Title:
NOVEL COMPOUNDS HAVING ANTIOXIDANT AND ANTI-INFLAMMATORY ACTIVITIES DUE TO COMPETITION WITH LPS FOR BINDING TO TLR4, AND MEDICAL USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2016/032127
Kind Code:
A3
Abstract:
The present invention relates to novel compounds having antioxidant and anti-inflammatory effects of inhibiting the activity of macrophages due to competition with LPS for binding to TLR4, and a medical use thereof. The compounds, according to the present invention, have antioxidant and anti-inflammatory activities, and thus can be used for geriatric disease prevention or inflammation treatment. In addition, the compounds compete with LPS for binding to TLR4-MD2, in particular, thereby being used as a pharmaceutical composition useful in the prevention and treatment of sepsis, metabolic diseases, or cardiovascular diseases, or as a health food, by means of the competition with LPS for binding to TLR4-MD2.
Inventors:
CHUNG HAE YOUNG (KR)
MOON HYUNG RYONG (KR)
MOON KYOUNG MI (KR)
PARK YUN JUNG (KR)
KIM NAM-DEUK (KR)
PARK JI YOUNG (KR)
KIM HYE RIM (KR)
KIM CHEOL MIN (KR)
JEONG JI WON (KR)
MOON HYUNG RYONG (KR)
MOON KYOUNG MI (KR)
PARK YUN JUNG (KR)
KIM NAM-DEUK (KR)
PARK JI YOUNG (KR)
KIM HYE RIM (KR)
KIM CHEOL MIN (KR)
JEONG JI WON (KR)
Application Number:
PCT/KR2015/007655
Publication Date:
May 06, 2016
Filing Date:
July 23, 2015
Export Citation:
Assignee:
PUSAN NAT UNIV IND COOP FOUND (KR)
International Classes:
C07D239/10; A23L33/10; A61K31/505; A61K31/513; A61P29/00
Domestic Patent References:
| WO2010136804A1 | 2010-12-02 | |||
| WO2003074497A1 | 2003-09-12 |
Foreign References:
| US20060025405A1 | 2006-02-02 | |||
| US6413936B1 | 2002-07-02 |
Other References:
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KOZLOV, N. ET AL.: "Synthesis of Arylmethylpyrimidinetriones and Pyrimidoquinolinediones with Fluorescent and Nonlinear-Optical Properties", RUSSIAN JOURNAL OF APPLIED CHEMISTRY, vol. 80, no. 7, 2007, pages 1101 - 1104
GOUDGAON, N. M ET AL.: "Synthesis and Antimicrobial Activities of Novel 5-Substituted Pyrimidin-2, 4, 6-Triones", J OURNAL OF THE INDIAN CHEMICAL SOCIETY, vol. 87, no. 6, 2010, pages 743 - 748
SAWANT, R. L. ET AL.: "QSAR and Docking Study for Rate of Mushroom Tyrosinase Inhibition by Some 5-Benzylidene Barbiturate Derivatives", INTERNATIONAL JOURNAL OF DRUG DESIGN AND DISCOVERY, vol. 4, no. 2, 2013, pages 1077 - 1082
JURSIC, B. S. ET AL.: "Mono C-alkylation and Mono C-benzylation of Barbituric Acids through Zinc/Acid Reduction of Acyl, Benzylidene, and Alkylidene Barbiturate Intermediates", TETRAHEDRON LETTERS, vol. 44, no. 10, 2003, pages 2203 - 2210, XP004410042, DOI: doi:10.1016/S0040-4039(03)00111-4
KUJUNDZIC, N. ET AL.: "Synthesis and Antibacterial Effect of Derivatives of 5-(3,4,5-Trimethoxybenzyl)Pyrimidine, Tetrahydropyrimidine, -Hexahydropyrimidine and -Hydantoin", CROATICA CHEMICA ACTA, vol. 61, no. 1, 1988, pages 121 - 135, XP009070565
