WO2007027564A3 - Process for preparing gemcitabine and associated intermediates - Google Patents

Process for preparing gemcitabine and associated intermediates Download PDF

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Publication number
WO2007027564A3
WO2007027564A3 PCT/US2006/033431 US2006033431W WO2007027564A3 WO 2007027564 A3 WO2007027564 A3 WO 2007027564A3 US 2006033431 W US2006033431 W US 2006033431W WO 2007027564 A3 WO2007027564 A3 WO 2007027564A3
Authority
WO
WIPO (PCT)
Prior art keywords
ester
process
intermediates
methylbenzylcarbonyl
deoxy
Prior art date
Application number
PCT/US2006/033431
Other languages
French (fr)
Other versions
WO2007027564A2 (en
Inventor
Jingshan Shen
Yafei Li
Joseph Kaspi
Original Assignee
Chemagis Ltd
Perrigo Company
Jingshan Shen
Yafei Li
Joseph Kaspi
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
Priority to US71221705P priority Critical
Priority to US60/712,217 priority
Application filed by Chemagis Ltd, Perrigo Company, Jingshan Shen, Yafei Li, Joseph Kaspi filed Critical Chemagis Ltd
Publication of WO2007027564A2 publication Critical patent/WO2007027564A2/en
Publication of WO2007027564A3 publication Critical patent/WO2007027564A3/en

Links

Classifications

    • 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
    • C07H19/067Pyrimidine radicals with ribosyl as the saccharide radical
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of products other than chlorine, adipic acid, caprolactam, or chlorodifluoromethane, e.g. bulk or fine chemicals or pharmaceuticals
    • Y02P20/55Synthetic design, e.g. reducing the use of auxiliary or protecting groups

Abstract

Provided is a process for preparing gemcitabine or a salt thereof, which preferably includes removing at least a substantial portion of the α anomer of a N-1-protected-2'-deoxy-2',2'-difluoro-cytidine-3',5'-diester from an anomeric mixture thereof; removing the 3'-ester, the 5'-ester and the N-protecting group; and optionally forming a salt. The 3'-ester and 5'-ester can be the same or different and at least one of the esters preferably is cinnamoyl, benzoyl, 1-naphthoyl, 1-naphthylmethylcarbonyl, 2-methylbenzylcarbonyl, 4-methylbenzylcarbonyl or 9-fluorenylmethyloxycarbonyl ester. Also provided are novel intermediates, including but not limited to 2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-diesters, and methods of producing such intermediates.
PCT/US2006/033431 2005-08-29 2006-08-28 Process for preparing gemcitabine and associated intermediates WO2007027564A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US71221705P true 2005-08-29 2005-08-29
US60/712,217 2005-08-29

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2008529146A JP2009506118A (en) 2005-08-29 2006-08-28 Method for producing gemcitabine and related intermediates
EP06802423A EP1931693A2 (en) 2005-08-29 2006-08-28 Process for preparing gemcitabine and associated intermediates

Publications (2)

Publication Number Publication Date
WO2007027564A2 WO2007027564A2 (en) 2007-03-08
WO2007027564A3 true WO2007027564A3 (en) 2007-06-07

Family

ID=37809396

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/033431 WO2007027564A2 (en) 2005-08-29 2006-08-28 Process for preparing gemcitabine and associated intermediates

Country Status (5)

Country Link
EP (1) EP1931693A2 (en)
JP (1) JP2009506118A (en)
KR (1) KR20080039502A (en)
CN (1) CN101296934A (en)
WO (1) WO2007027564A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100741310B1 (en) * 2006-08-01 2007-07-13 (주) 유일팜테크 Naphthalene 2-carboxylate derivative useful for synthesizing gemcitabine and a method for preparing the same
WO2008117955A1 (en) * 2007-03-23 2008-10-02 Dongwoo Syntech Co., Ltd. Process for preparing of 2'-deoxy-2'2'-difluorocytidine
US20080262215A1 (en) * 2007-04-23 2008-10-23 Chemagis Ltd. Gemcitabine production process
CN100475832C (en) * 2007-05-31 2009-04-08 南京卡文迪许生物工程技术有限公司;许永翔 Novel highly-solid selectively synthesizing gemcitabine process and intermediate
KR100957756B1 (en) * 2007-12-12 2010-05-12 동우신테크 주식회사 Process for preparing of 2'-deoxy-2'2'-difluorocytidine
CN101492482B (en) * 2008-12-17 2010-09-29 美中能特医药化学科技(荆州)有限公司 Synthesis process of the industrial production of gemcitabine hydrochloride
CN101899079B (en) 2009-05-30 2012-09-12 鲁南制药集团股份有限公司 Preparation, separation and purification method of Decitabine

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4097665A (en) * 1974-11-22 1978-06-27 Asahi Kasei Kogyo Kabushiki Kaisha Diacylnucleosides and process for preparing the same
US4751221A (en) * 1985-10-18 1988-06-14 Sloan-Kettering Institute For Cancer Research 2-fluoro-arabinofuranosyl purine nucleosides
US4965374A (en) * 1987-08-28 1990-10-23 Eli Lilly And Company Process for and intermediates of 2',2'-difluoronucleosides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4097665A (en) * 1974-11-22 1978-06-27 Asahi Kasei Kogyo Kabushiki Kaisha Diacylnucleosides and process for preparing the same
US4751221A (en) * 1985-10-18 1988-06-14 Sloan-Kettering Institute For Cancer Research 2-fluoro-arabinofuranosyl purine nucleosides
US4965374A (en) * 1987-08-28 1990-10-23 Eli Lilly And Company Process for and intermediates of 2',2'-difluoronucleosides

Also Published As

Publication number Publication date
KR20080039502A (en) 2008-05-07
EP1931693A2 (en) 2008-06-18
JP2009506118A (en) 2009-02-12
WO2007027564A2 (en) 2007-03-08
CN101296934A (en) 2008-10-29

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