WO2002059128A3 - Process for preparing clopidogrel - Google Patents

Process for preparing clopidogrel Download PDF

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Publication number
WO2002059128A3
WO2002059128A3 PCT/IN2002/000012 IN0200012W WO02059128A3 WO 2002059128 A3 WO2002059128 A3 WO 2002059128A3 IN 0200012 W IN0200012 W IN 0200012W WO 02059128 A3 WO02059128 A3 WO 02059128A3
Authority
WO
WIPO (PCT)
Prior art keywords
optically active
compounds
racemic
formula
bromine
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/IN2002/000012
Other languages
French (fr)
Other versions
WO2002059128A2 (en
Inventor
Bipin Pandey
Vidya Bhushan Lohray
Braj Bhushan Lohray
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.)
Zydus Lifesciences Ltd
Original Assignee
Cadila Healthcare 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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26324902&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2002059128(A3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from IN84MU2001 external-priority patent/IN191030B/en
Priority to JP2002559430A priority Critical patent/JP5000841B2/en
Priority to EP02710298A priority patent/EP1353928B1/en
Priority to MXPA03006133A priority patent/MXPA03006133A/en
Priority to KR1020037009826A priority patent/KR100632748B1/en
Priority to DK02710298T priority patent/DK1353928T3/en
Priority to AU2002228325A priority patent/AU2002228325B2/en
Priority to DE60217062T priority patent/DE60217062T2/en
Priority to EA200300831A priority patent/EA006198B2/en
Application filed by Cadila Healthcare Ltd filed Critical Cadila Healthcare Ltd
Priority to CNB02803998XA priority patent/CN100338068C/en
Priority to BR0207064-2A priority patent/BR0207064A/en
Priority to CA2436323A priority patent/CA2436323C/en
Publication of WO2002059128A2 publication Critical patent/WO2002059128A2/en
Publication of WO2002059128A3 publication Critical patent/WO2002059128A3/en
Priority to NO20032898A priority patent/NO327807B1/en
Anticipated expiration legal-status Critical
Priority to CY20071100280T priority patent/CY1106346T1/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic 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
    • C07D495/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention discloses a process for the preparation of thieno[3,2-c]pyridine derivatives of general formula (I), in either racemic or optically active (+) or (-) forms and their salts, wherein X, the substituent on benzene ring represents either a hydrogen or halogen atom such as fluorine, chlorine, bromine or iodine. The present invention also describes a process for preparing the compounds of general formula (II), in either racemic or optically active (+) or (-) forms and their salts, where X, the substituent on benzene ring represents either a hydrogen or halogen atom such as fluorine, chlorine, bromine or iodine. The compounds represented by formulae (I) and (II) have one asymmetric carbon and hence, the optically active compounds of formula (I) or of formula (ii), may be obtained either by resolving the racemic intermediate/final product or using an optically active intermediate. The compounds of the invention are pharmacologically active and have significant anti-aggregating and anti-thrombotic properties.
PCT/IN2002/000012 2001-01-24 2002-01-21 Process for preparing clopidogrel Ceased WO2002059128A2 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
BR0207064-2A BR0207064A (en) 2001-01-24 2002-01-21 Process for the preparation of a compound
CA2436323A CA2436323C (en) 2001-01-24 2002-01-21 Process for preparing clopidogrel
CNB02803998XA CN100338068C (en) 2001-01-24 2002-01-21 Process for preparing clopidogrel
MXPA03006133A MXPA03006133A (en) 2001-01-24 2002-01-21 Process for preparing clopidogrel.
KR1020037009826A KR100632748B1 (en) 2001-01-24 2002-01-21 Method for preparing thieno [3,2-C] pyridine derivative
DK02710298T DK1353928T3 (en) 2001-01-24 2002-01-21 Process for the preparation of clopidogrel
AU2002228325A AU2002228325B2 (en) 2001-01-24 2002-01-21 Process for preparing clopidogrel
DE60217062T DE60217062T2 (en) 2001-01-24 2002-01-21 PROCESS FOR THE PREPARATION OF CLOPIDOGREL
EA200300831A EA006198B2 (en) 2001-01-24 2002-01-21 Process for preparing clopidogrel
JP2002559430A JP5000841B2 (en) 2001-01-24 2002-01-21 Method for producing clopidogrel
EP02710298A EP1353928B1 (en) 2001-01-24 2002-01-21 Process for preparing clopidogrel
NO20032898A NO327807B1 (en) 2001-01-24 2003-06-24 Process for the preparation of clopidogrel
CY20071100280T CY1106346T1 (en) 2001-01-24 2007-02-28 METHOD FOR THE PREPARATION OF THE CLOPIDOGREL COMPOUND

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN84MU2001 IN191030B (en) 2001-01-24 2001-01-24
IN84/MUM/2001 2001-01-24
US10/054,101 2001-10-22
US10/054,101 US6635763B2 (en) 2001-01-24 2001-10-22 Process to prepare clopidogrel

Publications (2)

Publication Number Publication Date
WO2002059128A2 WO2002059128A2 (en) 2002-08-01
WO2002059128A3 true WO2002059128A3 (en) 2002-12-19

