HRP20120748T1 - Heterocikliäśki spoj i farmaceutski sastavi koji ga sadrže - Google Patents
Heterocikliäśki spoj i farmaceutski sastavi koji ga sadrže Download PDFInfo
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- HRP20120748T1 HRP20120748T1 HRP20120748AT HRP20120748T HRP20120748T1 HR P20120748 T1 HRP20120748 T1 HR P20120748T1 HR P20120748A T HRP20120748A T HR P20120748AT HR P20120748 T HRP20120748 T HR P20120748T HR P20120748 T1 HRP20120748 T1 HR P20120748T1
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- HR
- Croatia
- Prior art keywords
- methyl
- group
- yloxy
- carbonyl
- indol
- Prior art date
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 18
- 125000005843 halogen group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 7
- 125000002252 acyl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- ITRPVLHSVPWCHG-UHFFFAOYSA-N 3,4-dichloro-n-methyl-n-[2-[1-methyl-2-[4-[(4-propan-2-yloxyphenyl)methyl]piperazine-1-carbonyl]indol-6-yl]oxypyrimidin-5-yl]benzenesulfonamide Chemical compound C1=CC(OC(C)C)=CC=C1CN1CCN(C(=O)C=2N(C3=CC(OC=4N=CC(=CN=4)N(C)S(=O)(=O)C=4C=C(Cl)C(Cl)=CC=4)=CC=C3C=2)C)CC1 ITRPVLHSVPWCHG-UHFFFAOYSA-N 0.000 claims 2
- JLJVWPWLCJLEHC-UHFFFAOYSA-N 3,4-dichloro-n-methyl-n-[6-[1-methyl-2-[4-[(4-propan-2-yloxyphenyl)methyl]piperazine-1-carbonyl]indol-6-yl]oxypyridin-3-yl]benzenesulfonamide Chemical compound C1=CC(OC(C)C)=CC=C1CN1CCN(C(=O)C=2N(C3=CC(OC=4N=CC(=CC=4)N(C)S(=O)(=O)C=4C=C(Cl)C(Cl)=CC=4)=CC=C3C=2)C)CC1 JLJVWPWLCJLEHC-UHFFFAOYSA-N 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 230000004761 fibrosis Effects 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- -1 indoldiyl groups Chemical group 0.000 claims 2
- MTPYRLFHLKIEAP-UHFFFAOYSA-N n,4-dimethyl-n-[6-[[2-[4-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]piperazine-1-carbonyl]-1h-indol-6-yl]oxy]pyridin-3-yl]benzenesulfonamide Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(C)C(C=N1)=CC=C1OC(C=C1N2)=CC=C1C=C2C(=O)N(CC1)CCN1CC1=CC=C(OCC(F)(F)F)C=C1 MTPYRLFHLKIEAP-UHFFFAOYSA-N 0.000 claims 2
- WPVDJRSZMIZZGP-UHFFFAOYSA-N n-[2-[2-[4-[(4-methoxyphenyl)methyl]piperazine-1-carbonyl]-1-methylindol-5-yl]oxypyrimidin-5-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(OC)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(NC(=O)C=5C=CC(=CC=5)C(F)(F)F)=CN=4)C=C3C=2)C)CC1 WPVDJRSZMIZZGP-UHFFFAOYSA-N 0.000 claims 2
- MENIQRIABKGKIU-UHFFFAOYSA-N n-[6-[1-methyl-2-[4-(2-methylpropyl)piperazine-1-carbonyl]indol-5-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1CN(CC(C)C)CCN1C(=O)C1=CC2=CC(OC=3N=CC(NC(=O)C=4C=CC(=CC=4)C(F)(F)F)=CC=3)=CC=C2N1C MENIQRIABKGKIU-UHFFFAOYSA-N 0.000 claims 2
- IWPAXBFFZINSPZ-UHFFFAOYSA-N n-[6-[1-methyl-2-[4-[[4-(thiadiazol-4-yl)phenyl]methyl]piperazine-1-carbonyl]indol-6-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=C2N(C)C(C(=O)N3CCN(CC=4C=CC(=CC=4)C=4N=NSC=4)CC3)=CC2=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 IWPAXBFFZINSPZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- VKBHNIGWRRDSEM-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-[6-[2-[4-[(4-ethoxyphenyl)methyl]piperazine-1-carbonyl]-1-methylindol-5-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(OCC)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)C=C3C=2)C)CC1 VKBHNIGWRRDSEM-BTJKTKAUSA-N 0.000 claims 1
- UGIKDEDIVSBESY-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-[6-[2-[4-[(4-methoxyphenyl)methyl]piperazine-1-carbonyl]-1-methylindol-5-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(OC)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)C=C3C=2)C)CC1 UGIKDEDIVSBESY-BTJKTKAUSA-N 0.000 claims 1
