NO332411B1 - Fremgangsmate for fremstilling av 1,3-difenylprop-2-en-1-on-derivater - Google Patents
Fremgangsmate for fremstilling av 1,3-difenylprop-2-en-1-on-derivater Download PDFInfo
- Publication number
- NO332411B1 NO332411B1 NO20060087A NO20060087A NO332411B1 NO 332411 B1 NO332411 B1 NO 332411B1 NO 20060087 A NO20060087 A NO 20060087A NO 20060087 A NO20060087 A NO 20060087A NO 332411 B1 NO332411 B1 NO 332411B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- compound
- substituted
- diphenylprop
- tert
- Prior art date
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- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical class C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 238000000034 method Methods 0.000 claims abstract description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 20
- -1 thionitroso group Chemical group 0.000 claims description 19
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 238000005882 aldol condensation reaction Methods 0.000 claims description 5
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 5
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 238000007792 addition Methods 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- QFMNMSJTKVHTSY-UHFFFAOYSA-N 1-phenylethanethione Chemical compound CC(=S)C1=CC=CC=C1 QFMNMSJTKVHTSY-UHFFFAOYSA-N 0.000 claims description 2
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical class OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 claims description 2
- 125000005130 alkyl carbonyl thio group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 2
- ACOOSTZBTYEGER-UHFFFAOYSA-N thiobenzaldehyde Chemical compound S=CC1=CC=CC=C1 ACOOSTZBTYEGER-UHFFFAOYSA-N 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 33
- DQFBYFPFKXHELB-UHFFFAOYSA-N chalcone Chemical group C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 abstract description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- 238000010898 silica gel chromatography Methods 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000007429 general method Methods 0.000 description 18
- 238000000746 purification Methods 0.000 description 18
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 14
- UYGBSRJODQHNLQ-UHFFFAOYSA-N 4-hydroxy-3,5-dimethylbenzaldehyde Chemical compound CC1=CC(C=O)=CC(C)=C1O UYGBSRJODQHNLQ-UHFFFAOYSA-N 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000012707 chemical precursor Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- IGVNJALYNQVQIT-UHFFFAOYSA-N tert-butyl 2-bromo-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)Br IGVNJALYNQVQIT-UHFFFAOYSA-N 0.000 description 9
- BZLYUDJOVAMKIB-UHFFFAOYSA-N 2-hydroxy-1,3-diphenylprop-2-en-1-one Chemical compound C=1C=CC=CC=1C(=O)C(O)=CC1=CC=CC=C1 BZLYUDJOVAMKIB-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000007738 vacuum evaporation Methods 0.000 description 6
