EA028673B1 - ПИРИМИДО[4,5-b]ХИНОЛИН-4,5(3H,10H)ДИОНЫ В КАЧЕСТВЕ СУПРЕССОРОВ НОНСЕНС МУТАЦИЙ - Google Patents

Info

Publication number

EA028673B1

EA028673B1 EA201591105A EA201591105A EA028673B1 EA 028673 B1 EA028673 B1 EA 028673B1 EA 201591105 A EA201591105 A EA 201591105A EA 201591105 A EA201591105 A EA 201591105A EA 028673 B1 EA028673 B1 EA 028673B1

Authority

EA

Eurasian Patent Office

Prior art keywords

quinoline

dione

methyl

isopropyl

phenylpyrimido

Prior art date

2012-12-13

Links

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• Global Dossier
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• 108020004485 Nonsense Codon Proteins 0.000 title claims description 52
• 230000037434 nonsense mutation Effects 0.000 title claims description 51
• 150000001875 compounds Chemical class 0.000 claims abstract description 146
• 150000003839 salts Chemical class 0.000 claims abstract description 45
• 239000003814 drug Substances 0.000 claims abstract description 14
• 238000002360 preparation method Methods 0.000 claims abstract description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 153
• -1 3,5-dimethylphenyl Chemical group 0.000 claims description 90
• 229910052739 hydrogen Inorganic materials 0.000 claims description 53
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 53
• 239000001257 hydrogen Substances 0.000 claims description 51
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 42
• 229910052736 halogen Inorganic materials 0.000 claims description 38
• 150000002367 halogens Chemical class 0.000 claims description 38
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
• 150000002431 hydrogen Chemical class 0.000 claims description 34
• 201000010099 disease Diseases 0.000 claims description 33
• 125000003545 alkoxy group Chemical group 0.000 claims description 29
• 125000001424 substituent group Chemical group 0.000 claims description 29
• 125000004122 cyclic group Chemical group 0.000 claims description 26
• 230000000694 effects Effects 0.000 claims description 24
• 238000000034 method Methods 0.000 claims description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
• 125000005842 heteroatom Chemical group 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 22
• 229920006395 saturated elastomer Polymers 0.000 claims description 22
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 21
• 239000001301 oxygen Chemical group 0.000 claims description 21
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
• 125000002950 monocyclic group Chemical group 0.000 claims description 20
• 229910052717 sulfur Chemical group 0.000 claims description 20
• 239000011593 sulfur Chemical group 0.000 claims description 20
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 19
• 125000003282 alkyl amino group Chemical group 0.000 claims description 19
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
• 239000003513 alkali Substances 0.000 claims description 13
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 12
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 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 5
• 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 5
• 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 4
• 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 4
• 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 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
• NZVURNMUTOYLSG-UHFFFAOYSA-N 2-(dimethylamino)-3-phenyl-10h-pyrimido[4,5-b]quinoline-4,5-dione Chemical compound CN(C)C1=NC=2NC3=CC=CC=C3C(=O)C=2C(=O)N1C1=CC=CC=C1 NZVURNMUTOYLSG-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• NMBXOVKFWROLHT-UHFFFAOYSA-N 3-cyclopentyl-10-methyl-4,5-dioxo-2-propan-2-ylpyrimido[4,5-b]quinoline-7-carbonitrile Chemical compound CC(C)C1=NC=2N(C)C3=CC=C(C#N)C=C3C(=O)C=2C(=O)N1C1CCCC1 NMBXOVKFWROLHT-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 3
• 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 3
• 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 3
• 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 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
• 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 2
• 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 2
• AEDFEQWPTBPSDH-UHFFFAOYSA-N 3-cyclopentyl-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)N1C1CCCC1 AEDFEQWPTBPSDH-UHFFFAOYSA-N 0.000 claims description 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• SCUCYCRANOULJA-UHFFFAOYSA-N 2-butan-2-yl-3-cyclopentyl-10-methylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound CCC(C)C1=NC=2N(C)C3=CC=CC=C3C(=O)C=2C(=O)N1C1CCCC1 SCUCYCRANOULJA-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• 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 2
• GSLKFMBDBYFCBT-UHFFFAOYSA-N 2-cyclobutyl-3-(2,6-dichlorophenyl)-10-methylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound C1(CCC1)C=1N(C(C2=C(N(C3=CC=CC=C3C2=O)C)N1)=O)C1=C(C=CC=C1Cl)Cl GSLKFMBDBYFCBT-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• 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 2
• 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 2
• 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 2
• ZTEAZYFBTUQHFV-UHFFFAOYSA-N 2-hexyl-10-methyl-3-phenylpyrimido[4,5-b]quinoline-4,5-dione Chemical compound C(CCCCC)C=1N(C(C2=C(N(C3=CC=CC=C3C2=O)C)N1)=O)C1=CC=CC=C1 ZTEAZYFBTUQHFV-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• 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 2
• 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 2
• 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 2
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