RU2011100781A - 2-пиридил-замещенные имидазолы в качестве ингибиторов alk5 и/или alk4 - Google Patents
2-пиридил-замещенные имидазолы в качестве ингибиторов alk5 и/или alk4 Download PDFInfo
- Publication number
- RU2011100781A RU2011100781A RU2011100781/04A RU2011100781A RU2011100781A RU 2011100781 A RU2011100781 A RU 2011100781A RU 2011100781/04 A RU2011100781/04 A RU 2011100781/04A RU 2011100781 A RU2011100781 A RU 2011100781A RU 2011100781 A RU2011100781 A RU 2011100781A
- Authority
- RU
- Russia
- Prior art keywords
- imidazol
- methylpyridin
- quinoline
- fluoro
- methyl
- Prior art date
Links
- -1 2-Pyridyl-Substituted Imidazoles Chemical class 0.000 title claims abstract 87
- 101000799189 Homo sapiens Activin receptor type-1B Proteins 0.000 title claims 3
- 102100034134 Activin receptor type-1B Human genes 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 15
- 125000004122 cyclic group Chemical group 0.000 claims abstract 13
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract 11
- 125000003118 aryl group Chemical group 0.000 claims abstract 9
- 150000002367 halogens Chemical class 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 9
- 125000005842 heteroatom Chemical group 0.000 claims abstract 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 6
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 4
- 125000001424 substituent group Chemical group 0.000 claims abstract 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract 3
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 2
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 238000000034 method Methods 0.000 claims 10
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 8
- 241000124008 Mammalia Species 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- FJFDWTGEEXMENV-UHFFFAOYSA-N 2-[2-[(3-chlorophenyl)methyl]-4-(4-methoxyphenyl)-1H-imidazol-5-yl]-6-methylpyridine 2-[4-(4-chlorophenyl)-2-[[3-(trifluoromethyl)phenyl]methyl]-1H-imidazol-5-yl]-6-methylpyridine Chemical compound ClC1=CC=C(C=C1)C=1N=C(NC1C1=NC(=CC=C1)C)CC1=CC(=CC=C1)C(F)(F)F.ClC=1C=C(CC=2NC(=C(N2)C2=CC=C(C=C2)OC)C2=NC(=CC=C2)C)C=CC1 FJFDWTGEEXMENV-UHFFFAOYSA-N 0.000 claims 4
- PUGXCELHUHOMOZ-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]anilino]ethanol Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(NCCO)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 PUGXCELHUHOMOZ-UHFFFAOYSA-N 0.000 claims 4
- HVPVJQMSTXTZLD-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]-n,n-dimethylethanamine Chemical compound C1=C(F)C(OCCN(C)C)=CC(CC=2NC(=C(N=2)C=2C=C3C=CC=NC3=CC=2)C=2N=C(C)C=CC=2)=C1 HVPVJQMSTXTZLD-UHFFFAOYSA-N 0.000 claims 4
- FBACCGUPAHKVEQ-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]acetamide Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OCC(N)=O)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 FBACCGUPAHKVEQ-UHFFFAOYSA-N 0.000 claims 4
- MELFLWJNWMRMJM-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]acetic acid Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OCC(O)=O)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 MELFLWJNWMRMJM-UHFFFAOYSA-N 0.000 claims 4
- NOHQXYWIGVREJK-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]ethanol Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OCCO)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 NOHQXYWIGVREJK-UHFFFAOYSA-N 0.000 claims 4
- UWYYRRSLCUSOET-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]acetic acid Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OCC(O)=O)C(F)=CC=3)N2)C=2C=C3N=CC=NC3=CC=2)=N1 UWYYRRSLCUSOET-UHFFFAOYSA-N 0.000 claims 4
- FTJHQSXYADHSAY-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]ethanamine Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OCCN)C(F)=CC=3)N2)C=2C=C3N=CC=NC3=CC=2)=N1 FTJHQSXYADHSAY-UHFFFAOYSA-N 0.000 claims 4
- LTSBAKXZLZWTJR-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]ethanol Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OCCO)C(F)=CC=3)N2)C=2C=C3N=CC=NC3=CC=2)=N1 LTSBAKXZLZWTJR-UHFFFAOYSA-N 0.000 claims 4
