ZA200108331B - Benzimidazole compound crystal. - Google Patents
Benzimidazole compound crystal. Download PDFInfo
- Publication number
- ZA200108331B ZA200108331B ZA200108331A ZA200108331A ZA200108331B ZA 200108331 B ZA200108331 B ZA 200108331B ZA 200108331 A ZA200108331 A ZA 200108331A ZA 200108331 A ZA200108331 A ZA 200108331A ZA 200108331 B ZA200108331 B ZA 200108331B
- Authority
- ZA
- South Africa
- Prior art keywords
- crystal
- benzimidazole
- methyl
- cellulose
- trifluoroethoxy
- Prior art date
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- 239000013078 crystal Substances 0.000 title claims description 51
- -1 Benzimidazole compound Chemical class 0.000 title description 26
- 150000003839 salts Chemical class 0.000 claims description 32
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
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- 231100000397 ulcer Toxicity 0.000 claims description 9
- 230000001079 digestive effect Effects 0.000 claims description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 6
- 238000004458 analytical method Methods 0.000 claims description 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 description 44
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- 230000003287 optical effect Effects 0.000 description 18
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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JP17150999 | 1999-06-17 |
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ZA200108331A ZA200108331B (en) | 1999-06-17 | 2001-10-10 | Benzimidazole compound crystal. |
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AR (5) | AR031069A1 (forum.php) |
AT (1) | ATE391126T1 (forum.php) |
AU (1) | AU778820B2 (forum.php) |
BE (1) | BE2014C017I2 (forum.php) |
BR (1) | BRPI0011674B8 (forum.php) |
CA (1) | CA2375201C (forum.php) |
CY (2) | CY1110384T1 (forum.php) |
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IL (2) | IL145996A0 (forum.php) |
MX (1) | MXPA01012642A (forum.php) |
MY (1) | MY125399A (forum.php) |
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NZ (1) | NZ515702A (forum.php) |
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Families Citing this family (95)
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US5840737A (en) | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
US6489346B1 (en) * | 1996-01-04 | 2002-12-03 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
US20040224989A1 (en) * | 1999-01-29 | 2004-11-11 | Barberich Timothy J. | S-lansoprazole compositions and methods |
TWI289557B (en) * | 1999-06-17 | 2007-11-11 | Takeda Chemical Industries Ltd | A crystal of a hydrate of (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole |
WO2001002389A1 (fr) * | 1999-06-30 | 2001-01-11 | Takeda Chemical Industries, Ltd. | Cristaux de composes benzimidazole |
AU2001252595A1 (en) | 2000-04-28 | 2001-11-12 | Takeda Chemical Industries Ltd. | Process for producing optically active sulfoxide derivative |