Family

ID=26324902

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2002/000012 Ceased WO2002059128A2 (en) 2001-01-24 2002-01-21 Process for preparing clopidogrel

Country Status (17)

Country Link
EP (1) EP1353928B1 (en)
JP (1) JP5000841B2 (en)
KR (1) KR20060040758A (en)
CN (1) CN100338068C (en)
AT (1) ATE349451T1 (en)
AU (1) AU2002228325B2 (en)
BR (1) BR0207064A (en)
CA (1) CA2436323C (en)
CY (1) CY1106346T1 (en)
DE (1) DE60217062T2 (en)
DK (1) DK1353928T3 (en)
EA (1) EA006198B2 (en)
ES (1) ES2278010T3 (en)
MX (1) MXPA03006133A (en)
NO (1) NO327807B1 (en)
PL (1) PL365281A1 (en)
WO (1) WO2002059128A2 (en)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN191030B (en) * 2001-01-24 2003-09-13 Cadila Healthcare Ltd
GB0125708D0 (en) * 2001-10-26 2001-12-19 Generics Uk Ltd Novel compounds and processes
US6767913B2 (en) 2001-12-18 2004-07-27 Teva Pharmaceutical Industries Ltd. Crystal forms iii, iv, v, and novel amorphous form of clopidogrel hydrogensulfate, processes for their preparation, processes for the preparation of form i, compositions containing the new forms and methods of administering the new forms
US7074928B2 (en) 2002-01-11 2006-07-11 Teva Pharmaceutical Industries, Ltd. Polymorphs of clopidogrel hydrogensulfate
IL166593A0 (en) 2002-08-02 2006-01-15 Racemization and enantiomer separation of clopidogrel
US6800759B2 (en) 2002-08-02 2004-10-05 Teva Pharmaceutical Industries Ltd. Racemization and enantiomer separation of clopidogrel
WO2004074215A1 (en) * 2003-02-03 2004-09-02 Sunil Sadanand Nadkarni Process for preparation of clopidogrel, its salts and pharmaceutical compositions
CA2530449C (en) * 2003-07-02 2010-03-23 Egis Gyogyszergyar Rt. Process for the preparation of crystalline polymorph of a platelet aggregation inhibitor drug
KR20060026121A (en) 2003-07-02 2006-03-22 에지스 지오기스제르기아르 알티. Method for preparing an amorphous form of a platelet aggregation inhibitory drug
PT1680430E (en) 2003-11-03 2010-04-26 Cadila Healthcare Ltd Processes for preparing form i of (s)-(+)- clopidogrel bisulfate
CA2457459A1 (en) * 2004-02-11 2005-08-11 Brantford Chemicals Inc. Resolution of racemates of methyl alpha-5-(4,5,6,7-tetrahydro(3,2-c)thienopyridyl)-(2-chlorophenyl) acetate
KR100553398B1 (en) * 2004-03-12 2006-02-16 한미약품 주식회사 Process for preparing thieno [3,2-c] pyridine derivatives and intermediates used therein
CN1938319B (en) 2004-04-09 2010-05-12 韩美药品株式会社 Crystalline clopidogrel naphthalenesulfonate or hydrate thereof, preparation method thereof, and pharmaceutical composition containing same
CZ295920B6 (en) * 2004-10-18 2005-11-16 Zentiva, A. S Process for preparing clopidogrel
CN100406568C (en) * 2005-02-18 2008-07-30 淮北市辉克药业有限公司 Process of clopidogrel
CZ299213B6 (en) * 2005-03-08 2008-05-21 Zentiva, A. S Racemization process of methyl ester R(-)isomer of (2-chlorophenyl)-6,7 ûdihydro-thieno[3,2-c]pyridine-5(4H)-acetic acid
KR100678287B1 (en) * 2005-06-23 2007-02-02 한미약품 주식회사 Method for preparing clopidogrel and intermediates used therein
CN100463909C (en) * 2005-09-08 2009-02-25 浙江华海药业股份有限公司 A kind of synthetic method of thienotetrahydropyridine acetonitrile compound
CN100417653C (en) * 2005-09-08 2008-09-10 浙江华海药业股份有限公司 Preparation method of thienotetrahydropyridine acetic acid and salt thereof
WO2007028337A1 (en) * 2005-09-08 2007-03-15 Zhejiang Huahai Pharmaceutical Co., Ltd. Preparation of clopidogrel and its analogues methyl tetrahydrothienopyridine acetate compounds
CN100390180C (en) * 2005-12-15 2008-05-28 上海应用技术学院 Preparation method of clopidogrel and salt thereof
KR101235117B1 (en) 2005-12-26 2013-02-20 에스케이케미칼주식회사 Process for the preparation of S-(+)-clopidogrel by optical resolution
CN100396687C (en) * 2006-05-26 2008-06-25 浙江海翔药业股份有限公司 The preparation method of (+)-(S-)-clopidogrel bisulfate (I type)
WO2007144895A1 (en) * 2006-06-12 2007-12-21 Cadila Healthcare Limited Process for the preparation of (s) - (+)-clopidogrel
SI22383A (en) * 2006-09-22 2008-04-30 Krka, Tovarna Zdravil, D.D., Novo Mesto New procedure of synthesis of klopidogrel and new form of its pharmaceutically acceptable salts
PL380849A1 (en) * 2006-10-17 2008-04-28 Adamed Spółka Z Ograniczoną Odpowiedzialnością Crystalline form of racemic methyl 0 - (2-chlorophenyl) - 6, 7 - dihydrothiene [3, 2 - c] pyridil -5 (4H) - acetate, method for its manufacture and its application
WO2008146249A1 (en) * 2007-05-30 2008-12-04 Wockhardt Research Centre Processes for the preparation of clopidogrel
JP2011506950A (en) * 2007-12-14 2011-03-03 ジェネリクス・（ユーケー）・リミテッド HPLC method for the analysis of clopidogrel
EP2107061A1 (en) 2008-04-02 2009-10-07 Krka Tovarna Zdravil, D.D., Novo Mesto Process for the preparation of optically enriched clopidogrel
KR100990949B1 (en) * 2008-06-09 2010-10-29 엔자이텍 주식회사 Method for preparing clopidogrel and its derivatives
CN101787033B (en) * 2010-03-16 2011-08-31 天津市中央药业有限公司 Method for synthesizing related substance C of clopidogrel hydrogen sulfate
CN101812071A (en) * 2010-05-10 2010-08-25 杭州和素化学技术有限公司 Method for processing mother liquor obtained by splitting clopidogrel hydrogen sulfate intermediate
CN102241690B (en) 2010-05-13 2015-08-12 天津药物研究院 Thienopyridine ester derivative, the Preparation Method And The Use of one class nitrile group-containing
CN101845050A (en) * 2010-06-01 2010-09-29 上虞京新药业有限公司 Method for preparing clopidogrel
CN101962388B (en) * 2010-10-14 2012-12-19 天津药物研究院 Acetamide derivatives, preparation method and application thereof
CN101974016A (en) * 2010-10-14 2011-02-16 天津药物研究院 Amide compound and preparation method and applications thereof
CN104045652A (en) * 2014-07-09 2014-09-17 沈健芬 Preparation method of clopidogrel intermediate compound
CN110627808B (en) * 2018-06-21 2022-04-01 江苏同禾药业有限公司 Recovery treatment process of clopidogrel hydrogen sulfate splitting mother liquor

