WO2002062786A1 - Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1h-benzimidazoles - Google Patents
Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1h-benzimidazoles Download PDFInfo
- Publication number
- WO2002062786A1 WO2002062786A1 PCT/US2002/003225 US0203225W WO02062786A1 WO 2002062786 A1 WO2002062786 A1 WO 2002062786A1 US 0203225 W US0203225 W US 0203225W WO 02062786 A1 WO02062786 A1 WO 02062786A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- process according
- oxidation
- methyl
- formula
- methoxy
- Prior art date
Links
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
Definitions
- the present invention relates to novel processes of preparing substituted 2-(2- pyridylmethyl) suli ⁇ nyl--. H-benzimidazoles .
- H-benzimidazoles are known gastric proton pump inhibitors. These include omeprazole (5-methoxy-2-[[(4-methoxy-3,5-dimethyl- 2-pyridyl) methyl] sulfmyl]-iH-benzimidazole), lansoprazole (2-[[[3-methyl-4-(2,2,2- trifluoro-ethoxy)-2-pyridinyl]methyl]sulfinyl]-- 7 H-benzimidazole), pantoprazole (5- (difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-iH-benzimidazole, and rabeprazole (2- [ [ [4-(3 -methoxy-propoxy)-3 -methyl-2-pyidin
- TBHP tert-butyl hydroperoxide
- the present invention provides a process for preparing a thioester compound of formula A:
- Rj, R 2 , and - 4 are each selected from the group consisting of hydrogen, substituted or unsubstituted lower alkyl and substituted or unsubstituted lower alkoxy; and R 3 is selected from the group consisting of hydrogen and substituted or unsubstituted lower alkyl, comprising reacting a thioether compound of formula B
- Ri . through 4 are as in formula A, with an oxidizing agent to produce selective oxidation of the thioether compound of formula B to form the thioester compound of formula A.
- the present invention further provides a process for preparing a thioester compound of compound of formula A, comprising reacting a thioether compound of formula B with Oxone (Oxone monopersulphate).
- the present invention further provides a process for preparing a thioester compound of compound of formula A, comprising reacting a thioether compound of formula B with tert- butyl hydroperoxide (TBHP) in the presence of a catalyst selected from the group consisting of vanadyl (IN) acetylacetonate, sodium metavanadate and vanadium pentoxide.
- TBHP tert- butyl hydroperoxide
- the substituted 2-(2-pyridylmethyl)sulfmyl-iH-benzimidazoles prepared according to the process of the present invention yield the desired products in a relatively high yield with only small amounts of the corresponding sulphone as by-product.
- An object of the present invention is to provide an improved process of selective oxidation of 5-methoxy-2-[[(4-methoxy-3 ,5-dimethyl-2-pyridyl)methyl]thio]-iH- benzimidazole (MPB) that utilizes a non-hazardous oxidant and results in the selective production of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfmyl]-iH- benzimidazole (omeprazole), i.e., the corresponding sulphoxide, with only minor amounts of 5-methoxy-2[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulphonyl]benzimidazole.
- Another object of the present invention is to provide an improved process of selective oxidation of 2-[[[3-methyl-4-(2,2,2-trifluoro-ethoxy)-2-pyridinyl]methyl]thio]- H- benzimidazole that utilizes a non-hazardous oxidant and results in the selective production of 2-[[[3-methyl-4-(2,2,2-trifluoro-ethoxy)-2-pyridinyl]methyl]sulfinyl]-- 7 H-benzimidazole (lansoprazole), i.e., the corresponding sulphoxide, with only minor amounts of 2-[[[3-methyl- 4-(2,2,2-trifluoro-ethoxy)-2-pyridinyl]methyl]sulphonyl]-iH-benzimidazole.
- Another object of the present invention is to provide an improved process of selective oxidation of 5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-iH- benzimidazole that utilizes a non-hazardous oxidant and results in the selective production of 5 -(difluoromethoxy)-2- [ [(3 ,4-dimethoxy-2-pyridinyl)methyl] sulfinyl] -iH-benzimidazole
- Another object of the present invention is to provide an improved process of selective oxidation of 2-[[[4-(3-methoxy-propoxy)-3-methyl-2-pyidinyl]methyl]thio]-iH- benzimidazole that utilizes a non-hazardous oxidant and results in the selective production of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl) methyl]sulfinyl]-7H-benzimidazole (rabeprazole), i.e., the corresponding sulphoxide, with only minor amounts of 5-methoxy- 2 [[(4-methoxy-3 , 5 -dimethyl-2-pyridyl)methyl] sulphonyl] -i H-benzimidazole.
