JP2011530513A5

JP2011530513A5 -

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Publication number: JP2011530513A5
Authority: JP; Japan
Prior art keywords: phenyl; methyl; pyrido; dihydro; phthalazin
Prior art date: 2009-07-27
Legal status : Granted

Application number

JP2011522113A

Other languages

English (en)

Japanese (ja)

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JP2011530513A (ja

JP5984389B2 (ja

Filing date

2009-07-27

Publication date

2012-09-13

2009-07-27 Application filed filed Critical

2009-07-27 Priority claimed from PCT/US2009/051879 external-priority patent/WO2010017055A2/en

2011-12-22 Publication of JP2011530513A publication Critical patent/JP2011530513A/ja

2012-09-13 Publication of JP2011530513A5 publication Critical patent/JP2011530513A5/ja

2016-09-06 Application granted granted Critical

2016-09-06 Publication of JP5984389B2 publication Critical patent/JP5984389B2/ja

Status Active legal-status Critical Current

2029-07-27 Anticipated expiration legal-status Critical

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239000000203 mixture Substances 0.000 claims description 51
150000001875 compounds Chemical class 0.000 claims description 45
-1 hydroxyalkylene Chemical group 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 43
239000000651 prodrug Substances 0.000 claims description 38
229940002612 prodrug Drugs 0.000 claims description 38
239000012453 solvate Substances 0.000 claims description 36
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
WGZMUTVUDVLUJL-UHFFFAOYSA-N 12-phenyl-11-pyridin-2-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2C=CC=CC=2)C1C1=CC=CC=N1 WGZMUTVUDVLUJL-UHFFFAOYSA-N 0.000 claims description 4
VZYOBZPMHSMQGJ-UHFFFAOYSA-N 12-phenyl-11-pyridin-4-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2C=CC=CC=2)C1C1=CC=NC=C1 VZYOBZPMHSMQGJ-UHFFFAOYSA-N 0.000 claims description 4
BHZVOOWIZQGXNS-UHFFFAOYSA-N 3-[4-(methylaminomethyl)phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CNC)=CC=C1N1C(=O)C(C=CC=C2NCC3)=C2C3=N1 BHZVOOWIZQGXNS-UHFFFAOYSA-N 0.000 claims description 4
RTUFESSLZGXXEW-UHFFFAOYSA-N 12-[3-(methylaminomethyl)phenyl]-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CNCC1=CC=CC(C2C=3C4=C(C(NN=3)=O)C=CC=C4NC2C=2C=CC=CC=2)=C1 RTUFESSLZGXXEW-UHFFFAOYSA-N 0.000 claims description 3
QRRXIQPVIZSLHQ-UHFFFAOYSA-N 12-phenyl-11-[4-(pyrrolidin-1-ylmethyl)phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2C=CC=CC=2)C1C(C=C1)=CC=C1CN1CCCC1 QRRXIQPVIZSLHQ-UHFFFAOYSA-N 0.000 claims description 3
HWGQMRYQVZSGDQ-UHFFFAOYSA-N 7-fluoro-11-(4-fluorophenyl)-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1C(C(N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 HWGQMRYQVZSGDQ-UHFFFAOYSA-N 0.000 claims description 3
XZGBCSIHOXHHNM-UHFFFAOYSA-N methyl 2,3-bis[4-(diethoxymethyl)phenyl]-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound C1=CC(C(OCC)OCC)=CC=C1C1C(C=2C=CC(=CC=2)C(OCC)OCC)C(=O)C2=C(C(=O)OC)C=CC=C2N1 XZGBCSIHOXHHNM-UHFFFAOYSA-N 0.000 claims description 3
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
SOMLCVOFFCJGNU-IRXDYDNUSA-N (11R,12S)-11-(4-fluorophenyl)-12-(1-methylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1[C@@H]([C@@H](N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 SOMLCVOFFCJGNU-IRXDYDNUSA-N 0.000 claims description 2
VGCYLQAHCSEGLE-HOTGVXAUSA-N (11R,12S)-11-(4-fluorophenyl)-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1[C@@H]([C@@H](N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 VGCYLQAHCSEGLE-HOTGVXAUSA-N 0.000 claims description 2
OWJGUHRNNJVRHR-OALUTQOASA-N (11R,12S)-11-[4-[(dimethylamino)methyl]phenyl]-7-fluoro-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1[C@H](N1)[C@H](C=2N(N=CN=2)C)C2=NNC(=O)C3=C2C1=CC(F)=C3 OWJGUHRNNJVRHR-OALUTQOASA-N 0.000 claims description 2
LJXPYHXSPQXFKB-IRXDYDNUSA-N (11R,12S)-7-fluoro-11-(4-fluorophenyl)-12-(1-methylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1[C@@H]([C@@H](N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 LJXPYHXSPQXFKB-IRXDYDNUSA-N 0.000 claims description 2
HWGQMRYQVZSGDQ-HOTGVXAUSA-N (11R,12S)-7-fluoro-11-(4-fluorophenyl)-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1[C@@H]([C@@H](N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 HWGQMRYQVZSGDQ-HOTGVXAUSA-N 0.000 claims description 2
JMRVJHACGJMVJK-IRXDYDNUSA-N (11R,12S)-7-fluoro-12-(1-methylimidazol-2-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1[C@@H]([C@@H](N1)C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 JMRVJHACGJMVJK-IRXDYDNUSA-N 0.000 claims description 2
RJXIQUMBMLJTTJ-HOTGVXAUSA-N (11R,12S)-7-fluoro-12-(2-methyl-1,2,4-triazol-3-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1[C@@H]([C@@H](N1)C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 RJXIQUMBMLJTTJ-HOTGVXAUSA-N 0.000 claims description 2
SOMLCVOFFCJGNU-IAGOWNOFSA-N (11S,12R)-11-(4-fluorophenyl)-12-(1-methylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1[C@H]([C@H](N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 SOMLCVOFFCJGNU-IAGOWNOFSA-N 0.000 claims description 2
VGCYLQAHCSEGLE-HZPDHXFCSA-N (11S,12R)-11-(4-fluorophenyl)-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1[C@H]([C@H](N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 VGCYLQAHCSEGLE-HZPDHXFCSA-N 0.000 claims description 2
OWJGUHRNNJVRHR-RTBURBONSA-N (11S,12R)-11-[4-[(dimethylamino)methyl]phenyl]-7-fluoro-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1[C@@H](N1)[C@@H](C=2N(N=CN=2)C)C2=NNC(=O)C3=C2C1=CC(F)=C3 OWJGUHRNNJVRHR-RTBURBONSA-N 0.000 claims description 2
LJXPYHXSPQXFKB-IAGOWNOFSA-N (11S,12R)-7-fluoro-11-(4-fluorophenyl)-12-(1-methylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1[C@H]([C@H](N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 LJXPYHXSPQXFKB-IAGOWNOFSA-N 0.000 claims description 2
JMRVJHACGJMVJK-IAGOWNOFSA-N (11S,12R)-7-fluoro-12-(1-methylimidazol-2-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1[C@H]([C@H](N1)C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 JMRVJHACGJMVJK-IAGOWNOFSA-N 0.000 claims description 2
HLMLLKFCRNXDCU-UHFFFAOYSA-N 10-ethyl-11,12-diphenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C=12C3=NNC(=O)C2=CC=CC=1N(CC)C(C=1C=CC=CC=1)C3C1=CC=CC=C1 HLMLLKFCRNXDCU-UHFFFAOYSA-N 0.000 claims description 2
