ZA200510137B - Novel aminobenzophenone compounds - Google Patents
Novel aminobenzophenone compounds Download PDFInfo
- Publication number
- ZA200510137B ZA200510137B ZA200510137A ZA200510137A ZA200510137B ZA 200510137 B ZA200510137 B ZA 200510137B ZA 200510137 A ZA200510137 A ZA 200510137A ZA 200510137 A ZA200510137 A ZA 200510137A ZA 200510137 B ZA200510137 B ZA 200510137B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- chloro
- phenylamino
- methyl
- phenyl
- Prior art date
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- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 408
- -1 hydroxy, mercapto Chemical class 0.000 claims description 112
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 230000001131 transforming effect Effects 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 11
- 125000001246 bromo group Chemical group Br* 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 239000012634 fragment Substances 0.000 claims description 8
- 208000027866 inflammatory disease Diseases 0.000 claims description 8
- 125000002524 organometallic group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 230000002757 inflammatory effect Effects 0.000 claims description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- ZABMHLDQFJHDSC-UHFFFAOYSA-N 2,3-dihydro-1,3-oxazole Chemical compound C1NC=CO1 ZABMHLDQFJHDSC-UHFFFAOYSA-N 0.000 claims description 2
- KTGIBLRIUZHZAA-UHFFFAOYSA-N 2-[[3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-4-methylbenzoyl]amino]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)F)=CC=2)Cl)=C1 KTGIBLRIUZHZAA-UHFFFAOYSA-N 0.000 claims description 2
- PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims description 2
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 claims description 2
- LXOSPZGRIOERRZ-UHFFFAOYSA-N 3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-4-methyl-n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)F)=CC=2)Cl)=C1 LXOSPZGRIOERRZ-UHFFFAOYSA-N 0.000 claims description 2
- SBTIWZSOKRDDRA-UHFFFAOYSA-N 3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-n,4-dimethylbenzamide Chemical compound CNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)F)=CC=2)Cl)=C1 SBTIWZSOKRDDRA-UHFFFAOYSA-N 0.000 claims description 2
- YDXKBKBLZDYNGS-UHFFFAOYSA-N 3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-n-(2-hydroxyethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Cl)C=C1F YDXKBKBLZDYNGS-UHFFFAOYSA-N 0.000 claims description 2
- BYYIDGKWOKCMFR-UHFFFAOYSA-N 3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-n-(2-methoxyethyl)-4-methylbenzamide Chemical compound COCCNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)F)=CC=2)Cl)=C1 BYYIDGKWOKCMFR-UHFFFAOYSA-N 0.000 claims description 2
- FVEDXXPVSCVQFB-UHFFFAOYSA-N 3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-n-[2-(dimethylamino)ethyl]-4-methylbenzamide Chemical compound CN(C)CCNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)F)=CC=2)Cl)=C1 FVEDXXPVSCVQFB-UHFFFAOYSA-N 0.000 claims description 2
