WO2016032127A3 - Novel compounds having antioxidant and anti-inflammatory activities due to competition with lps for binding to tlr4, and medical use thereof - Google Patents

Novel compounds having antioxidant and anti-inflammatory activities due to competition with lps for binding to tlr4, and medical use thereof Download PDF

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Publication number
WO2016032127A3
WO2016032127A3 PCT/KR2015/007655 KR2015007655W WO2016032127A3 WO 2016032127 A3 WO2016032127 A3 WO 2016032127A3 KR 2015007655 W KR2015007655 W KR 2015007655W WO 2016032127 A3 WO2016032127 A3 WO 2016032127A3
Authority
WO
WIPO (PCT)
Prior art keywords
tlr4
lps
binding
competition
antioxidant
Prior art date
Application number
PCT/KR2015/007655
Other languages
French (fr)
Korean (ko)
Other versions
WO2016032127A2 (en
Inventor
정해영
문형룡
문경미
박윤정
김남득
박지영
김혜림
김철민
정지원
Original Assignee
부산대학교 산학협력단
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020150101640A external-priority patent/KR101686872B1/en
Application filed by 부산대학교 산학협력단 filed Critical 부산대학교 산학협력단
Publication of WO2016032127A2 publication Critical patent/WO2016032127A2/en
Publication of WO2016032127A3 publication Critical patent/WO2016032127A3/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
    • C07D239/10—Oxygen or sulfur atoms

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

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.
PCT/KR2015/007655 2014-08-25 2015-07-23 Novel compounds having antioxidant and anti-inflammatory activities due to competition with lps for binding to tlr4, and medical use thereof WO2016032127A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20140110853 2014-08-25
KR10-2014-0110853 2014-08-25
KR10-2015-0101640 2015-07-17
KR1020150101640A KR101686872B1 (en) 2014-08-25 2015-07-17 New compounds having anti-inflammatory and anti oxidatant activity through TLR4 binding competition with LPS and medical use thereof

Publications (2)

Publication Number Publication Date
WO2016032127A2 WO2016032127A2 (en) 2016-03-03
WO2016032127A3 true WO2016032127A3 (en) 2016-05-06

Family

ID=55400777

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2015/007655 WO2016032127A2 (en) 2014-08-25 2015-07-23 Novel compounds having antioxidant and anti-inflammatory activities due to competition with lps for binding to tlr4, and medical use thereof

Country Status (1)

Country Link
WO (1) WO2016032127A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3475264A4 (en) 2016-06-28 2020-04-15 University Of Kentucky Research Foundation Prostaglandin e synthase inhibitors and methods for utilizing the same
CN108276354B (en) * 2018-02-06 2020-02-18 山西医科大学 TLR4/MD2 inhibitor and application thereof in anti-inflammatory drugs

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6413936B1 (en) * 1995-10-30 2002-07-02 Glycorex Ab Glycomimetics as selectin antagonists and pharmaceuticals having antiinflammatory activity
WO2003074497A1 (en) * 2002-03-01 2003-09-12 Pintex Pharmaceutical, Inc. Pin1-modulating compounds and methods of use thereof
US20060025405A1 (en) * 2004-07-02 2006-02-02 Corcept Therapeutics, Inc. Modified pyrimidine glucocorticoid receptor modulators
WO2010136804A1 (en) * 2009-05-28 2010-12-02 Aston University Pyrimidine derivatives for use as antibiotics

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6413936B1 (en) * 1995-10-30 2002-07-02 Glycorex Ab Glycomimetics as selectin antagonists and pharmaceuticals having antiinflammatory activity
WO2003074497A1 (en) * 2002-03-01 2003-09-12 Pintex Pharmaceutical, Inc. Pin1-modulating compounds and methods of use thereof
US20060025405A1 (en) * 2004-07-02 2006-02-02 Corcept Therapeutics, Inc. Modified pyrimidine glucocorticoid receptor modulators
WO2010136804A1 (en) * 2009-05-28 2010-12-02 Aston University Pyrimidine derivatives for use as antibiotics

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
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 *
ARPYAN, A. A. ET AL.: "Synthesis of Some Substituted 5-(P-Alkoxybenzyl) -Pyrimidines", ARMYANSKII KHIMICHESKII ZHURNAL, vol. 20, no. 1, 1967, pages 61 - 67 *
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 *
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 *
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 *
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 *
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 *
MCADOO, M. H. ET AL.: "Inhibition of the Cathepsin D-Type Proteinase of Macrophages by Pepstatin, a Specific Pepsin Inhibitor, and Other Substances", INFECTION AND IMMUNITY, vol. 7, no. 4, 1973, pages 655 - 665 *
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 *
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 *

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Publication number Publication date
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