Title:
NAPHTHOQUINONE COMPOUND AND NUCLEAR FACTOR KAPPA-B (NF-κB) INHIBITOR COMPRISING SAME AS ACTIVE INGREDIENT
Document Type and Number:
WIPO Patent Application WO/2017/099210
Kind Code:
A1
Abstract:
The present invention addresses the problem of providing a novel nuclear factor κB (NF-κB) inhibitor. An NF-κB inhibitor that comprises, as an active ingredient, a naphthoquinone compound represented by general formula (1) or a pharmaceutically acceptable salt thereof. [In general formula (1): R1 and R2 are the same or different and represent a hydrogen atom or a group selected from the group consisting of a hydroxy group, a 2-methyl-5-hydroxy-1,4-naphthoquinone group, an alkyl or alkenyl group optionally having a carbonyl group and an alkyl group optionally having a hydroxy group; R3 represents a hydroxy group or an alkyl group having 1-4 carbon atoms; R4 represents a hydroxy group or an oxo group; and the broken line represents a single bond or a double bond.)
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Inventors:
NOZAKI HIROSHI (JP)
YAMADA MASASHI (JP)
YAMADA MASASHI (JP)
Application Number:
PCT/JP2016/086669
Publication Date:
June 15, 2017
Filing Date:
December 09, 2016
Export Citation:
Assignee:
POLA PHARMA INC (JP)
International Classes:
A61K31/122; A61P29/00; A61P35/00; A61P43/00; C07C49/747; C07C50/32; C07C50/38
Foreign References:
| CN103204771A | 2013-07-17 |
Other References:
OHIRA, SUSUMU ET AL.: "New naphthoquinone and monoterpenoid from Plumbago zeylanica", TETRAHEDRON LETT, vol. 55, 2014, pages 6554 - 6556, XP029018536
SANDUR, SK ET AL.: "Plumbagin (5-hydroxy-2- methyl-1,4-naphthoquinone) suppresses NF-kappaB activation and NF-kappaB-regulated gene products through modulation of p65 and IkappaBalpha kinase activation, leading to potentiation of apoptosis induced by cytokine and chemotherapeutic agents.", J BIOL CHEM., vol. 281, no. 25, 2006, pages 17023 - 17033, XP055389251
JAMAL, M.S. ET AL.: "Anticancer Compound Plumbagin and Its Molecular Targets: A Structural Insight into the Inhibitory Mechanisms Using Computational Approaches", PLOS ONE., vol. 9, no. 2, 2014, pages e87309, XP055389252, Retrieved from the Internet [retrieved on 20161221]
LUO, P. ET AL.: "Anti-inflammatory and Analgesic Effect of Plumbagin through Inhibition of Nuclear Factor-KB Activation", JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, vol. 335, no. 3, 2010, pages 735 - 742, XP055389257
WEI, Y ET AL.: "Anti-fibrotic effect of plumbagin on CC14-lesioned rats.", CELL PHYSIOL BIOCHEM., vol. 35, no. 4, March 2015 (2015-03-01), pages 1599 - 1608, XP055389261, Retrieved from the Internet [retrieved on 20161221]
THAO, NP ET AL.: "In vitro anti-inflammatory components isolated from the carnivorous plant Nepenthes mirabilis (Lour.) Rafarin.", PHARM BIOL., vol. 54, no. 4, July 2015 (2015-07-01), pages 588 - 594, XP055389267, Retrieved from the Internet [retrieved on 20161221]
TOKUNAGA, T ET AL.: "Cytotoxic Antifeedant from Dionaea muscipula Ellis: A Defensive Mechanism of Carnivorous Plants against Predators", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 77, no. 3, 2004, pages 537 - 541
SHEEJA E ET AL.: "Bioassay-guided isolation of anti-inflammatory and antinociceptive compound from Plumbago zeylanica leaf.", PHARM BIOL., vol. 48, no. 4, 2010, pages 381 - 387, XP055389299
DATABASE REGISTRY [O] 9 February 2015 (2015-02-09), XP055389302, retrieved from STN accession no. 1646099-69-5 Database accession no. 1646099-69-5
DATABASE REGISTRY 26 May 2016 (2016-05-26), "Catalog Name: FCH Group Reagents for Synthesis", XP055389303, retrieved from STN accession no. 1933677-85-0 Database accession no. 1933677-85-0
SANDUR, SK ET AL.: "Plumbagin (5-hydroxy-2- methyl-1,4-naphthoquinone) suppresses NF-kappaB activation and NF-kappaB-regulated gene products through modulation of p65 and IkappaBalpha kinase activation, leading to potentiation of apoptosis induced by cytokine and chemotherapeutic agents.", J BIOL CHEM., vol. 281, no. 25, 2006, pages 17023 - 17033, XP055389251
JAMAL, M.S. ET AL.: "Anticancer Compound Plumbagin and Its Molecular Targets: A Structural Insight into the Inhibitory Mechanisms Using Computational Approaches", PLOS ONE., vol. 9, no. 2, 2014, pages e87309, XP055389252, Retrieved from the Internet
LUO, P. ET AL.: "Anti-inflammatory and Analgesic Effect of Plumbagin through Inhibition of Nuclear Factor-KB Activation", JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, vol. 335, no. 3, 2010, pages 735 - 742, XP055389257
WEI, Y ET AL.: "Anti-fibrotic effect of plumbagin on CC14-lesioned rats.", CELL PHYSIOL BIOCHEM., vol. 35, no. 4, March 2015 (2015-03-01), pages 1599 - 1608, XP055389261, Retrieved from the Internet
THAO, NP ET AL.: "In vitro anti-inflammatory components isolated from the carnivorous plant Nepenthes mirabilis (Lour.) Rafarin.", PHARM BIOL., vol. 54, no. 4, July 2015 (2015-07-01), pages 588 - 594, XP055389267, Retrieved from the Internet
TOKUNAGA, T ET AL.: "Cytotoxic Antifeedant from Dionaea muscipula Ellis: A Defensive Mechanism of Carnivorous Plants against Predators", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 77, no. 3, 2004, pages 537 - 541
SHEEJA E ET AL.: "Bioassay-guided isolation of anti-inflammatory and antinociceptive compound from Plumbago zeylanica leaf.", PHARM BIOL., vol. 48, no. 4, 2010, pages 381 - 387, XP055389299
DATABASE REGISTRY [O] 9 February 2015 (2015-02-09), XP055389302, retrieved from STN accession no. 1646099-69-5 Database accession no. 1646099-69-5
DATABASE REGISTRY 26 May 2016 (2016-05-26), "Catalog Name: FCH Group Reagents for Synthesis", XP055389303, retrieved from STN accession no. 1933677-85-0 Database accession no. 1933677-85-0
Attorney, Agent or Firm:
THE PATENT CORPORATE BODY ARUGA PATENT OFFICE (JP)
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