N,N'-bis-[(.beta.-hydroxy-.beta.-phenyl)-ethyl]-polymethylenediamines and salts thereof

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.

We claim:

1. A compound of the formula ##STR42## wherein R.sub.1 is hydrogen or methyl,

m is 0 or an integer from 1 to 8, inclusive, and

Ar is ##STR43## where R.sub.2 is hydrogen or hydroxyl, ##STR44## where R.sub.3 is hydroxy-lower alkyl, or ##STR45## where R.sub.6 is hydrogen, amino or hydroxyl,

X is chlorine or bromine, and

Y is hydrogen, chlorine or bromine

or a non-toxic, pharmacologically acceptable acid addition salt thereof.

2. A compound of claim 1, wherein

R.sub.1 is hydrogen or methyl,

m is an integer from 2 to 6, inclusive and

Ar is ##STR46## where R.sub.3 is hydroxy-methyl or hydroxy-ethyl, or ##STR47## where R.sub.6 is hydroxyl or amino, and

Y is hydrogen or chlorine,

or a non-toxic, pharmacologically acceptable acid addition salt thereof.

3. A compound of claim 1, wherein

R.sub.1 is hydrogen or methyl,

m is 2 or 4, and

Ar is 3,5-dihydroxy-phenyl, 3-hydroxymethyl-4-hydroxy-phenyl, 2-chloro-4-hydroxy-phenyl or 3,5-dichloro-4-amino-phenyl,

or a non-toxic, pharmacologically acceptable acid addition salt thereof.

4. A compound of claim 3, which is N,N'-bis-[.beta.-hydroxy-.beta.-(3', 5'-dihydroxy-phenyl)-ethyl]-2,5-dimethyl-2,5-diamino-hexane or a non-toxic, pharmacologically acceptable acid addition salt thereof.

5. A compound of claim 3, which is N,N'-bis-[.beta.-hydroxy-.beta.-(3'-hydroxymethyl-4'-hydroxy-phenyl)-ethyl ]-2,5-dimethyl-2,5-diamino-hexane or a non-toxic, pharmacologically acceptable acid addition salt thereof.

6. A compound of claim 3, which is N,N'-bis-[.beta.-hydroxy-.beta.-(3'-hydroxymethyl-4'-hydroxy-phenyl)-ethyl ]-1,6-diamino-hexane or a non-toxic, pharmacologically acceptable acid addition salt thereof.

7. A compound of claim 3, which is N,N'-bis-[.beta.-hydroxy-.beta.-(3',5'-dihydroxy-phenyl)-ethyl]-1,6-diamin o-hexane or a non-toxic, pharmacologically acceptable acid addition salt thereof.