- UJZSUCCUXURVBM-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-[6-[2-[4-[(5-ethoxypyridin-2-yl)methyl]piperazine-1-carbonyl]-1-methylindol-5-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide Chemical compound OC(=O)\C=C/C(O)=O.N1=CC(OCC)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)C=C3C=2)C)CC1 UJZSUCCUXURVBM-BTJKTKAUSA-N 0.000 claims 1
- KWSLCZKPAQCYPG-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-[6-[2-[4-[[4-(difluoromethoxy)phenyl]methyl]piperazine-1-carbonyl]-1-methylindol-5-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide Chemical compound OC(=O)\C=C/C(O)=O.C=1C=C(OC=2C=C3C=C(N(C)C3=CC=2)C(=O)N2CCN(CC=3C=CC(OC(F)F)=CC=3)CC2)N=CC=1N(C)C(=O)C1=CC=C(C(F)(F)F)C=C1 KWSLCZKPAQCYPG-BTJKTKAUSA-N 0.000 claims 1
- ZOMCFJQUEJENMP-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-methyl-n-[6-[1-methyl-2-[4-[(6-propan-2-yloxypyridin-3-yl)methyl]piperazine-1-carbonyl]indol-5-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound OC(=O)\C=C/C(O)=O.C1=NC(OC(C)C)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)C=C3C=2)C)CC1 ZOMCFJQUEJENMP-BTJKTKAUSA-N 0.000 claims 1
- HSIPJRWCQFXACM-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-methyl-n-[6-[1-methyl-2-[4-[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]piperazine-1-carbonyl]indol-5-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound OC(=O)\C=C/C(O)=O.C=1C=C(OC=2C=C3C=C(N(C)C3=CC=2)C(=O)N2CCN(CC=3C=CC(OC(F)(F)C(F)F)=CC=3)CC2)N=CC=1N(C)C(=O)C1=CC=C(C(F)(F)F)C=C1 HSIPJRWCQFXACM-BTJKTKAUSA-N 0.000 claims 1
- XDBNXTFAMNUPRG-UHFFFAOYSA-N 2-chloro-n-[6-[1-methyl-2-[4-[(4-propan-2-yloxyphenyl)methyl]piperazine-1-carbonyl]indol-6-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(OC(C)C)=CC=C1CN1CCN(C(=O)C=2N(C3=CC(OC=4N=CC(NC(=O)C=5C(=CC(=CC=5)C(F)(F)F)Cl)=CC=4)=CC=C3C=2)C)CC1 XDBNXTFAMNUPRG-UHFFFAOYSA-N 0.000 claims 1
- JRYBLIYBQGIKAL-UHFFFAOYSA-N 2-chloro-n-[6-[1-methyl-2-[4-[(4-propan-2-yloxyphenyl)methyl]piperazine-1-carbonyl]indol-6-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide;hydrobromide Chemical compound Br.C1=CC(OC(C)C)=CC=C1CN1CCN(C(=O)C=2N(C3=CC(OC=4N=CC(NC(=O)C=5C(=CC(=CC=5)C(F)(F)F)Cl)=CC=4)=CC=C3C=2)C)CC1 JRYBLIYBQGIKAL-UHFFFAOYSA-N 0.000 claims 1
- VNZMRMYUROSNFV-UHFFFAOYSA-N 4-methoxy-n-methyl-n-[6-[1-methyl-2-[4-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]piperazine-1-carbonyl]indol-6-yl]oxypyridin-3-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C)C(C=N1)=CC=C1OC1=CC=C(C=C(C(=O)N2CCN(CC=3C=CC(OCC(F)(F)F)=CC=3)CC2)N2C)C2=C1 VNZMRMYUROSNFV-UHFFFAOYSA-N 0.000 claims 1
- FSIJKVLFODXZKC-UHFFFAOYSA-N 4-methoxy-n-methyl-n-[6-[1-methyl-2-[4-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]piperazine-1-carbonyl]indol-6-yl]oxypyridin-3-yl]benzenesulfonamide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1S(=O)(=O)N(C)C(C=N1)=CC=C1OC1=CC=C(C=C(C(=O)N2CCN(CC=3C=CC(OCC(F)(F)F)=CC=3)CC2)N2C)C2=C1 FSIJKVLFODXZKC-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000004093 cyano group Chemical class *C#N 0.000 claims 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- RBGFDJMJLJYHKP-UHFFFAOYSA-N n,4-dimethyl-n-[6-[1-methyl-2-[4-[(4-propan-2-yloxyphenyl)methyl]piperazine-1-carbonyl]indol-6-yl]oxypyridin-3-yl]benzenesulfonamide Chemical compound C1=CC(OC(C)C)=CC=C1CN1CCN(C(=O)C=2N(C3=CC(OC=4N=CC(=CC=4)N(C)S(=O)(=O)C=4C=CC(C)=CC=4)=CC=C3C=2)C)CC1 RBGFDJMJLJYHKP-UHFFFAOYSA-N 0.000 claims 1
- NWERJODKEJPZQD-UHFFFAOYSA-N n-[6-[1,4-dimethyl-2-[4-[(4-propan-2-ylphenyl)methyl]piperazine-1-carbonyl]indol-5-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(C)C)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)C(C)=C3C=2)C)CC1 NWERJODKEJPZQD-UHFFFAOYSA-N 0.000 claims 1