- RIMVKMGPBRMPLF-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[(2,4,5-trifluorophenyl)methyl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C(=CC(F)=C(F)C=3)F)N2)C=2C=C3OCOC3=CC=2)=N1 RIMVKMGPBRMPLF-UHFFFAOYSA-N 0.000 claims 4
- ATPGFJSTYOQRHN-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[(3-chlorophenyl)methyl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(Cl)C=CC=3)N2)C=2C=C3OCOC3=CC=2)=N1 ATPGFJSTYOQRHN-UHFFFAOYSA-N 0.000 claims 4
- SDESXCNUVAHSRC-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[(3-fluorophenyl)methyl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(F)C=CC=3)N2)C=2C=C3OCOC3=CC=2)=N1 SDESXCNUVAHSRC-UHFFFAOYSA-N 0.000 claims 4
- KGHLFZDFFHSWSU-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[[3-(trifluoromethyl)phenyl]methyl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C=CC=3)C(F)(F)F)N2)C=2C=C3OCOC3=CC=2)=N1 KGHLFZDFFHSWSU-UHFFFAOYSA-N 0.000 claims 4
- NDFBPBOILTYFDS-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-[(3-fluorophenyl)methyl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(F)C=CC=3)N2)C=2C=CC(Cl)=CC=2)=N1 NDFBPBOILTYFDS-UHFFFAOYSA-N 0.000 claims 4
- XXKJPBGNWVIGIX-UHFFFAOYSA-N 2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]benzoic acid Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C(F)=CC=3)C(O)=O)N2)C=2C=C3C=CC=NC3=CC=2)=N1 XXKJPBGNWVIGIX-UHFFFAOYSA-N 0.000 claims 4
- NLZJTJXVZCEGKR-UHFFFAOYSA-N 2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]benzonitrile Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C(F)=CC=3)C#N)N2)C=2C=C3C=CC=NC3=CC=2)=N1 NLZJTJXVZCEGKR-UHFFFAOYSA-N 0.000 claims 4
- FYNWYMYWFIXHNO-UHFFFAOYSA-N 2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenol Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(O)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 FYNWYMYWFIXHNO-UHFFFAOYSA-N 0.000 claims 4
- PXQCXPMOMFHUNZ-UHFFFAOYSA-N 2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]methyl]benzamide Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C(F)=CC=3)C(N)=O)N2)C=2C=C3N=CC=NC3=CC=2)=N1 PXQCXPMOMFHUNZ-UHFFFAOYSA-N 0.000 claims 4
- DISRINLOFKCEPS-UHFFFAOYSA-N 2-fluoro-n-(2-hydroxyethyl)-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]benzamide Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C(F)=CC=3)C(=O)NCCO)N2)C=2C=C3C=CC=NC3=CC=2)=N1 DISRINLOFKCEPS-UHFFFAOYSA-N 0.000 claims 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 4
- GDHRYJIYXAMPCO-UHFFFAOYSA-N 2-methyl-6-[5-(6-methylpyridin-2-yl)-2-[(3-methylsulfonylphenyl)methyl]-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C=CC=3)S(C)(=O)=O)N2)C=2C=C3C=CC(C)=NC3=CC=2)=N1 GDHRYJIYXAMPCO-UHFFFAOYSA-N 0.000 claims 4
- RPUOUCYLDBVTBW-UHFFFAOYSA-N 3-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]-n,n-dimethylpropan-1-amine Chemical compound C1=C(F)C(OCCCN(C)C)=CC(CC=2NC(=C(N=2)C=2C=C3C=CC=NC3=CC=2)C=2N=C(C)C=CC=2)=C1 RPUOUCYLDBVTBW-UHFFFAOYSA-N 0.000 claims 4
- NCKIYFLKUIKXCF-UHFFFAOYSA-N 4-[2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]ethyl]morpholine Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OCCN4CCOCC4)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 NCKIYFLKUIKXCF-UHFFFAOYSA-N 0.000 claims 4
- MXXWWBIRBJHCOT-UHFFFAOYSA-N 6-[2-[(3-chloro-4-methoxyphenyl)methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoxaline Chemical compound C1=C(Cl)C(OC)=CC=C1CC1=NC(C=2C=C3N=CC=NC3=CC=2)=C(C=2N=C(C)C=CC=2)N1 MXXWWBIRBJHCOT-UHFFFAOYSA-N 0.000 claims 4
- LEPAPZHGHRWTDX-UHFFFAOYSA-N 6-[2-[(3-fluorophenyl)methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]-2-methylquinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(F)C=CC=3)N2)C=2C=C3C=CC(C)=NC3=CC=2)=N1 LEPAPZHGHRWTDX-UHFFFAOYSA-N 0.000 claims 4
