JP2007530570A5 - - Google Patents
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- JP2007530570A5 JP2007530570A5 JP2007505143A JP2007505143A JP2007530570A5 JP 2007530570 A5 JP2007530570 A5 JP 2007530570A5 JP 2007505143 A JP2007505143 A JP 2007505143A JP 2007505143 A JP2007505143 A JP 2007505143A JP 2007530570 A5 JP2007530570 A5 JP 2007530570A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- imidazol
- phenyl
- compounds
- effective amount
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 99
- 239000000203 mixture Substances 0.000 claims 57
- 230000003110 anti-inflammatory effect Effects 0.000 claims 40
- 210000000265 leukocyte Anatomy 0.000 claims 39
- 230000007115 recruitment Effects 0.000 claims 39
- 125000001424 substituent group Chemical group 0.000 claims 21
- 239000003112 inhibitor Substances 0.000 claims 20
- 230000001404 mediated effect Effects 0.000 claims 20
- 239000008194 pharmaceutical composition Substances 0.000 claims 20
- 229940075993 receptor modulator Drugs 0.000 claims 20
- 102000005962 receptors Human genes 0.000 claims 20
- 108020003175 receptors Proteins 0.000 claims 20
- 230000002401 inhibitory effect Effects 0.000 claims 19
- 125000000217 alkyl group Chemical group 0.000 claims 18
- -1 hydroxy, amino Chemical group 0.000 claims 17
- 206010061218 Inflammation Diseases 0.000 claims 12
- 230000004054 inflammatory process Effects 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- 125000004122 cyclic group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 230000004044 response Effects 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000006045 Spondylarthropathies Diseases 0.000 claims 2
- 206010047115 Vasculitis Diseases 0.000 claims 2
- 201000004339 autoimmune neuropathy Diseases 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 201000005671 spondyloarthropathy Diseases 0.000 claims 2
- UDKANNDWYRRQOQ-UHFFFAOYSA-N 1,2-dimethyl-4-[3-[4-[4-phenyl-5-(trifluoromethyl)-1h-imidazol-2-yl]phenoxy]propyl]piperazine Chemical compound C1CN(C)C(C)CN1CCCOC1=CC=C(C=2NC(=C(N=2)C=2C=CC=CC=2)C(F)(F)F)C=C1 UDKANNDWYRRQOQ-UHFFFAOYSA-N 0.000 claims 1
- MNNYISHPDMQFHZ-UHFFFAOYSA-N 1-(4-methylpiperazin-1-yl)-3-[5-[5-methyl-4-[4-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]pyridin-2-yl]oxypropan-1-one Chemical compound C1CN(C)CCN1C(=O)CCOC1=CC=C(C=2NC(C)=C(N=2)C=2C=CC(=CC=2)C(F)(F)F)C=N1 MNNYISHPDMQFHZ-UHFFFAOYSA-N 0.000 claims 1
- TYUUIESDBRAOMF-UHFFFAOYSA-N 1-[3-[2-chloro-4-(1h-imidazol-2-yl)phenoxy]propyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC=CN=2)C=C1Cl TYUUIESDBRAOMF-UHFFFAOYSA-N 0.000 claims 1
- AKRQRMAWBKXPDT-UHFFFAOYSA-N 1-[3-[2-chloro-4-[4-phenyl-5-(trifluoromethyl)-1h-imidazol-2-yl]phenoxy]propyl]-4-methyl-1,4-diazepane Chemical compound C1CN(C)CCCN1CCCOC1=CC=C(C=2NC(=C(N=2)C=2C=CC=CC=2)C(F)(F)F)C=C1Cl AKRQRMAWBKXPDT-UHFFFAOYSA-N 0.000 claims 1
