ES2709034T3 - Pirimido[4,5-b]quinolina-4,5 (3h,10h)-dionas como supresores de mutaciones sin sentido - Google Patents

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Publication number

ES2709034T3

ES2709034T3 ES13826612T ES13826612T ES2709034T3 ES 2709034 T3 ES2709034 T3 ES 2709034T3 ES 13826612 T ES13826612 T ES 13826612T ES 13826612 T ES13826612 T ES 13826612T ES 2709034 T3 ES2709034 T3 ES 2709034T3

Authority

ES

Spain

Prior art keywords

alkyl

quinoline

dione

amino

cycloalkyl

Prior art date

2012-12-13

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 108020004485 Nonsense Codon Proteins 0.000 title claims abstract description 54
• 230000037434 nonsense mutation Effects 0.000 title claims abstract description 53
• MJZUERYJESLETK-UHFFFAOYSA-N 1,10-dihydropyrimido[4,5-b]quinoline-4,5-dione Chemical class N1C2=CC=CC=C2C(=O)C2=C1NC=NC2=O MJZUERYJESLETK-UHFFFAOYSA-N 0.000 title description 3
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 432
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 187
• 150000002367 halogens Chemical class 0.000 claims abstract description 186
• 150000001875 compounds Chemical class 0.000 claims abstract description 169
• 125000004122 cyclic group Chemical group 0.000 claims abstract description 169
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 167
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 157
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 154
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 142
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 142
• 239000001257 hydrogen Substances 0.000 claims abstract description 142
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 121
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 107
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 102
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 101
• 125000003118 aryl group Chemical group 0.000 claims abstract description 85
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 83
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 80
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 73
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 73
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 72
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 72
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 72
• 239000001301 oxygen Chemical group 0.000 claims abstract description 72
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 72
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 71
• 229910052717 sulfur Chemical group 0.000 claims abstract description 71
• 239000011593 sulfur Chemical group 0.000 claims abstract description 71
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 66
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 66
• 150000003839 salts Chemical class 0.000 claims abstract description 61
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract description 52
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 46
• 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 45
• 201000010099 disease Diseases 0.000 claims abstract description 38
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims abstract description 36
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 36
• 239000003814 drug Substances 0.000 claims abstract description 23
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 16
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 16
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 13
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 9
• 125000006413 ring segment Chemical group 0.000 claims abstract description 8
• 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 7
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 62