- CFJWRNVHKYLWAX-UHFFFAOYSA-N 3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-n-ethyl-4-methylbenzamide Chemical compound CCNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)F)=CC=2)Cl)=C1 CFJWRNVHKYLWAX-UHFFFAOYSA-N 0.000 claims description 2
- LMYZOKRALXAYNX-UHFFFAOYSA-N 3-[2-chloro-4-(4-fluoro-2-methylanilino)benzoyl]-n-(2-hydroxyethyl)-4-methylbenzamide Chemical compound CC1=CC(F)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC(C(=O)NCCO)=CC=C1C LMYZOKRALXAYNX-UHFFFAOYSA-N 0.000 claims description 2
- XCKSSFFKYWEBNU-UHFFFAOYSA-N 3-[2-chloro-4-(4-fluoro-2-methylanilino)benzoyl]-n-(2-methoxyethyl)-4-methylbenzamide Chemical compound COCCNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)C)=CC=2)Cl)=C1 XCKSSFFKYWEBNU-UHFFFAOYSA-N 0.000 claims description 2
- JJUAQVCEBGVHBS-UHFFFAOYSA-N 3-[4-(2-aminoanilino)-2-chlorobenzoyl]-n-(2-methoxyethyl)-4-methylbenzamide Chemical compound COCCNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC=CC=3)N)=CC=2)Cl)=C1 JJUAQVCEBGVHBS-UHFFFAOYSA-N 0.000 claims description 2
- FSJLRPIFRXFXFY-UHFFFAOYSA-N 3-[4-(2-aminoanilino)-2-chlorobenzoyl]-n-ethyl-4-methylbenzamide Chemical compound CCNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC=CC=3)N)=CC=2)Cl)=C1 FSJLRPIFRXFXFY-UHFFFAOYSA-N 0.000 claims description 2
- GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 claims description 2
- IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 claims description 2
- IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 claims description 2
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- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 2
- POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 claims description 2
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- SVIYTFWTTLUJNE-UHFFFAOYSA-N [3-[2-chloro-4-(4-fluoro-2-methylanilino)benzoyl]-4-methylphenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)C)=CC=2)Cl)=C1 SVIYTFWTTLUJNE-UHFFFAOYSA-N 0.000 claims description 2
- QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 claims description 2
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- 150000003536 tetrazoles Chemical class 0.000 claims description 2
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- OTXWXCGYQLTHPZ-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-(2,3-dihydroxypropoxy)-2-fluorophenyl]methanone Chemical compound OCC(O)COC1=CC=C(F)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 OTXWXCGYQLTHPZ-UHFFFAOYSA-N 0.000 claims 1
- YATJQLMEBIHACT-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-(3-hydroxybutylamino)-2-methylphenyl]methanone Chemical compound CC(O)CCNC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 YATJQLMEBIHACT-UHFFFAOYSA-N 0.000 claims 1
- UWFSJCZMUKJSKI-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-(3-hydroxyprop-1-enyl)-2-methylphenyl]methanone Chemical compound CC1=CC=C(C=CCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F UWFSJCZMUKJSKI-UHFFFAOYSA-N 0.000 claims 1
- GNUIGSLAGTYHEC-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-(hydroxymethyl)-2-methoxyphenyl]methanone Chemical compound COC1=CC=C(CO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F GNUIGSLAGTYHEC-UHFFFAOYSA-N 0.000 claims 1
