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Title:
METHOD FOR SYNTHESIZING C-NUCLEOSIDE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2022/012630
Kind Code:
A1
Abstract:
Disclosed is a method for preparing a C-nucleoside compound represented by formula (III), or a salt thereof. The present method has a high reaction yield, is simple to operate, uses a single metal reagent, has stable reaction temperature conditions, does not require frequent changes to the reaction system during the operation process, is suitable for scaled-up synthesis, is suitable for large-scale production of Remdesivir, and has low costs.

Inventors:
QIN YONG (CN)
ZHONG WU (CN)
XUE FEI (CN)
LIU XIAOYU (CN)
WANG YU (CN)
ZHOU XIAOHAN (CN)
LIU BO (CN)
WANG KE (CN)
YANG LIKAI (CN)
ZHOU RUIJIE (CN)
XIAO YAXIN (CN)
XUE FANGLIN (CN)
ZHANG MINJIE (CN)
SONG HAO (CN)
ZHENG ZHIBING (CN)
LI SONG (CN)
Application Number:
PCT/CN2021/106520
Publication Date:
January 20, 2022
Filing Date:
July 15, 2021
Export Citation:
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Assignee:
UNIV SICHUAN (CN)
ACAD OF MILITARY MEDICAL SCIENCES (CN)
CHENGDU AUPONE PHARMACEUTICAL CO LTD (CN)
International Classes:
C07H15/18; C07F7/10; C07H1/00; C07H15/04; C07H15/10
Domestic Patent References:
WO2014035140A22014-03-06
WO2014042433A22014-03-20
WO2011035250A12011-03-24
WO2014042433A22014-03-20
WO2014035140A22014-03-06
Foreign References:
CN111793101A2020-10-20
CN105899216A2016-08-24
CN109748921A2019-05-14
CN103153314A2013-06-12
CN202010692306A2020-07-17
Other References:
XUE FEI, ZHOU XINBO, ZHOU RUIJIE, ZHOU XIAOHAN, XIAO DIAN, GU ERIC, GUO XIAOWEN, XIANG JI, WANG KE, YANG LIKAI, ZHONG WU, QIN YONG: "Improvement of the C -glycosylation Step for the Synthesis of Remdesivir", ORGANIC PROCESS RESEARCH & DEVELOPMENT, AMERICAN CHEMICAL SOCIETY, US, vol. 24, no. 9, 18 September 2020 (2020-09-18), US , pages 1772 - 1777, XP055852847, ISSN: 1083-6160, DOI: 10.1021/acs.oprd.0c00310
AESOP CHO, OLIVER L. SAUNDERS, THOMAS BUTLER, LIJUN ZHANG, JIE XU, JENNIFER E. VELA, JOY Y. FENG, ADRIAN S. RAY, CHOUNG U. KIM: "Synthesis and antiviral activity of a series of 1′-substituted 4-aza-7,9-dideazaadenosine C-nucleosides", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 22, no. 8, 1 April 2012 (2012-04-01), AMSTERDAM, NL , pages 2705 - 2707, XP055238769, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2012.02.105
SAMMY E. METOBO; JIE XU; OLIVER L. SAUNDERS; THOMAS BUTLER; EVANGELOS AKTOUDIANAKIS; AESOP CHO; CHOUNG U. KIM;: "Practical synthesis of 1-substituted Tubercidin C-nucleoside analogs", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 53, no. 5, 11 November 2011 (2011-11-11), Amsterdam , NL , pages 484 - 486, XP028346649, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2011.11.055
AESOP CHO; LIJUN ZHANG; JIE XU; DARIUS BABUSIS; THOMAS BUTLER; RICK LEE; OLIVER L. SAUNDERS; TING WANG; JAY PARRISH; JASON PERRY; : "Synthesis and characterization of 2--Me branched-nucleosides as HCV polymerase inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 22, no. 12, 10 April 2012 (2012-04-10), AMSTERDAM, NL , pages 4127 - 4132, XP028509350, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2012.04.065
AESOP CHO, LIJUN ZHANG, JIE XU, RICK LEE, THOMAS BUTLER, SAMMY METOBO, VANGELIS AKTOUDIANAKIS, WILLARD LEW, HONG YE, MICHAEL CLARK: "Discovery of the First C -Nucleoside HCV Polymerase Inhibitor (GS-6620) with Demonstrated Antiviral Response in HCV Infected Patients", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 57, no. 5, 13 March 2014 (2014-03-13), US , pages 1812 - 1825, XP055257191, ISSN: 0022-2623, DOI: 10.1021/jm400201a
SINA BAVARI ET AL.: "subsequently improved the addition reaction of this step", NATURE, vol. 531, 2016, pages 381 - 385
BIOORG. MED. CHEM. LETT., vol. 22, 2012, pages 2705 - 2707
Attorney, Agent or Firm:
CCPIT PATENT AND TRADEMARK LAW OFFICE (CN)
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