JP5886326B2 - 三環式キナーゼ阻害薬 - Google Patents

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Publication number

JP5886326B2

JP5886326B2 JP2013556755A JP2013556755A JP5886326B2 JP 5886326 B2 JP5886326 B2 JP 5886326B2 JP 2013556755 A JP2013556755 A JP 2013556755A JP 2013556755 A JP2013556755 A JP 2013556755A JP 5886326 B2 JP5886326 B2 JP 5886326B2

Authority

JP

Japan

Prior art keywords

pyrimido

amino

imidazo

pyrimidin

phenyl

Prior art date

2011-02-28

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.)

Expired - Fee Related

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• 229940043355 kinase inhibitor Drugs 0.000 title description 10
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 10
• -1 heteroaryl Aryl Chemical group 0.000 claims description 530
• 150000001875 compounds Chemical class 0.000 claims description 365
• 125000005843 halogen group Chemical group 0.000 claims description 191
• 125000001072 heteroaryl group Chemical group 0.000 claims description 184
• 125000003118 aryl group Chemical group 0.000 claims description 180
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 178
• 125000001424 substituent group Chemical group 0.000 claims description 161
• 125000000217 alkyl group Chemical group 0.000 claims description 155
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 127
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 114
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 102
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 99
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 80
• 229910052799 carbon Inorganic materials 0.000 claims description 67
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 55
• 229910052736 halogen Inorganic materials 0.000 claims description 48
• 125000004043 oxo group Chemical group O=* 0.000 claims description 45
• 150000002367 halogens Chemical class 0.000 claims description 41
• 229910052739 hydrogen Inorganic materials 0.000 claims description 41
• 125000001624 naphthyl group Chemical group 0.000 claims description 38
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 37
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 37
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 36
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 36
• 150000003839 salts Chemical class 0.000 claims description 34
• BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims description 29
• 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 description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 23
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 20
• 125000001188 haloalkyl group Chemical group 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 15
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
• 125000000169 tricyclic heterocycle group Chemical group 0.000 claims description 11
• 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 description 10
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• UKAFWJUARMVPPH-UHFFFAOYSA-N 8h-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C1=NC=C2C(=O)N=CNC2=N1 UKAFWJUARMVPPH-UHFFFAOYSA-N 0.000 claims description 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 6
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
• 238000006467 substitution reaction Methods 0.000 claims description 6
• 229910052727 yttrium Inorganic materials 0.000 claims description 6
• PLCPXNHZGVDLBL-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-(3-methyl-4-piperazin-1-ylanilino)-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(N2CCNCC2)C(C)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl PLCPXNHZGVDLBL-UHFFFAOYSA-N 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
• 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 description 4
• ABVBVZIBDDRXHB-UHFFFAOYSA-N 12-[4-(4-methylpiperazin-1-yl)anilino]-7-[2-(trifluoromethyl)phenyl]-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)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)C(F)(F)F)C3=NC=CN3C2=N1 ABVBVZIBDDRXHB-UHFFFAOYSA-N 0.000 claims description 4
