EP1831236A4 - METHOD FOR PREPARING 2'-DEOXY-2 ', 2'-DIFLUOROCYTIDINE - Google Patents

METHOD FOR PREPARING 2'-DEOXY-2 ', 2'-DIFLUOROCYTIDINE

Info

Publication number
EP1831236A4
EP1831236A4 EP05823850.2A EP05823850A EP1831236A4 EP 1831236 A4 EP1831236 A4 EP 1831236A4 EP 05823850 A EP05823850 A EP 05823850A EP 1831236 A4 EP1831236 A4 EP 1831236A4
Authority
EP
European Patent Office
Prior art keywords
formula
difluorocytidine
deoxy
preparing
nucleoside
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP05823850.2A
Other languages
German (de)
French (fr)
Other versions
EP1831236A1 (en
Inventor
Jaeheon Lee
Gha Seung Park
Moonsub Lee
Hyo-Jeong Bang
Jae Chul Lee
Cheol Kyong Kim
Chang-Ju Choi
Han Kyong Kim
Hoe Chul Lee
Young-Kil Chang
Gwan Sun Lee
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hanmi Science Co Ltd
Original Assignee
Hanmi Science Co Ltd
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 claimed from PCT/KR2005/001954 external-priority patent/WO2006070985A1/en
Application filed by Hanmi Science Co Ltd filed Critical Hanmi Science Co Ltd
Publication of EP1831236A1 publication Critical patent/EP1831236A1/en
Publication of EP1831236A4 publication Critical patent/EP1831236A4/en
Withdrawn legal-status Critical Current

Links

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

Landscapes

  • 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)

Abstract

This invention relates to an improved method for stereoselectively preparing 2¢¥-deoxy-2¢¥,2¢¥-difluorocytidine of formula (I), which comprises the steps of reacting a 1-halo ribofuranose compound of formula (III) with a nucleobase of formula (IV) in a solvent to obtain a nucleoside of formula (II) with removing the silyl halide of formula (V) produced during the reaction; and deprotecting the nucleoside of formula (II) to obtain 2¢¥-deoxy-2¢¥,2¢¥-difluorocytidine of formula (I).
EP05823850.2A 2004-12-30 2005-12-29 METHOD FOR PREPARING 2'-DEOXY-2 ', 2'-DIFLUOROCYTIDINE Withdrawn EP1831236A4 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
KR20040116316 2004-12-30
PCT/KR2005/001954 WO2006070985A1 (en) 2004-12-30 2005-06-23 METHOD FOR THE PREPARATION OF 2#-DEOXY-2#,2#-DIFLUOROCYTIDINE
PCT/KR2005/004633 WO2006071090A1 (en) 2004-12-30 2005-12-29 Method for the preparation of 2'-deoxy-2',2'-difluorocytidine

Publications (2)

Publication Number Publication Date
EP1831236A1 EP1831236A1 (en) 2007-09-12
EP1831236A4 true EP1831236A4 (en) 2013-11-20

Family

ID=36615168

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05823850.2A Withdrawn EP1831236A4 (en) 2004-12-30 2005-12-29 METHOD FOR PREPARING 2'-DEOXY-2 ', 2'-DIFLUOROCYTIDINE

Country Status (6)

Country Link
EP (1) EP1831236A4 (en)
CN (1) CN101010329B (en)
AU (1) AU2005320374B2 (en)
BR (1) BRPI0514718A (en)
NO (1) NO20070865L (en)
WO (1) WO2006071090A1 (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008531680A (en) * 2005-03-04 2008-08-14 ダブール・ファーマ・リミテッド Intermediates and methods for the preparation of 21-deoxy-21,21-difluoro-D-ribofuranosyl nucleosides enriched in beta anomers
CN100475832C (en) 2007-05-31 2009-04-08 南京卡文迪许生物工程技术有限公司 Novel highly-solid selectively synthesizing gemcitabine process and intermediate
CN101381387B (en) * 2007-09-06 2011-08-31 上海希迪制药有限公司 Method for preparing 2'-deoxy-2',2'-difluoro-beta-cytidine hydrochlorate
TWI415858B (en) * 2007-11-06 2013-11-21 Pharmaessentia Corp Novel synthesis of β-nucleosides
JP2011524369A (en) * 2008-06-12 2011-09-01 サイノファーム タイワン リミテッド Crystalline polymorphism of gemcitabine base
WO2010029574A2 (en) * 2008-08-18 2010-03-18 Vishwanath Kannan An improved process for the preparation of gemcitabine and its intermediates using novel protecting groups and ion exchange resins
CN102617484B (en) * 2011-06-30 2014-05-14 江苏豪森药业股份有限公司 Process for recycling cytosine during preparing process of gemcitabine hydrochloride
CN102617483B (en) * 2011-06-30 2013-04-24 江苏豪森药业股份有限公司 Process for recycling cytosine during preparing process of gemcitabine hydrochloride
CN102432654A (en) * 2011-09-26 2012-05-02 宋云龙 Gemcitabine amide derivative and preparation method and application thereof
CN103224541B (en) * 2013-04-27 2015-07-01 江苏豪森药业股份有限公司 Gemcitabine alpha-isomer conversion recovery process
CN106317147B (en) * 2015-07-06 2018-11-27 扬州硒瑞恩生物医药科技有限公司 nucleoside compound and preparation method thereof
CN109305992A (en) * 2017-07-28 2019-02-05 江苏先声药业有限公司 A kind of preparation method of azacitidine

