CA2402635C - Method for oxidizing a thioether group into a sulfoxide group - Google Patents
Method for oxidizing a thioether group into a sulfoxide group Download PDFInfo
- Publication number
- CA2402635C CA2402635C CA002402635A CA2402635A CA2402635C CA 2402635 C CA2402635 C CA 2402635C CA 002402635 A CA002402635 A CA 002402635A CA 2402635 A CA2402635 A CA 2402635A CA 2402635 C CA2402635 C CA 2402635C
- Authority
- CA
- Canada
- Prior art keywords
- thioether
- oxidation
- group
- carbon atoms
- methyl
- 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
- 238000000034 method Methods 0.000 title claims abstract description 55
- 125000000101 thioether group Chemical group 0.000 title claims description 12
- 125000003375 sulfoxide group Chemical group 0.000 title claims description 5
- 230000001590 oxidative effect Effects 0.000 title description 2
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 40
- 230000003647 oxidation Effects 0.000 claims abstract description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 claims abstract description 19
- 229940045872 sodium percarbonate Drugs 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 150000002751 molybdenum Chemical class 0.000 claims abstract description 7
- PLITYYGQMDTHMM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfanyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1SCC1=CC=CC=N1 PLITYYGQMDTHMM-UHFFFAOYSA-N 0.000 claims abstract description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 150000003568 thioethers Chemical class 0.000 claims description 30
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical group [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 claims description 17
- 235000018660 ammonium molybdate Nutrition 0.000 claims description 17
- 229940010552 ammonium molybdate Drugs 0.000 claims description 17
- 239000011609 ammonium molybdate Substances 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 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 12
- 238000003786 synthesis reaction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- 150000003462 sulfoxides Chemical class 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 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 6
- 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 claims description 2
- 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 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 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 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 claims 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000002243 precursor Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 229910052720 vanadium Inorganic materials 0.000 description 6
- 229910052750 molybdenum Inorganic materials 0.000 description 5
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000011733 molybdenum Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 150000001204 N-oxides Chemical class 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- -1 alkylhydroperoxides Chemical class 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- MFWFDRBPQDXFRC-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;vanadium Chemical compound [V].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MFWFDRBPQDXFRC-LNTINUHCSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 150000003682 vanadium compounds Chemical class 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 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 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 125000001137 3-hydroxypropoxy group Chemical group [H]OC([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 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 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical class C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000007882 Gastritis Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 239000012425 OXONE® Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 1
