GB902617A - Improvements in or relating to therapeutically-active alkylamines - Google Patents

Abstract

The invention comprises compounds of the formula <FORM:0902617/IV (b)/1> and acid addition salts and acyl derivatives thereof, wherein R1 is hydrogen, hydroxy, methyl or methoxy, R2 is hydrogen, methyl or an acyl radical of a hydrocarbon monocarboxylic acid of 1-4 carbon atoms, R3 is an alkyl group of 1-5 carbon atoms, an alkenyl, alkynyl, hydroxyalkynyl or alkoxyalkynyl group of up to 8 carbon atoms or a cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, a -methylbenzyl, phenyl, benzyl or hydroxy-, methyl-, methoxy-, ethoxy-, chloro- or bromosubstituted phenyl or benzyl radical and R4 is hydrogen, hydroxy, methoxy or an alkanoyloxy radical of 1-4 carbon atoms; and the preparation of these compounds by reacting a phenoxyethyl halide with a propylamine or by reacting a phenoxyethylamine with an appropriate propyl halide. Other methods of preparation include N-alkylation of a phenoxyethyl-propylamine, to introduce a group R2, such as a methyl group, reaction of 2 : 3-dibromo - propene - (1) with N-(2-(21-methoxyphenoxy)-ethyl)-N-methyl-3-aminopropanol followed by dehydrohalogenation of the N-bromopropenyloxy-propyl product to give N-(3-(21-propynyl - 1 - oxy) - propyl) - N - methyl-2-(21-methoxyphenoxy) ethylamine and the preparation of N-(3-amyloxy-2-hydroxypropyl)-2-(21-hydroxyphenoxy) ethylamine by hydrogenolysis of the corresponding 2-(21-benzyloxyphenoxy) compound. The acyl derivatives and salts such as the hydrochlorides, sulphates, acetates, phosphates, citrates, pamoates, embonates, amsonates, tartrates, ascorbates and di-(p-toloyl)-tartrates are made by conventional methods of acylation and salt formation. Pharmaceutical preparations having hypotensive, sedative, adrenaline potentiation and adrenolytic activity comprise the above compounds of the invention in admixture with a pharmaceutical carrier. The preparations may be administered orally, for example as tablets, capsules, elixirs or suspensions or parenterally e.g. intra-muscularly or subcutaneously as sterile solutions in water or isotonic saline or glucose solution. The first Provisional Specification includes products wherein R1 is an alkoxy group of 1 or 2 carbon atoms or chloro or bromo, R2 may be a C1-4 alkyl radical, the definitions of R3 and R4 are wider and the phenoxyethyl group may have a methyl substituent in the a -position.