- FBRVHEGYHPYJNR-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-(hydroxymethyl)-2-methylphenyl]methanone Chemical compound CC1=CC=C(CO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F FBRVHEGYHPYJNR-UHFFFAOYSA-N 0.000 claims 1
- YTXVWPZKRCYNAK-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]-2-fluorophenyl]methanone Chemical compound O1C(C)(C)OCC1COC1=CC=C(F)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 YTXVWPZKRCYNAK-UHFFFAOYSA-N 0.000 claims 1
- OGFASUGUCYIQIX-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[3-(hydroxymethyl)phenyl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(C=2C=C(CO)C=CC=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F OGFASUGUCYIQIX-UHFFFAOYSA-N 0.000 claims 1
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- AROIYBOLSSDZST-UHFFFAOYSA-N [2-chloro-4-(2-nitroanilino)phenyl]-[2-fluoro-5-(2-morpholin-4-ylethoxy)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC(OCCN2CCOCC2)=CC=C1F AROIYBOLSSDZST-UHFFFAOYSA-N 0.000 claims 1
- RAXVYQAINRWSKE-UHFFFAOYSA-N [2-chloro-4-(2-nitroanilino)phenyl]-[5-(2,3-dihydroxypropoxy)-2-fluorophenyl]methanone Chemical compound OCC(O)COC1=CC=C(F)C(C(=O)C=2C(=CC(NC=3C(=CC=CC=3)[N+]([O-])=O)=CC=2)Cl)=C1 RAXVYQAINRWSKE-UHFFFAOYSA-N 0.000 claims 1
- BZFDYOHIMVBPQS-UHFFFAOYSA-N [2-chloro-4-(4-chloro-2-methylanilino)phenyl]-[5-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]-2-fluorophenyl]methanone Chemical compound CC1=CC(Cl)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC(OCC2OC(C)(C)OC2)=CC=C1F BZFDYOHIMVBPQS-UHFFFAOYSA-N 0.000 claims 1
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- FEWHRUNYKPXYRP-UHFFFAOYSA-N [2-chloro-4-(4-fluoroanilino)phenyl]-[2-fluoro-5-(3-hydroxypropoxy)phenyl]methanone Chemical compound OCCCOC1=CC=C(F)C(C(=O)C=2C(=CC(NC=3C=CC(F)=CC=3)=CC=2)Cl)=C1 FEWHRUNYKPXYRP-UHFFFAOYSA-N 0.000 claims 1
- QGBZIJTVIMOLRL-UHFFFAOYSA-N [3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methoxyphenyl]methyl acetate Chemical compound COC1=CC=C(COC(C)=O)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F QGBZIJTVIMOLRL-UHFFFAOYSA-N 0.000 claims 1
- NPKSUFINUFBBEM-UHFFFAOYSA-N [3-[2-chloro-4-(4-fluoro-2-methylanilino)benzoyl]-4-methylphenyl]-morpholin-4-ylmethanone Chemical compound CC1=CC=C(C(=O)N2CCOCC2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1C NPKSUFINUFBBEM-UHFFFAOYSA-N 0.000 claims 1
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- AGKHRKSGHYUOEB-UHFFFAOYSA-N [4-(4-bromo-2-nitroanilino)-2-chlorophenyl]-[4-(2-fluoroethoxy)-2-methylphenyl]methanone Chemical compound CC1=CC(OCCF)=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1[N+]([O-])=O AGKHRKSGHYUOEB-UHFFFAOYSA-N 0.000 claims 1
- UDYCWNUXAUPQNV-UHFFFAOYSA-N [4-(4-fluoro-2-methylanilino)-2-nitrophenyl]-[2-methyl-5-(2-morpholin-4-ylethoxy)phenyl]methanone Chemical compound CC1=CC(F)=CC=C1NC(C=C1[N+]([O-])=O)=CC=C1C(=O)C1=CC(OCCN2CCOCC2)=CC=C1C UDYCWNUXAUPQNV-UHFFFAOYSA-N 0.000 claims 1
