WO2003089408A3 - Optically active substituted pyridinylmethyl-sulphinyl-benzimidazole and salts - Google Patents

Optically active substituted pyridinylmethyl-sulphinyl-benzimidazole and salts Download PDF

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Publication number
WO2003089408A3
WO2003089408A3 PCT/IN2003/000164 IN0300164W WO03089408A3 WO 2003089408 A3 WO2003089408 A3 WO 2003089408A3 IN 0300164 W IN0300164 W IN 0300164W WO 03089408 A3 WO03089408 A3 WO 03089408A3
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WO
WIPO (PCT)
Prior art keywords
benzimidazole
methoxy
pyridinylmethyl
alkali
earth metal
Prior art date
Application number
PCT/IN2003/000164
Other languages
French (fr)
Other versions
WO2003089408A2 (en
Inventor
Rajamannar Thennati
Rajeev Budhdev Rehani
Rohit Ravikant Soni
Vijay Chhangamal Chhabada
Vijaykumar Muljibhai Patel
Original Assignee
Sun Pharmaceutical Ind Ltd
Rajamannar Thennati
Rajeev Budhdev Rehani
Rohit Ravikant Soni
Vijay Chhangamal Chhabada
Vijaykumar Muljibhai Patel
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sun Pharmaceutical Ind Ltd, Rajamannar Thennati, Rajeev Budhdev Rehani, Rohit Ravikant Soni, Vijay Chhangamal Chhabada, Vijaykumar Muljibhai Patel filed Critical Sun Pharmaceutical Ind Ltd
Priority to AU2003262375A priority Critical patent/AU2003262375A1/en
Publication of WO2003089408A2 publication Critical patent/WO2003089408A2/en
Publication of WO2003089408A3 publication Critical patent/WO2003089408A3/en

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    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The present invention relates to an enantioselective catalytic oxidation process for preparation of an optically active enantiomer or an enantiomerically enriched form of substituted pyridinylmethyl-sulphinyl-benzimidazole comprising enantioselective catalytic oxidation of a substituted pyridinylmethyl prochiral sulphide derivative of benzimidazole with an oxidizing agent in an organic solvent in the presence of a base and a catalyst comprising titanium or vanadium complexed with a chiral monodentate ligand. The present invention also relates to alkali or alkaline earth metal salts of S-enantiomer of 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinylmethyl)sulfinyl]-1H-benzimidazole substantially free of sulfone impurity. The present invention also relates to a process for purification of alkali or alkaline earth metal salts of S-enantiomer of 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinylmethyl)sulfinyl]-1H-benzimidazole comprising treatment of the said alkali or alkaline earth metal salt having a sulfone impurity with a solvent system comprising an organic solvent selected from ketone and nitrile, and isolating the alkali or alkaline earth metal salt of S-enantiomer of 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinylmethyl)sulfinyl]-1H-benzimidazole which is substantially free of sulfone impurity.
PCT/IN2003/000164 2002-04-22 2003-04-21 Optically active substituted pyridinylmethyl-sulphinyl-benzimidazole and salts WO2003089408A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003262375A AU2003262375A1 (en) 2002-04-22 2003-04-21 Optically active substituted pyridinylmethyl-sulphinyl-benzimidazole and salts

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN365/MUM/2002 2002-04-22
IN299/MUM/2002 2002-04-22
IN365MU2002 2002-04-22
IN299MU2002 2002-04-22

Publications (2)

Publication Number Publication Date
WO2003089408A2 WO2003089408A2 (en) 2003-10-30
WO2003089408A3 true WO2003089408A3 (en) 2004-02-05

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2003/000164 WO2003089408A2 (en) 2002-04-22 2003-04-21 Optically active substituted pyridinylmethyl-sulphinyl-benzimidazole and salts

Country Status (2)

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AU (1) AU2003262375A1 (en)
WO (1) WO2003089408A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102813651B (en) * 2011-06-07 2015-02-11 成都国为医药科技有限公司 Pharmaceutical composition containing esomeprazole sodium, and preparation method thereof

