HRP20030269A2 - Aryl or heteroaryl fused imidazole compounds as anti-inflammatory and analgesic agents - Google Patents
Aryl or heteroaryl fused imidazole compounds as anti-inflammatory and analgesic agentsInfo
- Publication number
- HRP20030269A2 HRP20030269A2 HR20030269A HRP20030269A HRP20030269A2 HR P20030269 A2 HRP20030269 A2 HR P20030269A2 HR 20030269 A HR20030269 A HR 20030269A HR P20030269 A HRP20030269 A HR P20030269A HR P20030269 A2 HRP20030269 A2 HR P20030269A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- ethyl
- amino
- phenyl
- carbonyl
- Prior art date
Links
- 125000003118 aryl group Chemical group 0.000 title claims description 129
- 150000002460 imidazoles Chemical class 0.000 title description 16
- 125000001072 heteroaryl group Chemical group 0.000 title description 3
- 239000000730 antalgic agent Substances 0.000 title description 2
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 230000003110 anti-inflammatory effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 372
- -1 oxopiperidyl Chemical group 0.000 claims description 254
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 216
- 229910052736 halogen Inorganic materials 0.000 claims description 149
- 150000002367 halogens Chemical group 0.000 claims description 148
- 125000002950 monocyclic group Chemical group 0.000 claims description 117
- 238000000034 method Methods 0.000 claims description 105
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 102
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 87
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 83
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 80
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 229910052717 sulfur Inorganic materials 0.000 claims description 64
- 125000005842 heteroatom Chemical group 0.000 claims description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
- 229910052757 nitrogen Inorganic materials 0.000 claims description 57
- 125000002619 bicyclic group Chemical group 0.000 claims description 56
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 42
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 40
- 229910052760 oxygen Inorganic materials 0.000 claims description 39
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 37
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 32
- 125000002947 alkylene group Chemical group 0.000 claims description 31
- 125000006239 protecting group Chemical group 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 28
- 239000000460 chlorine Substances 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 24
- 239000005977 Ethylene Substances 0.000 claims description 24
- 125000004414 alkyl thio group Chemical group 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 23
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 23
- 125000004043 oxo group Chemical group O=* 0.000 claims description 23
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 22
- 125000005936 piperidyl group Chemical group 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- 125000001544 thienyl group Chemical group 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 15
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 15
- 125000000335 thiazolyl group Chemical group 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 208000035475 disorder Diseases 0.000 claims description 12
- 125000003161 (C1-C6) alkylene group Chemical class 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- GZFUZUFRJAEXPD-UHFFFAOYSA-N 1-[2-[4-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)phenyl]ethyl]-3-thiophen-2-ylsulfonylurea Chemical compound CCC1=NC2=C(C)C=C(C)N=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=CS1 GZFUZUFRJAEXPD-UHFFFAOYSA-N 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 6
