JP2008538117A - トリヒドロキシポリ不飽和エイコサノイド誘導体 - Google Patents
トリヒドロキシポリ不飽和エイコサノイド誘導体 Download PDFInfo
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- JP2008538117A JP2008538117A JP2008504239A JP2008504239A JP2008538117A JP 2008538117 A JP2008538117 A JP 2008538117A JP 2008504239 A JP2008504239 A JP 2008504239A JP 2008504239 A JP2008504239 A JP 2008504239A JP 2008538117 A JP2008538117 A JP 2008538117A
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- aryl
- compound
- alkyl
- heteroaryl
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- 150000002066 eicosanoids Chemical class 0.000 title abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 85
- 238000002360 preparation method Methods 0.000 claims abstract description 19
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 14
- 201000011510 cancer Diseases 0.000 claims abstract description 14
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
- 230000002159 abnormal effect Effects 0.000 claims abstract description 13
- 230000028709 inflammatory response Effects 0.000 claims abstract description 13
- 230000008569 process Effects 0.000 claims abstract description 12
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 11
- 230000004663 cell proliferation Effects 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 130
- 125000003118 aryl group Chemical group 0.000 claims description 124
- 125000000217 alkyl group Chemical group 0.000 claims description 110
- 125000001072 heteroaryl group Chemical group 0.000 claims description 94
- 229910052739 hydrogen Inorganic materials 0.000 claims description 87
- 239000001257 hydrogen Substances 0.000 claims description 87
- 150000002431 hydrogen Chemical class 0.000 claims description 80
- 125000003545 alkoxy group Chemical group 0.000 claims description 77
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 63
- 238000010168 coupling process Methods 0.000 claims description 53
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 52
- 125000004104 aryloxy group Chemical group 0.000 claims description 46
- 125000003282 alkyl amino group Chemical group 0.000 claims description 41
- -1 bell Chemical compound 0.000 claims description 39
- 239000011701 zinc Substances 0.000 claims description 38
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 37
- 239000011737 fluorine Substances 0.000 claims description 37
- 229910052731 fluorine Inorganic materials 0.000 claims description 37
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
- 238000005859 coupling reaction Methods 0.000 claims description 35
- 229910052725 zinc Inorganic materials 0.000 claims description 35
- 230000008878 coupling Effects 0.000 claims description 34
- 239000011777 magnesium Substances 0.000 claims description 31
- 229910052749 magnesium Inorganic materials 0.000 claims description 31
- 239000000460 chlorine Substances 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 125000005256 alkoxyacyl group Chemical group 0.000 claims description 28
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 28
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 27
- 125000002252 acyl group Chemical group 0.000 claims description 27
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 27
- 229910052700 potassium Inorganic materials 0.000 claims description 27
- 239000011734 sodium Substances 0.000 claims description 27
- 229910052708 sodium Inorganic materials 0.000 claims description 27
- 229910052794 bromium Inorganic materials 0.000 claims description 26
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 150000001768 cations Chemical class 0.000 claims description 17
- 238000005984 hydrogenation reaction Methods 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 125000004442 acylamino group Chemical group 0.000 claims description 15
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 12
- 150000003751 zinc Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 150000001345 alkine derivatives Chemical class 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- 150000003857 carboxamides Chemical class 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 8
- 125000004437 phosphorous atom Chemical group 0.000 claims description 8
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 8
- 125000005035 acylthio group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000001879 copper Chemical class 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 239000011981 lindlar catalyst Substances 0.000 claims description 6
- 238000005828 desilylation reaction Methods 0.000 claims description 5
- 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 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004112 carboxyamino group Chemical group [H]OC(=O)N([H])[*] 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 238000006317 isomerization reaction Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 claims 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 claims 4
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 3
- 239000003125 aqueous solvent Substances 0.000 claims 3
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims 1
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 claims 1
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 claims 1
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 claims 1
- 229940127007 Compound 39 Drugs 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 229940126540 compound 41 Drugs 0.000 claims 1
- 229940125936 compound 42 Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 29
- 206010061218 Inflammation Diseases 0.000 abstract description 9
- 230000004054 inflammatory process Effects 0.000 abstract description 9
- 208000023275 Autoimmune disease Diseases 0.000 abstract description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 abstract description 5
- 230000002265 prevention Effects 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 239000000543 intermediate Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 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
- 239000002243 precursor Substances 0.000 description 15