- Another object of the present invention is to provide an improved process of preparing omeprazole while the amount of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl] sulphonyl]-iH-benzimidazole (SOMP) as by-product when the reaction proceeds to completion, is typically within the range of about 1 to about 4.5% by weight of the crude product mixture.
- SOMP 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl] sulphonyl]-iH-benzimidazole
- Another object of the present invention is to provide an improved process of preparing lansoprazole while the amount of 2-[[[3-methyl-4-(2,2,2-trifluoro-ethoxy)-2-pyridinyl] methyl]sulphonyl]--.H-benzimidazole as by-product when the reaction proceeds to completion, is typically within the range of about 1 to about 4.5% by weight of the crude product mixture.
- Another object of the present invention is to provide an improved process of preparing pantoprazole while the amount of 5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl) methyl]sulphonyl]-iH-benzimidazole as by-product when the reaction proceeds to completion, is typically within the range of about 1 to about 4.5% by weight of the crude product mixture.
- Another object of the present invention is to provide an improved process of preparing rabeprazole while the amount of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl) methyl]sulphonyl]-iH-benzimidazole as by-product when the reaction proceeds to completion, is typically within the range of about 1 to about 4.5% by weight of the crude product mixture.
- the present invention provides a process for preparing a thioester compound of formula A:
- R ls R , and P are each selected from the group consisting of hydrogen, substituted or unsubstituted lower alkyl and substituted or unsubstituted lower alkoxy; and R 3 is selected from the group consisting of hydrogen and substituted or unsubstituted lower alkyl, comprising reacting a thioether compound of formula B
- the present invention provides the preparation of substituted 2-(2- pyridylmethyl)sulfinyl-iH-benzimidazoles of formula A, wherein Ri is methyl; R 2 is methoxy; R 3 is methyl and R- t is methoxy.
- the compound is omeprazole.
- the present invention provides the preparation of substituted 2-(2- pyridylmethyl)sulfinyl-iH-benzimidazoles of formula A, wherein Ri . is methyl; R 2 is
- R 3 is hydrogen and R4 is hydrogen.
- the compound is lansoprazole.
- the present invention provides the preparation of substituted 2-(2- pyridylmethyl)sulfinyl--.
- the compound is pantoprazole.
- the present invention provides the preparation of substituted 2-(2- pyridylmethyl)sulfinyl-iH-benzimidazoles of formula A, wherein Ri . is methyl; R 2 is MeOC ⁇ 2 C ⁇ 2 C ⁇ O, R 3 is hydrogen and R is hydrogen.
- the compound is rabeprazole.
- the oxidation is performed with tert-butyl hydroperoxide (TBHP) in the presence of a catalyst selected from the group consisting of vanadyl bis-acetylacetonate, sodium meta-vanadate and vanadium pentoxide.
- a catalyst selected from the group consisting of vanadyl bis-acetylacetonate, sodium meta-vanadate and vanadium pentoxide.
- the catalyst is vanadyl bis-acetylacetonate.
- the molar ratio of tert-butyl hydroperoxide (TBHP) to a compound of formula B is in the range of about 1.15 to about 4.5.
- the compound of formula A includes 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2- pyridyl)methyl]thio]-lH-benzimidazole, 2[[[3-methyl-4-(2,2,2-trifluoro-ethoxy)-2- pyridinyl]methyl]thio]-lH-benzimidazole, 5-(difluoromethoxy)-2-[[3,4-dimethoxy-2- pyridinyl)methyl]thio]-lH-benzimidazole, and 2-[[[4-(3-methoxy-propoxy)-3-methyl-2- pyridinyl]methyl]thio]-lH-benzimidazole.
- the molar ratio of vanadyl bis-acetylacetonate to the compound of formula B is from about 0.01 to about 0.6.
- the oxidation by tert-butyl hydroperoxide (TB ⁇ P) in the presence of a catalyst is performed in an organic solvent selected from the group consisting of toluene, lower alkanols and ethyl acetate.
