ES2547571T3 - Compuestos tricíclicos e inhibidores de PBK que los contienen - Google Patents

Info

Publication number

ES2547571T3

ES2547571T3 ES11763307.3T ES11763307T ES2547571T3 ES 2547571 T3 ES2547571 T3 ES 2547571T3 ES 11763307 T ES11763307 T ES 11763307T ES 2547571 T3 ES2547571 T3 ES 2547571T3

Authority

ES

Spain

Prior art keywords

quinolin

phenyl

hydroxy

oxo

hydroxytiene

Prior art date

2010-03-29

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.)

Active

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 51
• 239000003112 inhibitor Substances 0.000 title description 7
• -1 hydroxyethylamino Chemical group 0.000 claims abstract description 1284
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 414
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 223
• 239000001257 hydrogen Chemical group 0.000 claims abstract description 222
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 165
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 133
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 128
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 126
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 104
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 89
• 150000002367 halogens Chemical group 0.000 claims abstract description 89
• 125000001424 substituent group Chemical group 0.000 claims abstract description 79
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 72
• 150000002431 hydrogen Chemical group 0.000 claims abstract description 70
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 64
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 52
• 150000003839 salts Chemical class 0.000 claims abstract description 44
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 37
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 29
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
• 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 27
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract description 17
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 15
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
• 125000003118 aryl group Chemical group 0.000 claims abstract description 9
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 9
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 8
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 7
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims abstract description 7
• 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 135
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 115
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 108
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 95
• 125000005936 piperidyl group Chemical group 0.000 claims description 59
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 42
• 125000004193 piperazinyl group Chemical group 0.000 claims description 28
• 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 26
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 23
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 21
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 19
• 125000005999 2-bromoethyl group Chemical group 0.000 claims description 18
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 18
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 17
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 15
• 206010028980 Neoplasm Diseases 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
• 201000011510 cancer Diseases 0.000 claims description 13
• ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 claims description 13
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• CIIFKVFOVFJZDM-UHFFFAOYSA-N quinoline-8-carbonitrile Chemical compound C1=CN=C2C(C#N)=CC=CC2=C1 CIIFKVFOVFJZDM-UHFFFAOYSA-N 0.000 claims description 9
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 8
• AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 claims description 8
• DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 claims description 8
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 7
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
• 239000004202 carbamide Substances 0.000 claims description 6
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 6
• ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
• CZGLYGAHZNUYMY-UHFFFAOYSA-N 8-hydroxy-9-(1H-indazol-6-yl)-5H-thieno[2,3-c]quinolin-4-one Chemical compound C1=C2C=NNC2=CC(C2=C3C=4C=CSC=4C(=O)NC3=CC=C2O)=C1 CZGLYGAHZNUYMY-UHFFFAOYSA-N 0.000 claims description 5
• IQHLQFVWLCCILI-UHFFFAOYSA-N 8-hydroxy-9-(1h-pyrrolo[2,3-b]pyridin-5-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound N1=C2NC=CC2=CC(C2=C3C=4C=CSC=4C(=O)NC3=CC=C2O)=C1 IQHLQFVWLCCILI-UHFFFAOYSA-N 0.000 claims description 5
• YEOTWNGESBWCKL-UHFFFAOYSA-N 8-hydroxy-9-(3,4,5-trifluorophenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC(F)=C(F)C(F)=C1 YEOTWNGESBWCKL-UHFFFAOYSA-N 0.000 claims description 5
• VKPNODPBVWQIDH-UHFFFAOYSA-N 8-hydroxy-9-(3,4,5-trihydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC(O)=C(O)C(O)=C1 VKPNODPBVWQIDH-UHFFFAOYSA-N 0.000 claims description 5
• CHYRZPZOSVMSHU-UHFFFAOYSA-N 8-hydroxy-9-(3-hydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=CC(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)=C1 CHYRZPZOSVMSHU-UHFFFAOYSA-N 0.000 claims description 5
• IBBFRKJQXTXZDA-UHFFFAOYSA-N 8-hydroxy-9-[4-(4-methylpiperazin-1-yl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1CN(C)CCN1C1=CC=C(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)C=C1 IBBFRKJQXTXZDA-UHFFFAOYSA-N 0.000 claims description 5
• HDIYECOPFHOBAY-UHFFFAOYSA-N 8-hydroxy-9-[4-(4-methylsulfonylpiperazin-1-yl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1CN(S(=O)(=O)C)CCN1C1=CC=C(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)C=C1 HDIYECOPFHOBAY-UHFFFAOYSA-N 0.000 claims description 5
• NFPKWIUGEYURJP-UHFFFAOYSA-N 8-hydroxy-9-[4-(methylaminomethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CNC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 NFPKWIUGEYURJP-UHFFFAOYSA-N 0.000 claims description 5
• DNPAILKTOGMGHY-UHFFFAOYSA-N 8-hydroxy-9-pyridin-4-yl-5H-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=NC=C1 DNPAILKTOGMGHY-UHFFFAOYSA-N 0.000 claims description 5
• VNYADQQBHVFOQA-UHFFFAOYSA-N 8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CCNCC1 VNYADQQBHVFOQA-UHFFFAOYSA-N 0.000 claims description 5
• UJVSPDNKCJRNMD-UHFFFAOYSA-N 8-methoxy-9-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CCN(S(C)(=O)=O)CC1 UJVSPDNKCJRNMD-UHFFFAOYSA-N 0.000 claims description 5
• BXLXAHVNKSNDOS-UHFFFAOYSA-N 8-methoxy-9-(1h-pyrrolo[2,3-b]pyridin-5-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound N1=C2NC=CC2=CC(C2=C3C=4C=CSC=4C(=O)NC3=CC=C2OC)=C1 BXLXAHVNKSNDOS-UHFFFAOYSA-N 0.000 claims description 5
• MNMCSWHMRLNWAN-UHFFFAOYSA-N 8-methoxy-9-(4-piperazin-1-ylphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1N1CCNCC1 MNMCSWHMRLNWAN-UHFFFAOYSA-N 0.000 claims description 5
• MTHCRNFWWVFGQD-UHFFFAOYSA-N 8-methoxy-9-[4-(2-piperidin-1-ylethoxy)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1OCCN1CCCCC1 MTHCRNFWWVFGQD-UHFFFAOYSA-N 0.000 claims description 5
• WISBHINJSCDTRW-UHFFFAOYSA-N 8-methoxy-9-[4-(methylaminomethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CNC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 WISBHINJSCDTRW-UHFFFAOYSA-N 0.000 claims description 5
• 102220540772 E3 ubiquitin-protein ligase CHIP_R72A_mutation Human genes 0.000 claims description 5
• 102220483127 Gasdermin-A_R73A_mutation Human genes 0.000 claims description 5
• 102220550773 KATNB1-like protein 1_R71A_mutation Human genes 0.000 claims description 5
• 102220545870 Vacuolar protein sorting-associated protein 41 homolog_R74A_mutation Human genes 0.000 claims description 5
• 102220545880 Vacuolar protein sorting-associated protein 41 homolog_R75A_mutation Human genes 0.000 claims description 5
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 4
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 4
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• FSWSJPMIDVZHAO-UHFFFAOYSA-N 6-fluoro-8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(F)=C2NC(=O)C=3SC=CC=3C2=C1C1=CCNCC1 FSWSJPMIDVZHAO-UHFFFAOYSA-N 0.000 claims description 4
• JYIYWWJXISZCBJ-UHFFFAOYSA-N 8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CCNCC1 JYIYWWJXISZCBJ-UHFFFAOYSA-N 0.000 claims description 4
• CORMOCRLITWIBP-UHFFFAOYSA-N 8-hydroxy-9-(4-hydroxy-3-methoxyphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(O)C(OC)=CC(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)=C1 CORMOCRLITWIBP-UHFFFAOYSA-N 0.000 claims description 4
• NHZZDHMAWQRUFV-UHFFFAOYSA-N 8-hydroxy-9-(4-hydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(O)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 NHZZDHMAWQRUFV-UHFFFAOYSA-N 0.000 claims description 4
• WARPWRWOPLRWNL-UHFFFAOYSA-N 8-hydroxy-9-(4-methylsulfonylphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 WARPWRWOPLRWNL-UHFFFAOYSA-N 0.000 claims description 4
• BZEIRDSCZXTXMX-OWOJBTEDSA-N 8-hydroxy-9-[(e)-3-(3-hydroxypyrrolidin-1-yl)prop-1-enyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1C(O)CCN1C\C=C\C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 BZEIRDSCZXTXMX-OWOJBTEDSA-N 0.000 claims description 4
• HQELCFHNXXRUAA-UHFFFAOYSA-N 8-hydroxy-9-[3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1CN(C)CCN1CCOC1=CC=CC(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)=C1 HQELCFHNXXRUAA-UHFFFAOYSA-N 0.000 claims description 4
• JTORDYUXYKYKMZ-UHFFFAOYSA-N 8-hydroxy-9-[3-hydroxy-5-(trifluoromethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound FC(F)(F)C1=CC(O)=CC(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)=C1 JTORDYUXYKYKMZ-UHFFFAOYSA-N 0.000 claims description 4
• LUPPIISCWHVUQD-UHFFFAOYSA-N 8-hydroxy-9-[4-(2-piperidin-1-ylethoxy)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1OCCN1CCCCC1 LUPPIISCWHVUQD-UHFFFAOYSA-N 0.000 claims description 4