CA2701704C (en) * | 2000-05-15 | 2011-09-06 | Takeda Pharmaceutical Company Limited | Process for producing crystal |
CA2775616C (en) | 2000-08-04 | 2013-09-17 | Takeda Pharmaceutical Company Limited | Salts of benzimidazole compound and application thereof |
CA2436825C (en) * | 2000-12-01 | 2011-01-18 | Takeda Chemical Industries, Ltd. | Process for the crystallization of (r)- or (s)-lansoprazole |
DK1459737T3 (da) | 2001-10-17 | 2013-01-02 | Takeda Pharmaceutical | Granulat indeholdende syreustabilt kemisk middel i stor mængde |
KR100467100B1 (ko) * | 2002-03-20 | 2005-01-24 | 일양약품주식회사 | 2-[(4-메톡시-3-메틸)-2-피리디닐]메틸설피닐-5-(1H-피롤-1-릴)-1H-벤즈이미다졸 또는 이의 Nа염을 함유하는주사제의 제조방법 |
PL373539A1 (en) * | 2002-03-27 | 2005-09-05 | Teva Pharmaceutical Industries Ltd. | Lansoprazole polymorphs and processes for preparation thereof |
MY148805A (en) | 2002-10-16 | 2013-05-31 | Takeda Pharmaceutical | Controlled release preparation |
EP2596792A1 (en) * | 2002-10-16 | 2013-05-29 | Takeda Pharmaceutical Company Limited | Stable solid preparations |
US20050220870A1 (en) * | 2003-02-20 | 2005-10-06 | Bonnie Hepburn | Novel formulation, omeprazole antacid complex-immediate release for rapid and sustained suppression of gastric acid |
CA2516600C (en) | 2003-03-24 | 2011-04-05 | Eisai Co., Ltd. | Process for production of sulfoxide proton pump inhibitors in the amorphous state |
CA2529255A1 (en) * | 2003-06-20 | 2004-12-29 | Ch Chemicals (Pty) Ltd | Polyurethane-based cementitious liner |
EP1648416A4 (en) * | 2003-07-18 | 2012-03-28 | Santarus Inc | PHARMACEUTICAL FORMULATIONS FOR INHIBITING THE ACIDIC ACIDIFICATION AND MANUFACTURING AND USE METHOD |
MXPA06000524A (es) * | 2003-07-18 | 2006-08-11 | Santarus Inc | Formulacion farmaceutica y metodo para tratar desordenes gastrointestinales provocados por acido. |
US8993599B2 (en) | 2003-07-18 | 2015-03-31 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
US20070292498A1 (en) * | 2003-11-05 | 2007-12-20 | Warren Hall | Combinations of proton pump inhibitors, sleep aids, buffers and pain relievers |
JP2007522217A (ja) * | 2004-02-10 | 2007-08-09 | サンタラス インコーポレイティッド | プロトンポンプ阻害剤、緩衝剤および非ステロイド系抗炎症薬の組み合わせ |
WO2005117870A2 (en) * | 2004-04-16 | 2005-12-15 | Santarus, Inc. | Combination of proton pump inhibitor, buffering agent, and prokinetic agent |
US8815916B2 (en) | 2004-05-25 | 2014-08-26 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
US8906940B2 (en) | 2004-05-25 | 2014-12-09 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
CA2570916C (en) | 2004-06-16 | 2013-06-11 | Tap Pharmaceutical Products, Inc. | Pulsed release dosage form of a ppi |
EP2264025B1 (en) | 2004-09-13 | 2013-11-06 | Takeda Pharmaceutical Company Limited | Method for producing lansoprazole |
ES2675581T3 (es) | 2005-02-25 | 2018-07-11 | Takeda Pharmaceutical Company Limited | Método para producir gránulos de un compuesto de bencimidazol recubiertos |
