CN109232278A - 多不饱和羟基脂肪酸的药学上可接受的盐 - Google Patents
多不饱和羟基脂肪酸的药学上可接受的盐 Download PDFInfo
- Publication number
- CN109232278A CN109232278A CN201811061377.2A CN201811061377A CN109232278A CN 109232278 A CN109232278 A CN 109232278A CN 201811061377 A CN201811061377 A CN 201811061377A CN 109232278 A CN109232278 A CN 109232278A
- Authority
- CN
- China
- Prior art keywords
- salt
- weight
- pharmaceutical composition
- hetre
- lysine
- 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
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 210
- -1 unsaturated hydroxy fatty acid Chemical class 0.000 title description 79
- 235000014113 dietary fatty acids Nutrition 0.000 title description 6
- 239000000194 fatty acid Substances 0.000 title description 6
- 229930195729 fatty acid Natural products 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 50
- 102000009515 Arachidonate 15-Lipoxygenase Human genes 0.000 claims abstract description 43
- 108010048907 Arachidonate 15-lipoxygenase Proteins 0.000 claims abstract description 43
- 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 83
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 76
- 239000002253 acid Substances 0.000 claims description 74
- 239000008194 pharmaceutical composition Substances 0.000 claims description 66
- 239000004472 Lysine Substances 0.000 claims description 49
- 229960003646 lysine Drugs 0.000 claims description 49
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 44
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 26
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 17
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 17
- 229960003104 ornithine Drugs 0.000 claims description 17
- XUJWOMMOEOHPFP-UHFFFAOYSA-N (all-Z)-8,11-Eicosadienoic acid Natural products CCCCCCCCC=CCC=CCCCCCCC(O)=O XUJWOMMOEOHPFP-UHFFFAOYSA-N 0.000 claims description 16
- XUJWOMMOEOHPFP-OKLKQMLOSA-N 8,11-Eicosadienoic acid Chemical compound CCCCCCCC\C=C\C\C=C\CCCCCCC(O)=O XUJWOMMOEOHPFP-OKLKQMLOSA-N 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 13
- 229960003194 meglumine Drugs 0.000 claims description 13
- 229910052708 sodium Inorganic materials 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 11
- 150000001336 alkenes Chemical class 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 10
- 238000003860 storage Methods 0.000 claims description 9
- 229960005141 piperazine Drugs 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 229940083542 sodium Drugs 0.000 claims description 5
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 4
- 208000004930 Fatty Liver Diseases 0.000 claims description 4
- 206010019708 Hepatic steatosis Diseases 0.000 claims description 4
- 206010000496 acne Diseases 0.000 claims description 4
- 208000010706 fatty liver disease Diseases 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 231100000240 steatosis hepatitis Toxicity 0.000 claims description 4
- JSFATNQSLKRBCI-UHFFFAOYSA-N 15-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC(O)C=CC=CCC=CCC=CCCCC(O)=O JSFATNQSLKRBCI-UHFFFAOYSA-N 0.000 claims description 3
- 206010015150 Erythema Diseases 0.000 claims description 3
- 231100000321 erythema Toxicity 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 201000001119 neuropathy Diseases 0.000 claims description 3
- 230000007823 neuropathy Effects 0.000 claims description 3
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 3
- OEYKGJFTEBHJCL-PDBXOOCHSA-N (9z,12z,15z)-octadeca-9,12,15-trieneperoxoic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OO OEYKGJFTEBHJCL-PDBXOOCHSA-N 0.000 claims 1