- 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
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000005647 linker group Chemical group 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000001225 therapeutic effect Effects 0.000 description 10
- 125000002947 alkylene group Chemical group 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 8
- 235000020777 polyunsaturated fatty acids Nutrition 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
- 229940126543 compound 14 Drugs 0.000 description 7
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- 239000007788 liquid Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
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- 239000012267 brine Substances 0.000 description 6
- 229940126214 compound 3 Drugs 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 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
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 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
- JOOXPROVXQFFEQ-UHFFFAOYSA-N C(CCCCC(CC=CC=CCCC(C)=O)=O)(=O)OO[Si](C)(C)C(C)(C)C Chemical compound C(CCCCC(CC=CC=CCCC(C)=O)=O)(=O)OO[Si](C)(C)C(C)(C)C JOOXPROVXQFFEQ-UHFFFAOYSA-N 0.000 description 4
- 0 C=CC=C[C@](CC#C)C(C1C2)C1C2C(CC*1)C1C1C(CCCCC2CC2)=CC1 Chemical compound C=CC=C[C@](CC#C)C(C1C2)C1C2C(CC*1)C1C1C(CCCCC2CC2)=CC1 0.000 description 4
- 229910021595 Copper(I) iodide Inorganic materials 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
- 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
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- 150000002632 lipids Chemical class 0.000 description 4
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- 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
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- 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 compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 125000005282 allenyl group Chemical group 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
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- 150000001721 carbon Chemical group 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Heart & Thoracic Surgery (AREA)
- Cardiology (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)
Applications Claiming Priority (2)
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| 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 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2012128022A Division JP2012162576A (ja) | 2005-03-29 | 2012-06-05 | トリヒドロキシポリ不飽和エイコサノイド誘導体 |
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| JP2014061270A Pending JP2014122240A (ja) | 2005-03-29 | 2014-03-25 | トリヒドロキシポリ不飽和エイコサノイド誘導体 |
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| EP (1) | EP1863753B1 (enExample) |
| JP (3) | JP2008538117A (enExample) |
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| CA (1) | CA2603371C (enExample) |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011500568A (ja) * | 2007-10-12 | 2011-01-06 | リゾルヴィクス・ファーマシューティカルズ・インコーポレイテッド | 眼病治療のための組成物及び方法 |
| JP2011184408A (ja) * | 2010-03-10 | 2011-09-22 | Japan Science & Technology Agency | 水系溶媒中での含窒素化合物の製造方法 |
| JP2012162576A (ja) * | 2005-03-29 | 2012-08-30 | Univ Of Southern California | トリヒドロキシポリ不飽和エイコサノイド誘導体 |
| JP2012523459A (ja) * | 2009-04-13 | 2012-10-04 | シー．ティー．リゾルブ サール | 炎症を処置するための組成物及び方法 |
| JP2022046501A (ja) * | 2015-11-23 | 2022-03-23 | レトロトップ、 インコーポレイテッド | １，４－ジエン系の部位特異的同位体標識 |
| US11779910B2 (en) | 2020-02-21 | 2023-10-10 | Biojiva Llc | Processes for isotopic modification of polyunsaturated fatty acids and derivatives thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| IL151299A0 (en) * | 2000-02-16 | 2003-04-10 | Brigham & Womens Hospital | Aspirin-triggered lipid mediators |
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| US8481772B2 (en) | 2002-04-01 | 2013-07-09 | University Of Southern California | Trihydroxy polyunsaturated eicosanoid derivatives |
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| EP1755537A4 (en) * | 2004-04-14 | 2009-12-09 | Univ Boston | METHOD AND COMPOSITIONS FOR PREVENTING OR TREATING PERIODONTOPATHIA |
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| WO2007090162A2 (en) * | 2006-01-31 | 2007-08-09 | Martek Biosciences Corporation | OXYLIPINS FROM STEARIDONIC ACID AND γ-LINOLENIC ACID AND METHODS OF MAKING AND USING THE SAME |
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| JP2012162576A (ja) * | 2005-03-29 | 2012-08-30 | Univ Of Southern California | トリヒドロキシポリ不飽和エイコサノイド誘導体 |
| JP2011500568A (ja) * | 2007-10-12 | 2011-01-06 | リゾルヴィクス・ファーマシューティカルズ・インコーポレイテッド | 眼病治療のための組成物及び方法 |
| JP2014037437A (ja) * | 2007-10-12 | 2014-02-27 | Resolvyx Pharmaceuticals Inc | 眼病治療のための組成物及び方法 |
| JP2012523459A (ja) * | 2009-04-13 | 2012-10-04 | シー．ティー．リゾルブ サール | 炎症を処置するための組成物及び方法 |
| JP2011184408A (ja) * | 2010-03-10 | 2011-09-22 | Japan Science & Technology Agency | 水系溶媒中での含窒素化合物の製造方法 |
| JP2022046501A (ja) * | 2015-11-23 | 2022-03-23 | レトロトップ、 インコーポレイテッド | １，４－ジエン系の部位特異的同位体標識 |
| JP7355801B2 (ja) | 2015-11-23 | 2023-10-03 | レトロトップ、 インコーポレイテッド | １，４－ジエン系の部位特異的同位体標識 |
| US12060324B2 (en) | 2015-11-23 | 2024-08-13 | Biojiva Llc | Site-specific isotopic labeling of 1,4-diene systems |
| US11779910B2 (en) | 2020-02-21 | 2023-10-10 | Biojiva Llc | Processes for isotopic modification of polyunsaturated fatty acids and derivatives thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0609767A2 (pt) | 2010-04-27 |
| EP1863753B1 (en) | 2017-09-20 |
| MX352197B (es) | 2017-11-13 |
| WO2006105058A3 (en) | 2007-04-12 |
| JP2012162576A (ja) | 2012-08-30 |
| CN101203481A (zh) | 2008-06-18 |
| MX2007012022A (es) | 2011-06-16 |
| EP1863753A2 (en) | 2007-12-12 |
| CA2603371A1 (en) | 2006-10-05 |
| US7582785B2 (en) | 2009-09-01 |
| JP2014122240A (ja) | 2014-07-03 |
| US20050228047A1 (en) | 2005-10-13 |
| WO2006105058A2 (en) | 2006-10-05 |
| AU2006230136B2 (en) | 2011-11-03 |
| AU2006230136A1 (en) | 2006-10-05 |
| CA2603371C (en) | 2013-05-28 |
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