3,4-(Bis-substituted)-1,2,5-oxdiazole 2-oxides, their use and pharmaceutical formulations containing them

US4356178A · kind A · utility

Assignee

• Cassella Aktiengesellschaft · DE

Inventors

• Karl Schonafinger · Alzenau, DE
• Rudi Beyerle · Frankfurt, DE
• Anton Mogilev · Frankfurt am Main, DE
• Helmut Bohn · Schöneck, DE
• Melitta Just · Langen, DE
• Piero Martorana · Bad Homburg vor der Höhe, DE
• Rolf-Eberhard Nitz · Frankfurt am Main, DE

Key dates

• Filing date: Dec 18, 1981
• Grant date: Oct 26, 1982
• Expiry date: Dec 18, 2001

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D271/08
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Pharmacologically-valuable 3,4-(bis-substituted)-1,2,5-oxdiazole 2-oxides of formula I ##STR1## [wherein R denotes --NHR.sup.1, --NR.sup.2 R.sup.3, --NHR.sup.4 OR.sup.2, --NHR.sup.5 COR.sup.6 or ##STR2## R.sup.1 denotes alkyl having from 1 to 6 C atoms or cycloalkyl having 4 to 7 ring C atoms, R.sup.2 and R.sup.3 denote alkyl having from 1 to 4 C atoms, R.sup.4 denotes an alkylene radical of the formula --C.sub.n H.sub.2n --(wherein n denotes 2, 3 or 4), R.sup.5 denotes an alkylene radical of the formula --C.sub.m H.sub.2m -- (wherein m denotes 1, 2 or 3), R.sup.6 denotes --OR.sup.2, --NHR.sup.1, --NR.sup.2 R.sup.3 or --NH.sub.2, X denotes --(CH.sub.2).sub.p --, --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 -- or ##STR3## and p is 4, 5 of 6] and their pharmacologically-acceptable acid-addition compounds are prepared by elimination of hydrogen chloride from a hydroxamoyl chloride of the formula EQU R--CO--C(Cl).dbd.NOH (II) and dimerization. If desired, the resulting reaction product is subsequently converted into an acid-addition compound. The compounds and pharmaceutical preparations thereof are useful for treating and for prophylaxis of cardiovascular diseases.