JP2017515836A5 - - Google Patents
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- Publication number
- JP2017515836A5 JP2017515836A5 JP2016567364A JP2016567364A JP2017515836A5 JP 2017515836 A5 JP2017515836 A5 JP 2017515836A5 JP 2016567364 A JP2016567364 A JP 2016567364A JP 2016567364 A JP2016567364 A JP 2016567364A JP 2017515836 A5 JP2017515836 A5 JP 2017515836A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- methyl
- phenyl
- pyrazolo
- fluoro
- 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
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 81
- 125000000623 heterocyclic group Chemical group 0.000 claims 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 61
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 55
- 125000005843 halogen group Chemical group 0.000 claims 53
- -1 amino, phenyl Chemical group 0.000 claims 51
- 125000001072 heteroaryl group Chemical group 0.000 claims 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims 36
- 125000001624 naphthyl group Chemical group 0.000 claims 34
- 229910052799 carbon Inorganic materials 0.000 claims 32
- 229910052739 hydrogen Inorganic materials 0.000 claims 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 31
- 229910052757 nitrogen Inorganic materials 0.000 claims 30
- 125000004430 oxygen atom Chemical group O* 0.000 claims 25
- 229910052760 oxygen Inorganic materials 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 23
- 125000001424 substituent group Chemical group 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000004434 sulfur atom Chemical group 0.000 claims 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims 17
- 239000012453 solvate Substances 0.000 claims 13
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 238000010276 construction Methods 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 229920006395 saturated elastomer Polymers 0.000 claims 8
- 125000004104 aryloxy group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 5
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 5
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 4
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims 4
- 235000005152 nicotinamide Nutrition 0.000 claims 4
- 239000011570 nicotinamide Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- SOUUBYMKVDZNMX-UHFFFAOYSA-N N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]-(2-morpholin-4-ylethyl)amino]methyl]phenyl]-N-methylmethanesulfonamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)N(CCN1CCOCC1)CC1=C(C=CC=C1)N(S(=O)(=O)C)C)C=NN2 SOUUBYMKVDZNMX-UHFFFAOYSA-N 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- UROXANZIWZQDLE-UHFFFAOYSA-N 1-[6-(2-ethyl-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]-N,N-dimethylpyrrolidine-3-sulfonamide Chemical compound C(C)C1=C(C=CC(=C1)O)C1=CC2=C(C(=N1)N1CC(CC1)S(=O)(=O)N(C)C)C=NN2 UROXANZIWZQDLE-UHFFFAOYSA-N 0.000 claims 1
- USRHJLBPRGSTRN-UHFFFAOYSA-N 2-(2,2,2-trifluoroethyl)phenol Chemical compound OC1=CC=CC=C1CC(F)(F)F USRHJLBPRGSTRN-UHFFFAOYSA-N 0.000 claims 1
- JCWGFKMAGZQXMM-UHFFFAOYSA-N 2-[4-amino-2-[[2-[benzenesulfonyl(methyl)amino]-5-hydroxyphenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]pyridin-3-yl]-2-iminoacetamide Chemical compound CN(C1=CC=C(O)C=C1CNC1=C(C(=N)C(N)=O)C(N)=CC(=N1)C1=CC(F)=C(O)C=C1CC(F)(F)F)S(=O)(=O)C1=CC=CC=C1 JCWGFKMAGZQXMM-UHFFFAOYSA-N 0.000 claims 1
- ARRUYBCRZQEXRU-UHFFFAOYSA-N 2-[4-amino-2-[[2-[ethyl(ethylsulfonyl)amino]phenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]pyridin-3-yl]-2-iminoacetamide Chemical compound CCN(C1=CC=CC=C1CNC1=C(C(=N)C(N)=O)C(N)=CC(=N1)C1=CC(F)=C(O)C=C1CC(F)(F)F)S(=O)(=O)CC ARRUYBCRZQEXRU-UHFFFAOYSA-N 0.000 claims 1
