WO2008101448A4 - Method of manufacturing 1-(2-deoxy-alpha-d-erythro-pentofuranosyl)-5-azacytosine - Google Patents

Method of manufacturing 1-(2-deoxy-alpha-d-erythro-pentofuranosyl)-5-azacytosine Download PDF

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Publication number
WO2008101448A4
WO2008101448A4 PCT/CZ2008/000019 CZ2008000019W WO2008101448A4 WO 2008101448 A4 WO2008101448 A4 WO 2008101448A4 CZ 2008000019 W CZ2008000019 W CZ 2008000019W WO 2008101448 A4 WO2008101448 A4 WO 2008101448A4
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WIPO (PCT)
Prior art keywords
group
carbon atoms
azacytosine
deoxy
pentofuranosyl
Prior art date
Application number
PCT/CZ2008/000019
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French (fr)
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WO2008101448A2 (en
WO2008101448A3 (en
Inventor
Antonin Holy
Miroslav Otmar
Alois Piskala
Original Assignee
Ustav Organicke Chemie A Bioch
Antonin Holy
Miroslav Otmar
Alois Piskala
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Application filed by Ustav Organicke Chemie A Bioch, Antonin Holy, Miroslav Otmar, Alois Piskala filed Critical Ustav Organicke Chemie A Bioch
Publication of WO2008101448A2 publication Critical patent/WO2008101448A2/en
Publication of WO2008101448A3 publication Critical patent/WO2008101448A3/en
Publication of WO2008101448A4 publication Critical patent/WO2008101448A4/en

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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
    • C07H19/12—Triazine radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

This invention relates to a method of manufacturing 1-(2-deoxy-alpha-D-erythro-pentofuranosyl)-5-azacytosine by the treatment of protected alkyl or aralkyl 2-deoxy-D-erythro-pentofuranoside with silylated 5-azacytosine in the presence of Lewis acid and subsequent removal the protecting groups.

Claims

AMENDED CLAIMS received by the International Bureau on 12 January 2009(12.01.2009)
1. A method of manufacturing of l-(2-deoxy-alpha-D-eryr/iro-pentofuranosyl)-5- azacytosine of the formula I,
Figure imgf000002_0001
characterized in that the protected 2'-deoxy-D-er>tfΛ/O-pentofuranoside of the general formula II,
Figure imgf000002_0002
wherein R1 represents an alkyl group having 1 to 6 carbon atoms or aralkyl group having 7 to 10 carbons, being eventually substituted on aromatic ring with an alkyl group having 1 to 3 carbon atoms, halogen, methoxy group or nitro group, and R represents an alkanoyl group having 1 to 6 carbon atoms or aralkanoyl group having 7 to 11 carbon atoms, being eventually substituted on aromatic ring with an alkyl group having 1 to 3 carbons, halogen, methoxy group or nitro group, or aroyl having 7 to 11 carbon atoms, being eventually substituted on aromatic ring with an alkyl group having 1 to 3 carbon atoms, halogen, methoxy group or nitro group, is reacted with O^V-bis- (trialkylsilyl)-5-azacytosine of the general formula III,
PCT/CZ2008/000019 2007-02-20 2008-02-19 Method of manufacturing 1-(2-deoxy-alpha-d-erythro-pentofuranosyl)-5-azacytosine WO2008101448A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CZ20070136A CZ2007136A3 (en) 2007-02-20 2007-02-20 Process for preparing 1-(2-deoxy-alpha-D-erythro-pentofuranosyl)-5-azacytosine
CZPV2007-136 2007-02-20

Publications (3)

Publication Number Publication Date
WO2008101448A2 WO2008101448A2 (en) 2008-08-28
WO2008101448A3 WO2008101448A3 (en) 2009-02-05
WO2008101448A4 true WO2008101448A4 (en) 2009-03-19

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PCT/CZ2008/000019 WO2008101448A2 (en) 2007-02-20 2008-02-19 Method of manufacturing 1-(2-deoxy-alpha-d-erythro-pentofuranosyl)-5-azacytosine

Country Status (2)

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CZ (1) CZ2007136A3 (en)
WO (1) WO2008101448A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010129211A2 (en) * 2009-04-27 2010-11-11 Dr. Reddy's Laboratories Ltd. Preparation of decitabine
US9913822B2 (en) 2012-04-04 2018-03-13 Halozyme, Inc. Combination therapy with an anti-hyaluronan agent and therapeutic agent
CN103232512B (en) * 2013-04-13 2015-12-09 连云港杰瑞药业有限公司 A kind of method preparing the Decitabine precursor of β-enrichment
US20190351031A1 (en) 2018-05-16 2019-11-21 Halozyme, Inc. Methods of selecting subjects for combination cancer therapy with a polymer-conjugated soluble ph20

Also Published As

Publication number Publication date
CZ2007136A3 (en) 2008-08-27
WO2008101448A2 (en) 2008-08-28
WO2008101448A3 (en) 2009-02-05

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