WO2004087702A3 - Procede de preparation enantioselective de derives de sulfoxydes. - Google Patents

Procede de preparation enantioselective de derives de sulfoxydes.

Info

Publication number
WO2004087702A3
WO2004087702A3 PCT/FR2004/000778 FR2004000778W WO2004087702A3 WO 2004087702 A3 WO2004087702 A3 WO 2004087702A3 FR 2004000778 W FR2004000778 W FR 2004000778W WO 2004087702 A3 WO2004087702 A3 WO 2004087702A3
Authority
WO
WIPO (PCT)
Prior art keywords
enantioselective
sulphoxide
enantioselective preparation
nucleus
preparation
Prior art date
Application number
PCT/FR2004/000778
Other languages
English (en)
Other versions
WO2004087702A2 (fr
Inventor
Avraham Cohen
Suzy Charbit
Francois Schutze
Frederic Martinet
Original Assignee
Sidem Pharma
Avraham Cohen
Suzy Charbit
Francois Schutze
Frederic Martinet
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
Priority claimed from FR0303914A external-priority patent/FR2852956B1/fr
Priority claimed from FR0314679A external-priority patent/FR2863611B1/fr
Application filed by Sidem Pharma, Avraham Cohen, Suzy Charbit, Francois Schutze, Frederic Martinet filed Critical Sidem Pharma
Priority to CA002520157A priority Critical patent/CA2520157A1/fr
Priority to JP2006505762A priority patent/JP2006523201A/ja
Priority to EP04742382A priority patent/EP1608649A2/fr
Priority to US10/551,037 priority patent/US20060281782A1/en
Publication of WO2004087702A2 publication Critical patent/WO2004087702A2/fr
Publication of WO2004087702A3 publication Critical patent/WO2004087702A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé de préparation énantiosélective de dérivés substitués de sulfoxydes. Le procédé consiste à effectuer une oxydation énantiosélective d'un sulfure de formule générale (I) ci-après A - CH2 - S - B (I) dans laquelle A est un noyau pyridyle diversement substitué et B un reste hétérocyclique comportant un noyau benzimidazole ou imidazo-pyridyle, au moyen d'un agent oxydant en présence d'un catalyseur à base de tungstène ou de vanadium et d'unligand chiral, suivie le cas échéant d'une salification par une base, pour obtenir le sulfoxyde A - CH2 - SO - B (Ia). Application à la préparation énantiosélective de composés tels que les énantiomères du ténatoprazole et d'autres sulfoxydes comparables.
PCT/FR2004/000778 2003-03-28 2004-03-26 Procede de preparation enantioselective de derives de sulfoxydes. WO2004087702A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002520157A CA2520157A1 (fr) 2003-03-28 2004-03-26 Procede de preparation enantioselective de derives de sulfoxydes
JP2006505762A JP2006523201A (ja) 2003-03-28 2004-03-26 スルホキシド誘導体をエナンチオ選択的に調製する方法
EP04742382A EP1608649A2 (fr) 2003-03-28 2004-03-26 Procede de preparation enantioselective de derives de sulfoxydes.
US10/551,037 US20060281782A1 (en) 2003-03-28 2004-03-26 Method for the enantioselective preparation of sulphoxide derivatives

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR0303914 2003-03-28
FR0303914A FR2852956B1 (fr) 2003-03-28 2003-03-28 Procede de preparation enantioselective de derives de sulfoxydes
FR0314679A FR2863611B1 (fr) 2003-12-15 2003-12-15 Procede de preparation enantioselective de derives de sulfoxydes
FR0314679 2003-12-15

Publications (2)

Publication Number Publication Date
WO2004087702A2 WO2004087702A2 (fr) 2004-10-14
WO2004087702A3 true WO2004087702A3 (fr) 2004-11-11

Family

ID=33133109

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2004/000778 WO2004087702A2 (fr) 2003-03-28 2004-03-26 Procede de preparation enantioselective de derives de sulfoxydes.

Country Status (6)

Country Link
US (1) US20060281782A1 (fr)
EP (1) EP1608649A2 (fr)
JP (1) JP2006523201A (fr)
KR (1) KR20060002878A (fr)
CA (1) CA2520157A1 (fr)
WO (1) WO2004087702A2 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2871800B1 (fr) * 2004-06-17 2006-08-25 Sidem Pharma Sa Sa Sel de sodium monohydrate du s-tenatoprazole et application en therapeutique
CA2597632C (fr) * 2005-03-25 2012-05-15 Livzon Pharmaceutical Group Inc. Derives de sulfoxyde substitues, methodes de synthese desdits derives et applications desdits derives
EP1801110A1 (fr) 2005-12-22 2007-06-27 KRKA, tovarna zdravil, d.d., Novo mesto Sel d'arginine d'ésoméprazole
WO2007088559A1 (fr) * 2006-02-01 2007-08-09 Jubilant Organosys Limited Procédé de production de sulphoxydes substitués
CN1810803B (zh) * 2006-02-17 2010-11-17 中国科学院上海有机化学研究所 高对映体选择性制备(s)-奥美拉唑的方法
JP2009196894A (ja) * 2006-10-13 2009-09-03 Eisai R & D Management Co Ltd スルフィニルベンズイミダゾール化合物またはその塩の製造方法
JP5492417B2 (ja) 2006-10-13 2014-05-14 エーザイ・アール・アンド・ディー・マネジメント株式会社 胃酸分泌抑制作用を有するベンズイミダゾール化合物
US7531666B2 (en) * 2007-06-26 2009-05-12 Syn-Tech Chem. & Pharm. Co., Ltd. Method for preparing 2-(2-pyridinylmethylsulfinyl) benzimidazoles
EP2264024A1 (fr) 2008-10-14 2010-12-22 LEK Pharmaceuticals d.d. Procédé de préparation d'inhibiteurs de la pompe à protons énantiomériquement enrichis
BR112012001078A8 (pt) * 2009-07-16 2016-05-03 Bayer Cropscience Ag Processo para preparação de derivados de sulfóxido de 3-triazolila quirais
WO2016104668A1 (fr) * 2014-12-26 2016-06-30 国立大学法人 東京大学 Procédé de fabrication d'un composé inhibiteur de la pompe à protons ayant une activité optique
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

