SK10792003A3 - Spôsob výroby substituovaných 2-(2-pyridylmetyl) sulfinyl -1H-benzimidazolov - Google Patents
Spôsob výroby substituovaných 2-(2-pyridylmetyl) sulfinyl -1H-benzimidazolov Download PDFInfo
- Publication number
- SK10792003A3 SK10792003A3 SK1079-2003A SK10792003A SK10792003A3 SK 10792003 A3 SK10792003 A3 SK 10792003A3 SK 10792003 A SK10792003 A SK 10792003A SK 10792003 A3 SK10792003 A3 SK 10792003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- methyl
- oxidation
- formula
- methoxy
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 45
- HBDKFZNDMVLSHM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfinyl)-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=N1 HBDKFZNDMVLSHM-UHFFFAOYSA-N 0.000 title abstract description 10
- 238000004519 manufacturing process Methods 0.000 title description 8
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 53
- 230000003647 oxidation Effects 0.000 claims description 43
- 238000007254 oxidation reaction Methods 0.000 claims description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- -1 thioester compound Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 239000007800 oxidant agent Substances 0.000 claims description 14
- 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 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 229960000381 omeprazole Drugs 0.000 claims description 10
- 150000003568 thioethers Chemical class 0.000 claims description 10
- 239000006227 byproduct Substances 0.000 claims description 9
- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 claims description 9
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 claims description 8
- 150000003457 sulfones Chemical class 0.000 claims description 8
- IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 claims description 7
- 229960003174 lansoprazole Drugs 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 229960005019 pantoprazole Drugs 0.000 claims description 7
- CQKAPARXKPTKBK-UHFFFAOYSA-N tert-butylazanium;bromide Chemical compound Br.CC(C)(C)N CQKAPARXKPTKBK-UHFFFAOYSA-N 0.000 claims description 7
- 125000005287 vanadyl group Chemical group 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
- 229960004157 rabeprazole Drugs 0.000 claims description 6
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000003444 phase transfer catalyst Substances 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 11
- FSJSYDFBTIVUFD-XHTSQIMGSA-N (e)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C/C(C)=O.C\C(O)=C/C(C)=O FSJSYDFBTIVUFD-XHTSQIMGSA-N 0.000 description 10
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 9
- 235000010262 sodium metabisulphite Nutrition 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 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 8
- 238000003756 stirring Methods 0.000 description 8
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 7
- 150000003462 sulfoxides Chemical class 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- 239000004296 sodium metabisulphite Substances 0.000 description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 6
- CCHLMSUZHFPSFC-UHFFFAOYSA-N 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfanyl]-1h-benzimidazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CSC1=NC2=CC=CC=C2N1 CCHLMSUZHFPSFC-UHFFFAOYSA-N 0.000 description 5
- BSXAHDOWMOSVAP-UHFFFAOYSA-N 2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfanyl]-1h-benzimidazole Chemical compound COCCCOC1=CC=NC(CSC=2NC3=CC=CC=C3N=2)=C1C BSXAHDOWMOSVAP-UHFFFAOYSA-N 0.000 description 5
