SG184376A1 - Trycyclic compounds and pbk inhibitors containing the same - Google Patents

Info

Publication number

SG184376A1

SG184376A1 SG2012072807A SG2012072807A SG184376A1 SG 184376 A1 SG184376 A1 SG 184376A1 SG 2012072807 A SG2012072807 A SG 2012072807A SG 2012072807 A SG2012072807 A SG 2012072807A SG 184376 A1 SG184376 A1 SG 184376A1

Authority

SG

Singapore

Prior art keywords

quinolin

phenyl

hydroxy

hydroxythieno

dihydrothieno

Prior art date

2010-03-29

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 153
• 239000003112 inhibitor Substances 0.000 title claims abstract description 9
• 201000010099 disease Diseases 0.000 claims abstract description 34
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 22
• 201000011510 cancer Diseases 0.000 claims abstract description 19
• 125000000217 alkyl group Chemical group 0.000 claims description 573
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 328
• 229910052739 hydrogen Inorganic materials 0.000 claims description 312
• 239000001257 hydrogen Substances 0.000 claims description 309
• -1 cyano, nitro, amino Chemical group 0.000 claims description 292
• 229910052792 caesium Inorganic materials 0.000 claims description 193
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 193
• 238000000034 method Methods 0.000 claims description 183
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 172
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 172
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 150
• 125000001424 substituent group Chemical group 0.000 claims description 150
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 143
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 132
• 150000002431 hydrogen Chemical class 0.000 claims description 129
• 150000003839 salts Chemical class 0.000 claims description 115
• 229910052736 halogen Inorganic materials 0.000 claims description 112
• 150000002367 halogens Chemical class 0.000 claims description 104
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 100
• 125000005936 piperidyl group Chemical group 0.000 claims description 96
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 93
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 87
• 125000003545 alkoxy group Chemical group 0.000 claims description 85
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 81
• 229910052799 carbon Inorganic materials 0.000 claims description 78
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 58
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 57
• 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 claims description 54
• 125000003118 aryl group Chemical group 0.000 claims description 54
• 125000001072 heteroaryl group Chemical group 0.000 claims description 51
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 50
• 125000004193 piperazinyl group Chemical group 0.000 claims description 48
• 102100026753 Lymphokine-activated killer T-cell-originated protein kinase Human genes 0.000 claims description 46
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 42
• 125000002757 morpholinyl group Chemical group 0.000 claims description 39
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 33
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 28
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 26
• 230000001419 dependent effect Effects 0.000 claims description 25
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 24
• 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 22
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims description 22
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 22
• 125000003342 alkenyl group Chemical group 0.000 claims description 21
• 125000002393 azetidinyl group Chemical group 0.000 claims description 20
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 20
• 108091053735 lin-4 stem-loop Proteins 0.000 claims description 19
• 108091032363 lin-4-1 stem-loop Proteins 0.000 claims description 19
• 108091028008 lin-4-2 stem-loop Proteins 0.000 claims description 19
