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Title:
NAHLSGEN OPTICAL RESOLUTION METHOD
Document Type and Number:
WIPO Patent Application WO/2018/051972
Kind Code:
A1
Abstract:
Provided is a method for separating the four optical isomers of Nahlsgen. According to the present invention, a method for producing a mixture of D-2-amino-4-[(Rp)-(3-carboxymethylphenoxy)(methoxy)phosphoryl]butanoic acid hydrate and L-2-amino-4-[(Sp)-(3-carboxymethylphenoxy)(methoxy)phosphoryl]butanoic acid hydrate is characterized by comprising a step of: subjecting a mixture of the four optical isomers represented by the following formula (1') to fractional crystallization using water or a mixed solvent of water and a water-soluble organic solvent, and causing a mixture of a compound represented by the following formula (1-1'-1) and a compound represented by the following formula (1-4'-1) to deposit.

Inventors:
WATANABE, Bunta (36-1 Yoshida-honmachi, Sakyo-ku, Kyoto-sh, Kyoto 01, 〒6068501, JP)
YOSHIOKA, Ryuzo (2-16-12-106, Kounai Takatsuki-sh, Osaka 07, 〒5690007, JP)
ISHIDA, Hideaki (1513-1-B201, Oaza Higashisue Ube-sh, Yamaguchi 06, 〒7590206, JP)
Application Number:
JP2017/032829
Publication Date:
March 22, 2018
Filing Date:
September 12, 2017
Export Citation:
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Assignee:
KYOTO UNIVERSITY (36-1, Yoshida-honmachi Sakyo-ku, Kyoto-sh, Kyoto 01, 〒6068501, JP)
International Classes:
C07F9/40; A61P17/00; C07B57/00; C07B63/00; A61K31/662; A61P37/08
Domestic Patent References:
WO2007066705A12007-06-14
Other References:
TERZYAN, SIMON S. ET AL.: "STRUCTURES OF THE FREE ENZYME, INHIBITOR-BOUND TETRAHEDRAL TRANSITION STATES, AND GLUTAMATE-BOUND ENZYME REVEAL NOVEL MOVEMENT WITHIN THE ACTIVE SITE DURING CATALYSIS", J. BIOL. CHEM., 26 May 2015 (2015-05-26), XP055497548, Retrieved from the Internet [retrieved on 20171010]
HAN, LIYOU ET AL.: "- Design, synthesis, and evaluation of gamma-phosphono diester analogues of glutamate as highly potent inhibitors and active site probes of gamma-glutamyl transpeptidase", BIOCHEMISTRY, vol. 46, no. 5, 2007, pages 1432 - 1447, XP002491849
KAMIYAMA, AKANE ET AL.: "Phosphonate-based irreversible inhibitors of human c-glutamyl transpeptidase (GGT). GGsTop is a non-toxic and highly selective inhibitor with critical electrostatic interaction with an active-site residue Lys562 for enhanced inhibitory activity", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 24, 2016, pages 5340 - 5352, XP029763054
WATANABE, BUNTA ET AL., TETRAHEDRON LETTERS, vol. 58, 8 August 2017 (2017-08-08), pages 3700 - 3703, XP085164776
Attorney, Agent or Firm:
GOTO & CO. (2-18, Kobai-cho Kita-ku, Osaka-sh, Osaka 38, 〒5300038, JP)
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