- UOTFYIGUHJGCCF-UHFFFAOYSA-N 1-[3-[3-chloro-4-(4,5-dimethyl-1h-imidazol-2-yl)phenoxy]propyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC(C)=C(C)N1 UOTFYIGUHJGCCF-UHFFFAOYSA-N 0.000 claims 1
- LWUGEDSDNLDXBV-UHFFFAOYSA-N 1-[3-[3-chloro-4-(4,5-diphenyl-1h-imidazol-2-yl)phenoxy]propyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 LWUGEDSDNLDXBV-UHFFFAOYSA-N 0.000 claims 1
- UIMORZQCYMONNX-UHFFFAOYSA-N 1-[3-[3-chloro-4-[4-phenyl-5-(trifluoromethyl)-1h-imidazol-2-yl]phenoxy]propyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC(C=2C=CC=CC=2)=C(C(F)(F)F)N1 UIMORZQCYMONNX-UHFFFAOYSA-N 0.000 claims 1
- CHERCHYBVKWSIU-UHFFFAOYSA-N 1-[3-[4-[4,5-bis(2-chlorophenyl)-1h-imidazol-2-yl]-3-chlorophenoxy]propyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC(C=2C(=CC=CC=2)Cl)=C(C=2C(=CC=CC=2)Cl)N1 CHERCHYBVKWSIU-UHFFFAOYSA-N 0.000 claims 1
- MZRIVHQUAOBBDF-UHFFFAOYSA-N 1-[3-[4-[4,5-bis(3-methoxyphenyl)-1h-imidazol-2-yl]-2-fluorophenoxy]propyl]-4-methylpiperazine Chemical compound COC1=CC=CC(C2=C(NC(=N2)C=2C=C(F)C(OCCCN3CCN(C)CC3)=CC=2)C=2C=C(OC)C=CC=2)=C1 MZRIVHQUAOBBDF-UHFFFAOYSA-N 0.000 claims 1
- OIBIRADZMCPFQO-UHFFFAOYSA-N 1-[3-[4-[4,5-bis(3-methoxyphenyl)-1h-imidazol-2-yl]-3-chlorophenoxy]propyl]-4-methylpiperazine Chemical compound COC1=CC=CC(C2=C(NC(=N2)C=2C(=CC(OCCCN3CCN(C)CC3)=CC=2)Cl)C=2C=C(OC)C=CC=2)=C1 OIBIRADZMCPFQO-UHFFFAOYSA-N 0.000 claims 1
- BSSXHWSFCAKOHB-UHFFFAOYSA-N 1-[3-[4-[4,5-bis(4-bromophenyl)-1h-imidazol-2-yl]-3-chlorophenoxy]propyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC(C=2C=CC(Br)=CC=2)=C(C=2C=CC(Br)=CC=2)N1 BSSXHWSFCAKOHB-UHFFFAOYSA-N 0.000 claims 1
- PZOSJTGCZXZWLU-UHFFFAOYSA-N 1-[3-[4-[4,5-bis(4-fluorophenyl)-1h-imidazol-2-yl]-3-chlorophenoxy]propyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC(C=2C=CC(F)=CC=2)=C(C=2C=CC(F)=CC=2)N1 PZOSJTGCZXZWLU-UHFFFAOYSA-N 0.000 claims 1
- HZFUMUFABCLMBX-UHFFFAOYSA-N 1-[3-[4-[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]-3-chlorophenoxy]propyl]-4-methylpiperazine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(C=2C(=CC(OCCCN3CCN(C)CC3)=CC=2)Cl)=N1 HZFUMUFABCLMBX-UHFFFAOYSA-N 0.000 claims 1
- HRFYWOPBFPBNDW-UHFFFAOYSA-N 1-[3-[4-[4,5-bis(4-methylphenyl)-1h-imidazol-2-yl]-3-chlorophenoxy]propyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC(C=2C=CC(C)=CC=2)=C(C=2C=CC(C)=CC=2)N1 HRFYWOPBFPBNDW-UHFFFAOYSA-N 0.000 claims 1
- RQCSELTYGFAPRE-UHFFFAOYSA-N 1-[3-[4-[4-(4-chlorophenyl)-5-methyl-1h-imidazol-2-yl]-3-methylphenoxy]-2-methylpropyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC(C)COC(C=C1C)=CC=C1C(NC=1C)=NC=1C1=CC=C(Cl)C=C1 RQCSELTYGFAPRE-UHFFFAOYSA-N 0.000 claims 1
- SOFDNFMIVCRDDK-UHFFFAOYSA-N 1-[4-[4-(4-chlorophenyl)-5-methyl-1h-imidazol-2-yl]-3-methylphenoxy]-3-(4-methylpiperazin-1-yl)propan-2-ol Chemical compound C1CN(C)CCN1CC(O)COC(C=C1C)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)=C(C)N1 SOFDNFMIVCRDDK-UHFFFAOYSA-N 0.000 claims 1
