ZA200508108B - Imidazole derivatives for treatment of allergic and hyperproliferative disorders - Google Patents
Imidazole derivatives for treatment of allergic and hyperproliferative disorders Download PDFInfo
- Publication number
- ZA200508108B ZA200508108B ZA200508108A ZA200508108A ZA200508108B ZA 200508108 B ZA200508108 B ZA 200508108B ZA 200508108 A ZA200508108 A ZA 200508108A ZA 200508108 A ZA200508108 A ZA 200508108A ZA 200508108 B ZA200508108 B ZA 200508108B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- imidazol
- substituted
- formula
- species
- Prior art date
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- 150000002460 imidazoles Chemical class 0.000 title claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 17
- 238000011282 treatment Methods 0.000 title description 11
- 230000000172 allergic effect Effects 0.000 title description 2
- 208000010668 atopic eczema Diseases 0.000 title description 2
- 230000003463 hyperproliferative effect Effects 0.000 title description 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 208000006673 asthma Diseases 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- -1 camphoryl Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- 125000001624 naphthyl group Chemical group 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 20
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 17
- 230000004663 cell proliferation Effects 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- 239000003112 inhibitor Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 125000003367 polycyclic group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
- 206010020751 Hypersensitivity Diseases 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 5
- 239000000048 adrenergic agonist Substances 0.000 claims description 5
- 239000002246 antineoplastic agent Substances 0.000 claims description 5
- 230000002757 inflammatory effect Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 208000024891 symptom Diseases 0.000 claims description 5
- 201000009961 allergic asthma Diseases 0.000 claims description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 4
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 4
- 239000000739 antihistaminic agent Substances 0.000 claims description 4
- 239000003246 corticosteroid Substances 0.000 claims description 4
- 231100000614 poison Toxicity 0.000 claims description 4
- 239000002574 poison Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 239000000812 cholinergic antagonist Substances 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000002571 phosphodiesterase inhibitor Substances 0.000 claims description 3
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 2
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 claims description 2
- 231100000632 Spindle poison Toxicity 0.000 claims description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 2
