JP2018520201A5 - - Google Patents
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- JP2018520201A5 JP2018520201A5 JP2018503142A JP2018503142A JP2018520201A5 JP 2018520201 A5 JP2018520201 A5 JP 2018520201A5 JP 2018503142 A JP2018503142 A JP 2018503142A JP 2018503142 A JP2018503142 A JP 2018503142A JP 2018520201 A5 JP2018520201 A5 JP 2018520201A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- pyrrolo
- amino
- triazin
- amine
- 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.)
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- 239000001257 hydrogen Substances 0.000 claims 67
- 229910052739 hydrogen Inorganic materials 0.000 claims 67
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 50
- -1 3-Fluoropyridin-4-yl Chemical group 0.000 claims 42
- 150000002431 hydrogen Chemical class 0.000 claims 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 24
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 15
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 9
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 235000005152 nicotinamide Nutrition 0.000 claims 7
- 239000011570 nicotinamide Substances 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 150000001412 amines Chemical class 0.000 claims 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229960004979 fampridine Drugs 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- CZUNBUWXQDQTQD-UHFFFAOYSA-N CCC1=CN2N=C(N=C(NC3=C(F)C=NC=C3)C2=C1)C1=NC(OC)=CC=C1 Chemical compound CCC1=CN2N=C(N=C(NC3=C(F)C=NC=C3)C2=C1)C1=NC(OC)=CC=C1 CZUNBUWXQDQTQD-UHFFFAOYSA-N 0.000 claims 2
- DITADRLTSRJSDB-UHFFFAOYSA-N FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=CC(=NC=C1)NC(C)=O)=CC=C2)(F)F Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=CC(=NC=C1)NC(C)=O)=CC=C2)(F)F DITADRLTSRJSDB-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- QROKOTBWFZITJZ-UHFFFAOYSA-N n-pyridin-2-ylacetamide Chemical compound CC(=O)NC1=CC=CC=N1 QROKOTBWFZITJZ-UHFFFAOYSA-N 0.000 claims 2
- KGRPHHFLPMPUBB-UHFFFAOYSA-N pyrrolo[2,1-f][1,2,4]triazine Chemical compound C1=NC=NN2C=CC=C21 KGRPHHFLPMPUBB-UHFFFAOYSA-N 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 102000052185 transforming growth factor beta receptor activity proteins Human genes 0.000 claims 2
- 108700015056 transforming growth factor beta receptor activity proteins Proteins 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- WOKGXNSTAOLINW-QFIPXVFZSA-N (1R)-2-[[4-[(3-fluoropyridin-4-yl)amino]-2-pyridin-2-ylpyrrolo[2,1-f][1,2,4]triazin-5-yl]methylamino]-1-phenylethanol Chemical compound O[C@@H](CNCC1=C2N(C=C1)N=C(N=C2NC1=C(F)C=NC=C1)C1=NC=CC=C1)C1=CC=CC=C1 WOKGXNSTAOLINW-QFIPXVFZSA-N 0.000 claims 1
- DYADHZMPBOSGOL-LJQANCHMSA-N (3R)-3-fluoro-4-[[4-[(3-fluoropyridin-4-yl)amino]-2-(6-methoxypyridin-2-yl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]methylamino]-2-methylbutan-2-ol Chemical compound F[C@@H](C(C)(O)C)CNCC=1C=C2C(=NC(=NN2C=1)C1=NC(=CC=C1)OC)NC1=C(C=NC=C1)F DYADHZMPBOSGOL-LJQANCHMSA-N 0.000 claims 1