- Another preferred embodiment of the present invention is that the oxidation is performed in an organic solvent such as toluene, a lower alkanol, preferably isopropanol or ethyl acetate. Most preferable solvent is toluene or isopropanol.
- organic solvent such as toluene, a lower alkanol, preferably isopropanol or ethyl acetate. Most preferable solvent is toluene or isopropanol.
- the oxidation of substituted 2-(2-pyridylmethyl)sulfinyl-7H- benzimidazoles of formula A is performed at temperature ranging from about -10 °C to about 30°C.
- the oxidation of substituted 2-(2-pyridylmethyl)sulfinyl-7H- benzimidazoles of formula A is performed over a period of about 2 to about 10 hours.
- the oxidation is performed in the presence of Oxone ® (Oxone monopersulphate).
- the molar ratio between Oxone ® (Oxone monopersulphate) and the compound of formula B is from about 1.25 to about 1.6:1, most preferably about 1.4 to about 1.6:1.
- the oxidation by Oxone ® is performed in the presence of an aqueous organic solvent.
- the organic solvent is acetone, methanol or in two-phase system (C ⁇ 2 C1 2 / H 2 O, (ethyl acetate / H 2 O) in the presence of phase-transferred catalyst (e.g. TBAB). More preferably, the oxidation is performed in about 5% aqueous methanol.
- the oxidation of substituted 2-(2-pyridylmethyl)sulfinyl-7H- benzimidazoles of formula A is performed in a two-phase system selected from (C ⁇ 2 C1 2 /
- oxidation of substituted 2-(2-pyridylmethyl)sulfinyl-iH- benzimidazoles of formula A is performed in the presence of tert-butyl ammonium bromide (TBAB).
- TBAB tert-butyl ammonium bromide
- the oxidation by Oxone ® (Oxone monopersulphate) is performed at a temperature ranging from about — 10°C to about 30°C over a time period of about 2 to about 10 hours.
- the oxidation conditions of the present invention result in the production of the compound of formula A, wherein the amount of sulphone derivative is less than about 0.5% (wt/wt) of the final product preferably less than 0.2% (wt/wt).
- the pure products prepared in according to the disclosed method include pantoprazole, lansoprazole, omeprazole and rabeprazole.
- Example 6 Changes of Experimental Conditions and Yields The above described processes of Example 1 and Example 2 were repeated while using the conditions given in Table I below, to give the following results:
- Example 7 Comparison with the Method disclosed by Canadian Patent 1.263,119 4 mg (0.06% molar) NO (acac) 2 were added to suspension of 9 grams of 5-methoxy-2- [[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-lH-benzimidazole (MPB) in 66 ml ethanol at room temperature. 35 ml of 35% aqueous hydrogen peroxide (150% mol) was added at room temperature with no visible exotherm, the mixture was then stirred. After 12 hours the reaction mixture still contained 65% of untreated MPB and only 32% omeprazole. Prolongation of the reaction time did not lead to further production of omeprazole.
- MPB 5-methoxy-2- [[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-lH-benzimidazole
- Example 9 Changes of Experimental Conditions and Yields The above described reaction of Example 8 was repeated while using the conditions given in Table II below, to give the following results: Table ⁇
- Oxone ® 3.5 ml (5.69 mmol) Oxone ® is added. The mixture is stirred for 4 hours at 0°C and a further lgram (mmol) Oxone ® is added and stirring continues for 1.5 hours. A solution of 0.8 gram sodium metabisulfite in 20ml water is added dropwise over 5-10 minutes. After further stirring the resultant precipitate is filtered, washed successively with water and 50% aqueous methanol and dried. Purity is 98.1%.
