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Title:
METHOD FOR PRODUCING PROTON PUMP INHIBITOR COMPOUND HAVING OPTICAL ACTIVITY
Document Type and Number:
WIPO Patent Application WO/2016/104668
Kind Code:
A1
Abstract:
Through a method for producing an optically active sulfoxide of formula 2 or a salt thereof by oxidizing a sulfide of formula 1 or salt thereof by means of hydrogen peroxide using an iron salt in the presence of a chiral ligand of formula 3, a high-purity proton pump inhibitor compound having optical activity can be safely and inexpensively prepared at high yield and in an enantioselective manner. [In the formula, A represents CH or N; R1 represents a hydrogen atom, an alkyl optionally substituted by a halogen, or an alkoxy optionally substituted by a halogen; R2 may represent one to three units, each independently representing an alkyl, a dialkylamine, or an alkoxy optionally substituted by a halogen or an alkoxy; each R3 independently represents a hydrogen atom, a halogen, a cyano, etc; R4 represents a tertiary alkyl; and * and ** each represent an R arrangement or an S arrangement.]

Inventors:
NAKAMURA, Eiichi (3-1 Hongo 7-chome, Bunkyo-k, Tokyo 54, 〒1138654, JP)
ILIES, Laurean (3-1 Hongo 7-chome, Bunkyo-k, Tokyo 54, 〒1138654, JP)
ODERAOTOSHI, Yoji (2-11, Shinbashi-cho, Kadoma-sh, Osaka 80, 〒5718580, JP)
IZUMI, Takuhiro (2-11, Shinbashi-cho, Kadoma-sh, Osaka 80, 〒5718580, JP)
NISHIGUCHI, Shigenobu (2-11, Shinbashi-cho, Kadoma-sh, Osaka 80, 〒5718580, JP)
Application Number:
JP2015/086163
Publication Date:
June 30, 2016
Filing Date:
December 25, 2015
Export Citation:
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Assignee:
THE UNIVERSITY OF TOKYO (3-1 Hongo 7-chome, Bunkyo-ku Tokyo, 54, 〒1138654, JP)
TOWA PHARMACEUTICAL CO., LTD. (2-11, Shinbashi-cho Kadoma-sh, Osaka 80, 〒5718580, JP)
International Classes:
C07D401/12; A61K31/4439; A61P1/04; A61P43/00; C07C251/24; C07B61/00; C07F15/02
Domestic Patent References:
WO2001083473A12001-11-08
WO2006112442A12006-10-26
WO2008047681A12008-04-24
WO2003089408A22003-10-30
WO2010043601A12010-04-22
Foreign References:
JPH10504290A1998-04-28
JP2006523201A2006-10-12
JP2006516261A2006-06-29
Other References:
TORU TAKESHI ET AL.: "Asymmetric Synthesis of Chiral Sulfoxides", ORGANOSULFUR CHEMISTRY IN ASYMMETRIC SYNTHESIS., 2008, pages 1 - 29, XP055461794
O'MAHONY GRAHAM E. ET AL.: "Copper-Catalyzed Asymmetric Oxidation of Sulfides", JOURNAL OF ORGANIC CHEMISTRY, vol. 77, no. 7, 2012, pages 3288 - 3296, XP055460373
O'MAHONY GRAHAM E. ET AL.: "Investigation of steric and electronic effects in the copper- catalysed asymmetric oxidation of sulfides", TETRAHEDRON, vol. 69, no. 47, 2013, pages 10168 - 10184, XP028756307, DOI: doi:10.1016/j.tet.2013.08.063
BOLM CARSTEN ET AL.: "Iron-Catalyzed Asymmetric Sulfide Oxidation with Aqueous Hydrogen Peroxide", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 42, no. 44, 2003, pages 5487 - 5489, XP055460375
BOLM CARSTEN ET AL.: "Highly Enantioselective Iron-Catalyzed Sulfide Oxidation with Aqueous Hydrogen Peroxide under Simple Reaction Conditions", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 43, no. 32, 2004, pages 4225 - 4228, XP002745768, DOI: doi:10.1002/anie.200460236
BOLM CARSTEN ET AL.: "Investigations on the Iron-Catalyzed Asymmetric Sulfide Oxidation", CHEMISTRY - A EUROPEAN JOURNAL, vol. 11, no. 4, 2005, pages 1086 - 1092, XP002745769, DOI: doi:10.1002/chem.200400857
KELLY PADRAIG ET AL.: "Asymmetric Synthesis of Aryl Benzyl Sulfoxides by Vanadium-Catalysed Oxidation: A Combination of Enantioselective Sulfide Oxidation and Kinetic Resolution in Sulfoxide Oxidation", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 19, 2006, pages 4500 - 4509, XP055460381
BUHLER STEFANIE ET AL.: "Chiral Sulfoxides as Metabolites of 2-Thioimidazole-Based p38r Mitogen-Activated Protein Kinase Inhibitors: Enantioselective Synthesis and Biological Evaluation", JOURNAL OF MEDICINAL CHEMISTRY, vol. 54, no. 9, 2011, pages 3283 - 3297, XP055460383
See also references of EP 3239146A4
Attorney, Agent or Firm:
SAKAMOTO, Tomohiro (13 Yotsuya 2-chome, Shinjuku-ku Tokyo, 04, 〒1600004, JP)
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