Benzazepine derivatives, their pharmaceutical compositions and method of use

US4490369A · kind A · utility

Assignee

• Dr. Karl Thomae GmbH · DE

Inventors

• Manfred Reiffen · Biberach, DE
• Joachim Heider · Warthausen, DE
• Norbert Hauel · Schemmerhofen, DE
• Volkhard Austel · Biberach, DE
• Wolfgang Eberlein · Biberach, DE
• Walter Kobinger · Wien, AT
• Christian Lillie · Wien, AT
• Klaus Noll · Cologne, DE
• Helmut Pieper · Lohr am Main, DE
• Gerd Kruger
• Johannes Keck · Zell am Harmersbach, DE

Key dates

• Filing date: Nov 2, 1983
• Grant date: Dec 25, 1984
• Expiry date: Nov 2, 2003

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D491/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Compounds of the formula ##STR1## wherein A is --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --NH--CO--, --CH.sub.2 --CO-- or ##STR2## where R.sub.7 is alkyl of 1 to 3 carbon atoms, and PA1 B is methylene, carbonyl or thiocarbonyl, or PA1 A is --CO--CO--, --N.dbd.CH--, ##STR3## where R.sub.8 is hydrogen or alkyl of 1 to 3 carbon atoms substituted by a phenyl, methoxyphenyl or dimethoxyphenyl, and PA1 B is methylene; PA1 E is n-alkylene of 2 to 4 carbon atoms optionally substituted by an alkyl of 1 to 3 carbon atoms, 2-hydroxy-n-propylene, 2-hydroxy-n-butylene or 3-hydroxy-n-butylene; PA1 G is n-alkylene of 1 to 5 carbon atoms optionally substituted by an alkyl of 1 to 3 carbon atoms, wherein one methylene group of an n-alkylene of 2 to 5 carbon atoms can be replaced by a carbonyl group, with the proviso that B represents a methylene or carbonyl group, or methylene-n-hydroxy-alkylene of 1 to 4 carbon atoms, where the methylene group is attached to the nitrogen atom; and PA1 R.sub.1 to R.sub.5 are simple substituents of various types; and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as bradycardiacs.