KR20010020386A - 포스포디에스테라제 4를 억제하는 디아제피노인돌론 - Google Patents

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Publication number

KR20010020386A

KR20010020386A KR1019997010008A KR19997010008A KR20010020386A KR 20010020386 A KR20010020386 A KR 20010020386A KR 1019997010008 A KR1019997010008 A KR 1019997010008A KR 19997010008 A KR19997010008 A KR 19997010008A KR 20010020386 A KR20010020386 A KR 20010020386A

Authority

KR

South Korea

Prior art keywords

oxo

methyl

phenyl

dihydro

quinazolin

Prior art date

1997-04-30

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.)

Ceased

Links

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• ZWOMUDQWODQGQH-UHFFFAOYSA-N 1H-pyrrolo[2,3-g][1,2]benzodiazepin-2-one Chemical class C1=CC2=NN=CC=CC2=C2C1=CC(=O)N2 ZWOMUDQWODQGQH-UHFFFAOYSA-N 0.000 title claims description 41
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 title description 8
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 title description 8
• 238000000034 method Methods 0.000 claims abstract description 135
• 150000001875 compounds Chemical class 0.000 claims abstract description 109
• 208000006673 asthma Diseases 0.000 claims abstract description 10
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims abstract description 7
• 206010065687 Bone loss Diseases 0.000 claims abstract description 5
• 206010012438 Dermatitis atopic Diseases 0.000 claims abstract description 5
• 206010067125 Liver injury Diseases 0.000 claims abstract description 5
• 201000008937 atopic dermatitis Diseases 0.000 claims abstract description 5
• 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
• 206010040070 Septic Shock Diseases 0.000 claims abstract description 3
• 230000036303 septic shock Effects 0.000 claims abstract description 3
• -1 2,5-dimethyl-4-oxo-4H-quinazolin-3-yl Chemical group 0.000 claims description 115
• 239000000203 mixture Substances 0.000 claims description 101
• 239000000460 chlorine Substances 0.000 claims description 95
• 239000000543 intermediate Substances 0.000 claims description 70
• 239000002904 solvent Substances 0.000 claims description 56
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
• 150000001412 amines Chemical class 0.000 claims description 38
• 239000002253 acid Substances 0.000 claims description 35
• 239000001257 hydrogen Substances 0.000 claims description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 35
• KCKIKSJECTZLJA-UHFFFAOYSA-N indol-4-one Chemical compound O=C1C=CC=C2N=CC=C12 KCKIKSJECTZLJA-UHFFFAOYSA-N 0.000 claims description 33
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
• 150000002431 hydrogen Chemical class 0.000 claims description 26
• 150000003839 salts Chemical class 0.000 claims description 20
• 239000002609 medium Substances 0.000 claims description 17
• 150000002148 esters Chemical class 0.000 claims description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
• 238000006243 chemical reaction Methods 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• GSXVPNLAOHBBKA-UHFFFAOYSA-N 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-4-oxoquinazoline-7-carboxylic acid Chemical compound C=1C(C)=CC=2CCN(C(C(N=3)N4C(C5=CC=C(C=C5N=C4C)C(O)=O)=O)=O)C=2C=1C=3C1=CC=CC=C1 GSXVPNLAOHBBKA-UHFFFAOYSA-N 0.000 claims description 11
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 11
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 10
• HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 claims description 9
• 230000009435 amidation Effects 0.000 claims description 9
• 238000007112 amidation reaction Methods 0.000 claims description 9
• 150000001408 amides Chemical class 0.000 claims description 9
• 125000000524 functional group Chemical group 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• RTDDGJVVKVRATF-UHFFFAOYSA-N 1,10-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7,9-pentaen-12-one Chemical group O=C1CN=Cc2cccc3ccn1c23 RTDDGJVVKVRATF-UHFFFAOYSA-N 0.000 claims description 7
• 229910021529 ammonia Inorganic materials 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 230000002829 reductive effect Effects 0.000 claims description 7
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 150000002466 imines Chemical class 0.000 claims description 6
• 230000007935 neutral effect Effects 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• 208000011231 Crohn disease Diseases 0.000 claims description 5
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 5
• 229910052987 metal hydride Inorganic materials 0.000 claims description 5
• 150000004681 metal hydrides Chemical class 0.000 claims description 5
• DAJBLWXUFLHGGH-DEOSSOPVSA-N (11S)-11-(2-methyl-4-oxoquinazolin-3-yl)-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound N([C@H](C(N1CCC=2C=CC=C3C1=2)=O)N1C(=O)C2=CC=CC=C2N=C1C)=C3C1=CC=CC=C1 DAJBLWXUFLHGGH-DEOSSOPVSA-N 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
• 239000004472 Lysine Substances 0.000 claims description 4
• 230000006181 N-acylation Effects 0.000 claims description 4
• 239000003377 acid catalyst Substances 0.000 claims description 4
• 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 4
• 235000008206 alpha-amino acids Nutrition 0.000 claims description 4
• 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 4
• 239000004220 glutamic acid Substances 0.000 claims description 4
• 239000002243 precursor Substances 0.000 claims description 4
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
• 239000000376 reactant Substances 0.000 claims description 4
• 229910052979 sodium sulfide Inorganic materials 0.000 claims description 4
• GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 4
• PKVZSJLYYVGXRM-QHCPKHFHSA-N (11S)-11-(2-methyl-4-oxopyrido[3,4-d]pyrimidin-3-yl)-6-nitro-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound N([C@H](C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N1C(=O)C2=CC=NC=C2N=C1C)=C3C1=CC=CC=C1 PKVZSJLYYVGXRM-QHCPKHFHSA-N 0.000 claims description 3
• GCQYMZYZLNYUSY-VWLOTQADSA-N (11S)-11-(5-fluoro-2-methyl-4-oxoquinazolin-3-yl)-6-methyl-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound C=1C(C)=CC=2CCN(C([C@@H](N=3)N4C(C5=C(F)C=CC=C5N=C4C)=O)=O)C=2C=1C=3C1=CC=CC=C1 GCQYMZYZLNYUSY-VWLOTQADSA-N 0.000 claims description 3
• YJLSARIGMMOOGK-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-4-oxoquinazoline-7-carboxylate Chemical compound C=1C(C)=CC=2CCN(C3=O)C=2C=1C(C=1C=CC=CC=1)=NC3N(C(C1=CC=2)=O)C(C)=NC1=CC=2C(=O)OC1=C(F)C(F)=C(F)C(F)=C1F YJLSARIGMMOOGK-UHFFFAOYSA-N 0.000 claims description 3
• UQPGREVGZRHTAK-UHFFFAOYSA-N 11-(2,5-dimethyl-4-oxoquinazolin-3-yl)-6-nitro-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound CC1=NC2=CC=CC(C)=C2C(=O)N1C(C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N=C3C1=CC=CC=C1 UQPGREVGZRHTAK-UHFFFAOYSA-N 0.000 claims description 3