OVSNPTZKZPHLSC-UHFFFAOYSA-N 11,12-bis(1-methylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1C(N1)C(C=2N(C=CN=2)C)C2=NNC(=O)C3=C2C1=CC=C3 OVSNPTZKZPHLSC-UHFFFAOYSA-N 0.000 claims description 2
XCTHABQHPYGJGY-UHFFFAOYSA-N 11,12-bis(4-fluorophenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(F)=CC=C1C(N1)C(C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 XCTHABQHPYGJGY-UHFFFAOYSA-N 0.000 claims description 2
ALFPJVGIQSAMIR-UHFFFAOYSA-N 11,12-bis[3-(methylaminomethyl)phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CNCC1=CC=CC(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=C(CNC)C=CC=2)=C1 ALFPJVGIQSAMIR-UHFFFAOYSA-N 0.000 claims description 2
HGZOJDBSTWKIKE-UHFFFAOYSA-N 11,12-bis[3-[(dimethylamino)methyl]phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN(C)CC1=CC=CC(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=C(CN(C)C)C=CC=2)=C1 HGZOJDBSTWKIKE-UHFFFAOYSA-N 0.000 claims description 2
UWMAULNVNHANQX-UHFFFAOYSA-N 11,12-bis[3-[4-(2-methylpropanoyl)piperazine-1-carbonyl]phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1CN(C(=O)C(C)C)CCN1C(=O)C1=CC=CC(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=C(C=CC=2)C(=O)N2CCN(CC2)C(=O)C(C)C)=C1 UWMAULNVNHANQX-UHFFFAOYSA-N 0.000 claims description 2
UMCZUCYEMNNRPS-UHFFFAOYSA-N 11,12-bis[4-[(dimethylamino)methyl]phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(N1)C(C=2C=CC(CN(C)C)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 UMCZUCYEMNNRPS-UHFFFAOYSA-N 0.000 claims description 2
PVKRHCUUSZTERO-UHFFFAOYSA-N 11,12-bis[4-[(dimethylamino)methyl]phenyl]-7-fluoro-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(N1)C(C=2C=CC(CN(C)C)=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 PVKRHCUUSZTERO-UHFFFAOYSA-N 0.000 claims description 2
ULPMFQRNYGWKAD-UHFFFAOYSA-N 11,12-dipyridin-2-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2N=CC=CC=2)C1C1=CC=CC=N1 ULPMFQRNYGWKAD-UHFFFAOYSA-N 0.000 claims description 2
SUVRIGMVTIDCKN-UHFFFAOYSA-N 11,12-dipyridin-3-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2C=NC=CC=2)C1C1=CC=CN=C1 SUVRIGMVTIDCKN-UHFFFAOYSA-N 0.000 claims description 2
UHFNBDDZLDMOPG-UHFFFAOYSA-N 11,12-dipyridin-4-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2C=CN=CC=2)C1C1=CC=NC=C1 UHFNBDDZLDMOPG-UHFFFAOYSA-N 0.000 claims description 2
PRMNVDYRVPGJAB-UHFFFAOYSA-N 11-(1-methylimidazol-2-yl)-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1C(N1)C(C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 PRMNVDYRVPGJAB-UHFFFAOYSA-N 0.000 claims description 2
MZEQOWHGLGJDMY-UHFFFAOYSA-N 11-(4-fluorophenyl)-12-(1,3-thiazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(F)=CC=C1C(N1)C(C=2SC=CN=2)C2=NNC(=O)C3=C2C1=CC=C3 MZEQOWHGLGJDMY-UHFFFAOYSA-N 0.000 claims description 2
CSHDQHUGFZDWGM-UHFFFAOYSA-N 11-(4-fluorophenyl)-12-(1,4,5-trimethylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C(C)=C(C)N=C1C(C(N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 CSHDQHUGFZDWGM-UHFFFAOYSA-N 0.000 claims description 2
SYKVBQHDIBKULJ-UHFFFAOYSA-N 11-(4-fluorophenyl)-12-(1-methylimidazo[4,5-c]pyridin-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N=1C2=CN=CC=C2N(C)C=1C(C=1C2=C(C(NN=1)=O)C=CC=C2N1)C1C1=CC=C(F)C=C1 SYKVBQHDIBKULJ-UHFFFAOYSA-N 0.000 claims description 2
SOMLCVOFFCJGNU-UHFFFAOYSA-N 11-(4-fluorophenyl)-12-(1-methylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1C(C(N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 SOMLCVOFFCJGNU-UHFFFAOYSA-N 0.000 claims description 2
XGKMLUSRYKRTAG-UHFFFAOYSA-N 11-(4-fluorophenyl)-12-(1-methyltriazol-4-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1=NN(C)C=C1C(C(N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 XGKMLUSRYKRTAG-UHFFFAOYSA-N 0.000 claims description 2
VGCYLQAHCSEGLE-UHFFFAOYSA-N 11-(4-fluorophenyl)-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1C(C(N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 VGCYLQAHCSEGLE-UHFFFAOYSA-N 0.000 claims description 2
ZIRPGYGWZRNPEW-UHFFFAOYSA-N 11-(4-fluorophenyl)-12-(4-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=NN=C1C(C(N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 ZIRPGYGWZRNPEW-UHFFFAOYSA-N 0.000 claims description 2
WTDQEXDLIXNPGY-UHFFFAOYSA-N 11-(4-fluorophenyl)-12-methyl-12-(1-methylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1C(C(N1)C=2C=CC(F)=CC=2)(C)C2=NNC(=O)C3=C2C1=CC=C3 WTDQEXDLIXNPGY-UHFFFAOYSA-N 0.000 claims description 2
XRLDTMSBRPPGJH-UHFFFAOYSA-N 11-(4-fluorophenyl)-12-methyl-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1C(C(N1)C=2C=CC(F)=CC=2)(C)C2=NNC(=O)C3=C2C1=CC=C3 XRLDTMSBRPPGJH-UHFFFAOYSA-N 0.000 claims description 2
WSTWDLOACXLTML-UHFFFAOYSA-N 11-[3-(methylaminomethyl)phenyl]-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CNCC1=CC=CC(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=CC=CC=2)=C1 WSTWDLOACXLTML-UHFFFAOYSA-N 0.000 claims description 2
CFSDNTVKFODIGC-UHFFFAOYSA-N 11-[3-(morpholin-4-ylmethyl)phenyl]-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2C=CC=CC=2)C1C(C=1)=CC=CC=1CN1CCOCC1 CFSDNTVKFODIGC-UHFFFAOYSA-N 0.000 claims description 2
SNFZYJVSHCYGBE-UHFFFAOYSA-N 11-[3-[(dimethylamino)methyl]phenyl]-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN(C)CC1=CC=CC(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=CC=CC=2)=C1 SNFZYJVSHCYGBE-UHFFFAOYSA-N 0.000 claims description 2
DDDWCXKAHSQDHC-UHFFFAOYSA-N 11-[4-(azetidin-1-ylmethyl)phenyl]-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2C=CC=CC=2)C1C(C=C1)=CC=C1CN1CCC1 DDDWCXKAHSQDHC-UHFFFAOYSA-N 0.000 claims description 2
MPDITHVJPWECHH-UHFFFAOYSA-N 11-[4-(diethylaminomethyl)phenyl]-12-(4-fluorophenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(CC)CC)=CC=C1C(N1)C(C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 MPDITHVJPWECHH-UHFFFAOYSA-N 0.000 claims description 2
OKSPTCOQOHGNIJ-UHFFFAOYSA-N 11-[4-(diethylaminomethyl)phenyl]-12-(4-methylphenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(CC)CC)=CC=C1C(N1)C(C=2C=CC(C)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 OKSPTCOQOHGNIJ-UHFFFAOYSA-N 0.000 claims description 2
