HRP20090494T1 - Supstituirani pirolopiridini, pripravak koji ih sadrži, postupak njihovog dobivanja i njihova upotreba - Google Patents
Supstituirani pirolopiridini, pripravak koji ih sadrži, postupak njihovog dobivanja i njihova upotreba Download PDFInfo
- Publication number
- HRP20090494T1 HRP20090494T1 HR20090494T HRP20090494T HRP20090494T1 HR P20090494 T1 HRP20090494 T1 HR P20090494T1 HR 20090494 T HR20090494 T HR 20090494T HR P20090494 T HRP20090494 T HR P20090494T HR P20090494 T1 HRP20090494 T1 HR P20090494T1
- Authority
- HR
- Croatia
- Prior art keywords
- phenyl
- pyrrolo
- carboxamide
- pyridine
- ureido
- Prior art date
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- 150000005255 pyrrolopyridines Chemical class 0.000 title 1
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- -1 (C1-C3)alkylOH Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 108091000080 Phosphotransferase Proteins 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 102000020233 phosphotransferase Human genes 0.000 claims 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- 101100481408 Danio rerio tie2 gene Proteins 0.000 claims 2
- 101100481410 Mus musculus Tek gene Proteins 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229910052744 lithium Inorganic materials 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 1
- MGBBMMGUPULGGI-UHFFFAOYSA-N 3-[4-[(2,5-dimethoxyphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound COC1=CC=C(OC)C(NC(=O)NC=2C=CC(=CC=2)C=2C3=CC=CN=C3NC=2C(N)=O)=C1 MGBBMMGUPULGGI-UHFFFAOYSA-N 0.000 claims 1
- FCAGMTQWSOYTFP-UHFFFAOYSA-N 3-[4-[(2,5-dimethoxyphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=C(OC)C(NC(=O)NC=2C=CC(=CC=2)C=2C3=CC=NC=C3NC=2C(N)=O)=C1 FCAGMTQWSOYTFP-UHFFFAOYSA-N 0.000 claims 1
- JGUIDHASKFORMW-UHFFFAOYSA-N 3-[4-[(2,5-dimethylphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound CC1=CC=C(C)C(NC(=O)NC=2C=CC(=CC=2)C=2C3=CC=CN=C3NC=2C(N)=O)=C1 JGUIDHASKFORMW-UHFFFAOYSA-N 0.000 claims 1
- CTDVCODGQXJTRT-UHFFFAOYSA-N 3-[4-[(2-fluoro-5-methylphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=C(F)C(NC(=O)NC=2C=CC(=CC=2)C=2C3=CC=NC=C3NC=2C(N)=O)=C1 CTDVCODGQXJTRT-UHFFFAOYSA-N 0.000 claims 1
- SHRJKKHKJVUVMX-UHFFFAOYSA-N 3-[4-[(2-fluorophenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=NC=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1F SHRJKKHKJVUVMX-UHFFFAOYSA-N 0.000 claims 1
- ULPVYLKZUMTHNO-UHFFFAOYSA-N 3-[4-[(2-fluorophenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1F ULPVYLKZUMTHNO-UHFFFAOYSA-N 0.000 claims 1
- DQRZKRBWOJQLQB-UHFFFAOYSA-N 3-[4-[(2-methoxy-5-methylphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound COC1=CC=C(C)C=C1NC(=O)NC1=CC=C(C=2C3=CC=NC=C3NC=2C(N)=O)C=C1 DQRZKRBWOJQLQB-UHFFFAOYSA-N 0.000 claims 1
- PDYNVUIHKRNIFF-UHFFFAOYSA-N 3-[4-[(2-methoxyphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=C(C=2C3=CC=CN=C3NC=2C(N)=O)C=C1 PDYNVUIHKRNIFF-UHFFFAOYSA-N 0.000 claims 1
