AU2006230136B2 - Trihydroxy polyunsaturated eicosanoid derivatives - Google Patents
Trihydroxy polyunsaturated eicosanoid derivatives Download PDFInfo
- Publication number
- AU2006230136B2 AU2006230136B2 AU2006230136A AU2006230136A AU2006230136B2 AU 2006230136 B2 AU2006230136 B2 AU 2006230136B2 AU 2006230136 A AU2006230136 A AU 2006230136A AU 2006230136 A AU2006230136 A AU 2006230136A AU 2006230136 B2 AU2006230136 B2 AU 2006230136B2
- Authority
- AU
- Australia
- Prior art keywords
- aryl
- alkyl
- heteroaryl
- perfluoroalkyl
- 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.)
- Ceased
Links
- 150000002066 eicosanoids Chemical class 0.000 title abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 60
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 206010061218 Inflammation Diseases 0.000 claims abstract description 17
- 230000004054 inflammatory process Effects 0.000 claims abstract description 17
- 201000010099 disease Diseases 0.000 claims abstract description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
- 230000002159 abnormal effect Effects 0.000 claims abstract description 15
- 230000004663 cell proliferation Effects 0.000 claims abstract description 15
- 230000028709 inflammatory response Effects 0.000 claims abstract description 15
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 13
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 13
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 13
- 201000011510 cancer Diseases 0.000 claims abstract description 13
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims description 114
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 125000001072 heteroaryl group Chemical group 0.000 claims description 87
- 150000001875 compounds Chemical class 0.000 claims description 86
- 229910052739 hydrogen Inorganic materials 0.000 claims description 72
- 239000001257 hydrogen Substances 0.000 claims description 71
- 125000003545 alkoxy group Chemical group 0.000 claims description 66
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 56
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 50
- 125000000623 heterocyclic group Chemical group 0.000 claims description 41
- 125000002837 carbocyclic group Chemical group 0.000 claims description 40
- 125000004104 aryloxy group Chemical group 0.000 claims description 33
- 125000001153 fluoro group Chemical group F* 0.000 claims description 33
- 125000003282 alkyl amino group Chemical group 0.000 claims description 31
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 31
- 229910052749 magnesium Inorganic materials 0.000 claims description 24
- 229910052725 zinc Inorganic materials 0.000 claims description 24
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 22
- 150000001768 cations Chemical class 0.000 claims description 22
- 229910052700 potassium Inorganic materials 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 21
- 125000005256 alkoxyacyl group Chemical group 0.000 claims description 21
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 21
- 229910052708 sodium Inorganic materials 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 9
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 24
- 206010003246 arthritis Diseases 0.000 claims 3
- 238000002360 preparation method Methods 0.000 abstract description 17
- 230000002265 prevention Effects 0.000 abstract description 4
- 238000010168 coupling process Methods 0.000 description 51
- 150000002431 hydrogen Chemical group 0.000 description 43
- -1 alkenyl boron compound Chemical class 0.000 description 34
- 238000005859 coupling reaction Methods 0.000 description 32
- 239000000243 solution Substances 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000000543 intermediate Substances 0.000 description 28
- 239000011701 zinc Substances 0.000 description 27
- 239000000047 product Substances 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
- 230000008878 coupling Effects 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 150000001299 aldehydes Chemical class 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000011777 magnesium Substances 0.000 description 16