- 102000007537 Type II DNA Topoisomerases Human genes 0.000 claims description 2
- 108010046308 Type II DNA Topoisomerases Proteins 0.000 claims description 2
- 208000030961 allergic reaction Diseases 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 230000001387 anti-histamine Effects 0.000 claims description 2
- 230000000340 anti-metabolite Effects 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 229940121375 antifungal agent Drugs 0.000 claims description 2
- 229940100197 antimetabolite Drugs 0.000 claims description 2
- 239000002256 antimetabolite Substances 0.000 claims description 2
- 239000003443 antiviral agent Substances 0.000 claims description 2
- 229940121357 antivirals Drugs 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 241000894007 species Species 0.000 claims 43
- 150000003839 salts Chemical class 0.000 claims 15
- JBNVRLURWDLBOD-UHFFFAOYSA-N 2-nitrobenzenecarboximidamide Chemical class NC(=N)C1=CC=CC=C1[N+]([O-])=O JBNVRLURWDLBOD-UHFFFAOYSA-N 0.000 claims 8
- QJVFPOMUIKCQED-UHFFFAOYSA-N cycloheptanecarboxamide Chemical compound NC(=O)C1CCCCCC1 QJVFPOMUIKCQED-UHFFFAOYSA-N 0.000 claims 8
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 4
- 230000002862 amidating effect Effects 0.000 claims 4
- 230000003301 hydrolyzing effect Effects 0.000 claims 4
- 239000004615 ingredient Substances 0.000 claims 4
- RHJVIGLEIFVHIJ-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1[CH]CCCC1 RHJVIGLEIFVHIJ-UHFFFAOYSA-N 0.000 claims 3
- SWBDKCMOLSUXRH-UHFFFAOYSA-N 2-nitrobenzonitrile Chemical class [O-][N+](=O)C1=CC=CC=C1C#N SWBDKCMOLSUXRH-UHFFFAOYSA-N 0.000 claims 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 229960003966 nicotinamide Drugs 0.000 claims 2
- 235000005152 nicotinamide Nutrition 0.000 claims 2
- 239000011570 nicotinamide Substances 0.000 claims 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 2
- 150000003919 1,2,3-triazines Chemical class 0.000 claims 1
- 150000003920 1,2,4-triazines Chemical class 0.000 claims 1
- 150000000182 1,3,5-triazines Chemical class 0.000 claims 1
- DMMQAIQJALWYLK-UHFFFAOYSA-N 2-methyl-n-[4-[2-[4-[(4-methylcyclohexanecarbonyl)amino]phenyl]-1h-imidazol-5-yl]phenyl]cyclohexane-1-carboxamide Chemical compound C1CC(C)CCC1C(=O)NC1=CC=C(C=2NC(=CN=2)C=2C=CC(NC(=O)C3C(CCCC3)C)=CC=2)C=C1 DMMQAIQJALWYLK-UHFFFAOYSA-N 0.000 claims 1
- VSKXJRZPVDLHFY-UHFFFAOYSA-N 2-methylcyclohexane-1-carboxylic acid Chemical compound CC1CCCCC1C(O)=O VSKXJRZPVDLHFY-UHFFFAOYSA-N 0.000 claims 1
- DIVSHDBWAVBSKM-UHFFFAOYSA-N 3,4-dichloro-n-[4-[5-[4-[(4-methylcyclohexanecarbonyl)amino]phenyl]-1h-imidazol-2-yl]phenyl]benzamide Chemical compound C1CC(C)CCC1C(=O)NC1=CC=C(C=2NC(=NC=2)C=2C=CC(NC(=O)C=3C=C(Cl)C(Cl)=CC=3)=CC=2)C=C1 DIVSHDBWAVBSKM-UHFFFAOYSA-N 0.000 claims 1
- GXNVLLULQVZGKP-UHFFFAOYSA-N 4-[2-(4-benzamidophenyl)-1h-imidazol-5-yl]-n-cycloheptylbenzamide Chemical compound C=1C=C(C=2NC(=NC=2)C=2C=CC(NC(=O)C=3C=CC=CC=3)=CC=2)C=CC=1C(=O)NC1CCCCCC1 GXNVLLULQVZGKP-UHFFFAOYSA-N 0.000 claims 1
