3-amino-propyloxyphenyl derivatives, their preparation and pharmaceutical compositions containing them

US5051445A · kind A · utility

Assignee

• William M. Louis · AU

Inventors

• William J. Louis · Melbourne, AU
• Max Peter Seiler · Riehen, CH
• Andre Stoll · Birsfelden, CH

Key dates

• Filing date: Jun 11, 1990
• Grant date: Sep 24, 1991
• Expiry date: Jun 11, 2010

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P27/02
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

##STR1## wherein (A) R is O(CH.sub.2).sub.2 O-R.sub.3 and PA2 (a) R.sub.1 and R.sub.5 are hydrogen and R.sub.3 is n-propyl, isobutyl, cyclopentylmethyl, benzyl or 2-(p-fluorophenyl)ethyl; PA2 (b) R.sub.1 is fluorine and R.sub.5 is hydrogen and R.sub.3 is n-propyl; PA2 (c) R.sub.1 is methyl and R.sub.5 is hydrogen and R.sub.3 is cyclopropylmethyl; PA2 (d) R.sub.1 is cyano and R.sub.5 is hydrogen and R.sub.3 is n-propyl; PA2 (e) R.sub.1 is hydrogen, R.sub.5 is methyl and R.sub.3 is alkyl of 2 to 5 carbon atoms, cycloalkylmethyl of 5 to 7 carbon atoms in the cycloalkyl part thereof or --(CH.sub.2).sub.n --R' wherein n is 0, 1 or 2 and R' is phenyl or monofluorophenyl; or PA1 (B) R is hydroxy, R.sub.1 is fluorine and R.sub.5 is hydrogen, and their physiologically hydrolysable derivatives, in which at least one hydroxy group is in esterified form, and their salts, elicit highly cardioselective beta 1 adrenoceptor blockade, and in most cases cardiospecific blockade, and relevant cardiotonic activity. These compounds can be used as therapeutic agents. One obtains these compounds by 3-amino-2-oxypropylation of the respective substituted phenol.