KR100511238B1 - 클로피도그렐 황산수소염의 다형체 형태 - Google Patents
클로피도그렐 황산수소염의 다형체 형태 Download PDFInfo
- Publication number
- KR100511238B1 KR100511238B1 KR10-2000-7014164A KR20007014164A KR100511238B1 KR 100511238 B1 KR100511238 B1 KR 100511238B1 KR 20007014164 A KR20007014164 A KR 20007014164A KR 100511238 B1 KR100511238 B1 KR 100511238B1
- Authority
- KR
- South Korea
- Prior art keywords
- hydrogen sulfate
- clopidogrel hydrogen
- clopidogrel
- polymorph
- mother liquor
- Prior art date
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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B7/00—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Metallurgy (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Compounds Of Unknown Constitution (AREA)
Abstract
Description
d(Å) | I/I 0 |
4.11 | 100.0 |
6.86 | 61.7 |
3.87 | 61.4 |
3.60 | 56.3 |
4.80 | 55.8 |
5.01 | 44.4 |
3.74 | 37.9 |
6.49 | 33.1 |
5.66 | 29.8 |
d(Å) | I/I 0 |
9.60 | 100.0 |
3.49 | 58.8 |
3.83 | 52.0 |
3.80 | 42.5 |
4.31 | 39.0 |
8.13 | 37.2 |
4.80 | 25.5 |
3.86 | 19.1 |
5.80 | 16.8 |
4.95 | 16.8 |
형태 1 | 형태 2 | |
융점 (℃) | 181.2 | 176.0 |
용융 엔탈피 (J/g) | 77 | 87 |
형태 1 | 형태 2 | ||
파장 (cm-1) | % 투과율 | 파장 (cm-1) | % 투과율 |
2987 | 42 | 2551 | 43 |
1753 | 14 | 1753 | 13.4 |
1222 | 16 | 1497 | 63.7 |
1175 | 12 | 1189 | 18 |
841 | 40 | 1029 | 33.2 |
공간 군 결정계 | 사방결정계 P2 1 2 1 2 1 |
단위 셀의 치수 | |
a | 10.321 (6) Å |
b | 20.118 (9) Å |
c | 9.187 (7) Å |
α | 90 도 |
β | 90 도 |
γ | 90 도 |
부피 | 1908 (2) Å3 |
Z | 4 |
밀도 (계산값) | 1.462 g/㎤ |
합쳐진 반사 | 2134 |
인자 R | 0.0473 |
Claims (12)
- 분말 X-선 회절분석도가 약 4.11; 6.86; 3.60; 5.01; 3.74; 6.49; 5.66 Å에서의 평면간 거리로 표현되는 특성 피크를 나타내는 클로피도그렐 황산수소염의 결정성 (+)-(S) 다형체(형태 2).
- 적외선 스펙트럼이 2551, 1497, 1189 및 1029 cm-1에서 특성 흡광도를 나타내고, 각각의 투과율 백분율이 약 43, 63.7, 18, 33.2인 클로피도그렐 황산수소염의 결정성 (+)-(S) 다형체(형태 2).
- 176 ± 3℃의 융점을 갖는 클로피도그렐 황산수소염의 결정성 (+)-(S) 다형체(형태 2).
- 8.77, 9.62, 10.55, 12.27, 12.89, 13.06, 13.63, 15.61, 16.37, 17.15, 17.69, 18.49, 19.30, 19.73, 20.11, 21.15, 21.62, 21.90, 22.96, 23.44, 23.75, 24.69, 25.02, 25.64, 25.94, 26.24, 26.54, 27.45, 27.64, 27.99, 29.07, 29.49, 30.73, 31.54, 31.72, 32.29, 32.96, 33.74, 34.22, 34.72, 35.65, 36.76, 37.19, 37.43, 37.87, 38.59 Å에서 특성 피크를 갖는 분말 X-선 회절분석도를 특징으로 하는 클로피도그렐 황산수소염의 결정성 다형체(형태 2).