• ORTUEIOFGQMZRR-UHFFFAOYSA-N 8-hydroxy-9-[4-(2-piperidin-1-ylethylamino)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1NCCN1CCCCC1 ORTUEIOFGQMZRR-UHFFFAOYSA-N 0.000 claims description 4
• DPUHVKWFBIZDLM-UHFFFAOYSA-N 8-hydroxy-9-[4-(hydroxymethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CO)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 DPUHVKWFBIZDLM-UHFFFAOYSA-N 0.000 claims description 4
• ZTMOUJUDDNQUIH-UHFFFAOYSA-N 8-hydroxy-9-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1CN(C)CCN1CC1=CC=C(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)C=C1 ZTMOUJUDDNQUIH-UHFFFAOYSA-N 0.000 claims description 4
• BHONOBSHASPSOG-UHFFFAOYSA-N 8-hydroxy-9-[4-[(piperidin-3-ylamino)methyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1CNC1CCCNC1 BHONOBSHASPSOG-UHFFFAOYSA-N 0.000 claims description 4
• BCLRKKDBVFJBNT-UHFFFAOYSA-N 8-hydroxy-9-[4-[(propan-2-ylamino)methyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CNC(C)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 BCLRKKDBVFJBNT-UHFFFAOYSA-N 0.000 claims description 4
• SOYBPCQYRXLUCK-UHFFFAOYSA-N 8-hydroxy-9-[4-[1-(2-methylsulfonylethylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(NCCS(C)(=O)=O)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 SOYBPCQYRXLUCK-UHFFFAOYSA-N 0.000 claims description 4
• HUBLRWPBQWKPKA-UHFFFAOYSA-N 8-hydroxy-9-naphthalen-2-yl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC=CC2=CC(C3=C4C=5C=CSC=5C(=O)NC4=CC=C3O)=CC=C21 HUBLRWPBQWKPKA-UHFFFAOYSA-N 0.000 claims description 4
• WFWMEHHYMQPVGO-UHFFFAOYSA-N 8-methoxy-9-(1-piperidin-4-ylpyrazol-4-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(=C1)C=NN1C1CCNCC1 WFWMEHHYMQPVGO-UHFFFAOYSA-N 0.000 claims description 4
• QXHXAOKQRDPTIK-UHFFFAOYSA-N 8-methoxy-9-(5-methoxypyridin-3-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CN=CC(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2OC)=C1 QXHXAOKQRDPTIK-UHFFFAOYSA-N 0.000 claims description 4
• BPBBAFGLERHFJM-UHFFFAOYSA-N 8-methoxy-9-[3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=1)=CC=CC=1OCCN1CCN(C)CC1 BPBBAFGLERHFJM-UHFFFAOYSA-N 0.000 claims description 4
• YMNVPLLINOBESY-UHFFFAOYSA-N 8-methoxy-9-[4-(1-piperidin-1-ylethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1C(C)N1CCCCC1 YMNVPLLINOBESY-UHFFFAOYSA-N 0.000 claims description 4
• JMSAMZBXGUPEHM-UHFFFAOYSA-N 8-methoxy-9-[4-(4-methylpiperazin-1-yl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1N1CCN(C)CC1 JMSAMZBXGUPEHM-UHFFFAOYSA-N 0.000 claims description 4
• LGDFBLUWQATQMB-UHFFFAOYSA-N 8-methoxy-9-[4-(4-methylpiperazine-1-carbonyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1C(=O)N1CCN(C)CC1 LGDFBLUWQATQMB-UHFFFAOYSA-N 0.000 claims description 4
• ZKDTYXXRBUIPOE-UHFFFAOYSA-N 8-methoxy-9-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1CN1CCN(C)CC1 ZKDTYXXRBUIPOE-UHFFFAOYSA-N 0.000 claims description 4
• VHUVDXOKWOHXRE-UHFFFAOYSA-N 8-methoxy-9-[4-[1-(2-methylsulfonylethylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)NCCS(C)(=O)=O)C=C1 VHUVDXOKWOHXRE-UHFFFAOYSA-N 0.000 claims description 4
• KLAGCKUDEZKBSG-UHFFFAOYSA-N 8-methoxy-9-[4-[2-(2-methylsulfonylethylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCNCCS(C)(=O)=O)C=C1 KLAGCKUDEZKBSG-UHFFFAOYSA-N 0.000 claims description 4
• OETLNMOJNONWOY-LBPRGKRZSA-N 9-[4-[(2r)-1-aminopropan-2-yl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](CN)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 OETLNMOJNONWOY-LBPRGKRZSA-N 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 4
• 238000011282 treatment Methods 0.000 claims description 4
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 3
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 3
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
• OQLFLCJMFVODGI-UHFFFAOYSA-N 6-fluoro-8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC(F)=C2NC(=O)C=3SC=CC=3C2=C1C1=CCNCC1 OQLFLCJMFVODGI-UHFFFAOYSA-N 0.000 claims description 3
• XWMZMQPUMXKNCF-UHFFFAOYSA-N 8-hydroxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1CNCC2=CC(C3=C4C=5C=CSC=5C(=O)NC4=CC=C3O)=CC=C21 XWMZMQPUMXKNCF-UHFFFAOYSA-N 0.000 claims description 3
• NRQBKMOSNRFRRG-UHFFFAOYSA-N 8-hydroxy-9-(1-methyl-2,3-dihydroindol-5-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C=1C=C2N(C)CCC2=CC=1C(C1=2)=C(O)C=CC=2NC(=O)C2=C1C=CS2 NRQBKMOSNRFRRG-UHFFFAOYSA-N 0.000 claims description 3
• GMWKSTUBBNVTNS-UHFFFAOYSA-N 8-hydroxy-9-(1-piperidin-4-ylpyrazol-4-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(=C1)C=NN1C1CCNCC1 GMWKSTUBBNVTNS-UHFFFAOYSA-N 0.000 claims description 3
• PDQAKFLQBUATMZ-UHFFFAOYSA-N 8-hydroxy-9-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C2CN(C)CCC2=CC=C1C(C1=2)=C(O)C=CC=2NC(=O)C2=C1C=CS2 PDQAKFLQBUATMZ-UHFFFAOYSA-N 0.000 claims description 3
• ALHZCIJAHFVRDE-UHFFFAOYSA-N 8-hydroxy-9-(4-piperazin-1-ylphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1N1CCNCC1 ALHZCIJAHFVRDE-UHFFFAOYSA-N 0.000 claims description 3
• TYZAXENLMRBPEC-NSCUHMNNSA-N 8-hydroxy-9-[(e)-3-(2-methylsulfonylethylamino)prop-1-enyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C(/C=C/CNCCS(=O)(=O)C)=C(O)C=CC=2NC(=O)C2=C1C=CS2 TYZAXENLMRBPEC-NSCUHMNNSA-N 0.000 claims description 3
• OVSLYFNHAIXXEF-UHFFFAOYSA-N 8-hydroxy-9-[4-(1-hydroxyethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(O)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 OVSLYFNHAIXXEF-UHFFFAOYSA-N 0.000 claims description 3
• WBKBOJJKNZSLIG-UHFFFAOYSA-N 8-hydroxy-9-[4-(1-piperidin-1-ylethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C=1C=C(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)C=CC=1C(C)N1CCCCC1 WBKBOJJKNZSLIG-UHFFFAOYSA-N 0.000 claims description 3
• PIECCKNCIBEOQW-UHFFFAOYSA-N 8-hydroxy-9-[4-(1-pyrrolidin-1-ylethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C=1C=C(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)C=CC=1C(C)N1CCCC1 PIECCKNCIBEOQW-UHFFFAOYSA-N 0.000 claims description 3
• NCBXPJLOXWWSLY-UHFFFAOYSA-N 8-hydroxy-9-[4-(2-hydroxyethylsulfonyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(S(=O)(=O)CCO)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 NCBXPJLOXWWSLY-UHFFFAOYSA-N 0.000 claims description 3
• VAJKWUITQNVKAZ-UHFFFAOYSA-N 8-hydroxy-9-[4-(4-methylpiperazine-1-carbonyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)C=C1 VAJKWUITQNVKAZ-UHFFFAOYSA-N 0.000 claims description 3
• MUBSOHALWXFKRO-UHFFFAOYSA-N 8-hydroxy-9-[4-[(2-methylsulfonylethylamino)methyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CNCCS(=O)(=O)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 MUBSOHALWXFKRO-UHFFFAOYSA-N 0.000 claims description 3
• GBQAAGRAHOOTMD-UHFFFAOYSA-N 8-methoxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1CNCC2=CC(C3=C4C=5C=CSC=5C(=O)NC4=CC=C3OC)=CC=C21 GBQAAGRAHOOTMD-UHFFFAOYSA-N 0.000 claims description 3
• XCDBVYBTMCZCNS-ONEGZZNKSA-N 8-methoxy-9-[(e)-3-(2-methylsulfonylethylamino)prop-1-enyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C12=C(\C=C\CNCCS(C)(=O)=O)C(OC)=CC=C2NC(=O)C2=C1C=CS2 XCDBVYBTMCZCNS-ONEGZZNKSA-N 0.000 claims description 3
• AACXEIZAHGONCA-UHFFFAOYSA-N 8-methoxy-9-[4-(1-pyrrolidin-1-ylethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1C(C)N1CCCC1 AACXEIZAHGONCA-UHFFFAOYSA-N 0.000 claims description 3
• ZNNRZQWFGFNITF-UHFFFAOYSA-N 8-methoxy-9-[4-(2-piperidin-1-ylethylamino)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1NCCN1CCCCC1 ZNNRZQWFGFNITF-UHFFFAOYSA-N 0.000 claims description 3
• BTDVLKDJMCRFLG-UHFFFAOYSA-N 9-(2,3-dihydro-1h-indol-5-yl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C2NCCC2=CC(C2=C3C=4C=CSC=4C(=O)NC3=CC=C2O)=C1 BTDVLKDJMCRFLG-UHFFFAOYSA-N 0.000 claims description 3
• HMVHRGULQZCBMZ-UHFFFAOYSA-N 9-[3-(aminomethyl)phenyl]-8-hydroxy-2-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound S1C(C)=CC(C=23)=C1C(=O)NC3=CC=C(O)C=2C1=CC=CC(CN)=C1 HMVHRGULQZCBMZ-UHFFFAOYSA-N 0.000 claims description 3
• YLOILQKJJQZBAK-UHFFFAOYSA-N 9-[4-(aminomethyl)phenyl]-8-hydroxy-2-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound S1C(C)=CC(C=23)=C1C(=O)NC3=CC=C(O)C=2C1=CC=C(CN)C=C1 YLOILQKJJQZBAK-UHFFFAOYSA-N 0.000 claims description 3
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 3
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
• HPQRQAOVNXWEEQ-UHFFFAOYSA-N quinoline-8-carboxamide Chemical compound C1=CN=C2C(C(=O)N)=CC=CC2=C1 HPQRQAOVNXWEEQ-UHFFFAOYSA-N 0.000 claims description 3
• KAGAJDBIXZAIED-UHFFFAOYSA-N 2-[5-(8-methoxy-6-methyl-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)pyridin-2-yl]-2-methylpropanenitrile Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)(C)C#N)N=C1 KAGAJDBIXZAIED-UHFFFAOYSA-N 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• VGLHOZOMRLVVBW-SNVBAGLBSA-N 6-bromo-8-hydroxy-9-[4-[(1r)-1-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](C)NC)=CC=C1C1=C(O)C=C(Br)C2=C1C(C=CS1)=C1C(=O)N2 VGLHOZOMRLVVBW-SNVBAGLBSA-N 0.000 claims description 2
• PDZFIQDSXQSTJD-UHFFFAOYSA-N 6-bromo-8-hydroxy-9-[4-[2-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCNC)=CC=C1C1=C(O)C=C(Br)C2=C1C(C=CS1)=C1C(=O)N2 PDZFIQDSXQSTJD-UHFFFAOYSA-N 0.000 claims description 2
• OUQVHDLOVIJYGR-UHFFFAOYSA-N 6-bromo-8-methoxy-9-[4-[2-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCNC)=CC=C1C1=C(OC)C=C(Br)C2=C1C(C=CS1)=C1C(=O)N2 OUQVHDLOVIJYGR-UHFFFAOYSA-N 0.000 claims description 2
• XXHKBVIHHAEOKF-SNVBAGLBSA-N 6-chloro-8-hydroxy-9-[4-[(1r)-1-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](C)NC)=CC=C1C1=C(O)C=C(Cl)C2=C1C(C=CS1)=C1C(=O)N2 XXHKBVIHHAEOKF-SNVBAGLBSA-N 0.000 claims description 2
• XXHKBVIHHAEOKF-JTQLQIEISA-N 6-chloro-8-hydroxy-9-[4-[(1s)-1-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](C)NC)=CC=C1C1=C(O)C=C(Cl)C2=C1C(C=CS1)=C1C(=O)N2 XXHKBVIHHAEOKF-JTQLQIEISA-N 0.000 claims description 2
• UISKFSKGRDJBFK-UHFFFAOYSA-N 6-chloro-8-hydroxy-9-[4-[2-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCNC)=CC=C1C1=C(O)C=C(Cl)C2=C1C(C=CS1)=C1C(=O)N2 UISKFSKGRDJBFK-UHFFFAOYSA-N 0.000 claims description 2