- JSSUYMWUQFVPRG-UHFFFAOYSA-N 2-[4-amino-2-[[2-[ethyl(methylsulfonyl)amino]-5-methylphenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]pyridin-3-yl]-2-iminoacetamide Chemical compound CCN(C1=CC=C(C)C=C1CNC1=C(C(=N)C(N)=O)C(N)=CC(=N1)C1=CC(F)=C(O)C=C1CC(F)(F)F)S(C)(=O)=O JSSUYMWUQFVPRG-UHFFFAOYSA-N 0.000 claims 1
- UPWGYUGLBMSEMX-UHFFFAOYSA-N 2-[4-amino-2-[[2-[ethyl(methylsulfonyl)amino]-5-methylpyridin-3-yl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]pyridin-3-yl]-2-iminoacetamide Chemical compound CCN(C1=NC=C(C)C=C1CNC1=C(C(=N)C(N)=O)C(N)=CC(=N1)C1=CC(F)=C(O)C=C1CC(F)(F)F)S(C)(=O)=O UPWGYUGLBMSEMX-UHFFFAOYSA-N 0.000 claims 1
- TWLJIKCVSLJUIM-UHFFFAOYSA-N 2-[4-amino-2-[[5-chloro-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]pyridin-3-yl]-2-iminoacetamide Chemical compound CN(C1=CC=C(Cl)C=C1CNC1=C(C(=N)C(N)=O)C(N)=CC(=N1)C1=CC(F)=C(O)C=C1CC(F)(F)F)S(C)(=O)=O TWLJIKCVSLJUIM-UHFFFAOYSA-N 0.000 claims 1
- IJHPBWFDHMKENG-UHFFFAOYSA-N 2-[4-amino-6-(2-cyclopropyl-5-fluoro-4-hydroxyphenyl)-2-[[2-[methyl(methylsulfonyl)amino]phenyl]methylamino]pyridin-3-yl]-2-imino-N-methylacetamide Chemical compound CNC(=O)C(=N)c1c(N)cc(nc1NCc1ccccc1N(C)S(C)(=O)=O)-c1cc(F)c(O)cc1C1CC1 IJHPBWFDHMKENG-UHFFFAOYSA-N 0.000 claims 1
- ZNVOURRPUATFRP-UHFFFAOYSA-N 2-[4-amino-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-2-[[2-[2-hydroxyethyl(methylsulfonyl)amino]phenyl]methylamino]pyridin-3-yl]-2-iminoacetamide Chemical compound CS(=O)(=O)N(CCO)C1=CC=CC=C1CNC1=C(C(=N)C(N)=O)C(N)=CC(=N1)C1=CC(F)=C(O)C=C1CC(F)(F)F ZNVOURRPUATFRP-UHFFFAOYSA-N 0.000 claims 1
- FBOHXIKPCPPBCA-UHFFFAOYSA-N 2-[4-amino-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-2-[[2-[methyl(pyridin-3-ylsulfonyl)amino]phenyl]methylamino]pyridin-3-yl]-2-iminoacetamide Chemical compound CN(C1=CC=CC=C1CNC1=C(C(=N)C(N)=O)C(N)=CC(=N1)C1=CC(F)=C(O)C=C1CC(F)(F)F)S(=O)(=O)C1=CC=CN=C1 FBOHXIKPCPPBCA-UHFFFAOYSA-N 0.000 claims 1
- ZOLFPEWMVUHAGI-UHFFFAOYSA-N 2-[4-amino-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-2-[[5-hydroxy-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]pyridin-3-yl]-2-imino-N-methylacetamide Chemical compound CNC(=O)C(=N)c1c(N)cc(nc1NCc1cc(O)ccc1N(C)S(C)(=O)=O)-c1cc(F)c(O)cc1CC(F)(F)F ZOLFPEWMVUHAGI-UHFFFAOYSA-N 0.000 claims 1
- YEDJPXKZPPPMNF-UHFFFAOYSA-N 2-[4-amino-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-2-[[5-hydroxy-2-[methyl(pyridin-3-ylsulfonyl)amino]phenyl]methylamino]pyridin-3-yl]-2-imino-N-methylacetamide Chemical compound CNC(=O)C(=N)c1c(N)cc(nc1NCc1cc(O)ccc1N(C)S(=O)(=O)c1cccnc1)-c1cc(F)c(O)cc1CC(F)(F)F YEDJPXKZPPPMNF-UHFFFAOYSA-N 0.000 claims 1
- RAOSMRQNSKDBMX-UHFFFAOYSA-N 2-[4-amino-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-2-[[5-methyl-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]pyridin-3-yl]-2-imino-N-methylacetamide Chemical compound CNC(=O)C(=N)c1c(N)cc(nc1NCc1cc(C)ccc1N(C)S(C)(=O)=O)-c1cc(F)c(O)cc1CC(F)(F)F RAOSMRQNSKDBMX-UHFFFAOYSA-N 0.000 claims 1
- WKRKSQPZCXXBLG-UHFFFAOYSA-N 2-[4-amino-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-2-[[5-methyl-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]pyridin-3-yl]-2-iminoacetamide Chemical compound CN(C1=CC=C(C)C=C1CNC1=C(C(=N)C(N)=O)C(N)=CC(=N1)C1=CC(F)=C(O)C=C1CC(F)(F)F)S(C)(=O)=O WKRKSQPZCXXBLG-UHFFFAOYSA-N 0.000 claims 1
- NDNPKPHRUSXHAY-UHFFFAOYSA-N 2-[4-amino-6-[[2-[benzenesulfonyl(methyl)amino]phenyl]methylamino]-2-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]pyrimidin-5-yl]-2-iminoacetamide Chemical compound CN(C1=CC=CC=C1CNC1=C(C(=N)C(N)=O)C(N)=NC(=N1)C1=CC(F)=C(O)C=C1CC(F)(F)F)S(=O)(=O)C1=CC=CC=C1 NDNPKPHRUSXHAY-UHFFFAOYSA-N 0.000 claims 1
- AXUAAROKDDFUCI-UHFFFAOYSA-N 2-fluoro-4-[4-(2-methylpropylamino)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-5-(2,2,2-trifluoroethyl)phenol Chemical compound FC1=C(C=C(C(=C1)C1=NC(=C2C(=N1)NN=C2)NCC(C)C)CC(F)(F)F)O AXUAAROKDDFUCI-UHFFFAOYSA-N 0.000 claims 1