- CGFOUOBDUSKFJL-UHFFFAOYSA-N 6-[2-[(4-bromophenyl)methyl]-5-(6-methoxypyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound COC1=CC=CC(C2=C(N=C(CC=3C=CC(Br)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 CGFOUOBDUSKFJL-UHFFFAOYSA-N 0.000 claims 4
- TVGPFGGNFUVDRS-UHFFFAOYSA-N 6-[2-[(6-chloropyridin-2-yl)methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3N=C(Cl)C=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 TVGPFGGNFUVDRS-UHFFFAOYSA-N 0.000 claims 4
- IAWCLCUGCPNIBF-UHFFFAOYSA-N 6-[2-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoxaline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C(=C(C=CC=3)C(F)(F)F)F)N2)C=2C=C3N=CC=NC3=CC=2)=N1 IAWCLCUGCPNIBF-UHFFFAOYSA-N 0.000 claims 4
- XGDMEUBKWXUHIE-UHFFFAOYSA-N 6-[2-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoxaline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)N2)C=2C=C3N=CC=NC3=CC=2)=N1 XGDMEUBKWXUHIE-UHFFFAOYSA-N 0.000 claims 4
- HJEGDRFCTDDUOI-UHFFFAOYSA-N 6-[2-[[4-fluoro-3-(2-methoxyethoxy)phenyl]methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound C1=C(F)C(OCCOC)=CC(CC=2NC(=C(N=2)C=2C=C3C=CC=NC3=CC=2)C=2N=C(C)C=CC=2)=C1 HJEGDRFCTDDUOI-UHFFFAOYSA-N 0.000 claims 4
- UIAJCOFJULVZHA-UHFFFAOYSA-N 6-[2-[[4-fluoro-3-(2-pyrrolidin-1-ylethoxy)phenyl]methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OCCN4CCCC4)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 UIAJCOFJULVZHA-UHFFFAOYSA-N 0.000 claims 4
- NUOODYCXSYUSIV-UHFFFAOYSA-N 6-[2-[[4-fluoro-3-(2h-tetrazol-5-yl)phenyl]methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C(F)=CC=3)C=3NN=NN=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 NUOODYCXSYUSIV-UHFFFAOYSA-N 0.000 claims 4
- SPJMKJAXEJEEAI-UHFFFAOYSA-N 6-[2-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C(F)=CC=3)C(F)(F)F)N2)C=2C=C3C=CC=NC3=CC=2)=N1 SPJMKJAXEJEEAI-UHFFFAOYSA-N 0.000 claims 4
- VUMBDAOKNPPDER-UHFFFAOYSA-N 6-[2-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoxaline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C(F)=CC=3)C(F)(F)F)N2)C=2C=C3N=CC=NC3=CC=2)=N1 VUMBDAOKNPPDER-UHFFFAOYSA-N 0.000 claims 4
- BCGYYKZBQMKDRL-UHFFFAOYSA-N 6-[5-(6-bromopyridin-2-yl)-2-[(3-chlorophenyl)methyl]-1H-imidazol-4-yl]quinoline 2-methyl-6-[5-(6-methylpyridin-2-yl)-2-[[3-(trifluoromethyl)phenyl]methyl]-1H-imidazol-4-yl]quinoline Chemical compound CC1=NC2=CC=C(C=C2C=C1)C=1N=C(NC1C1=NC(=CC=C1)C)CC1=CC(=CC=C1)C(F)(F)F.BrC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)Cl)C=1C=C2C=CC=NC2=CC1 BCGYYKZBQMKDRL-UHFFFAOYSA-N 0.000 claims 4
- ZCJNSFZKYCFMGO-UHFFFAOYSA-N 6-[5-(6-bromopyridin-2-yl)-2-[(3-fluorophenyl)methyl]-1H-imidazol-4-yl]-2-methylquinoline 2-[4-(4-methoxyphenyl)-2-[[3-(trifluoromethyl)phenyl]methyl]-1H-imidazol-5-yl]-6-methylpyridine Chemical compound COC1=CC=C(C=C1)C=1N=C(NC1C1=NC(=CC=C1)C)CC1=CC(=CC=C1)C(F)(F)F.BrC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)F)C=1C=C2C=CC(=NC2=CC1)C ZCJNSFZKYCFMGO-UHFFFAOYSA-N 0.000 claims 4
- WRMSWOPLPPJNBC-UHFFFAOYSA-N 6-[5-(6-bromopyridin-2-yl)-2-[[3-(trifluoromethyl)phenyl]methyl]-1H-imidazol-4-yl]quinoline 6-[5-(6-methylpyridin-2-yl)-2-[(3-methylsulfonylphenyl)methyl]-1H-imidazol-4-yl]quinoline Chemical compound BrC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)C(F)(F)F)C=1C=C2C=CC=NC2=CC1.CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)S(=O)(=O)C)C=1C=C2C=CC=NC2=CC1 WRMSWOPLPPJNBC-UHFFFAOYSA-N 0.000 claims 4
- NZJADIIOVAHUKP-UHFFFAOYSA-N 6-[5-(6-bromopyridin-2-yl)-2-[[3-(trifluoromethyl)phenyl]methyl]-1h-imidazol-4-yl]-2-methylquinoline Chemical compound C1=CC2=NC(C)=CC=C2C=C1C(=C(N1)C=2N=C(Br)C=CC=2)N=C1CC1=CC=CC(C(F)(F)F)=C1 NZJADIIOVAHUKP-UHFFFAOYSA-N 0.000 claims 4
- AQSMATYMYCPRBW-UHFFFAOYSA-N 6-[5-(6-methylpyridin-2-yl)-2-[[2-(trifluoromethyl)phenyl]methyl]-1h-imidazol-4-yl]quinoxaline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C(=CC=CC=3)C(F)(F)F)N2)C=2C=C3N=CC=NC3=CC=2)=N1 AQSMATYMYCPRBW-UHFFFAOYSA-N 0.000 claims 4
