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
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- 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
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- RU
- Russia
- Prior art keywords
- imidazol
- methylpyridin
- quinoline
- fluoro
- methyl
- Prior art date
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- -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
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- 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
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- 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
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- 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
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- 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
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- 208000002847 Surgical Wound Diseases 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
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- 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
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- 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
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- 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
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- 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
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/155,984 US20080319012A1 (en) | 2004-04-21 | 2008-06-12 | 2-Pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
| US12/155,984 | 2008-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2011100781A true RU2011100781A (ru) | 2012-07-20 |
Family
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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 (enExample) |
| EP (1) | EP2303860A4 (enExample) |
| JP (1) | JP2011522877A (enExample) |
| KR (1) | KR101654859B1 (enExample) |
| CN (1) | CN102083811B (enExample) |
| AU (1) | AU2009259021A1 (enExample) |
| BR (1) | BRPI0909899A2 (enExample) |
| CA (1) | CA2727607A1 (enExample) |
| IL (1) | IL209915A (enExample) |
| MX (1) | MX2010013549A (enExample) |
| RU (1) | RU2011100781A (enExample) |
| WO (1) | WO2009150547A2 (enExample) |
| ZA (1) | ZA201100277B (enExample) |
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 |
| WO2009123316A1 (ja) * | 2008-04-04 | 2009-10-08 | 武田薬品工業株式会社 | 複素環誘導体及びその用途 |
| 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 |
| US8080568B1 (en) * | 2010-06-29 | 2011-12-20 | Ewha University - Industry Collaboration Foundation | 2-pyridyl substituted imidazoles as therapeutic ALK5 and/or ALK4 inhibitors |
| WO2012106343A2 (en) | 2011-02-01 | 2012-08-09 | The Board Of Trustees Of The University Of Illinois | Hdac inhibitors and therapeutic methods using the same |
| EP2731949B1 (en) * | 2011-07-13 | 2018-04-04 | TiumBio Co., Ltd. | 2-pyridyl substituted imidazoles as alk5 and/or alk4 inhibitors |
| MX2021006831A (es) | 2018-12-11 | 2021-07-02 | Theravance Biopharma R&D Ip Llc | Inhibidores de alk5. |
| CN114728941A (zh) * | 2019-11-22 | 2022-07-08 | 施万生物制药研发Ip有限责任公司 | 作为alk5抑制剂的经取代的1,5-萘啶或喹啉 |
| EP4087657A1 (en) | 2020-01-08 | 2022-11-16 | Synthis Therapeutics, Inc. | Alk5 inhibitor conjugates and uses thereof |
| 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 |
| EP4219453A4 (en) | 2020-09-28 | 2024-10-09 | Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd. | PYRAZOLE COMPOUND AND ITS PREPARATION METHOD AND ITS USE |
| WO2024258967A1 (en) | 2023-06-13 | 2024-12-19 | Synthis Therapeutics, Inc. | Anti-cd5 antibodies and their uses |
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 |
| AR029803A1 (es) * | 2000-02-21 | 2003-07-16 | Smithkline Beecham Plc | Imidazoles sustituidos con piridilo y composiciones farmaceuticas que las comprenden |
| 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 |
| OA12928A (en) * | 2002-09-18 | 2006-10-13 | Pfizer Prod Inc | Novel imidazole compounds as transforming growth factor (TGF) inhibitors. |
| US7250434B2 (en) * | 2003-12-22 | 2007-07-31 | Janssen Pharmaceutica N.V. | CCK-1 receptor modulators |
| US8420685B2 (en) * | 2004-04-21 | 2013-04-16 | Sk Chemicals Co., Ltd. | 2-pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
| US20080319012A1 (en) * | 2004-04-21 | 2008-12-25 | In2Gen 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 |
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2008
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2009
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- 2009-06-11 KR KR1020117000260A patent/KR101654859B1/ko not_active Expired - Fee Related
- 2009-06-11 WO PCT/IB2009/006398 patent/WO2009150547A2/en not_active Ceased
- 2009-06-11 RU RU2011100781/04A patent/RU2011100781A/ru not_active Application Discontinuation
- 2009-06-11 BR BRPI0909899A patent/BRPI0909899A2/pt not_active IP Right Cessation
- 2009-06-11 EP EP09762075A patent/EP2303860A4/en not_active Withdrawn
- 2009-06-11 CN CN200980121870.1A patent/CN102083811B/zh not_active Expired - Fee Related
- 2009-06-11 AU AU2009259021A patent/AU2009259021A1/en not_active Abandoned
- 2009-06-11 JP JP2011513075A patent/JP2011522877A/ja active Pending
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2010
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2011
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- 2011-06-22 US US13/067,737 patent/US20130245066A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IL209915A0 (en) | 2011-02-28 |
| KR20110022662A (ko) | 2011-03-07 |
| ZA201100277B (en) | 2012-03-28 |
| EP2303860A4 (en) | 2011-07-06 |
| CA2727607A1 (en) | 2009-12-17 |
| MX2010013549A (es) | 2011-06-22 |
| US20080319012A1 (en) | 2008-12-25 |
| CN102083811A (zh) | 2011-06-01 |
| JP2011522877A (ja) | 2011-08-04 |
| AU2009259021A1 (en) | 2009-12-17 |
| BRPI0909899A2 (pt) | 2016-02-16 |
| KR101654859B1 (ko) | 2016-09-07 |
| US20130245066A1 (en) | 2013-09-19 |
| WO2009150547A3 (en) | 2010-08-26 |
| WO2009150547A2 (en) | 2009-12-17 |
| IL209915A (en) | 2015-10-29 |
| EP2303860A2 (en) | 2011-04-06 |
| CN102083811B (zh) | 2014-01-22 |
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| Date | Code | Title | Description |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20140514 |