ZA200305652B - Processes for the production of substituted 2-(2-pyridyl-methyl) sulfinyl-1H-benzimidazoles. - Google Patents
Processes for the production of substituted 2-(2-pyridyl-methyl) sulfinyl-1H-benzimidazoles. Download PDFInfo
- Publication number
- ZA200305652B ZA200305652B ZA200305652A ZA200305652A ZA200305652B ZA 200305652 B ZA200305652 B ZA 200305652B ZA 200305652 A ZA200305652 A ZA 200305652A ZA 200305652 A ZA200305652 A ZA 200305652A ZA 200305652 B ZA200305652 B ZA 200305652B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- process according
- sulfone
- product
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 67
- 238000004519 manufacturing process Methods 0.000 title claims description 21
- 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 description 6
- 230000003647 oxidation Effects 0.000 claims description 66
- 238000007254 oxidation reaction Methods 0.000 claims description 66
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- -1 thioester compound Chemical class 0.000 claims description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- 239000006227 byproduct Substances 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 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 28
- 150000003457 sulfones Chemical class 0.000 claims description 28
- 150000003568 thioethers Chemical class 0.000 claims description 28
- 229960000381 omeprazole Drugs 0.000 claims description 26
- 239000007800 oxidant agent Substances 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 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 20
- 229960003174 lansoprazole Drugs 0.000 claims description 20
- 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 20
- 229960005019 pantoprazole Drugs 0.000 claims description 20
- 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 20
- 229960004157 rabeprazole Drugs 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 229910001868 water Inorganic materials 0.000 claims description 12
- 239000012425 OXONE® Substances 0.000 claims description 11
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 125000005287 vanadyl group Chemical group 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
- 239000003444 phase transfer catalyst Substances 0.000 claims description 5
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 claims description 5
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- 101710130181 Protochlorophyllide reductase A, chloroplastic Proteins 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 18
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 230000001590 oxidative effect Effects 0.000 description 6
- CQKAPARXKPTKBK-UHFFFAOYSA-N tert-butylazanium;bromide Chemical compound Br.CC(C)(C)N CQKAPARXKPTKBK-UHFFFAOYSA-N 0.000 description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-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
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 5
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 5
- 235000010262 sodium metabisulphite Nutrition 0.000 description 5
- 125000001174 sulfone group Chemical group 0.000 description 5
- 229910052720 vanadium Inorganic materials 0.000 description 5
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 5
- 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 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- RMGVZKRVHHSUIM-UHFFFAOYSA-L dithionate(2-) Chemical compound [O-]S(=O)(=O)S([O-])(=O)=O RMGVZKRVHHSUIM-UHFFFAOYSA-L 0.000 description 4
- 231100001261 hazardous Toxicity 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 229940001584 sodium metabisulfite Drugs 0.000 description 4
- 239000012043 crude product Substances 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 239000012467 final product Substances 0.000 description 2
- 239000000612 proton pump inhibitor Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000007970 thio esters Chemical group 0.000 description 2
- 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 1
- SRUQARLMFOLRDN-UHFFFAOYSA-N 1-(2,4,5-Trihydroxyphenyl)-1-butanone Chemical compound CCCC(=O)C1=CC(O)=C(O)C=C1O SRUQARLMFOLRDN-UHFFFAOYSA-N 0.000 description 1
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- KSAPYRIVHFAQGR-UHFFFAOYSA-N 1-sulfanylbenzimidazole Chemical compound C1=CC=C2N(S)C=NC2=C1 KSAPYRIVHFAQGR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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
- 102100039386 Ketimine reductase mu-crystallin Human genes 0.000 description 1
- 101000772180 Lithobates catesbeianus Transthyretin Proteins 0.000 description 1
- 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 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 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
- 230000015572 biosynthetic process 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
- 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 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
- 150000002976 peresters Chemical class 0.000 description 1
- 229940126409 proton pump inhibitor Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26616201P | 2001-02-02 | 2001-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200305652B true ZA200305652B (en) | 2004-07-22 |
Family