- HFEPISBERRHVSZ-UHFFFAOYSA-N 4-chloro-n-[4-[5-[4-(cyclohexanecarbonylamino)phenyl]-1h-imidazol-2-yl]phenyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1=CC=C(C=2NC(=CN=2)C=2C=CC(NC(=O)C3CCCCC3)=CC=2)C=C1 HFEPISBERRHVSZ-UHFFFAOYSA-N 0.000 claims 1
- VABMLWOXAMWZIU-UHFFFAOYSA-N 4-chloro-n-[4-[5-[4-[(4-methylcyclohexanecarbonyl)amino]phenyl]-1h-imidazol-2-yl]phenyl]benzamide Chemical compound C1CC(C)CCC1C(=O)NC1=CC=C(C=2NC(=NC=2)C=2C=CC(NC(=O)C=3C=CC(Cl)=CC=3)=CC=2)C=C1 VABMLWOXAMWZIU-UHFFFAOYSA-N 0.000 claims 1
- VJIQFMPZZPZZDF-UHFFFAOYSA-N 4-fluoro-n-[4-[5-[4-[(4-methylcyclohexanecarbonyl)amino]phenyl]-1h-imidazol-2-yl]phenyl]benzamide Chemical compound C1CC(C)CCC1C(=O)NC1=CC=C(C=2NC(=NC=2)C=2C=CC(NC(=O)C=3C=CC(F)=CC=3)=CC=2)C=C1 VJIQFMPZZPZZDF-UHFFFAOYSA-N 0.000 claims 1
- TVMWUZGCXROGPR-UHFFFAOYSA-N 4-methoxy-n-[4-[5-[4-[(4-methylcyclohexanecarbonyl)amino]phenyl]-1h-imidazol-2-yl]phenyl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=C(C=2NC(=CN=2)C=2C=CC(NC(=O)C3CCC(C)CC3)=CC=2)C=C1 TVMWUZGCXROGPR-UHFFFAOYSA-N 0.000 claims 1
- NGORKRLCNYGWLW-UHFFFAOYSA-N N-[4-[2-[4-(cycloheptylamino)phenyl]-1H-imidazol-5-yl]phenyl]cyclohexanecarboxamide Chemical compound C1CCCCC1C(=O)NC(C=C1)=CC=C1C(N1)=CN=C1C(C=C1)=CC=C1NC1CCCCCC1 NGORKRLCNYGWLW-UHFFFAOYSA-N 0.000 claims 1
- UKTJKWOKKZDVBF-UHFFFAOYSA-N N-[4-[2-[4-[(2-methylcyclohexyl)amino]phenyl]-1H-imidazol-5-yl]phenyl]cyclohexanecarboxamide Chemical compound CC1CCCCC1NC1=CC=C(C=2NC(=CN=2)C=2C=CC(NC(=O)C3CCCCC3)=CC=2)C=C1 UKTJKWOKKZDVBF-UHFFFAOYSA-N 0.000 claims 1
- 241000282887 Suidae Species 0.000 claims 1
- 101710183280 Topoisomerase Proteins 0.000 claims 1
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 150000008371 chromenes Chemical class 0.000 claims 1
- 150000001907 coumarones Chemical class 0.000 claims 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims 1
- 150000002240 furans Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 150000002461 imidazolidines Chemical class 0.000 claims 1
- 150000002475 indoles Chemical class 0.000 claims 1
- 150000002537 isoquinolines Chemical class 0.000 claims 1
- 150000003854 isothiazoles Chemical class 0.000 claims 1
- 150000002545 isoxazoles Chemical class 0.000 claims 1
- 150000002780 morpholines Chemical class 0.000 claims 1
- YJWQFYWRRATRAC-UHFFFAOYSA-N n-[3-[2-[3-(adamantane-1-carbonylamino)phenyl]-1h-imidazol-5-yl]phenyl]adamantane-1-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)NC1=CC=CC(C=2NC(=NC=2)C=2C=C(NC(=O)C34CC5CC(CC(C5)C3)C4)C=CC=2)=C1 YJWQFYWRRATRAC-UHFFFAOYSA-N 0.000 claims 1
- XQQABVZZCCEIAW-UHFFFAOYSA-N n-[3-[2-[3-(pyridine-2-carbonylamino)phenyl]-1h-imidazol-5-yl]phenyl]pyridine-2-carboxamide Chemical compound C=1C=CC=NC=1C(=O)NC(C=1)=CC=CC=1C(N1)=CN=C1C(C=1)=CC=CC=1NC(=O)C1=CC=CC=N1 XQQABVZZCCEIAW-UHFFFAOYSA-N 0.000 claims 1