• KKJJJKJXPGVUNZ-UHFFFAOYSA-N 6-chloro-8-methoxy-9-[4-[2-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCNC)=CC=C1C1=C(OC)C=C(Cl)C2=C1C(C=CS1)=C1C(=O)N2 KKJJJKJXPGVUNZ-UHFFFAOYSA-N 0.000 claims description 2
• INPMRBKFXHPFQW-GFCCVEGCSA-N 6-ethyl-8-hydroxy-9-[4-[(1r)-1-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(CC)=CC(O)=C1C1=CC=C([C@@H](C)NC)C=C1 INPMRBKFXHPFQW-GFCCVEGCSA-N 0.000 claims description 2
• OUVMMTWUDVNCFP-UHFFFAOYSA-N 8-hydroxy-6-methyl-9-(4-piperidin-3-ylphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C(C=C1)=CC=C1C1CCCNC1 OUVMMTWUDVNCFP-UHFFFAOYSA-N 0.000 claims description 2
• IFFYITVQSYHAGC-UHFFFAOYSA-N 8-hydroxy-6-methyl-9-[4-(2-methylsulfinylethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C1=CC=C(CCS(C)=O)C=C1 IFFYITVQSYHAGC-UHFFFAOYSA-N 0.000 claims description 2
• ZOGVSVYKILFCFK-UHFFFAOYSA-N 8-hydroxy-6-methyl-9-[4-(methylsulfonylmethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C1=CC=C(CS(C)(=O)=O)C=C1 ZOGVSVYKILFCFK-UHFFFAOYSA-N 0.000 claims description 2
• KJIHSMCYJZTBDW-GFCCVEGCSA-N 8-hydroxy-6-methyl-9-[4-[(1r)-1-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](C)NC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 KJIHSMCYJZTBDW-GFCCVEGCSA-N 0.000 claims description 2
• NNVWBRBPCKJEJW-UHFFFAOYSA-N 8-hydroxy-6-methyl-9-[4-[2-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCNC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 NNVWBRBPCKJEJW-UHFFFAOYSA-N 0.000 claims description 2
• MXABPZVZYZPTEO-UHFFFAOYSA-N 8-hydroxy-9-(4-pentylphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCCCC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 MXABPZVZYZPTEO-UHFFFAOYSA-N 0.000 claims description 2
• FRMJTNDSGRNERX-UHFFFAOYSA-N 8-hydroxy-9-[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(=C1)C=NN1CCN1CCOCC1 FRMJTNDSGRNERX-UHFFFAOYSA-N 0.000 claims description 2
• FXANUBVWYFUQAN-UHFFFAOYSA-N 8-hydroxy-9-[2-[4-(methylaminomethyl)piperidin-1-yl]ethyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1CC(CNC)CCN1CCC1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 FXANUBVWYFUQAN-UHFFFAOYSA-N 0.000 claims description 2
• QHOGQOHOYBGNCD-UHFFFAOYSA-N 8-hydroxy-9-[4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1C1=CCNCC1 QHOGQOHOYBGNCD-UHFFFAOYSA-N 0.000 claims description 2
• OUYUQVWSEPALFY-UHFFFAOYSA-N 8-hydroxy-9-[4-(1-hydroxypropyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(O)CC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 OUYUQVWSEPALFY-UHFFFAOYSA-N 0.000 claims description 2
• OSGRWJPZSSPUAY-UHFFFAOYSA-N 8-hydroxy-9-[4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(O)C(F)(F)F)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 OSGRWJPZSSPUAY-UHFFFAOYSA-N 0.000 claims description 2
• KPVVNPXGNTZHTK-UHFFFAOYSA-N 8-hydroxy-9-[4-(4-hydroxybutyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCCCO)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 KPVVNPXGNTZHTK-UHFFFAOYSA-N 0.000 claims description 2
• ALOPZMQAIBUMHR-UHFFFAOYSA-N 8-hydroxy-9-[4-(4-hydroxypiperidin-4-yl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1C1(O)CCNCC1 ALOPZMQAIBUMHR-UHFFFAOYSA-N 0.000 claims description 2
• GUEFWAUMLRUJFE-LLVKDONJSA-N 8-hydroxy-9-[4-[(1r)-1-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](C)NC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 GUEFWAUMLRUJFE-LLVKDONJSA-N 0.000 claims description 2
• OVSLYFNHAIXXEF-SNVBAGLBSA-N 8-hydroxy-9-[4-[(1r)-1-hydroxyethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](O)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 OVSLYFNHAIXXEF-SNVBAGLBSA-N 0.000 claims description 2
• GUEFWAUMLRUJFE-NSHDSACASA-N 8-hydroxy-9-[4-[(1s)-1-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](C)NC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 GUEFWAUMLRUJFE-NSHDSACASA-N 0.000 claims description 2
• JHHUNTNXOHKEGQ-HNNXBMFYSA-N 8-hydroxy-9-[4-[(1s)-1-(methylamino)propyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](NC)CC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 JHHUNTNXOHKEGQ-HNNXBMFYSA-N 0.000 claims description 2
• OVSLYFNHAIXXEF-JTQLQIEISA-N 8-hydroxy-9-[4-[(1s)-1-hydroxyethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](O)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 OVSLYFNHAIXXEF-JTQLQIEISA-N 0.000 claims description 2
• YOVKJYDIJCCSOV-LBPRGKRZSA-N 8-hydroxy-9-[4-[(2r)-1-(methylamino)propan-2-yl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](C)CNC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 YOVKJYDIJCCSOV-LBPRGKRZSA-N 0.000 claims description 2
• YOVKJYDIJCCSOV-GFCCVEGCSA-N 8-hydroxy-9-[4-[(2s)-1-(methylamino)propan-2-yl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](C)CNC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 YOVKJYDIJCCSOV-GFCCVEGCSA-N 0.000 claims description 2
• CFKUJJZQSSHZPT-UHFFFAOYSA-N 8-hydroxy-9-[4-[2-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCNC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 CFKUJJZQSSHZPT-UHFFFAOYSA-N 0.000 claims description 2
• WKIIZUPWGYVQSE-UHFFFAOYSA-N 8-hydroxy-9-[4-[hydroxy(1,3-thiazol-2-yl)methyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C=1C=C(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)C=CC=1C(O)C1=NC=CS1 WKIIZUPWGYVQSE-UHFFFAOYSA-N 0.000 claims description 2
• MWRDFNNGVGEHQQ-UHFFFAOYSA-N 8-methoxy-6-methyl-9-(4-piperidin-3-ylphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1C1CCCNC1 MWRDFNNGVGEHQQ-UHFFFAOYSA-N 0.000 claims description 2
• PMKLZYGNTVEEEM-UHFFFAOYSA-N 8-methoxy-6-methyl-9-[4-(2-methylsulfinylethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCS(C)=O)C=C1 PMKLZYGNTVEEEM-UHFFFAOYSA-N 0.000 claims description 2
• RZMXLDKXNJIQTL-UHFFFAOYSA-N 8-methoxy-6-methyl-9-[4-(methylsulfonylmethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CS(C)(=O)=O)C=C1 RZMXLDKXNJIQTL-UHFFFAOYSA-N 0.000 claims description 2
• INSXCHLFWDLFGN-CYBMUJFWSA-N 8-methoxy-6-methyl-9-[4-[(1r)-1-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](C)NC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 INSXCHLFWDLFGN-CYBMUJFWSA-N 0.000 claims description 2
• FLOKZOFNWSJEII-UHFFFAOYSA-N 8-methoxy-6-methyl-9-[4-[2-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCNC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 FLOKZOFNWSJEII-UHFFFAOYSA-N 0.000 claims description 2
• DFHBZEXLZYGAMM-UHFFFAOYSA-N 8-methoxy-9-[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(=C1)C=NN1CCN1CCOCC1 DFHBZEXLZYGAMM-UHFFFAOYSA-N 0.000 claims description 2
• IERBJNIBYYFGOB-UHFFFAOYSA-N 8-methoxy-9-[2-(piperidin-4-ylamino)ethyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1CCNC1CCNCC1 IERBJNIBYYFGOB-UHFFFAOYSA-N 0.000 claims description 2
• ATAJJEBIIMGXAS-UHFFFAOYSA-N 8-methoxy-9-[2-[4-(methylaminomethyl)piperidin-1-yl]ethyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1CC(CNC)CCN1CCC1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 ATAJJEBIIMGXAS-UHFFFAOYSA-N 0.000 claims description 2
• JLFIHMOMYJJSNK-UHFFFAOYSA-N 8-methoxy-9-[4-(1-methoxyethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(C)OC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 JLFIHMOMYJJSNK-UHFFFAOYSA-N 0.000 claims description 2
• KWVUNLXKOZBNPQ-UHFFFAOYSA-N 8-methoxy-9-[4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(O)C(F)(F)F)C=C1 KWVUNLXKOZBNPQ-UHFFFAOYSA-N 0.000 claims description 2
• XRZNWKLGDLAKCQ-LBPRGKRZSA-N 8-methoxy-9-[4-[(1s)-1-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](C)NC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 XRZNWKLGDLAKCQ-LBPRGKRZSA-N 0.000 claims description 2
• MAWBXVBOFBSAKF-INIZCTEOSA-N 8-methoxy-9-[4-[(1s)-1-(methylamino)propyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](NC)CC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 MAWBXVBOFBSAKF-INIZCTEOSA-N 0.000 claims description 2
• MZXFISVQLXLFES-CYBMUJFWSA-N 8-methoxy-9-[4-[(2s)-1-(methylamino)propan-2-yl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](C)CNC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 MZXFISVQLXLFES-CYBMUJFWSA-N 0.000 claims description 2
• UWNHAAMTGMBUKA-UHFFFAOYSA-N 8-methoxy-9-[4-[2-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCNC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 UWNHAAMTGMBUKA-UHFFFAOYSA-N 0.000 claims description 2
• ONDHFIOKVDXRBG-UHFFFAOYSA-N 9-[4-(1-aminobutan-2-yl)phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(CN)CC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 ONDHFIOKVDXRBG-UHFFFAOYSA-N 0.000 claims description 2
• IVTXKZOAEFIJGG-UHFFFAOYSA-N 9-[4-(1-aminobutan-2-yl)phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(CN)CC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 IVTXKZOAEFIJGG-UHFFFAOYSA-N 0.000 claims description 2
• VQKSOYZVZHKANT-UHFFFAOYSA-N 9-[4-(1-aminoethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(N)C)=CC=C1C1=CC=CC2=C1C(C=CS1)=C1C(=O)N2 VQKSOYZVZHKANT-UHFFFAOYSA-N 0.000 claims description 2
• SFDGEUZYJDXBSA-UHFFFAOYSA-N 9-[4-(1-aminoethyl)phenyl]-8-(difluoromethyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(N)C)=CC=C1C1=C(C(F)F)C=CC2=C1C(C=CS1)=C1C(=O)N2 SFDGEUZYJDXBSA-UHFFFAOYSA-N 0.000 claims description 2
• WNNBRJAKIHWJKB-UHFFFAOYSA-N 9-[4-(1-aminoethyl)phenyl]-8-(hydroxymethyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(N)C)=CC=C1C1=C(CO)C=CC2=C1C(C=CS1)=C1C(=O)N2 WNNBRJAKIHWJKB-UHFFFAOYSA-N 0.000 claims description 2
• YLYUPCCLFIVUFG-UHFFFAOYSA-N 9-[4-(1-aminoethyl)phenyl]-8-[(2-hydroxyethylamino)methyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(N)C)=CC=C1C1=C(CNCCO)C=CC2=C1C(C=CS1)=C1C(=O)N2 YLYUPCCLFIVUFG-UHFFFAOYSA-N 0.000 claims description 2
• LNRLTANCPMMQGN-UHFFFAOYSA-N 9-[4-(1-aminoethyl)phenyl]-8-hydroxy-6-(hydroxymethyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(N)C)=CC=C1C1=C(O)C=C(CO)C2=C1C(C=CS1)=C1C(=O)N2 LNRLTANCPMMQGN-UHFFFAOYSA-N 0.000 claims description 2