- HUEXJRRSSHIGFJ-VQIMIIECSA-N (3R,4R)-4-amino-1-[[4-[(3-fluoropyridin-4-yl)amino]-2-pyridin-2-ylpyrrolo[2,1-f][1,2,4]triazin-5-yl]methyl]piperidin-3-ol Chemical compound N[C@H]1[C@@H](CN(CC1)CC=1C=CN2N=C(N=C(C2=1)NC1=C(C=NC=C1)F)C1=NC=CC=C1)O HUEXJRRSSHIGFJ-VQIMIIECSA-N 0.000 claims 1
- KRZJRNZICWNMOA-GXSJLCMTSA-N (3s,4r)-4,8-dihydroxy-3-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@@H](O)[C@@H](OC)CC(=O)C2=C1O KRZJRNZICWNMOA-GXSJLCMTSA-N 0.000 claims 1
- SZBIFEUGEPUYLA-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-pyridin-3-ylmethanone Chemical compound C1CC(O)CCN1C(=O)C1=CC=CN=C1 SZBIFEUGEPUYLA-UHFFFAOYSA-N 0.000 claims 1
- QALWNDKPDOXZOK-UHFFFAOYSA-N 1-N-[[4-[(3-fluoropyridin-4-yl)amino]-2-pyridin-2-ylpyrrolo[2,1-f][1,2,4]triazin-5-yl]methyl]-4-N,4-N-dimethylcyclohexane-1,4-diamine Chemical compound FC=1C=NC=CC=1NC1=NC(=NN2C1=C(C=C2)CNC1CCC(CC1)N(C)C)C1=NC=CC=C1 QALWNDKPDOXZOK-UHFFFAOYSA-N 0.000 claims 1
- QNKZXPXFGIFQFD-UHFFFAOYSA-N 1-[[2-[6-(difluoromethyl)pyridin-2-yl]-4-[(3-fluoropyridin-4-yl)amino]pyrrolo[2,1-f][1,2,4]triazin-5-yl]methylamino]-2-methylpropan-2-ol Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)F)=C(C=C2)CNCC(C)(O)C)F QNKZXPXFGIFQFD-UHFFFAOYSA-N 0.000 claims 1
- KSMGVZIGENFECE-UHFFFAOYSA-N 1-[[4-[(3-fluoropyridin-4-yl)amino]-2-[6-(trifluoromethyl)pyridin-2-yl]pyrrolo[2,1-f][1,2,4]triazin-5-yl]methylamino]-2-methylpropan-2-ol Chemical compound FC=1C=NC=CC=1NC1=NC(=NN2C1=C(C=C2)CNCC(C)(O)C)C1=NC(=CC=C1)C(F)(F)F KSMGVZIGENFECE-UHFFFAOYSA-N 0.000 claims 1
- SJTNMAYUGDTESD-UHFFFAOYSA-N 1-[[4-[(3-fluoropyridin-4-yl)amino]-2-pyridin-2-ylpyrrolo[2,1-f][1,2,4]triazin-5-yl]methylamino]-2-methylpropan-2-ol Chemical compound FC=1C=NC=CC=1NC1=NC(=NN2C1=C(C=C2)CNCC(C)(O)C)C1=NC=CC=C1 SJTNMAYUGDTESD-UHFFFAOYSA-N 0.000 claims 1
- HNHSBRVSFUOXLK-UHFFFAOYSA-N 1-[[4-[[2-(ethylamino)pyridin-4-yl]amino]-2-pyridin-2-ylpyrrolo[2,1-f][1,2,4]triazin-5-yl]methylamino]-2-methylpropan-2-ol Chemical compound C(C)NC1=NC=CC(=C1)NC1=NC(=NN2C1=C(C=C2)CNCC(C)(O)C)C1=NC=CC=C1 HNHSBRVSFUOXLK-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- FVSJLIMMUAYMPR-UHFFFAOYSA-N 2-(2-methylsulfanylpyrimidin-4-yl)-N-pyridin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine Chemical compound CSC1=NC=CC(=N1)C1=NN2C(C(=N1)NC1=CC=NC=C1)=CC=C2 FVSJLIMMUAYMPR-UHFFFAOYSA-N 0.000 claims 1
- JLLWVFJRANPTOC-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-1-[4-[(3-fluoropyridin-4-yl)amino]-2-(6-methoxypyridin-2-yl)pyrrolo[2,1-f][1,2,4]triazin-5-yl]ethanol Chemical compound FC1(CCN(CC1)CC(O)C=1C=CN2N=C(N=C(C2=1)NC1=C(C=NC=C1)F)C1=NC(=CC=C1)OC)F JLLWVFJRANPTOC-UHFFFAOYSA-N 0.000 claims 1
- FBSDACQZDSAUDP-UHFFFAOYSA-N 2-(5-fluoro-6-methylpyridin-2-yl)-N-(3-fluoropyridin-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine Chemical compound FC=1C=NC=CC=1NC1=NC(=NN2C1=CC=C2)C1=NC(=C(C=C1)F)C FBSDACQZDSAUDP-UHFFFAOYSA-N 0.000 claims 1