- CWWJGUPPMFHHBU-UHFFFAOYSA-N 3-ethyl-4-[4-(4-methoxypiperidin-1-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]phenol Chemical compound CCC1=CC(O)=CC=C1C1=NC(N2CCC(CC2)OC)=C2C=NNC2=C1 CWWJGUPPMFHHBU-UHFFFAOYSA-N 0.000 claims 1
- WBJKFNOYTALWJK-UHFFFAOYSA-N 3-ethyl-4-[4-(6-fluoro-3,4-dihydro-1H-isoquinolin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]phenol Chemical compound CCC1=CC(O)=CC=C1C1=NC(N2CCC3=CC(F)=CC=C3C2)=C2C=NNC2=C1 WBJKFNOYTALWJK-UHFFFAOYSA-N 0.000 claims 1
- COIIDULXTXBYHQ-UHFFFAOYSA-N 3-ethyl-4-[4-(6-methoxy-7-phenylmethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]phenol Chemical compound CCC1=CC(O)=CC=C1C1=NC(N2CCC3=C(C2)C=C(OCC2=CC=CC=C2)C(OC)=C3)=C2C=NNC2=C1 COIIDULXTXBYHQ-UHFFFAOYSA-N 0.000 claims 1
- CMXPYUOPFJEEGA-UHFFFAOYSA-N 3-ethyl-4-[4-(8-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]phenol Chemical compound CCC1=CC(O)=CC=C1C1=NC(N2CCC3=C(C2)C(OC)=CC=C3)=C2C=NNC2=C1 CMXPYUOPFJEEGA-UHFFFAOYSA-N 0.000 claims 1
- IFOCLNIXUQUORY-UHFFFAOYSA-N 3-ethyl-4-[4-[6-(2-methoxyethoxy)-3,4-dihydro-1H-isoquinolin-2-yl]-1H-pyrazolo[4,3-c]pyridin-6-yl]phenol Chemical compound CCC1=CC(O)=CC=C1C1=NC(N2CCC3=CC(OCCOC)=CC=C3C2)=C2C=NNC2=C1 IFOCLNIXUQUORY-UHFFFAOYSA-N 0.000 claims 1
- SIIZUOGQMGVPBG-UHFFFAOYSA-N 3-ethyl-4-[4-[6-(4-methylimidazol-1-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-1H-pyrazolo[4,3-c]pyridin-6-yl]phenol Chemical compound CCC1=CC(O)=CC=C1C1=NC(N2CCC3=CC(=CC=C3C2)N2C=NC(C)=C2)=C2C=NNC2=C1 SIIZUOGQMGVPBG-UHFFFAOYSA-N 0.000 claims 1
- YDHPBDFTCLQXLO-UHFFFAOYSA-N 4-(cyclopentylmethylamino)-6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C1(CCCC1)CNC1=NC(=CC2=C1C(=NN2)C(=O)NC)C2=C(C=C(C(=C2)F)O)CC YDHPBDFTCLQXLO-UHFFFAOYSA-N 0.000 claims 1
- FRFUERGTAKOJMH-UHFFFAOYSA-N 4-(cyclopentylmethylamino)-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C1(CCCC1)CNC1=NC(=CC2=C1C(=NN2)C(=O)NC)C2=C(C=C(C(=C2)F)O)CC(F)(F)F FRFUERGTAKOJMH-UHFFFAOYSA-N 0.000 claims 1
- CXIDCFNHQRBJIW-UHFFFAOYSA-N 4-[3-(5-benzyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-2-yl)-4-(2-methylsulfanylethylamino)-1H-pyrazolo[4,3-c]pyridin-6-yl]-2-fluoro-5-(2,2,2-trifluoroethyl)phenol Chemical compound C(C1=CC=CC=C1)N1CC2=C(CC1)NC(=N2)C2=NNC1=C2C(=NC(=C1)C1=CC(=C(C=C1CC(F)(F)F)O)F)NCCSC CXIDCFNHQRBJIW-UHFFFAOYSA-N 0.000 claims 1
- YQQBFOUZJCRRKZ-UHFFFAOYSA-N 4-[3-(5-benzyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-2-yl)-4-[(3-hydroxy-2-methylpropyl)amino]-2H-pyrazolo[3,4-d]pyrimidin-6-yl]-2-fluoro-5-(2,2,2-trifluoroethyl)phenol Chemical compound C(C1=CC=CC=C1)N1CC2=C(CC1)NC(=N2)C2=NNC1=NC(=NC(=C12)NCC(CO)C)C1=CC(=C(C=C1CC(F)(F)F)O)F YQQBFOUZJCRRKZ-UHFFFAOYSA-N 0.000 claims 1
- JGMXYKHNJPQLKS-UHFFFAOYSA-N 4-[3-[6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[5-hydroxy-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-2H-pyrazolo[3,4-d]pyrimidin-3-yl]-1H-1,2,4-triazol-5-yl]piperidine-1-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=NC(=C2C(=N1)NN=C2C=2NC(=NN2)C2CCN(CC2)C(=O)N)NCC2=C(C=CC(=C2)O)N(S(=O)(=O)C)C)CC(F)(F)F)O JGMXYKHNJPQLKS-UHFFFAOYSA-N 0.000 claims 1
- FTSYURCNSVPOMF-UHFFFAOYSA-N 4-[4-(2-cyclopropylethylamino)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-2-fluoro-5-(2,2,2-trifluoroethyl)phenol Chemical compound C1(CC1)CCNC1=C2C(=NC(=N1)C1=CC(=C(C=C1CC(F)(F)F)O)F)NN=C2 FTSYURCNSVPOMF-UHFFFAOYSA-N 0.000 claims 1
- WEEHDGQBNPRIDK-UHFFFAOYSA-N 4-[4-(5-chloro-3,4-dihydro-1H-isoquinolin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]-3-ethylphenol Chemical compound CCC1=CC(O)=CC=C1C1=NC(N2CCC3=C(Cl)C=CC=C3C2)=C2C=NNC2=C1 WEEHDGQBNPRIDK-UHFFFAOYSA-N 0.000 claims 1
- NPDVLJJNPGUOET-UHFFFAOYSA-N 4-[4-(7,8-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]-3-ethylphenol Chemical compound CCC1=CC(O)=CC=C1C1=NC(N2CCC3=C(C2)C(OC)=C(OC)C=C3)=C2C=NNC2=C1 NPDVLJJNPGUOET-UHFFFAOYSA-N 0.000 claims 1