- IDFPPGWWPYAHSB-UHFFFAOYSA-N 3-[4-[(2-methoxyphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=C(C=2C3=CC=NC=C3NC=2C(N)=O)C=C1 IDFPPGWWPYAHSB-UHFFFAOYSA-N 0.000 claims 1
- YYLIMKHJORJAJE-UHFFFAOYSA-N 3-[4-[(2-methylphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)NC1=CC=C(C=2C3=CC=NC=C3NC=2C(N)=O)C=C1 YYLIMKHJORJAJE-UHFFFAOYSA-N 0.000 claims 1
- CWOFZMYOJDUQPI-UHFFFAOYSA-N 3-[4-[(3,4-dimethoxyphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1NC(=O)NC1=CC=C(C=2C3=CC=CN=C3NC=2C(N)=O)C=C1 CWOFZMYOJDUQPI-UHFFFAOYSA-N 0.000 claims 1
- JAKZUVPXWHORRT-UHFFFAOYSA-N 3-[4-[(3,4-dimethoxyphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(OC)C(OC)=CC=C1NC(=O)NC1=CC=C(C=2C3=CC=NC=C3NC=2C(N)=O)C=C1 JAKZUVPXWHORRT-UHFFFAOYSA-N 0.000 claims 1
- QYKZBKDOZVSQNT-UHFFFAOYSA-N 3-[4-[(3,4-dimethylphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC(=O)NC1=CC=C(C=2C3=CC=NC=C3NC=2C(N)=O)C=C1 QYKZBKDOZVSQNT-UHFFFAOYSA-N 0.000 claims 1
- HVYXWQZZIUYTPY-UHFFFAOYSA-N 3-[4-[(3,5-dimethylphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound CC1=CC(C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C3=CC=NC=C3NC=2C(N)=O)=C1 HVYXWQZZIUYTPY-UHFFFAOYSA-N 0.000 claims 1
- KNGFTOOCHUHPMI-UHFFFAOYSA-N 3-[4-[(3-chloro-4-fluorophenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C(Cl)=C1 KNGFTOOCHUHPMI-UHFFFAOYSA-N 0.000 claims 1
- BLFUAOVQOPWUNZ-UHFFFAOYSA-N 3-[4-[(3-chlorophenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 BLFUAOVQOPWUNZ-UHFFFAOYSA-N 0.000 claims 1
- DENIIUNLFAWVQS-UHFFFAOYSA-N 3-[4-[(3-ethylphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound CCC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C3=CC=CN=C3NC=2C(N)=O)=C1 DENIIUNLFAWVQS-UHFFFAOYSA-N 0.000 claims 1
- HTFPJYFDVJPYDS-UHFFFAOYSA-N 3-[4-[(3-ethylphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound CCC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C3=CC=NC=C3NC=2C(N)=O)=C1 HTFPJYFDVJPYDS-UHFFFAOYSA-N 0.000 claims 1
- WTYDLQWZVVMFFL-UHFFFAOYSA-N 3-[4-[(3-fluorophenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=NC=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(F)=C1 WTYDLQWZVVMFFL-UHFFFAOYSA-N 0.000 claims 1
- XJGDPYNKTYROOL-UHFFFAOYSA-N 3-[4-[(3-fluorophenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(F)=C1 XJGDPYNKTYROOL-UHFFFAOYSA-N 0.000 claims 1
- KCYZJDWJXRYGLM-UHFFFAOYSA-N 3-[4-[(3-methoxyphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound COC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C3=CC=CN=C3NC=2C(N)=O)=C1 KCYZJDWJXRYGLM-UHFFFAOYSA-N 0.000 claims 1
- PQKYIUTYZUMUDA-UHFFFAOYSA-N 3-[4-[(3-methoxyphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C3=CC=NC=C3NC=2C(N)=O)=C1 PQKYIUTYZUMUDA-UHFFFAOYSA-N 0.000 claims 1
- DAFHBNOWOJLDKA-UHFFFAOYSA-N 3-[4-[(3-methylphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C3=CC=CN=C3NC=2C(N)=O)=C1 DAFHBNOWOJLDKA-UHFFFAOYSA-N 0.000 claims 1
