JP2010519311A5 - - Google Patents
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- JP2010519311A5 JP2010519311A5 JP2009550992A JP2009550992A JP2010519311A5 JP 2010519311 A5 JP2010519311 A5 JP 2010519311A5 JP 2009550992 A JP2009550992 A JP 2009550992A JP 2009550992 A JP2009550992 A JP 2009550992A JP 2010519311 A5 JP2010519311 A5 JP 2010519311A5
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- JP
- Japan
- Prior art keywords
- acid
- epimer
- dtran
- oil
- ddan
- 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.)
- Pending
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- 238000000034 method Methods 0.000 claims description 123
- 239000003921 oil Substances 0.000 claims description 96
- 235000019198 oils Nutrition 0.000 claims description 96
- 150000002026 docosanoids Chemical class 0.000 claims description 79
- 235000020978 long-chain polyunsaturated fatty acids Nutrition 0.000 claims description 78
- 239000000203 mixture Substances 0.000 claims description 54
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 52
- MZQXAWAWDWCIKG-SPSBLGDNSA-N Avenoleic acid Chemical compound CCC[C@@H](O)C\C=C/C\C=C/CCCCCCCC(O)=O MZQXAWAWDWCIKG-SPSBLGDNSA-N 0.000 claims description 51
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 47
- 150000002066 eicosanoids Chemical class 0.000 claims description 42
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 39
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 37
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 34
- 239000004593 Epoxy Substances 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 29
- 235000021342 arachidonic acid Nutrition 0.000 claims description 27
- 229940114079 arachidonic acid Drugs 0.000 claims description 27
- PRHHYVQTPBEDFE-UHFFFAOYSA-N eicosatrienoic acid Natural products CCCCCC=CCC=CCCCCC=CCCCC(O)=O PRHHYVQTPBEDFE-UHFFFAOYSA-N 0.000 claims description 24
- OFQCOOYKKCPSTN-UHFFFAOYSA-N 17-hydroxydocosa-2,4-dienoic acid Chemical compound CCCCCC(O)CCCCCCCCCCCC=CC=CC(O)=O OFQCOOYKKCPSTN-UHFFFAOYSA-N 0.000 claims description 23
- 206010061218 Inflammation Diseases 0.000 claims description 23
- 230000004054 inflammatory process Effects 0.000 claims description 23
- 230000004770 neurodegeneration Effects 0.000 claims description 21
- BBWMTEYXFFWPIF-CJBMEHDJSA-N (2e,4e,6e)-icosa-2,4,6-trienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C=C\C(O)=O BBWMTEYXFFWPIF-CJBMEHDJSA-N 0.000 claims description 20
- AHANXAKGNAKFSK-PDBXOOCHSA-N all-cis-icosa-11,14,17-trienoic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCCCC(O)=O AHANXAKGNAKFSK-PDBXOOCHSA-N 0.000 claims description 20
- HVGRZDASOHMCSK-UHFFFAOYSA-N (Z,Z)-13,16-docosadienoic acid Natural products CCCCCC=CCC=CCCCCCCCCCCCC(O)=O HVGRZDASOHMCSK-UHFFFAOYSA-N 0.000 claims description 19
- CVCXSNONTRFSEH-UHFFFAOYSA-N docosa-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCCCCCC=CC=CC(O)=O CVCXSNONTRFSEH-UHFFFAOYSA-N 0.000 claims description 19
- KFINXCASWPGHEW-UHFFFAOYSA-N (9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid Natural products CCC=CCC=CC(O)C(O)C(O)CCCCCCCC(O)=O KFINXCASWPGHEW-UHFFFAOYSA-N 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- WBBQTNCISCKUMU-PDBXOOCHSA-N (13Z,16Z,19Z)-docosatrienoic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCCCCCC(O)=O WBBQTNCISCKUMU-PDBXOOCHSA-N 0.000 claims description 16
- -1 Eicosatrienoic acid, eicosatrienoic acid oxylipin derivatives Chemical class 0.000 claims description 15
- 208000024891 symptom Diseases 0.000 claims description 14
- SSLIVPIZGUYFPN-UHFFFAOYSA-N 17-hydroxydocosa-2,4,6-trienoic acid Chemical compound CCCCCC(O)CCCCCCCCCC=CC=CC=CC(O)=O SSLIVPIZGUYFPN-UHFFFAOYSA-N 0.000 claims description 13
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 230000001580 bacterial effect Effects 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- NOOOCZGLJNDCDR-UHFFFAOYSA-N 6-hydroxyicosa-2,4,6-trienoic acid Chemical compound CCCCCCCCCCCCCC=C(O)C=CC=CC(O)=O NOOOCZGLJNDCDR-UHFFFAOYSA-N 0.000 claims description 9
