NO327984B1 - Substituerte pyridinoner, farmasoytiske preparater inneholdende slike forbindelser, slike forbindelser for anvendelse som medikament for behandling av sykdommer samt anvendelse av slike forbindelser for fremstilling av medikamenter for behandling av sykdommer - Google Patents
Substituerte pyridinoner, farmasoytiske preparater inneholdende slike forbindelser, slike forbindelser for anvendelse som medikament for behandling av sykdommer samt anvendelse av slike forbindelser for fremstilling av medikamenter for behandling av sykdommer Download PDFInfo
- Publication number
- NO327984B1 NO327984B1 NO20043820A NO20043820A NO327984B1 NO 327984 B1 NO327984 B1 NO 327984B1 NO 20043820 A NO20043820 A NO 20043820A NO 20043820 A NO20043820 A NO 20043820A NO 327984 B1 NO327984 B1 NO 327984B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- methyl
- bromo
- oxy
- difluorobenzyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 236
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 33
- 239000003814 drug Substances 0.000 title claims description 8
- 201000010099 disease Diseases 0.000 title description 15
- 238000004519 manufacturing process Methods 0.000 title description 9
- 239000008194 pharmaceutical composition Chemical class 0.000 title description 7
- 150000005299 pyridinones Chemical class 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 170
- 238000002360 preparation method Methods 0.000 claims description 148
- 229910052736 halogen Inorganic materials 0.000 claims description 121
- 150000002367 halogens Chemical class 0.000 claims description 121
- 229910052739 hydrogen Inorganic materials 0.000 claims description 72
- -1 hydroxy, hydroxy Chemical group 0.000 claims description 72
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 68
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 40
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 35
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000004193 piperazinyl group Chemical group 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 24
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 102100040247 Tumor necrosis factor Human genes 0.000 claims description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 21
- 125000003386 piperidinyl group Chemical group 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 17
- 208000035475 disorder Diseases 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 230000001404 mediated effect Effects 0.000 claims description 11
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- 230000004054 inflammatory process Effects 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 206010061218 Inflammation Diseases 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 125000002757 morpholinyl group Chemical group 0.000 claims description 9
- USRKMHMDWVNWLX-UHFFFAOYSA-N 1-benzyl-3-bromo-4-[(3-chlorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC=CC=2)C(C)=CC=1OCC1=CC=CC(Cl)=C1 USRKMHMDWVNWLX-UHFFFAOYSA-N 0.000 claims description 8
- 101000715731 Xenopus laevis Cerberus Proteins 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- KNCDMZFDFYDADF-UHFFFAOYSA-N 1-benzyl-4-[(3-chlorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound C=1C(=O)N(CC=2C=CC=CC=2)C(C)=CC=1OCC1=CC=CC(Cl)=C1 KNCDMZFDFYDADF-UHFFFAOYSA-N 0.000 claims description 7
- CBOJIVFOPAIKRA-UHFFFAOYSA-N 1-benzyl-6-methyl-4-phenylmethoxypyridin-2-one Chemical compound C=1C(=O)N(CC=2C=CC=CC=2)C(C)=CC=1OCC1=CC=CC=C1 CBOJIVFOPAIKRA-UHFFFAOYSA-N 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 206010003246 arthritis Diseases 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- BGSKLTFWWOSTJG-UHFFFAOYSA-N 1-benzyl-3-bromo-6-methyl-4-phenylmethoxypyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC=CC=2)C(C)=CC=1OCC1=CC=CC=C1 BGSKLTFWWOSTJG-UHFFFAOYSA-N 0.000 claims description 5
- KCAJXIDMCNPGHZ-UHFFFAOYSA-N PH 797804 Chemical compound CNC(=O)C1=CC=C(C)C(N2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 KCAJXIDMCNPGHZ-UHFFFAOYSA-N 0.000 claims description 5
- 230000002685 pulmonary effect Effects 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- KZKMIYIQLWQAOL-UHFFFAOYSA-N 3-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(N2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 KZKMIYIQLWQAOL-UHFFFAOYSA-N 0.000 claims description 4