SMEYDFMJRBDOTA-UHFFFAOYSA-N 11-[4-(diethylaminomethyl)phenyl]-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(CC)CC)=CC=C1C(N1)C(C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 SMEYDFMJRBDOTA-UHFFFAOYSA-N 0.000 claims description 2
CFOVOOTVQLBORK-UHFFFAOYSA-N 11-[4-(hydroxymethyl)phenyl]-12-[4-[4-(2-methylpropanoyl)piperazine-1-carbonyl]phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1CN(C(=O)C(C)C)CCN1C(=O)C1=CC=C(C2C=3C4=C(C(NN=3)=O)C=CC=C4NC2C=2C=CC(CO)=CC=2)C=C1 CFOVOOTVQLBORK-UHFFFAOYSA-N 0.000 claims description 2
WQCHPMOBAQVOCU-UHFFFAOYSA-N 11-[4-(hydroxymethyl)phenyl]-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CO)=CC=C1C(N1)C(C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 WQCHPMOBAQVOCU-UHFFFAOYSA-N 0.000 claims description 2
IKPPQLWWWLTQLH-UHFFFAOYSA-N 11-[4-(methylaminomethyl)phenyl]-12-[4-[4-(2-methylpropanoyl)piperazine-1-carbonyl]phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CNC)=CC=C1C(N1)C(C=2C=CC(=CC=2)C(=O)N2CCN(CC2)C(=O)C(C)C)C2=NNC(=O)C3=C2C1=CC=C3 IKPPQLWWWLTQLH-UHFFFAOYSA-N 0.000 claims description 2
NJUKGKLKQXMYSA-UHFFFAOYSA-N 11-[4-(methylaminomethyl)phenyl]-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CNC)=CC=C1C(N1)C(C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 NJUKGKLKQXMYSA-UHFFFAOYSA-N 0.000 claims description 2
FUZJZKQTWVCACG-UHFFFAOYSA-N 11-[4-(morpholin-4-ylmethyl)phenyl]-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2C=CC=CC=2)C1C(C=C1)=CC=C1CN1CCOCC1 FUZJZKQTWVCACG-UHFFFAOYSA-N 0.000 claims description 2
ZSHDOFASTVISRB-UHFFFAOYSA-N 11-[4-[(3,4-dimethylpiperazin-1-yl)methyl]phenyl]-12-(4-fluorophenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1CN(C)C(C)CN1CC1=CC=C(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=CC(F)=CC=2)C=C1 ZSHDOFASTVISRB-UHFFFAOYSA-N 0.000 claims description 2
ABBFNDUPPGZAAV-UHFFFAOYSA-N 11-[4-[(4-ethyl-3-methylpiperazin-1-yl)methyl]phenyl]-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1C(C)N(CC)CCN1CC1=CC=C(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=CC=CC=2)C=C1 ABBFNDUPPGZAAV-UHFFFAOYSA-N 0.000 claims description 2
RLURHVAYHYLCSD-UHFFFAOYSA-N 11-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-12-(4-fluorophenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1CN(CC)CCN1CC1=CC=C(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=CC(F)=CC=2)C=C1 RLURHVAYHYLCSD-UHFFFAOYSA-N 0.000 claims description 2
VFXDUEQGTCMORE-UHFFFAOYSA-N 11-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1CN(CC)CCN1CC1=CC=C(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=CC=CC=2)C=C1 VFXDUEQGTCMORE-UHFFFAOYSA-N 0.000 claims description 2
IBTSZGGZYOHTBG-UHFFFAOYSA-N 11-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1CN(C)CCN1CC1=CC=C(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=CC=CC=2)C=C1 IBTSZGGZYOHTBG-UHFFFAOYSA-N 0.000 claims description 2
BZGNYYGLLLBBFO-UHFFFAOYSA-N 11-[4-[(dimethylamino)methyl]phenyl]-12-(1-methylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(N1)C(C=2N(C=CN=2)C)C2=NNC(=O)C3=C2C1=CC=C3 BZGNYYGLLLBBFO-UHFFFAOYSA-N 0.000 claims description 2
AUBDNOLDYOOXQW-UHFFFAOYSA-N 11-[4-[(dimethylamino)methyl]phenyl]-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(N1)C(C=2N(N=CN=2)C)C2=NNC(=O)C3=C2C1=CC=C3 AUBDNOLDYOOXQW-UHFFFAOYSA-N 0.000 claims description 2
NOGLQGFBESEBOK-UHFFFAOYSA-N 11-[4-[(dimethylamino)methyl]phenyl]-12-(4-ethylphenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CC)=CC=C1C(C(N1)C=2C=CC(CN(C)C)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 NOGLQGFBESEBOK-UHFFFAOYSA-N 0.000 claims description 2
QOITWWGIMYRLSV-UHFFFAOYSA-N 11-[4-[(dimethylamino)methyl]phenyl]-12-(4-fluorophenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(N1)C(C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 QOITWWGIMYRLSV-UHFFFAOYSA-N 0.000 claims description 2
UFIRGOYQXUGEGK-UHFFFAOYSA-N 11-[4-[(dimethylamino)methyl]phenyl]-12-(4-methoxyphenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(OC)=CC=C1C(C(N1)C=2C=CC(CN(C)C)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 UFIRGOYQXUGEGK-UHFFFAOYSA-N 0.000 claims description 2
GVSORFPHFXQBDJ-UHFFFAOYSA-N 11-[4-[(dimethylamino)methyl]phenyl]-12-(4-methylphenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(N1)C(C=2C=CC(C)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 GVSORFPHFXQBDJ-UHFFFAOYSA-N 0.000 claims description 2
PRXUVUNGLYWTRB-UHFFFAOYSA-N 11-[4-[(dimethylamino)methyl]phenyl]-12-(4-propan-2-ylphenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(C(C)C)=CC=C1C(C(N1)C=2C=CC(CN(C)C)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 PRXUVUNGLYWTRB-UHFFFAOYSA-N 0.000 claims description 2
DPNQHTQSOHHDTC-UHFFFAOYSA-N 11-[4-[(dimethylamino)methyl]phenyl]-12-[4-[4-(2-methylpropanoyl)piperazine-1-carbonyl]phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1CN(C(=O)C(C)C)CCN1C(=O)C1=CC=C(C2C=3C4=C(C(NN=3)=O)C=CC=C4NC2C=2C=CC(CN(C)C)=CC=2)C=C1 DPNQHTQSOHHDTC-UHFFFAOYSA-N 0.000 claims description 2
JIVGZFFEZKZOGK-UHFFFAOYSA-N 11-[4-[(dimethylamino)methyl]phenyl]-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(N1)C(C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 JIVGZFFEZKZOGK-UHFFFAOYSA-N 0.000 claims description 2
OWJGUHRNNJVRHR-UHFFFAOYSA-N 11-[4-[(dimethylamino)methyl]phenyl]-7-fluoro-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(N1)C(C=2N(N=CN=2)C)C2=NNC(=O)C3=C2C1=CC(F)=C3 OWJGUHRNNJVRHR-UHFFFAOYSA-N 0.000 claims description 2
AYGBRSIXAPSSRF-UHFFFAOYSA-N 11-[4-[(dimethylamino)methyl]phenyl]-7-fluoro-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(N1)C(C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 AYGBRSIXAPSSRF-UHFFFAOYSA-N 0.000 claims description 2
FTDBTZMEJQSXIP-UHFFFAOYSA-N 11-[4-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]phenyl]-12-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1CN(C(=O)C=2C=CC(=CC=2)C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=CC=CC=2)CCN1C(=O)C1CC1 FTDBTZMEJQSXIP-UHFFFAOYSA-N 0.000 claims description 2
WXZYPXUBMABSFM-UHFFFAOYSA-N 11-phenyl-12-(1,3-thiazol-5-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2SC=NC=2)C1C1=CC=CC=C1 WXZYPXUBMABSFM-UHFFFAOYSA-N 0.000 claims description 2
