GB1236078A - Substituted azetidinols - Google Patents

Abstract

1,236,078. Substituted azetidinols. BEECHAM GROUP Ltd. 20 June, 1969 [4 July, 1968], No. 31969/68. Heading C2C. Novel substituted azetidinols of the Formula I wherein R is optionally substituted alkyl having 2 or more carbon atoms, cycloalkyl, aralkyl, aryl, alkoxycarbonyl or aryloxycarbonyl, or together with the quaternized nitrogen atom to which it is attached forms a cyclic structure, R 1 is OH or when R is alkoxy- or aryloxycarbonyl R 1 may be OH esterified by the same alkoxy- or aryloxy-carbonyl group; and R 2 is aryl and acid addition and quaternary ammonium salts of those compounds containing a basic N atom are prepared, when R is optionally substituted alkyl, cycloalkyl, aralkyl or aryl, by reacting the appropriate 2-arylepichlorohydrins with primary amines of the formula RNH 2 , and, if desired, forming the free bases and optionally converting these to acid addition or quaternary ammonium salts, or when R is alkoxy- or aryloxy-carbonyl and R 1 is OH esterified by the same alkoxy- or aryloxy-carbonyl group, by reacting azetidinols of Formula I above in which R is t.-butyl with alkyl- or aryl-chloroformates. Quaternary ammonium salts are obtained by reacting 2-arylepichlorohydrins with secondary amines of the formula R 3 R 4 NH in which R 3 and R 4 are optionally substituted alkyl, aryl or aralkyl or together with the nitrogen atom to which they are attached, form a cyclic structure. Pharmaceutical compositions, having activity on the central nervous system as depressants, contain the above novel compounds or salts thereof and pharmaceutically acceptable carriers.