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 6
- 241000282412 Homo Species 0.000 claims description 6
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003180 prostaglandins Chemical class 0.000 claims description 6
- SSDHSAQPLKZVRY-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-3-[2-[4-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)phenyl]ethyl]urea Chemical compound CCC1=NC2=C(C)C=C(C)N=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=CC=C1Cl SSDHSAQPLKZVRY-UHFFFAOYSA-N 0.000 claims description 5
- ITZFODVISQIQFV-UHFFFAOYSA-N 1-[4-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)phenyl]propan-2-yl n-(4-methylphenyl)sulfonylcarbamate Chemical compound CCC1=NC2=C(C)C=C(C)N=C2N1C(C=C1)=CC=C1CC(C)OC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 ITZFODVISQIQFV-UHFFFAOYSA-N 0.000 claims description 5
- FLDDGZZYHSLLJW-UHFFFAOYSA-N 1-(5-chlorothiophen-2-yl)sulfonyl-3-[2-[4-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)phenyl]ethyl]urea Chemical compound CCC1=NC2=C(C)C=C(C)N=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(Cl)S1 FLDDGZZYHSLLJW-UHFFFAOYSA-N 0.000 claims description 4
- HZVLFTCYCLXTGV-UHFFFAOYSA-N 1-[2-[4-(2-ethyl-4,6-dimethylimidazo[4,5-c]pyridin-1-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=C(C)N=C(C)C=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 HZVLFTCYCLXTGV-UHFFFAOYSA-N 0.000 claims description 4
- DHQNPIRWIIQAKM-UHFFFAOYSA-N 1-[2-[4-(2-ethyl-5,6-dimethylimidazo[4,5-b]pyridin-3-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=CC(C)=C(C)N=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 DHQNPIRWIIQAKM-UHFFFAOYSA-N 0.000 claims description 4
- MQBXOQQOCIUETP-UHFFFAOYSA-N 1-[2-[4-(2-ethyl-5-hydroxybenzimidazol-1-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=CC(O)=CC=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 MQBXOQQOCIUETP-UHFFFAOYSA-N 0.000 claims description 4
- OZTHHJWONRMDRZ-UHFFFAOYSA-N 1-[2-[4-(2-ethyl-6-methoxybenzimidazol-1-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=CC=C(OC)C=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 OZTHHJWONRMDRZ-UHFFFAOYSA-N 0.000 claims description 4
- QGRORJBNJHUPRK-UHFFFAOYSA-N 1-[2-[4-(5-cyano-2-ethylbenzimidazol-1-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=CC(C#N)=CC=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 QGRORJBNJHUPRK-UHFFFAOYSA-N 0.000 claims description 4
- FIXXXBYFTUXZLG-UHFFFAOYSA-N 1-[2-[4-(6-ethyl-[1,3]dioxolo[4,5-f]benzimidazol-7-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=CC=3OCOC=3C=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 FIXXXBYFTUXZLG-UHFFFAOYSA-N 0.000 claims description 4
- JEJBRXQXDMSKME-UHFFFAOYSA-N 1-[2-[4-[5,7-dimethyl-2-(1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-3-yl]phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NCCC1=CC=C(N2C3=NC(C)=CC(C)=C3N=C2C2=NNC=C2)C=C1 JEJBRXQXDMSKME-UHFFFAOYSA-N 0.000 claims description 4
- ZVHXCMFIZUHPFN-UHFFFAOYSA-N 1-[2-[4-[5,7-dimethyl-2-(methylamino)imidazo[4,5-b]pyridin-3-yl]phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CNC1=NC2=C(C)C=C(C)N=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 ZVHXCMFIZUHPFN-UHFFFAOYSA-N 0.000 claims description 4
- UEXRPEOZBKYETI-UHFFFAOYSA-N 1-[2-[4-[5,7-dimethyl-2-[2-(1,3-thiazol-2-yl)ethyl]imidazo[4,5-b]pyridin-3-yl]phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NCCC1=CC=C(N2C3=NC(C)=CC(C)=C3N=C2CCC=2SC=CN=2)C=C1 UEXRPEOZBKYETI-UHFFFAOYSA-N 0.000 claims description 4