VLTMPRIFWDKLHQ-UHFFFAOYSA-N 11-phenyl-12-(1-propylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CCCN1C=CN=C1C(C(N1)C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 VLTMPRIFWDKLHQ-UHFFFAOYSA-N 0.000 claims description 2
KYAGVYTXWXXWHD-UHFFFAOYSA-N 11-phenyl-12-(3-propan-2-ylimidazol-4-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CC(C)N1C=NC=C1C(C(N1)C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 KYAGVYTXWXXWHD-UHFFFAOYSA-N 0.000 claims description 2
MVPQSIVTBUKUSY-UHFFFAOYSA-N 11-phenyl-12-propan-2-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C2=CC=CC(C(NN=3)=O)=C2C=3C(C(C)C)C1C1=CC=CC=C1 MVPQSIVTBUKUSY-UHFFFAOYSA-N 0.000 claims description 2
QYXYABNALJXNKZ-UHFFFAOYSA-N 12-(1-ethylimidazol-2-yl)-11-(4-fluorophenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CCN1C=CN=C1C(C(N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 QYXYABNALJXNKZ-UHFFFAOYSA-N 0.000 claims description 2
SMIKAHXAXXLYMI-UHFFFAOYSA-N 12-(1-ethylimidazol-2-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CCN1C=CN=C1C(C(N1)C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 SMIKAHXAXXLYMI-UHFFFAOYSA-N 0.000 claims description 2
CTJVRVJDSGFGEA-UHFFFAOYSA-N 12-(1-methylimidazol-2-yl)-11-[4-(pyrrolidin-1-ylmethyl)phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1C(C(N1)C=2C=CC(CN3CCCC3)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 CTJVRVJDSGFGEA-UHFFFAOYSA-N 0.000 claims description 2
CTGPUFQNQVNVGF-UHFFFAOYSA-N 12-(1-methylimidazol-2-yl)-11-[4-(trifluoromethyl)phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1C(C(N1)C=2C=CC(=CC=2)C(F)(F)F)C2=NNC(=O)C3=C2C1=CC=C3 CTGPUFQNQVNVGF-UHFFFAOYSA-N 0.000 claims description 2
YQARNKZGTURPLI-UHFFFAOYSA-N 12-(1-methylimidazol-2-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1C(C(N1)C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 YQARNKZGTURPLI-UHFFFAOYSA-N 0.000 claims description 2
QATZPBYHOYKNMN-UHFFFAOYSA-N 12-(1H-imidazol-2-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2NC=CN=2)C1C1=CC=CC=C1 QATZPBYHOYKNMN-UHFFFAOYSA-N 0.000 claims description 2
GOMMADJURTTYPW-UHFFFAOYSA-N 12-(2-methyl-1,2,4-triazol-3-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1C(C(N1)C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 GOMMADJURTTYPW-UHFFFAOYSA-N 0.000 claims description 2
GZBPWRIBXCQPHB-UHFFFAOYSA-N 12-(3-methylimidazol-4-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=NC=C1C(C(N1)C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 GZBPWRIBXCQPHB-UHFFFAOYSA-N 0.000 claims description 2
RJHIEEYCHBKHRK-UHFFFAOYSA-N 12-(4-chlorophenyl)-11-[4-(diethylaminomethyl)phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(CC)CC)=CC=C1C(N1)C(C=2C=CC(Cl)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 RJHIEEYCHBKHRK-UHFFFAOYSA-N 0.000 claims description 2
WKMSUEXXCDSEOG-UHFFFAOYSA-N 12-(4-chlorophenyl)-11-[4-[(dimethylamino)methyl]phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(N1)C(C=2C=CC(Cl)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 WKMSUEXXCDSEOG-UHFFFAOYSA-N 0.000 claims description 2
VGUVBXCQHQGENU-UHFFFAOYSA-N 12-(4-fluorophenyl)-11-(1-methylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1C(N1)C(C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 VGUVBXCQHQGENU-UHFFFAOYSA-N 0.000 claims description 2
KUIGPJNDZAUOJX-UHFFFAOYSA-N 12-(4-fluorophenyl)-11-(1H-imidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(F)=CC=C1C(C(N1)C=2NC=CN=2)C2=NNC(=O)C3=C2C1=CC=C3 KUIGPJNDZAUOJX-UHFFFAOYSA-N 0.000 claims description 2
CBAIESABPSTGFG-UHFFFAOYSA-N 12-(4-fluorophenyl)-11-(4-pyrrolidin-2-ylphenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(F)=CC=C1C(C(N1)C=2C=CC(=CC=2)C2NCCC2)C2=NNC(=O)C3=C2C1=CC=C3 CBAIESABPSTGFG-UHFFFAOYSA-N 0.000 claims description 2
RVUQNSXNDVYEDF-UHFFFAOYSA-N 12-(4-fluorophenyl)-11-[4-(1-methylpyrrolidin-2-yl)phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1CCCC1C1=CC=C(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=CC(F)=CC=2)C=C1 RVUQNSXNDVYEDF-UHFFFAOYSA-N 0.000 claims description 2
AQVSDVJMZPJLBR-UHFFFAOYSA-N 12-(4-fluorophenyl)-11-[4-(piperazin-1-ylmethyl)phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(F)=CC=C1C(C(N1)C=2C=CC(CN3CCNCC3)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 AQVSDVJMZPJLBR-UHFFFAOYSA-N 0.000 claims description 2
LMDYVMNOLJGYBG-UHFFFAOYSA-N 12-(4-fluorophenyl)-11-[4-(pyrrolidin-1-ylmethyl)phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(F)=CC=C1C(C(N1)C=2C=CC(CN3CCCC3)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 LMDYVMNOLJGYBG-UHFFFAOYSA-N 0.000 claims description 2
BCTNIKPOLPXQQL-UHFFFAOYSA-N 12-(4-fluorophenyl)-11-[4-[(3-methylpiperazin-1-yl)methyl]phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1CNC(C)CN1CC1=CC=C(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=CC(F)=CC=2)C=C1 BCTNIKPOLPXQQL-UHFFFAOYSA-N 0.000 claims description 2
ZDRMTXUXJOHGQQ-UHFFFAOYSA-N 12-(4-fluorophenyl)-11-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1CN(C)CCN1CC1=CC=C(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=CC(F)=CC=2)C=C1 ZDRMTXUXJOHGQQ-UHFFFAOYSA-N 0.000 claims description 2
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BCUUMIVUHGODBA-UHFFFAOYSA-N 12-(5-methyl-1H-imidazol-2-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CC1=CNC(C2C=3C4=C(C(NN=3)=O)C=CC=C4NC2C=2C=CC=CC=2)=N1 BCUUMIVUHGODBA-UHFFFAOYSA-N 0.000 claims description 2
VMNGIDZDFSFMKU-UHFFFAOYSA-N 12-(furan-3-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C2=COC=C2)C1C1=CC=CC=C1 VMNGIDZDFSFMKU-UHFFFAOYSA-N 0.000 claims description 2
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CQDYKRDOOVHNCO-UHFFFAOYSA-N 12-[3-[(cyclopropylamino)methyl]phenyl]-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2C=C(CNC3CC3)C=CC=2)C1C1=CC=CC=C1 CQDYKRDOOVHNCO-UHFFFAOYSA-N 0.000 claims description 2
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LMIBJOZRXQDHOQ-UHFFFAOYSA-N 12-[3-[(dimethylamino)methyl]phenyl]-11-pyridin-3-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN(C)CC1=CC=CC(C2C=3C4=C(C(NN=3)=O)C=CC=C4NC2C=2C=NC=CC=2)=C1 LMIBJOZRXQDHOQ-UHFFFAOYSA-N 0.000 claims description 2
