2-Acylaminomethyl-1,4-benzodiazepine derivatives and their salts and pharmaceutical compositions thereof

US4325957A · kind A · utility

Assignee

• Kali-Chemie Pharma GmbH · DE

Inventors

• Horst Zeugner
• Dietmar Roemer · Pfullendorf, DE
• Hans Liepmann · Hannover, DE
• Wolfgang Milkowski

Key dates

• Filing date: Dec 23, 1980
• Grant date: Apr 20, 1982
• Expiry date: Dec 23, 2000

Classification

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

Abstract

Novel 2-acylaminomethyl-1H-2,3-dihydro-1,4-benzodiazepine derivatives are disclosed which possess the Formula I ##STR1## wherein R.sub.1 represents hydrogen, lower akyl, lower alkenyl or cyclopropylmethyl; PA1 R.sub.2 represents hydrogen, lower alkyl or lower alkenyl; PA1 R.sub.3 represents a group of the formula a, b, c or d; ##STR2## wherein R is hydrogen or C.sub.1 -C.sub.3 - alkyl; PA1 R.sub.4 is hydrogen, lower alkyl, lower alkoxy, nitro or halogen, and PA1 R.sub.4 ' is hydrogen or C.sub.1 -C.sub.4 - alkyl and the aromatic groups A and B may be unsubstituted or substituted by 1 to 3 substituents such as halogen, lower alkylthio, lower alkoxy, lower alkyl, hydroxy, nitro, trifluoromethyl or methylenedioxy or ethylenedioxy and optical isomers and acid addition salts of the compounds. In addition to psycho pharmacological, diuretic and antiarrhythmic properties, the novel compounds of Formula I possess primarily outstanding analgesic activities and are low in toxicity. The compounds are prepared by acylating 2-aminomethyl-1,4-benzodiazepine derivatives with corresponding carbonic acid derivatives. Furthermore, 2-azidomethyl-1,4-benzodiazepine derivatives are disclosed which provi…