- RWTZOYDKFYIGHY-UHFFFAOYSA-N 1-[2-[4-[6-chloro-2-(2-hydroxypropan-2-yl)-5-(trifluoromethyl)benzimidazol-1-yl]phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NCCC1=CC=C(N2C3=CC(Cl)=C(C=C3N=C2C(C)(C)O)C(F)(F)F)C=C1 RWTZOYDKFYIGHY-UHFFFAOYSA-N 0.000 claims description 4
- QMHYCEZPVUGVHC-UHFFFAOYSA-N 2-[4-(2-butyl-4,6-dimethylimidazo[4,5-c]pyridin-1-yl)phenyl]ethyl n-(4-methylphenyl)sulfonylcarbamate Chemical compound CCCCC1=NC2=C(C)N=C(C)C=C2N1C(C=C1)=CC=C1CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 QMHYCEZPVUGVHC-UHFFFAOYSA-N 0.000 claims description 4
- YNSMPQCCKLYELZ-UHFFFAOYSA-N 2-[4-(2-ethyl-4,6-dimethylimidazo[4,5-c]pyridin-1-yl)phenyl]ethyl n-(4-methylphenyl)sulfonylcarbamate Chemical compound CCC1=NC2=C(C)N=C(C)C=C2N1C(C=C1)=CC=C1CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 YNSMPQCCKLYELZ-UHFFFAOYSA-N 0.000 claims description 4
- MHDGNBXHAQYYLD-UHFFFAOYSA-N 2-[4-(2-tert-butyl-4,6-dimethylimidazo[4,5-c]pyridin-1-yl)phenyl]ethyl n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OCCC1=CC=C(N2C3=CC(C)=NC(C)=C3N=C2C(C)(C)C)C=C1 MHDGNBXHAQYYLD-UHFFFAOYSA-N 0.000 claims description 4
- JVMVTFXZGSJKKP-UHFFFAOYSA-N 2-[4-(4,6-dimethyl-2-phenylimidazo[4,5-c]pyridin-1-yl)phenyl]ethyl N-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OCCC1=CC=C(N2C3=CC(C)=NC(C)=C3N=C2C=2C=CC=CC=2)C=C1 JVMVTFXZGSJKKP-UHFFFAOYSA-N 0.000 claims description 4
- KTLAVEBBQHWJJN-UHFFFAOYSA-N 2-[4-(5-carbamoyl-6-chloro-2-ethylbenzimidazol-1-yl)phenyl]ethyl n-(4-methylphenyl)sulfonylcarbamate Chemical compound CCC1=NC2=CC(C(N)=O)=C(Cl)C=C2N1C(C=C1)=CC=C1CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 KTLAVEBBQHWJJN-UHFFFAOYSA-N 0.000 claims description 4
- SJHCUHKHHDSHCB-UHFFFAOYSA-N 2-[4-(6-chloro-2-ethyl-5-methylsulfonylbenzimidazol-1-yl)phenyl]ethyl N-(4-methylphenyl)sulfonylcarbamate Chemical compound CCC1=NC2=CC(S(C)(=O)=O)=C(Cl)C=C2N1C(C=C1)=CC=C1CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 SJHCUHKHHDSHCB-UHFFFAOYSA-N 0.000 claims description 4
- RBSJXTXVNALVKT-UHFFFAOYSA-N 2-[4-[2-(2-acetamidopropan-2-yl)-6-chloro-5-(trifluoromethyl)benzimidazol-1-yl]phenyl]ethyl n-(4-methylphenyl)sulfonylcarbamate Chemical compound CC(=O)NC(C)(C)C1=NC2=CC(C(F)(F)F)=C(Cl)C=C2N1C(C=C1)=CC=C1CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 RBSJXTXVNALVKT-UHFFFAOYSA-N 0.000 claims description 4
- REFVNSKTXLSTND-UHFFFAOYSA-N 2-[4-[4,6-dimethyl-2-(3-phenylpropyl)imidazo[4,5-c]pyridin-1-yl]phenyl]ethyl N-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OCCC1=CC=C(N2C3=CC(C)=NC(C)=C3N=C2CCCC=2C=CC=CC=2)C=C1 REFVNSKTXLSTND-UHFFFAOYSA-N 0.000 claims description 4
- VFGIXMWNVHDPQH-UHFFFAOYSA-N 2-[4-[5,7-dimethyl-2-(methylamino)imidazo[4,5-b]pyridin-3-yl]phenyl]ethyl n-(4-methylphenyl)sulfonylcarbamate Chemical compound CNC1=NC2=C(C)C=C(C)N=C2N1C(C=C1)=CC=C1CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 VFGIXMWNVHDPQH-UHFFFAOYSA-N 0.000 claims description 4
- APGKXMQZKWNPEM-UHFFFAOYSA-N 2-[4-[6-chloro-2-(1h-pyrazol-5-yl)-5-(trifluoromethyl)benzimidazol-1-yl]phenyl]ethyl n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OCCC1=CC=C(N2C3=CC(Cl)=C(C=C3N=C2C2=NNC=C2)C(F)(F)F)C=C1 APGKXMQZKWNPEM-UHFFFAOYSA-N 0.000 claims description 4
- ZMJAHOBWGODFND-UHFFFAOYSA-N 2-[4-[6-chloro-2-ethyl-5-(trifluoromethyl)benzimidazol-1-yl]phenyl]ethyl N-(5-methylpyridin-2-yl)sulfonylcarbamate Chemical compound CCC1=NC2=CC(C(F)(F)F)=C(Cl)C=C2N1C(C=C1)=CC=C1CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=N1 ZMJAHOBWGODFND-UHFFFAOYSA-N 0.000 claims description 4
- RLOZEDWNVFSNCG-UHFFFAOYSA-N 2-[4-[6-chloro-2-ethyl-5-(trifluoromethyl)benzimidazol-1-yl]phenyl]ethyl n-(2-chlorophenyl)sulfonylcarbamate Chemical compound CCC1=NC2=CC(C(F)(F)F)=C(Cl)C=C2N1C(C=C1)=CC=C1CCOC(=O)NS(=O)(=O)C1=CC=CC=C1Cl RLOZEDWNVFSNCG-UHFFFAOYSA-N 0.000 claims description 4
