NO328651B1 - Syreaddisjonssalter av et hydropyridinderivat, medikamenter som inneholder disse, anvendelse av saltene til fremstilling av medikamenter og fremgangsmate for fremstilling av syreaddisjonssaltene av hydropyridinderivatet - Google Patents
Syreaddisjonssalter av et hydropyridinderivat, medikamenter som inneholder disse, anvendelse av saltene til fremstilling av medikamenter og fremgangsmate for fremstilling av syreaddisjonssaltene av hydropyridinderivatet Download PDFInfo
- Publication number
- NO328651B1 NO328651B1 NO20030022A NO20030022A NO328651B1 NO 328651 B1 NO328651 B1 NO 328651B1 NO 20030022 A NO20030022 A NO 20030022A NO 20030022 A NO20030022 A NO 20030022A NO 328651 B1 NO328651 B1 NO 328651B1
- Authority
- NO
- Norway
- Prior art keywords
- fluorobenzyl
- acetoxy
- tetrahydrothieno
- pyridine
- cyclopropylcarbonyl
- Prior art date
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
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- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- NGHMEZWZOZEZOH-UHFFFAOYSA-N silicic acid;hydrate Chemical compound O.O[Si](O)(O)O NGHMEZWZOZEZOH-UHFFFAOYSA-N 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000205396 | 2000-07-06 | ||
| JP2000266780 | 2000-09-04 | ||
| PCT/JP2001/005764 WO2002004461A1 (fr) | 2000-07-06 | 2001-07-03 | Sels d'addition acides de dérivés hydropyridine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20030022D0 NO20030022D0 (no) | 2003-01-03 |
| NO20030022L NO20030022L (no) | 2003-03-05 |
| NO328651B1 true NO328651B1 (no) | 2010-04-19 |
Family
ID=26595526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20030022A NO328651B1 (no) | 2000-07-06 | 2003-01-03 | Syreaddisjonssalter av et hydropyridinderivat, medikamenter som inneholder disse, anvendelse av saltene til fremstilling av medikamenter og fremgangsmate for fremstilling av syreaddisjonssaltene av hydropyridinderivatet |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6693115B2 (fr) |
| EP (2) | EP1728794B1 (fr) |
| KR (6) | KR20120062906A (fr) |
| CN (1) | CN1214031C (fr) |
| AT (2) | ATE346071T1 (fr) |
| AU (2) | AU2001267916B2 (fr) |
| BR (1) | BR0112168A (fr) |
| CA (2) | CA2703697C (fr) |
| CY (3) | CY1107554T1 (fr) |
| CZ (1) | CZ302990B6 (fr) |
| DE (2) | DE60134508D1 (fr) |
| DK (2) | DK1298132T3 (fr) |
| ES (2) | ES2308633T3 (fr) |
| HK (2) | HK1051362A1 (fr) |
| HU (2) | HU230762B1 (fr) |
| IL (2) | IL153546A0 (fr) |
| MX (1) | MXPA03000031A (fr) |
| NO (1) | NO328651B1 (fr) |
| NZ (1) | NZ523416A (fr) |
| PL (1) | PL208386B1 (fr) |
| PT (2) | PT1728794E (fr) |
| RU (1) | RU2238275C1 (fr) |
| TW (1) | TWI290927B (fr) |
| WO (1) | WO2002004461A1 (fr) |
Families Citing this family (100)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1350511B1 (fr) | 2000-12-25 | 2008-09-10 | Daiichi Sankyo Company, Limited | Compositions medicales contenant de l'aspirine |
