WO2003066637A1 - Polymorphs of clopidogrel hydrochloride and their use as antithrombic compounds - Google Patents
Polymorphs of clopidogrel hydrochloride and their use as antithrombic compounds Download PDFInfo
- Publication number
- WO2003066637A1 WO2003066637A1 PCT/HU2002/000157 HU0200157W WO03066637A1 WO 2003066637 A1 WO2003066637 A1 WO 2003066637A1 HU 0200157 W HU0200157 W HU 0200157W WO 03066637 A1 WO03066637 A1 WO 03066637A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dihydro
- methyl
- pyridine
- thieno
- chlorophenyl
- Prior art date
Links
- XIHVAFJSGWDBGA-RSAXXLAASA-N methyl (2s)-2-(2-chlorophenyl)-2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)acetate;hydrochloride Chemical compound Cl.C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl XIHVAFJSGWDBGA-RSAXXLAASA-N 0.000 title claims description 33
- 150000001875 compounds Chemical class 0.000 title description 8
- 229950010560 clopidogrel hydrochloride Drugs 0.000 title description 6
- 230000001407 anti-thrombic effect Effects 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 40
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- 230000002785 anti-thrombosis Effects 0.000 claims abstract description 10
- 210000001772 blood platelet Anatomy 0.000 claims abstract description 10
- 150000004677 hydrates Chemical class 0.000 claims abstract description 10
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 10
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims abstract description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 63
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 40
- 239000004480 active ingredient Substances 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 239000000010 aprotic solvent Substances 0.000 claims description 17
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 17
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- 239000003880 polar aprotic solvent Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 7
- 239000012752 auxiliary agent Substances 0.000 claims description 7
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 239000003146 anticoagulant agent Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 239000002798 polar solvent Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 14
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000005552 B01AC04 - Clopidogrel Substances 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic alcohols Chemical class 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 229960003009 clopidogrel Drugs 0.000 description 2
- 229950010477 clopidogrel hydrogen sulphate Drugs 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 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 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000008122 artificial sweetener Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- FYGDTMLNYKFZSV-MRCIVHHJSA-N dextrin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1O[C@@H]1[C@@H](CO)OC(O[C@@H]2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-MRCIVHHJSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (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)
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2004-7012110A KR20040079987A (ko) | 2002-02-06 | 2002-12-20 | 클로피도그렐 히드로클로라이드의 다형체 및 이의 항혈전화합물로서의 용도 |
SK336-2004A SK3362004A3 (sk) | 2002-02-06 | 2002-12-20 | Polymorfy hydrochloridu clopidogrelu a ich použitie ako antitrombotických zlúčenín |
US10/504,042 US20050113406A1 (en) | 2002-02-06 | 2002-12-20 | Polymorphs of clopidogrel hydrochloride and their use as antithrombic compounds |
AU2002353251A AU2002353251A1 (en) | 2002-02-06 | 2002-12-20 | Polymorphs of clopidogrel hydrochloride and their use as antithrombic compounds |