- CAOBQETXKBUMDD-UHFFFAOYSA-N n-[6-[1,4-dimethyl-2-[4-[(4-propan-2-ylphenyl)methyl]piperazine-1-carbonyl]indol-5-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide;hydrobromide Chemical compound Br.C1=CC(C(C)C)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)C(C)=C3C=2)C)CC1 CAOBQETXKBUMDD-UHFFFAOYSA-N 0.000 claims 1
- RQRONONYMJXTNR-UHFFFAOYSA-N n-[6-[2-[4-[(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]piperazine-1-carbonyl]-1-methylindol-6-yl]oxypyridin-3-yl]-n,4-dimethylbenzenesulfonamide Chemical compound C=1C=C(OC=2C=C3N(C)C(C(=O)N4CCN(CC=5C=C6OC(F)(F)OC6=CC=5)CC4)=CC3=CC=2)N=CC=1N(C)S(=O)(=O)C1=CC=C(C)C=C1 RQRONONYMJXTNR-UHFFFAOYSA-N 0.000 claims 1
- IOAUJGUIVGXWEB-UHFFFAOYSA-N n-[6-[2-[4-[(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]piperazine-1-carbonyl]-1-methylindol-6-yl]oxypyridin-3-yl]-n,4-dimethylbenzenesulfonamide;hydrochloride Chemical compound Cl.C=1C=C(OC=2C=C3N(C)C(C(=O)N4CCN(CC=5C=C6OC(F)(F)OC6=CC=5)CC4)=CC3=CC=2)N=CC=1N(C)S(=O)(=O)C1=CC=C(C)C=C1 IOAUJGUIVGXWEB-UHFFFAOYSA-N 0.000 claims 1
- DNYMJZPUGLOMQF-UHFFFAOYSA-N n-[6-[2-[4-[(4-cyanophenyl)methyl]piperazine-1-carbonyl]-1-methylindol-6-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide Chemical compound C=1C=C(OC=2C=C3N(C)C(C(=O)N4CCN(CC=5C=CC(=CC=5)C#N)CC4)=CC3=CC=2)N=CC=1N(C)C(=O)C1=CC=C(C(F)(F)F)C=C1 DNYMJZPUGLOMQF-UHFFFAOYSA-N 0.000 claims 1
- NZXPQUNGARTCMG-UHFFFAOYSA-N n-[6-[2-[4-[(4-cyanophenyl)methyl]piperazine-1-carbonyl]-1-methylindol-6-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide;hydrobromide Chemical compound Br.C=1C=C(OC=2C=C3N(C)C(C(=O)N4CCN(CC=5C=CC(=CC=5)C#N)CC4)=CC3=CC=2)N=CC=1N(C)C(=O)C1=CC=C(C(F)(F)F)C=C1 NZXPQUNGARTCMG-UHFFFAOYSA-N 0.000 claims 1
- HJTWVWHWVSFHSQ-UHFFFAOYSA-N n-[6-[2-[4-[(4-ethoxyphenyl)methyl]piperazine-1-carbonyl]-1-methylindol-5-yl]oxy-2-methylpyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide Chemical compound C1=CC(OCC)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=C(C)C(N(C)C(=O)C=5C=CC(=CC=5)C(F)(F)F)=CC=4)C=C3C=2)C)CC1 HJTWVWHWVSFHSQ-UHFFFAOYSA-N 0.000 claims 1
- KQHIEENBCNHBPM-UHFFFAOYSA-N n-[6-[2-[4-[(4-ethoxyphenyl)methyl]piperazine-1-carbonyl]-1-methylindol-5-yl]oxy-2-methylpyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide;hydrobromide Chemical compound Br.C1=CC(OCC)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=C(C)C(N(C)C(=O)C=5C=CC(=CC=5)C(F)(F)F)=CC=4)C=C3C=2)C)CC1 KQHIEENBCNHBPM-UHFFFAOYSA-N 0.000 claims 1
- CNULTVATQGJEBT-UHFFFAOYSA-N n-[6-[2-[4-[(4-ethoxyphenyl)methyl]piperazine-1-carbonyl]-1-methylindol-5-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide Chemical compound C1=CC(OCC)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)C=C3C=2)C)CC1 CNULTVATQGJEBT-UHFFFAOYSA-N 0.000 claims 1
- GVUKRCXQHXPZJK-UHFFFAOYSA-N n-[6-[2-[4-[(4-ethylphenyl)methyl]piperazine-1-carbonyl]-1-methylindol-5-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide Chemical compound C1=CC(CC)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)C=C3C=2)C)CC1 GVUKRCXQHXPZJK-UHFFFAOYSA-N 0.000 claims 1
- PQUQQZKSFNWFJX-UHFFFAOYSA-N n-[6-[2-[4-[(4-ethylphenyl)methyl]piperazine-1-carbonyl]-1-methylindol-5-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CC)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)C=C3C=2)C)CC1 PQUQQZKSFNWFJX-UHFFFAOYSA-N 0.000 claims 1
- GESYHGSWCSTVGU-UHFFFAOYSA-N n-[6-[2-[4-[(4-methoxyphenyl)methyl]piperazine-1-carbonyl]-1-methylindol-5-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide Chemical compound C1=CC(OC)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)C=C3C=2)C)CC1 GESYHGSWCSTVGU-UHFFFAOYSA-N 0.000 claims 1
