Title:
O-SUBSTITUTED SERINE DERIVATIVE PRODUCTION METHOD
Document Type and Number:
WIPO Patent Application WO/2020/095983
Kind Code:
A1
Abstract:
It was discovered that a cyclic sulfamidate could be produced by reacting an aminoacid derivative with a cyclization reagent.
In addition, it was discovered that an O-substituted serine derivative could be produced by reacting the cyclic sulfamidate with an alcohol.
Inventors:
ISHIZAWA TAKENORI (JP)
Application Number:
PCT/JP2019/043626
Publication Date:
May 14, 2020
Filing Date:
November 07, 2019
Export Citation:
Assignee:
CHUGAI PHARMACEUTICAL CO LTD (JP)
International Classes:
C07C227/18; C07C229/22; C07C269/00; C07C269/04; C07C269/06; C07C271/22; C07D307/42; C07D333/16; C07B61/00
Domestic Patent References:
| WO2010053050A1 | 2010-05-14 |
Foreign References:
| US4535167A | 1985-08-13 |
Other References:
MALHOTRA, RAJESH ET AL.: "Efficient asymmetric synthesis of N-protected-- aryloxyamino acids via regioselective ring opening of serine sulfamidate carboxylic acid", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 12, no. 33, 2014, pages 6507 - 6515, XP055707311, ISSN: 1477-0539, DOI: 10.1039/C4OB01047G
NAVO, CLAUDIO D. ET AL.: "Oxygen by Carbon Replacement at the Glycosidic Linkage Modulates the Sugar Conformation in Tn Antigen Mimics", ACS OMEGA, vol. 3, no. 12, 24 December 2018 (2018-12-24), pages 18142 - 18152, XP055707324, ISSN: 2470-1343, DOI: 10.1021/acsomega.8b02576
BOLEK, SYLWIA ET AL.: "Ring opening reactions of cyclic sulfamidates. Synthesis of beta -fluoroaryl alanines and derivatives of 4,4-difluoroglutamic acid", JOURNAL OF FLUORINE CHEMISTRY, vol. 217, 10 November 2018 (2018-11-10), pages 13 - 21, XP055707377, ISSN: 0022-1139, DOI: 10.1016/j.jfluchem.2018.11.003
FUTURE MED. CHEM., vol. 1, 2009, pages 1289 - 1310
J. MED. CHEM., vol. 53, no. 15, 2010, pages 5716 - 5726
TETRAHEDRON LETTERS, vol. 53, 2012, pages 3225 - 3229
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 2, 1992, pages 579 - 582
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 136, 2014, pages 12469 - 12478
ORGANIC AND BIOMOLECULAR CHEMISTRY, vol. 12, 2014, pages 6507 - 6515
"Greene's, ''Protective Groups in Organic Synthesis", 2014, JOHN WILEY & SONS
SHIMOKAWA ET AL., BIOORG. MED. CHEM. LETT., vol. 19, no. 1, 2009, pages 92 - 95
PRASHAD ET AL., ORG. LETT., vol. 5, no. 2, 2003, pages 125 - 128
SHIMOKAWA ET AL., BIOORG. MED. CHEM., vol. 19, no. 1, 2009, pages 92 - 95
See also references of EP 3878836A4
NAVO, CLAUDIO D. ET AL.: "Oxygen by Carbon Replacement at the Glycosidic Linkage Modulates the Sugar Conformation in Tn Antigen Mimics", ACS OMEGA, vol. 3, no. 12, 24 December 2018 (2018-12-24), pages 18142 - 18152, XP055707324, ISSN: 2470-1343, DOI: 10.1021/acsomega.8b02576
BOLEK, SYLWIA ET AL.: "Ring opening reactions of cyclic sulfamidates. Synthesis of beta -fluoroaryl alanines and derivatives of 4,4-difluoroglutamic acid", JOURNAL OF FLUORINE CHEMISTRY, vol. 217, 10 November 2018 (2018-11-10), pages 13 - 21, XP055707377, ISSN: 0022-1139, DOI: 10.1016/j.jfluchem.2018.11.003
FUTURE MED. CHEM., vol. 1, 2009, pages 1289 - 1310
J. MED. CHEM., vol. 53, no. 15, 2010, pages 5716 - 5726
TETRAHEDRON LETTERS, vol. 53, 2012, pages 3225 - 3229
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 2, 1992, pages 579 - 582
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 136, 2014, pages 12469 - 12478
ORGANIC AND BIOMOLECULAR CHEMISTRY, vol. 12, 2014, pages 6507 - 6515
"Greene's, ''Protective Groups in Organic Synthesis", 2014, JOHN WILEY & SONS
SHIMOKAWA ET AL., BIOORG. MED. CHEM. LETT., vol. 19, no. 1, 2009, pages 92 - 95
PRASHAD ET AL., ORG. LETT., vol. 5, no. 2, 2003, pages 125 - 128
SHIMOKAWA ET AL., BIOORG. MED. CHEM., vol. 19, no. 1, 2009, pages 92 - 95
See also references of EP 3878836A4
Attorney, Agent or Firm:
HARUNA, Masao et al. (JP)
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