JP2017515836A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- BPDPCRMNEGZLFA-UHFFFAOYSA-N 4-[[2-[ethyl(ethylsulfonyl)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)CC BPDPCRMNEGZLFA-UHFFFAOYSA-N 0.000 claims 1
- 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
- SSTDGUWFIWWWOY-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[2-[(3-hydroxyphenyl)sulfonyl-methylamino]phenyl]methylamino]-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)N(C)S(=O)(=O)C1=CC(=CC=C1)O)C(=NN2)C(=O)NC)CC(F)(F)F)O SSTDGUWFIWWWOY-UHFFFAOYSA-N 0.000 claims 1
- VIBLFDMXFZFHAT-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[2-[2-hydroxyethyl(methylsulfonyl)amino]phenyl]methylamino]-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)C)CCO)CC(F)(F)F)O VIBLFDMXFZFHAT-UHFFFAOYSA-N 0.000 claims 1
- OHJSXUGZVUQCOA-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[2-[2-hydroxyethyl(methylsulfonyl)amino]phenyl]methylamino]-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)N(S(=O)(=O)C)CCO)C(=NN2)C(=O)NC)CC(F)(F)F)O OHJSXUGZVUQCOA-UHFFFAOYSA-N 0.000 claims 1
- GFFJKARVAMIQEE-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[2-[2-methoxyethylsulfonyl(methyl)amino]phenyl]methylamino]-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)N(C)S(=O)(=O)CCOC)C(=NN2)C(=O)NC)CC(F)(F)F)O GFFJKARVAMIQEE-UHFFFAOYSA-N 0.000 claims 1
- IZAMCANGXNJSFB-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[2-[methyl(3-morpholin-4-ylpropylsulfonyl)amino]phenyl]methylamino]-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)CCCN1CCOCC1)C)C(=NN2)C(=O)N)CC(F)(F)F)O IZAMCANGXNJSFB-UHFFFAOYSA-N 0.000 claims 1
- WZBOJPGRAWGCAD-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-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)C)C)C(=NN2)C(=O)N)CC(F)(F)F)O WZBOJPGRAWGCAD-UHFFFAOYSA-N 0.000 claims 1
- VEWTZPFUPWZJAM-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-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)C)C)CC(F)(F)F)O VEWTZPFUPWZJAM-UHFFFAOYSA-N 0.000 claims 1
- GAPIQUXUWVOCGJ-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-N-(6-methylpyridin-3-yl)-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)C)C)C(=NN2)C(=O)NC=2C=NC(=CC2)C)CC(F)(F)F)O GAPIQUXUWVOCGJ-UHFFFAOYSA-N 0.000 claims 1
- RGWGGKUGOBJLKL-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[2-[methyl(methylsulfonyl)amino]pyridin-3-yl]methylamino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC=1C(=NC=CC1)N(S(=O)(=O)C)C)C(=NN2)C(=O)N)CC(F)(F)F)O RGWGGKUGOBJLKL-UHFFFAOYSA-N 0.000 claims 1
- ABQICQLAAZYVLN-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[2-[methyl-(6-methylpyridin-3-yl)sulfonylamino]phenyl]methylamino]-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)C=1C=NC(=CC1)C)C)C(=NN2)C(=O)N)CC(F)(F)F)O ABQICQLAAZYVLN-UHFFFAOYSA-N 0.000 claims 1
- BZENPXKJXYPNIH-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[2-fluoro-6-[methyl(methylsulfonyl)amino]phenyl]methylamino]-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=C1N(S(=O)(=O)C)C)F)C(=NN2)C(=O)NC)CC(F)(F)F)O BZENPXKJXYPNIH-UHFFFAOYSA-N 0.000 claims 1
- XGUJFKWJNPKJFG-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[4-hydroxy-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC1=C(C=C(C=C1)O)N(S(=O)(=O)C)C)C(=NN2)C(=O)N)CC(F)(F)F)O XGUJFKWJNPKJFG-UHFFFAOYSA-N 0.000 claims 1
- FALMJPFUCBVHKL-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[4-hydroxy-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-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=C(C=C1)O)N(S(=O)(=O)C)C)C(=NN2)C(=O)NC)CC(F)(F)F)O FALMJPFUCBVHKL-UHFFFAOYSA-N 0.000 claims 1
- FVSNUPHIAUYOMX-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[5-fluoro-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-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)F)N(S(=O)(=O)C)C)C(=NN2)C(=O)N)CC(F)(F)F)O FVSNUPHIAUYOMX-UHFFFAOYSA-N 0.000 claims 1
- YTUPKMRTOPNCOT-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[5-fluoro-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-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)F)N(S(=O)(=O)C)C)C(=NN2)C(=O)NC)CC(F)(F)F)O YTUPKMRTOPNCOT-UHFFFAOYSA-N 0.000 claims 1