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- UKILEIRWOYBGEJ-UHFFFAOYSA-N 6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfanyl]-1h-benzimidazole Chemical compound COC1=CC=NC(CSC=2NC3=CC(OC(F)F)=CC=C3N=2)=C1OC UKILEIRWOYBGEJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 231100001261 hazardous Toxicity 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- IXEQEYRTSRFZEO-UHFFFAOYSA-N Omeprazole sulfone Chemical compound N1C2=CC(OC)=CC=C2N=C1S(=O)(=O)CC1=NC=C(C)C(OC)=C1C IXEQEYRTSRFZEO-UHFFFAOYSA-N 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- FSJSYDFBTIVUFD-SUKNRPLKSA-N (z)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FSJSYDFBTIVUFD-SUKNRPLKSA-N 0.000 description 2
- FCJYMBZQIJDMMM-UHFFFAOYSA-N 1H-Benzimidazole, 5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfonyl]- Chemical compound COC1=CC=NC(CS(=O)(=O)C=2NC3=CC(OC(F)F)=CC=C3N=2)=C1OC FCJYMBZQIJDMMM-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 2
- KNYNPBSPFHFPML-UHFFFAOYSA-N 2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfonyl]-1h-benzimidazole Chemical compound COCCCOC1=CC=NC(CS(=O)(=O)C=2NC3=CC=CC=C3N=2)=C1C KNYNPBSPFHFPML-UHFFFAOYSA-N 0.000 description 2
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 2
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 2
- TVMJMCGRSSSSDJ-UHFFFAOYSA-N lansoprazole sulfone Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)(=O)C1=NC2=CC=CC=C2N1 TVMJMCGRSSSSDJ-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
- 229910001935 vanadium oxide Inorganic materials 0.000 description 2
- OZURYZAHRAPLJF-UHFFFAOYSA-N 2-(phenylsulfanylmethyl)pyridine Chemical class C=1C=CC=NC=1CSC1=CC=CC=C1 OZURYZAHRAPLJF-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 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
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 150000007970 thio esters Chemical group 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26616201P | 2001-02-02 | 2001-02-02 | |
| PCT/US2002/003225 WO2002062786A1 (en) | 2001-02-02 | 2002-02-04 | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1h-benzimidazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK10792003A3 true SK10792003A3 (sk) | 2004-07-07 |
Family
ID=23013433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1079-2003A SK10792003A3 (sk) | 2001-02-02 | 2002-02-04 | Spôsob výroby substituovaných 2-(2-pyridylmetyl) sulfinyl -1H-benzimidazolov |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US7129358B2 (cs) |
| EP (2) | EP1363901A4 (cs) |
| JP (1) | JP2004524303A (cs) |
| KR (1) | KR20040029966A (cs) |
| CN (3) | CN1876647A (cs) |
| CA (1) | CA2436467A1 (cs) |
| CZ (1) | CZ20032351A3 (cs) |
| DE (1) | DE02706135T1 (cs) |
| ES (1) | ES2209678T1 (cs) |
| HR (1) | HRP20030691A2 (cs) |
| HU (1) | HUP0303144A3 (cs) |
| IS (1) | IS6897A (cs) |
| MX (1) | MXPA03006904A (cs) |
| NO (1) | NO20033433L (cs) |
| PL (1) | PL368563A1 (cs) |
| SK (1) | SK10792003A3 (cs) |
| WO (1) | WO2002062786A1 (cs) |
| YU (1) | YU61103A (cs) |
| ZA (1) | ZA200305652B (cs) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA03006904A (es) | 2001-02-02 | 2004-12-06 | Teva Pharma | Procesos para la produccion de 2-(2-piridilmetil) sulfinil - 1h - bencimidazoles sustituidos. |
| US20040010151A1 (en) * | 2002-03-27 | 2004-01-15 | Nina Finkelstein | Lansoprazole polymorphs and processes for preparation thereof |
| WO2004011455A1 (en) * | 2002-07-26 | 2004-02-05 | Teva Pharmaceutical Industries Ltd. | Preparation of lansoprazole and related compounds |
