RU2416608C2 - Ароматическое соединение - Google Patents
Ароматическое соединение Download PDFInfo
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- RU2416608C2 RU2416608C2 RU2007108298/04A RU2007108298A RU2416608C2 RU 2416608 C2 RU2416608 C2 RU 2416608C2 RU 2007108298/04 A RU2007108298/04 A RU 2007108298/04A RU 2007108298 A RU2007108298 A RU 2007108298A RU 2416608 C2 RU2416608 C2 RU 2416608C2
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- RU
- Russia
- Prior art keywords
- group
- lower alkyl
- contain
- substituent
- alkyl group
- Prior art date
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- 150000001491 aromatic compounds Chemical class 0.000 title claims 61
- 150000001875 compounds Chemical class 0.000 claims abstract 56
- 206010016654 Fibrosis Diseases 0.000 claims abstract 8
- 230000004761 fibrosis Effects 0.000 claims abstract 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 5
- 125000000217 alkyl group Chemical group 0.000 claims 131
- 125000001424 substituent group Chemical group 0.000 claims 77
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 65
- 150000003839 salts Chemical class 0.000 claims 52
- 125000005843 halogen group Chemical group 0.000 claims 46
- 125000002947 alkylene group Chemical group 0.000 claims 34
- -1 1,2,3,4-tetrazolyl Chemical group 0.000 claims 33
- 125000003545 alkoxy group Chemical group 0.000 claims 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 24
- 125000002252 acyl group Chemical group 0.000 claims 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 21
- 229910052757 nitrogen Inorganic materials 0.000 claims 21
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims 14
- 125000003277 amino group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- 125000004434 sulfur atom Chemical group 0.000 claims 12
- 125000004043 oxo group Chemical group O=* 0.000 claims 11
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 claims 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 125000002883 imidazolyl group Chemical group 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 125000003386 piperidinyl group Chemical group 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- 125000004450 alkenylene group Chemical group 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 3
- VCRIHQNKYCRBQU-UHFFFAOYSA-N 1-[6-[4-[3-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-3-oxopropyl]phenoxy]pyridin-3-yl]-3-(3,4-dichlorophenyl)-1-ethylurea Chemical compound C=1C=C(OC=2C=CC(CCC(=O)N3CCN(CC=4C=C5OCOC5=CC=4)CC3)=CC=2)N=CC=1N(CC)C(=O)NC1=CC=C(Cl)C(Cl)=C1 VCRIHQNKYCRBQU-UHFFFAOYSA-N 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 2
- IYIFLLBEVVTNTE-UHFFFAOYSA-N ethyl 4-[3-[3-methyl-4-[5-[[4-(trifluoromethyl)benzoyl]amino]pyridin-2-yl]oxyphenyl]-2-oxo-1,3-diazinan-1-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1C(=O)N(C=2C=C(C)C(OC=3N=CC(NC(=O)C=4C=CC(=CC=4)C(F)(F)F)=CC=3)=CC=2)CCC1 IYIFLLBEVVTNTE-UHFFFAOYSA-N 0.000 claims 2
- PVTKHDNYPIHWEI-UHFFFAOYSA-N n-[6-[4-(4-benzylpiperazine-1-carbonyl)phenoxy]pyridin-3-yl]-3,4-dichlorobenzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)NC(C=N1)=CC=C1OC1=CC=C(C(=O)N2CCN(CC=3C=CC=CC=3)CC2)C=C1 PVTKHDNYPIHWEI-UHFFFAOYSA-N 0.000 claims 2
- FZZLMQOSLZYGTF-UHFFFAOYSA-N n-[6-[4-(4-benzylpiperazine-1-carbonyl)phenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC(C=N1)=CC=C1OC1=CC=C(C(=O)N2CCN(CC=3C=CC=CC=3)CC2)C=C1 FZZLMQOSLZYGTF-UHFFFAOYSA-N 0.000 claims 2