- JSFATNQSLKRBCI-VAEKSGALSA-N 15-HETE Natural products CCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O JSFATNQSLKRBCI-VAEKSGALSA-N 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- 235000018977 lysine Nutrition 0.000 description 41
- 239000000463 material Substances 0.000 description 41
- 102000003820 Lipoxygenases Human genes 0.000 description 39
- 108090000128 Lipoxygenases Proteins 0.000 description 39
- 238000000034 method Methods 0.000 description 33
- 238000004458 analytical method Methods 0.000 description 32
- HNICUWMFWZBIFP-BSZOFBHHSA-N 13-HODE Chemical compound CCCCCC(O)\C=C\C=C/CCCCCCCC(O)=O HNICUWMFWZBIFP-BSZOFBHHSA-N 0.000 description 31
- 239000002904 solvent Substances 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 26
- 238000000634 powder X-ray diffraction Methods 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- 239000012065 filter cake Substances 0.000 description 21
- 239000012535 impurity Substances 0.000 description 21
- 159000000000 sodium salts Chemical class 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- HOBAELRKJCKHQD-UHFFFAOYSA-N (8Z,11Z,14Z)-8,11,14-eicosatrienoic acid Natural products CCCCCC=CCC=CCC=CCCCCCCC(O)=O HOBAELRKJCKHQD-UHFFFAOYSA-N 0.000 description 19
- HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 239000000725 suspension Substances 0.000 description 15
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 14
- 229960004488 linolenic acid Drugs 0.000 description 14
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 14
- 238000001228 spectrum Methods 0.000 description 14
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 150000004885 piperazines Chemical class 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 230000003321 amplification Effects 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 238000003199 nucleic acid amplification method Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 8
- HZRUTVAFDWTKGD-JEDNCBNOSA-N (2s)-2,6-diaminohexanoic acid;hydrate Chemical compound O.NCCCC[C@H](N)C(O)=O HZRUTVAFDWTKGD-JEDNCBNOSA-N 0.000 description 7
- 230000003213 activating effect Effects 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 7
- 238000000113 differential scanning calorimetry Methods 0.000 description 7
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 238000012216 screening Methods 0.000 description 7
- 238000001757 thermogravimetry curve Methods 0.000 description 7
- 230000009102 absorption Effects 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000006184 cosolvent Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000003937 drug carrier Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 125000004193 piperazinyl group Chemical group 0.000 description 6
- 238000002390 rotary evaporation Methods 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- DWNBOPVKNPVNQG-LURJTMIESA-N (2s)-4-hydroxy-2-(propylamino)butanoic acid Chemical compound CCCN[C@H](C(O)=O)CCO DWNBOPVKNPVNQG-LURJTMIESA-N 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 235000019766 L-Lysine Nutrition 0.000 description 5
- 238000005388 cross polarization Methods 0.000 description 5
- 239000002178 crystalline material Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 5
- 229940011051 isopropyl acetate Drugs 0.000 description 5
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000013508 migration Methods 0.000 description 5
- 230000005012 migration Effects 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 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 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000007872 degassing Methods 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000010985 leather Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- 101710150697 Inositol monophosphatase 1 Proteins 0.000 description 3
