WO2009151256A3 - 클로피도크렐 및 그의 유도체의 제조방법 - Google Patents

클로피도크렐 및 그의 유도체의 제조방법 Download PDF

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Publication number
WO2009151256A3
WO2009151256A3 PCT/KR2009/003083 KR2009003083W WO2009151256A3 WO 2009151256 A3 WO2009151256 A3 WO 2009151256A3 KR 2009003083 W KR2009003083 W KR 2009003083W WO 2009151256 A3 WO2009151256 A3 WO 2009151256A3
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WO
WIPO (PCT)
Prior art keywords
derivatives
clopidogrel
present
active
enzyme
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PCT/KR2009/003083
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English (en)
French (fr)
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WO2009151256A2 (ko
Inventor
황순욱
김광수
김영진
정천오
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엔자이텍(주)
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Application filed by 엔자이텍(주) filed Critical 엔자이텍(주)
Priority to RU2010154156/04A priority Critical patent/RU2469039C2/ru
Priority to JP2011512392A priority patent/JP2011522535A/ja
Priority to CN2009801215031A priority patent/CN102056931A/zh
Priority to US12/996,733 priority patent/US20110087028A1/en
Priority to EP09762643A priority patent/EP2298777A4/en
Publication of WO2009151256A2 publication Critical patent/WO2009151256A2/ko
Publication of WO2009151256A3 publication Critical patent/WO2009151256A3/ko

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

본 발명은 클로피도그렐 및 그의 유도체를 제조하는 방법에 관한 것으로, 보다 상세하게는, 라세믹 2-클로로페닐글리신 알킬 에스테르로부터 효소를 이용한 가수분해 반응을 통해 광학 활성체인 (S)-2-클로로페닐글리신 알킬 에스테르를 제조하고, 이를 중간체로 사용하여 혈소판 응집 억제 활성을 가지는 (S)-클로피도그렐 및 그의 유도체를 제조하는 방법에 관한 것이다. 본 발명에 따르면, 본 발명에 따른 클로피도그렐 및 그의 유도체 제조방법은 제조공정이 단순하고, 광할 분할제의 사용 없이 소량의 효소만을 사용함에 따라 생산비용을 절감할 수 있으며, 고광학 순도로 얻어진 (S)-2-클로로페닐글리신 알킬 에스테르를 중간체로 사용함으로써 고광학 순도를 가지는 클레피도그렐 및 그의 유도체의 대량생산에 적합할 뿐만 아니라, 제조공정에서 독성이 강할 물질을 사용하지 않아 환경보호에도 기여할 수 있다.
PCT/KR2009/003083 2008-06-09 2009-06-09 클로피도크렐 및 그의 유도체의 제조방법 WO2009151256A2 (ko)

Priority Applications (5)

Application Number Priority Date Filing Date Title
RU2010154156/04A RU2469039C2 (ru) 2008-06-09 2009-06-09 Способ получения клопидогреля и его производных
JP2011512392A JP2011522535A (ja) 2008-06-09 2009-06-09 クロピドグレル及びその誘導体の製造方法
CN2009801215031A CN102056931A (zh) 2008-06-09 2009-06-09 氯吡格雷及其衍生物的制备方法
US12/996,733 US20110087028A1 (en) 2008-06-09 2009-06-09 Method for preparing clopidogrel and its derivatives
EP09762643A EP2298777A4 (en) 2008-06-09 2009-06-09 PROCESS FOR THE PREPARATION OF CLOPIDOGREL AND ITS DERIVATIVES

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020080053815A KR100990949B1 (ko) 2008-06-09 2008-06-09 클로피도그렐 및 그의 유도체의 제조방법
KR10-2008-0053815 2008-06-09

Publications (2)

Publication Number Publication Date
WO2009151256A2 WO2009151256A2 (ko) 2009-12-17
WO2009151256A3 true WO2009151256A3 (ko) 2010-03-18

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2009/003083 WO2009151256A2 (ko) 2008-06-09 2009-06-09 클로피도크렐 및 그의 유도체의 제조방법

Country Status (7)

Country Link
US (1) US20110087028A1 (ko)
EP (1) EP2298777A4 (ko)
JP (1) JP2011522535A (ko)
KR (1) KR100990949B1 (ko)
CN (1) CN102056931A (ko)
RU (1) RU2469039C2 (ko)
WO (1) WO2009151256A2 (ko)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6495691B1 (en) * 2001-07-06 2002-12-17 Brantford Chemicals Inc. Process for the preparation of tetrahydrothieno[3,2-c]pyridine derivatives
US20040176637A1 (en) * 2003-03-03 2004-09-09 Robert C. C. Wu Process for preparation of 2-chlorophenylglycine derivatives and enantiomerically separation
US20070225320A1 (en) * 2006-03-27 2007-09-27 Eswaraiah Sajja Process for preparing clopidogrel