- VDOZUOGOAFISEB-UHFFFAOYSA-N 4-[4-(cyclopropylmethylamino)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-2-fluoro-5-(2,2,2-trifluoroethyl)phenol Chemical compound C1(CC1)CNC1=C2C(=NC(=N1)C1=CC(=C(C=C1CC(F)(F)F)O)F)NN=C2 VDOZUOGOAFISEB-UHFFFAOYSA-N 0.000 claims 1
- CMXWVULJKRWIIY-UHFFFAOYSA-N 4-[[2-[benzenesulfonyl(ethyl)amino]-5-hydroxyphenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)N(C1=C(CNC2=NC(=CC3=C2C(=NN3)C(=O)N)C3=C(C=C(C(=C3)F)O)CC(F)(F)F)C=C(C=C1)O)S(=O)(=O)C1=CC=CC=C1 CMXWVULJKRWIIY-UHFFFAOYSA-N 0.000 claims 1
- BJWUXIJMNZSUKD-UHFFFAOYSA-N 4-[[2-[benzenesulfonyl(ethyl)amino]-5-hydroxyphenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-2H-pyrazolo[3,4-d]pyrimidine-3-carboxamide Chemical compound C(C)N(S(=O)(=O)C1=CC=CC=C1)C1=C(CNC2=C3C(=NC(=N2)C2=C(C=C(C(=C2)F)O)CC(F)(F)F)NN=C3C(=O)N)C=C(C=C1)O BJWUXIJMNZSUKD-UHFFFAOYSA-N 0.000 claims 1
- VIECEYSWSIRBPV-UHFFFAOYSA-N 4-[[2-[benzenesulfonyl(ethyl)amino]-5-hydroxyphenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)N(C1=C(CNC2=NC(=CC3=C2C(=NN3)C(=O)NC)C3=C(C=C(C(=C3)F)O)CC(F)(F)F)C=C(C=C1)O)S(=O)(=O)C1=CC=CC=C1 VIECEYSWSIRBPV-UHFFFAOYSA-N 0.000 claims 1
- LVAQBJKPQFFYKV-UHFFFAOYSA-N 4-[[2-[benzenesulfonyl(ethyl)amino]-5-hydroxyphenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-2H-pyrazolo[3,4-d]pyrimidine-3-carboxamide Chemical compound C(C)N(S(=O)(=O)C1=CC=CC=C1)C1=C(CNC2=C3C(=NC(=N2)C2=C(C=C(C(=C2)F)O)CC(F)(F)F)NN=C3C(=O)NC)C=C(C=C1)O LVAQBJKPQFFYKV-UHFFFAOYSA-N 0.000 claims 1
- QCICTFWGEABKRH-UHFFFAOYSA-N 4-[[2-[benzenesulfonyl(methyl)amino]-5-hydroxyphenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC1=C(C=CC(=C1)O)N(S(=O)(=O)C1=CC=CC=C1)C)C(=NN2)C(=O)NC)CC(F)(F)F)O QCICTFWGEABKRH-UHFFFAOYSA-N 0.000 claims 1
- XADRUNJQTCTANO-UHFFFAOYSA-N 4-[[2-[benzenesulfonyl(methyl)amino]-5-hydroxyphenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-2H-pyrazolo[3,4-d]pyrimidine-3-carboxamide Chemical compound CN(S(=O)(=O)C1=CC=CC=C1)C1=C(CNC2=C3C(=NC(=N2)C2=C(C=C(C(=C2)F)O)CC(F)(F)F)NN=C3C(=O)NC)C=C(C=C1)O XADRUNJQTCTANO-UHFFFAOYSA-N 0.000 claims 1
- XSERXIPKYAQNID-UHFFFAOYSA-N 4-[[2-[benzenesulfonyl(methyl)amino]phenyl]methylamino]-6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCC1=C(C=CC=C1)N(S(=O)(=O)C1=CC=CC=C1)C)C(=NN2)C(=O)N XSERXIPKYAQNID-UHFFFAOYSA-N 0.000 claims 1
- VBOICNCFGWEKKD-UHFFFAOYSA-N 4-[[2-[benzenesulfonyl(methyl)amino]phenyl]methylamino]-6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-2H-pyrazolo[3,4-d]pyrimidine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=NC(=C2C(=N1)NN=C2C(=O)N)NCC2=C(C=CC=C2)N(S(=O)(=O)C2=CC=CC=C2)C VBOICNCFGWEKKD-UHFFFAOYSA-N 0.000 claims 1
- XQLGJMGMGPHVGJ-UHFFFAOYSA-N 4-[[2-[benzenesulfonyl(methyl)amino]phenyl]methylamino]-6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCC1=C(C=CC=C1)N(S(=O)(=O)C1=CC=CC=C1)C)C(=NN2)C(=O)NC XQLGJMGMGPHVGJ-UHFFFAOYSA-N 0.000 claims 1
- ZUSBJVMMJXWILX-UHFFFAOYSA-N 4-[[2-[benzenesulfonyl(methyl)amino]phenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC1=C(C=CC=C1)N(S(=O)(=O)C1=CC=CC=C1)C)C(=NN2)C(=O)N)CC(F)(F)F)O ZUSBJVMMJXWILX-UHFFFAOYSA-N 0.000 claims 1
- FSPWFVDHHHVWMS-UHFFFAOYSA-N 4-[[2-[benzenesulfonyl(methyl)amino]phenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-2H-pyrazolo[3,4-d]pyrimidine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=NC(=C2C(=N1)NN=C2C(=O)N)NCC2=C(C=CC=C2)N(S(=O)(=O)C2=CC=CC=C2)C)CC(F)(F)F)O FSPWFVDHHHVWMS-UHFFFAOYSA-N 0.000 claims 1
- RYQQIWSTVBYSJY-UHFFFAOYSA-N 4-[[2-[dimethylsulfamoyl(methyl)amino]phenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound CNC(=O)c1n[nH]c2cc(nc(NCc3ccccc3N(C)S(=O)(=O)N(C)C)c12)-c1cc(F)c(O)cc1CC(F)(F)F RYQQIWSTVBYSJY-UHFFFAOYSA-N 0.000 claims 1
