1-(Indol-4-yloxy)-3-(2-substituted amino)-2-propanols and pharmaceutical use thereof

US4235919A · kind A · utility

Assignee

• Sandoz AG · CH

Inventor

• Richard Berthold · Binningen, CH

Key dates

• Filing date: Jul 17, 1978
• Grant date: Nov 25, 1980
• Expiry date: Jul 17, 1998

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D209/42
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The compounds of formula I ##STR1## wherein R is a group ##STR2## wherein A is alkylene of 2 to 5 carbon atoms, PA1 X is a bond, oxygen or sulfur, PA1 R.sub.3 is hydrogen, hydroxy, alkoxy of 1 to 4 carbon atoms, halogen of atomic member of from 9 to 35, cyano, carbamoyl or a group NHCOR.sub.d, wherein R.sub.d is alkyl of 1 to 4 carbon atoms, and PA1 R.sub.4 is hydrogen and, when R.sub.3 is alkoxy of 1 to 4 carbon atoms, R.sub.4 additionally may be alkoxy of 1 to 4 carbon atoms or, when R.sub.3 is halogen of atomic number of from 9 to 35, R.sub.4 additionally may be halogen of atomic number of from 9 to 35 either PA2 (i) R.sub.1 is hydrogen or methyl and PA2 R.sub.2 is cyano, CONR.sub.a R.sub.b, COOR.sub.c or CH.sub.2 OR.sub.e, wherein R.sub.a, R.sub.b, R.sub.c and R.sub.e independently are hydrogen or alkyl of 1 to 4 carbon atoms, PA2 or PA2 (ii) either R.sub.1 is methyl and R.sub.2 is halogen of atomic number of from 17 to 35 PA2 or R.sub.1 is halogen of atomic number of from 17 to 35 and R.sub.2 is hydrogen or methyl, PA2 with the provisos that PA3 (a) X is separated from the nitrogen atom of the 3-amino-2-hydroxypropoxy chain by at least 2 carbon atoms, PA3 (b) when X is a bond,…