• DVCFSMPQEKMGAH-UHFFFAOYSA-N 12-[4-(4-methylpiperazin-1-yl)anilino]-7-phenyl-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)=CC=C1NC1=NC=C2C(=O)N(C=3C=CC=CC=3)C3=NC=CN3C2=N1 DVCFSMPQEKMGAH-UHFFFAOYSA-N 0.000 claims description 4
• PCLRXBXXCJHMTF-UHFFFAOYSA-N 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]-N-cyclohexylbenzamide Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CN=C(NC=3C=CC(=CC=3)C(=O)NC3CCCCC3)N=C2N2C=CN=C21 PCLRXBXXCJHMTF-UHFFFAOYSA-N 0.000 claims description 4
• SPYJRXAJCSHASW-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-(4-piperidin-2-ylanilino)-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)C3NCCCC3)N=C2N2C=CN=C21 SPYJRXAJCSHASW-UHFFFAOYSA-N 0.000 claims description 4
• DNDPQMUPODMFQA-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-(4-pyrrolidin-2-ylanilino)-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)C3NCCC3)N=C2N2C=CN=C21 DNDPQMUPODMFQA-UHFFFAOYSA-N 0.000 claims description 4
• WLBVSRCBCIYMAZ-UHFFFAOYSA-N 7-(2,6-difluorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-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)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)F)C3=NC=CN3C2=N1 WLBVSRCBCIYMAZ-UHFFFAOYSA-N 0.000 claims description 4
• SVFMGEMTWAECKS-UHFFFAOYSA-N 7-(2,6-dimethylphenyl)-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(C)C=CC=C1C SVFMGEMTWAECKS-UHFFFAOYSA-N 0.000 claims description 4
• FPMBIKCMUSPCLI-UHFFFAOYSA-N 7-(2-chloro-4-methylphenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-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)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC(C)=CC=3)Cl)C3=NC=CN3C2=N1 FPMBIKCMUSPCLI-UHFFFAOYSA-N 0.000 claims description 4
• QUTZVOUNNKGPFD-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-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)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C3=NC=CN3C2=N1 QUTZVOUNNKGPFD-UHFFFAOYSA-N 0.000 claims description 4
• ZGBTXCDUOKJJGB-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[(4,4-dimethyl-2-propan-2-yl-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(C)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl ZGBTXCDUOKJJGB-UHFFFAOYSA-N 0.000 claims description 4
• GKAGRSUWJGSEAR-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-(hydroxymethyl)-4-(4-methyl-1,4-diazepan-1-yl)anilino]-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)CCCN1C(C(=C1)CO)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 GKAGRSUWJGSEAR-UHFFFAOYSA-N 0.000 claims description 4
• QEQAQSMIISYCKJ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[3-ethyl-4-(4-methylpiperazin-1-yl)anilino]-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(N2CCN(C)CC2)C(CC)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl QEQAQSMIISYCKJ-UHFFFAOYSA-N 0.000 claims description 4
• SUMCRTBWSMDICB-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(1,4-diazepan-1-yl)-3-methylanilino]-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=CC=CC=C1Cl SUMCRTBWSMDICB-UHFFFAOYSA-N 0.000 claims description 4
• BSIGDYDOKKECNI-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(1H-pyrazol-4-yl)anilino]-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)C3=CNN=C3)N=C2N2C=CN=C21 BSIGDYDOKKECNI-UHFFFAOYSA-N 0.000 claims description 4
• OFLUWBFGEJMLNG-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-2,3,4,5,7,11,13-heptazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NN=NN3C2=N1 OFLUWBFGEJMLNG-UHFFFAOYSA-N 0.000 claims description 4
• IICGNJDSNUEEHR-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-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)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 IICGNJDSNUEEHR-UHFFFAOYSA-N 0.000 claims description 4
• LWKBFYGLHVKLIW-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[2-(cyclohexylmethyl)-4,4-dimethyl-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 C1C2=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5)Cl)C5=NC=CN54)=O)=CN=3)=CC=C2C(C)(C)CN1CC1CCCCC1 LWKBFYGLHVKLIW-UHFFFAOYSA-N 0.000 claims description 4