- SFIVNQRKHWCDQO-UHFFFAOYSA-N 3-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]benzamide Chemical compound BrC=1C(=O)N(C=2C=C(C=CC=2)C(N)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F SFIVNQRKHWCDQO-UHFFFAOYSA-N 0.000 claims description 4
- PFMILNLGQLSMLX-UHFFFAOYSA-N 3-acetyl-1-(2-chlorophenyl)-6-methyl-4-phenylmethoxypyridin-2-one Chemical compound C1=C(C)N(C=2C(=CC=CC=2)Cl)C(=O)C(C(=O)C)=C1OCC1=CC=CC=C1 PFMILNLGQLSMLX-UHFFFAOYSA-N 0.000 claims description 4
- MTKLAIZXVSRBCS-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[[4-(2-hydroxypropan-2-yl)phenyl]methyl]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(=CC=2)C(C)(C)O)C(C)=CC=1OCC1=CC=C(F)C=C1F MTKLAIZXVSRBCS-UHFFFAOYSA-N 0.000 claims description 4
- SDCBHCVRLBVZQX-UHFFFAOYSA-N 4-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]benzamide Chemical compound BrC=1C(=O)N(C=2C=CC(=CC=2)C(N)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F SDCBHCVRLBVZQX-UHFFFAOYSA-N 0.000 claims description 4
- HVUPCGDITCGWTG-UHFFFAOYSA-N 4-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]-n-(2-hydroxyethyl)benzamide Chemical compound BrC=1C(=O)N(CC=2C=CC(=CC=2)C(=O)NCCO)C(C)=CC=1OCC1=CC=C(F)C=C1F HVUPCGDITCGWTG-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 4
- XIAJFWOACHIGML-UHFFFAOYSA-N 1-[[2-(aminomethyl)phenyl]methyl]-3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C(=CC=CC=2)CN)C(C)=CC=1OCC1=CC=C(F)C=C1F XIAJFWOACHIGML-UHFFFAOYSA-N 0.000 claims description 3
- NWWGASAIFNYQIF-UHFFFAOYSA-N 1-[[4-(aminomethyl)phenyl]methyl]-3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(CN)=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F NWWGASAIFNYQIF-UHFFFAOYSA-N 0.000 claims description 3
- RGZWOMIPFLICAI-UHFFFAOYSA-N 2-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]benzamide Chemical compound BrC=1C(=O)N(CC=2C(=CC=CC=2)C(N)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F RGZWOMIPFLICAI-UHFFFAOYSA-N 0.000 claims description 3
- WYGTZMORWGQIPR-UHFFFAOYSA-N 3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 WYGTZMORWGQIPR-UHFFFAOYSA-N 0.000 claims description 3
- LWSGIZCOBNMXTH-UHFFFAOYSA-N 3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]benzamide Chemical compound BrC=1C(=O)N(CC=2C=C(C=CC=2)C(N)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F LWSGIZCOBNMXTH-UHFFFAOYSA-N 0.000 claims description 3
- IJHZHMDMJCJCDV-UHFFFAOYSA-N 3-bromo-1-(2,6-dichlorophenyl)-4-[(4-fluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(C=2C(=CC=CC=2Cl)Cl)C(C)=CC=1OCC1=CC=C(F)C=C1 IJHZHMDMJCJCDV-UHFFFAOYSA-N 0.000 claims description 3
- KBFGSUTZQQUJCZ-UHFFFAOYSA-N 3-bromo-1-(2,6-dimethylphenyl)-4-[(4-fluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound CC1=CC=CC(C)=C1N1C(=O)C(Br)=C(OCC=2C=CC(F)=CC=2)C=C1C KBFGSUTZQQUJCZ-UHFFFAOYSA-N 0.000 claims description 3
- CFCCLYABTGQRRK-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[(4-hydroxyphenyl)methyl]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(O)=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F CFCCLYABTGQRRK-UHFFFAOYSA-N 0.000 claims description 3
- CDXILCRPUHVRAP-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[5-(2-hydroxypropan-2-yl)-2-methylphenyl]-6-methylpyridin-2-one Chemical compound CC1=CC=C(C(C)(C)O)C=C1N1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C CDXILCRPUHVRAP-UHFFFAOYSA-N 0.000 claims description 3
- DIDKAZVJVLTZIN-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-1-[5-(hydroxymethyl)-2-methylphenyl]-6-methylpyridin-2-one Chemical compound CC1=CC=C(CO)C=C1N1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C DIDKAZVJVLTZIN-UHFFFAOYSA-N 0.000 claims description 3
- NNRZDPMJVSZIGC-UHFFFAOYSA-N 3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-1-[[4-(methylaminomethyl)phenyl]methyl]pyridin-2-one Chemical compound C1=CC(CNC)=CC=C1CN1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C NNRZDPMJVSZIGC-UHFFFAOYSA-N 0.000 claims description 3
- ASWPKEVNQRQXHL-UHFFFAOYSA-N 3-chloro-4-[(2,4-difluorophenyl)methoxy]-1-[5-(hydroxymethyl)-2-methylphenyl]-6-methylpyridin-2-one Chemical compound CC1=CC=C(CO)C=C1N1C(=O)C(Cl)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C ASWPKEVNQRQXHL-UHFFFAOYSA-N 0.000 claims description 3