- BBBBCYBALPILFW-UHFFFAOYSA-N n-[6-[4-[3-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-3-oxopropyl]phenoxy]pyridin-3-yl]-3,4-dichlorobenzenesulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC(C=N1)=CC=C1OC(C=C1)=CC=C1CCC(=O)N1CCN(CC=2C=C3OCOC3=CC=2)CC1 BBBBCYBALPILFW-UHFFFAOYSA-N 0.000 claims 2
- IPVQHBSBOMALEV-UHFFFAOYSA-N n-[6-[4-[3-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-3-oxopropyl]phenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC(C=N1)=CC=C1OC(C=C1)=CC=C1CCC(=O)N1CCN(CC=2C=C3OCOC3=CC=2)CC1 IPVQHBSBOMALEV-UHFFFAOYSA-N 0.000 claims 2
- IKWNOQNPFAGRJU-UHFFFAOYSA-N n-[6-[4-[4-[2-(4-benzylpiperazin-1-yl)-2-oxoethyl]piperidin-1-yl]-2-methylphenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound CC1=CC(N2CCC(CC(=O)N3CCN(CC=4C=CC=CC=4)CC3)CC2)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 IKWNOQNPFAGRJU-UHFFFAOYSA-N 0.000 claims 2
- IKYWKWULXXNJNR-UHFFFAOYSA-N n-[6-[4-[4-[2-(4-benzylpiperazin-1-yl)-2-oxoethyl]piperidin-1-yl]phenoxy]pyridin-3-yl]-3,4-dichlorobenzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)NC(C=N1)=CC=C1OC1=CC=C(N2CCC(CC(=O)N3CCN(CC=4C=CC=CC=4)CC3)CC2)C=C1 IKYWKWULXXNJNR-UHFFFAOYSA-N 0.000 claims 2
- XQVHQTGKFUZGSX-UHFFFAOYSA-N n-[6-[4-[4-[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]piperazin-1-yl]phenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC(C=N1)=CC=C1OC1=CC=C(N2CCN(CC(=O)N3CCN(CC=4C=C5OCOC5=CC=4)CC3)CC2)C=C1 XQVHQTGKFUZGSX-UHFFFAOYSA-N 0.000 claims 2
- UZUJZBJAIUBOKH-UHFFFAOYSA-N n-[6-[4-[4-[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]piperidin-1-yl]-2-methoxyphenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound COC1=CC(N2CCC(CC(=O)N3CCN(CC=4C=C5OCOC5=CC=4)CC3)CC2)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 UZUJZBJAIUBOKH-UHFFFAOYSA-N 0.000 claims 2
- KFQVTENRPXJECI-UHFFFAOYSA-N n-[6-[4-[4-[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]piperidin-1-yl]-2-methylphenoxy]pyridin-3-yl]-3,4-dichlorobenzamide Chemical compound CC1=CC(N2CCC(CC(=O)N3CCN(CC=4C=C5OCOC5=CC=4)CC3)CC2)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 KFQVTENRPXJECI-UHFFFAOYSA-N 0.000 claims 2
- ZOQYNJSQNYKPEP-UHFFFAOYSA-N n-[6-[4-[4-[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]piperidin-1-yl]-2-methylphenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound CC1=CC(N2CCC(CC(=O)N3CCN(CC=4C=C5OCOC5=CC=4)CC3)CC2)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 ZOQYNJSQNYKPEP-UHFFFAOYSA-N 0.000 claims 2
- YZDNPUONKNABQI-UHFFFAOYSA-N n-[6-[4-[4-[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]piperidin-1-yl]phenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC(C=N1)=CC=C1OC1=CC=C(N2CCC(CC(=O)N3CCN(CC=4C=C5OCOC5=CC=4)CC3)CC2)C=C1 YZDNPUONKNABQI-UHFFFAOYSA-N 0.000 claims 2
- GQARPRTVAQKYLO-UHFFFAOYSA-N n-[6-[4-[[2-(4-benzylpiperazin-1-yl)-2-oxoethyl]-methylamino]-2-methylphenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C=1C=C(OC=2N=CC(NC(=O)C=3C=CC(=CC=3)C(F)(F)F)=CC=2)C(C)=CC=1N(C)CC(=O)N(CC1)CCN1CC1=CC=CC=C1 GQARPRTVAQKYLO-UHFFFAOYSA-N 0.000 claims 2
- XCKZLGMOEKSFMV-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-ethylamino]-2-fluorophenoxy]pyridin-3-yl]-3,4-dichlorobenzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(CC)C(C=C1F)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 XCKZLGMOEKSFMV-UHFFFAOYSA-N 0.000 claims 2
- VKGPHDJWABVYHZ-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-ethylamino]-2-fluorophenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(CC)C(C=C1F)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 VKGPHDJWABVYHZ-UHFFFAOYSA-N 0.000 claims 2
