EA006198B2 - Способ получения клопидогрела - Google Patents

Способ получения клопидогрела

Info

Publication number
EA006198B2
EA006198B2 EA200300831A EA200300831A EA006198B2 EA 006198 B2 EA006198 B2 EA 006198B2 EA 200300831 A EA200300831 A EA 200300831A EA 200300831 A EA200300831 A EA 200300831A EA 006198 B2 EA006198 B2 EA 006198B2
Authority
EA
Eurasian Patent Office
Prior art keywords
optically active
compounds
racemic
formula
bromine
Prior art date
Application number
EA200300831A
Other languages
English (en)
Other versions
EA200300831A1 (ru
EA006198B1 (ru
Inventor
Бипин Пандей
Видья Бхушан Лохрей
Брадж Бхушан Лохрей
Original Assignee
Кадила Хелзкэр Лтд.
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=EA006198(B2) "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
Application filed by Кадила Хелзкэр Лтд. filed Critical Кадила Хелзкэр Лтд.
Publication of EA200300831A1 publication Critical patent/EA200300831A1/ru
Publication of EA006198B1 publication Critical patent/EA006198B1/ru
Publication of EA006198B2 publication Critical patent/EA006198B2/ru

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

Abstract

Настоящее изобретение описывает способ получения производных тиено[3,2-с]пиридина общей формулы (I), или в рацемической, или в оптически активной (+) или (-) формах, и их солей, где X, заместитель на бензольном кольце, обозначает атом водорода или галогена, такой как фтор, хлор, бром или иод. Настоящее изобретение также описывает способ получения соединений общей формулы (II), или в рацемической, или в оптически активной (+) или (-) формах, и их солей, где X, заместитель на бензольном кольце, обозначает атом водорода или галогена, такой как фтор, хлор, бром или иод. Соединения, представленные формулой (I) и (II), имеют один асимметрический атом углерода, и, следовательно, оптически активные соединения формулы (I) или (II) могут быть получены либо при разделении рацемического промежуточного/готового продукта, либо при использовании оптически активного промежуточного соединения. Соединения настоящего изобретения являются фармакологически активными и имеют существенные антиагрегирующие и антитромботические свойства.
EA200300831A 2001-01-24 2002-01-21 Способ получения клопидогрела EA006198B2 (ru)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN84MU2001 IN191030B (ru) 2001-01-24 2001-01-24
US10/054,101 US6635763B2 (en) 2001-01-24 2001-10-22 Process to prepare clopidogrel
PCT/IN2002/000012 WO2002059128A2 (en) 2001-01-24 2002-01-21 Process for preparing clopidogrel

Publications (3)

Publication Number Publication Date
EA200300831A1 EA200300831A1 (ru) 2003-12-25
EA006198B1 EA006198B1 (ru) 2005-10-27
EA006198B2 true EA006198B2 (ru) 2007-10-26

Family

ID=26324902

Family Applications (1)

Application Number Title Priority Date Filing Date
EA200300831A EA006198B2 (ru) 2001-01-24 2002-01-21 Способ получения клопидогрела

Country Status (17)