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 55
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 54
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 51
• -1 3,5-dimethylphenyl Chemical group 0.000 claims description 43
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 32
• 125000003282 alkyl amino group Chemical group 0.000 claims description 20
• 125000004429 atom Chemical group 0.000 claims description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims description 18
• 229940079593 drug Drugs 0.000 claims description 15
• AJTVCXKJEWUISC-UHFFFAOYSA-N 10-methyl-3-phenyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 AJTVCXKJEWUISC-UHFFFAOYSA-N 0.000 claims description 10
• AFLBQLGPVYRZJR-UHFFFAOYSA-N 10-methyl-2-pentyl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCCCCC1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 AFLBQLGPVYRZJR-UHFFFAOYSA-N 0.000 claims description 7
• QGXVTZRIRPNXAA-UHFFFAOYSA-N 10-methyl-3-phenyl-2-propylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCCC1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 QGXVTZRIRPNXAA-UHFFFAOYSA-N 0.000 claims description 7
• RZDACIUIPZFAOS-UHFFFAOYSA-N 2-ethyl-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCC1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 RZDACIUIPZFAOS-UHFFFAOYSA-N 0.000 claims description 7
• YRIYCZQXKIZHNK-UHFFFAOYSA-N 3-(3,5-dimethylphenyl)-10-methyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC(C)=CC(C)=C1 YRIYCZQXKIZHNK-UHFFFAOYSA-N 0.000 claims description 7
• WQQLNMTUVMLBTP-UHFFFAOYSA-N 3-(3,5-dimethylphenyl)-10-methyl-2-propylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCCC1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC(C)=CC(C)=C1 WQQLNMTUVMLBTP-UHFFFAOYSA-N 0.000 claims description 7
• OKGWETOVKKQGOC-UHFFFAOYSA-N 3-(3,5-dimethylphenyl)-2-ethyl-10-methylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCC1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC(C)=CC(C)=C1 OKGWETOVKKQGOC-UHFFFAOYSA-N 0.000 claims description 7
• YIWNPOLQIUGSPL-UHFFFAOYSA-N 3-cyclopentyl-2-propan-2-yl-10-prop-2-enylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(CC=C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1CCCC1 YIWNPOLQIUGSPL-UHFFFAOYSA-N 0.000 claims description 7
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
• XUOTZAUZHWCGHL-UHFFFAOYSA-N 2-cyclobutyl-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CN1C2=CC=CC=C2C(=O)C(C(N2C=3C=CC=CC=3)=O)=C1N=C2C1CCC1 XUOTZAUZHWCGHL-UHFFFAOYSA-N 0.000 claims description 6
• PMPNXFKPNSJZJF-UHFFFAOYSA-N 3-(3,5-dimethylphenyl)-10-methyl-2-pentylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCCCCC1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC(C)=CC(C)=C1 PMPNXFKPNSJZJF-UHFFFAOYSA-N 0.000 claims description 6
• SJIVMSFHBQNOKF-UHFFFAOYSA-N 3-cyclohexyl-10-methyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1CCCCC1 SJIVMSFHBQNOKF-UHFFFAOYSA-N 0.000 claims description 6
• OOCZRFRDHDLJRA-UHFFFAOYSA-N 3-cyclohexyl-10-methyl-2-propylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCCC1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1CCCCC1 OOCZRFRDHDLJRA-UHFFFAOYSA-N 0.000 claims description 6
• GYHLYFIGSOVXRL-UHFFFAOYSA-N 3-cyclopentyl-10-methyl-2-pentylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCCCCC1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1CCCC1 GYHLYFIGSOVXRL-UHFFFAOYSA-N 0.000 claims description 6
• BQFAXUQGGXIZMM-UHFFFAOYSA-N 3-cyclopentyl-10-methyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1CCCC1 BQFAXUQGGXIZMM-UHFFFAOYSA-N 0.000 claims description 6
• MKINHZSCOUWIHE-UHFFFAOYSA-N 3-cyclopentyl-10-methyl-2-propylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCCC1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1CCCC1 MKINHZSCOUWIHE-UHFFFAOYSA-N 0.000 claims description 6
