CA2536842C - Benzotropolone derivatives and modulation of inflammatory response - Google Patents

Benzotropolone derivatives and modulation of inflammatory response Download PDF

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Publication number
CA2536842C
CA2536842C CA2536842A CA2536842A CA2536842C CA 2536842 C CA2536842 C CA 2536842C CA 2536842 A CA2536842 A CA 2536842A CA 2536842 A CA2536842 A CA 2536842A CA 2536842 C CA2536842 C CA 2536842C
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CA
Canada
Prior art keywords
gallate
compound
benzotropolone
compounds
acetone
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Fee Related
Application number
CA2536842A
Other languages
English (en)
French (fr)
Other versions
CA2536842A1 (en
Inventor
Chi-Tang Ho
Geetha Ghai
Shengmin Sang
Jin-Woo Jhoo
Mou-Tuan Huang
Robert T. Rosen
Slavik Dushenkov
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rutgers, The State University of New Jersey
WellGen Inc
Original Assignee
Rutgers, The State University of New Jersey
WellGen Inc
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
Application filed by Rutgers, The State University of New Jersey, WellGen Inc filed Critical Rutgers, The State University of New Jersey
Publication of CA2536842A1 publication Critical patent/CA2536842A1/en
Application granted granted Critical
Publication of CA2536842C publication Critical patent/CA2536842C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/18—Antioxidants, e.g. antiradicals
    • 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]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/38—Unsaturated compounds containing keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
    • C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/12—One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Biochemistry (AREA)
  • Toxicology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2536842A 2003-08-29 2004-08-30 Benzotropolone derivatives and modulation of inflammatory response Expired - Fee Related CA2536842C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10/652,813 US7087790B2 (en) 2003-08-29 2003-08-29 Benzotropolone derivatives and modulation of inflammatory response
US10/652,813 2003-08-29
PCT/US2004/028164 WO2005021479A1 (en) 2003-08-29 2004-08-30 Benzotropolone derivatives and modulation of inflammatory response

Publications (2)

Publication Number Publication Date
CA2536842A1 CA2536842A1 (en) 2005-03-10
CA2536842C true CA2536842C (en) 2014-10-07

Family

ID=34217746

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2536842A Expired - Fee Related CA2536842C (en) 2003-08-29 2004-08-30 Benzotropolone derivatives and modulation of inflammatory response

Country Status (6)