- 102100035679 Inositol monophosphatase 1 Human genes 0.000 description 3
- 101710150707 Inositol monophosphatase 2 Proteins 0.000 description 3
- 102100021608 Inositol monophosphatase 2 Human genes 0.000 description 3
- 101710150706 Inositol monophosphatase 3 Proteins 0.000 description 3
- 101710109188 Putative inositol monophosphatase 3 Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 235000015165 citric acid Nutrition 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 235000018417 cysteine Nutrition 0.000 description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 3
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 229940088679 drug related substance Drugs 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 239000004519 grease Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000004537 pulping Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000012056 semi-solid material Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000009210 therapy by ultrasound Methods 0.000 description 3
- MNSWITGNWZSAMC-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl prop-2-enoate Chemical compound FC(F)(F)C(C(F)(F)F)OC(=O)C=C MNSWITGNWZSAMC-UHFFFAOYSA-N 0.000 description 2
- 206010067484 Adverse reaction Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 101100021671 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) LPX1 gene Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000006838 adverse reaction Effects 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000012296 anti-solvent Substances 0.000 description 2
- 229940114079 arachidonic acid Drugs 0.000 description 2
- 235000021342 arachidonic acid Nutrition 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
- 230000005496 eutectics Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- BCUMPULZWNQMKD-UHFFFAOYSA-N methanol;propan-2-yl acetate Chemical compound OC.CC(C)OC(C)=O BCUMPULZWNQMKD-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 150000003956 methylamines Chemical class 0.000 description 2
- 238000001000 micrograph Methods 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- GSUOAUYYFHAZTQ-ZSCHJXSPSA-N (2S)-2,6-diaminohexanoic acid 15-hydroperoxyicosa-5,8,11,13-tetraenoic acid Chemical compound NCCCC[C@H](N)C(O)=O.CCCCCC(OO)C=CC=CCC=CCC=CCCCC(O)=O GSUOAUYYFHAZTQ-ZSCHJXSPSA-N 0.000 description 1
- ZSXSPIFKGXFOGN-ZSCHJXSPSA-N (2S)-2,6-diaminohexanoic acid 15-hydroxyicosa-5,8,11,13-tetraenoic acid Chemical compound NCCCC[C@H](N)C(O)=O.CCCCCC(O)C=CC=CCC=CCC=CCCCC(O)=O ZSXSPIFKGXFOGN-ZSCHJXSPSA-N 0.000 description 1
- OIZLSGZXLWRCLY-IGBDUZKASA-N (3R,4R,5S,6R)-6-(hydroxymethyl)-3-(methylamino)oxane-2,4,5-triol (2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CN[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OIZLSGZXLWRCLY-IGBDUZKASA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- HNICUWMFWZBIFP-IRQZEAMPSA-N 13(S)-HODE Chemical compound CCCCC[C@H](O)\C=C\C=C/CCCCCCCC(O)=O HNICUWMFWZBIFP-IRQZEAMPSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- XPHYFROVBIGQJG-UHFFFAOYSA-N C1CNCCN1.CCCCCC(O)C=CC=CCC=CCC=CCCCC(O)=O Chemical compound C1CNCCN1.CCCCCC(O)C=CC=CCC=CCC=CCCCC(O)=O XPHYFROVBIGQJG-UHFFFAOYSA-N 0.000 description 1
- QMBAZKPATOBOSX-UHFFFAOYSA-N C1CNCCN1.CCCCCC(OO)C=CC=CCC=CCC=CCCCC(O)=O Chemical compound C1CNCCN1.CCCCCC(OO)C=CC=CCC=CCC=CCCCC(O)=O QMBAZKPATOBOSX-UHFFFAOYSA-N 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- HENKTYXKCALFRM-JEDNCBNOSA-N N[C@@H](CCCCN)C(=O)O.CO Chemical compound N[C@@H](CCCCN)C(=O)O.CO HENKTYXKCALFRM-JEDNCBNOSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 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 description 1