- GWWQYLLOZKEZBB-UHFFFAOYSA-N 6-[5-(6-methylpyridin-2-yl)-2-[[3-(trifluoromethoxy)phenyl]methyl]-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OC(F)(F)F)C=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 GWWQYLLOZKEZBB-UHFFFAOYSA-N 0.000 claims 4
- FSZHDCDWVYITGA-UHFFFAOYSA-N 6-[5-(6-methylpyridin-2-yl)-2-[[3-(trifluoromethoxy)phenyl]methyl]-1h-imidazol-4-yl]quinoxaline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OC(F)(F)F)C=CC=3)N2)C=2C=C3N=CC=NC3=CC=2)=N1 FSZHDCDWVYITGA-UHFFFAOYSA-N 0.000 claims 4
- VQQKSXCXPRMTJB-UHFFFAOYSA-N 6-[5-(6-methylpyridin-2-yl)-2-[[4-(trifluoromethyl)phenyl]methyl]-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=CC(=CC=3)C(F)(F)F)N2)C=2C=C3C=CC=NC3=CC=2)=N1 VQQKSXCXPRMTJB-UHFFFAOYSA-N 0.000 claims 4
- ALDUHHYZTGPWQE-UHFFFAOYSA-N 6-[5-(6-methylpyridin-2-yl)-2-[[4-(trifluoromethyl)phenyl]methyl]-1h-imidazol-4-yl]quinoxaline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=CC(=CC=3)C(F)(F)F)N2)C=2C=C3N=CC=NC3=CC=2)=N1 ALDUHHYZTGPWQE-UHFFFAOYSA-N 0.000 claims 4
- SPDKJWOSWGZPTA-UHFFFAOYSA-N BrC1=CC=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC=CC=C2)C=C1.BrC1=CC=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C1 Chemical compound BrC1=CC=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC=CC=C2)C=C1.BrC1=CC=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C1 SPDKJWOSWGZPTA-UHFFFAOYSA-N 0.000 claims 4
- CFWFRAPHXOYVCD-UHFFFAOYSA-N BrC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)Cl)C=1C=C2C=CC(=NC2=CC1)C.BrC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC(=NC3=CC2)C)C2=NC(=CC=C2)Br)C=CC1 Chemical compound BrC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)Cl)C=1C=C2C=CC(=NC2=CC1)C.BrC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC(=NC3=CC2)C)C2=NC(=CC=C2)Br)C=CC1 CFWFRAPHXOYVCD-UHFFFAOYSA-N 0.000 claims 4
- BSIRSUPRXMDVOT-UHFFFAOYSA-N BrC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)Br)C=CC1.BrC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)F)C=1C=C2C=CC=NC2=CC1 Chemical compound BrC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)Br)C=CC1.BrC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)F)C=1C=C2C=CC=NC2=CC1 BSIRSUPRXMDVOT-UHFFFAOYSA-N 0.000 claims 4
- SHUMCZVELKFLEY-UHFFFAOYSA-N CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=NC=CC=C1)C=1C=C2C=CC=NC2=CC1.FC1=C(N)C=C(C=C1)CC=1NC(=C(N1)C=1C=C2N=CC=NC2=CC1)C1=NC(=CC=C1)C Chemical compound CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=NC=CC=C1)C=1C=C2C=CC=NC2=CC1.FC1=C(N)C=C(C=C1)CC=1NC(=C(N1)C=1C=C2N=CC=NC2=CC1)C1=NC(=CC=C1)C SHUMCZVELKFLEY-UHFFFAOYSA-N 0.000 claims 4
- SUQSVSNGLCSZKN-UHFFFAOYSA-N ClC1=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC(=C1)Cl.ClC=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1Cl Chemical compound ClC1=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC(=C1)Cl.ClC=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1Cl SUQSVSNGLCSZKN-UHFFFAOYSA-N 0.000 claims 4
- LTDRSAZDAPORGS-UHFFFAOYSA-N ClC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC(=NC3=CC2)C)C2=NC(=CC=C2)C)C=CC1.BrC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC(=NC3=CC2)C)C2=NC(=CC=C2)C)C=CC1 Chemical compound ClC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC(=NC3=CC2)C)C2=NC(=CC=C2)C)C=CC1.BrC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC(=NC3=CC2)C)C2=NC(=CC=C2)C)C=CC1 LTDRSAZDAPORGS-UHFFFAOYSA-N 0.000 claims 4
- YAFNBOLZGXJOKF-UHFFFAOYSA-N ClC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1.BrC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1 Chemical compound ClC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1.BrC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1 YAFNBOLZGXJOKF-UHFFFAOYSA-N 0.000 claims 4
- IRYKRQHDCQIIQZ-UHFFFAOYSA-N FC1=C(C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C1)[N+](=O)[O-].CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)N1CCCC1)C=1C=C2C=CC=NC2=CC1 Chemical compound FC1=C(C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C1)[N+](=O)[O-].CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)N1CCCC1)C=1C=C2C=CC=NC2=CC1 IRYKRQHDCQIIQZ-UHFFFAOYSA-N 0.000 claims 4