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 239000002243 precursor Substances 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000003342 alkenyl group Chemical group 0.000 description 12
- 125000005647 linker group Chemical group 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 125000002947 alkylene group Chemical group 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 11
- 238000005984 hydrogenation reaction Methods 0.000 description 11
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 11
- 230000001225 therapeutic effect Effects 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 125000001246 bromo group Chemical group Br* 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 125000004442 acylamino group Chemical group 0.000 description 9
- 125000005518 carboxamido group Chemical group 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 8
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 7
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 7
- 150000001345 alkine derivatives Chemical class 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 229940126543 compound 14 Drugs 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 230000001404 mediated effect Effects 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 150000003751 zinc Chemical class 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 230000008901 benefit Effects 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229940126214 compound 3 Drugs 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000005035 acylthio group Chemical group 0.000 description 5
- 150000008052 alkyl sulfonates Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 125000005228 aryl sulfonate group Chemical group 0.000 description 5
- 125000005110 aryl thio group Chemical group 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000010949 copper Chemical group 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 150000002617 leukotrienes Chemical class 0.000 description 5
- 125000004043 oxo group Chemical group O=* 0.000 description 5
- 125000004437 phosphorous atom Chemical group 0.000 description 5
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 5
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 4
- 101710134784 Agnoprotein Proteins 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229930184725 Lipoxin Natural products 0.000 description 4
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 4
- 125000005282 allenyl group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000004071 biological effect Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000004113 cell culture Methods 0.000 description 4
- 229940127204 compound 29 Drugs 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000011981 lindlar catalyst Substances 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 150000002639 lipoxins Chemical class 0.000 description 4
- 238000006772 olefination reaction Methods 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 150000003180 prostaglandins Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 229940126639 Compound 33 Drugs 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- WLLIXJBWWFGEHT-UHFFFAOYSA-N [tert-butyl(dimethyl)silyl] trifluoromethanesulfonate Chemical compound CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F WLLIXJBWWFGEHT-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 229910052796 boron Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000002612 dispersion medium Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- AZOAIZOTNGTVSA-GFCCVEGCSA-N methyl (5s)-5-[tert-butyl(dimethyl)silyl]oxyhept-6-ynoate Chemical compound COC(=O)CCC[C@@H](C#C)O[Si](C)(C)C(C)(C)C AZOAIZOTNGTVSA-GFCCVEGCSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000010703 silicon Chemical group 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 229910001961 silver nitrate Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 239000011135 tin Chemical group 0.000 description 3
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 2