- YFJCJTRBQHCXLT-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[5-fluoro-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-N-methyl-2H-pyrazolo[3,4-d]pyrimidine-3-carboxamide Chemical compound FC=1C=CC(=C(CNC2=C3C(=NC(=N2)C2=C(C=C(C(=C2)F)O)CC(F)(F)F)NN=C3C(=O)NC)C1)N(S(=O)(=O)C)C YFJCJTRBQHCXLT-UHFFFAOYSA-N 0.000 claims 1
- WLMZXCCBYNGDFJ-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[5-fluoro-2-[methyl(methylsulfonyl)amino]pyridin-3-yl]methylamino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC=1C(=NC=C(C1)F)N(S(=O)(=O)C)C)C(=NN2)C(=O)N)CC(F)(F)F)O WLMZXCCBYNGDFJ-UHFFFAOYSA-N 0.000 claims 1
- DLASUPFNNLSLRG-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[5-hydroxy-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-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)C)C)C(=NN2)C(=O)N)CC(F)(F)F)O DLASUPFNNLSLRG-UHFFFAOYSA-N 0.000 claims 1
- GLXGLDSWNNNCCD-UHFFFAOYSA-N 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]pyrimidine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=NC(=C2C(=N1)NN=C2C(=O)N)NCC2=C(C=CC(=C2)O)N(S(=O)(=O)C)C)CC(F)(F)F)O GLXGLDSWNNNCCD-UHFFFAOYSA-N 0.000 claims 1
- DMDLUSXJFJBYLZ-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-4-[[5-methyl-2-[methyl(methylsulfonyl)amino]pyridin-3-yl]methylamino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound CN(C1=NC=C(C)C=C1CNC1=C2C(NN=C2C(N)=O)=CC(=N1)C1=CC(F)=C(O)C=C1CC(F)(F)F)S(C)(=O)=O DMDLUSXJFJBYLZ-UHFFFAOYSA-N 0.000 claims 1
- ITFMLFRJDZKLQP-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-[6-(2-hydroxyethylamino)pyridin-3-yl]-4-[[5-hydroxy-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-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)C)C)C(=NN2)C(=O)NC=2C=NC(=CC2)NCCO)CC(F)(F)F)O ITFMLFRJDZKLQP-UHFFFAOYSA-N 0.000 claims 1
- ACPNNKQFKKBIQX-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-[6-(2-hydroxyethylamino)pyridin-3-yl]-4-[[5-hydroxy-2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-2H-pyrazolo[3,4-d]pyrimidine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=NC(=C2C(=N1)NN=C2C(=O)NC=2C=NC(=CC2)NCCO)NCC2=C(C=CC(=C2)O)N(S(=O)(=O)C)C)CC(F)(F)F)O ACPNNKQFKKBIQX-UHFFFAOYSA-N 0.000 claims 1
- SVRYJVCODHDAJL-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-4-(2-methylpropylamino)-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC(C)C)C(=NN2)C(=O)NC)CC(F)(F)F)O SVRYJVCODHDAJL-UHFFFAOYSA-N 0.000 claims 1
- ALGHXSFRWUBSAW-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-4-[[2-(sulfamoylmethyl)phenyl]methylamino]-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)CS(N)(=O)=O)C(=NN2)C(=O)NC)CC(F)(F)F)O ALGHXSFRWUBSAW-UHFFFAOYSA-N 0.000 claims 1
- YTDNMQPIDMGVDR-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-4-[[2-[methyl(methylsulfamoyl)amino]phenyl]methylamino]-2H-pyrazolo[3,4-d]pyrimidine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=NC(=C2C(=N1)NN=C2C(=O)NC)NCC2=C(C=CC=C2)N(S(NC)(=O)=O)C)CC(F)(F)F)O YTDNMQPIDMGVDR-UHFFFAOYSA-N 0.000 claims 1
- YJSHIGLIYUPAIT-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-4-[[2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-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)C)C)C(=NN2)C(=O)NC)CC(F)(F)F)O YJSHIGLIYUPAIT-UHFFFAOYSA-N 0.000 claims 1
- CTIGWPUYJNZPKR-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-4-[[2-[methyl(methylsulfonyl)amino]phenyl]methylamino]-2H-pyrazolo[3,4-d]pyrimidine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=NC(=C2C(=N1)NN=C2C(=O)NC)NCC2=C(C=CC=C2)N(S(=O)(=O)C)C)CC(F)(F)F)O CTIGWPUYJNZPKR-UHFFFAOYSA-N 0.000 claims 1
- YLPWYGHYVHZHHC-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-4-[[2-[methyl(methylsulfonyl)amino]pyridin-3-yl]methylamino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC=1C(=NC=CC1)N(S(=O)(=O)C)C)C(=NN2)C(=O)NC)CC(F)(F)F)O YLPWYGHYVHZHHC-UHFFFAOYSA-N 0.000 claims 1
- BBQPXRWWGFVMOX-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-4-[[2-[methyl(pyridin-3-ylsulfonyl)amino]phenyl]methylamino]-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)C=1C=NC=CC1)C)C(=NN2)C(=O)NC)CC(F)(F)F)O BBQPXRWWGFVMOX-UHFFFAOYSA-N 0.000 claims 1