• FMBORYIZQRKJLK-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[4,4-dimethyl-2-(4,4,4-trifluorobutyl)-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(CCCC(F)(F)F)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl FMBORYIZQRKJLK-UHFFFAOYSA-N 0.000 claims description 4
• UXOLVCNWZNMQMB-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[4,4-dimethyl-2-(pyridin-3-ylmethyl)-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 C1C2=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5)Cl)C5=NC=CN54)=O)=CN=3)=CC=C2C(C)(C)CN1CC1=CC=CN=C1 UXOLVCNWZNMQMB-UHFFFAOYSA-N 0.000 claims description 4
• HKBWWKPGTXQPIA-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[[4,4-dimethyl-2-(thiophen-3-ylmethyl)-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 C1C2=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5)Cl)C5=NC=CN54)=O)=CN=3)=CC=C2C(C)(C)CN1CC=1C=CSC=1 HKBWWKPGTXQPIA-UHFFFAOYSA-N 0.000 claims description 4
• XEYIRLOQTLKFHY-UHFFFAOYSA-N 7-(2-chlorophenyl)-3-methyl-12-[4-(4-methylpiperazin-1-yl)anilino]-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)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=C(C)N3C2=N1 XEYIRLOQTLKFHY-UHFFFAOYSA-N 0.000 claims description 4
• WVNQOFKQYRFPIJ-UHFFFAOYSA-N 7-cyclohexyl-12-[4-(4-methylpiperazin-1-yl)anilino]-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)=CC=C1NC1=NC=C2C(=O)N(C3CCCCC3)C3=NC=CN3C2=N1 WVNQOFKQYRFPIJ-UHFFFAOYSA-N 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• VJRKBAPOWFAEMZ-RDJZCZTQSA-N 12-[4-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-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 C([C@]1(NC[C@]2([H])C1)[H])N2C(C=C1)=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl VJRKBAPOWFAEMZ-RDJZCZTQSA-N 0.000 claims description 3
• VIOAAWUARYASTN-UHFFFAOYSA-N 12-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)N=C2N2C=CN=C21 VIOAAWUARYASTN-UHFFFAOYSA-N 0.000 claims description 3
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• 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 description 2
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• QAHYGGLTHWWEOT-UHFFFAOYSA-N 12-[(2-acetyl-4,4-dimethyl-1,3-dihydroisoquinolin-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=C2C(C)(C)CN(C(=O)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl QAHYGGLTHWWEOT-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• BQXGAXHVZLYFLW-UHFFFAOYSA-N 12-[4-(4-acetylpiperazin-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(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 BQXGAXHVZLYFLW-UHFFFAOYSA-N 0.000 claims description 2
• RAOFCVHAVATOES-UHFFFAOYSA-N 12-[4-(4-methylpiperazin-1-yl)anilino]-7-[2-(trifluoromethoxy)phenyl]-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)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)OC(F)(F)F)C3=NC=CN3C2=N1 RAOFCVHAVATOES-UHFFFAOYSA-N 0.000 claims description 2
• GSNIAXMXBBAXNE-UHFFFAOYSA-N 12-[4-[(1-acetylpiperidin-4-yl)amino]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(=O)C)CCC1NC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 GSNIAXMXBBAXNE-UHFFFAOYSA-N 0.000 claims description 2
• VJRKBAPOWFAEMZ-NVXWUHKLSA-N 12-[4-[(1R,4R)-2,5-diazabicyclo[2.2.1]heptan-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 C([C@@]1(NC[C@@]2([H])C1)[H])N2C(C=C1)=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl VJRKBAPOWFAEMZ-NVXWUHKLSA-N 0.000 claims description 2
• KVIAXHIZFPEROL-ZHRRBRCNSA-N 12-[4-[(3aR,6aR)-5-methyl-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrol-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 C([C@@H]1CN(C[C@@H]11)C)CN1C(C=C1)=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl KVIAXHIZFPEROL-ZHRRBRCNSA-N 0.000 claims description 2
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• CAFTYPPLMPBFKG-FQEVSTJZSA-N 12-[4-[(8aS)-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)N3C[C@@H]4CCCN4CC3)N=C2N2C=CN=C21 CAFTYPPLMPBFKG-FQEVSTJZSA-N 0.000 claims description 2
