CA2603371C - Trihydroxy polyunsaturated eicosanoid derivatives - Google Patents
Trihydroxy polyunsaturated eicosanoid derivatives Download PDFInfo
- Publication number
- CA2603371C CA2603371C CA2603371A CA2603371A CA2603371C CA 2603371 C CA2603371 C CA 2603371C CA 2603371 A CA2603371 A CA 2603371A CA 2603371 A CA2603371 A CA 2603371A CA 2603371 C CA2603371 C CA 2603371C
- Authority
- CA
- Canada
- Prior art keywords
- aryl
- alkyl
- compound
- heteroaryl
- hydrogen
- 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.)
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- 150000002066 eicosanoids Chemical class 0.000 title abstract description 22
- 206010061218 Inflammation Diseases 0.000 claims abstract description 13
- 230000004054 inflammatory process Effects 0.000 claims abstract description 13
- 201000010099 disease Diseases 0.000 claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
- 230000028709 inflammatory response Effects 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims description 125
- 150000001875 compounds Chemical class 0.000 claims description 108
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- 125000001072 heteroaryl group Chemical group 0.000 claims description 100
- 239000001257 hydrogen Substances 0.000 claims description 85
- 229910052739 hydrogen Inorganic materials 0.000 claims description 85
- 125000003545 alkoxy group Chemical group 0.000 claims description 77
- 150000002431 hydrogen Chemical class 0.000 claims description 75
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 64
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 63
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 44
- 125000000623 heterocyclic group Chemical group 0.000 claims description 42
- 125000004104 aryloxy group Chemical group 0.000 claims description 41
- 125000002837 carbocyclic group Chemical group 0.000 claims description 41
- 125000003282 alkyl amino group Chemical group 0.000 claims description 35
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 35
- 125000001153 fluoro group Chemical group F* 0.000 claims description 31
- 229910052749 magnesium Inorganic materials 0.000 claims description 26
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 24
- 150000001768 cations Chemical class 0.000 claims description 24
- 229910052700 potassium Inorganic materials 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 229910052708 sodium Inorganic materials 0.000 claims description 24
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 24
- 125000002252 acyl group Chemical group 0.000 claims description 23
- 125000005256 alkoxyacyl group Chemical group 0.000 claims description 23
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 23
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- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 6
- 238000000034 method Methods 0.000 abstract description 69
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- 230000002265 prevention Effects 0.000 abstract description 4
- 238000010168 coupling process Methods 0.000 description 51
- -1 alkenyl boron compound Chemical class 0.000 description 41
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Rheumatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
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| US11/093,757 US7582785B2 (en) | 2002-04-01 | 2005-03-29 | Trihydroxy polyunsaturated eicosanoid derivatives |
| US11/093,757 | 2005-03-29 | ||
| PCT/US2006/011222 WO2006105058A2 (en) | 2005-03-29 | 2006-03-28 | Trihydroxy polyunsaturated eicosanoid derivatives |
Publications (2)
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| CA2603371A1 CA2603371A1 (en) | 2006-10-05 |
| CA2603371C true CA2603371C (en) | 2013-05-28 |
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| US7582785B2 (en) | 2002-04-01 | 2009-09-01 | University Of Southern California | Trihydroxy polyunsaturated eicosanoid derivatives |
| US7902257B2 (en) | 2002-04-01 | 2011-03-08 | University Of Southern California | Trihydroxy polyunsaturated eicosanoid |
| US8481772B2 (en) | 2002-04-01 | 2013-07-09 | University Of Southern California | Trihydroxy polyunsaturated eicosanoid derivatives |
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| US7759395B2 (en) * | 2002-08-12 | 2010-07-20 | The Brigham And Women's Hospital, Inc. | Use of docosatrienes, resolvins and their stable analogs in the treatment of airway diseases and asthma |
| WO2004078143A2 (en) * | 2003-03-05 | 2004-09-16 | The Brigham And Women's Hospital Inc. | Methods for identification and uses of anti-inflammatory receptors for eicosapentaenoic acid analogs |
| EP1755537A4 (en) * | 2004-04-14 | 2009-12-09 | Univ Boston | METHOD AND COMPOSITIONS FOR PREVENTING OR TREATING PERIODONTOPATHIA |
| US7893106B2 (en) * | 2004-11-19 | 2011-02-22 | Martek Biosciences, Corporation | Oxylipins from stearidonic acid and γ-linolenic acid and methods of making and using the same |
| KR20070090928A (ko) * | 2004-11-19 | 2007-09-06 | 마텍 바이오싸이언스스 코포레이션 | 장쇄 다가불포화 지방산으로부터의 옥시리핀, 및 이의 제조방법 및 사용 방법 |
