SE521100C2 - Förfarande för framställning av en bensimidazolförening - Google Patents
Förfarande för framställning av en bensimidazolföreningInfo
- Publication number
- SE521100C2 SE521100C2 SE9504503A SE9504503A SE521100C2 SE 521100 C2 SE521100 C2 SE 521100C2 SE 9504503 A SE9504503 A SE 9504503A SE 9504503 A SE9504503 A SE 9504503A SE 521100 C2 SE521100 C2 SE 521100C2
- Authority
- SE
- Sweden
- Prior art keywords
- methoxy
- pyridinyl
- dimethyl
- methyl
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- -1 benzimidazole compound Chemical class 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002904 solvent Substances 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 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 abstract description 14
- 229960000381 omeprazole Drugs 0.000 claims abstract description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 12
- 239000000543 intermediate Substances 0.000 claims abstract description 8
- 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 claims abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 8
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229940050176 methyl chloride Drugs 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- SRKVJDYNPSMHJM-UHFFFAOYSA-N 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine Chemical compound COC1=C(C)C=NC(CCl)=C1C SRKVJDYNPSMHJM-UHFFFAOYSA-N 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 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 abstract description 7
- 239000000376 reactant Substances 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 3
- 238000002955 isolation Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (41)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9504503A SE521100C2 (sv) | 1995-12-15 | 1995-12-15 | Förfarande för framställning av en bensimidazolförening |
| UA98052782A UA62921C2 (en) | 1995-12-15 | 1996-05-12 | A process for the synthesis of benzimidazole compound |
| ZA9610067A ZA9610067B (en) | 1995-12-15 | 1996-11-29 | Method for the synthesis of a benzimidazole compound |
| TNTNSN96148A TNSN96148A1 (fr) | 1995-12-15 | 1996-12-02 | Methode pour la synthese d'un benzimidazole. |
| ARP960105459A AR004834A1 (es) | 1995-12-15 | 1996-12-02 | Procedimiento de la manufactura de (5-metoxi-2[[(4-metoxi-3,5-dimetil-2- piridinil)-metil]-sulfinil]-1h-bencimidazol (omeprazol) |
| TW085114881A TW460474B (en) | 1995-12-15 | 1996-12-03 | Process for the manufacture of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulphinyl]-1H-benzimidazole |
| MA24415A MA24026A1 (fr) | 1995-12-15 | 1996-12-04 | Methode pour la synthese d'un benzimidazole |
| DZ960182A DZ2137A1 (fr) | 1995-12-15 | 1996-12-04 | Méthode pour la synthèse d'un benzimidazole. |
| YU64296A YU49420B (sh) | 1995-12-15 | 1996-12-04 | Postupak sinteze benzimidazolskog jedinjenja |
| PL96327334A PL186132B1 (pl) | 1995-12-15 | 1996-12-05 | Sposób wytwarzania 5-metoksy-2-[[(4-metoksy-3,5-dimetylo-2-pirydynylo)metylo]sulfinylo]-1H-benzimidazolu |
| IL12485696A IL124856A (en) | 1995-12-15 | 1996-12-05 | Process for the production of omeprazole |
| DE0868423T DE868423T1 (de) | 1995-12-15 | 1996-12-05 | Verfahren zur herstellung einer benzimidazolverbindung |
