CA2574651C - Preparation of alkyl-substituted 2-deoxy-2-fluoro-d-ribofuranosyl pyrimidines and purines and their derivatives - Google Patents

Preparation of alkyl-substituted 2-deoxy-2-fluoro-d-ribofuranosyl pyrimidines and purines and their derivatives Download PDF

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Publication number
CA2574651C
CA2574651C CA2574651A CA2574651A CA2574651C CA 2574651 C CA2574651 C CA 2574651C CA 2574651 A CA2574651 A CA 2574651A CA 2574651 A CA2574651 A CA 2574651A CA 2574651 C CA2574651 C CA 2574651C
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Canada
Prior art keywords
compound
alkyl
substituted
trityl
independently
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Expired - Lifetime
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CA2574651A
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English (en)
French (fr)
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CA2574651A1 (en
Inventor
Peiyuan Wang
Wojciech Stec
Byoung-Kwon Chun
Junxing Shi
Jinfa Du
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Gilead Sciences Inc
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Pharmasset Inc
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Priority to CA2735079A priority Critical patent/CA2735079C/en
Publication of CA2574651A1 publication Critical patent/CA2574651A1/en
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Publication of CA2574651C publication Critical patent/CA2574651C/en
Anticipated expiration legal-status Critical
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
    • 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
    • C07H19/173—Purine radicals with 2-deoxyribosyl as the saccharide radical
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • 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
    • C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
    • C07H5/06—Aminosugars
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Virology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2574651A 2004-07-21 2005-07-21 Preparation of alkyl-substituted 2-deoxy-2-fluoro-d-ribofuranosyl pyrimidines and purines and their derivatives Expired - Lifetime CA2574651C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2735079A CA2735079C (en) 2004-07-21 2005-07-21 Preparation of alkyl-substituted 2-deoxy-2-fluoro-d-ribofuranosyl pyrimidines and purines and their derivatives

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US58986604P 2004-07-21 2004-07-21
US60/589,866 2004-07-21
US60823004P 2004-09-09 2004-09-09
US60/608,230 2004-09-09
PCT/US2005/025916 WO2006012440A2 (en) 2004-07-21 2005-07-21 Preparation of alkyl-substituted 2-deoxy-2-fluoro-d-ribofuranosyl pyrimidines and purines and their derivatives

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA2735079A Division CA2735079C (en) 2004-07-21 2005-07-21 Preparation of alkyl-substituted 2-deoxy-2-fluoro-d-ribofuranosyl pyrimidines and purines and their derivatives

Publications (2)

Publication Number Publication Date
CA2574651A1 CA2574651A1 (en) 2006-02-02
CA2574651C true CA2574651C (en) 2013-05-21

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ID=35786706

Family Applications (2)

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CA2574651A Expired - Lifetime CA2574651C (en) 2004-07-21 2005-07-21 Preparation of alkyl-substituted 2-deoxy-2-fluoro-d-ribofuranosyl pyrimidines and purines and their derivatives
CA2735079A Expired - Lifetime CA2735079C (en) 2004-07-21 2005-07-21 Preparation of alkyl-substituted 2-deoxy-2-fluoro-d-ribofuranosyl pyrimidines and purines and their derivatives

Family Applications After (1)

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CA2735079A Expired - Lifetime CA2735079C (en) 2004-07-21 2005-07-21 Preparation of alkyl-substituted 2-deoxy-2-fluoro-d-ribofuranosyl pyrimidines and purines and their derivatives

Country Status (16)

Country Link
EP (2) EP1773856B1 (https=)
JP (2) JP5078612B2 (https=)
KR (2) KR101236669B1 (https=)
CN (1) CN102199181B (https=)
AT (1) ATE543789T1 (https=)
AU (2) AU2005267051B2 (https=)
CA (2) CA2574651C (https=)
DK (1) DK1773856T3 (https=)
ES (1) ES2386005T3 (https=)
IL (2) IL180832A (https=)
MX (1) MX2007000803A (https=)
NZ (1) NZ552927A (https=)
PL (1) PL1773856T3 (https=)
PT (1) PT1773856E (https=)
RU (1) RU2407747C2 (https=)
WO (1) WO2006012440A2 (https=)

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MX2009006156A (es) * 2006-12-18 2009-06-19 Hoffmann La Roche Proceso para preparar 3,5-di-omicron-acil-2-fluoro-2-c-metil-d-rib ono-gamma-lactona.
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KR20110098849A (ko) 2008-12-23 2011-09-01 파마셋 인코포레이티드 뉴클레오시드 유사체
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PT2609923T (pt) 2010-03-31 2017-08-30 Gilead Pharmasset Llc Processo para a cristalização de 2-(((s)- (perfluorofenoxi)(fenoxi)fosforil)amino)propanoato de (s)-isopropilo
JP5716500B2 (ja) 2010-06-03 2015-05-13 セントラル硝子株式会社 （２Ｒ）−２−フルオロ−２−Ｃ−メチル−Ｄ−リボノ−γ−ラクトン類前駆体の製造方法
AU2011336632B2 (en) 2010-11-30 2015-09-03 Gilead Pharmasset Llc Compounds
EP2691409B1 (en) 2011-03-31 2018-02-21 Idenix Pharmaceuticals LLC. Compounds and pharmaceutical compositions for the treatment of viral infections
EA201391264A1 (ru) 2011-04-13 2014-03-31 Джилид Сайэнс, Инк. 1'-замещенные пиримидиновые n-нуклеозидные аналоги для противовирусного лечения
PL2709613T5 (pl) 2011-09-16 2020-12-14 Gilead Pharmasset Llc Metody leczenia hcv
US8889159B2 (en) 2011-11-29 2014-11-18 Gilead Pharmasset Llc Compositions and methods for treating hepatitis C virus
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Also Published As

Publication number Publication date
IL180832A0 (en) 2007-06-03
WO2006012440A3 (en) 2006-07-27
JP5351919B2 (ja) 2013-11-27
CN102199181A (zh) 2011-09-28
ES2386005T3 (es) 2012-08-07
MX2007000803A (es) 2007-04-02
EP2348029A1 (en) 2011-07-27
HK1106249A1 (en) 2008-03-07
NZ552927A (en) 2010-05-28
KR20070114344A (ko) 2007-12-03
JP2008507547A (ja) 2008-03-13
RU2407747C2 (ru) 2010-12-27
AU2011200941B2 (en) 2011-11-24
CA2735079C (en) 2013-11-05
JP5078612B2 (ja) 2012-11-21
EP1773856A2 (en) 2007-04-18
DK1773856T3 (da) 2012-05-21
IL180832A (en) 2011-07-31
RU2007106574A (ru) 2008-08-27
CN102199181B (zh) 2014-09-17
WO2006012440A2 (en) 2006-02-02
JP2011148817A (ja) 2011-08-04
WO2006012440A8 (en) 2011-06-16
ATE543789T1 (de) 2012-02-15
PL1773856T3 (pl) 2013-01-31
PT1773856E (pt) 2012-05-14
AU2005267051B2 (en) 2011-07-14
CA2735079A1 (en) 2006-02-02
AU2011200941C1 (en) 2012-05-10
KR101236669B1 (ko) 2013-02-22
CA2574651A1 (en) 2006-02-02
AU2005267051A1 (en) 2006-02-02
KR20110034699A (ko) 2011-04-05
IL211606A0 (en) 2011-05-31
AU2011200941A1 (en) 2011-03-24
EP1773856A4 (en) 2010-10-13
KR101235548B1 (ko) 2013-02-21
EP1773856B1 (en) 2012-02-01

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