NO314306B1 - Fremgangsmåte for syntese av benzimidazolforbindelse - Google Patents
Fremgangsmåte for syntese av benzimidazolforbindelse Download PDFInfo
- Publication number
- NO314306B1 NO314306B1 NO19982624A NO982624A NO314306B1 NO 314306 B1 NO314306 B1 NO 314306B1 NO 19982624 A NO19982624 A NO 19982624A NO 982624 A NO982624 A NO 982624A NO 314306 B1 NO314306 B1 NO 314306B1
- Authority
- NO
- Norway
- Prior art keywords
- methoxy
- carried out
- solvent
- omeprazole
- main solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 46
- -1 Benzimidazole Compound Chemical class 0.000 title claims description 9
- 230000015572 biosynthetic process Effects 0.000 title description 3
- 238000003786 synthesis reaction Methods 0.000 title description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 26
- 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 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000000746 purification Methods 0.000 claims description 9
- 238000002955 isolation Methods 0.000 claims description 7
- 239000013067 intermediate product Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000006184 cosolvent Substances 0.000 claims description 4
- 239000003444 phase transfer catalyst Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical group [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 229960000381 omeprazole Drugs 0.000 description 21
- 239000000243 solution Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- PSEPRWKZZJWRCB-UHFFFAOYSA-N (4-methoxy-3,5-dimethylpyridin-2-yl)methanol Chemical compound COC1=C(C)C=NC(CO)=C1C PSEPRWKZZJWRCB-UHFFFAOYSA-N 0.000 description 5
- XURCIPRUUASYLR-UHFFFAOYSA-N Omeprazole sulfide Chemical compound N=1C2=CC(OC)=CC=C2NC=1SCC1=NC=C(C)C(OC)=C1C XURCIPRUUASYLR-UHFFFAOYSA-N 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 4
- 239000011736 potassium bicarbonate Substances 0.000 description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- USSBDBZGEDUBHE-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate Chemical compound [Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O USSBDBZGEDUBHE-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
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
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)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9504503A SE521100C2 (sv) | 1995-12-15 | 1995-12-15 | Förfarande för framställning av en bensimidazolförening |
| PCT/SE1996/001603 WO1997022603A1 (en) | 1995-12-15 | 1996-12-05 | Method for the synthesis of a benzimidazole compound |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO982624L NO982624L (no) | 1998-06-08 |
| NO982624D0 NO982624D0 (no) | 1998-06-08 |
| NO314306B1 true NO314306B1 (no) | 2003-03-03 |
Family
ID=20400614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19982624A NO314306B1 (no) | 1995-12-15 | 1998-06-08 | Fremgangsmåte for syntese av benzimidazolforbindelse |
Country Status (40)
| Country | Link |
|---|---|
| US (1) | US5958955A (de) |
| EP (1) | EP0868423B1 (de) |
| JP (1) | JP3523267B2 (de) |
| KR (1) | KR100433436B1 (de) |
| CN (1) | CN1113879C (de) |
| AR (1) | AR004834A1 (de) |
| AT (1) | ATE205201T1 (de) |
| AU (1) | AU704422B2 (de) |
| CA (1) | CA2238864C (de) |
| CO (1) | CO4750654A1 (de) |
| CZ (1) | CZ288661B6 (de) |
| DE (2) | DE868423T1 (de) |
| DK (1) | DK0868423T3 (de) |
| DZ (1) | DZ2137A1 (de) |