- QLOJGOJQPPDPKW-UHFFFAOYSA-N 4-[[2-[ethyl(ethylsulfonyl)amino]phenyl]methylamino]-6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)N(C1=C(CNC2=NC(=CC3=C2C(=NN3)C(=O)NC)C3=C(C=C(C(=C3)F)O)CC)C=CC=C1)S(=O)(=O)CC QLOJGOJQPPDPKW-UHFFFAOYSA-N 0.000 claims 1
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- SXLQVQAYOSDJEP-UHFFFAOYSA-N 4-[[2-[ethyl(methylsulfonyl)amino]-5-fluorophenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)N(S(=O)(=O)C)C1=C(CNC2=NC(=CC3=C2C(=NN3)C(=O)N)C3=C(C=C(C(=C3)F)O)CC(F)(F)F)C=C(C=C1)F SXLQVQAYOSDJEP-UHFFFAOYSA-N 0.000 claims 1
- LPUWSAMCJAKXRH-UHFFFAOYSA-N 4-[[2-[ethyl(methylsulfonyl)amino]-5-fluoropyridin-3-yl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)N(C1=NC=C(C=C1CNC1=NC(=CC2=C1C(=NN2)C(=O)N)C2=C(C=C(C(=C2)F)O)CC(F)(F)F)F)S(=O)(=O)C LPUWSAMCJAKXRH-UHFFFAOYSA-N 0.000 claims 1
- QVLMKSBYGOHJSQ-UHFFFAOYSA-N 4-[[2-[ethyl(methylsulfonyl)amino]-5-hydroxyphenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)N(C1=C(CNC2=NC(=CC3=C2C(=NN3)C(=O)NC)C3=C(C=C(C(=C3)F)O)CC(F)(F)F)C=C(C=C1)O)S(=O)(=O)C QVLMKSBYGOHJSQ-UHFFFAOYSA-N 0.000 claims 1
- ZEPIDCBLPYNVQL-UHFFFAOYSA-N 4-[[2-[ethyl(methylsulfonyl)amino]phenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)N(C1=C(CNC2=NC(=CC3=C2C(=NN3)C(=O)N)C3=C(C=C(C(=C3)F)O)CC(F)(F)F)C=CC=C1)S(=O)(=O)C ZEPIDCBLPYNVQL-UHFFFAOYSA-N 0.000 claims 1
- JOEBIMBXEJJOMZ-UHFFFAOYSA-N 4-[[2-[ethyl(methylsulfonyl)amino]phenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)N(C1=C(CNC2=NC(=CC3=C2C(=NN3)C(=O)NC)C3=C(C=C(C(=C3)F)O)CC(F)(F)F)C=CC=C1)S(=O)(=O)C JOEBIMBXEJJOMZ-UHFFFAOYSA-N 0.000 claims 1
- RCEYXWYCVAOBSB-UHFFFAOYSA-N 4-[[2-[ethyl(methylsulfonyl)amino]phenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-2H-pyrazolo[3,4-d]pyrimidine-3-carboxamide Chemical compound C(C)N(S(=O)(=O)C)C1=C(CNC2=C3C(=NC(=N2)C2=C(C=C(C(=C2)F)O)CC(F)(F)F)NN=C3C(=O)NC)C=CC=C1 RCEYXWYCVAOBSB-UHFFFAOYSA-N 0.000 claims 1
- MRRNVQZSOMWWPU-UHFFFAOYSA-N 4-[[2-[ethyl(methylsulfonyl)amino]pyridin-3-yl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)N(C1=NC=CC=C1CNC1=NC(=CC2=C1C(=NN2)C(=O)N)C2=C(C=C(C(=C2)F)O)CC(F)(F)F)S(=O)(=O)C MRRNVQZSOMWWPU-UHFFFAOYSA-N 0.000 claims 1
- DTYDHPKDBIRYMB-UHFFFAOYSA-N 4-[[2-[ethyl(methylsulfonyl)amino]pyridin-3-yl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)N(C1=NC=CC=C1CNC1=NC(=CC2=C1C(=NN2)C(=O)NC)C2=C(C=C(C(=C2)F)O)CC(F)(F)F)S(=O)(=O)C DTYDHPKDBIRYMB-UHFFFAOYSA-N 0.000 claims 1
- HXZSBQWDFDSUBB-UHFFFAOYSA-N 4-[[2-[ethylsulfonyl(methyl)amino]phenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)S(=O)(=O)N(C1=C(CNC2=NC(=CC3=C2C(=NN3)C(=O)NC)C3=C(C=C(C(=C3)F)O)CC(F)(F)F)C=CC=C1)C HXZSBQWDFDSUBB-UHFFFAOYSA-N 0.000 claims 1
- HODUUEJTANAPBD-UHFFFAOYSA-N 4-[[3-[benzenesulfonyl(methyl)amino]pyrazin-2-yl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC1=NC=CN=C1N(S(=O)(=O)C1=CC=CC=C1)C)C(=NN2)C(=O)NC)CC(F)(F)F)O HODUUEJTANAPBD-UHFFFAOYSA-N 0.000 claims 1
- YFOBCCOOEQSQOX-UHFFFAOYSA-N 4-[[3-[ethyl(methylsulfonyl)amino]pyrazin-2-yl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)N(C=1C(=NC=CN1)CNC1=NC(=CC2=C1C(=NN2)C(=O)N)C2=C(C=C(C(=C2)F)O)CC(F)(F)F)S(=O)(=O)C YFOBCCOOEQSQOX-UHFFFAOYSA-N 0.000 claims 1
- AGPZQPUPJARSNJ-UHFFFAOYSA-N 4-[[5-chloro-2-[ethyl(methylsulfonyl)amino]phenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound ClC=1C=CC(=C(CNC2=NC(=CC3=C2C(=NN3)C(=O)N)C3=C(C=C(C(=C3)F)O)CC(F)(F)F)C1)N(S(=O)(=O)C)CC AGPZQPUPJARSNJ-UHFFFAOYSA-N 0.000 claims 1
- BIQHCRZPQPUHNT-UHFFFAOYSA-N 4-[[5-chloro-2-[ethyl(methylsulfonyl)amino]pyridin-3-yl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound ClC=1C=C(C(=NC1)N(S(=O)(=O)C)CC)CNC1=NC(=CC2=C1C(=NN2)C(=O)N)C2=C(C=C(C(=C2)F)O)CC(F)(F)F BIQHCRZPQPUHNT-UHFFFAOYSA-N 0.000 claims 1
- OQPWVPLYTPQQIY-UHFFFAOYSA-N 4-[[5-chloro-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound ClC=1C=CC(=C(CNC2=NC(=CC3=C2C(=NN3)C(=O)NC)C3=C(C=C(C(=C3)F)O)CC(F)(F)F)C1)N(S(=O)(=O)C)C OQPWVPLYTPQQIY-UHFFFAOYSA-N 0.000 claims 1