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US20040242642A1 (en) * 2002-11-18 2004-12-02 Dr. Reddy's Laboratories Limited Crystalline esomeprazole compounds and process for the preparation thereof
WO2004056804A2 (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
FR2852956B1 (en) * 2003-03-28 2006-08-04 Negma Gild PROCESS FOR THE ENANTIOSELECTIVE PREPARATION OF SULFOXIDE DERIVATIVES
KR20060002878A (en) * 2003-03-28 2006-01-09 지뎀 파마 Method for the enantioselective preparation of sulphoxide derivatives
FR2863611B1 (en) * 2003-12-15 2006-03-24 Sidem Pharma Sa PROCESS FOR THE ENANTIOSELECTIVE PREPARATION OF SULFOXIDE DERIVATIVES
CN1842525A (en) 2003-05-05 2006-10-04 兰贝克赛实验室有限公司 Barium salt of benzimidazole derivative
SE0400410D0 (en) 2004-02-20 2004-02-20 Astrazeneca Ab New compounds
WO2005082888A1 (en) * 2004-03-01 2005-09-09 Milen Merkez Ilac Endustrisi A.S. Process for the preparation of magnesium salt of omeprazole
NZ551970A (en) 2004-06-24 2010-01-29 Astrazeneca Ab New process for the preparation of crystal modifications for use in the preparation of esomeprazole sodium salt
ES2246149B1 (en) * 2004-07-02 2007-06-01 Esteve Quimica, S.A. SOLID FORMS OF S-OMEPRAZOL MAGNETIC SALT AND PROCEDURES FOR PREPARATION.
FR2876101B1 (en) * 2004-10-05 2007-03-02 Sidem Pharma Sa Sa PROCESS FOR THE ENANTIOSELECTIVE PREPARATION OF SULFOXIDE DERIVATIVES
DE602005016705D1 (en) 2004-10-11 2009-10-29 Ranbaxy Lab Ltd METHOD FOR PRODUCING SUBSTITUTED SULFOXIDE
CA2597632C (en) * 2005-03-25 2012-05-15 Livzon Pharmaceutical Group Inc. Substituted sulfoxide compounds, methods for preparing the same and use thereof
DE102005061720B3 (en) * 2005-12-22 2006-10-19 Ratiopharm Gmbh Preparing optically active omeprazole enantiomers, useful to treat stomach diseases, comprises oxidizing prochiral sulfide compound with oxidizing agent in presence of titanium complex catalyst and reacting the catalyst with chiral diols
US7553857B2 (en) 2005-12-23 2009-06-30 Lek Pharmaceuticals D.D. S-omeprazole magnesium
US8063074B2 (en) 2006-05-04 2011-11-22 Dr. Reddy's Laboratories Limited Polymorphic forms of esomeprazole sodium
US7786309B2 (en) 2006-06-09 2010-08-31 Apotex Pharmachem Inc. Process for the preparation of esomeprazole and salts thereof
EP2000468A1 (en) 2007-05-09 2008-12-10 Dr. Reddy's Laboratories Ltd. Esomeprazole salts and processes for preparation thereof
US8106210B2 (en) * 2007-10-08 2012-01-31 Hetero Drugs Limited Polymorphs of esomeprazole salts
EP2143722A1 (en) 2008-07-09 2010-01-13 Lek Pharmaceuticals D.D. Process for preparation of esomeprazole sodium of high chemical purity and new forms of esomeprazole sodium
EP2264024A1 (en) 2008-10-14 2010-12-22 LEK Pharmaceuticals d.d. Process for the preparation of enantiomerically enriched proton pump inhibitors
US8680284B2 (en) * 2010-02-12 2014-03-25 Esteve Quimica, S.A. Preparation process of the sodium salt of esomeprazole
CN102850323A (en) * 2011-06-30 2013-01-02 秦引林 Refining method of esomeprazole sodium
CN102351847B (en) * 2011-09-21 2013-01-23 南京优科制药有限公司 Industrial method for refining esomeprazole sodium salt
CN102408412A (en) * 2011-10-25 2012-04-11 广东华南药业集团有限公司 (S)-omeprazole preparation method with high antipode selectivity
CN103420979B (en) * 2012-05-17 2016-04-20 广州莱泰制药有限公司 The process for purification of Esomeprazole sodium
WO2016104668A1 (en) * 2014-12-26 2016-06-30 国立大学法人 東京大学 Method for producing proton pump inhibitor compound having optical activity
CN105566298A (en) * 2016-02-16 2016-05-11 顾伟 Method for preparing esomeprazole sodium
CN107056752A (en) * 2017-04-01 2017-08-18 上海华源医药科技发展有限公司 A kind of preparation method of esomeprazole potassium

Citations (3)

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WO1998054171A1 (en) * 1997-05-30 1998-12-03 Astra Aktiebolag Novel form of s-omeprazole
US5948789A (en) * 1994-07-15 1999-09-07 Astra Aktiebolag Process for synthesis of substituted sulphoxides
EP1277752A1 (en) * 2000-04-28 2003-01-22 Takeda Chemical Industries, Ltd. Process for producing optically active sulfoxide derivative

Patent Citations (3)

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US5948789A (en) * 1994-07-15 1999-09-07 Astra Aktiebolag Process for synthesis of substituted sulphoxides
WO1998054171A1 (en) * 1997-05-30 1998-12-03 Astra Aktiebolag Novel form of s-omeprazole
EP1277752A1 (en) * 2000-04-28 2003-01-22 Takeda Chemical Industries, Ltd. Process for producing optically active sulfoxide derivative

Non-Patent Citations (1)

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Title
COTTON H., ET AL.: "Asymmetric synthesis of esomeprazole", TETRAHEDRON ASYMMETRY, vol. 11, 2000, pages 3819 - 3825, XP004224163, DOI: doi:10.1016/S0957-4166(00)00352-9 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102813651B (en) * 2011-06-07 2015-02-11 成都国为医药科技有限公司 Pharmaceutical composition containing esomeprazole sodium, and preparation method thereof

Also Published As

Publication number Publication date
AU2003262375A1 (en) 2003-11-03
WO2003089408A2 (en) 2003-10-30
AU2003262375A8 (en) 2003-11-03

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