- VYIRSVCHAJORFX-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-ethylamino]-2-methoxyphenoxy]pyridin-3-yl]-3,4-dichlorobenzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(CC)C(C=C1OC)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 VYIRSVCHAJORFX-UHFFFAOYSA-N 0.000 claims 2
- UGLGSVLDVIYPPG-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-ethylamino]-2-methoxyphenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(CC)C(C=C1OC)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 UGLGSVLDVIYPPG-UHFFFAOYSA-N 0.000 claims 2
- CHAQXINYJKQZMH-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-ethylamino]-2-methylphenoxy]pyridin-3-yl]-3,4-dichlorobenzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(CC)C(C=C1C)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 CHAQXINYJKQZMH-UHFFFAOYSA-N 0.000 claims 2
- LBGOIPPUEFIVMG-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-ethylamino]phenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(CC)C(C=C1)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 LBGOIPPUEFIVMG-UHFFFAOYSA-N 0.000 claims 2
- UDNKVOHTPKWHCA-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-methylamino]-2-fluorophenoxy]pyridin-3-yl]-3,4-dichlorobenzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(C)C(C=C1F)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 UDNKVOHTPKWHCA-UHFFFAOYSA-N 0.000 claims 2
- IXHDKWKRLQESPZ-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-methylamino]-2-fluorophenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(C)C(C=C1F)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 IXHDKWKRLQESPZ-UHFFFAOYSA-N 0.000 claims 2
- FXIONCHYQNGSOI-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-methylamino]-2-methoxyphenoxy]pyridin-3-yl]-3,4-dichlorobenzamide Chemical compound COC1=CC(N(C)CC(=O)N2CCN(CC=3C=C4OCOC4=CC=3)CC2)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 FXIONCHYQNGSOI-UHFFFAOYSA-N 0.000 claims 2
- QPVHOXACWAMPIP-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-methylamino]-2-methoxyphenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound COC1=CC(N(C)CC(=O)N2CCN(CC=3C=C4OCOC4=CC=3)CC2)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 QPVHOXACWAMPIP-UHFFFAOYSA-N 0.000 claims 2
- AZTVZBRJJMBBLX-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-methylamino]-2-methylphenoxy]pyridin-3-yl]-2-fluoro-4-(trifluoromethyl)benzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(C)C(C=C1C)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1F AZTVZBRJJMBBLX-UHFFFAOYSA-N 0.000 claims 2
- AKBBIACRZIXUJF-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-methylamino]-2-methylphenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(C)C(C=C1C)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 AKBBIACRZIXUJF-UHFFFAOYSA-N 0.000 claims 2
- UBHVZIGQCBCZLZ-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-methylamino]phenoxy]pyridin-3-yl]-3,4-dichlorobenzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(C)C(C=C1)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 UBHVZIGQCBCZLZ-UHFFFAOYSA-N 0.000 claims 2
- WUCCUXLWDSCJHJ-UHFFFAOYSA-N n-[6-[4-[[2-[4-[4-(4-fluorobenzoyl)phenyl]piperazin-1-yl]-2-oxoethyl]-methylamino]-2-methoxyphenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound COC1=CC(N(C)CC(=O)N2CCN(CC2)C=2C=CC(=CC=2)C(=O)C=2C=CC(F)=CC=2)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 WUCCUXLWDSCJHJ-UHFFFAOYSA-N 0.000 claims 2
- HZSVPLYJEBYHJG-UHFFFAOYSA-N n-[6-[[4-[3-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-3-oxopropyl]phenyl]methylamino]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC(C=N1)=CC=C1NCC(C=C1)=CC=C1CCC(=O)N1CCN(CC=2C=C3OCOC3=CC=2)CC1 HZSVPLYJEBYHJG-UHFFFAOYSA-N 0.000 claims 2