- 238000007630 basic procedure Methods 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
- NYCVSSWORUBFET-UHFFFAOYSA-M sodium;bromite Chemical compound [Na+].[O-]Br=O NYCVSSWORUBFET-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ESP200000595 | 2000-03-13 | ||
| ES200000595A ES2163372B1 (es) | 2000-03-13 | 2000-03-13 | Procedimiento de oxidacion de un grupo tioeter a sulfoxido. |
| PCT/ES2001/000088 WO2001068594A1 (es) | 2000-03-13 | 2001-03-08 | Procedimiento de oxidacion de un grupo tioeter a sulfoxido |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2402635A1 CA2402635A1 (en) | 2001-09-20 |
| CA2402635C true CA2402635C (en) | 2008-07-08 |
Family
ID=8492674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002402635A Expired - Fee Related CA2402635C (en) | 2000-03-13 | 2001-03-08 | Method for oxidizing a thioether group into a sulfoxide group |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6603009B2 (enExample) |
| EP (1) | EP1270555B1 (enExample) |
| JP (1) | JP5041646B2 (enExample) |
| KR (1) | KR100657094B1 (enExample) |
| CN (1) | CN1229341C (enExample) |
| AT (1) | ATE274492T1 (enExample) |
| AU (2) | AU2001237452B9 (enExample) |
| CA (1) | CA2402635C (enExample) |
| DE (1) | DE60105139T2 (enExample) |
| ES (2) | ES2163372B1 (enExample) |
| HU (1) | HUP0301885A2 (enExample) |
| MX (1) | MXPA02008961A (enExample) |
| NO (1) | NO20024239L (enExample) |
| NZ (1) | NZ521071A (enExample) |
| PT (1) | PT1270555E (enExample) |
| WO (1) | WO2001068594A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1363901A4 (en) * | 2001-02-02 | 2005-08-31 | Teva Pharma | PROCESS FOR PREPARING SUBSTITUTED 2- (2-PYRIDYLMETHYL) SULFINYL-1H-BENZIMIDAZOLENE |
| KR100464174B1 (ko) * | 2002-03-06 | 2005-01-03 | 코오롱유화주식회사 | 설피닐 벤즈이미다졸 유도체의 제조방법 |
| EP1501824B1 (en) | 2002-08-21 | 2007-10-10 | Teva Pharmaceutical Industries Ltd | A method for the purification of lansoprazole |
| EP1465890B1 (en) | 2002-11-18 | 2007-04-04 | Teva Pharmaceutical Industries Ltd. | Stable lansoprazole containing more than 500 ppm, up to about 3,000 ppm water and more than 200 ppm, up to about 5,000 ppm alcohol |
| US7507829B2 (en) | 2002-12-19 | 2009-03-24 | Teva Pharmaceuticals Industries, Ltd | Solid states of pantoprazole sodium, processes for preparing them and processes for preparing known pantoprazole sodium hydrates |
| EP1485373A1 (en) | 2003-02-05 | 2004-12-15 | Teva Pharmaceutical Industries Limited | Method of stabilizing lansoprazole |
| CA2528993A1 (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 |
| AU2005268056B2 (en) | 2004-08-06 | 2008-07-31 | Eisai R&D Management Co., Ltd. | Salts of benzimidazole derivative with amines and process for production thereof |
| PL1802584T3 (pl) | 2004-10-11 | 2010-03-31 | Ranbaxy Laboratories Ltd | Sposób wytwarzania podstawionych sulfotlenków |
| KR100771659B1 (ko) | 2005-03-23 | 2007-10-30 | 주식회사 카이로제닉스 | 판토프라졸 및 그 중간체의 제조방법 |
| 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 |
| WO2009066309A2 (en) * | 2007-07-12 | 2009-05-28 | Cadila Healthcare Limited | Process for preparation of omeprazole |
| WO2009010937A1 (en) * | 2007-07-17 | 2009-01-22 | Ranbaxy Laboratories Limited | Process for the preparation op pantoprazole sodium and pantoprazole sodium sesquihydrate |
| CN102161633A (zh) * | 2011-02-22 | 2011-08-24 | 苏州科同生物医药科技有限公司 | 亚砜类有机化合物的制备方法 |
| CN103044399B (zh) * | 2011-10-12 | 2014-08-06 | 北大方正集团有限公司 | 一种雷贝拉唑及其钠盐的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2026761A6 (es) * | 1990-10-31 | 1992-05-01 | Genesis Para La Investigacion | Procedimiento de obtencion del omeprazol. |
| ES2036948B1 (es) * | 1991-11-21 | 1994-09-01 | Genesis Para La Investigacion | Procedimiento de obtencion de compuestos derivados de piridina. |
| ES2060541B1 (es) * | 1993-02-26 | 1995-11-16 | Vinas Lab | Nuevo procedimiento para la sintesis de un derivado de 2-(2-piridilmetilsufinil) bencimidazol, y nuevos productos intermedios obtenidos con el mismo. |
