HRP20160757T1 - Postupak za proizvodnju polimorfnog oblika i od klopidogrel-vodik-sulfata - Google Patents
Postupak za proizvodnju polimorfnog oblika i od klopidogrel-vodik-sulfata Download PDFInfo
- Publication number
- HRP20160757T1 HRP20160757T1 HRP20160757TT HRP20160757T HRP20160757T1 HR P20160757 T1 HRP20160757 T1 HR P20160757T1 HR P20160757T T HRP20160757T T HR P20160757TT HR P20160757 T HRP20160757 T HR P20160757T HR P20160757 T1 HRP20160757 T1 HR P20160757T1
- Authority
- HR
- Croatia
- Prior art keywords
- clopidogrel
- sulfuric acid
- methylene chloride
- temperature
- solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 11
- 229950010477 clopidogrel hydrogen sulphate Drugs 0.000 title claims 3
- FDEODCTUSIWGLK-UHFFFAOYSA-N hydrogen sulfate;hydron;methyl 2-(2-chlorophenyl)-2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)acetate Chemical compound OS(O)(=O)=O.C1CC=2SC=CC=2CN1C(C(=O)OC)C1=CC=CC=C1Cl FDEODCTUSIWGLK-UHFFFAOYSA-N 0.000 title claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 8
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical class C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 claims 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- 239000005552 B01AC04 - Clopidogrel Substances 0.000 claims 5
- 229960003009 clopidogrel Drugs 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- -1 alkyl acetate Chemical compound 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
Claims (11)
1. Postupak proizvodnje polimorfnog oblika I od klopidogrel-vodik-sulfata,
naznačen time, da se provodi sljedeće:
(a) opcijski se sol klopidogrela pretvara u bazu klopidogrela,
(b) otopina baze klopidogrela se dobiva u otapalu, pri čemu je otapalo smjesa etilacetata s metilenkloridom, koja sadrži do 10 masenih % metilenklorida,
(c) otopina baze klopidogrela reagira sa sumpornom kiselinom, pri čemu se temperatura dobivene smjese za vrijeme reakcijskog koraka (c) održava u rasponu od -20 do 5°C, i
(d) klopidogrel-vodik-sulfat se obnavlja u oblik I.
2. Postupak prema zahtjevu 1, naznačen time, da smjesa sadrži od jednog do pet masenih % metilenklorida.
3. Postupak prema bilo kojem od zahtjeva 1 do 2, naznačen time, da se sumporna kiselina upotrebljava u obliku otopine u organskom otapalu.
4. Postupak prema zahtjevu 3, naznačen time, da organsko otapalo je etilacetat.
5. Postupak prema zahtjevu 3 ili 4, naznačen time, da je otopina sumporne kiseline u organskom otapalu, pripravljena na temperaturi koja je manja od 0°C, a poželjno iznosi od -5 do -15°C.
6. Postupak prema bilo kojem od zahtjeva 1 do 5, naznačen time, da se upotrebljava najviše do 0,9 ekvivalenata sumporne kiseline u odnosu na bazu klopidogrela.
7. Postupak prema bilo kojem od zahtjeva 1 do 6, naznačen time, da se temperatura smjese koja se dobiva reakcijom u koraku (c), održava u rasponu od -15 do 0°C.
8. Postupak prema bilo kojem od zahtjeva 1 do 7, naznačen time, da se reakcijska smjesa koja je dobivena nakon dovršenog koraka (c), održava na temperaturi od -15 do 0°C uz miješanje, najmanje u vremenu od jednog sata, poželjno od 2 do 4 sata.
9. Postupak prema bilo kojem od zahtjeva 1 do 8, naznačen time, da se reakcijskoj smjesi koja je dobivena nakon dovršenog koraka (c), omogućava zagrijavanje na sobnu temperaturu uz miješanje, dok je brzina zagrijavanja od 0,5 do 6°C na sat.
10. Postupak prema bilo kojem od zahtjeva 1 do 9, naznačen time, da se korak (a) provodi pomoću neutralizacije soli klopidogrela s vodenom anorganskom bazom.
