JP2012500215A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012500215A5 JP2012500215A5 JP2011523198A JP2011523198A JP2012500215A5 JP 2012500215 A5 JP2012500215 A5 JP 2012500215A5 JP 2011523198 A JP2011523198 A JP 2011523198A JP 2011523198 A JP2011523198 A JP 2011523198A JP 2012500215 A5 JP2012500215 A5 JP 2012500215A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- imidazo
- cyclopropanecarboxamide
- hetero
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 cyano, thio, oxy, hydroxy, carbonyloxy Chemical group 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims 54
- 125000000217 alkyl group Chemical group 0.000 claims 31
- 125000003118 aryl group Chemical group 0.000 claims 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims 23
- 125000001424 substituent group Chemical group 0.000 claims 21
- 125000004104 aryloxy group Chemical group 0.000 claims 12
- 150000001602 bicycloalkyls Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000001475 halogen functional group Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 6
- 229940124530 sulfonamide Drugs 0.000 claims 6
- 150000003456 sulfonamides Chemical class 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- ALNWINGRKKGNMD-UHFFFAOYSA-N n-[6-([1,2,4]triazolo[4,3-a]pyridin-3-ylsulfanyl)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C=1N2N=C(SC=3N4C=CC=CC4=NN=3)C=CC2=NC=1NC(=O)C1CC1 ALNWINGRKKGNMD-UHFFFAOYSA-N 0.000 claims 1
- WFSUAOWAVNRMCN-CYBMUJFWSA-N n-[6-[(1r)-1-[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C=1N2C([C@H](C)C3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)=NN=C2C=CC=1C=1C=NN(C)C=1 WFSUAOWAVNRMCN-CYBMUJFWSA-N 0.000 claims 1
- WFSUAOWAVNRMCN-ZDUSSCGKSA-N n-[6-[(1s)-1-[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C=1N2C([C@@H](C)C3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)=NN=C2C=CC=1C=1C=NN(C)C=1 WFSUAOWAVNRMCN-ZDUSSCGKSA-N 0.000 claims 1
- FKTKPXQETWSUSX-UHFFFAOYSA-N n-[6-[(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound N12C=C(Br)C=CC2=NN=C1SC(=NN1C=2)C=CC1=NC=2NC(=O)C1CC1 FKTKPXQETWSUSX-UHFFFAOYSA-N 0.000 claims 1
- KJNQDZHUOHOAGD-UHFFFAOYSA-N n-[6-[(6-bromobenzotriazol-1-yl)methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C12=CC(Br)=CC=C2N=NN1CC(=NN1C=2)C=CC1=NC=2NC(=O)C1CC1 KJNQDZHUOHOAGD-UHFFFAOYSA-N 0.000 claims 1
- GZMBHSVIOOMWLE-UHFFFAOYSA-N n-[6-[(6-chloro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound N12C=C(Cl)C=CC2=NN=C1SC(=NN1C=2)C=CC1=NC=2NC(=O)C1CC1 GZMBHSVIOOMWLE-UHFFFAOYSA-N 0.000 claims 1
- ORZIAZMNRSURHH-UHFFFAOYSA-N n-[6-[(6-cyano-[1,2,4]triazolo[4,3-a]pyridin-3-yl)sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C=1N2N=C(SC=3N4C=C(C=CC4=NN=3)C#N)C=CC2=NC=1NC(=O)C1CC1 ORZIAZMNRSURHH-UHFFFAOYSA-N 0.000 claims 1
- SSMPUPDWLNBDHF-UHFFFAOYSA-N n-[6-[(6-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound N12C=C(C)C=CC2=NN=C1SC(=NN1C=2)C=CC1=NC=2NC(=O)C1CC1 SSMPUPDWLNBDHF-UHFFFAOYSA-N 0.000 claims 1
- VYVBXMSJYKDMLU-UHFFFAOYSA-N n-[6-[(6-methylbenzotriazol-1-yl)methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C12=CC(C)=CC=C2N=NN1CC(=NN1C=2)C=CC1=NC=2NC(=O)C1CC1 VYVBXMSJYKDMLU-UHFFFAOYSA-N 0.000 claims 1
- GCARGFKBVKYNFF-UHFFFAOYSA-N n-[6-[(6-phenylbenzotriazol-1-yl)methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1CC1C(=O)NC(N=C1C=C2)=CN1N=C2CN(C1=C2)N=NC1=CC=C2C1=CC=CC=C1 GCARGFKBVKYNFF-UHFFFAOYSA-N 0.000 claims 1
- WTYAYKFCCKOZDL-UHFFFAOYSA-N n-[6-[(6-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound N12C=C(C(C)C)C=CC2=NN=C1SC(=NN1C=2)C=CC1=NC=2NC(=O)C1CC1 WTYAYKFCCKOZDL-UHFFFAOYSA-N 0.000 claims 1
- TYKNDNGQRYAKDG-UHFFFAOYSA-N n-[6-[1-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound N=1N=C2C=CC(Br)=CN2C=1C(C)C(=NN1C=2)C=CC1=NC=2NC(=O)C1CC1 TYKNDNGQRYAKDG-UHFFFAOYSA-N 0.000 claims 1