ID=23013433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200305652A ZA200305652B (en) | 2001-02-02 | 2002-02-04 | Processes for the production of substituted 2-(2-pyridyl-methyl) sulfinyl-1H-benzimidazoles. |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US7129358B2 (cs) |
| EP (2) | EP1970374A1 (cs) |
| JP (1) | JP2004524303A (cs) |
| KR (1) | KR20040029966A (cs) |
| CN (3) | CN100347167C (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 |
|---|---|---|---|---|
| HRP20030691A2 (en) * | 2001-02-02 | 2005-04-30 | Teva Pharmaceutical Industries Ltd. | Processes for the production of substituted 2-(2-pyridylmethyl)sulfinyl-benzimidazoles |
| AU2003224779A1 (en) * | 2002-03-27 | 2003-10-13 | Teva Pharmaceutical Industries Ltd. | Lansoprazole polymorphs and processes for preparation thereof |
| AU2003268034A1 (en) * | 2002-07-26 | 2004-02-16 | Teva Pharmaceutical Industries Ltd. | Preparation of lansoprazole and related compounds |
| AU2003258335A1 (en) * | 2002-08-21 | 2004-03-11 | Teva Pharmaceutical Industries Ltd. | A method for the purification of lansoprazole |
| JP2005527638A (ja) * | 2002-11-18 | 2005-09-15 | テバ ファーマシューティカル インダストリーズ リミティド | ５００ｐｐｍより多く約３０００ｐｐｍまでの水および２００ｐｐｍより多く約５０００ｐｐｍまでのアルコールを含有する安定ランソプラゾール |
| CA2510849A1 (en) | 2002-12-19 | 2004-07-08 | Teva Pharmaceutical Industries Ltd | Solid states of pantoprazole sodium, processes for preparing them and processes for preparing known pantoprazole sodium hydrates |
| US7678816B2 (en) * | 2003-02-05 | 2010-03-16 | Teva Pharmaceutical Industries Ltd. | Method of stabilizing lansoprazole |
| EP1601667A2 (en) * | 2003-03-12 | 2005-12-07 | Teva Pharmaceutical Industries Limited | Crystalline and amorphous solids of pantoprazole and processes for their preparation |
| EP1615913A2 (en) * | 2003-06-10 | 2006-01-18 | Teva Pharmaceutical Industries Limited | 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 |
| ZA200706613B (en) | 2004-12-16 | 2009-03-25 | Cipla Ltd | Process |
| EP1681056A1 (en) | 2005-01-14 | 2006-07-19 | Krka Tovarna Zdravil, D.D., Novo Mesto | Process for preparing lansoprazole |
| EP1893602A2 (en) * | 2005-05-06 | 2008-03-05 | Medichem, S.A. | Pantoprazole free acid form iii |
| 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 |
| WO1993006097A1 (en) | 1991-09-20 | 1993-04-01 | Merck & Co., Inc. | Novel process for the preparation of anti-ulcer agents |
| 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 |
| EE04576B1 (et) * | 1997-12-08 | 2006-02-15 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Suposiit happes ebapüsivate toimeainete tarbeks, selle valmistamismeetod, toimeaineühik ja selle valmistamismeetod ning preparaat |
| 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. |
| HRP20030691A2 (en) | 2001-02-02 | 2005-04-30 | Teva Pharmaceutical Industries Ltd. | Processes for the production of substituted 2-(2-pyridylmethyl)sulfinyl-benzimidazoles |
-
2002
- 2002-02-04 HR HR20030691A patent/HRP20030691A2/xx not_active Application Discontinuation
- 2002-02-04 PL PL02368563A patent/PL368563A1/xx not_active Application Discontinuation
- 2002-02-04 ZA ZA200305652A patent/ZA200305652B/en unknown
- 2002-02-04 EP EP08010970A patent/EP1970374A1/en not_active Ceased
- 2002-02-04 MX MXPA03006904A patent/MXPA03006904A/es not_active Application Discontinuation
- 2002-02-04 CN CNB028044851A patent/CN100347167C/zh not_active Expired - Fee Related
- 2002-02-04 CN CNA200510086094XA patent/CN1781918A/zh active Pending
- 2002-02-04 ES ES02706135T patent/ES2209678T1/es active Pending
- 2002-02-04 CZ CZ20032351A patent/CZ20032351A3/cs unknown
- 2002-02-04 DE DE0001363901T patent/DE02706135T1/de active Pending
- 2002-02-04 YU YU61103A patent/YU61103A/sh 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 US US10/066,850 patent/US7129358B2/en not_active Expired - Fee Related
- 2002-02-04 KR KR10-2003-7010217A patent/KR20040029966A/ko not_active Ceased
- 2002-02-04 WO PCT/US2002/003225 patent/WO2002062786A1/en active Application Filing
- 2002-02-04 SK SK1079-2003A patent/SK10792003A3/sk not_active Application Discontinuation
- 2002-02-04 HU HU0303144A patent/HUP0303144A3/hu unknown
- 2002-02-04 CN CNA2006100819206A patent/CN1876647A/zh active Pending
- 2002-02-04 EP EP02706135A patent/EP1363901A4/en not_active Withdrawn
-
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 |
|---|---|
| NO20033433L (no) | 2003-09-25 |
| CN1876647A (zh) | 2006-12-13 |
| KR20040029966A (ko) | 2004-04-08 |
| HRP20030691A2 (en) | 2005-04-30 |
| IS6897A (is) | 2003-07-29 |
| MXPA03006904A (es) | 2004-12-06 |
| EP1363901A1 (en) | 2003-11-26 |
| HUP0303144A2 (hu) | 2004-03-01 |
| NO20033433D0 (no) | 2003-08-01 |
| CN1489585A (zh) | 2004-04-14 |
| WO2002062786A1 (en) | 2002-08-15 |
| CZ20032351A3 (cs) | 2004-08-18 |
| DE02706135T1 (de) | 2004-05-19 |
| US20080091024A1 (en) | 2008-04-17 |
| EP1363901A4 (en) | 2005-08-31 |
| CA2436467A1 (en) | 2002-08-15 |
| CN100347167C (zh) | 2007-11-07 |
| ES2209678T1 (es) | 2004-07-01 |
| JP2004524303A (ja) | 2004-08-12 |
| US7129358B2 (en) | 2006-10-31 |
| CN1781918A (zh) | 2006-06-07 |
| US20030036554A1 (en) | 2003-02-20 |
| YU61103A (sh) | 2006-05-25 |
| SK10792003A3 (sk) | 2004-07-07 |
| HUP0303144A3 (en) | 2007-08-28 |
| EP1970374A1 (en) | 2008-09-17 |
| PL368563A1 (en) | 2005-04-04 |
| US20060293363A1 (en) | 2006-12-28 |
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