BG107699A - Арилни или хетероарилни кондензирани имидазолови съединения с противовъзпалително и обезболвяващо действие - Google Patents
Арилни или хетероарилни кондензирани имидазолови съединения с противовъзпалително и обезболвяващо действие Download PDFInfo
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- BG107699A BG107699A BG107699A BG10769903A BG107699A BG 107699 A BG107699 A BG 107699A BG 107699 A BG107699 A BG 107699A BG 10769903 A BG10769903 A BG 10769903A BG 107699 A BG107699 A BG 107699A
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- Prior art keywords
- ethyl
- alkyl
- amino
- phenyl
- carbonyl
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- 125000003118 aryl group Chemical group 0.000 title claims abstract description 142
- 150000002460 imidazoles Chemical class 0.000 title description 17
- 125000001072 heteroaryl group Chemical group 0.000 title description 10
- 230000003110 anti-inflammatory effect Effects 0.000 title description 3
- 239000000730 antalgic agent Substances 0.000 title 1
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- -1 pain Chemical class 0.000 claims abstract description 413
- 150000001875 compounds Chemical class 0.000 claims abstract description 388
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 346
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 120
- 125000005843 halogen group Chemical group 0.000 claims abstract description 113
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 70
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 67
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 66
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 65
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 54
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 26
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 24
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 8
- 150000003180 prostaglandins Chemical class 0.000 claims abstract description 7
- 230000001404 mediated effect Effects 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 124
- 125000003545 alkoxy group Chemical group 0.000 claims description 112
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 103
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 93
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 54
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 47
- 239000000460 chlorine Substances 0.000 claims description 41
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 40
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
- 229910052794 bromium Inorganic materials 0.000 claims description 31
- 125000000304 alkynyl group Chemical group 0.000 claims description 30
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 28
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 27
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 27
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 25
- 239000005977 Ethylene Substances 0.000 claims description 25
- 125000002947 alkylene group Chemical group 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 22
- 125000005936 piperidyl group Chemical group 0.000 claims description 22
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 20
- 230000000903 blocking effect Effects 0.000 claims description 20
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- 125000000335 thiazolyl group Chemical group 0.000 claims description 16
- 125000001544 thienyl group Chemical group 0.000 claims description 16
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 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
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 229910052727 yttrium Inorganic materials 0.000 claims description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 239000003937 drug carrier Substances 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
