyl)- benzoquinone and other 4- or 5- substituted, and 4,5 - disubstituted anologues; 2 - (21- amino-5<SP>1</SP>-fluorophenyl)hydroquinone. Pharmaceutical compositions comprising a compoundof Formula (I) together with a suitable carrier have anti-inflammatory activity and certain compositions also have anti-pyretic, analgesic, diuretic, anti-fibrinolytic and hypoglycemic activity. The composition may be administered orally, rectally, parenterally or topically.