- GNAKSJFLNAFDNE-UHFFFAOYSA-N n-[6-[1-(6-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound N=1N=C2C=CC(C)=CN2C=1C(C)C(=NN1C=2)C=CC1=NC=2NC(=O)C1CC1 GNAKSJFLNAFDNE-UHFFFAOYSA-N 0.000 claims 1
- MASNWNCJSOOOGH-UHFFFAOYSA-N n-[6-[1-([1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound N=1N=C2C=CC=CN2C=1C(C)C(=NN1C=2)C=CC1=NC=2NC(=O)C1CC1 MASNWNCJSOOOGH-UHFFFAOYSA-N 0.000 claims 1
- WFSUAOWAVNRMCN-UHFFFAOYSA-N n-[6-[1-[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=CC2=NC(NC(=O)C3CC3)=CN2N=C1C(C)C(N1C=2)=NN=C1C=CC=2C=1C=NN(C)C=1 WFSUAOWAVNRMCN-UHFFFAOYSA-N 0.000 claims 1
- OQOPDUGLGQROGM-UHFFFAOYSA-N n-[6-[1-[6-(1h-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=CC2=NC(NC(=O)C3CC3)=CN2N=C1C(C)C(N1C=2)=NN=C1C=CC=2C=1C=NNC=1 OQOPDUGLGQROGM-UHFFFAOYSA-N 0.000 claims 1
- RJHARAZILAVQSP-UHFFFAOYSA-N n-[6-[1-[6-(3-fluorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=CC2=NC(NC(=O)C3CC3)=CN2N=C1C(C)C(N1C=2)=NN=C1C=CC=2C1=CC=CC(F)=C1 RJHARAZILAVQSP-UHFFFAOYSA-N 0.000 claims 1
- JQPUGSRTYXNQGL-UHFFFAOYSA-N n-[6-[1-[6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=CC2=NC(NC(=O)C3CC3)=CN2N=C1C(C)C(N1C=2)=NN=C1C=CC=2C1=CC=C(F)C=C1 JQPUGSRTYXNQGL-UHFFFAOYSA-N 0.000 claims 1
- JHMWKWMSFPFTDZ-UHFFFAOYSA-N n-[6-[1-[6-(4-methylthiophen-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=CC2=NC(NC(=O)C3CC3)=CN2N=C1C(C)C(N1C=2)=NN=C1C=CC=2C1=CC(C)=CS1 JHMWKWMSFPFTDZ-UHFFFAOYSA-N 0.000 claims 1
- GEQJKGQOFFTPFU-UHFFFAOYSA-N n-[6-[[6-(1-methyl-6-oxopyridin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=CC(=O)N(C)C=C1C1=CN2C(SC3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)=NN=C2C=C1 GEQJKGQOFFTPFU-UHFFFAOYSA-N 0.000 claims 1
- FCMZAHYEDNBFKS-UHFFFAOYSA-N n-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=NN(C)C=C1C1=CN2C(SC3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)=NN=C2C=C1 FCMZAHYEDNBFKS-UHFFFAOYSA-N 0.000 claims 1
- HQYWUQYKIZIEDW-UHFFFAOYSA-N n-[6-[[6-(1-methylpyrazol-4-yl)benzotriazol-1-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=NN(C)C=C1C1=CC=C(N=NN2CC3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)C2=C1 HQYWUQYKIZIEDW-UHFFFAOYSA-N 0.000 claims 1
- NMXHXKZEFCNNHN-UHFFFAOYSA-N n-[6-[[6-(2-hydroxypropan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound N12C=C(C(C)(O)C)C=CC2=NN=C1SC(=NN1C=2)C=CC1=NC=2NC(=O)C1CC1 NMXHXKZEFCNNHN-UHFFFAOYSA-N 0.000 claims 1
- ULOGDSGFRXTWPA-UHFFFAOYSA-N n-[6-[[6-(2-morpholin-4-yl-1,3-thiazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1CC1C(=O)NC(N=C1C=C2)=CN1N=C2SC(N1C=2)=NN=C1C=CC=2C(N=1)=CSC=1N1CCOCC1 ULOGDSGFRXTWPA-UHFFFAOYSA-N 0.000 claims 1
- CZFZQBFVIQWXNQ-UHFFFAOYSA-N n-[6-[[6-(2h-tetrazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1CC1C(=O)NC(N=C1C=C2)=CN1N=C2SC(N1C=2)=NN=C1C=CC=2C=1N=NNN=1 CZFZQBFVIQWXNQ-UHFFFAOYSA-N 0.000 claims 1
- RWKYNAFGOPDCQF-UHFFFAOYSA-N n-[6-[[6-(3,5-difluorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]-difluoromethyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound FC1=CC(F)=CC(C2=CN3C(=NN=C3C=C2)C(F)(F)C2=NN3C=C(NC(=O)C4CC4)N=C3C=C2)=C1 RWKYNAFGOPDCQF-UHFFFAOYSA-N 0.000 claims 1
- CGGCGLGNXZZJEI-UHFFFAOYSA-N n-[6-[[6-(3,5-dimethyl-1h-pyrazol-4-yl)benzotriazol-1-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound CC1=NNC(C)=C1C1=CC=C(N=NN2CC3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)C2=C1 CGGCGLGNXZZJEI-UHFFFAOYSA-N 0.000 claims 1
- AVPYTUNWVIXVIS-UHFFFAOYSA-N n-[6-[[6-(3-fluorophenyl)benzotriazol-1-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound FC1=CC=CC(C=2C=C3N(CC4=NN5C=C(NC(=O)C6CC6)N=C5C=C4)N=NC3=CC=2)=C1 AVPYTUNWVIXVIS-UHFFFAOYSA-N 0.000 claims 1