- 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
- 239000003814 drug Substances 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 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
- RXUWRKNOUPUCNP-UHFFFAOYSA-N 1-[2-[4-(6-acetyl-2-ethylbenzimidazol-1-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=CC=C(C(C)=O)C=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 RXUWRKNOUPUCNP-UHFFFAOYSA-N 0.000 claims description 4
- YDZNQEMQWNXSGF-UHFFFAOYSA-N 1-[2-[4-(6-chloro-2-ethyl-5-methylsulfonylbenzimidazol-1-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=CC(S(C)(=O)=O)=C(Cl)C=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 YDZNQEMQWNXSGF-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
- 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
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
- 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 3
- 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 3
- LZRDBVMHYJZYKK-UHFFFAOYSA-N 1-[2-[4-(2-butyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCCCC1=NC2=C(C)C=C(C)N=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 LZRDBVMHYJZYKK-UHFFFAOYSA-N 0.000 claims description 3
- XSQBHPPAOXQETA-UHFFFAOYSA-N 1-[2-[4-(2-ethyl-4,5-dimethylbenzimidazol-1-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=C(C)C(C)=CC=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 XSQBHPPAOXQETA-UHFFFAOYSA-N 0.000 claims description 3
- RKBRFPVIJVMSEM-UHFFFAOYSA-N 1-[2-[4-(5,6-dichloro-2-ethylimidazo[4,5-b]pyridin-3-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=CC(Cl)=C(Cl)N=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 RKBRFPVIJVMSEM-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- GFMMZVFKQDQZHJ-UHFFFAOYSA-N 1-[2-[4-[2-ethyl-5-(2-hydroxypropan-2-yl)benzimidazol-1-yl]phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=CC(C(C)(C)O)=CC=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 GFMMZVFKQDQZHJ-UHFFFAOYSA-N 0.000 claims description 3
- GQGGVKWIQFESMF-UHFFFAOYSA-N 1-[2-[4-[5,7-dimethyl-2-(2-methylpropyl)imidazo[4,5-b]pyridin-3-yl]phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CC(C)CC1=NC2=C(C)C=C(C)N=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 GQGGVKWIQFESMF-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 3
- 125000004419 alkynylene group Chemical group 0.000 claims description 3
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims description 3
- GDMPUWXHOZINFC-UHFFFAOYSA-N (4-methylphenyl) n-sulfonylcarbamate Chemical compound CC1=CC=C(OC(=O)N=S(=O)=O)C=C1 GDMPUWXHOZINFC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 2
- CMTOMNMETHIQAO-UHFFFAOYSA-N 1-(2-bromophenyl)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=C1Br CMTOMNMETHIQAO-UHFFFAOYSA-N 0.000 claims description 2
- OJIFDBSNXCGHBQ-UHFFFAOYSA-N 1-(3-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(Cl)=C1 OJIFDBSNXCGHBQ-UHFFFAOYSA-N 0.000 claims description 2
- XCVHOHHHDQCOBD-UHFFFAOYSA-N 1-(4-chloro-3-nitrophenyl)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)C([N+]([O-])=O)=C1 XCVHOHHHDQCOBD-UHFFFAOYSA-N 0.000 claims description 2
- ITYQCVLIFYKIKM-UHFFFAOYSA-N 1-(4-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=C(Cl)C=C1 ITYQCVLIFYKIKM-UHFFFAOYSA-N 0.000 claims description 2
- MPEDBVWYHJKTBI-UHFFFAOYSA-N 1-(5-bromothiophen-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(Br)S1 MPEDBVWYHJKTBI-UHFFFAOYSA-N 0.000 claims description 2
- IBFDKPDVDWAFLS-UHFFFAOYSA-N 1-[2-[4-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)phenyl]ethyl]-1-methyl-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=C(C)C=C(C)N=C2N1C(C=C1)=CC=C1CCN(C)C(=O)NS(=O)(=O)C1=CC=C(C)C=C1 IBFDKPDVDWAFLS-UHFFFAOYSA-N 0.000 claims description 2
- UBBBCBCWMHKSKB-UHFFFAOYSA-N 1-[2-[4-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)phenyl]ethyl]-3-(4-phenylphenyl)sulfonylurea Chemical compound CCC1=NC2=C(C)C=C(C)N=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 UBBBCBCWMHKSKB-UHFFFAOYSA-N 0.000 claims description 2
