GB1279877A - Alkanolamine derivatives - Google Patents

Abstract

1279877 Alkanolamine derivatives PFIZER Ltd 15 Dec 1970 [17 Dec 1969 20 May 1970] 61414/69 and 24360/70 Heading C2C The invention comprises novel alkanolamine derivatives of the formula where R<SP>1</SP> is carboxamide, C 1-4 alkoxycarbonylamino, or carbamoyl, which may be separated from the benzene ring by CH 2 or CH 2 CH 2 ; R<SP>2</SP> and R<SP>3</SP> each are H or C 1-4 alkyl; R<SP>4</SP> is carboxamido, sulphonamido, C 1-4 alkoxycarbonylamino, carbamoyl or sulphamoyl which may be separated from benzene ring by CH 2 or CH 2 CH 2 ; R<SP>5</SP> is H, C 1-4 alkyl, C 1-4 alkanoyl or benzyl; X is O or S; Y is O, S, SO, SO 2 , imino, or a direct link; n is 1, 2 or 3 when Y is other than a direct link, and is 0 to 4 when Y is a direct link; and each of the benzene rings attached to X and Y may be substituted with one or more halogen atoms, or C 1-4 alkyl, C 1-4 alkoxy, C 2-4 alkenyl or C 2-4 alkenyloxy; the aldehyde condensation products of these compounds in which R<SP>5</SP> is H with formaldehyde or an aliphatic aldehyde containing up to 5 carbon atoms, the esters of compounds in which the 2-OH group is esterified with a C 1-4 alkanoic acid, and the pharmaceutically acceptable acid addition salts of those compounds possessing basic N atoms. The compounds (R<SP>5</SP> not alkanoyl) are prepared by reacting compounds of the formula in which Z is halogen or any suitable leaving group with the appropriate amines, or by reacting the corresponding amines with compounds of the formula Alternatively compounds in which R<SP>3</SP> and R<SP>5</SP> are both H may be obtained by reacting amines of the formula with aldehydes and ketones of the formula to give the corresponding Schiff's bases and hydrogenating the product. Compounds in which R<SP>1</SP> is a carbonamido radical of the formula R<SP>6</SP>NH, where R<SP>6</SP> is a carboxylic acyl radical may also be obtained by acylating the corresponding amines. The aldehyde condensation products are esters which are prepared by reacting the appropriate compound of Formula I above with the corresponding aldehydes and acids. Pharmaceutical compositions, suitable for oral or parenteral administration, contain the above novel compounds or acid addition salts thereof and pharmaceutically acceptable carriers. The compounds are blockers of #-adrenergic receptors and exert an inhibitory action on myocardial #-receptors.