- BRQCTFOAORTYKM-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-4-[[2-[methyl(sulfamoyl)amino]phenyl]methylamino]-2H-pyrazolo[3,4-d]pyrimidine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=NC(=C2C(=N1)NN=C2C(=O)NC)NCC2=C(C=CC=C2)N(S(N)(=O)=O)C)CC(F)(F)F)O BRQCTFOAORTYKM-UHFFFAOYSA-N 0.000 claims 1
- CVAKSHSZMWJDKV-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-4-[[2-[methyl-(6-methylpyridin-3-yl)sulfonylamino]phenyl]methylamino]-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)C=1C=NC(=CC1)C)C)C(=NN2)C(=O)NC)CC(F)(F)F)O CVAKSHSZMWJDKV-UHFFFAOYSA-N 0.000 claims 1
- FYFZJBPUSMVYQV-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-4-[[3-[methyl(methylsulfonyl)amino]pyrazin-2-yl]methylamino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound FC=1C(=CC(=C(C=1)C1=CC2=C(C(=N1)NCC1=NC=CN=C1N(S(=O)(=O)C)C)C(=NN2)C(=O)NC)CC(F)(F)F)O FYFZJBPUSMVYQV-UHFFFAOYSA-N 0.000 claims 1
- CNLKMAASBAEKQE-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-4-[[3-[methyl(methylsulfonyl)amino]pyrazin-2-yl]methylamino]-2H-pyrazolo[3,4-d]pyrimidine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=NC(=C2C(=N1)NN=C2C(=O)NC)NCC2=NC=CN=C2N(S(=O)(=O)C)C)CC(F)(F)F)O CNLKMAASBAEKQE-UHFFFAOYSA-N 0.000 claims 1
- LJUBVCFXZLDDMF-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-4-[[3-[methyl(methylsulfonyl)amino]pyridin-2-yl]methylamino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC1=NC=CC=C1N(S(=O)(=O)C)C)C(=NN2)C(=O)NC)CC(F)(F)F)O LJUBVCFXZLDDMF-UHFFFAOYSA-N 0.000 claims 1
- ILQBVOMILHZYSA-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-4-[[4-[methyl(methylsulfonyl)amino]pyridin-3-yl]methylamino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC=1C=NC=CC1N(S(=O)(=O)C)C)C(=NN2)C(=O)NC)CC(F)(F)F)O ILQBVOMILHZYSA-UHFFFAOYSA-N 0.000 claims 1
- IASHJKDORLDCHI-UHFFFAOYSA-N 6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-N-methyl-4-[[5-methyl-2-[methyl(methylsulfonyl)amino]pyridin-3-yl]methylamino]-1H-pyrazolo[4,3-c]pyridine-3-carboxamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC=1C(=NC=C(C1)C)N(S(=O)(=O)C)C)C(=NN2)C(=O)NC)CC(F)(F)F)O IASHJKDORLDCHI-UHFFFAOYSA-N 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000000884 Airway Obstruction Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010003645 Atopy Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 206010048962 Brain oedema Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- 206010006482 Bronchospasm Diseases 0.000 claims 1
- WLSGICXJGRNXSD-UHFFFAOYSA-N CCC(C=C(C(F)=C1)O)=C1C1=CC(NN=C2)=C2C(NCC2=C(CS(NC)(=O)=O)C=CC=C2)=N1 Chemical compound CCC(C=C(C(F)=C1)O)=C1C1=CC(NN=C2)=C2C(NCC2=C(CS(NC)(=O)=O)C=CC=C2)=N1 WLSGICXJGRNXSD-UHFFFAOYSA-N 0.000 claims 1
- 241000222122 Candida albicans Species 0.000 claims 1
- 206010007134 Candida infections Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 208000005171 Dysmenorrhea Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 206010018634 Gouty Arthritis Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
- 208000016300 Idiopathic chronic eosinophilic pneumonia Diseases 0.000 claims 1
- 206010061216 Infarction Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000000112 Myalgia Diseases 0.000 claims 1
- XONBARUEJCFVDL-UHFFFAOYSA-N N-[2-(dimethylamino)ethyl]-2-[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]-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound CN(C)CCNC(=O)N1CCc2nc([nH]c2C1)-c1[nH]nc2nc(nc(NCc3cc(O)ccc3N(C)S(C)(=O)=O)c12)-c1cc(F)c(O)cc1CC(F)(F)F XONBARUEJCFVDL-UHFFFAOYSA-N 0.000 claims 1
- AFPLYFPFUPHZMR-UHFFFAOYSA-N N-[2-[6-(2-ethyl-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]-3,4-dihydro-1H-isoquinolin-5-yl]methanesulfonamide formic acid Chemical compound C(=O)O.C(C)C1=C(C=CC(=C1)O)C1=CC2=C(C(=N1)N1CC3=CC=CC(=C3CC1)NS(=O)(=O)C)C=NN2 AFPLYFPFUPHZMR-UHFFFAOYSA-N 0.000 claims 1
- BNFVZQQKLUNCFL-UHFFFAOYSA-N N-[2-[[2-(3,4-dimethoxyphenyl)ethyl-[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]-N-methylmethanesulfonamide hydrochloride Chemical compound Cl.COC=1C=C(C=CC1OC)CCN(C1=NC(=CC2=C1C=NN2)C2=C(C=C(C(=C2)F)O)CC)CC2=C(C=CC=C2)N(S(=O)(=O)C)C BNFVZQQKLUNCFL-UHFFFAOYSA-N 0.000 claims 1