ES2259269B1 (es) | 2005-03-03 | 2007-11-01 | Esteve Quimica, S.A. | Procedimiento para la preparacion de derivados de 2-(2-piridilmetilsulfinil)-bencimidazol opticamente activos. |
BRPI0617987A2 (pt) * | 2005-10-06 | 2011-08-16 | Auspex Pharmaceuticals Inc | composição, composição farmacêutica, forma de dosagem efervescente, composição farmacêutica oral de comprimidos unitários múltiplos, forma de dosagem farmacêutica de liberação prolongada, forma de dosagem farmacêutica revestida entérica, forma de dosagem farmacêutica estável para administração oral a sujeitos mamìferos, método para tratamento de doenças relacionadas a ácido gástrico pela inibição de secreção de ácido gástrico, método para tratamento de uma infecção bacteriana provocada ou mediada por helicobacter pylori, processo para preparar um composto da fórmula 3, processo para preparar um composto da fórmula 5, uso de um composto da fórmula 1 para a preparação de um medicamento para tratamento de doenças relacionadas a ácido gástrico, pela inibição de secreção de ácido gástrico, uso de um composto da fórmula 1 para a preparação de um medicamento para tratamento de uma infecção bacteriana provocada ou mediada por helicobacter pylori uso de um composto da fórmula 1 para a preparação de um medicamento para tratamento de doenças relecionadas a ácido gástrico pela inibição de secreção de ácido gástrico |
KR20080081071A (ko) | 2005-12-28 | 2008-09-05 | 다케다 야쿠힌 고교 가부시키가이샤 | 방출 제어 고형 제제 |
KR100758600B1 (ko) | 2006-01-05 | 2007-09-13 | 주식회사 대웅제약 | 란소프라졸 결정형 a의 제조방법 |
US20090092658A1 (en) * | 2007-10-05 | 2009-04-09 | Santarus, Inc. | Novel formulations of proton pump inhibitors and methods of using these formulations |
US20100093804A1 (en) * | 2006-12-07 | 2010-04-15 | Hetero Drugs Limited | novel crystalline form of lansoprazole |
JP5366558B2 (ja) | 2006-12-28 | 2013-12-11 | 武田薬品工業株式会社 | 口腔内崩壊性固形製剤 |
CN104069088A (zh) * | 2007-10-12 | 2014-10-01 | 武田制药北美公司 | 与食物摄入无关的治疗胃肠病症的方法 |
NZ593629A (en) * | 2007-12-18 | 2012-11-30 | Watson Pharma Private Ltd | Stable amorphous R-lansoprazole prepared by optically resolving racemic lansoprazole |
EP2292612A3 (en) * | 2007-12-31 | 2011-05-04 | Takeda Pharmaceutical Company Limited | Crystalline solvated forms of (r)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1h-benzimidazole |
AR070972A1 (es) * | 2008-03-10 | 2010-05-19 | Takeda Pharmaceutical | Cristal de compuestos de bencimidazol (lansoprazol) |
NZ588407A (en) * | 2008-03-11 | 2012-07-27 | Takeda Pharmaceutical | Orally-disintegrating solid preparation |
WO2009117489A1 (en) * | 2008-03-18 | 2009-09-24 | Dr. Reddy's Laboratories Ltd. | Dexlansoprazole process and polymorphs |
US20090263475A1 (en) * | 2008-04-21 | 2009-10-22 | Nagaraju Manne | Dexlansoprazole compositions |
WO2010079504A2 (en) | 2008-05-14 | 2010-07-15 | Watson Pharma Private Limited | Stable r(+)-lansoprazole amine salt and a process for preparing the same |
