Bicyclo[3.1.0]hexyl-substituted carbonylaminophenoxy cardiovascular agents

US4177280A · kind A · utility

Assignee

• Syntex (U.S.A.) LLC · US

Inventors

• Karl G. Untch · Los Altos, US
• Belig Berkoz · Los Altos, US
• Stefan Unger · Palo Alto, US

Key dates

• Filing date: Jul 3, 1978
• Grant date: Dec 4, 1979
• Expiry date: Jul 3, 1998

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D263/06
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

1-Alkylamino-3-(4-[(endobicyclo[3.1.0]hex-6-yl)alkylure ido]-1-phenoxy)-2-propanol and substituted derivatives thereof; 1-alkylamino-3-(4-[(endobicyclo[3.1.0]hex-6-yl)-alkylcarbonylamino]-1-phen oxy)-2-propanol and substituted derivatives thereof; and 1-alkylamino-3-(4-[(endobicyclo-[3.1.0]hex-6-yl)alkoxycarbonylamino]-1-phe noxy)-2-propanol and substituted derivatives thereof as well as methods for preparing such compounds are disclosed. 5-(4-[(Endobicyclo[3.1.0]hex-6-yl)alkylureido]-1-phenoxy) methyl-3-alkyl-2-optionally substituted oxazolidine and derivatives thereof; 5-(4-[(endobicyclo[3.1.0]hex-6-yl alkylcarbonylamino]-1-phenoxy)methyl-3-alkyl-2-optionally substituted oxazolidine and derivatives thereof; and 5-(4-[(endobicyclo[3.1.0]hex-6-yl)alkoxycarbonylamino]-1-phenoxy)methyl-3- alkyl-2-optionally substituted oxazolidine and derivatives thereof and methods for preparing these compounds are also disclosed. These compounds exhibit cardiovascular activity and are useful in the treatment of abnormal heart conditions as well as hypertension in mammals. The bicyclo-2-propanols are prepared by treatment of the corresponding 1,2-epoxy-3-(4-[(endobicyclo[3.1.0]hex-6-yl)alkylureido, …