| EE (1) | EE03768B1 (de) |
| EG (1) | EG23859A (de) |
| ES (1) | ES2125210T3 (de) |
| HK (1) | HK1010539A1 (de) |
| HR (1) | HRP960581B1 (de) |
| HU (1) | HUP9900110A3 (de) |
| IL (1) | IL124856A (de) |
| IS (1) | IS1891B (de) |
| MA (1) | MA24026A1 (de) |
| MX (1) | MX9804603A (de) |
| MY (1) | MY115661A (de) |
| NO (1) | NO314306B1 (de) |
| NZ (1) | NZ324482A (de) |
| PL (1) | PL186132B1 (de) |
| PT (1) | PT868423E (de) |
| RU (1) | RU2166502C2 (de) |
| SE (1) | SE521100C2 (de) |
| SI (1) | SI0868423T1 (de) |
| SK (1) | SK282347B6 (de) |
| TN (1) | TNSN96148A1 (de) |
| TR (1) | TR199801070T2 (de) |
| TW (1) | TW460474B (de) |
| UA (1) | UA62921C2 (de) |
| WO (1) | WO1997022603A1 (de) |
| YU (1) | YU49420B (de) |
| ZA (1) | ZA9610067B (de) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE521100C2 (sv) * | 1995-12-15 | 2003-09-30 | Astra Ab | Förfarande för framställning av en bensimidazolförening |
| 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 |
| SK283805B6 (sk) | 1996-09-09 | 2004-02-03 | Slovakofarma, A. S. | Spôsob prípravy omeprazolu |
| US6303787B1 (en) * | 1998-05-27 | 2001-10-16 | Natco Pharma Limited | Intermediates and an improved process for the preparation of Omeprazole employing the said intermediates |
| 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 |
| US6166213A (en) * | 1998-08-11 | 2000-12-26 | Merck & Co., Inc. | Omeprazole process and compositions thereof |
| IL142703A (en) | 1998-11-10 | 2006-04-10 | Astrazeneca Ab | Crystalline form of omeprazole |
| UA72748C2 (en) * | 1998-11-10 | 2005-04-15 | Astrazeneca Ab | A novel crystalline form of omeprazole |
| DE19951960C2 (de) | 1999-10-28 | 2002-06-27 | Gruenenthal Gmbh | Verfahren zur Herstellung als Ulkustherapeutika geeigneter Benzimidazol-Derivate |
| EP1469839A2 (de) * | 2002-01-25 | 2004-10-27 | Santarus, Inc. | Transmukosale verabreichung von protonenpumpeninhibitoren |
| SE0203092D0 (en) | 2002-10-18 | 2002-10-18 | Astrazeneca Ab | Method for the synthesis of a benzimidazole compound |
| US8993599B2 (en) | 2003-07-18 | 2015-03-31 | 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 |
| US8906940B2 (en) | 2004-05-25 | 2014-12-09 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| ZA200706613B (en) * | 2004-12-16 | 2009-03-25 | Cipla Ltd | Process |
| CN100393712C (zh) * | 2006-01-23 | 2008-06-11 | 中国科学院成都有机化学有限公司 | 苯并咪唑型质子泵抑止剂及其前体的改进制备和分离纯化方法 |
| WO2007122686A1 (ja) * | 2006-04-14 | 2007-11-01 | Eisai R & D Management Co., Ltd. | ベンズイミダゾール化合物 |
| NZ579136A (en) * | 2007-02-21 | 2012-05-25 | Cipla Ltd | Process for the preparation of esomeprazole magnesium dihydrate |
| CN101492459B (zh) * | 2008-01-25 | 2011-04-27 | 山东轩竹医药科技有限公司 | 含烷氧乙酰基二氢异噁唑并吡啶化合物 |
| CN101497603B (zh) * | 2008-01-30 | 2012-11-07 | 山东轩竹医药科技有限公司 | 含有被烷氧烷胺氧基取代的吡啶的苯并咪唑衍生物 |
| CN103664885A (zh) * | 2013-12-12 | 2014-03-26 | 武汉工程大学 | 苯并咪唑型质子泵抑制剂中间体的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US461997A (en) * | 1891-10-27 | Sand-pump or other pipes | ||
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| 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 |
| US4619997A (en) * | 1984-09-06 | 1986-10-28 | The Upjohn Company | Substituted 2-pyridylmethylthio and sulfinyl-benzimidazoles as gastric antisecretory agents |
| IL76839A (en) * | 1984-10-31 | 1988-08-31 | Byk Gulden Lomberg Chem Fab | Picoline derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
