JP4402174B2 - 新規な化合物形態 - Google Patents
新規な化合物形態 Download PDFInfo
- Publication number
- JP4402174B2 JP4402174B2 JP52868598A JP52868598A JP4402174B2 JP 4402174 B2 JP4402174 B2 JP 4402174B2 JP 52868598 A JP52868598 A JP 52868598A JP 52868598 A JP52868598 A JP 52868598A JP 4402174 B2 JP4402174 B2 JP 4402174B2
- Authority
- JP
- Japan
- Prior art keywords
- omeprazole
- solvent
- neutral
- solution
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical group 0.000 title description 3
- 229960000381 omeprazole Drugs 0.000 claims description 123
- 230000007935 neutral effect Effects 0.000 claims description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 66
- 239000000243 solution Substances 0.000 claims description 44
- 239000002904 solvent Substances 0.000 claims description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 39
- 239000013078 crystal Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000002425 crystallisation Methods 0.000 claims description 12
- 230000008025 crystallization Effects 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000012296 anti-solvent Substances 0.000 claims description 9
- 238000001704 evaporation Methods 0.000 claims description 9
- 210000004211 gastric acid Anatomy 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 7
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 7
- 159000000000 sodium salts Chemical class 0.000 claims description 6
- 208000024891 symptom Diseases 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- -1 alkali metal salt Chemical class 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 208000000689 peptic esophagitis Diseases 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 2
- 239000011259 mixed solution Substances 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 11
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 8
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- SUBDBMMJDZJVOS-XMMPIXPASA-N (R)-omeprazole Chemical compound C([S@@](=O)C=1NC2=CC=C(C=C2N=1)OC)C1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-XMMPIXPASA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 206010019375 Helicobacter infections Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 239000003699 antiulcer agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 208000000718 duodenal ulcer Diseases 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000027119 gastric acid secretion Effects 0.000 description 2
- 201000000052 gastrinoma Diseases 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 208000007882 Gastritis Diseases 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 206010042220 Stress ulcer Diseases 0.000 description 1
- 206010046274 Upper gastrointestinal haemorrhage Diseases 0.000 description 1
- 201000008629 Zollinger-Ellison syndrome Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 208000015419 gastrin-producing neuroendocrine tumor Diseases 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000000711 polarimetry Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Images
Classifications
-
- 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
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9604793A SE510666C2 (sv) | 1996-12-20 | 1996-12-20 | Nya Kristallmodifikationer |
| SE9604793-1 | 1996-12-20 | ||
| PCT/SE1997/002125 WO1998028294A1 (en) | 1996-12-20 | 1997-12-16 | A novel compound form |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001507025A JP2001507025A (ja) | 2001-05-29 |
| JP4402174B2 true JP4402174B2 (ja) | 2010-01-20 |
Family
ID=20405146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52868598A Expired - Fee Related JP4402174B2 (ja) | 1996-12-20 | 1997-12-16 | 新規な化合物形態 |
Country Status (36)
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6699885B2 (en) | 1996-01-04 | 2004-03-02 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and methods of using same |
| US5840737A (en) | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
| US6645988B2 (en) | 1996-01-04 | 2003-11-11 | Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of 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 |