- 삭제
- 제 1 항에 따른 분말 X-선 회절분석도 및 제 2 항에 따른 적외선 스펙트럼을 특징으로 하는 클로피도그렐 황산수소염의 결정성 다형체(형태 2).
- 3 내지 6 개월 후에 클로피도그렐 황산수소염 형태 2의 결정을 얻기 위해 (+)-(S)-클로피도그렐 황산수소염 형태 1을 결정화하여 얻은 수성 아세톤 모액을 염석시키는 것을 특징으로 하는, 제 1 항 내지 제 3 항 중 어느 한 항에 따른 (+)-(S)-클로피도그렐 황산수소염 형태 2를 제조하는 방법.
- 제 7 항에 있어서, (+)-(S)-클로피도그렐 황산수소염 형태 1을 결정화하여 얻은 수성 아세톤 모액이 0.3 내지 1%의 물을 함유하는 것을 특징으로 하는 방법.
- 제 7 항에 있어서, (+)-(S)-클로피도그렐 황산수소염 형태 1을 결정화하여 얻은 수성 아세톤 모액이 약 10% 이하의 클로피도그렐 황산수소염을 함유하는 것을 특징으로 하고, 이 양은 황산수소염으로의 전환 중 사용된 메틸(+)-(S)-α-(2-클로로페닐)-4,5,6,7-테트라히드로티에노[3,2-c]피리디닐-5-아세테이트 캄포르술폰산염의 양으로부터 계산된 것인 방법.
- 제 7 항에 있어서, (+)-(S)-클로피도그렐 황산수소염 형태 1을 결정화하여 얻은 수성 아세톤 모액이 40℃ 미만의 온도에서 3 내지 6 개월의 기간 후에 클로피도그렐 황산수소염 형태 2를 천천히 방출하는 것을 특징으로 하는 방법.
- (a) 메틸(+)-(S)-α-(2-클로로페닐)-4,5,6,7-테트라히드로티에노[3,2-c]피리디닐-5-아세테이트 캄포르술폰산염을 유기 용매에 녹이고,(b) 캄포르술폰산을 탄산칼륨의 수성 알칼리 용액으로 추출하고 물로 세척하고,(c) 유기상을 감압하에서 농축시키고 농축 잔류물을 아세톤에 넣고,94-96% 황산을 첨가하고 혼합물을 클로피도그렐 황산수소염 형태 2로 시딩하고, 생성물을 결정화하고, 혼합물을 냉각하고, 여과하고, 결정을 세척하고 이어서 감압하에 건조하여 클로피도그렐 황산수소염 형태 2를 얻는 것을 특징으로 하는 클로피도그렐 황산수소염 형태 2를 제조하는 방법.