| SE9002043D0 (sv) * | 1990-06-07 | 1990-06-07 | Astra Ab | Improved method for synthesis |
| NZ244301A (en) * | 1991-09-20 | 1994-08-26 | Merck & Co Inc | Preparation of 2-pyridylmethylsulphinylbenzimidazole and pyridoimidazole derivatives from the corresponding sulphenyl compounds |
| SE521100C2 (sv) * | 1995-12-15 | 2003-09-30 | Astra Ab | Förfarande för framställning av en bensimidazolförening |
-
1995
- 1995-12-15 SE SE9504503A patent/SE521100C2/sv not_active IP Right Cessation
-
1996
- 1996-05-12 UA UA98052782A patent/UA62921C2/uk unknown
- 1996-11-29 ZA ZA9610067A patent/ZA9610067B/xx unknown
- 1996-12-02 AR ARP960105459A patent/AR004834A1/es active IP Right Grant
- 1996-12-02 TN TNTNSN96148A patent/TNSN96148A1/fr unknown
- 1996-12-03 TW TW085114881A patent/TW460474B/zh not_active IP Right Cessation
- 1996-12-04 MA MA24415A patent/MA24026A1/fr unknown
- 1996-12-04 YU YU64296A patent/YU49420B/sh unknown
- 1996-12-04 DZ DZ960182A patent/DZ2137A1/fr active
- 1996-12-05 CN CN96199057A patent/CN1113879C/zh not_active Expired - Fee Related
- 1996-12-05 TR TR1998/01070T patent/TR199801070T2/xx unknown
- 1996-12-05 EE EE9800183A patent/EE03768B1/xx not_active IP Right Cessation
- 1996-12-05 SI SI9630367T patent/SI0868423T1/xx unknown
- 1996-12-05 AT AT96942702T patent/ATE205201T1/de not_active IP Right Cessation
- 1996-12-05 IL IL12485696A patent/IL124856A/en not_active IP Right Cessation
- 1996-12-05 PL PL96327334A patent/PL186132B1/pl not_active IP Right Cessation
- 1996-12-05 DE DE0868423T patent/DE868423T1/de active Pending
- 1996-12-05 US US08/776,222 patent/US5958955A/en not_active Expired - Lifetime
- 1996-12-05 RU RU98110659/04A patent/RU2166502C2/ru not_active IP Right Cessation
- 1996-12-05 DE DE69615052T patent/DE69615052T2/de not_active Expired - Fee Related
- 1996-12-05 KR KR10-1998-0704454A patent/KR100433436B1/ko not_active IP Right Cessation
- 1996-12-05 WO PCT/SE1996/001603 patent/WO1997022603A1/en active IP Right Grant
- 1996-12-05 SK SK768-98A patent/SK282347B6/sk not_active IP Right Cessation
- 1996-12-05 NZ NZ324482A patent/NZ324482A/xx unknown
- 1996-12-05 AU AU11550/97A patent/AU704422B2/en not_active Ceased
- 1996-12-05 PT PT96942702T patent/PT868423E/pt unknown
- 1996-12-05 CA CA002238864A patent/CA2238864C/en not_active Expired - Fee Related
- 1996-12-05 HU HU9900110A patent/HUP9900110A3/hu unknown
- 1996-12-05 JP JP52269797A patent/JP3523267B2/ja not_active Expired - Fee Related
- 1996-12-05 EP EP96942702A patent/EP0868423B1/de not_active Expired - Lifetime
- 1996-12-05 ES ES96942702T patent/ES2125210T3/es not_active Expired - Lifetime
- 1996-12-05 DK DK96942702T patent/DK0868423T3/da active
- 1996-12-05 CZ CZ19981685A patent/CZ288661B6/cs not_active IP Right Cessation
- 1996-12-09 HR HR960581A patent/HRP960581B1/xx not_active IP Right Cessation
- 1996-12-11 CO CO96065025A patent/CO4750654A1/es unknown
- 1996-12-13 MY MYPI96005252A patent/MY115661A/en unknown
- 1996-12-14 EG EG112296A patent/EG23859A/xx active
-
1998
- 1998-05-22 IS IS4750A patent/IS1891B/is unknown
- 1998-06-08 NO NO19982624A patent/NO314306B1/no not_active IP Right Cessation
- 1998-06-09 MX MX9804603A patent/MX9804603A/es not_active IP Right Cessation
- 1998-10-29 HK HK98111601A patent/HK1010539A1/xx not_active IP Right Cessation
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| MM1K | Lapsed by not paying the annual fees |