| SI20019A (sl) * | 1998-07-13 | 2000-02-29 | LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. | Izboljšan postopek sinteze 5-metoksi -2-/(4-metoksi-3,5-dimetil-2-piridil)metil/ sulfinil-1H-benzimidazola |
| UA72748C2 (en) * | 1998-11-10 | 2005-04-15 | Astrazeneca Ab | A novel crystalline form of omeprazole |
| IL142703A (en) | 1998-11-10 | 2006-04-10 | Astrazeneca Ab | Crystalline form of omeprazole |
| JP3926936B2 (ja) * | 1998-11-16 | 2007-06-06 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | スルホキシド誘導体・アセトン錯体およびその製造法 |
| SE9804003D0 (sv) | 1998-11-23 | 1998-11-23 | Astra Ab | A method of producing drug particles |
| SE9900274D0 (sv) | 1999-01-28 | 1999-01-28 | Astra Ab | New compound |
| JP2000344739A (ja) * | 1999-06-01 | 2000-12-12 | Sumitomo Chem Co Ltd | Ｎ−保護−アゼチジン−２−カルボン酸の製造方法 |
| 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 |
| SE0000774D0 (sv) * | 2000-03-08 | 2000-03-08 | Astrazeneca Ab | New formulation |
| SE0000773D0 (sv) * | 2000-03-08 | 2000-03-08 | Astrazeneca Ab | New formulation |
| CN100562318C (zh) * | 2000-05-15 | 2009-11-25 | 武田药品工业株式会社 | 晶体的制备方法 |
| GB0016040D0 (en) * | 2000-06-29 | 2000-08-23 | Glaxo Group Ltd | Novel process for preparing crystalline particles |
| AU2001276721A1 (en) | 2000-08-04 | 2002-02-18 | Takeda Chemical Industries Ltd. | Salts of benzimidazole compound and use thereof |
| SI20875A (sl) | 2001-04-25 | 2002-10-31 | LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. | Kristalna oblika omeprazola |
| US8206741B2 (en) | 2001-06-01 | 2012-06-26 | Pozen Inc. | Pharmaceutical compositions for the coordinated delivery of NSAIDs |
| IL159129A0 (en) | 2001-06-01 | 2004-05-12 | Pozen Inc | PHARMACEUTICAL COMPOSITIONS FOR THE COORDINATED DELIVERY OF NSAIDs |
| GB2376231A (en) | 2001-06-06 | 2002-12-11 | Cipla Ltd | Benzimidazole-cyclodextrin inclusion complex |
| SE0102993D0 (sv) | 2001-09-07 | 2001-09-07 | Astrazeneca Ab | New self emulsifying drug delivery system |
| CA2491118A1 (en) * | 2002-06-27 | 2004-01-08 | Dr. Reddy's Laboratories Limited | A process for preparation of optically pure or optically enriched sulfoxide compounds, including amorphous esomeprazole and salts thereof |
| US7169793B2 (en) | 2002-06-27 | 2007-01-30 | Dr. Reddy's Laboratories Limited | Process for preparation of optically pure or optically enriched sulfoxide compounds, including amorphous esomeprazole and salts thereof |
| WO2004020436A1 (en) * | 2002-08-30 | 2004-03-11 | Reddy's Laboratories Limited | Amorphous hydrates of esomeprazole magnesium and process for the preparation thereof |
| AU2003273000A1 (en) | 2002-10-16 | 2004-05-04 | Takeda Pharmaceutical Company Limited | Stable solid preparations |
| US20040235903A1 (en) * | 2002-10-22 | 2004-11-25 | Khanna Mahavir Singh | Amorphous form of esomeprazole salts |
| US20040242642A1 (en) * | 2002-11-18 | 2004-12-02 | Dr. Reddy's Laboratories Limited | Crystalline esomeprazole compounds and process for the preparation thereof |
| MXPA05009183A (es) * | 2003-02-28 | 2005-10-20 | Ranbaxy Lab Ltd | Polimorfos de s-omeprazol. |
| JP4787017B2 (ja) * | 2003-03-24 | 2011-10-05 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | スルホキシド誘導体またはその塩のアモルファスの製造方法 |
| CN1842525A (zh) * | 2003-05-05 | 2006-10-04 | 兰贝克赛实验室有限公司 | 苯并咪唑衍生物的钡盐 |
| US8993599B2 (en) | 2003-07-18 | 2015-03-31 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| SE0400410D0 (sv) | 2004-02-20 | 2004-02-20 | Astrazeneca Ab | New compounds |
| US8906940B2 (en) | 2004-05-25 | 2014-12-09 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| US8815916B2 (en) | 2004-05-25 | 2014-08-26 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| EP1768668A2 (en) | 2004-06-16 | 2007-04-04 | Tap Pharmaceutical Products, Inc. | Multiple ppi dosage form |
| US8658799B2 (en) * | 2004-06-24 | 2014-02-25 | Astrazeneca Ab | Process for the preparation of crystalline modifications for use in the preparation of esomeperazole sodium salt |
| ES2246149B1 (es) * | 2004-07-02 | 2007-06-01 | Esteve Quimica, S.A. | Formas solidas de la sal magnesica de s-omeprazol y procedimientos para su preparacion. |