• NSNDMKNVWQNEBL-UHFFFAOYSA-N 3-cyclopentyl-2-propan-2-yl-10h-pyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2NC3=CC=CC=C3C(=O)C=2C(=O)N1C1CCCC1 NSNDMKNVWQNEBL-UHFFFAOYSA-N 0.000 claims description 6
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
• KIDUCMGZPJQLPG-UHFFFAOYSA-N 2-ethylsulfanyl-3-phenyl-10h-pyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCSC1=NC=2NC3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 KIDUCMGZPJQLPG-UHFFFAOYSA-N 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• YLGSYGGBTZEXLF-UHFFFAOYSA-N 10-(2-aminoethyl)-2-cyclobutyl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound NCCN1C2=CC=CC=C2C(=O)C(C(N2C=3C=CC=CC=3)=O)=C1N=C2C1CCC1 YLGSYGGBTZEXLF-UHFFFAOYSA-N 0.000 claims description 4
• GVSJTYPPSYDOAF-UHFFFAOYSA-N 10-(2-aminoethyl)-3-phenyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(CCN)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 GVSJTYPPSYDOAF-UHFFFAOYSA-N 0.000 claims description 4
• CDVMEKWXTQEFKG-UHFFFAOYSA-N 10-(2-hydroxyethyl)-3-phenyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(CCO)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 CDVMEKWXTQEFKG-UHFFFAOYSA-N 0.000 claims description 4
• UHFVRKUPSAXREP-UHFFFAOYSA-N 10-(2-methoxyethyl)-3-phenyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound COCCN1C2=CC=CC=C2C(=O)C(C2=O)=C1N=C(C(C)C)N2C1=CC=CC=C1 UHFVRKUPSAXREP-UHFFFAOYSA-N 0.000 claims description 4
• ZJUNGAAJIKQNRK-UHFFFAOYSA-N 10-methyl-2-(3-methylcyclobutyl)-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound C1C(C)CC1C(N(C1=O)C=2C=CC=CC=2)=NC2=C1C(=O)C1=CC=CC=C1N2C ZJUNGAAJIKQNRK-UHFFFAOYSA-N 0.000 claims description 4
• OSKDZKXJXWZSAV-UHFFFAOYSA-N 10-methyl-2-pentan-3-yl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCC(CC)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 OSKDZKXJXWZSAV-UHFFFAOYSA-N 0.000 claims description 4
• FXQBTMJYASRROA-UHFFFAOYSA-N 10-methyl-2-propan-2-yl-3-(2-propan-2-ylphenyl)pyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=CC=CC=C1N1C(=O)C(C(=O)C2=CC=CC=C2N2C)=C2N=C1C(C)C FXQBTMJYASRROA-UHFFFAOYSA-N 0.000 claims description 4
• KANGOBNCEMBZOT-UHFFFAOYSA-N 10-methyl-2-propan-2-yl-3-[2-(trifluoromethyl)phenyl]pyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1C(F)(F)F KANGOBNCEMBZOT-UHFFFAOYSA-N 0.000 claims description 4
• PMBWCSIBCMQYQI-UHFFFAOYSA-N 10-methyl-3-(2-methylphenyl)-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1C PMBWCSIBCMQYQI-UHFFFAOYSA-N 0.000 claims description 4
• APZCBQVPJBUHOY-UHFFFAOYSA-N 10-methyl-3-(oxan-3-yl)-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1CCCOC1 APZCBQVPJBUHOY-UHFFFAOYSA-N 0.000 claims description 4
• DOGZGVKBERKLDE-UHFFFAOYSA-N 10-methyl-3-(oxan-4-yl)-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound C(C)(C)C=1N(C(C2=C(N(C3=CC=CC=C3C2=O)C)N1)=O)C1CCOCC1 DOGZGVKBERKLDE-UHFFFAOYSA-N 0.000 claims description 4
• FXYDGAUFBLVZKG-UHFFFAOYSA-N 10-methyl-3-piperidin-1-yl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1N1CCCCC1 FXYDGAUFBLVZKG-UHFFFAOYSA-N 0.000 claims description 4
• UNRFXCUBWGBIFZ-UHFFFAOYSA-N 2,8-dihydroquinoline-6,7-dione Chemical compound N=1CC=CC2=CC(C(CC=12)=O)=O UNRFXCUBWGBIFZ-UHFFFAOYSA-N 0.000 claims description 4
• IPOXGFINNYJLNF-UHFFFAOYSA-N 2-(3,3-dimethylcyclobutyl)-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CN1C2=CC=CC=C2C(=O)C(C(N2C=3C=CC=CC=3)=O)=C1N=C2C1CC(C)(C)C1 IPOXGFINNYJLNF-UHFFFAOYSA-N 0.000 claims description 4
• YDNBJEBDWYMWLI-UHFFFAOYSA-N 2-(3-methoxycyclobutyl)-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound C1C(OC)CC1C(N(C1=O)C=2C=CC=CC=2)=NC2=C1C(=O)C1=CC=CC=C1N2C YDNBJEBDWYMWLI-UHFFFAOYSA-N 0.000 claims description 4
