GB1471751A - Piperidine derivatives - Google Patents

Abstract

1471751 Piperidine derivatives SANDOZ Ltd 13 May 1974 [17 May 1973 (7)] 20971/74 Heading C2C Novel piperidine derivatives of the general formula wherein n is 1, 2 or 3, R 1 is C 1-4 alkyl, R 2 is hydrogen or C 1-4 alkyl, R 3 is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, C 1-4 alkyl, C 1-3 alkoxy or C 1-3 alkylthio, A and B together with the double bond form a benzene ring, or a benzene ring substituted by chlorine, bromine, fluorine, trifluoromethyl, C 1-4 alkyl, C 1-3 alkoxy or C 1-3 alkylthio, or A is sulphur and A and B together with the double bond form a thiophene ring, or a thiophene ring substituted in the α position to the sulphur by chlorine, bromine or C 1-4 alkyl, and Y is ethylene or vinylene, when A and B together with the double bond form a benzene ring, or a benzene ring substituted by chlorine, bromine, fluorine, trifluoromethyl, C 1-4 alkyl, C 1-3 alkoxy or C 1-3 alkylthio, or when A is sulphur and A and B together with the double bond form a thiophene ring, or a thiopene ring substituted in the α position to the sulphur by chlorine, bromine or C 1-4 alkyl, or Y is oxygen, methyleneoxy, methylenethio or a group wherein R 4 and R 5 are independently C 1-3 alkyl, when A and B together with the double bond form a benzene ring, or a benzene ring substituted by chlorine, bromine, fluorine, trifluoromethyl, C 1-4 alkyl, C 1-3 alkoxy or C 1-3 alkylthio, or Y is sulphur, when A is sulphur and A and B together with the double bond form a thiophene ring, and acid addition salts thereof are prepared by alkylating a compound of the general formula with a compound of the general formula Z-CO-R 1 , wherein Z is (a) wherein R 2 and n are as defined above, and X is the acid radical of a reactive ester, to produce a compound of Formula I, or (b) CH 2 =CR 2 - wherein R 2 is as defined above, to produce a compound of Formula I wherein n is 1, followed optionally by salification of the product. Compounds II are prepared by acylating a compound of the general formula with Cl-COOAlkyl and hydrolysing the resulting urethane. Pharmaceutical compositions having sedativeneuroleptic and muscle-relaxing activity comprise, as active ingredient, a compound I or pharmaceutically acceptable acid addition salt thereof, in association with a pharmaceutical carrier or diluent.