- PHRSDLZWVTXEOY-RUDMXATFSA-N (e)-3-(4-hydroxy-3,5-dimethylphenyl)-1-(4-methylsulfanylphenyl)prop-2-en-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)\C=C\C1=CC(C)=C(O)C(C)=C1 PHRSDLZWVTXEOY-RUDMXATFSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- VHLOANBRCFGJQF-UHFFFAOYSA-N tert-butyl 2,6-dimethyl-4-[3-(4-methylsulfanylphenyl)-3-oxoprop-1-enyl]-3-propan-2-yloxybenzoate Chemical compound CSC1=CC=C(C=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)OC(C)(C)C)C)OC(C)C)=O VHLOANBRCFGJQF-UHFFFAOYSA-N 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- 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 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- KTNCXTLDIMCSPC-UHFFFAOYSA-N 1-(4-bromophenyl)-3-(4-hydroxy-3,5-dimethylphenyl)prop-2-en-1-one Chemical compound CC1=C(O)C(C)=CC(C=CC(=O)C=2C=CC(Br)=CC=2)=C1 KTNCXTLDIMCSPC-UHFFFAOYSA-N 0.000 description 2
- IDNZQWAOIWOIKU-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(4-hydroxy-3,5-dimethylphenyl)prop-2-en-1-one Chemical compound CC1=C(O)C(C)=CC(C=CC(=O)C=2C=CC(Cl)=CC=2)=C1 IDNZQWAOIWOIKU-UHFFFAOYSA-N 0.000 description 2
- HYOULSUKZMZLCA-UHFFFAOYSA-N 1-(4-hexoxyphenyl)-3-(4-hydroxy-3,5-dimethylphenyl)prop-2-en-1-one Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)C=CC1=CC(C)=C(O)C(C)=C1 HYOULSUKZMZLCA-UHFFFAOYSA-N 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940126543 compound 14 Drugs 0.000 description 2
- 229940126142 compound 16 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PQAPZPBWWMAMNQ-UHFFFAOYSA-N tert-butyl 4-[3-(2-methoxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoate Chemical compound COC1=C(C=CC=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)OC(C)(C)C)C)OC(C)C)=O PQAPZPBWWMAMNQ-UHFFFAOYSA-N 0.000 description 2
- UAYFKWJMLFSUQX-UHFFFAOYSA-N tert-butyl 4-[3-(4-bromophenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoate Chemical compound BrC1=CC=C(C=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)OC(C)(C)C)C)OC(C)C)=O UAYFKWJMLFSUQX-UHFFFAOYSA-N 0.000 description 2
- NXLNJFKRZXNAOC-UHFFFAOYSA-N tert-butyl 4-[3-(4-chloro-2-methoxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoate Chemical compound COC1=C(C=CC(=C1)Cl)C(C=CC1=C(C(=C(C(=C1)C)C(=O)OC(C)(C)C)C)OC(C)C)=O NXLNJFKRZXNAOC-UHFFFAOYSA-N 0.000 description 2
- UVYOKRBWZAUPRA-UHFFFAOYSA-N tert-butyl 4-[3-(4-hexoxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoate Chemical compound C(CCCCC)OC1=CC=C(C=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)OC(C)(C)C)C)OC(C)C)=O UVYOKRBWZAUPRA-UHFFFAOYSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-UHFFFAOYSA-N 0.000 description 1
- KBZYKWXKOWQIOQ-UHFFFAOYSA-N 1-(4-chloro-2-methoxyphenyl)-3-(4-hydroxy-3,5-dimethyl-2-propan-2-yloxyphenyl)prop-2-en-1-one Chemical compound COC1=C(C=CC(=C1)Cl)C(C=CC1=C(C(=C(C(=C1)C)O)C)OC(C)C)=O KBZYKWXKOWQIOQ-UHFFFAOYSA-N 0.000 description 1
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- JECUZQLBQKNEMW-UHFFFAOYSA-N 1-(4-methylsulfanylphenyl)ethanone Chemical compound CSC1=CC=C(C(C)=O)C=C1 JECUZQLBQKNEMW-UHFFFAOYSA-N 0.000 description 1
- GKDRHFHWMMGOHF-UHFFFAOYSA-N 2-hexan-3-yloxy-1-phenylethanone Chemical compound CCCC(CC)OCC(=O)C1=CC=CC=C1 GKDRHFHWMMGOHF-UHFFFAOYSA-N 0.000 description 1
- YRNDGUSDBCARGC-UHFFFAOYSA-N 2-methoxyacetophenone Chemical compound COCC(=O)C1=CC=CC=C1 YRNDGUSDBCARGC-UHFFFAOYSA-N 0.000 description 1
- ZMUPDKKJNALSOB-UHFFFAOYSA-N 3-(4-hydroxy-3,5-dimethylphenyl)-1-(2-methoxyphenyl)prop-2-en-1-one Chemical compound COC1=CC=CC=C1C(=O)C=CC1=CC(C)=C(O)C(C)=C1 ZMUPDKKJNALSOB-UHFFFAOYSA-N 0.000 description 1
- DBJLTPPYJLSWMX-UHFFFAOYSA-N 3-(4-hydroxy-3,5-dimethylphenyl)prop-2-enal Chemical compound CC1=CC(C=CC=O)=CC(C)=C1O DBJLTPPYJLSWMX-UHFFFAOYSA-N 0.000 description 1