| BR0312778A (pt) * | 2002-07-18 | 2005-05-03 | Sankyo Co | Composição farmacêutica para prevenção ou tratamento de arteriosclerose ou doenças derivadas de arteriosclerose, e, usos de um antagonista de receptor de adp e de um inibidor de acat |
| JP2006525328A (ja) * | 2003-05-05 | 2006-11-09 | イーライ リリー アンド カンパニー | 心疾患の治療方法 |
| US20060099261A1 (en) * | 2004-11-08 | 2006-05-11 | Biokey, Inc. | Methods and formulations for making controlled release oral dosage form |
| US8586085B2 (en) * | 2004-11-08 | 2013-11-19 | Biokey, Inc. | Methods and formulations for making pharmaceutical compositions containing bupropion |
| US20060099262A1 (en) * | 2004-11-08 | 2006-05-11 | Biokey, Inc. | Methods and formulations for making controlled release oral dosage form |
| CN1318428C (zh) * | 2005-02-23 | 2007-05-30 | 天津药物研究院 | 噻吩并吡啶取代的乙酰肼衍生物 |
| TWI318571B (en) * | 2005-06-10 | 2009-12-21 | Lilly Co Eli | Formulation of a thienopyridine platelet aggregation inhibitor |
| CN101198329A (zh) * | 2005-06-17 | 2008-06-11 | 伊莱利利公司 | 普拉格雷给药方案 |
| EP1940399A2 (fr) * | 2005-08-19 | 2008-07-09 | Eli Lilly & Company | Utilisation des inhibiteurs de type par-1/par-4 pour le traitement de maladies vasculaires |
| US8056072B2 (en) | 2005-10-31 | 2011-11-08 | Microsoft Corporation | Rebootless display driver upgrades |
| JP5844028B2 (ja) | 2006-04-04 | 2016-01-13 | ケージー アクキュイシチオン エルエルシー | 抗血小板薬及び酸阻害薬を含む経口剤形 |
| TWI392681B (zh) * | 2006-04-06 | 2013-04-11 | Daiichi Sankyo Co Ltd | 高純度普拉格雷及其酸加成鹽之製法 |
| WO2008000418A2 (fr) * | 2006-06-27 | 2008-01-03 | Sandoz Ag | Nouveau procédé de préparation de sel |
| WO2008060934A2 (fr) * | 2006-11-14 | 2008-05-22 | Acusphere, Inc. | Formulations d'agents de tetrahydropyridine antiplaquettes pour administration parentale ou orale |
| KR101442862B1 (ko) * | 2006-12-07 | 2014-09-22 | 다이이찌 산쿄 가부시키가이샤 | 만니톨 또는 유당을 함유하는 고형 제제 |
| BRPI0719529B8 (pt) * | 2006-12-07 | 2021-05-25 | Daiichi Sankyo Co Ltd | método para produzir uma preparação sólida |
| WO2008072532A1 (fr) * | 2006-12-07 | 2008-06-19 | Daiichi Sankyo Company, Limited | Composition pharmaceutique présentant une stabilité au stockage améliorée |
| CA2671975C (fr) * | 2006-12-07 | 2013-10-29 | Daiichi Sankyo Company, Limited | Preparation revetue d'un film ayant une stabilite amelioree |
| CA2671979C (fr) | 2006-12-07 | 2014-02-04 | Daiichi Sankyo Company, Limited | Composition pharmaceutique contenant de l'hydroxypropylcellulose faiblement substituee |
| EP2123656B1 (fr) * | 2007-03-02 | 2014-06-11 | Daiichi Sankyo Company, Limited | Procédé de production de chlorhydrate de prasugrel de grande pureté |
| KR20150041173A (ko) | 2007-04-27 | 2015-04-15 | 사이덱스 파마슈티칼스, 인크. | 클로피도그렐 및 설포알킬 에테르 사이클로덱스트린을 함유하는 제형 및 사용 방법 |
| CZ302135B6 (cs) * | 2007-07-09 | 2010-11-10 | Zentiva, A. S. | Zpusob výroby 5-[2-cyklopropyl-1-(2-fluorfenyl)-2-oxoethyl]-4, 5, 6, 7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu (prasugrelu) |
| US20100261908A1 (en) * | 2007-11-09 | 2010-10-14 | Dr. Reddy's Laboratories Ltd. | Processes for the preparation of prasugrel , and its salts and polymorphs |