- 208000030961 allergic reaction Diseases 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 238000005842 biochemical reaction Methods 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 210000000222 eosinocyte Anatomy 0.000 description 1
- ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 1
- NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000016507 interphase Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 229960002306 lysine monohydrate Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- XTFYUWSABZVIFD-UHFFFAOYSA-N propan-2-ol;propan-2-yl acetate Chemical compound CC(C)O.CC(C)OC(C)=O XTFYUWSABZVIFD-UHFFFAOYSA-N 0.000 description 1
- ZJLBPXHQYXCWNP-UHFFFAOYSA-N propan-2-one;propan-2-yl acetate Chemical compound CC(C)=O.CC(C)OC(C)=O ZJLBPXHQYXCWNP-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- PRMTWKJDVXRLBZ-UHFFFAOYSA-M sodium 15-hydroperoxyicosa-5,8,11,13-tetraenoate Chemical compound [Na+].O(O)C(C=CC=CCC=CCC=CCCCC(=O)[O-])CCCCC PRMTWKJDVXRLBZ-UHFFFAOYSA-M 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- RQVLCLFGGVMPGP-UHFFFAOYSA-M sodium;15-hydroxyicosa-5,8,11,13-tetraenoate Chemical compound [Na+].CCCCCC(O)C=CC=CCC=CCC=CCCCC([O-])=O RQVLCLFGGVMPGP-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
-
- 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
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/26—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one amino group bound to the carbon skeleton, e.g. lysine
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- 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
-
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/10—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with one amino group and at least two hydroxy groups bound to the carbon skeleton
-
- 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/04—Preparation of hydrazides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Biomedical Technology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361904600P | 2013-11-15 | 2013-11-15 | |
| US61/904,600 | 2013-11-15 | ||
| CN201480071412.2A CN105899485B (zh) | 2013-11-15 | 2014-11-17 | 多不饱和羟基脂肪酸的药学上可接受的盐 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480071412.2A Division CN105899485B (zh) | 2013-11-15 | 2014-11-17 | 多不饱和羟基脂肪酸的药学上可接受的盐 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109232278A true CN109232278A (zh) | 2019-01-18 |
Family
ID=52669635
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811061377.2A Pending CN109232278A (zh) | 2013-11-15 | 2014-11-17 | 多不饱和羟基脂肪酸的药学上可接受的盐 |
| CN201480071412.2A Expired - Fee Related CN105899485B (zh) | 2013-11-15 | 2014-11-17 | 多不饱和羟基脂肪酸的药学上可接受的盐 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480071412.2A Expired - Fee Related CN105899485B (zh) | 2013-11-15 | 2014-11-17 | 多不饱和羟基脂肪酸的药学上可接受的盐 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US10017453B2 (https=) |
| EP (3) | EP3878835A1 (https=) |
| JP (3) | JP2016538288A (https=) |
| CN (2) | CN109232278A (https=) |
| ES (1) | ES2727387T3 (https=) |
| WO (1) | WO2015071766A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3129008A1 (en) * | 2015-12-18 | 2017-06-22 | Afimmune Limited | Compositions comprising 15-hepe and methods of using the same |
| WO2018168860A1 (ja) * | 2017-03-14 | 2018-09-20 | イビデン株式会社 | 植物賦活剤 |
| US20210315851A1 (en) | 2020-04-03 | 2021-10-14 | Afimmune Limited | Compositions comprising 15-hepe and methods of treating or preventing hematologic disorders, and/or related diseases |
| US20220133669A1 (en) | 2020-10-30 | 2022-05-05 | Ds Biopharma Limited | Pharmaceutical compositions comprising 15-hetre and methods of use thereof |
