Title:
METHOD FOR PRODUCING (2S)-2-[(1H-PYRAZOL-1-YL)METHYL]-1,3-OXAZINANE DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2019/013244
Kind Code:
A1
Abstract:
Provided is a novel method for producing a (2S)-2-[(1H-pyrazol-1-yl)methyl]-1,3-oxazinane derivative. More specifically, a method for producing a (2S)-2-[(1H-pyrazol-1-yl)methyl]-1,3-oxazinane derivative represented by formula (1) is provided, and the method comprises reacting 3-aminopropan-1-ol with glyoxylic acid.
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Inventors:
MATSUBARA TAKAAKI (JP)
URABE HIROKI (JP)
SUZUKI RYO (JP)
FUTAMURA AYA (JP)
KINOSHITA RYO (JP)
HATTORI NOBUTAKA (JP)
TABUSE HIDEAKI (JP)
IMURA KOREAKI (JP)
OTAKE NORIKAZU (JP)
URABE HIROKI (JP)
SUZUKI RYO (JP)
FUTAMURA AYA (JP)
KINOSHITA RYO (JP)
HATTORI NOBUTAKA (JP)
TABUSE HIDEAKI (JP)
IMURA KOREAKI (JP)
OTAKE NORIKAZU (JP)
Application Number:
PCT/JP2018/026160
Publication Date:
January 17, 2019
Filing Date:
July 11, 2018
Export Citation:
Assignee:
TAISHO PHARMACEUTICAL CO LTD (JP)
International Classes:
C07D413/14; A61K31/5355; A61P25/20; C07D265/06
Domestic Patent References:
| WO2013187467A1 | 2013-12-19 | |||
| WO2015087853A1 | 2015-06-18 | |||
| WO2001094322A1 | 2001-12-13 | |||
| WO2013187467A1 | 2013-12-19 | |||
| WO2015087853A1 | 2015-06-18 |
Foreign References:
| JP2015131803A | 2015-07-23 | |||
| JP2015131803A | 2015-07-23 |
Other References:
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SVETLIK, J. ET AL.: "Synthesis of some pyrazolo[1,5‐c][1,3]benzoxazines and a new 5H‐pyrazolo[1,5‐c][1,3,2]benzoxazaphosphorine ring system", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 42, no. 6, 2005, pages 1143 - 1147, XP055662934, ISSN: 0022-152X, DOI: 10.1002/jhet.5570420616
KAREL M. J. BRANDSJOSEPH F. PAYACKJONATHAN D. ROSENTODD D. NELSONALEXANDER CANDELARIOMARK A. HUFFMANMATTHEW M. ZHAOJING LIBRIDGETT: "Efficient Synthesis of NK1 Receptor Antagonist Aprepitant Using a Crystallization-Induced Diastereoselective Transformation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 125, no. 8, 30 January 2003 (2003-01-30), pages 2129 - 2135, XP002742845, ISSN: 0002-7863, DOI: 10.1021/ja027458g
PERRON-SIERRA, F.M.: "Synthesis of a novel dioxan sialic acid analog", TETRAHEDRON LETTERS, vol. 45, no. 21, 2004, pages 4163 - 4166, XP085010730, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2004.03.135
ZHU Y. ET AL., PHARMACOL. SCI., vol. 92, 2003, pages 259 - 266
ZEITZER J.M. ET AL., TRENDS PHARMACOL. SCI., vol. 27, 2006, pages 368 - 374
MARCUS J.N., J. COMP. NEUROL, vol. 435, 2001, pages 6 - 25
TRIVEDI J.P. ET AL., FEBSLETT, vol. 438, 1998, pages 71 - 75
YAMANAKA A., BIOCHEM. BIOPHYS. RES. COMMUN., vol. 290, 2002, pages 1237 - 1245
HAGAN J.J. ET AL., PROC. NATL. ACAD. SCI. USA, vol. 96, 1999, pages 10911 - 10916
NAKAMURA T. ET AL., BRAIN RES., vol. 873, 2000, pages 181 - 187
SMITH M.I., NEUROSCI. LETT., vol. 341, 2003, pages 256 - 258
BRISBARE-ROCH C. ET AL., NAT. MED., vol. 13, 2007, pages 150 - 155
COX C.D. ET AL., J. MED. CHEM., vol. 53, 2010, pages 5320 - 5332
SVETLIK JAN ET AL., J. HETEROCYCLIC CHEM., vol. 42, no. 6, 2005, pages 1143 - 1147
See also references of EP 3653623A4
SVETLIK, J. ET AL.: "Synthesis of some pyrazolo[1,5‐c][1,3]benzoxazines and a new 5H‐pyrazolo[1,5‐c][1,3,2]benzoxazaphosphorine ring system", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 42, no. 6, 2005, pages 1143 - 1147, XP055662934, ISSN: 0022-152X, DOI: 10.1002/jhet.5570420616
KAREL M. J. BRANDSJOSEPH F. PAYACKJONATHAN D. ROSENTODD D. NELSONALEXANDER CANDELARIOMARK A. HUFFMANMATTHEW M. ZHAOJING LIBRIDGETT: "Efficient Synthesis of NK1 Receptor Antagonist Aprepitant Using a Crystallization-Induced Diastereoselective Transformation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 125, no. 8, 30 January 2003 (2003-01-30), pages 2129 - 2135, XP002742845, ISSN: 0002-7863, DOI: 10.1021/ja027458g
PERRON-SIERRA, F.M.: "Synthesis of a novel dioxan sialic acid analog", TETRAHEDRON LETTERS, vol. 45, no. 21, 2004, pages 4163 - 4166, XP085010730, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2004.03.135
ZHU Y. ET AL., PHARMACOL. SCI., vol. 92, 2003, pages 259 - 266
ZEITZER J.M. ET AL., TRENDS PHARMACOL. SCI., vol. 27, 2006, pages 368 - 374
MARCUS J.N., J. COMP. NEUROL, vol. 435, 2001, pages 6 - 25
TRIVEDI J.P. ET AL., FEBSLETT, vol. 438, 1998, pages 71 - 75
YAMANAKA A., BIOCHEM. BIOPHYS. RES. COMMUN., vol. 290, 2002, pages 1237 - 1245
HAGAN J.J. ET AL., PROC. NATL. ACAD. SCI. USA, vol. 96, 1999, pages 10911 - 10916
NAKAMURA T. ET AL., BRAIN RES., vol. 873, 2000, pages 181 - 187
SMITH M.I., NEUROSCI. LETT., vol. 341, 2003, pages 256 - 258
BRISBARE-ROCH C. ET AL., NAT. MED., vol. 13, 2007, pages 150 - 155
COX C.D. ET AL., J. MED. CHEM., vol. 53, 2010, pages 5320 - 5332
SVETLIK JAN ET AL., J. HETEROCYCLIC CHEM., vol. 42, no. 6, 2005, pages 1143 - 1147
See also references of EP 3653623A4
Attorney, Agent or Firm:
ONO, SHINJIRO et al. (JP)
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