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• MHOWYCRQHGHKCI-UHFFFAOYSA-N 12-[[2-(cyclopropanecarbonyl)spiro[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 ClC1=CC(F)=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CN(C4)C(=O)C4CC4)=CC=3)N=C2N2C=CN=C21 MHOWYCRQHGHKCI-UHFFFAOYSA-N 0.000 claims description 2
• UOLZCRZBSIDSIC-UHFFFAOYSA-N 12-[[2-(cyclopropanecarbonyl)spiro[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)C(=O)C4CC4)=CC=3)N=C2N2C=CN=C21 UOLZCRZBSIDSIC-UHFFFAOYSA-N 0.000 claims description 2
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• GFTMSJAEEHGADR-UHFFFAOYSA-N 12-anilino-7-(3-methoxy-2-methylphenyl)-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound COC1=CC=CC(N2C(C3=CN=C(NC=4C=CC=CC=4)N=C3N3C=CN=C32)=O)=C1C GFTMSJAEEHGADR-UHFFFAOYSA-N 0.000 claims description 2
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• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
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• KZXXQNYTTLEMPA-SFHVURJKSA-N 7-(2,6-dichlorophenyl)-12-[4-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]anilino]-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](N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 KZXXQNYTTLEMPA-SFHVURJKSA-N 0.000 claims description 2
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• VKZXXMSHMVGZMM-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[2-(4-methylpiperazin-1-yl)ethyl]anilino]-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)CCN1CCC(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 VKZXXMSHMVGZMM-UHFFFAOYSA-N 0.000 claims description 2
• ZCMFFRXYWPAMAF-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[2-(dimethylamino)ethyl-ethylamino]anilino]-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(CCN(C)C)CC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 ZCMFFRXYWPAMAF-UHFFFAOYSA-N 0.000 claims description 2
• KXAUNTOLVMSJKJ-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 KXAUNTOLVMSJKJ-UHFFFAOYSA-N 0.000 claims description 2
• RSDUPIFHAPXDBX-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[4-(dimethylamino)piperidine-1-carbonyl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CC(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 RSDUPIFHAPXDBX-UHFFFAOYSA-N 0.000 claims description 2
• GNCAELHTYLWVAX-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[propan-2-yl-[2-(propan-2-ylamino)ethyl]amino]anilino]-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(C(C)C)CCNC(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 GNCAELHTYLWVAX-UHFFFAOYSA-N 0.000 claims description 2
• BWUMKXXNVDKXLR-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-piperazin-1-yl-3-(trifluoromethyl)anilino]-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(N2CCNCC2)C(C(F)(F)F)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl BWUMKXXNVDKXLR-UHFFFAOYSA-N 0.000 claims description 2
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• AMBRIFCKYYVDGS-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[[2-(2-methylpropanoyl)spiro[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(=O)C(C)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl AMBRIFCKYYVDGS-UHFFFAOYSA-N 0.000 claims description 2
• GEPSQLANSSBBBA-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[[2-(dimethylamino)-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(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(Cl)C=CC=C1Cl GEPSQLANSSBBBA-UHFFFAOYSA-N 0.000 claims description 2
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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 description 2
• GMKXOFPMGDEEAV-UHFFFAOYSA-N 7-(2-chloro-3-hydroxyphenyl)-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 OC1=CC=CC(N2C(C3=CN=C(NC=4C=C5C(C6(CC6)CNC5)=CC=4)N=C3N3C=CN=C32)=O)=C1Cl GMKXOFPMGDEEAV-UHFFFAOYSA-N 0.000 claims description 2
• MUBBWOHVMUIKIR-UHFFFAOYSA-N 7-(2-chloro-4,6-difluorophenyl)-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=C(F)C=C1Cl MUBBWOHVMUIKIR-UHFFFAOYSA-N 0.000 claims description 2
