HRP20020271A2 - Tricyclic inhibitors of poly(adp-ribose) polymerases - Google Patents

Info

Publication number

HRP20020271A2

HRP20020271A2 HR20020271A HRP20020271A HRP20020271A2 HR P20020271 A2 HRP20020271 A2 HR P20020271A2 HR 20020271 A HR20020271 A HR 20020271A HR P20020271 A HRP20020271 A HR P20020271A HR P20020271 A2 HRP20020271 A2 HR P20020271A2

Authority

HR

Croatia

Prior art keywords

aryl

cycloalkyl

alkynyl

heterocycloalkyl

alkenyl

Prior art date

1999-08-31

Links

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• Global Dossier
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• 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 title claims description 78
• 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 title claims description 68
• 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 title claims description 67
• 239000003112 inhibitor Substances 0.000 title description 9
• 150000001875 compounds Chemical class 0.000 claims description 197
• 125000003118 aryl group Chemical group 0.000 claims description 187
• 229910052757 nitrogen Inorganic materials 0.000 claims description 181
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 169
• 125000001072 heteroaryl group Chemical group 0.000 claims description 156
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 143
• 125000000304 alkynyl group Chemical group 0.000 claims description 140
• 238000000034 method Methods 0.000 claims description 140
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 139
• 125000003342 alkenyl group Chemical group 0.000 claims description 132
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 119
• 125000000217 alkyl group Chemical group 0.000 claims description 92
• -1 alkylnyl Chemical group 0.000 claims description 89
• 229910052736 halogen Inorganic materials 0.000 claims description 66
• 150000002367 halogens Chemical class 0.000 claims description 66
• 125000001424 substituent group Chemical group 0.000 claims description 59
• 150000003839 salts Chemical class 0.000 claims description 50
• 239000012453 solvate Substances 0.000 claims description 37
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
• 229940002612 prodrug Drugs 0.000 claims description 36
• 239000000651 prodrug Substances 0.000 claims description 36
• 239000002207 metabolite Substances 0.000 claims description 35
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
• 239000003795 chemical substances by application Substances 0.000 claims description 32
• 229910052760 oxygen Inorganic materials 0.000 claims description 32
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
• 230000000694 effects Effects 0.000 claims description 27
• 229910052717 sulfur Inorganic materials 0.000 claims description 27
• 230000002401 inhibitory effect Effects 0.000 claims description 26
• 230000005764 inhibitory process Effects 0.000 claims description 24
• 102000004190 Enzymes Human genes 0.000 claims description 21
• 108090000790 Enzymes Proteins 0.000 claims description 21
• 241000124008 Mammalia Species 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• 125000004104 aryloxy group Chemical group 0.000 claims description 7
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
• 238000003556 assay Methods 0.000 claims description 6
• 231100000135 cytotoxicity Toxicity 0.000 claims description 6
• 230000003013 cytotoxicity Effects 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 238000012360 testing method Methods 0.000 claims description 5
• 108010017601 Tankyrases Proteins 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
• 101710179684 Poly [ADP-ribose] polymerase Proteins 0.000 claims 14
• 102100023712 Poly [ADP-ribose] polymerase 1 Human genes 0.000 claims 14
• 229910000272 alkali metal oxide Inorganic materials 0.000 claims 4
• 125000005017 substituted alkenyl group Chemical group 0.000 claims 3
• 102100037664 Poly [ADP-ribose] polymerase tankyrase-1 Human genes 0.000 claims 2
• 150000001345 alkine derivatives Chemical class 0.000 claims 1
• 125000004404 heteroalkyl group Chemical group 0.000 claims 1
• 239000000825 pharmaceutical preparation Substances 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 453
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 424
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 284
• 239000007787 solid Substances 0.000 description 255
• 238000005160 1H NMR spectroscopy Methods 0.000 description 234
• 229910052739 hydrogen Inorganic materials 0.000 description 182
• 229910052799 carbon Inorganic materials 0.000 description 176
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 176
• 235000019439 ethyl acetate Nutrition 0.000 description 141
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 110
• 239000000047 product Substances 0.000 description 85
• 239000002904 solvent Substances 0.000 description 81
• 238000006243 chemical reaction Methods 0.000 description 76
• 239000000243 solution Substances 0.000 description 71
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 64
• 239000011541 reaction mixture Substances 0.000 description 64
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 56
• 238000002844 melting Methods 0.000 description 52
• 230000008018 melting Effects 0.000 description 52
• 239000000741 silica gel Substances 0.000 description 52
• 229910002027 silica gel Inorganic materials 0.000 description 52
• 229960001866 silicon dioxide Drugs 0.000 description 52
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
• 238000003818 flash chromatography Methods 0.000 description 42
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 40
• CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 37
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 33
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 32
• 235000019341 magnesium sulphate Nutrition 0.000 description 32
• 238000002360 preparation method Methods 0.000 description 32
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 31
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
• 239000000203 mixture Substances 0.000 description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
• 150000004985 diamines Chemical class 0.000 description 26
• 239000012044 organic layer Substances 0.000 description 23
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 150000001299 aldehydes Chemical class 0.000 description 21
• 238000000746 purification Methods 0.000 description 21
• 235000002639 sodium chloride Nutrition 0.000 description 21
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
• 238000000354 decomposition reaction Methods 0.000 description 18
• 238000004128 high performance liquid chromatography Methods 0.000 description 18
• 230000035484 reaction time Effects 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 16
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
• 238000004809 thin layer chromatography Methods 0.000 description 15
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 14
• 239000012661 PARP inhibitor Substances 0.000 description 14
• 229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 description 14
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
• 150000001412 amines Chemical class 0.000 description 13
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 11
• 150000002576 ketones Chemical class 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 235000019198 oils Nutrition 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
• 238000004440 column chromatography Methods 0.000 description 10
• 239000012043 crude product Substances 0.000 description 10
• 238000006268 reductive amination reaction Methods 0.000 description 10
• 238000011282 treatment Methods 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
• 108091026813 Poly(ADPribose) Proteins 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 9
• 239000012074 organic phase Substances 0.000 description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
• MFUIXAMVRWIMMR-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenyl]-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-9-one Chemical compound C1=CC(OCCO)=CC=C1C1=NC2=CC=CC3=C2N1CCNC3=O MFUIXAMVRWIMMR-UHFFFAOYSA-N 0.000 description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 8
• 208000006011 Stroke Diseases 0.000 description 8
• 229960000583 acetic acid Drugs 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 239000003054 catalyst Substances 0.000 description 8
• 230000006378 damage Effects 0.000 description 8
• 230000018109 developmental process Effects 0.000 description 8
• 201000010099 disease Diseases 0.000 description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
• 239000000284 extract Substances 0.000 description 8
• 150000003951 lactams Chemical class 0.000 description 8
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 8
• 230000002829 reductive effect Effects 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• 238000010626 work up procedure Methods 0.000 description 8
• QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 7
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
• SEKJSSBJKFLZIT-UHFFFAOYSA-N LSM-1988 Chemical compound C1=CC(CN(C)C)=CC=C1C1=NC2=CC=CC3=C2N1CCNC3=O SEKJSSBJKFLZIT-UHFFFAOYSA-N 0.000 description 7
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
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• 230000004770 neurodegeneration Effects 0.000 description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
• 235000017557 sodium bicarbonate Nutrition 0.000 description 7
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
• 238000003756 stirring Methods 0.000 description 7
• NXVQPQIEEULMJF-UHFFFAOYSA-N 1-[4-(2-hydroxy-ethyl)-phenyl]-8,9-dihydro-7h-2,7,9a-triaza-benzo[cd]azulen-6-one Chemical compound C1=CC(CCO)=CC=C1C(N1CC2)=NC=C3C1=C2NC(=O)C=C3 NXVQPQIEEULMJF-UHFFFAOYSA-N 0.000 description 6
• DBYXBLQLOHDHBJ-UHFFFAOYSA-N 4-(4-fluoro-6-oxo-6,7,8,9-tetrahydro-2,7,9a-triaza-benzo[cd]azulen-1-yl)-benzaldehyde Chemical compound N=1C=C2C(F)=CC(=O)NC(CC3)=C2N3C=1C1=CC=C(C=O)C=C1 DBYXBLQLOHDHBJ-UHFFFAOYSA-N 0.000 description 6
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
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• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
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• PEVSPCKJWXKQHX-UHFFFAOYSA-N chembl189670 Chemical compound C=1C(C2=3)=CC=CC=3C(=O)NCCN2C=1C1=CC=CC=C1 PEVSPCKJWXKQHX-UHFFFAOYSA-N 0.000 description 6
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• 230000008569 process Effects 0.000 description 6
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• PLRACCBDVIHHLZ-UHFFFAOYSA-N 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine Chemical compound C1N(C)CCC(C=2C=CC=CC=2)=C1 PLRACCBDVIHHLZ-UHFFFAOYSA-N 0.000 description 5
• HWKGSASWPKYULS-UHFFFAOYSA-N 2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-9-one Chemical compound N=1C(C2=3)=CC=CC=3C(=O)NCCN2C=1C(C=C1)=CC=C1OCCN1CCCC1 HWKGSASWPKYULS-UHFFFAOYSA-N 0.000 description 5
• GVEMORXNDBIEEV-UHFFFAOYSA-N 2-methylsulfinyl-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-9-one Chemical compound O=C1NCCN2C(S(=O)C)=NC3=CC=CC1=C32 GVEMORXNDBIEEV-UHFFFAOYSA-N 0.000 description 5
• WGRAEBLYNODYOI-UHFFFAOYSA-N 4-(9-oxo-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-2-yl)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=NC2=CC=CC3=C2N1CCNC3=O WGRAEBLYNODYOI-UHFFFAOYSA-N 0.000 description 5
• HCESKYHVILECLD-UHFFFAOYSA-N 9-iodo-1,2,3,4-tetrahydro-1,4-benzodiazepin-5-one Chemical compound N1CCNC(=O)C2=C1C(I)=CC=C2 HCESKYHVILECLD-UHFFFAOYSA-N 0.000 description 5
• VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 5
• 102000003960 Ligases Human genes 0.000 description 5
• 108090000364 Ligases Proteins 0.000 description 5
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
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• 230000003389 potentiating effect Effects 0.000 description 5
• 238000003786 synthesis reaction Methods 0.000 description 5
• SURVUDPNZQGEJD-UHFFFAOYSA-N 1,4-diazepin-5-one Chemical compound O=C1C=CN=CC=N1 SURVUDPNZQGEJD-UHFFFAOYSA-N 0.000 description 4
• VTIPDOHASBURQC-UHFFFAOYSA-N 1-(4-piperidin-4-yl-phenyl)-8,9-dihydro-7h-2,7,9a-triaza-benzo[cd]azulen-6-one Chemical compound N=1C=C2C=CC(=O)NC(CC3)=C2N3C=1C(C=C1)=CC=C1C1CCNCC1 VTIPDOHASBURQC-UHFFFAOYSA-N 0.000 description 4
• QPASZTZXNVXHCZ-UHFFFAOYSA-N 2-(4-pyridin-4-ylphenyl)-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-9-one Chemical compound N=1C(C2=3)=CC=CC=3C(=O)NCCN2C=1C(C=C1)=CC=C1C1=CC=NC=C1 QPASZTZXNVXHCZ-UHFFFAOYSA-N 0.000 description 4
• XVFLDOZQTOHKLK-UHFFFAOYSA-N 2-[4-(diethoxymethyl)phenyl]-6-fluoro-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-9-one Chemical compound C1=CC(C(OCC)OCC)=CC=C1C1=NC2=CC(F)=CC3=C2N1CCNC3=O XVFLDOZQTOHKLK-UHFFFAOYSA-N 0.000 description 4
• QYWGTZFAVMKMTH-UHFFFAOYSA-N 2-[4-(thiomorpholin-4-ylmethyl)phenyl]-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-9-one Chemical compound N=1C(C2=3)=CC=CC=3C(=O)NCCN2C=1C(C=C1)=CC=C1CN1CCSCC1 QYWGTZFAVMKMTH-UHFFFAOYSA-N 0.000 description 4
• JIXQFXKGXBGVDC-UHFFFAOYSA-N 2-benzylsulfanyl-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-9-one Chemical compound N=1C(C2=3)=CC=CC=3C(=O)NCCN2C=1SCC1=CC=CC=C1 JIXQFXKGXBGVDC-UHFFFAOYSA-N 0.000 description 4
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