- PUDLKZRNMJRZAW-UHFFFAOYSA-N n-[6-[[4-[4-[2-(4-benzylpiperazin-1-yl)-2-oxoethyl]piperidin-1-yl]phenyl]methylamino]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC(C=N1)=CC=C1NCC1=CC=C(N2CCC(CC(=O)N3CCN(CC=4C=CC=CC=4)CC3)CC2)C=C1 PUDLKZRNMJRZAW-UHFFFAOYSA-N 0.000 claims 2
- GXODLQRRPZQCKL-UHFFFAOYSA-N n-[6-[[4-[4-[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]piperidin-1-yl]phenyl]methylamino]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC(C=N1)=CC=C1NCC1=CC=C(N2CCC(CC(=O)N3CCN(CC=4C=C5OCOC5=CC=4)CC3)CC2)C=C1 GXODLQRRPZQCKL-UHFFFAOYSA-N 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000005493 quinolyl group Chemical group 0.000 claims 2
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 1
- CJCZHHOTEVGOEE-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-n-[3-methyl-4-[5-[[4-(trifluoromethyl)phenoxy]methyl]pyridin-2-yl]oxyphenyl]-2-oxoacetamide Chemical compound CC1=CC(NC(=O)C(=O)N2CCN(CC=3C=C4OCOC4=CC=3)CC2)=CC=C1OC(N=C1)=CC=C1COC1=CC=C(C(F)(F)F)C=C1 CJCZHHOTEVGOEE-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 241001104043 Syringa Species 0.000 claims 1
- 235000004338 Syringa vulgaris Nutrition 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 239000012634 fragment Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 206010061989 glomerulosclerosis Diseases 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- LWMGFJJYBYFSPD-UHFFFAOYSA-N n-[6-[4-[3-[4-(1,3-benzodioxol-5-ylmethyl)piperazine-1-carbonyl]piperidin-1-yl]phenoxy]pyridin-3-yl]-3,4-dichlorobenzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)NC(C=N1)=CC=C1OC1=CC=C(N2CC(CCC2)C(=O)N2CCN(CC=3C=C4OCOC4=CC=3)CC2)C=C1 LWMGFJJYBYFSPD-UHFFFAOYSA-N 0.000 claims 1
- KFYRMAHKLJXILS-UHFFFAOYSA-N n-[6-[4-[4-[2-(4-benzylpiperazin-1-yl)-2-oxoethyl]piperidin-1-yl]phenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC(C=N1)=CC=C1OC1=CC=C(N2CCC(CC(=O)N3CCN(CC=4C=CC=CC=4)CC3)CC2)C=C1 KFYRMAHKLJXILS-UHFFFAOYSA-N 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 102000008186 Collagen Human genes 0.000 abstract 1
- 108010035532 Collagen Proteins 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229920001436 collagen Polymers 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 230000001629 suppression Effects 0.000 abstract 1
Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/18—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to carbon atoms of six-membered aromatic rings
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
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- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers
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- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
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- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/75—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/58—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
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- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
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- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
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- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
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| JP2004230092 | 2004-08-06 | ||
| JP2004-230092 | 2004-08-06 | ||
| JP2005090149 | 2005-03-25 | ||
| JP2005-090149 | 2005-03-25 |
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| RU2007108298A RU2007108298A (ru) | 2008-09-20 |
| RU2416608C2 true RU2416608C2 (ru) | 2011-04-20 |