- 활성 성분으로서 제 1 항에 따른 클로피도그렐 황산수소염의 형태 2 다형체를 1종 이상의 약학적 부형제와 함께 함유하는 혈전증의 예방 또는 치료용 약학 조성물.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9807464A FR2779726B1 (fr) | 1998-06-15 | 1998-06-15 | Forme polymorphe de l'hydrogenosulfate de clopidogrel |
FR98/07,464 | 1998-06-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20010052835A KR20010052835A (ko) | 2001-06-25 |
KR100511238B1 true KR100511238B1 (ko) | 2005-08-31 |
Family
ID=9527349
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR10-2000-7014164A KR100511238B1 (ko) | 1998-06-15 | 1999-06-10 | 클로피도그렐 황산수소염의 다형체 형태 |
Country Status (44)
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011052940A2 (ko) * | 2009-10-29 | 2011-05-05 | 동아제약주식회사 | 클로피도그랠 황산수소염 ⅰ형 제조방법 |
Families Citing this family (84)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2792836B3 (fr) | 1999-04-30 | 2001-07-27 | Sanofi Sa | Composition pharmaceutique sous forme unitaire contenant de l'aspirine et de l'hydrogenosulfate de clopidogrel |
US7304078B2 (en) | 2002-04-16 | 2007-12-04 | Schering Corporation | Thrombin receptor antagonists |
CA2363053C (en) * | 2001-11-09 | 2011-01-25 | Bernard Charles Sherman | Clopidogrel bisulfate tablet formulation |
IL162461A0 (en) * | 2001-12-18 | 2005-11-20 | Teva Pharma | Polymorphs of clopidogrel hydrogensulfate |
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 |
HUP0200438A3 (en) * | 2002-02-06 | 2003-10-28 | Egis Gyogyszergyar Nyilvanosan | Novel clopidogrel hydrochloride polymorphs, process for the preparation thereof, their use and pharmaceutical compositions containing them |
ATE390425T1 (de) * | 2002-05-31 | 2008-04-15 | Schering Corp | Xanthin-phosphodiesterase-v-hemmer polymorphe |
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 |
CZ297472B6 (cs) * | 2002-08-27 | 2006-12-13 | Zentiva, A.S. | Zpusob výroby clopidogrelu hydrogensulfátu krystalické formy I |
US20040067995A1 (en) * | 2002-10-02 | 2004-04-08 | Wong Pancras C. | Novel combination of a factor Xa inhibitor and clopidogrel |
ITMI20022228A1 (it) * | 2002-10-21 | 2004-04-22 | Dinamite Dipharma S P A | Sali di clopidogrel con acidi alchil-solforici. |
AU2003285841A1 (en) * | 2002-11-28 | 2004-06-18 | Anpharm Przedsiebiorstwo Farmaceutyczne S.A. | A process for the preparation of crystalline form 1 or clopidogrel hydrogen sulfate |
DE10307343B4 (de) * | 2003-02-21 | 2005-10-06 | Volkswagen Ag | On-Board-Diagnosevorrichtung und On-Board-Diagnoseverfahren für Kraftfahrzeuge |
AU2003216707A1 (en) * | 2003-03-10 | 2004-09-30 | Hetero Drugs Limited | Amorphous clopidogrel hydrogen sulfate |
EP1603920A1 (en) * | 2003-03-12 | 2005-12-14 | Cadila Healthcare Ltd. | Polymorph and amorphous form of (s)-(+)-clopidogrel bisulfate |
EP2113506A3 (en) * | 2003-04-25 | 2010-02-24 | Cadila Healthcare Limited | Salts of clopidogrel and process for preparation |