| US20090318394A1 (en) * | 2004-11-19 | 2009-12-24 | Julie Nauroth | Long Chain Polyunsaturated Fatty Acids and Methods of Making and Using the Same |
| US20060293288A1 (en) * | 2005-01-07 | 2006-12-28 | Serhan Charles N | Use of resolvins to treat gastrointestinal diseases |
| WO2007041440A2 (en) * | 2005-10-03 | 2007-04-12 | The Brigham And Women's Hospital, Inc. | Anti-inflammatory actions of neuroprotectin d1/protectin d1 and its natural stereoisomers |
| US8636986B2 (en) * | 2005-11-18 | 2014-01-28 | The Forsyth Institute | Treatment and prevention of bone loss using resolvins |
| WO2007090162A2 (en) * | 2006-01-31 | 2007-08-09 | Martek Biosciences Corporation | OXYLIPINS FROM STEARIDONIC ACID AND γ-LINOLENIC ACID AND METHODS OF MAKING AND USING THE SAME |
| CA2650607A1 (en) * | 2006-04-28 | 2007-11-08 | Resolvyx Pharmaceuticals, Inc. | Compositions and methods for the treatment of cardiovascular disease |
| WO2008011085A1 (en) * | 2006-07-19 | 2008-01-24 | Resolvyx Pharmaceuticals, Inc. | Compositions and methods for the treatment of mucositis |
| US20080161274A1 (en) * | 2006-10-26 | 2008-07-03 | Resolvyx Pharmaceuticals, Inc. | Compounds and methods for inhibition of bone loss |
| WO2008070129A2 (en) * | 2006-12-05 | 2008-06-12 | Resolvyx Pharmaceuticals, Inc. | Compositions and methods for the treatment of inflammatory disease |
| US20110190389A1 (en) * | 2007-02-20 | 2011-08-04 | Linda Arterburn | Oxylipins from long chain polyunsaturated fatty acids and methods of making and using the same |
| CA2699483A1 (en) * | 2007-09-14 | 2009-03-26 | Resolvyx Pharmaceuticals, Inc. | Compositions and methods for modulating immune function |
| KR20150115959A (ko) * | 2007-10-12 | 2015-10-14 | 레솔빅스 파마슈티칼즈, 인코퍼레이티드 | 안과 질환의 치료를 위한 옥실리핀 화합물 |
| US20110027841A1 (en) * | 2007-12-21 | 2011-02-03 | Martek Biosciences Corporation | Method for preparation of oxylipins |
| US20110190242A1 (en) * | 2008-09-23 | 2011-08-04 | Resolvyx Pharmaceuticals, Inc. | Compositions and methods for the treatment of inflammatory disease |
| WO2010095706A1 (ja) | 2009-02-20 | 2010-08-26 | 国立大学法人東京大学 | 新規抗炎症性化合物 |
| TW201039815A (en) * | 2009-04-13 | 2010-11-16 | Resolvyx Pharmaceuticals Inc | Compositions and methods for the treatment of inflammation |
| JP5184565B2 (ja) * | 2010-03-10 | 2013-04-17 | 独立行政法人科学技術振興機構 | 水系溶媒中での含窒素化合物の製造方法 |
| CN103396350B (zh) * | 2012-01-09 | 2014-11-05 | 浙江师范大学 | 一种利用顺式-1-卤-2-氯代烯烃合成维生素a的方法 |
| PL2887923T3 (pl) | 2012-08-24 | 2023-08-14 | Sun Pharmaceutical Industries Limited | Preparat okulistyczny polioksylipidu lub polioksylowego kwasu tłuszczowego i leczenie chorób oczu |
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| WO2014115098A1 (en) * | 2013-01-26 | 2014-07-31 | Mahesh Kandula | Compositions and methods for the treatment of neurological diseases and inflammation |
| US9682034B2 (en) | 2015-03-10 | 2017-06-20 | Elc Management Llc | Methods and compositions for treating skin to resolve inflammation and screening for actives that stimulate pro-resolution pathways |
| ES2895062T3 (es) | 2015-03-18 | 2022-02-17 | Forsyth Dental Infirmary For Children | Métodos para estabilizar placas ateroscleróticas usando lipoxinas, resolvinas y análogos de las mismas |
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| EP3950649A1 (en) * | 2015-11-23 | 2022-02-09 | Retrotope, Inc. | Site-specific isotopic labeling of 1, 4-diene systems |
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2005
- 2005-03-29 US US11/093,757 patent/US7582785B2/en not_active Expired - Fee Related
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2006
- 2006-03-28 MX MX2007012022A patent/MX2007012022A/es active IP Right Grant
- 2006-03-28 WO PCT/US2006/011222 patent/WO2006105058A2/en not_active Ceased
- 2006-03-28 EP EP06748789.2A patent/EP1863753B1/en not_active Not-in-force
- 2006-03-28 AU AU2006230136A patent/AU2006230136B2/en not_active Ceased
- 2006-03-28 CN CNA2006800180987A patent/CN101203481A/zh active Pending
- 2006-03-28 MX MX2014005826A patent/MX352197B/es unknown
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- 2006-03-28 BR BRPI0609767-7A patent/BRPI0609767A2/pt not_active Application Discontinuation
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2012
- 2012-06-05 JP JP2012128022A patent/JP2012162576A/ja active Pending
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2014
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Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0609767A2 (pt) | 2010-04-27 |
| EP1863753B1 (en) | 2017-09-20 |
| JP2008538117A (ja) | 2008-10-09 |
| MX352197B (es) | 2017-11-13 |
| WO2006105058A3 (en) | 2007-04-12 |
| JP2012162576A (ja) | 2012-08-30 |
| CN101203481A (zh) | 2008-06-18 |
| MX2007012022A (es) | 2011-06-16 |
| EP1863753A2 (en) | 2007-12-12 |
| CA2603371A1 (en) | 2006-10-05 |
| US7582785B2 (en) | 2009-09-01 |
| JP2014122240A (ja) | 2014-07-03 |
| US20050228047A1 (en) | 2005-10-13 |
| WO2006105058A2 (en) | 2006-10-05 |
| AU2006230136B2 (en) | 2011-11-03 |
| AU2006230136A1 (en) | 2006-10-05 |
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