| FR3148365A1 (fr) * | 2023-05-04 | 2024-11-08 | Pierre Fabre Dermo-Cosmetique | Oxylipines dans le traitement de la séborrhée et/ou de l’acné |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1387503A (zh) * | 1999-11-09 | 2002-12-25 | 爱尔康公司 | 羟基二十碳四烯酸盐,用于治疗干眼病的组合物和方法 |
| WO2004072013A1 (ja) * | 2003-02-14 | 2004-08-26 | Taisho Pharmaceutical Co.,Ltd. | ヒドロキシエイコサジエン酸化合物 |
| CN102448453A (zh) * | 2009-05-01 | 2012-05-09 | 伊奎特德有限公司 | 多不饱和脂肪酸在治疗神经损伤中的用途 |
| WO2013112876A1 (en) * | 2012-01-26 | 2013-08-01 | Dignity Sciences Limited | Antimicrobial compositions comprising dgla, 15-ohepa and/or 15-hetre and methods of use thereof |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3055923A (en) * | 1960-03-25 | 1962-09-25 | Baxter Laboratories Inc | Fatty acid salts |
| IE47777B1 (en) | 1978-01-23 | 1984-06-13 | Efamol Ltd | Pharmaceutical and dietary composition comprising gamma-linolenic acids |
| US5352700A (en) | 1988-01-14 | 1994-10-04 | Anders Frithz | Use of essential fatty acids for the preparation of a drug for the treatment of infantile seborrheic eczema |
| GB9111900D0 (en) | 1991-06-03 | 1991-07-24 | Efamol Holdings | Fatty acid compositions |
| JPH05186342A (ja) | 1992-01-10 | 1993-07-27 | Fujirebio Inc | 免疫調節作用を併せもつ抗炎症剤 |
| US5807884A (en) * | 1992-10-30 | 1998-09-15 | Emory University | Treatment for atherosclerosis and other cardiovascular and inflammatory diseases |
| GB9301446D0 (en) | 1993-01-26 | 1993-03-17 | Scotia Holdings Plc | Internal radiation damage |
| AU683027B2 (en) | 1993-01-27 | 1997-10-30 | Scotia Holdings Plc | Triglycerides |
| US5696166A (en) * | 1995-10-31 | 1997-12-09 | Yanni; John M. | Compositions containing hydroxyeicosatetraenoic acid derivatives and methods of use in treating dry eye disorders |
| KR19990071477A (ko) * | 1996-09-20 | 1999-09-27 | 아테로제닉스, 인코포레이티드 | 염증성질환의진단방법및매개체 |
| GB9715444D0 (en) | 1997-07-22 | 1997-09-24 | Scotia Holdings Plc | Therapeutic and dietary compositions |
| JP2002515480A (ja) * | 1998-05-15 | 2002-05-28 | ユニバーシティ オブ バーモント | １６−ヒドロキシエイコサテトラエン酸の新規アナログ |
| JP2000191525A (ja) | 1998-12-25 | 2000-07-11 | Nof Corp | 皮膚外用剤組成物 |
| EP1762557B1 (en) | 2000-02-16 | 2011-04-06 | The Brigham And Women's Hospital, Inc. | Aspirin-triggered lipid mediators |
| US20020188024A1 (en) | 2000-08-23 | 2002-12-12 | Chilton Floyd H. | Fatty acid-containing emulsion with increased bioavailability |
| DE10121252A1 (de) | 2001-04-30 | 2002-11-07 | Christos C Zouboulis | Behandlung der Akne |
| JP2005179211A (ja) | 2003-12-17 | 2005-07-07 | Idemitsu Kosan Co Ltd | 皮膚外用剤組成物 |
| EP1711173A2 (en) | 2003-12-31 | 2006-10-18 | Igennus Limited | Formulation containing an eicosapentaenoic acid or an ester thereof and a triterpene or ester thereof |
| WO2005102309A2 (en) | 2004-04-26 | 2005-11-03 | Ltb4 Sweden Ab | In vivo release of endogenous anti-microbial mediators by leukotriene b4 (ltb4) administration |
| US7666447B2 (en) | 2004-10-08 | 2010-02-23 | Pharmanutrients | Compositions including Krill extracts and conjugated linoleic acid and methods of using same |
| 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 |
| EP3581178B1 (en) | 2005-02-14 | 2023-08-30 | Suntory Holdings Limited | Composition containing dihomo-(gamma)-linolenic acid (dgla) as active ingredient |
| TW200711649A (en) | 2005-06-17 | 2007-04-01 | Combinatorx Inc | Combination therapy for the treatment of immunoinflammatory disorders |
| EP3285072B1 (en) | 2006-08-08 | 2020-04-15 | Metabolon, Inc. | Markers of non-alcoholic fatty liver disease (nafld) and non-alcoholic steatohepatitis (nash) and methods of use thereof |
| JP5101894B2 (ja) | 2007-01-15 | 2012-12-19 | サントリーホールディングス株式会社 | 高度不飽和脂肪酸及びこれを含有する脂質の製造方法 |