- UQOGXMJMRXRATD-UHFFFAOYSA-N n-[4-[2-(4-benzamidophenyl)-1h-imidazol-5-yl]phenyl]cycloheptanecarboxamide Chemical compound C1CCCCCC1C(=O)NC(C=C1)=CC=C1C(N1)=CN=C1C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1 UQOGXMJMRXRATD-UHFFFAOYSA-N 0.000 claims 1
- BYZOBCHATKWXHK-UHFFFAOYSA-N n-[4-[2-[3-(pyridine-2-carbonylamino)phenyl]-1h-imidazol-5-yl]phenyl]pyridine-2-carboxamide Chemical compound C=1C=CC=NC=1C(=O)NC(C=C1)=CC=C1C(N1)=CN=C1C(C=1)=CC=CC=1NC(=O)C1=CC=CC=N1 BYZOBCHATKWXHK-UHFFFAOYSA-N 0.000 claims 1
- UFJSXYPUSMAJBZ-UHFFFAOYSA-N n-[4-[2-[4-(cyclohexanecarbonylamino)phenyl]-1h-imidazol-5-yl]phenyl]cycloheptanecarboxamide Chemical compound C1CCCCC1C(=O)NC(C=C1)=CC=C1C(N1)=NC=C1C(C=C1)=CC=C1NC(=O)C1CCCCCC1 UFJSXYPUSMAJBZ-UHFFFAOYSA-N 0.000 claims 1
- HDUWRKKKWMOMBN-UHFFFAOYSA-N n-[4-[2-[4-(pyridine-3-carbonylamino)phenyl]-1h-imidazol-5-yl]phenyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC(C=C1)=CC=C1C(N1)=CN=C1C(C=C1)=CC=C1NC(=O)C1=CC=CN=C1 HDUWRKKKWMOMBN-UHFFFAOYSA-N 0.000 claims 1
- NXULCFSOIIXRQV-UHFFFAOYSA-N n-[4-[2-[4-[(2,3,4,5,6-pentafluorobenzoyl)amino]phenyl]-1h-imidazol-5-yl]phenyl]pyridine-3-carboxamide Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1C(=O)NC1=CC=C(C=2NC(=CN=2)C=2C=CC(NC(=O)C=3C=NC=CC=3)=CC=2)C=C1 NXULCFSOIIXRQV-UHFFFAOYSA-N 0.000 claims 1
- DQUIILWMJDPCDH-UHFFFAOYSA-N n-[4-[2-[4-[(3,4-dichlorobenzoyl)amino]phenyl]-1h-imidazol-5-yl]phenyl]cycloheptanecarboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)NC1=CC=C(C=2NC(=CN=2)C=2C=CC(NC(=O)C3CCCCCC3)=CC=2)C=C1 DQUIILWMJDPCDH-UHFFFAOYSA-N 0.000 claims 1
- OKYHFGAYXOIQOC-UHFFFAOYSA-N n-[4-[2-[4-[(3,4-dichlorobenzoyl)amino]phenyl]-1h-imidazol-5-yl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)NC1=CC=C(C=2NC(=CN=2)C=2C=CC(NC(=O)C=3C=NC=CC=3)=CC=2)C=C1 OKYHFGAYXOIQOC-UHFFFAOYSA-N 0.000 claims 1
- FSBUVKFEQKPAAS-UHFFFAOYSA-N n-[4-[2-[4-[(4-fluorobenzoyl)amino]phenyl]-1h-imidazol-5-yl]phenyl]cycloheptanecarboxamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=CC=C(C=2NC(=CN=2)C=2C=CC(NC(=O)C3CCCCCC3)=CC=2)C=C1 FSBUVKFEQKPAAS-UHFFFAOYSA-N 0.000 claims 1
- JNVYUAXPLLVOBD-UHFFFAOYSA-N n-[4-[2-[4-[(4-nitrobenzoyl)amino]phenyl]-1h-imidazol-5-yl]phenyl]cycloheptanecarboxamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NC1=CC=C(C=2NC(=CN=2)C=2C=CC(NC(=O)C3CCCCCC3)=CC=2)C=C1 JNVYUAXPLLVOBD-UHFFFAOYSA-N 0.000 claims 1
- NQANDIMEGYQOQV-UHFFFAOYSA-N n-[4-[5-[3-(adamantane-1-carbonylamino)phenyl]-1h-imidazol-2-yl]phenyl]adamantane-1-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)NC1=CC=C(C=2NC(=CN=2)C=2C=C(NC(=O)C34CC5CC(CC(C5)C3)C4)C=CC=2)C=C1 NQANDIMEGYQOQV-UHFFFAOYSA-N 0.000 claims 1
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- FHCWAHVAJAIOLK-UHFFFAOYSA-N n-[4-[5-[4-[(2-methylcyclohexanecarbonyl)amino]phenyl]-1h-imidazol-2-yl]phenyl]cycloheptanecarboxamide Chemical compound CC1CCCCC1C(=O)NC1=CC=C(C=2NC(=NC=2)C=2C=CC(NC(=O)C3CCCCCC3)=CC=2)C=C1 FHCWAHVAJAIOLK-UHFFFAOYSA-N 0.000 claims 1