- XHNTZJGMEUREFG-UHFFFAOYSA-N 1-methyl-4-[3-[3-methyl-4-[5-methyl-4-(2-methylpropyl)-1h-imidazol-2-yl]phenoxy]propyl]piperidine Chemical compound CC1=C(CC(C)C)NC(C=2C(=CC(OCCCC3CCN(C)CC3)=CC=2)C)=N1 XHNTZJGMEUREFG-UHFFFAOYSA-N 0.000 claims 1
- MBPWDHXHDHDZSM-UHFFFAOYSA-N 1-methyl-4-[3-[3-methyl-4-[5-methyl-4-[3-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]phenoxy]propyl]piperidine Chemical compound C1CN(C)CCC1CCCOC(C=C1C)=CC=C1C1=NC(C=2C=C(C=CC=2)C(F)(F)F)=C(C)N1 MBPWDHXHDHDZSM-UHFFFAOYSA-N 0.000 claims 1
- ALTLGIMYHDUBLC-UHFFFAOYSA-N 1-methyl-4-[3-[4-(5-methyl-4-thiophen-2-yl-1h-imidazol-2-yl)phenoxy]propyl]piperidine Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC(C)=C(N=2)C=2SC=CC=2)C=C1 ALTLGIMYHDUBLC-UHFFFAOYSA-N 0.000 claims 1
- FZNDOCMBAXXQLF-UHFFFAOYSA-N 1-methyl-4-[3-[4-[4-phenyl-5-(trifluoromethyl)-1h-imidazol-2-yl]naphthalen-1-yl]oxypropyl]piperidine Chemical compound C1CN(C)CCC1CCCOC(C1=CC=CC=C11)=CC=C1C1=NC(C=2C=CC=CC=2)=C(C(F)(F)F)N1 FZNDOCMBAXXQLF-UHFFFAOYSA-N 0.000 claims 1
- CPNJCWCRUKRHTR-UHFFFAOYSA-N 1-methyl-4-[3-[5-[5-methyl-4-[3-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]pyridin-2-yl]oxypropyl]piperazine Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC(C)=C(N=2)C=2C=C(C=CC=2)C(F)(F)F)C=N1 CPNJCWCRUKRHTR-UHFFFAOYSA-N 0.000 claims 1
- ODTKOBJQMATOTJ-UHFFFAOYSA-N 1-methyl-4-[4-[3-[4-phenyl-5-(trifluoromethyl)-1h-imidazol-2-yl]phenoxy]butyl]piperidine Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC(=C(N=2)C=2C=CC=CC=2)C(F)(F)F)=C1 ODTKOBJQMATOTJ-UHFFFAOYSA-N 0.000 claims 1
- KUTRHUXVQZBEDN-UHFFFAOYSA-N 1-methyl-4-[4-[3-methyl-6-[5-methyl-4-[3-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]pyridin-2-yl]oxybutyl]piperazine Chemical compound C1CN(C)CCN1CCCCOC1=NC(C=2NC(C)=C(N=2)C=2C=C(C=CC=2)C(F)(F)F)=CC=C1C KUTRHUXVQZBEDN-UHFFFAOYSA-N 0.000 claims 1
- NEFDJVHXDLBIOY-UHFFFAOYSA-N 1-methyl-4-[4-[4-[5-methyl-4-[3-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]pyridin-2-yl]oxybutyl]-1,4-diazepane Chemical compound C1CN(C)CCCN1CCCCOC1=CC(C=2NC(C)=C(N=2)C=2C=C(C=CC=2)C(F)(F)F)=CC=N1 NEFDJVHXDLBIOY-UHFFFAOYSA-N 0.000 claims 1
- QXEZQVFBNVAISF-UHFFFAOYSA-N 2,4-dimethyl-1-[3-[4-[4-phenyl-5-(trifluoromethyl)-1h-imidazol-2-yl]phenoxy]propyl]piperazine Chemical compound CC1CN(C)CCN1CCCOC1=CC=C(C=2NC(=C(N=2)C=2C=CC=CC=2)C(F)(F)F)C=C1 QXEZQVFBNVAISF-UHFFFAOYSA-N 0.000 claims 1
- SKXDALOMIKGDPF-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4,5,6,7-tetrahydro-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C(N1)=NC2=C1CCCC2 SKXDALOMIKGDPF-UHFFFAOYSA-N 0.000 claims 1
- IKTQQVDXAPTDFV-UHFFFAOYSA-N 2-[3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=NC=CC=C3N=2)=C1 IKTQQVDXAPTDFV-UHFFFAOYSA-N 0.000 claims 1