• 125000004076 pyridyl group Chemical group 0.000 claims description 19
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 15
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 15
• 125000002883 imidazolyl group Chemical group 0.000 claims description 14
• CIIFKVFOVFJZDM-UHFFFAOYSA-N quinoline-8-carbonitrile Chemical compound C1=CN=C2C(C#N)=CC=CC2=C1 CIIFKVFOVFJZDM-UHFFFAOYSA-N 0.000 claims description 14
• 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 claims description 13
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 13
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 13
• 125000000304 alkynyl group Chemical group 0.000 claims description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• RSOJSFYJLQADDM-UHFFFAOYSA-N ethanesulfonamide Chemical compound [CH2]CS(N)(=O)=O RSOJSFYJLQADDM-UHFFFAOYSA-N 0.000 claims description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 125000002541 furyl group Chemical group 0.000 claims description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
• 125000001544 thienyl group Chemical group 0.000 claims description 10
• 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 9
• 241001024304 Mino Species 0.000 claims description 9
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• JVLFMTZUPSBCNJ-UHFFFAOYSA-N 3,5-difluoropyridin-2-amine Chemical compound NC1=NC=C(F)C=C1F JVLFMTZUPSBCNJ-UHFFFAOYSA-N 0.000 claims description 8
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 8
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 8
• BXFXDABQQRHCLL-UHFFFAOYSA-N quinolin-8-yl methanesulfonate Chemical compound C1=CN=C2C(OS(=O)(=O)C)=CC=CC2=C1 BXFXDABQQRHCLL-UHFFFAOYSA-N 0.000 claims description 8
• WUXOMAMRJLJIHQ-UHFFFAOYSA-N 7,8-dihydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=C(O)C(O)=CC=2NC(=O)C2=C1C=CS2 WUXOMAMRJLJIHQ-UHFFFAOYSA-N 0.000 claims description 7
• GHPWGXZMQRABPC-UHFFFAOYSA-N 7,9-dihydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound O=C1NC2=CC(O)=CC(O)=C2C2=C1SC=C2 GHPWGXZMQRABPC-UHFFFAOYSA-N 0.000 claims description 7
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
• 125000001931 aliphatic group Chemical group 0.000 claims description 7
• AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 claims description 7
• 125000003566 oxetanyl group Chemical group 0.000 claims description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• USQCUKQZXOWUDF-YWZLYKJASA-N 6-chloro-n-[(3s)-1-[(2s)-1-(4-methyl-5-oxo-1,4-diazepan-1-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]naphthalene-2-sulfonamide Chemical compound O=C([C@@H](N1C([C@@H](NS(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N1CCN(C)C(=O)CC1 USQCUKQZXOWUDF-YWZLYKJASA-N 0.000 claims description 6
• UDLWPNDDGXJCSJ-UHFFFAOYSA-N 7,9-dimethoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound O=C1NC2=CC(OC)=CC(OC)=C2C2=C1SC=C2 UDLWPNDDGXJCSJ-UHFFFAOYSA-N 0.000 claims description 6
• HKVVKCDJTRNWQI-UHFFFAOYSA-N 9-[2-(diethylamino)-2,3-dihydro-1h-inden-5-yl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C2CC(N(CC)CC)CC2=CC=C1C(C1=2)=C(O)C=CC=2NC(=O)C2=C1C=CS2 HKVVKCDJTRNWQI-UHFFFAOYSA-N 0.000 claims description 6
• CQVWOXVVCUGWCR-UHFFFAOYSA-N 9-[4-[2-(dimethylamino)ethyl]phenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCN(C)C)C=C1 CQVWOXVVCUGWCR-UHFFFAOYSA-N 0.000 claims description 6
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 6
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 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
• DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 claims description 6
• 125000005955 1H-indazolyl group Chemical group 0.000 claims description 5
• KANYEOCVJXABMX-UHFFFAOYSA-N 2-[[2-(dimethylamino)ethylamino]methyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound O=C1NC2=CC=C(O)C=C2C2=C1SC(CNCCN(C)C)=C2 KANYEOCVJXABMX-UHFFFAOYSA-N 0.000 claims description 5
