Heterocyclic compounds

US4378361A · kind A · utility

Assignee

• Boehringer Ingelheim GmbH · DE

Inventors

• Kurt Schromm · Ingelheim am Rhein, DE
• Anton Mentrup · Mainz, DE
• Ernst-Otto Renth · Ingelheim am Rhein, DE
• Armin Fugner · Gau-Algesheim, DE
• Ilse Streller · Stromberg, DE

Key dates

• Filing date: Jul 22, 1981
• Grant date: Mar 29, 1983
• Expiry date: Jul 22, 2001

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D249/18
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Compounds of the formula ##STR1## wherein Het is ##STR2## n is an integer from 1 to 4, inclusive, preferably 2 or 3, R.sub.1 is H or acyl, PA0 R.sub.2 is H, R.sub.1 O, --NHSO.sub.2 R.sub.7, --NHCOR.sub.8, --NHCONHR.sub.8, --NH--CH.sub.2 --C.sub.6 H.sub.4 --R.sub.9, --CH.sub.2 OH, --CH.sub.2 SO.sub.2 R.sub.7, --CONHR.sub.8, halogen or --CN, PA0 R.sub.3 is H, halogen, R.sub.7 or --OR.sub.7, PA0 R.sub.2 and R.sub.3 together with each other are ##STR3## R.sub.4 is H, --CH.sub.3 or --C.sub.2 H.sub.5, R.sub.5 and R.sub.6 are each H or --CH.sub.3, PA0 R.sub.7 is C.sub.1 -C.sub.4 alkyl, PA0 R.sub.8 is H or C.sub.1 -C.sub.4 alkyl, PA0 R.sub.9 is H, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy optionally interrupted by oxygen, PA0 R.sub.10 and R.sub.12 are each H, CH.sub.3, Cl or OCH.sub.3, or together methylenedioxy, PA0 X is ##STR4## or N, and Z is --CH.sub.2 or --CO; in the form of racemates, enantiomers, diastereoisomeric antipode pairs, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as the salts are useful as bronchospasmolytics, spasmolytics, muscle-relaxants, antiallergics and hypotensives.