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 8
- OFACCCIBXRARJU-UHFFFAOYSA-N 13,16-dihydroxydocosa-2,4-dienoic acid Chemical compound CCCCCCC(O)CCC(O)CCCCCCCC=CC=CC(O)=O OFACCCIBXRARJU-UHFFFAOYSA-N 0.000 claims description 7
- PQJZOMXEAZSUON-UHFFFAOYSA-N 13-hydroxydocosa-2,4,6-trienoic acid Chemical compound CCCCCCCCCC(O)CCCCCC=CC=CC=CC(O)=O PQJZOMXEAZSUON-UHFFFAOYSA-N 0.000 claims description 7
- 239000010775 animal oil Substances 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- BZNFDQMYXKOGQK-UHFFFAOYSA-N 20-hydroxydocosa-2,4,6-trienoic acid Chemical compound CCC(O)CCCCCCCCCCCCC=CC=CC=CC(O)=O BZNFDQMYXKOGQK-UHFFFAOYSA-N 0.000 claims description 6
- XJMKJLJRBGUPAQ-UHFFFAOYSA-N CCCCCCCCC(O)CCCCCC(O)CCCCC(O)=O.CCC(O)CCCCCCC(O)CCCC=CC=CC=CC(O)=O Chemical compound CCCCCCCCC(O)CCCCCC(O)CCCCC(O)=O.CCC(O)CCCCCCC(O)CCCC=CC=CC=CC(O)=O XJMKJLJRBGUPAQ-UHFFFAOYSA-N 0.000 claims description 6
- IGZDHDRBQYDCMM-UHFFFAOYSA-N 11-hydroxyicosa-2,4,6-trienoic acid Chemical compound CCCCCCCCCC(O)CCCC=CC=CC=CC(O)=O IGZDHDRBQYDCMM-UHFFFAOYSA-N 0.000 claims description 5
- IUKXMNDGTWTNTP-OAHXIXLCSA-N 15(S)-HETrE Chemical compound CCCCC[C@H](O)\C=C\C=C/C\C=C/CCCCCCC(O)=O IUKXMNDGTWTNTP-OAHXIXLCSA-N 0.000 claims description 5
- NHLOFNUZMRWUMM-UHFFFAOYSA-N 8-hydroxyicosa-2,4,6-trienoic acid Chemical compound CCCCCCCCCCCCC(O)C=CC=CC=CC(O)=O NHLOFNUZMRWUMM-UHFFFAOYSA-N 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 5
- 235000016709 nutrition Nutrition 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- HUYAECUZIZUGRC-UHFFFAOYSA-N 5-hydroxyicosa-2,4,6-trienoic acid Chemical compound CCCCCCCCCCCCCC=CC(O)=CC=CC(O)=O HUYAECUZIZUGRC-UHFFFAOYSA-N 0.000 claims description 4
- IQLUYYHUNSSHIY-HZUMYPAESA-N eicosatetraenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C=C\C(O)=O IQLUYYHUNSSHIY-HZUMYPAESA-N 0.000 claims description 4
- CRLWRPLRCSJNAG-UHFFFAOYSA-N 18-hydroxyicosa-2,4,6-trienoic acid Chemical compound CCC(O)CCCCCCCCCCC=CC=CC=CC(O)=O CRLWRPLRCSJNAG-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- NZZBEQXZQODERA-UHFFFAOYSA-N OC(CCCC=CC=CC=CC(=O)O)CCCCCCC(CC)O.OC(C=CC=CC(=O)O)=CCCCCC(CCCCCCCC)O Chemical compound OC(CCCC=CC=CC=CC(=O)O)CCCCCCC(CC)O.OC(C=CC=CC(=O)O)=CCCCCC(CCCCCCCC)O NZZBEQXZQODERA-UHFFFAOYSA-N 0.000 claims description 2
- PWCLGRZBVAZIGI-UHFFFAOYSA-N icosa-15,17,19-trien-3-ol Chemical compound CCC(CCCCCCCCCCCC=CC=CC=C)O PWCLGRZBVAZIGI-UHFFFAOYSA-N 0.000 claims description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 2
- DQRSJOZDBPWTCH-UHFFFAOYSA-N docosa-1,3,5-triene Chemical compound CCCCCCCCCCCCCCCCC=CC=CC=C DQRSJOZDBPWTCH-UHFFFAOYSA-N 0.000 claims 3
- 235000013311 vegetables Nutrition 0.000 claims 1
- 235000021294 Docosapentaenoic acid Nutrition 0.000 description 148
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 description 125
- 235000021292 Docosatetraenoic acid Nutrition 0.000 description 41
- FPRKGXIOSIUDSE-SYACGTDESA-N (2z,4z,6z,8z)-docosa-2,4,6,8-tetraenoic acid Chemical compound CCCCCCCCCCCCC\C=C/C=C\C=C/C=C\C(O)=O FPRKGXIOSIUDSE-SYACGTDESA-N 0.000 description 34
- 102000004190 Enzymes Human genes 0.000 description 30
- 108090000790 Enzymes Proteins 0.000 description 30
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 25
- 244000005700 microbiome Species 0.000 description 23
- 241000196324 Embryophyta Species 0.000 description 19
- 102000001554 Hemoglobins Human genes 0.000 description 18
- 108010054147 Hemoglobins Proteins 0.000 description 18
- 239000000758 substrate Substances 0.000 description 17
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 14
- 229940090949 docosahexaenoic acid Drugs 0.000 description 13
- 102100024902 Cytochrome P450 4F2 Human genes 0.000 description 12
- 101000909122 Homo sapiens Cytochrome P450 4F2 Proteins 0.000 description 12
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 10