| ES96942702T ES2125210T3 (es) | 1995-12-15 | 1996-12-05 | Metodo para la sintesis de un compuesto de bencimidazol. |
| RU98110659/04A RU2166502C2 (ru) | 1995-12-15 | 1996-12-05 | Способ производства 5-метокси-2-[[(4-метокси-3,5-диметил-2-пиридинил)-метил]сульфинил]-1н-бенз имидазола |
| CZ19981685A CZ288661B6 (cs) | 1995-12-15 | 1996-12-05 | Způsob výroby 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazolu |
| HK98111601.1A HK1010539B (en) | 1995-12-15 | 1996-12-05 | Method for the synthesis of a benzimidazole compound |
| NZ324482A NZ324482A (en) | 1995-12-15 | 1996-12-05 | Process for the synthesis of omeprazole |
| AU11550/97A AU704422B2 (en) | 1995-12-15 | 1996-12-05 | Method for the synthesis of a benzimidazole compound |
| PT96942702T PT868423E (pt) | 1995-12-15 | 1996-12-05 | Metodo para a sintese de um composto de benzimidazole |
| PCT/SE1996/001603 WO1997022603A1 (en) | 1995-12-15 | 1996-12-05 | Method for the synthesis of a benzimidazole compound |
| DK96942702T DK0868423T3 (da) | 1995-12-15 | 1996-12-05 | Fremgangsmåde til syntese af en benzimidazolforbindelse |
| US08/776,222 US5958955A (en) | 1995-12-15 | 1996-12-05 | Method for the synthesis of a benzimidazole compound |
| SI9630367T SI0868423T1 (en) | 1995-12-15 | 1996-12-05 | Method for the synthesis of a benzimidazole compound |
| AT96942702T ATE205201T1 (de) | 1995-12-15 | 1996-12-05 | Verfahren zur herstellung einer benzimidazolverbindung |
| KR10-1998-0704454A KR100433436B1 (ko) | 1995-12-15 | 1996-12-05 | 벤즈이미다졸화합물의합성방법 |
| EP96942702A EP0868423B1 (en) | 1995-12-15 | 1996-12-05 | Method for the synthesis of a benzimidazole compound |
| TR1998/01070T TR199801070T2 (xx) | 1995-12-15 | 1996-12-05 | Benzimidazol bile�i�inin sentezi i�in bir y�ntem |
| JP52269797A JP3523267B2 (ja) | 1995-12-15 | 1996-12-05 | ベンゾイミダゾール化合物の合成法 |
| EE9800183A EE03768B1 (et) | 1995-12-15 | 1996-12-05 | Meetod bensimidasoolühendi sünteesiks |
| HU9900110A HUP9900110A3 (en) | 1995-12-15 | 1996-12-05 | Novel process for the synthesis of omeprazole |
| CA002238864A CA2238864C (en) | 1995-12-15 | 1996-12-05 | Method for the synthesis of a benzimidazole compound |
| DE69615052T DE69615052T2 (de) | 1995-12-15 | 1996-12-05 | Verfahren zur herstellung einer benzimidazolverbindung |
| SK768-98A SK282347B6 (sk) | 1995-12-15 | 1996-12-05 | Spôsob prípravy benzimidazolovej zlúčeniny |
| CN96199057A CN1113879C (zh) | 1995-12-15 | 1996-12-05 | 苯并咪唑化合物的合成方法 |
| HR960581A HRP960581B1 (en) | 1995-12-15 | 1996-12-09 | Method for the synthesis of a benzimidazole compound |
| CO96065025A CO4750654A1 (es) | 1995-12-15 | 1996-12-11 | Proceso para la sintesis de un compuesto omeprazol |
| MYPI96005252A MY115661A (en) | 1995-12-15 | 1996-12-13 | Method for the synthesis of a benzimidazole compound |
| EG112296A EG23859A (en) | 1995-12-15 | 1996-12-14 | Method for the synthesis of a benzimidazole compound |
| IS4750A IS1891B (is) | 1995-12-15 | 1998-05-22 | Aðferð við að nýmynda bensimídasólefnasamband |
| NO19982624A NO314306B1 (no) | 1995-12-15 | 1998-06-08 | Fremgangsmåte for syntese av benzimidazolforbindelse |
| MX9804603A MX9804603A (es) | 1995-12-15 | 1998-06-09 | Metodo para la sintesis de un compuesto de benzimidazol. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9504503A SE521100C2 (sv) | 1995-12-15 | 1995-12-15 | Förfarande för framställning av en bensimidazolförening |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE9504503D0 SE9504503D0 (sv) | 1995-12-15 |