- MPXARXLCPOKVQD-UHFFFAOYSA-N 3-[4-[(3-methylphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C3=CC=NC=C3NC=2C(N)=O)=C1 MPXARXLCPOKVQD-UHFFFAOYSA-N 0.000 claims 1
- CEKLMAUFSMVXLB-UHFFFAOYSA-N 3-[4-[(4-fluorophenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=NC=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C=C1 CEKLMAUFSMVXLB-UHFFFAOYSA-N 0.000 claims 1
- NCNCBECTRSADAZ-UHFFFAOYSA-N 3-[4-[(4-methoxyphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=C(C=2C3=CC=NC=C3NC=2C(N)=O)C=C1 NCNCBECTRSADAZ-UHFFFAOYSA-N 0.000 claims 1
- DPSHZQXWMQFFDX-UHFFFAOYSA-N 3-[4-[(4-methylphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound C1=CC(C)=CC=C1NC(=O)NC1=CC=C(C=2C3=CC=CN=C3NC=2C(N)=O)C=C1 DPSHZQXWMQFFDX-UHFFFAOYSA-N 0.000 claims 1
- YCIOPZSNUPQDST-UHFFFAOYSA-N 3-[4-[(4-methylphenyl)carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound C1=CC(C)=CC=C1NC(=O)NC1=CC=C(C=2C3=CC=NC=C3NC=2C(N)=O)C=C1 YCIOPZSNUPQDST-UHFFFAOYSA-N 0.000 claims 1
- LFPVBDOXISJQKW-UHFFFAOYSA-N 3-[4-[[2-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C(F)(F)F LFPVBDOXISJQKW-UHFFFAOYSA-N 0.000 claims 1
- BPBWXRZYRSEPGN-UHFFFAOYSA-N 3-[4-[[2-acetamido-5-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC(=O)NC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=C(C=2C3=CC=NC=C3NC=2C(N)=O)C=C1 BPBWXRZYRSEPGN-UHFFFAOYSA-N 0.000 claims 1
- LYWRCKCWPJKLEH-UHFFFAOYSA-N 3-[4-[[2-chloro-5-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=NC=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1Cl LYWRCKCWPJKLEH-UHFFFAOYSA-N 0.000 claims 1
- XEYUGPBCBBJELO-UHFFFAOYSA-N 3-[4-[[2-chloro-5-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1Cl XEYUGPBCBBJELO-UHFFFAOYSA-N 0.000 claims 1
- ODTQNBLVLYUPEM-UHFFFAOYSA-N 3-[4-[[2-fluoro-3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=NC=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1F ODTQNBLVLYUPEM-UHFFFAOYSA-N 0.000 claims 1
- ZXQRJJWWONVJDP-UHFFFAOYSA-N 3-[4-[[2-fluoro-3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1F ZXQRJJWWONVJDP-UHFFFAOYSA-N 0.000 claims 1
- BDKXAKGVSWBPES-UHFFFAOYSA-N 3-[4-[[2-fluoro-5-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=NC=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F BDKXAKGVSWBPES-UHFFFAOYSA-N 0.000 claims 1
- UOBQJVRDRREQMU-UHFFFAOYSA-N 3-[4-[[2-fluoro-5-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F UOBQJVRDRREQMU-UHFFFAOYSA-N 0.000 claims 1
- YCYVCBQVRBIIDZ-UHFFFAOYSA-N 3-[4-[[2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=C(C=2C3=CC=CN=C3NC=2C(N)=O)C=C1 YCYVCBQVRBIIDZ-UHFFFAOYSA-N 0.000 claims 1
- RVCMSWRIKYSIAK-UHFFFAOYSA-N 3-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=NC=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 RVCMSWRIKYSIAK-UHFFFAOYSA-N 0.000 claims 1
- LRWDWYRTZVWCIG-UHFFFAOYSA-N 3-[4-[[3-chloro-4-(difluoromethoxy)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(OC(F)F)C(Cl)=C1 LRWDWYRTZVWCIG-UHFFFAOYSA-N 0.000 claims 1