EA200600137A1 (ru) | 2003-07-02 | 2006-06-30 | Эгиш Дьёдьсердьяр Рт. | Способ получения аморфной формы ингибитора агрегации тромбоцитов |
US20070142637A1 (en) * | 2003-07-02 | 2007-06-21 | Egis Gyogyszergyar Rt. | Process for the preparation of crystalline polymorph of a platelet aggregation inhibitor drug |
JP2007516934A (ja) * | 2003-08-04 | 2007-06-28 | ウォックハート・リミテッド | (+)−(s)−クロピドグレル重硫酸塩形態−iの新規な製造方法 |
DE10337773A1 (de) * | 2003-08-13 | 2005-03-24 | Krka Tovarna Zdravil, D.D. | Kristallisation von festen Formen von Clopidogrel-Additionssalzen |
GB0321256D0 (en) * | 2003-09-11 | 2003-10-08 | Generics Uk Ltd | Novel crystalline compounds |
EP1680430B1 (en) | 2003-11-03 | 2010-01-20 | 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 |
RU2006133842A (ru) * | 2004-02-24 | 2008-03-27 | Зигфрид Дженерикс Интерэшнл Аг (Ch) | Фармакологически приемлемые соли клопидогрела |
EP1772455A3 (en) * | 2004-03-05 | 2007-06-27 | IPCA Laboratories Limited | Industrial process for preparation a polmorph of clopidogrel hydrogen sulphate |
BRPI0418726A (pt) * | 2004-04-09 | 2007-09-11 | Hanmi Pharm Ind Co Ltd | naftalenossulfonato de clopidogrel cristalino ou hidrato do mesmo, método para sua preparação e composição farmacêutica contendo o mesmo |
SI1740593T1 (sl) * | 2004-04-19 | 2016-08-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Postopek za pripravo polimorfne oblike I klopidogrel hidrogen sulfata |
AU2005236046A1 (en) * | 2004-04-20 | 2005-11-03 | Sanofi-Aventis | Clopidogrel salt and polymorphic forms thereof |
EA010831B1 (ru) * | 2004-04-20 | 2008-12-30 | Санофи-Авентис | ПОЛИМОРФНАЯ ФОРМА D ГИДРОБРОМИДА МЕТИЛ-(+)-(S)-α-(2-ХЛОРФЕНИЛ)-6,7-ДИГИДРОТИЕНО[3,2-C]ПИРИДИН-5(4H)-АЦЕТАТА |
US7829720B2 (en) * | 2004-05-04 | 2010-11-09 | Bristol-Myers Squibb Company | Process for preparing atazanavir bisulfate and novel forms |
EP1704152A2 (en) * | 2004-09-21 | 2006-09-27 | Teva Pharmaceutical Industries Ltd | Crystalline clopidogrel hydrobromide and processes for preparation thereof |
US7446200B2 (en) * | 2004-10-04 | 2008-11-04 | Usv, Ltd. | Rapid resolution process of clopidogrel base and a process for preparation of clopidogrel bisulfate polymorph-form I |
CA2567806C (en) * | 2005-02-15 | 2011-04-26 | Usv Limited | Rapid resolution process of clopidogrel base and a process for preparation of clopidogrel bisulfate polymorph - form i |
EP1693375A1 (en) * | 2005-02-21 | 2006-08-23 | KRKA, tovarna zdravil, d.d., Novo mesto | Process for preparing clopidrogel hydrogen sulfate of form I |
US20060223845A1 (en) * | 2005-02-24 | 2006-10-05 | Eran Turgeman | Clopidogrel base suitable for pharmaceutical formulation and preparation thereof |
US7772398B2 (en) * | 2005-03-11 | 2010-08-10 | Dr. Reddy's Laboratories, Inc. | Process for making crystalline form I of clopidogrel hydrogen sulphate |
JP2008540546A (ja) * | 2005-05-10 | 2008-11-20 | エラン ファーマ インターナショナル リミテッド | ナノ粒子クロピドグレル製剤 |