• PRLYORQJMCNPDP-UHFFFAOYSA-N 9-[4-(aminomethyl)phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CN)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 PRLYORQJMCNPDP-UHFFFAOYSA-N 0.000 claims description 5
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
• 125000003725 azepanyl group Chemical group 0.000 claims description 5
• 125000004069 aziridinyl group Chemical group 0.000 claims description 5
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 5
• XVCOANMZANWKPN-UHFFFAOYSA-N 1-(3,4-dihydroxyphenyl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C3=CC(O)=CC=C3NC(=O)C=2SC=C1C1=CC=C(O)C(O)=C1 XVCOANMZANWKPN-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
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• DMUYVMYUXRQRER-UHFFFAOYSA-N 7,8-dimethoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)C2=C1C=CS2 DMUYVMYUXRQRER-UHFFFAOYSA-N 0.000 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 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
• GCUXYSAOIHUXSW-UHFFFAOYSA-N 8-hydroxy-9-phenyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=CC=C1 GCUXYSAOIHUXSW-UHFFFAOYSA-N 0.000 claims description 4
• 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 claims description 4
• GRFNKXDTGNQDOH-UHFFFAOYSA-N 8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C12=CC(OC)=CC=C2NC(=O)C2=C1C=CS2 GRFNKXDTGNQDOH-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• PKEIPTUWCNZABP-UHFFFAOYSA-N 8-nitro-5h-thieno[2,3-c]quinolin-4-one Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)C2=C1C=CS2 PKEIPTUWCNZABP-UHFFFAOYSA-N 0.000 claims description 4
• ZYEQOJAHRSUOCF-UHFFFAOYSA-N 9-(3-acetylphenyl)-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=CC(C(C)=O)=C1 ZYEQOJAHRSUOCF-UHFFFAOYSA-N 0.000 claims description 4
• ZSOYCPHDLQHJFO-UHFFFAOYSA-N 9-(3-aminophenyl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound NC1=CC=CC(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)=C1 ZSOYCPHDLQHJFO-UHFFFAOYSA-N 0.000 claims description 4
• HFBFJEYXOOLKEH-UHFFFAOYSA-N 9-(4-acetylphenyl)-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)=O)C=C1 HFBFJEYXOOLKEH-UHFFFAOYSA-N 0.000 claims description 4
• UUFRKVNSHDQAQR-UHFFFAOYSA-N 9-[4-(2-aminoethyl)-2-bromo-5-hydroxyphenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(O)C(CCN)=CC(Br)=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 UUFRKVNSHDQAQR-UHFFFAOYSA-N 0.000 claims description 4
• 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 claims description 4
• RTGGXEUXYBKUPH-NSHDSACASA-N 9-[4-[(2r)-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@H](CN)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 RTGGXEUXYBKUPH-NSHDSACASA-N 0.000 claims description 4
• PSICKIVVSWXRBR-JTQLQIEISA-N 9-[4-[(2r)-1-aminopropan-2-yl]phenyl]-6-bromo-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@H](CN)C)=CC=C1C1=C(O)C=C(Br)C2=C1C(C=CS1)=C1C(=O)N2 PSICKIVVSWXRBR-JTQLQIEISA-N 0.000 claims description 4
• 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 claims description 4
• QOZYMUQOKYGGAL-UHFFFAOYSA-N 9-[4-[1-(dimethylamino)ethyl]phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(N(C)C)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 QOZYMUQOKYGGAL-UHFFFAOYSA-N 0.000 claims description 4
• QTZCMMCLZHAQPZ-UHFFFAOYSA-N 9-bromo-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C12=C(Br)C(O)=CC=C2NC(=O)C2=C1C=CS2 QTZCMMCLZHAQPZ-UHFFFAOYSA-N 0.000 claims description 4
• PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 claims description 4
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 4
• 239000004202 carbamide Substances 0.000 claims description 4
• 239000003937 drug carrier Substances 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
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
• 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 claims description 4
• ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 claims description 4
• PXMYGNBQBZWICC-UHFFFAOYSA-N 1,8-dihydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C12=CC(O)=CC=C2NC(=O)C2=C1C(O)=CS2 PXMYGNBQBZWICC-UHFFFAOYSA-N 0.000 claims description 3