• VBIZBFXISRBSQP-UHFFFAOYSA-N 2-(3-methoxypropyl)-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound COCCCC1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 VBIZBFXISRBSQP-UHFFFAOYSA-N 0.000 claims description 4
• HPBWLSHITILJGA-UHFFFAOYSA-N 2-(4-methoxybutyl)-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound COCCCCC1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 HPBWLSHITILJGA-UHFFFAOYSA-N 0.000 claims description 4
• ROFPZFAMQLCEHM-UHFFFAOYSA-N 2-(dimethylamino)-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CN(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 ROFPZFAMQLCEHM-UHFFFAOYSA-N 0.000 claims description 4
• TWBNGWUKGVLXDW-UHFFFAOYSA-N 2-butyl-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCCCC1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 TWBNGWUKGVLXDW-UHFFFAOYSA-N 0.000 claims description 4
• MQNROLMZODTCLU-UHFFFAOYSA-N 2-cyclobutyl-10-(2-hydroxyethyl)-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound OCCN1C2=CC=CC=C2C(=O)C(C(N2C=3C=CC=CC=3)=O)=C1N=C2C1CCC1 MQNROLMZODTCLU-UHFFFAOYSA-N 0.000 claims description 4
• RDMZIKXXHILBBJ-UHFFFAOYSA-N 2-cyclobutyl-3-phenyl-10h-pyrimido[4,5-b]quinoline-4,5-dione Chemical compound C1CCC1C1=NC=2NC3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 RDMZIKXXHILBBJ-UHFFFAOYSA-N 0.000 claims description 4
• MVBSDSAQVLFZKR-UHFFFAOYSA-N 2-cyclopentyl-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CN1C2=CC=CC=C2C(=O)C(C(N2C=3C=CC=CC=3)=O)=C1N=C2C1CCCC1 MVBSDSAQVLFZKR-UHFFFAOYSA-N 0.000 claims description 4
• SXOVPDSRBVJYOK-UHFFFAOYSA-N 2-cyclopropyl-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CN1C2=CC=CC=C2C(=O)C(C(N2C=3C=CC=CC=3)=O)=C1N=C2C1CC1 SXOVPDSRBVJYOK-UHFFFAOYSA-N 0.000 claims description 4
• JVHOJZICPPHKQV-UHFFFAOYSA-N 2-heptyl-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCCCCCCC1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 JVHOJZICPPHKQV-UHFFFAOYSA-N 0.000 claims description 4
• DZSKHIMLIIZWQK-UHFFFAOYSA-N 2-tert-butyl-3-cyclopentyl-10-methylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CN1C2=CC=CC=C2C(=O)C(C2=O)=C1N=C(C(C)(C)C)N2C1CCCC1 DZSKHIMLIIZWQK-UHFFFAOYSA-N 0.000 claims description 4
• HCBOGFQXDPFJHD-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-10-methyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=C(Cl)C=CC=C1Cl HCBOGFQXDPFJHD-UHFFFAOYSA-N 0.000 claims description 4
• XUFSQHNFIVPDAO-UHFFFAOYSA-N 3-(2-bromophenyl)-10-methyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1Br XUFSQHNFIVPDAO-UHFFFAOYSA-N 0.000 claims description 4
• JOBBNECOHYFSNQ-UHFFFAOYSA-N 3-(2-chlorophenyl)-10-methyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1Cl JOBBNECOHYFSNQ-UHFFFAOYSA-N 0.000 claims description 4
• XWSUEPKHTKUPCW-UHFFFAOYSA-N 3-(2-fluorophenyl)-10-methyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1F XWSUEPKHTKUPCW-UHFFFAOYSA-N 0.000 claims description 4
• NHGKPNJAMXQUOK-UHFFFAOYSA-N 3-(2-methoxyphenyl)-10-methyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound COC1=CC=CC=C1N1C(=O)C(C(=O)C2=CC=CC=C2N2C)=C2N=C1C(C)C NHGKPNJAMXQUOK-UHFFFAOYSA-N 0.000 claims description 4
• GWIMOQDSJAIBBL-UHFFFAOYSA-N 3-(3-chlorophenyl)-10-methyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CC(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC(Cl)=C1 GWIMOQDSJAIBBL-UHFFFAOYSA-N 0.000 claims description 4
• MSQFXAYKUKJJGP-UHFFFAOYSA-N 3-(3-methoxyphenyl)-10-methyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound COC1=CC=CC(N2C(C=3C(=O)C4=CC=CC=C4N(C)C=3N=C2C(C)C)=O)=C1 MSQFXAYKUKJJGP-UHFFFAOYSA-N 0.000 claims description 4
• XSZRSVDMMTZQJG-UHFFFAOYSA-N 3-cyclopentyl-10-ethyl-2-propan-2-ylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCN1C2=CC=CC=C2C(=O)C(C2=O)=C1N=C(C(C)C)N2C1CCCC1 XSZRSVDMMTZQJG-UHFFFAOYSA-N 0.000 claims description 4
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