AU2008323683B2 - Anti-inflammatory quinic acid derivatives for oral administration - Google Patents
Anti-inflammatory quinic acid derivatives for oral administration Download PDFInfo
- Publication number
- AU2008323683B2 AU2008323683B2 AU2008323683A AU2008323683A AU2008323683B2 AU 2008323683 B2 AU2008323683 B2 AU 2008323683B2 AU 2008323683 A AU2008323683 A AU 2008323683A AU 2008323683 A AU2008323683 A AU 2008323683A AU 2008323683 B2 AU2008323683 B2 AU 2008323683B2
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- Australia
- Prior art keywords
- compound
- compounds
- inflammatory
- quinic acid
- quinic
- 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.)
- Ceased
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- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000000464 low-speed centrifugation Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
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- NJSJBTVAKUBCKG-UHFFFAOYSA-N propylazanide Chemical group CCC[NH-] NJSJBTVAKUBCKG-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 description 1
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- 230000036303 septic shock Effects 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
- JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
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- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
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- 230000002103 transcriptional effect Effects 0.000 description 1
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- 239000009637 wintergreen oil Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- UCRLQOPRDMGYOA-DFTDUNEMSA-L zinc;(4r)-4-[[(2s)-2-[[(4r)-2-[(1s,2s)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2s,3s)-1-[[(3s,6r,9s,12r,15s,18r,21s)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2s)-butan-2-yl]-6-(carbox Chemical compound [Zn+2].C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC([O-])=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2NC=NC=2)C(=O)N[C@H](CC([O-])=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 UCRLQOPRDMGYOA-DFTDUNEMSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
-
- 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
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US261107P | 2007-11-09 | 2007-11-09 | |
| US61/002,611 | 2007-11-09 | ||
| PCT/US2008/083068 WO2009062200A1 (en) | 2007-11-09 | 2008-11-10 | Anti-inflammatory quinic acid derivatives for oral administration |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2008323683A1 AU2008323683A1 (en) | 2009-05-14 |
| AU2008323683B2 true AU2008323683B2 (en) | 2014-10-02 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2008323683A Ceased AU2008323683B2 (en) | 2007-11-09 | 2008-11-10 | Anti-inflammatory quinic acid derivatives for oral administration |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8115031B2 (enExample) |
| EP (1) | EP2219445A4 (enExample) |
| JP (1) | JP5660898B2 (enExample) |
| AU (1) | AU2008323683B2 (enExample) |
| CA (1) | CA2713394C (enExample) |
| WO (1) | WO2009062200A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101284799B (zh) * | 2007-03-23 | 2013-04-03 | 浙江医药股份有限公司新昌制药厂 | 咖啡酰奎宁酸含氮衍生物及其制备方法和其药物组合物及用途 |
| WO2010132504A1 (en) | 2009-05-11 | 2010-11-18 | University Of Tennessee Research Foundation | Anti-inflammatory quinic acid derivatives for radioprotection/radiomitigation |
| US10369133B2 (en) | 2013-07-23 | 2019-08-06 | The University Of Tennessee Research Foundation | Immunosuppressive compounds and therapeutics |
| TWI481600B (zh) * | 2013-07-24 | 2015-04-21 | Nat Applied Res Laboratories | 一種奎尼酸衍生物、其製程及其用途 |
| US11883457B1 (en) | 2022-09-06 | 2024-01-30 | Optigenex Inc. | Method of enhancing cognition in individuals with at least normal cognition |
| CN117547562A (zh) * | 2023-05-09 | 2024-02-13 | 北京农学院 | 一种用于抗炎的虎耳草提取物及其制备方法和用途 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4044120A (en) * | 1974-04-17 | 1977-08-23 | Wilkinson Sword Limited | Compounds having a physiological cooling effect, and compositions containing them |