| HU230261B1 (hu) * | 2007-11-27 | 2015-11-30 | Egis Gyógyszergyár Nyilvánosan Működő Részvénytársaság | Eljárás gyógyszeripari intermedierek előállítására |
| CN101177430A (zh) * | 2007-12-11 | 2008-05-14 | 鲁南制药集团股份有限公司 | 氢化吡啶衍生物及其盐的制备方法 |
| EP2257556A1 (fr) | 2008-02-06 | 2010-12-08 | Helm AG | Sels de prasugrel avec des propriétés améliorées |
| WO2009129983A1 (fr) * | 2008-04-21 | 2009-10-29 | Ratiopharm Gmbh | Sels d'addition avec des acides de prasugrel et compositions pharmaceutiques les comprenant |
| PL2112155T3 (pl) | 2008-04-25 | 2011-03-31 | Sandoz Ag | Wodorosiarczan (VI) 2-acetoksy-5-(α-cyklopropylokarbonylo-2-fluorobenzylo)-4,5,6,7-tetrahydrotieno[3,2-c]pirydyny i sposób jego otrzymywania |
| US20090281136A1 (en) * | 2008-05-08 | 2009-11-12 | Sandeep Mhetre | Prasugrel pharmaceutical formulations |
| US20130303477A1 (en) * | 2008-05-13 | 2013-11-14 | The Medicines Company | Maintenance of Platelet Inhibition During Antiplatelet Therapy |
| WO2009140092A1 (fr) | 2008-05-13 | 2009-11-19 | The Medicines Company | Conservation de l'inhibition de plaquettes durant une thérapie anti-plaquettes |
| US20120141468A1 (en) | 2008-05-13 | 2012-06-07 | Lisa Ruderman Chen | Maintenance of platelet inhibition during antiplatelet therapy |
| US9427448B2 (en) | 2009-11-11 | 2016-08-30 | The Medicines Company | Methods of treating, reducing the incidence of, and/or preventing ischemic events |
| US8759316B2 (en) * | 2008-05-13 | 2014-06-24 | The Medicines Company | Maintenance of platelet inhibition during antiplatelet therapy |
| KR20110045034A (ko) | 2008-08-02 | 2011-05-03 | 루난 파마슈티컬 그룹 코퍼레이션 | 프라수그렐 황산수소염 및 이의 약제학적 조성물 및 용도 |
| EP2398468B1 (fr) | 2009-02-17 | 2016-11-30 | KRKA, D.D., Novo Mesto | Compositions pharmaceutiques comprenant du prasugrel ou ses sels d'addition d'acide pharmaceutiquement acceptables, et leurs procédés de préparation |
| WO2010111951A1 (fr) | 2009-03-31 | 2010-10-07 | 上海医药工业研究院 | Cristaux de bromhydrate de prasugrel |
| AU2010233089B2 (en) | 2009-04-10 | 2016-05-26 | Tufts Medical Center, Inc. | Par-1 activation by metalloproteinase-1 (MMP-1) |
| KR101743591B1 (ko) | 2009-05-13 | 2017-06-20 | 사이덱스 파마슈티칼스, 인크. | 프라수그렐 및 사이클로덱스트린 유도체를 포함하는 약학 조성물 및 그의 제조 및 사용 방법 |
| EP2451816A4 (fr) * | 2009-07-06 | 2013-02-27 | Glenmark Generics Ltd | Forme cristalline d'hydrobromure de prasugrel et son procédé de préparation |
| DE102009036646A1 (de) | 2009-08-07 | 2011-02-10 | Ratiopharm Gmbh | Prasugrel in nicht-kristalliner Form und pharmazeutische Zusammensetzung davon |
| CN101993447A (zh) | 2009-08-26 | 2011-03-30 | 浙江华海药业股份有限公司 | 一种人工合成普拉格雷的方法 |
| WO2011036533A1 (fr) | 2009-09-23 | 2011-03-31 | Glenmark Pharmaceuticals Limited | Composition pharmaceutique contenant du prasugrel et du triflusal |
| EA028885B1 (ru) | 2009-11-11 | 2018-01-31 | Чиези Фармачеутичи С.П.А. | Способы лечения или предотвращения тромбоза стента и инфаркта миокарда (варианты) |