- HZWGPERGVBIRCQ-UHFFFAOYSA-N 4-(3-bromo-2-oxo-4-phenylmethoxypyridin-1-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1N1C(=O)C(Br)=C(OCC=2C=CC=CC=2)C=C1 HZWGPERGVBIRCQ-UHFFFAOYSA-N 0.000 claims description 3
- PHGFIDCHPGXZAU-UHFFFAOYSA-N 4-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]benzamide Chemical compound BrC=1C(=O)N(CC=2C=CC(=CC=2)C(N)=O)C(C)=CC=1OCC1=CC=C(F)C=C1F PHGFIDCHPGXZAU-UHFFFAOYSA-N 0.000 claims description 3
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims description 3
- 208000002193 Pain Diseases 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- UNBMAKZTWQAXTR-UHFFFAOYSA-N ethyl 3-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]benzoate Chemical compound CCOC(=O)C1=CC=CC(N2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 UNBMAKZTWQAXTR-UHFFFAOYSA-N 0.000 claims description 3
- KUABDEOJFTXNLI-UHFFFAOYSA-N methyl 3-[[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]methyl]benzoate Chemical compound COC(=O)C1=CC=CC(CN2C(C(Br)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 KUABDEOJFTXNLI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- CYEZJYAMLNTSKN-VOTSOKGWSA-N (e)-2-methylhept-3-ene Chemical compound CCC\C=C\C(C)C CYEZJYAMLNTSKN-VOTSOKGWSA-N 0.000 claims description 2
- LUVJHJDVISUMCN-UHFFFAOYSA-N 1-benzyl-3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F LUVJHJDVISUMCN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- ZQLPVBNKJHIHFZ-UHFFFAOYSA-N 3-[3-bromo-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-n-(2-hydroxyethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCO)C=C1N1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C ZQLPVBNKJHIHFZ-UHFFFAOYSA-N 0.000 claims description 2
- PJPBTNREUVPPLY-UHFFFAOYSA-N 3-[3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-4-fluoro-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(F)C(N2C(C(Cl)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 PJPBTNREUVPPLY-UHFFFAOYSA-N 0.000 claims description 2
- UVYXMJXLBYAVTQ-UHFFFAOYSA-N 3-[3-chloro-4-[(2,4-difluorophenyl)methoxy]-6-methyl-2-oxopyridin-1-yl]-n,4-dimethylbenzamide Chemical compound CNC(=O)C1=CC=C(C)C(N2C(C(Cl)=C(OCC=3C(=CC(F)=CC=3)F)C=C2C)=O)=C1 UVYXMJXLBYAVTQ-UHFFFAOYSA-N 0.000 claims description 2
- FHKNUUOAUZKVDT-UHFFFAOYSA-N 3-bromo-1-(2,6-dichlorophenyl)-4-[(2,6-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(C=2C(=CC=CC=2Cl)Cl)C(C)=CC=1OCC1=C(F)C=CC=C1F FHKNUUOAUZKVDT-UHFFFAOYSA-N 0.000 claims description 2
- DGKNVUBVVYMFQC-UHFFFAOYSA-N 3-bromo-1-(2,6-difluorophenyl)-4-[(2,4-difluorophenyl)methoxy]-6-(hydroxymethyl)pyridin-2-one Chemical compound BrC=1C(=O)N(C=2C(=CC=CC=2F)F)C(CO)=CC=1OCC1=CC=C(F)C=C1F DGKNVUBVVYMFQC-UHFFFAOYSA-N 0.000 claims description 2
- WWKDYZXSYNVDLC-UHFFFAOYSA-N 3-bromo-1-(2,6-dimethylphenyl)-6-methyl-4-[(2,4,6-trifluorophenyl)methoxy]pyridin-2-one Chemical compound CC1=CC=CC(C)=C1N1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2F)F)C=C1C WWKDYZXSYNVDLC-UHFFFAOYSA-N 0.000 claims description 2
- ZTLOWDPOVPKXNN-UHFFFAOYSA-N 3-bromo-1-(3,5-dibromo-2,6-difluoro-4-hydroxyphenyl)-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(C=2C(=C(Br)C(O)=C(Br)C=2F)F)C(C)=CC=1OCC1=CC=C(F)C=C1F ZTLOWDPOVPKXNN-UHFFFAOYSA-N 0.000 claims description 2
- BFQGTSKLUZCTMV-UHFFFAOYSA-N 3-bromo-1-[2,4-difluoro-6-[2-hydroxyethyl(methyl)amino]phenyl]-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound OCCN(C)C1=CC(F)=CC(F)=C1N1C(=O)C(Br)=C(OCC=2C(=CC(F)=CC=2)F)C=C1C BFQGTSKLUZCTMV-UHFFFAOYSA-N 0.000 claims description 2
- CPOYXKVGUFVISK-UHFFFAOYSA-N 3-bromo-1-[[3-(bromomethyl)phenyl]methyl]-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=C(CBr)C=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F CPOYXKVGUFVISK-UHFFFAOYSA-N 0.000 claims description 2
- LBTDIEUCSWVXQS-UHFFFAOYSA-N 3-bromo-1-[[4-(bromomethyl)phenyl]methyl]-4-[(2,4-difluorophenyl)methoxy]-6-methylpyridin-2-one Chemical compound BrC=1C(=O)N(CC=2C=CC(CBr)=CC=2)C(C)=CC=1OCC1=CC=C(F)C=C1F LBTDIEUCSWVXQS-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 2004-09-13 NO NO20043820A patent/NO327984B1/no not_active IP Right Cessation
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2005
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2006
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2009
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