Country Link
US (2) US7087790B2 (enExample)
EP (1) EP1663931B1 (enExample)
JP (1) JP4846581B2 (enExample)
CN (1) CN1852881B (enExample)
CA (1) CA2536842C (enExample)
WO (1) WO2005021479A1 (enExample)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7087790B2 (en) * 2003-08-29 2006-08-08 Rutgers, The State University Of New Jersey Benzotropolone derivatives and modulation of inflammatory response
CA2608651A1 (en) * 2005-05-24 2006-11-30 Wellgen, Inc. Compositions and methods for the prevention and treatment of conditions associated with inflammation
WO2008019985A1 (en) * 2006-08-14 2008-02-21 Unilever Plc Method of purifying theaflavins
EP3238544A1 (en) 2008-03-21 2017-11-01 Rutgers, The State University of New Jersey Use of tea-derived, theaflavin enriched extract to increase exercise performance and reduce exercise recovery time
WO2009156324A2 (en) * 2008-06-25 2009-12-30 Basf Se Use of benzotropolone derivatives as uv absorbers and antioxidants and their use in sunscreens and/or cosmetic compositions
RU2396244C1 (ru) * 2008-12-23 2010-08-10 Тихоокеанский Институт Биоорганической Химии Дальневосточного Отделения Российской Академии Наук (Тибох Дво Ран) Способ получения пурпурогаллина
ES2643463T3 (es) 2009-05-21 2017-11-23 Suntory Holdings Limited Agente antiobesidad que comprende un compuesto que contiene un anillo de benzotropolona
BR112012007685B1 (pt) * 2009-10-06 2024-03-05 Basf Se Uso de derivados de benzotropolona
US8282970B2 (en) * 2009-10-07 2012-10-09 Jiahgsu Dehe Bio-Tech Co., Ltd Theaflavin compositions, related processes and methods of use
US20110082198A1 (en) * 2009-10-07 2011-04-07 Jiangsu Dehe Bio-Tech Co., Ltd. Theaflavin compositions, production, and methods to control physiological disorders in mammals
JP5424424B2 (ja) * 2011-10-03 2014-02-26 国立大学法人 鹿児島大学 抗炎症剤または抗炎症作用を有する飲食品
EP2879669A4 (en) * 2012-07-29 2016-04-13 Univ Colorado Regents ANTAGONISTS OF THE TOLL LIKE RECEPTOR 1/2 COMPLEX
JP2014148530A (ja) * 2014-04-21 2014-08-21 Amazonia Fitomedicamentos Ltda ラノスタ−８，２４−ジエン−３−オールの薬学的使用
JP6628970B2 (ja) * 2015-03-09 2020-01-15 サントリーホールディングス株式会社 ベンゾトロポロン環含有化合物を定量する方法
EP3370523A4 (en) 2015-11-04 2019-12-18 The Penn State Research Foundation CONNECTIONS, COMPOSITIONS AND METHOD FOR COLORING EDIBLE MATERIALS
WO2018096088A1 (en) * 2016-11-24 2018-05-31 Universiteit Antwerpen Halogenated benzotropolones as atg4b inhibitors
WO2020018474A2 (en) 2018-07-16 2020-01-23 Ziegler Gregory Ray Compounds, compositions, and methods for coloring edible materials
CN114869878B (zh) * 2022-04-08 2024-02-23 南通大学 表儿茶素没食子酸酯在制备治疗高原脑水肿药物中的应用
JP2024056384A (ja) * 2022-10-11 2024-04-23 ライオン・スペシャリティ・ケミカルズ株式会社 炎症性因子産生抑制剤

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3812266A (en) * 1972-01-31 1974-05-21 Lipton T Inc Green tea conversion using tannase and natural tea enzymes
TW381092B (en) 1995-07-07 2000-02-01 Otsuka Pharma Co Ltd Novel benzimidazole derivatives for use in treating arteriosclerotic diseases
US6469053B1 (en) 1996-04-02 2002-10-22 Mars Incorporated Use of procyanidins in the maintenance of vascular health and modulation of the inflammatory response
US5861415A (en) 1996-07-12 1999-01-19 Sami Chemicals & Extracts, Ltd. Bioprotectant composition, method of use and extraction process of curcuminoids
ATE207068T1 (de) 1997-07-15 2001-11-15 Unilever Nv Verbesserungen bezüglich auf theaflavin erzeugung
GB9902777D0 (en) * 1999-02-08 1999-03-31 Unilever Plc Cold water infusing leaf tea
CA2383224C (en) 1999-09-21 2010-12-07 Geetha Ghai Extracts of orange peel for prevention and treatment of cancer
US6348224B1 (en) 2000-03-16 2002-02-19 Lipton, Division Of Conopco, Inc. Black tea manufacture
AU2001261004B2 (en) 2000-03-22 2006-07-13 Mars, Incorporated The use of cocoa procyanidins combined with acetylsalicyclic acid as an anti-platelet therapy
JP3694733B2 (ja) 2000-06-29 2005-09-14 独立行政法人農業・生物系特定産業技術研究機構 抗アレルギー剤
US7087790B2 (en) * 2003-08-29 2006-08-08 Rutgers, The State University Of New Jersey Benzotropolone derivatives and modulation of inflammatory response

Also Published As

Publication number Publication date
US20050049284A1 (en) 2005-03-03
CA2536842A1 (en) 2005-03-10
WO2005021479A1 (en) 2005-03-10
US20060241154A1 (en) 2006-10-26
US7087790B2 (en) 2006-08-08
US7288680B2 (en) 2007-10-30
JP4846581B2 (ja) 2011-12-28
EP1663931A4 (en) 2006-10-18
CN1852881B (zh) 2010-09-29
JP2007504168A (ja) 2007-03-01
EP1663931B1 (en) 2013-04-10
CN1852881A (zh) 2006-10-25
EP1663931A1 (en) 2006-06-07

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