- ZQBRQCQLTRMVKC-UHFFFAOYSA-N n-[4-[5-[4-[(4-methylcyclohexanecarbonyl)amino]phenyl]-1h-imidazol-2-yl]phenyl]benzamide Chemical compound C1CC(C)CCC1C(=O)NC1=CC=C(C=2NC(=NC=2)C=2C=CC(NC(=O)C=3C=CC=CC=3)=CC=2)C=C1 ZQBRQCQLTRMVKC-UHFFFAOYSA-N 0.000 claims 1
- WWESIRDPRVQYGL-UHFFFAOYSA-N n-[4-[5-[4-[(4-methylcyclohexanecarbonyl)amino]phenyl]-1h-imidazol-2-yl]phenyl]cycloheptanecarboxamide Chemical compound C1CC(C)CCC1C(=O)NC1=CC=C(C=2NC(=NC=2)C=2C=CC(NC(=O)C3CCCCCC3)=CC=2)C=C1 WWESIRDPRVQYGL-UHFFFAOYSA-N 0.000 claims 1
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- FNQCHPDFESLYJJ-UHFFFAOYSA-N n-cycloheptyl-4-[2-[4-[(4-methylcyclohexanecarbonyl)amino]phenyl]-1h-imidazol-5-yl]benzamide Chemical compound C1CC(C)CCC1C(=O)NC1=CC=C(C=2NC(=CN=2)C=2C=CC(=CC=2)C(=O)NC2CCCCCC2)C=C1 FNQCHPDFESLYJJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 1
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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| US46209003P | 2003-04-10 | 2003-04-10 |
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| US6911462B2 (en) * | 1998-05-22 | 2005-06-28 | Avanir Pharmaceuticals | Benzimidazole compounds for regulating IgE |
| US6919366B2 (en) * | 1998-05-22 | 2005-07-19 | Avanir Pharmaceuticals | Benzimidazole derivatives as modulators of IgE |
| ES2291455T3 (es) * | 2001-03-12 | 2008-03-01 | Avanir Pharmaceuticals | Compuestos de bencimidazol para modular ige e inhibir la proliferacion celular. |
| TW200304820A (en) * | 2002-03-25 | 2003-10-16 | Avanir Pharmaceuticals | Use of benzimidazole analogs in the treatment of cell proliferation |
| TWI276631B (en) * | 2002-09-12 | 2007-03-21 | Avanir Pharmaceuticals | Phenyl-aza-benzimidazole compounds for modulating IgE and inhibiting cellular proliferation |
| AU2003270426A1 (en) | 2002-09-12 | 2004-04-30 | Avanir Pharmaceuticals | PHENYL-INDOLE COMPOUNDS FOR MODULATING IgE AND INHIBITING CELLULAR PROLIFERATION |
| AU2004263190A1 (en) * | 2003-08-08 | 2005-02-17 | Avanir Pharmaceuticals | Selective pharmacologic inhibition of protein trafficking and related methods of treating human diseases |
| CN101022728B (zh) * | 2004-03-25 | 2012-08-08 | 詹森药业有限公司 | 咪唑化合物 |
| WO2007132307A1 (en) * | 2006-05-09 | 2007-11-22 | Pfizer Products Inc. | Cycloalkylamino acid derivatives and pharmaceutical compositions thereof |
| PE20080948A1 (es) | 2006-07-25 | 2008-09-10 | Irm Llc | Derivados de imidazol como moduladores de la senda de hedgehog |
| US9187485B2 (en) | 2007-02-02 | 2015-11-17 | Baylor College Of Medicine | Methods and compositions for the treatment of cancer and related hyperproliferative disorders |
| US9447049B2 (en) | 2010-03-01 | 2016-09-20 | University Of Tennessee Research Foundation | Compounds for treatment of cancer |