| EP1300406B1 (en) * | 1997-07-11 | 2004-10-06 | Eisai Co., Ltd. | Method for producing pyridine compound |
| US6437189B1 (en) * | 1997-12-12 | 2002-08-20 | Bayer Corporation | Synthesis of sulfoxides via selective oxidation of sulfides with a perborate or a percarbonate |
| ES2185459B1 (es) * | 2000-10-02 | 2003-12-16 | Dinamite Dipharma Spa | Procedimiento para la obtencion de pantoprazol y compuestos intermedios para el mismo. |
-
2000
- 2000-03-13 ES ES200000595A patent/ES2163372B1/es not_active Expired - Fee Related
-
2001
- 2001-03-08 CA CA002402635A patent/CA2402635C/en not_active Expired - Fee Related
- 2001-03-08 NZ NZ521071A patent/NZ521071A/en unknown
- 2001-03-08 PT PT01909846T patent/PT1270555E/pt unknown
- 2001-03-08 MX MXPA02008961A patent/MXPA02008961A/es active IP Right Grant
- 2001-03-08 HU HU0301885A patent/HUP0301885A2/hu unknown
- 2001-03-08 WO PCT/ES2001/000088 patent/WO2001068594A1/es not_active Ceased
- 2001-03-08 DE DE60105139T patent/DE60105139T2/de not_active Expired - Lifetime
- 2001-03-08 CN CNB018064620A patent/CN1229341C/zh not_active Expired - Fee Related
- 2001-03-08 EP EP01909846A patent/EP1270555B1/en not_active Expired - Lifetime
- 2001-03-08 JP JP2001567691A patent/JP5041646B2/ja not_active Expired - Fee Related
- 2001-03-08 AU AU2001237452A patent/AU2001237452B9/en not_active Ceased
- 2001-03-08 KR KR1020027011987A patent/KR100657094B1/ko not_active Expired - Fee Related
- 2001-03-08 ES ES01909846T patent/ES2227145T3/es not_active Expired - Lifetime
- 2001-03-08 AT AT01909846T patent/ATE274492T1/de not_active IP Right Cessation
- 2001-03-08 US US10/204,506 patent/US6603009B2/en not_active Expired - Fee Related
- 2001-03-08 AU AU3745201A patent/AU3745201A/xx active Pending
-
2002
- 2002-09-05 NO NO20024239A patent/NO20024239L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT1270555E (pt) | 2005-01-31 |
| NO20024239D0 (no) | 2002-09-05 |
| ES2227145T3 (es) | 2005-04-01 |
| HUP0301885A2 (hu) | 2003-09-29 |
| ES2163372B1 (es) | 2003-05-01 |
| ATE274492T1 (de) | 2004-09-15 |
| DE60105139D1 (de) | 2004-09-30 |
| US20030028030A1 (en) | 2003-02-06 |
| CN1418188A (zh) | 2003-05-14 |
| JP5041646B2 (ja) | 2012-10-03 |
| WO2001068594A1 (es) | 2001-09-20 |
| AU2001237452B9 (en) | 2005-01-27 |
| DE60105139T2 (de) | 2005-09-15 |
| CA2402635A1 (en) | 2001-09-20 |
| CN1229341C (zh) | 2005-11-30 |
| ES2163372A1 (es) | 2002-01-16 |
| NO20024239L (no) | 2002-09-05 |
| AU3745201A (en) | 2001-09-24 |
| AU2001237452B2 (en) | 2005-01-13 |
| KR100657094B1 (ko) | 2006-12-12 |
| NZ521071A (en) | 2004-05-28 |
| MXPA02008961A (es) | 2004-10-15 |
| EP1270555A1 (en) | 2003-01-02 |
| US6603009B2 (en) | 2003-08-05 |
| JP2003527370A (ja) | 2003-09-16 |
| EP1270555B1 (en) | 2004-08-25 |
| KR20030007461A (ko) | 2003-01-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2402635C (en) | Method for oxidizing a thioether group into a sulfoxide group | |
| US20080091024A1 (en) | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1H-benzimidazoles | |
| EP2125783A2 (en) | Process for the preparation of esomeprazole magnesium dihydrate | |
| JP5031362B2 (ja) | 製薬的方法、及び該方法により製造された化合物 | |
| KR101370844B1 (ko) | 판토프라졸 소듐의 제조방법 | |
| US20040138466A1 (en) | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1H-benzimidazoles | |
| KR100464174B1 (ko) | 설피닐 벤즈이미다졸 유도체의 제조방법 | |
| HK1048805A1 (en) | Method for producing therapeutic agents for ulcers | |
| HK1055942A (en) | Procedure for oxidizing of a thioether group to a sulfoxide group | |
| KR100783020B1 (ko) | 2-메틸클로라이드 피리딘 유도체 및 이를 이용한 벤즈이미다졸 유도체의 제조 방법 | |
| AU2002240242A1 (en) | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1H-benzimidazoles | |
| KR20020026016A (ko) | 금속촉매를 이용한 설피닐 화합물의 제조방법 | |
| KR20090041023A (ko) | 2-(2-피리딜메틸)설피닐-1에이치-벤즈이미다졸의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |