SK282491B6 - Pyridazíndióny, spôsob a medziprodukty na ich výrobu, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

Info

Publication number

SK282491B6

SK282491B6 SK504-96A SK50496A SK282491B6 SK 282491 B6 SK282491 B6 SK 282491B6 SK 50496 A SK50496 A SK 50496A SK 282491 B6 SK282491 B6 SK 282491B6

Authority

SK

Slovakia

Prior art keywords

chloro

quinoline

hydroxy

dione

tetrahydropyridazino

Prior art date

1993-10-22

Links

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• 238000000034 method Methods 0.000 title claims abstract description 62
• 230000008569 process Effects 0.000 title claims abstract description 18
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 13
• MYKHANQTTIRZJK-UHFFFAOYSA-N pyridazine-3,4-dione Chemical class O=C1C=CN=NC1=O MYKHANQTTIRZJK-UHFFFAOYSA-N 0.000 title claims abstract description 9
• 238000002360 preparation method Methods 0.000 title claims description 28
• 239000000543 intermediate Substances 0.000 title abstract description 34
• 150000001875 compounds Chemical class 0.000 claims abstract description 340
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 78
• 125000003118 aryl group Chemical group 0.000 claims abstract description 55
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 52
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 40
• 150000003839 salts Chemical class 0.000 claims abstract description 38
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 38
• 125000001424 substituent group Chemical class 0.000 claims abstract description 21
• 208000012902 Nervous system disease Diseases 0.000 claims abstract description 7
• 208000025966 Neurological disease Diseases 0.000 claims abstract description 7
• 230000002265 prevention Effects 0.000 claims abstract description 5
• 239000003257 excitatory amino acid Substances 0.000 claims abstract description 3
• 230000002461 excitatory amino acid Effects 0.000 claims abstract description 3
• -1 oxa a zole Chemical compound 0.000 claims description 207
• 229910052799 carbon Inorganic materials 0.000 claims description 181
• 229910052739 hydrogen Inorganic materials 0.000 claims description 170
• 229910052757 nitrogen Inorganic materials 0.000 claims description 149
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 134
• 125000004432 carbon atom Chemical group C* 0.000 claims description 122
• 125000000217 alkyl group Chemical group 0.000 claims description 105
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 58
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 58
• 125000005842 heteroatom Chemical group 0.000 claims description 41
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 41
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 38
• 239000001301 oxygen Substances 0.000 claims description 38
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 35
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 33
• 239000011593 sulfur Substances 0.000 claims description 33
• 239000002253 acid Substances 0.000 claims description 32
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 31
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 26
• 125000005605 benzo group Chemical group 0.000 claims description 25
• 229910052736 halogen Inorganic materials 0.000 claims description 25
• 150000002367 halogens Chemical class 0.000 claims description 24
• 125000005843 halogen group Chemical group 0.000 claims description 22
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 21
• 150000001721 carbon Chemical group 0.000 claims description 20
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 19
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• 125000001544 thienyl group Chemical group 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 150000003536 tetrazoles Chemical group 0.000 claims description 14
• 150000003852 triazoles Chemical class 0.000 claims description 14
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
• 150000002431 hydrogen Chemical class 0.000 claims description 12
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 11
• 230000006378 damage Effects 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 10
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 10
• PSTDMIAVUUYOOQ-UHFFFAOYSA-N 7-chloro-2-(4-methoxy-2-methylphenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound CC1=CC(OC)=CC=C1N1C(=O)C(C(=O)C2=CC=C(Cl)C=C2N2)=C2C(=O)N1 PSTDMIAVUUYOOQ-UHFFFAOYSA-N 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 10
• 125000002541 furyl group Chemical group 0.000 claims description 10
• 150000002429 hydrazines Chemical class 0.000 claims description 10
• 239000003960 organic solvent Substances 0.000 claims description 10
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 150000001412 amines Chemical class 0.000 claims description 9
• 229960001231 choline Drugs 0.000 claims description 9
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• 229940079593 drug Drugs 0.000 claims description 9
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 9
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 9
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 9
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 8
• 208000006011 Stroke Diseases 0.000 claims description 8
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 8
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 7
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
• 210000004556 brain Anatomy 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 6
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 6
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 6
• 150000001408 amides Chemical group 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 6
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 5
• HAIUNXBMBCLTKF-UHFFFAOYSA-N 7-chloro-2-(4-hydroxyphenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound C1=CC(O)=CC=C1N1C(=O)C(C(=O)C2=CC=C(Cl)C=C2N2)=C2C(=O)N1 HAIUNXBMBCLTKF-UHFFFAOYSA-N 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 159000000000 sodium salts Chemical class 0.000 claims description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
• 239000003153 chemical reaction reagent Substances 0.000 claims description 4
• 239000003795 chemical substances by application Substances 0.000 claims description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 230000000926 neurological effect Effects 0.000 claims description 4
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
• FORBFXBAXOOJDD-UHFFFAOYSA-N 2-(4-bromophenyl)-7-chloro-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound C=1C(Cl)=CC=C(C2=O)C=1NC(C(N1)=O)=C2C(=O)N1C1=CC=C(Br)C=C1 FORBFXBAXOOJDD-UHFFFAOYSA-N 0.000 claims description 3
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
• 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 3
• YSTYYCMNJZPZCN-UHFFFAOYSA-N 7,9-dichloro-2-(2,4-dimethylphenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound CC1=CC(C)=CC=C1N1C(=O)C(C(=O)C2=C(Cl)C=C(Cl)C=C2N2)=C2C(=O)N1 YSTYYCMNJZPZCN-UHFFFAOYSA-N 0.000 claims description 3
• XUDZYRYUTGACPZ-UHFFFAOYSA-N 7-chloro-2-(4-chloro-2-methylphenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound CC1=CC(Cl)=CC=C1N1C(=O)C(C(=O)C2=CC=C(Cl)C=C2N2)=C2C(=O)N1 XUDZYRYUTGACPZ-UHFFFAOYSA-N 0.000 claims description 3
• QOFXIJNPFLDIOI-UHFFFAOYSA-N 7-chloro-2-[4-(trifluoromethoxy)phenyl]-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C(=O)C(C(=O)C2=CC=C(Cl)C=C2N2)=C2C(=O)N1 QOFXIJNPFLDIOI-UHFFFAOYSA-N 0.000 claims description 3
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
• 150000007513 acids Chemical class 0.000 claims description 3
• 239000011575 calcium Substances 0.000 claims description 3
• 229910052791 calcium Inorganic materials 0.000 claims description 3
• 150000001735 carboxylic acids Chemical group 0.000 claims description 3
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
• 208000037906 ischaemic injury Diseases 0.000 claims description 3
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 239000007800 oxidant agent Substances 0.000 claims description 3
• 125000005429 oxyalkyl group Chemical group 0.000 claims description 3
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
• FBRMKRCMNDRSHJ-UHFFFAOYSA-N 7-chloro-2-(2,4-dimethylphenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound CC1=CC(C)=CC=C1N1C(=O)C(C(=O)C2=CC=C(Cl)C=C2N2)=C2C(=O)N1 FBRMKRCMNDRSHJ-UHFFFAOYSA-N 0.000 claims description 2
