JP2014506929A5 - - Google Patents
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- JP2014506929A5 JP2014506929A5 JP2013556755A JP2013556755A JP2014506929A5 JP 2014506929 A5 JP2014506929 A5 JP 2014506929A5 JP 2013556755 A JP2013556755 A JP 2013556755A JP 2013556755 A JP2013556755 A JP 2013556755A JP 2014506929 A5 JP2014506929 A5 JP 2014506929A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimido
- amino
- imidazo
- pyrimidin
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 heteroaryl Aryl Chemical group 0.000 claims 62
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 37
- 125000003118 aryl group Chemical group 0.000 claims 35
- 125000001072 heteroaryl group Chemical group 0.000 claims 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 32
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 31
- 125000005843 halogen group Chemical group 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 125000001424 substituent group Chemical group 0.000 claims 25
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 18
- 229910052799 carbon Inorganic materials 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 125000004043 oxo group Chemical group O=* 0.000 claims 11
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 8
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 8
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 5
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 5
- 125000001624 naphthyl group Chemical group 0.000 claims 5
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- HYVBUDMPUNEJHM-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(2-fluoroethylamino)-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CC(NCCF)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl HYVBUDMPUNEJHM-UHFFFAOYSA-N 0.000 claims 2
- NNQKGOSIJAERJY-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(cyclopropylamino)-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound FC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4CC(CC4=CC=3)NC3CC3)N=C2N2C=CN=C21 NNQKGOSIJAERJY-UHFFFAOYSA-N 0.000 claims 2
- QXZZUBFQRVTJCD-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(diethylamino)-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CC(N(CC)CC)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl QXZZUBFQRVTJCD-UHFFFAOYSA-N 0.000 claims 2
- VEYHNBOUKBIXHN-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(propylamino)-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CC(NCCC)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl VEYHNBOUKBIXHN-UHFFFAOYSA-N 0.000 claims 2
- LAMLNRBJGRMUNN-KKFHFHRHSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-[(3S)-3-fluoropyrrolidin-1-yl]-2,3-dihydro-1H-inden-5-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1[C@@H](F)CCN1C1CC2=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5F)Cl)C5=NC=CN54)=O)=CN=3)=CC=C2C1 LAMLNRBJGRMUNN-KKFHFHRHSA-N 0.000 claims 2
- FAPREGZSIDHQBT-UHFFFAOYSA-N C1=NC=C2C(=O)NC3=NC=CN3C2=N1 Chemical compound C1=NC=C2C(=O)NC3=NC=CN3C2=N1 FAPREGZSIDHQBT-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000000169 tricyclic heterocycle group Chemical group 0.000 claims 2
- MXNPKUQHTFLYOQ-UHFFFAOYSA-N 1-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]phenyl]-N,N-diethylpiperidine-3-carboxamide Chemical compound C1C(C(=O)N(CC)CC)CCCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 MXNPKUQHTFLYOQ-UHFFFAOYSA-N 0.000 claims 1
- WSKYCBFAXMTTQI-UHFFFAOYSA-N 1-[4-[[7-(2-chlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]phenyl]-N-methylmethanesulfonamide Chemical compound C1=CC(CS(=O)(=O)NC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 WSKYCBFAXMTTQI-UHFFFAOYSA-N 0.000 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- WSTMFUSTYZOYDL-UHFFFAOYSA-N 12-(1,2,3-benzothiadiazol-5-ylamino)-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4N=NSC4=CC=3)N=C2N2C=CN=C21 WSTMFUSTYZOYDL-UHFFFAOYSA-N 0.000 claims 1