EP02788271A EP1474427A1 (en) | 2002-02-06 | 2002-12-20 | Polymorphs of clopidogrel hydrochloride and their use as antithrombic compounds |
EA200401025A EA007119B1 (ru) | 2002-02-06 | 2002-12-20 | Полиморфы клопидогреля гидрохлориа и их применение в качестве антитромботических соединений |
JP2003566010A JP2005522441A (ja) | 2002-02-06 | 2002-12-20 | クロピドグレル塩酸塩の多形体及び抗トロンビン化合物としての使用 |
IS7385A IS7385A (is) | 2002-02-06 | 2004-08-05 | Fjölgervingar klópídógrelhýdróklóríðs og notkun þeirra sem andsegaefnasambanda |
HRP20040741 HRP20040741A2 (en) | 2002-02-06 | 2004-08-17 | Polymorphs of clopidogrel hydrochloride and their use as antithrombic compounds |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HUP0200438 | 2002-02-06 | ||
HU0200438A HUP0200438A3 (en) | 2002-02-06 | 2002-02-06 | Novel clopidogrel hydrochloride polymorphs, process for the preparation thereof, their use and pharmaceutical compositions containing them |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003066637A1 true WO2003066637A1 (en) | 2003-08-14 |
Family
ID=89980128
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/HU2002/000157 WO2003066637A1 (en) | 2002-02-06 | 2002-12-20 | Polymorphs of clopidogrel hydrochloride and their use as antithrombic compounds |
Country Status (15)
Country | Link |
---|---|
US (1) | US20050113406A1 (WO2017193030A1) |
EP (1) | EP1474427A1 (WO2017193030A1) |
JP (1) | JP2005522441A (WO2017193030A1) |
KR (1) | KR20040079987A (WO2017193030A1) |
AU (1) | AU2002353251A1 (WO2017193030A1) |
BG (1) | BG108868A (WO2017193030A1) |
CZ (1) | CZ2004901A3 (WO2017193030A1) |
EA (1) | EA007119B1 (WO2017193030A1) |
HR (1) | HRP20040741A2 (WO2017193030A1) |
HU (1) | HUP0200438A3 (WO2017193030A1) |
IS (1) | IS7385A (WO2017193030A1) |
PL (1) | PL370038A1 (WO2017193030A1) |
SK (1) | SK3362004A3 (WO2017193030A1) |
WO (1) | WO2003066637A1 (WO2017193030A1) |
YU (1) | YU69604A (WO2017193030A1) |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005026174A1 (en) * | 2003-09-11 | 2005-03-24 | Generics [Uk] Limited | Novel crystalline polymorphs of clopidogrel |
WO2005068471A1 (en) * | 2004-01-13 | 2005-07-28 | Zentiva, A.S. | New crystalline forms of clopidogrel hydrobromide and methods of their preparation |
WO2005097804A1 (en) * | 2004-04-09 | 2005-10-20 | Hanmi Pharm. Co., Ltd. | Crystalline clopidogrel naphthalenesulfonate or hydrate thereof, method for preparing same and pharmaceutical composition containing same |
WO2005103059A1 (en) * | 2004-04-20 | 2005-11-03 | Sanofi-Aventis | Clopidogrel salt and polymorphic forms thereof |
WO2005117866A1 (en) * | 2004-06-01 | 2005-12-15 | Ivax Pharmaceuticals S.R.O. | Amorphous clopidogrel hydrochloride and its antithrombotic use |
EP1674468A1 (en) * | 2004-12-21 | 2006-06-28 | Ratiopharm GmbH | Polymorphs of clopidogrel hydrobromide |
EP1693375A1 (en) * | 2005-02-21 | 2006-08-23 | KRKA, tovarna zdravil, d.d., Novo mesto | Process for preparing clopidrogel hydrogen sulfate of form I |
WO2005104663A3 (en) * | 2004-03-05 | 2006-09-28 | Ipca Lab Ltd | Industrial process for preparation of clopidogrel hydrogen sulphate |
WO2007029096A2 (en) * | 2005-09-05 | 2007-03-15 | Ranbaxy Laboratories Limited | Novel polymorphic forms of clopidogrel hydrochloride |
WO2007029080A1 (en) * | 2005-09-05 | 2007-03-15 | Ranbaxy Laboratories Limited | Preparation of form i of clopidogrel hydrochloride |
WO2007073095A1 (en) * | 2005-12-22 | 2007-06-28 | Sk Chemicals Co., Ltd. | Process for the preparation of (s)-(+)-clopidogrel on a solid-phase |
WO2007074995A1 (en) * | 2005-12-26 | 2007-07-05 | Sk Chemicals Co., Ltd. | Process for the preparation of s-(+)-clopidogrel by optical resolution |
JP2007533744A (ja) * | 2004-04-20 | 2007-11-22 | サノフイ−アベンテイス | (+)−(S)−α−(2−クロロフェニル)−6,7−ジヒドロチエノ[3,2−C]ピリジン−5(4H)酢酸メチル臭化水素酸塩、クロピドロゲル(clopidrogel)臭化水素酸塩の多形体型 |
