Title:
NOVEL STIRIPENTOL DERIVATIVE AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2022/025242
Kind Code:
A1
Abstract:
The present invention provides a novel compound that can be used as a lactate dehydrogenase inhibitor and as an active ingredient of pharmaceuticals such as antiepileptic agents and anticancer agents, in particular, a novel compound having excellent metabolic stability. The novel compound is represented by formula (1). In formula (1), R represents an arbitrary substituent (for example, an aromatic or non-aromatic 3- to 14-membered monovalent substituent that may be unsubstituted or substituted, or monocyclic or polycyclic), and Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, and Ri each represent a hydrogen atom or an arbitrary substituent (for example, all Ra to Ri are hydrogen atoms, or Re, Rf, Rg, Rh, and Ri each are a hydrogen atom, and at least one among Ra, Rb, Rc, and Rd is an arbitrary substituent).
Inventors:
INOUE TSUYOSHI (JP)
SADA NAGISA (JP)
SADA NAGISA (JP)
Application Number:
PCT/JP2021/028307
Publication Date:
February 03, 2022
Filing Date:
July 30, 2021
Export Citation:
Assignee:
NAT UNIV CORPORATION OKAYAMA UNIV (JP)
International Classes:
A61P25/08; A61K31/36; A61K31/381; A61K31/443; A61P35/00; A61P43/00; C07D317/50; C07D405/10; C07D409/10
Domestic Patent References:
| WO2016129583A1 | 2016-08-18 | |||
| WO2016129583A1 | 2016-08-18 | |||
| WO2014115764A1 | 2014-07-31 |
Foreign References:
| FR2253503A2 | 1975-07-04 | |||
| CN108276376A | 2018-07-13 | |||
| JPH0381072B2 | 1991-12-26 | |||
| US10350192B2 | 2019-07-16 | |||
| JP6194322B2 | 2017-09-06 |
Other References:
CHANG, M. ET AL.: "NBS-mediated cyclization of trans-cinnamic alcohols", TETRAHEDRON, vol. 69, no. 31, 2013, pages 6364 - 6370, XP028570800, DOI: 10.1016/j.tet.2013.05.110
KOPPOLU, S. R. ET AL.: "Triflic acid promoted direct a-alkylation of unactivated ketones using benzylic alcohols via in situ formed acetals", JOURNAL OF ORGANIC CHEMISTRY, vol. 79, no. 13, 2014, pages 6069 - 6078, XP055903409
YUAN, Z. ET AL.: "Tandem 1,6- addition/cyclization/vinylcyclopropane rearrangement at low temperature under metal-free conditions: an approach to spiro[4.5]cyclohexadienones", CHEMICAL COMMUNICATIONS, vol. 53, no. 24, 2017, Cambridge, United Kingdom, pages 3485 - 3488, XP055903413
KRISHNA, J. ET AL.: "Sequential one-pot approach for the synthesis of functionalized phthalans via Heck-reduction-cyclization (HRC) reactions", RSC ADVANCES, vol. 5, no. 34, 2015, pages 26749 - 26761, XP055903416
RAMA VINOD UCHIL, JOSHI VIDYA: "Selective reductions of substituted a-(1,2,4-triazol-1-yl)chalcones with NaBH4 and Al-isopropoxide: synthesis of substituted (±) c<- (4-chlorophenyl) -beta- (phenylmethylene)-1H-1,2,4-triazole- 1-ethanols having potential bacteriostatic and agro-based fungicidal activity", INDIAN JOURNAL OF CHEMISTRY, vol. 41 B, no. 3, 1 January 2002 (2002-01-01), pages 631 - 634, XP093024347