• MIUZKHQKIKYNFA-UHFFFAOYSA-N 7-(2-chloro-4,6-difluorophenyl)-12-[4-(4-methylpiperazin-1-yl)anilino]-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)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC(F)=CC=3F)Cl)C3=NC=CN3C2=N1 MIUZKHQKIKYNFA-UHFFFAOYSA-N 0.000 claims description 2
• DGMFLJDUBAOBPV-UHFFFAOYSA-N 7-(2-chloro-4,6-difluorophenyl)-12-[[2-(dimethylamino)-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(C)C)CC2=CC=C1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=C(F)C=C1Cl DGMFLJDUBAOBPV-UHFFFAOYSA-N 0.000 claims description 2
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• 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 description 2
• 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 description 2
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• DATCYIARXKPUBJ-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[4-(1-methylpiperidin-4-yl)anilino]-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)CCC1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C3=NC=CN3C2=N1 DATCYIARXKPUBJ-UHFFFAOYSA-N 0.000 claims description 2
• IWQIFPYCRKJXGB-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3F)Cl)C3=NC=CN3C2=N1 IWQIFPYCRKJXGB-UHFFFAOYSA-N 0.000 claims description 2
• HKDAOTQPQFTQGZ-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(2-hydroxyacetyl)-4,4-dimethyl-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(=O)CO)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl HKDAOTQPQFTQGZ-UHFFFAOYSA-N 0.000 claims description 2
• AKGKWVTWFBVCPK-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(2-methylpropanoyl)spiro[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(=O)C(C)C)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl AKGKWVTWFBVCPK-UHFFFAOYSA-N 0.000 claims description 2
• JAQWMUMGNOQMGD-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(cyclopentanecarbonyl)spiro[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 FC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CN(C4)C(=O)C4CCCC4)=CC=3)N=C2N2C=CN=C21 JAQWMUMGNOQMGD-UHFFFAOYSA-N 0.000 claims description 2
• SCGBGGVRWINOLJ-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(cyclopropanecarbonyl)-4,4-dimethyl-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(=O)C3CC3)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl SCGBGGVRWINOLJ-UHFFFAOYSA-N 0.000 claims description 2
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• BETMOIKLRDEYNF-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-(3,5-difluoro-4-piperazin-1-ylanilino)-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(F)=C(N2CCNCC2)C(F)=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=CC=CC=C1Cl BETMOIKLRDEYNF-UHFFFAOYSA-N 0.000 claims description 2
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• JZMDEGGHLUISMB-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[3-(trifluoromethyl)piperidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1C(C(F)(F)F)CCCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 JZMDEGGHLUISMB-UHFFFAOYSA-N 0.000 claims description 2
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• ICOWOOZKFOHYEH-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[4-(dimethylamino)piperidin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CC(N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 ICOWOOZKFOHYEH-UHFFFAOYSA-N 0.000 claims description 2
• ZIVISXMJPANONQ-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[4-(oxetan-3-yl)piperazin-1-yl]anilino]-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)N3CCN(CC3)C3COC3)N=C2N2C=CN=C21 ZIVISXMJPANONQ-UHFFFAOYSA-N 0.000 claims description 2
• DPYHKUBAWKDQGM-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[4-[2-(dimethylamino)ethyl]piperazin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(CCN(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 DPYHKUBAWKDQGM-UHFFFAOYSA-N 0.000 claims description 2
• GIZSAAKJRUZMGS-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[4-[3-(dimethylamino)propyl]piperazin-1-yl]anilino]-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(CCCN(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 GIZSAAKJRUZMGS-UHFFFAOYSA-N 0.000 claims description 2