EP2309985B1 (en) * | 2008-07-28 | 2018-03-14 | Takeda Pharmaceutical Company Limited | Pharmaceutical composition |
WO2010039885A2 (en) * | 2008-09-30 | 2010-04-08 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of dexlansoprazole |
IT1391758B1 (it) * | 2008-11-11 | 2012-01-27 | Dipharma Francis Srl | Procedimento per la preparazione di dexlansoprazolo amorfo |
WO2010056059A2 (en) * | 2008-11-14 | 2010-05-20 | Hanmi Pharm. Co., Ltd. | Novel crystalline dexlansoprazole and pharmaceutical composition comprising same |
IT1391776B1 (it) * | 2008-11-18 | 2012-01-27 | Dipharma Francis Srl | Procedimento per la preparazione di dexlansoprazolo |
IT1392813B1 (it) | 2009-02-06 | 2012-03-23 | Dipharma Francis Srl | Forme cristalline di dexlansoprazolo |
US20110009637A1 (en) * | 2009-02-10 | 2011-01-13 | Dario Braga | Crystals of Dexlansoprazole |
WO2011004387A2 (en) * | 2009-06-18 | 2011-01-13 | Matrix Laboratories Ltd | Process for the preparation of dexlansoprazole polymorphic forms |
IT1395118B1 (it) * | 2009-07-29 | 2012-09-05 | Dipharma Francis Srl | Procedimento per la preparazione di dexlansoprazolo cristallino |
CN108383804A (zh) | 2009-11-12 | 2018-08-10 | 特罗菲克斯制药股份有限公司 | 神经营养蛋白模拟化合物及其盐的晶型 |
US10273219B2 (en) | 2009-11-12 | 2019-04-30 | Pharmatrophix, Inc. | Crystalline forms of neurotrophin mimetic compounds and their salts |
CN102108076B (zh) * | 2009-12-23 | 2014-07-23 | 江苏豪森医药集团有限公司 | 制备无定形右兰索拉唑的方法 |
AU2011210328A1 (en) | 2010-01-29 | 2012-08-16 | Ranbaxy Laboratories Limited | Process for the preparation of crystalline forms of dexlansoprazole |
US20110189271A1 (en) * | 2010-02-02 | 2011-08-04 | Vishal Lad | Pharmaceutical formulations of acid-labile drugs |
AU2011234003B2 (en) * | 2010-03-31 | 2013-09-19 | Sun Pharmaceutical Industries Limited | Process for the preparation of dexlansoprazole |
WO2011121546A1 (en) | 2010-03-31 | 2011-10-06 | Ranbaxy Laboratories Limited | Salts of dexlansoprazole and their preparation |
EP2384747A3 (en) | 2010-05-05 | 2012-01-18 | Sanovel Ilac Sanayi ve Ticaret A.S. | Oral Tablet Compositions Of Dexlansoprazole |
EP2384746A3 (en) | 2010-05-05 | 2012-03-07 | Sanovel Ilac Sanayi ve Ticaret A.S. | Dual release oral tablet compositions of dexlansoprazole |
EP2384745A3 (en) | 2010-05-05 | 2012-01-18 | Sanovel Ilac Sanayi ve Ticaret A.S. | Modified release pharmaceutical compositions of dexlansoprazole |
WO2012001705A2 (en) | 2010-06-29 | 2012-01-05 | Cadila Healthcare Limited | Pharmaceutical compositions of (r)-lansoprazole |
WO2012074110A1 (ja) | 2010-12-03 | 2012-06-07 | 武田薬品工業株式会社 | 口腔内崩壊錠 |
KR20140007364A (ko) | 2010-12-27 | 2014-01-17 | 다케다 야쿠힌 고교 가부시키가이샤 | 구강내 붕괴정 |
EP2663306A4 (en) * | 2011-01-12 | 2014-01-01 | Hetero Research Foundation | POLYMORPHS OF DEXLANSOPRAZOLE SALTS |
WO2012104805A1 (en) | 2011-02-01 | 2012-08-09 | Ranbaxy Laboratories Limited | Process for the preparation of dexlansoprazole |
WO2012111024A1 (en) | 2011-02-18 | 2012-08-23 | Suven Nishtaa Pharma Pvt Ltd | Pharmaceutical compositions of dexlansoprazole |