- CFYZZUMUBPACPF-UHFFFAOYSA-N 12-(1,3-benzothiazol-6-ylamino)-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4SC=NC4=CC=3)N=C2N2C=CN=C21 CFYZZUMUBPACPF-UHFFFAOYSA-N 0.000 claims 1
- AOFIYKYYKPEQEY-UHFFFAOYSA-N 12-(4-aminoanilino)-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=CC(N)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 AOFIYKYYKPEQEY-UHFFFAOYSA-N 0.000 claims 1
- LPWIXQTVUKDQPE-UHFFFAOYSA-N 12-(4-bromoanilino)-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(Br)=CC=3)N=C2N2C=CN=C21 LPWIXQTVUKDQPE-UHFFFAOYSA-N 0.000 claims 1
- XBXHHAXUUZSAER-UHFFFAOYSA-N 12-(4-cyclohexylanilino)-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C3CCCCC3)N=C2N2C=CN=C21 XBXHHAXUUZSAER-UHFFFAOYSA-N 0.000 claims 1
- ZQLRREONZSVIQO-UHFFFAOYSA-N 12-[(1-acetyl-2,3-dihydroindol-6-yl)amino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2N(C(=O)C)CCC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl ZQLRREONZSVIQO-UHFFFAOYSA-N 0.000 claims 1
- XQCSSURHRLCVFQ-UHFFFAOYSA-N 12-[(2-acetyl-3,4-dihydro-1H-isoquinolin-6-yl)amino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2CN(C(=O)C)CCC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl XQCSSURHRLCVFQ-UHFFFAOYSA-N 0.000 claims 1
- ZOERDVHQLNAKHE-UHFFFAOYSA-N 12-[(2-acetyl-3,4-dihydro-1H-isoquinolin-7-yl)amino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2CN(C(=O)C)CCC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl ZOERDVHQLNAKHE-UHFFFAOYSA-N 0.000 claims 1
- UEQZOEVKMMEQFQ-UHFFFAOYSA-N 12-[(2-acetyl-4,4-dimethyl-1,3-dihydroisoquinolin-7-yl)amino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(C(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl UEQZOEVKMMEQFQ-UHFFFAOYSA-N 0.000 claims 1
- WYUGYFWIJUABRJ-UHFFFAOYSA-N 12-[(2-acetylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-7-(2,6-dichloro-4-fluorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=C(F)C=C1Cl WYUGYFWIJUABRJ-UHFFFAOYSA-N 0.000 claims 1
- GKAIUFLVMQMDHO-UHFFFAOYSA-N 12-[(2-acetylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl GKAIUFLVMQMDHO-UHFFFAOYSA-N 0.000 claims 1
- CWGJVAOSKXUZTO-UHFFFAOYSA-N 12-[(2-acetylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-7-(2-chloro-6-fluorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl CWGJVAOSKXUZTO-UHFFFAOYSA-N 0.000 claims 1
- WJRROINZDMTREW-UHFFFAOYSA-N 12-[(2-acetylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl WJRROINZDMTREW-UHFFFAOYSA-N 0.000 claims 1
- IDVBIPAGPCIDPV-UHFFFAOYSA-N 12-[(2-cyclopropylsulfonylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CN(C4)S(=O)(=O)C4CC4)=CC=3)N=C2N2C=CN=C21 IDVBIPAGPCIDPV-UHFFFAOYSA-N 0.000 claims 1
- LDPUHXKJRAXDON-UHFFFAOYSA-N 12-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-7-propan-2-yl-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound N=1C=C2C(=O)N(C(C)C)C3=NC=CN3C2=NC=1NC(C=1)=CC=C2C=1CN(C)CC21CC1 LDPUHXKJRAXDON-UHFFFAOYSA-N 0.000 claims 1
- PLQFKOCDZHKHRX-UHFFFAOYSA-N 12-[3-chloro-4-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)anilino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C(=C1)C(F)(F)F)=C(Cl)C=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 PLQFKOCDZHKHRX-UHFFFAOYSA-N 0.000 claims 1
- OXBXLTUEEZXRSD-UHFFFAOYSA-N 12-[3-chloro-4-(4-methylpiperazin-1-yl)anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C(=C1)Cl)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 OXBXLTUEEZXRSD-UHFFFAOYSA-N 0.000 claims 1
- QVYKKSXEJXHNGJ-UHFFFAOYSA-N 12-[3-chloro-4-(4-methylpiperazin-1-yl)anilino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C(=C1)Cl)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 QVYKKSXEJXHNGJ-UHFFFAOYSA-N 0.000 claims 1
- PWNBRPDHBMSFSF-UHFFFAOYSA-N 12-[4-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl)anilino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC4CCCCN4CC3)N=C2N2C=CN=C21 PWNBRPDHBMSFSF-UHFFFAOYSA-N 0.000 claims 1