- DCVOMGDWHZCNLH-UHFFFAOYSA-N 1-[2-[4-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)phenyl]ethyl]-3-naphthalen-1-ylsulfonylurea Chemical compound C1=CC=C2C(S(=O)(=O)NC(=O)NCCC3=CC=C(C=C3)N3C4=NC(C)=CC(C)=C4N=C3CC)=CC=CC2=C1 DCVOMGDWHZCNLH-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- PUETWJKTSRUGDU-UHFFFAOYSA-N 1-[2-[4-(2-ethyl-7-methylbenzimidazol-1-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=CC=CC(C)=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 PUETWJKTSRUGDU-UHFFFAOYSA-N 0.000 claims description 2
- WPMBBXBTXCWNCZ-UHFFFAOYSA-N 1-[2-[4-(4-chloro-2-ethylbenzimidazol-1-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=C(Cl)C=CC=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 WPMBBXBTXCWNCZ-UHFFFAOYSA-N 0.000 claims description 2
- PJBCMGNUMXMKAS-UHFFFAOYSA-N 1-[2-[4-(5-chloro-2-ethyl-7-methylimidazo[4,5-b]pyridin-3-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=C(C)C=C(Cl)N=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 PJBCMGNUMXMKAS-UHFFFAOYSA-N 0.000 claims description 2
- RSXKMRPPWWLXMI-UHFFFAOYSA-N 1-[2-[4-(5-chloro-6-methylbenzimidazol-1-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NCCC1=CC=C(N2C3=CC(C)=C(Cl)C=C3N=C2)C=C1 RSXKMRPPWWLXMI-UHFFFAOYSA-N 0.000 claims description 2
- DNIARSNMMRQNKE-UHFFFAOYSA-N 1-[2-[4-(6-cyano-2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=C(C)C(C#N)=C(C)N=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 DNIARSNMMRQNKE-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- JKPPWQNNVYZCJS-UHFFFAOYSA-N 1-[2-[4-[6-chloro-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=C2)C(F)(F)F)C=C1 JKPPWQNNVYZCJS-UHFFFAOYSA-N 0.000 claims description 2
- NKJLJAMWLOQYMJ-UHFFFAOYSA-N 1-[3-(dihydroxyamino)phenyl]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(N(O)O)=C1 NKJLJAMWLOQYMJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006418 4-methylphenylsulfonyl group Chemical group 0.000 claims description 2
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- 235000010288 sodium nitrite Nutrition 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
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- 230000009870 specific binding Effects 0.000 description 1
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- 229960005322 streptomycin Drugs 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 239000000375 suspending agent Substances 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 150000003564 thiocarbonyl compounds Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000003354 tissue distribution assay Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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- QIVBCDIJIAJPQS-UHFFFAOYSA-M tryptophanate Chemical compound C1=CC=C2C(CC(N)C([O-])=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-M 0.000 description 1
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- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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| PCT/IB2001/001940 WO2002032900A2 (en) | 2000-10-19 | 2001-10-15 | Aryl or heteroaryl fused imidazole compounds as anti-inflammatory and analgesic agents |
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| EP1382603B1 (en) * | 2001-04-26 | 2008-07-23 | Eisai R&D Management Co., Ltd. | Nitrogenous fused-ring compound having pyrazolyl group as substituent and medicinal composition thereof |
| CA2482382A1 (en) * | 2002-04-12 | 2003-10-23 | Pfizer Inc. | Pyrazole compounds as anti-inflammatory and analgesic agents |
| MXPA04009243A (es) | 2002-04-12 | 2005-06-08 | Pfizer | Uso de ligandos para el receptor ep4 en el tratamiento de enfermedades vinculadas a il-6. |
| WO2003086390A1 (en) * | 2002-04-12 | 2003-10-23 | Pfizer Japan Inc. | Imidazole compounds as anti-inflammatory and analgesic agents |