Abstract
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE0001363901T DE02706135T1 (en) | 2001-02-02 | 2002-02-04 | METHOD FOR PRODUCING SUBSTITUTED 2- (2-PYRIDYLMETHYL) SULFINYL-1H-BENZIMIDAZOLES |
HU0303144A HUP0303144A3 (en) | 2001-02-02 | 2002-02-04 | Process for the production of substituted 2-(2-pyridylmethyl)sulfinyl-1h-benzimidazoles |
CA002436467A CA2436467A1 (en) | 2001-02-02 | 2002-02-04 | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1h-benzimidazoles |
KR10-2003-7010217A KR20040029966A (en) | 2001-02-02 | 2002-02-04 | Processes for the production of substituted 2-(2-pyridylmethyl)sulfinyl-1h-benzimidazoles |
JP2002563139A JP2004524303A (en) | 2001-02-02 | 2002-02-04 | Method for producing substituted 2- (2-pyridylmethyl) sulfinyl-1H-benzimidazoles |
SK1079-2003A SK10792003A3 (en) | 2001-02-02 | 2002-02-04 | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1H-benzimidazoles |
MXPA03006904A MXPA03006904A (en) | 2001-02-02 | 2002-02-04 | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1h-benzimidazoles. |
EP02706135A EP1363901A4 (en) | 2001-02-02 | 2002-02-04 | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1h-benzimidazoles |
IS6897A IS6897A (en) | 2001-02-02 | 2003-07-29 | Methods for Preparing Exchanged 2- (2-Pyridylmethyl) Sulphinyl-1H-Benzimidazole |
NO20033433A NO20033433L (en) | 2001-02-02 | 2003-08-01 | Process for the preparation of 2- (2-pyridylmethyl) sulfinyl-1H-benzimidazole |
HR20030691A HRP20030691A2 (en) | 2001-02-02 | 2003-09-01 | Processes for the production of substituted 2-(2-pyridylmethyl)sulfinyl-benzimidazoles |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US26616201P | 2001-02-02 | 2001-02-02 | |
US60/266,162 | 2001-02-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002062786A1 true WO2002062786A1 (en) | 2002-08-15 |
Family
ID=23013433
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2002/003225 WO2002062786A1 (en) | 2001-02-02 | 2002-02-04 | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1h-benzimidazoles |
Country Status (19)
Country | Link |
---|---|
US (3) | US7129358B2 (en) |
EP (2) | EP1970374A1 (en) |
JP (1) | JP2004524303A (en) |
KR (1) | KR20040029966A (en) |
CN (3) | CN1781918A (en) |
CA (1) | CA2436467A1 (en) |
CZ (1) | CZ20032351A3 (en) |
DE (1) | DE02706135T1 (en) |
ES (1) | ES2209678T1 (en) |
HR (1) | HRP20030691A2 (en) |
HU (1) | HUP0303144A3 (en) |
IS (1) | IS6897A (en) |
MX (1) | MXPA03006904A (en) |
NO (1) | NO20033433L (en) |
PL (1) | PL368563A1 (en) |
SK (1) | SK10792003A3 (en) |
WO (1) | WO2002062786A1 (en) |
YU (1) | YU61103A (en) |
ZA (1) | ZA200305652B (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004011455A1 (en) * | 2002-07-26 | 2004-02-05 | Teva Pharmaceutical Industries Ltd. | Preparation of lansoprazole and related compounds |
WO2004111029A3 (en) * | 2003-06-10 | 2005-11-17 | Teva Pharma | Process for preparing 2-[(pyridinyl)methyl]sulfinyl-substituted benzimidazoles and novel chlorinated derivatives of pantoprazole |
EP1681056A1 (en) * | 2005-01-14 | 2006-07-19 | Krka Tovarna Zdravil, D.D., Novo Mesto | Process for preparing lansoprazole |
US7129358B2 (en) | 2001-02-02 | 2006-10-31 | Teva Pharmaceutical Industries Ltd. | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1H-benzimidazoles |
JP2008502665A (en) * | 2004-06-17 | 2008-01-31 | シデム ファーマ ソシエテ アノニム | S-tenatoprazole sodium salt monohydrate and its use in therapy |
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 |
US8691995B2 (en) | 2004-12-16 | 2014-04-08 | Cipla Limited | Process |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005533755A (en) * | 2002-03-27 | 2005-11-10 | 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 | Lansoprazole polymorph and process for its preparation |
WO2004018454A1 (en) * | 2002-08-21 | 2004-03-04 | Teva Pharmaceutical Industries Ltd. | A method for the purification of lansoprazole |