- SNQPEUNZVMAASK-UHFFFAOYSA-N n-[6-[2-[4-[(5-ethoxypyridin-2-yl)methyl]piperazine-1-carbonyl]-1-methylindol-5-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide Chemical compound N1=CC(OCC)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)C=C3C=2)C)CC1 SNQPEUNZVMAASK-UHFFFAOYSA-N 0.000 claims 1
- CCXPRWDNBZGYQW-UHFFFAOYSA-N n-[6-[2-[4-[2-(4-methoxyphenyl)ethylamino]piperidine-1-carbonyl]-1-methylindol-5-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(OC)=CC=C1CCNC1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(NC(=O)C=5C=CC(=CC=5)C(F)(F)F)=CC=4)C=C3C=2)C)CC1 CCXPRWDNBZGYQW-UHFFFAOYSA-N 0.000 claims 1
- QZRZYZHTCBDJTD-UHFFFAOYSA-N n-[6-[2-[4-[2-(4-methoxyphenyl)ethylamino]piperidine-1-carbonyl]-1-methylindol-5-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OC)=CC=C1CCNC1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(NC(=O)C=5C=CC(=CC=5)C(F)(F)F)=CC=4)C=C3C=2)C)CC1 QZRZYZHTCBDJTD-UHFFFAOYSA-N 0.000 claims 1
- XNESAIFRXZZYMK-UHFFFAOYSA-N n-[6-[2-[4-[[4-(1,3-difluoropropan-2-yloxy)phenyl]methyl]piperazine-1-carbonyl]-1-methylindol-6-yl]oxypyridin-3-yl]-2-methyl-4-(trifluoromethyl)benzamide Chemical compound CC1=CC(C(F)(F)F)=CC=C1C(=O)NC(C=N1)=CC=C1OC1=CC=C(C=C(C(=O)N2CCN(CC=3C=CC(OC(CF)CF)=CC=3)CC2)N2C)C2=C1 XNESAIFRXZZYMK-UHFFFAOYSA-N 0.000 claims 1
- UNLAFCYWNFVVCQ-UHFFFAOYSA-N n-[6-[2-[4-[[4-(1,3-difluoropropan-2-yloxy)phenyl]methyl]piperazine-1-carbonyl]-1-methylindol-6-yl]oxypyridin-3-yl]-2-methyl-4-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.CC1=CC(C(F)(F)F)=CC=C1C(=O)NC(C=N1)=CC=C1OC1=CC=C(C=C(C(=O)N2CCN(CC=3C=CC(OC(CF)CF)=CC=3)CC2)N2C)C2=C1 UNLAFCYWNFVVCQ-UHFFFAOYSA-N 0.000 claims 1
- SSHPZPWUXXDWIN-UHFFFAOYSA-N n-[6-[2-[4-[[4-(1,3-difluoropropan-2-yloxy)phenyl]methyl]piperazine-1-carbonyl]-1-methylindol-6-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethoxy)benzamide Chemical compound C=1C=C(OC=2C=C3N(C)C(C(=O)N4CCN(CC=5C=CC(OC(CF)CF)=CC=5)CC4)=CC3=CC=2)N=CC=1N(C)C(=O)C1=CC=C(OC(F)(F)F)C=C1 SSHPZPWUXXDWIN-UHFFFAOYSA-N 0.000 claims 1
- OXAJRLVKUWBNDS-UHFFFAOYSA-N n-[6-[2-[4-[[4-(1,3-difluoropropan-2-yloxy)phenyl]methyl]piperazine-1-carbonyl]-1-methylindol-6-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethoxy)benzamide;hydrobromide Chemical compound Br.C=1C=C(OC=2C=C3N(C)C(C(=O)N4CCN(CC=5C=CC(OC(CF)CF)=CC=5)CC4)=CC3=CC=2)N=CC=1N(C)C(=O)C1=CC=C(OC(F)(F)F)C=C1 OXAJRLVKUWBNDS-UHFFFAOYSA-N 0.000 claims 1
- DOIZFZCCTVIJHB-UHFFFAOYSA-N n-[6-[2-[4-[[4-(1,3-difluoropropan-2-yloxy)phenyl]methyl]piperazine-1-carbonyl]-1-methylindol-6-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide Chemical compound C=1C=C(OC=2C=C3N(C)C(C(=O)N4CCN(CC=5C=CC(OC(CF)CF)=CC=5)CC4)=CC3=CC=2)N=CC=1N(C)C(=O)C1=CC=C(C(F)(F)F)C=C1 DOIZFZCCTVIJHB-UHFFFAOYSA-N 0.000 claims 1
- BAFZPZSVPFVLGK-UHFFFAOYSA-N n-[6-[2-[4-[[4-(1,3-difluoropropan-2-yloxy)phenyl]methyl]piperazine-1-carbonyl]-1-methylindol-6-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide;hydrobromide Chemical compound Br.C=1C=C(OC=2C=C3N(C)C(C(=O)N4CCN(CC=5C=CC(OC(CF)CF)=CC=5)CC4)=CC3=CC=2)N=CC=1N(C)C(=O)C1=CC=C(C(F)(F)F)C=C1 BAFZPZSVPFVLGK-UHFFFAOYSA-N 0.000 claims 1
- UBBWYZSITCQSJO-UHFFFAOYSA-N n-[6-[2-[4-[[4-(difluoromethoxy)phenyl]methyl]piperazine-1-carbonyl]-1-methylindol-5-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethyl)benzamide Chemical compound C=1C=C(OC=2C=C3C=C(N(C)C3=CC=2)C(=O)N2CCN(CC=3C=CC(OC(F)F)=CC=3)CC2)N=CC=1N(C)C(=O)C1=CC=C(C(F)(F)F)C=C1 UBBWYZSITCQSJO-UHFFFAOYSA-N 0.000 claims 1
- UBYLEGRPRFXNJW-UHFFFAOYSA-N n-[6-[2-[4-[[4-(difluoromethoxy)phenyl]methyl]piperazine-1-carbonyl]-1-methylindol-6-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethoxy)benzamide Chemical compound C=1C=C(OC=2C=C3N(C)C(C(=O)N4CCN(CC=5C=CC(OC(F)F)=CC=5)CC4)=CC3=CC=2)N=CC=1N(C)C(=O)C1=CC=C(OC(F)(F)F)C=C1 UBYLEGRPRFXNJW-UHFFFAOYSA-N 0.000 claims 1
