IE38872B1 - Propanolamine derivatives - Google Patents

Abstract

1398738 Propanolamines PFIZER Ltd 4 Dec 1973 [5 Dec 1972] 56046/72 Heading C2C The invention comprises propanolamines of the formula wherein R is H or a group that is readily removable by hydrolysis or hydrogenolysis, R<SP>1</SP> is halogen, C 1-4 alkyl, C 2-4 alkenyl, C 1-4 alkoxy or C 2-4 alkenyloxy, and R<SP>2</SP> is H, benzyl or C 1-4 alkenoyl, the carboxylic acid ester of the compounds of the above formula in which the 2- hydroxy group is esterified with a C 1-4 alkanoic acid, the condensation products of those compounds of the above formula in which R<SP>2</SP> is H with an aldehyde of the formula R<SP>3</SP>CHO when R<SP>3</SP> is H or C 1-4 alkyl, and the pharmaceutical acceptable acid addition salts of those compounds containing basic nitrogen atoms. The compounds are prepared by reacting epoxy compounds of the formula wherein R is a protecting group for the hydroxyl group with 1 - benzylamino - 2 - (4 - carbamoylphenoxy)ethane or 1 - amino - 2 - (4- carbamoylphenoxy)ethane, or by reacting amines of the formulµ provided R<SP>2</SP> is not C 1-4 alkanoyl, with compounds of the formulµ respectively, wherein R 2 is halogen, benzenesulphonyloxy or p-toluenesulphonyloxy, or by reacting the appropriate 3-phenoxy-2-hydroxypropylamine with 2 - (4 - carbamoylphenoxy)- acetaldehyde and by hydrogenating the resulting Schiff's base. The protecting group may then be removed from the compound thus obtained and, if desired the resulting compounds may be esterified, acylated, reacted with aldehydes of the formula R 3 CHO, or converted to acid addition salts. 1 - (4 - Benzyloxy - 2 - methylphenoxy)- 2,3 - epoxy - propane is obtained by reacting 4-benzyloxy-2-methylphenol with epichlorohydrin. Pharmaceutical compositions, suitable for oral or parenteral administration, contain the above novel compounds or acid addition salts thereof and pharmaceutically acceptable carriers. The compounds possess #-adrenergic blocking antivity. [GB1398738A]