LQBGRIWERALITD-UHFFFAOYSA-N 12-[3-[(dimethylamino)methyl]phenyl]-11-pyridin-4-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN(C)CC1=CC=CC(C2C=3C4=C(C(NN=3)=O)C=CC=C4NC2C=2C=CN=CC=2)=C1 LQBGRIWERALITD-UHFFFAOYSA-N 0.000 claims description 2
CHBWIIGDWAJIKC-UHFFFAOYSA-N 12-[3-[(dimethylamino)methyl]phenyl]-7-fluoro-11-pyridin-4-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN(C)CC1=CC=CC(C2C=3C4=C(C(NN=3)=O)C=C(F)C=C4NC2C=2C=CN=CC=2)=C1 CHBWIIGDWAJIKC-UHFFFAOYSA-N 0.000 claims description 2
XSMXYXAKAFPLMH-UHFFFAOYSA-N 12-[3-[4-(2-methylpropanoyl)piperazine-1-carbonyl]phenyl]-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1CN(C(=O)C(C)C)CCN1C(=O)C1=CC=CC(C2C=3C4=C(C(NN=3)=O)C=CC=C4NC2C=2C=CC=CC=2)=C1 XSMXYXAKAFPLMH-UHFFFAOYSA-N 0.000 claims description 2
TZXHLGONNRQYGL-UHFFFAOYSA-N 12-[3-[4-(2-methylpropanoyl)piperazine-1-carbonyl]phenyl]-11-pyridin-4-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1CN(C(=O)C(C)C)CCN1C(=O)C1=CC=CC(C2C=3C4=C(C(NN=3)=O)C=CC=C4NC2C=2C=CN=CC=2)=C1 TZXHLGONNRQYGL-UHFFFAOYSA-N 0.000 claims description 2
GSLIQRZFQCDPHC-UHFFFAOYSA-N 12-[3-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]phenyl]-11-[4-[(dimethylamino)methyl]phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(N1)C(C=2C=C(C=CC=2)C(=O)N2CCN(CC2)C(=O)C2CC2)C2=NNC(=O)C3=C2C1=CC=C3 GSLIQRZFQCDPHC-UHFFFAOYSA-N 0.000 claims description 2
YYEBEAXJDIOIQF-UHFFFAOYSA-N 12-[3-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]phenyl]-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1CN(C(=O)C=2C=C(C=CC=2)C2C=3C4=C(C(NN=3)=O)C=CC=C4NC2C=2C=CC=CC=2)CCN1C(=O)C1CC1 YYEBEAXJDIOIQF-UHFFFAOYSA-N 0.000 claims description 2
YGXACEVMNQTDLA-UHFFFAOYSA-N 12-[4-(hydroxymethyl)phenyl]-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CO)=CC=C1C(C(N1)C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 YGXACEVMNQTDLA-UHFFFAOYSA-N 0.000 claims description 2
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PFINSAFXLCPDMX-UHFFFAOYSA-N 12-[4-[(dimethylamino)methyl]phenyl]-11-pyridin-4-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(C(N1)C=2C=CN=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 PFINSAFXLCPDMX-UHFFFAOYSA-N 0.000 claims description 2
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BKVXRYVTBJOFQZ-UHFFFAOYSA-N 12-[4-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]phenyl]-11-[4-(methylaminomethyl)phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CNC)=CC=C1C(N1)C(C=2C=CC(=CC=2)C(=O)N2CCN(CC2)C(=O)C2CC2)C2=NNC(=O)C3=C2C1=CC=C3 BKVXRYVTBJOFQZ-UHFFFAOYSA-N 0.000 claims description 2
MUJKSTBHWXHLOQ-UHFFFAOYSA-N 12-[4-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]phenyl]-11-[4-[(dimethylamino)methyl]phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(N1)C(C=2C=CC(=CC=2)C(=O)N2CCN(CC2)C(=O)C2CC2)C2=NNC(=O)C3=C2C1=CC=C3 MUJKSTBHWXHLOQ-UHFFFAOYSA-N 0.000 claims description 2
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YDZCSPPNLINWHX-UHFFFAOYSA-N 12-phenyl-11-[4-(piperazin-1-ylmethyl)phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2C=CC=CC=2)C1C(C=C1)=CC=C1CN1CCNCC1 YDZCSPPNLINWHX-UHFFFAOYSA-N 0.000 claims description 2
PPSSQDTVKHJDKZ-UHFFFAOYSA-N 12-phenyl-11-piperidin-4-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2C=CC=CC=2)C1C1CCNCC1 PPSSQDTVKHJDKZ-UHFFFAOYSA-N 0.000 claims description 2
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AGZALKKRMJUXQH-UHFFFAOYSA-N ethyl 2,3-bis[4-[(dimethylamino)methyl]phenyl]-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(CN(C)C)=CC=2)C1C1=CC=C(CN(C)C)C=C1 AGZALKKRMJUXQH-UHFFFAOYSA-N 0.000 claims 1
BNRLBPNSVWUZKD-UHFFFAOYSA-N ethyl 2,3-bis[4-[(dimethylamino)methyl]phenyl]-7-fluoro-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC(F)=CC=2NC(C=2C=CC(CN(C)C)=CC=2)C1C1=CC=C(CN(C)C)C=C1 BNRLBPNSVWUZKD-UHFFFAOYSA-N 0.000 claims 1
JLGPFSKXEWLDDV-UHFFFAOYSA-N ethyl 2-(1-benzylimidazol-2-yl)-3-(4-fluorophenyl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2N(C=CN=2)CC=2C=CC=CC=2)C1C1=CC=C(F)C=C1 JLGPFSKXEWLDDV-UHFFFAOYSA-N 0.000 claims 1
VSLKDXFTHQOUKY-UHFFFAOYSA-N ethyl 2-(1-methylimidazol-2-yl)-4-oxo-3-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2N(C=CN=2)C)C1C1=CC=CC=C1 VSLKDXFTHQOUKY-UHFFFAOYSA-N 0.000 claims 1
CMBUDXREQLLSLB-UHFFFAOYSA-N ethyl 2-(4-chlorophenyl)-3-(1-methylimidazol-2-yl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(Cl)=CC=2)C1C1=NC=CN1C CMBUDXREQLLSLB-UHFFFAOYSA-N 0.000 claims 1
QMLOUPZROANHTG-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-2-methyl-3-(1-methylimidazol-2-yl)-4-oxo-1,3-dihydroquinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C)(C=2C=CC(F)=CC=2)C1C1=NC=CN1C QMLOUPZROANHTG-UHFFFAOYSA-N 0.000 claims 1
BFNAOOLMSQCZEJ-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-3-(1-methylimidazo[4,5-c]pyridin-2-yl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical class N=1C2=CN=CC=C2N(C)C=1C1C(=O)C=2C(C(=O)OCC)=CC=CC=2NC1C1=CC=C(F)C=C1 BFNAOOLMSQCZEJ-UHFFFAOYSA-N 0.000 claims 1
AFPGKRAPONIVMT-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-3-(1-methylimidazol-2-yl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(F)=CC=2)C1C1=NC=CN1C AFPGKRAPONIVMT-UHFFFAOYSA-N 0.000 claims 1
QDEYAJCMBLULRU-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-3-methyl-3-(1-methylimidazol-2-yl)-4-oxo-1,2-dihydroquinoline-5-carboxylate Chemical compound N=1C=CN(C)C=1C1(C)C(=O)C=2C(C(=O)OCC)=CC=CC=2NC1C1=CC=C(F)C=C1 QDEYAJCMBLULRU-UHFFFAOYSA-N 0.000 claims 1
KZZSMVAEZMEDRW-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-3-methyl-3-(2-methyl-1,2,4-triazol-3-yl)-4-oxo-1,2-dihydroquinoline-5-carboxylate Chemical compound N=1C=NN(C)C=1C1(C)C(=O)C=2C(C(=O)OCC)=CC=CC=2NC1C1=CC=C(F)C=C1 KZZSMVAEZMEDRW-UHFFFAOYSA-N 0.000 claims 1
NNWVSDMVLZLPAH-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-4-oxo-3-(1,3-thiazol-2-yl)-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(F)=CC=2)C1C1=NC=CS1 NNWVSDMVLZLPAH-UHFFFAOYSA-N 0.000 claims 1
XIMILWYBBQYQSQ-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-4-oxo-3-(1,4,5-trimethylimidazol-2-yl)-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(F)=CC=2)C1C1=NC(C)=C(C)N1C XIMILWYBBQYQSQ-UHFFFAOYSA-N 0.000 claims 1
IAMPCRSWOPNYRZ-UHFFFAOYSA-N ethyl 2-[3-(diethoxymethyl)phenyl]-4-oxo-3-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound CCOC(OCC)C1=CC=CC(C2C(C(=O)C3=C(C(=O)OCC)C=CC=C3N2)C=2C=CC=CC=2)=C1 IAMPCRSWOPNYRZ-UHFFFAOYSA-N 0.000 claims 1