CA2840309A1 (en) * | 2011-06-21 | 2012-12-27 | Ranbaxy Laboratories Limited | Process for the preparation of dexlansoprazole |
CN102875532B (zh) * | 2011-07-15 | 2015-05-13 | 上海睿智化学研究有限公司 | 一种(r)-兰索拉唑异丙胺盐及其晶型和制备方法 |
CN102875530A (zh) * | 2011-07-15 | 2013-01-16 | 上海睿智化学研究有限公司 | 一种(r)-兰索拉唑叔丁胺盐及其晶型和制备方法 |
CN102875531B (zh) * | 2011-07-15 | 2015-08-19 | 上海睿智化学研究有限公司 | 一种(r)-兰索拉唑无水晶型及其制备方法 |
CN102234265B (zh) * | 2011-08-08 | 2013-11-20 | 天津市汉康医药生物技术有限公司 | 兰索拉唑化合物 |
ES2561098T3 (es) | 2011-11-30 | 2016-02-24 | Takeda Pharmaceutical Company Limited | Comprimido recubierto en seco |
WO2013088109A1 (en) | 2011-12-16 | 2013-06-20 | Oxagen Limited | Combination of crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
WO2013140120A1 (en) | 2012-03-22 | 2013-09-26 | Cipla Limited | Glycerol solvate forms of (r) - 2 - [ [ [3 -methyl -4 (2,2, 2 - trifluoroethoxy) pyridin- 2 - yl] methyl] sulphinyl] - 1h - ben zimidazole |
WO2013179194A1 (en) | 2012-05-31 | 2013-12-05 | Ranbaxy Laboratories Limited | Process for the preparation of crystalline dexlansoprazole |
CN103709139B (zh) * | 2012-10-09 | 2016-12-21 | 上海汇伦生命科技有限公司 | 无水右兰索拉唑的制备方法 |
CN104177333A (zh) * | 2013-05-24 | 2014-12-03 | 四川海思科制药有限公司 | 一种理化性质稳定的(r)-2-[[[3-甲基-4-(2,2,2-三氟乙氧基)-2-吡啶基]甲基]亚磺酰基]-1h-苯并咪唑 |
CN104650035A (zh) * | 2013-11-25 | 2015-05-27 | 天津市汉康医药生物技术有限公司 | 右兰索拉唑倍半水合物化合物 |
CN103664889B (zh) * | 2013-12-19 | 2014-11-19 | 悦康药业集团有限公司 | 一种兰索拉唑化合物 |
WO2015155307A1 (en) | 2014-04-11 | 2015-10-15 | Sanovel Ilac Sanayi Ve Ticaret A.S. | Pharmaceutical combinations of rivaroxaban and proton pump inhibitors |
US10130618B2 (en) | 2014-04-11 | 2018-11-20 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Pharmaceutical combinations of dabigatran and proton pump inhibitors |
CN104844576B (zh) * | 2015-04-28 | 2017-03-08 | 山东罗欣药业集团股份有限公司 | 一种兰索拉唑或右旋兰索拉唑晶型化合物及其制备方法 |
CN104829594A (zh) * | 2015-05-15 | 2015-08-12 | 苗怡文 | 一种治疗胃溃疡的药物兰索拉唑化合物 |
CN105017218A (zh) * | 2015-07-01 | 2015-11-04 | 合肥安德生制药有限公司 | 一种右兰索拉唑晶型及其制备方法 |
CN104958276A (zh) * | 2015-07-30 | 2015-10-07 | 青岛蓝盛洋医药生物科技有限责任公司 | 一种治疗胃溃疡的药物兰索拉唑组合物胶囊 |
CN104997738A (zh) * | 2015-08-10 | 2015-10-28 | 青岛蓝盛洋医药生物科技有限责任公司 | 一种治疗胃病的药物兰索拉唑组合物干混悬剂 |
CN105399728B (zh) * | 2015-12-20 | 2017-11-28 | 寿光富康制药有限公司 | 一种适用于工业化生产的右兰索拉唑的处理方法 |
CN108164507A (zh) * | 2016-12-07 | 2018-06-15 | 天津药物研究院有限公司 | 一种右兰索拉唑单晶及其制备方法和用途 |
TR201701461A2 (tr) | 2017-01-31 | 2018-08-27 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Dekslansoprazolün Enterik Kaplı Farmasötik Kompozisyonları |
CN106866630B (zh) * | 2017-04-01 | 2018-08-07 | 上海华源医药科技发展有限公司 | 一种右兰索拉唑的制备方法 |
CN107011329A (zh) * | 2017-05-05 | 2017-08-04 | 广州大光制药有限公司 | 兰索拉唑一水合物晶型及其结晶制备方法 |
CN108794450B (zh) * | 2018-07-24 | 2022-08-19 | 浙江恒康药业股份有限公司 | 制备无定型右旋兰索拉唑的方法 |
EP4598528A1 (en) | 2022-10-04 | 2025-08-13 | Arsenil Zabirnyk | Inhibition of aortic valve calcification |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6150978A (ja) | 1984-08-16 | 1986-03-13 | Takeda Chem Ind Ltd | ピリジン誘導体およびその製造法 |
