CA2224155C - 1-(2-deoxy-2-fluoro-4-thio-beta-d-arabinofuranosyl)cytosine - Google Patents

1-(2-deoxy-2-fluoro-4-thio-beta-d-arabinofuranosyl)cytosine Download PDF

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Publication number
CA2224155C
CA2224155C CA002224155A CA2224155A CA2224155C CA 2224155 C CA2224155 C CA 2224155C CA 002224155 A CA002224155 A CA 002224155A CA 2224155 A CA2224155 A CA 2224155A CA 2224155 C CA2224155 C CA 2224155C
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Canada
Prior art keywords
compound
formula
group
compound represented
fluoro
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Expired - Lifetime
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CA002224155A
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English (en)
French (fr)
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CA2224155A1 (en
Inventor
Yuichi Yoshimura
Kenji Kitano
Shinji Miura
Haruhiko Machida
Mikari Watanabe
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Libramedicina Inc
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Yamasa Corp
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06Pyrimidine radicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30Hetero atoms other than halogen
    • C07D333/32Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16Purine radicals
    • C07H19/20Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA002224155A 1996-04-09 1997-04-09 1-(2-deoxy-2-fluoro-4-thio-beta-d-arabinofuranosyl)cytosine Expired - Lifetime CA2224155C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
JP111968/1996 1996-04-09
JP11196896 1996-04-09
JP215082/1996 1996-07-26
JP21508296 1996-07-26
JP27863196 1996-09-30
JP278631/1996 1996-09-30
PCT/JP1997/001206 WO1997038001A1 (en) 1996-04-09 1997-04-09 1-(2-DEOXY-2-FLUORO-4-THIO-β-D-ARABINOFURANOSYL)CYTOSINES

Publications (2)

Publication Number Publication Date
CA2224155A1 CA2224155A1 (en) 1997-10-16
CA2224155C true CA2224155C (en) 2004-10-26

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ID=27312140

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002224155A Expired - Lifetime CA2224155C (en) 1996-04-09 1997-04-09 1-(2-deoxy-2-fluoro-4-thio-beta-d-arabinofuranosyl)cytosine

Country Status (10)

Country Link
US (1) US6147058A (enExample)
EP (1) EP0841344B1 (enExample)
JP (1) JP3657008B2 (enExample)
AT (1) ATE224909T1 (enExample)
CA (1) CA2224155C (enExample)
DE (1) DE69715774T2 (enExample)
DK (1) DK0841344T3 (enExample)
ES (1) ES2182061T3 (enExample)
PT (1) PT841344E (enExample)
WO (1) WO1997038001A1 (enExample)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107011168A (zh) * 2012-08-13 2017-08-04 富士胶片株式会社 1‑(2‑脱氧‑2‑氟‑4‑硫代‑β‑D‑阿拉伯呋喃糖基)胞嘧啶的合成中间体和硫代核苷的合成中间体
US10385089B2 (en) 2014-10-31 2019-08-20 Fujifilm Corporation Thionucleoside derivative or salt thereof, and pharmaceutical composition
US11141421B2 (en) 2018-01-29 2021-10-12 Fujifilm Corporation Antitumor agent for biliary tract cancer and method for treating biliary tract cancer
US11369625B2 (en) 2016-08-31 2022-06-28 Fujifilm Corporation Anti-tumor agent, anti-tumor effect enhancer, and anti-tumor kit