- WLKCSMCLEKGITB-MXTKCVSJSA-N 15(R)-HEPE Chemical compound CC\C=C/C[C@@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O WLKCSMCLEKGITB-MXTKCVSJSA-N 0.000 description 2
- LRWYBGFSVUBWMO-UAAZXLHOSA-N 18(R)-HEPE Chemical compound CC[C@@H](O)\C=C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O LRWYBGFSVUBWMO-UAAZXLHOSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 229940114079 arachidonic acid Drugs 0.000 description 2
- 235000021342 arachidonic acid Nutrition 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940125810 compound 20 Drugs 0.000 description 2
- 229940125833 compound 23 Drugs 0.000 description 2
- 229940125961 compound 24 Drugs 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 238000005828 desilylation reaction Methods 0.000 description 2
- 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 2
- 229940079593 drug Drugs 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000007951 isotonicity adjuster Substances 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- UWYKUBJFERKTAF-UHFFFAOYSA-N propa-1,2-dienylboronic acid Chemical class OB(O)C=C=C UWYKUBJFERKTAF-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000006884 silylation reaction Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- QTMVYYCJLZDPHL-ZPUQHVIOSA-N (2e,4e)-5-bromopenta-2,4-dien-1-ol Chemical compound OC\C=C\C=C\Br QTMVYYCJLZDPHL-ZPUQHVIOSA-N 0.000 description 1
- LYKGPRIUUSPHNN-CYBMUJFWSA-N (2r)-2-[tert-butyl(dimethyl)silyl]oxy-5-trimethylsilylpent-4-ynal Chemical compound CC(C)(C)[Si](C)(C)O[C@@H](C=O)CC#C[Si](C)(C)C LYKGPRIUUSPHNN-CYBMUJFWSA-N 0.000 description 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- RXWOHFUULDINMC-UHFFFAOYSA-N 2-(3-nitrothiophen-2-yl)acetic acid Chemical compound OC(=O)CC=1SC=CC=1[N+]([O-])=O RXWOHFUULDINMC-UHFFFAOYSA-N 0.000 description 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- CCDIQUQSSJKISS-UHFFFAOYSA-N 3-bromoprop-1-ene hydrobromide Chemical compound Br.BrCC=C CCDIQUQSSJKISS-UHFFFAOYSA-N 0.000 description 1
- AOPOCGPBAIARAV-UHFFFAOYSA-N 5,12,18-trihydroxyicosa-6,8,10,14,16-pentaenoic acid Chemical compound CCC(O)C=CC=CCC(O)C=CC=CC=CC(O)CCCC(O)=O AOPOCGPBAIARAV-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229910017770 Cu—Ag Inorganic materials 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241001181114 Neta Species 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- 229920001710 Polyorthoester Polymers 0.000 description 1
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 1
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 description 1
- VIHUZWIWUDOHCO-VBDKHZPGSA-N [(4r,5e,7e)-8-bromo-4-[tert-butyl(dimethyl)silyl]oxyocta-5,7-dien-1-ynyl]-trimethylsilane Chemical compound C[Si](C)(C)C#CC[C@@H](O[Si](C)(C)C(C)(C)C)\C=C\C=C\Br VIHUZWIWUDOHCO-VBDKHZPGSA-N 0.000 description 1
- PGTXKIZLOWULDJ-UHFFFAOYSA-N [Mg].[Zn] Chemical compound [Mg].[Zn] PGTXKIZLOWULDJ-UHFFFAOYSA-N 0.000 description 1
- JDHAWWHSIABIDZ-UHFFFAOYSA-N [tert-butyl(dimethyl)silyl]oxy trifluoromethanesulfonate Chemical compound CC(C)(C)[Si](C)(C)OOS(=O)(=O)C(F)(F)F JDHAWWHSIABIDZ-UHFFFAOYSA-N 0.000 description 1
- 239000003070 absorption delaying agent Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 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
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000003833 bile salt Substances 0.000 description 1
- 229940093761 bile salts Drugs 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 229920000249 biocompatible polymer Polymers 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 229940125878 compound 36 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- XEBCWEDRGPSHQH-YUMQZZPRSA-N dipropan-2-yl (2s,3s)-2,3-dihydroxybutanedioate Chemical compound CC(C)OC(=O)[C@@H](O)[C@H](O)C(=O)OC(C)C XEBCWEDRGPSHQH-YUMQZZPRSA-N 0.000 description 1
- 239000002552 dosage form Substances 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