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| RU2007108298/04A RU2416608C2 (ru) | 2004-08-06 | 2005-08-03 | Ароматическое соединение |
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| EP (1) | EP1773797A2 (https=) |
| JP (2) | JP4154613B2 (https=) |
| KR (1) | KR100927563B1 (https=) |
| CN (1) | CN1993339B (https=) |
| AR (1) | AR050448A1 (https=) |
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| BR (1) | BRPI0514150A (https=) |
| CA (1) | CA2573223C (https=) |
| IL (1) | IL180884A (https=) |
| MX (1) | MX2007001215A (https=) |
| MY (1) | MY148905A (https=) |
| RU (1) | RU2416608C2 (https=) |
| TW (1) | TWI353983B (https=) |
| WO (1) | WO2006014012A2 (https=) |
| ZA (1) | ZA200700811B (https=) |
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- 2005-08-03 ZA ZA200700811A patent/ZA200700811B/xx unknown
- 2005-08-03 EP EP05780290A patent/EP1773797A2/en not_active Withdrawn
- 2005-08-03 KR KR1020077002786A patent/KR100927563B1/ko not_active Expired - Fee Related
- 2005-08-03 MX MX2007001215A patent/MX2007001215A/es active IP Right Grant
- 2005-08-03 AU AU2005268030A patent/AU2005268030B2/en not_active Ceased
- 2005-08-03 CA CA2573223A patent/CA2573223C/en not_active Expired - Fee Related
- 2005-08-03 RU RU2007108298/04A patent/RU2416608C2/ru not_active IP Right Cessation
- 2005-08-03 CN CN2005800266964A patent/CN1993339B/zh not_active Expired - Fee Related
- 2005-08-03 US US11/659,689 patent/US8188277B2/en not_active Expired - Fee Related
- 2005-08-03 WO PCT/JP2005/014611 patent/WO2006014012A2/en not_active Ceased
- 2005-08-03 BR BRPI0514150-8A patent/BRPI0514150A/pt not_active IP Right Cessation
- 2005-08-05 MY MYPI20053673A patent/MY148905A/en unknown
- 2005-08-05 AR ARP050103285A patent/AR050448A1/es unknown
- 2005-08-08 JP JP2005229066A patent/JP4154613B2/ja not_active Expired - Fee Related
- 2005-08-08 TW TW094126788A patent/TWI353983B/zh not_active IP Right Cessation
-
2007
- 2007-01-22 IL IL180884A patent/IL180884A/en not_active IP Right Cessation
- 2007-11-20 JP JP2007300664A patent/JP4931775B2/ja not_active Expired - Fee Related
-
2012
- 2012-02-29 US US13/409,090 patent/US20120238750A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001089412A (ja) * | 1999-09-22 | 2001-04-03 | Otsuka Pharmaceut Co Ltd | ベンゼン誘導体またはその医薬的に許容される塩 |
| JP2001089450A (ja) * | 1999-09-22 | 2001-04-03 | Otsuka Pharmaceut Co Ltd | ピリジン誘導体含有医薬製剤 |
| JP2004035475A (ja) * | 2002-07-03 | 2004-02-05 | Ajinomoto Co Inc | TGFβ作用抑制剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0514150A (pt) | 2007-11-27 |
| JP4154613B2 (ja) | 2008-09-24 |
| CN1993339B (zh) | 2013-05-22 |
| ZA200700811B (en) | 2008-10-29 |
| AU2005268030A1 (en) | 2006-02-09 |
| IL180884A0 (en) | 2007-07-04 |
| CN1993339A (zh) | 2007-07-04 |
| WO2006014012A2 (en) | 2006-02-09 |
| AR050448A1 (es) | 2006-10-25 |
| WO2006014012A3 (en) | 2006-12-07 |
| IL180884A (en) | 2013-10-31 |
| MX2007001215A (es) | 2007-04-17 |
| US8188277B2 (en) | 2012-05-29 |
| JP2006298893A (ja) | 2006-11-02 |
| HK1101824A1 (en) | 2007-10-26 |
| US20070270422A1 (en) | 2007-11-22 |
| CA2573223C (en) | 2013-05-21 |
| US20120238750A1 (en) | 2012-09-20 |
| JP2008133278A (ja) | 2008-06-12 |
| TW200619214A (en) | 2006-06-16 |
| KR20070103351A (ko) | 2007-10-23 |
| KR100927563B1 (ko) | 2009-11-23 |
| MY148905A (en) | 2013-06-14 |
| AU2005268030B2 (en) | 2009-02-19 |
| RU2007108298A (ru) | 2008-09-20 |
| JP4931775B2 (ja) | 2012-05-16 |
| TWI353983B (en) | 2011-12-11 |
| EP1773797A2 (en) | 2007-04-18 |
| CA2573223A1 (en) | 2006-02-09 |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20160804 |