ZA200402188B - 1H-imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity. - Google Patents
1H-imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity. Download PDFInfo
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- ZA200402188B ZA200402188B ZA200402188A ZA200402188A ZA200402188B ZA 200402188 B ZA200402188 B ZA 200402188B ZA 200402188 A ZA200402188 A ZA 200402188A ZA 200402188 A ZA200402188 A ZA 200402188A ZA 200402188 B ZA200402188 B ZA 200402188B
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- South Africa
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- imidazole
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- 230000001270 agonistic effect Effects 0.000 title description 8
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- 125000001424 substituent group Chemical group 0.000 claims description 15
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- DBNQIOANXZVWIP-UHFFFAOYSA-N n,n-dimethyl-1,1-bis[(2-methylpropan-2-yl)oxy]methanamine Chemical compound CC(C)(C)OC(N(C)C)OC(C)(C)C DBNQIOANXZVWIP-UHFFFAOYSA-N 0.000 description 1
- IVMOOXFELCCOMP-UHFFFAOYSA-N n-(1-adamantyl)-1-(4-chlorophenyl)-2-[4-chloro-2-(trifluoromethyl)phenyl]imidazole-4-carboxamide Chemical compound FC(F)(F)C1=CC(Cl)=CC=C1C1=NC(C(=O)NC23CC4CC(CC(C4)C2)C3)=CN1C1=CC=C(Cl)C=C1 IVMOOXFELCCOMP-UHFFFAOYSA-N 0.000 description 1
- HXLFSLVUWNBRDT-UHFFFAOYSA-N n-(azepan-1-yl)-1-(4-bromophenyl)-2-(2,4-dichlorophenyl)imidazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1C1=NC(C(=O)NN2CCCCCC2)=CN1C1=CC=C(Br)C=C1 HXLFSLVUWNBRDT-UHFFFAOYSA-N 0.000 description 1
- UNINKSRMOUERSC-UHFFFAOYSA-N n-(azepan-1-yl)-1-(4-chloropyridin-2-yl)-2-(2,4-dichlorophenyl)-5-ethylimidazole-4-carboxamide Chemical compound C=1C(Cl)=CC=NC=1N1C(CC)=C(C(=O)NN2CCCCCC2)N=C1C1=CC=C(Cl)C=C1Cl UNINKSRMOUERSC-UHFFFAOYSA-N 0.000 description 1
- GUNCGMZWTDRAJL-UHFFFAOYSA-N n-(azepan-1-yl)-1-(4-chloropyridin-2-yl)-2-(2,4-dichlorophenyl)-5-methylimidazole-4-carboxamide Chemical compound C=1C(Cl)=CC=NC=1N1C(C)=C(C(=O)NN2CCCCCC2)N=C1C1=CC=C(Cl)C=C1Cl GUNCGMZWTDRAJL-UHFFFAOYSA-N 0.000 description 1
- SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical compound FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 description 1
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- RYQNMPVOTHTFIF-UHFFFAOYSA-N n-benzyl-1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-n-methylimidazole-4-carboxamide Chemical compound C=1N(C=2C=CC(Cl)=CC=2)C(C=2C(=CC(Cl)=CC=2)Cl)=NC=1C(=O)N(C)CC1=CC=CC=C1 RYQNMPVOTHTFIF-UHFFFAOYSA-N 0.000 description 1
- NMJMVGDVVZUPOP-UHFFFAOYSA-N n-cyclohexyl-2-(1,5-dimethylpyrrol-2-yl)-5-ethyl-1-phenylimidazole-4-carboxamide Chemical compound C=1C=CC=CC=1N1C(CC)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(C)N1C NMJMVGDVVZUPOP-UHFFFAOYSA-N 0.000 description 1
- VSXOYDKSPXUUIJ-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dichlorophenyl)-1-(2,5-difluorophenyl)-5-ethylimidazole-4-carboxamide Chemical compound C=1C(F)=CC=C(F)C=1N1C(CC)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl VSXOYDKSPXUUIJ-UHFFFAOYSA-N 0.000 description 1
- USKQSLWBDDIJSQ-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-5-methylimidazole-4-carboxamide Chemical compound C=1C=C(F)C=CC=1N1C(C)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl USKQSLWBDDIJSQ-UHFFFAOYSA-N 0.000 description 1
- XJWCYWLSWSGANR-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)-5-methylimidazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NC2CCCCC2)=C1C XJWCYWLSWSGANR-UHFFFAOYSA-N 0.000 description 1
- TWRSTCDKXCLFEK-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)imidazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NC2CCCCC2)=C1 TWRSTCDKXCLFEK-UHFFFAOYSA-N 0.000 description 1
- SBNWHIPARXVTSU-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dichlorophenyl)-1-pyridin-3-ylimidazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1C1=NC(C(=O)NC2CCCCC2)=CN1C1=CC=CN=C1 SBNWHIPARXVTSU-UHFFFAOYSA-N 0.000 description 1
- FBFGYIWCXJGEAG-UHFFFAOYSA-N n-cyclohexyl-2-(2,5-dichlorophenyl)-5-methyl-1-phenylimidazole-4-carboxamide Chemical compound C=1C=CC=CC=1N1C(C)=C(C(=O)NC2CCCCC2)N=C1C1=CC(Cl)=CC=C1Cl FBFGYIWCXJGEAG-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
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- 239000002287 radioligand Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
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Classifications
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- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
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- C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
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- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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ZA200402188A ZA200402188B (en) | 2001-09-21 | 2004-03-18 | 1H-imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity. |
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EP (1) | EP1438296B1 (uk) |
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AU2002319627A1 (en) | 2001-07-20 | 2003-03-03 | Merck And Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
US7109216B2 (en) | 2001-09-21 | 2006-09-19 | Solvay Pharmaceuticals B.V. | 1H-imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity |
HN2002000266A (es) | 2001-09-24 | 2003-11-16 | Bayer Corp | Preparacion y uso de derivados de imidazol para el tratamiento de la obesidad. |
US20060100196A1 (en) * | 2001-09-24 | 2006-05-11 | Andrea Gailunas | Substituted amines for the treatment of alzheimer's disease |
EP1496838B1 (en) | 2002-03-12 | 2010-11-03 | Merck Sharp & Dohme Corp. | Substituted amides |
AU2003275242B2 (en) | 2002-09-27 | 2010-03-04 | Merck Sharp & Dohme Corp. | Substituted pyrimidines |
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