• KUUKWPWCBMKITD-UHFFFAOYSA-N 9-[4-(1-aminopropan-2-yl)anilino]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1NC1=CC=C(C(C)CN)C=C1 KUUKWPWCBMKITD-UHFFFAOYSA-N 0.000 claims description 2
• BVAGHNZNCMQOEW-UHFFFAOYSA-N 9-[4-(2-amino-1-fluoroethyl)phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(F)CN)C=C1 BVAGHNZNCMQOEW-UHFFFAOYSA-N 0.000 claims description 2
• BDWGECYBUREAJY-UHFFFAOYSA-N 9-[4-(2-amino-1-hydroxyethyl)phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(O)CN)C=C1 BDWGECYBUREAJY-UHFFFAOYSA-N 0.000 claims description 2
• DKFRLZXGZIQKDF-UHFFFAOYSA-N 9-[4-(2-aminopropan-2-yl)phenyl]-2-(benzenesulfonyl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(C)(N)C)=CC=C1C1=C(O)C=CC2=C1C(C=C(S1)S(=O)(=O)C=3C=CC=CC=3)=C1C(=O)N2 DKFRLZXGZIQKDF-UHFFFAOYSA-N 0.000 claims description 2
• POTNGNAKXOTMIQ-UHFFFAOYSA-N 9-[4-(2-aminopropan-2-yl)phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C1=CC=C(C(C)(C)N)C=C1 POTNGNAKXOTMIQ-UHFFFAOYSA-N 0.000 claims description 2
• PKJUJTYYMYNCFT-UHFFFAOYSA-N 9-[4-(2-aminopropyl)phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CC(N)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 PKJUJTYYMYNCFT-UHFFFAOYSA-N 0.000 claims description 2
• ZZALMQFMTCLAPG-UHFFFAOYSA-N 9-[4-(aminomethyl)phenyl]-8-(2-morpholin-4-ylethoxy)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CN)=CC=C1C(C=1C=2C=CSC=2C(=O)NC=1C=C1)=C1OCCN1CCOCC1 ZZALMQFMTCLAPG-UHFFFAOYSA-N 0.000 claims description 2
• CGUWNYDGDUJONC-PXYINDEMSA-N 9-[4-[(2r)-1-aminopropan-2-yl]phenyl]-8-hydroxy-2-(1-hydroxyethyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound S1C(C(O)C)=CC(C=23)=C1C(=O)NC3=CC=C(O)C=2C1=CC=C([C@@H](C)CN)C=C1 CGUWNYDGDUJONC-PXYINDEMSA-N 0.000 claims description 2
• BKECLKGMYTZOIX-ZDUSSCGKSA-N 9-[4-[(2r)-1-aminopropan-2-yl]phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C([C@@H](C)CN)C=C1 BKECLKGMYTZOIX-ZDUSSCGKSA-N 0.000 claims description 2
• OETLNMOJNONWOY-GFCCVEGCSA-N 9-[4-[(2s)-1-aminopropan-2-yl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](CN)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 OETLNMOJNONWOY-GFCCVEGCSA-N 0.000 claims description 2
• BAGJPDYVOWKTFN-UHFFFAOYSA-N 9-[4-[2-aminoethyl(methyl)amino]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(N(CCN)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 BAGJPDYVOWKTFN-UHFFFAOYSA-N 0.000 claims description 2
• AKYWESRXKMVCBM-UHFFFAOYSA-N 9-[4-[3-(aminomethyl)pentan-3-yl]phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(CC)(CN)CC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 AKYWESRXKMVCBM-UHFFFAOYSA-N 0.000 claims description 2
• AEUTUPWPCBNJFJ-UHFFFAOYSA-N 9-[6-(1-aminopropan-2-yl)pyridin-3-yl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=NC(C(CN)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 AEUTUPWPCBNJFJ-UHFFFAOYSA-N 0.000 claims description 2
• SWPDOGBONBFCBM-UHFFFAOYSA-N 9-[6-(1-aminopropan-2-yl)pyridin-3-yl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)CN)N=C1 SWPDOGBONBFCBM-UHFFFAOYSA-N 0.000 claims description 2
• CGQLUDAJRJTENG-UHFFFAOYSA-N 9-[6-(2-aminoethoxy)pyridin-3-yl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C1=CC=C(OCCN)N=C1 CGQLUDAJRJTENG-UHFFFAOYSA-N 0.000 claims description 2
• NNQZIMRMLNHQMJ-UHFFFAOYSA-N 9-amino-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C12=C(N)C(OC)=CC(C)=C2NC(=O)C2=C1C=CS2 NNQZIMRMLNHQMJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims description 2
• KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
• 229960003966 nicotinamide Drugs 0.000 claims description 2
• 235000005152 nicotinamide Nutrition 0.000 claims description 2
• 239000011570 nicotinamide Substances 0.000 claims description 2
• NIFLNJLWZZABMI-UHFFFAOYSA-N quinoline-6-carbonitrile Chemical compound N1=CC=CC2=CC(C#N)=CC=C21 NIFLNJLWZZABMI-UHFFFAOYSA-N 0.000 claims description 2
• QSTRDZKAPUTJCL-ZDUSSCGKSA-N 8-hydroxy-6-methyl-9-[4-[(2r)-1-(methylamino)propan-2-yl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](C)CNC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 QSTRDZKAPUTJCL-ZDUSSCGKSA-N 0.000 claims 2
• MQYDMKMSBNAVGG-LLVKDONJSA-N 6-chloro-8-hydroxy-9-[4-[(2s)-1-(methylamino)propan-2-yl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](C)CNC)=CC=C1C1=C(O)C=C(Cl)C2=C1C(C=CS1)=C1C(=O)N2 MQYDMKMSBNAVGG-LLVKDONJSA-N 0.000 claims 1
• SJVBKIJJPQBWCC-AWEZNQCLSA-N 8-hydroxy-6-methyl-9-[4-[(2r)-1-(methylamino)butan-2-yl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](CNC)CC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 SJVBKIJJPQBWCC-AWEZNQCLSA-N 0.000 claims 1
• QSTRDZKAPUTJCL-CYBMUJFWSA-N 8-hydroxy-6-methyl-9-[4-[(2s)-1-(methylamino)propan-2-yl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](C)CNC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 QSTRDZKAPUTJCL-CYBMUJFWSA-N 0.000 claims 1
• WFMVDHKPGZGFJZ-UHFFFAOYSA-N 8-hydroxy-6-methyl-9-[4-[3-methyl-1-(methylamino)butan-2-yl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(C(C)C)CNC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 WFMVDHKPGZGFJZ-UHFFFAOYSA-N 0.000 claims 1
• QEZZJWCBFRIFFR-HNNXBMFYSA-N 8-methoxy-6-methyl-9-[4-[(2r)-1-(methylamino)butan-2-yl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](CNC)CC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 QEZZJWCBFRIFFR-HNNXBMFYSA-N 0.000 claims 1
• ODPZHVOWWJJQLR-AWEZNQCLSA-N 8-methoxy-6-methyl-9-[4-[(2r)-1-(methylamino)propan-2-yl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](C)CNC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 ODPZHVOWWJJQLR-AWEZNQCLSA-N 0.000 claims 1
• ODPZHVOWWJJQLR-CQSZACIVSA-N 8-methoxy-6-methyl-9-[4-[(2s)-1-(methylamino)propan-2-yl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](C)CNC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 ODPZHVOWWJJQLR-CQSZACIVSA-N 0.000 claims 1
• FNDUIBOVMHQIHB-UHFFFAOYSA-N 8-methoxy-6-methyl-9-[4-[3-methyl-1-(methylamino)butan-2-yl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(C(C)C)CNC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 FNDUIBOVMHQIHB-UHFFFAOYSA-N 0.000 claims 1
• YKHYZDATSATHHW-UHFFFAOYSA-N 8-methoxy-9-[2-(piperidin-3-ylmethylamino)ethyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1CCNCC1CCCNC1 YKHYZDATSATHHW-UHFFFAOYSA-N 0.000 claims 1
• XRZNWKLGDLAKCQ-GFCCVEGCSA-N 8-methoxy-9-[4-[(1r)-1-(methylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](C)NC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 XRZNWKLGDLAKCQ-GFCCVEGCSA-N 0.000 claims 1
• MZXFISVQLXLFES-ZDUSSCGKSA-N 8-methoxy-9-[4-[(2r)-1-(methylamino)propan-2-yl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](C)CNC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 MZXFISVQLXLFES-ZDUSSCGKSA-N 0.000 claims 1
• YBMIPLDRKSHPID-UHFFFAOYSA-N 9-[6-(2-aminoethylamino)pyridin-3-yl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C1=CC=C(NCCN)N=C1 YBMIPLDRKSHPID-UHFFFAOYSA-N 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
• 229910052799 carbon Inorganic materials 0.000 claims 1
• STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims 1
• APRJFNLVTJWEPP-UHFFFAOYSA-M n,n-diethylcarbamate Chemical compound CCN(CC)C([O-])=O APRJFNLVTJWEPP-UHFFFAOYSA-M 0.000 claims 1
• DWLVWMUCHSLGSU-UHFFFAOYSA-M n,n-dimethylcarbamate Chemical compound CN(C)C([O-])=O DWLVWMUCHSLGSU-UHFFFAOYSA-M 0.000 claims 1
• AHIHJODVQGBOND-UHFFFAOYSA-M propan-2-yl carbonate Chemical compound CC(C)OC([O-])=O AHIHJODVQGBOND-UHFFFAOYSA-M 0.000 claims 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
• 125000004432 carbon atom Chemical group C* 0.000 abstract description 12
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 989
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 484
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 284
• 238000004128 high performance liquid chromatography Methods 0.000 description 234
• 238000005160 1H NMR spectroscopy Methods 0.000 description 226
• 244000257039 Duranta repens Species 0.000 description 157
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 116
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 105
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 104
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 102
• 229910052796 boron Inorganic materials 0.000 description 96
• 229940092727 claro Drugs 0.000 description 88
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 78
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 78
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 58
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 55
• 102100026753 Lymphokine-activated killer T-cell-originated protein kinase Human genes 0.000 description 54
• 108010014971 PDZ-binding kinase Proteins 0.000 description 54
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 47
• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 45
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 43
• 229910015845 BBr3 Inorganic materials 0.000 description 39
• 229910052731 fluorine Inorganic materials 0.000 description 38
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 34
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 27
• 239000000463 material Substances 0.000 description 26
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 23
• COLGMZQCAPDJEQ-UHFFFAOYSA-N 5h-thieno[2,3-c]quinolin-4-one Chemical compound O=C1NC2=CC=CC=C2C2=C1SC=C2 COLGMZQCAPDJEQ-UHFFFAOYSA-N 0.000 description 22
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 22
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
• 125000004076 pyridyl group Chemical group 0.000 description 12
• 125000002393 azetidinyl group Chemical group 0.000 description 11
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
• 125000003226 pyrazolyl group Chemical group 0.000 description 10
• 239000007832 Na2SO4 Substances 0.000 description 9
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
• 241000718541 Tetragastris balsamifera Species 0.000 description 9
• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 9
