Resolution method for axis chiral enantiomers of lesinurad

US11365180B2 · kind B2 · utility

Assignee

• CHINA RESOURCES SAIKE PHARMACEUTICAL CO., LTD. · CN

Inventors

• Deqian Bian · Beijing, CN
• Moyi Liu · Beijing, CN
• Yan Yang · Beijing, CN
• Fangze Chi · Beijing, CN

Key dates

• Filing date: Apr 26, 2019
• Grant date: Jun 21, 2022
• Expiry date: Apr 26, 2039

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07B57/00
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

A resolution method of axial chiral enantiomers of lesinurad (2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid) adopts inexpensive and readily available quinoline natural products and derivatives thereof, such as quinine, cinchonine, quinidine or cinconidine as resolving agents to react with lesinurad racemate in an organic solvent to form a salt, and the salt is dissociated by acidification so as to obtain optically pure (R)- or (S)-2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid. The method can give axial chiral enantiomer of lesinurad in R configuration with a chiral purity ee of up to 100% and a total yield of 90% or more. The obtained axial chiral enantiomer of lesinurad in S configuration can reach a chiral purity ee of up to 99.9% and a total yield of 80% or more.