- WZULFGLWRRTFDD-UHFFFAOYSA-N N-[2-[[[3-(4,5-dimethyl-1H-imidazol-2-yl)-6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]-N-methylmethanesulfonamide Chemical compound CC=1N=C(NC1C)C1=NNC2=C1C(=NC(=C2)C2=C(C=C(C(=C2)F)O)CC)NCC2=C(C=CC=C2)N(S(=O)(=O)C)C WZULFGLWRRTFDD-UHFFFAOYSA-N 0.000 claims 1
- FDPKESOBEFZQRO-UHFFFAOYSA-N N-[2-[[[3-(5-acetyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-2-yl)-6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-2H-pyrazolo[3,4-d]pyrimidin-4-yl]amino]methyl]-4-hydroxyphenyl]-N-methylmethanesulfonamide Chemical compound CN(C1=CC=C(O)C=C1CNC1=C2C(NN=C2C2=NC3=C(CCN(C3)C(C)=O)N2)=NC(=N1)C1=CC(F)=C(O)C=C1CC(F)(F)F)S(C)(=O)=O FDPKESOBEFZQRO-UHFFFAOYSA-N 0.000 claims 1
- PKZMHAUKZNLATM-UHFFFAOYSA-N N-[2-[[[6-(2-ethyl-4-hydroxy-6-methylphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]-N-methylmethanesulfonamide Chemical compound C(C)C1=C(C(=CC(=C1)O)C)C1=CC2=C(C(=N1)NCC1=C(C=CC=C1)N(S(=O)(=O)C)C)C=NN2 PKZMHAUKZNLATM-UHFFFAOYSA-N 0.000 claims 1
- PRTNMIOJOGYKDQ-UHFFFAOYSA-N N-[2-[[[6-(2-ethyl-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]-3-methylphenyl]-N-methylmethanesulfonamide Chemical compound CCc1cc(O)ccc1-c1cc2[nH]ncc2c(NCc2c(C)cccc2N(C)S(C)(=O)=O)n1 PRTNMIOJOGYKDQ-UHFFFAOYSA-N 0.000 claims 1
- IYPWKCDAGXWKTK-UHFFFAOYSA-N N-[2-[[[6-(2-ethyl-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]-N-methylmethanesulfonamide hydrochloride Chemical compound Cl.C(C)C1=C(C=CC(=C1)O)C1=CC2=C(C(=N1)NCC1=C(C=CC=C1)N(S(=O)(=O)C)C)C=NN2 IYPWKCDAGXWKTK-UHFFFAOYSA-N 0.000 claims 1
- YQRRCRKOWPMKKB-UHFFFAOYSA-N N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]amino]methyl]phenyl]-N-methylmethanesulfonamide hydrochloride Chemical compound Cl.C(C)C1=C(C=C(C(=C1)O)F)C1=NC(=C2C(=N1)NN=C2)NCC2=C(C=CC=C2)N(S(=O)(=O)C)C YQRRCRKOWPMKKB-UHFFFAOYSA-N 0.000 claims 1
- DLRRKWRHEGCCOS-UHFFFAOYSA-N N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]-methylamino]methyl]phenyl]-N-methylmethanesulfonamide hydrochloride Chemical compound Cl.C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)N(C)CC1=C(C=CC=C1)N(S(=O)(=O)C)C)C=NN2 DLRRKWRHEGCCOS-UHFFFAOYSA-N 0.000 claims 1
- BMZPTDVPNTYCJK-UHFFFAOYSA-N N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]-propylamino]methyl]-4-methylphenyl]-N-methylmethanesulfonamide Chemical compound C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)N(CCC)CC1=C(C=CC(=C1)C)N(S(=O)(=O)C)C)C=NN2 BMZPTDVPNTYCJK-UHFFFAOYSA-N 0.000 claims 1
- UVUFBQMWXOMULF-UHFFFAOYSA-N N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]-N-(2-hydroxyethyl)methanesulfonamide 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)CCO)C=NN2 UVUFBQMWXOMULF-UHFFFAOYSA-N 0.000 claims 1
- SKJBDRHSNRVMMZ-UHFFFAOYSA-N N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]-N-methylethanesulfonamide hydrochloride Chemical compound Cl.C(C)C1=C(C=C(C(=C1)O)F)C1=CC2=C(C(=N1)NCC1=C(C=CC=C1)N(S(=O)(=O)CC)C)C=NN2 SKJBDRHSNRVMMZ-UHFFFAOYSA-N 0.000 claims 1
- SVPLUHZQTZJNAJ-UHFFFAOYSA-N N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]-N-propylmethanesulfonamide 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)CCC)C=NN2 SVPLUHZQTZJNAJ-UHFFFAOYSA-N 0.000 claims 1
- BEEJICRDGFYLFA-UHFFFAOYSA-N N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-3-(1H-imidazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]-N-methylmethanesulfonamide 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=2NC=CN2 BEEJICRDGFYLFA-UHFFFAOYSA-N 0.000 claims 1
- LQAXEHYPRXVRIJ-UHFFFAOYSA-N N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-3-(5-methyl-1H-imidazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]-N-methylmethanesulfonamide 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=2NC=C(N2)C LQAXEHYPRXVRIJ-UHFFFAOYSA-N 0.000 claims 1
- UBUCJPDCTYNDHN-UHFFFAOYSA-N N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-3-pyrazol-1-yl-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]-N-methylmethanesulfonamide 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)N2N=CC=C2 UBUCJPDCTYNDHN-UHFFFAOYSA-N 0.000 claims 1
- OCHNNQQTHRHVOJ-UHFFFAOYSA-N N-[2-[[[6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-1H-pyrazolo[4,3-c]pyridin-4-yl]-methylamino]methyl]phenyl]-N-methylmethanesulfonamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)N(C)CC1=C(C=CC=C1)N(S(=O)(=O)C)C)C=NN2)CC(F)(F)F)O OCHNNQQTHRHVOJ-UHFFFAOYSA-N 0.000 claims 1