| ES2927660T3 (es) | 2008-06-16 | 2022-11-10 | Univ Tennessee Res Found | Compuestos para el tratamiento del cáncer |
| US9029408B2 (en) | 2008-06-16 | 2015-05-12 | Gtx, Inc. | Compounds for treatment of cancer |
| RU2506260C2 (ru) * | 2008-06-25 | 2014-02-10 | Энвиво Фармасьютикалз, Инк. | 1,2-дизамещенные гетероциклические соединения |
| KR20120130777A (ko) | 2010-03-01 | 2012-12-03 | 유니버시티 오브 테네시 리서치 파운데이션 | 암 치료용 화합물 |
| TWI640507B (zh) | 2013-11-05 | 2018-11-11 | 拜耳作物科學股份有限公司 | 用於控制節肢動物的新穎化合物（三） |
| EP3237413A4 (en) | 2014-12-23 | 2018-09-12 | FGH Biotech | Compositions of fatostatin based heterocyclic compounds and uses thereof |
| CN109476635B (zh) | 2016-04-29 | 2021-07-13 | Fgh生物科技公司 | 用于治疗疾病的二取代吡唑类化合物 |
| EP3510027B1 (en) | 2016-09-07 | 2022-11-02 | FGH BioTech, Inc. | Di-substituted pyrazole compounds for the treatment of diseases |
| WO2018140504A1 (en) * | 2017-01-24 | 2018-08-02 | Patel Manoj K | Compositions and methods for blocking sodium channels |
| CN108191667B (zh) * | 2018-01-04 | 2021-03-26 | 利尔化学股份有限公司 | 2-硝基-4-三氟甲基苯甲酸甲酯的制备方法 |
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| US5206257A (en) * | 1987-03-05 | 1993-04-27 | May & Baker Limited | Pesticidal method using 2-phenylimidazole derivatives |
| JP2630432B2 (ja) * | 1987-08-24 | 1997-07-16 | コニカ株式会社 | 新規なシアンカプラーを含有するハロゲン化銀カラー写真感光材料 |
| JPH01224759A (ja) * | 1988-03-03 | 1989-09-07 | Konica Corp | 新規なシアンカプラーを含有するハロゲン化銀写真感光材料 |
| JPH01225949A (ja) * | 1988-03-04 | 1989-09-08 | Konica Corp | ハロゲン化銀写真感光材料 |
| JPH01262546A (ja) * | 1988-04-13 | 1989-10-19 | Konica Corp | 新規なシアンカプラーを含有するハロゲン化銀写真感光材料 |
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| JPH03245140A (ja) * | 1990-02-23 | 1991-10-31 | Konica Corp | 新規なシアンカプラーを含有するハロゲン化銀写真感光材料 |
| US5656762A (en) * | 1990-12-28 | 1997-08-12 | Neurogen Corporation | 4-piperidino-and piperazinomethyl-2-phenylimidazole derivatives, dopamine receptor subtype specific ligands |
| JPH09304897A (ja) * | 1996-05-10 | 1997-11-28 | Konica Corp | 新規なシアンカプラーを含有するハロゲン化銀写真感光材料 |
| TW467902B (en) * | 1996-07-31 | 2001-12-11 | Bristol Myers Squibb Co | Diphenyl heterocycles as potassium channel modulators |
| CA2232467A1 (en) * | 1997-03-20 | 1998-09-20 | Richard A. Glennon | Imidazoles with serotonin receptor binding activity |
| GB0007405D0 (en) * | 2000-03-27 | 2000-05-17 | Smithkline Beecham Corp | Compounds |
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| AU2004229466A1 (en) | 2004-10-28 |
| MXJL05000041A (es) | 2005-12-22 |
| TW200503695A (en) | 2005-02-01 |
| JP2006522820A (ja) | 2006-10-05 |
| RU2005134670A (ru) | 2006-06-10 |
| BRPI0409097A (pt) | 2006-04-11 |
| AR045886A1 (es) | 2005-11-16 |
| PL378919A1 (pl) | 2006-06-12 |
| CA2521841A1 (en) | 2004-10-28 |
| WO2004091610A1 (en) | 2004-10-28 |
| CN1826111A (zh) | 2006-08-30 |
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| EP1613310A1 (en) | 2006-01-11 |
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