- MOBQPEPZKOOZLN-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-N-[3-(3-morpholin-4-ylpropoxy)pyridin-4-yl]pyrrolo[2,1-f][1,2,4]triazin-4-amine Chemical compound CC1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)OCCCN1CCOCC1)=CC=C2 MOBQPEPZKOOZLN-UHFFFAOYSA-N 0.000 claims 1
- OZGNJCIBAIISAW-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-N-phenyl-4-(pyridin-4-ylamino)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide Chemical compound CC1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=CC=NC=C1)=CC(=C2)C(=O)NC1=CC=CC=C1 OZGNJCIBAIISAW-UHFFFAOYSA-N 0.000 claims 1
- FDDQNLYIICJTKT-UHFFFAOYSA-N 2-[2-(1,1-dioxo-1,4-thiazinan-4-yl)ethylamino]-1-[4-[(3-fluoropyridin-4-yl)amino]-2-(6-methoxypyridin-2-yl)pyrrolo[2,1-f][1,2,4]triazin-5-yl]ethanol Chemical compound COc1cccc(n1)-c1nc(Nc2ccncc2F)c2c(ccn2n1)C(O)CNCCN1CCS(=O)(=O)CC1 FDDQNLYIICJTKT-UHFFFAOYSA-N 0.000 claims 1
- QPJBKWSBPBAGFP-UHFFFAOYSA-N 2-[6-(difluoromethyl)pyridin-2-yl]-5-[(4,4-difluoropiperidin-1-yl)methyl]-N-(3-fluoropyridin-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)F)=C(C=C2)CN1CCC(CC1)(F)F)F QPJBKWSBPBAGFP-UHFFFAOYSA-N 0.000 claims 1
- IBRBAQVPWKWKSG-UHFFFAOYSA-N 2-amino-N-[4-[(3-fluoropyridin-4-yl)amino]-2-(6-methoxypyridin-2-yl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]acetamide Chemical compound NCC(=O)NC=1C=C2C(=NC(=NN2C=1)C1=NC(=CC=C1)OC)NC1=C(C=NC=C1)F IBRBAQVPWKWKSG-UHFFFAOYSA-N 0.000 claims 1
- DXVXGQDTEZKMLS-UHFFFAOYSA-N 2-pyridin-2-yl-N-pyridin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine Chemical compound N1=C(C=CC=C1)C1=NN2C(C(=N1)NC1=CC=NC=C1)=CC=C2 DXVXGQDTEZKMLS-UHFFFAOYSA-N 0.000 claims 1
- GIJVUYWUMOEEJF-UHFFFAOYSA-N 3-[[4-[(3-fluoropyridin-4-yl)amino]-2-pyridin-2-ylpyrrolo[2,1-f][1,2,4]triazin-5-yl]methylamino]adamantan-1-ol Chemical compound OC12CC3CC(C1)CC(C3)(C2)NCC1=C2N(C=C1)N=C(N=C2NC1=CC=NC=C1F)C1=CC=CC=N1 GIJVUYWUMOEEJF-UHFFFAOYSA-N 0.000 claims 1
- PTXZFJRSOOXAJD-UHFFFAOYSA-N 4-N-[2-(6-methoxypyridin-2-yl)-5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yl]-2-N-(2-morpholin-4-ylethyl)pyridine-2,4-diamine Chemical compound COC1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=CC(=NC=C1)NCCN1CCOCC1)=C(C=C2)C PTXZFJRSOOXAJD-UHFFFAOYSA-N 0.000 claims 1
- LZJABIHXXPLMEI-UHFFFAOYSA-N 4-N-[[4-[(3-fluoropyridin-4-yl)amino]-2-pyridin-2-ylpyrrolo[2,1-f][1,2,4]triazin-5-yl]methyl]cyclohexane-1,4-diamine Chemical compound NC1CCC(CC1)NCC1=C2N(C=C1)N=C(N=C2NC1=C(F)C=NC=C1)C1=NC=CC=C1 LZJABIHXXPLMEI-UHFFFAOYSA-N 0.000 claims 1
- AENKGRGSOYZWCJ-UHFFFAOYSA-N 4-[(2-pyridin-2-ylpyrrolo[2,1-f][1,2,4]triazin-4-yl)amino]pyridine-3-carboxamide Chemical compound N1=C(C=CC=C1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)C(=O)N)=CC=C2 AENKGRGSOYZWCJ-UHFFFAOYSA-N 0.000 claims 1
- DFLOTDBXWMAOKF-UHFFFAOYSA-N 4-[(3-fluoropyridin-4-yl)amino]-2-(6-methylpyridin-2-yl)pyrrolo[2,1-f][1,2,4]triazine-7-carboxylic acid Chemical compound FC=1C=NC=CC=1NC1=NC(=NN2C1=CC=C2C(=O)O)C1=NC(=CC=C1)C DFLOTDBXWMAOKF-UHFFFAOYSA-N 0.000 claims 1