| AU2003293409A1 (en) | 2002-12-09 | 2004-06-30 | Karl K. Johe | Method for discovering neurogenic agents |
| US8293488B2 (en) | 2002-12-09 | 2012-10-23 | Neuralstem, Inc. | Method for screening neurogenic agents |
| KR20050084445A (ko) * | 2002-12-20 | 2005-08-26 | 다이노젠 파마세우티컬스, 인코포레이티드 | α₂δ 서브유닛 칼슘 채널 모듈레이터를 이용한 무통증방광 질환의 치료방법 |
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| JP4185097B2 (ja) * | 2003-03-13 | 2008-11-19 | 出光興産株式会社 | 新規含窒素複素環誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
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| US7271271B2 (en) * | 2004-06-28 | 2007-09-18 | Amgen Sf, Llc | Imidazolo-related compounds, compositions and methods for their use |
| WO2006055685A2 (en) | 2004-11-17 | 2006-05-26 | Neuralstem, Inc. | Transplantation of human neural cells for treatment of neurodegenerative conditions |
| AU2005316091B2 (en) * | 2004-12-17 | 2011-12-01 | Merck Canada Inc. | 2-(phenyl or heterocyclic)-1H-phenantrho[9,10-D]imidazoles as mPGES-1 inhibitors |
| US7442716B2 (en) * | 2004-12-17 | 2008-10-28 | Merck Frosst Canada Ltd. | 2-(phenyl or heterocyclic)-1H-phenantrho[9,10-d]imidazoles as mPGES-1 inhibitors |
| US7534796B2 (en) | 2005-02-18 | 2009-05-19 | Wyeth | Imidazo[4,5-b]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7538113B2 (en) | 2005-02-18 | 2009-05-26 | Wyeth | 4-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7582634B2 (en) | 2005-02-18 | 2009-09-01 | Wyeth | 7-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
| IN2014DN09939A (enExample) | 2005-03-11 | 2015-08-14 | Raqualia Pharma Inc | |
| US7531542B2 (en) | 2005-05-18 | 2009-05-12 | Wyeth | Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor |
| US7582636B2 (en) | 2005-05-26 | 2009-09-01 | Wyeth | Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of Gonadotropin Releasing Hormone receptor |
| AU2006327243A1 (en) * | 2005-12-21 | 2007-06-28 | Decode Genetics Ehf | N-linked aryl heteroaryl inhibitors of LTA4H for treating inflammation |
| EP2019675A4 (en) * | 2006-05-02 | 2011-03-02 | Merck Frosst Canada Ltd | METHOD FOR THE TREATMENT OR PREVENTION OF NEOPLASIA |
| CL2007002994A1 (es) * | 2006-10-19 | 2008-02-08 | Wyeth Corp | Compuestos derivados heterociclicos que contienen sulfamoilo, inhibidores de hsp90; composicion farmaceutica; y uso para el tratamiento del cancer, tal como cancer de mama, de colon y prostata, entre otros. |
| WO2008116304A1 (en) * | 2007-03-26 | 2008-10-02 | Merck Frosst Canada Ltd. | Naphthalene and quinoline sulfonylurea derivatives as ep4 receptor antagonists |
| DE102007037579B4 (de) | 2007-08-09 | 2012-05-16 | Emc Microcollections Gmbh | Neue Benzimidazol-2-yl-alkylamine und ihre Anwendung als mikrobizide Wirkstoffe |
| WO2009029622A2 (en) * | 2007-08-27 | 2009-03-05 | Siga Technologies, Inc. | Antiviral drugs for treatment of arenavirus infection |
| JP2011509990A (ja) | 2008-01-22 | 2011-03-31 | オキサジェン リミテッド | Crth2アンタゴニスト活性を有する化合物 |
| MX2011003166A (es) * | 2008-09-25 | 2011-04-27 | Merck Frosst Canada Ltd | Derivados de sulfonilurea beta-carbolina como antagonistas del receptor ep4. |
| JPWO2010087425A1 (ja) | 2009-01-30 | 2012-08-02 | 国立大学法人京都大学 | 前立腺癌の進行抑制剤および進行抑制方法 |
| US8921391B2 (en) | 2009-04-22 | 2014-12-30 | Raqualia Pharma Inc. | Selective EP4 receptor antagonistic substance for treatment of cancer |
| KR101041561B1 (ko) * | 2009-12-21 | 2011-06-15 | 짚라인코리아 (주) | 비행용 착용복 |
| CN102770159A (zh) * | 2010-02-22 | 2012-11-07 | 拉夸里亚创药株式会社 | Ep-4受体拮抗剂在治疗il-23介导疾病中的用途 |
| RU2013108868A (ru) | 2010-07-28 | 2014-09-10 | Ньюралстем, Инк. | Способы лечения и/или реверсии нейродегенеративных заболеваний и/или расстройств |
| SMT201700008T1 (it) | 2010-09-21 | 2017-03-08 | Eisai R&D Man Co Ltd | Composizione farmaceutica |
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