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 10
- 102000003820 Lipoxygenases Human genes 0.000 description 10
- 108090000128 Lipoxygenases Proteins 0.000 description 10
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 10
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 102000011730 Arachidonate 12-Lipoxygenase Human genes 0.000 description 6
- 108010076676 Arachidonate 12-lipoxygenase Proteins 0.000 description 6
- 102000009515 Arachidonate 15-Lipoxygenase Human genes 0.000 description 6
- 108010048907 Arachidonate 15-lipoxygenase Proteins 0.000 description 6
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 6
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 6
- 102000010907 Cyclooxygenase 2 Human genes 0.000 description 6
- 108010037462 Cyclooxygenase 2 Proteins 0.000 description 6
- 108010000561 Cytochrome P-450 CYP2C8 Proteins 0.000 description 6
- 102100029359 Cytochrome P450 2C8 Human genes 0.000 description 6
- 102100027567 Cytochrome P450 4A11 Human genes 0.000 description 6
- 102100027419 Cytochrome P450 4B1 Human genes 0.000 description 6
- 102100024916 Cytochrome P450 4F11 Human genes 0.000 description 6
- 102100024918 Cytochrome P450 4F12 Human genes 0.000 description 6
- 102100024901 Cytochrome P450 4F3 Human genes 0.000 description 6
- 101000725111 Homo sapiens Cytochrome P450 4A11 Proteins 0.000 description 6
- 101000909111 Homo sapiens Cytochrome P450 4F11 Proteins 0.000 description 6
- 101000909108 Homo sapiens Cytochrome P450 4F12 Proteins 0.000 description 6
- 101000909121 Homo sapiens Cytochrome P450 4F3 Proteins 0.000 description 6
- 101000653005 Homo sapiens Thromboxane-A synthase Proteins 0.000 description 6
- 102100033075 Prostacyclin synthase Human genes 0.000 description 6
- 101710179550 Prostacyclin synthase Proteins 0.000 description 6
- 102000015846 Prostacyclin synthases Human genes 0.000 description 6
- 102100029437 Serine/threonine-protein kinase A-Raf Human genes 0.000 description 6
- 102100030973 Thromboxane-A synthase Human genes 0.000 description 6
- 108010018719 cytochrome P-450 CYP4B1 Proteins 0.000 description 6
- 230000037361 pathway Effects 0.000 description 6
- 108010064377 prostacyclin synthetase Proteins 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 4
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 4
- 229960001138 acetylsalicylic acid Drugs 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 210000002540 macrophage Anatomy 0.000 description 4
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 230000001877 deodorizing effect Effects 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 3
- 239000004090 neuroprotective agent Substances 0.000 description 3
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-N 0.000 description 2
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 101000668058 Infectious salmon anemia virus (isolate Atlantic salmon/Norway/810/9/99) RNA-directed RNA polymerase catalytic subunit Proteins 0.000 description 2
- 102000003777 Interleukin-1 beta Human genes 0.000 description 2
- 108090000193 Interleukin-1 beta Proteins 0.000 description 2
- 241000592344 Spermatophyta Species 0.000 description 2
- 210000001744 T-lymphocyte Anatomy 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003399 chemotactic effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000020667 long-chain omega-3 fatty acid Nutrition 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 210000000440 neutrophil Anatomy 0.000 description 2
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 2
- 229940012843 omega-3 fatty acid Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 description 1
- DXTGFALYZGNEET-UHFFFAOYSA-N 11,18-dihydroxyicosa-2,4,6-trienoic acid Chemical compound CCC(O)CCCCCCC(O)CCCC=CC=CC=CC(O)=O DXTGFALYZGNEET-UHFFFAOYSA-N 0.000 description 1
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- FALVPIPHNAYLQX-UHFFFAOYSA-N CCC(CCCCCCCCCCCCCC=CC=CC=C)O Chemical compound CCC(CCCCCCCCCCCCCC=CC=CC=C)O FALVPIPHNAYLQX-UHFFFAOYSA-N 0.000 description 1