| US4582855A (en) * | 1981-11-12 | 1986-04-15 | American Hospital Supply Corporation | Aromatic and esters of hydroxypropylamines |
| WO2007105753A1 (ja) * | 2006-03-16 | 2007-09-20 | Astellas Pharma Inc. | トリアゾール誘導体またはその塩 |
| WO2008116385A1 (fr) * | 2007-03-23 | 2008-10-02 | Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory | Dérivés d'acide caféyl quinique contenant de l'azote, et procédé de préparation, composition pharmaceutique et leur utilisation |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6017A (en) * | 1849-01-09 | Die for bending ttjbe-skelps | ||
| US7020A (en) * | 1850-01-15 | Improvement in harvesting-mac mines | ||
| US2918477A (en) * | 1954-12-28 | 1959-12-22 | Alberti Carlo Giuseppe | Caffeic esters of quinic acid and quinic acid amide and syntheses thereof |
| US2866734A (en) * | 1956-12-05 | 1958-12-30 | Us Vitamin Corp | 3-pyridylethyl 2, 4-oxazolidinediones and process |
| GB1460593A (en) * | 1973-06-22 | 1977-01-06 | Ici Ltd | Ethanolamine derivatives |
| US3968211A (en) * | 1974-02-11 | 1976-07-06 | The Upjohn Company | Compositions and methods of use of amidines for anti-arrhythmic purposes |
| JPS61251616A (ja) * | 1985-04-30 | 1986-11-08 | Agency Of Ind Science & Technol | 溶質の放出量の制御方法 |
| HU906340D0 (en) * | 1986-10-13 | 1991-04-29 | Sandoz Ag | Synthesis in solid phase for producing peptonic alcohols |
| US6964784B2 (en) * | 2002-03-07 | 2005-11-15 | Optigenex, Inc. | Method of preparation and composition of a water soluble extract of the bioactive component of the plant species uncaria for enhancing immune, anti-inflammatory, anti-tumor and dna repair processes of warm blooded animals |
| WO2005035534A1 (ja) * | 2003-10-08 | 2005-04-21 | Ono Pharmaceutical Co., Ltd. | 複素ビシクロ環および複素トリシクロ環化合物およびその医薬 |
| US7482378B2 (en) * | 2004-05-28 | 2009-01-27 | Millenium Specialty Chemicals, Inc. | Physiological cooling compositions |
| US8436006B2 (en) * | 2004-08-06 | 2013-05-07 | Jansssen Pharmaceutica N.V. | 2-amino-quinazoline derivatives useful as inhibitors of β-secretase (BACE) |
| WO2007103719A2 (en) * | 2006-03-03 | 2007-09-13 | Incyte Corporation | MODULATORS OF 11-β HYDROXYL STEROID DEHYDROGENASE TYPE 1, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS OF USING THE SAME |
-
2008
- 2008-11-10 AU AU2008323683A patent/AU2008323683B2/en not_active Ceased
- 2008-11-10 CA CA2713394A patent/CA2713394C/en not_active Expired - Fee Related
- 2008-11-10 JP JP2010533331A patent/JP5660898B2/ja not_active Expired - Fee Related
- 2008-11-10 WO PCT/US2008/083068 patent/WO2009062200A1/en not_active Ceased
- 2008-11-10 EP EP08847594.2A patent/EP2219445A4/en not_active Withdrawn
- 2008-11-10 US US12/268,432 patent/US8115031B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4044120A (en) * | 1974-04-17 | 1977-08-23 | Wilkinson Sword Limited | Compounds having a physiological cooling effect, and compositions containing them |
| US4582855A (en) * | 1981-11-12 | 1986-04-15 | American Hospital Supply Corporation | Aromatic and esters of hydroxypropylamines |
| WO2007105753A1 (ja) * | 2006-03-16 | 2007-09-20 | Astellas Pharma Inc. | トリアゾール誘導体またはその塩 |
| WO2008116385A1 (fr) * | 2007-03-23 | 2008-10-02 | Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory | Dérivés d'acide caféyl quinique contenant de l'azote, et procédé de préparation, composition pharmaceutique et leur utilisation |
Non-Patent Citations (2)
| Title |
|---|
| ELLIOT, J. D.et al. Journal of the Chemical Society, Perkin Transactions 1., 1981, pages 1782-1789 * |
| ITSENKO, O. et al. Journal of Organic Chemistry., 2004, Vol. 69, Pages 4356-4360 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2219445A4 (en) | 2013-05-29 |
| US20090234015A1 (en) | 2009-09-17 |
| JP5660898B2 (ja) | 2015-01-28 |
| WO2009062200A1 (en) | 2009-05-14 |
| CA2713394A1 (en) | 2009-05-14 |
| EP2219445A1 (en) | 2010-08-25 |
| AU2008323683A1 (en) | 2009-05-14 |
| JP2011503110A (ja) | 2011-01-27 |
| US8115031B2 (en) | 2012-02-14 |
| CA2713394C (en) | 2016-01-19 |
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