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940079360 enema for constipation Drugs 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- IECPWNUMDGFDKC-MZJAQBGESA-N fusidic acid Chemical class O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C(O)=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C IECPWNUMDGFDKC-MZJAQBGESA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000011905 homologation Methods 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- RGORHHTZBFPFQX-KDBPLMPXSA-N methyl (5s,6z,8e,10e,12r,14z,16e,18r)-5,12,18-trihydroxyicosa-6,8,10,14,16-pentaenoate Chemical compound CC[C@@H](O)\C=C\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(=O)OC RGORHHTZBFPFQX-KDBPLMPXSA-N 0.000 description 1
- IJBLOXLWUHZBNV-YTDQXZNZSA-N methyl (5s,8e,10e,12r)-5,12-bis[[tert-butyl(dimethyl)silyl]oxy]pentadeca-8,10-dien-6,14-diynoate Chemical compound COC(=O)CCC[C@H](O[Si](C)(C)C(C)(C)C)C#C\C=C\C=C\[C@@H](CC#C)O[Si](C)(C)C(C)(C)C IJBLOXLWUHZBNV-YTDQXZNZSA-N 0.000 description 1
- FACURJOXBRSAHH-DOWYHOLBSA-N methyl (5s,8e,10e,12r,16e,18r)-5,12,18-tris[[tert-butyl(dimethyl)silyl]oxy]icosa-8,10,16-trien-6,14-diynoate Chemical compound CC(C)(C)[Si](C)(C)O[C@H](CC)\C=C\C#CC[C@@H](O[Si](C)(C)C(C)(C)C)\C=C\C=C\C#C[C@@H](O[Si](C)(C)C(C)(C)C)CCCC(=O)OC FACURJOXBRSAHH-DOWYHOLBSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000009456 molecular mechanism Effects 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 239000006218 nasal suppository Substances 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 239000004633 polyglycolic acid Substances 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 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
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- MHQWKCPSFOYFQM-AAXQSMANSA-N tert-butyl-[(e,3r)-1-iodopent-1-en-3-yl]oxy-dimethylsilane Chemical compound I/C=C/[C@@H](CC)O[Si](C)(C)C(C)(C)C MHQWKCPSFOYFQM-AAXQSMANSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- STMPXDBGVJZCEX-UHFFFAOYSA-N triethylsilyl trifluoromethanesulfonate Chemical compound CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F STMPXDBGVJZCEX-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
-
- 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)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2012200616A AU2012200616B2 (en) | 2005-03-29 | 2012-02-03 | Trihydroxy polyunsaturated eicosanoid derivatives |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/093,757 | 2005-03-29 | ||
| US11/093,757 US7582785B2 (en) | 2002-04-01 | 2005-03-29 | Trihydroxy polyunsaturated eicosanoid derivatives |
| PCT/US2006/011222 WO2006105058A2 (en) | 2005-03-29 | 2006-03-28 | Trihydroxy polyunsaturated eicosanoid derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2012200616A Division AU2012200616B2 (en) | 2005-03-29 | 2012-02-03 | Trihydroxy polyunsaturated eicosanoid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2006230136A1 AU2006230136A1 (en) | 2006-10-05 |
| AU2006230136B2 true AU2006230136B2 (en) | 2011-11-03 |
Family
ID=36645579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006230136A Ceased AU2006230136B2 (en) | 2005-03-29 | 2006-03-28 | Trihydroxy polyunsaturated eicosanoid derivatives |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7582785B2 (OSRAM) |
| EP (1) | EP1863753B1 (OSRAM) |
| JP (3) | JP2008538117A (OSRAM) |
| CN (1) | CN101203481A (OSRAM) |
| AU (1) | AU2006230136B2 (OSRAM) |
| BR (1) | BRPI0609767A2 (OSRAM) |
| CA (1) | CA2603371C (OSRAM) |
| MX (2) | MX352197B (OSRAM) |
| WO (1) | WO2006105058A2 (OSRAM) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE344226T1 (de) | 2000-02-16 | 2006-11-15 | Brigham & Womens Hospital | Aspirin-ausgelöste lipidmediatoren |
| AU2002365167A1 (en) * | 2001-12-18 | 2003-07-09 | The Brigham And Women's Hospital | Inhibition or prevention of infection by bacteria with epa, dha or analogs |
| US8481772B2 (en) | 2002-04-01 | 2013-07-09 | University Of Southern California | Trihydroxy polyunsaturated eicosanoid derivatives |
| US7902257B2 (en) | 2002-04-01 | 2011-03-08 | University Of Southern California | Trihydroxy polyunsaturated eicosanoid |
| US7582785B2 (en) * | 2002-04-01 | 2009-09-01 | University Of Southern California | Trihydroxy polyunsaturated eicosanoid derivatives |
| 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 |