| US10376532B2 (en) | 2009-11-11 | 2019-08-13 | Chiesi Farmaceutici, S.P.A. | Methods of treating, reducing the incidence of, and/or preventing ischemic events |
| CZ2009763A3 (cs) | 2009-11-16 | 2011-05-25 | Zentiva, K. S. | Zpusob výroby vysoce cistého 5-[2-cyklopropyl-1-(2-fluorfenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu známého pod nechráneným názvem prasugrel a jeho nových farmaceuticky prijatelných solí. |
| CZ2009762A3 (cs) | 2009-11-16 | 2011-05-25 | Zentiva, K. S. | Nové soli 5-[2-cyklopropyl-1-(2-fluorfenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu známého pod nechráneným názvem prasugrel a zpusob jejich výroby |
| CZ2009828A3 (cs) | 2009-12-09 | 2011-06-22 | Zentiva, K.S. | Zpusob prípravy hydrochloridu 5-[2-cyklopropyl-1-(2-fluorfenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu (prasugrelu hydrochloridu) v polymorfní forme B |
| HU229035B1 (en) * | 2009-12-21 | 2013-07-29 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | Process for producing prasurgel |
| WO2011092720A2 (fr) * | 2010-02-01 | 2011-08-04 | Msn Laboratories Limited | Composition pharmaceutique de prasugrel et ses sels pharmaceutiquement acceptables |
| EP2360159A1 (fr) * | 2010-02-11 | 2011-08-24 | Ratiopharm GmbH | Prasugrel de forme cristalline et micronisée et composition pharmaceutique le contenant |
| EP2545059A1 (fr) | 2010-03-09 | 2013-01-16 | Synthon BV | Procédé de préparation de prasugrel |
| KR101184915B1 (ko) | 2010-03-11 | 2012-09-21 | 한미사이언스 주식회사 | 고순도 프라수그렐의 제조방법 |
| CA2788764A1 (fr) | 2010-03-23 | 2011-09-29 | Alembic Pharmaceuticals Limited | Procede de preparation du sel hcl de prasugrel |
| EP2377520A1 (fr) | 2010-03-24 | 2011-10-19 | Ratiopharm GmbH | Composition pharmaceutique du prasugrel |
| CN102212068A (zh) * | 2010-04-06 | 2011-10-12 | 刘桂坤 | 噻吩衍生物及其制备方法和在药物上的应用 |
| KR20120052381A (ko) | 2010-04-08 | 2012-05-23 | 테바 파마슈티컬 인더스트리즈 리미티드 | 프라수그렐 염의 결정형 |
| CN102212071B (zh) * | 2010-04-08 | 2014-03-26 | 上海医药工业研究院 | 普拉格雷盐酸盐乙酸溶剂合物及其结晶和制备方法 |
| EP2560644B1 (fr) | 2010-04-19 | 2016-06-29 | Cadila Healthcare Limited | Composition pharmaceutique comprenant des agents antiplaquettaires et un agent stimulant l'érythropoïèse |
| WO2012001486A1 (fr) * | 2010-06-28 | 2012-01-05 | Mayuka Labs Pvt. Ltd. | Procédé perfectionné pour la préparation de chlorhydrate de prasugrel et de ses intermédiaires |
| TR201006802A1 (tr) * | 2010-08-17 | 2012-03-21 | Sanovel İlaç San. Ve Ti̇c. A.Ş. | Prasugrelin oral yolla dağılan formülasyonları. |
| TR201007926A1 (tr) | 2010-07-19 | 2012-02-21 | Sanovel İlaç San.Ve Ti̇c.A.Ş. | Prasugrel tablet formülasyonları. |
| EP2409685A3 (fr) | 2010-07-19 | 2012-02-01 | Sanovel Ilac Sanayi ve Ticaret A.S. | Formulations de prasugrel à désintégration orale |
| TR201005900A1 (tr) | 2010-07-19 | 2012-02-21 | Sanovel İlaç San. Ve Ti̇c. A.Ş. | Geliştirilmiş stabiliteye sahip prasugrel granülleri. |
| WO2012023145A2 (fr) * | 2010-08-18 | 2012-02-23 | Hetero Research Foundation | Particules cristallines de chlorhydrate de prasugrel |
