GB1206527A - Pharmaceutically active 4-phenylbicyclo-[2.2.2]-octane and oct-2-ene-1-carboxamides and derivatives thereof - Google Patents

Abstract

1,206,527. Derivatives of 4-phenylbicyclo- [2,2,2]-octane and octenes. E.I. DU PONT DE NEMOURS & CO. 6 Dec., 1968 [8 Dec., 1967], No. 58119/68. Heading C2C. Novel derivatives of 4-phenylbicyclo-[2,2,2]- octane and octene of the formula wherein A is a single or double bond; R 1 is H, OH, OCH 3 , OC 2 H 5 , OC 3 H 7 , OC 4 H 9 or RCO.O-, R being a C 1-12 alkyl group; and R 2 is NHOH, NR 3 R 4 or NHNR 5 R 6 , where each of R 3 and R 4 or of R 5 and R 6 , which can be the same or different, are H, CH 3 or C 2 H 5 or together with the N atom form a pyrrolidino, piperidino or morpholino group are prepared by one of the following methods: (a) compounds in which R 2 is NHOH or NR 3 R 4 by refluxing the appropriate compound in which R 2 in the above general formula is OH with thionyl chloride and then adding to the mixture hydroxylamine or an amine of the formula HNR 3 R 4 in an aqueous solution; (b) compounds in which R 2 is NR 3 R 4 also by heating a compound of the above general formula in which R 2 is OH or C 1-4 alkoxy group with an amine of the formula HNR 3 R 4 ; (c) compounds in which R 2 is NHNR 5 R 6 by reacting a compound in which R 2 is a C 1-4 alkoxy group with a hydrazine of formula H 2 NNR 5 R 6 ; (d) compounds in which R is RCO.O by esterification of the corresponding compound of the above general formula in which R is OH. 4 - (p - Methoxyphenyl) - bicyclo - [2,2,2]- octane-1-carboxylic acid chloride is obtained by reacting the corresponding acid with thionyl chloride. Pharmaceutical compositions, suitable for oral, parenteral or rectal administration contain as the active ingredient one of the above novel compounds together with pharmaceutically acceptable diluents or carriers. The compositions are used as antifertility agents to prevent pregnancy.