ADZHIBEKYAN, A. C. ET AL.: "Some 5- and N-arylsubstituted Barbiturates and their Biological Properties", ARMYANSKII KHIMICHESKII ZHURNAL, vol. 28, no. 9, 1975, pages 741 - 746, XP009055735
GRIGORYAN, L. A. ET AL.: "Arylsulphonic Acid Derivatives. IV. Sulfamido Derivatives of 5-(P-Alkoxybenzyl)Pyrimidines", ARMYANSKII KHIMICHESKII ZHUMAL, vol. 28, no. 9, 1975, pages 704 - 708
ARPYAN, A. A. ET AL.: "Synthesis of Some Substituted 5-(P-Alkoxybenzyl) -Pyrimidines", ARMYANSKII KHIMICHESKII ZHURNAL, vol. 20, no. 1, 1967, pages 61 - 67
VIEIRA, A. A. ET AL.: "Synthesis and In Vivo Evaluation of 5-(Chloro-5-Benzyl-Barbiturates as New Central Nervous System Depressants", JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, vol. 22, no. 2, 2011, pages 364 - 371
KOZLOV, N. ET AL.: "Synthesis of Arylmethylpyrimidinetriones and Pyrimidoquinolinediones with Fluorescent and Nonlinear-Optical Properties", RUSSIAN JOURNAL OF APPLIED CHEMISTRY, vol. 80, no. 7, 2007, pages 1101 - 1104
GOUDGAON, N. M ET AL.: "Synthesis and Antimicrobial Activities of Novel 5-Substituted Pyrimidin-2, 4, 6-Triones", J OURNAL OF THE INDIAN CHEMICAL SOCIETY, vol. 87, no. 6, 2010, pages 743 - 748
SAWANT, R. L. ET AL.: "QSAR and Docking Study for Rate of Mushroom Tyrosinase Inhibition by Some 5-Benzylidene Barbiturate Derivatives", INTERNATIONAL JOURNAL OF DRUG DESIGN AND DISCOVERY, vol. 4, no. 2, 2013, pages 1077 - 1082
JURSIC, B. S. ET AL.: "Mono C-alkylation and Mono C-benzylation of Barbituric Acids through Zinc/Acid Reduction of Acyl, Benzylidene, and Alkylidene Barbiturate Intermediates", TETRAHEDRON LETTERS, vol. 44, no. 10, 2003, pages 2203 - 2210, XP004410042, DOI: doi:10.1016/S0040-4039(03)00111-4
KUJUNDZIC, N. ET AL.: "Synthesis and Antibacterial Effect of Derivatives of 5-(3,4,5-Trimethoxybenzyl)Pyrimidine, Tetrahydropyrimidine, -Hexahydropyrimidine and -Hydantoin", CROATICA CHEMICA ACTA, vol. 61, no. 1, 1988, pages 121 - 135, XP009070565
ADZHIBEKYAN, A. C. ET AL.: "Some 5- and N-arylsubstituted Barbiturates and their Biological Properties", ARMYANSKII KHIMICHESKII ZHURNAL, vol. 28, no. 9, 1975, pages 741 - 746, XP009055735
GRIGORYAN, L. A. ET AL.: "Arylsulphonic Acid Derivatives. IV. Sulfamido Derivatives of 5-(P-Alkoxybenzyl)Pyrimidines", ARMYANSKII KHIMICHESKII ZHUMAL, vol. 28, no. 9, 1975, pages 704 - 708
ARPYAN, A. A. ET AL.: "Synthesis of Some Substituted 5-(P-Alkoxybenzyl) -Pyrimidines", ARMYANSKII KHIMICHESKII ZHURNAL, vol. 20, no. 1, 1967, pages 61 - 67
VIEIRA, A. A. ET AL.: "Synthesis and In Vivo Evaluation of 5-(Chloro-5-Benzyl-Barbiturates as New Central Nervous System Depressants", JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, vol. 22, no. 2, 2011, pages 364 - 371
Attorney, Agent or Firm:
TAEBAEK INTELLECTUAL PROPERTY LAW FIRM (151Gasandigital 1-roGeumcheon-gu, Seoul 153-803, KR)
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