| HUP1000565A2 (en) | 2010-10-22 | 2012-05-02 | Egis Gyogyszergyar Nyrt | Process for the preparation of pharmaceutically active compound and intermediers |
| CN101985450B (zh) * | 2010-11-02 | 2012-07-11 | 北京赛科药业有限责任公司 | 普拉格雷盐及其制备方法 |
| CN102532157A (zh) * | 2010-12-16 | 2012-07-04 | 瑞阳制药有限公司 | 普拉格雷的可药用酸加成盐化合物及其制备方法 |
| CZ305314B6 (cs) * | 2010-12-30 | 2015-07-29 | Zentiva, K.S. | Nový hydrobromid formy C 5-[2-cyklopropyl-1-(2-fluorofenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu známého pod nechráněným názvem prasugrel a způsob jeho výroby |
| CN102199163A (zh) * | 2011-04-01 | 2011-09-28 | 中国药科大学 | 2-羟基四氢噻吩并吡啶衍生物及其制备方法与在制药中的用途 |
| CN102746318A (zh) * | 2011-04-20 | 2012-10-24 | 上海信谊药厂有限公司 | 用于制备普拉格雷盐酸盐的方法 |
| US9788539B2 (en) | 2011-05-17 | 2017-10-17 | Velico Medical, Inc. | Platelet protection solution having beta-galactosidase and sialidase inhibitors |
| US9609861B2 (en) | 2011-05-17 | 2017-04-04 | Velico Medical Inc. | Platelet additive solution having a β-galactosidase inhibitor |
| CN103702556A (zh) | 2011-05-17 | 2014-04-02 | 维利科医疗公司 | 使用唾液酸酶抑制剂改进的血小板保存 |
| CN102838618A (zh) | 2011-06-22 | 2012-12-26 | 广东东阳光药业有限公司 | 一种制备普拉格雷的方法及普拉格雷盐酸盐新晶型 |
| EP2736509B1 (fr) | 2011-07-28 | 2015-09-23 | Laboratorios Lesvi, S.L. | Procédé pour la préparation de prasugrel |
| CN103102355A (zh) * | 2011-11-09 | 2013-05-15 | 丁克 | 具有旋光性的四氢噻吩并吡啶化合物 |
| CZ2011872A3 (cs) | 2011-12-22 | 2013-07-03 | Zentiva, K.S. | Farmaceutická formulace prasugrelu hydrobromidu |
| US8603537B2 (en) | 2012-04-02 | 2013-12-10 | Egis Pharmaceuticals Plc | Prasugrel containing quickly released stable oral pharmaceutical compositions |
| EP2722037A1 (fr) | 2012-10-19 | 2014-04-23 | Sanovel Ilac Sanayi ve Ticaret A.S. | Formulations de prasugrel |
| EP2722036A1 (fr) | 2012-10-19 | 2014-04-23 | Sanovel Ilac Sanayi ve Ticaret A.S. | Formulations orales solides de prasugrel |
| PL402028A1 (pl) | 2012-12-12 | 2014-06-23 | Instytut Farmaceutyczny | Sposób wytwarzania postaci polimorficznej B chlorowodorku prasugrelu o czystości farmaceutycznej |
| HU230649B1 (hu) | 2013-01-24 | 2017-05-29 | Egis Gyógyszergyár Nyilvánosan Működő Részvénytársaság | Javított eljárás prasugrel gyógyszeripari hatóanyag és az 1-ciklopropil-2-(2-fluorofenil)-etanon intermedier előállítására |
| WO2014120886A1 (fr) | 2013-01-30 | 2014-08-07 | Velico Medical, Inc. | Solution additive plaquettaire ayant un peptide formant un hydrogel à auto-assemblage |
| KR102235732B1 (ko) | 2013-12-26 | 2021-04-02 | 에스케이플래닛 주식회사 | 쿠폰 관리 시스템 및 방법, 그리고 이를 위한 장치 및 컴퓨터 프로그램이 기록된 기록매체 |
| DE102014108210A1 (de) | 2014-06-11 | 2015-12-17 | Dietrich Gulba | Rodentizid |
| EP2979693A1 (fr) | 2014-08-01 | 2016-02-03 | Zaklady Farmaceutyczne Polpharma SA | Composition pharmaceutique comprenant du prasugrel ou un sel pharmaceutiquement acceptable de celui-ci et son procédé de préparation |
| CN104479502A (zh) * | 2014-12-31 | 2015-04-01 | 江阴市天邦涂料股份有限公司 | 一种水性防腐涂料 |