- XIQFPULYCWONED-UHFFFAOYSA-N [4-(4-fluoro-2-methylanilino)-2-nitrophenyl]-[5-(3-hydroxypropoxy)-2-methylphenyl]methanone Chemical compound CC1=CC(F)=CC=C1NC(C=C1[N+]([O-])=O)=CC=C1C(=O)C1=CC(OCCCO)=CC=C1C XIQFPULYCWONED-UHFFFAOYSA-N 0.000 claims 1
- SCVOTJUXPHAPDG-UHFFFAOYSA-N [4-(4-fluoro-2-methylanilino)-2-nitrophenyl]-[5-[(4-methoxyphenyl)methoxy]-2-methylphenyl]methanone Chemical compound C1=CC(OC)=CC=C1COC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)C)=CC=2)[N+]([O-])=O)=C1 SCVOTJUXPHAPDG-UHFFFAOYSA-N 0.000 claims 1
- DZCUDBPLYZWETC-UHFFFAOYSA-N [4-[2-(3-aminoprop-1-enyl)anilino]-2-chlorophenyl]-[2-methyl-4-[2-(oxan-2-yloxy)ethoxy]phenyl]methanone Chemical compound C=1C=C(C(=O)C=2C(=CC(NC=3C(=CC=CC=3)C=CCN)=CC=2)Cl)C(C)=CC=1OCCOC1CCCCO1 DZCUDBPLYZWETC-UHFFFAOYSA-N 0.000 claims 1
- FJIZKTJLLBAUKH-UHFFFAOYSA-N [5-(2,3-dihydroxypropoxy)-2-methylphenyl]-[4-(4-fluoro-2-methylanilino)-2-nitrophenyl]methanone Chemical compound CC1=CC=C(OCC(O)CO)C=C1C(=O)C(C(=C1)[N+]([O-])=O)=CC=C1NC1=CC=C(F)C=C1C FJIZKTJLLBAUKH-UHFFFAOYSA-N 0.000 claims 1
- NMEOIZUQCRVGOE-UHFFFAOYSA-N [5-(3-bromopropoxy)-2-chlorophenyl]-[2-chloro-4-(2,6-difluoroanilino)phenyl]methanone Chemical compound FC1=CC=CC(F)=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC(OCCCBr)=CC=C1Cl NMEOIZUQCRVGOE-UHFFFAOYSA-N 0.000 claims 1
- NUPWXPNRUXHBKG-UHFFFAOYSA-N [5-(azidomethyl)-2-methylphenyl]-[2-chloro-4-(2,4-difluoroanilino)phenyl]methanone Chemical compound CC1=CC=C(CN=[N+]=[N-])C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F NUPWXPNRUXHBKG-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- OTKPPUXRIADSGD-PPRNARJGSA-N avoparcina Chemical compound O([C@@H]1C2=CC=C(C(=C2)Cl)OC=2C=C3C=C(C=2O[C@H]2C([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@@H]2O[C@@H](C)[C@H](O)[C@H](N)C2)OC2=CC=C(C=C2)[C@@H](O)[C@H](C(N[C@H](C(=O)N[C@H]3C(=O)N[C@H]2C(=O)N[C@@H]1C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)C=1C=CC(O)=CC=1)=O)NC(=O)[C@H](NC)C=1C=CC(O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)=CC=1)[C@H]1C[C@@H](N)[C@@H](O)[C@H](C)O1 OTKPPUXRIADSGD-PPRNARJGSA-N 0.000 claims 1
- OFXXQIJUOUGSJZ-UHFFFAOYSA-N benzyl n-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]carbamate Chemical compound C1=C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)C(C)=CC=C1NC(=O)OCC1=CC=CC=C1 OFXXQIJUOUGSJZ-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 150000001879 copper Chemical class 0.000 claims 1
- BFXLJWUGRPGMFU-UHFFFAOYSA-N dipropoxyphosphinothioyl n,n-diethylcarbamodithioate;sulfane Chemical compound S.CCCOP(=S)(OCCC)SC(=S)N(CC)CC BFXLJWUGRPGMFU-UHFFFAOYSA-N 0.000 claims 1
- DFBKLUNHFCTMDC-GKRDHZSOSA-N endrin Chemical compound C([C@@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@@H]2[C@H]2[C@@H]1O2 DFBKLUNHFCTMDC-GKRDHZSOSA-N 0.000 claims 1
- JPGQOUSTVILISH-UHFFFAOYSA-N enflurane Chemical compound FC(F)OC(F)(F)C(F)Cl JPGQOUSTVILISH-UHFFFAOYSA-N 0.000 claims 1
- ASVSIUHRASYRQY-UHFFFAOYSA-N ethyl 2-[[2-[[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylbenzoyl]amino]acetyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)CNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 ASVSIUHRASYRQY-UHFFFAOYSA-N 0.000 claims 1