- SGCYAXWXICQIQQ-UHFFFAOYSA-N n-[6-[2-[4-[[4-(difluoromethoxy)phenyl]methyl]piperazine-1-carbonyl]-1-methylindol-6-yl]oxypyridin-3-yl]-n-methyl-4-(trifluoromethoxy)benzamide;hydrobromide Chemical compound Br.C=1C=C(OC=2C=C3N(C)C(C(=O)N4CCN(CC=5C=CC(OC(F)F)=CC=5)CC4)=CC3=CC=2)N=CC=1N(C)C(=O)C1=CC=C(OC(F)(F)F)C=C1 SGCYAXWXICQIQQ-UHFFFAOYSA-N 0.000 claims 1
- LPENCIAXRNEJHN-UHFFFAOYSA-N n-methyl-n-[6-[1-methyl-2-[4-[(4-propan-2-yloxyphenyl)methyl]piperazine-1-carbonyl]indol-6-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(OC(C)C)=CC=C1CN1CCN(C(=O)C=2N(C3=CC(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)=CC=C3C=2)C)CC1 LPENCIAXRNEJHN-UHFFFAOYSA-N 0.000 claims 1
- AFUKUYKCIPEBLI-UHFFFAOYSA-N n-methyl-n-[6-[1-methyl-2-[4-[(4-propan-2-yloxyphenyl)methyl]piperazine-1-carbonyl]indol-6-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide;hydrobromide Chemical compound Br.C1=CC(OC(C)C)=CC=C1CN1CCN(C(=O)C=2N(C3=CC(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)=CC=C3C=2)C)CC1 AFUKUYKCIPEBLI-UHFFFAOYSA-N 0.000 claims 1
- DXTWALFOCFSJPM-UHFFFAOYSA-N n-methyl-n-[6-[1-methyl-2-[4-[(4-propoxyphenyl)methyl]piperazine-1-carbonyl]indol-6-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(OCCC)=CC=C1CN1CCN(C(=O)C=2N(C3=CC(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)=CC=C3C=2)C)CC1 DXTWALFOCFSJPM-UHFFFAOYSA-N 0.000 claims 1
- FQERORZCLLPZPJ-UHFFFAOYSA-N n-methyl-n-[6-[1-methyl-2-[4-[(4-propoxyphenyl)methyl]piperazine-1-carbonyl]indol-6-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide;hydrobromide Chemical compound Br.C1=CC(OCCC)=CC=C1CN1CCN(C(=O)C=2N(C3=CC(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)=CC=C3C=2)C)CC1 FQERORZCLLPZPJ-UHFFFAOYSA-N 0.000 claims 1
- SZASZDATBXBLMG-UHFFFAOYSA-N n-methyl-n-[6-[1-methyl-2-[4-[(6-propan-2-yloxypyridin-3-yl)methyl]piperazine-1-carbonyl]indol-5-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=NC(OC(C)C)=CC=C1CN1CCN(C(=O)C=2N(C3=CC=C(OC=4N=CC(=CC=4)N(C)C(=O)C=4C=CC(=CC=4)C(F)(F)F)C=C3C=2)C)CC1 SZASZDATBXBLMG-UHFFFAOYSA-N 0.000 claims 1
- IYPUAUZPYQSWET-UHFFFAOYSA-N n-methyl-n-[6-[1-methyl-2-[4-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]piperazine-1-carbonyl]indol-6-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C=1C=C(OC=2C=C3N(C)C(C(=O)N4CCN(CC=5C=CC(OCC(F)(F)F)=CC=5)CC4)=CC3=CC=2)N=CC=1N(C)C(=O)C1=CC=C(C(F)(F)F)C=C1 IYPUAUZPYQSWET-UHFFFAOYSA-N 0.000 claims 1
- MEBZGWPJNBFVEL-UHFFFAOYSA-N n-methyl-n-[6-[1-methyl-2-[4-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]piperazine-1-carbonyl]indol-6-yl]oxypyridin-3-yl]-4-(trifluoromethyl)benzamide;hydrobromide Chemical compound Br.C=1C=C(OC=2C=C3N(C)C(C(=O)N4CCN(CC=5C=CC(OCC(F)(F)F)=CC=5)CC4)=CC3=CC=2)N=CC=1N(C)C(=O)C1=CC=C(C(F)(F)F)C=C1 MEBZGWPJNBFVEL-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
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Claims (11)
1. Heterociklički spoj ili njegova sol, naznačen time, da je predstavljen općom formulom (1):
[image]
gdje R1 je R5-Z1-skupina, R5-B-N(R6)-skupina, R5-N(R6)-B-skupina, R5-N(R7)-skupina,
R5-N (R8)-CO-N(R9)-skupina, R5-N(R10)-CS-N(R11)-skupina, R5-SO2-N(R12)-skupina,
R5-CO-B1-skupina, R5-B2CO-N(R12a)-skupina, R5-B9-SO2-N(R47)-skupina, R5-O-B10-SO2-N(R48)-skupina ili skupina predstavljena općom formulom:
[image]
gdje Z1 je C1-6 alkilen skupina ili C2-6 alkenilen skupina;
R5 je 5- do 15-člana monociklička, diciklička, ili triciklička zasićena ili nezasićena heterociklička skupina koja ima 1 do 4 atoma dušika, atoma kisika ili atoma sumpora