EA200800041A1 (ru) * | 2005-06-13 | 2008-04-28 | Элан Фарма Интернэшнл Лтд. | Составы с наночастицами клопидогреля, содержащие комбинацию клопидогреля и аспирина |
KR20070009851A (ko) * | 2005-07-14 | 2007-01-19 | 씨제이 주식회사 | 클로피도그렐 황산수소염 함유 약학 조성물 |
US7994322B2 (en) * | 2005-09-05 | 2011-08-09 | Cadila Healthcare Limited | Processes for the preparation of different forms of (S)-(+)-clopidogrel besylate |
CA2618187C (en) * | 2005-09-21 | 2011-06-21 | Chong Kun Dang Pharmaceutical Corp. | Novel resinate complex of s-clopidogrel and production method thereof |
WO2007091253A2 (en) * | 2006-02-06 | 2007-08-16 | C.T.S. Ltd. | Pharmaceutical compositions comprising clopidogrel and vitamins which reduce homocysteine levels |
US20070225320A1 (en) * | 2006-03-27 | 2007-09-27 | Eswaraiah Sajja | Process for preparing clopidogrel |
US20100145053A1 (en) * | 2006-04-05 | 2010-06-10 | Cadila Healthcare Limited | Modified release clopidogrel formulation |
KR20090013794A (ko) * | 2006-04-27 | 2009-02-05 | 인드-스위프트 래버러토리즈 리미티드 | 클로피도그렐 히드로겐 설페이트의 다형태의 제조방법 |
EP2044066A2 (en) * | 2006-06-06 | 2009-04-08 | Bristol-Myers Squibb Company | Crystalline forms of n-[5-[[[5-(1,1-dimethylethyl)-2-oxazolyl]methyl] thio]-2-thiazolyl]-4-piperidinecarboxamide |
EP1931682A2 (en) * | 2006-08-03 | 2008-06-18 | Teva Pharmaceutical Industries Ltd. | Process for preparing clopidogrel bisulphate |
DE602007012121D1 (de) * | 2006-09-04 | 2011-03-03 | Ranbaxy Lab Ltd | Verbessertes verfahren zur herstellung von clopidogrel und pharmazeutisch unbedenklichen salzen davon |
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 |
WO2008060934A2 (en) * | 2006-11-14 | 2008-05-22 | Acusphere, Inc. | Formulations of tetrahydropyridine antiplatelet agents for parenteral or oral administration |
KR20080055356A (ko) * | 2006-12-15 | 2008-06-19 | 에스케이케미칼주식회사 | 보관안정성이 우수한 클로피도그렐 함유 포접 복합체 |
EP2120879A2 (en) * | 2006-12-22 | 2009-11-25 | Schering Corporation | Disintegration promoters in solid dose wet granulation formulations |
EP2114957A4 (en) * | 2007-01-29 | 2011-06-08 | Ipca Lab Ltd | PROCESS FOR THE PREPARATION OF A CRYSTALLINE FORM 1 OF A CLOPIDOGREL HYDROGEN SULFATE |
EP1970054A3 (en) | 2007-03-14 | 2009-06-03 | Ranbaxy Laboratories Limited | Clopidogrel tablets |
PL382055A1 (pl) * | 2007-03-23 | 2008-09-29 | Koźluk Tomasz Nobilus Ent | Sposób wytwarzania formy krystalicznej 1 wodorosiarczanu klopidogrelu |
EP2152078B8 (en) | 2007-04-27 | 2021-03-17 | CyDex Pharmaceuticals, Inc. | Formulations containing clopidogrel and sulfoalkyl ether cyclodextrin and methods of use |
WO2009080469A1 (en) * | 2007-12-24 | 2009-07-02 | Sandoz Ag | Process for the preparation of clopidogrel bisulphate form i |
PT2095815E (pt) * | 2008-02-26 | 2012-02-03 | Lesvi Laboratorios Sl | Formulações farmacêuticas contendo clopidogrel |
EP2107061A1 (en) | 2008-04-02 | 2009-10-07 | Krka Tovarna Zdravil, D.D., Novo Mesto | Process for the preparation of optically enriched clopidogrel |