- JXGCGQUKUMGPEZ-UHFFFAOYSA-N FC1=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC=C1F.FC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C(C1)F Chemical compound FC1=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC=C1F.FC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C(C1)F JXGCGQUKUMGPEZ-UHFFFAOYSA-N 0.000 claims 4
- NPRQWFNBCJRQGM-UHFFFAOYSA-N FC1=C(N)C=C(C=C1)CC=1NC(=C(N1)C=1C=C2C=CC=NC2=CC1)C1=NC(=CC=C1)C.FC1=C(C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C1)[N+](=O)[O-] Chemical compound FC1=C(N)C=C(C=C1)CC=1NC(=C(N1)C=1C=C2C=CC=NC2=CC1)C1=NC(=CC=C1)C.FC1=C(C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C1)[N+](=O)[O-] NPRQWFNBCJRQGM-UHFFFAOYSA-N 0.000 claims 4
- GRSMBGMVBMLADD-UHFFFAOYSA-N FC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1.CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)C(F)(F)F)C=1C=C2C=CC=NC2=CC1 Chemical compound FC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1.CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)C(F)(F)F)C=1C=C2C=CC=NC2=CC1 GRSMBGMVBMLADD-UHFFFAOYSA-N 0.000 claims 4
- RDMXFLVGSLZUSW-UHFFFAOYSA-N FC=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C(C1)F.FC=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1F Chemical compound FC=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=C(C1)F.FC=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1F RDMXFLVGSLZUSW-UHFFFAOYSA-N 0.000 claims 4
- JDDLUTLZFUSMEA-UHFFFAOYSA-N FC=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1OC.BrC=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1F Chemical compound FC=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1OC.BrC=1C=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1F JDDLUTLZFUSMEA-UHFFFAOYSA-N 0.000 claims 4
- DIUPBDXWGYGBIO-UHFFFAOYSA-N [2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenyl]methanol Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(CO)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 DIUPBDXWGYGBIO-UHFFFAOYSA-N 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- FJPQGUFPOGUGBI-UHFFFAOYSA-N methyl 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]acetate Chemical compound C1=C(F)C(OCC(=O)OC)=CC(CC=2NC(=C(N=2)C=2C=C3C=CC=NC3=CC=2)C=2N=C(C)C=CC=2)=C1 FJPQGUFPOGUGBI-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 4
- WYCQBIWEJILRMC-UHFFFAOYSA-N 6-[2-[(2-fluorophenyl)methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C(=CC=CC=3)F)N2)C=2C=C3C=CC=NC3=CC=2)=N1 WYCQBIWEJILRMC-UHFFFAOYSA-N 0.000 claims 3
- FIFUGUDHVKLCRY-UHFFFAOYSA-N 6-[2-[[2-fluoro-3-(trifluoromethyl)phenyl]methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C(=C(C=CC=3)C(F)(F)F)F)N2)C=2C=C3C=CC=NC3=CC=2)=N1 FIFUGUDHVKLCRY-UHFFFAOYSA-N 0.000 claims 3
- USLPFXRMCJDERG-UHFFFAOYSA-N 6-[5-(6-methylpyridin-2-yl)-2-[[4-(trifluoromethoxy)phenyl]methyl]-1h-imidazol-4-yl]quinoxaline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=CC(OC(F)(F)F)=CC=3)N2)C=2C=C3N=CC=NC3=CC=2)=N1 USLPFXRMCJDERG-UHFFFAOYSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 230000002440 hepatic effect Effects 0.000 claims 3
- 201000002793 renal fibrosis Diseases 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 206010019668 Hepatic fibrosis Diseases 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- ASNSTHNIXXBVJO-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]ethanamine Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OCCN)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 ASNSTHNIXXBVJO-UHFFFAOYSA-N 0.000 claims 1
- ZAFIFISGEVSCHQ-UHFFFAOYSA-N 6-[2-[(3-bromo-4-fluorophenyl)methyl]-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl]quinoline 6-[2-[(3,4-difluorophenyl)methyl]-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl]quinoline Chemical compound BrC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1F.FC=1C=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC1F ZAFIFISGEVSCHQ-UHFFFAOYSA-N 0.000 claims 1