- IIBFYYLZJNZFKP-UHFFFAOYSA-N 2-[4-(1-methylpiperidin-4-yl)butoxy]-4-[4-phenyl-5-(trifluoromethyl)-1h-imidazol-2-yl]pyridine Chemical compound C1CN(C)CCC1CCCCOC1=CC(C=2NC(=C(N=2)C=2C=CC=CC=2)C(F)(F)F)=CC=N1 IIBFYYLZJNZFKP-UHFFFAOYSA-N 0.000 claims 1
- ILILMAZRLJBOAW-UHFFFAOYSA-N 2-[4-(1-methylpiperidin-4-yl)butoxy]-4-[5-methyl-4-[3-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]pyridine Chemical compound C1CN(C)CCC1CCCCOC1=CC(C=2NC(C)=C(N=2)C=2C=C(C=CC=2)C(F)(F)F)=CC=N1 ILILMAZRLJBOAW-UHFFFAOYSA-N 0.000 claims 1
- HAJZDGRVIYLJEJ-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-5-methyl-1h-imidazol-2-yl]-6-[4-(1-methylpiperidin-4-yl)butoxy]pyridine Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC(C)=C(N=2)C=2C=CC(Cl)=CC=2)=N1 HAJZDGRVIYLJEJ-UHFFFAOYSA-N 0.000 claims 1
- XABDNAXZGWOGOU-UHFFFAOYSA-N 3-chloro-2-[4-(1-methylpiperidin-4-yl)butoxy]-4-[4-phenyl-5-(trifluoromethyl)-1h-imidazol-2-yl]pyridine Chemical compound C1CN(C)CCC1CCCCOC1=NC=CC(C=2NC(=C(N=2)C=2C=CC=CC=2)C(F)(F)F)=C1Cl XABDNAXZGWOGOU-UHFFFAOYSA-N 0.000 claims 1
- KIZIWPWNRRYFEX-UHFFFAOYSA-N 4-[2-[4-[4-(4-chlorophenyl)-5-methyl-1h-imidazol-2-yl]-3-methylphenoxy]ethoxy]-1-methylpiperidine Chemical compound C1CN(C)CCC1OCCOC(C=C1C)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)=C(C)N1 KIZIWPWNRRYFEX-UHFFFAOYSA-N 0.000 claims 1
- FRBMXTVQNCPELT-UHFFFAOYSA-N 4-[3-[3-chloro-4-[4-(3,5-dichlorophenyl)-5-methyl-1h-imidazol-2-yl]phenoxy]propyl]-1-methylpiperidine Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC(C=2C=C(Cl)C=C(Cl)C=2)=C(C)N1 FRBMXTVQNCPELT-UHFFFAOYSA-N 0.000 claims 1
- PNEITGHFQLBYNA-UHFFFAOYSA-N 4-[3-[3-chloro-4-[4-(4-chlorophenyl)-5-methyl-1h-imidazol-2-yl]phenoxy]propyl]-1-ethylpiperidine Chemical compound C1CN(CC)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)=C(C)N1 PNEITGHFQLBYNA-UHFFFAOYSA-N 0.000 claims 1
- KFMSUHVISDKWFO-UHFFFAOYSA-N 4-[3-[3-chloro-4-[4-(4-chlorophenyl)-5-methyl-1h-imidazol-2-yl]phenoxy]propyl]-1-methylpiperidine Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)=C(C)N1 KFMSUHVISDKWFO-UHFFFAOYSA-N 0.000 claims 1
- CUADEYRLQBPWLW-UHFFFAOYSA-N 4-[3-[3-chloro-4-[4-(4-chlorophenyl)-5-methyl-1h-imidazol-2-yl]phenoxy]propyl]piperidine Chemical compound CC=1NC(C=2C(=CC(OCCCC3CCNCC3)=CC=2)Cl)=NC=1C1=CC=C(Cl)C=C1 CUADEYRLQBPWLW-UHFFFAOYSA-N 0.000 claims 1
- GFUNQXVTJSPORM-UHFFFAOYSA-N 4-[3-[3-chloro-4-[5-methyl-4-(2-methylpropyl)-1h-imidazol-2-yl]phenoxy]propyl]-1-methylpiperidine Chemical compound CC1=C(CC(C)C)NC(C=2C(=CC(OCCCC3CCN(C)CC3)=CC=2)Cl)=N1 GFUNQXVTJSPORM-UHFFFAOYSA-N 0.000 claims 1
- BWHCVHAGHADODQ-UHFFFAOYSA-N 4-[3-[4-[4,5-bis(3-methoxyphenyl)-1h-imidazol-2-yl]-3-chlorophenoxy]propyl]-1-methylpiperidine Chemical compound COC1=CC=CC(C2=C(NC(=N2)C=2C(=CC(OCCCC3CCN(C)CC3)=CC=2)Cl)C=2C=C(OC)C=CC=2)=C1 BWHCVHAGHADODQ-UHFFFAOYSA-N 0.000 claims 1