• 229910052938 sodium sulfate Inorganic materials 0.000 description 9
• 235000011152 sodium sulphate Nutrition 0.000 description 9
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 8
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 8
• 229910000085 borane Inorganic materials 0.000 description 8
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
• 235000011114 ammonium hydroxide Nutrition 0.000 description 7
• 239000002585 base Substances 0.000 description 7
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
• 230000001419 dependent effect Effects 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
• 125000002541 furyl group Chemical group 0.000 description 6
• 125000005842 heteroatom Chemical group 0.000 description 6
• 125000002883 imidazolyl group Chemical group 0.000 description 6
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 description 6
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 6
• 125000001544 thienyl group Chemical group 0.000 description 6
• 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 description 5
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical group [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
• 240000002319 Citrus sinensis Species 0.000 description 5
• 102220497176 Small vasohibin-binding protein_T47D_mutation Human genes 0.000 description 5
• 210000004027 cell Anatomy 0.000 description 5
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
• 125000005955 1H-indazolyl group Chemical group 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
• 102220541603 Centrin-1_R22A_mutation Human genes 0.000 description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
• 102220475856 Keratin, type I cytoskeletal 10_R21A_mutation Human genes 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 4
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 4
• OWCDMRFUFMERMZ-UHFFFAOYSA-N benzenesulfonamide;hydrochloride Chemical compound Cl.NS(=O)(=O)C1=CC=CC=C1 OWCDMRFUFMERMZ-UHFFFAOYSA-N 0.000 description 4
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
• 125000005587 carbonate group Chemical group 0.000 description 4
• 230000014509 gene expression Effects 0.000 description 4
• 150000002500 ions Chemical class 0.000 description 4
• 230000011278 mitosis Effects 0.000 description 4
• IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
• 239000012453 solvate Substances 0.000 description 4
• 241000670727 Amida Species 0.000 description 3
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
• 241000238366 Cephalopoda Species 0.000 description 3
• 241001446467 Mama Species 0.000 description 3
• 238000005481 NMR spectroscopy Methods 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 125000003277 amino group Chemical group 0.000 description 3
• 125000003725 azepanyl group Chemical group 0.000 description 3
• 125000004069 aziridinyl group Chemical group 0.000 description 3
• 125000005605 benzo group Chemical group 0.000 description 3
• 125000005621 boronate group Chemical group 0.000 description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 230000000694 effects Effects 0.000 description 3
• XLZLNCSZYWPDRJ-UHFFFAOYSA-N ethanesulfonamide;hydrochloride Chemical compound Cl.CCS(N)(=O)=O XLZLNCSZYWPDRJ-UHFFFAOYSA-N 0.000 description 3
• MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 3
• 150000002430 hydrocarbons Chemical group 0.000 description 3
• 125000002632 imidazolidinyl group Chemical group 0.000 description 3
• 229910052740 iodine Inorganic materials 0.000 description 3
• 230000009021 linear effect Effects 0.000 description 3
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
• 238000000034 method Methods 0.000 description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
• 125000003566 oxetanyl group Chemical group 0.000 description 3
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
• 125000003831 tetrazolyl group Chemical group 0.000 description 3
• SWYXNZSVZIMOSF-VQHVLOKHSA-N (e)-3-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)-2-methylprop-2-enenitrile Chemical compound C12=C(\C=C(/C)C#N)C(OC)=CC=C2NC(=O)C2=C1C=CS2 SWYXNZSVZIMOSF-VQHVLOKHSA-N 0.000 description 2
• SORUMIWSFRGDCF-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfanyl-4-nitrobenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1SC1=CC=C(F)C=C1 SORUMIWSFRGDCF-UHFFFAOYSA-N 0.000 description 2
• QDMWCSIVFJZKSD-UHFFFAOYSA-N 3-[(4-bromophenyl)methyl]-1-(4-fluorophenyl)pyrrolidine-2,5-dione Chemical compound C1=CC(F)=CC=C1N1C(=O)C(CC=2C=CC(Br)=CC=2)CC1=O QDMWCSIVFJZKSD-UHFFFAOYSA-N 0.000 description 2
• ZVMQNPSOQBOZOE-UHFFFAOYSA-N 9-[4-[1-(dimethylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(N(C)C)C)=CC=C1C1=CC=CC2=C1C(C=CS1)=C1C(=O)N2 ZVMQNPSOQBOZOE-UHFFFAOYSA-N 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
• 206010006187 Breast cancer Diseases 0.000 description 2
• 208000026310 Breast neoplasm Diseases 0.000 description 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
• 241000324343 Causa Species 0.000 description 2
• 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• 102220475869 Keratin, type I cytoskeletal 10_R12A_mutation Human genes 0.000 description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
• 102220595577 Major vault protein_R24A_mutation Human genes 0.000 description 2
• 102220595571 Major vault protein_R52A_mutation Human genes 0.000 description 2
• 108090000744 Mitogen-Activated Protein Kinase Kinases Proteins 0.000 description 2
• 102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 description 2
• 102220587413 N-acetylserotonin O-methyltransferase-like protein_R23A_mutation Human genes 0.000 description 2
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
• 102220558655 Nuclear protein 1_R51A_mutation Human genes 0.000 description 2
• 240000001987 Pyrus communis Species 0.000 description 2
• 241001521328 Ruta Species 0.000 description 2
• 235000003976 Ruta Nutrition 0.000 description 2
• 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• 241000292525 Titanio Species 0.000 description 2
• RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
• 125000003342 alkenyl group Chemical group 0.000 description 2
• 125000000304 alkynyl group Chemical group 0.000 description 2
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
• 125000005872 benzooxazolyl group Chemical group 0.000 description 2
• 210000000601 blood cell Anatomy 0.000 description 2
• 229910000024 caesium carbonate Inorganic materials 0.000 description 2
• 239000003814 drug Substances 0.000 description 2
• 229940079593 drug Drugs 0.000 description 2
• HQOBZYOPKFTLLE-UHFFFAOYSA-N ethyl 2-[(4-bromophenyl)methyl]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5h-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate Chemical compound O=C1N2C(C=3C=CC(OC)=CC=3)C(C(=O)OCC)=C(C)N=C2SC1CC1=CC=C(Br)C=C1 HQOBZYOPKFTLLE-UHFFFAOYSA-N 0.000 description 2
• 235000019439 ethyl acetate Nutrition 0.000 description 2
• 235000019253 formic acid Nutrition 0.000 description 2
• 239000000499 gel Substances 0.000 description 2
• 230000012010 growth Effects 0.000 description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
• 230000002401 inhibitory effect Effects 0.000 description 2
• 238000007918 intramuscular administration Methods 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
• 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 2
• SZWLZSXCHWTRCF-UHFFFAOYSA-N n-[5-[(4-fluorophenyl)methyl]-1,3-thiazol-2-yl]-3,4-dihydro-2h-chromene-3-carboxamide Chemical compound C1=CC(F)=CC=C1CC(S1)=CN=C1NC(=O)C1CC2=CC=CC=C2OC1 SZWLZSXCHWTRCF-UHFFFAOYSA-N 0.000 description 2
• 229910052757 nitrogen Inorganic materials 0.000 description 2
• 210000000056 organ Anatomy 0.000 description 2
• 235000015927 pasta Nutrition 0.000 description 2
• 239000000047 product Substances 0.000 description 2
• BXFXDABQQRHCLL-UHFFFAOYSA-N quinolin-8-yl methanesulfonate Chemical compound C1=CN=C2C(OS(=O)(=O)C)=CC=CC2=C1 BXFXDABQQRHCLL-UHFFFAOYSA-N 0.000 description 2
• YUWOECMFUBVGSE-UHFFFAOYSA-N quinolin-8-yl trifluoromethanesulfonate Chemical compound C1=CN=C2C(OS(=O)(=O)C(F)(F)F)=CC=CC2=C1 YUWOECMFUBVGSE-UHFFFAOYSA-N 0.000 description 2
• ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 description 2
• 235000005806 ruta Nutrition 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• 229910000104 sodium hydride Inorganic materials 0.000 description 2
• 229910052717 sulfur Inorganic materials 0.000 description 2
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• 125000000335 thiazolyl group Chemical group 0.000 description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 1
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
• 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 description 1
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
• CRPTXKKKIGGDBX-UHFFFAOYSA-N (z)-but-2-ene Chemical group [CH2]C=CC CRPTXKKKIGGDBX-UHFFFAOYSA-N 0.000 description 1
• GSMCDXGKZOUAET-UHFFFAOYSA-N (z)-pent-2-ene Chemical group C[CH]C=CC GSMCDXGKZOUAET-UHFFFAOYSA-N 0.000 description 1
• BYIQVAUNWASMFP-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(O)=CC=C1C1=CSC2=C1C1=CC=CC=C1NC2=O BYIQVAUNWASMFP-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
• PMJPVEVUFKWVNB-UHFFFAOYSA-N 1-methyl-2-(4-nitrophenyl)sulfanylbenzene Chemical compound CC1=CC=CC=C1SC1=CC=C([N+]([O-])=O)C=C1 PMJPVEVUFKWVNB-UHFFFAOYSA-N 0.000 description 1
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
• QCXXSTHKXNBIPF-UHFFFAOYSA-M 2,2-dimethyl-1,3-dihydroisoindol-2-ium;bromide Chemical compound [Br-].C1=CC=C2C[N+](C)(C)CC2=C1 QCXXSTHKXNBIPF-UHFFFAOYSA-M 0.000 description 1
• HIJZBROSVFKSCP-UHFFFAOYSA-N 2-(4-bromophenyl)pyrrolidine Chemical compound C1=CC(Br)=CC=C1C1NCCC1 HIJZBROSVFKSCP-UHFFFAOYSA-N 0.000 description 1
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• 125000006119 2-ethylbutyl sulfinyl group Chemical group 0.000 description 1