US20090264460A1 (en) * | 2008-04-21 | 2009-10-22 | Mamta Mishra | Clopidogrel pharmaceutical formulations |
JP2012523438A (ja) | 2009-04-10 | 2012-10-04 | タフツ メディカル センター インコーポレイテッド | メタロプロテイナーゼ−1(mmp−1)によるpar−1活性化 |
HUE047755T2 (hu) | 2009-05-13 | 2020-05-28 | Cydex Pharmaceuticals Inc | Prasugrelt és ciklodextrin-származékokat tartalmazó gyógyszerkészítmények, eljárás ezek elõállítására és alkalmazásra |
WO2011010318A1 (en) * | 2009-07-23 | 2011-01-27 | Praveen Laboratories Private Limited | Process for the preparation of clopidogrel polymorphous form 1 using seed chrystals |
WO2011042804A2 (en) | 2009-10-08 | 2011-04-14 | Jubliant Life Sciences Limited | An improved process for the preparation of clopidogrel hydrogen sulfate form i |
WO2011051976A2 (en) | 2009-10-30 | 2011-05-05 | Matrix Laboratories Ltd | An improved process for the preparation of clopidogrel bisulfate form i |
CN101766573B (zh) | 2010-02-05 | 2013-02-13 | 上海安必生制药技术有限公司 | 硫酸氢氯吡格雷固体制剂的制备工艺 |
WO2011125069A1 (en) | 2010-03-22 | 2011-10-13 | Rpg Life Sciences Limited | A process for preparation of crystalline form i of clopidogrel bisulfate |
EP2560644B1 (en) | 2010-04-19 | 2016-06-29 | Cadila Healthcare Limited | A pharmaceutical composition comprising antiplatelet agents and an erythropoiesis stimulating agent |
EP2675813A4 (en) | 2011-06-27 | 2014-04-30 | Ipca Lab Ltd | ANTI THROMBOSIS CONNECTIONS |
KR101324862B1 (ko) * | 2011-07-12 | 2013-11-01 | (주)에이에스텍 | 클로피도그렐 황산수소염의 구형 입자, 이를 포함하는 약학적 조성물 및 이의 제조방법 |
CN102367257B (zh) * | 2011-11-21 | 2014-05-07 | 天津红日药业股份有限公司 | 氯吡格雷盐酸盐的单晶晶型,它们的制备及应用 |
WO2014118802A1 (en) | 2013-01-31 | 2014-08-07 | Pharmazell Gmbh | An improved process for the preparation of clopidogrel bisulfate form-i |
JP5905165B2 (ja) | 2013-08-02 | 2016-04-20 | サノフイ | アセチルサリチル酸およびクロピドグレルを含む医薬錠剤 |
CN103524528A (zh) * | 2013-09-16 | 2014-01-22 | 吉林省博大伟业制药有限公司 | 一种改进的ⅱ型硫酸氢氯吡格雷结晶制备方法 |
HUP1400294A2 (hu) | 2014-06-13 | 2015-12-28 | Skillpharm Kft | Clopidogrel új alkalmazása |
KR101710922B1 (ko) | 2015-06-03 | 2017-02-28 | 경동제약 주식회사 | 클로피도그렐 황산염 결정형 i형의 제조방법 |
CN107698620A (zh) | 2015-06-23 | 2018-02-16 | 江苏天士力帝益药业有限公司 | 一种氘代噻吩并哌啶衍生物、制备方法及其应用 |
US20200129440A1 (en) | 2017-01-23 | 2020-04-30 | Dong Wha Pharm. Co., Ltd. | Complex formulation comprising hmg-coa reductase inhibitor and clopidogrel |
CN107163060B (zh) * | 2017-05-24 | 2021-03-02 | 常州制药厂有限公司 | 一种硫酸氢氯吡格雷晶型ii制备方法 |
CN107337683B (zh) * | 2017-08-16 | 2019-08-16 | 中荣凯特(北京)生物科技有限公司 | 一种噻吩并吡啶类衍生物硫酸氢盐的晶型ⅱ及其制备方法和应用 |
CN109438467B (zh) * | 2018-11-14 | 2021-03-26 | 四川青木制药有限公司 | 一种硫酸氢氯吡格雷ⅱ型球形结晶的制备方法 |
WO2023012479A1 (en) | 2021-08-03 | 2023-02-09 | Liqmeds Worldwide Limited | An oral pharmaceutical solution of clopidogrel |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4847265A (en) * | 1987-02-17 | 1989-07-11 | Sanofi | Dextro-rotatory enantiomer of methyl alpha-5 (4,5,6,7-tetrahydro (3,2-c) thieno pyridyl) (2-chlorophenyl)-acetate and the pharmaceutical compositions containing it |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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. |
