Phenoxy-alkanolamine derivatives

Claim 2

An alkanolamine derivative selected from a compound of the formula: ##STR30## wherein A is alkylene of from 2 to 12 carbon atoms; wherein R 1 is hydrogen, alkyl, halogenoalkyl, alkenyl or cycloalkyl each of up to 10 carbon atoms, or aryl of the formula: ##STR31## wherein wherein R 2 and R 3 , which may be the same or different, each is hydrogen, halogen, hydroxy, amino, nitro or cyano, or alkyl, cycloalkyl, alkenyl, alkoxy, alkylthio, alkenyloxy or alkanoyl each of up to 6 carbon atoms, and wherein R 12 and R 13 , which may be the same or different, each is hydrogen, halogen, hydroxy, amino, nitro or cyano, or alkyl, alkenyl, alkoxy, alkenyloxy or alkanoyl each of up to 6 carbon atoms, or wherein R 12 and R 13 together are trimethylene, tetramethylene, propenylene, but-2-enylene or buta-1,3-dienylene such that together with the adjacent benzene ring they form respectively indanyl, 5,6,7,8-tetrahydronaphthyl, indenyl, 5,8-dihydronaphthyl or naphthyl; wherein R 4 stands for a substituent of the formula: R.sup.15 R.sup.16 N--CO--Q-- r.sup.15 r.sup.16 n--co--nh--q-- r.sup.15 r.sup.16 n--co--q.sup.1 --o-- or Ti R 16 --X--NR 15 --Q-- wherein Q is a direct link or is alkylene or alkenylene each of up to 6 carbon atoms; wherein Q 1 is alkylene of up to 6 carbon atoms; wherein R 15 is hydrogen or alkyl of up to 6 carbon atoms; wherein R 16 is hydrogen, or alkenyl, cycloalkyl, hydroxyalkyl or alkoxyalkyl each of up to 6 carbon atoms, or alkyl, aryl, aralkyl or aralkenyl each of up to 10 carbon atoms; wherein X is carbonyl and wherein Y is a direct link, or is alkylene, oxyalkylene or alkyleneoxy each of up to 6 carbon atoms, or, except when R 1 is hydrogen, is oxygen; and a non-toxic, pharmaceutically-acceptable acid-addition salt thereof.

Claim 3

An alkanolamine derivative as claimed in claim 1 selected from a compound of the formula stated in claim 1 wherein A is ethylene, trimethylene, tetramethylene, hexamethylene, dodecamethylene, 1-methylethylene, 2-methylethylene or 1,1-dimethylethylene; wherein R 1 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, n-octyl, trifluoromethyl, allyl, cyclopropyl, cyclopentyl or cyclohexyl or aryl of the formula: ##STR32## wherein R 2 or R 3 , which may be the same or different, each is hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, amino, nitro, cyano, methyl, ethyl, n-propyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl, methoxy, isopropoxy, methylthio, allyloxy, propargyloxy, formyl or acetyl, R 12 and R 13 , which may be the same or different, each is hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, amino, nitro, cyano, methyl, ethyl, n-propyl, allyl, methoxy, isopropoxy, allyloxy, propargyloxy, formyl or acetyl, or wherein R 12 and R 13 together form trimethylene, tetramethylene, propenylene, but-2-enylene or buta-1,3-dienylene; wherein R 4 has the meaning stated in claim 1 wherein Q is a direct link or is methylene, ethylene, trimethylene, ethylidene, 1-methyl-ethylene or vinylene, wherein Q 1 is methylene, ethylene, trimethylene, ethylidene or 1-methylethylene, wherein R 15 is hydrogen or methyl and wherein R 16 is hydrogen, ally., cyclopropyl, cyclopentyl, cyclohexyl, 2-hydroxyethyl, 3-hydroxypropyl, 2-hydroxy-1-methylethyl, 2-hydroxy-1,1-dimethylethyl, β-methoxyethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-nonyl, phenyl, p-tolyl, p-tolyl, p-chlorophenyl, benzyl or styryl; wherein X is carbonyl and wherein Y is a direct link or is methylene, ethylene, oxymethylene, methyleneoxy, ethyleneoxy, trimethyleneoxy, 1-methylethylideneoxy or 1-methylpropylideneoxy, or, except when R 1 is hydrogen, is oxygen; and a non-toxic, pharmaceutically-acceptable acid-addition salt thereof.