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1442420A (en) * 2003-04-08 2003-09-17 深圳市汉德森技术有限公司 Method of preparing 2'-deoxy-2',2'-difluoro-beta-nucleoside or its medical salt using 1,6-dehydro-beta-D-glucose as raw material

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5223608A (en) * 1987-08-28 1993-06-29 Eli Lilly And Company Process for and intermediates of 2',2'-difluoronucleosides
US5606048A (en) * 1992-06-22 1997-02-25 Eli Lilly And Company Stereoselective glycosylation process for preparing 2'-Deoxy-2', 2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides
US5371210A (en) * 1992-06-22 1994-12-06 Eli Lilly And Company Stereoselective fusion glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides
JPH0673086A (en) * 1992-06-22 1994-03-15 Eli Lilly & Co Stereoselective anionic glycosylation method
US5401861A (en) * 1992-06-22 1995-03-28 Eli Lilly And Company Low temperature process for preparing alpha-anomer enriched 2-deoxy-2,2-difluoro-D-ribofuranosyl sulfonates

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1442420A (en) * 2003-04-08 2003-09-17 深圳市汉德森技术有限公司 Method of preparing 2'-deoxy-2',2'-difluoro-beta-nucleoside or its medical salt using 1,6-dehydro-beta-D-glucose as raw material

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BARDOS, THOMAS J. ET AL: "Stereoselective synthesis of the anomeric 5-mercapto-2'-deoxyuridines and of some other anomeric 2-deoxy-D-erythropentonucleosides", TETRAHEDRON LETTERS, vol. 16, 1966, pages 1759 - 1764, XP002713325, ISSN: 0040-4039 *
KOTICK, MICHAEL P. ET AL: "Synthesis of 5-s-substituted 2'-deoxyuridines. Study of the factors influencing the stereoselectivity of the silyl modification of the Hilbert-Johnson reaction", JOURNAL OF ORGANIC CHEMISTRY, vol. 34, no. 12, 1969, pages 3806 - 3813, XP002713326, ISSN: 0022-3263 *
See also references of WO2006071090A1 *
VORBRUEGGEN, HELMUT ET AL: "Synthesis of nucleosides", ORGANIC REACTIONS, 2000, (HOBOKEN, NJ, UNITED STATES), XP002713324 *

Also Published As

Publication number Publication date
EP1831236A1 (en) 2007-09-12
NO20070865L (en) 2007-04-24
WO2006071090A1 (en) 2006-07-06
AU2005320374B2 (en) 2009-01-08
CN101010329B (en) 2011-06-08
BRPI0514718A (en) 2008-07-01
CN101010329A (en) 2007-08-01
AU2005320374A1 (en) 2006-07-06

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR

RIN1 Information on inventor provided before grant (corrected)

Inventor name: KIM, HAN KYONG

Inventor name: CHOI, CHANG-JU

Inventor name: CHANG, YOUNG-KIL

Inventor name: LEE, HOE CHUL

Inventor name: LEE, JAEHEON

Inventor name: PARK, GHA SEUNG

Inventor name: KIM, CHEOL KYONG

Inventor name: LEE, JAE CHUL

Inventor name: BANG, HYO-JEONG

Inventor name: LEE, MOONSUB

Inventor name: LEE, GWAN SUN

DAX Request for extension of the european patent (deleted)
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Owner name: HANMI HOLDINGS CO., LTD.

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: HANMI SCIENCE CO., LTD.

RIC1 Information provided on ipc code assigned before grant

Ipc: C07H 19/04 20060101AFI20130923BHEP

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