- KYZUYGBVLZMXTB-UHFFFAOYSA-N 4-[[5-chloro-2-[methyl(methylsulfonyl)amino]pyridin-3-yl]methylamino]-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound ClC=1C=C(C(=NC1)N(S(=O)(=O)C)C)CNC1=NC(=CC2=C1C(=NN2)C(=O)N)C2=C(C=C(C(=C2)F)O)CC(F)(F)F KYZUYGBVLZMXTB-UHFFFAOYSA-N 0.000 claims 1
- QWDYLODPTOMLDU-UHFFFAOYSA-N 4-chloro-3-[1-[6-(2-ethyl-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]azetidin-3-yl]oxybenzonitrile Chemical compound CCC1=CC(O)=CC=C1C1=NC(N2CC(C2)OC2=CC(=CC=C2Cl)C#N)=C2C=NNC2=C1 QWDYLODPTOMLDU-UHFFFAOYSA-N 0.000 claims 1
- COAUOAVYHZTIMG-UHFFFAOYSA-N 6-(2-cyclopropyl-5-fluoro-4-hydroxyphenyl)-N-methyl-4-[[2-[methyl(methylsulfonyl)amino]pyridin-3-yl]methylamino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C1(CC1)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCC=1C(=NC=CC1)N(S(=O)(=O)C)C)C(=NN2)C(=O)NC COAUOAVYHZTIMG-UHFFFAOYSA-N 0.000 claims 1
- VMCSVMRRMNTTNV-UHFFFAOYSA-N 6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)ethylamino]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCCC1=CC=C(C=C1)O)C(=NN2)C(=O)NC VMCSVMRRMNTTNV-UHFFFAOYSA-N 0.000 claims 1
- LNRYTDNWEWDQCY-UHFFFAOYSA-N 6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-4-[[2-[ethyl(methylsulfonyl)amino]phenyl]methylamino]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCC1=C(C=CC=C1)N(S(=O)(=O)C)CC)C(=NN2)C(=O)NC LNRYTDNWEWDQCY-UHFFFAOYSA-N 0.000 claims 1
- YFVIZNVKXROZSI-UHFFFAOYSA-N 6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-4-[[2-[ethylsulfonyl(methyl)amino]phenyl]methylamino]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCC1=C(C=CC=C1)N(C)S(=O)(=O)CC)C(=NN2)C(=O)NC YFVIZNVKXROZSI-UHFFFAOYSA-N 0.000 claims 1
- OFIWBEPUSOANRX-UHFFFAOYSA-N 6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-4-[[2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-N-(6-methylpyridin-3-yl)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCC1=C(C=CC=C1)N(S(=O)(=O)C)C)C(=NN2)C(=O)NC=2C=NC(=CC2)C OFIWBEPUSOANRX-UHFFFAOYSA-N 0.000 claims 1
- NBQIWMZOJLUOPZ-UHFFFAOYSA-N 6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-4-[[4-hydroxy-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCC1=C(C=C(C=C1)O)N(S(=O)(=O)C)C)C(=NN2)C(=O)N NBQIWMZOJLUOPZ-UHFFFAOYSA-N 0.000 claims 1
- LGAVUEXTUHVZEO-UHFFFAOYSA-N 6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-4-[[4-hydroxy-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCC1=C(C=C(C=C1)O)N(S(=O)(=O)C)C)C(=NN2)C(=O)NC LGAVUEXTUHVZEO-UHFFFAOYSA-N 0.000 claims 1
- IPHYEMRMCZKRFY-UHFFFAOYSA-N 6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-4-[[5-hydroxy-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-N-methyl-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCC1=C(C=CC(=C1)O)N(S(=O)(=O)C)C)C(=NN2)C(=O)NC IPHYEMRMCZKRFY-UHFFFAOYSA-N 0.000 claims 1
- SLDNTHWIALNKOG-UHFFFAOYSA-N 6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-N-methyl-4-(2-methylpropylamino)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCC(C)C)C(=NN2)C(=O)NC SLDNTHWIALNKOG-UHFFFAOYSA-N 0.000 claims 1
- GTGNVCWEJRBFQX-CQSZACIVSA-N 6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-N-methyl-4-[[(1R)-1-[2-[methyl(methylsulfonyl)amino]phenyl]ethyl]amino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)N[C@H](C)C1=C(C=CC=C1)N(S(=O)(=O)C)C)C(=NN2)C(=O)NC GTGNVCWEJRBFQX-CQSZACIVSA-N 0.000 claims 1
- GTGNVCWEJRBFQX-AWEZNQCLSA-N 6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-N-methyl-4-[[(1S)-1-[2-[methyl(methylsulfonyl)amino]phenyl]ethyl]amino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)N[C@@H](C)C1=C(C=CC=C1)N(S(=O)(=O)C)C)C(=NN2)C(=O)NC GTGNVCWEJRBFQX-AWEZNQCLSA-N 0.000 claims 1
- KZIWMYSRNRBZJV-UHFFFAOYSA-N 6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-N-methyl-4-[[2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCC1=C(C=CC=C1)N(S(=O)(=O)C)C)C(=NN2)C(=O)NC KZIWMYSRNRBZJV-UHFFFAOYSA-N 0.000 claims 1