AU2003294405A1 (en) * | 2002-11-18 | 2004-06-15 | 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 |
EP1485373A1 (en) * | 2003-02-05 | 2004-12-15 | Teva Pharmaceutical Industries Limited | Method of stabilizing lansoprazole |
ES2245277T1 (en) * | 2003-03-12 | 2006-01-01 | Teva Pharmaceutical Industries Limited | SOLIDOS CRYSTALS AND AMORPHES OF PANTOPRAZOL AND PROCEDURES FOR THEIR PREPARATION. |
CA2607583A1 (en) * | 2005-05-06 | 2007-04-05 | Medichem, S.A. | Pantoprazole free acid form iii |
CN1919844B (en) * | 2006-09-01 | 2010-05-12 | 武汉工程大学 | Method for aqueous phase oxo-synthesis of iansoprazole |
US20100113527A1 (en) * | 2008-09-30 | 2010-05-06 | 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 (en) * | 2017-03-17 | 2022-11-04 | 江苏豪森药业集团有限公司 | Preparation method of rabeprazole analogue |
CN111072633A (en) * | 2019-12-19 | 2020-04-28 | 山东达因海洋生物制药股份有限公司 | Preparation method of esomeprazole magnesium trihydrate |
CN112174934B (en) * | 2020-10-15 | 2023-12-22 | 成都百泉生物医药科技有限公司 | Synthesis method and synthesis equipment of omeprazole |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5391752A (en) * | 1991-09-20 | 1995-02-21 | Merck & Co., Inc. | Process for the preparation of antiulcer agents |
WO1999047514A1 (en) * | 1998-03-17 | 1999-09-23 | Knoll Aktiengesellschaft | Chemical process for the production of sulphinyl derivatives by oxidation of the corresponding co-derivatives with perborates |
WO2000002876A1 (en) * | 1998-07-13 | 2000-01-20 | LEK, tovarna farmacevtskih in kemičnih izdelkov, d.d. | Improved process of synthesis of 5-methoxy- 2-[(4-methoxy- 3,5-dimethyl- 2-pyridyl)methyl]sulfinyl-1h-benzimidazole |
WO2001068594A1 (en) * | 2000-03-13 | 2001-09-20 | Esteve Quimica, S.A. | Method for oxidizing a thioether group into a sulfoxide group |
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 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1140119A (en) | 1978-04-03 | 1983-01-25 | Joseph Torremans | N-heterocyclyl-4-piperidinamines |
SE7804231L (en) | 1978-04-14 | 1979-10-15 | Haessle Ab | Gastric acid secretion |
GB2069492B (en) | 1980-02-20 | 1984-02-29 | Wyeth John & Brother Ltd | Sulphur compounds |
SE8300736D0 (en) * | 1983-02-11 | 1983-02-11 | Haessle Ab | NOVEL PHARMACOLOGICALLY ACTIVE COMPOUNDS |
DK171989B1 (en) | 1987-08-04 | 1997-09-08 | Takeda Chemical Industries Ltd | Process for the preparation of 2- (2-pyridylmethylsulfinyl) benzimidazoles |
SE9002043D0 (en) | 1990-06-07 | 1990-06-07 | Astra Ab | IMPROVED METHOD FOR SYNTHESIS |
ES2063705B1 (en) * | 1993-06-14 | 1995-07-16 | S A L V A T Lab Sa | INTERMEDIATE FOR THE SYNTHESIS OF LANSOPRAZOLE AND ITS PROCEDURE FOR OBTAINING. |
SK283805B6 (en) * | 1996-09-09 | 2004-02-03 | Slovakofarma, A. S. | Method of omeprazole preparation |
SE9704183D0 (en) | 1997-11-14 | 1997-11-14 | Astra Ab | New process |
SI1037634T1 (en) * | 1997-12-08 | 2006-02-28 | Altana Pharma Ag | Oral administration form comprising a proton pump inhibitor (e.g.pantoprazole) |
JP4047993B2 (en) * | 1999-01-04 | 2008-02-13 | 理想科学工業株式会社 | Stencil printing method |
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 |
CN1781918A (en) | 2001-02-02 | 2006-06-07 | 特瓦制药工业有限公司 | Process for producing thioester compound |
-
2002
- 2002-02-04 CN CNA200510086094XA patent/CN1781918A/en active Pending
- 2002-02-04 HU HU0303144A patent/HUP0303144A3/en unknown
- 2002-02-04 CZ CZ20032351A patent/CZ20032351A3/en unknown
- 2002-02-04 MX MXPA03006904A patent/MXPA03006904A/en not_active Application Discontinuation
- 2002-02-04 EP EP08010970A patent/EP1970374A1/en not_active Ceased
- 2002-02-04 CN CNA2006100819206A patent/CN1876647A/en active Pending
- 2002-02-04 JP JP2002563139A patent/JP2004524303A/en active Pending
- 2002-02-04 DE DE0001363901T patent/DE02706135T1/en active Pending
- 2002-02-04 YU YU61103A patent/YU61103A/en unknown