- POKYHMDDVRBKFS-UHFFFAOYSA-N 2-[4-[6-chloro-2-ethyl-5-(trifluoromethyl)benzimidazol-1-yl]phenyl]ethyl-(4-methylphenyl)sulfonylcarbamic acid Chemical compound CCC1=NC2=CC(C(F)(F)F)=C(Cl)C=C2N1C(C=C1)=CC=C1CCN(C(O)=O)S(=O)(=O)C1=CC=C(C)C=C1 POKYHMDDVRBKFS-UHFFFAOYSA-N 0.000 claims description 4
- PALWWWZOWRHBCC-UHFFFAOYSA-N 2-[4-[6-chloro-2-pyridin-2-yl-5-(trifluoromethyl)benzimidazol-1-yl]phenyl]ethyl n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OCCC1=CC=C(N2C3=CC(Cl)=C(C=C3N=C2C=2N=CC=CC=2)C(F)(F)F)C=C1 PALWWWZOWRHBCC-UHFFFAOYSA-N 0.000 claims description 4
- RSQDGXWJQTWVSG-UHFFFAOYSA-N 2-[4-[6-chloro-2-pyridin-4-yl-5-(trifluoromethyl)benzimidazol-1-yl]phenyl]ethyl n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OCCC1=CC=C(N2C3=CC(Cl)=C(C=C3N=C2C=2C=CN=CC=2)C(F)(F)F)C=C1 RSQDGXWJQTWVSG-UHFFFAOYSA-N 0.000 claims description 4
- QOJMQWIXZYYYLV-UHFFFAOYSA-N 2-[5-[6-chloro-2-ethyl-5-(trifluoromethyl)benzimidazol-1-yl]pyridin-2-yl]ethyl n-(4-methylphenyl)sulfonylcarbamate Chemical compound CCC1=NC2=CC(C(F)(F)F)=C(Cl)C=C2N1C(C=N1)=CC=C1CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 QOJMQWIXZYYYLV-UHFFFAOYSA-N 0.000 claims description 4
- SVVQTRMBGDIUDL-UHFFFAOYSA-N 2-[6-[6-chloro-2-ethyl-5-(trifluoromethyl)benzimidazol-1-yl]pyridin-3-yl]ethyl N-(4-methylphenyl)sulfonylcarbamate Chemical compound CCC1=NC2=CC(C(F)(F)F)=C(Cl)C=C2N1C(N=C1)=CC=C1CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 SVVQTRMBGDIUDL-UHFFFAOYSA-N 0.000 claims description 4
- MOBSEOODRXRKSY-UHFFFAOYSA-N 2-ethyl-4,6-dimethyl-1-[4-[2-[(4-methylphenyl)sulfonylcarbamoylamino]ethyl]phenyl]benzimidazole-5-carboxamide Chemical compound CCC1=NC2=C(C)C(C(N)=O)=C(C)C=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 MOBSEOODRXRKSY-UHFFFAOYSA-N 0.000 claims description 4
- 125000006418 4-methylphenylsulfonyl group Chemical group 0.000 claims description 4
- WLKMZINZFGUOBX-UHFFFAOYSA-N 6-chloro-2-ethyl-1-[4-[2-[(4-methylphenyl)sulfonylcarbamoylamino]ethyl]phenyl]benzimidazole-5-carboxamide Chemical compound CCC1=NC2=CC(C(N)=O)=C(Cl)C=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 WLKMZINZFGUOBX-UHFFFAOYSA-N 0.000 claims description 4
- AJZMANQISJQJQM-UHFFFAOYSA-N 6-chloro-2-ethyl-1-[4-[2-[methyl-[(4-methylphenyl)sulfonylcarbamoyl]amino]ethyl]phenyl]benzimidazole-5-carboxamide Chemical compound CCC1=NC2=CC(C(N)=O)=C(Cl)C=C2N1C(C=C1)=CC=C1CCN(C)C(=O)NS(=O)(=O)C1=CC=C(C)C=C1 AJZMANQISJQJQM-UHFFFAOYSA-N 0.000 claims description 4
- HSRIKZQJOBFQGC-KRWDZBQOSA-N [(2s)-1-[4-[6-chloro-2-ethyl-5-(trifluoromethyl)benzimidazol-1-yl]phenyl]propan-2-yl] n-(4-methylphenyl)sulfonylcarbamate Chemical compound O([C@@H](C)CC1=CC=C(C=C1)N1C2=CC(Cl)=C(C=C2N=C1CC)C(F)(F)F)C(=O)NS(=O)(=O)C1=CC=C(C)C=C1 HSRIKZQJOBFQGC-KRWDZBQOSA-N 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 3
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Classifications
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- 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
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US24182500P | 2000-10-19 | 2000-10-19 | |
PCT/IB2001/001940 WO2002032900A2 (en) | 2000-10-19 | 2001-10-15 | Aryl or heteroaryl fused imidazole compounds as anti-inflammatory and analgesic agents |
Publications (1)
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HRP20030269A2 true HRP20030269A2 (en) | 2005-02-28 |
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HR20030269A HRP20030269A2 (en) | 2000-10-19 | 2003-04-09 | Aryl or heteroaryl fused imidazole compounds as anti-inflammatory and analgesic agents |
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