AR069319A1 - Metodo para preparar capecitabina y compuesto intermediario de trialquil carbonato. - Google Patents

Metodo para preparar capecitabina y compuesto intermediario de trialquil carbonato.

Info

Publication number
AR069319A1
AR069319A1 ARP080104968A ARP080104968A AR069319A1 AR 069319 A1 AR069319 A1 AR 069319A1 AR P080104968 A ARP080104968 A AR P080104968A AR P080104968 A ARP080104968 A AR P080104968A AR 069319 A1 AR069319 A1 AR 069319A1
Authority
AR
Argentina
Prior art keywords
formula
compound
carbonate
preparing
trialquil
Prior art date
Application number
ARP080104968A
Other languages
English (en)
Inventor
Cheol-Hyun Park
Yong-Hoon An
Jin Hee Kim
Yoon Ju Lee
Jaeheon Lee
Yang Weon Ki
Young-Kil Chang
Gwan Sun Lee
Gha-Seung Park
Original Assignee
Hanmi Pharmaceutical 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 Hanmi Pharmaceutical Co Ltd filed Critical Hanmi Pharmaceutical Co Ltd
Publication of AR069319A1 publication Critical patent/AR069319A1/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • 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
    • 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

Landscapes

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

Abstract

Reivindicacion 1: Un método para preparar capecitabina de formula 1, caracterizado por los pasos de: (1) hidrolizar un compuesto metilacetonida de formula 2 para obtener un compuesto triol de formula 3; (2) hacer reaccionar el compuesto de formula 3 con un haloalquil formato de formula 4 en presencia de una mezcla de piridina y trietilamina para obtener un compuesto trialquil carbonato rico en beta-anomero de formula 5; (3) realizar una glicosilacion del compuesto de formula 5 usando 5-fluorocitosina en presencia de un ácido para obtener un compuesto dialcoxicarbonil citidina de formula 6; (4) realizar carbamoilacion del compuesto de formula 6 usando n-pentil cloroformato para obtener un compuesto carbamoilcitidina de formula 7; y (5) desproteger los grupos protectores hidroxi carbonato del compuesto de formula 7: en donde, X es cloro, bromo o iodo; y R es metilo o etilo. Reivindicacion 7: Un método para preparar un compuesto trialquil carbonato de formula caracterizado porque comprende los pasos de: (1) hidrolizar un compuesto metilacetonida de formula 2 para obtener un compuesto triol de formula 3; y (2) permitir que el compuesto de formula 3 reaccione con un haloalquil formato de formula 4 en presencia de una mezcla de piridina y trietilamina para obtener un trialquil carbonato rico en beta-anomero de formula 5: en donde X y R tienen el mismo significado que el definido en la reivindicacion 1.
ARP080104968A 2007-11-19 2008-11-14 Metodo para preparar capecitabina y compuesto intermediario de trialquil carbonato. AR069319A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1020070118062A KR101013312B1 (ko) 2007-11-19 2007-11-19 카페시타빈의 제조방법 및 이에 사용되는 β-아노머가강화된 트리알킬카보네이트 화합물의 제조방법

Publications (1)

Publication Number Publication Date
AR069319A1 true AR069319A1 (es) 2010-01-13

Family

ID=40667680

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP080104968A AR069319A1 (es) 2007-11-19 2008-11-14 Metodo para preparar capecitabina y compuesto intermediario de trialquil carbonato.

Country Status (18)

Country Link
US (1) US8097706B2 (es)
EP (1) EP2220090A4 (es)
JP (1) JP2011503228A (es)
KR (1) KR101013312B1 (es)
CN (1) CN101861320A (es)
AR (1) AR069319A1 (es)
AU (1) AU2008327061B2 (es)
BR (1) BRPI0820494A8 (es)
CA (1) CA2704815C (es)
CL (1) CL2008003386A1 (es)
IL (1) IL205832A0 (es)
MX (1) MX2010005015A (es)
NZ (1) NZ585129A (es)
PE (1) PE20091358A1 (es)
RU (1) RU2439064C1 (es)
TW (1) TWI356061B (es)
WO (1) WO2009066892A1 (es)
ZA (1) ZA201003216B (es)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110021769A1 (en) * 2009-07-23 2011-01-27 Scinopharm Taiwan Ltd. Process for Producing Fluorocytidine Derivatives
CN102516338B (zh) * 2011-12-09 2014-04-02 海南锦瑞制药股份有限公司 一种卡培他滨化合物、其药物组合物及其制备方法
CN103374052B (zh) * 2012-04-19 2016-04-20 齐鲁制药有限公司 卡培他滨晶型及其制备方法
US10435429B2 (en) 2017-10-03 2019-10-08 Nucorion Pharmaceuticals, Inc. 5-fluorouridine monophosphate cyclic triester compounds
WO2019143860A1 (en) * 2018-01-19 2019-07-25 Nucorion Pharmaceuticals, Inc. 5-fluorouracil compounds
US11427550B2 (en) 2018-01-19 2022-08-30 Nucorion Pharmaceuticals, Inc. 5-fluorouracil compounds
CN115605492A (zh) 2020-04-21 2023-01-13 配体制药股份有限公司（Us） 核苷酸前药化合物

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1135258A (en) 1979-06-15 1982-11-09 Richard D'souza Process for the preparation of 5'deoxy-5-fluorouridine
US5272949A (en) * 1992-09-23 1993-12-28 Buckeye Bluegrass Farms, Inc. Device for cutting sod grown over plastic sheeting
TW254946B (es) 1992-12-18 1995-08-21 Hoffmann La Roche
AU671491B2 (en) * 1992-12-18 1996-08-29 F. Hoffmann-La Roche Ag N-oxycarbonyl substituted 5'-deoxy-5-fluorcytidines
US5476932A (en) * 1994-08-26 1995-12-19 Hoffmann-La Roche Inc. Process for producing N4-acyl-5'-deoxy-5-fluorocytidine derivatives
KR100908363B1 (ko) * 2007-02-28 2009-07-20 한미약품 주식회사 트라이-Ｏ-아세틸-5-데옥시-β-Ｄ-라이보퓨라노즈의입체선택적 제조방법 및 이의 분리방법

Also Published As

Publication number Publication date
US20100249395A1 (en) 2010-09-30
US8097706B2 (en) 2012-01-17
EP2220090A1 (en) 2010-08-25
CN101861320A (zh) 2010-10-13
AU2008327061B2 (en) 2011-03-24
CA2704815A1 (en) 2009-05-28
CL2008003386A1 (es) 2009-04-13
TWI356061B (en) 2012-01-11
EP2220090A4 (en) 2011-03-16
TW200927754A (en) 2009-07-01
RU2439064C1 (ru) 2012-01-10
PE20091358A1 (es) 2009-09-23
WO2009066892A1 (en) 2009-05-28
BRPI0820494A8 (pt) 2015-11-03
CA2704815C (en) 2012-03-13
BRPI0820494A2 (pt) 2015-06-16
KR101013312B1 (ko) 2011-02-09
NZ585129A (en) 2011-11-25
ZA201003216B (en) 2011-07-27
KR20090051595A (ko) 2009-05-22
JP2011503228A (ja) 2011-01-27
IL205832A0 (en) 2010-11-30
MX2010005015A (es) 2010-05-27
AU2008327061A1 (en) 2009-05-28

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