- RQABHZNOPXTHMH-UHFFFAOYSA-N 3-[4-[[3-fluoro-5-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=NC=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC(F)=CC(C(F)(F)F)=C1 RQABHZNOPXTHMH-UHFFFAOYSA-N 0.000 claims 1
- SUXDHTDMDRXBGJ-UHFFFAOYSA-N 3-[4-[[3-fluoro-5-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC(F)=CC(C(F)(F)F)=C1 SUXDHTDMDRXBGJ-UHFFFAOYSA-N 0.000 claims 1
- ACGPYOWFCHVPGP-UHFFFAOYSA-N 3-[4-[[4-(difluoromethoxy)phenyl]carbamoylamino]phenyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide 3-[4-[(3,5-dimethoxyphenyl)carbamoylamino]phenyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound COc1cc(NC(=O)Nc2ccc(cc2)-c2c([nH]c3ncccc23)C(N)=O)cc(OC)c1.NC(=O)c1[nH]c2ncccc2c1-c1ccc(NC(=O)Nc2ccc(OC(F)F)cc2)cc1 ACGPYOWFCHVPGP-UHFFFAOYSA-N 0.000 claims 1
- QGSDUATVCISSMT-UHFFFAOYSA-N 3-[4-[[4-(difluoromethoxy)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(OC(F)F)C=C1 QGSDUATVCISSMT-UHFFFAOYSA-N 0.000 claims 1
- CRCNVPNDXOHKAF-UHFFFAOYSA-N 3-[4-[[4-(trifluoromethoxy)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=NC=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(OC(F)(F)F)C=C1 CRCNVPNDXOHKAF-UHFFFAOYSA-N 0.000 claims 1
- HYSOFXVKXIWMQE-UHFFFAOYSA-N 3-[4-[[4-(trifluoromethoxy)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(OC(F)(F)F)C=C1 HYSOFXVKXIWMQE-UHFFFAOYSA-N 0.000 claims 1
- GSAOSHXRQNXPOA-UHFFFAOYSA-N 3-[4-[[4-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=NC=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 GSAOSHXRQNXPOA-UHFFFAOYSA-N 0.000 claims 1
- ZCVCLBKOQMSPTA-UHFFFAOYSA-N 3-[4-[[4-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 ZCVCLBKOQMSPTA-UHFFFAOYSA-N 0.000 claims 1
- AMUIKWYWKCZFSH-UHFFFAOYSA-N 3-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=NC=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 AMUIKWYWKCZFSH-UHFFFAOYSA-N 0.000 claims 1
- WOSPKCCVQFMECJ-UHFFFAOYSA-N 3-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 WOSPKCCVQFMECJ-UHFFFAOYSA-N 0.000 claims 1
- HJWTUXBYYUVBGI-UHFFFAOYSA-N 3-[4-[[4-fluoro-3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=NC=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C(C(F)(F)F)=C1 HJWTUXBYYUVBGI-UHFFFAOYSA-N 0.000 claims 1
- PXEBGGZWHFCFHD-UHFFFAOYSA-N 3-[4-[[4-fluoro-3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound NC(=O)C=1NC2=CN=CC=C2C=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C(C(F)(F)F)=C1 PXEBGGZWHFCFHD-UHFFFAOYSA-N 0.000 claims 1
- HZMQKLDKHZFKPS-UHFFFAOYSA-N 3-[4-[[4-methyl-3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1NC(=O)NC1=CC=C(C=2C3=CC=CN=C3NC=2C(N)=O)C=C1 HZMQKLDKHZFKPS-UHFFFAOYSA-N 0.000 claims 1
- DYSNLIKKYJQYLP-UHFFFAOYSA-N 3-[4-[[4-methyl-3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1NC(=O)NC1=CC=C(C=2C3=CC=NC=C3NC=2C(N)=O)C=C1 DYSNLIKKYJQYLP-UHFFFAOYSA-N 0.000 claims 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 1