UDRVOHBVRQMMLA-UHFFFAOYSA-N ethyl 2-[3-(dimethylcarbamoyl)-4-fluorophenyl]-3-(1-methylimidazol-2-yl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=C(C(F)=CC=2)C(=O)N(C)C)C1C1=NC=CN1C UDRVOHBVRQMMLA-UHFFFAOYSA-N 0.000 claims 1
JUUBLEGOUCGPNS-UHFFFAOYSA-N ethyl 2-[4-(diethoxymethyl)phenyl]-3-(1-methylimidazol-2-yl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound C1=CC(C(OCC)OCC)=CC=C1C1C(C=2N(C=CN=2)C)C(=O)C2=C(C(=O)OCC)C=CC=C2N1 JUUBLEGOUCGPNS-UHFFFAOYSA-N 0.000 claims 1
HKSOUYFBQAXMFT-UHFFFAOYSA-N ethyl 2-[4-(diethoxymethyl)phenyl]-3-(4-fluorophenyl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound C1=CC(C(OCC)OCC)=CC=C1C1C(C=2C=CC(F)=CC=2)C(=O)C2=C(C(=O)OCC)C=CC=C2N1 HKSOUYFBQAXMFT-UHFFFAOYSA-N 0.000 claims 1
VLJNAKQPNOBPCB-UHFFFAOYSA-N ethyl 2-[4-(diethoxymethyl)phenyl]-3-[4-(dimethylcarbamoyl)phenyl]-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound C1=CC(C(OCC)OCC)=CC=C1C1C(C=2C=CC(=CC=2)C(=O)N(C)C)C(=O)C2=C(C(=O)OCC)C=CC=C2N1 VLJNAKQPNOBPCB-UHFFFAOYSA-N 0.000 claims 1
CETZJSDMWAMDQS-UHFFFAOYSA-N ethyl 2-[4-(diethylaminomethyl)phenyl]-3-(4-methylphenyl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(CN(CC)CC)=CC=2)C1C1=CC=C(C)C=C1 CETZJSDMWAMDQS-UHFFFAOYSA-N 0.000 claims 1
WNMFIRUEGFTIHK-UHFFFAOYSA-N ethyl 2-[4-(dimethoxymethyl)phenyl]-3-(4-fluorophenyl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(=CC=2)C(OC)OC)C1C1=CC=C(F)C=C1 WNMFIRUEGFTIHK-UHFFFAOYSA-N 0.000 claims 1
OFIPRZSZUPZKJK-UHFFFAOYSA-N ethyl 2-[4-(dimethylcarbamoyl)phenyl]-3-(1-methylimidazol-2-yl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(=CC=2)C(=O)N(C)C)C1C1=NC=CN1C OFIPRZSZUPZKJK-UHFFFAOYSA-N 0.000 claims 1
UFZKDIBUZREHJX-UHFFFAOYSA-N ethyl 2-[4-(dimethylcarbamoyl)phenyl]-3-(4-fluorophenyl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(=CC=2)C(=O)N(C)C)C1C1=CC=C(F)C=C1 UFZKDIBUZREHJX-UHFFFAOYSA-N 0.000 claims 1
VIUDEMJYYAZHRC-UHFFFAOYSA-N ethyl 2-[4-[(dimethylamino)methyl]phenyl]-3-(2-methyl-1,2,4-triazol-3-yl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(CN(C)C)=CC=2)C1C1=NC=NN1C VIUDEMJYYAZHRC-UHFFFAOYSA-N 0.000 claims 1
UTSXBBQJMADPAT-UHFFFAOYSA-N ethyl 2-[4-[(dimethylamino)methyl]phenyl]-3-(4-ethylphenyl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(CN(C)C)=CC=2)C1C1=CC=C(CC)C=C1 UTSXBBQJMADPAT-UHFFFAOYSA-N 0.000 claims 1
MGSZKKQOYRAIHK-UHFFFAOYSA-N ethyl 2-[4-[(dimethylamino)methyl]phenyl]-3-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(CN(C)C)=CC=2)C1C1=CC=C(OC)C=C1 MGSZKKQOYRAIHK-UHFFFAOYSA-N 0.000 claims 1
FDGAXXMCWOSFDQ-UHFFFAOYSA-N ethyl 2-[4-[(dimethylamino)methyl]phenyl]-3-(4-methylphenyl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(CN(C)C)=CC=2)C1C1=CC=C(C)C=C1 FDGAXXMCWOSFDQ-UHFFFAOYSA-N 0.000 claims 1
IBMMVYWTVCWIJK-UHFFFAOYSA-N ethyl 2-[4-[(dimethylamino)methyl]phenyl]-4-oxo-3-(4-propan-2-ylphenyl)-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(CN(C)C)=CC=2)C1C1=CC=C(C(C)C)C=C1 IBMMVYWTVCWIJK-UHFFFAOYSA-N 0.000 claims 1
PMLSVPVZWNEAFX-UHFFFAOYSA-N ethyl 2-[4-[(dimethylamino)methyl]phenyl]-4-oxo-3-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(CN(C)C)=CC=2)C1C1=CC=C(C(F)(F)F)C=C1 PMLSVPVZWNEAFX-UHFFFAOYSA-N 0.000 claims 1
FHYABALFAPKGSY-UHFFFAOYSA-N ethyl 2-[4-[(dimethylamino)methyl]phenyl]-7-fluoro-3-(4-fluorophenyl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC(F)=CC=2NC(C=2C=CC(CN(C)C)=CC=2)C1C1=CC=C(F)C=C1 FHYABALFAPKGSY-UHFFFAOYSA-N 0.000 claims 1
YCCXFZGOZRYWFT-UHFFFAOYSA-N ethyl 2-[4-[(dimethylamino)methyl]phenyl]-7-fluoro-4-oxo-3-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC(F)=CC=2NC(C=2C=CC(CN(C)C)=CC=2)C1C1=CC=CC=C1 YCCXFZGOZRYWFT-UHFFFAOYSA-N 0.000 claims 1
VMUZNERDVGESPZ-UHFFFAOYSA-N ethyl 3-(1-ethylimidazol-2-yl)-2-(4-fluorophenyl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(F)=CC=2)C1C1=NC=CN1CC VMUZNERDVGESPZ-UHFFFAOYSA-N 0.000 claims 1
YQMPKXOVNKXSLT-UHFFFAOYSA-N ethyl 3-(1-methylimidazol-2-yl)-4-oxo-2-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(=CC=2)C(F)(F)F)C1C1=NC=CN1C YQMPKXOVNKXSLT-UHFFFAOYSA-N 0.000 claims 1
ILONNCGILZLJGK-UHFFFAOYSA-N ethyl 3-(1-methylimidazol-2-yl)-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC=CC=2)C1C1=NC=CN1C ILONNCGILZLJGK-UHFFFAOYSA-N 0.000 claims 1
VWOQEXBULGUSBQ-UHFFFAOYSA-N ethyl 3-(2-methyl-1,2,4-triazol-3-yl)-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC=CC=2)C1C1=NC=NN1C VWOQEXBULGUSBQ-UHFFFAOYSA-N 0.000 claims 1
MBYIYRLBEXDWAI-UHFFFAOYSA-N ethyl 3-(3-methylimidazol-4-yl)-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC=CC=2)C1C1=CN=CN1C MBYIYRLBEXDWAI-UHFFFAOYSA-N 0.000 claims 1
CVYBMONEKPAWRS-UHFFFAOYSA-N ethyl 3-(4,5-dimethyl-1,2,4-triazol-3-yl)-2-(4-fluorophenyl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical class O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(F)=CC=2)C1C1=NN=C(C)N1C CVYBMONEKPAWRS-UHFFFAOYSA-N 0.000 claims 1
AKRWOGBSNIVRMV-UHFFFAOYSA-N ethyl 3-(4-chlorophenyl)-2-[4-(diethylaminomethyl)phenyl]-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(CN(CC)CC)=CC=2)C1C1=CC=C(Cl)C=C1 AKRWOGBSNIVRMV-UHFFFAOYSA-N 0.000 claims 1
QTMZSDDJAPNTKM-UHFFFAOYSA-N ethyl 3-(4-chlorophenyl)-2-[4-[(dimethylamino)methyl]phenyl]-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(CN(C)C)=CC=2)C1C1=CC=C(Cl)C=C1 QTMZSDDJAPNTKM-UHFFFAOYSA-N 0.000 claims 1
FJDHDENLVOQGCL-UHFFFAOYSA-N ethyl 3-(4-fluorophenyl)-2-(1-methylimidazol-2-yl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2N(C=CN=2)C)C1C1=CC=C(F)C=C1 FJDHDENLVOQGCL-UHFFFAOYSA-N 0.000 claims 1
NUARACIRZFRIAM-UHFFFAOYSA-N ethyl 3-(4-fluorophenyl)-2-[4-(1-methylpyrrolidin-2-yl)phenyl]-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(=CC=2)C2N(CCC2)C)C1C1=CC=C(F)C=C1 NUARACIRZFRIAM-UHFFFAOYSA-N 0.000 claims 1
ARYGCRPNACTOEN-UHFFFAOYSA-N ethyl 3-(4-fluorophenyl)-3-hydroxy-2-(1-methylimidazol-2-yl)-4-oxo-1,2-dihydroquinoline-5-carboxylate Chemical compound C=1C=C(F)C=CC=1C1(O)C(=O)C=2C(C(=O)OCC)=CC=CC=2NC1C1=NC=CN1C ARYGCRPNACTOEN-UHFFFAOYSA-N 0.000 claims 1
FALWQPRYPOXNCS-UHFFFAOYSA-N ethyl 3-(furan-3-yl)-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC=CC=2)C1C=1C=COC=1 FALWQPRYPOXNCS-UHFFFAOYSA-N 0.000 claims 1
