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WO2009106745A3 - Procede de preparation enantioselective de sulfoxydes - Google Patents

Procede de preparation enantioselective de sulfoxydes Download PDF

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Publication number
WO2009106745A3
WO2009106745A3 PCT/FR2008/001818 FR2008001818W WO2009106745A3 WO 2009106745 A3 WO2009106745 A3 WO 2009106745A3 FR 2008001818 W FR2008001818 W FR 2008001818W WO 2009106745 A3 WO2009106745 A3 WO 2009106745A3
Authority
WO
WIPO (PCT)
Prior art keywords
general formula
enantio
sulphoxides
pyridyle
preparation
Prior art date
Application number
PCT/FR2008/001818
Other languages
English (en)
Other versions
WO2009106745A2 (fr
Inventor
Avraham Cohen
Henri Kagan
François SCHUTZE
Suzy Charbit
Stéphane BERNAD
Original Assignee
Sidem Pharma Sa
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 Sidem Pharma Sa filed Critical Sidem Pharma Sa
Publication of WO2009106745A2 publication Critical patent/WO2009106745A2/fr
Publication of WO2009106745A3 publication Critical patent/WO2009106745A3/fr

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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
    • 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)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Catalysts (AREA)

Abstract

L'invention concerne la préparation énantiosélective d'énantiomères de sulfoxydes. Le procédé de préparation de sulfoxydes de formule générale (I) ci-après : A-SO-CH2-B (I) dans laquelle A est un noyau benzimidazole ou imidazo- pyridyle, et B est un noyau pyridyle, consiste à coupler un sulfinate chiral de formule générale (II) A-(SO)-OR (II) dans laquelle R est un groupement inducteur de chiralité, ledit sulfinate étant sous forme d'un diastéréoisomère, avec un composé organométallique de formule générale (III) B-CH2-Y (III) dans laquelle Y représente un reste d'organolithien ou d ' organomagnésien. Application à la préparation de dérivés utiles en thérapeutique.
PCT/FR2008/001818 2007-12-27 2008-12-23 Procede de preparation enantioselective de sulfoxydes WO2009106745A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0709147A FR2925899B1 (fr) 2007-12-27 2007-12-27 Procede de preparation enantioselective de sulfoxydes.
FR0709147 2007-12-27

Publications (2)

Publication Number Publication Date
WO2009106745A2 WO2009106745A2 (fr) 2009-09-03
WO2009106745A3 true WO2009106745A3 (fr) 2009-10-22

Family

ID=39682712

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2008/001818 WO2009106745A2 (fr) 2007-12-27 2008-12-23 Procede de preparation enantioselective de sulfoxydes

Country Status (2)

Country Link
FR (1) FR2925899B1 (fr)
WO (1) WO2009106745A2 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5948789A (en) * 1994-07-15 1999-09-07 Astra Aktiebolag Process for synthesis of substituted sulphoxides
EP0652872B1 (fr) * 1993-05-28 2000-11-08 AstraZeneca AB Sel de magnesium optiquement pur de compose de pyridinylmethyle sulfinyl-1h-benzimidazole
WO2006037894A1 (fr) * 2004-10-05 2006-04-13 Sidem Pharma S.A. Procede de preparation enantioselective de derives de sulfoxydes.
EP1992619A1 (fr) * 2007-05-18 2008-11-19 Quimica Sintetica, S.A. Procédé de préparation de 2-(2-pyridylmethyl)-sulfinyl-1H-benzimidazoles et produits intermédiaires utilisés dans ce procédé

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5756531A (en) * 1996-04-30 1998-05-26 Abbott Laboratories Iminoxy derivatives of indole and indene compounds as inhibitors of prostaglandin biosynthesis
CA2476162A1 (fr) * 2002-02-13 2003-08-21 Takeda Chemical Industries, Ltd. Inhibiteur de jnk

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0652872B1 (fr) * 1993-05-28 2000-11-08 AstraZeneca AB Sel de magnesium optiquement pur de compose de pyridinylmethyle sulfinyl-1h-benzimidazole
US5948789A (en) * 1994-07-15 1999-09-07 Astra Aktiebolag Process for synthesis of substituted sulphoxides
WO2006037894A1 (fr) * 2004-10-05 2006-04-13 Sidem Pharma S.A. Procede de preparation enantioselective de derives de sulfoxydes.
EP1992619A1 (fr) * 2007-05-18 2008-11-19 Quimica Sintetica, S.A. Procédé de préparation de 2-(2-pyridylmethyl)-sulfinyl-1H-benzimidazoles et produits intermédiaires utilisés dans ce procédé

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HOUPIS I N ET AL: "Nickel Catalyzed Addition of Organozincates to Optically Pure Vinylic Sulfoxides. Synthesis of the Phosphodiesterase IV Inhibitor L-765,527 (CDP-840)", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, vol. 38, no. 41, 13 October 1997 (1997-10-13), pages 7131 - 7134, XP004091700, ISSN: 0040-4039 *

Also Published As

Publication number Publication date
FR2925899A1 (fr) 2009-07-03
FR2925899B1 (fr) 2012-12-21
WO2009106745A2 (fr) 2009-09-03

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