| US6909004B2 (en) * | 2002-08-21 | 2005-06-21 | Teva Pharmaceutical Industries Ltd. | Method for the purification of lansoprazole |
| ES2237354T3 (es) * | 2002-11-18 | 2007-11-01 | Teva Pharmaceutical Industries Ltd. | Lansoprazol estable que contiene mas de 500 ppm, hasta aproximadamente 3.000 ppm de agua y mas de 200 ppm, hasta aproximadamente 5.000 ppm de alcohol. |
| EP1572680A2 (en) | 2002-12-19 | 2005-09-14 | Eva Pharmaceutical Industries Ltd. | Solid states of pantoprazole sodium, known pantoprazole sodium hydrates, processes for their preparation. |
| US7678816B2 (en) * | 2003-02-05 | 2010-03-16 | Teva Pharmaceutical Industries Ltd. | Method of stabilizing lansoprazole |
| ES2245277T1 (es) * | 2003-03-12 | 2006-01-01 | Teva Pharmaceutical Industries Limited | Solidos cristalinos y amorfos de pantoprazol y procedimientos para su preparacion. |
| WO2004111029A2 (en) * | 2003-06-10 | 2004-12-23 | Teva Pharmaceutical Industries Ltd. | Process for preparing 2-[(pyridinyl)methyl]sulfinyl-substituted benzimidazoles and novel chlorinated derivatives of pantoprazole |
| FR2871800B1 (fr) * | 2004-06-17 | 2006-08-25 | Sidem Pharma Sa Sa | Sel de sodium monohydrate du s-tenatoprazole et application en therapeutique |
| DE112005003147T5 (de) | 2004-12-16 | 2008-01-17 | Cipla Ltd. | Verfahren |
| EP1681056A1 (en) * | 2005-01-14 | 2006-07-19 | Krka Tovarna Zdravil, D.D., Novo Mesto | Process for preparing lansoprazole |
| AR054113A1 (es) * | 2005-05-06 | 2007-06-06 | Medichem Sa | Forma cristalina solida de pantoprazol como acido libre, sales derivadas del mismo y proceso para su preparacion |
| CN1919844B (zh) * | 2006-09-01 | 2010-05-12 | 武汉工程大学 | 水相氧化合成兰索拉唑的方法 |
| WO2010039885A2 (en) * | 2008-09-30 | 2010-04-08 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of dexlansoprazole |
| WO2010134099A1 (en) * | 2009-05-21 | 2010-11-25 | Cadila Healthcare Limited | One pot process for preparing omeprazole and related compounds |
| CN108623564B (zh) * | 2017-03-17 | 2022-11-04 | 江苏豪森药业集团有限公司 | 一种雷贝拉唑类似物的制备方法 |
| CN111072633A (zh) * | 2019-12-19 | 2020-04-28 | 山东达因海洋生物制药股份有限公司 | 一种埃索美拉唑镁三水合物的制备方法 |
| CN112174934B (zh) * | 2020-10-15 | 2023-12-22 | 成都百泉生物医药科技有限公司 | 一种奥美拉唑的合成方法及其合成设备 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1140119A (en) | 1978-04-03 | 1983-01-25 | Joseph Torremans | N-heterocyclyl-4-piperidinamines |
| SE7804231L (sv) | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| GB2069492B (en) | 1980-02-20 | 1984-02-29 | Wyeth John & Brother Ltd | Sulphur compounds |
| SE8300736D0 (sv) * | 1983-02-11 | 1983-02-11 | Haessle Ab | Novel pharmacologically active compounds |
| DK171989B1 (da) | 1987-08-04 | 1997-09-08 | Takeda Chemical Industries Ltd | Fremgangsmåde til fremstilling af 2-(2-pyridylmethylsulfinyl)-benzimidazoler |
| 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 |
| ES2063705B1 (es) * | 1993-06-14 | 1995-07-16 | S A L V A T Lab Sa | Intermedio para la sintesis de lansoprazol y su procedimiento de obtencion. |
| SK283805B6 (sk) * | 1996-09-09 | 2004-02-03 | Slovakofarma, A. S. | Spôsob prípravy omeprazolu |
| SE9704183D0 (sv) * | 1997-11-14 | 1997-11-14 | Astra Ab | New process |
| AU751066B2 (en) * | 1997-12-08 | 2002-08-08 | Nycomed Gmbh | Novel administration form comprising an acid-labile active compound |
| GB9805558D0 (en) * | 1998-03-17 | 1998-05-13 | Knoll Ag | Chemical process` |
| 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 |