• PSBBIANZFFGOJW-UHFFFAOYSA-N 1-(3-aminopiperidin-1-yl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1C(N)CCCN1C1=CSC2=C1C1=CC(O)=CC=C1NC2=O PSBBIANZFFGOJW-UHFFFAOYSA-N 0.000 claims description 3
• FXMKAJSOOOHCAV-UHFFFAOYSA-N 2-(3,4-dihydroxyphenyl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C=1C=2C3=CC(O)=CC=C3NC(=O)C=2SC=1C1=CC=C(O)C(O)=C1 FXMKAJSOOOHCAV-UHFFFAOYSA-N 0.000 claims description 3
• QASKEMJRNRJZAD-UHFFFAOYSA-N 2-(3-aminopiperidine-1-carbonyl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1C(N)CCCN1C(=O)C1=CC(C2=CC(O)=CC=C2NC2=O)=C2S1 QASKEMJRNRJZAD-UHFFFAOYSA-N 0.000 claims description 3
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
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• KEGONDKQNSQDHW-UHFFFAOYSA-N 9-(4-chloro-3-fluorophenyl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(Cl)C(F)=C1 KEGONDKQNSQDHW-UHFFFAOYSA-N 0.000 claims description 3
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• CVKNJZMPNYETLN-UHFFFAOYSA-N 9-(6-aminopyridin-3-yl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=NC(N)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 CVKNJZMPNYETLN-UHFFFAOYSA-N 0.000 claims description 3
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• YWSNTIVSKIYMTO-OWOJBTEDSA-N 9-[(e)-3-(3-aminoazetidin-1-yl)prop-1-enyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1C(N)CN1C\C=C\C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 YWSNTIVSKIYMTO-OWOJBTEDSA-N 0.000 claims description 3
• RUORIMOJVYOCHO-NSCUHMNNSA-N 9-[(e)-3-(3-aminoazetidin-1-yl)prop-1-enyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1\C=C\CN1CC(N)C1 RUORIMOJVYOCHO-NSCUHMNNSA-N 0.000 claims description 3
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• WTWYRHMDGRRMFB-UHFFFAOYSA-N 9-[3-(aminomethyl)phenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=CC(CN)=C1 WTWYRHMDGRRMFB-UHFFFAOYSA-N 0.000 claims description 3
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• NJLGUAYKHSLYDW-UHFFFAOYSA-N 9-[3-chloro-4-(diethylaminomethyl)phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(Cl)C(CN(CC)CC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 NJLGUAYKHSLYDW-UHFFFAOYSA-N 0.000 claims description 3
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• 125000005605 benzo group Chemical group 0.000 claims description 2
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• 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 1
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• 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 1
• 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 1
• FWFZCKJDMAOCMI-UHFFFAOYSA-N 8-hydroxy-9-[4-(imidazol-1-ylmethyl)phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1CN1C=CN=C1 FWFZCKJDMAOCMI-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 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 claims 1
• 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 1
• 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 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
• 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 1
• 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 1
• 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 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
• 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 1
• 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 1
• DKSWSXAXYFMXDL-UHFFFAOYSA-N 8-morpholin-4-yl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C2C=3C=CSC=3C(=O)NC2=CC=C1N1CCOCC1 DKSWSXAXYFMXDL-UHFFFAOYSA-N 0.000 claims 1
• SZGHMAYCPPJWRF-UHFFFAOYSA-N 9-(1-ethyl-2,3-dihydroindol-5-yl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C=1C=C2N(CC)CCC2=CC=1C(C1=2)=C(O)C=CC=2NC(=O)C2=C1C=CS2 SZGHMAYCPPJWRF-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• GADRBFWJPDJDEM-UHFFFAOYSA-N 9-(3h-benzimidazol-5-yl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C2NC=NC2=CC(C2=C3C=4C=CSC=4C(=O)NC3=CC=C2O)=C1 GADRBFWJPDJDEM-UHFFFAOYSA-N 0.000 claims 1