WO2008004249A2 (en) * | 2006-07-04 | 2008-01-10 | Msn Laboratories Limited | An improved process for the preparation of clopidogrel and its pharmaceutically acceptable salts |
WO2008060934A2 (en) * | 2006-11-14 | 2008-05-22 | Acusphere, Inc. | Formulations of tetrahydropyridine antiplatelet agents for parenteral or oral administration |
EP1970054A2 (en) | 2007-03-14 | 2008-09-17 | Ranbaxy Laboratories Limited | Clopidogrel tablets |
WO2008134600A1 (en) | 2007-04-27 | 2008-11-06 | Cydex Pharmaceuticals, Inc. | Formulations containing clopidogrel and sulfoalkyl ether cyclodextrin and methods of use |
EP2107061A1 (en) | 2008-04-02 | 2009-10-07 | Krka Tovarna Zdravil, D.D., Novo Mesto | Process for the preparation of optically enriched clopidogrel |
CN102120745A (zh) * | 2011-01-31 | 2011-07-13 | 天津红日药业股份有限公司 | 一种盐酸氯吡格雷的晶型ⅰ及其制备方法和用途 |
CN102367257A (zh) * | 2011-11-21 | 2012-03-07 | 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 |
US8835407B2 (en) | 2009-05-13 | 2014-09-16 | Cydex Pharmaceuticals, Inc. | Pharmaceutical compositions comprising prasugrel and cyclodextrin derivatives and methods of making and using the same |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100742134B1 (ko) * | 2006-02-07 | 2007-07-24 | 경동제약 주식회사 | 결정성S-(+)-메틸-2-(2-클로로페닐)-2-(6,7-디히드로티에노[3,2-c]피리딘-5(4H)-일)아세테이트·캄실레이트를 포함하는약학적 조성물 |
WO2008146249A1 (en) * | 2007-05-30 | 2008-12-04 | Wockhardt Research Centre | Processes for the preparation of clopidogrel |
WO2012123958A1 (en) | 2011-02-14 | 2012-09-20 | Cadila Healthcare Limited | Highly pure salts of clopidogrel free of genotoxic impurities |
HUP1400294A2 (hu) | 2014-06-13 | 2015-12-28 | Skillpharm Kft | Clopidogrel új alkalmazása |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0099802A1 (fr) * | 1982-07-13 | 1984-02-01 | Elf Sanofi | Nouveaux dérivés de la thiéno-(3,2-c) pyridine, leur procédé de préparation et leur application thérapeutique |
EP0281459A1 (fr) * | 1987-02-17 | 1988-09-07 | Sanofi | Enantiomère dextrogyre de l'alpha-(tétrahydro-4,5,6,7 thiéno (3,2-c)pyridyl-5) (chloro-2 phényl)-acétate de méthyle, son procédé de préparation et les compositions pharmaceutiques le renfermant |
WO1999065915A1 (fr) * | 1998-06-15 | 1999-12-23 | Sanofi-Synthelabo | Forme polymorphe de l'hydrogenosulfate de clopidogrel |
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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. |
HU225504B1 (en) * | 1997-05-13 | 2007-01-29 | Sanofi Aventis | Novel halophenyl-(2-(2-thienyl)-ethylamino)-acetonitriles and process for producing them |
HU226421B1 (en) * | 1998-11-09 | 2008-12-29 | Sanofi Aventis | Process for racemizing optically active 2-(2-chlorophenyl)-2-(2-(2-thienyl)-ethylamino)-acetamides |
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EP0099802A1 (fr) * | 1982-07-13 | 1984-02-01 | Elf Sanofi | Nouveaux dérivés de la thiéno-(3,2-c) pyridine, leur procédé de préparation et leur application thérapeutique |
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Also Published As
Publication number | Publication date |
---|---|
HUP0200438A2 (hu) | 2003-09-29 |
PL370038A1 (en) | 2005-05-16 |
BG108868A (en) | 2005-09-30 |
EA200401025A1 (ru) | 2004-12-30 |
EP1474427A1 (en) | 2004-11-10 |
CZ2004901A3 (cs) | 2005-02-16 |
KR20040079987A (ko) | 2004-09-16 |
IS7385A (is) | 2004-08-05 |
HRP20040741A2 (en) | 2004-12-31 |
JP2005522441A (ja) | 2005-07-28 |
EA007119B1 (ru) | 2006-06-30 |
HU0200438D0 (en) | 2002-04-29 |
SK3362004A3 (sk) | 2005-03-04 |
YU69604A (sh) | 2006-08-17 |
US20050113406A1 (en) | 2005-05-26 |
HUP0200438A3 (en) | 2003-10-28 |
AU2002353251A1 (en) | 2003-09-02 |
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