- LHJQRRRYVRGAFZ-UHFFFAOYSA-N 6-[5-(6-methylpyridin-2-yl)-2-[[2-(trifluoromethyl)phenyl]methyl]-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C(=CC=CC=3)C(F)(F)F)N2)C=2C=C3C=CC=NC3=CC=2)=N1 LHJQRRRYVRGAFZ-UHFFFAOYSA-N 0.000 claims 1
- 208000007122 AIDS-Associated Nephropathy Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000032544 Cicatrix Diseases 0.000 claims 1
- 206010056370 Congestive cardiomyopathy Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 201000003066 Diffuse Scleroderma Diseases 0.000 claims 1
- 201000010046 Dilated cardiomyopathy Diseases 0.000 claims 1
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- RCTMDNRTNONOSN-UHFFFAOYSA-N FC1=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC=C1C(F)(F)F.CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)OC1=CC=CC=C1)C=1C=C2N=CC=NC2=CC1 Chemical compound FC1=C(CC=2NC(=C(N2)C=2C=C3C=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC=C1C(F)(F)F.CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=CC(=CC=C1)OC1=CC=CC=C1)C=1C=C2N=CC=NC2=CC1 RCTMDNRTNONOSN-UHFFFAOYSA-N 0.000 claims 1
- CDUDXLZDCGNQMC-UHFFFAOYSA-N FC1=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC=C1.CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=C(C=C(C(=C1)F)F)F)C=1C=C2C=CC=NC2=CC1 Chemical compound FC1=C(CC=2NC(=C(N2)C=2C=C3N=CC=NC3=CC2)C2=NC(=CC=C2)C)C=CC=C1.CC1=CC=CC(=N1)C1=C(N=C(N1)CC1=C(C=C(C(=C1)F)F)F)C=1C=C2C=CC=NC2=CC1 CDUDXLZDCGNQMC-UHFFFAOYSA-N 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 206010070737 HIV associated nephropathy Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
- 206010023421 Kidney fibrosis Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 208000005777 Lupus Nephritis Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 208000009525 Myocarditis Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 208000004362 Penile Induration Diseases 0.000 claims 1
- 208000020758 Peyronie disease Diseases 0.000 claims 1
- 208000002158 Proliferative Vitreoretinopathy Diseases 0.000 claims 1
- 206010037437 Pulmonary thrombosis Diseases 0.000 claims 1
- 208000032056 Radiation Fibrosis Syndrome Diseases 0.000 claims 1
- 206010067953 Radiation fibrosis Diseases 0.000 claims 1
- 206010038934 Retinopathy proliferative Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 208000002847 Surgical Wound Diseases 0.000 claims 1
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 1
- 206010042953 Systemic sclerosis Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 206010057469 Vascular stenosis Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 210000003445 biliary tract Anatomy 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 201000001981 dermatomyositis Diseases 0.000 claims 1
- 210000004207 dermis Anatomy 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 230000009429 distress Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 231100000283 hepatitis Toxicity 0.000 claims 1
- 230000001969 hypertrophic effect Effects 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 claims 1
- 201000001881 impotence Diseases 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- 208000011379 keloid formation Diseases 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 230000005976 liver dysfunction Effects 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 208000021971 neovascular inflammatory vitreoretinopathy Diseases 0.000 claims 1
- 230000007658 neurological function Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 231100000614 poison Toxicity 0.000 claims 1
- 208000005987 polymyositis Diseases 0.000 claims 1
- 230000006785 proliferative vitreoretinopathy Effects 0.000 claims 1
- 230000029058 respiratory gaseous exchange Effects 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 231100000241 scar Toxicity 0.000 claims 1