• 125000006149 2-ethylbutyl sulfonyl group Chemical group 0.000 description 1
• 125000004913 2-ethylbutylamino group Chemical group C(C)C(CN*)CC 0.000 description 1
• 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 1
• 125000004918 2-methyl-2-pentyl group Chemical group CC(C)(CCC)* 0.000 description 1
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 1
• 125000004919 3-methyl-2-pentyl group Chemical group CC(C(C)*)CC 0.000 description 1
• 125000004921 3-methyl-3-pentyl group Chemical group CC(CC)(CC)* 0.000 description 1
• VLBIFNCUKNKYMD-UHFFFAOYSA-N 3-methylbut-1-ene Chemical group [CH2]C(C)C=C VLBIFNCUKNKYMD-UHFFFAOYSA-N 0.000 description 1
• 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
• ALBQXDHCMLLQMB-UHFFFAOYSA-N 4-phenylbenzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1C1=CC=CC=C1 ALBQXDHCMLLQMB-UHFFFAOYSA-N 0.000 description 1
• HAJSOFXLKFWERP-UHFFFAOYSA-N 5-bromo-2-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=C(Br)C=N1 HAJSOFXLKFWERP-UHFFFAOYSA-N 0.000 description 1
• RXGXIUOMURUNLV-HNNXBMFYSA-N 6-chloro-8-hydroxy-9-[4-[(1s)-1-(methylamino)propyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](NC)CC)=CC=C1C1=C(O)C=C(Cl)C2=C1C(C=CS1)=C1C(=O)N2 RXGXIUOMURUNLV-HNNXBMFYSA-N 0.000 description 1
• OTOOMNLVTOLNDO-UHFFFAOYSA-N 6-fluoro-8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)-5h-thieno[2,3-c]quinolin-4-one;hydrochloride Chemical compound Cl.COC1=CC(F)=C2NC(=O)C=3SC=CC=3C2=C1C1=CCNCC1 OTOOMNLVTOLNDO-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• OSJDAAWCZVSARC-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1C(N)CCCN1C1=CC=C(NC(=O)C2=C3C=CS2)C3=C1 OSJDAAWCZVSARC-UHFFFAOYSA-N 0.000 description 1
• JINGBYVUFAYDQK-UHFFFAOYSA-N 8-(4-hydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(O)=CC=C1C1=CC=C(NC(=O)C2=C3C=CS2)C3=C1 JINGBYVUFAYDQK-UHFFFAOYSA-N 0.000 description 1
• RGLAPZFAXMKYGJ-CURYUGHLSA-N 8-[(3r)-3-aminopyrrolidin-1-yl]-2-(3,4-dihydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one;dihydrochloride Chemical compound Cl.Cl.C1[C@H](N)CCN1C1=CC=C(NC(=O)C2=C3C=C(S2)C=2C=C(O)C(O)=CC=2)C3=C1 RGLAPZFAXMKYGJ-CURYUGHLSA-N 0.000 description 1
• VXMLDEHONAKIDN-SECBINFHSA-N 8-[(3r)-3-aminopyrrolidin-1-yl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1[C@H](N)CCN1C1=CC=C(NC(=O)C2=C3C=CS2)C3=C1 VXMLDEHONAKIDN-SECBINFHSA-N 0.000 description 1
• FGJQRGSWKYZTJF-GXKRWWSZSA-N 8-[(3s)-3-aminopyrrolidin-1-yl]-2-(4-hydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N)CCN1C1=CC=C(NC(=O)C2=C3C=C(S2)C=2C=CC(O)=CC=2)C3=C1 FGJQRGSWKYZTJF-GXKRWWSZSA-N 0.000 description 1
• VXMLDEHONAKIDN-VIFPVBQESA-N 8-[(3s)-3-aminopyrrolidin-1-yl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1[C@@H](N)CCN1C1=CC=C(NC(=O)C2=C3C=CS2)C3=C1 VXMLDEHONAKIDN-VIFPVBQESA-N 0.000 description 1
• UVBVMGGRHAHDKF-UHFFFAOYSA-N 8-hydroxy-1,2,3,5-tetrahydrocyclopenta[c]quinolin-4-one Chemical compound C12=CC(O)=CC=C2NC(=O)C2=C1CCC2 UVBVMGGRHAHDKF-UHFFFAOYSA-N 0.000 description 1
• AXEIAYGXFBTRGB-UHFFFAOYSA-N 8-hydroxy-1-(4-hydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(O)=CC=C1C1=CSC2=C1C1=CC(O)=CC=C1NC2=O AXEIAYGXFBTRGB-UHFFFAOYSA-N 0.000 description 1
• IIIZAWOYAGMVAI-UHFFFAOYSA-N 8-hydroxy-1-methyl-3,5-dihydropyrrolo[2,3-c]quinolin-4-one Chemical compound C12=CC(O)=CC=C2NC(=O)C2=C1C(C)=CN2 IIIZAWOYAGMVAI-UHFFFAOYSA-N 0.000 description 1
• KSBQEIVGQXRPTE-UHFFFAOYSA-N 8-hydroxy-1-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C12=CC(O)=CC=C2NC(=O)C2=C1C(C)=CS2 KSBQEIVGQXRPTE-UHFFFAOYSA-N 0.000 description 1
• UUFOMVOYZDQBCL-UHFFFAOYSA-N 8-hydroxy-1-piperazin-1-yl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C3=CC(O)=CC=C3NC(=O)C=2SC=C1N1CCNCC1 UUFOMVOYZDQBCL-UHFFFAOYSA-N 0.000 description 1
• PUZFGEPGURMRMA-UHFFFAOYSA-N 8-hydroxy-2-(3-hydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=CC(C=2SC3=C(C4=CC(O)=CC=C4NC3=O)C=2)=C1 PUZFGEPGURMRMA-UHFFFAOYSA-N 0.000 description 1
• DELHFABCDMXAES-UHFFFAOYSA-N 8-hydroxy-2-(4-hydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(O)=CC=C1C1=CC(C2=CC(O)=CC=C2NC2=O)=C2S1 DELHFABCDMXAES-UHFFFAOYSA-N 0.000 description 1
• JFCWTVWWCATXFS-UHFFFAOYSA-N 8-hydroxy-2-(hydroxymethyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound O=C1NC2=CC=C(O)C=C2C2=C1SC(CO)=C2 JFCWTVWWCATXFS-UHFFFAOYSA-N 0.000 description 1
• LUANYKDGOHQLCG-UHFFFAOYSA-N 8-hydroxy-2-[(piperidin-3-ylamino)methyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound C=1C=2C3=CC(O)=CC=C3NC(=O)C=2SC=1CNC1CCCNC1 LUANYKDGOHQLCG-UHFFFAOYSA-N 0.000 description 1
• WIVNKCLTKSNCPB-UHFFFAOYSA-N 8-hydroxy-2-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound O=C1NC2=CC=C(O)C=C2C2=C1SC(C)=C2 WIVNKCLTKSNCPB-UHFFFAOYSA-N 0.000 description 1
• QDZMYXDZMLMTKW-UHFFFAOYSA-N 8-hydroxy-3-methyl-5h-pyrrolo[2,3-c]quinolin-4-one Chemical compound O=C1NC2=CC=C(O)C=C2C2=C1N(C)C=C2 QDZMYXDZMLMTKW-UHFFFAOYSA-N 0.000 description 1
• WFMSDZQYKMADIC-UHFFFAOYSA-N 8-hydroxy-5-methylthieno[2,3-c]quinolin-4-one Chemical compound O=C1N(C)C2=CC=C(O)C=C2C2=C1SC=C2 WFMSDZQYKMADIC-UHFFFAOYSA-N 0.000 description 1
• ZXJDYRKDGGYEAN-UHFFFAOYSA-N 8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)-1,2,3,5-tetrahydrocyclopenta[c]quinolin-4-one;hydrochloride Chemical compound Cl.OC1=CC=C2NC(=O)C=3CCCC=3C2=C1C1=CCNCC1 ZXJDYRKDGGYEAN-UHFFFAOYSA-N 0.000 description 1
• ZAKZGHPLIHIUKN-UHFFFAOYSA-N 8-hydroxy-9-(5-hydroxypyridin-3-yl)-1,2,3,5-tetrahydrocyclopenta[c]quinolin-4-one;hydrochloride Chemical compound Cl.OC1=CN=CC(C=2C=3C=4CCCC=4C(=O)NC=3C=CC=2O)=C1 ZAKZGHPLIHIUKN-UHFFFAOYSA-N 0.000 description 1
• SDMKRJSSPOUUTR-UHFFFAOYSA-N 8-hydroxy-9-[4-(1-pyrrolidin-1-ylethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one;hydrochloride Chemical compound Cl.C=1C=C(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)C=CC=1C(C)N1CCCC1 SDMKRJSSPOUUTR-UHFFFAOYSA-N 0.000 description 1
• WTBTUTIFZHFNQX-UHFFFAOYSA-N 8-hydroxy-9-[4-[(propan-2-ylamino)methyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one;hydrochloride Chemical compound Cl.C1=CC(CNC(C)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 WTBTUTIFZHFNQX-UHFFFAOYSA-N 0.000 description 1
• YPSXGURLEKYHBE-UHFFFAOYSA-N 8-hydroxy-9-[4-[1-(2-methylsulfonylethylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one;hydrochloride Chemical compound Cl.C1=CC(C(NCCS(C)(=O)=O)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 YPSXGURLEKYHBE-UHFFFAOYSA-N 0.000 description 1
• AAIRXTJUNOKVMC-UHFFFAOYSA-N 8-methoxy-1,2,3,5-tetrahydrocyclopenta[c]quinolin-4-one Chemical compound C12=CC(OC)=CC=C2NC(=O)C2=C1CCC2 AAIRXTJUNOKVMC-UHFFFAOYSA-N 0.000 description 1
• KUXNLIVPMNMRAB-UHFFFAOYSA-N 8-methoxy-3-methyl-5h-pyrrolo[2,3-c]quinolin-4-one Chemical compound C12=CC(OC)=CC=C2NC(=O)C2=C1C=CN2C KUXNLIVPMNMRAB-UHFFFAOYSA-N 0.000 description 1
• AHBAVEISISHBAS-UHFFFAOYSA-N 8-methoxy-5-methylthieno[2,3-c]quinolin-4-one Chemical compound C12=CC(OC)=CC=C2N(C)C(=O)C2=C1C=CS2 AHBAVEISISHBAS-UHFFFAOYSA-N 0.000 description 1
• FKHPKLVTFSZKPO-UHFFFAOYSA-N 8-methoxy-5h-[1,3]thiazolo[4,5-c]quinolin-4-one Chemical compound C12=CC(OC)=CC=C2NC(=O)C2=C1SC=N2 FKHPKLVTFSZKPO-UHFFFAOYSA-N 0.000 description 1
• ZPFFUACAULEMKK-UHFFFAOYSA-N 8-methoxy-9-(5-methoxypyridin-3-yl)-1,2,3,5-tetrahydrocyclopenta[c]quinolin-4-one hydrochloride Chemical compound Cl.COC1=C(C=2C3=C(C(NC2C=C1)=O)CCC3)C=3C=NC=C(C3)OC ZPFFUACAULEMKK-UHFFFAOYSA-N 0.000 description 1
• RFAPXMQTCWRIQD-UHFFFAOYSA-N 8-methoxy-9-[4-(1-piperidin-1-ylethyl)phenyl]-5H-thieno[2,3-c]quinolin-4-one hydrochloride Chemical compound Cl.COC1=C(C=2C3=C(C(NC2C=C1)=O)SC=C3)C3=CC=C(C=C3)C(C)N3CCCCC3 RFAPXMQTCWRIQD-UHFFFAOYSA-N 0.000 description 1
• VIPRFCNFSKFCJJ-UHFFFAOYSA-N 8-methoxy-9-[4-(4-methylpiperazin-1-yl)phenyl]-5H-thieno[2,3-c]quinolin-4-one dihydrochloride Chemical compound Cl.Cl.COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1N1CCN(C)CC1 VIPRFCNFSKFCJJ-UHFFFAOYSA-N 0.000 description 1
• CPNIXBIUEZLZLA-UHFFFAOYSA-N 8-methoxy-9-[4-[1-(2-methylsulfonylethylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one;hydrochloride Chemical compound Cl.COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)NCCS(C)(=O)=O)C=C1 CPNIXBIUEZLZLA-UHFFFAOYSA-N 0.000 description 1
• JWNHEGZUCDVEHD-UHFFFAOYSA-N 8-methoxy-9-[4-[2-(2-methylsulfonylethylamino)ethyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one;hydrochloride Chemical compound Cl.COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCNCCS(C)(=O)=O)C=C1 JWNHEGZUCDVEHD-UHFFFAOYSA-N 0.000 description 1
• JMOYYSJZMMBWNG-UHFFFAOYSA-N 8-pyridin-3-yl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C2C=3C=CSC=3C(=O)NC2=CC=C1C1=CC=CN=C1 JMOYYSJZMMBWNG-UHFFFAOYSA-N 0.000 description 1
• IXCKNVYTNAOSIS-UHFFFAOYSA-N 9-[3-(2-aminoethyl)anilino]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1NC1=CC=CC(CCN)=C1 IXCKNVYTNAOSIS-UHFFFAOYSA-N 0.000 description 1
• QHIBTJXISNFQDY-UHFFFAOYSA-N 9-[3-fluoro-4-[1-(methylamino)propan-2-yl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(F)C(C(C)CNC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 QHIBTJXISNFQDY-UHFFFAOYSA-N 0.000 description 1
• JNLCSZJEPDANGR-UHFFFAOYSA-N 9-[3-fluoro-4-[1-(methylamino)propan-2-yl]phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(F)C(C(C)CNC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 JNLCSZJEPDANGR-UHFFFAOYSA-N 0.000 description 1
• DPFAWEDZWWWJGK-UHFFFAOYSA-N 9-[3-fluoro-4-[2-(methylamino)ethyl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(F)C(CCNC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 DPFAWEDZWWWJGK-UHFFFAOYSA-N 0.000 description 1
• QAFXYRAIXUIELT-UHFFFAOYSA-N 9-[3-fluoro-4-[2-(methylamino)ethyl]phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(F)C(CCNC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 QAFXYRAIXUIELT-UHFFFAOYSA-N 0.000 description 1
• RBVUTEUJQFFXBF-UHFFFAOYSA-N 9-[4-(1-amino-2,2,2-trifluoroethyl)phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C1=CC=C(C(N)C(F)(F)F)C=C1 RBVUTEUJQFFXBF-UHFFFAOYSA-N 0.000 description 1