| GB0802116D0 (en) | 2008-02-05 | 2008-03-12 | Natural Enviromental Res Counc | Treatment |
| US20110105510A1 (en) | 2008-06-17 | 2011-05-05 | Hiroshi Ishikawa | Prophylactic/ameliorating or therapeutic agent for non-alcoholic steatohepatitis |
| GB0907413D0 (en) | 2009-04-29 | 2009-06-10 | Equateq Ltd | Novel methods |
| US10154977B2 (en) | 2011-03-25 | 2018-12-18 | The Brigham And Women's Hospital, Inc. | Anti-inflammatory particles |
| US20120264824A1 (en) | 2011-04-15 | 2012-10-18 | Mochida Pharmaceutical Co., Ltd. | Compositions and methods for treating non-alcoholic steatohepatitis |
| RU2014119948A (ru) | 2011-10-19 | 2015-11-27 | Дигнити Сайенсиз Лимитед | ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ, СОДЕРЖАЩИЕ DGLA И/ИЛИ 15-HETrE, И СПОСОБЫ ИХ ПРИМЕНЕНИЯ |
| US8293790B2 (en) | 2011-10-19 | 2012-10-23 | Dignity Sciences Limited | Pharmaceutical compositions comprising DGLA and benzoyl peroxide and methods of use thereof |
| JP2015500639A (ja) | 2011-11-29 | 2015-01-08 | ディグニティ サイエンシス リミテッド | ２０−炭素脂肪酸を含む組成物ならびにその製造方法および使用方法 |
| RS57777B1 (sr) | 2012-01-06 | 2018-12-31 | Omthera Pharmaceuticals Inc | Dpa-obogaćene kompozicije omega-3 polinezasićenih masnih kiselina u obliku slobodne kiseline |
| US20130267598A1 (en) | 2012-02-23 | 2013-10-10 | Dignity Sciences Limited | Pharmaceutical compositions comprising dgla, 15-ohepa, and/or 15-hetre and methods of reducing sebum production using same |
| WO2013150386A2 (en) | 2012-04-04 | 2013-10-10 | Pronova Biopharma Norge As | Compositions comprising omega-3 fatty acids and vitamin d for acne vulgaris and/or eczema, and methods and uses thereof |
| DK2858496T3 (da) | 2012-05-10 | 2023-07-24 | Solutex Na Llc | Olier med anti-inflammatorisk aktivitet, som indeholder naturlige specialiserede pro-afhjælpningsmediatorer og deres forløbere |
| WO2014022816A2 (en) | 2012-08-03 | 2014-02-06 | Dignity Sciences Limited | Pharmaceutical compositions comprising 15-hetre and methods of treating or preventing arthritis using same |
| GB201301626D0 (en) | 2013-01-30 | 2013-03-13 | Dignity Sciences Ltd | Composition comprising 15-OHEPA and methods of using the same |
| EP3091959A4 (en) | 2014-01-10 | 2017-09-20 | Dignity Sciences Limited | Pharmaceutical compositions comprising 15-hepe and methods of treating asthma and lung disorders using same |
| US9682055B2 (en) | 2014-06-04 | 2017-06-20 | Dignity Sciences Limted | Pharmaceutical compositions comprising DGLA and use of same |
| MA41120A (fr) | 2014-12-02 | 2017-10-10 | Afimmune Ltd | Compositions comprenant le 15-hepe et méthodes de traitement ou de prévention de la fibrose à l'aide de celles-ci |
| CA3129008A1 (en) | 2015-12-18 | 2017-06-22 | Afimmune Limited | Compositions comprising 15-hepe and methods of using the same |
| CA3027867A1 (en) | 2016-01-07 | 2017-07-13 | Ds Biopharma Limited | Pharmaceutical compositions comprising dgla and use of same |
-
2014
- 2014-11-17 JP JP2016530882A patent/JP2016538288A/ja active Pending
- 2014-11-17 CN CN201811061377.2A patent/CN109232278A/zh active Pending
- 2014-11-17 WO PCT/IB2014/003027 patent/WO2015071766A1/en not_active Ceased
- 2014-11-17 US US14/543,638 patent/US10017453B2/en active Active
- 2014-11-17 EP EP21159762.0A patent/EP3878835A1/en not_active Withdrawn
- 2014-11-17 EP EP19157319.5A patent/EP3546446A1/en not_active Withdrawn
- 2014-11-17 CN CN201480071412.2A patent/CN105899485B/zh not_active Expired - Fee Related
- 2014-11-17 EP EP14843234.7A patent/EP3068757B1/en active Active
- 2014-11-17 ES ES14843234T patent/ES2727387T3/es active Active
-
2017
- 2017-12-01 US US15/828,700 patent/US10544088B2/en not_active Expired - Fee Related