-
1998
- 1998-06-15 FR FR9807464A patent/FR2779726B1/fr not_active Expired - Lifetime
-
1999
- 1999-06-10 CN CN99807458A patent/CN1128805C/zh not_active Expired - Lifetime
- 1999-06-10 US US09/623,333 patent/US6429210B1/en not_active Expired - Lifetime
- 1999-06-10 HU HU0104343A patent/HU225871B1/hu unknown
- 1999-06-10 AT AT99923711T patent/ATE222256T1/de active
- 1999-06-10 TR TR2000/03417T patent/TR200003417T2/xx unknown
- 1999-06-10 WO PCT/FR1999/001371 patent/WO1999065915A1/fr active IP Right Grant
- 1999-06-10 KR KR10-2000-7014164A patent/KR100511238B1/ko not_active IP Right Cessation
- 1999-06-10 OA OA1200000343A patent/OA11567A/en unknown
- 1999-06-10 AP APAP/P/2000/001979A patent/AP1344A/en active
- 1999-06-10 ID IDW20002434A patent/ID28264A/id unknown
- 1999-06-10 AU AU40483/99A patent/AU752170B2/en not_active Expired
- 1999-06-10 IL IL13979099A patent/IL139790A0/xx unknown
- 1999-06-10 ME MEP-2000-777A patent/ME00686B/me unknown
- 1999-06-10 RS YUP-777/00A patent/RS49870B/sr unknown
- 1999-06-10 EA EA200001187A patent/EA002386B1/ru not_active IP Right Cessation
- 1999-06-10 PL PL344998A patent/PL201894B1/pl unknown
- 1999-06-10 ES ES99923711T patent/ES2181439T3/es not_active Expired - Lifetime
- 1999-06-10 EE EEP200000745A patent/EE03972B1/xx unknown
- 1999-06-10 PT PT99923711T patent/PT1087976E/pt unknown
- 1999-06-10 EP EP99923711A patent/EP1087976B1/fr not_active Expired - Lifetime
- 1999-06-10 DE DE69902536T patent/DE69902536T2/de not_active Expired - Lifetime
- 1999-06-10 NZ NZ507914A patent/NZ507914A/xx not_active IP Right Cessation
- 1999-06-10 BR BR9911219-1A patent/BR9911219A/pt not_active Application Discontinuation
- 1999-06-10 CA CA002334870A patent/CA2334870C/en not_active Expired - Fee Related
- 1999-06-10 DK DK99923711T patent/DK1087976T3/da active
- 1999-06-10 CZ CZ20004637A patent/CZ299654B6/cs not_active IP Right Cessation
- 1999-06-10 JP JP2000554740A patent/JP3641584B2/ja not_active Expired - Lifetime
- 1999-06-10 SK SK1909-2000A patent/SK286340B6/sk not_active IP Right Cessation
- 1999-06-12 DZ DZ990117A patent/DZ2817A1/xx active
- 1999-06-14 EG EG71099A patent/EG24015A/xx active
- 1999-06-14 MY MYPI99002428A patent/MY129439A/en unknown
- 1999-06-15 CO CO99037210A patent/CO5040084A1/es unknown
- 1999-06-15 TW TW088110001A patent/TW562805B/zh not_active IP Right Cessation
- 1999-06-16 AR ARP990102869A patent/AR014854A1/es not_active Application Discontinuation
- 1999-07-04 SA SA99200321A patent/SA99200321B1/ar unknown
- 1999-09-06 UY UY25693A patent/UY25693A1/es not_active Application Discontinuation
- 1999-10-06 UA UA2000116344A patent/UA70323C2/uk unknown
-
2000
- 2000-11-07 ZA ZA200006386A patent/ZA200006386B/en unknown
- 2000-11-17 IS IS5716A patent/IS2469B/is unknown
