WO2010029574A3 - An improved process for the preparation of gemcitabine and its intermediates using novel protecting groups and ion exchange resins - Google Patents

An improved process for the preparation of gemcitabine and its intermediates using novel protecting groups and ion exchange resins Download PDF

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Publication number
WO2010029574A3
WO2010029574A3 PCT/IN2009/000452 IN2009000452W WO2010029574A3 WO 2010029574 A3 WO2010029574 A3 WO 2010029574A3 IN 2009000452 W IN2009000452 W IN 2009000452W WO 2010029574 A3 WO2010029574 A3 WO 2010029574A3
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WO
WIPO (PCT)
Prior art keywords
period
gemcitabine
added
improved process
dibenzoate
Prior art date
Application number
PCT/IN2009/000452
Other languages
French (fr)
Other versions
WO2010029574A2 (en
Inventor
Vishwanath Kannan
Vishwanathan Kash
Original Assignee
Vishwanath Kannan
Vishwanathan Kash
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Vishwanath Kannan, Vishwanathan Kash filed Critical Vishwanath Kannan
Publication of WO2010029574A2 publication Critical patent/WO2010029574A2/en
Publication of WO2010029574A3 publication Critical patent/WO2010029574A3/en

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Classifications

    • 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
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
    • 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)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

An improved process for preparing gemcitabine or salts thereof, comprising the following steps, dissolved 2-Deoxy-2,2- difluoro-D-ribofuranose-3,5-dibenzoate in an organic solvent and allowed to cool to 0 to 10 degree centigrade temperature, stirred for a period of 1 to 2 hours to this triethylamine is added for a period of 2 to 10 minutes, an indigenous protecting compound added under constant stirring, solvents were distilled off, and to the residual volume IN HCL is added until to form a clear solution adjusted the PH of about 2, further to this an ethyl acetate was added followed by washing the organic phase using NaHCo3, water and brine solution, the organic phase was dried over MgSo4, concentrated the above reaction mixture under reduced pressure to obtain a crude 2-deoxy-2,2-difluoro-D- riboufuranose-3,5-dibenzoate-l-arylateas an oil phase, above product is dissolved in dry methanol under constant stirring using Ion exhange resin for a period of 15 to 25 hours at 30 to 45 degree centigrade temperature, which gives pure gemcitabine hydrochloride.
PCT/IN2009/000452 2008-08-18 2009-08-13 An improved process for the preparation of gemcitabine and its intermediates using novel protecting groups and ion exchange resins WO2010029574A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1748MU2008 2008-08-18
IN1748/MUM/2008 2008-08-18

Publications (2)

Publication Number Publication Date
WO2010029574A2 WO2010029574A2 (en) 2010-03-18
WO2010029574A3 true WO2010029574A3 (en) 2011-01-06

Family

ID=42005584

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2009/000452 WO2010029574A2 (en) 2008-08-18 2009-08-13 An improved process for the preparation of gemcitabine and its intermediates using novel protecting groups and ion exchange resins

Country Status (1)

Country Link
WO (1) WO2010029574A2 (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006071090A1 (en) * 2004-12-30 2006-07-06 Hanmi Pharm. Co., Ltd. Method for the preparation of 2'-deoxy-2',2'-difluorocytidine
WO2006070985A1 (en) * 2004-12-30 2006-07-06 Hanmi Pharm. Co., Ltd. METHOD FOR THE PREPARATION OF 2#-DEOXY-2#,2#-DIFLUOROCYTIDINE

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006071090A1 (en) * 2004-12-30 2006-07-06 Hanmi Pharm. Co., Ltd. Method for the preparation of 2'-deoxy-2',2'-difluorocytidine
WO2006070985A1 (en) * 2004-12-30 2006-07-06 Hanmi Pharm. Co., Ltd. METHOD FOR THE PREPARATION OF 2#-DEOXY-2#,2#-DIFLUOROCYTIDINE

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHOU, T. S. ET AL.: "Stereospecific synthesis of 2-deoxy-2,2- difluororibonolactone and its use in the preparation of 2'-deoxy- 2',2'-difluoro-beta-D-ribofuranosyl pyrimidine nucleosides: the key role of selective crystallization", SYNTHESIS, 1992, pages 565 - 70 *
DATABASE CASREACT accession no. STN Database accession no. 117:131482 *
DATABASE CASREACT accession no. STN Database accession no. 150:564073 *
WANG, YINGHUA ET AL.: "Synthesis of gemcitabine hydrochloride", ZHONGGUO YIYAO GONGYE ZAZHI, vol. 38, no. 4, 2007, pages 249 - 251 *

Also Published As

Publication number Publication date
WO2010029574A2 (en) 2010-03-18

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