- KFZPTHFHLAAPLY-UHFFFAOYSA-N 12-[4-(1,4-diazepan-1-yl)-3-methylanilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C(N2CCNCCC2)C(C)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl KFZPTHFHLAAPLY-UHFFFAOYSA-N 0.000 claims 1
- SARRXSLLADDAOE-UHFFFAOYSA-N 12-[4-(2,7-diazaspiro[3.4]octan-2-yl)anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC4(C3)CNCC4)N=C2N2C=CN=C21 SARRXSLLADDAOE-UHFFFAOYSA-N 0.000 claims 1
- KWDCBYJISYZLLU-UHFFFAOYSA-N 12-[4-(2,7-diazaspiro[3.5]nonan-2-yl)anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC4(C3)CCNCC4)N=C2N2C=CN=C21 KWDCBYJISYZLLU-UHFFFAOYSA-N 0.000 claims 1
- PMWSRMFYNLXUOL-UHFFFAOYSA-N 12-[4-(2,7-diazaspiro[3.5]nonan-7-yl)anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CCC4(CNC4)CC3)N=C2N2C=CN=C21 PMWSRMFYNLXUOL-UHFFFAOYSA-N 0.000 claims 1
- CQQNPOAQLYKSME-UHFFFAOYSA-N 12-[4-(2-acetyl-2,7-diazaspiro[3.5]nonan-7-yl)anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1N(C(=O)C)CC21CCN(C=1C=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5Cl)Cl)C5=NC=CN54)=O)=CN=3)=CC=1)CC2 CQQNPOAQLYKSME-UHFFFAOYSA-N 0.000 claims 1
- ZJEYDTIPPFWMNI-UHFFFAOYSA-N 12-[4-(3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)anilino]-7-(2,6-dichlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC4CCCN4CC3)N=C2N2C=CN=C21 ZJEYDTIPPFWMNI-UHFFFAOYSA-N 0.000 claims 1
- CAFTYPPLMPBFKG-UHFFFAOYSA-N 12-[4-(3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)anilino]-7-(2-chlorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)N3CC4CCCN4CC3)N=C2N2C=CN=C21 CAFTYPPLMPBFKG-UHFFFAOYSA-N 0.000 claims 1
- TWJWRKWSQONEGU-UHFFFAOYSA-N 12-[4-(4-acetylpiperazin-1-yl)anilino]-7-(2-chloro-6-fluorophenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C3=NC=CN3C2=N1 TWJWRKWSQONEGU-UHFFFAOYSA-N 0.000 claims 1
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- AAXQXVYTVSHGLS-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[[4,4-dimethyl-2-(2,2,2-trifluoroethyl)-1,3-dihydroisoquinolin-7-yl]amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(CC(F)(F)F)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl AAXQXVYTVSHGLS-UHFFFAOYSA-N 0.000 claims 1
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- HZXKSYNUISSDRZ-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-(spiro[2,3-dihydro-1H-isoquinoline-4,1'-cyclopropane]-7-ylamino)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound FC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CNC4)=CC=3)N=C2N2C=CN=C21 HZXKSYNUISSDRZ-UHFFFAOYSA-N 0.000 claims 1
- USWYVRFQYIOSJC-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[(1,1,2,3,3-pentamethylisoindol-5-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1=C2C(C)(C)N(C)C(C)(C)C2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl USWYVRFQYIOSJC-UHFFFAOYSA-N 0.000 claims 1
- SSDVHDBNZJIQMX-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[(1,1,2-trimethyl-3H-isoindol-5-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)N(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl SSDVHDBNZJIQMX-UHFFFAOYSA-N 0.000 claims 1
- LZNRTNXWTSKNMC-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl LZNRTNXWTSKNMC-UHFFFAOYSA-N 0.000 claims 1
- YFRNHMAIZOCUPR-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[(2-methylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl YFRNHMAIZOCUPR-UHFFFAOYSA-N 0.000 claims 1
- ZSAHIYGOYSATRM-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[(2-methylsulfonylspiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C3(CC3)CN(S(=O)(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl ZSAHIYGOYSATRM-UHFFFAOYSA-N 0.000 claims 1
- YBPDRUNRDRQNJG-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[(2-pyrrolidin-1-yl-2,3-dihydro-1H-inden-5-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound FC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4CC(CC4=CC=3)N3CCCC3)N=C2N2C=CN=C21 YBPDRUNRDRQNJG-UHFFFAOYSA-N 0.000 claims 1
