WO2012102560A3 - Novel 4-0-methylhonokiol derivative and composition containing same as active ingredient for treatment of inflammatory diseases - Google Patents

Novel 4-0-methylhonokiol derivative and composition containing same as active ingredient for treatment of inflammatory diseases Download PDF

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Publication number
WO2012102560A3
WO2012102560A3 PCT/KR2012/000616 KR2012000616W WO2012102560A3 WO 2012102560 A3 WO2012102560 A3 WO 2012102560A3 KR 2012000616 W KR2012000616 W KR 2012000616W WO 2012102560 A3 WO2012102560 A3 WO 2012102560A3
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WIPO (PCT)
Prior art keywords
inflammatory diseases
novel
treatment
composition containing
active ingredient
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Application number
PCT/KR2012/000616
Other languages
French (fr)
Korean (ko)
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WO2012102560A2 (en
Inventor
한상배
정재경
곽영신
서승용
이기호
송석길
홍진태
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주식회사 바이오랜드
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Publication of WO2012102560A2 publication Critical patent/WO2012102560A2/en
Publication of WO2012102560A3 publication Critical patent/WO2012102560A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • 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
    • A61K31/075—Ethers or acetals
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • A61K31/09—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon having two or more such linkages
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
    • C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/28—Ethers with hydroxy compounds containing oxirane rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Epidemiology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention provides a novel methylhonokiol derivative and a composition containing the same as an active ingredient for the treatment, prevention or improvement of inflammatory diseases. The methylhonokiol derivative of the invention inhibits COX-2(Cyclooxigenase-2) activities, thereby ensuring anti-inflammatory activities. Therefore, the methylhonokiol derivative of the invention can be developed as a therapeutic agent for various inflammatory diseases and as an active component of functional health foods.
PCT/KR2012/000616 2011-01-26 2012-01-26 Novel 4-0-methylhonokiol derivative and composition containing same as active ingredient for treatment of inflammatory diseases WO2012102560A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2011-0007844 2011-01-26
KR1020110007844A KR101386068B1 (en) 2011-01-26 2011-01-26 Novel 4-Ｏ-Methylhonokiol Derivatives and Composition for Treating Inflammatory Disease Comprising the Same as Active Ingredient

Publications (2)

Publication Number Publication Date
WO2012102560A2 WO2012102560A2 (en) 2012-08-02
WO2012102560A3 true WO2012102560A3 (en) 2012-10-18

Family

ID=46581294

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2012/000616 WO2012102560A2 (en) 2011-01-26 2012-01-26 Novel 4-0-methylhonokiol derivative and composition containing same as active ingredient for treatment of inflammatory diseases

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KR (1) KR101386068B1 (en)
WO (1) WO2012102560A2 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2986587B1 (en) 2013-04-17 2023-11-22 Sharon Anavi-Goffer Cb2 receptor ligands for the treatment of psychiatric disorders
KR101941221B1 (en) * 2017-12-14 2019-01-22 (주)솔빛피앤에프 Composition for preventing, improving or treating macular degeneration comprising Phragmitis Rhizoma extract
CN113999191B (en) * 2021-11-25 2023-07-18 大连理工大学 Novel bio-based epoxy resin containing active ester side group and preparation method thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080105526A (en) * 2007-05-31 2008-12-04 주식회사 바이오랜드 Composition comprising an extract of magnolia officinalis rehd. et wils. or 4-o-methylhonokiol isolated therefrom having anti-inflammatory, anti-allergy and anti-wrinkle activity
KR100919625B1 (en) * 2007-08-31 2009-09-30 서울대학교산학협력단 The composition comprising the extract or purified extract of Magnolia cortex for preventing and treating fatty liver diseases, and a method for preparing purified extract

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080105526A (en) * 2007-05-31 2008-12-04 주식회사 바이오랜드 Composition comprising an extract of magnolia officinalis rehd. et wils. or 4-o-methylhonokiol isolated therefrom having anti-inflammatory, anti-allergy and anti-wrinkle activity
KR100919625B1 (en) * 2007-08-31 2009-09-30 서울대학교산학협력단 The composition comprising the extract or purified extract of Magnolia cortex for preventing and treating fatty liver diseases, and a method for preparing purified extract

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
OH, JU HOON ET AL.: "Anti-inflammatory effect of 4-O-methylhonokiol, a novel compound isolated from Magnolia officinalis through inhibition ofNF-kB", CHEMICO-BIOLOGICAL INTERACTIONS, vol. 180, 2009, pages 506 - 514, XP026194297, DOI: doi:10.1016/j.cbi.2009.03.014 *
SOLANKI, P. R ET AL.: "Synthesis and Physical Properties of Some Substitued Pyrazole and Isoxazole Complexes with Co (II), Ni (III) and Cu (II) Metal Ions", J. IND. COUNCIL CHEM., vol. 24, 2007, pages 43 - 45 *

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Publication number Publication date
KR101386068B1 (en) 2014-04-21
WO2012102560A2 (en) 2012-08-02
KR20120086538A (en) 2012-08-03

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