- VPGQFNQVPBTTMT-UHFFFAOYSA-N n-[6-[[6-(5-methoxypyridin-3-yl)benzotriazol-1-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound COC1=CN=CC(C=2C=C3N(CC4=NN5C=C(NC(=O)C6CC6)N=C5C=C4)N=NC3=CC=2)=C1 VPGQFNQVPBTTMT-UHFFFAOYSA-N 0.000 claims 1
- JLMGTCPELQRLMG-UHFFFAOYSA-N n-[6-[[6-(5-methyl-1h-1,2,4-triazol-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound N1C(C)=NC(C2=CN3C(SC4=NN5C=C(NC(=O)C6CC6)N=C5C=C4)=NN=C3C=C2)=N1 JLMGTCPELQRLMG-UHFFFAOYSA-N 0.000 claims 1
- MKYNYJHUMGUEAH-UHFFFAOYSA-N n-[6-[[6-(5-methylsulfonylpyridin-3-yl)benzotriazol-1-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound CS(=O)(=O)C1=CN=CC(C=2C=C3N(CC4=NN5C=C(NC(=O)C6CC6)N=C5C=C4)N=NC3=CC=2)=C1 MKYNYJHUMGUEAH-UHFFFAOYSA-N 0.000 claims 1
- LYHSBJXOKTVBJV-UHFFFAOYSA-N n-[6-[[6-(6-methoxypyridin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound COC1=CC=CC(C2=CN3C(SC4=NN5C=C(NC(=O)C6CC6)N=C5C=C4)=NN=C3C=C2)=N1 LYHSBJXOKTVBJV-UHFFFAOYSA-N 0.000 claims 1
- HELDPUYIPKAPQX-UHFFFAOYSA-N n-[6-[[6-(6-methoxypyridin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=NC(OC)=CC=C1C1=CN2C(SC3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)=NN=C2C=C1 HELDPUYIPKAPQX-UHFFFAOYSA-N 0.000 claims 1
- FGLMJHOXJVYCKV-UHFFFAOYSA-N n-[6-[[6-(6-morpholin-4-ylpyridin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1CC1C(=O)NC(N=C1C=C2)=CN1N=C2SC(N1C=2)=NN=C1C=CC=2C(C=N1)=CC=C1N1CCOCC1 FGLMJHOXJVYCKV-UHFFFAOYSA-N 0.000 claims 1
- LJHQKJFEYKWXTN-UHFFFAOYSA-N n-[6-[[6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound N12C=C(C(F)(F)F)C=CC2=NN=C1SC(=NN1C=2)C=CC1=NC=2NC(=O)C1CC1 LJHQKJFEYKWXTN-UHFFFAOYSA-N 0.000 claims 1
- FQDDRFSAPPQWTO-UHFFFAOYSA-N n-[6-[[6-[1-(2-hydroxyethyl)pyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=NN(CCO)C=C1C1=CN2C(SC3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)=NN=C2C=C1 FQDDRFSAPPQWTO-UHFFFAOYSA-N 0.000 claims 1
- FGELHXDQPILSFH-UHFFFAOYSA-N n-[6-[[6-[1-(2-hydroxyethyl)pyrazol-4-yl]benzotriazol-1-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=NN(CCO)C=C1C1=CC=C(N=NN2CC3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)C2=C1 FGELHXDQPILSFH-UHFFFAOYSA-N 0.000 claims 1
- VQELKEMGMRUXAU-UHFFFAOYSA-N n-[6-[[6-[1-(2-methoxyethyl)pyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=NN(CCOC)C=C1C1=CN2C(SC3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)=NN=C2C=C1 VQELKEMGMRUXAU-UHFFFAOYSA-N 0.000 claims 1
- BRCNYCPTIIMSKO-GOSISDBHSA-N n-[6-[[6-[1-[(2r)-2,3-dihydroxypropyl]pyrazol-4-yl]benzotriazol-1-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=NN(C[C@@H](O)CO)C=C1C1=CC=C(N=NN2CC3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)C2=C1 BRCNYCPTIIMSKO-GOSISDBHSA-N 0.000 claims 1
- BRCNYCPTIIMSKO-SFHVURJKSA-N n-[6-[[6-[1-[(2s)-2,3-dihydroxypropyl]pyrazol-4-yl]benzotriazol-1-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=NN(C[C@H](O)CO)C=C1C1=CC=C(N=NN2CC3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)C2=C1 BRCNYCPTIIMSKO-SFHVURJKSA-N 0.000 claims 1
- MPNQAGOPPMLZRC-UHFFFAOYSA-N n-[6-[[6-[2-(3-hydroxypropylamino)pyrimidin-5-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=NC(NCCCO)=NC=C1C1=CN2C(SC3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)=NN=C2C=C1 MPNQAGOPPMLZRC-UHFFFAOYSA-N 0.000 claims 1
- KLMZSMRUVIPPJV-UHFFFAOYSA-N n-[6-[[6-[3-(3-hydroxypropyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound OCCCC1=CC=CC(C2=CN3C(SC4=NN5C=C(NC(=O)C6CC6)N=C5C=C4)=NN=C3C=C2)=C1 KLMZSMRUVIPPJV-UHFFFAOYSA-N 0.000 claims 1
- HOTXCQQRCQCCJM-UHFFFAOYSA-N n-[6-[difluoro-(6-pyridin-3-yl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=CC2=NC(NC(=O)C3CC3)=CN2N=C1C(F)(F)C(N1C=2)=NN=C1C=CC=2C1=CC=CN=C1 HOTXCQQRCQCCJM-UHFFFAOYSA-N 0.000 claims 1
- XMQIGPJCPYDBPW-UHFFFAOYSA-N n-[6-[difluoro-(6-pyridin-4-yl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=CC2=NC(NC(=O)C3CC3)=CN2N=C1C(F)(F)C(N1C=2)=NN=C1C=CC=2C1=CC=NC=C1 XMQIGPJCPYDBPW-UHFFFAOYSA-N 0.000 claims 1