- BLQYOWGGVHHDIR-UHFFFAOYSA-N Cc1ccc(C)c(NC(=O)Nc2ccc(cc2)-c2c([nH]c3cnccc23)C(N)=O)c1.COc1cc(NC(=O)Nc2ccc(cc2)-c2c([nH]c3cnccc23)C(N)=O)cc(OC)c1 Chemical compound Cc1ccc(C)c(NC(=O)Nc2ccc(cc2)-c2c([nH]c3cnccc23)C(N)=O)c1.COc1cc(NC(=O)Nc2ccc(cc2)-c2c([nH]c3cnccc23)C(N)=O)cc(OC)c1 BLQYOWGGVHHDIR-UHFFFAOYSA-N 0.000 claims 1
- RXXQHASHEMRUAS-UHFFFAOYSA-N Cc1ccc(NC(=O)Nc2ccc(cc2)-c2c([nH]c3ncccc23)C(N)=O)cc1C.COc1ccc(C)cc1NC(=O)Nc1ccc(cc1)-c1c([nH]c2ncccc12)C(N)=O Chemical compound Cc1ccc(NC(=O)Nc2ccc(cc2)-c2c([nH]c3ncccc23)C(N)=O)cc1C.COc1ccc(C)cc1NC(=O)Nc1ccc(cc1)-c1c([nH]c2ncccc12)C(N)=O RXXQHASHEMRUAS-UHFFFAOYSA-N 0.000 claims 1
- 102000015792 Cyclin-Dependent Kinase 2 Human genes 0.000 claims 1
- 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims 1
- TVRJPCXRDBFXGL-UHFFFAOYSA-N NC(=O)c1[nH]c2cnccc2c1-c1ccc(NC(=O)Nc2ccc(F)cc2)cc1.NC(=O)c1[nH]c2cnccc2c1-c1ccc(NC(=O)Nc2cccc(c2)C(F)(F)F)cc1 Chemical compound NC(=O)c1[nH]c2cnccc2c1-c1ccc(NC(=O)Nc2ccc(F)cc2)cc1.NC(=O)c1[nH]c2cnccc2c1-c1ccc(NC(=O)Nc2cccc(c2)C(F)(F)F)cc1 TVRJPCXRDBFXGL-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000005441 aurora Substances 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0504173A FR2884821B1 (fr) | 2005-04-26 | 2005-04-26 | Pyrrolopyridines substitues, compositions les contenant, procede de fabrication et utilisation |
| PCT/FR2006/000925 WO2006114520A2 (fr) | 2005-04-26 | 2006-04-26 | Pyrrolopyridines substitues, compositions les contenant, procede de fabrication et utilisation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20090494T1 true HRP20090494T1 (hr) | 2009-10-31 |
Family
ID=35517344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20090494T HRP20090494T1 (hr) | 2005-04-26 | 2009-09-16 | Supstituirani pirolopiridini, pripravak koji ih sadrži, postupak njihovog dobivanja i njihova upotreba |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US7947706B2 (pl) |
| EP (1) | EP1877409B1 (pl) |
| JP (1) | JP2008539211A (pl) |
| KR (1) | KR20080007229A (pl) |
| CN (1) | CN101166739A (pl) |
| AR (1) | AR061386A1 (pl) |
| AT (1) | ATE433976T1 (pl) |
| AU (1) | AU2006239105A1 (pl) |
| BR (1) | BRPI0613161A2 (pl) |
| CA (1) | CA2605744A1 (pl) |
| CR (1) | CR9463A (pl) |
| CY (1) | CY1109369T1 (pl) |
| DE (1) | DE602006007337D1 (pl) |
| DK (1) | DK1877409T3 (pl) |
| DO (1) | DOP2006000096A (pl) |
| EA (1) | EA012983B1 (pl) |
| ES (1) | ES2328629T3 (pl) |
| FR (1) | FR2884821B1 (pl) |
| GT (1) | GT200600174A (pl) |
| HR (1) | HRP20090494T1 (pl) |
| IL (1) | IL186523A0 (pl) |
| MA (1) | MA29480B1 (pl) |
| MX (1) | MX2007013084A (pl) |
| NO (1) | NO20075918L (pl) |
| PA (1) | PA8671301A1 (pl) |
| PE (1) | PE20071420A1 (pl) |
| PL (1) | PL1877409T3 (pl) |
| PT (1) | PT1877409E (pl) |
| RS (1) | RS51136B (pl) |
| SI (1) | SI1877409T1 (pl) |
| TN (1) | TNSN07360A1 (pl) |
| TW (1) | TW200718701A (pl) |
| WO (1) | WO2006114520A2 (pl) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| JP2010505962A (ja) * | 2006-10-09 | 2010-02-25 | 武田薬品工業株式会社 | キナーゼ阻害剤 |
| JP2010505961A (ja) * | 2006-10-09 | 2010-02-25 | タケダ サン ディエゴ インコーポレイテッド | キナーゼ阻害剤 |
