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Title:
METHOD FOR PRODUCING OPTICALLY ACTIVE BICYCLO [3.1.0] HEXANE DERIVATIVE USING OXYGEN
Document Type and Number:
WIPO Patent Application WO/2011/061934
Kind Code:
A1
Abstract:
The disclosed method for producing a bicyclo [3.1.0] hexane represented by formula I or a salt thereof contains: a step for causing oxygen to act on a non-optically-active compound represented by formula II causing an asymmetric acylation reaction and a highly-stereoselective conversion to the optically active compound represented by formula III; and a step for converting the compound represented by formula III to the compound represented by formula I or a salt thereof.

Inventors:
SASAKI, Joji (24-1, Takada 3-chome, Toshima-k, Tokyo 33, 〒1708633, JP)
Application Number:
JP2010/006756
Publication Date:
May 26, 2011
Filing Date:
November 18, 2010
Export Citation:
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Assignee:
TAISHO PHARMACEUTICAL CO.,LTD. (24-1, Takada 3-chome Toshima-k, Tokyo 33, 〒1708633, JP)
大正製薬株式会社 (〒33 東京都豊島区高田3丁目24番1号 Tokyo, 〒1708633, JP)
International Classes:
C07C67/303; C07C69/753; C12P7/62; C07B53/00; C07B57/00; C07B61/00
Domestic Patent References:
WO2009142184A12009-11-26
WO2003061698A12003-07-31
WO2005000790A12005-01-06
WO2005000791A12005-01-06
WO2002000595A12002-01-03
Foreign References:
JPH0952887A1997-02-25
Other References:
NAKAZATO ATSURO ET AL.: "Synthesis, in Vitro Pharmacology, Structure-Activity Relationships, and Pharmacokinetics of 3-Alkoxy-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic Acid Derivatives as Potent and Selective Group II Metabotropic Glutamate Receptor Antagonists", JOURNAL OF MEDICINAL CHEMISTRY, vol. 47, no. 18, 26 August 2004 (2004-08-26), pages 4570 - 4587, XP008157980
YASUHARA AKITO ET AL.: "Synthesis, in vitro pharmacology, and structure-activity relationships of 2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as mGluR2 antagonists", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 14, no. 10, 15 May 2006 (2006-05-15), pages 3405 - 3420, XP008157938
YASUHARA AKITO ET AL.: "Prodrugs of 3-(3,4-dichlorobenzyloxy)-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (MGS0039): A potent and orally active group II mGluR antagonist with antidepressant-like potential", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 14, no. 12, 15 June 2006 (2006-06-15), pages 4193 - 4207, XP008157987
ZHANG FEI ET AL.: "Enantioselective Preparation of Ring-Fused 1-Fluorocyclopropane-1-carboxylate Derivatives: En Route to mGluR 2 Receptor Agonist MGS0028", ORGANIC LETTERS, vol. 6, no. 21, 14 October 2004 (2004-10-14), pages 3775 - 3777, XP008157968
WONG AUDREY ET AL.: "Reactive resin facilitated preparation of an enantiopure fluorobicycloketone", ORGANIC & BIOMOLECULAR CHEMISTRY, no. 2, 2004, pages 168 - 174, XP008157985
See also references of EP 2502897A4
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Attorney, Agent or Firm:
HAYAMI, Shinji (Gotanda TG Bldg. 9F, 9-2 Nishi-Gotanda 7-chome, Shinagawa-k, Tokyo 31, 〒1410031, JP)
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