- NCXKHJVCIXQDQS-UHFFFAOYSA-N n-[6-[difluoro-(6-pyrimidin-5-yl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=CC2=NC(NC(=O)C3CC3)=CN2N=C1C(F)(F)C(N1C=2)=NN=C1C=CC=2C1=CN=CN=C1 NCXKHJVCIXQDQS-UHFFFAOYSA-N 0.000 claims 1
- YNGHGMBWDNBWBQ-UHFFFAOYSA-N n-[6-[difluoro-[6-(1,2-oxazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=CC2=NC(NC(=O)C3CC3)=CN2N=C1C(F)(F)C(N1C=2)=NN=C1C=CC=2C=1C=NOC=1 YNGHGMBWDNBWBQ-UHFFFAOYSA-N 0.000 claims 1
- RLLSEIXUTRQGNA-UHFFFAOYSA-N n-[6-[difluoro-[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=NN(C)C=C1C1=CN2C(C(F)(F)C3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)=NN=C2C=C1 RLLSEIXUTRQGNA-UHFFFAOYSA-N 0.000 claims 1
- KMKWOFVNLGNWLW-UHFFFAOYSA-N n-[6-[difluoro-[6-(1h-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=CC2=NC(NC(=O)C3CC3)=CN2N=C1C(F)(F)C(N1C=2)=NN=C1C=CC=2C=1C=NNC=1 KMKWOFVNLGNWLW-UHFFFAOYSA-N 0.000 claims 1
- PBDLUWAGUUXNKJ-UHFFFAOYSA-N n-[6-[difluoro-[6-(3-fluoro-5-methylphenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound CC1=CC(F)=CC(C2=CN3C(=NN=C3C=C2)C(F)(F)C2=NN3C=C(NC(=O)C4CC4)N=C3C=C2)=C1 PBDLUWAGUUXNKJ-UHFFFAOYSA-N 0.000 claims 1
- OVVAHDLCJNXTNL-UHFFFAOYSA-N n-[6-[difluoro-[6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=CC(F)=CC=C1C1=CN2C(C(F)(F)C3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)=NN=C2C=C1 OVVAHDLCJNXTNL-UHFFFAOYSA-N 0.000 claims 1
- BIONEVAVXHPZTJ-UHFFFAOYSA-N n-[6-[difluoro-[6-(4-methylpyridin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound CC1=CC=NC=C1C1=CN2C(C(F)(F)C3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)=NN=C2C=C1 BIONEVAVXHPZTJ-UHFFFAOYSA-N 0.000 claims 1
- REKAVUXKANWUSF-UHFFFAOYSA-N n-[6-[difluoro-[6-(4-methylthiophen-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound CC1=CSC(C2=CN3C(=NN=C3C=C2)C(F)(F)C2=NN3C=C(NC(=O)C4CC4)N=C3C=C2)=C1 REKAVUXKANWUSF-UHFFFAOYSA-N 0.000 claims 1
- NHOMIIHALTUSHC-UHFFFAOYSA-N n-[6-[difluoro-[6-(4-propan-2-ylphenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=CC(C(C)C)=CC=C1C1=CN2C(C(F)(F)C3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)=NN=C2C=C1 NHOMIIHALTUSHC-UHFFFAOYSA-N 0.000 claims 1
- SRZUMNMDFICJJY-UHFFFAOYSA-N n-[6-[difluoro-[6-(6-methoxypyridin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=NC(OC)=CC=C1C1=CN2C(C(F)(F)C3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)=NN=C2C=C1 SRZUMNMDFICJJY-UHFFFAOYSA-N 0.000 claims 1
- SKJQBGWUQLADAF-UHFFFAOYSA-N n-[6-[difluoro-[6-[1-(2-hydroxyethyl)pyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide Chemical compound C1=NN(CCO)C=C1C1=CN2C(C(F)(F)C3=NN4C=C(NC(=O)C5CC5)N=C4C=C3)=NN=C2C=C1 SKJQBGWUQLADAF-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- DIRYQDWFXAFIAN-UHFFFAOYSA-N BrC=1C=CC=2N(C1)C(=NN2)SC=2C=CC=1N(N2)C=CN1 Chemical compound BrC=1C=CC=2N(C1)C(=NN2)SC=2C=CC=1N(N2)C=CN1 DIRYQDWFXAFIAN-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8895908P | 2008-08-14 | 2008-08-14 | |
| US61/088,959 | 2008-08-14 | ||
| US11791008P | 2008-11-25 | 2008-11-25 | |
| US61/117,910 | 2008-11-25 | ||
| US16100709P | 2009-03-17 | 2009-03-17 | |
| US61/161,007 | 2009-03-17 | ||
| PCT/US2009/053913 WO2010019899A1 (en) | 2008-08-14 | 2009-08-14 | cMET INHIBITORS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012500215A JP2012500215A (ja) | 2012-01-05 |
| JP2012500215A5 true JP2012500215A5 (OSRAM) | 2012-09-06 |
| JP5469666B2 JP5469666B2 (ja) | 2014-04-16 |
Family
ID=41202532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011523198A Expired - Fee Related JP5469666B2 (ja) | 2008-08-14 | 2009-08-14 | ｃＭＥＴ阻害剤 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US8178534B2 (OSRAM) |
| EP (1) | EP2313407B1 (OSRAM) |
