Bis-phenoxypropanolamine derivatives are prepared. These compounds have .beta.-adrenergic stimulant activity particularly as selective bronchodilators.

Compounds of the formula ##STR1## WHEREIN R.sub.1 is hydrogen or methyl, m is 0 or an integer from 1 to 8, inclusive, and Ar is ##STR2## WHERE R is hydrogen or acyl, and R.sub.2 is hydrogen or --OR, as defined above, ##STR3## WHERE R has the meanings defined above, and R.sub.3 is hydroxy-lower alkyl, --NH--CO--R.sub.4, --NH--SO.sub.2 --R.sub.5, --CH.sub.2 --NH--CO--R.sub.4, --CH.sub.2 --NH--SO.sub.2 --R.sub.5 or --CH.sub.2 --NH--CO--NH--R.sub.4, where R.sub.4 is hydrogen or lower alkyl, and R.sub.5 is lower alkyl or di-lower alkyl-amino, ##STR4## WHERE R.sub.6 is hydrogen, amino or hydroxyl, X is chlorine or bromine, and Y is hydrogen, chlorine or bromine or ##STR5## WHERE R has the meanings defined above, and A is a saturated or unsaturated 5- to 6-membered ring, And their non-toxic, pharmacologically acceptable acid addition salts; the compounds as well as their salts are useful as bronchospasmolytics, uterine spasmolytics, antipruritics and antiallergics.

The invention provides compounds of the general formula (I) ##STR1## and physiologically acceptable acid addition salts, metabolically labile esters and solvates thereof in which R.sup.1 represents a halogen atom or a methyl, ethyl, n-propyl or n-butyl group; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each represent hydrogen atoms or one or two of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 represent a methy or ethyl group; X represents a C.sub.4-7 alkylene chain optionally substituted by one or more C.sub.1-4 alkyl or hydroxyl groups; or optionally containing one or two double or triple bonds; or optionally interrupted by an oxygen or sulphur atom, or by a sulphone (--SO.sub.2 --) or urea (--NHCONH--) group; and Y represents a phenyl ring optionally carrying one to three substituents selected from hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, amino, carboxamido, C.sub.1-4 alkylsulphonylamino and nitro groups and halogen atoms with the proviso that when X is a C.sub.4-7 alkylene chain optionally containing one double bond then Y cannot represent phenyl or phenyl carrying one substituent which is halogen. The compounds according to the invention decrease total peripheral vascular resistance, increase cardiac output and produce a fall in blood pressure. They may be used in the treatment or prophylaxis of renal insuficiency and cardiovascular disorders such as hypertension, ischaemic heart disease or heart failure, for example acute or congestive heart failure.

N,N'-Bis[2-(3-substituted-4-hydroxyphenyl)-ethyl or -2-hydroxyethyl]-polymethylenediamines having .beta.-adrenergic stimulant activity particularly as selective bronchodilators, are prepared generally by condensation of an N-benzylphenethylamine with a polymethylene dihalide or by reaction of an .beta.-bromoacetophenone with an N,N'-dibenzyl-polymethylenediamine, with further operations depending on the nature of the 3-substituent, and subsequently hydrogenating catalytically with for example palladium-on-carbon. The key intermediates are also part of the invention.