- IOCOZGHPXHMJEK-UHFFFAOYSA-N 6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-N-methyl-4-[[2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-2H-pyrazolo[3,4-d]pyrimidine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=NC(=C2C(=N1)NN=C2C(=O)NC)NCC2=C(C=CC=C2)N(S(=O)(=O)C)C IOCOZGHPXHMJEK-UHFFFAOYSA-N 0.000 claims 1
- HUKBNTKAEHEDEF-UHFFFAOYSA-N 6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-N-methyl-4-[[2-[methyl(sulfamoyl)amino]phenyl]methylamino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCC1=C(C=CC=C1)N(S(N)(=O)=O)C)C(=NN2)C(=O)NC HUKBNTKAEHEDEF-UHFFFAOYSA-N 0.000 claims 1
- GLHCQBBMHMUVQE-UHFFFAOYSA-N 6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-N-methyl-4-[[5-methyl-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCC1=C(C=CC(=C1)C)N(S(=O)(=O)C)C)C(=NN2)C(=O)NC GLHCQBBMHMUVQE-UHFFFAOYSA-N 0.000 claims 1
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Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2948587C (en) | 2014-05-14 | 2018-07-17 | Pfizer Inc. | Pyrazolopyridines and pyrazolopyrimidines |
| TWI714528B (zh) | 2014-05-14 | 2021-01-01 | 瑞士商諾華公司 | 甲醯胺衍生物 |
| EP3712152B1 (en) | 2015-11-03 | 2021-01-13 | Topivert Pharma Limited | 4,5,6,7-tetrahydro-1h-imidazo[4,5-c]pyridine and 1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepine derivatives as janus kinase inhibitors |
| KR20180073687A (ko) * | 2015-11-03 | 2018-07-02 | 세라밴스 바이오파마 알앤디 아이피, 엘엘씨 | 호흡기 질환의 치료를 위한 jak 키나제 저해제 화합물 |
| EP3371185B1 (en) | 2015-11-03 | 2020-09-30 | Topivert Pharma Limited | 4,5,6,7-tetrahydro-1h-imidazo[4,5-c]pyridine and 1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepine derivatives as janus kinase inhibitors |
| AU2018231035B2 (en) | 2017-03-09 | 2021-09-09 | Theravance Biopharma R&D Ip, Llc | Fused imidazo-piperidine JAK inhibitors |
| JP7096268B2 (ja) | 2017-05-01 | 2022-07-05 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | Ｊａｋ阻害剤化合物の結晶形態 |
| EP3609498A1 (en) | 2017-05-01 | 2020-02-19 | Theravance Biopharma R&D IP, LLC | Methods of treatment using a jak inhibitor compound |
| AR111495A1 (es) | 2017-05-01 | 2019-07-17 | Theravance Biopharma R&D Ip Llc | Compuestos de imidazo-piperidina fusionada como inhibidores de jak |
| TW201920150A (zh) * | 2017-08-01 | 2019-06-01 | 美商施萬生物製藥研發 Ip有限責任公司 | 作為jak激酶抑制劑之吡唑并及三唑并雙環化合物 |
| BR112020008850A2 (pt) | 2017-11-03 | 2020-10-20 | Aclaris Therapeutics, Inc. | composto, composição farmacêutica e método para tratar uma doença mediada por jak1 e jak3 |
| CN119080779A (zh) | 2018-08-10 | 2024-12-06 | 阿克拉瑞斯治疗股份有限公司 | 吡咯并嘧啶itk抑制剂 |
| CN110833555B (zh) * | 2018-08-15 | 2023-03-24 | 广西梧州制药（集团）股份有限公司 | 吡唑并嘧啶衍生物在治疗溃疡性结肠炎的用途 |
| AU2019335199A1 (en) | 2018-09-04 | 2021-03-11 | Theravance Biopharma R&D Ip, Llc | Process for preparing jak inhibitors and intermediates thereof |
| US10836763B2 (en) | 2018-09-04 | 2020-11-17 | Theravance Biopharma R&D Ip, Llc | 5 to 7 membered heterocyclic amides as JAK inhibitors |
| JP7324836B2 (ja) | 2018-09-04 | 2023-08-10 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | Ｊａｋ阻害剤としてのジメチルアミノアゼチジンアミド |
| KR20210084512A (ko) | 2018-10-29 | 2021-07-07 | 세라밴스 바이오파마 알앤디 아이피, 엘엘씨 | Jak 억제제로서 2-아자비시클로 헥산 화합물 |
| CN113498352A (zh) | 2019-01-23 | 2021-10-12 | 施万生物制药研发Ip有限责任公司 | 作为jak抑制剂的咪唑并[1,5-a]吡啶、1,2,4-三唑并[4,3-a]吡啶和咪唑并[1,5-a]吡嗪 |
| HUE067145T2 (hu) * | 2019-02-25 | 2024-10-28 | Henan Medinno Pharmaceutical Tech Co Ltd | JAK inhibitor vegyület és alkalmazása |
| CN114075199A (zh) * | 2020-08-14 | 2022-02-22 | 河南迈英诺医药科技有限公司 | Jak抑制剂化合物及其用途 |
| CN114075200A (zh) * | 2020-08-14 | 2022-02-22 | 河南迈英诺医药科技有限公司 | 用于治疗重症肺炎的jak抑制剂化合物 |
| AU2020265828A1 (en) | 2019-05-02 | 2021-09-09 | Aclaris Therapeutics, Inc. | Substituted pyrrolopyridines as JAK inhibitors |