DK171989B1 (da) * | 1987-08-04 | 1997-09-08 | Takeda Chemical Industries Ltd | Fremgangsmåde til fremstilling af 2-(2-pyridylmethylsulfinyl)-benzimidazoler |
DE4035455A1 (de) | 1990-11-08 | 1992-05-14 | Byk Gulden Lomberg Chem Fab | Enantiomerentrennung |
SE504459C2 (sv) | 1994-07-15 | 1997-02-17 | Astra Ab | Förfarande för framställning av substituerade sulfoxider |
GB9423968D0 (en) | 1994-11-28 | 1995-01-11 | Astra Ab | Resolution |
HRP960232A2 (en) | 1995-07-03 | 1998-02-28 | Astra Ab | A process for the optical purification of compounds |
US5840737A (en) * | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
US6043263A (en) | 1996-11-12 | 2000-03-28 | Byk Gulden Lomberg Chemische Fabrik Gmbh | (2,3-dihydrobenzofuranyl)-thiazoles as phosphodiesterase inhibitors |
TW385306B (en) * | 1996-11-14 | 2000-03-21 | Takeda Chemical Industries Ltd | Method for producing crystals of benzimidazole derivatives |
EP0941102A1 (en) * | 1996-11-22 | 1999-09-15 | The Procter & Gamble Company | Compositions for the treatment of gastrointestinal disorders containing bismuth and nsaid |
SE510666C2 (sv) | 1996-12-20 | 1999-06-14 | Astra Ab | Nya Kristallmodifikationer |
CA2320963A1 (en) | 1998-01-30 | 1999-08-05 | Sepracor, Inc. | R-lansoprazole compositions and methods |
EP1056457A4 (en) | 1998-01-30 | 2006-10-25 | Sepracor Inc | S-LANSOPRAZOLE COMPOSITIONS AND METHODS OF USE |
AU3596199A (en) * | 1998-05-06 | 1999-11-23 | Kobenhavns Universitet | Treatment of celiac disease |
TWI289557B (en) * | 1999-06-17 | 2007-11-11 | Takeda Chemical Industries Ltd | A crystal of a hydrate of (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole |
JP3283252B2 (ja) * | 1999-06-17 | 2002-05-20 | 武田薬品工業株式会社 | ベンズイミダゾール化合物の結晶 |
WO2001002389A1 (fr) * | 1999-06-30 | 2001-01-11 | Takeda Chemical Industries, Ltd. | Cristaux de composes benzimidazole |
CN1117747C (zh) * | 2000-06-19 | 2003-08-13 | 中国科学院成都有机化学研究所 | 光学纯兰索拉唑的制备方法 |
EP2596792A1 (en) * | 2002-10-16 | 2013-05-29 | Takeda Pharmaceutical Company Limited | Stable solid preparations |
CA2516600C (en) * | 2003-03-24 | 2011-04-05 | Eisai Co., Ltd. | Process for production of sulfoxide proton pump inhibitors in the amorphous state |
WO2006069159A2 (en) * | 2004-12-20 | 2006-06-29 | Dr. Reddy's Laboratories Ltd. | Pharmaceutical compositions comprising amorphous benzimidazole compounds |
WO2006067599A2 (en) * | 2004-12-23 | 2006-06-29 | Ranbaxy Laboratories Limited | Stable oral benzimidazole compositions and process of preparation thereof |
US20060210637A1 (en) * | 2005-03-17 | 2006-09-21 | Qpharma, Llc | Stable tablet dosage forms of proton pump inhibitors |
NZ593629A (en) * | 2007-12-18 | 2012-11-30 | Watson Pharma Private Ltd | Stable amorphous R-lansoprazole prepared by optically resolving racemic lansoprazole |
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