| SE9504503L SE9504503L (sv) | 1997-06-16 |
| SE521100C2 true SE521100C2 (sv) | 2003-09-30 |
Family
ID=20400614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE9504503A SE521100C2 (sv) | 1995-12-15 | 1995-12-15 | Förfarande för framställning av en bensimidazolförening |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US5958955A (cs) |
| EP (1) | EP0868423B1 (cs) |
| JP (1) | JP3523267B2 (cs) |
| KR (1) | KR100433436B1 (cs) |
| CN (1) | CN1113879C (cs) |
| AR (1) | AR004834A1 (cs) |
| AT (1) | ATE205201T1 (cs) |
| AU (1) | AU704422B2 (cs) |
| CA (1) | CA2238864C (cs) |
| CO (1) | CO4750654A1 (cs) |
| CZ (1) | CZ288661B6 (cs) |
| DE (2) | DE868423T1 (cs) |
| DK (1) | DK0868423T3 (cs) |
| DZ (1) | DZ2137A1 (cs) |
| EE (1) | EE03768B1 (cs) |
| EG (1) | EG23859A (cs) |
| ES (1) | ES2125210T3 (cs) |
| HR (1) | HRP960581B1 (cs) |
| HU (1) | HUP9900110A3 (cs) |
| IL (1) | IL124856A (cs) |
| IS (1) | IS1891B (cs) |
| MA (1) | MA24026A1 (cs) |
| MX (1) | MX9804603A (cs) |
| MY (1) | MY115661A (cs) |
| NO (1) | NO314306B1 (cs) |
| NZ (1) | NZ324482A (cs) |
| PL (1) | PL186132B1 (cs) |
| PT (1) | PT868423E (cs) |
| RU (1) | RU2166502C2 (cs) |
| SE (1) | SE521100C2 (cs) |
| SI (1) | SI0868423T1 (cs) |
| SK (1) | SK282347B6 (cs) |
| TN (1) | TNSN96148A1 (cs) |
| TR (1) | TR199801070T2 (cs) |
| TW (1) | TW460474B (cs) |
| UA (1) | UA62921C2 (cs) |
| WO (1) | WO1997022603A1 (cs) |
| YU (1) | YU49420B (cs) |
| ZA (1) | ZA9610067B (cs) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE521100C2 (sv) * | 1995-12-15 | 2003-09-30 | Astra Ab | Förfarande för framställning av en bensimidazolförening |
| US6489346B1 (en) * | 1996-01-04 | 2002-12-03 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of 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 |
| 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 |
| 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 |
| 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 |
| RU2247120C2 (ru) * | 1999-10-28 | 2005-02-27 | Грюненталь Гмбх | Способ получения противоязвенных терапевтических средств |
| DE19951960C2 (de) * | 1999-10-28 | 2002-06-27 | Gruenenthal Gmbh | Verfahren zur Herstellung als Ulkustherapeutika geeigneter Benzimidazol-Derivate |
| MXPA04007169A (es) * | 2002-01-25 | 2004-10-29 | Santarus Inc | Suministro transmucosal de inhibidores de bomba de protones. |
| 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 |
| 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 |
| JP5355893B2 (ja) * | 2004-12-16 | 2013-11-27 | シプラ・リミテッド | パントプラゾールナトリウムの製造方法 |
| 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 YU YU64296A patent/YU49420B/sh unknown
- 1996-12-04 MA MA24415A patent/MA24026A1/fr unknown
- 1996-12-04 DZ DZ960182A patent/DZ2137A1/fr active
- 1996-12-05 PL PL96327334A patent/PL186132B1/pl not_active IP Right Cessation
- 1996-12-05 DK DK96942702T patent/DK0868423T3/da active
- 1996-12-05 WO PCT/SE1996/001603 patent/WO1997022603A1/en active IP Right Grant
- 1996-12-05 AU AU11550/97A patent/AU704422B2/en not_active Ceased
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