| EP2216318B1 (en) | 2002-08-12 | 2018-10-10 | Brigham And Women's Hospital | Resolvins: Biotemplates for therapeutic interventions |
| 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 |
| WO2005105025A1 (en) * | 2004-04-14 | 2005-11-10 | Boston University | Methods and compositions for preventing or treating periodontal diseases |
| 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 |
| US20090318394A1 (en) * | 2004-11-19 | 2009-12-24 | Julie Nauroth | Long Chain Polyunsaturated Fatty Acids and Methods of Making and Using the Same |
| NZ555394A (en) * | 2004-11-19 | 2010-07-30 | Martek Biosciences Corp | Oxylipins from long chain polyunsaturated fatty acids including docosapentaenoic acid and docosatetraenoic acid (DPA and DTA) 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 |
| WO2007061783A1 (en) * | 2005-11-18 | 2007-05-31 | Trustees Of Boston University | Treatment and prevention of bone loss using resolvins |
| US20090320148A1 (en) * | 2006-01-31 | 2009-12-24 | Martek Biosciences Corporation | Oxylipins from stearidonic acid and gamma-linolenic acid and methods of making and using the same |
| WO2007127377A2 (en) * | 2006-04-28 | 2007-11-08 | Resolvyx Pharmaceuticals, Inc. | Combinations comprising omega-3 fatty acid compounds for the treatment of cardiovascular disease |
| CA2658361C (en) * | 2006-07-19 | 2013-04-23 | Resolvyx Pharmaceuticals, Inc. | Ophthalmic formulations for the treatment of inflammation |
| EP2131833A2 (en) * | 2006-10-26 | 2009-12-16 | Resolvyx Pharmaceuticals, Inc. | Use of resolvins 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 |
| EP2120920A4 (en) * | 2007-02-20 | 2011-06-15 | Martek Biosciences Corp | OXYLIPINES OF LONG-CHAIN MULTIPLE-UNSATURATED FATTY ACIDS AND METHOD FOR THEIR PREPARATION AND USE |
| AU2008301895A1 (en) * | 2007-09-14 | 2009-03-26 | Resolvyx Pharmaceuticals, Inc. | Oxylipin compounds for treating autoimmune diseases |
| KR20100080798A (ko) * | 2007-10-12 | 2010-07-12 | 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 |
| US8853437B2 (en) | 2009-02-20 | 2014-10-07 | The University Of Tokyo | Anti-inflammatory compounds |
| 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 |
| HRP20230559T1 (hr) | 2012-08-24 | 2023-09-15 | Sun Pharmaceutical Industries Limited | Oftalmička formulacija polioksil lipida ili polioksil masne kiseline i tretman očnih stanja |
| US9770426B2 (en) | 2013-01-11 | 2017-09-26 | Massachusetts Eye And Ear Infirmary | CYP450 lipid metabolites reduce inflammation and angiogenesis |
| WO2014115098A1 (en) * | 2013-01-26 | 2014-07-31 | Mahesh Kandula | Compositions and methods for the treatment of neurological diseases and inflammation |
| KR20170122808A (ko) | 2015-03-10 | 2017-11-06 | 이엘씨 매니지먼트 엘엘씨 | 염증을 해소하도록 피부를 치료하고 해소촉진 경로를 자극하는 활성성분에 대해 스크리닝하기 위한 방법 및 조성물 |
| WO2016149582A1 (en) | 2015-03-18 | 2016-09-22 | The Forsyth Institute | Methods for stabilizing atherosclerotic plaques using lipoxins, resolvins, and analogs thereof |
| ES2974821T3 (es) | 2015-11-10 | 2024-07-01 | Sun Pharmaceutical Ind Ltd | Formulaciones tópicas y usos de las mismas |
| EP3380452B1 (en) * | 2015-11-23 | 2021-03-24 | Retrotope, Inc. | Site-specific isotopic labeling of 1, 4-diene systems |
| WO2017205582A1 (en) | 2016-05-27 | 2017-11-30 | Forsyth Dental Infirmary For Children | Compositions and methods of treating cancer using lipid agonists and receptors thereof |
| US11779910B2 (en) | 2020-02-21 | 2023-10-10 | Biojiva Llc | Processes for isotopic modification of polyunsaturated fatty acids and derivatives thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003084305A2 (en) * | 2002-04-01 | 2003-10-16 | University Of Southern California | Trihydroxy polyunsaturated eicosanoids |
| WO2003105776A2 (en) * | 2002-06-17 | 2003-12-24 | Resolvyx Pharmaceuticals | ANALOGUES OF LIPID MEDIATORS DERIVED FROM OMEGA-3 PUFAs AND METHODS OF USE |
| US20040116408A1 (en) * | 2002-08-12 | 2004-06-17 | Serhan Charles N. | Resolvins: biotemplates for novel therapeutic interventions |