- 2002-02-04 ES ES02706135T patent/ES2209678T1/en active Pending
- 2002-02-04 CN CNB028044851A patent/CN100347167C/en not_active Expired - Fee Related
- 2002-02-04 EP EP02706135A patent/EP1363901A4/en not_active Withdrawn
- 2002-02-04 PL PL02368563A patent/PL368563A1/en not_active Application Discontinuation
- 2002-02-04 WO PCT/US2002/003225 patent/WO2002062786A1/en active Application Filing
- 2002-02-04 KR KR10-2003-7010217A patent/KR20040029966A/en not_active Application Discontinuation
- 2002-02-04 US US10/066,850 patent/US7129358B2/en not_active Expired - Fee Related
- 2002-02-04 SK SK1079-2003A patent/SK10792003A3/en not_active Application Discontinuation
- 2002-02-04 ZA ZA200305652A patent/ZA200305652B/en unknown
- 2002-02-04 CA CA002436467A patent/CA2436467A1/en not_active Abandoned
-
2003
- 2003-07-29 IS IS6897A patent/IS6897A/en unknown
- 2003-08-01 NO NO20033433A patent/NO20033433L/en not_active Application Discontinuation
- 2003-09-01 HR HR20030691A patent/HRP20030691A2/en 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
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5391752A (en) * | 1991-09-20 | 1995-02-21 | Merck & Co., Inc. | Process for the preparation of antiulcer agents |
WO1999047514A1 (en) * | 1998-03-17 | 1999-09-23 | Knoll Aktiengesellschaft | Chemical process for the production of sulphinyl derivatives by oxidation of the corresponding co-derivatives with perborates |
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 |
WO2000002876A1 (en) * | 1998-07-13 | 2000-01-20 | LEK, tovarna farmacevtskih in kemičnih izdelkov, d.d. | Improved process of synthesis of 5-methoxy- 2-[(4-methoxy- 3,5-dimethyl- 2-pyridyl)methyl]sulfinyl-1h-benzimidazole |
WO2001068594A1 (en) * | 2000-03-13 | 2001-09-20 | Esteve Quimica, S.A. | Method for oxidizing a thioether group into a sulfoxide group |
Non-Patent Citations (1)
Title |
---|
See also references of EP1363901A4 * |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7129358B2 (en) | 2001-02-02 | 2006-10-31 | Teva Pharmaceutical Industries Ltd. | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1H-benzimidazoles |
WO2004011455A1 (en) * | 2002-07-26 | 2004-02-05 | Teva Pharmaceutical Industries Ltd. | Preparation of lansoprazole and related compounds |
US7915423B2 (en) | 2002-12-19 | 2011-03-29 | Teva Pharmaceutical Industries, Ltd. | Solid states of pantoprazole sodium, processes for preparing them and processes for preparing known pantoprazole sodium hydrates |
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 |
US7683177B2 (en) | 2003-06-10 | 2010-03-23 | Teva Pharmaceutical Industries Ltd | Process for preparing 2-[(pyridinyl)methyl]sulfinyl-substituted benzimidazoles and novel chlorinated derivatives of pantoprazole |
WO2004111029A3 (en) * | 2003-06-10 | 2005-11-17 | Teva Pharma | Process for preparing 2-[(pyridinyl)methyl]sulfinyl-substituted benzimidazoles and novel chlorinated derivatives of pantoprazole |
JP2008502665A (en) * | 2004-06-17 | 2008-01-31 | シデム ファーマ ソシエテ アノニム | S-tenatoprazole sodium salt monohydrate and its use in therapy |
US8691995B2 (en) | 2004-12-16 | 2014-04-08 | Cipla Limited | Process |
WO2006074952A1 (en) * | 2005-01-14 | 2006-07-20 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Process for preparing lansoprazole |
EP1681056A1 (en) * | 2005-01-14 | 2006-07-19 | Krka Tovarna Zdravil, D.D., Novo Mesto | Process for preparing lansoprazole |
US7662968B2 (en) | 2005-01-14 | 2010-02-16 | KRKA tovarna zdravil, d.d.. | Process for preparing lansoprazole |
EP2308492A1 (en) | 2005-01-14 | 2011-04-13 | KRKA, tovarna zdravil, d.d., Novo mesto | Process for preparing lansoprazole |
EA015043B1 (en) * | 2005-01-14 | 2011-04-29 | Крка, Товарна Здравил, Д.Д., Ново Место | Process for preparing lansoprazole |
CN101137371B (en) * | 2005-01-14 | 2011-05-25 | 克卡制药新梅斯托股份公司 | Process for preparing lansoprazole |