- PTVNEBPLXVYSBC-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[(4,4-dimethyl-2,3-dihydro-1H-isoquinolin-7-yl)amino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C=1C=C2C(C)(C)CNCC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl PTVNEBPLXVYSBC-UHFFFAOYSA-N 0.000 claims 1
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| US201161447405P | 2011-02-28 | 2011-02-28 | |
| US61/447,405 | 2011-02-28 | ||
| PCT/US2012/026685 WO2012161812A1 (en) | 2011-02-28 | 2012-02-27 | Tricyclic inhibitors of kinases |
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|---|---|
| JP2014506929A JP2014506929A (ja) | 2014-03-20 |
| JP2014506929A5 true JP2014506929A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-04-16 |
| JP5886326B2 JP5886326B2 (ja) | 2016-03-16 |
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| JP2013556755A Expired - Fee Related JP5886326B2 (ja) | 2011-02-28 | 2012-02-27 | 三環式キナーゼ阻害薬 |
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| WO2014026125A1 (en) | 2012-08-10 | 2014-02-13 | Incyte Corporation | Pyrazine derivatives as fgfr inhibitors |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| ES2657451T3 (es) | 2013-04-19 | 2018-03-05 | Incyte Holdings Corporation | Heterocíclicos bicíclicos como inhibidores del FGFR |
| JPWO2015029447A1 (ja) * | 2013-08-30 | 2017-03-02 | 興和株式会社 | 光学活性カルビノール化合物の製造方法 |
| GB201322602D0 (en) * | 2013-12-19 | 2014-02-05 | Almac Discovery Ltd | Pharmaceutical compounds |
| CA2945196C (en) | 2014-04-10 | 2020-02-18 | Dalhousie University | Treatment of parkinson's disease through arfgap1 inhibition |
| EP3185860A4 (en) * | 2014-08-29 | 2018-08-29 | The Board of Regents of the University of Texas System | Novel capsazepine analogs for the treatment of cancer and other proliferative diseases |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| CN107438607B (zh) | 2015-02-20 | 2021-02-05 | 因赛特公司 | 作为fgfr抑制剂的双环杂环 |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| EP3543242B1 (en) * | 2016-11-16 | 2024-01-03 | Impact Therapeutics (Shanghai), Inc | 8,9-dihydroimidazole[1,2-a]pyrimido[5,4-e]pyrimidine-5(6h)-ketone compound |
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| WO2019011228A1 (zh) * | 2017-07-10 | 2019-01-17 | 上海瑛派药业有限公司 | 咪唑并[1,2-b]嘧啶并[4,5-d]哒嗪-5(6H)-酮类化合物及其应用 |
| US11897867B2 (en) | 2017-08-04 | 2024-02-13 | Bayer Aktiengesellschaft | 6-phenyl-4,5-dihydropyridazin-3(2H)-one derivatives as PDE3A and PDE3B inhibitors for treating cancer |
| JOP20200024A1 (ar) | 2017-08-04 | 2020-02-02 | Bayer Ag | مركبات ثنائي هيدروكساديازينون |
| CN107821390A (zh) * | 2017-10-13 | 2018-03-23 | 南京扬子鸿利源化学品有限责任公司 | 一种甲基磺草酮油悬浮剂及其制备方法 |
| HUE067795T2 (hu) | 2017-11-01 | 2024-11-28 | Wuxi Biocity Biopharmaceutics Co Ltd | WEE1 inhibitorként szolgáló makrociklusos vegyület és annak alkalmazásai |
| JP7568512B2 (ja) | 2018-05-04 | 2024-10-16 | インサイト・コーポレイション | Fgfr阻害剤の塩 |
| FI3788047T3 (fi) | 2018-05-04 | 2024-11-02 | Incyte Corp | Fgft-estäjän kiinteitä muotoja ja menetelmiä niiden valmistamiseksi |
| CN108727249A (zh) * | 2018-07-07 | 2018-11-02 | 台州学院 | 3-二氟甲基哌啶盐酸盐及其衍生物的合成方法 |
| AU2019348120A1 (en) * | 2018-09-27 | 2021-05-06 | Betta Pharmaceuticals Co., Ltd | FGFR4 inhibitor and use thereof |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
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| EP3917915A1 (en) | 2019-02-01 | 2021-12-08 | Bayer Aktiengesellschaft | 1,2,4-triazin-3(2h)-one compounds for the treatment of hyperproliferative diseases |
| US11384083B2 (en) | 2019-02-15 | 2022-07-12 | Incyte Corporation | Substituted spiro[cyclopropane-1,5′-pyrrolo[2,3-d]pyrimidin]-6′(7′h)-ones as CDK2 inhibitors |
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| WO2020205560A1 (en) | 2019-03-29 | 2020-10-08 | Incyte Corporation | Sulfonylamide compounds as cdk2 inhibitors |
| WO2020221358A1 (zh) | 2019-04-30 | 2020-11-05 | 石家庄智康弘仁新药开发有限公司 | Wee1抑制剂化合物的晶型及其应用 |