| US20090298884A1 (en) * | 2005-05-06 | 2009-12-03 | Glenmark Generics Ltd. | Esomeprazole Strontium Salt, Process For Its Preparation and Pharmaceutical Compositions Containing Same |
| US8247566B2 (en) * | 2005-06-08 | 2012-08-21 | Lek Pharmaceuticals D.D. | Crystalline solvate of omeprazole sodium |
| US7563812B2 (en) | 2005-06-15 | 2009-07-21 | Hetero Drugs Limited | Amorphous esomeprazole hydrate |
| NL2000126C2 (nl) * | 2005-07-15 | 2008-01-29 | Solvay | Werkwijze voor de vervaardiging van eptifibatide. |
| US20070043085A1 (en) * | 2005-08-19 | 2007-02-22 | Glenmark Pharmaceuticals Limited | Process for the preparation of amorphous form of neutral esomeprazole |
| US7576219B2 (en) | 2005-10-26 | 2009-08-18 | Hanmi Pharm. Co., Ltd | Crystalline S-omeprazole strontium hydrate, method for preparing same, and pharmaceutical composition containing same |
| WO2007054951A1 (en) * | 2005-11-14 | 2007-05-18 | Hetero Drugs Limited | Process for amorphous esomeprazole |
| BRPI0619158A2 (pt) * | 2005-12-05 | 2011-09-20 | Astrazeneca Ab | processo para preparar forma que não que não seja sal de esomeprazol, composto, formulação farmacêutica, e, método de tratamento |
| EP1801110A1 (en) | 2005-12-22 | 2007-06-27 | KRKA, tovarna zdravil, d.d., Novo mesto | Esomeprazole arginine salt |
| SI1973896T1 (sl) | 2005-12-28 | 2009-08-31 | Union Quimico Farma | Postopek priprave (S) - enantiomere omeprazola |
| EP2000468A1 (en) * | 2007-05-09 | 2008-12-10 | Dr. Reddy's Laboratories Ltd. | Esomeprazole salts and processes for preparation thereof |
| WO2009047775A2 (en) * | 2007-10-08 | 2009-04-16 | Hetero Drugs Limited | Polymorphs of esomeprazole salts |
| NZ588379A (en) | 2008-03-10 | 2012-07-27 | Takeda Pharmaceutical | Crystal of benzimidazole compound |
| EP2143722A1 (en) | 2008-07-09 | 2010-01-13 | Lek Pharmaceuticals D.D. | Process for preparation of esomeprazole sodium of high chemical purity and new forms of esomeprazole sodium |
| AU2009290712A1 (en) | 2008-09-09 | 2010-03-18 | Astrazeneca Ab | Method for delivering a pharmaceutical composition to patient in need thereof |
| EA201290026A1 (ru) | 2009-06-25 | 2012-07-30 | Астразенека Аб | Способ лечения пациента, имеющего риск развития язвы, связанной с приемом нестероидных противовоспалительных средств (nsaid) |
| EP2510089B1 (en) | 2009-12-08 | 2015-10-21 | Codexis, Inc. | Synthesis of prazole compounds |
| HUE037616T2 (hu) | 2010-12-08 | 2018-09-28 | Codexis Inc | Biokatalizátorok és eljárások armodafinil szintéziséhez |
| EA028049B1 (ru) | 2011-12-28 | 2017-10-31 | Поузен Инк. | Улучшенные композиции и способы доставки омепразола и ацетилсалициловой кислоты |
| RU2501549C1 (ru) | 2012-08-30 | 2013-12-20 | Авва Девелопмент Лтд | Фармацевтическая композиция для лечения гастроэзофагеальной рефлюксной болезни |
| CN107043367A (zh) * | 2017-05-26 | 2017-08-15 | 重庆莱美隆宇药业有限公司 | 一种中性s‑奥美拉唑的干燥工艺 |
| WO2024075017A1 (en) | 2022-10-04 | 2024-04-11 | Zabirnyk Arsenii | Inhibition of aortic valve calcification |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| SE8301182D0 (sv) * | 1983-03-04 | 1983-03-04 | Haessle Ab | Novel compounds |
| GB2189698A (en) * | 1986-04-30 | 1987-11-04 | Haessle Ab | Coated omeprazole tablets |
| SE9002043D0 (sv) * | 1990-06-07 | 1990-06-07 | Astra Ab | Improved method for synthesis |
| DE4035455A1 (de) * | 1990-11-08 | 1992-05-14 | Byk Gulden Lomberg Chem Fab | Enantiomerentrennung |
| US5877192A (en) * | 1993-05-28 | 1999-03-02 | Astra Aktiebolag | Method for the treatment of gastric acid-related diseases and production of medication using (-) enantiomer of omeprazole |
| SE9301830D0 (sv) * | 1993-05-28 | 1993-05-28 | Ab Astra | New compounds |
| SE9302396D0 (sv) * | 1993-07-09 | 1993-07-09 | Ab Astra | A novel compound form |
| WO1996001623A1 (en) * | 1994-07-08 | 1996-01-25 | Astra Aktiebolag | Multiple unit tableted dosage form i |
-
1996
- 1996-12-20 SE SE9604793A patent/SE510666C2/sv unknown
-
1997
- 1997-12-08 TW TW086118449A patent/TW538039B/zh not_active IP Right Cessation
- 1997-12-09 ZA ZA9711046A patent/ZA9711046B/xx unknown
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