| WO2016122421A1 (fr) | 2015-01-29 | 2016-08-04 | Pharmactive Ilaç Sanayi Ve Ticaret A.Ş. | Compositions pharmaceutiques stables contenant une base de prasugrel |
| EP3106151A1 (fr) | 2015-06-19 | 2016-12-21 | Sanovel Ilac Sanayi ve Ticaret A.S. | Compositions pharmaceutiques de bromhydrate de prasugrel |
| EP3156049A1 (fr) | 2015-10-15 | 2017-04-19 | Alembic Pharmaceuticals Limited | Composition pharmaceutique de prasugrel |
| EP3158993A1 (fr) | 2015-10-22 | 2017-04-26 | Zaklady Farmaceutyczne Polpharma SA | Procédé pour préparer un comprimé contenant du prasugrel ou des sels pharmaceutiquement acceptables de celui-ci |
| HU231079B1 (hu) | 2016-06-23 | 2020-06-29 | Richter Gedeon Nyrt. | Eljárás nagytisztaságú Prasugrel előállítására bromopentil szennyezés eltávolításával |
| WO2018073437A1 (fr) | 2016-10-21 | 2018-04-26 | Laboratorios Lesvi, Sl | Formulations pharmaceutiques de prasugrel et ses procédés de préparation |
| CN106632391A (zh) * | 2016-12-23 | 2017-05-10 | 山东鲁抗医药股份有限公司 | 一种盐酸普拉格雷化合物及其制备方法和含有盐酸普拉格雷的药物组合物 |
| WO2018234565A1 (fr) | 2017-06-23 | 2018-12-27 | Chiesi Farmaceutici S.P.A. | Procédé de prévention de thrombose de shunt de l'artère systémique-pulmonaire |
| KR102063862B1 (ko) | 2018-08-09 | 2020-01-08 | 한국기술교육대학교 산학협력단 | Qr코드 기반의 공유시점관리 시스템 |
| KR102485021B1 (ko) | 2020-11-18 | 2023-01-05 | 효성중공업 주식회사 | 델타구조 반도체변압기 기반 에너지 저장장치의 SoC 균등제어 장치 및 방법 |
| KR102491932B1 (ko) | 2020-11-18 | 2023-01-27 | 현대엠시스템즈 주식회사 | 통신 방식 가변형 원격 모니터링 제어 시스템 및 방법 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4141894A (en) * | 1976-11-02 | 1979-02-27 | Eli Lilly And Company | Trans-5a-aryl-decahydrobenzazepines |
| FR2576901B1 (fr) | 1985-01-31 | 1987-03-20 | Sanofi Sa | Nouveaux derives de l'acide a-(oxo-2 hexahydro-2,4,5,6,7,7a thieno (3,2-c) pyridyl-5) phenyl acetique, leur procede de preparation et leur application therapeutique |
| JP2506376B2 (ja) * | 1987-07-16 | 1996-06-12 | 三菱化学株式会社 | ２−（４−メチルアミノブトキシ）ジフェニルメタン・塩酸塩の製造方法 |
| FI101150B (fi) | 1991-09-09 | 1998-04-30 | Sankyo Co | Menetelmä lääkeaineina käyttökelpoisten tetrahydrotienopyridiinin johd annaisten valmistamiseksi |
| US5342851A (en) * | 1992-10-07 | 1994-08-30 | Mcneil-Ppc, Inc. | Substituted thiazole derivatives useful as platelet aggregation inhibitors |
| JPH07188168A (ja) * | 1993-12-28 | 1995-07-25 | Fujisawa Pharmaceut Co Ltd | ジヒドロピリジン化合物およびその製造方法 |
| EP1350511B1 (fr) * | 2000-12-25 | 2008-09-10 | Daiichi Sankyo Company, Limited | Compositions medicales contenant de l'aspirine |
| CZ2009762A3 (cs) | 2009-11-16 | 2011-05-25 | Zentiva, K. S. | Nové soli 5-[2-cyklopropyl-1-(2-fluorfenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu známého pod nechráneným názvem prasugrel a zpusob jejich výroby |
| CZ305314B6 (cs) | 2010-12-30 | 2015-07-29 | Zentiva, K.S. | Nový hydrobromid formy C 5-[2-cyklopropyl-1-(2-fluorofenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu známého pod nechráněným názvem prasugrel a způsob jeho výroby |
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