ZA200302722B - 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 agents. Download PDFInfo
- Publication number
- ZA200302722B ZA200302722B ZA200302722A ZA200302722A ZA200302722B ZA 200302722 B ZA200302722 B ZA 200302722B ZA 200302722 A ZA200302722 A ZA 200302722A ZA 200302722 A ZA200302722 A ZA 200302722A ZA 200302722 B ZA200302722 B ZA 200302722B
- Authority
- ZA
- South Africa
- Prior art keywords
- ethyl
- alkyl
- amino
- phenyl
- halo
- Prior art date
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- 125000003118 aryl group Chemical group 0.000 title claims description 65
- 125000001072 heteroaryl group Chemical group 0.000 title description 4
- 239000000730 antalgic agent Substances 0.000 title description 2
- 150000002460 imidazoles Chemical class 0.000 title description 2
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 230000003110 anti-inflammatory effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 212
- -1 cyano, indanyl Chemical group 0.000 claims description 111
- 125000003545 alkoxy group Chemical group 0.000 claims description 96
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 90
- 125000002950 monocyclic group Chemical group 0.000 claims description 59
- 125000005843 halogen group Chemical group 0.000 claims description 56
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 229910052717 sulfur Inorganic materials 0.000 claims description 35
- 125000002619 bicyclic group Chemical group 0.000 claims description 34
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 32
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000005842 heteroatom Chemical group 0.000 claims description 31
- 125000002947 alkylene group Chemical group 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 125000000304 alkynyl group Chemical group 0.000 claims description 25
- 125000004414 alkyl thio group Chemical group 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004043 oxo group Chemical group O=* 0.000 claims description 11
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000005936 piperidyl group Chemical group 0.000 claims description 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 9
- 150000003180 prostaglandins Chemical class 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 125000004419 alkynylene group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 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 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- 239000002831 pharmacologic agent Substances 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 25
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 7
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 6
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 6
- VATAIZDYZPAXOX-UHFFFAOYSA-N (4-methylphenyl)sulfonylcarbamic acid Chemical compound CC1=CC=C(S(=O)(=O)NC(O)=O)C=C1 VATAIZDYZPAXOX-UHFFFAOYSA-N 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 4
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 3
- 239000005977 Ethylene Substances 0.000 claims 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 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 2
- 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 2
- 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 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- DJCKGBKRWDFMCI-UHFFFAOYSA-N 1-(1-benzothiophen-2-ylsulfonyl)-3-[2-[4-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)phenyl]ethyl]urea Chemical compound C1=CC=C2SC(S(=O)(=O)NC(=O)NCCC3=CC=C(C=C3)N3C4=NC(C)=CC(C)=C4N=C3CC)=CC2=C1 DJCKGBKRWDFMCI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- GPYDLTMRLWLKHM-UHFFFAOYSA-N 1-[2-[4-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)phenyl]ethyl]-3-naphthalen-2-ylsulfonylurea Chemical compound C1=CC=CC2=CC(S(=O)(=O)NC(=O)NCCC3=CC=C(C=C3)N3C4=NC(C)=CC(C)=C4N=C3CC)=CC=C21 GPYDLTMRLWLKHM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CBFFANHNQPPLPD-UHFFFAOYSA-N 1-[2-[4-(5,6-dichloro-2-ethylbenzimidazol-1-yl)phenyl]ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCC1=NC2=CC(Cl)=C(Cl)C=C2N1C(C=C1)=CC=C1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 CBFFANHNQPPLPD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims 1
- 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 1
- 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 1
- 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 1
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| 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. |
| JP2005532291A (ja) * | 2002-04-12 | 2005-10-27 | ファイザー株式会社 | 抗炎症薬および鎮痛薬としてのピラゾール化合物 |
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