- 230000037387 scars Effects 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 239000003440 toxic substance Substances 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
- 231100000397 ulcer Toxicity 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 8
- 125000005843 halogen group Chemical group 0.000 abstract 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Ceramic Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Gastroenterology & Hepatology (AREA)
- Diabetes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/155,984 | 2008-06-12 | ||
| US12/155,984 US20080319012A1 (en) | 2004-04-21 | 2008-06-12 | 2-Pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2011100781A true RU2011100781A (ru) | 2012-07-20 |
Family
ID=41417193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2011100781/04A RU2011100781A (ru) | 2008-06-12 | 2009-06-11 | 2-пиридил-замещенные имидазолы в качестве ингибиторов alk5 и/или alk4 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20080319012A1 (https=) |
| EP (1) | EP2303860A4 (https=) |
| JP (1) | JP2011522877A (https=) |
| KR (1) | KR101654859B1 (https=) |
| CN (1) | CN102083811B (https=) |
| AU (1) | AU2009259021A1 (https=) |
| BR (1) | BRPI0909899A2 (https=) |
| CA (1) | CA2727607A1 (https=) |
| IL (1) | IL209915A (https=) |
| MX (1) | MX2010013549A (https=) |
| RU (1) | RU2011100781A (https=) |
| WO (1) | WO2009150547A2 (https=) |
| ZA (1) | ZA201100277B (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080319012A1 (en) * | 2004-04-21 | 2008-12-25 | In2Gen Co., Ltd. | 2-Pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
| CA2720343A1 (en) * | 2008-04-04 | 2009-10-08 | Takeda Pharmaceutical Company Limited | Heterocyclic derivative and use thereof |
| US8080568B1 (en) | 2010-06-29 | 2011-12-20 | Ewha University - Industry Collaboration Foundation | 2-pyridyl substituted imidazoles as therapeutic ALK5 and/or ALK4 inhibitors |
| USRE47141E1 (en) | 2010-06-29 | 2018-11-27 | EWHA University—Industry Collaboration Foundation | Methods of treating fibrosis, cancer and vascular injuries |
| US8513222B2 (en) | 2010-06-29 | 2013-08-20 | EWHA University—Industry Collaboration Foundation | Methods of treating fibrosis, cancer and vascular injuries |
| AU2012212323A1 (en) | 2011-02-01 | 2013-09-12 | The Board Of Trustees Of The University Of Illinois | HDAC inhibitors and therapeutic methods using the same |
| AU2012281281B2 (en) * | 2011-07-13 | 2017-06-01 | Tiumbio Co., Ltd | 2-pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
| BR112021011224A2 (pt) | 2018-12-11 | 2021-08-24 | Theravance Biopharma R&D Ip, Llc | Inibidores de alk5 |
| KR20220104208A (ko) * | 2019-11-22 | 2022-07-26 | 세라밴스 바이오파마 알앤디 아이피, 엘엘씨 | Alk5 억제제로서 치환된 1,5-나프티리딘 또는 퀴놀린 |
| JP2023509760A (ja) | 2020-01-08 | 2023-03-09 | シンシス セラピューティクス，インコーポレイテッド | Ａｌｋ５阻害剤複合体およびその使用 |
| AR122711A1 (es) * | 2020-06-25 | 2022-09-28 | Alchemedicine Inc | COMPUESTO HETEROCÍCLICO COMO INHIBIDOR DE CASEÍNA QUINASA 1d Y/O QUINASA 5 TIPO RECEPTOR DE ACTIVINA |
| WO2022063050A1 (zh) | 2020-09-28 | 2022-03-31 | 四川科伦博泰生物医药股份有限公司 | 吡唑类化合物及其制备方法和用途 |
| CN121712526A (zh) | 2023-06-13 | 2026-03-20 | 辛瑟斯治疗股份有限公司 | 抗cd5抗体及其用途 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60001229T2 (de) | 1999-04-09 | 2003-10-30 | Smithkline Beecham Corp., Philadelphia | Triarylimidazole |
| CO5271680A1 (es) * | 2000-02-21 | 2003-04-30 | Smithkline Beecham Corp | Compuestos |
| GB0007405D0 (en) | 2000-03-27 | 2000-05-17 | Smithkline Beecham Corp | Compounds |
| GB0100762D0 (en) | 2001-01-11 | 2001-02-21 | Smithkline Beecham Plc | Novel use |
| EP1391452A4 (en) | 2001-05-25 | 2005-10-26 | Mochida Pharm Co Ltd | 4-HYDROXPIPERIDIN DERIVATIVE ANALGETIC EFFECT |
| AR039241A1 (es) | 2002-04-04 | 2005-02-16 | Biogen Inc | Heteroarilos trisustituidos y metodos para su produccion y uso de los mismos |
| MXPA05002981A (es) * | 2002-09-18 | 2005-06-22 | Pfizer Prod Inc | Nuevos compuestos de imidazol como inhibidores del factor de crecimiento transformante (tgf). |