• FKMLEKVIYSANCY-UHFFFAOYSA-N 11-(2,6-dimethyl-4-oxoquinazolin-3-yl)-6-nitro-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound O=C1C2=CC(C)=CC=C2N=C(C)N1C(C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N=C3C1=CC=CC=C1 FKMLEKVIYSANCY-UHFFFAOYSA-N 0.000 claims description 3
• PNFWYEXLXYPSPZ-UHFFFAOYSA-N 11-(2,7-dimethyl-4-oxoquinazolin-3-yl)-6-nitro-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound C=1C(C)=CC=C(C2=O)C=1N=C(C)N2C(C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N=C3C1=CC=CC=C1 PNFWYEXLXYPSPZ-UHFFFAOYSA-N 0.000 claims description 3
• LUQNQFIQFJBKRV-UHFFFAOYSA-N 11-(2,8-dimethyl-4-oxoquinazolin-3-yl)-6-nitro-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound CC1=NC2=C(C)C=CC=C2C(=O)N1C(C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N=C3C1=CC=CC=C1 LUQNQFIQFJBKRV-UHFFFAOYSA-N 0.000 claims description 3
• RGERZKVLIURXPY-UHFFFAOYSA-N 11-(2-methyl-4-oxoquinazolin-3-yl)-6-nitro-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound CC1=NC2=CC=CC=C2C(=O)N1C(C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N=C3C1=CC=CC=C1 RGERZKVLIURXPY-UHFFFAOYSA-N 0.000 claims description 3
• AZQNANWJQLZKCT-UHFFFAOYSA-N 11-(5-chloro-2-methyl-4-oxoquinazolin-3-yl)-6-methyl-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound C=1C(C)=CC=2CCN(C(C(N=3)N4C(C5=C(Cl)C=CC=C5N=C4C)=O)=O)C=2C=1C=3C1=CC=CC=C1 AZQNANWJQLZKCT-UHFFFAOYSA-N 0.000 claims description 3
• HXSPYSYFRCKEPX-UHFFFAOYSA-N 11-(5-chloro-2-methyl-4-oxoquinazolin-3-yl)-6-nitro-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound CC1=NC2=CC=CC(Cl)=C2C(=O)N1C(C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N=C3C1=CC=CC=C1 HXSPYSYFRCKEPX-UHFFFAOYSA-N 0.000 claims description 3
• FGVLFFGUYNXWKT-UHFFFAOYSA-N 11-[2-(methoxymethyl)-4-oxoquinazolin-3-yl]-6-methyl-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound COCC1=NC2=CC=CC=C2C(=O)N1C(C(N1CCC=2C=C(C)C=C3C1=2)=O)N=C3C1=CC=CC=C1 FGVLFFGUYNXWKT-UHFFFAOYSA-N 0.000 claims description 3
• MEULVEMAASHPAZ-UHFFFAOYSA-N 2-acetyloxyethyl 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-4-oxoquinazoline-7-carboxylate Chemical compound C=1C(C(=O)OCCOC(=O)C)=CC=C(C2=O)C=1N=C(C)N2C(C(N1CCC=2C=C(C)C=C3C1=2)=O)N=C3C1=CC=CC=C1 MEULVEMAASHPAZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
• IFMSCYUQRZNAFK-UHFFFAOYSA-N 2-methoxyethyl 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-4-oxoquinazoline-7-carboxylate Chemical compound C=1C(C(=O)OCCOC)=CC=C(C2=O)C=1N=C(C)N2C(C(N1CCC=2C=C(C)C=C3C1=2)=O)N=C3C1=CC=CC=C1 IFMSCYUQRZNAFK-UHFFFAOYSA-N 0.000 claims description 3
• AJGTXMYFYOYFFV-UHFFFAOYSA-N 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-4-oxoquinazoline-5-carboxylic acid Chemical compound C=1C(C)=CC=2CCN(C(C(N=3)N4C(C5=C(C(O)=O)C=CC=C5N=C4C)=O)=O)C=2C=1C=3C1=CC=CC=C1 AJGTXMYFYOYFFV-UHFFFAOYSA-N 0.000 claims description 3
• WPSKYVMJHNFMOZ-UHFFFAOYSA-N 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-4-oxoquinazoline-7-carbonitrile Chemical compound C=1C(C)=CC=2CCN(C(C(N=3)N4C(C5=CC=C(C=C5N=C4C)C#N)=O)=O)C=2C=1C=3C1=CC=CC=C1 WPSKYVMJHNFMOZ-UHFFFAOYSA-N 0.000 claims description 3
• WWCKONRFPLGFIA-UHFFFAOYSA-N 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-4-oxoquinazoline-7-carboxamide Chemical compound C=1C(C)=CC=2CCN(C(C(N=3)N4C(C5=CC=C(C=C5N=C4C)C(N)=O)=O)=O)C=2C=1C=3C1=CC=CC=C1 WWCKONRFPLGFIA-UHFFFAOYSA-N 0.000 claims description 3