- 2000-11-20 IL IL139790A patent/IL139790A/en unknown
- 2000-11-27 BG BG104987A patent/BG64508B1/bg unknown
- 2000-12-14 HR HR970350A patent/HRP20000863B1/xx not_active IP Right Cessation
- 2000-12-14 NO NO20006395A patent/NO327161B1/no not_active IP Right Cessation
-
2001
- 2001-06-21 HK HK01104337A patent/HK1033829A1/xx not_active IP Right Cessation
-
2002
- 2002-06-21 US US10/177,092 patent/US6504030B1/en not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4847265A (en) * | 1987-02-17 | 1989-07-11 | Sanofi | Dextro-rotatory enantiomer of methyl alpha-5 (4,5,6,7-tetrahydro (3,2-c) thieno pyridyl) (2-chlorophenyl)-acetate and the pharmaceutical compositions containing it |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011052940A2 (ko) * | 2009-10-29 | 2011-05-05 | 동아제약주식회사 | 클로피도그랠 황산수소염 ⅰ형 제조방법 |
WO2011052940A3 (ko) * | 2009-10-29 | 2011-10-20 | 동아제약주식회사 | 클로피도그랠 황산수소염 ⅰ형 제조방법 |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR100511238B1 (ko) | 클로피도그렐 황산수소염의 다형체 형태 | |
US5488150A (en) | Crystals of N-(trans-4-isopropylcyclohexycarbonyl)-D-phenylalanine and methods for preparing them | |
US5463116A (en) | Crystals of N- (trans-4-isopropylcyclohexlycarbonyl)-D-phenylalanine and methods for preparing them | |
CA2464961A1 (en) | Polymorphous forms of rosiglitazone maleate | |
KR20030042038A (ko) | 온단세트론 히드로클로라이드의 신규한 결정 형태 및용매화물 형태와 이들의 제조 방법 | |
KR19980064286A (ko) | 다형태를 갖는 독사조신 메실레이트의 새로운 형태(제 1형) | |
BRPI0602206B1 (pt) | forma polimórfica a de dexcetoprofeno trometamol e composições que a contém | |
KR100659927B1 (ko) | 다형태를갖는독사조신메실레이트의새로운형태(제iii형) | |
EP1693375A1 (en) | Process for preparing clopidrogel hydrogen sulfate of form I | |
KR19980064287A (ko) | 다형태를 갖는 독사조신 메실레이트의 새로운 형태(제 ii 형) | |
MXPA00012557A (en) | Polymorphic clopidogrel hydrogenesulphate form | |
JP2707012B2 (ja) | N−tert−ブチル−1−メチル−3,3−ジフェニルプロピルアミン塩酸塩の結晶多形およびその製造方法 | |
JPH05155822A (ja) | N−tert−ブチル−1−メチル−3,3−ジフェニルプロピルアミン塩酸塩の結晶多形およびその製造方法 | |
JP5442198B2 (ja) | 医薬化合物の結晶形 | |
JP2007516166A (ja) | 血小板凝集阻害剤の無晶形の製法 | |
PT761656E (pt) | Forma cristalina de tazofelona((+,-)-5-((3,5-bis(1,1-dimetiletil)-4-hidroxifenil)metil)-4-tiazolidinona) | |
JPH01290661A (ja) | 多形的に純粋なターフェナジンの製造 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
A302 | Request for accelerated examination | ||
E902 | Notification of reason for refusal | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
FPAY | Annual fee payment |
Payment date: 20120802 Year of fee payment: 8 |
|
FPAY | Annual fee payment |
Payment date: 20130801 Year of fee payment: 9 |
|
FPAY | Annual fee payment |
Payment date: 20150717 Year of fee payment: 11 |
|
FPAY | Annual fee payment |
Payment date: 20160720 Year of fee payment: 12 |
|
FPAY | Annual fee payment |
Payment date: 20170719 Year of fee payment: 13 |
|
FPAY | Annual fee payment |
Payment date: 20180730 Year of fee payment: 14 |
|
EXPY | Expiration of term |