- OGCBQYBVQDHUSX-UHFFFAOYSA-N ethyl 2-[[2-[[3-[2-chloro-4-(2,6-difluoroanilino)benzoyl]-4-methoxybenzoyl]amino]acetyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)CNC(=O)C1=CC=C(OC)C(C(=O)C=2C(=CC(NC=3C(=CC=CC=3F)F)=CC=2)Cl)=C1 OGCBQYBVQDHUSX-UHFFFAOYSA-N 0.000 claims 1
- OMPPHYIYQWXETF-UHFFFAOYSA-N ethyl 2-[[2-[[3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-4-methylbenzoyl]amino]acetyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)CNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)F)=CC=2)Cl)=C1 OMPPHYIYQWXETF-UHFFFAOYSA-N 0.000 claims 1
- IICLYCCTMMRTJU-UHFFFAOYSA-N ethyl 2-[[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylbenzoyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 IICLYCCTMMRTJU-UHFFFAOYSA-N 0.000 claims 1
- KBJVSCCTXCINGW-UHFFFAOYSA-N ethyl 3-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 KBJVSCCTXCINGW-UHFFFAOYSA-N 0.000 claims 1
- RXFPQSHPDLKREP-UHFFFAOYSA-N ethyl n-[2-[3-chloro-4-[5-(2-hydroxyethylcarbamoyl)-2-methylbenzoyl]anilino]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC(C(=O)NCCO)=CC=C1C RXFPQSHPDLKREP-UHFFFAOYSA-N 0.000 claims 1
- RMVPJHMHLQMZBY-UHFFFAOYSA-N ethyl n-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]carbamate Chemical compound CCOC(=O)NC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 RMVPJHMHLQMZBY-UHFFFAOYSA-N 0.000 claims 1
- DGXVRRWWENFKEF-UHFFFAOYSA-N methyl 4-[[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylbenzoyl]amino]thiophene-3-carboxylate Chemical compound COC(=O)C1=CSC=C1NC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 DGXVRRWWENFKEF-UHFFFAOYSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- YUQLNSOEEAHREP-UHFFFAOYSA-N n-(2-acetamidoethyl)-3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylbenzamide Chemical compound CC(=O)NCCNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 YUQLNSOEEAHREP-UHFFFAOYSA-N 0.000 claims 1
- FDVLYRHDZTVLAV-UHFFFAOYSA-N n-(2-amino-2-oxoethyl)-3-(4-anilino-2-chlorobenzoyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCC(N)=O)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1 FDVLYRHDZTVLAV-UHFFFAOYSA-N 0.000 claims 1
- IHCHOVVAJBADAH-UHFFFAOYSA-N n-[2-hydroxy-4-(1h-pyrazol-4-yl)phenyl]-6-methoxy-3,4-dihydro-2h-chromene-3-carboxamide Chemical compound C1C2=CC(OC)=CC=C2OCC1C(=O)NC(C(=C1)O)=CC=C1C=1C=NNC=1 IHCHOVVAJBADAH-UHFFFAOYSA-N 0.000 claims 1
- HTISLVRHMBAGCF-UHFFFAOYSA-N n-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-1-phenylmethanesulfonamide Chemical compound C1=C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)C(C)=CC=C1NS(=O)(=O)CC1=CC=CC=C1 HTISLVRHMBAGCF-UHFFFAOYSA-N 0.000 claims 1
- DWYGLMPQNKNHJL-UHFFFAOYSA-N n-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-2,6-dioxo-1,3-diazinane-4-carboxamide Chemical compound C1=C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)C(C)=CC=C1NC(=O)C1CC(=O)NC(=O)N1 DWYGLMPQNKNHJL-UHFFFAOYSA-N 0.000 claims 1