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0005129A1 (fr) * 1978-04-14 1979-10-31 Aktiebolaget Hässle Pyridylsulfinylbenzimidazoles substitués, compositions pharmaceutiques les renfermant et les intermédiaires pour leur préparation
EP0137417A1 (fr) * 1983-10-08 1985-04-17 Bayer Ag Procédé pour la préparation d'aminobenzène-alkyl sulfones ou d'aminobenzène-alkyl sulfoxydes
EP0302720A1 (fr) * 1987-08-04 1989-02-08 Takeda Chemical Industries, Ltd. Préparation de composés 2-(2-pyridylméthylsulfinyl)-benzimidazoliques
WO1996002535A1 (fr) * 1994-07-15 1996-02-01 Astra Aktiebolag Procede de synthese de sulfoxydes substitues
WO2003089408A2 (fr) * 2002-04-22 2003-10-30 Sun Pharmaceutical Industries Limited Pyridinylmethyl-sulphinyl-benzimidazole substitue optiquement actif et sels

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5374730A (en) * 1993-11-04 1994-12-20 Torcan Chemical Ltd. Preparation of omeprazole and lansoprazole

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0005129A1 (fr) * 1978-04-14 1979-10-31 Aktiebolaget Hässle Pyridylsulfinylbenzimidazoles substitués, compositions pharmaceutiques les renfermant et les intermédiaires pour leur préparation
EP0137417A1 (fr) * 1983-10-08 1985-04-17 Bayer Ag Procédé pour la préparation d'aminobenzène-alkyl sulfones ou d'aminobenzène-alkyl sulfoxydes
EP0302720A1 (fr) * 1987-08-04 1989-02-08 Takeda Chemical Industries, Ltd. Préparation de composés 2-(2-pyridylméthylsulfinyl)-benzimidazoliques
WO1996002535A1 (fr) * 1994-07-15 1996-02-01 Astra Aktiebolag Procede de synthese de sulfoxydes substitues
US5948789A (en) * 1994-07-15 1999-09-07 Astra Aktiebolag Process for synthesis of substituted sulphoxides
WO2003089408A2 (fr) * 2002-04-22 2003-10-30 Sun Pharmaceutical Industries Limited Pyridinylmethyl-sulphinyl-benzimidazole substitue optiquement actif et sels

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
COTTON H ET AL: "Asymmetric synthesis of esomeprazole", TETRAHEDRON: ASYMMETRY, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 11, no. 18, 22 September 2000 (2000-09-22), pages 3819 - 3825, XP004224163, ISSN: 0957-4166 *
DONNOLI M I ET AL: "Catalytic Asymmetric Oxidation of Aryl Sulfides with a Ti/H2O/(R,R)-Diphenylethane-1,2-diol Complex: a Versatile and Highly Enantioselective Oxidation Protocol", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 63, 1998, pages 9392 - 9395, XP002269765, ISSN: 0022-3263 *
LUETJENS H ET AL: "New Chiral C3-Symmetric Triols as Ligands for Vanadium and Titanium Complexes", ORGANOMETALLICS, WASHINGTON, DC, US, vol. 16, 1997, pages 5869 - 5878, XP002269762, ISSN: 0276-7333 *
PITCHEN P ET AL: "AN EFFICIENT ASYMMETRI OXIDATION OF SULFIDES TO SULFOXIDES", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 106, 26 December 1984 (1984-12-26), pages 8188 - 8193, XP000644322, ISSN: 0002-7863 *
VELDE VAN DE F ET AL: "Biocatalytic and biomimetic oxidations with vanadium", JOURNAL OF INORGANIC BIOCHEMISTRY, NEW YORK, NY, US, vol. 80, 2000, pages 81 - 89, XP002269763 *

Also Published As

Publication number Publication date
CA2520157A1 (fr) 2004-10-14
WO2004087702A2 (fr) 2004-10-14
JP2006523201A (ja) 2006-10-12
KR20060002878A (ko) 2006-01-09
US20060281782A1 (en) 2006-12-14
EP1608649A2 (fr) 2005-12-28

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