• GPGMAJAUNDQOFX-UHFFFAOYSA-N 9-[4-(1-amino-2,2,2-trifluoroethyl)phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(N)C(F)(F)F)C=C1 GPGMAJAUNDQOFX-UHFFFAOYSA-N 0.000 description 1
• HSXLGERSFRXVRF-UHFFFAOYSA-N 9-[4-(1-amino-2-methylpropan-2-yl)phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C1=CC=C(C(C)(C)CN)C=C1 HSXLGERSFRXVRF-UHFFFAOYSA-N 0.000 description 1
• LAGPGMHMXFXNFJ-UHFFFAOYSA-N 9-[4-(1-amino-2-methylpropan-2-yl)phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)(C)CN)C=C1 LAGPGMHMXFXNFJ-UHFFFAOYSA-N 0.000 description 1
• ZRHFRDOZGCEQFQ-UHFFFAOYSA-N 9-[4-(1-amino-3-methylbutan-2-yl)-3-fluorophenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(F)C(C(CN)C(C)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 ZRHFRDOZGCEQFQ-UHFFFAOYSA-N 0.000 description 1
• GOJKTBGMQIQPEP-UHFFFAOYSA-N 9-[4-(1-amino-3-methylbutan-2-yl)-3-fluorophenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(CN)C(C)C)C(F)=C1 GOJKTBGMQIQPEP-UHFFFAOYSA-N 0.000 description 1
• KQNDXKBBEGZVOX-UHFFFAOYSA-N 9-[4-(1-amino-3-methylbutan-2-yl)phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(CN)C(C)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 KQNDXKBBEGZVOX-UHFFFAOYSA-N 0.000 description 1
• ZCOUKRXDKXZBIW-UHFFFAOYSA-N 9-[4-(1-aminoethyl)phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(N)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 ZCOUKRXDKXZBIW-UHFFFAOYSA-N 0.000 description 1
• TWQRRJYTICORNX-UHFFFAOYSA-N 9-[4-(1-aminopropan-2-yl)-3-chlorophenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(Cl)C(C(CN)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 TWQRRJYTICORNX-UHFFFAOYSA-N 0.000 description 1
• UMCFZRKTYOWGKC-UHFFFAOYSA-N 9-[4-(1-aminopropan-2-yl)-3-chlorophenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)CN)C(Cl)=C1 UMCFZRKTYOWGKC-UHFFFAOYSA-N 0.000 description 1
• RTGGXEUXYBKUPH-UHFFFAOYSA-N 9-[4-(1-aminopropan-2-yl)-3-fluorophenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(F)C(C(CN)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 RTGGXEUXYBKUPH-UHFFFAOYSA-N 0.000 description 1
• VGJCBNKCXZASKA-UHFFFAOYSA-N 9-[4-(1-aminopropan-2-yl)-3-fluorophenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)CN)C(F)=C1 VGJCBNKCXZASKA-UHFFFAOYSA-N 0.000 description 1
• DMQMLGPXXTUMQR-UHFFFAOYSA-N 9-[4-(1-aminopropan-2-yl)anilino]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(CN)C)=CC=C1NC1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 DMQMLGPXXTUMQR-UHFFFAOYSA-N 0.000 description 1
• QASRRTOKJYIWGI-UHFFFAOYSA-N 9-[4-(2-aminoethyl)-3-chlorophenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C1=CC=C(CCN)C(Cl)=C1 QASRRTOKJYIWGI-UHFFFAOYSA-N 0.000 description 1
• OVRIQAGBWVZFJO-UHFFFAOYSA-N 9-[4-(2-aminoethyl)-3-chlorophenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCN)C(Cl)=C1 OVRIQAGBWVZFJO-UHFFFAOYSA-N 0.000 description 1
• XKBLATUMVDPEFV-UHFFFAOYSA-N 9-[4-(2-aminoethyl)-3-fluorophenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C1=CC=C(CCN)C(F)=C1 XKBLATUMVDPEFV-UHFFFAOYSA-N 0.000 description 1
• BTAJIQAIKJOVJN-UHFFFAOYSA-N 9-[4-(2-aminoethyl)-3-fluorophenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCN)C(F)=C1 BTAJIQAIKJOVJN-UHFFFAOYSA-N 0.000 description 1
• MDDWEOQYSSJPOL-UHFFFAOYSA-N 9-[4-(2-aminoethyl)anilino]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1NC1=CC=C(CCN)C=C1 MDDWEOQYSSJPOL-UHFFFAOYSA-N 0.000 description 1
• XURGKYYHQOZIKO-UHFFFAOYSA-N 9-[4-(2-aminoethyl)anilino]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1NC1=CC=C(CCN)C=C1 XURGKYYHQOZIKO-UHFFFAOYSA-N 0.000 description 1
• SKDPRRGUNJCYCL-UHFFFAOYSA-N 9-[4-(2-aminoethyl)phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C1=CC=C(CCN)C=C1 SKDPRRGUNJCYCL-UHFFFAOYSA-N 0.000 description 1
• RQPFSZQKJLIHFG-UHFFFAOYSA-N 9-[4-(2-aminoethyl)phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCN)C=C1 RQPFSZQKJLIHFG-UHFFFAOYSA-N 0.000 description 1
• MDNLVSCIHNSQDE-UHFFFAOYSA-N 9-[4-(2-aminopropan-2-yl)phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)(C)N)C=C1 MDNLVSCIHNSQDE-UHFFFAOYSA-N 0.000 description 1
• HUYVGKHUSCVUIT-UHFFFAOYSA-N 9-[4-(2-aminopropyl)phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CC(C)N)C=C1 HUYVGKHUSCVUIT-UHFFFAOYSA-N 0.000 description 1
• PCINWAXYQWHXML-UHFFFAOYSA-N 9-[4-(3-aminopropyl)phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C1=CC=C(CCCN)C=C1 PCINWAXYQWHXML-UHFFFAOYSA-N 0.000 description 1
• VLTSCZIXZTVKQJ-UHFFFAOYSA-N 9-[4-(3-aminopropyl)phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCCN)C=C1 VLTSCZIXZTVKQJ-UHFFFAOYSA-N 0.000 description 1
• MSQBJJUXSXHDTC-UHFFFAOYSA-N 9-[4-(aminomethyl)anilino]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1NC1=CC=C(CN)C=C1 MSQBJJUXSXHDTC-UHFFFAOYSA-N 0.000 description 1
• HJRVZJQXEHPEDZ-UHFFFAOYSA-N 9-[4-(aminomethyl)anilino]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1NC1=CC=C(CN)C=C1 HJRVZJQXEHPEDZ-UHFFFAOYSA-N 0.000 description 1
• UZGKQBUDEIMMDO-UHFFFAOYSA-N 9-[4-(aminomethyl)phenyl]-8-hydroxy-1,2,3,5-tetrahydrocyclopenta[c]quinolin-4-one;hydrochloride Chemical compound Cl.C1=CC(CN)=CC=C1C1=C(O)C=CC2=C1C(CCC1)=C1C(=O)N2 UZGKQBUDEIMMDO-UHFFFAOYSA-N 0.000 description 1
• BZDJKZIYNUDNEU-UHFFFAOYSA-N 9-[4-(aminomethyl)phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C1=CC=C(CN)C=C1 BZDJKZIYNUDNEU-UHFFFAOYSA-N 0.000 description 1
• ZCOUKRXDKXZBIW-LLVKDONJSA-N 9-[4-[(1r)-1-aminoethyl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](N)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 ZCOUKRXDKXZBIW-LLVKDONJSA-N 0.000 description 1
• FDWSLLOJTBCQIA-MRXNPFEDSA-N 9-[4-[(1r)-1-aminopropyl]phenyl]-8-hydroxy-5,6-dimethylthieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](N)CC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2C FDWSLLOJTBCQIA-MRXNPFEDSA-N 0.000 description 1
• RZGRZSXTMYGDRI-OAHLLOKOSA-N 9-[4-[(1r)-1-aminopropyl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](N)CC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 RZGRZSXTMYGDRI-OAHLLOKOSA-N 0.000 description 1
• KCLWEERDMRRSAJ-MRXNPFEDSA-N 9-[4-[(1r)-1-aminopropyl]phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](N)CC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 KCLWEERDMRRSAJ-MRXNPFEDSA-N 0.000 description 1
• ZCOUKRXDKXZBIW-NSHDSACASA-N 9-[4-[(1s)-1-aminoethyl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](N)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 ZCOUKRXDKXZBIW-NSHDSACASA-N 0.000 description 1
• NKHFPXBXOALGHP-KRWDZBQOSA-N 9-[4-[(2r)-1-(diethylamino)butan-2-yl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](CN(CC)CC)CC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 NKHFPXBXOALGHP-KRWDZBQOSA-N 0.000 description 1
• BWPLRMDLLUFRMK-INIZCTEOSA-N 9-[4-[(2r)-1-(diethylamino)propan-2-yl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](C)CN(CC)CC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 BWPLRMDLLUFRMK-INIZCTEOSA-N 0.000 description 1
• FFRVOVQJVWRQBR-HNNXBMFYSA-N 9-[4-[(2r)-1-(dimethylamino)butan-2-yl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](CN(C)C)CC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 FFRVOVQJVWRQBR-HNNXBMFYSA-N 0.000 description 1
• IINFJOMDFKUTTM-INIZCTEOSA-N 9-[4-[(2r)-1-(dimethylamino)butan-2-yl]phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](CN(C)C)CC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 IINFJOMDFKUTTM-INIZCTEOSA-N 0.000 description 1
• XCFRUAOZMVFDPQ-AWEZNQCLSA-N 9-[4-[(2r)-1-(dimethylamino)propan-2-yl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](CN(C)C)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 XCFRUAOZMVFDPQ-AWEZNQCLSA-N 0.000 description 1
• IVTXKZOAEFIJGG-AWEZNQCLSA-N 9-[4-[(2r)-1-aminobutan-2-yl]phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](CN)CC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 IVTXKZOAEFIJGG-AWEZNQCLSA-N 0.000 description 1
• DVVYXQWKBDYQAC-LSLKUGRBSA-N 9-[4-[(2r)-1-aminopropan-2-yl]phenyl]-2-(1-hydroxyethyl)-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC(C(C)O)=CC=3C2=C1C1=CC=C([C@@H](C)CN)C=C1 DVVYXQWKBDYQAC-LSLKUGRBSA-N 0.000 description 1
• IYAGEOALNDABFU-LBPRGKRZSA-N 9-[4-[(2r)-1-aminopropan-2-yl]phenyl]-8-hydroxy-2,6-dimethyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](CN)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=C(C)S1)=C1C(=O)N2 IYAGEOALNDABFU-LBPRGKRZSA-N 0.000 description 1
• HXETTYGETVMKDV-ZDUSSCGKSA-N 9-[4-[(2r)-1-aminopropan-2-yl]phenyl]-8-methoxy-2,6-dimethyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC(C)=CC=3C2=C1C1=CC=C([C@@H](C)CN)C=C1 HXETTYGETVMKDV-ZDUSSCGKSA-N 0.000 description 1
• XCFRUAOZMVFDPQ-CQSZACIVSA-N 9-[4-[(2s)-1-(dimethylamino)propan-2-yl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](CN(C)C)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 XCFRUAOZMVFDPQ-CQSZACIVSA-N 0.000 description 1
• BKECLKGMYTZOIX-CYBMUJFWSA-N 9-[4-[(2s)-1-aminopropan-2-yl]phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C([C@H](C)CN)C=C1 BKECLKGMYTZOIX-CYBMUJFWSA-N 0.000 description 1
• PTHNXQKURHKHTJ-UHFFFAOYSA-N 9-[4-[1-(aminomethyl)cyclobutyl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C(C=C1)=CC=C1C1(CN)CCC1 PTHNXQKURHKHTJ-UHFFFAOYSA-N 0.000 description 1
• KNXPAGANDXONSK-UHFFFAOYSA-N 9-[4-[1-(aminomethyl)cyclobutyl]phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1C1(CN)CCC1 KNXPAGANDXONSK-UHFFFAOYSA-N 0.000 description 1
• UFFWPCOIHLQCSD-UHFFFAOYSA-N 9-[4-[1-(aminomethyl)cyclopropyl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C(C=C1)=CC=C1C1(CN)CC1 UFFWPCOIHLQCSD-UHFFFAOYSA-N 0.000 description 1
• PUJFKJQMXFZQGI-UHFFFAOYSA-N 9-[4-[1-(aminomethyl)cyclopropyl]phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1C1(CN)CC1 PUJFKJQMXFZQGI-UHFFFAOYSA-N 0.000 description 1
• CYPGOUKOOALODJ-UHFFFAOYSA-N 9-[4-[1-(dimethylamino)-3-methylbutan-2-yl]phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(CN(C)C)C(C)C)C=C1 CYPGOUKOOALODJ-UHFFFAOYSA-N 0.000 description 1