| WO2008063888A2 (en) | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| WO2008078100A2 (en) | 2006-12-22 | 2008-07-03 | Astex Therapeutics Limited | Tricyclic amine derivatives as protein tyrosine kinase inhibitors |
| CN101679408B (zh) * | 2006-12-22 | 2016-04-27 | Astex治疗学有限公司 | 作为fgfr抑制剂的双环杂环化合物 |
| BRPI0814423B1 (pt) | 2007-07-17 | 2022-04-19 | Plexxikon, Inc | Compostos que modulam quinase e composição farmacêutica compreendendo os mesmos |
| GB0720038D0 (en) * | 2007-10-12 | 2007-11-21 | Astex Therapeutics Ltd | New compounds |
| GB0720041D0 (en) | 2007-10-12 | 2007-11-21 | Astex Therapeutics Ltd | New Compounds |
| GB0810902D0 (en) | 2008-06-13 | 2008-07-23 | Astex Therapeutics Ltd | New compounds |
| DE102008052943A1 (de) | 2008-10-23 | 2010-04-29 | Merck Patent Gmbh | Azaindolderivate |
| AR078033A1 (es) | 2009-04-03 | 2011-10-12 | Plexxikon Inc | Una dispersion solida, que contiene al compuesto {3-[5-(4-(cloro-fenil)-1h-pirrolo[2,3-b]piridina-3-carbonil]-2,4-difluor-fenil}-amida del acido propano-1-sulfonico, composiciones y formulaciones que comprenden a dicha dispersion solida; metodos para fabricar dicha dispersion solida, formas 1 y 2 de |
| GB0906472D0 (en) | 2009-04-15 | 2009-05-20 | Astex Therapeutics Ltd | New compounds |
| GB0906470D0 (en) | 2009-04-15 | 2009-05-20 | Astex Therapeutics Ltd | New compounds |
| US20110030037A1 (en) * | 2009-07-07 | 2011-02-03 | Vadim Olshansky | Zone migration in network access |
| US8329724B2 (en) | 2009-08-03 | 2012-12-11 | Hoffmann-La Roche Inc. | Process for the manufacture of pharmaceutically active compounds |
| ES2633317T3 (es) | 2009-11-06 | 2017-09-20 | Plexxikon, Inc. | Compuestos y métodos para la modulación de quinasas, e indicaciones para ello |
| MA34948B1 (fr) | 2011-02-07 | 2014-03-01 | Plexxikon Inc | Composes et procedes de modulation de kinase, et leurs indications |
| TWI558702B (zh) | 2011-02-21 | 2016-11-21 | 普雷辛肯公司 | 醫藥活性物質的固態形式 |
| EP2855477A4 (en) * | 2012-05-29 | 2015-11-18 | Merck Sharp & Dohme | BARYARY COMPOUNDS, ISOTOPICALLY MARKED |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| US20140275082A1 (en) | 2013-03-14 | 2014-09-18 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
| GB201310464D0 (en) * | 2013-06-12 | 2013-07-24 | Lytix Biopharma As | Compounds |
| GB201310460D0 (en) * | 2013-06-12 | 2013-07-24 | Lytix Biopharma As | Compounds |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3254843B2 (ja) * | 1993-08-09 | 2002-02-12 | 三菱ウェルファーマ株式会社 | 新規縮合ヘテロ環誘導体 |
| US6335342B1 (en) * | 2000-06-19 | 2002-01-01 | Pharmacia & Upjohn S.P.A. | Azaindole derivatives, process for their preparation, and their use as antitumor agents |
| GB0115109D0 (en) | 2001-06-21 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| US7427623B2 (en) * | 2001-09-11 | 2008-09-23 | Smithkline Beecham Corporation | 4-Amino-2,3-disubstituted thieno[2,3-d]pyrimidines and pharmacetical compositions thereof |