- UDIJBMFAHNPMBI-UHFFFAOYSA-N 4-[[2-(6-methoxypyridin-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]pyridine-3-carboxamide Chemical compound COC1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)C(=O)N)=CC=C2 UDIJBMFAHNPMBI-UHFFFAOYSA-N 0.000 claims 1
- YDVAQJIQIQABII-UHFFFAOYSA-N 4-[[2-(6-methylpyridin-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]-N-(2-piperidin-1-ylethyl)pyridine-3-carboxamide Chemical compound CC1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)C(=O)NCCN1CCCCC1)=CC=C2 YDVAQJIQIQABII-UHFFFAOYSA-N 0.000 claims 1
- LMVFSIOXYQMPKC-UHFFFAOYSA-N 4-[[2-[6-(difluoromethyl)pyridin-2-yl]pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]-N-(1,3-oxazol-4-ylmethyl)pyridine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)C(=O)NCC=1N=COC=1)=CC=C2)F LMVFSIOXYQMPKC-UHFFFAOYSA-N 0.000 claims 1
- LRVURNNKHCTTAA-UHFFFAOYSA-N 4-[[2-[6-(difluoromethyl)pyridin-2-yl]pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]-N-(1H-1,2,4-triazol-5-ylmethyl)pyridine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)C(=O)NCC1=NNC=N1)=CC=C2)F LRVURNNKHCTTAA-UHFFFAOYSA-N 0.000 claims 1
- JFKCNVRFODXGGL-UHFFFAOYSA-N 4-[[2-[6-(difluoromethyl)pyridin-2-yl]pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]-N-(2-hydroxyethyl)pyridine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)C(=O)NCCO)=CC=C2)F JFKCNVRFODXGGL-UHFFFAOYSA-N 0.000 claims 1
- DTXRINDVZOOVKE-UHFFFAOYSA-N 4-[[2-[6-(difluoromethyl)pyridin-2-yl]pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]-N-(3,3,3-trifluoropropyl)pyridine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)C(=O)NCCC(F)(F)F)=CC=C2)F DTXRINDVZOOVKE-UHFFFAOYSA-N 0.000 claims 1
- PBAFSXNZOHGUAX-UHFFFAOYSA-N 4-[[2-[6-(difluoromethyl)pyridin-2-yl]pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]-N-(oxan-4-yl)pyridine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)C(=O)NC1CCOCC1)=CC=C2)F PBAFSXNZOHGUAX-UHFFFAOYSA-N 0.000 claims 1
- XKWYUBOVLSEUGF-UHFFFAOYSA-N 4-[[2-[6-(difluoromethyl)pyridin-2-yl]pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]-N-(pyridin-2-ylmethyl)pyridine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)C(=O)NCC1=NC=CC=C1)=CC=C2)F XKWYUBOVLSEUGF-UHFFFAOYSA-N 0.000 claims 1
- NPZJLJUYMKFJMB-OXQOHEQNSA-N 4-[[2-[6-(difluoromethyl)pyridin-2-yl]pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]-N-[(1R,2R)-2-hydroxycyclohexyl]pyridine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)C(=O)N[C@H]1[C@@H](CCCC1)O)=CC=C2)F NPZJLJUYMKFJMB-OXQOHEQNSA-N 0.000 claims 1
- CZNZBPUYVZWCFL-BEFAXECRSA-N 4-[[2-[6-(difluoromethyl)pyridin-2-yl]pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]-N-[(1R,2S)-2-hydroxycyclopentyl]pyridine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)C(=O)N[C@H]1[C@H](CCC1)O)=CC=C2)F CZNZBPUYVZWCFL-BEFAXECRSA-N 0.000 claims 1
- NPZJLJUYMKFJMB-JXFKEZNVSA-N 4-[[2-[6-(difluoromethyl)pyridin-2-yl]pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]-N-[(1S,2S)-2-hydroxycyclohexyl]pyridine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)C(=O)N[C@@H]1[C@H](CCCC1)O)=CC=C2)F NPZJLJUYMKFJMB-JXFKEZNVSA-N 0.000 claims 1