| JP4047993B2 (ja) * | 1999-01-04 | 2008-02-13 | 理想科学工業株式会社 | 孔版印刷方法 |
| US6245913B1 (en) * | 1999-06-30 | 2001-06-12 | Wockhardt Europe Limited | Synthetic procedure for 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methylthio]-IH-benzimidazole hydrochloride and its conversion to omeprazole |
| ES2163372B1 (es) * | 2000-03-13 | 2003-05-01 | Esteve Quimica Sa | Procedimiento de oxidacion de un grupo tioeter a sulfoxido. |
| MXPA03006904A (es) | 2001-02-02 | 2004-12-06 | Teva Pharma | Procesos para la produccion de 2-(2-piridilmetil) sulfinil - 1h - bencimidazoles sustituidos. |
-
2002
- 2002-02-04 MX MXPA03006904A patent/MXPA03006904A/es not_active Application Discontinuation
- 2002-02-04 YU YU61103A patent/YU61103A/sh unknown
- 2002-02-04 WO PCT/US2002/003225 patent/WO2002062786A1/en active Application Filing
- 2002-02-04 HU HU0303144A patent/HUP0303144A3/hu unknown
- 2002-02-04 DE DE0001363901T patent/DE02706135T1/de active Pending
- 2002-02-04 ZA ZA200305652A patent/ZA200305652B/en unknown
- 2002-02-04 EP EP02706135A patent/EP1363901A4/en not_active Withdrawn
- 2002-02-04 US US10/066,850 patent/US7129358B2/en not_active Expired - Fee Related
- 2002-02-04 CZ CZ20032351A patent/CZ20032351A3/cs unknown
- 2002-02-04 CA CA002436467A patent/CA2436467A1/en not_active Abandoned
- 2002-02-04 JP JP2002563139A patent/JP2004524303A/ja active Pending
- 2002-02-04 CN CNA2006100819206A patent/CN1876647A/zh active Pending
- 2002-02-04 KR KR10-2003-7010217A patent/KR20040029966A/ko not_active Ceased
- 2002-02-04 CN CNB028044851A patent/CN100347167C/zh not_active Expired - Fee Related
- 2002-02-04 HR HR20030691A patent/HRP20030691A2/xx not_active Application Discontinuation
- 2002-02-04 EP EP08010970A patent/EP1970374A1/en not_active Ceased
- 2002-02-04 PL PL02368563A patent/PL368563A1/xx not_active Application Discontinuation
- 2002-02-04 CN CNA200510086094XA patent/CN1781918A/zh active Pending
- 2002-02-04 SK SK1079-2003A patent/SK10792003A3/sk not_active Application Discontinuation
- 2002-02-04 ES ES02706135T patent/ES2209678T1/es active Pending
-
2003
- 2003-07-29 IS IS6897A patent/IS6897A/is unknown
- 2003-08-01 NO NO20033433A patent/NO20033433L/no not_active Application Discontinuation
-
2006
- 2006-09-05 US US11/514,964 patent/US20060293363A1/en not_active Abandoned
-
2007
- 2007-10-09 US US11/973,744 patent/US20080091024A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IS6897A (is) | 2003-07-29 |
| CN1781918A (zh) | 2006-06-07 |
| EP1363901A4 (en) | 2005-08-31 |
| NO20033433D0 (no) | 2003-08-01 |
| US20030036554A1 (en) | 2003-02-20 |
| CA2436467A1 (en) | 2002-08-15 |
| CN100347167C (zh) | 2007-11-07 |
| HUP0303144A3 (en) | 2007-08-28 |
| MXPA03006904A (es) | 2004-12-06 |
| US20080091024A1 (en) | 2008-04-17 |
| NO20033433L (no) | 2003-09-25 |
| DE02706135T1 (de) | 2004-05-19 |
| CZ20032351A3 (cs) | 2004-08-18 |
| CN1489585A (zh) | 2004-04-14 |
| HUP0303144A2 (hu) | 2004-03-01 |
| US7129358B2 (en) | 2006-10-31 |
| EP1970374A1 (en) | 2008-09-17 |
| US20060293363A1 (en) | 2006-12-28 |
| WO2002062786A1 (en) | 2002-08-15 |
| EP1363901A1 (en) | 2003-11-26 |
| ZA200305652B (en) | 2004-07-22 |
| PL368563A1 (en) | 2005-04-04 |
| HRP20030691A2 (en) | 2005-04-30 |
| ES2209678T1 (es) | 2004-07-01 |
| JP2004524303A (ja) | 2004-08-12 |
| YU61103A (sh) | 2006-05-25 |
| KR20040029966A (ko) | 2004-04-08 |
| CN1876647A (zh) | 2006-12-13 |
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| Date | Code | Title | Description |
|---|---|---|---|
| FC9A | Refused patent application |