KWANBRODIE, N ENGL J MED, vol. 342, 2000, pages 314 - 319
NEAL ET AL., LANCET NEUROL, vol. 7, 2008, pages 500 - 506
SADA ET AL., SCIENCE, vol. 347, 2015, pages 1362 - 1367
CHIRON ET AL., LANCET, vol. 356, 2000, pages 1638 - 1642
QUILICHINI ET AL., EPILEPSIA, vol. 47, 2006, pages 704 - 716
FANTIN ET AL., CANCER CELL, vol. 9, 2006, pages 425 - 434
XIE ET AL., CELL METAB, vol. 19, 2014, pages 795 - 809
LE ET AL., PROC NATL ACAD SCI USA, vol. 107, 2010, pages 2037 - 2042
GRANCHI ET AL., J MED CHEM, vol. 54, 2011, pages 1599 - 1612
BILLIARD ET AL., CANCER METAB, vol. 1, 2013, pages 1 - 19
LE DUDAL ET AL., J CLIN INVEST, vol. 129, 2019, pages 2571 - 2577
FUJIWARA ET AL., J ANESTH, vol. 34, 2020, pages 373 - 381
RIBAN ET AL., NEUROSCIENCE, vol. 112, 2002, pages 101 - 111
See also references of EP 4190401A4
KOPPOLU, S. R. ET AL.: "Triflic acid promoted direct a-alkylation of unactivated ketones using benzylic alcohols via in situ formed acetals", JOURNAL OF ORGANIC CHEMISTRY, vol. 79, no. 13, 2014, pages 6069 - 6078, XP055903409
YUAN, Z. ET AL.: "Tandem 1,6- addition/cyclization/vinylcyclopropane rearrangement at low temperature under metal-free conditions: an approach to spiro[4.5]cyclohexadienones", CHEMICAL COMMUNICATIONS, vol. 53, no. 24, 2017, Cambridge, United Kingdom, pages 3485 - 3488, XP055903413
KRISHNA, J. ET AL.: "Sequential one-pot approach for the synthesis of functionalized phthalans via Heck-reduction-cyclization (HRC) reactions", RSC ADVANCES, vol. 5, no. 34, 2015, pages 26749 - 26761, XP055903416
RAMA VINOD UCHIL, JOSHI VIDYA: "Selective reductions of substituted a-(1,2,4-triazol-1-yl)chalcones with NaBH4 and Al-isopropoxide: synthesis of substituted (±) c<- (4-chlorophenyl) -beta- (phenylmethylene)-1H-1,2,4-triazole- 1-ethanols having potential bacteriostatic and agro-based fungicidal activity", INDIAN JOURNAL OF CHEMISTRY, vol. 41 B, no. 3, 1 January 2002 (2002-01-01), pages 631 - 634, XP093024347
KWANBRODIE, N ENGL J MED, vol. 342, 2000, pages 314 - 319
NEAL ET AL., LANCET NEUROL, vol. 7, 2008, pages 500 - 506
SADA ET AL., SCIENCE, vol. 347, 2015, pages 1362 - 1367
CHIRON ET AL., LANCET, vol. 356, 2000, pages 1638 - 1642
QUILICHINI ET AL., EPILEPSIA, vol. 47, 2006, pages 704 - 716
FANTIN ET AL., CANCER CELL, vol. 9, 2006, pages 425 - 434
XIE ET AL., CELL METAB, vol. 19, 2014, pages 795 - 809
LE ET AL., PROC NATL ACAD SCI USA, vol. 107, 2010, pages 2037 - 2042
GRANCHI ET AL., J MED CHEM, vol. 54, 2011, pages 1599 - 1612
BILLIARD ET AL., CANCER METAB, vol. 1, 2013, pages 1 - 19
LE DUDAL ET AL., J CLIN INVEST, vol. 129, 2019, pages 2571 - 2577
FUJIWARA ET AL., J ANESTH, vol. 34, 2020, pages 373 - 381
RIBAN ET AL., NEUROSCIENCE, vol. 112, 2002, pages 101 - 111
See also references of EP 4190401A4
Attorney, Agent or Firm:
UMEDA Shinsuke et al. (JP)
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