(pri čemu heterociklički prsten može biti supstituiran s 1 do 3 skupine odabrane iz skupine koju čine okso skupina; C1-6 alkoksi skupina opcijski supstituirana s jednim ili više halogen atoma; C1-6 alkil skupina opcijski supstituirana s jednim ili više halogen atoma; halogen atomi; C1-6 alkilsulfonil skupine; fenil skupine opcijski supstituirane na fenilnom prstenu,
s jednom ili više opcijski halogeniranim C1-6 alkil skupinama; C1-6 alkiltio skupine; pirolil skupine; benzoil skupina; C1-6 alkanoil skupine; C1-6 alkoksikarbonil skupine;
C1-6 alkilendioksi skupine; piridil skupine; i amino skupine koje mogu imati najmanje jedan supstituent odabran iz skupine koju čine C1-6 alkil skupine i C1-6 alkanoil skupine), opcijski halogenirane C1-6 alkil skupine, cikloalkil skupine, naftil skupina koja može imati na naftalen prstenu, 1 do 3 supstituenta odabrana iz skupine koju čine C1-6 alkil skupine,
halogen atomi, i amino skupine opcijski supstituirane s najmanje jednim supstituentom odabranim iz skupine koju čine C1-6 alkil skupine i C1-6 alkanoil skupine, ili je to skupina predstavljena općom formulom:
[image]
gdje R13je atom vodika, hidroksi skupina, karboksi skupina, halogen atom, C1-6 alkil skupina opcijski supstituirana s jednim ili više halogen atoma, C1-6 alkoksi skupina opcijski supstituirana s jednim ili više halogen atoma ili C1-6 alkoksi skupine; C1-6 alkanoiloksi skupina, C1-6 alkoksikarbonil skupina, C1-6 alkoksikarbonil skupina-supstituirana
C1-6 alkil skupina, cijano skupina, fenil skupina, nitro skupina, C2-6 alkanoilamino skupina, C1-6 alkilendioksi skupina, fenoksi skupina, pirazolil skupina opcijski supstituirana s jednom ili više C1-6 alkil skupina, oksazolil skupina, ili pirolil skupina;
m je cijeli broj od 1 do 5, i kada m je bilo koji od 2 do 5, tada 2 do 5 od R13 mogu biti isti ili različiti;
R47 i R48 su atom vodika ili C1-6 alkil skupina;
R6 je atom vodika, C1-6 alkil skupina opcijski supstituirana s jednom ili više C1-6 alkoksi skupina, C1-6alkanoil skupina, C1-6 alkilsulfonil skupina, ili fenil C1-6 alkil skupina;
B je -CO-skupina ili C1-6 alkilen skupina;
R7 je atom vodika ili C1-6 alkil skupina;
R8, R9, R10 i R11 su atom vodika ili C1-6 alkil skupina;
R12 i R12a su atom vodika ili C1-6 alkil skupina;
B1 i B3 su C1-6 alkilen skupina;
n je 0 ili 1;
B2 je C2-6 alkenilen skupina;
B9 je C1-6 alkilen skupina ili C2-6 alkenilen skupina;
B10 je C1-6 alkilen skupina;
R2 je atom vodika ili C1-6 alkil skupina;
Y je CH ili N;
A1 je heterociklički prsten odabran iz skupine koju čine indoldiil skupine i indolindiil skupine, gdje heterociklički prsten može imati najmanje jedan supstituent;
T je -N(R14)-B4-CO-skupina, -B5-CO-skupina ili -CO-skupina;
R14 je atom vodika, C1-6 alkil skupina opcijski supstituirana s jednim ili više halogen atoma, cikloalkil skupina, cikloalkilkarbonil skupina, C1-6 alkanoil skupina opcijski supstituirana s jednim ili više halogen atoma, C2-6 alkenil skupina, amino supstituirana C1-6 alkanoil skupina opcijski supstituirana s jednom ili više C1-6 alkil skupina, ili C1-6 alkilsulfonil skupina;
B4 je C1-6 alkilen skupina;
B5 je C2-6 alkenilen skupina ili C1-6 alkilen skupina opcijski supstituirana s jednom ili više hidroksi skupina; i
R3 i R4, zajedno s atomom dušika na koji su vezani, vežu se međusobno, izravno ili preko atoma dušika, ili atoma sumpora, i od 5- do 10-člani heterociklički prsten, gdje zasićeni heterociklički prsten je piperazin prsten s jednom benzil skupinom koja može imati najmanje jedan supstituent.
2. Heterociklički spoj ili njegova sol prema zahtjevu 1, naznačen time, da R1 je R5-SO2-N(R12)-skupina ili R5-B-N(R6)-skupina, gdje je R5 skupina predstavljena općom formulom:
[image]
gdje su m, B, R13, R12 i R6 isti kao što je gore određeno.