| WO2005089744A2 (en) * | 2004-03-17 | 2005-09-29 | The Brigham And Women's Hospital, Inc. | Use of docosatrienes, resolvins and their stable analogs in the treatment of airway diseases and asthma |
Family Cites Families (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3023A (en) * | 1843-03-30 | peters | ||
| GB2033745B (en) | 1978-05-26 | 1983-08-17 | Wellcome Found | Fatty acid and derivatives thereof for use in treatment or prophylaxis of thromboembolic conditions |
| US4442099A (en) | 1981-11-27 | 1984-04-10 | Research Corporation | Leukotriene analogues |
| US4567290A (en) | 1981-11-27 | 1986-01-28 | Research Corporation | Leukotriene analogues |
| US4576758A (en) | 1984-06-01 | 1986-03-18 | The Upjohn Company | Anti-inflammatory lipoxin B analogs |
| US4759880A (en) | 1984-09-27 | 1988-07-26 | Research Corporation | Alkanoarachidonic acids |
| US4710521A (en) | 1986-07-25 | 1987-12-01 | The Celotex Corporation | Catalyst mixtures for polyisocyanurate foam |
| US5136501A (en) | 1989-05-26 | 1992-08-04 | Reuters Limited | Anonymous matching system |
| CA2082418A1 (en) | 1990-05-07 | 1991-12-28 | Barry I. Bockow | Methods and preparations of stable, deodorized oils and pharmaceutical compositions thereof |
| US5087790A (en) | 1991-06-12 | 1992-02-11 | University Of Southern California | Method for olefination of carbonyl compounds using titanocene derivatives |
| US5177046A (en) | 1991-09-20 | 1993-01-05 | Air Products And Chemicals, Inc. | Amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes |
| US5409955A (en) | 1993-05-13 | 1995-04-25 | Bockow; Barry I. | Compositions and methods for inhibiting uterine contractility |
| US6048897A (en) | 1993-06-15 | 2000-04-11 | Brigham And Women's Hospital | Lipoxin compounds and their use in treating cell proliferative disorders |
| US6030917A (en) | 1996-07-23 | 2000-02-29 | Symyx Technologies, Inc. | Combinatorial synthesis and analysis of organometallic compounds and catalysts |
| US5752238A (en) | 1994-11-03 | 1998-05-12 | Intel Corporation | Consumer-driven electronic information pricing mechanism |
| US5594732A (en) | 1995-03-03 | 1997-01-14 | Intecom, Incorporated | Bridging and signalling subsystems and methods for private and hybrid communications systems including multimedia systems |
| US5801280A (en) | 1995-04-07 | 1998-09-01 | Sumitomo Chemical Company, Limited | Processes for preparing optically active alcohols and optically active amines |
| US5845265A (en) | 1995-04-26 | 1998-12-01 | Mercexchange, L.L.C. | Consignment nodes |
| US5756789A (en) | 1995-06-08 | 1998-05-26 | Texaco, Inc. | Synthesis of metal--containing aluminophosphates with layered structure |
| AU1122997A (en) | 1995-11-07 | 1997-06-11 | Cadis, Inc. | Search engine for remote object oriented database management system |
| US5870717A (en) | 1995-11-13 | 1999-02-09 | International Business Machines Corporation | System for ordering items over computer network using an electronic catalog |
| US5995943A (en) | 1996-04-01 | 1999-11-30 | Sabre Inc. | Information aggregation and synthesization system |
| US5878400A (en) | 1996-06-17 | 1999-03-02 | Trilogy Development Group, Inc. | Method and apparatus for pricing products in multi-level product and organizational groups |
| US5842040A (en) | 1996-06-18 | 1998-11-24 | Storage Technology Corporation | Policy caching method and apparatus for use in a communication device based on contents of one data unit in a subset of related data units |
| WO1998000398A1 (en) | 1996-06-28 | 1998-01-08 | University Of Southern California | Method for the synthesis of amines and amino acids with organoboron derivatives |
| US6602817B1 (en) | 1998-10-23 | 2003-08-05 | University Of Southern California | Combination approach to chiral reagents or catalysts having amine or amino alcohol ligands |
| US5890138A (en) | 1996-08-26 | 1999-03-30 | Bid.Com International Inc. | Computer auction system |
| US5861399A (en) | 1996-07-17 | 1999-01-19 | Heart Care Partners | Methods and compositions for the rapid and enduring relief of inadequate myocardial function |
| US5896379A (en) | 1996-08-26 | 1999-04-20 | Motorola, Inc. | Network node for packet switching with selective data processing and method therefor |