- SHOKWHLEACINRX-UHFFFAOYSA-N 4-[3-(2-methoxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoic acid Chemical compound COC1=C(C=CC=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)O)C)OC(C)C)=O SHOKWHLEACINRX-UHFFFAOYSA-N 0.000 description 1
- CFMGACOOXDRGTH-UHFFFAOYSA-N 4-[3-(4-bromophenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoic acid Chemical compound BrC1=CC=C(C=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)O)C)OC(C)C)=O CFMGACOOXDRGTH-UHFFFAOYSA-N 0.000 description 1
- KTIRWVUQFYPEMT-UHFFFAOYSA-N 4-[3-(4-chloro-2-methoxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoic acid Chemical compound COC1=C(C=CC(=C1)Cl)C(C=CC1=C(C(=C(C(=C1)C)C(=O)O)C)OC(C)C)=O KTIRWVUQFYPEMT-UHFFFAOYSA-N 0.000 description 1
- WFGYKQQMHKGWGK-UHFFFAOYSA-N 4-[3-(4-hexoxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoic acid Chemical compound C(CCCCC)OC1=CC=C(C=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)O)C)OC(C)C)=O WFGYKQQMHKGWGK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
- OPAXADMAZRWQED-UHFFFAOYSA-N COC1=C(C)C(C(O)=O)=C(C)C=C1C=CC(=O)C1=CC(C)=CS1 Chemical compound COC1=C(C)C(C(O)=O)=C(C)C=C1C=CC(=O)C1=CC(C)=CS1 OPAXADMAZRWQED-UHFFFAOYSA-N 0.000 description 1
- QDMONAIGPRKTII-UHFFFAOYSA-N CSc1ccc(cc1)C(=O)C=Cc1cc(C)c(C(=O)OC(C)C)c(C)c1OC(C)C Chemical compound CSc1ccc(cc1)C(=O)C=Cc1cc(C)c(C(=O)OC(C)C)c(C)c1OC(C)C QDMONAIGPRKTII-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 101100258328 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-2 gene Proteins 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 208000035269 cancer or benign tumor Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000009759 skin aging Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- VCZDPYZOAFJZBZ-UHFFFAOYSA-N tert-butyl 4-[3-(4-chlorophenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoate Chemical compound CC(C)Oc1c(C)c(C(=O)OC(C)(C)C)c(C)cc1C=CC(=O)c1ccc(Cl)cc1 VCZDPYZOAFJZBZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- 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
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
- C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0308354A FR2857361B1 (fr) | 2003-07-08 | 2003-07-08 | PREPARATION DE DERIVES DE 1,3-DIPHENYPROP-2-¼n-1-one |
| PCT/FR2004/001797 WO2005005369A1 (fr) | 2003-07-08 | 2004-07-08 | Preparation de derives de 1,3-diphenylprop-2-en-1-one |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20060087L NO20060087L (no) | 2006-02-07 |
| NO332411B1 true NO332411B1 (no) | 2012-09-17 |
Family
ID=33522868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20060087A NO332411B1 (no) | 2003-07-08 | 2006-01-06 | Fremgangsmate for fremstilling av 1,3-difenylprop-2-en-1-on-derivater |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US7385082B2 (zh) |
| EP (1) | EP1644312B1 (zh) |
| JP (1) | JP2007516189A (zh) |
| KR (1) | KR20060030110A (zh) |
| CN (1) | CN1819986B (zh) |
| AT (1) | ATE468317T1 (zh) |
| AU (1) | AU2004255905B2 (zh) |
| BR (1) | BRPI0412370A (zh) |
| CA (1) | CA2531443C (zh) |
| DE (1) | DE602004027251D1 (zh) |
| DK (1) | DK1644312T3 (zh) |
| EA (1) | EA010410B1 (zh) |
| ES (1) | ES2343803T3 (zh) |
| FR (1) | FR2857361B1 (zh) |
| IL (1) | IL172825A (zh) |
| MX (1) | MXPA06000159A (zh) |
| NO (1) | NO332411B1 (zh) |