3. Heterociklički spoj ili njegova sol prema zahtjevu 1, naznačen time, da je odabran iz skupine koju čine:
4,N-dimetil-N-[6-(2-{4-[4-(2,2,2-trifluoroetoksi)benzil]piperazin-1-karbonil}-1H-indol-6-iloksi)piridin-3-il]benzolsulfonamid,
3,4-dikloro-N-(2-{2-[4-(4-izopropoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}pirimidin-5-il)-N-metilbenzolsulfonamid,
N-[6-(2-{4-[(4-metoksibenzil)metilamino]piperidin-1-karbonil}-1-metil-1H-indol-5-iloksi)piridin-3-il]-4-trifluorometilbenzamid,
2-kloro-N-(6-{2-[4-(4-izopropoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}piridin-3-il)-4-trifluorometilbenzamid,
N-[6-(2-{4-[4-(2-fluoro-1-fluorometiletoksi)benzil]piperazin-1-karbonil}-1-metil-1H-indol-6-iloksi)piridin-3-il]-N-metil-4-trifluorometoksibenzamid,
N-[6-(2-{4-[(E)-3-(4-metoksifenil)alil]piperazin-1-karbonil}-1-metil-1H-indol-5-iloksi)piridin-3-il]-4-trifluorometilbenzamid,
N-(2-{2-[4-(4-metoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}pirimidin-5-il)-4-trifluorometilbenzamid,
N-(6-{2-[4-(4-difluorometoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid,
N-(6-{2-[4-(6-izopropoksipiridin-3-ilmetil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid,
N-(6-{2-[4-(4-izopropilbenzil)piperazin-1-karbonil]-1,4-dimetil-1H-indol-5-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid,
N-metil-N-[6-(1-metil-2-{4-[4-(2,2,2-trifluoroetoksi)benzil]piperazin-1-karbonil}-1H-indol-6-iloksi)piridin-3-il]-4-trifluorometilbenzamid,
N-(6-{2-[4-(4-difluorometoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}piridin-3-il)-N-metil-4-trifluorometoksibenzamid,
N-{6-[2-(4-izobutilpiperazin-1-karbonil)-1-metil-1H-indol-5-iloksi]piridin-3-il}-4-trifluorometilbenzamid,
N-[6-(1-metil-2-{4-[2-(4-trifluorometilfenil)tiazol-5-ilmetilpiperazin-1-karbonil}-1H-indol-5-iloksi)piridin-3-il]-4-trifluorometilbenzamid,
4-metoksi-N-metil-N-[6-(1-metil-2-{4-[4-(2,2,2-trifluoroetoksi)benzil]piperazin-1-karbonil}-1H-indol-6-iloksi)piridin-3-il]benzolsulfonamid,
N-(6-{2-[4-(4-metoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid,
N-(6-{2-[4-(4-etoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}-2-metilpiridin-3-il)-N-metil-4-trifluorometilbenzamid,
N-(6-{2-[4-(4-etilbenzil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid,
N-(2-{2-[4-(4-izopropoksibenzil)piperazin-1-karbonil]-1-metil-1H-indo1-6-iloksi}pirimidin-5-il)-N-metil-4-trifluorometilbenzamid,
N-(6-{1-metil-2-[4-(4-[1,2,3]tiadiazol-4-ilbenzil)piperazin-1-karbonil]-1H-indol-6-iloksi}piridin-3-il)-4-trifluorometilbenzamid,
N-[6-(2-{4-[4-(2-fluoro-1-fluorometiletoksi)benzil]piperazin-1-karbon il}-1-metil-1H-indol-6-iloksi)piridin-3-il]-N-metil-4-trifluorometilbenzamid,
N-[6-(2-{4-[4-(2-fluoro-1-fluorometiletoksi)benzil]piperazin-1-karbon il}-1-metil-1H-indol-6-iloksi)piridin-3-il]-2-metil-4-trifluorometilbenzamid,
N-(6-{2-[4-(4-cijanobenzil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid,
N-(6-{2-[4-(4-etoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid,
N-metil-N-[6-(1-metil-2-{4-[4-(1,1,2,2-tetrafluoroetoksi)benzil]piperazin-1-karbonil}-1H-indol-5-iloksi)piridin-3-il]-4-trifluorometilbenzamid,
N-(6-{2-[4-(5-etoksipiridin-2-ilmetil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid,
N-metil-N-(6-{1-metil-2-[4-(4-propoksibenzil)piperazin-1-karbonil]-1H-indol-6-iloksi}piridin-3-il)-4-trifluorometilbenzamid,
N-(6-{2-[4-(4-izopropoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid,
3,4-dikloro-N-(6-{2-[4-(4-izopropoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}piridin-3-il)-N-metilbenzolsulfonamid,
N-(6-{2-[4-(4-izopropoksibenzil)piperazin-1-karbonil]-1-metil-1H-indo1-6-iloksi}piridin-3-il)-4,N-dimetil-benzolsulfonamid,
i
N-(6-{2-[4-(2,2-difluorobenzo[1,3]dioksol-5-ilmetil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}piridin-3-il)-4,N-dimetil-benzolsulfonamid.