- JXOXUJYWERDDED-UHFFFAOYSA-N N-[2-[[[6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]-4-methylphenyl]-N-methylmethanesulfonamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC1=C(C=CC(=C1)C)N(S(=O)(=O)C)C)C=NN2)CC(F)(F)F)O JXOXUJYWERDDED-UHFFFAOYSA-N 0.000 claims 1
- BAOKZYRJYNKFFE-UHFFFAOYSA-N N-[2-[[[6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]-N-methylmethanesulfonamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC1=C(C=CC=C1)N(S(=O)(=O)C)C)C=NN2)CC(F)(F)F)O BAOKZYRJYNKFFE-UHFFFAOYSA-N 0.000 claims 1
- OXKQPGPWFAXWHG-UHFFFAOYSA-N N-[2-[[[6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-3-(5-methyl-1H-1,2,4-triazol-3-yl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]-N-methylmethanesulfonamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC1=C(C=CC=C1)N(S(=O)(=O)C)C)C(=NN2)C2=NN=C(N2)C)CC(F)(F)F)O OXKQPGPWFAXWHG-UHFFFAOYSA-N 0.000 claims 1
- AGUMKAOMHYENGL-UHFFFAOYSA-N N-[2-[[[6-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-3-pyrazol-1-yl-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]-N-methylmethanesulfonamide Chemical compound FC=1C(=CC(=C(C1)C1=CC2=C(C(=N1)NCC1=C(C=CC=C1)N(S(=O)(=O)C)C)C(=NN2)N2N=CC=C2)CC(F)(F)F)O AGUMKAOMHYENGL-UHFFFAOYSA-N 0.000 claims 1
- TZKUPTPHFBSWOE-UHFFFAOYSA-N N-[2-[[[6-amino-2-[5-fluoro-4-hydroxy-2-(2,2,2-trifluoroethyl)phenyl]-5-(4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-2-carboximidoyl)pyrimidin-4-yl]amino]methyl]-4-hydroxyphenyl]-N-methylmethanesulfonamide Chemical compound CN(c1ccc(O)cc1CNc1nc(nc(N)c1C(=N)c1nc2CCNCc2[nH]1)-c1cc(F)c(O)cc1CC(F)(F)F)S(C)(=O)=O TZKUPTPHFBSWOE-UHFFFAOYSA-N 0.000 claims 1
- GOWSWSWWCGQTIR-UHFFFAOYSA-N N-[2-[[ethyl-[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]-4-methylphenyl]-N-methylmethanesulfonamide Chemical compound C(C)N(C1=NC(=CC2=C1C=NN2)C2=C(C=C(C(=C2)F)O)CC)CC2=C(C=CC(=C2)C)N(S(=O)(=O)C)C GOWSWSWWCGQTIR-UHFFFAOYSA-N 0.000 claims 1
- JQXNVZJPDDQDGO-UHFFFAOYSA-N N-[4-[2-[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]-[[2-[methyl(methylsulfonyl)amino]phenyl]methyl]amino]ethyl]phenyl]methanesulfonamide hydrochloride Chemical compound Cl.CCc1cc(O)c(F)cc1-c1cc2[nH]ncc2c(n1)N(CCc1ccc(NS(C)(=O)=O)cc1)Cc1ccccc1N(C)S(C)(=O)=O JQXNVZJPDDQDGO-UHFFFAOYSA-N 0.000 claims 1
- ILCNZXQJMVPCQE-UHFFFAOYSA-N N-[4-chloro-2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]-N-methylmethanesulfonamide hydrochloride Chemical compound Cl.ClC1=CC(=C(C=C1)N(S(=O)(=O)C)C)CNC1=NC(=CC2=C1C=NN2)C2=C(C=C(C(=C2)F)O)CC ILCNZXQJMVPCQE-UHFFFAOYSA-N 0.000 claims 1
- OYAQOINYWAAURV-UHFFFAOYSA-N N-benzyl-2-[6-(2-ethyl-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]-3,4-dihydro-1H-isoquinoline-5-carboxamide Chemical compound CCC1=CC(O)=CC=C1C1=NC(N2CCC3=C(C2)C=CC=C3C(=O)NCC2=CC=CC=C2)=C2C=NNC2=C1 OYAQOINYWAAURV-UHFFFAOYSA-N 0.000 claims 1
- FLQXDWBNLQNAKN-UHFFFAOYSA-N N-butyl-N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]methanesulfonamide Chemical compound C(CCC)N(S(=O)(=O)C)C1=C(C=CC=C1)CNC1=NC(=CC2=C1C=NN2)C2=C(C=C(C(=C2)F)O)CC FLQXDWBNLQNAKN-UHFFFAOYSA-N 0.000 claims 1
- XMLDADRUZCWXPO-UHFFFAOYSA-N N-ethyl-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)NC(=O)C1=NNC2=C1C(=NC(=C2)C2=C(C=C(C(=C2)F)O)CC(F)(F)F)NCC2=NC=CN=C2N(S(=O)(=O)C)CC XMLDADRUZCWXPO-UHFFFAOYSA-N 0.000 claims 1
- ISHGHOIPAQNGDU-UHFFFAOYSA-N N-ethyl-N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]-methylamino]methyl]-4-methylphenyl]methanesulfonamide Chemical compound C(C)N(S(=O)(=O)C)C1=C(C=C(C=C1)C)CN(C)C1=NC(=CC2=C1C=NN2)C2=C(C=C(C(=C2)F)O)CC ISHGHOIPAQNGDU-UHFFFAOYSA-N 0.000 claims 1
- OADJPANQYFMKJV-UHFFFAOYSA-N N-ethyl-N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]-methylamino]methyl]phenyl]methanesulfonamide hydrochloride Chemical compound Cl.C(C)N(S(=O)(=O)C)C1=C(C=CC=C1)CN(C)C1=NC(=CC2=C1C=NN2)C2=C(C=C(C(=C2)F)O)CC OADJPANQYFMKJV-UHFFFAOYSA-N 0.000 claims 1
- SNOHDVRRWIEMML-UHFFFAOYSA-N N-ethyl-N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]ethanesulfonamide hydrochloride Chemical compound Cl.C(C)N(S(=O)(=O)CC)C1=C(C=CC=C1)CNC1=NC(=CC2=C1C=NN2)C2=C(C=C(C(=C2)F)O)CC SNOHDVRRWIEMML-UHFFFAOYSA-N 0.000 claims 1
- OHJZQNUSVLPWKN-UHFFFAOYSA-N N-ethyl-N-[2-[[[6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]amino]methyl]phenyl]methanesulfonamide Chemical compound C(C)N(S(=O)(=O)C)C1=C(C=CC=C1)CNC1=NC(=CC2=C1C=NN2)C2=C(C=C(C(=C2)F)O)CC OHJZQNUSVLPWKN-UHFFFAOYSA-N 0.000 claims 1
- 206010028735 Nasal congestion Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims 1
- 208000011191 Pulmonary vascular disease Diseases 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 208000002200 Respiratory Hypersensitivity Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038910 Retinitis Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 206010039094 Rhinitis perennial Diseases 0.000 claims 1
- 208000036071 Rhinorrhea Diseases 0.000 claims 1
- 206010039101 Rhinorrhoea Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 201000010001 Silicosis Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 206010042496 Sunburn Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046914 Vaginal infection Diseases 0.000 claims 1
- 201000008100 Vaginitis Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- PAEPZXVORXSCRP-UHFFFAOYSA-N [3-ethyl-4-[4-(3-phenoxyazetidin-1-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]phenyl] formate Chemical compound C(=O)OC1=CC(=C(C=C1)C1=CC2=C(C(=N1)N1CC(C1)OC1=CC=CC=C1)C=NN2)CC PAEPZXVORXSCRP-UHFFFAOYSA-N 0.000 claims 1
- RKXXPUWGONIRST-UHFFFAOYSA-N [3-ethyl-4-[4-[2-(4-phenylphenyl)ethylamino]-1H-pyrazolo[4,3-c]pyridin-6-yl]phenyl] formate Chemical compound C(=O)OC1=CC(=C(C=C1)C1=CC2=C(C(=N1)NCCC1=CC=C(C=C1)C1=CC=CC=C1)C=NN2)CC RKXXPUWGONIRST-UHFFFAOYSA-N 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 206010069351 acute lung injury Diseases 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 230000010085 airway hyperresponsiveness Effects 0.000 claims 1
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 208000006752 brain edema Diseases 0.000 claims 1
- 201000009267 bronchiectasis Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 230000007885 bronchoconstriction Effects 0.000 claims 1
- 125000006309 butyl amino group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 201000003984 candidiasis Diseases 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 201000009323 chronic eosinophilic pneumonia Diseases 0.000 claims 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000005713 exacerbation Effects 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 238000011010 flushing procedure Methods 0.000 claims 1
- 230000007574 infarction Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 238000002483 medication Methods 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000013465 muscle pain Diseases 0.000 claims 1
- 201000006938 muscular dystrophy Diseases 0.000 claims 1
- 210000004165 myocardium Anatomy 0.000 claims 1
- JVWBPNRQROCNMH-UHFFFAOYSA-N n-methyl-1h-pyrazole-4-sulfonamide Chemical compound CNS(=O)(=O)C=1C=NNC=1 JVWBPNRQROCNMH-UHFFFAOYSA-N 0.000 claims 1
- 201000008383 nephritis Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 230000003959 neuroinflammation Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 208000005987 polymyositis Diseases 0.000 claims 1
- 201000003651 pulmonary sarcoidosis Diseases 0.000 claims 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 230000035939 shock Effects 0.000 claims 1
- 201000009890 sinusitis Diseases 0.000 claims 1
- 201000005671 spondyloarthropathy Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 239000003053 toxin Substances 0.000 claims 1
- 231100000765 toxin Toxicity 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461993138P | 2014-05-14 | 2014-05-14 | |
| US61/993,138 | 2014-05-14 | ||
| PCT/IB2015/053174 WO2015173683A1 (en) | 2014-05-14 | 2015-04-30 | Pyrazolopyridines and pyrazolopyrimidines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017515836A JP2017515836A (ja) | 2017-06-15 |
| JP2017515836A5 true JP2017515836A5 (enExample) | 2018-05-31 |
| JP6663857B2 JP6663857B2 (ja) | 2020-03-13 |
Family
ID=53264695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016567364A Expired - Fee Related JP6663857B2 (ja) | 2014-05-14 | 2015-04-30 | ピラゾロピリジンおよびピラゾロピリミジン |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US9518052B2 (enExample) |
| EP (1) | EP3143021B1 (enExample) |
| JP (1) | JP6663857B2 (enExample) |
| KR (1) | KR20170002623A (enExample) |
| CN (1) | CN106459048A (enExample) |
| AP (1) | AP2016009562A0 (enExample) |
| AR (1) | AR100438A1 (enExample) |
| AU (1) | AU2015260905A1 (enExample) |
| CA (1) | CA2948587C (enExample) |
| CL (1) | CL2016002888A1 (enExample) |
| CR (1) | CR20160525A (enExample) |
| CU (1) | CU20160167A7 (enExample) |
| DO (1) | DOP2016000298A (enExample) |
| EA (1) | EA201650029A1 (enExample) |
| EC (1) | ECSP16087271A (enExample) |
| ES (1) | ES2737696T3 (enExample) |
| GE (2) | GEP20186921B (enExample) |
| IL (1) | IL248970A0 (enExample) |
| MD (1) | MD20160121A2 (enExample) |
| MX (1) | MX2016014878A (enExample) |
| NI (1) | NI201600170A (enExample) |
| PE (1) | PE20161475A1 (enExample) |
| PH (1) | PH12016502228A1 (enExample) |
| SG (1) | SG11201609139WA (enExample) |
| SV (1) | SV2016005318A (enExample) |
| TN (1) | TN2016000503A1 (enExample) |
| TW (1) | TWI591067B (enExample) |
| UY (1) | UY36121A (enExample) |
| WO (1) | WO2015173683A1 (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170002623A (ko) | 2014-05-14 | 2017-01-06 | 화이자 인코포레이티드 | 피라졸로피리딘 및 피라졸로피리미딘 |
| US9403810B2 (en) | 2014-05-14 | 2016-08-02 | Novartis Ag | Carboxamide derivatives |
| WO2017077283A1 (en) | 2015-11-03 | 2017-05-11 | 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 |
| DK3371185T3 (da) | 2015-11-03 | 2020-11-30 | Topivert Pharma Ltd | 4,5,6,7-tetrahydro-1h-imidazo[4,5-c]pyridin og 1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepinderivater som janus-kinase-inhibitorer |
| UA123633C2 (uk) * | 2015-11-03 | 2021-05-05 | Тереванс Байофарма Ар Енд Ді Айпі, Елелсі | Сполуки інгібітору jak-кінази для лікування респіраторного захворювання |
| WO2018165392A1 (en) | 2017-03-09 | 2018-09-13 | Theravance Biopharma R&D Ip, Llc | Jak inhibitors containing a 4-membered heterocyclic amide |
| WO2018204233A1 (en) | 2017-05-01 | 2018-11-08 | Theravance Biopharma R&D Ip, Llc | Methods of treatment using a jak inhibitor compound |
| KR20200003121A (ko) | 2017-05-01 | 2020-01-08 | 세라밴스 바이오파마 알앤디 아이피, 엘엘씨 | Jak 저해제 화합물의 결정형 |
| AR111495A1 (es) | 2017-05-01 | 2019-07-17 | Theravance Biopharma R&D Ip Llc | Compuestos de imidazo-piperidina fusionada como inhibidores de jak |
| AU2018312349A1 (en) | 2017-08-01 | 2020-02-06 | Theravance Biopharma R&D Ip, Llc | Pyrazolo and triazolo bicyclic compounds as JAK kinase inhibitors |
| KR102821964B1 (ko) | 2017-11-03 | 2025-06-19 | 어클라리스 쎄라퓨틱스, 인코포레이티드 | 치환된 피롤로피리미딘 jak 억제제 및 이의 제조 및 사용 방법 |
| US11554120B2 (en) * | 2018-08-03 | 2023-01-17 | Bristol-Myers Squibb Company | 1H-pyrazolo[4,3-d]pyrimidine compounds as toll-like receptor 7 (TLR7) agonists and methods and uses therefor |
| 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 |
| FI3837258T3 (fi) | 2018-09-04 | 2024-05-27 | Theravance Biopharma R&D Ip Llc | Dimetyyliaminoatsetidiiniamideja jak-estäjinä |
| JP2021535176A (ja) | 2018-09-04 | 2021-12-16 | 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阻害剤およびその中間体を調製するためのプロセス |
| UA127328C2 (uk) | 2018-09-04 | 2023-07-19 | Тереванс Байофарма Ар Енд Ді Айпі, Елелсі | 5-7-членні гетероциклічні аміди як інгібітори jak |
| 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 |
| CN114075199B (zh) * | 2020-08-14 | 2026-03-10 | 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 |
| CA3138544A1 (en) | 2019-05-02 | 2020-11-05 | Aclaris Therapeutics, Inc. | Substituted pyrrolopyridines as jak inhibitors |
| US20220235043A1 (en) * | 2019-07-31 | 2022-07-28 | Aclaris Therapeutics, Inc. | Substituted sulfonamide pyrrolopyridines as jak inhibitors |
| JP7580136B2 (ja) * | 2019-12-30 | 2024-11-11 | 路良 | Ｊａｋ阻害剤化合物及びその使用 |
| TWI885039B (zh) | 2020-01-13 | 2025-06-01 | 美商邊際分析公司 | 經取代吡唑并嘧啶及其用途 |
| 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 |
| 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 |
| JP2023541601A (ja) | 2020-09-10 | 2023-10-03 | プレシリックス・ナームローゼ・ベンノートシヤープ | Ｆａｐに対する抗体フラグメント |
| EP4359402B1 (en) | 2021-06-25 | 2026-03-11 | Theravance Biopharma R&D IP, LLC | Imidazolo indazole compounds as jak inhibitors |
| 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 |
| AU2023264245A1 (en) | 2022-05-02 | 2024-12-19 | Precirix N.V. | Pre-targeting |
| WO2025217560A1 (en) * | 2024-04-12 | 2025-10-16 | Theravance Biopharma R&D Ip, Llc | Triazolo indazole compounds as jak inhibitors |
| WO2025240333A1 (en) * | 2024-05-13 | 2025-11-20 | The Texas A&M University System | Jak3 targeted smart drugs and uses thereof |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| WO2000035296A1 (en) | 1996-11-27 | 2000-06-22 | Wm. Wrigley Jr. Company | Improved release of medicament active agents from a chewing gum coating |
| 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 |
| WO2004046107A1 (en) | 2002-11-19 | 2004-06-03 | 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 |
| CN101678215B (zh) | 2007-04-18 | 2014-10-01 | 辉瑞产品公司 | 用于治疗异常细胞生长的磺酰胺衍生物 |
| EA201000484A1 (ru) * | 2007-10-16 | 2010-12-30 | ВАЙЕТ ЭлЭлСи | Тиенопиримидиновые и пиразолопиримидиновые соединения и их применение в качестве ингибиторов киназы mtor и киназы pi3 |
| CA2705303A1 (en) * | 2007-11-07 | 2009-05-14 | Foldrx Pharmaceuticals, Inc. | Modulation of protein trafficking |
| 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 |
| CA2712267A1 (en) * | 2008-01-15 | 2009-07-23 | Wyeth Llc | 3h-[1,2,3]triazolo[4,5-d]pyrimidine compounds, their use as mtor kinase and pi3 kinase inhibitors, and their syntheses |
| US8987280B2 (en) * | 2008-01-30 | 2015-03-24 | Genentech, Inc. | Pyrazolopyrimidine PI3K inhibitor compounds and methods of use |
| 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 |
| EP2361902A4 (en) | 2008-11-21 | 2012-04-25 | Astellas Pharma Inc | 4,6-DIAMINONICOTINSÄUREAMIDVERBINDUNG |
| EP2408772B1 (en) * | 2009-03-19 | 2015-07-01 | 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 |
| KR20170002623A (ko) | 2014-05-14 | 2017-01-06 | 화이자 인코포레이티드 | 피라졸로피리딘 및 피라졸로피리미딘 |
-
2015
- 2015-04-30 KR KR1020167034627A patent/KR20170002623A/ko not_active Ceased
- 2015-04-30 PE PE2016002225A patent/PE20161475A1/es not_active Application Discontinuation
- 2015-04-30 EP EP15724365.0A patent/EP3143021B1/en active Active
- 2015-04-30 EA EA201650029A patent/EA201650029A1/ru unknown
- 2015-04-30 CN CN201580036211.3A patent/CN106459048A/zh active Pending
- 2015-04-30 MX MX2016014878A patent/MX2016014878A/es unknown
- 2015-04-30 MD MDA20160121A patent/MD20160121A2/ro not_active Application Discontinuation
- 2015-04-30 TN TN2016000503A patent/TN2016000503A1/en unknown
- 2015-04-30 GE GEAP201514322A patent/GEP20186921B/en unknown
- 2015-04-30 AU AU2015260905A patent/AU2015260905A1/en not_active Abandoned
- 2015-04-30 CA CA2948587A patent/CA2948587C/en not_active Expired - Fee Related
- 2015-04-30 GE GEAP201814322A patent/GEAP201814322A/en unknown
- 2015-04-30 CR CR20160525A patent/CR20160525A/es unknown
- 2015-04-30 SG SG11201609139WA patent/SG11201609139WA/en unknown
- 2015-04-30 AP AP2016009562A patent/AP2016009562A0/en unknown
- 2015-04-30 JP JP2016567364A patent/JP6663857B2/ja not_active Expired - Fee Related
- 2015-04-30 ES ES15724365T patent/ES2737696T3/es active Active
- 2015-04-30 WO PCT/IB2015/053174 patent/WO2015173683A1/en not_active Ceased
- 2015-05-13 US US14/710,631 patent/US9518052B2/en active Active
- 2015-05-13 AR ARP150101493A patent/AR100438A1/es unknown
- 2015-05-13 TW TW104115312A patent/TWI591067B/zh not_active IP Right Cessation
- 2015-05-13 UY UY0001036121A patent/UY36121A/es not_active Application Discontinuation
-
2016
- 2016-11-03 US US15/342,601 patent/US10022376B2/en active Active
- 2016-11-09 PH PH12016502228A patent/PH12016502228A1/en unknown
- 2016-11-11 DO DO2016000298A patent/DOP2016000298A/es unknown
- 2016-11-11 EC ECIEPI201687271A patent/ECSP16087271A/es unknown
- 2016-11-11 SV SV2016005318A patent/SV2016005318A/es unknown
- 2016-11-11 CU CUP2016000167A patent/CU20160167A7/es unknown
- 2016-11-11 NI NI201600170A patent/NI201600170A/es unknown
- 2016-11-14 IL IL248970A patent/IL248970A0/en unknown
- 2016-11-14 CL CL2016002888A patent/CL2016002888A1/es unknown