• UNSCMXDBQPKWDV-UHFFFAOYSA-N 7-chloro-2-(3-chloro-4-methoxyphenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound C1=C(Cl)C(OC)=CC=C1N1C(=O)C(C(=O)C2=CC=C(Cl)C=C2N2)=C2C(=O)N1 UNSCMXDBQPKWDV-UHFFFAOYSA-N 0.000 claims description 2
• XMHFPIBAEYGEJA-UHFFFAOYSA-N 7-chloro-2-(3-fluorophenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound FC1=CC=CC(N2C(C=3C(=O)C4=CC=C(Cl)C=C4NC=3C(=O)N2)=O)=C1 XMHFPIBAEYGEJA-UHFFFAOYSA-N 0.000 claims description 2
• AQJSEDCGGNVVOK-UHFFFAOYSA-N 7-chloro-2-(4-chlorophenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C(=O)C2=CC=C(Cl)C=C2N2)=C2C(=O)N1 AQJSEDCGGNVVOK-UHFFFAOYSA-N 0.000 claims description 2
• RRSOSCNRVYVSQT-UHFFFAOYSA-N 7-chloro-2-(4-hydroxy-2-methylphenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound CC1=CC(O)=CC=C1N1C(=O)C(C(=O)C2=CC=C(Cl)C=C2N2)=C2C(=O)N1 RRSOSCNRVYVSQT-UHFFFAOYSA-N 0.000 claims description 2
• KBHNHJRGBBULFU-UHFFFAOYSA-N 7-chloro-2-(4-methylphenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound C1=CC(C)=CC=C1N1C(=O)C(C(=O)C2=CC=C(Cl)C=C2N2)=C2C(=O)N1 KBHNHJRGBBULFU-UHFFFAOYSA-N 0.000 claims description 2
• YVHYWXHSGFPRDE-UHFFFAOYSA-N 7-chloro-2-(4-phenylmethoxyphenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound C=1C(Cl)=CC=C(C2=O)C=1NC(C(N1)=O)=C2C(=O)N1C(C=C1)=CC=C1OCC1=CC=CC=C1 YVHYWXHSGFPRDE-UHFFFAOYSA-N 0.000 claims description 2
• CPQWTIJUVHNNKP-UHFFFAOYSA-N 7-chloro-2-(6-methoxypyridin-3-yl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound C1=NC(OC)=CC=C1N1C(=O)C(C(=O)C2=CC=C(Cl)C=C2N2)=C2C(=O)N1 CPQWTIJUVHNNKP-UHFFFAOYSA-N 0.000 claims description 2
• QHPMRRCXNQNGFV-UHFFFAOYSA-N 8-nitro-2-phenyl-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound O=C1C2=CC([N+](=O)[O-])=CC=C2NC(C(N2)=O)=C1C(=O)N2C1=CC=CC=C1 QHPMRRCXNQNGFV-UHFFFAOYSA-N 0.000 claims description 2
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
• 150000001540 azides Chemical class 0.000 claims description 2
• 230000008878 coupling Effects 0.000 claims description 2
• 238000010168 coupling process Methods 0.000 claims description 2
• 238000005859 coupling reaction Methods 0.000 claims description 2
• 201000010099 disease Diseases 0.000 claims description 2
• 208000035475 disorder Diseases 0.000 claims description 2
• 230000002140 halogenating effect Effects 0.000 claims description 2
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
• 125000000101 thioether group Chemical group 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
• XKBSSCVZPRNPKC-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-7-chloro-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(N2C(C=3C(=O)C4=CC=C(Cl)C=C4NC=3C(=O)N2)=O)=C1 XKBSSCVZPRNPKC-UHFFFAOYSA-N 0.000 claims 1
• WYKDEYRJWDEURF-UHFFFAOYSA-N 4-(7-chloro-1,4,10-trioxo-3,5-dihydropyridazino[4,5-b]quinolin-2-yl)-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1N1C(=O)C(C(=O)C2=CC=C(Cl)C=C2N2)=C2C(=O)N1 WYKDEYRJWDEURF-UHFFFAOYSA-N 0.000 claims 1
• ZRMKDOVBZQZKTB-UHFFFAOYSA-N 7-chloro-2-(2,3-dimethylphenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound CC1=CC=CC(N2C(C=3C(=O)C4=CC=C(Cl)C=C4NC=3C(=O)N2)=O)=C1C ZRMKDOVBZQZKTB-UHFFFAOYSA-N 0.000 claims 1
• VVCWCZGCUOJJLL-UHFFFAOYSA-N 7-chloro-2-(2,4-dichlorophenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound ClC1=CC(Cl)=CC=C1N1C(=O)C(C(=O)C2=CC=C(Cl)C=C2N2)=C2C(=O)N1 VVCWCZGCUOJJLL-UHFFFAOYSA-N 0.000 claims 1
• BNSGQKSSAMPIAU-UHFFFAOYSA-N 7-chloro-2-(2,5-difluorophenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound FC1=CC=C(F)C(N2C(C=3C(=O)C4=CC=C(Cl)C=C4NC=3C(=O)N2)=O)=C1 BNSGQKSSAMPIAU-UHFFFAOYSA-N 0.000 claims 1
• VHRFGSOEHKQJBX-UHFFFAOYSA-N 7-chloro-2-(2,5-dihydroxyphenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound OC1=CC=C(O)C(N2C(C=3C(=O)C4=CC=C(Cl)C=C4NC=3C(=O)N2)=O)=C1 VHRFGSOEHKQJBX-UHFFFAOYSA-N 0.000 claims 1
• NPSAUPSWUBKCND-UHFFFAOYSA-N 7-chloro-2-(2,5-dimethoxyphenyl)-3,5-dihydropyridazino[4,5-b]quinoline-1,4,10-trione Chemical compound COC1=CC=C(OC)C(N2C(C=3C(=O)C4=CC=C(Cl)C=C4NC=3C(=O)N2)=O)=C1 NPSAUPSWUBKCND-UHFFFAOYSA-N 0.000 claims 1
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