- VQRKIVQDLSMEDF-UHFFFAOYSA-N 4-[3-[4-[4,5-bis(4-fluorophenyl)-1h-imidazol-2-yl]-3-chlorophenoxy]propyl]-1-methylpiperidine Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC(C=2C=CC(F)=CC=2)=C(C=2C=CC(F)=CC=2)N1 VQRKIVQDLSMEDF-UHFFFAOYSA-N 0.000 claims 1
- WKQQHQGMLVOSMU-UHFFFAOYSA-N 4-[3-[4-[4-(3,5-dichlorophenyl)-5-methyl-1h-imidazol-2-yl]-3-methylphenoxy]propyl]-1-methylpiperidine Chemical compound C1CN(C)CCC1CCCOC(C=C1C)=CC=C1C1=NC(C=2C=C(Cl)C=C(Cl)C=2)=C(C)N1 WKQQHQGMLVOSMU-UHFFFAOYSA-N 0.000 claims 1
- FEONYCYIUYLWLW-UHFFFAOYSA-N 4-[3-[4-[4-(4-chlorophenyl)-5-methyl-1h-imidazol-2-yl]-3-methylphenoxy]propyl]-1-methylpiperidine Chemical compound C1CN(C)CCC1CCCOC(C=C1C)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)=C(C)N1 FEONYCYIUYLWLW-UHFFFAOYSA-N 0.000 claims 1
- KKXRDHXBSLYFMY-UHFFFAOYSA-N 4-[3-[4-[5-(cyclopropylmethyl)-4-[3-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]-3-methylphenoxy]propyl]-1-methylpiperidine Chemical compound C1CN(C)CCC1CCCOC(C=C1C)=CC=C1C(N1)=NC(C=2C=C(C=CC=2)C(F)(F)F)=C1CC1CC1 KKXRDHXBSLYFMY-UHFFFAOYSA-N 0.000 claims 1
- PXGUBYXRWCDGAL-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-5-(trifluoromethyl)-1h-imidazol-2-yl]-2-[4-(1-methylpiperidin-4-yl)butoxy]pyrimidine Chemical compound C1CN(C)CCC1CCCCOC1=NC=CC(C=2NC(=C(N=2)C=2C=CC(Cl)=CC=2)C(F)(F)F)=N1 PXGUBYXRWCDGAL-UHFFFAOYSA-N 0.000 claims 1
- ABMUEXSWEJWLMU-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-5-methyl-1h-imidazol-2-yl]-2-[4-(1-methylpiperidin-4-yl)butoxy]pyridine Chemical compound C1CN(C)CCC1CCCCOC1=CC(C=2NC(C)=C(N=2)C=2C=CC(Cl)=CC=2)=CC=N1 ABMUEXSWEJWLMU-UHFFFAOYSA-N 0.000 claims 1
- ZKWJZTIYVJUZED-UHFFFAOYSA-N 4-[4-[3-[4-(4-chlorophenyl)-5-methyl-1h-imidazol-2-yl]phenoxy]butyl]-1-methylpiperidine Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC(C)=C(N=2)C=2C=CC(Cl)=CC=2)=C1 ZKWJZTIYVJUZED-UHFFFAOYSA-N 0.000 claims 1
- ZMFBLGMBNHQABI-UHFFFAOYSA-N 4-methyl-2-[3-(1-methylpiperidin-4-yl)propoxy]-5-[5-methyl-4-[3-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]pyridine Chemical compound C1CN(C)CCC1CCCOC1=CC(C)=C(C=2NC(C)=C(N=2)C=2C=C(C=CC=2)C(F)(F)F)C=N1 ZMFBLGMBNHQABI-UHFFFAOYSA-N 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- NKGKHOSZSZREDX-UHFFFAOYSA-N 5-[4-(3,5-dichlorophenyl)-5-methyl-1h-imidazol-2-yl]-2-[3-(1-methylpiperidin-4-yl)propoxy]pyridine Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC(C)=C(N=2)C=2C=C(Cl)C=C(Cl)C=2)C=N1 NKGKHOSZSZREDX-UHFFFAOYSA-N 0.000 claims 1
- GHHVEGIIHRCQIA-UHFFFAOYSA-N 5-[4-(4-chlorophenyl)-5-methyl-1h-imidazol-2-yl]-2-[3-(1-methylpiperidin-4-yl)propoxy]pyridine Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC(C)=C(N=2)C=2C=CC(Cl)=CC=2)C=N1 GHHVEGIIHRCQIA-UHFFFAOYSA-N 0.000 claims 1