• QFHRVSWEKINXQM-UHFFFAOYSA-N 9-(6-tert-butylpyridin-3-yl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=NC(C(C)(C)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 QFHRVSWEKINXQM-UHFFFAOYSA-N 0.000 claims 1
• IGIJIXHBKRGQDU-UHFFFAOYSA-N 9-(cyclohexen-1-yl)-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CCCCC1 IGIJIXHBKRGQDU-UHFFFAOYSA-N 0.000 claims 1
• PZTVAYVNCXMOST-AATRIKPKSA-N 9-[(e)-3-[2-(diethylamino)ethylamino]prop-1-enyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C(/C=C/CNCCN(CC)CC)=C(O)C=CC=2NC(=O)C2=C1C=CS2 PZTVAYVNCXMOST-AATRIKPKSA-N 0.000 claims 1
• XBZAPCBNWNTFCA-OWOJBTEDSA-N 9-[(e)-3-[4-(aminomethyl)piperidin-1-yl]prop-1-enyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1CC(CN)CCN1C\C=C\C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 XBZAPCBNWNTFCA-OWOJBTEDSA-N 0.000 claims 1
• IRPFRMRFMSYFHO-NSCUHMNNSA-N 9-[(e)-3-[4-(aminomethyl)piperidin-1-yl]prop-1-enyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1\C=C\CN1CCC(CN)CC1 IRPFRMRFMSYFHO-NSCUHMNNSA-N 0.000 claims 1
• PAFBRXPIXZIPER-UHFFFAOYSA-N 9-[1-[1-(dimethylamino)propan-2-yl]pyrazol-4-yl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=NN(C(CN(C)C)C)C=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 PAFBRXPIXZIPER-UHFFFAOYSA-N 0.000 claims 1
• LFPOFRCFVSGFEM-UHFFFAOYSA-N 9-[1-[1-(dimethylamino)propan-2-yl]pyrazol-4-yl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C=1C=NN(C(C)CN(C)C)C=1 LFPOFRCFVSGFEM-UHFFFAOYSA-N 0.000 claims 1
• YGZHSXUZCBVIHI-UHFFFAOYSA-N 9-[2-[4-[(dimethylamino)methyl]piperidin-1-yl]ethyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1CCN1CCC(CN(C)C)CC1 YGZHSXUZCBVIHI-UHFFFAOYSA-N 0.000 claims 1
• DNRFMSJVTXHVCU-UHFFFAOYSA-N 9-[3-[3-(dimethylamino)piperidin-1-yl]propyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1C(N(C)C)CCCN1CCCC1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 DNRFMSJVTXHVCU-UHFFFAOYSA-N 0.000 claims 1
• ODJVUEBCTWTGLT-UHFFFAOYSA-N 9-[3-[3-(dimethylamino)pyrrolidin-1-yl]propyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1C(N(C)C)CCN1CCCC1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 ODJVUEBCTWTGLT-UHFFFAOYSA-N 0.000 claims 1
• XEXVQKJIGTWYTN-UHFFFAOYSA-N 9-[3-chloro-4-[2-(ethylamino)ethyl]phenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(Cl)C(CCNCC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 XEXVQKJIGTWYTN-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
• KUHQUAWXAIOBAL-UHFFFAOYSA-N 9-[3-fluoro-4-[3-methyl-1-(methylamino)butan-2-yl]phenyl]-8-hydroxy-6-methyl-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(F)C(C(C(C)C)CNC)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 KUHQUAWXAIOBAL-UHFFFAOYSA-N 0.000 claims 1
• VFKPCRHUQGCDEA-UHFFFAOYSA-N 9-[4-(1-amino-2,2,2-trifluoroethyl)phenyl]-6-bromo-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(Br)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(N)C(F)(F)F)C=C1 VFKPCRHUQGCDEA-UHFFFAOYSA-N 0.000 claims 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 claims 1
• HNJUVAMATZSEDH-UHFFFAOYSA-N 9-[4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)(C)CN)C(F)=C1 HNJUVAMATZSEDH-UHFFFAOYSA-N 0.000 claims 1
• XFUUFHCEJFPNBH-UHFFFAOYSA-N 9-[4-(1-amino-2-methylpropan-2-yl)phenyl]-6-bromo-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(Br)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)(C)CN)C=C1 XFUUFHCEJFPNBH-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
• DBULRPQRUMLHAH-UHFFFAOYSA-N 9-[4-(1-amino-3-methylbutan-2-yl)phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(CN)C(C)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 DBULRPQRUMLHAH-UHFFFAOYSA-N 0.000 claims 1
• DZEHGHKHXFYSNM-UHFFFAOYSA-N 9-[4-(1-aminobutan-2-yl)phenyl]-6-chloro-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(CN)CC)=CC=C1C1=C(O)C=C(Cl)C2=C1C(C=CS1)=C1C(=O)N2 DZEHGHKHXFYSNM-UHFFFAOYSA-N 0.000 claims 1
• OEQJTJOPTYKIGK-UHFFFAOYSA-N 9-[4-(1-aminobutan-2-yl)phenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(CN)CC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 OEQJTJOPTYKIGK-UHFFFAOYSA-N 0.000 claims 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 claims 1