11. Postupak prema zahtjevu 10, naznačena time, da se sol klopidogrela otapa u otapalu, poželjno u metilenkloridu, kloroformu ili u alkilacetatu.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410009028 CN1690060A (zh) | 2004-04-19 | 2004-04-19 | 一种制备i型硫酸氯吡格雷的方法 |
| SI200400122A SI21749A (sl) | 2004-04-21 | 2004-04-21 | Postopek za pripravo polimorfne oblike I klopidogrel hidrogen sulfata |
| EP05734224.8A EP1740593B1 (en) | 2004-04-19 | 2005-04-19 | Processes for the preparation of clopidogrel hydrogen sulfate polymorphic form i |
| PCT/EP2005/004160 WO2005100364A1 (en) | 2004-04-19 | 2005-04-19 | Processes for the preparation of clopidogrel hydrogen sulfate polymorphic form i |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20160757T1 true HRP20160757T1 (hr) | 2016-08-12 |
Family
ID=34965241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20160757TT HRP20160757T1 (hr) | 2004-04-19 | 2016-06-28 | Postupak za proizvodnju polimorfnog oblika i od klopidogrel-vodik-sulfata |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7999106B2 (hr) |
| EP (1) | EP1740593B1 (hr) |
| EA (1) | EA010198B1 (hr) |
| ES (1) | ES2577303T3 (hr) |
| HR (1) | HRP20160757T1 (hr) |
| HU (1) | HUE029459T2 (hr) |
| NO (1) | NO339878B1 (hr) |
| PL (1) | PL1740593T3 (hr) |
| SI (1) | SI1740593T1 (hr) |
| WO (1) | WO2005100364A1 (hr) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7772398B2 (en) * | 2005-03-11 | 2010-08-10 | Dr. Reddy's Laboratories, Inc. | Process for making crystalline form I of clopidogrel hydrogen sulphate |
| US20090093635A1 (en) * | 2006-03-09 | 2009-04-09 | Sandor Garadnay | PROCESS FOR MAKING POLYMORPH FROM I OF (S) - (+) -METHYL-ALPHA- (2-CHLOROPHENYL) -6, 7-DYHIDRO-THIENO- [3, 2-c] PYRIDINE-5 (4H) -ACETATE HYDROGEN SULFATE |
| EP1931682A2 (en) * | 2006-08-03 | 2008-06-18 | Teva Pharmaceutical Industries Ltd. | Process for preparing clopidogrel bisulphate |
| WO2008032995A1 (en) * | 2006-09-15 | 2008-03-20 | Boryung Pharmaceutical Co., Ltd | Clopidogrel(+)-camphorsulfonate salt, method of preparing the same and a pharmaceutical composition comprising the same |
| 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 |
| WO2008068569A2 (en) * | 2006-12-01 | 2008-06-12 | Wockhardt Research Centre | Processes for the preparation of clopidogrel hydrochloride |
| 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 |
| PL382055A1 (pl) * | 2007-03-23 | 2008-09-29 | Koźluk Tomasz Nobilus Ent | Sposób wytwarzania formy krystalicznej 1 wodorosiarczanu klopidogrelu |
| EP2107061A1 (en) | 2008-04-02 | 2009-10-07 | Krka Tovarna Zdravil, D.D., Novo Mesto | Process for the preparation of optically enriched clopidogrel |
| 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 |
| WO2011125069A1 (en) * | 2010-03-22 | 2011-10-13 | Rpg Life Sciences Limited | A process for preparation of crystalline form i of clopidogrel bisulfate |
| CN103360406A (zh) * | 2012-03-26 | 2013-10-23 | 黑龙江福和华星制药集团股份有限公司 | 一种制备i型硫酸氢氯吡格雷的方法 |
| CN102924474B (zh) * | 2012-11-08 | 2015-04-01 | 浙江海翔药业股份有限公司 | 一种氯吡格雷硫酸氢盐晶型ⅰ的制备方法 |
| SG11201603130TA (en) | 2013-10-22 | 2016-05-30 | Chiesi Farma Spa | Process for the preparation of a pde4 inhibitor |
| US10238650B2 (en) | 2015-03-06 | 2019-03-26 | Beyondspring Pharmaceuticals, Inc. | Method of treating cancer associated with a RAS mutation |
| KR101710922B1 (ko) | 2015-06-03 | 2017-02-28 | 경동제약 주식회사 | 클로피도그렐 황산염 결정형 i형의 제조방법 |