- OESKMZMMXIDUNS-UHFFFAOYSA-N 5-bromo-2-[4-(1-methylpiperidin-4-yl)butoxy]-4-[5-methyl-4-[3-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]pyridine Chemical compound C1CN(C)CCC1CCCCOC1=CC(C=2NC(C)=C(N=2)C=2C=C(C=CC=2)C(F)(F)F)=C(Br)C=N1 OESKMZMMXIDUNS-UHFFFAOYSA-N 0.000 claims 1
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| EA011242B1 (ru) * | 2004-03-25 | 2009-02-27 | Янссен Фармацевтика Н.В. | Производные имидазола |
| GB0525068D0 (en) | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| WO2007117400A2 (en) * | 2006-03-31 | 2007-10-18 | Janssen Pharmaceutica N.V. | Benzoimidazol-2-yl pyridines as modulators of the histamine h4 receptor |
| WO2007117399A2 (en) * | 2006-03-31 | 2007-10-18 | Janssen Pharmaceutica N.V. | Benzoimidazol-2-yl pyrimidines and pyrazines as modulators of the histamine h4 receptor |
| WO2007120690A2 (en) * | 2006-04-10 | 2007-10-25 | Janssen Pharmaceutica N.V. | Combination histamine h1r and h4r antagonist therapy for treating pruritus |
| AU2007272956B2 (en) * | 2006-07-11 | 2013-05-02 | Janssen Pharmaceutica, N.V. | Benzofuro-and benzothienopyryimidine modulators of the histamine H4 receptor |
| US7985745B2 (en) | 2006-10-02 | 2011-07-26 | Abbott Laboratories | Method for pain treatment |
| CL2008000467A1 (es) * | 2007-02-14 | 2008-08-22 | Janssen Pharmaceutica Nv | Compuestos derivados de 2-aminopirimidina, moduladores del receptor histamina h4; su procedimiento de preparacion; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar un trastorno inflamatorio seleccionado de alegia, asma |
| TW200924781A (en) | 2007-09-14 | 2009-06-16 | Janssen Pharmaceutica Nv | Thieno- and furo-pyrimidine modulators of the histamine H4 receptor |
| WO2009079001A1 (en) * | 2007-12-18 | 2009-06-25 | Janssen Pharmaceutica N.V. | Bicyclic heteroaryl-substituted imidazoles as modulators of the histamine h4 receptor |
| BRPI0915526A2 (pt) | 2008-06-12 | 2016-01-26 | Janssen Pharmaceutica Nv | uso de um antagonista da histamina h4 para o tratamento de aderências pós-operatórias |
| US9371311B2 (en) | 2008-06-30 | 2016-06-21 | Janssen Pharmaceutica Nv | Benzoimidazol-2-yl pyrimidine derivatives |
| SG192446A1 (en) | 2008-06-30 | 2013-08-30 | Janssen Pharmaceutica Nv | Process for the preparation of benzoimidazol-2-yl pyrimidine derivatives |
| US9145396B2 (en) | 2008-12-01 | 2015-09-29 | Targacept, Inc. | Synthesis and novel salt forms of (R)-5-((E)-2-pyrrolidin-3ylvinyl)pyrimidine |
| PL3279195T3 (pl) * | 2008-12-01 | 2020-12-14 | Oyster Point Pharma, Inc. | Synteza i nowe postacie soli (R)-5-((E)-2-pirolidyn-3-ylowinylo)pirymidyny |
| EP2201982A1 (en) | 2008-12-24 | 2010-06-30 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Histamine H4 receptor antagonists for the treatment of vestibular disorders |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| ES2612001T4 (es) | 2009-08-20 | 2018-02-07 | Yeda Research & Development Company, Ltd. | Terapia de baja frecuencia con acetato de glatirámero |