- ACNDCFIEGZPDFX-UHFFFAOYSA-N n-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-2-(2-methoxyethoxy)acetamide Chemical compound COCCOCC(=O)NC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 ACNDCFIEGZPDFX-UHFFFAOYSA-N 0.000 claims 1
- SFYNBPCWLINGFA-UHFFFAOYSA-N n-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-2-hydroxybenzamide Chemical compound C1=C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)C(C)=CC=C1NC(=O)C1=CC=CC=C1O SFYNBPCWLINGFA-UHFFFAOYSA-N 0.000 claims 1
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US48948803P | 2003-07-24 | 2003-07-24 |
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JP (1) | JP4939216B2 (es) |
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AU (1) | AU2004259264B2 (es) |
BR (1) | BRPI0412893A (es) |
CA (1) | CA2530302C (es) |
DE (1) | DE602004027504D1 (es) |
DK (1) | DK1658263T3 (es) |
ES (1) | ES2346972T3 (es) |
HK (1) | HK1090350A1 (es) |
HR (1) | HRP20100418T1 (es) |
IL (1) | IL172429A0 (es) |
IS (1) | IS2761B (es) |
MX (1) | MXPA06000708A (es) |
MY (1) | MY142988A (es) |
NO (1) | NO20060230L (es) |
NZ (1) | NZ544178A (es) |
PT (1) | PT1658263E (es) |
RU (1) | RU2396250C2 (es) |
TW (1) | TWI337075B (es) |
UA (1) | UA85559C2 (es) |
WO (1) | WO2005009940A1 (es) |
ZA (1) | ZA200510137B (es) |
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MX2007001215A (es) | 2004-08-06 | 2007-04-17 | Otsuka Pharma Co Ltd | Compuestos aromaticos. |
UA90698C2 (en) * | 2004-12-13 | 2010-05-25 | Лео Фарма А/С | Triazole substituted aminobenzophenone compounds |
KR101411167B1 (ko) | 2005-04-13 | 2014-06-23 | 아스텍스 테라퓨틱스 리미티드 | 하이드록시벤즈아미드 유도체 및 hsp90 억제제로서의이의 용도 |
EP1940767A2 (en) * | 2005-09-07 | 2008-07-09 | Plexxikon, Inc. | Pparactive compounds |
CN101321529B (zh) | 2005-12-05 | 2012-09-05 | 大塚制药株式会社 | 作为抗肿瘤剂的二芳基醚衍生物 |
US20080293775A1 (en) * | 2005-12-15 | 2008-11-27 | Astrazeneca Ab | Substituted Diphenylethers, -Amines, -Sulfides and -Methanes for the Treatment of Respiratory Disease |
US7754725B2 (en) | 2006-03-01 | 2010-07-13 | Astex Therapeutics Ltd. | Dihydroxyphenyl isoindolymethanones |
KR100932093B1 (ko) * | 2006-09-27 | 2009-12-16 | 주식회사종근당 | 미세소관 형성 저해제로서 유용한 벤조페논 유도체 |
UA95978C2 (ru) | 2006-10-02 | 2011-09-26 | Оцука Фармас'Ютікел Ко., Лтд. | Ингибитор активации stat3/5 |
WO2008044045A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
JP5721949B2 (ja) | 2006-10-12 | 2015-05-20 | アステックス、セラピューティックス、リミテッドAstex Therapeutics Limited | 複合薬剤 |
JP5518478B2 (ja) | 2006-10-12 | 2014-06-11 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
JP5528806B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
CN101981029B (zh) * | 2008-03-26 | 2014-04-02 | 株式会社钟根堂 | 用于抑制微管形成的苯甲酮噻唑衍生物及其制备方法 |
GB0806527D0 (en) | 2008-04-11 | 2008-05-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
WO2010074776A2 (en) * | 2008-06-16 | 2010-07-01 | The University Of Tennessee Research Foundation | Compounds for the treatment of cancer |
US9029408B2 (en) | 2008-06-16 | 2015-05-12 | Gtx, Inc. | Compounds for treatment of cancer |
US8822513B2 (en) | 2010-03-01 | 2014-09-02 | Gtx, Inc. | Compounds for treatment of cancer |