| US5912006A (en) | 1996-08-28 | 1999-06-15 | Eboc, Inc. | Compositions and methods for alleviating discomforting menstrual pain |
| US5946467A (en) | 1996-09-20 | 1999-08-31 | Novell, Inc. | Application-level, persistent packeting apparatus and method |
| US20020055539A1 (en) | 1996-10-02 | 2002-05-09 | Bockow Barry I. | Compositions and methods for treating cardiovascular conditions |
| EP1016009A4 (en) | 1996-10-25 | 2002-06-05 | Ipf Inc | SYSTEM AND METHOD FOR MANAGING AND TRANSMITTING INFORMATION RELATING TO CONSUMER PRODUCTS OVER THE INTERNET |
| JPH10152448A (ja) * | 1996-11-20 | 1998-06-09 | Fuji Photo Film Co Ltd | 不飽和化合物の水素化方法および重水素化方法 |
| WO1998046588A2 (en) | 1997-04-11 | 1998-10-22 | Neorx Corporation | Compounds and therapies for the prevention of vascular and non-vascular pathologies |
| US5878423A (en) | 1997-04-21 | 1999-03-02 | Bellsouth Corporation | Dynamically processing an index to create an ordered set of questions |
| US6006264A (en) | 1997-08-01 | 1999-12-21 | Arrowpoint Communications, Inc. | Method and system for directing a flow between a client and a server |
| US6038668A (en) | 1997-09-08 | 2000-03-14 | Science Applications International Corporation | System, method, and medium for retrieving, organizing, and utilizing networked data |
| US6030715A (en) | 1997-10-09 | 2000-02-29 | The University Of Southern California | Azlactone-related dopants in the emissive layer of an OLED |
| US6259699B1 (en) | 1997-12-30 | 2001-07-10 | Nexabit Networks, Llc | System architecture for and method of processing packets and/or cells in a common switch |
| AU3843999A (en) | 1998-05-07 | 1999-11-23 | Elan Corporation, Plc | Solvent/cosolvent free microemulsion and emulsion preconcentrate drug delivery systems |
| US6377937B1 (en) | 1998-05-28 | 2002-04-23 | Paskowitz Associates | Method and system for more effective communication of characteristics data for products and services |
| US6069109A (en) | 1998-07-01 | 2000-05-30 | Union Carbide Chemicals & Plastics Technology Corporation | Process for the production of half-sandwich transition metal based catalyst precursors |
| US6336138B1 (en) | 1998-08-25 | 2002-01-01 | Hewlett-Packard Company | Template-driven approach for generating models on network services |
| US6336105B1 (en) | 1998-11-16 | 2002-01-01 | Trade Access Inc. | System and method for representing data and providing electronic non-repudiation in a negotiations system |
| DE19855426A1 (de) | 1998-12-02 | 2000-06-08 | Wolfgang Langhoff | Mittel zur Therapie und Prophylaxe von rheumatisch-arthritischen Erkrankungen und zur Prophylaxe von cardiovaskulären Erkrankungen |
| US6272474B1 (en) | 1999-02-08 | 2001-08-07 | Crisostomo B. Garcia | Method for monitoring and trading stocks via the internet displaying bid/ask trade bars |
| US6397212B1 (en) | 1999-03-04 | 2002-05-28 | Peter Biffar | Self-learning and self-personalizing knowledge search engine that delivers holistic results |
| US6427132B1 (en) | 1999-08-31 | 2002-07-30 | Accenture Llp | System, method and article of manufacture for demonstrating E-commerce capabilities via a simulation on a network |
| US6415270B1 (en) | 1999-09-03 | 2002-07-02 | Omnihub, Inc. | Multiple auction coordination method and system |
| ATE344226T1 (de) | 2000-02-16 | 2006-11-15 | Brigham & Womens Hospital | Aspirin-ausgelöste lipidmediatoren |
| DE10049271A1 (de) * | 2000-09-28 | 2002-04-11 | Basf Ag | Verfahren zur katalytischen Reduktion von Alkinverbindungen |
| AU2002365167A1 (en) | 2001-12-18 | 2003-07-09 | The Brigham And Women's Hospital | Inhibition or prevention of infection by bacteria with epa, dha or analogs |
| US7582785B2 (en) | 2002-04-01 | 2009-09-01 | University Of Southern California | Trihydroxy polyunsaturated eicosanoid derivatives |
| 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 |
| US20060293288A1 (en) | 2005-01-07 | 2006-12-28 | Serhan Charles N | Use of resolvins to treat gastrointestinal diseases |
| KR20100080798A (ko) * | 2007-10-12 | 2010-07-12 | 레솔빅스 파마슈티칼즈, 인코퍼레이티드 | 안과 질환의 치료를 위한 옥실리핀 화합물 |