• GXVHQVVZHYYVLX-UHFFFAOYSA-N 9-[4-(1-aminopropan-2-yl)-3-fluorophenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)CN)C(F)=C1 GXVHQVVZHYYVLX-UHFFFAOYSA-N 0.000 claims 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 claims 1
• 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 1
• ZKGSCDQJANFTPN-UHFFFAOYSA-N 9-[4-(2-amino-1-cyclopentylethyl)phenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1C(CN)C1CCCC1 ZKGSCDQJANFTPN-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• RZYATRYMIRLKFM-UHFFFAOYSA-N 9-[4-(2-amino-2-methylpropyl)phenyl]-6-bromo-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CC(C)(N)C)=CC=C1C1=C(O)C=C(Br)C2=C1C(C=CS1)=C1C(=O)N2 RZYATRYMIRLKFM-UHFFFAOYSA-N 0.000 claims 1
• XDQLBWQOAVPUFS-UHFFFAOYSA-N 9-[4-(2-amino-2-methylpropyl)phenyl]-6-bromo-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(Br)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CC(C)(C)N)C=C1 XDQLBWQOAVPUFS-UHFFFAOYSA-N 0.000 claims 1
• IAUBYDQYZZTRLF-UHFFFAOYSA-N 9-[4-(2-amino-2-methylpropyl)phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CC(C)(N)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 IAUBYDQYZZTRLF-UHFFFAOYSA-N 0.000 claims 1
• GPZQOMVFHFACNU-UHFFFAOYSA-N 9-[4-(2-aminoethyl)-3-fluorophenyl]-6-cyclopropyl-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(F)C(CCN)=CC=C1C(C=1C=2C=CSC=2C(=O)NC=11)=C(O)C=C1C1CC1 GPZQOMVFHFACNU-UHFFFAOYSA-N 0.000 claims 1
• CSYFFTHQKKHNHF-UHFFFAOYSA-N 9-[4-(2-aminoethyl)-3-fluorophenyl]-6-cyclopropyl-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C=12NC(=O)C=3SC=CC=3C2=C(C=2C=C(F)C(CCN)=CC=2)C(OC)=CC=1C1CC1 CSYFFTHQKKHNHF-UHFFFAOYSA-N 0.000 claims 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 claims 1
• SSKKPZIWGIQQGD-UHFFFAOYSA-N 9-[4-(2-aminoethyl)phenyl]-6-chloro-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCN)=CC=C1C1=C(O)C=C(Cl)C2=C1C(C=CS1)=C1C(=O)N2 SSKKPZIWGIQQGD-UHFFFAOYSA-N 0.000 claims 1
• 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 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 claims 1
• LCAHCDNOYSALLV-UHFFFAOYSA-N 9-[4-(3-amino-1-hydroxypropyl)phenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(O)CCN)C=C1 LCAHCDNOYSALLV-UHFFFAOYSA-N 0.000 claims 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 claims 1
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• GSQPLFIKUWANBP-HNNXBMFYSA-N tert-butyl n-methyl-n-[(2r)-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl]carbamate Chemical compound C1=CC([C@H](CN(C)C(=O)OC(C)(C)C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 GSQPLFIKUWANBP-HNNXBMFYSA-N 0.000 description 1
• GSQPLFIKUWANBP-OAHLLOKOSA-N tert-butyl n-methyl-n-[(2s)-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl]carbamate Chemical compound C1=CC([C@@H](CN(C)C(=O)OC(C)(C)C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 GSQPLFIKUWANBP-OAHLLOKOSA-N 0.000 description 1
• PARGGKARAWEVQO-UHFFFAOYSA-N tert-butyl n-methyl-n-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate Chemical compound C1=CC(CCN(C)C(=O)OC(C)(C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 PARGGKARAWEVQO-UHFFFAOYSA-N 0.000 description 1
• DPCJGNAOBDBZTM-UHFFFAOYSA-N tert-butyl n-methyl-n-[3-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butyl]carbamate Chemical compound C1=CC(C(CN(C)C(=O)OC(C)(C)C)C(C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 DPCJGNAOBDBZTM-UHFFFAOYSA-N 0.000 description 1
• BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
• 230000002381 testicular Effects 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
• BWHDROKFUHTORW-UHFFFAOYSA-N tri-tert-butylphosphine Substances CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
• 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
• 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
• 235000019798 tripotassium phosphate Nutrition 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1