Enantiospecific synthesis of S-(+)-5,6-dihydro-4-(R-amino)-4H-thieno(2,3-b)thiopyran-2-sulfonamide-7, 7-dioxide

US5157129A · kind A · utility

Assignee

• MERCK & CO., INC. · US

Inventors

• Thomas J. Blacklock · Clark, US
• Todd K. Jones · Solana Beach, US
• Edward J. J. Grabowski · Westfield, US
• David J. Mathre · Skillman, US
• Julie J. Mohan · Edison, US
• Paul Sohar · Hackettstown, US
• F. Edward Roberts · Princeton, US
• Lyndon C. Xavier · Edison, US

Key dates

• Filing date: Apr 18, 1990
• Grant date: Oct 20, 1992
• Expiry date: Apr 18, 2010

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P27/02
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

5,6-Dihydro-4-(R-amino)-4H-thieno[2,3-b]-thiopyran-2-sulfonamide-7,7-dioxid e is a potent carbonic anhydrase inhibitor useful in the treatment of ocular hypertension and glaucoma. The S-(+)-enantiomer of that compound, the more active enantiomer, is prepared by a process involving an intermediate step of an enantioselective reduction of a carbonyl group employing an oxazaborolidine chiral catalyst.