| USRE49251E1 (en) | 2010-01-04 | 2022-10-18 | Mapi Pharma Ltd. | Depot systems comprising glatiramer or pharmacologically acceptable salt thereof |
| WO2011092290A1 (en) | 2010-02-01 | 2011-08-04 | Novartis Ag | Pyrazolo[5,1b]oxazole derivatives as crf-1 receptor antagonists |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| EP2531490B1 (en) | 2010-02-02 | 2014-10-15 | Novartis AG | Cyclohexyl amide derivatives as crf receptor antagonists |
| AR086554A1 (es) | 2011-05-27 | 2014-01-08 | Novartis Ag | Derivados de la piperidina 3-espirociclica como agonistas de receptores de la ghrelina |
| JP2015525202A (ja) | 2012-05-03 | 2015-09-03 | ノバルティス アーゲー | グレリン受容体アゴニストとしての２，７−ジアザ−スピロ［４，５］デカ−７−イル誘導体のｌ−リンゴ酸塩およびその結晶形態 |
| EP3378476A1 (en) | 2012-06-08 | 2018-09-26 | Sensorion | H4 receptor inhibitors for treating tinnitus |
| PT2964229T (pt) | 2013-03-06 | 2020-03-23 | Janssen Pharmaceutica Nv | Moduladores de piridina benzimidazol-2-ilo do recetor h4 de histamina |
| US10414766B2 (en) * | 2015-12-15 | 2019-09-17 | Alembic Pharmaceuticals Limited | Polymorph of Riociguat and its process for the preparation |
| US12097292B2 (en) | 2016-08-28 | 2024-09-24 | Mapi Pharma Ltd. | Process for preparing microparticles containing glatiramer acetate |
| HUE071047T2 (hu) | 2016-08-31 | 2025-07-28 | Mapi Pharma Ltd | Glatiramer-acetátot tartalmazó depórendszerek |
| CN110382052A (zh) | 2017-03-26 | 2019-10-25 | Mapi医药公司 | 用于治疗进展型形式的多发性硬化症的格拉替雷储库系统 |
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| US4187213A (en) * | 1978-01-09 | 1980-02-05 | Eastman Kodak Company | Multiheterocyclic ultraviolet stabilizers and their use in organic compositions |
| FR2665161B1 (fr) * | 1990-07-26 | 1992-11-27 | Esteve Labor Dr | Nouveaux derives de benzimidazole, leur preparation et leur application en tant que medicaments. |
| AU8154998A (en) * | 1997-06-19 | 1999-01-04 | Smithkline Beecham Corporation | Novel aryloxy substituted pyrimidine imidazole compounds |
| DE59911249D1 (de) * | 1998-11-03 | 2005-01-13 | Abbott Gmbh & Co Kg | Substituierte 2-phenylbenzimidazole, deren herstellung und anwendung |
| CZ2003686A3 (cs) * | 2000-08-08 | 2003-08-13 | Ortho Mcneil Pharmaceutical, Inc. | Neimidazolové aryloxypiperidiny |
| WO2004014900A1 (en) * | 2002-08-09 | 2004-02-19 | Eli Lilly And Company | Benzimidazoles and benzothiazoles as inhibitors of map kinase |
| SE0202462D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | Novel use |
| CN1826111A (zh) * | 2003-04-10 | 2006-08-30 | 阿文尼尔药品公司 | 用于治疗变应性和过增生性疾病的咪唑衍生物 |
| EP1673348B1 (en) * | 2003-09-30 | 2009-04-01 | Janssen Pharmaceutica N.V. | Benzoimidazole compounds |
| EA011242B1 (ru) * | 2004-03-25 | 2009-02-27 | Янссен Фармацевтика Н.В. | Производные имидазола |
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