Title:
METHOD FOR PREPARING 4'-THIO-5-AZA-2'-DEOXYCYTIDINE
Document Type and Number:
WIPO Patent Application WO/2023/239190
Kind Code:
A1
Abstract:
The present invention relates to a method for preparing 4'-thio-5-aza-2'-deoxycytidine which exhibits DNMT1 inhibitory activity. The production method according to the present invention can enhance reaction efficiency through efficient process development and can stereoselectively prepare 4'-thio-5-aza-2'-deoxycytidine, and thus is economical and appropriate for mass production.
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Inventors:
JUNG DOO YOUNG (KR)
LEE JIN SOO (KR)
CHO HYUN YONG (KR)
KIM AH REUM (KR)
SEO MUN SIK (KR)
CHOI JUN YOUNG (KR)
LEE JIN SOO (KR)
CHO HYUN YONG (KR)
KIM AH REUM (KR)
SEO MUN SIK (KR)
CHOI JUN YOUNG (KR)
Application Number:
PCT/KR2023/007909
Publication Date:
December 14, 2023
Filing Date:
June 09, 2023
Export Citation:
Assignee:
PINOTBIO INC (KR)
ST PHARM CO LTD (KR)
ST PHARM CO LTD (KR)
International Classes:
C07H19/12; A61K31/706; C07F7/18
Domestic Patent References:
| WO2014152513A1 | 2014-09-25 | |||
| WO2019152459A1 | 2019-08-08 |
Other References:
HARAGUCHI KAZUHIRO; KUMAMOTO HIROKI; KONNO KIJU; YAGI HIDEKI; TATANO YUTAKA; ODANAKA YUKI; SHIMBARA MATSUBAYASHI SATOKO; SNOECK RO: "Synthesis of 4′-substituted 2′-deoxy-4′-thiocytidines and its evaluation for antineoplastic and antiviral activities", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 75, no. 33, 3 July 2019 (2019-07-03), AMSTERDAM, NL , pages 4542 - 4555, XP085749669, ISSN: 0040-4020, DOI: 10.1016/j.tet.2019.06.044
WISHKA DONN G., LOPEZ OMAR D., RUDCHENKO VLADIMIR F., HUANG GUANGFEI, BAHDE ROBERT, KUMAR VINEET, DENYSENKO SERGIY M., ZHANG LIANH: "The development of β-selective glycosylation reactions with benzyl substituted 2-deoxy-1,4-dithio-D- erythro -pentofuranosides: enabling practical multi-gram syntheses of 4'-Thio-2'-deoxycytidine (T-dCyd) and 5-aza-4’-thio-2’-deoxycytidine (aza-T-dCyd) to support clinical development", NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS, TAYLOR & FRANCIS, US, vol. 40, no. 1, 2 January 2021 (2021-01-02), US , pages 68 - 95, XP055901503, ISSN: 1525-7770, DOI: 10.1080/15257770.2020.1832694
HARAGUCHI KAZUHIRO, HORII CHIKAFUMI, YOSHIMURA YUICHI, ARIGA FUMIKO, TADOKORO AYA, TANAKA HIROMICHI: "An Access to the β-Anomer of 4′-Thio-C-ribonucleosides: Hydroboration of 1- C -Aryl- or 1- C -Heteroaryl-4-thiofuranoid Glycals and Its Regiochemical Outcome", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 76, no. 21, 4 November 2011 (2011-11-04), pages 8658 - 8669, XP093114538, ISSN: 0022-3263, DOI: 10.1021/jo201100n
WISHKA DONN G., LOPEZ OMAR D., RUDCHENKO VLADIMIR F., HUANG GUANGFEI, BAHDE ROBERT, KUMAR VINEET, DENYSENKO SERGIY M., ZHANG LIANH: "The development of β-selective glycosylation reactions with benzyl substituted 2-deoxy-1,4-dithio-D- erythro -pentofuranosides: enabling practical multi-gram syntheses of 4'-Thio-2'-deoxycytidine (T-dCyd) and 5-aza-4’-thio-2’-deoxycytidine (aza-T-dCyd) to support clinical development", NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS, TAYLOR & FRANCIS, US, vol. 40, no. 1, 2 January 2021 (2021-01-02), US , pages 68 - 95, XP055901503, ISSN: 1525-7770, DOI: 10.1080/15257770.2020.1832694
HARAGUCHI KAZUHIRO, HORII CHIKAFUMI, YOSHIMURA YUICHI, ARIGA FUMIKO, TADOKORO AYA, TANAKA HIROMICHI: "An Access to the β-Anomer of 4′-Thio-C-ribonucleosides: Hydroboration of 1- C -Aryl- or 1- C -Heteroaryl-4-thiofuranoid Glycals and Its Regiochemical Outcome", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 76, no. 21, 4 November 2011 (2011-11-04), pages 8658 - 8669, XP093114538, ISSN: 0022-3263, DOI: 10.1021/jo201100n
Attorney, Agent or Firm:
KIM, Kyeongkyo et al. (KR)
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