YZUSZEHUZBZCLI-UHFFFAOYSA-N ethyl 3-[4-(diethoxymethyl)phenyl]-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound C1=CC(C(OCC)OCC)=CC=C1C1C(=O)C2=C(C(=O)OCC)C=CC=C2NC1C1=CC=CC=C1 YZUSZEHUZBZCLI-UHFFFAOYSA-N 0.000 claims 1
OJNUOMQBJLXTPR-UHFFFAOYSA-N ethyl 3-[4-(dimethylcarbamoyl)phenyl]-2-(4-fluorophenyl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC(F)=CC=2)C1C1=CC=C(C(=O)N(C)C)C=C1 OJNUOMQBJLXTPR-UHFFFAOYSA-N 0.000 claims 1
HOIALGDPPDVTAU-UHFFFAOYSA-N ethyl 4-hydroxy-2-oxo-3-phenyl-1h-quinoline-5-carboxylate Chemical compound OC=1C=2C(C(=O)OCC)=CC=CC=2NC(=O)C=1C1=CC=CC=C1 HOIALGDPPDVTAU-UHFFFAOYSA-N 0.000 claims 1
ZQANTAZPSYEVAK-UHFFFAOYSA-N ethyl 4-oxo-2,3-diphenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC=CC=2)C1C1=CC=CC=C1 ZQANTAZPSYEVAK-UHFFFAOYSA-N 0.000 claims 1
PMEMMBQUJSKOSW-UHFFFAOYSA-N ethyl 4-oxo-2,3-dipyridin-2-yl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2N=CC=CC=2)C1C1=CC=CC=N1 PMEMMBQUJSKOSW-UHFFFAOYSA-N 0.000 claims 1
IFGWEUSAKMZUIY-UHFFFAOYSA-N ethyl 4-oxo-2,3-dipyridin-3-yl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=NC=CC=2)C1C1=CC=CN=C1 IFGWEUSAKMZUIY-UHFFFAOYSA-N 0.000 claims 1
LNLCAJICVHWCAT-UHFFFAOYSA-N ethyl 4-oxo-2,3-dipyridin-4-yl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CN=CC=2)C1C1=CC=NC=C1 LNLCAJICVHWCAT-UHFFFAOYSA-N 0.000 claims 1
UUQDAVUKLNEOHO-UHFFFAOYSA-N ethyl 4-oxo-2-phenyl-3-(1-propylimidazol-2-yl)-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound CCCN1C=CN=C1C1C(=O)C2=C(C(=O)OCC)C=CC=C2NC1C1=CC=CC=C1 UUQDAVUKLNEOHO-UHFFFAOYSA-N 0.000 claims 1
VAWVQRIWDYJWJX-UHFFFAOYSA-N ethyl 4-oxo-2-phenyl-3-(3-propan-2-ylimidazol-4-yl)-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CC=CC=2)C1C1=CN=CN1C(C)C VAWVQRIWDYJWJX-UHFFFAOYSA-N 0.000 claims 1
PADYOQFMXVPDCD-UHFFFAOYSA-N ethyl 4-oxo-3-phenyl-2-pyridin-4-yl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC=CC=2NC(C=2C=CN=CC=2)C1C1=CC=CC=C1 PADYOQFMXVPDCD-UHFFFAOYSA-N 0.000 claims 1
ZBBMHIITTFMSMN-UHFFFAOYSA-N ethyl 7-chloro-3-(1-methylimidazol-2-yl)-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC(Cl)=CC=2NC(C=2C=CC=CC=2)C1C1=NC=CN1C ZBBMHIITTFMSMN-UHFFFAOYSA-N 0.000 claims 1
MOEJGSWWRPRROK-UHFFFAOYSA-N ethyl 7-fluoro-2-(1-methylimidazol-2-yl)-4-oxo-3-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC(F)=CC=2NC(C=2N(C=CN=2)C)C1C1=CC=CC=C1 MOEJGSWWRPRROK-UHFFFAOYSA-N 0.000 claims 1
XGJNOGVXMBNWHT-UHFFFAOYSA-N ethyl 7-fluoro-2-(4-fluorophenyl)-3-(2-methyl-1,2,4-triazol-3-yl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC(F)=CC=2NC(C=2C=CC(F)=CC=2)C1C1=NC=NN1C XGJNOGVXMBNWHT-UHFFFAOYSA-N 0.000 claims 1
GHNGFTLWJHAYKC-UHFFFAOYSA-N ethyl 7-fluoro-3-(1-methylimidazol-2-yl)-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC(F)=CC=2NC(C=2C=CC=CC=2)C1C1=NC=CN1C GHNGFTLWJHAYKC-UHFFFAOYSA-N 0.000 claims 1
LIHOBKPSYULLFA-UHFFFAOYSA-N ethyl 7-fluoro-3-(2-methyl-1,2,4-triazol-3-yl)-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC(F)=CC=2NC(C=2C=CC=CC=2)C1C1=NC=NN1C LIHOBKPSYULLFA-UHFFFAOYSA-N 0.000 claims 1
ITTPXLUQKQOEPA-UHFFFAOYSA-N ethyl 7-fluoro-3-(4-fluorophenyl)-2-(1-methylimidazol-2-yl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OCC)=CC(F)=CC=2NC(C=2N(C=CN=2)C)C1C1=CC=C(F)C=C1 ITTPXLUQKQOEPA-UHFFFAOYSA-N 0.000 claims 1
ZVYVPGLRVWUPMP-FYSMJZIKSA-N exatecan Chemical compound C1C[C@H](N)C2=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC3=CC(F)=C(C)C1=C32 ZVYVPGLRVWUPMP-FYSMJZIKSA-N 0.000 claims 1
229950009429 exatecan Drugs 0.000 claims 1
208000005017 glioblastoma Diseases 0.000 claims 1
201000005787 hematologic cancer Diseases 0.000 claims 1
208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 1
150000002460 imidazoles Chemical class 0.000 claims 1
125000002883 imidazolyl group Chemical group 0.000 claims 1
230000001771 impaired effect Effects 0.000 claims 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
208000027866 inflammatory disease Diseases 0.000 claims 1
239000003112 inhibitor Substances 0.000 claims 1
230000005764 inhibitory process Effects 0.000 claims 1
230000005865 ionizing radiation Effects 0.000 claims 1
208000037906 ischaemic injury Diseases 0.000 claims 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
208000032839 leukemia Diseases 0.000 claims 1
201000005202 lung cancer Diseases 0.000 claims 1
208000020816 lung neoplasm Diseases 0.000 claims 1
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238000004519 manufacturing process Methods 0.000 claims 1
201000001441 melanoma Diseases 0.000 claims 1
GLFOCQJMOGFBDZ-UHFFFAOYSA-N methyl 2,3-bis(4-fluorophenyl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=CC(F)=CC=2)C1C1=CC=C(F)C=C1 GLFOCQJMOGFBDZ-UHFFFAOYSA-N 0.000 claims 1
WHFIRCSNBYLHPE-UHFFFAOYSA-N methyl 2,3-bis[3-[4-(2-methylpropanoyl)piperazine-1-carbonyl]phenyl]-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=C(C=CC=2)C(=O)N2CCN(CC2)C(=O)C(C)C)C1C(C=1)=CC=CC=1C(=O)N1CCN(C(=O)C(C)C)CC1 WHFIRCSNBYLHPE-UHFFFAOYSA-N 0.000 claims 1
MHDPPWLYRPZMSG-UHFFFAOYSA-N methyl 2,3-bis[4-[(dimethylamino)methyl]phenyl]-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=CC(CN(C)C)=CC=2)C1C1=CC=C(CN(C)C)C=C1 MHDPPWLYRPZMSG-UHFFFAOYSA-N 0.000 claims 1
VGHUTAOZZJDHNR-UHFFFAOYSA-N methyl 2-(1-methylimidazol-2-yl)-4-oxo-3-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2N(C=CN=2)C)C1C1=CC=CC=C1 VGHUTAOZZJDHNR-UHFFFAOYSA-N 0.000 claims 1
ZWXSRTHTJMAHHP-UHFFFAOYSA-N methyl 2-[3-(diethoxymethyl)phenyl]-4-oxo-3-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound CCOC(OCC)C1=CC=CC(C2C(C(=O)C3=C(C(=O)OC)C=CC=C3N2)C=2C=CC=CC=2)=C1 ZWXSRTHTJMAHHP-UHFFFAOYSA-N 0.000 claims 1
LRCKJNAWURRNHP-UHFFFAOYSA-N methyl 2-[4-(diethoxymethyl)phenyl]-3-[4-[4-(2-methylpropanoyl)piperazine-1-carbonyl]phenyl]-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical class C1=CC(C(OCC)OCC)=CC=C1C1C(C=2C=CC(=CC=2)C(=O)N2CCN(CC2)C(=O)C(C)C)C(=O)C2=C(C(=O)OC)C=CC=C2N1 LRCKJNAWURRNHP-UHFFFAOYSA-N 0.000 claims 1
RKAASDXHANACTJ-UHFFFAOYSA-N methyl 2-[4-(dimethoxymethyl)phenyl]-3-(4-fluorophenyl)-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound C1=CC(C(OC)OC)=CC=C1C1C(C=2C=CC(F)=CC=2)C(=O)C2=C(C(=O)OC)C=CC=C2N1 RKAASDXHANACTJ-UHFFFAOYSA-N 0.000 claims 1
