DI (1R)-(-)camphosulfonic acid) salt, preparation thereof and use thereof

US5652366A · kind A · utility

Assignee

• Rhone-Poulenc Rorer Pharmaceuticals Inc. · US

Inventors

• Alfred P. Spada · Lansdale, US
• Cynthia Fink · Lebanon, US
• Michael R. Myers · Fishers, US
• Laurence W. Reilly, Jr. · Yorktown Heights, US
• Benoit J. Vanasse · Collegeville, US

Key dates

• Filing date: Jun 7, 1995
• Grant date: Jul 29, 1997
• Expiry date: Jun 7, 2015

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07H19/16
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

This invention relates to di[(1 R)-(-)-camphosulfonic acid) salt of [1S-[1.alpha.,2.beta.,3.beta.,4.alpha.,(S*)]]-4-[7-[[2-(3-chloro-2-thienyl )-1-ethylethyl]amino]3 H-imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentanecarboxamide , and a process for preparing the compound, comprising reacting a reaction mixture of (-)-1.beta.-N-ethyl-2.alpha.,3.alpha.-isopropylidenedioxy-4.beta.-[3-amino -4-[2-(5-chloro-2-thienyl)-(1R)-1-ethylethyl]amino-2-pyridyl]aminocyclopent anecarboxamide and formamidine acetate, and then treating the reaction mixture with (1 R)-(-)-10-camphorsulfonic acid. The salt is useful in purifying [1 S-[1.alpha.,2.beta.,3.beta.,4.alpha.,(S*)]]-4-[7-[[2-(3-chloro-2-thienyl)- 1-ethylethyl]amino]-3 H-imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentanecarboxamide which possesses adenosine agonist activity and is useful as an anti-hypertensive, cardioprotective, anti-ischemic, and antilipolytic agent.