4. Heterociklički spoj ili njegova sol prema zahtjevu 1, naznačen time, da je odabran iz skupine koju čine:
4,N-dimetil-N-[6-(2-{4-[4-(2,2,2-trifluoroetoksi)benzil]piperazin-1-karbonil}-1H-indol-6-iloksi)-piridin-3-il]benzolsulfonamid,
3,4-dikloro-N-(2-{2-[4-(4-izopropoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}pirimidin-5-il)-N-metilbenzolsulfonamid,
N-[6-(2-{4-[(4-metoksibenzil)metilamino]piperidin-1-karbonil}-1-metil-1H-indol-5-iloksi)piridin-3-il]-4-trifluorometilbenzamid-oksalat,
2-kloro-N-(6-{2-[4-(4-izopropoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}piridin-3-il)-4-trifluorometilbenzamid-hidrobromid,
N-[6-(2-{4-[4-(2-fluoro-1-fluorometiletoksi)benzil]piperazin-1-karbonil}-1-metil-1H-indol-6-iloksi)piridin-3-il]-N-metil-4-trifluorometoksibenzamid-hidrobromid,
N-[6-(2-{4-[(E)-3-(4-metoksifenil)alil]piperazin-1-karbonil}-1-metil-1H-indol-5-iloksi)piridin-3-il]-4-trifluorometilbenzamid-metansulfonat,
N-(2-{2-[4-(4-metoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}pirimidin-5-il)-4-trifluorometilbenzamid,
N-(6-{2-[4-(4-difluorometoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid-maleat,
N-(6-{2-[4-(6-izopropoksipiridin-3-ilmetil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid-maleat,
N-(6-{2-[4-(4-izopropilbenzil)piperazin-1-karbonil]-1,4-dimetil-1H-indol-5-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid-hidrobromid,
N-metil-N-[6-(1-metil-2-{4-[4-(2,2,2-trifluoroetoksi)benzil]piperazin-1-karbonil}-1H-indol-6-iloksi)piridin-3-il]-4-trifluorometilbenzamid-hidrobromid,
N-(6-{2-[4-(4-difluorometoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}piridin-3-il)-N-metil-4-trifluorometoksibenzamid-hidrobromid,
N-{6-[2-(4-izobutilpiperazin-1-karbonil)-1-metil-1H-indol-5-iloksi]piridin-3-il}-4-trifluorometilbenzamid,
N-[6-(1-metil-2-{4-[2-(4-trifluorometilfenil)-tiazol-5-ilmetilpiperazin-1-karbonil}-1H-indol-5-iloksi)piridin-3-il]-4-trifluorometilbenzamid-hidrobromid,
4-metoksi-N-metil-N-[6-(1-metil-2-{4-[4-(2,2,2-trifluoroetoksi)benzil]piperazin-1-karbonil}-1H-indol-6-iloksi)piridin-3-il]benzolsulfonamid-hidroklorid,
N-(6-{2-[4-(4-metoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid-maleat,
N-(6-{2-[4-(4-etoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}-2-metilpiridin-3-il)-N-metil-4-trifluorometilbenzamid-hidrobromid,
N-(6-{2-[4-(4-etilbenzil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid-oksalat,
N-(2-{2-[4-(4-izopropoksibenzil)piperazin-1-karbonil]-1-metil-1H-indo1-6-iloksi}pirimidin-5-il)-N-metil-4-trifluorometilbenzamid-hidroklorid,
N-(6-{1-metil-2-[4-(4-[1,2,3]tiadiazol-4-ilbenzil)piperazin-1-karbonil]-1H-indol-6-iloksi}piridin-3-il)-4-trifluorometilbenzamid,
N-[6-(2-{4-[4-(2-fluoro-1-fluorometiletoksi)benzil]piperazin-1-karbonil}-1-metil-1H-indol-6-iloksi)piridin-3-il]-N-metil-4-trifluorometilbenzamid-hidrobromid,
N-[6-(2-{4-[4-(2-fluoro-1-fluorometiletoksi)benzil]piperazin-1-karbonil}-1-metil-1H-indol-6-iloksi)piridin-3-il]-2-metil-4-trifluorometilbenzamid-hidroklorid,
N-(6-{2-[4-(4-cijanobenzil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid-hidrobromid,
N-(6-{2-[4-(4-etoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid-maleat,
N-metil-N-[6-(1-metil-2-{4-[4-(1,1,2,2-tetrafluoroetoksi)benzil]piperazin-1-karbonil}-1H-indol-5-iloksi)piridin-3-il]-4-trifluorometilbenzamid-maleat,
N-(6-{2-[4-(5-etoksipiridin-2-ilmetil)piperazin-1-karbonil]-1-metil-1H-indol-5-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid-maleat,
N-metil-N-(6-{1-metil-2-[4-(4-propoksibenzil)piperazin-1-karbonil]-1H-indol-6-iloksi}piridin-3-il)-4-trifluorometilbenzamid-hidrobromid,
N-(6-{2-[4-(4-izopropoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}piridin-3-il)-N-metil-4-trifluorometilbenzamid-hidrobromid,
3,4-dikloro-N-(6-{2-[4-(4-izopropoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}piridin-3-il)-N-metilbenzolsulfonamid,
N-(6-{2-[4-(4-izopropoksibenzil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}piridin-3-il)-4,N-dimetil-benzolsulfonamid,
i
N-(6-{2-[4-(2,2-difluorobenzo[1,3]dioksol-5-ilmetil)piperazin-1-karbonil]-1-metil-1H-indol-6-iloksi}piridin-3-il)-4,N-dimetil-benzolsulfonamid-hidroklorid.
5. Farmaceutski sastav, naznačen time, da obuhvaća heterociklički spoj ili njegovu sol, kako je predstavljen općom formulom (1) prema zahtjevu 1, te farmakološki prihvatljive nosače.
6. Farmaceutski sastav prema zahtjevu 5, naznačen time, da je za uporabu u postupku prevencije ili liječenja fibroze.
7. Farmaceutski sastav prema zahtjevu 5, naznačen time, da je za uporabu u postupku prevencije ili liječenja tumora.
8. Heterociklički spoj ili njegova sol, kako je predstavljen općom formulom (1) prema zahtjevu 1, naznačen time, da se upotrebljava kao farmaceutski sastav.
9. Heterociklički spoj ili njegova sol, kako je predstavljen općom formulom (1) prema zahtjevu 1, naznačen time, da se upotrebljava u proizvodnji farmaceutskog sastava.
10. Uporaba heterocikličkog spoja ili njegove soli predstavljenog općom formulom (1) prema zahtjevu 1, naznačena time, da je za proizvodnju farmaceutskog sastava.
11. Heterociklički spoj ili njegova sol, kako je predstavljen općom formulom (1) prema zahtjevu 1, naznačen time, da se upotrebljava u postupku prevencije i/ili liječenja fibroze i/ili tumora.
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