Oxygen substituted derivatives of nucleophile-nitric oxide adducts as nitric oxide donor prodrugs

US5366997A · kind A · utility

Assignee

• The United States of America as Represented by the Secretary of the Department of Health and Human Services · US

Inventors

• Larry K. Keefer · Bethesda, US
• Tambra M. Dunams · Florence, US
• Joseph E. Saavedra · Thurmont, US

Key dates

• Filing date: Sep 23, 1992
• Grant date: Nov 22, 1994
• Expiry date: Sep 23, 2012

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C307/02
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

There are disclosed cardiovascularly active compounds possessing antihypertensive properties, and pharmaceutical compositions containing these agents and a method of treating cardiovascular disorders with the compounds. The active components of the pharmaceutical compositions are compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are independently chosen from straight chain and branched chain alkyl and olefinic groups, which may be unsubstituted or substituted; or R.sub.1 and R.sub.2 together with the nitrogen atom they are bonded to form a heterocyclic group; and R.sub.3 is a pharmaceutically acceptable organic group selected from alkyl and olefinic groups which may be unsubstituted or substituted, acyl, a sulfonyl, sulfinyl, sulfenyl, carbonate, or carbamate derivative; or R.sub.3 is a group of the formula--(CH.sub.2).sub.n ONN(O)NR.sub.1 R.sub.2, wherein n is 2-8, and R.sub.1 and R.sub.2 are as described above. Novel compounds are disclosed wherein at least one of R.sub.1, R.sub.2 and R.sub.3 is an olefinic group or heteroatom-substituted straight or branched chain alkyl or olefinic group. Novel methods of synthesizing the compounds are also disclosed.