WO2007070804A3 - Process for preparing gemcitabine and associated intermediates - Google Patents

Process for preparing gemcitabine and associated intermediates Download PDF

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Publication number
WO2007070804A3
WO2007070804A3 PCT/US2006/061940 US2006061940W WO2007070804A3 WO 2007070804 A3 WO2007070804 A3 WO 2007070804A3 US 2006061940 W US2006061940 W US 2006061940W WO 2007070804 A3 WO2007070804 A3 WO 2007070804A3
Authority
WO
WIPO (PCT)
Prior art keywords
gemcitabine
intermediates
dimethyldioxolan
erythro
difluoro
Prior art date
Application number
PCT/US2006/061940
Other languages
French (fr)
Other versions
WO2007070804A2 (en
Inventor
Vladimir Naddaka
Eyal Klopfer
Shady Saeed
Dionne Montvilisky
Oded Arad
Joseph Kaspi
Original Assignee
Chemagis Ltd
Perrigo Company
Vladimir Naddaka
Eyal Klopfer
Shady Saeed
Dionne Montvilisky
Oded Arad
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
Application filed by Chemagis Ltd, Perrigo Company, Vladimir Naddaka, Eyal Klopfer, Shady Saeed, Dionne Montvilisky, Oded Arad, Joseph Kaspi filed Critical Chemagis Ltd
Publication of WO2007070804A2 publication Critical patent/WO2007070804A2/en
Publication of WO2007070804A3 publication Critical patent/WO2007070804A3/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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)

Abstract

Provided is a process for preparing gemcitabine and intermediates useful in the production of gemcitabine. Exemplary intermediates include mixtures of D-erythro and D-threo diastereomers of ethyl 3-(N-carbamoyloxy)-2,2-difluoro-3-(2,2-dimethyldioxolan-4-yl)propionates, from which a preferred isomer can be separated, e.g., by selective crystallization, in accordance with the invention. Also provided are novel alkyl (D-erythro)-3-hydroxy-2,2-difluoro-3-(2,2-dimethyldioxolan-4-yl)propionate intermediates, and novel ribo lactones, which can be used for producing gemcitabine.
PCT/US2006/061940 2005-12-13 2006-12-12 Process for preparing gemcitabine and associated intermediates WO2007070804A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US74968905P 2005-12-13 2005-12-13
US60/749,689 2005-12-13

Publications (2)

Publication Number Publication Date
WO2007070804A2 WO2007070804A2 (en) 2007-06-21
WO2007070804A3 true WO2007070804A3 (en) 2008-01-03

Family

ID=38163614

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/061940 WO2007070804A2 (en) 2005-12-13 2006-12-12 Process for preparing gemcitabine and associated intermediates

Country Status (3)

Country Link
KR (1) KR20080094890A (en)
CN (1) CN101356165A (en)
WO (1) WO2007070804A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109651459B (en) * 2019-01-24 2020-09-08 江苏八巨药业有限公司 Preparation method of gemcitabine intermediate methanesulfonyl ester
CN111393546B (en) * 2020-03-31 2021-08-03 浙江康特生物科技有限公司 Preparation of chelate resin and application of chelate resin in removing cobalt ions in kit purified water

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5521294A (en) * 1995-01-18 1996-05-28 Eli Lilly And Company 2,2-difluoro-3-carbamoyl ribose sulfonate compounds and process for the preparation of beta nucleosides
US5945547A (en) * 1987-08-28 1999-08-31 Eli Lilly And Company Imtermediate in process to make 2', 2'-difluoronucleosides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5945547A (en) * 1987-08-28 1999-08-31 Eli Lilly And Company Imtermediate in process to make 2', 2'-difluoronucleosides
US5521294A (en) * 1995-01-18 1996-05-28 Eli Lilly And Company 2,2-difluoro-3-carbamoyl ribose sulfonate compounds and process for the preparation of beta nucleosides

Also Published As

Publication number Publication date
KR20080094890A (en) 2008-10-27
CN101356165A (en) 2009-01-28
WO2007070804A2 (en) 2007-06-21

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