Alkanolamine derivatives

摘要

Novel compounds of the general formula (wherein R2 represents an alkyl radical optionally carrying one or more hydroxy, alkoxy or aryloxy substituents, an aralkyl radical optionally carrying one or more halogen or alkoxy substituents, or a cycloalkyl or alkenyl radical, R3 represents H or an alkyl radical, R4 represents an acyl radical (including sulphonyl), and the ring A may optionally be further substituted by one or more alkyl radicals, or by the radical -CH = CH-CH = CH- to complete a naphthalene ring) are prepared by reacting a compound of the general formula (wherein X represents the group or the group -CH.OH.CH2Halogen), or a mixture of such compounds in which X has both meanings, with an amine R2NH2, or, when R2 is not an a -arylalkyl radical, by hydrogenolysis of a corresponding compound containing an a -arylalkyl radical in place of the H atom attached to the side-chain N atom. The resulting alkanolamine derivatives may be converted into acid addition salts, and these may be treated with an acylating agent to esterify the hydroxy group in the 2-position of the propanol side-chain, or the free alkanolamines or their acid addition salts may be reacted with aldehydes R5.CHO to form oxazolidines of the general formula (wherein R5 represents H or an alkyl radical) or acid-addition salts thereof. Starting materials.-Compounds of the second general formula above are prepared by reacting the corresponding phenols with an epihalohydrin. The N-(a -arylalkyl)-amino starting materials for the alternative process are prepared by acylating the corresponding compounds containing a substituent R3NH- instead of R3R4N- in the ring A. Other starting materials and intermediates described are: 1 - (2 - and 4 - nitrophenoxy) - 3 - (N - benzylisopropylamino) - 2 - propanol (as hydrochlorides), and the corresponding aminophenoxy compounds. Pharmaceutical compositions, e.g. tablets, capsules, solutions, suspensions, emulsions or dispersible powders, having b -adrenergic blocking activity, comprise one or more of the free or esterified alkanolamines or the oxazolidines, or the acid addition salts thereof, in association with a pharmaceutically acceptable diluent or carrier.