US9447049B2 (en) | 2010-03-01 | 2016-09-20 | University Of Tennessee Research Foundation | Compounds for treatment of cancer |
WO2010028192A1 (en) | 2008-09-03 | 2010-03-11 | Repligen Corporation | Compositions including 6-aminohexanoic acid derivatives as hdac inhibitors |
BR112012015433B8 (pt) | 2009-12-22 | 2020-03-03 | Leo Pharma As | composição farmacêutica substancialmente anidra para aplicação cutânea |
NZ601001A (en) | 2009-12-22 | 2014-07-25 | Leo Pharma As | Pharmaceutical composition comprising solvent mixture and a vitamin d derivative or analogue |
CA2785253A1 (en) | 2009-12-22 | 2011-06-30 | Leo Pharma A/S | Calcipotriol monohydrate nanocrystals |
CA2791738C (en) | 2010-03-01 | 2020-06-09 | Gtx, Inc. | Aryl imidazolyl compounds for the treatment of cancer |
US8912184B1 (en) | 2010-03-01 | 2014-12-16 | Alzheimer's Institute Of America, Inc. | Therapeutic and diagnostic methods |
US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
WO2012118782A1 (en) | 2011-02-28 | 2012-09-07 | Repligen Corporation | Histone deacetylase inhibitors |
TW201329025A (zh) | 2011-11-01 | 2013-07-16 | Astex Therapeutics Ltd | 醫藥化合物 |
KR101229365B1 (ko) * | 2012-07-02 | 2013-02-18 | 대한민국 | 〔z〕n〔3〔2,4디플루오로페닐아미노〕1〔4나이트로페닐〕3옥소프로프1엔2일〕2메톡시벤즈아마이드를 유효성분으로 함유하는 신경퇴행성 질환 예방 및 치료용 약학적 조성물 |
DK2970139T3 (en) | 2013-03-15 | 2018-08-13 | Biomarin Pharm Inc | HDAC inhibitors |
CN103926794B (zh) * | 2014-04-29 | 2017-11-14 | 常州强力电子新材料股份有限公司 | 一种含有二苯甲酮衍生物光引发剂的光固化组合物 |
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Publication number | Priority date | Publication date | Assignee | Title |
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GB9701453D0 (en) * | 1997-01-24 | 1997-03-12 | Leo Pharm Prod Ltd | Aminobenzophenones |
ATE277897T1 (de) * | 1999-07-16 | 2004-10-15 | Leo Pharma As | Aminobenzophenone als inhibitoren von il-1beta und tnf-alpha |
US6555710B1 (en) * | 1999-07-16 | 2003-04-29 | Leo Pharmaceutical Products Ltd A/S Lovens Kemiske Fabrik Produktionsaktieselskab | Aminobenzophenones as inhibitors of IL-1 β and TNF-α |
US6566554B1 (en) | 1999-07-16 | 2003-05-20 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | Aminobenzophenones as inhibitors of IL-1β and TNF-α |
US6750253B1 (en) | 1999-07-16 | 2004-06-15 | Leo Pharmaceutical Products Ltd. A/S | Aminobenzophenones as inhibitors of il-1β and tnf-α |
US6624199B1 (en) * | 1999-07-16 | 2003-09-23 | Leo Pharmaceuticals Products Ltd. A/S | Aminobenzophenones |
PL356049A1 (en) * | 1999-12-06 | 2004-06-14 | Leo Pharma A/S | Aminobenzophenones as inhibitors of il-1beta and tnf-alpha |
KR20080064908A (ko) * | 2000-06-28 | 2008-07-09 | 테바 파마슈티컬 인더스트리즈 리미티드 | 카르베딜올 |
US20020165286A1 (en) * | 2000-12-08 | 2002-11-07 | Hanne Hedeman | Dermal anti-inflammatory composition |
GB0107368D0 (en) * | 2001-03-23 | 2001-05-16 | Novartis Ag | Organic compounds |
KR100896667B1 (ko) * | 2001-08-28 | 2009-05-14 | 레오 파마 에이/에스 | 신규한 아미노벤조페논 및 이를 포함하는 약제학적 조성물 |
-
2004
- 2004-07-09 CN CN2004800213784A patent/CN1826310B/zh not_active Expired - Fee Related
