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WO2012018235A3 - Method for preparing decitabine with improved yield and purity - Google Patents

Method for preparing decitabine with improved yield and purity Download PDF

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Publication number
WO2012018235A3
WO2012018235A3 PCT/KR2011/005724 KR2011005724W WO2012018235A3 WO 2012018235 A3 WO2012018235 A3 WO 2012018235A3 KR 2011005724 W KR2011005724 W KR 2011005724W WO 2012018235 A3 WO2012018235 A3 WO 2012018235A3
Authority
WO
WIPO (PCT)
Prior art keywords
purity
decitabine
preparing
improved yield
present
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.)
Ceased
Application number
PCT/KR2011/005724
Other languages
French (fr)
Korean (ko)
Other versions
WO2012018235A2 (en
Inventor
김광일
오상봉
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.)
KPX LIFE SCIENCE CO Ltd
Original Assignee
KPX LIFE 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
Application filed by KPX LIFE SCIENCE CO Ltd filed Critical KPX LIFE SCIENCE CO Ltd
Publication of WO2012018235A2 publication Critical patent/WO2012018235A2/en
Publication of WO2012018235A3 publication Critical patent/WO2012018235A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Saccharide Compounds (AREA)

Abstract

The present invention relates to a method for preparing decitabine with improved yield and purity, and more particularly, to a method for preparing decitabine with improved yield and purity that comprises a step (step 1) of enabling 1,3,5-triacetyl-2-deocyribose, and 5-azacytosine in which a silyl group is introduced, to react in a methylene chloride or EDC solvent in the presence of a TMSO triflate Lewis acid; a step (step 2) of obtaining an intermediate product by crystallizing the reaction product obtained in step 1 using ethyl acetate as a recrystallization solvent; and a step (step 3) of obtaining, from the crystallized intermediate product obtained in step 2, decitabine as an end product in which an acetyl group is deprotected. According to the present invention, the formation of isomers may be minimized by using a novel starting material and a method for synthesizing same, and the purity of a final product may be improved to 99.5% or higher by means og a novel precursor which is crystallized into the form of a free amine instead of a protected amine. Therefore, the method of the present invention may be effectively utilized in preparing decitabine with high purity and high yield.
PCT/KR2011/005724 2010-08-05 2011-08-04 Method for preparing decitabine with improved yield and purity Ceased WO2012018235A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020100075554A KR101241321B1 (en) 2010-08-05 2010-08-05 Improved preparation method of Decitabine
KR10-2010-0075554 2010-08-05

Publications (2)

Publication Number Publication Date
WO2012018235A2 WO2012018235A2 (en) 2012-02-09
WO2012018235A3 true WO2012018235A3 (en) 2012-05-03

Family

ID=45559932

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2011/005724 Ceased WO2012018235A2 (en) 2010-08-05 2011-08-04 Method for preparing decitabine with improved yield and purity

Country Status (2)

Country Link
KR (1) KR101241321B1 (en)
WO (1) WO2012018235A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103897008A (en) * 2012-12-28 2014-07-02 石药集团中奇制药技术（石家庄）有限公司 Method for preparing decitabine and intermediate thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20060008297A (en) * 2003-03-20 2006-01-26 마이크로 바이올로지카 퀴미카 이 파마슈티카 리미티드 Method for preparing 2'-deoxy-β-L-nucleoside
WO2006099132A1 (en) * 2005-03-11 2006-09-21 Supergen, Inc. Azacytosine analogs and derivatives
WO2010017547A1 (en) * 2008-08-08 2010-02-11 Scinopharm Taiwan Ldt. Process for making 5-azacytosine nucleosides and their derivatives
KR20100064387A (en) * 2007-10-10 2010-06-14 시락 아게 Method of producing 2'-deoxy-5-azacytidine (decitabine)

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20060008297A (en) * 2003-03-20 2006-01-26 마이크로 바이올로지카 퀴미카 이 파마슈티카 리미티드 Method for preparing 2'-deoxy-β-L-nucleoside
WO2006099132A1 (en) * 2005-03-11 2006-09-21 Supergen, Inc. Azacytosine analogs and derivatives
KR20100064387A (en) * 2007-10-10 2010-06-14 시락 아게 Method of producing 2'-deoxy-5-azacytidine (decitabine)
WO2010017547A1 (en) * 2008-08-08 2010-02-11 Scinopharm Taiwan Ldt. Process for making 5-azacytosine nucleosides and their derivatives

Also Published As

Publication number Publication date
WO2012018235A2 (en) 2012-02-09
KR20120013537A (en) 2012-02-15
KR101241321B1 (en) 2013-03-11

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