Claim 4

An alkanolamine derivative as claimed in claim 1 which is selected from a compound of the formula: ##STR33## wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene; wherein R 1 is hydrogen or alkyl, alkenyl or cycloalkyl each of up to 6 carbon atoms, or aryl of the formula: ##STR34## wherein R 12 and R 13 , which may be the same or different, each is hydrogen, halogen, hydroxy, amino, nitro or cyano, or alkyl, alkenyl, alkoxy or alkenyloxy each of up to 6 carbon atoms; wherein R 16 is alkyl or hydroxyalkyl each of up to 6 carbon atoms; and wherein Y is a direct link or is methylene or methyleneoxy; and a non-toxic, pharmaceutically-acceptable acid-addition salt thereof.

Claim 5

An alkanolamine derivative as claimed in claim 3 selected from a compound of the formula stated in claim 3 wherein A has the meaning stated in claim 3, R 1 is hydrogen, or alkyl of up to 6 carbon atoms, or unsubstituted phenyl, Y is a direct link or is methylene, and R 16 is methyl or 2-hydroxyethyl, and a non-toxic, pharmaceutically-acceptable acid-addition salt thereof.

Claim 6

An alkanolamine derivative as claimed in claim 1 which is selected from a compound of the formula: ##STR35## wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene, R 1 is hydrogen or alkyl or alkenyl each of up to 6 carbon atoms, or unsubstituted phenyl, X is carbonyl and Y is a direct link or is methylene, and a non-toxic, pharmaceutically-acceptable acid-addition salt thereof.

Claim 7

A compound claimed in claim 1 which is selected from 1-o-(N-β-hydroxyethylcarbamoylmethoxy)phenoxy-3-β-phenylacetamidoethylamino-2-propanol; 1-o-(N-methylcarbamoylmethoxy)phenoxy-3-β-acetamidoethylamino-2-propanol; 1-o-(N-methylcarbamoylmethoxy)phenoxy-3-β-isobutyramidoethylamino-2-propanol; 1-o-(N-methylcarbamoylmethoxy)phenoxy-3-β-phenylacetamidoethylamino-2-propanol; 1-o-(N-methylcarbamoylmethoxy)phenoxy-3-β-(o-allylphenoxy)-acetamidoethylamino-2-propanol; 1-o-(N-methylcarbamoylmethoxy)phenoxy-3-(1,1-dimethyl-2-isobutyramidoethyl)amino-2-propanol; 1-o-(N-β-hydroxyethylcarbamoylmethoxy)phenoxy-3-β-isobutyramidoethylamino-2-propanol; 1-o-(N-β-hydroxyethylcarbamoylmethoxy)phenoxy-3-(1-methyl-2-phenylacetamidoethyl)amino-2-propanol; 1-o-carbamoylphenoxy-3-β-isobutyramidoethylamino-2-propanol; 1-o-carbamoylphenoxy-3-β-phenylacetamidoethylamino-2-propanol; 1-o-carbamoylphenoxy-3-(1-methyl-2-phenylacetamidoethyl)amino-2-propanol; 1-(2-ethyl-4-propionamidophenoxy)-3-β-phenylacetamidoethylamino-2-propanol; and a non-toxic, pharmaceutically-acceptable acid-addition salt thereof.

Claim 8

An acid-addition salt as claimed in claim 1 which is a hydrochloride, hydrobromide, phosphate, sulphate, oxalate, lactate, tartrate, acetate, salicylate, citrate, benzoate, β-naphthoate, adipate, fumarate or 1,1-methylene-bis-(2-hydroxy-3-naphthoate).