GB1436893A — Tetrahydrocarbazole derivatives and process for their manufa cture

USPTO Abstract

1436893 Tetrahydrocarbazole derivatives SCHERING AG 14 May 1973 [25 May 1972] 22795/73 Heading C2C The invention comprises compounds of formula and their salts, wherein R 1 and R 3 are each H or C 1-4 alkyl; R 2 is A-X where (a) A is C 1-4 alkylene and X is OH, NH 2 , AcNH, N 3 or TsO, or (b) (when R 1 , R 3 , R 4 and R 5 are not all simultaneously H) A is (CH 2 ) 0-1 and X is CO 2 H, CO 2 alkyl, CONH 2 or CN; R 4 is H, F, C 2-6 alkyl, CF 3 , C 3-6 alkoxy, NO 2 , CO 2 H, NH 2 , OH or CN, or (when R 5 # H) Cl; and R 5 is (in the 5-, 7- or 8-position) H, halogen, C 1-4 alkyl, or C 1-6 alkoxy, or R 4 -R 5 is 6,7-OCH 2 O. These compounds are prepared in examples by, reacting R 4 R 5 C 6 H 3 NH 2 with R 3 -substituted-2- R2 - 6 - Y - cyclohexanone (Y=halogen), or R 4 R 5 C 6 H 3 NR 1 -NH 2 with R 3 -substituted-2- R 2 -cyclohexanone; or by hydrolysis of esters or nitriles to acids, ammonolysis of esters to amides, acetylation of an aminomethyl compound (itself obtained by reducing the analogue containing -CH 2 N 3 or -CONH 2 ) reduction of esters to -CH 2 OH compounds, and conversion of the latter to its tosylate and thus to the corresponding azide. Intermediates prepared are (1) an analogue of I where R 2 is -CO 2 CO 2 Et, and (2) ethyl 3 - bromo - 5 - methyl - 2 - oxocyclohexanecarboxylate. Therapeutic compositions which may be administered in the conventional forms, comprise compounds of the above formula, which have blood sugar lowering, antifungal, fertilityinhibiting and anti-inflammatory activity.