| NZ (1) | NZ544792A (zh) |
| PL (1) | PL213226B1 (zh) |
| SG (1) | SG129448A1 (zh) |
| WO (1) | WO2005005369A1 (zh) |
| ZA (1) | ZA200601040B (zh) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2841900B1 (fr) * | 2002-07-08 | 2007-03-02 | Genfit S A | Nouveaux derives de 1,3-diphenylprop-2-en-1-one substitues, preparation et utilisations |
| FR2841784B1 (fr) | 2002-07-08 | 2007-03-02 | Composition a base de derives de 1,3-diphenylprop-2en-1-one substitues, preparation et utilisations | |
| CN102647982B (zh) | 2009-11-26 | 2014-10-15 | 基恩菲特公司 | 使用1,3-二苯基丙-2-烯-1-酮衍生物治疗肝脏疾患 |
| WO2011080276A1 (en) | 2009-12-29 | 2011-07-07 | Genfit | Pharmaceutical combinations comprising a dpp-4 inhibitor and a 1,3-diphenylprop-2-en-1-one derivative |
| HUE035810T2 (en) | 2010-05-17 | 2018-05-28 | Genfit | An improved method for producing chalcone derivatives |
| EP2948137B1 (en) * | 2013-01-18 | 2018-11-14 | Genfit | Methods of treatment of fibrosis and cancers |
| EP3416629A4 (en) | 2016-02-16 | 2019-08-07 | CoNCERT Pharmaceuticals, Inc. | DEUTERATED GFT-505 |
| CN106674069B (zh) * | 2016-12-06 | 2018-05-11 | 上海博志研新药物技术有限公司 | Gft505及其中间体的制备方法 |
| CA3051146A1 (en) * | 2017-01-22 | 2018-07-26 | Crystal Pharmaceutical (Suzhou) Co., Ltd. | Crystal form of gft-505 and preparation method and use thereof |
| WO2018153933A1 (en) | 2017-02-21 | 2018-08-30 | Genfit | Combination of a ppar agonist with a fxr agonist |
| CA3071202A1 (en) | 2017-08-04 | 2019-02-07 | Advitech Advisory And Technologies Sa | Process for the preparation of elafibranor and novel synthesis intermediates |
| EP3710425A1 (en) | 2017-11-16 | 2020-09-23 | Teva Pharmaceuticals International GmbH | Solid state forms of elafibranor |
| CN109608318A (zh) * | 2019-01-31 | 2019-04-12 | 上海生农生化制品股份有限公司 | 一种戊唑醇中间体α的工业合成方法 |
| CN110156648A (zh) * | 2019-05-30 | 2019-08-23 | 河北科技大学 | 一种Elafibranor中间体的制备方法 |
| CN110143902B (zh) * | 2019-06-12 | 2021-06-04 | 天津科技大学 | 含硒查尔酮衍生物Compound 1和合成方法及在抗非酒精性脂肪肝炎药物中的应用 |
| CN110143890B (zh) * | 2019-06-12 | 2020-12-22 | 天津科技大学 | 一种查尔酮衍生物和合成方法及其在制备抗非酒精性脂肪肝炎药物中的应用 |
| US20230008367A1 (en) | 2019-09-26 | 2023-01-12 | Abionyx Pharma Sa | Compounds useful for treating liver diseases |
| CN113121394B (zh) * | 2019-12-30 | 2022-11-08 | 中国药科大学 | 一种苯氧乙酸类衍生物的制备方法 |
| AU2021275381A1 (en) | 2020-05-18 | 2022-11-24 | Genfit | Elafibranor for the treatment of primary sclerosing cholangitis |
| MX2023002159A (es) | 2020-08-26 | 2023-03-01 | Genfit | Composiciones y metodos para el tratamiento de la colangitis biliar primaria. |
| WO2022189856A1 (en) | 2021-03-08 | 2022-09-15 | Abionyx Pharma Sa | Compounds useful for treating liver diseases |
| CN113230240B (zh) * | 2021-03-22 | 2022-12-27 | 广州医科大学 | 1,3-二苯基丙-2-烯-1-酮衍生物及其应用 |
| WO2022238448A1 (en) | 2021-05-11 | 2022-11-17 | Genfit | Elafibranor derivatives agonists of ppar for use in the treatment of sepsis |
| WO2022238450A1 (en) | 2021-05-11 | 2022-11-17 | Genfit | Ppar-agonists for use in the treatment of liver failure |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2359621C2 (de) * | 1973-11-30 | 1982-11-18 | Hoechst Ag, 6000 Frankfurt | Antiviral wirksame Alkalimetall- oder Ammoniumsalze der Polyacrylsäure |
| GB8426424D0 (en) * | 1984-10-19 | 1984-11-28 | Biorex Laboratories Ltd | Chalcone derivatives |
