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.
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Inventors:
SASAKI JOJI (JP)
Application Number:
PCT/JP2010/006756
Publication Date:
May 26, 2011
Filing Date:
November 18, 2010
Export Citation:
Assignee:
TAISHO PHARMACEUTICAL CO LTD (JP)
SASAKI JOJI (JP)
SASAKI JOJI (JP)
International Classes:
C07C67/303; C07C69/753; C12P7/62; C07B53/00; C07B57/00; C07B61/00
Domestic Patent References:
| WO2009142184A1 | 2009-11-26 | |||
| WO2003061698A1 | 2003-07-31 | |||
| WO2005000790A1 | 2005-01-06 | |||
| WO2005000791A1 | 2005-01-06 | |||
| WO2002000595A1 | 2002-01-03 |
Foreign References:
| JPH0952887A | 1997-02-25 |
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
SCIENCE, vol. 258, 1992, pages 597 - 603
TRENDS PHARMACOL. SCI., vol. 11, 1990, pages 508 - 515
TRENDS PHARMACOL. SCI., vol. 14, 1993, pages 13 - 20
J. MED. CHEM., vol. 47, 2004, pages 4570 - 4587
BIOORG. MED. CHEM., vol. 14, 2006, pages 3405 - 3420
BIOORG. MED. CHEM., vol. 14, 2006, pages 4193 - 4207
ORG. LETT., vol. 6, 2004, pages 3775 - 3777
J. MED. CHEM., vol. 43, 2000, pages 4893 - 4909
TETRAHEDRON, vol. 57, 2001, pages 7487 - 7493
ORG. BIOMOL. CHEM., vol. 2, 2004, pages 168 - 174
J. AM. CHEM. SOC., vol. 82, 1960, pages 4328
ORG. SYNTH., vol. 42, 1962, pages 50
ORG. LETT., vol. 7, 2005, pages 4573
SYNLETT, vol. 827, 1995
TETRAHEDRON LETTERS, vol. 37, 1996, pages 7131
ORG. LETT., vol. 2, 2000, pages 4189
See also references of EP 2502897A4
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
SCIENCE, vol. 258, 1992, pages 597 - 603
TRENDS PHARMACOL. SCI., vol. 11, 1990, pages 508 - 515
TRENDS PHARMACOL. SCI., vol. 14, 1993, pages 13 - 20
J. MED. CHEM., vol. 47, 2004, pages 4570 - 4587
BIOORG. MED. CHEM., vol. 14, 2006, pages 3405 - 3420
BIOORG. MED. CHEM., vol. 14, 2006, pages 4193 - 4207
ORG. LETT., vol. 6, 2004, pages 3775 - 3777
J. MED. CHEM., vol. 43, 2000, pages 4893 - 4909
TETRAHEDRON, vol. 57, 2001, pages 7487 - 7493
ORG. BIOMOL. CHEM., vol. 2, 2004, pages 168 - 174
J. AM. CHEM. SOC., vol. 82, 1960, pages 4328
ORG. SYNTH., vol. 42, 1962, pages 50
ORG. LETT., vol. 7, 2005, pages 4573
SYNLETT, vol. 827, 1995
TETRAHEDRON LETTERS, vol. 37, 1996, pages 7131
ORG. LETT., vol. 2, 2000, pages 4189
See also references of EP 2502897A4
Attorney, Agent or Firm:
HAYAMI, SHINJI (JP)
Shinji Hayami (JP)
Shinji Hayami (JP)
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