| US7250434B2 (en) * | 2003-12-22 | 2007-07-31 | Janssen Pharmaceutica N.V. | CCK-1 receptor modulators |
| US20080319012A1 (en) | 2004-04-21 | 2008-12-25 | In2Gen Co., Ltd. | 2-Pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
| US8420685B2 (en) * | 2004-04-21 | 2013-04-16 | Sk Chemicals Co., Ltd. | 2-pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
| KR100749566B1 (ko) * | 2004-04-21 | 2007-08-16 | 이화여자대학교 산학협력단 | Ａｌｋ5 및/또는 ａｌｋ4 억제제로 유효한 2-피리딜이치환된 이미다졸 유도체 |
-
2008
- 2008-06-12 US US12/155,984 patent/US20080319012A1/en not_active Abandoned
-
2009
- 2009-06-11 CA CA2727607A patent/CA2727607A1/en not_active Abandoned
- 2009-06-11 CN CN200980121870.1A patent/CN102083811B/zh not_active Expired - Fee Related
- 2009-06-11 MX MX2010013549A patent/MX2010013549A/es active IP Right Grant
- 2009-06-11 WO PCT/IB2009/006398 patent/WO2009150547A2/en not_active Ceased
- 2009-06-11 AU AU2009259021A patent/AU2009259021A1/en not_active Abandoned
- 2009-06-11 RU RU2011100781/04A patent/RU2011100781A/ru not_active Application Discontinuation
- 2009-06-11 KR KR1020117000260A patent/KR101654859B1/ko not_active Expired - Fee Related
- 2009-06-11 EP EP09762075A patent/EP2303860A4/en not_active Withdrawn
- 2009-06-11 JP JP2011513075A patent/JP2011522877A/ja active Pending
- 2009-06-11 BR BRPI0909899A patent/BRPI0909899A2/pt not_active IP Right Cessation
-
2010
- 2010-12-09 IL IL209915A patent/IL209915A/en not_active IP Right Cessation
-
2011
- 2011-01-10 ZA ZA2011/00277A patent/ZA201100277B/en unknown
- 2011-06-22 US US13/067,737 patent/US20130245066A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2727607A1 (en) | 2009-12-17 |
| KR101654859B1 (ko) | 2016-09-07 |
| CN102083811A (zh) | 2011-06-01 |
| EP2303860A2 (en) | 2011-04-06 |
| EP2303860A4 (en) | 2011-07-06 |
| WO2009150547A3 (en) | 2010-08-26 |
| KR20110022662A (ko) | 2011-03-07 |
| ZA201100277B (en) | 2012-03-28 |
| CN102083811B (zh) | 2014-01-22 |
| US20080319012A1 (en) | 2008-12-25 |
| JP2011522877A (ja) | 2011-08-04 |
| IL209915A0 (en) | 2011-02-28 |
| BRPI0909899A2 (pt) | 2016-02-16 |
| IL209915A (en) | 2015-10-29 |
| US20130245066A1 (en) | 2013-09-19 |
| AU2009259021A1 (en) | 2009-12-17 |
| WO2009150547A2 (en) | 2009-12-17 |
| MX2010013549A (es) | 2011-06-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2011100781A (ru) | 2-пиридил-замещенные имидазолы в качестве ингибиторов alk5 и/или alk4 | |
| JP2011522877A5 (https=) | ||
| RU2014105169A (ru) | 2-пиридилзамещенные имидазолы в качестве ингибиторов alk5 и/или alk4 | |
| JP5542713B2 (ja) | 腎機能障害の治療用の医薬の製造のためのドーパミン−ｄ３−レセプターリガンドの使用 | |
| RU2348627C2 (ru) | Ингибиторы тирозинкиназ | |
| JP2020526561A5 (https=) | ||
| RU2008141509A (ru) | Mglur5 модуляторы 1 | |
| JP2005506308A5 (https=) | ||
| JP2015517566A5 (https=) | ||
| JP2008509187A5 (https=) | ||
| JP2003528810A5 (https=) | ||
| JP2008513498A5 (https=) | ||
| RU2010125220A (ru) | Ненуклеозидные ингибиторы обратной транскриптазы | |
| RU2009114857A (ru) | Гетероциклические органические соединения | |
| JP2007511203A5 (https=) | ||
| JP2008503484A5 (https=) | ||
| RU2009148673A (ru) | Производные пиразинона и их применение для лечения легочных заболеваний | |
| RU2008141511A (ru) | Конденсированные гетероциклические соединения и их применение в качестве модуляторов mglur5 | |
| JP2004525149A5 (https=) | ||
| RU2007101236A (ru) | Новые гидантоиновые производные для лечения обструктивных заболеваний дыхательных путей | |
| RU2009111113A (ru) | Мидуляторы mglur5 | |
| JP2009538873A5 (https=) | ||
| RU2006146632A (ru) | Производные хиназолинона, полезные в качестве ванилоидных антагонистов | |
| RU2012139828A (ru) | Производные пиразолопиперидина в качестве ингибиторов nadph-оксидазы | |
| SI3038622T1 (en) | Heterocyclic compounds and methods of use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20140514 |