-
2019
- 2019-11-26 JP JP2019212877A patent/JP6818851B2/ja not_active Expired - Fee Related
- 2019-12-05 US US16/704,289 patent/US20200181064A1/en not_active Abandoned
-
2020
- 2020-12-28 JP JP2020218615A patent/JP2021073194A/ja active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1387503A (zh) * | 1999-11-09 | 2002-12-25 | 爱尔康公司 | 羟基二十碳四烯酸盐,用于治疗干眼病的组合物和方法 |
| WO2004072013A1 (ja) * | 2003-02-14 | 2004-08-26 | Taisho Pharmaceutical Co.,Ltd. | ヒドロキシエイコサジエン酸化合物 |
| CN102448453A (zh) * | 2009-05-01 | 2012-05-09 | 伊奎特德有限公司 | 多不饱和脂肪酸在治疗神经损伤中的用途 |
| WO2013112876A1 (en) * | 2012-01-26 | 2013-08-01 | Dignity Sciences Limited | Antimicrobial compositions comprising dgla, 15-ohepa and/or 15-hetre and methods of use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| US10544088B2 (en) | 2020-01-28 |
| EP3068757B1 (en) | 2019-02-27 |
| US10017453B2 (en) | 2018-07-10 |
| JP2020055825A (ja) | 2020-04-09 |
| US20200181064A1 (en) | 2020-06-11 |
| WO2015071766A1 (en) | 2015-05-21 |
| JP6818851B2 (ja) | 2021-01-20 |
| US20180118655A1 (en) | 2018-05-03 |
| EP3878835A1 (en) | 2021-09-15 |
| EP3546446A1 (en) | 2019-10-02 |
| JP2021073194A (ja) | 2021-05-13 |
| US20150152034A1 (en) | 2015-06-04 |
| CN105899485A (zh) | 2016-08-24 |
| EP3068757A1 (en) | 2016-09-21 |
| ES2727387T3 (es) | 2019-10-15 |
| CN105899485B (zh) | 2018-10-19 |
| JP2016538288A (ja) | 2016-12-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109232278A (zh) | 多不饱和羟基脂肪酸的药学上可接受的盐 | |
| EP2697238B1 (en) | Solid forms of antiretroviral compounds, process for the preparation and their pharmaceutical composition thereof | |
| UA120508C2 (uk) | Комплекси сиролімусу і його похідних, спосіб їх отримання і фармацевтичні композиції, що містять зазначені комплекси | |
| JP2009504728A (ja) | 高い安定性及び溶出性を有する医薬製剤、及びその製造方法 | |
| EP3719014A1 (en) | Solid forms of an akt inhibiting pyrimidinyl-cyclopentane compound, compositions and methods thereof | |
| JP2009519343A (ja) | エンテロスタチンの非吸湿性組成物 | |
| LU83363A1 (fr) | Compositions antitumeurs | |
| JP4015954B2 (ja) | トシル酸スプラタスト結晶 | |
| TW202432120A (zh) | 注射用組合物、包含其之醫藥調配物以及製備該組合物之方法 | |
| JP2001354553A (ja) | 安定化されたユビデカレノン組成物およびユビデカレノン組成物の安定化方法 | |
| Mishra et al. | Solubility enhancement of clarithromycin using solid dispersion and effervescence assisted fusion technique | |
| CN1311823C (zh) | 靛玉红磷脂复合物及其制备方法 | |
| CN107200720B (zh) | 一种晶ⅱ型物质、其制法和其药物组合物与用途 | |
| AU2020298031A1 (en) | Succinate prodrug, compositions containing the succinate prodrug and uses thereof | |
| US12606518B2 (en) | Crystalline form of L-serine and process of preparing same | |
| JPH0474123A (ja) | 安定な活性型ビタミンｄ↓３類製剤 | |
| TWI361078B (en) | Stabilized leukotriene b4 (ltb4) agent pharmaceutical formulation | |
| CN107200719B (zh) | 990207-22-1一种晶vii型物质、其制法和其药物组合物与用途 | |
| CA2891822A1 (en) | Crystalline bortezomib process | |
| ES2984774T3 (es) | Procedimiento para la preparación de compuestos orgánicos férricos | |
| WO2008122425A2 (en) | Oral compositions containing tacrolimus in amorphous form | |
| CN102770416A (zh) | 美他沙酮共晶体 | |
| HK40016232A (en) | Pharmaceutically acceptable salts of polyunsaturated hydroxy fatty acids | |
| WO2022229761A1 (en) | SOLID FORM OF 2-CHLORO-2'-DEOXY-ADENOSINE COMPLEX WITH HPβCD | |
| WO1998029136A1 (en) | Stabilized tricyclic compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| TA01 | Transfer of patent application right | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20210517 Address after: Ai Erlandubailin Applicant after: DIGNITY SCIENCES LTD. Address before: Ai Erlandubailin Applicant before: DS Biopharmaceutical Co.,Ltd. |
|
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20190118 |