| WO2010039531A1 (en) * | 2008-09-23 | 2010-04-08 | Resolvyx Pharmaceuticals, Inc. | Therapeutic compounds |
| US20120122816A1 (en) * | 2009-02-05 | 2012-05-17 | Resolvyx Pharmaceuticals, Inc. | Compositions and methods for organ preservation |
| TW201039815A (en) * | 2009-04-13 | 2010-11-16 | Resolvyx Pharmaceuticals Inc | Compositions and methods for the treatment of inflammation |
-
2005
- 2005-03-29 US US11/093,757 patent/US7582785B2/en not_active Expired - Fee Related
-
2006
- 2006-03-28 MX MX2014005826A patent/MX352197B/es unknown
- 2006-03-28 BR BRPI0609767-7A patent/BRPI0609767A2/pt not_active Application Discontinuation
- 2006-03-28 AU AU2006230136A patent/AU2006230136B2/en not_active Ceased
- 2006-03-28 EP EP06748789.2A patent/EP1863753B1/en not_active Not-in-force
- 2006-03-28 WO PCT/US2006/011222 patent/WO2006105058A2/en not_active Ceased
- 2006-03-28 CA CA2603371A patent/CA2603371C/en not_active Expired - Fee Related
- 2006-03-28 CN CNA2006800180987A patent/CN101203481A/zh active Pending
- 2006-03-28 MX MX2007012022A patent/MX2007012022A/es active IP Right Grant
- 2006-03-28 JP JP2008504239A patent/JP2008538117A/ja active Pending
-
2012
- 2012-06-05 JP JP2012128022A patent/JP2012162576A/ja active Pending
-
2014
- 2014-03-25 JP JP2014061270A patent/JP2014122240A/ja active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003084305A2 (en) * | 2002-04-01 | 2003-10-16 | University Of Southern California | Trihydroxy polyunsaturated eicosanoids |
| WO2003105776A2 (en) * | 2002-06-17 | 2003-12-24 | Resolvyx Pharmaceuticals | ANALOGUES OF LIPID MEDIATORS DERIVED FROM OMEGA-3 PUFAs AND METHODS OF USE |
| US20040116408A1 (en) * | 2002-08-12 | 2004-06-17 | Serhan Charles N. | Resolvins: biotemplates for novel therapeutic interventions |
| WO2005089744A2 (en) * | 2004-03-17 | 2005-09-29 | The Brigham And Women's Hospital, Inc. | Use of docosatrienes, resolvins and their stable analogs in the treatment of airway diseases and asthma |
Non-Patent Citations (1)
| Title |
|---|
| ARITA et al. Journal of Experimental Medicine, 7 March 2005, vol. 201 (5), pp. 713-722 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2007012022A (es) | 2011-06-16 |
| AU2006230136A1 (en) | 2006-10-05 |
| CA2603371A1 (en) | 2006-10-05 |
| US20050228047A1 (en) | 2005-10-13 |
| CA2603371C (en) | 2013-05-28 |
| JP2008538117A (ja) | 2008-10-09 |
| MX352197B (es) | 2017-11-13 |
| CN101203481A (zh) | 2008-06-18 |
| JP2012162576A (ja) | 2012-08-30 |
| WO2006105058A2 (en) | 2006-10-05 |
| WO2006105058A3 (en) | 2007-04-12 |
| BRPI0609767A2 (pt) | 2010-04-27 |
| JP2014122240A (ja) | 2014-07-03 |
| US7582785B2 (en) | 2009-09-01 |
| EP1863753B1 (en) | 2017-09-20 |
| EP1863753A2 (en) | 2007-12-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2006230136B2 (en) | Trihydroxy polyunsaturated eicosanoid derivatives | |
| EP2022775B1 (en) | Trihydroxy polyunsaturated eicosanoids | |
| US8461201B2 (en) | Trihydroxy polyunsaturated eicosanoid derivatives | |
| CN1157818A (zh) | 1α，26-二羟基-D-高维生素D3 | |
| TWI541227B (zh) | 乙烯基硼化合物至２－取代－４－氧基－環戊－２－烯－１－酮的金屬催化不對稱１，４－共軛加成產生前列腺素和前列腺素類似物 | |
| AU2012200616B2 (en) | Trihydroxy polyunsaturated eicosanoid derivatives | |
| US8802874B2 (en) | Trihydroxy polyunsaturated eicosanoid derivatives | |
| US20250288549A1 (en) | Synthetic process for production of lipoxin b4 and analogues thereof | |
| HK1122791A (en) | Trihydroxy polyunsaturated eicosanoid derivatives | |
| Zhu | Total Synthesis of Specialized Pro-Resolving Lipid Mediators and Their Analogs | |
| USRE43038E1 (en) | Compound having antitumor activity and process for producing the same | |
| Zhang | The Total Synthesis of () 7-HDHA | |
| Hasselstrøm | Synthetic efforts towards an analog of the SPM PD1n-3 DPA | |
| Yang | Synthetic studies of new lipid mediators | |
| CN104812386A (zh) | 治疗的化合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period | ||
| NB | Applications allowed - extensions of time section 223(2) |
Free format text: THE TIME IN WHICH TO REQUEST EXAMINATION HAS BEEN EXTENDED TO 18 MAR 2010. |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |