JP2009529047A5 - - Google Patents
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- JP2009529047A5 JP2009529047A5 JP2008558335A JP2008558335A JP2009529047A5 JP 2009529047 A5 JP2009529047 A5 JP 2009529047A5 JP 2008558335 A JP2008558335 A JP 2008558335A JP 2008558335 A JP2008558335 A JP 2008558335A JP 2009529047 A5 JP2009529047 A5 JP 2009529047A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- pyrazolo
- phenyl
- yloxy
- fluorophenyl
- 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.)
- Pending
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- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 111
- 125000000217 alkyl group Chemical group 0.000 claims 60
- 125000000623 heterocyclic group Chemical group 0.000 claims 54
- -1 cyclopropylidene Chemical group 0.000 claims 53
- 125000003118 aryl group Chemical group 0.000 claims 49
- 125000001072 heteroaryl group Chemical group 0.000 claims 46
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 34
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 28
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 28
- 229910052801 chlorine Inorganic materials 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 25
- 229910052731 fluorine Inorganic materials 0.000 claims 25
- 229910052794 bromium Inorganic materials 0.000 claims 24
- 125000004452 carbocyclyl group Chemical group 0.000 claims 23
- 229910005965 SO 2 Inorganic materials 0.000 claims 21
- 229910052740 iodine Inorganic materials 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims 17
- 125000003342 alkenyl group Chemical group 0.000 claims 15
- 125000000304 alkynyl group Chemical group 0.000 claims 15
- 125000004429 atom Chemical group 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 11
- 229920006395 saturated elastomer Polymers 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- ABWZEYVKVVURNN-UHFFFAOYSA-N C1=CC(=CC=C1N2C(=O)C(=CC=N2)C(=O)N)F.Cl.Cl Chemical compound C1=CC(=CC=C1N2C(=O)C(=CC=N2)C(=O)N)F.Cl.Cl ABWZEYVKVVURNN-UHFFFAOYSA-N 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- FEHLGOYZDFFMND-UHFFFAOYSA-N cyclopropane-1,1-dicarboxamide Chemical compound NC(=O)C1(C(N)=O)CC1 FEHLGOYZDFFMND-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 1
- QAVYDPMCCPMIMA-UHFFFAOYSA-N 1-(1,3-benzoxazol-2-yl)-n-[4-[[3-[4-(dimethylamino)piperidin-1-yl]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]cyclopropane-1-carboxamide Chemical compound C1CC(N(C)C)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C4(CC4)C=4OC5=CC=CC=C5N=4)=CC=3)F)=C12 QAVYDPMCCPMIMA-UHFFFAOYSA-N 0.000 claims 1
- FXUKPCLDNDAEHQ-UHFFFAOYSA-N 1-[3-fluoro-4-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-3-pyridin-2-ylurea Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)NC1=CC=CC=N1 FXUKPCLDNDAEHQ-UHFFFAOYSA-N 0.000 claims 1
- IKSRPHLQEGXXGS-UHFFFAOYSA-N 1-n'-(4-fluorophenyl)-1-n'-[4-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]cyclopropane-1,1-dicarboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C=C1)=CC=C1N(C=1C=CC(F)=CC=1)C(=O)C1(C(N)=O)CC1 IKSRPHLQEGXXGS-UHFFFAOYSA-N 0.000 claims 1
- YTMOLVGYLBFYEJ-UHFFFAOYSA-N 1-n'-[3-fluoro-4-[[3-[2-(4-methylpiperazin-1-yl)ethyl]-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-1-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound C1CN(C)CCN1CCC1=NNC2=NC=CC(OC=3C(=CC(=CC=3)N(C(=O)C3(CC3)C(N)=O)C=3C=CC(F)=CC=3)F)=C12 YTMOLVGYLBFYEJ-UHFFFAOYSA-N 0.000 claims 1
- RQDGTOYZOBSJDZ-UHFFFAOYSA-N 1-n'-[3-fluoro-4-[[3-[3-(methylcarbamoyl)phenyl]-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-1-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound CNC(=O)C1=CC=CC(C=2C3=C(OC=4C(=CC(=CC=4)N(C(=O)C4(CC4)C(N)=O)C=4C=CC(F)=CC=4)F)C=CN=C3NN=2)=C1 RQDGTOYZOBSJDZ-UHFFFAOYSA-N 0.000 claims 1
- LHMHIVIVMVOYLE-UHFFFAOYSA-N 1-n'-[3-fluoro-4-[[3-[5-[(4-methylpiperazin-1-yl)methyl]furan-3-yl]-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-1-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound C1CN(C)CCN1CC1=CC(C=2C3=C(OC=4C(=CC(=CC=4)N(C(=O)C4(CC4)C(N)=O)C=4C=CC(F)=CC=4)F)C=CN=C3NN=2)=CO1 LHMHIVIVMVOYLE-UHFFFAOYSA-N 0.000 claims 1
- DUJXTXVAJACGSD-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)-n-[4-[[3-[4-(dimethylamino)piperidin-1-yl]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]acetamide Chemical compound C1CC(N(C)C)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)CC=4OC5=CC=CC=C5N=4)=CC=3)F)=C12 DUJXTXVAJACGSD-UHFFFAOYSA-N 0.000 claims 1
- XIHLQKAIDPWUBD-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-[3-fluoro-4-[[3-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C5=CNN=C5)=NNC=4N=CC=3)=CC=2)=CC=N1 XIHLQKAIDPWUBD-UHFFFAOYSA-N 0.000 claims 1
- CBFAVFULWUWDGH-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]pyrimidin-5-yl]-3-oxopyridazine-4-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(N=C1)=NC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 CBFAVFULWUWDGH-UHFFFAOYSA-N 0.000 claims 1
- CAHHJGBCLQZQOM-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-fluoro-4-[(3-piperazin-1-yl-1h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(N5CCNCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 CAHHJGBCLQZQOM-UHFFFAOYSA-N 0.000 claims 1
- SPCVWZIVKSEQKR-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-fluoro-4-[(3-piperidin-4-yl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C5CCNCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 SPCVWZIVKSEQKR-UHFFFAOYSA-N 0.000 claims 1
- CLLRKPIKZGXPNG-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-fluoro-4-[(3-pyridin-3-yl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C=5C=NC=CC=5)=NNC=4N=CC=3)=CC=2)=CC=N1 CLLRKPIKZGXPNG-UHFFFAOYSA-N 0.000 claims 1
- RWTYLSUDJBYXHX-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-fluoro-4-[[3-(1,2,3,6-tetrahydropyridin-4-yl)-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C=5CCNCC=5)=NNC=4N=CC=3)=CC=2)=CC=N1 RWTYLSUDJBYXHX-UHFFFAOYSA-N 0.000 claims 1
- RCERBRZFXRIRIT-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-fluoro-4-[[3-(1-piperidin-4-ylpyrazol-4-yl)-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C5=CN(N=C5)C5CCNCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 RCERBRZFXRIRIT-UHFFFAOYSA-N 0.000 claims 1
- IDWKWRRAUUARSD-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-fluoro-4-[[3-(4-piperazin-1-ylphenyl)-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C=5C=CC(=CC=5)N5CCNCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 IDWKWRRAUUARSD-UHFFFAOYSA-N 0.000 claims 1
- UUMQLVCYOXAKEC-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-fluoro-4-[[3-(4-propan-2-ylpiperazine-1-carbonyl)-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1CN(C(C)C)CCN1C(=O)C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 UUMQLVCYOXAKEC-UHFFFAOYSA-N 0.000 claims 1
- SWFJTRDTGFQNNG-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-fluoro-4-[[3-(4-pyrrolidin-1-ylpiperidin-1-yl)-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(N5CCC(CC5)N5CCCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 SWFJTRDTGFQNNG-UHFFFAOYSA-N 0.000 claims 1
- ARWJOZPFUSMKES-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-fluoro-4-[[3-(piperidin-4-ylamino)-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(NC5CCNCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 ARWJOZPFUSMKES-UHFFFAOYSA-N 0.000 claims 1
- LMNNRVRRULMESK-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-fluoro-4-[[3-(piperidin-4-ylmethyl)-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(CC5CCNCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 LMNNRVRRULMESK-UHFFFAOYSA-N 0.000 claims 1
- YKYQEFHSHJBTAO-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-fluoro-4-[[3-(pyrrolidin-3-ylamino)-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(NC5CNCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 YKYQEFHSHJBTAO-UHFFFAOYSA-N 0.000 claims 1
- DJFGVFOSGODYGW-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-fluoro-4-[[3-[(1-propan-2-ylpiperidin-4-yl)amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1CN(C(C)C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 DJFGVFOSGODYGW-UHFFFAOYSA-N 0.000 claims 1
- QYHCRZYLKDBYKA-HSZRJFAPSA-N 2-(4-fluorophenyl)-n-[3-fluoro-4-[[3-[(2r)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(N5[C@H](CCC5)CN5CCCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 QYHCRZYLKDBYKA-HSZRJFAPSA-N 0.000 claims 1
- SICGKDJUHCIWIA-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[6-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]pyridin-3-yl]-3-oxopyridazine-4-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(N=C1)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 SICGKDJUHCIWIA-UHFFFAOYSA-N 0.000 claims 1
- HIGVKGMGGRNDOG-UHFFFAOYSA-N 2-(cyclohexylmethyl)-5-[3-fluoro-4-[[3-[4-(morpholine-4-carbonyl)phenyl]-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-methylpyrimidin-4-one Chemical compound N=1C=C(C=2C=C(F)C(OC=3C=4C(C=5C=CC(=CC=5)C(=O)N5CCOCC5)=NNC=4N=CC=3)=CC=2)C(=O)N(C)C=1CC1CCCCC1 HIGVKGMGGRNDOG-UHFFFAOYSA-N 0.000 claims 1
- ZEHHLYMHSQRGNJ-UHFFFAOYSA-N 2-(cyclopropylmethylamino)-5-[3-fluoro-4-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-3-methylpyrimidin-4-one Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NCC1CC1 ZEHHLYMHSQRGNJ-UHFFFAOYSA-N 0.000 claims 1
- ZICAZXCZHGFFQS-UHFFFAOYSA-N 2-[3-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]anilino]-n-(4-fluorophenyl)pyridine-3-carboxamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC=4C(=CC=CN=4)C(=O)NC=4C=CC(F)=CC=4)=CC=3)F)=C12 ZICAZXCZHGFFQS-UHFFFAOYSA-N 0.000 claims 1
- LDUGMDDJWJCONU-UHFFFAOYSA-N 2-anilino-5-[3-fluoro-4-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-3-methylpyrimidin-4-one Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C(N1C)=O)=CN=C1NC1=CC=CC=C1 LDUGMDDJWJCONU-UHFFFAOYSA-N 0.000 claims 1
- BIQZYBBVDZAVPZ-UHFFFAOYSA-N 2-anilino-5-[3-fluoro-4-[[3-(4-fluorophenyl)-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-methylpyrimidin-4-one Chemical compound N=1C=C(C=2C=C(F)C(OC=3C=4C(C=5C=CC(F)=CC=5)=NNC=4N=CC=3)=CC=2)C(=O)N(C)C=1NC1=CC=CC=C1 BIQZYBBVDZAVPZ-UHFFFAOYSA-N 0.000 claims 1
- WFHKRJMKNVHPAS-UHFFFAOYSA-N 2-anilino-5-[3-fluoro-4-[[3-[4-(morpholine-4-carbonyl)phenyl]-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-methylpyrimidin-4-one Chemical compound N=1C=C(C=2C=C(F)C(OC=3C=4C(C=5C=CC(=CC=5)C(=O)N5CCOCC5)=NNC=4N=CC=3)=CC=2)C(=O)N(C)C=1NC1=CC=CC=C1 WFHKRJMKNVHPAS-UHFFFAOYSA-N 0.000 claims 1
- UBAWQZFXFMKRDQ-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-[3-fluoro-4-[(3-piperazin-1-yl-1h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-oxo-3-azabicyclo[3.1.0]hexane-1-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C2(C(=O)NC=3C=C(F)C(OC=4C=5C(N6CCNCC6)=NNC=5N=CC=4)=CC=3)CC2C1 UBAWQZFXFMKRDQ-UHFFFAOYSA-N 0.000 claims 1
- CWFPETGAOXZZMK-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-5-[3-fluoro-4-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]pyrimidin-4-one Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1C(C1=O)=CN=CN1CC1=CC=C(Cl)C=C1 CWFPETGAOXZZMK-UHFFFAOYSA-N 0.000 claims 1
- UWJXMGKPTGPXPO-UHFFFAOYSA-N 3-[3-fluoro-4-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-1,4-dihydroquinazolin-2-one Chemical compound C1C2=CC=CC=C2NC(=O)N1C(C=C1F)=CC=C1OC1=C2C(C)=NNC2=NC=C1 UWJXMGKPTGPXPO-UHFFFAOYSA-N 0.000 claims 1
- LFXAGJXLAYLHGR-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[3-fluoro-4-[[3-(4-propan-2-ylpiperazine-1-carbonyl)-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyrazine-2-carboxamide Chemical compound C1CN(C(C)C)CCN1C(=O)C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)C=CN=4)=O)=CC=3)F)=C12 LFXAGJXLAYLHGR-UHFFFAOYSA-N 0.000 claims 1
- DQPHFHDECJHGPS-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[3-fluoro-4-[[3-(piperidin-4-ylmethyl)-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyrazine-2-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(CC5CCNCC5)=NNC=4N=CC=3)=CC=2)=NC=C1 DQPHFHDECJHGPS-UHFFFAOYSA-N 0.000 claims 1
- WTWMYVHNSSMCSG-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[3-fluoro-4-[[3-[(1-propan-2-ylpiperidin-4-yl)amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyrazine-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)C=CN=4)=O)=CC=3)F)=C12 WTWMYVHNSSMCSG-UHFFFAOYSA-N 0.000 claims 1
- LAPVFEUWCXXCQS-UHFFFAOYSA-N 4-[4-[2-fluoro-4-[[1-[(4-fluorophenyl)carbamoyl]cyclopropanecarbonyl]amino]phenoxy]-2h-pyrazolo[3,4-b]pyridin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C4(CC4)C(=O)NC=4C=CC(F)=CC=4)=CC=3)F)=C12 LAPVFEUWCXXCQS-UHFFFAOYSA-N 0.000 claims 1
- KDJYKPDYWKWGKJ-UHFFFAOYSA-N 4-benzyl-n-[3-fluoro-4-[[3-[4-(morpholine-4-carbonyl)phenyl]-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxopyrazine-2-carboxamide Chemical compound C=1C=C(OC=2C=3C(C=4C=CC(=CC=4)C(=O)N4CCOCC4)=NNC=3N=CC=2)C(F)=CC=1NC(=O)C(C1=O)=NC=CN1CC1=CC=CC=C1 KDJYKPDYWKWGKJ-UHFFFAOYSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- YXCUZSXWFOTQIS-UHFFFAOYSA-N [3-[[4-[2-fluoro-4-[[2-(4-fluorophenyl)-3-oxopyridazine-4-carbonyl]amino]phenoxy]-1h-pyrazolo[3,4-b]pyridin-3-yl]amino]cyclohexyl] 2,2,2-trifluoroacetate Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(NC5CC(CCC5)OC(=O)C(F)(F)F)=NNC=4N=CC=3)=CC=2)=CC=N1 YXCUZSXWFOTQIS-UHFFFAOYSA-N 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 150000001717 carbocyclic compounds Chemical class 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- DCVLOIOMXXTLHE-UHFFFAOYSA-N methyl 4-[2-fluoro-4-[[2-(4-fluorophenyl)-3-oxopyridazine-4-carbonyl]amino]phenoxy]-2h-pyrazolo[3,4-b]pyridine-3-carboxylate Chemical compound C=12C(C(=O)OC)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 DCVLOIOMXXTLHE-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- PPPLBGVCEQCLFW-UHFFFAOYSA-N n-[2,3-difluoro-4-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1F)F)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 PPPLBGVCEQCLFW-UHFFFAOYSA-N 0.000 claims 1
- AKXLXFHSBDEXOA-UHFFFAOYSA-N n-[2,5-difluoro-4-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC(F)=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 AKXLXFHSBDEXOA-UHFFFAOYSA-N 0.000 claims 1
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- SRJUSQCMBAUMJH-UHFFFAOYSA-N n-[3-fluoro-4-(1-methyl-3-phenylpyrazolo[3,4-b]pyridin-4-yl)oxyphenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C12=C(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)C=CN=C2N(C)N=C1C1=CC=CC=C1 SRJUSQCMBAUMJH-UHFFFAOYSA-N 0.000 claims 1
- YUGBUKDMWDFNCT-UHFFFAOYSA-N n-[3-fluoro-4-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=CN1C1=CC=C(F)C=C1 YUGBUKDMWDFNCT-UHFFFAOYSA-N 0.000 claims 1
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- GHSFYNJGDFMLJF-UHFFFAOYSA-N n-[3-fluoro-4-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-methyl-3-oxopyridazine-4-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C1=CC=NN(C)C1=O GHSFYNJGDFMLJF-UHFFFAOYSA-N 0.000 claims 1
- FACGQBFORBZHTQ-UHFFFAOYSA-N n-[3-fluoro-4-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-oxopyrrolidine-3-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C1CCNC1=O FACGQBFORBZHTQ-UHFFFAOYSA-N 0.000 claims 1
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- RUUBBFCLUPQERU-UHFFFAOYSA-N n-[3-fluoro-4-[[3-(1-methyl-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrol-5-yl)-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1C2N(C)CCC2CN1C(C=12)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 RUUBBFCLUPQERU-UHFFFAOYSA-N 0.000 claims 1
- SVVDUAKUJFHGJD-UHFFFAOYSA-N n-[3-fluoro-4-[[3-(1-methylimidazol-2-yl)-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound CN1C=CN=C1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 SVVDUAKUJFHGJD-UHFFFAOYSA-N 0.000 claims 1
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- UGJBEVKDQMSDPR-UHFFFAOYSA-N n-[3-fluoro-4-[[3-(4-methylpiperazine-1-carbonyl)-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CN(C)CCN1C(=O)C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 UGJBEVKDQMSDPR-UHFFFAOYSA-N 0.000 claims 1
- RNQJUHKUZGBCNR-UHFFFAOYSA-N n-[3-fluoro-4-[[3-(oxan-4-ylamino)-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(NC5CCOCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 RNQJUHKUZGBCNR-UHFFFAOYSA-N 0.000 claims 1
- MQYOGDYNVXAYQA-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-1-(4-fluorophenyl)-2-oxoazepane-3-carboxamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C4C(N(C=5C=CC(F)=CC=5)CCCC4)=O)=CC=3)F)=C12 MQYOGDYNVXAYQA-UHFFFAOYSA-N 0.000 claims 1
- ZTESXMAKJAHPAE-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)C=CC=4)=O)=CC=3)F)=C12 ZTESXMAKJAHPAE-UHFFFAOYSA-N 0.000 claims 1
- MZABKBDFFVWSPY-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 MZABKBDFFVWSPY-UHFFFAOYSA-N 0.000 claims 1
- UONAEXMYVRONMC-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-oxo-2-pyridin-2-ylpyridazine-4-carboxamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5N=CC=CC=5)N=CC=4)=O)=CC=3)F)=C12 UONAEXMYVRONMC-UHFFFAOYSA-N 0.000 claims 1
- AYWOXSRJQVYOIJ-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-3-phenylbenzamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C=C(C=CC=4)C=4C=CC=CC=4)=CC=3)F)=C12 AYWOXSRJQVYOIJ-UHFFFAOYSA-N 0.000 claims 1
- LXJSRWDKZGPIHC-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[(1-methylpiperidin-4-yl)amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-4-(4-fluorophenyl)-3-oxopyrazine-2-carboxamide Chemical compound C1CN(C)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)C=CN=4)=O)=CC=3)F)=C12 LXJSRWDKZGPIHC-UHFFFAOYSA-N 0.000 claims 1
- LTGITATXWVOHAZ-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[(3-hydroxycyclohexyl)amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1C(O)CCCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 LTGITATXWVOHAZ-UHFFFAOYSA-N 0.000 claims 1
- JBMUNMIFFUSBKL-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-4-(4-fluorophenyl)-3-oxopyrazine-2-carboxamide Chemical compound CN1C(C2)CCC1CC2NC(C=12)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=NC=CN1C1=CC=C(F)C=C1 JBMUNMIFFUSBKL-UHFFFAOYSA-N 0.000 claims 1
- JOPQLIAQRRMRSE-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[4-(2-methoxyethyl)piperazin-1-yl]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CN(CCOC)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 JOPQLIAQRRMRSE-UHFFFAOYSA-N 0.000 claims 1
- BTYJBHVLVJLKTN-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[4-(methylamino)piperidin-1-yl]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CC(NC)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 BTYJBHVLVJLKTN-UHFFFAOYSA-N 0.000 claims 1
- IVTRVOWFNZWCSL-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[4-(methylcarbamoyl)phenyl]-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-1-methyl-2-oxopyrrolidine-3-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C4C(N(C)CC4)=O)=CC=3)F)=C12 IVTRVOWFNZWCSL-UHFFFAOYSA-N 0.000 claims 1
- VIZFVZDWCKQICZ-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[4-(morpholine-4-carbonyl)phenyl]-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C=5C=CC(=CC=5)C(=O)N5CCOCC5)=NNC=4N=CC=3)=CC=2)=CC=N1 VIZFVZDWCKQICZ-UHFFFAOYSA-N 0.000 claims 1
- QADUINPLQNGMAM-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[4-(morpholine-4-carbonyl)phenyl]-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-4-methyl-3-oxopyrazine-2-carboxamide Chemical compound O=C1N(C)C=CN=C1C(=O)NC(C=C1F)=CC=C1OC1=CC=NC2=C1C(C=1C=CC(=CC=1)C(=O)N1CCOCC1)=NN2 QADUINPLQNGMAM-UHFFFAOYSA-N 0.000 claims 1
- BUAHSOJGMDGSOU-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[[1-(2-fluoroethyl)piperidin-4-yl]amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1CN(CCF)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 BUAHSOJGMDGSOU-UHFFFAOYSA-N 0.000 claims 1
- NFUHTWNHZCURNS-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[[1-(2-hydroxyethyl)piperidin-4-yl]amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CN(CCO)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 NFUHTWNHZCURNS-UHFFFAOYSA-N 0.000 claims 1
- ZXELOZQYQABKCF-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[[1-(2-methoxyethyl)piperidin-4-yl]amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1CN(CCOC)CCC1NC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 ZXELOZQYQABKCF-UHFFFAOYSA-N 0.000 claims 1
- GAHXXXBESXMEQG-UHFFFAOYSA-N n-[3-fluoro-4-[[3-[methyl-(1-methylpiperidin-4-yl)amino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound N=1NC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C2C=1N(C)C1CCN(C)CC1 GAHXXXBESXMEQG-UHFFFAOYSA-N 0.000 claims 1
- SQQPXGFYGGHUCL-UHFFFAOYSA-N n-[4-[[3-(3-chlorophenyl)-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C(F)C(OC=3C=4C(C=5C=C(Cl)C=CC=5)=NNC=4N=CC=3)=CC=2)=CC=N1 SQQPXGFYGGHUCL-UHFFFAOYSA-N 0.000 claims 1
- ZHJSJSQWLMHTGQ-UHFFFAOYSA-N n-[4-[[3-[(1-ethylpiperidin-4-yl)methyl]-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-4-(4-fluorophenyl)-3-oxopyrazine-2-carboxamide Chemical compound C1CN(CC)CCC1CC1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)C=CN=4)=O)=CC=3)F)=C12 ZHJSJSQWLMHTGQ-UHFFFAOYSA-N 0.000 claims 1
- MYDPMRDRYKLTGU-HXUWFJFHSA-N n-[4-[[3-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1[C@H](N(C)C)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 MYDPMRDRYKLTGU-HXUWFJFHSA-N 0.000 claims 1
- RQLHHRJWUPJIFN-UHFFFAOYSA-N n-[4-[[3-[2-[(dimethylamino)methyl]piperidin-1-yl]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound CN(C)CC1CCCCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 RQLHHRJWUPJIFN-UHFFFAOYSA-N 0.000 claims 1
- DFSOIXFJBFCGHY-UHFFFAOYSA-N n-[4-[[3-[3-(dimethylamino)propylamino]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C=12C(NCCCN(C)C)=NNC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 DFSOIXFJBFCGHY-UHFFFAOYSA-N 0.000 claims 1
- QOENHNXLNBSTKP-UHFFFAOYSA-N n-[4-[[3-[4-(dimethylamino)phenyl]-2h-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 QOENHNXLNBSTKP-UHFFFAOYSA-N 0.000 claims 1
- NEFBUIHSRZKYJD-UHFFFAOYSA-N n-[4-[[3-[4-(dimethylamino)piperidin-1-yl]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C1CC(N(C)C)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)N=CC=4)=O)=CC=3)F)=C12 NEFBUIHSRZKYJD-UHFFFAOYSA-N 0.000 claims 1
- UGTRUZIPOLZFMT-UHFFFAOYSA-N n-[4-[[3-[4-(dimethylamino)piperidin-1-yl]-1h-pyrazolo[3,4-b]pyridin-4-yl]oxy]-3-fluorophenyl]-3-(4-fluorophenyl)-2-oxo-3-azabicyclo[3.1.0]hexane-1-carboxamide Chemical compound C1CC(N(C)C)CCN1C1=NNC2=NC=CC(OC=3C(=CC(NC(=O)C45C(C4)CN(C5=O)C=4C=CC(F)=CC=4)=CC=3)F)=C12 UGTRUZIPOLZFMT-UHFFFAOYSA-N 0.000 claims 1
- VJOLBFHEBPXHII-UHFFFAOYSA-N n-[5-chloro-2-fluoro-4-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound C=12C(C)=NNC2=NC=CC=1OC(C(=C1)Cl)=CC(F)=C1NC(=O)C(C1=O)=CC=NN1C1=CC=C(F)C=C1 VJOLBFHEBPXHII-UHFFFAOYSA-N 0.000 claims 1
- XYVCJSMWTFHTQN-UHFFFAOYSA-N n-benzyl-n-[3-fluoro-4-[(3-methyl-2h-pyrazolo[3,4-b]pyridin-4-yl)oxy]phenyl]acetamide Chemical compound C=1C=C(OC=2C=3C(C)=NNC=3N=CC=2)C(F)=CC=1N(C(=O)C)CC1=CC=CC=C1 XYVCJSMWTFHTQN-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 0 CN(***C1(*)C(C(*)(*)**)=*)C1=C Chemical compound CN(***C1(*)C(C(*)(*)**)=*)C1=C 0.000 description 1
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Families Citing this family (113)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4323957B2 (ja) * | 2002-01-22 | 2009-09-02 | バイオマテラ インコーポレイテッド | 生物分解性ポリマーの乾燥方法 |
| WO2006068760A2 (en) | 2004-11-19 | 2006-06-29 | The Regents Of The University Of California | Anti-inflammatory pyrazolopyrimidines |
| JP2009529047A (ja) * | 2006-03-07 | 2009-08-13 | アレイ バイオファーマ、インコーポレイテッド | ヘテロ二環系ピラゾール化合物およびその使用 |
| WO2008127226A2 (en) | 2006-04-04 | 2008-10-23 | The Regents Of The University Of California | P13 kinase antagonists |
| CA2655128A1 (en) * | 2006-06-08 | 2007-12-21 | Array Biopharma Inc. | Quinoline compounds and methods of use |
| MX2009001198A (es) * | 2006-08-16 | 2009-02-11 | Hoffmann La Roche | Inhibidores no nucleosidicos de la transcriptasa inversa. |
| US7776857B2 (en) * | 2007-04-05 | 2010-08-17 | Amgen Inc. | Aurora kinase modulators and method of use |
| CA2697795C (en) | 2007-08-29 | 2016-08-16 | Methylgene Inc. | Thieno[3,2,b]pyridinyl compounds as inhibitors of protein tyrosine kinase activity |
| WO2009046448A1 (en) | 2007-10-04 | 2009-04-09 | Intellikine, Inc. | Chemical entities and therapeutic uses thereof |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| CN104926815B (zh) | 2008-01-04 | 2017-11-03 | 英特利凯恩有限责任公司 | 某些化学实体、组合物和方法 |
| CN101959887B (zh) | 2008-01-08 | 2013-07-31 | 阵列生物制药公司 | 作为激酶抑制剂的吡咯并吡啶 |
| ES2392014T3 (es) | 2008-01-09 | 2012-12-03 | Array Biopharma, Inc. | Pirazolopiridinas como inhibidores de la cinasa |
| EP2235001B1 (en) * | 2008-01-23 | 2014-12-24 | Bristol-Myers Squibb Company | Process for preparing pyridinone compounds |
| WO2009095752A1 (en) * | 2008-01-29 | 2009-08-06 | Glenmark Pharmaceuticals, S.A. | Fused pyrazole derivatives as cannabinoid receptor modulators |
| EP2257293A2 (en) * | 2008-03-06 | 2010-12-08 | Genentech, Inc. | Combination therapy with c-met and egfr antagonists |
| WO2009114870A2 (en) | 2008-03-14 | 2009-09-17 | Intellikine, Inc. | Kinase inhibitors and methods of use |
| WO2009114874A2 (en) | 2008-03-14 | 2009-09-17 | Intellikine, Inc. | Benzothiazole kinase inhibitors and methods of use |
| EP2294062B1 (en) * | 2008-06-09 | 2013-08-21 | Bayer Intellectual Property GmbH | Substituted 4- (indazolyl) -1,4-dihydropyridines and methods of use thereof |
| JP5480891B2 (ja) * | 2008-06-09 | 2014-04-23 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | アネレート化４−（インダゾリル）−１，４−ジヒドロピリジン誘導体およびそれらの使用方法 |
| EP2313414B1 (en) | 2008-07-08 | 2015-11-04 | Intellikine, LLC | Kinase inhibitors and methods of use |
| WO2010006072A2 (en) | 2008-07-08 | 2010-01-14 | The Regents Of The University Of California | Mtor modulators and uses thereof |
| TWI365185B (en) * | 2008-07-24 | 2012-06-01 | Lilly Co Eli | Amidophenoxyindazoles useful as inhibitors of c-met |
| RS53350B (sr) | 2008-09-22 | 2014-10-31 | Array Biopharma, Inc. | Supstituisana jedinjenja imidazo[1,2-b]piridazina kao inhibitori trk kinaze |
| JP5731978B2 (ja) | 2008-09-26 | 2015-06-10 | インテリカイン， エルエルシー | 複素環キナーゼ阻害剤 |
| EP2532657B9 (en) * | 2008-10-14 | 2017-04-19 | Sunshine Lake Pharma Co., Ltd. | Compounds and methods of use |
| KR100961410B1 (ko) * | 2008-10-14 | 2010-06-09 | (주)네오팜 | 단백질 키나제 억제제로서 헤테로사이클릭 화합물 |
| DK2358720T3 (en) | 2008-10-16 | 2016-06-06 | Univ California | Heteroarylkinaseinhibitorer fused-ring |
| EP2350071B1 (en) | 2008-10-22 | 2014-01-08 | Array Biopharma, Inc. | SUBSTITUTED PYRAZOLO[1,5-a]PYRIMIDINE COMPOUNDS AS TRK KINASE INHIBITORS |
| US8476431B2 (en) | 2008-11-03 | 2013-07-02 | Itellikine LLC | Benzoxazole kinase inhibitors and methods of use |
| CA2743416A1 (en) * | 2008-11-13 | 2010-05-20 | Exelixis Inc. | Methods of preparing quinoline derivatives |
| TWI511956B (zh) | 2009-01-16 | 2015-12-11 | Exelixis Inc | 製備ｎ-（４-｛〔６，７-雙（甲氧基）喹啉-４-基〕氧基｝苯基）-ｎ’-（４-氟苯基）環丙烷-１，１-二甲醯胺之方法 |
| JP5789252B2 (ja) | 2009-05-07 | 2015-10-07 | インテリカイン， エルエルシー | 複素環式化合物およびその使用 |
| AR077468A1 (es) | 2009-07-09 | 2011-08-31 | Array Biopharma Inc | Compuestos de pirazolo (1,5 -a) pirimidina sustituidos como inhibidores de trk- quinasa |
| UA108618C2 (uk) | 2009-08-07 | 2015-05-25 | Застосування c-met-модуляторів в комбінації з темозоломідом та/або променевою терапією для лікування раку | |
| EP2789615B1 (en) * | 2009-08-11 | 2017-05-03 | Bristol-Myers Squibb Company | Azaindazoles as Btk kinase modulators and use thereof |
| DK2467141T3 (en) | 2009-08-17 | 2019-02-18 | Intellikine Llc | HETEROCYCLIC COMPOUNDS AND APPLICATIONS THEREOF |
| US8980899B2 (en) | 2009-10-16 | 2015-03-17 | The Regents Of The University Of California | Methods of inhibiting Ire1 |
| WO2011049988A2 (en) * | 2009-10-20 | 2011-04-28 | Eiger Biopharmaceuticals, Inc. | Indazoles to treat flaviviridae virus infection |
| JP5907564B2 (ja) * | 2010-03-01 | 2016-04-26 | ノヴァドラッグ，エルエルシー | ウィルス性疾患の治療のための組成物及び方法 |
| AU2011248441A1 (en) | 2010-04-29 | 2012-12-20 | Deciphera Pharmaceuticals, Llc | Pyridone amides and analogs exhibiting anti-cancer and anti-proliferative activites |
| PL3205654T3 (pl) | 2010-05-20 | 2019-08-30 | Array Biopharma, Inc. | Związki makrocykliczne jako inhibitory kinazy TRK |
| JP5951600B2 (ja) | 2010-05-21 | 2016-07-13 | インフィニティー ファーマシューティカルズ， インコーポレイテッド | キナーゼ調節のための、化合物、組成物および方法 |
| JP2013545749A (ja) | 2010-11-10 | 2013-12-26 | インフィニティー ファーマシューティカルズ， インコーポレイテッド | 複素環化合物及びその使用 |
| TWI674262B (zh) | 2011-01-10 | 2019-10-11 | 美商英菲尼提製藥股份有限公司 | 製備異喹啉酮之方法及異喹啉酮之固體形式 |
| EP2487159A1 (en) | 2011-02-11 | 2012-08-15 | MSD Oss B.V. | RorgammaT inhibitors |
| CN103491962B (zh) | 2011-02-23 | 2016-10-12 | 因特利凯有限责任公司 | 激酶抑制剂的组合及其用途 |
| RU2568258C2 (ru) | 2011-02-28 | 2015-11-20 | Саншайн Лейк Фарма Ко., Лтд | Замещенные соединения хинолина и способы их использования |
| WO2012127472A1 (en) * | 2011-03-22 | 2012-09-27 | Mapi Pharma Ltd. | Process and intermediates for the preparation of preladenant and related compounds |
| WO2013012915A1 (en) | 2011-07-19 | 2013-01-24 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| HK1198475A1 (en) | 2011-07-19 | 2015-05-08 | 无限药品股份有限公司 | Heterocyclic compounds and uses thereof |
| CA2844588A1 (en) * | 2011-08-10 | 2013-02-14 | Merck Patent Gmbh | Pyrido-pyrimidine derivatives |
| MX2014002542A (es) | 2011-08-29 | 2014-07-09 | Infinity Pharmaceuticals Inc | Compuestos heterociclicos y usos de los mismos. |
| MX370814B (es) | 2011-09-02 | 2020-01-08 | Univ California | Pirazolo[3,4-d]pirimidinas sustituidas y usos de las mismas. |
| WO2013043715A1 (en) | 2011-09-19 | 2013-03-28 | Genentech, Inc. | Combination treatments comprising c-met antagonists and b-raf antagonists |
| RU2501800C2 (ru) * | 2012-02-07 | 2013-12-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Пермский государственный национальный исследовательский университет" | 2-(6-АРИЛ-4-АРОИЛ-3-МЕТИЛ-1-ФЕНИЛ-1Н-ПИРАЗОЛО[3,4-b]ПИРИДИН-5-ИЛ)-2-ОКСО-N-АРИЛАЦЕТАМИДЫ И СПОСОБ ИХ ПОЛУЧЕНИЯ |
| WO2013152252A1 (en) | 2012-04-06 | 2013-10-10 | OSI Pharmaceuticals, LLC | Combination anti-cancer therapy |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US8828998B2 (en) | 2012-06-25 | 2014-09-09 | Infinity Pharmaceuticals, Inc. | Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors |
| WO2014026327A1 (en) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | 4-heteroaryl substituted benzoic acid compounds as rorgammat inhibitors and uses thereof |
| WO2014026330A1 (en) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | 3-AMINOCYCLOALKYL COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF |
| WO2014052669A1 (en) | 2012-09-26 | 2014-04-03 | The Regents Of The University Of California | Modulation of ire1 |
| DK2914296T4 (da) | 2012-11-01 | 2022-01-03 | Infinity Pharmaceuticals Inc | Behandling af cancere under anvendelse af PI3-kinase-isoform-modulatorer |
| SG11201502884TA (en) | 2012-11-08 | 2015-05-28 | Pfizer | Heteroaromatic compounds as dopamine d1 ligands |
| US9260426B2 (en) * | 2012-12-14 | 2016-02-16 | Arrien Pharmaceuticals Llc | Substituted 1H-pyrrolo [2, 3-b] pyridine and 1H-pyrazolo [3, 4-b] pyridine derivatives as salt inducible kinase 2 (SIK2) inhibitors |
| US9481667B2 (en) | 2013-03-15 | 2016-11-01 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
| CN105209042B (zh) | 2013-03-22 | 2019-03-08 | 米伦纽姆医药公司 | 催化性mtorc 1/2抑制剂与选择性极光a激酶抑制剂的组合 |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| JP6466924B2 (ja) | 2013-10-04 | 2019-02-06 | インフィニティー ファーマシューティカルズ， インコーポレイテッド | 複素環式化合物及びその使用 |
| CA2934667A1 (en) * | 2013-12-26 | 2015-07-02 | Ignyta, Inc. | Pyrazolo[1,5-a]pyridine derivatives and methods of their use |
| CN113620958A (zh) | 2014-03-19 | 2021-11-09 | 无限药品股份有限公司 | 用于治疗PI3K-γ介导的障碍的杂环化合物 |
| JP2017516458A (ja) | 2014-03-24 | 2017-06-22 | ジェネンテック， インコーポレイテッド | ｃ−ｍｅｔ拮抗剤による癌治療及びｃ−ｍｅｔ拮抗剤のＨＧＦ発現との相関 |
| WO2015160975A2 (en) | 2014-04-16 | 2015-10-22 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| AR101106A1 (es) | 2014-07-02 | 2016-11-23 | Pharmacyclics Llc | Inhibidores de tirosina quinasa de bruton |
| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CN107428760B (zh) | 2014-11-16 | 2021-04-27 | 阵列生物制药公司 | (s)-n-(5-((r)-2-(2,5-二氟苯基)-吡咯烷-1-基)-吡唑并[1,5-a]嘧啶-3-基)-3-羟基吡咯烷-1-甲酰胺硫酸氢盐的晶型 |
| US10221142B2 (en) | 2015-02-11 | 2019-03-05 | Merck Sharp & Dohme Corp. | Substituted pyrazole compounds as RORgammaT inhibitors and uses thereof |
| CN108290827B (zh) | 2015-07-31 | 2021-01-01 | 约翰霍普金斯大学 | 谷氨酰胺类似物的前药 |
| KR102787845B1 (ko) | 2015-09-14 | 2025-03-31 | 트웰브 테라퓨틱스, 아이엔씨. | 이소퀴놀리논의 고체형, 그의 제조 방법, 이를 포함하는 조성물 및 이를 사용하는 방법 |
| US9796711B2 (en) * | 2015-10-09 | 2017-10-24 | Abbvie S.Á.R.L. | Substituted pyrazolo[3,4-b]pyridin-6-carboxylic acids and method of use |
| BR112018008357A2 (en) | 2015-10-26 | 2018-11-27 | Loxo Oncology, Inc. | dot mutations in trk inhibitor resistant cancer and related methods |
| EP3368516B1 (en) | 2015-10-27 | 2020-07-15 | Merck Sharp & Dohme Corp. | SUBSTITUTED BICYCLIC PYRAZOLE COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF |
| US10287272B2 (en) | 2015-10-27 | 2019-05-14 | Merck Sharp & Dohme Corp. | Substituted indazole compounds as RORgammaT inhibitors and uses thereof |
| CA3002853A1 (en) | 2015-10-27 | 2017-05-04 | Merck Sharp & Dohme Corp. | Heteroaryl substituted benzoic acids as rorgammat inhibitors and uses thereof |
| US10759806B2 (en) | 2016-03-17 | 2020-09-01 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as PI3K kinase inhibitors |
| US10045991B2 (en) | 2016-04-04 | 2018-08-14 | Loxo Oncology, Inc. | Methods of treating pediatric cancers |
| FI3439662T3 (fi) | 2016-04-04 | 2024-09-04 | Loxo Oncology Inc | (s)-n-(5-((r)-2-(2,5-difluorifenyyli)pyrrolidin-1-yyli)pyratsolo[1,5-a]pyrimidin-3-yyli)-3-hydroksipyrrolidiini-1-karboksamidin nesteformulaatioita |
| HRP20201984T1 (hr) | 2016-05-18 | 2021-04-16 | Loxo Oncology, Inc. | Priprema (s)-n-(5-((r)-2-(2,5-difluorofenil)pirolidin-1-il)pirazolo[1,5-a]pirimidin-3-il)-3-hidroksipirolidin-1-karboksamida |
| EA202092441A1 (ru) | 2016-06-07 | 2021-05-21 | Джакобио Фармасьютикалс Ко., Лтд. | Новые гетероциклические производные, применимые в качестве ингибиторов shp2 |
| US10919914B2 (en) | 2016-06-08 | 2021-02-16 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| SG11201811237WA (en) | 2016-06-24 | 2019-01-30 | Infinity Pharmaceuticals Inc | Combination therapies |
| JOP20190092A1 (ar) | 2016-10-26 | 2019-04-25 | Array Biopharma Inc | عملية لتحضير مركبات بيرازولو[1، 5-a]بيريميدين وأملاح منها |
| JOP20190213A1 (ar) | 2017-03-16 | 2019-09-16 | Array Biopharma Inc | مركبات حلقية ضخمة كمثبطات لكيناز ros1 |
| US10988466B2 (en) | 2017-03-23 | 2021-04-27 | Jacobio Pharmaceuticals Co., Ltd. | Heterocyclic derivatives useful as SHP2 inhibitors |
| CN108948002A (zh) * | 2017-05-19 | 2018-12-07 | 厦门大学 | 五元并六元氮杂芳环类化合物、其制备方法、药用组合物及其应用 |
| WO2018228920A1 (en) | 2017-06-13 | 2018-12-20 | Bayer Pharma Aktiengesellschaft | Substituted pyrrolopyridine-derivatives |
| CA3079060A1 (en) | 2017-06-13 | 2018-12-20 | Bayer Pharma Aktiengesellschaft | Substituted pyrrolopyridine-derivatives as map4k1 modulators for the treatment of cancer diseases |
| CA3074381A1 (en) | 2017-06-13 | 2018-12-20 | Bayer Pharma Aktiengesellschaft | Substituted pyrrolopyridine-derivatives |
| CA3070013A1 (en) | 2017-07-18 | 2019-01-24 | Bayer Pharma Aktiengesellschaft | Substituted pyrrolopyridine-derivatives |
| WO2019121143A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Substituted cyclopropyl derivatives |
| MX2020006527A (es) | 2017-12-22 | 2020-09-17 | Sumitomo Chemical Co | Compuesto heterociclico y agente para controlar artropodos perjudiciales que contienen el mismo. |
| US11673897B2 (en) | 2018-01-26 | 2023-06-13 | Exelixis, Inc. | Compounds for the treatment of kinase-dependent disorders |
| CN112312909B (zh) | 2018-01-26 | 2024-07-02 | 埃克塞里艾克西斯公司 | 用于治疗激酶依赖性病症的化合物 |
| AU2019234574A1 (en) | 2018-03-12 | 2020-09-03 | Abbvie Inc. | Inhibitors of tyrosine kinase 2 mediated signaling |
| CA3102279A1 (en) | 2018-06-01 | 2019-12-05 | Cornell University | Combination therapy for pi3k-associated disease or disorder |
| UY38349A (es) * | 2018-08-30 | 2020-03-31 | Array Biopharma Inc | Compuestos de pirazolo[3,4-b]piridina como inhibidores de cinasas tam y met |
| US20210393623A1 (en) | 2018-09-26 | 2021-12-23 | Jacobio Pharmaceuticals Co., Ltd. | Novel Heterocyclic Derivatives Useful as SHP2 Inhibitors |
| EP3986559A1 (en) * | 2019-06-24 | 2022-04-27 | BenevolentAI Bio Limited | New compounds and methods |
| WO2021020362A1 (ja) * | 2019-07-29 | 2021-02-04 | 武田薬品工業株式会社 | 複素環化合物 |
| WO2021113436A1 (en) * | 2019-12-04 | 2021-06-10 | Arcus Biosciences, Inc. | Inhibitors of hif-2alpha |
| US20230150956A1 (en) * | 2020-02-10 | 2023-05-18 | Stemsynergy Therapeutics, Inc. | Myc inhibitors and uses thereof |
| WO2023137406A1 (en) * | 2022-01-12 | 2023-07-20 | Shenzhen Ionova Life Science Co., Ltd. | Heteroaryl compounds as hpk1 inhibitors and methods of using same |
| TW202413341A (zh) | 2022-09-23 | 2024-04-01 | 美商富曼西公司 | 吡唑醯胺殺昆蟲劑 |
Family Cites Families (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3773919A (en) | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| ZW12187A1 (en) | 1986-07-03 | 1989-02-01 | Janssen Pharmaceutica Nv | 4-(aroylamino)piperidinebutanamide derivatives |
| AU3262593A (en) | 1992-01-11 | 1993-08-03 | Schering Agrochemicals Limited | Biheterocyclic fungicidal compounds |
| US5252581A (en) | 1992-07-20 | 1993-10-12 | Hoechst-Roussel Pharmaceuticals Inc. | Substituted aminothienopyridines, pharmaceutical composition and use |
| DK0765327T3 (da) * | 1994-06-16 | 1999-11-29 | Pfizer | Pyrazolo- og pyrrolopyridiner |
| US5880141A (en) | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| EP0929520B1 (en) | 1996-08-23 | 2005-11-02 | Sugen, Inc. | Indolinone combinatorial libraries and related products and methods for the treatment of disease |
| EP0929553B1 (en) * | 1996-10-02 | 2005-03-16 | Novartis AG | Pyrimidine derivatives and processes for the preparation thereof |
| JP2002508324A (ja) | 1997-12-13 | 2002-03-19 | ブリストル−マイヤーズ スクイブ カンパニー | サイクリン依存性キナーゼ阻害剤としてのピラゾロ［３，４−ｂ］ピリジンの使用 |
| US6232320B1 (en) | 1998-06-04 | 2001-05-15 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
| GB9906566D0 (en) | 1999-03-23 | 1999-05-19 | Zeneca Ltd | Chemical compounds |
| US6297238B1 (en) | 1999-04-06 | 2001-10-02 | Basf Aktiengesellschaft | Therapeutic agents |
| US6921763B2 (en) * | 1999-09-17 | 2005-07-26 | Abbott Laboratories | Pyrazolopyrimidines as therapeutic agents |
| CA2385747A1 (en) | 1999-09-17 | 2001-03-22 | Gavin C. Hirst | Pyrazolopyrimidines as therapeutic agents |
| CA2407445A1 (en) | 2000-04-25 | 2001-11-01 | Bristol-Myers Squibb Company | Use of 5-thio-, sulfinyl- and sulfonylpyrazolo¬3,4-b|-pyridines as cyclin dependent kinase inhibitors |
| WO2001098301A1 (en) | 2000-06-20 | 2001-12-27 | Japan Tobacco Inc. | Pyrazolopyridine compounds and use thereof as drugs |
| JP2002020386A (ja) * | 2000-07-07 | 2002-01-23 | Ono Pharmaceut Co Ltd | ピラゾロピリジン誘導体 |
| WO2002096361A2 (en) | 2001-05-30 | 2002-12-05 | Sugen, Inc. | 5-aralkylsulfonyl-3- (pyrrol-2-ylmethylidene)-2-indolinone derivatives as kinase inhibitors |
| AR036040A1 (es) | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos de heteroarilo multiciclicos sustituidos con quinuclidinas y composiciones farmaceuticas que los contienen |
| DE60233736D1 (de) | 2001-06-22 | 2009-10-29 | Kirin Pharma K K | Chinolinderivat und chinazolinderivat, die die selbstphosphorylierung des hepatocytus-proliferator-rezeptors hemmen, und diese enthaltende medizinische zusammensetzung |
| WO2003022856A1 (en) | 2001-09-12 | 2003-03-20 | Pharmacia & Upjohn Company | Substituted 7-aza[2.2.1] bicycloheptanes for the treatment of diseases |
| JP2005516023A (ja) | 2001-12-19 | 2005-06-02 | スミスクライン ビーチャム コーポレーション | プロテインチロシンキナーゼ阻害剤としてのチエノピリミジン化合物 |
| JP4445753B2 (ja) | 2002-01-29 | 2010-04-07 | グラクソ グループ リミテッド | アミノピペリジン誘導体 |
| JP4508650B2 (ja) | 2002-01-29 | 2010-07-21 | グラクソ グループ リミテッド | アミノピペリジン化合物、当該化合物の製法および当該化合物を含有する医薬組成物 |
| US6790852B2 (en) | 2002-04-18 | 2004-09-14 | Hoffmann-La Roche Inc. | 2-(2,6-dichlorophenyl)-diarylimidazoles |
| TW200400034A (en) | 2002-05-20 | 2004-01-01 | Bristol Myers Squibb Co | Pyrazolo-pyrimidine aniline compounds useful as kinase inhibitors |
| GB0211649D0 (en) | 2002-05-21 | 2002-07-03 | Novartis Ag | Organic compounds |
| JP4754821B2 (ja) | 2002-06-20 | 2011-08-24 | プロキシマゲン・リミテッド | 肥満症、ｉｉ型糖尿病およびｃｎｓ障害の治療に有用な新規化合物 |
| TW200409637A (en) | 2002-06-26 | 2004-06-16 | Glaxo Group Ltd | Compounds |
| ES2294330T3 (es) | 2002-08-02 | 2008-04-01 | MERCK & CO., INC. | Derivados de furo(2,3-b)piridina sustituidos. |
| JP2006501217A (ja) * | 2002-08-12 | 2006-01-12 | スージェン・インコーポレーテッド | 新規キナーゼ阻害剤としての３−ピロリル−ピリドピラゾールおよび３−ピロリル−インダゾール |
| EP1539753B1 (en) | 2002-09-16 | 2009-09-09 | Glaxo Group Limited | Pyrazolo(3,4-b)pyridine compounds, and their use as phosphodiesterase inhibitors |
| GB0230045D0 (en) | 2002-12-23 | 2003-01-29 | Glaxo Group Ltd | Compounds |
| EP1549645A1 (en) | 2002-10-01 | 2005-07-06 | Johnson & Johnson Pharmaceutical Research & Development, Inc. | 4,6-diaminosubstituted-2-[oxy or aminoxy]-[1,3,5]triazines as protein tyrosine kinase inhibitors |
| AR042486A1 (es) | 2002-12-18 | 2005-06-22 | Glaxo Group Ltd | Compuesto de quinolina y naftiridina halosustituido en la posicion 3, procedimiento para preparar el compuesto, composicion farmaceutica que lo comprende y su uso para preparar dicha composicion . |
| ES2502490T3 (es) | 2003-02-26 | 2014-10-03 | Sugen, Inc. | Compuestos aminoheteroarílicos como inhibidores de proteín quinasas |
| CA2522595A1 (en) | 2003-04-03 | 2004-10-28 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| US7122548B2 (en) | 2003-07-02 | 2006-10-17 | Sugen, Inc. | Triazolotriazine compounds and uses thereof |
| BRPI0412040A (pt) | 2003-07-02 | 2006-09-05 | Sugen Inc | hidrazidas de indolinona como inibidores de c-met |
| US7037909B2 (en) | 2003-07-02 | 2006-05-02 | Sugen, Inc. | Tetracyclic compounds as c-Met inhibitors |
| AR045342A1 (es) | 2003-08-15 | 2005-10-26 | Merck & Co Inc | Inhibidores de quinesina mitotica |
| PL2392565T3 (pl) | 2003-09-26 | 2014-08-29 | Exelixis Inc | Modulatory c-Met i sposoby stosowania |
| CA2557004A1 (en) | 2003-12-19 | 2005-06-30 | Glaxo Group Limited | Pyrazolo [3,4-b] pyridine compounds, and their use as phosphodiesterase inhibitors |
| JP4805166B2 (ja) | 2003-12-22 | 2011-11-02 | バジリア ファルマスーチカ アーゲー | アロイルフランおよびアロイルチオフェン |
| WO2005070891A2 (en) | 2004-01-23 | 2005-08-04 | Amgen Inc | Compounds and methods of use |
| CA2557575A1 (en) * | 2004-02-27 | 2005-09-15 | F. Hoffmann-La Roche Ag | Fused derivatives of pyrazole |
| US7459562B2 (en) | 2004-04-23 | 2008-12-02 | Bristol-Myers Squibb Company | Monocyclic heterocycles as kinase inhibitors |
| TW200538453A (en) | 2004-04-26 | 2005-12-01 | Bristol Myers Squibb Co | Bicyclic heterocycles as kinase inhibitors |
| WO2005121125A1 (en) | 2004-06-09 | 2005-12-22 | Pfizer Inc. | Ether-linked heteroaryl compounds |
| US7439246B2 (en) | 2004-06-28 | 2008-10-21 | Bristol-Myers Squibb Company | Fused heterocyclic kinase inhibitors |
| US7173031B2 (en) | 2004-06-28 | 2007-02-06 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| WO2006014325A2 (en) * | 2004-07-02 | 2006-02-09 | Exelixis, Inc. | C-met modulators and method of use |
| JP2008521900A (ja) | 2004-11-30 | 2008-06-26 | アムジエン・インコーポレーテツド | キノリン及びキナゾリン類似体並びにがん治療のための医薬としてのその使用 |
| JP2008536927A (ja) | 2005-04-19 | 2008-09-11 | メルク エンド カムパニー インコーポレーテッド | Ｎ−アルキル−アザシクロアルキルｎｍｄａ／ｎｒ２ｂ拮抗物質 |
| US7470693B2 (en) | 2005-04-21 | 2008-12-30 | Bristol-Myers Squibb Company | Oxalamide derivatives as kinase inhibitors |
| JO2787B1 (en) | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| ES2623221T3 (es) | 2005-05-20 | 2017-07-10 | Methylgene Inc | Inhibidores de la señalización del receptor de VEGF y del receptor de HGF |
| FR2889526B1 (fr) | 2005-08-04 | 2012-02-17 | Aventis Pharma Sa | 7-aza-indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
| US7732613B2 (en) | 2005-09-14 | 2010-06-08 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| US7880004B2 (en) | 2005-09-15 | 2011-02-01 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| US7547782B2 (en) | 2005-09-30 | 2009-06-16 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| JP2009529047A (ja) * | 2006-03-07 | 2009-08-13 | アレイ バイオファーマ、インコーポレイテッド | ヘテロ二環系ピラゾール化合物およびその使用 |
| AR060061A1 (es) | 2006-03-22 | 2008-05-21 | Methylgene Inc | Inhibidores de la actividad de la proteina tirosina quinasa |
| CA2680625C (en) * | 2007-03-14 | 2016-02-23 | Ranbaxy Laboratories Limited | Pyrazolo (3, 4-b) pyridine derivatives as phosphodiesterase inhibitors |
| ES2526649T3 (es) * | 2007-12-21 | 2015-01-14 | F. Hoffmann-La Roche Ag | Compuestos heterocíclicos antivíricos |
-
2007
- 2007-03-06 JP JP2008558335A patent/JP2009529047A/ja active Pending
- 2007-03-06 RU RU2008139599/04A patent/RU2008139599A/ru not_active Application Discontinuation
- 2007-03-06 KR KR1020087024415A patent/KR20080110783A/ko not_active Withdrawn
- 2007-03-06 BR BRPI0708615-6A patent/BRPI0708615A2/pt not_active Application Discontinuation
- 2007-03-06 AU AU2007224020A patent/AU2007224020A1/en not_active Abandoned
- 2007-03-06 EP EP07752297A patent/EP2001880A2/en not_active Withdrawn
- 2007-03-06 CA CA002645137A patent/CA2645137A1/en not_active Abandoned
- 2007-03-06 US US11/714,342 patent/US7723330B2/en not_active Expired - Fee Related
- 2007-03-06 WO PCT/US2007/005583 patent/WO2007103308A2/en not_active Ceased
- 2007-03-06 MX MX2008011220A patent/MX2008011220A/es not_active Application Discontinuation
- 2007-03-07 AR ARP070100948A patent/AR059887A1/es unknown
- 2007-03-07 TW TW096107890A patent/TW200800996A/zh unknown
- 2007-03-07 CL CL2007000601A patent/CL2007000601A1/es unknown
-
2008
- 2008-08-21 IL IL193587A patent/IL193587A0/en unknown
- 2008-09-04 ZA ZA2008/07632A patent/ZA200807632B/en unknown
- 2008-09-19 MA MA31254A patent/MA31339B1/fr unknown
- 2008-09-30 CO CO08104090A patent/CO6140061A2/es unknown
- 2008-10-02 CR CR10338A patent/CR10338A/es unknown
- 2008-10-06 NO NO20084183A patent/NO20084183L/no not_active Application Discontinuation
- 2008-10-06 EC EC2008008791A patent/ECSP088791A/es unknown
-
2010
- 2010-01-26 US US12/693,975 patent/US20100256356A1/en not_active Abandoned
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