| JPH023670A (ja) * | 1988-06-22 | 1990-01-09 | Nippon Oil & Fats Co Ltd | アルキルチオカルコン誘導体 |
| JPH05255655A (ja) * | 1992-03-12 | 1993-10-05 | Kanebo Ltd | 紫外線吸収剤 |
| US5523302A (en) * | 1993-11-24 | 1996-06-04 | The Du Pont Merck Pharmaceutical Company | Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists |
| EP0947511A1 (en) * | 1998-03-30 | 1999-10-06 | F. Hoffmann-La Roche Ag | Derivatives of phenoxy acetic acid and of phenoxymethyl tetrazole having antitumor activity |
| JPH11302243A (ja) * | 1998-04-24 | 1999-11-02 | Mitsubishi Chemical Corp | ジエチレントリアミン５酢酸誘導体 |
-
2003
- 2003-07-08 FR FR0308354A patent/FR2857361B1/fr not_active Expired - Fee Related
-
2004
- 2004-07-08 EA EA200600197A patent/EA010410B1/ru not_active IP Right Cessation
- 2004-07-08 PL PL379543A patent/PL213226B1/pl unknown
- 2004-07-08 ES ES04767629T patent/ES2343803T3/es active Active
- 2004-07-08 US US10/563,057 patent/US7385082B2/en active Active
- 2004-07-08 MX MXPA06000159A patent/MXPA06000159A/es active IP Right Grant
- 2004-07-08 WO PCT/FR2004/001797 patent/WO2005005369A1/fr active Application Filing
- 2004-07-08 DE DE602004027251T patent/DE602004027251D1/de active Active
- 2004-07-08 NZ NZ544792A patent/NZ544792A/en not_active IP Right Cessation
- 2004-07-08 AU AU2004255905A patent/AU2004255905B2/en not_active Ceased
- 2004-07-08 CN CN2004800195644A patent/CN1819986B/zh active Active
- 2004-07-08 CA CA2531443A patent/CA2531443C/fr not_active Expired - Fee Related
- 2004-07-08 EP EP04767629A patent/EP1644312B1/fr active Active
- 2004-07-08 BR BRPI0412370-0A patent/BRPI0412370A/pt not_active Application Discontinuation
- 2004-07-08 KR KR1020067000562A patent/KR20060030110A/ko not_active Application Discontinuation
- 2004-07-08 DK DK04767629.1T patent/DK1644312T3/da active
- 2004-07-08 AT AT04767629T patent/ATE468317T1/de active
- 2004-07-08 SG SG200700644A patent/SG129448A1/en unknown
- 2004-07-08 JP JP2006518300A patent/JP2007516189A/ja active Pending
-
2005
- 2005-12-26 IL IL172825A patent/IL172825A/en unknown
-
2006
- 2006-01-06 NO NO20060087A patent/NO332411B1/no not_active IP Right Cessation
- 2006-02-06 ZA ZA200601040A patent/ZA200601040B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005005369A1 (fr) | 2005-01-20 |
| CN1819986A (zh) | 2006-08-16 |
| JP2007516189A (ja) | 2007-06-21 |
| FR2857361B1 (fr) | 2005-09-09 |
| EP1644312A1 (fr) | 2006-04-12 |
| KR20060030110A (ko) | 2006-04-07 |
| AU2004255905B2 (en) | 2010-11-18 |
| DE602004027251D1 (de) | 2010-07-01 |
| CN1819986B (zh) | 2011-02-02 |
| EP1644312B1 (fr) | 2010-05-19 |
| CA2531443C (fr) | 2012-05-01 |
| AU2004255905A1 (en) | 2005-01-20 |
| IL172825A0 (en) | 2006-06-11 |
| EA200600197A1 (ru) | 2006-06-30 |
| NZ544792A (en) | 2009-02-28 |
| CA2531443A1 (fr) | 2005-01-20 |
| SG129448A1 (en) | 2007-02-26 |
| MXPA06000159A (es) | 2006-03-21 |
| FR2857361A1 (fr) | 2005-01-14 |
| US20060142611A1 (en) | 2006-06-29 |
| ATE468317T1 (de) | 2010-06-15 |
| ES2343803T3 (es) | 2010-08-10 |
| DK1644312T3 (da) | 2010-08-23 |
| ZA200601040B (en) | 2007-05-30 |
| NO20060087L (no) | 2006-02-07 |
| US7385082B2 (en) | 2008-06-10 |
| PL213226B1 (pl) | 2013-01-31 |
| EA010410B1 (ru) | 2008-08-29 |
| IL172825A (en) | 2010-11-30 |
| PL379543A1 (pl) | 2006-10-02 |
| BRPI0412370A (pt) | 2006-09-05 |
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