| US11447494B2 (en) | 2019-05-01 | 2022-09-20 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| WO2020223469A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | N-(1-(methylsulfonyl)piperidin-4-yl)-4,5-di hydro-1h-imidazo[4,5-h]quinazolin-8-amine derivatives and related compounds as cyclin-dependent kinase 2 (cdk2) inhibitors for treating cancer |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| WO2021030537A1 (en) | 2019-08-14 | 2021-02-18 | Incyte Corporation | Imidazolyl pyrimidinylamine compounds as cdk2 inhibitors |
| CN112442049A (zh) * | 2019-09-03 | 2021-03-05 | 微境生物医药科技(上海)有限公司 | 作为Wee1抑制剂的嘧啶衍生物 |
| US12122767B2 (en) | 2019-10-01 | 2024-10-22 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| MX2022004390A (es) | 2019-10-11 | 2022-08-08 | Incyte Corp | Aminas biciclicas como inhibidores de la cinasa dependiente de ciclina 2 (cdk2). |
| WO2021076602A1 (en) | 2019-10-14 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CN114502559B (zh) * | 2019-10-16 | 2024-02-02 | 上海瑛派药业有限公司 | 二氢咪唑并嘧啶并嘧啶酮类化合物 |
| US11566028B2 (en) | 2019-10-16 | 2023-01-31 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| CA3163875A1 (en) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| AU2020395185A1 (en) | 2019-12-04 | 2022-06-02 | Incyte Corporation | Derivatives of an FGFR inhibitor |
| WO2021146424A1 (en) | 2020-01-15 | 2021-07-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CN115698006B (zh) | 2020-06-17 | 2024-03-29 | 微境生物医药科技(上海)有限公司 | 作为Wee-1抑制剂的吡唑并[3,4-d]嘧啶-3-酮衍生物 |
| US20240182447A1 (en) * | 2021-02-19 | 2024-06-06 | Wigen Biomedicine Technology (shanghai) Co., Ltd. | Fused ring compound as wee-1 inhibitor |
| TW202304459A (zh) | 2021-04-12 | 2023-02-01 | 美商英塞特公司 | 包含fgfr抑制劑及nectin-4靶向劑之組合療法 |
| BR112023022236A2 (pt) * | 2021-04-30 | 2024-02-06 | Wigen Biomedicine Tech Shanghai Co Ltd | Composto de fórmula geral (1) ou seu isômero, forma cristalina, sal farmaceuticamente aceitável, hidrato ou solvato; composição farmacêutica; e; uso do composto ou seu isômero, forma cristalina, sal farmaceuticamente aceitável, hidrato ou solvato |
| EP4352060A1 (en) | 2021-06-09 | 2024-04-17 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| TW202313611A (zh) | 2021-06-09 | 2023-04-01 | 美商英塞特公司 | 作為fgfr抑制劑之三環雜環 |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| US20250049798A1 (en) * | 2021-11-09 | 2025-02-13 | Hangzhou Glubio Pharmaceutical Co. Ltd. | Wee1 protein kinase degradation agent and use thereof |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| CN116836184B (zh) * | 2022-03-25 | 2025-07-25 | 药雅科技(上海)有限公司 | Wee1激酶抑制剂的制备及其应用 |
| WO2024199388A1 (zh) * | 2023-03-29 | 2024-10-03 | 微境生物医药科技(上海)有限公司 | 作为myt1抑制剂的化合物 |
| CN119039287A (zh) * | 2023-05-29 | 2024-11-29 | 中国药科大学 | 一类四氢吡啶并嘧啶酮衍生物及其制备方法与应用 |
| KR20250136774A (ko) * | 2024-03-08 | 2025-09-16 | 보로노이 주식회사 | 헤테로아릴 유도체 화합물 및 이의 용도 |
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| EP2213673B1 (en) * | 2007-10-23 | 2013-06-05 | Msd K.K. | Pyridone-substituted-dihydropyrazolopyrimidinone derivative |
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| CA2745970A1 (en) * | 2008-12-12 | 2010-06-17 | Msd K.K. | Dihydropyrimidopyrimidine derivative |
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2012
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- 2012-02-27 EP EP12716781.5A patent/EP2681221B1/en not_active Not-in-force
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- 2012-02-27 WO PCT/US2012/026685 patent/WO2012161812A1/en active Application Filing
- 2012-02-27 CA CA2827648A patent/CA2827648A1/en not_active Abandoned
- 2012-02-27 JP JP2013556755A patent/JP5886326B2/ja not_active Expired - Fee Related
- 2012-02-27 CN CN201280018862.6A patent/CN103703005A/zh active Pending
- 2012-02-27 MX MX2013009873A patent/MX340402B/es active IP Right Grant
- 2012-02-27 UY UY0001033925A patent/UY33925A/es not_active Application Discontinuation
- 2012-02-28 US US13/406,937 patent/US8710065B2/en active Active
- 2012-02-28 AR ARP120100641A patent/AR085502A1/es unknown