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7138384B1 (en) 1997-08-29 2006-11-21 The Regents Of The University Of California Modulators of DNA cytosine-5 methyltransferase and methods for use thereof
EP1058686B1 (en) 1998-02-25 2006-11-02 Emory University 2'-fluoronucleosides
JP5379347B2 (ja) * 2003-09-18 2013-12-25 アイシス ファーマシューティカルズ, インコーポレーテッド 4’−チオヌクレオシドおよびオリゴマー化合物
US7524831B2 (en) * 2005-03-02 2009-04-28 Schering Corporation Treatments for Flaviviridae virus infection
US8329925B2 (en) * 2009-12-18 2012-12-11 Libramedicina, Inc. Process for preparing substituted 1-O-acyl-2-deoxy-2-fluoro-4-thio-beta-D-arabinofuranoses
EP2388257A1 (en) 2010-05-20 2011-11-23 LibraMedicina, Inc. Process for preparing substituted 1-O-acyl-2-deoxy-2-fluoro-4-thio-ß-D-arabinofuranoses
RU2600734C2 (ru) 2012-03-28 2016-10-27 Фуджифилм Корпорэйшн СОЛЬ 1-(2-ДЕЗОКСИ-2-ФТОР-4-ТИО-β-D-АРАБИНОФУРАНОЗИЛ)ЦИТОЗИНА
US10005779B2 (en) 2013-06-05 2018-06-26 Idenix Pharmaceuticals Llc 1′,4′-thio nucleosides for the treatment of HCV
CN106061959B (zh) * 2014-02-18 2018-11-09 富士胶片株式会社 四氢噻吩骨架型糖化合物的制造方法及四氢噻吩骨架型糖化合物
JP6351107B2 (ja) * 2014-02-18 2018-07-04 富士フイルム株式会社 チオラン骨格型糖化合物の製造方法およびチオラン骨格型糖化合物
JP6204223B2 (ja) 2014-02-19 2017-09-27 富士フイルム株式会社 チオピラノース化合物等の製造方法
CN109553651B (zh) * 2015-04-03 2021-08-06 四川科伦博泰生物医药股份有限公司 4’-硫代核苷的新型化合物及其制备方法、药物组合物和应用
JP6450356B2 (ja) * 2016-02-29 2019-01-09 富士フイルム株式会社 液状医薬製剤
EA201990780A1 (ru) 2016-12-22 2019-11-29 Твердая форма соединения 4'-тио-2'-фторнуклеозид фосфамида и способ его получения и применения
US11266674B2 (en) 2017-09-01 2022-03-08 Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd. Pharmaceutical composition for tumor treatment or prevention, method, and use thereof
WO2019146129A1 (ja) * 2018-01-29 2019-08-01 富士フイルム株式会社 イソクエン酸デヒドロゲナーゼ変異を有する腫瘍に対する医薬組成物および抗腫瘍剤ならびにその利用
WO2019164010A1 (ja) * 2018-02-26 2019-08-29 富士フイルム株式会社 膀胱がん用抗腫瘍剤および膀胱がんの処置方法
CN111836628B (zh) 2018-03-13 2025-01-07 富士胶片株式会社 抗肿瘤剂、抗肿瘤效果增强剂及抗肿瘤用试剂盒
WO2020068657A1 (en) * 2018-09-25 2020-04-02 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services 2'-halogenated-4'-thio-2'-deoxy-5-azacytidine analogs and use thereof
CN112770731A (zh) * 2018-11-28 2021-05-07 四川科伦博泰生物医药股份有限公司 以4’-硫代核苷类化合物为活性成分的口服药物组合物、其制备方法及其用途
JP2022542697A (ja) * 2019-07-30 2022-10-06 ピノットバイオ,インコーポレイテッド 癌治療用ジヌクレオチド化合物及びその医薬用途
CN117794548A (zh) 2021-07-29 2024-03-29 富士胶片株式会社 针对bap1及pbrm1中的至少一个的功能下降的肿瘤的药物组合物及抗肿瘤剂

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE74701B1 (en) * 1989-10-04 1997-07-30 Univ Birmingham Further antiviral pyrimidine nucleosides
WO1996001834A1 (en) * 1994-07-12 1996-01-25 Yamasa Corporation 2'-deoxy-2'-(substituted or unsubstituted methylidene)-4'-thionucleoside
JPH0853490A (ja) * 1994-08-09 1996-02-27 Yamasa Shoyu Co Ltd 2’−デオキシ−2’,2’−ジハロゲノ−4’−チオヌクレオシド

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107011168A (zh) * 2012-08-13 2017-08-04 富士胶片株式会社 1‑(2‑脱氧‑2‑氟‑4‑硫代‑β‑D‑阿拉伯呋喃糖基)胞嘧啶的合成中间体和硫代核苷的合成中间体
CN107011168B (zh) * 2012-08-13 2020-06-09 富士胶片株式会社 胞嘧啶类的合成中间体和硫代核苷的合成中间体
US10385089B2 (en) 2014-10-31 2019-08-20 Fujifilm Corporation Thionucleoside derivative or salt thereof, and pharmaceutical composition
US11369625B2 (en) 2016-08-31 2022-06-28 Fujifilm Corporation Anti-tumor agent, anti-tumor effect enhancer, and anti-tumor kit
US11141421B2 (en) 2018-01-29 2021-10-12 Fujifilm Corporation Antitumor agent for biliary tract cancer and method for treating biliary tract cancer

Also Published As

Publication number Publication date
DK0841344T3 (da) 2002-12-23
DE69715774D1 (de) 2002-10-31
EP0841344A4 (enExample) 1998-05-13
EP0841344B1 (en) 2002-09-25
ATE224909T1 (de) 2002-10-15
WO1997038001A1 (en) 1997-10-16
EP0841344A1 (en) 1998-05-13
ES2182061T3 (es) 2003-03-01
PT841344E (pt) 2003-02-28
DE69715774T2 (de) 2003-05-15
CA2224155A1 (en) 1997-10-16
JP3657008B2 (ja) 2005-06-08
US6147058A (en) 2000-11-14

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