- CZNZBPUYVZWCFL-KXBFYZLASA-N 4-[[2-[6-(difluoromethyl)pyridin-2-yl]pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]-N-[(1S,2S)-2-hydroxycyclopentyl]pyridine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)C(=O)N[C@@H]1[C@H](CCC1)O)=CC=C2)F CZNZBPUYVZWCFL-KXBFYZLASA-N 0.000 claims 1
- JUWPKCGPZGFSEY-UHFFFAOYSA-N 4-[[2-[6-(difluoromethyl)pyridin-2-yl]pyrrolo[2,1-f][1,2,4]triazin-4-yl]amino]-N-[(5-ethyl-1,3,4-oxadiazol-2-yl)methyl]pyridine-3-carboxamide Chemical compound FC(C1=CC=CC(=N1)C1=NN2C(C(=N1)NC1=C(C=NC=C1)C(=O)NCC=1OC(=NN=1)CC)=CC=C2)F JUWPKCGPZGFSEY-UHFFFAOYSA-N 0.000 claims 1
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| EP3394056B1 (en) | 2015-12-22 | 2021-04-14 | Shy Therapeutics LLC | Compounds for the treatment of cancer and inflammatory disease |
| CA3066939A1 (en) | 2017-06-21 | 2018-12-27 | SHY Therapeutics LLC | Compounds that interact with the ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| US10653682B2 (en) * | 2017-10-26 | 2020-05-19 | Southern Research Institute | Oxadiazoles and thiadiazoles as TGF-β inhibitors |
| US12391705B2 (en) | 2018-12-19 | 2025-08-19 | Shy Therapeutics, Llc | Compounds that interact with the Ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| MX2021007738A (es) | 2018-12-27 | 2021-08-05 | Nexys Therapeutics Inc | Derivados de (piridin-2-il)amina como inhibidores de tgf-beta r1 (alk5) para el tratamiento de cancer. |
| CN111825675B (zh) * | 2019-04-15 | 2023-08-01 | 武汉朗来科技发展有限公司 | Rock抑制剂及其制备方法和用途 |
| CN112694477B (zh) * | 2019-10-22 | 2024-02-06 | 四川科伦博泰生物医药股份有限公司 | 吡唑并环类化合物，包含其的药物组合物，其制备方法及其用途 |
| CN114728965B (zh) * | 2020-01-21 | 2024-05-28 | 四川科伦博泰生物医药股份有限公司 | 吡啶并杂环类化合物、其制备方法及用途 |
| CN113620956B (zh) * | 2020-05-06 | 2023-06-13 | 赛诺哈勃药业（成都）有限公司 | 转化生长因子受体拮抗剂、其制备方法和应用 |
| JP2025512935A (ja) * | 2022-04-08 | 2025-04-22 | シャイ・セラピューティクス・エルエルシー | がん、炎症性疾患、ｒａｓ病、及び線維性疾患の処置のためのｒａｓスーパーファミリータンパク質と相互作用する化合物 |
| US20260028365A1 (en) * | 2022-07-14 | 2026-01-29 | Biogen Ma Inc. | Tyrosine kinase 2 inhibitors and uses thereof |
| WO2024155837A1 (en) * | 2023-01-19 | 2024-07-25 | Skyhawk Therapeutics, Inc. | Compositions useful for modulating splicing |
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| WO2004022559A1 (en) * | 2002-09-04 | 2004-03-18 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| WO2004065392A1 (en) | 2003-01-24 | 2004-08-05 | Smithkline Beecham Corporation | Condensed pyridines and pyrimidines and their use as alk-5 receptor ligands |
| WO2004087056A2 (en) * | 2003-03-28 | 2004-10-14 | Scios Inc. | BI-CYCLIC PYRIMIDINE INHIBITORS OF TGFβ |
| JP6104824B2 (ja) * | 2011-03-09 | 2017-03-29 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ピリド［２，３−ｂ］ピラジン誘導体およびそれらの治療的使用 |
| CN103450204B (zh) * | 2012-05-31 | 2016-08-17 | 中国科学院上海药物研究所 | 吡咯[2，1-f][1，2，4]并三嗪类化合物，其制备方法及用途 |
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