- 2004-07-09 DE DE602004027504T patent/DE602004027504D1/de active Active
- 2004-07-09 BR BRPI0412893-1A patent/BRPI0412893A/pt not_active IP Right Cessation
- 2004-07-09 DK DK04738987.9T patent/DK1658263T3/da active
- 2004-07-09 AU AU2004259264A patent/AU2004259264B2/en not_active Ceased
- 2004-07-09 RU RU2006105639/04A patent/RU2396250C2/ru not_active IP Right Cessation
- 2004-07-09 JP JP2006520673A patent/JP4939216B2/ja not_active Expired - Fee Related
- 2004-07-09 US US10/563,474 patent/US7977387B2/en not_active Expired - Fee Related
- 2004-07-09 AT AT04738987T patent/ATE469878T1/de active
- 2004-07-09 CA CA2530302A patent/CA2530302C/en not_active Expired - Fee Related
- 2004-07-09 MX MXPA06000708A patent/MXPA06000708A/es active IP Right Grant
- 2004-07-09 KR KR1020067001537A patent/KR101128275B1/ko not_active IP Right Cessation
- 2004-07-09 WO PCT/DK2004/000490 patent/WO2005009940A1/en active Search and Examination
- 2004-07-09 ES ES04738987T patent/ES2346972T3/es active Active
- 2004-07-09 ZA ZA200510137A patent/ZA200510137B/en unknown
- 2004-07-09 PT PT04738987T patent/PT1658263E/pt unknown
- 2004-07-09 NZ NZ544178A patent/NZ544178A/en not_active IP Right Cessation
- 2004-07-15 MY MYPI20042830A patent/MY142988A/en unknown
- 2004-07-22 AR ARP040102611A patent/AR045082A1/es unknown
- 2004-07-23 TW TW093122201A patent/TWI337075B/zh not_active IP Right Cessation
- 2004-09-07 UA UAA200601964A patent/UA85559C2/ru unknown
-
2005
- 2005-12-07 IL IL172429A patent/IL172429A0/en unknown
-
2006
- 2006-01-16 NO NO20060230A patent/NO20060230L/no not_active Application Discontinuation
- 2006-02-23 IS IS8323A patent/IS2761B/is unknown
- 2006-10-03 HK HK06110921.7A patent/HK1090350A1/xx not_active IP Right Cessation
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2010
- 2010-07-28 HR HR20100418T patent/HRP20100418T1/hr unknown
Also Published As
Publication number | Publication date |
---|---|
ES2346972T3 (es) | 2010-10-22 |
RU2006105639A (ru) | 2006-06-10 |
MY142988A (en) | 2011-02-14 |
AU2004259264A1 (en) | 2005-02-03 |
CN1826310B (zh) | 2010-07-21 |
HK1090350A1 (en) | 2006-12-22 |
DK1658263T3 (da) | 2010-09-27 |
IS2761B (is) | 2011-10-15 |
PT1658263E (pt) | 2010-09-06 |
KR101128275B1 (ko) | 2012-04-12 |
ATE469878T1 (de) | 2010-06-15 |
DE602004027504D1 (de) | 2010-07-15 |
MXPA06000708A (es) | 2006-04-19 |
NZ544178A (en) | 2008-11-28 |
CA2530302C (en) | 2013-12-03 |
AR045082A1 (es) | 2005-10-12 |
RU2396250C2 (ru) | 2010-08-10 |
IL172429A0 (en) | 2006-04-10 |
KR20060041270A (ko) | 2006-05-11 |
US20060166990A1 (en) | 2006-07-27 |
CA2530302A1 (en) | 2005-02-03 |
JP4939216B2 (ja) | 2012-05-23 |
UA85559C2 (en) | 2009-02-10 |
BRPI0412893A (pt) | 2006-10-03 |
US7977387B2 (en) | 2011-07-12 |
IS8323A (is) | 2006-02-23 |
NO20060230L (no) | 2006-01-16 |
TWI337075B (en) | 2011-02-11 |
WO2005009940A1 (en) | 2005-02-03 |
TW200509892A (en) | 2005-03-16 |
CN1826310A (zh) | 2006-08-30 |
HRP20100418T1 (hr) | 2010-09-30 |
JP2006528597A (ja) | 2006-12-21 |
AU2004259264B2 (en) | 2011-01-06 |
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