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

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IN191030B (ru) * 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
EP1606231A1 (en) * 2003-02-03 2005-12-21 Nadkarni, Sunil Sadanand Process for preparation of clopidogrel, its salts and pharmaceutical compositions
KR101155679B1 (ko) * 2003-07-02 2012-06-13 에지스 지오기스제르기아르 니일바노산 무코도 레스즈베니타르사사그 혈소판 응집 억제제 약물의 결정성 다형체를 제조하는 방법
US7396931B2 (en) 2003-07-02 2008-07-08 EGIS Gyógyszergyár Rt. Process for the preparation of amorphous form of a platelet aggregation inhibitor drug
WO2005063708A2 (en) 2003-11-03 2005-07-14 Cadila Healthcare Limited Processes for preparing different forms 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 (ko) * 2004-03-12 2006-02-16 한미약품 주식회사 티에노[3,2-ｃ]피리딘 유도체의 제조 방법 및 이에사용되는 중간체
CN1938319B (zh) 2004-04-09 2010-05-12 韩美药品株式会社 结晶氯吡格雷萘磺酸盐或其水合物、其制备方法及含其的药物组合物
CZ295920B6 (cs) * 2004-10-18 2005-11-16 Zentiva, A. S Způsob výroby klopidogrelu
CN100406568C (zh) * 2005-02-18 2008-07-30 淮北市辉克药业有限公司 氯吡格雷新生产工艺
CZ299213B6 (cs) * 2005-03-08 2008-05-21 Zentiva, A. S Zpusob racemizace R(-) izomeru methylesteru kyseliny (2-chlorfenyl)-6,7-dihydro-thieno[3,2-c]pyridin-5(4H)-octové
KR100678287B1 (ko) 2005-06-23 2007-02-02 한미약품 주식회사 클로피도그렐의 제조방법 및 이에 사용되는 중간체
CN100463909C (zh) * 2005-09-08 2009-02-25 浙江华海药业股份有限公司 一种噻吩并四氢吡啶乙腈化合物的合成方法
CN100417653C (zh) * 2005-09-08 2008-09-10 浙江华海药业股份有限公司 噻吩并四氢吡啶乙酸及其盐的制备方法
EP1942110A4 (en) * 2005-09-08 2010-08-04 Zhejiang Huahai Pharm Co Ltd PREPARATION OF CLOPIDOGREL AND ITS ANALOG METHYLTETRAHYDROTHIENOPYRIDINE ACETATE COMPOUNDS
CN100390180C (zh) * 2005-12-15 2008-05-28 上海应用技术学院 氯吡格雷及其盐的制备方法
KR101235117B1 (ko) 2005-12-26 2013-02-20 에스케이케미칼주식회사 광학분리에 의한 (ｓ)-(＋)-클로피도그렐의 제조방법
CN100396687C (zh) * 2006-05-26 2008-06-25 浙江海翔药业股份有限公司 (+)-(s-)-氯吡格雷硫酸氢盐(i型)的制备方法
WO2007144895A1 (en) * 2006-06-12 2007-12-21 Cadila Healthcare Limited Process for the preparation of (s) - (+)-clopidogrel
SI22383A (sl) * 2006-09-22 2008-04-30 Krka, Tovarna Zdravil, D.D., Novo Mesto Nov postopek sinteze klopidogrela in nove oblike njegovih farmacevtsko sprejemljivih soli
PL380849A1 (pl) * 2006-10-17 2008-04-28 Adamed Spółka Z Ograniczoną Odpowiedzialnością Krystaliczna postać racemicznego -(2-chlorofenylo)-6,7-dihydrotieno[3,2-c]pirydylo-5(4H)-octanu metylu, sposób jej wytwarzania i zastosowanie
EP2155756B1 (en) * 2007-05-30 2015-08-05 Wockhardt Limited Processes for the preparation of clopidogrel
WO2009077784A2 (en) * 2007-12-14 2009-06-25 Generics [Uk] Limited Hpcl method for analysing 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 (ko) * 2008-06-09 2010-10-29 엔자이텍 주식회사 클로피도그렐 및 그의 유도체의 제조방법
CN101787033B (zh) * 2010-03-16 2011-08-31 天津市中央药业有限公司 一种硫酸氢氯吡格雷有关物质c的合成方法
CN101812071A (zh) * 2010-05-10 2010-08-25 杭州和素化学技术有限公司 硫酸氢氯吡格雷中间体拆分后的母液处理方法
CN102241690B (zh) 2010-05-13 2015-08-12 天津药物研究院 一类含腈基的噻吩并吡啶酯类衍生物、其制备方法和用途
CN101845050A (zh) * 2010-06-01 2010-09-29 上虞京新药业有限公司 一种氯吡格雷的制备方法
CN101974016A (zh) * 2010-10-14 2011-02-16 天津药物研究院 酰胺类化合物及其制备方法和用途
CN101962388B (zh) * 2010-10-14 2012-12-19 天津药物研究院 乙酰胺衍生物及其制备方法和用途
CN104045652A (zh) * 2014-07-09 2014-09-17 沈健芬 一种氯吡格雷中间体的制备方法
CN110627808B (zh) * 2018-06-21 2022-04-01 江苏同禾药业有限公司 一种硫酸氢氯吡格雷拆分母液的回收处理工艺

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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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JPS5980664A (ja) * 1982-09-30 1984-05-10 Fujisawa Pharmaceut Co Ltd α−アリ−ル−α−ピリジル脂肪酸誘導体およびその製法
JPS60112762A (ja) * 1983-11-21 1985-06-19 Fujisawa Pharmaceut Co Ltd α−アリ−ル−α−ピリジル脂肪酸誘導体およびその製法
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.
FR2664276B1 (fr) * 1990-07-04 1992-10-23 Sanofi Sa Derive thienyl-2 glycidique, son procede de preparation et son utilisation comme intermediaire de synthese.

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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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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, Scheme 2 *
JERRY MARCH: "Advanced Organic Chemistry" 1992 , WILEY & SONS , NEW YORK XP002215119 198280 The HCN can be generated in situ from acetone cyanohydrin (see 6-49), avoiding the use of poisonous HCN. page 812 The addition of HCN ... This is an equilibrium reaction. page 964 Frequently it is the bisulfite addition product that is treated with CN- page 965 6-51 The addition of HCN to C=N and CN Bonds page 966 *
NAJER ET AL.: "Nitriles, amides, thioamides et acides alpha-phenyle alpha-tertioaminoacötiques" BULL. SOC. CHIM. FR., 1958, pages 1189-92, XP002215118, Nitrile alpha-phenyle, alpha-(tetrahydro-1,2,5,6)pyridinoacetiquw *

Also Published As

Publication number Publication date
NO20032898L (no) 2003-09-03
NO20032898D0 (no) 2003-06-24
WO2002059128A3 (en) 2002-12-19
BR0207064A (pt) 2004-03-30
JP5000841B2 (ja) 2012-08-15
NO327807B1 (no) 2009-09-28
CN1487943A (zh) 2004-04-07
CA2436323A1 (en) 2002-08-01
EA200300831A1 (ru) 2003-12-25
EA006198B1 (ru) 2005-10-27
JP2004522744A (ja) 2004-07-29
ES2278010T3 (es) 2007-08-01
AU2002228325B2 (en) 2006-05-04
EP1353928B1 (en) 2006-12-27
EP1353928A2 (en) 2003-10-22
MXPA03006133A (es) 2004-05-04
WO2002059128A2 (en) 2002-08-01
PL365281A1 (en) 2004-12-27
CY1106346T1 (el) 2011-10-12
DK1353928T3 (da) 2007-03-26
KR20060040758A (ko) 2006-05-10
DE60217062D1 (de) 2007-02-08
CA2436323C (en) 2012-02-21
CN100338068C (zh) 2007-09-19
DE60217062T2 (de) 2007-06-21
ATE349451T1 (de) 2007-01-15

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Legal Events

Date Code Title Description
DZ4A Eurasian patent assigned for amendment of claims
MM4A Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s)

Designated state(s): AM AZ BY KZ KG MD TJ TM RU