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Title:
RESOLUTION METHOD FOR AXIS CHIRAL ENANTIOMERS OF LESINURAD
Document Type and Number:
WIPO Patent Application WO/2019/214467
Kind Code:
A1
Abstract:
A resolution method for axis chiral enantiomers of Lesinurad (2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid). In said method, inexpensive and readily available quinoline natural products and derivatives thereof such as quinine, cinchonine, quinidine or cinchonidine are used as resolving agents to react with a Lesinurad racemate in an organic solvent to form a salt, and acidification is carried out to dissociate the salt so as to obtain an optically pure (R)-or (S)-2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid. This method is convenient to operate. The Lesinurad axis chiral enantiomer in the R configuration can achieve a chiral purity ee of 100% and a total yield of 90% or more. The Lesinurad axis chiral enantiomer in the S configuration can achieve a chiral purity ee of 99.9% and a total yield of 80% or more. Furthermore, the chiral resolving agents used are cheap, easy to obtain, and can be easily recovered and reused, reducing the separation cost and facilitating industrial production.

Inventors:
BIAN, Deqian (21st Floor, Block A Jinhaishang Rich Center,No. 402, Baiziwan Xili, Chaoyang, Beijing 4, 100124, CN)
LIU, Moyi (21st Floor, Block A Jinhaishang Rich Center,No. 402, Baiziwan Xili, Chaoyang, Beijing 4, 100124, CN)
YANG, Yan (21st Floor, Block A Jinhaishang Rich Center,No. 402, Baiziwan Xili, Chaoyang, Beijing 4, 100124, CN)
CHI, Fangze (21st Floor, Block A Jinhaishang Rich Center,No. 402, Baiziwan Xili, Chaoyang, Beijing 4, 100124, CN)
Application Number:
CN2019/084640
Publication Date:
November 14, 2019
Filing Date:
April 26, 2019
Export Citation:
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Assignee:
CHINA RESOURES SAIKE PHARMACEUTICAL CO., LTD. (21st Floor, Block A Jinhaishang Rich Center,No. 402, Baiziwan Xili, Chaoyang, Beijing 4, 100124, CN)
International Classes:
C07D249/12; A61K31/4196; A61P19/06; C07B57/00
Foreign References:
CN107098866A2017-08-29
CN105399694A2016-03-16
CN105622531A2016-06-01
CN101346386A2009-01-14
Other References:
WANG J.F.: "Discovery and Assessment of Atropisomers of (±)-Lesinurad", ACS MED. CHEM. LETT., vol. 8, no. 3, 9 March 2017 (2017-03-09), pages 299 - 203, XP055412834, ISSN: 1948-5875, DOI: 10.1021/acsmedchemlett.6b00465
Attorney, Agent or Firm:
BEIJING ORIGINTELLIGENCE IP LAW FIRM (LIU Yuanxia / HUANG, HailiRoom 1004, Tower E, Jiahua Building,No. 9, Shangdi 3rd Street, Haidian District, Beijing 5, 100085, CN)
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