- 241001467333 Thraustochytriaceae Species 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89070107P | 2007-02-20 | 2007-02-20 | |
| PCT/US2008/054456 WO2008103753A2 (en) | 2007-02-20 | 2008-02-20 | Oxylipins from long chain polyunsaturated fatty acids and methods of making and using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010519311A JP2010519311A (ja) | 2010-06-03 |
| JP2010519311A5 true JP2010519311A5 (enExample) | 2011-04-07 |
Family
ID=39710725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009550992A Pending JP2010519311A (ja) | 2007-02-20 | 2008-02-20 | 長鎖多価不飽和脂肪酸由来のオキシリピンならびにその作製およびその使用方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20110190389A1 (enExample) |
| EP (1) | EP2120920A4 (enExample) |
| JP (1) | JP2010519311A (enExample) |
| CN (1) | CN101663031A (enExample) |
| WO (1) | WO2008103753A2 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8324277B2 (en) | 2007-08-01 | 2012-12-04 | University of Pittsburgh—of the Commonwealth System of Higher Education | Nitrated-fatty acids modulation of type II diabetes |
| CN102083787A (zh) | 2008-05-01 | 2011-06-01 | 康普雷克萨公司 | 乙烯基取代的脂肪酸 |
| WO2009155439A2 (en) | 2008-06-19 | 2009-12-23 | University Of Utah Research Foundation | Use of nitrated lipids for treatment of side effects of toxic medical therapies |
| US20140024713A1 (en) | 2008-06-19 | 2014-01-23 | University Of Utah Research Foundation | Use of nitrated lipids for treatment of side effects of toxic medical therapies |
| US8927747B2 (en) * | 2008-09-16 | 2015-01-06 | The Brigham And Women's Hospital, Inc. | 14-hydroxy-docosahexaenoic acid compounds |
| 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 |
| FR2942964B1 (fr) * | 2009-03-16 | 2012-08-17 | Arkopharma Laboratoires | Stimulateur metabolique des ppaps a base d'esters d'acides gras libres insatures, composition huileuse et complement alimentaire les contenant |
| EP2283839A1 (en) * | 2009-06-30 | 2011-02-16 | Institut National des Sciences Appliquées de Lyon | Polyunsaturated hydroxylated molecule having an eze geometry and its use in therapy |
| JP2013500966A (ja) * | 2009-07-31 | 2013-01-10 | ユニバーシティー オブ ピッツバーグ − オブ ザ コモンウェルス システム オブ ハイヤー エデュケーション | 抗炎症剤としての脂肪酸 |
| US8686167B2 (en) | 2009-10-02 | 2014-04-01 | Complexa, Inc. | Heteroatom containing substituted fatty acids |
| EA035287B1 (ru) * | 2011-07-21 | 2020-05-25 | ДСМ АйПи АССЕТС Б.В. | Микроорганизмы, продуцирующие эйкозапентаеновую кислоту, композиции, содержащие жирные кислоты, и способы их получения и применения |
| WO2013028501A1 (en) | 2011-08-19 | 2013-02-28 | The University Of Utah Research Foundation | Combination therapy with nitrated lipids and inhibitors of the renin-angiotensin-aldosterone system |
| KR102162901B1 (ko) * | 2011-09-29 | 2020-10-08 | 피엘엑스 옵코 인코포레이티드 | 위장관을 따라 약물을 표적화 방출하기 위한 pH 감응성 담체, 그로부터의 조성물, 및 이들의 제조 및 사용 방법 |
| SG11201403805WA (en) | 2012-01-06 | 2014-08-28 | Omthera Pharmaceuticals Inc | Dpa-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form |
| US20150018417A1 (en) * | 2012-02-03 | 2015-01-15 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Fatty acids as anti-inflammatory agents |
| JP6173352B2 (ja) * | 2012-02-15 | 2017-08-02 | アニダ ファーマ インコーポレイテッド | 筋萎縮性側索硬化症の治療方法 |
| AR095182A1 (es) | 2012-05-07 | 2015-09-30 | Omthera Pharmaceuticals Inc | Composiciones de estatinas y ácidos grasos omega-3 |
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2008
- 2008-02-20 US US12/531,344 patent/US20110190389A1/en not_active Abandoned
- 2008-02-20 CN CN200880012827A patent/CN101663031A/zh active Pending
- 2008-02-20 JP JP2009550992A patent/JP2010519311A/ja active Pending
- 2008-02-20 EP EP08730288A patent/EP2120920A4/en not_active Withdrawn
- 2008-02-20 WO PCT/US2008/054456 patent/WO2008103753A2/en not_active Ceased
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