| HUE059348T2 (hu) | 2015-06-17 | 2022-11-28 | Otsuka America Pharmaceutical Inc | Kristályos vegyületek |
| RU2753543C1 (ru) | 2016-02-08 | 2021-08-17 | Бейондспринг Фармасьютикалс, Инк. | Композиции, содержащие тукаресол или его аналоги |
| WO2018129381A1 (en) | 2017-01-06 | 2018-07-12 | Beyondspring Pharmaceuticals, Inc. | Tubulin binding compounds and therapeutic use thereof |
| JP2020514412A (ja) | 2017-02-01 | 2020-05-21 | ビヨンドスプリング ファーマシューティカルズ，インコーポレイテッド | 好中球減少症の低減方法 |
| AU2018221379B2 (en) | 2017-02-16 | 2021-11-04 | ViiV Healthcare UK (No.3) Limited | Crystalline forms of cabotegravir sodium |
| KR20200112881A (ko) | 2018-01-24 | 2020-10-05 | 비욘드스프링 파마수티컬스, 인코포레이티드. | 플리나불린의 투여를 통해 혈소판감소증을 감소시키는 조성물 및 방법 |
| TW202028208A (zh) | 2018-10-09 | 2020-08-01 | 瑞士商諾華公司 | N-(4-氟-3-(6-(3-甲基吡啶-2-基)-[1,2,4]三唑并[1,5-a]嘧啶-2-基)苯基)-2,4-二甲基㗁唑-5-甲醯胺固體形式 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| FR2779726B1 (fr) | 1998-06-15 | 2001-05-18 | Sanofi Sa | Forme polymorphe de l'hydrogenosulfate de clopidogrel |
| WO2002018357A1 (en) | 2000-08-29 | 2002-03-07 | Rpg Life Sciences Limited | A ONE-POT PROCESS FOR THE PREPARATION OF PHARMACEUTICALLY ACCEPTABLE ACID ADDITION SALTS OF 4, 5, 6, 7 - TETRAHYDROTHIENO (3,2-c) PYRIDINE DERIVATIVES HAVING ANTITHROMBOTIC ACTIVITY |
| GB0125708D0 (en) | 2001-10-26 | 2001-12-19 | Generics Uk Ltd | Novel compounds and processes |
| IL162461A0 (en) | 2001-12-18 | 2005-11-20 | Teva Pharma | Polymorphs of clopidogrel hydrogensulfate |
| CA2495437A1 (en) | 2002-08-27 | 2004-03-11 | Yamanouchi Pharmaceutical Co., Ltd. | Novel crystal |
| CZ297472B6 (cs) * | 2002-08-27 | 2006-12-13 | Zentiva, A.S. | Zpusob výroby clopidogrelu hydrogensulfátu krystalické formy I |
| 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 |
| EP1603920A1 (en) | 2003-03-12 | 2005-12-14 | Cadila Healthcare Ltd. | Polymorph and amorphous form of (s)-(+)-clopidogrel bisulfate |
| 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 |
| EP1772455A3 (en) * | 2004-03-05 | 2007-06-27 | IPCA Laboratories Limited | Industrial process for preparation a polmorph of clopidogrel hydrogen sulphate |
-
2005
- 2005-04-19 SI SI200532079A patent/SI1740593T1/sl unknown
- 2005-04-19 ES ES05734224.8T patent/ES2577303T3/es active Active
- 2005-04-19 EP EP05734224.8A patent/EP1740593B1/en active Active
- 2005-04-19 PL PL05734224.8T patent/PL1740593T3/pl unknown
- 2005-04-19 EA EA200601822A patent/EA010198B1/ru not_active IP Right Cessation
- 2005-04-19 WO PCT/EP2005/004160 patent/WO2005100364A1/en active Application Filing
- 2005-04-19 HU HUE05734224A patent/HUE029459T2/en unknown
- 2005-04-19 US US11/568,075 patent/US7999106B2/en not_active Expired - Fee Related
-
2006
- 2006-11-20 NO NO20065321A patent/NO339878B1/no not_active IP Right Cessation
-
2016
- 2016-06-28 HR HRP20160757TT patent/HRP20160757T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1740593A1 (en) | 2007-01-10 |
| NO20065321L (no) | 2007-01-09 |
| ES2577303T3 (es) | 2016-07-14 |
| US7999106B2 (en) | 2011-08-16 |
| WO2005100364A1 (en) | 2005-10-27 |
| EA010198B1 (ru) | 2008-06-30 |
| US20090234123A1 (en) | 2009-09-17 |
| EP1740593B1 (en) | 2016-04-06 |
| HUE029459T2 (en) | 2017-02-28 |
| PL1740593T3 (pl) | 2016-09-30 |
| SI1740593T1 (sl) | 2016-08-31 |
| NO339878B1 (no) | 2017-02-13 |
| EA200601822A1 (ru) | 2007-02-27 |
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