| JP (1) | JP5469666B2 (OSRAM) |
| KR (1) | KR20110039383A (OSRAM) |
| CN (1) | CN102124005B (OSRAM) |
| AR (1) | AR072936A1 (OSRAM) |
| AU (1) | AU2009281822B2 (OSRAM) |
| BR (1) | BRPI0917808A2 (OSRAM) |
| CA (1) | CA2731108A1 (OSRAM) |
| CO (1) | CO6351724A2 (OSRAM) |
| CR (1) | CR20110135A (OSRAM) |
| DO (1) | DOP2011000050A (OSRAM) |
| EA (1) | EA019723B1 (OSRAM) |
| EC (1) | ECSP11010889A (OSRAM) |
| ES (1) | ES2608761T3 (OSRAM) |
| GE (1) | GEP20125652B (OSRAM) |
| IL (1) | IL210734A0 (OSRAM) |
| MA (1) | MA32615B1 (OSRAM) |
| MX (1) | MX2011001732A (OSRAM) |
| MY (1) | MY150542A (OSRAM) |
| NZ (1) | NZ590617A (OSRAM) |
| PE (1) | PE20110275A1 (OSRAM) |
| TW (1) | TWI455939B (OSRAM) |
| UY (1) | UY32049A (OSRAM) |
| WO (1) | WO2010019899A1 (OSRAM) |
| ZA (1) | ZA201100467B (OSRAM) |
Families Citing this family (82)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI417095B (zh) | 2006-03-15 | 2013-12-01 | Janssen Pharmaceuticals Inc | １，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途 |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| US20090197880A1 (en) * | 2007-07-13 | 2009-08-06 | Genelabs Technologies, Inc. | Anti-viral compounds, compositions, and methods of use |
| JP5433579B2 (ja) | 2007-09-14 | 2014-03-05 | ジャンセン ファーマシューティカルズ， インコーポレイテッド． | １，３−二置換−４−フェニル−１ｈ−ピリジン−２−オン |
| TWI475995B (zh) | 2007-09-14 | 2015-03-11 | Janssen Pharmaceuticals Inc | １’，３’－二取代－４－苯基－３，４，５，６－四氫－２ｈ，１’ｈ－〔１，４’〕聯吡啶基－２’－酮化物 |
| ATE516272T1 (de) | 2007-09-14 | 2011-07-15 | Ortho Mcneil Janssen Pharm | 1,3-disubstituierte 4-(aryl-x-phenyl)-1h-pyridin- 2-one |
| AU2008323287B2 (en) | 2007-11-14 | 2011-07-14 | Addex Pharma S.A. | Imidazo[1,2-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| JPWO2009128520A1 (ja) * | 2008-04-18 | 2011-08-04 | 塩野義製薬株式会社 | Ｐｉ３ｋ阻害活性を有する複素環化合物 |
| EP2344470B1 (en) | 2008-09-02 | 2013-11-06 | Janssen Pharmaceuticals, Inc. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
| RU2517181C2 (ru) | 2008-10-16 | 2014-05-27 | Орто-Макнейл-Янссен Фармасьютикалз, Инк. | Производные индола и бензоморфолина в качестве модулятора метаботропных глутаматных рецепторов |
| US8691813B2 (en) | 2008-11-28 | 2014-04-08 | Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| CN102439015B (zh) | 2009-05-12 | 2015-05-13 | 杨森制药有限公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物和其作为mGluR2受体的正向变构调节剂的用途 |
| ES2440001T3 (es) | 2009-05-12 | 2014-01-27 | Janssen Pharmaceuticals, Inc. | Derivados de 1,2,4-triazolo[4,3-A]piridina y su uso para el tratamiento o prevención de trastornos neurológicos y psiquiátricos |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| EP2343294A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Substituted triazolopyridines |
| PL2719699T3 (pl) | 2009-12-31 | 2016-01-29 | Hutchison Medipharma Ltd | Pewne triazolopirazyny, ich kompozycje i sposoby ich stosowania |
| EP2571878B1 (en) | 2010-05-17 | 2018-10-17 | Incozen Therapeutics Pvt. Ltd. | Novel 3,5-disubstitued-3h-imidazo[4,5-b]pyridine and 3,5- disubstitued -3h-[1,2,3]triazolo[4,5-b]pyridine compounds as modulators of protein kinases |
| WO2012003338A1 (en) * | 2010-07-01 | 2012-01-05 | Takeda Pharmaceutical Company Limited | COMBINATION OF A cMET INHIBITOR AND AN ANTIBODY TO HGF AND/OR cMET |
| CN103298810B (zh) | 2010-11-08 | 2016-03-16 | 杨森制药公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
| US8993591B2 (en) | 2010-11-08 | 2015-03-31 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a] pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors |
| WO2012062751A1 (en) | 2010-11-08 | 2012-05-18 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| WO2012088266A2 (en) | 2010-12-22 | 2012-06-28 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3 |