Citations (1)

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Publication number Priority date Publication date Assignee Title
US4529596A (en) * 1982-07-13 1985-07-16 Sanofi, S.A. Thieno [3,2-c] pyridine derivatives and their therapeutic application

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JPS60112762A (en) * 1983-11-21 1985-06-19 Fujisawa Pharmaceut Co Ltd Alpha-aryl-alpha-pyridyl fatty acid derivative and production thereof
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Patent Citations (1)

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Publication number Priority date Publication date Assignee Title
US4529596A (en) * 1982-07-13 1985-07-16 Sanofi, S.A. Thieno [3,2-c] pyridine derivatives and their therapeutic application

Non-Patent Citations (3)

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Title
ALAIN BURGOS, JOHN M. HERBERT AND IAIN SIMPSON: "ortho-Metalaton/Chlorination of Benzoic Acid Derivatives. Preparation of [benzene-U-13C]-rac-Clopidogrel ([benzene-U-13C]-rac-SR25990C)", J. LABELLED COMPD. RADIOPHARM., vol. 43, no. 9, 2000, pages 891 - 8, XP008008850 *
JERRY MARCH: "Advanced Organic Chemistry", 1992, WILEY & SONS, NEW YORK, XP002215119, 198280 *
NAJER ET AL.: "Nitriles, amides, thioamides et acides alpha-phenyle alpha-tertioaminoacötiques", BULL. SOC. CHIM. FR., 1958, pages 1189 - 92, XP002215118 *

Also Published As

Publication number Publication date
JP5000841B2 (en) 2012-08-15
NO20032898D0 (en) 2003-06-24
PL365281A1 (en) 2004-12-27
EP1353928B1 (en) 2006-12-27
DK1353928T3 (en) 2007-03-26
BR0207064A (en) 2004-03-30
EA200300831A1 (en) 2003-12-25
MXPA03006133A (en) 2004-05-04
CA2436323C (en) 2012-02-21
DE60217062T2 (en) 2007-06-21
ATE349451T1 (en) 2007-01-15
KR20060040758A (en) 2006-05-10
NO327807B1 (en) 2009-09-28
CN1487943A (en) 2004-04-07
CY1106346T1 (en) 2011-10-12
CN100338068C (en) 2007-09-19
EP1353928A2 (en) 2003-10-22
EA006198B1 (en) 2005-10-27
EA006198B2 (en) 2007-10-26
JP2004522744A (en) 2004-07-29
NO20032898L (en) 2003-09-03
AU2002228325B2 (en) 2006-05-04
WO2002059128A2 (en) 2002-08-01
DE60217062D1 (en) 2007-02-08
CA2436323A1 (en) 2002-08-01
ES2278010T3 (en) 2007-08-01

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