XRRYBBJVIHJYFG-UHFFFAOYSA-N methyl 2-[4-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]phenyl]-4-oxo-3-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=CC(=CC=2)C(=O)N2CCN(CC2)C(=O)C2CC2)C1C1=CC=CC=C1 XRRYBBJVIHJYFG-UHFFFAOYSA-N 0.000 claims 1
SIEFNWTVNGKFQC-UHFFFAOYSA-N methyl 3-(1-benzyl-4-methylimidazol-2-yl)-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=CC=CC=2)C1C1=NC(C)=CN1CC1=CC=CC=C1 SIEFNWTVNGKFQC-UHFFFAOYSA-N 0.000 claims 1
HYOQMCDTAHJJNN-UHFFFAOYSA-N methyl 3-(1-benzylimidazol-2-yl)-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=CC=CC=2)C1C1=NC=CN1CC1=CC=CC=C1 HYOQMCDTAHJJNN-UHFFFAOYSA-N 0.000 claims 1
PYGKJHATGDPARQ-UHFFFAOYSA-N methyl 3-(1-ethylimidazol-2-yl)-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound CCN1C=CN=C1C1C(=O)C2=C(C(=O)OC)C=CC=C2NC1C1=CC=CC=C1 PYGKJHATGDPARQ-UHFFFAOYSA-N 0.000 claims 1
UTTWJYUSDPHIRJ-UHFFFAOYSA-N methyl 3-[3-[4-(2-methylpropanoyl)piperazine-1-carbonyl]phenyl]-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=CC=CC=2)C1C(C=1)=CC=CC=1C(=O)N1CCN(C(=O)C(C)C)CC1 UTTWJYUSDPHIRJ-UHFFFAOYSA-N 0.000 claims 1
WVTPAFNONPVVPS-UHFFFAOYSA-N methyl 3-[3-[4-(2-methylpropanoyl)piperazine-1-carbonyl]phenyl]-4-oxo-2-pyridin-4-yl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=CN=CC=2)C1C(C=1)=CC=CC=1C(=O)N1CCN(C(=O)C(C)C)CC1 WVTPAFNONPVVPS-UHFFFAOYSA-N 0.000 claims 1
ZRXQYIOXNVIXPY-UHFFFAOYSA-N methyl 3-[3-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]phenyl]-2-[4-(diethoxymethyl)phenyl]-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound C1=CC(C(OCC)OCC)=CC=C1C1C(C=2C=C(C=CC=2)C(=O)N2CCN(CC2)C(=O)C2CC2)C(=O)C2=C(C(=O)OC)C=CC=C2N1 ZRXQYIOXNVIXPY-UHFFFAOYSA-N 0.000 claims 1
OUZQYBVCOBVBKI-UHFFFAOYSA-N methyl 3-[3-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]phenyl]-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=CC=CC=2)C1C(C=1)=CC=CC=1C(=O)N(CC1)CCN1C(=O)C1CC1 OUZQYBVCOBVBKI-UHFFFAOYSA-N 0.000 claims 1
JQZMMKIMDMZOMR-UHFFFAOYSA-N methyl 3-[4-(diethoxymethyl)phenyl]-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound C1=CC(C(OCC)OCC)=CC=C1C1C(=O)C2=C(C(=O)OC)C=CC=C2NC1C1=CC=CC=C1 JQZMMKIMDMZOMR-UHFFFAOYSA-N 0.000 claims 1
UCBNCRSHTDTCIF-UHFFFAOYSA-N methyl 3-[4-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]phenyl]-2-[4-(diethoxymethyl)phenyl]-4-oxo-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound C1=CC(C(OCC)OCC)=CC=C1C1C(C=2C=CC(=CC=2)C(=O)N2CCN(CC2)C(=O)C2CC2)C(=O)C2=C(C(=O)OC)C=CC=C2N1 UCBNCRSHTDTCIF-UHFFFAOYSA-N 0.000 claims 1
FMMPJUORDNWBKX-UHFFFAOYSA-N methyl 3-[4-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]phenyl]-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=CC=CC=2)C1C(C=C1)=CC=C1C(=O)N(CC1)CCN1C(=O)C1CC1 FMMPJUORDNWBKX-UHFFFAOYSA-N 0.000 claims 1
JMLKXJQUWDYENK-UHFFFAOYSA-N methyl 3-[4-[[methyl(phenylmethoxycarbonyl)amino]methyl]phenyl]-4-oxo-2-phenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=CC=CC=2)C1C(C=C1)=CC=C1CN(C)C(=O)OCC1=CC=CC=C1 JMLKXJQUWDYENK-UHFFFAOYSA-N 0.000 claims 1
QQCUYEOLFHGPIU-UHFFFAOYSA-N methyl 4-oxo-2,3-diphenyl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=CC=CC=2)C1C1=CC=CC=C1 QQCUYEOLFHGPIU-UHFFFAOYSA-N 0.000 claims 1
VQPCVIKMPUSHGG-UHFFFAOYSA-N methyl 4-oxo-2,3-dipyridin-2-yl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2N=CC=CC=2)C1C1=CC=CC=N1 VQPCVIKMPUSHGG-UHFFFAOYSA-N 0.000 claims 1
SYDGHCIRSOGKGK-UHFFFAOYSA-N methyl 4-oxo-2,3-dipyridin-3-yl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=NC=CC=2)C1C1=CC=CN=C1 SYDGHCIRSOGKGK-UHFFFAOYSA-N 0.000 claims 1
ZOZVIDBDYWXNBM-UHFFFAOYSA-N methyl 4-oxo-2,3-dipyridin-4-yl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=CN=CC=2)C1C1=CC=NC=C1 ZOZVIDBDYWXNBM-UHFFFAOYSA-N 0.000 claims 1
HTYLOAMVZIFWML-UHFFFAOYSA-N methyl 4-oxo-2-phenyl-3-(1,3-thiazol-5-yl)-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2C=CC=CC=2)C1C1=CN=CS1 HTYLOAMVZIFWML-UHFFFAOYSA-N 0.000 claims 1
WRLSQGQPVNAZND-UHFFFAOYSA-N methyl 4-oxo-2-phenyl-3-propan-2-yl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound CC(C)C1C(=O)C=2C(C(=O)OC)=CC=CC=2NC1C1=CC=CC=C1 WRLSQGQPVNAZND-UHFFFAOYSA-N 0.000 claims 1
NVEXNMMLCAENKO-UHFFFAOYSA-N methyl 4-oxo-3-phenyl-2-pyridin-2-yl-2,3-dihydro-1h-quinoline-5-carboxylate Chemical compound O=C1C=2C(C(=O)OC)=CC=CC=2NC(C=2N=CC=CC=2)C1C1=CC=CC=C1 NVEXNMMLCAENKO-UHFFFAOYSA-N 0.000 claims 1
MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical group COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 claims 1
201000006417 multiple sclerosis Diseases 0.000 claims 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
230000007135 neurotoxicity Effects 0.000 claims 1
231100000228 neurotoxicity Toxicity 0.000 claims 1
201000002528 pancreatic cancer Diseases 0.000 claims 1
208000008443 pancreatic carcinoma Diseases 0.000 claims 1
102000004169 proteins and genes Human genes 0.000 claims 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
101150010682 rad50 gene Proteins 0.000 claims 1
VHXNKPBCCMUMSW-FQEVSTJZSA-N rubitecan Chemical compound C1=CC([N+]([O-])=O)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VHXNKPBCCMUMSW-FQEVSTJZSA-N 0.000 claims 1
229950009213 rubitecan Drugs 0.000 claims 1
230000009291 secondary effect Effects 0.000 claims 1
230000036303 septic shock Effects 0.000 claims 1
VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 claims 1
229930192474 thiophene Natural products 0.000 claims 1
229960000303 topotecan Drugs 0.000 claims 1
UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims 1
208000019553 vascular disease Diseases 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
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239000007787 solid Substances 0.000 description 6
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
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ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
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238000004587 chromatography analysis Methods 0.000 description 1
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229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1

JP2011522113A 2008-08-06 2009-07-27 ポリ（ａｄｐ−リボース）ポリメラーゼ（ｐａｒｐ）のジヒドロピリドフタラジノン阻害剤 Active JP5984389B2 (ja)