| EP2755976B1 (en) | 2011-09-15 | 2018-07-18 | Novartis AG | 6-substituted 3-(quinolin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyridines as c-met tyrosine kinase inhibitors |
| CN103958509B (zh) * | 2011-09-15 | 2015-12-23 | 诺华股份有限公司 | 作为酪氨酸激酶抑制剂的6-取代的3-(喹啉-6-基硫代)-[1,2,4]三唑并[4,3-a]吡啶化合物 |
| CN103030654A (zh) * | 2011-10-09 | 2013-04-10 | 济南赛文医药技术有限公司 | 一种小分子c-Met蛋白激酶抑制剂 |
| WO2013135674A1 (en) * | 2012-03-12 | 2013-09-19 | Syngenta Participations Ag | Insecticidal 2-aryl-acetamide compounds |
| UA125503C2 (uk) | 2012-06-13 | 2022-04-13 | Інсайт Холдинґс Корпорейшн | Заміщені трициклічні сполуки як інгібітори fgfr |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| MY181497A (en) | 2013-04-19 | 2020-12-23 | Incyte Holdings Corp | Bicyclic heterocycles as fgfr inhibitors |
| EP2995618B1 (en) * | 2013-05-10 | 2019-01-09 | Jiangsu Hansoh Pharmaceutical Group Co., Ltd. | [1,2,4]triazol [4,3-a]pyridine derivate, preparation method therefor or medical application thereof |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| EP2818471A1 (en) * | 2013-06-27 | 2014-12-31 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Nitrogen bicyclic compounds as inhibitors for Scyl1 and Grk5 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| EP3424535A1 (en) | 2014-01-21 | 2019-01-09 | Janssen Pharmaceutica NV | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| PH12019500127B1 (en) | 2014-01-21 | 2022-05-04 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| WO2015123408A1 (en) | 2014-02-13 | 2015-08-20 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| TWI720451B (zh) | 2014-02-13 | 2021-03-01 | 美商英塞特控股公司 | 作為lsd1抑制劑之環丙胺 |
| WO2015123437A1 (en) | 2014-02-13 | 2015-08-20 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| US9670210B2 (en) | 2014-02-13 | 2017-06-06 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| WO2016007727A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| TWI687419B (zh) | 2014-07-10 | 2020-03-11 | 美商英塞特公司 | 作為ｌｓｄ１抑制劑之咪唑并吡啶及咪唑并吡嗪 |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| WO2016007736A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Imidazopyrazines as lsd1 inhibitors |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| CR20170390A (es) | 2015-02-20 | 2017-10-23 | Incyte Holdings Corp | Heterociclos biciclicos como inhibidores de fgfr |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| MX373154B (es) | 2015-04-03 | 2020-04-22 | Incyte Holdings Corp | Compuestos heterocíclicos como inhibidores de demetilasa 1 específica de lisina (lsd1). |
| RU2729630C2 (ru) | 2015-06-25 | 2020-08-11 | Тайхо Фармасьютикал Ко., Лтд. | Терапевтическое средство для фиброза |
| LT3334709T (lt) | 2015-08-12 | 2025-03-10 | Incyte Holdings Corporation | Lsd1 inhibitoriaus druskos |
| CN106924260B (zh) * | 2015-12-31 | 2018-05-25 | 北京浦润奥生物科技有限责任公司 | 化合物在制备用于治疗脑胶质瘤的药物中的用途 |
| TWI781920B (zh) | 2016-02-05 | 2022-11-01 | 美商戴納立製藥公司 | 化合物、組合物及方法 |
| UA125559C2 (uk) | 2016-04-22 | 2022-04-20 | Інсайт Корпорейшн | Композиції інгібітора lsd1 |
| KR20190084310A (ko) | 2016-11-23 | 2019-07-16 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 살충제로서의 2-[3-(알킬술포닐)-2H-인다졸-2-일]-3H-이미다조[4,5-b]피리딘 유도체 및 유사한 화합물 |
| PL3552017T3 (pl) | 2016-12-09 | 2022-08-08 | Denali Therapeutics Inc. | Związki użyteczne jako inhibitory RIPK1 |
| ES2991062T3 (es) | 2017-02-15 | 2024-12-02 | Taiho Pharmaceutical Co Ltd | Composición farmacéutica |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| US12280045B2 (en) | 2017-09-08 | 2025-04-22 | Taiho Pharmaceutical Co., Ltd. | Antitumor agent and antitumor effect potentiator |
| PE20210919A1 (es) | 2018-05-04 | 2021-05-19 | Incyte Corp | Sales de un inhibidor de fgfr |
