摘要 |
1,260,768. 1,2,3,4-Tetrahydrocarbazole derivatives. PFIZER Inc. 25 Nov., 1969 [28 Aug., 1969], No. 57725/69. Heading C2C. The invention comprises compounds of formula and their pharmaceutically acceptable acid addition salts, wherein R 1 and R 2 are each H, OH, F, Cl, Br, CF 3 , CF 3 O or (C 1-4 ) alkyl, alkoxy, alkanoyl, alkanoylamino or alkylthio, or R 1 R 2 is C 1-3 -alkylenedioxy; R 3 is C 1-4 alkyl; n is 1 or 2; and R 4 , R 5 are each H, C 1-4 alkyl or C 3-6 cycloalkyl, or NR 4 R 5 form a pyrrolidino, piperidino, piperazino, N-(C 1-3 alkyl)piperazino or morpholino ring. These compounds are prepared by (1) reducing the analogues having a carbamyl, carbamylmethyl, azidomethyl or cyanomethyl group in the 4-position, (2) replacing the 9-H atom by R 3 in the appropriate precursor, or (3) replacing 1 or 2 N-attached H atoms by the desired substituents in an N-unsubstituted aminoalkyl group. Intermediates.-Details are also given for the preparation of 4-carboxy- and 4-carboxymethyl-9- methyl-1,2,3,4-tetrahydrocarbazole, their alkyl esters, 4-hydroxymethyl-9-methyl-1,2,3,4-tetrahydrocarbazole and its tosylate. Therapeutic compositions for the treatment of diabetes by oral administration comprise compounds of the above formula.
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