• LHZSCNHIQYURJR-UHFFFAOYSA-N 9-[4-[1-(dimethylamino)propan-2-yl]-3-fluorophenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(F)C(C(CN(C)C)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 LHZSCNHIQYURJR-UHFFFAOYSA-N 0.000 description 1
• ZBQYCBMJUWWRTJ-UHFFFAOYSA-N 9-[4-[1-[(dimethylamino)methyl]cyclobutyl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C=1C=C(C=2C=3C=4C=CSC=4C(=O)NC=3C(C)=CC=2O)C=CC=1C1(CN(C)C)CCC1 ZBQYCBMJUWWRTJ-UHFFFAOYSA-N 0.000 description 1
• DJHGKEGGXJTDCS-UHFFFAOYSA-N 9-[4-[2-(dimethylamino)ethyl]phenyl]-8-methoxy-1,2,3,5-tetrahydrocyclopenta[c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3CCCC=3C2=C1C1=CC=C(CCN(C)C)C=C1 DJHGKEGGXJTDCS-UHFFFAOYSA-N 0.000 description 1
• CSZJZHLYNHJFSA-UHFFFAOYSA-N 9-[4-[2-(ethylamino)ethyl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCNCC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 CSZJZHLYNHJFSA-UHFFFAOYSA-N 0.000 description 1
• YTUUHSSLLSTDJY-UHFFFAOYSA-N 9-[4-[2-(ethylamino)ethyl]phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCNCC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 YTUUHSSLLSTDJY-UHFFFAOYSA-N 0.000 description 1
• HCGVONDWNWENOD-UHFFFAOYSA-N 9-[4-[2-(ethylamino)propyl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CC(C)NCC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 HCGVONDWNWENOD-UHFFFAOYSA-N 0.000 description 1
• UNUOZMOHLIFIOU-UHFFFAOYSA-N 9-[4-[2-[ethyl(methyl)amino]ethyl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCN(C)CC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 UNUOZMOHLIFIOU-UHFFFAOYSA-N 0.000 description 1
• BGUWDXMYBUBGMA-UHFFFAOYSA-N 9-[4-[2-[ethyl(methyl)amino]propyl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CC(C)N(C)CC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 BGUWDXMYBUBGMA-UHFFFAOYSA-N 0.000 description 1
• LTHAXYKMOMPHFU-UHFFFAOYSA-N 9-[4-[2-aminoethyl(methyl)amino]phenyl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(N(C)CCN)C=C1 LTHAXYKMOMPHFU-UHFFFAOYSA-N 0.000 description 1
• VHUUKIXUJMNSOT-UHFFFAOYSA-N 9-[4-[3-(aminomethyl)pentan-3-yl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(CC)(CN)CC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 VHUUKIXUJMNSOT-UHFFFAOYSA-N 0.000 description 1
• OWPBZQKATUOLHJ-UHFFFAOYSA-N 9-[4-[3-(diethylaminomethyl)pentan-3-yl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(CC)(CC)CN(CC)CC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 OWPBZQKATUOLHJ-UHFFFAOYSA-N 0.000 description 1
• UPTRIWOMOOHOBS-UHFFFAOYSA-N 9-[4-[3-[(dimethylamino)methyl]pentan-3-yl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(CC)(CN(C)C)CC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 UPTRIWOMOOHOBS-UHFFFAOYSA-N 0.000 description 1
• NJGQLCCCSREPIN-UHFFFAOYSA-N 9-[6-(2-aminoethoxy)pyridin-3-yl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(OCCN)N=C1 NJGQLCCCSREPIN-UHFFFAOYSA-N 0.000 description 1
• NQBNNZDHRBHSRS-UHFFFAOYSA-N 9-[6-(2-aminoethylamino)pyridin-3-yl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(NCCN)N=C1 NQBNNZDHRBHSRS-UHFFFAOYSA-N 0.000 description 1
• DSVHCRHNJVMXAM-UHFFFAOYSA-N 9-[6-(dimethylamino)pyridin-3-yl]-8-methoxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(N(C)C)N=C1 DSVHCRHNJVMXAM-UHFFFAOYSA-N 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• 208000011691 Burkitt lymphomas Diseases 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• 241001459693 Dipterocarpus zeylanicus Species 0.000 description 1
• 241001269524 Dura Species 0.000 description 1
• NKTDTMONXHODTI-UHFFFAOYSA-N EtCCMe Natural products CCC#CC NKTDTMONXHODTI-UHFFFAOYSA-N 0.000 description 1
• 239000007995 HEPES buffer Substances 0.000 description 1
• 208000002250 Hematologic Neoplasms Diseases 0.000 description 1
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
• 239000012448 Lithium borohydride Substances 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
• 241000124008 Mammalia Species 0.000 description 1
• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 1
• CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical group N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
• 229920001213 Polysorbate 20 Polymers 0.000 description 1
• 229910019020 PtO2 Inorganic materials 0.000 description 1
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
• AXORVIZLPOGIRG-QMMMGPOBSA-N R-BETA-METHYLPHENYLETHYLAMINE Chemical compound NC[C@H](C)C1=CC=CC=C1 AXORVIZLPOGIRG-QMMMGPOBSA-N 0.000 description 1
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
• 108020004459 Small interfering RNA Proteins 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• 239000007983 Tris buffer Substances 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 150000001450 anions Chemical class 0.000 description 1
• 230000006907 apoptotic process Effects 0.000 description 1
• 238000003556 assay Methods 0.000 description 1
• TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
• 230000027455 binding Effects 0.000 description 1
• 238000009739 binding Methods 0.000 description 1
• 125000005510 but-1-en-2-yl group Chemical group 0.000 description 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• 238000010609 cell counting kit-8 assay Methods 0.000 description 1
• 230000006369 cell cycle progression Effects 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
• 210000000349 chromosome Anatomy 0.000 description 1
• 125000004802 cyanophenyl group Chemical group 0.000 description 1
• 125000004122 cyclic group Chemical group 0.000 description 1
• 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 230000021953 cytokinesis Effects 0.000 description 1
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Substances CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 1
• 230000009977 dual effect Effects 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• MYFOYOXMFDOSPN-UHFFFAOYSA-N ethyl 2-bromo-4-phenyl-1,3-thiazole-5-carboxylate Chemical compound S1C(Br)=NC(C=2C=CC=CC=2)=C1C(=O)OCC MYFOYOXMFDOSPN-UHFFFAOYSA-N 0.000 description 1
• 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 238000001415 gene therapy Methods 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 238000002991 immunohistochemical analysis Methods 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 150000008040 ionic compounds Chemical class 0.000 description 1
• 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 229940043355 kinase inhibitor Drugs 0.000 description 1
• YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 1
• 229910001629 magnesium chloride Inorganic materials 0.000 description 1
• 230000021121 meiosis Effects 0.000 description 1
• 230000031864 metaphase Effects 0.000 description 1
• USJUUYYGHABIBU-UHFFFAOYSA-N methanesulfonamide;hydrochloride Chemical compound Cl.CS(N)(=O)=O USJUUYYGHABIBU-UHFFFAOYSA-N 0.000 description 1
• YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• MIINNLKAYPKZLE-UHFFFAOYSA-N n-(3-acetylphenyl)-5-bromothiophene-2-carboxamide Chemical compound CC(=O)C1=CC=CC(NC(=O)C=2SC(Br)=CC=2)=C1 MIINNLKAYPKZLE-UHFFFAOYSA-N 0.000 description 1
• ADSZPNMSCCQTBA-UHFFFAOYSA-N n-(4-bromophenyl)-2,2-dimethyloxane-4-carboxamide Chemical compound C1COC(C)(C)CC1C(=O)NC1=CC=C(Br)C=C1 ADSZPNMSCCQTBA-UHFFFAOYSA-N 0.000 description 1
• RRQPLRFBVLOSBI-UHFFFAOYSA-N n-[4-(8-hydroxy-4-oxo-1,2,3,5-tetrahydrocyclopenta[c]quinolin-9-yl)phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(O)C=CC2=C1C(CCC1)=C1C(=O)N2 RRQPLRFBVLOSBI-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000006095 n-butyl sulfinyl group Chemical group 0.000 description 1
• 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• 238000006386 neutralization reaction Methods 0.000 description 1
• 125000004433 nitrogen atom Chemical group N* 0.000 description 1
• 125000006574 non-aromatic ring group Chemical group 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 230000002018 overexpression Effects 0.000 description 1
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
• 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
• 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• 230000000750 progressive effect Effects 0.000 description 1
• 230000002062 proliferating effect Effects 0.000 description 1
• VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
• 230000031877 prophase Effects 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• MZPCTRNDYNHZQE-UHFFFAOYSA-N quinolin-8-yl acetate Chemical compound C1=CN=C2C(OC(=O)C)=CC=CC2=C1 MZPCTRNDYNHZQE-UHFFFAOYSA-N 0.000 description 1
• MKJDIDCKRPRJOU-UHFFFAOYSA-N quinolin-8-yl morpholine-4-carboxylate Chemical compound C=1C=CC2=CC=CN=C2C=1OC(=O)N1CCOCC1 MKJDIDCKRPRJOU-UHFFFAOYSA-N 0.000 description 1
• SQOGWLLYYCEMNN-UHFFFAOYSA-N quinolin-8-yl n,n-diethylcarbamate Chemical compound C1=CN=C2C(OC(=O)N(CC)CC)=CC=CC2=C1 SQOGWLLYYCEMNN-UHFFFAOYSA-N 0.000 description 1
• VCSGVHPHQVIBAP-UHFFFAOYSA-N quinolin-8-yl n,n-dimethylcarbamate Chemical compound C1=CN=C2C(OC(=O)N(C)C)=CC=CC2=C1 VCSGVHPHQVIBAP-UHFFFAOYSA-N 0.000 description 1
• 125000005493 quinolyl group Chemical group 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 230000001850 reproductive effect Effects 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 210000002863 seminiferous tubule Anatomy 0.000 description 1
• 239000012279 sodium borohydride Substances 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• 235000017550 sodium carbonate Nutrition 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000000243 solution Substances 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 230000004960 subcellular localization Effects 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
• 125000004434 sulfur atom Chemical group 0.000 description 1
• 230000002381 testicular Effects 0.000 description 1
• 125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 238000004809 thin layer chromatography Methods 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 229910001868 water Inorganic materials 0.000 description 1