Also Published As
Publication number | Publication date |
---|---|
EP1363901A4 (en) | 2005-08-31 |
PL368563A1 (en) | 2005-04-04 |
JP2004524303A (en) | 2004-08-12 |
ZA200305652B (en) | 2004-07-22 |
HUP0303144A3 (en) | 2007-08-28 |
CN1876647A (en) | 2006-12-13 |
SK10792003A3 (en) | 2004-07-07 |
CN1781918A (en) | 2006-06-07 |
ES2209678T1 (en) | 2004-07-01 |
US7129358B2 (en) | 2006-10-31 |
CZ20032351A3 (en) | 2004-08-18 |
US20060293363A1 (en) | 2006-12-28 |
DE02706135T1 (en) | 2004-05-19 |
EP1970374A1 (en) | 2008-09-17 |
YU61103A (en) | 2006-05-25 |
NO20033433L (en) | 2003-09-25 |
NO20033433D0 (en) | 2003-08-01 |
HRP20030691A2 (en) | 2005-04-30 |
KR20040029966A (en) | 2004-04-08 |
HUP0303144A2 (en) | 2004-03-01 |
US20080091024A1 (en) | 2008-04-17 |
CA2436467A1 (en) | 2002-08-15 |
CN100347167C (en) | 2007-11-07 |
US20030036554A1 (en) | 2003-02-20 |
MXPA03006904A (en) | 2004-12-06 |
CN1489585A (en) | 2004-04-14 |
EP1363901A1 (en) | 2003-11-26 |
IS6897A (en) | 2003-07-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US20060293363A1 (en) | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1H-benzimidazoles | |
CA2450433C (en) | Improved process for preparing benzimidazole-type compounds | |
AU2002321204A1 (en) | Improved process for preparing benzimidazole-type compounds | |
JP5031362B2 (en) | Pharmaceutical methods and compounds produced by the methods | |
JP5041646B2 (en) | Method for oxidizing a thioether group to a sulfoxide group | |
JP2003527370A5 (en) | ||
US20040138466A1 (en) | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1H-benzimidazoles | |
AU2002240242A1 (en) | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1H-benzimidazoles | |
US20090005570A1 (en) | Method for preparing 2- (2-pyridinylmethylsulfinyl) benzimidazoles | |
US20060128964A1 (en) | Method for preparing 2- (2-pyridylmethylsulphinyl) benzimidazoles | |
CZ20021467A3 (en) | Process for preparing ulcer therapeutics | |
KR100464174B1 (en) | A process for preparation of sulfinyl benzimidazole derivatives | |
EP1467987A1 (en) | Preparation of lansoprazole and related compounds |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: P-611/03 Country of ref document: YU |
|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG US UZ VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2003/05652 Country of ref document: ZA Ref document number: 200305652 Country of ref document: ZA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 726/MUMNP/2003 Country of ref document: IN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2436467 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: PA/a/2003/006904 Country of ref document: MX Ref document number: 157184 Country of ref document: IL |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020037010217 Country of ref document: KR Ref document number: 2002563139 Country of ref document: JP Ref document number: 028044851 Country of ref document: CN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 527491 Country of ref document: NZ |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2002706135 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2002240242 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 10792003 Country of ref document: SK |
|
WWE | Wipo information: entry into national phase |
Ref document number: PV2003-2351 Country of ref document: CZ Ref document number: P20030691A Country of ref document: HR |
|
WWP | Wipo information: published in national office |
Ref document number: 2002706135 Country of ref document: EP |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
WWP | Wipo information: published in national office |
Ref document number: 1020037010217 Country of ref document: KR |
|
WWP | Wipo information: published in national office |
Ref document number: PV2003-2351 Country of ref document: CZ |