• MNGFGZLQQZOPHM-UHFFFAOYSA-N 2-methyl-3-(6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-N-(2-morpholin-4-ylethyl)-4-oxoquinazoline-7-carboxamide Chemical compound C=1C(C)=CC=2CCN(C3=O)C=2C=1C(C=1C=CC=CC=1)=NC3N(C(C1=CC=2)=O)C(C)=NC1=CC=2C(=O)NCCN1CCOCC1 MNGFGZLQQZOPHM-UHFFFAOYSA-N 0.000 claims description 3
• GSXVPNLAOHBBKA-RUZDIDTESA-N 2-methyl-3-[(11R)-6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl]-4-oxoquinazoline-7-carboxylic acid Chemical compound C=1C(C)=CC=2CCN(C([C@H](N=3)N4C(C5=CC=C(C=C5N=C4C)C(O)=O)=O)=O)C=2C=1C=3C1=CC=CC=C1 GSXVPNLAOHBBKA-RUZDIDTESA-N 0.000 claims description 3
• GSXVPNLAOHBBKA-VWLOTQADSA-N 2-methyl-3-[(11S)-6-methyl-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl]-4-oxoquinazoline-7-carboxylic acid Chemical compound C=1C(C)=CC=2CCN(C([C@@H](N=3)N4C(C5=CC=C(C=C5N=C4C)C(O)=O)=O)=O)C=2C=1C=3C1=CC=CC=C1 GSXVPNLAOHBBKA-VWLOTQADSA-N 0.000 claims description 3
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• LQAPQOZOEQHAPS-UHFFFAOYSA-N 3-(6-amino-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-2-methyl-4-oxoquinazoline-7-carboxylic acid Chemical compound CC1=NC2=CC(C(O)=O)=CC=C2C(=O)N1C(C(N1CCC=2C=C(N)C=C3C1=2)=O)N=C3C1=CC=CC=C1 LQAPQOZOEQHAPS-UHFFFAOYSA-N 0.000 claims description 3
• QDPBNMRFDOTINQ-UHFFFAOYSA-N 3-(6-methoxy-12-oxo-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-11-yl)-2-methyl-4-oxoquinazoline-7-carboxylic acid Chemical compound C=1C(OC)=CC=2CCN(C(C(N=3)N4C(C5=CC=C(C=C5N=C4C)C(O)=O)=O)=O)C=2C=1C=3C1=CC=CC=C1 QDPBNMRFDOTINQ-UHFFFAOYSA-N 0.000 claims description 3
• UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 3
• ZCGHSRSNETYNGK-UHFFFAOYSA-N 6-amino-11-(2,5-dimethyl-4-oxoquinazolin-3-yl)-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(C)N1C(C(N1CCC=2C=C(N)C=C3C1=2)=O)N=C3C1=CC=CC=C1 ZCGHSRSNETYNGK-UHFFFAOYSA-N 0.000 claims description 3
• MAFQVPGPTOTYMX-UHFFFAOYSA-N 6-amino-11-(2,6-dimethyl-4-oxoquinazolin-3-yl)-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound O=C1C2=CC(C)=CC=C2N=C(C)N1C(C(N1CCC=2C=C(N)C=C3C1=2)=O)N=C3C1=CC=CC=C1 MAFQVPGPTOTYMX-UHFFFAOYSA-N 0.000 claims description 3
• OTCUEKHKDLNSDY-UHFFFAOYSA-N 6-amino-11-(2,8-dimethyl-4-oxoquinazolin-3-yl)-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound CC1=CC=CC(C2=O)=C1N=C(C)N2C(C(N1CCC=2C=C(N)C=C3C1=2)=O)N=C3C1=CC=CC=C1 OTCUEKHKDLNSDY-UHFFFAOYSA-N 0.000 claims description 3
• UPZQLUGOLBVHKF-UHFFFAOYSA-N 6-amino-11-(2-methyl-4-oxoquinazolin-3-yl)-9-phenyl-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound CC1=NC2=CC=CC=C2C(=O)N1C(C(N1CCC=2C=C(N)C=C3C1=2)=O)N=C3C1=CC=CC=C1 UPZQLUGOLBVHKF-UHFFFAOYSA-N 0.000 claims description 3
• ZSAGZZJKZGCMMI-UHFFFAOYSA-N 6-amino-9-phenyl-11-(2,6,8-trimethyl-4-oxoquinazolin-3-yl)-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound O=C1C2=CC(C)=CC(C)=C2N=C(C)N1C(C(N1CCC=2C=C(N)C=C3C1=2)=O)N=C3C1=CC=CC=C1 ZSAGZZJKZGCMMI-UHFFFAOYSA-N 0.000 claims description 3
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• HCUIGULJWLKGQI-UHFFFAOYSA-N 6-nitro-9-phenyl-11-(2,6,8-trimethyl-4-oxoquinazolin-3-yl)-1,10-diazatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one Chemical compound O=C1C2=CC(C)=CC(C)=C2N=C(C)N1C(C(N1CCC=2C=C(C=C3C1=2)[N+]([O-])=O)=O)N=C3C1=CC=CC=C1 HCUIGULJWLKGQI-UHFFFAOYSA-N 0.000 claims description 3
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