| BR112020022392A2 (pt) | 2018-05-04 | 2021-02-02 | Incyte Corporation | formas sólidas de um inibidor de fgfr e processos para preparação das mesmas |
| US10968200B2 (en) | 2018-08-31 | 2021-04-06 | Incyte Corporation | Salts of an LSD1 inhibitor and processes for preparing the same |
| WO2020102216A1 (en) | 2018-11-13 | 2020-05-22 | Incyte Corporation | Substituted heterocyclic derivatives as pi3k inhibitors |
| US11161838B2 (en) | 2018-11-13 | 2021-11-02 | Incyte Corporation | Heterocyclic derivatives as PI3K inhibitors |
| WO2020102198A1 (en) | 2018-11-13 | 2020-05-22 | Incyte Corporation | Heterocyclic derivatives as pi3k inhibitors |
| CA3122575A1 (en) | 2018-12-14 | 2020-06-18 | Beta Pharma, Inc. | Organophosphorus-substituted compounds as c-met inhibitors and therapeutic uses thereof |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| JP2022526713A (ja) | 2019-03-21 | 2022-05-26 | オンクセオ | がんの処置のための、キナーゼ阻害剤と組み合わせたＤｂａｉｔ分子 |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US12122767B2 (en) | 2019-10-01 | 2024-10-22 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| GEP20247679B (en) | 2019-10-14 | 2024-10-10 | Incyte Corp | Bicyclic heterocycles as fgfr inhibitors |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| KR20220098759A (ko) | 2019-11-08 | 2022-07-12 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 키나제 억제제에 대해 내성을 획득한 암의 치료 방법 |
| JP7720840B2 (ja) | 2019-12-04 | 2025-08-08 | インサイト・コーポレイション | Ｆｇｆｒ阻害剤としての三環式複素環 |
| PE20221504A1 (es) | 2019-12-04 | 2022-09-30 | Incyte Corp | Derivados de un inhibidor de fgfr |
| WO2021146424A1 (en) | 2020-01-15 | 2021-07-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| TW202304459A (zh) | 2021-04-12 | 2023-02-01 | 美商英塞特公司 | 包含ｆｇｆｒ抑制劑及ｎｅｃｔｉｎ－４靶向劑之組合療法 |
| CA3220155A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| TW202313611A (zh) | 2021-06-09 | 2023-04-01 | 美商英塞特公司 | 作為ｆｇｆｒ抑制劑之三環雜環 |
| IL314082A (en) | 2022-01-12 | 2024-09-01 | Denali Therapeutics Inc | Crystal forms of (S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazapin-3-yl)- H4- 1,2,4-triazole-3-carboxamide |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8719368D0 (en) | 1987-08-15 | 1987-09-23 | Wellcome Found | Heterocyclic compounds |
| US7723336B2 (en) | 2005-09-22 | 2010-05-25 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| US20070078136A1 (en) | 2005-09-22 | 2007-04-05 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| NZ568666A (en) | 2005-11-30 | 2011-09-30 | Vertex Pharma | [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazole derivative as inhibitors of c-Met |
| ME02736B (me) * | 2005-12-21 | 2017-10-20 | Janssen Pharmaceutica Nv | Triazolopiridazini kao modulatori tirozin kinaze |
| US8044049B2 (en) | 2006-08-04 | 2011-10-25 | Takeda Pharmaceutical Company Limited | Fused heterocyclic derivative and use thereof |
| JP2010500365A (ja) * | 2006-08-07 | 2010-01-07 | インサイト・コーポレイション | キナーゼ阻害剤としてのトリアゾロトリアジン |
| EP1900739A1 (en) | 2006-08-30 | 2008-03-19 | Cellzome Ag | Diazolodiazine derivatives as kinase inhibitors |
| AU2007292924A1 (en) | 2006-09-07 | 2008-03-13 | Biogen Idec Ma Inc. | IRAK modulators for treating an inflammatory condition, cell proliferative disorder, immune disorder |
| NZ575336A (en) | 2006-10-23 | 2012-04-27 | Sgx Pharmaceuticals Inc | Bicyclic triazoles as protein kinase modulators |
| BRPI0719333A2 (pt) * | 2006-11-22 | 2014-02-04 | Incyte Corp | Midazotriazinas e imidazopirimidinas como inbidores de cinase |
| PA8792501A1 (es) | 2007-08-09 | 2009-04-23 | Sanofi Aventis | Nuevos derivados de 6-triazolopiridacina-sulfanil benzotiazol y bencimidazol,su procedimiento de preparación,su aplicación como medicamentos,composiciones farmacéuticas y nueva utilización principalmente como inhibidores de met. |