| WO2003028724A1 (en) * | 2001-10-04 | 2003-04-10 | Smithkline Beecham Corporation | Chk1 kinase inhibitors |
| US7129225B2 (en) * | 2001-10-22 | 2006-10-31 | The Research Foundation Of State University Of New York | Protection against and treatment of hearing loss |
| IL164187A0 (en) * | 2002-03-28 | 2005-12-18 | Eisai Co Ltd | 7-Azaindole derivatives and pharmaceutical compositions containing the same |
| FR2878849B1 (fr) | 2004-12-06 | 2008-09-12 | Aventis Pharma Sa | Indoles substitues, compositions les contenant, procede de fabrication et utilisation |
-
2005
- 2005-04-26 FR FR0504173A patent/FR2884821B1/fr not_active Expired - Fee Related
-
2006
- 2006-04-25 PE PE2006000435A patent/PE20071420A1/es not_active Application Discontinuation
- 2006-04-25 AR ARP060101646A patent/AR061386A1/es unknown
- 2006-04-26 RS RSP-2009/0400A patent/RS51136B/sr unknown
- 2006-04-26 DK DK06743743T patent/DK1877409T3/da active
- 2006-04-26 BR BRPI0613161-1A patent/BRPI0613161A2/pt not_active IP Right Cessation
- 2006-04-26 MX MX2007013084A patent/MX2007013084A/es active IP Right Grant
- 2006-04-26 TW TW095114907A patent/TW200718701A/zh unknown
- 2006-04-26 ES ES06743743T patent/ES2328629T3/es active Active
- 2006-04-26 GT GT200600174A patent/GT200600174A/es unknown
- 2006-04-26 DE DE602006007337T patent/DE602006007337D1/de active Active
- 2006-04-26 JP JP2008508258A patent/JP2008539211A/ja active Pending
- 2006-04-26 EA EA200702329A patent/EA012983B1/ru not_active IP Right Cessation
- 2006-04-26 DO DO2006000096A patent/DOP2006000096A/es unknown
- 2006-04-26 PA PA20068671301A patent/PA8671301A1/es unknown
- 2006-04-26 PT PT06743743T patent/PT1877409E/pt unknown
- 2006-04-26 EP EP06743743A patent/EP1877409B1/fr active Active
- 2006-04-26 AU AU2006239105A patent/AU2006239105A1/en not_active Withdrawn
- 2006-04-26 SI SI200630396T patent/SI1877409T1/sl unknown
- 2006-04-26 CN CNA200680014034XA patent/CN101166739A/zh active Pending
- 2006-04-26 KR KR1020077024847A patent/KR20080007229A/ko not_active Application Discontinuation
- 2006-04-26 WO PCT/FR2006/000925 patent/WO2006114520A2/fr active Application Filing
- 2006-04-26 PL PL06743743T patent/PL1877409T3/pl unknown
- 2006-04-26 AT AT06743743T patent/ATE433976T1/de active
- 2006-04-26 CA CA002605744A patent/CA2605744A1/fr not_active Abandoned
-
2007
- 2007-09-21 TN TNP2007000360A patent/TNSN07360A1/en unknown
- 2007-10-09 IL IL186523A patent/IL186523A0/en unknown
- 2007-10-11 US US11/870,640 patent/US7947706B2/en not_active Expired - Fee Related
- 2007-10-22 CR CR9463A patent/CR9463A/es not_active Application Discontinuation
- 2007-11-16 NO NO20075918A patent/NO20075918L/no not_active Application Discontinuation
- 2007-11-22 MA MA30412A patent/MA29480B1/fr unknown
-
2009
- 2009-09-16 HR HR20090494T patent/HRP20090494T1/hr unknown
- 2009-09-16 CY CY20091100957T patent/CY1109369T1/el unknown
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