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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Publication of CA2224155A1 publication Critical patent/CA2224155A1/en
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Publication of CA2224155C publication Critical patent/CA2224155C/en
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Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic 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
    • C07D333/26—Heterocyclic 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/20—Purine 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)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic 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
JP278631/1996 1996-09-30
JP27863196 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

Family

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
WO1999043691A1 (en) * 1998-02-25 1999-09-02 Emory University 2'-fluoronucleosides
CA2538252C (en) * 2003-09-18 2014-02-25 Isis Pharmaceuticals, Inc. 4'-thionucleosides and oligomeric compounds
US7524831B2 (en) * 2005-03-02 2009-04-28 Schering Corporation Treatments for Flaviviridae virus infection
RU2559364C2 (ru) 2009-12-18 2015-08-10 Либрамедисина, Инк. СПОСОБ ПОЛУЧЕНИЯ ЗАМЕЩЕННЫХ 1-О-АЦИЛ-2-ДЕЗОКСИ-2-ФТОР-4-ТИО-β-D-АРАБИНОФУРАНОЗ
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
SG10201603288XA (en) * 2012-03-28 2016-05-30 Fujifilm Corp Salt Of 1-(2-Deoxy-2-Fluoro-4-Thio-beta-D-Arabinofuranosyl)Cytosine
US10005779B2 (en) 2013-06-05 2018-06-26 Idenix Pharmaceuticals Llc 1′,4′-thio nucleosides for the treatment of HCV
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
EP3109245B1 (en) 2014-02-18 2018-01-03 FUJIFILM Corporation Method for producting thiolane skeleton-type glycoconjugate, and thiolane skeleton-type glycoconjugate
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
WO2018113592A1 (zh) 2016-12-22 2018-06-28 四川科伦博泰生物医药股份有限公司 4'-硫代-2'-氟代核苷磷酰胺化合物的固体形式及其制备方法和用途
EP3677267A4 (en) 2017-09-01 2021-06-02 Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd. PHARMACEUTICAL COMPOSITION FOR TREATMENT OR PREVENTION OF TUMORS, METHOD AND USES THEREOF
TW201932120A (zh) * 2018-01-29 2019-08-16 日商富士軟片股份有限公司 用於具有異檸檬酸脫氫酶突變的腫瘤的藥物組成物與抗腫瘤劑及其應用
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
WO2019176984A1 (ja) 2018-03-13 2019-09-19 富士フイルム株式会社 抗腫瘍剤、抗腫瘍効果増強剤及び抗腫瘍用キット
EP3856754A1 (en) * 2018-09-25 2021-08-04 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
JPWO2023008511A1 (enExample) 2021-07-29 2023-02-02

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
US5811408A (en) * 1994-07-12 1998-09-22 Yamasa Corporation 2'-deoxy-2'-(substituted or unsubstituted)methylidene-4'-thionucleosides
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
PT841344E (pt) 2003-02-28
WO1997038001A1 (en) 1997-10-16
JP3657008B2 (ja) 2005-06-08
EP0841344B1 (en) 2002-09-25
DE69715774D1 (de) 2002-10-31
DE69715774T2 (de) 2003-05-15
EP0841344A4 (enExample) 1998-05-13
DK0841344T3 (da) 2002-12-23
US6147058A (en) 2000-11-14
EP0841344A1 (en) 1998-05-13
ATE224909T1 (de) 2002-10-15
ES2182061T3 (es) 2003-03-01
CA2224155A1 (en) 1997-10-16

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