| WO2021022178A1 (en) * | 2019-07-31 | 2021-02-04 | Aclaris Therapeutics, Inc. | Substituted sulfonamide pyrrolopyridines as jak inhibitors |
| WO2021136345A1 (zh) * | 2019-12-30 | 2021-07-08 | 路良 | Jak抑制剂化合物及其用途 |
| CN113101975B (zh) * | 2020-01-13 | 2022-04-22 | 万华化学集团股份有限公司 | 一种多膦配体催化剂体系及其在乙烯齐聚反应的应用 |
| MX2022008627A (es) | 2020-01-13 | 2022-11-08 | Verge Analytics Inc | Pirazolo-pirimidinas sustituidas y usos de las mismas. |
| TW202144343A (zh) | 2020-03-02 | 2021-12-01 | 美商施萬生物製藥研發 Ip有限責任公司 | Jak抑制劑化合物之結晶水合物 |
| CN111548269B (zh) * | 2020-04-29 | 2023-10-27 | 兰州大学 | 一种二芳基甲烷结构化合物的制备方法 |
| GB202010408D0 (en) * | 2020-07-07 | 2020-08-19 | Reviral Ltd | Pharmaceutical compounds |
| WO2022053651A2 (en) | 2020-09-10 | 2022-03-17 | Precirix N.V. | Antibody fragment against fap |
| JP2024524214A (ja) | 2021-06-25 | 2024-07-05 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | Ｊａｋ阻害剤としてのイミダゾロインダゾール化合物 |
| CN115557947B (zh) * | 2021-07-02 | 2024-04-02 | 成都百裕制药股份有限公司 | 吡唑并[4,3-c]吡啶衍生物及其在医药上的应用 |
| CN113480543B (zh) * | 2021-07-07 | 2022-05-17 | 无锡市第二人民医院 | 2,6,8-多取代咪唑并[1,2-a]吡嗪及其合成方法和应用 |
| WO2023203135A1 (en) | 2022-04-22 | 2023-10-26 | Precirix N.V. | Improved radiolabelled antibody |
| IL318992A (en) | 2022-05-02 | 2025-04-01 | Precirix N V | Cancer treatment through advance directives |
| WO2025217560A1 (en) * | 2024-04-12 | 2025-10-16 | Theravance Biopharma R&D Ip, Llc | Triazolo indazole compounds as jak inhibitors |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| WO2000035298A1 (en) | 1996-11-27 | 2000-06-22 | Wm. Wrigley Jr. Company | Chewing gum containing medicament active agents |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| US20030139427A1 (en) * | 2002-08-23 | 2003-07-24 | Osi Pharmaceuticals Inc. | Bicyclic pyrimidinyl derivatives and methods of use thereof |
| EP1562898A1 (en) | 2002-11-19 | 2005-08-17 | Takeda Pharmaceutical Company Limited | Indole derivatives as somatostatin agonists or antagonists |
| US20080234262A1 (en) * | 2007-03-21 | 2008-09-25 | Wyeth | Pyrazolopyrimidine analogs and their use as mtor kinase and pi3 kinase inhibitors |
| JP4782239B2 (ja) | 2007-04-18 | 2011-09-28 | ファイザー・プロダクツ・インク | 異常細胞増殖治療のためのスルホニルアミド誘導体 |
| CN101883774A (zh) * | 2007-10-16 | 2010-11-10 | 惠氏有限责任公司 | 噻吩并嘧啶和吡唑并嘧啶化合物及其用作mtor激酶和pi3激酶抑制剂的用途 |
| JP2011503103A (ja) * | 2007-11-07 | 2011-01-27 | フォールドアールエックス ファーマシューティカルズ インコーポレーティッド | タンパク質輸送の調節方法 |
| US20090149458A1 (en) * | 2007-11-27 | 2009-06-11 | Wyeth | PYRROLO[3,2-d]PYRIMIDINE COMPOUNDS AND THEIR USE AS PI3 KINASE AND mTOR KINASE INHIBITORS |
| CN102014914A (zh) * | 2008-01-15 | 2011-04-13 | 惠氏有限责任公司 | 3h-[1,2,3]三唑并[4,5-d]嘧啶化合物、其作为mtor激酶和pi3激酶抑制剂的用途、以及它们的合成 |
| JP5608099B2 (ja) * | 2008-01-30 | 2014-10-15 | ジェネンテック， インコーポレイテッド | ピラゾロピリミジンｐｉ３ｋ阻害剤化合物および使用方法 |
| US8163743B2 (en) * | 2008-06-05 | 2012-04-24 | GlaxoGroupLimited | 4-carboxamide indazole derivatives useful as inhibitors of PI3-kinases |
| WO2009153261A1 (en) * | 2008-06-18 | 2009-12-23 | Solvay Pharmaceuticals Gmbh | HYDROXYPHENYL-SUBSTITUTED PYRROLO[2,3d]PYRIMIDINE DERIVATIVES, PROCESSES AND INTERMEDIATE PRODUCTS FOR THEIR PREPARATION AND MEDICAMENTS CONTAINING THESE COMPOUNDS |
| JPWO2010058846A1 (ja) | 2008-11-21 | 2012-04-19 | アステラス製薬株式会社 | ４，６−ジアミノニコチンアミド化合物 |
| US20100317646A1 (en) * | 2009-03-19 | 2010-12-16 | Medical Research Council Technology | Compounds |
| WO2012045195A1 (en) | 2010-10-09 | 2012-04-12 | Abbott Laboratories | Pyrrolopyrimidines as fak and alk inhibiters for treatment of cancers and other diseases |
| US8575336B2 (en) * | 2011-07-27 | 2013-11-05 | Pfizer Limited | Indazoles |
| CA2948587C (en) | 2014-05-14 | 2018-07-17 | Pfizer Inc. | Pyrazolopyridines and pyrazolopyrimidines |
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