• GYVYBZGLYXUARW-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-[propan-2-yl-[2-(propan-2-ylamino)ethyl]amino]anilino]-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(C(C)C)CCNC(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 GYVYBZGLYXUARW-UHFFFAOYSA-N 0.000 claims description 2
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• RRUCAEDSIJXSMT-UHFFFAOYSA-N 7-(4-hydroxy-2-methylphenyl)-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 CC1=CC(O)=CC=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CNC4)=CC=3)N=C2N2C=CN=C21 RRUCAEDSIJXSMT-UHFFFAOYSA-N 0.000 claims description 2
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• BUJBUAPLAJWDLH-UHFFFAOYSA-N 7-[2-chloro-4-(trifluoromethyl)phenyl]-12-[4-(4-methylpiperazin-1-yl)anilino]-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)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC(=CC=3)C(F)(F)F)Cl)C3=NC=CN3C2=N1 BUJBUAPLAJWDLH-UHFFFAOYSA-N 0.000 claims description 2
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• YFXPXAIGNXNQIY-UHFFFAOYSA-N C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=S)C=1N1C=CN=C1N2C1=CC=CC=C1Cl Chemical compound C=1C=C2C3(CC3)CN(C)CC2=CC=1NC(N=1)=NC=C(C2=S)C=1N1C=CN=C1N2C1=CC=CC=C1Cl YFXPXAIGNXNQIY-UHFFFAOYSA-N 0.000 claims description 2
• HJTVIZPBTFNXGN-UHFFFAOYSA-N C=1C=C2C3(CC3)CN(CC(F)F)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl Chemical compound C=1C=C2C3(CC3)CN(CC(F)F)CC2=CC=1NC(N=1)=NC=C(C2=O)C=1N1C=CN=C1N2C1=C(F)C=CC=C1Cl HJTVIZPBTFNXGN-UHFFFAOYSA-N 0.000 claims description 2
• CLMIGLFZQQFETA-UHFFFAOYSA-N S1CC(=O)N(C(C)C)C1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 Chemical compound S1CC(=O)N(C(C)C)C1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NC=CN3C2=N1 CLMIGLFZQQFETA-UHFFFAOYSA-N 0.000 claims description 2
• 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
• INBLGJXWYYQNCP-UHFFFAOYSA-N methyl 4-[[7-(2,6-dichlorophenyl)-8-oxo-2,5,7,11,13-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-12-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 INBLGJXWYYQNCP-UHFFFAOYSA-N 0.000 claims description 2
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
• 239000012453 solvate Substances 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
• HHIFFEAVUYQZLV-UHFFFAOYSA-N 2-[[7-[[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]-4,4-dimethyl-1,3-dihydroisoquinolin-2-yl]methyl]benzonitrile Chemical compound C1C2=CC(NC=3N=C4C(C(N(C=5C(=CC=CC=5)Cl)C5=NC=CN54)=O)=CN=3)=CC=C2C(C)(C)CN1CC1=CC=CC=C1C#N HHIFFEAVUYQZLV-UHFFFAOYSA-N 0.000 claims 1
• MHZZCSSVPOHYON-UHFFFAOYSA-N 7-(2,6-dichloro-4-fluorophenyl)-12-[(6-piperazin-1-ylpyridin-3-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 ClC1=CC(F)=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=NC(=CC=3)N3CCNCC3)N=C2N2C=CN=C21 MHZZCSSVPOHYON-UHFFFAOYSA-N 0.000 claims 1
• LRGFEYBMQIRJDW-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-(piperidin-4-ylamino)anilino]-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(NC4CCNCC4)=CC=3)N=C2N2C=CN=C21 LRGFEYBMQIRJDW-UHFFFAOYSA-N 0.000 claims 1
• ZSNROWXRZIHBBO-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)-12-[4-[2-(dimethylamino)ethylamino]anilino]-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(NCCN(C)C)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3Cl)Cl)C3=NC=CN3C2=N1 ZSNROWXRZIHBBO-UHFFFAOYSA-N 0.000 claims 1
• PSVSKRQYABFVSD-UHFFFAOYSA-N 7-(2-chloro-6-fluorophenyl)-12-[[2-(cyclopropanecarbonyl)spiro[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 FC1=CC=CC(Cl)=C1N1C(=O)C2=CN=C(NC=3C=C4C(C5(CC5)CN(C4)C(=O)C4CC4)=CC=3)N=C2N2C=CN=C21 PSVSKRQYABFVSD-UHFFFAOYSA-N 0.000 claims 1
• HZLADDZBGLEJJV-UHFFFAOYSA-N 7-(2-chlorophenyl)-12-[4-(1,3-thiazol-2-yl)anilino]-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)C=3SC=CN=3)N=C2N2C=CN=C21 HZLADDZBGLEJJV-UHFFFAOYSA-N 0.000 claims 1
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