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2530247B1 (fr) * 1982-07-13 1986-05-16 Sanofi Sa Nouveaux derives de la thieno (3, 2-c) pyridine, leur procede de preparation et leur application therapeutique
FR2623810B2 (fr) 1987-02-17 1992-01-24 Sanofi Sa Sels de l'alpha-(tetrahydro-4,5,6,7 thieno(3,2-c) pyridyl-5) (chloro-2 phenyl) -acetate de methyle dextrogyre et compositions pharmaceutiques en contenant
FR2652575B1 (fr) * 1989-09-29 1992-01-24 Sanofi Sa Procede de preparation d'acides alpha-bromo phenylacetiques.
US5189170A (en) 1989-09-29 1993-02-23 Sanofi Process for the preparation of phenylacetic derivatives of thieno-pyridines
FR2664596B1 (fr) * 1990-07-10 1994-06-10 Sanofi Sa Procede de preparation d'un derive n-phenylacetique de tetrahydrothieno [3,2-c] pyridine et son intermediaire de synthese.
FR2760456B1 (fr) 1997-03-05 2000-05-12 Sanofi Sa Procede de preparation de derives de 2-thienyl-ethylamine
HU222283B1 (hu) 1997-05-13 2003-05-28 Sanofi-Synthelabo Eljárás tieno[3,2-c]piridin-származékok előállítására
FR2769313B1 (fr) 1997-10-06 2000-04-21 Sanofi Sa Derives d'esters hydroxyacetiques, leur procede de preparation et leur utilisation comme intermediaires de synthese
CN100338068C (zh) * 2001-01-24 2007-09-19 卡地拉健康护理有限公司 制备氯吡格雷的方法
EP1606231A1 (en) 2003-02-03 2005-12-21 Nadkarni, Sunil Sadanand Process for preparation of clopidogrel, its salts and pharmaceutical compositions
US6858734B2 (en) * 2003-04-23 2005-02-22 Rhodia Pharma Solutions Inc. Preparation of (S)-Clopidogrel and related compounds
KR100553398B1 (ko) * 2004-03-12 2006-02-16 한미약품 주식회사 티에노[3,2-c]피리딘 유도체의 제조 방법 및 이에사용되는 중간체
KR100681512B1 (ko) 2005-03-08 2007-02-09 주식회사 한서켐 클로피도그렐의 신규한 제조 중간체 및 이를 이용한 클로피도그렐의 제조방법
KR100678287B1 (ko) 2005-06-23 2007-02-02 한미약품 주식회사 클로피도그렐의 제조방법 및 이에 사용되는 중간체
KR101235117B1 (ko) 2005-12-26 2013-02-20 에스케이케미칼주식회사 광학분리에 의한 (s)-(+)-클로피도그렐의 제조방법
CN101121720B (zh) * 2007-09-14 2010-05-19 南开大学 硫酸氢氯吡格雷的制备方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6495691B1 (en) * 2001-07-06 2002-12-17 Brantford Chemicals Inc. Process for the preparation of tetrahydrothieno[3,2-c]pyridine derivatives
US20040176637A1 (en) * 2003-03-03 2004-09-09 Robert C. C. Wu Process for preparation of 2-chlorophenylglycine derivatives and enantiomerically separation
US20070225320A1 (en) * 2006-03-27 2007-09-27 Eswaraiah Sajja Process for preparing clopidogrel

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CLINTON A. KRUEGER ET AL.: "Ti-catalyzed enantioselective addition of cyanide to imines. A practical synthesis of optically pure a-amino acids", JOURNAL OF AMERICAN CHEMICAL SOCIETY, vol. 121, 1999, pages 4284 - 4285, XP002131541 *

Also Published As

Publication number Publication date
KR20090127714A (ko) 2009-12-14
RU2010154156A (ru) 2012-07-20
EP2298777A4 (en) 2012-03-14
CN102056931A (zh) 2011-05-11
JP2011522535A (ja) 2011-08-04
RU2469039C2 (ru) 2012-12-10
EP2298777A2 (en) 2011-03-23
US20110087028A1 (en) 2011-04-14
KR100990949B1 (ko) 2010-10-29
WO2009151256A2 (ko) 2009-12-17

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