| WO2009106577A1 (en) * | 2008-02-28 | 2009-09-03 | Novartis Ag | Imidazo [1,2-b] pyridazine derivatives for the treatment of c-met tyrosine kinase mediated disease |
-
2009
- 2009-08-13 UY UY0001032049A patent/UY32049A/es not_active Application Discontinuation
- 2009-08-14 NZ NZ590617A patent/NZ590617A/en not_active IP Right Cessation
- 2009-08-14 ES ES09791542.5T patent/ES2608761T3/es active Active
- 2009-08-14 CA CA2731108A patent/CA2731108A1/en not_active Abandoned
- 2009-08-14 AR ARP090103156A patent/AR072936A1/es unknown
- 2009-08-14 EP EP09791542.5A patent/EP2313407B1/en active Active
- 2009-08-14 WO PCT/US2009/053913 patent/WO2010019899A1/en not_active Ceased
- 2009-08-14 MY MYPI20110564 patent/MY150542A/en unknown
- 2009-08-14 AU AU2009281822A patent/AU2009281822B2/en not_active Expired - Fee Related
- 2009-08-14 CN CN200980131456.9A patent/CN102124005B/zh not_active Expired - Fee Related
- 2009-08-14 GE GEAP200912126A patent/GEP20125652B/en unknown
- 2009-08-14 MX MX2011001732A patent/MX2011001732A/es active IP Right Grant
- 2009-08-14 BR BRPI0917808A patent/BRPI0917808A2/pt not_active IP Right Cessation
- 2009-08-14 JP JP2011523198A patent/JP5469666B2/ja not_active Expired - Fee Related
- 2009-08-14 PE PE2011000152A patent/PE20110275A1/es not_active Application Discontinuation
- 2009-08-14 US US12/541,724 patent/US8178534B2/en not_active Expired - Fee Related
- 2009-08-14 EA EA201170295A patent/EA019723B1/ru not_active IP Right Cessation
- 2009-08-14 KR KR1020117005243A patent/KR20110039383A/ko not_active Ceased
- 2009-08-14 TW TW098127469A patent/TWI455939B/zh not_active IP Right Cessation
-
2011
- 2011-01-18 ZA ZA2011/00467A patent/ZA201100467B/en unknown
- 2011-01-18 IL IL210734A patent/IL210734A0/en unknown
- 2011-02-11 DO DO2011000050A patent/DOP2011000050A/es unknown
- 2011-03-07 MA MA33676A patent/MA32615B1/fr unknown
- 2011-03-11 CO CO11030354A patent/CO6351724A2/es active IP Right Grant
- 2011-03-14 EC EC2011010889A patent/ECSP11010889A/es unknown
- 2011-03-14 CR CR20110135A patent/CR20110135A/es unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012500215A5 (OSRAM) | ||
| KR102730859B1 (ko) | 아릴 및 헤테로아릴 치환된 인돌 화합물 | |
| JP6109192B2 (ja) | ピリダジンアミド化合物及びｓｙｋ阻害剤としてのそれらの使用 | |
| JP6978507B2 (ja) | Ｃｆｔｒ増強物質としてのピロロピリミジン | |
| AU2011240808B2 (en) | 5, 7-substituted-imidazo [1, 2-c] pyrimidines as inhibitors of JAK kinases | |
| DK2953952T3 (en) | MACROCYCLIC PYRIDAZININE DERIVATIVES | |
| WO2021115286A1 (zh) | 一种可用作shp2抑制剂的含氮杂原子的六元并五元芳环衍生物 | |
| AU2020203967A1 (en) | Amide-substituted heterocyclic compounds useful as modulators of il-12, il-23 and/or ifn alpha responses | |
| JP6139690B2 (ja) | ブルートンチロシンキナーゼの阻害剤 | |
| ES2271221T3 (es) | Derivados imidazo-pirimidina como ligandos para receptores gaba. | |
| JP6730200B2 (ja) | ホスホイノシチド３−キナーゼ阻害剤としてのインドリジン誘導体 | |
| CN102388055B (zh) | 咪唑并[2,1-b][1,3,4]噻二唑衍生物 | |
| SK15332002A3 (sk) | Imidazopyrimidínové a triazolopyrimidínové deriváty, spôsob ich prípravy, farmaceutický prostriedok obsahujúci tieto deriváty a použitie | |
| EA016028B1 (ru) | Конденсированные гетероциклические производные и их применение | |
| CA2726460A1 (en) | Novel phenyl-imidazopyridines and pyridazines | |
| KR20080053392A (ko) | Ｍｇｌｕｒ2 길항제로서 옥사다이아졸일 피라졸로-피리미딘 | |
| CA3151232A1 (en) | Pharmaceutical compounds | |
| ES2976515T3 (es) | Compuestos y composiciones para tratar afecciones asociadas con la actividad del receptor APJ | |
| WO2017046738A1 (en) | Triazolone compounds as perk inhibitors | |
| CN114502163A (zh) | 作为rho相关卷曲螺旋激酶(rock)抑制剂的乙炔基杂环 | |
| CA2723745A1 (en) | Fused pyrazine compounds useful for the treatment of degenerative and inflammatory diseases | |
| AU2015201991A1 (en) | 5, 7-substituted-imidazo [1, 2-c] pyrimidines as inhibitors of JAK kinases |