JP2013523749A5 - - Google Patents

Info

Publication number

JP2013523749A5

JP2013523749A5 JP2013502740A JP2013502740A JP2013523749A5 JP 2013523749 A5 JP2013523749 A5 JP 2013523749A5 JP 2013502740 A JP2013502740 A JP 2013502740A JP 2013502740 A JP2013502740 A JP 2013502740A JP 2013523749 A5 JP2013523749 A5 JP 2013523749A5

Authority

JP

Japan

Prior art keywords

quinolin

phenyl

hydroxy

hydroxythieno

oxo

Prior art date

2011-03-29

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.)

Granted

Links

• Espacenet
• Global Dossier
• Discuss

• -1 or Chemical group 0.000 claims description 185
• VLCMRTMCMQJSKM-UHFFFAOYSA-N phenyl-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C1=CC=CC=C1 VLCMRTMCMQJSKM-UHFFFAOYSA-N 0.000 claims description 45
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 17
• 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 13
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 12
• 150000001875 compounds Chemical class 0.000 claims description 11
• 150000003839 salts Chemical class 0.000 claims description 11
• 125000005999 2-bromoethyl group Chemical group 0.000 claims description 9
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 9
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• MMYHBULUVREXPP-ZDUSSCGKSA-N 8-[(3s)-3-aminopyrrolidin-1-yl]-2-(4-hydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1[C@@H](N)CCN1C1=CC=C(NC(=O)C2=C3C=C(S2)C=2C=CC(O)=CC=2)C3=C1 MMYHBULUVREXPP-ZDUSSCGKSA-N 0.000 claims description 6
• BOLQOFVUCLAHOY-UHFFFAOYSA-N 9-[4-(2-aminoethyl)phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCN)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 BOLQOFVUCLAHOY-UHFFFAOYSA-N 0.000 claims description 6
• 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 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
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 6
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 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 5
• XYKBFRBMVQKRHJ-GFCCVEGCSA-N 8-[(3r)-3-aminopyrrolidin-1-yl]-2-(3,4-dihydroxyphenyl)-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1[C@H](N)CCN1C1=CC=C(NC(=O)C2=C3C=C(S2)C=2C=C(O)C(O)=CC=2)C3=C1 XYKBFRBMVQKRHJ-GFCCVEGCSA-N 0.000 claims description 5
• 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 5
• 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 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 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 claims description 4
• 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 claims description 4
• 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 description 4
• RBGNHLPTMMSZMM-UHFFFAOYSA-N 9-(3-fluoro-4-hydroxyphenyl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C(F)C(O)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 RBGNHLPTMMSZMM-UHFFFAOYSA-N 0.000 claims description 4
• 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 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
• 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
• RTGGXEUXYBKUPH-LLVKDONJSA-N 9-[4-[(2s)-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-LLVKDONJSA-N 0.000 claims description 4
• SKYKQHGCAVDFER-UHFFFAOYSA-N 9-[6-(1-aminoethyl)pyridin-3-yl]-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)N)N=C1 SKYKQHGCAVDFER-UHFFFAOYSA-N 0.000 claims description 4
• GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 4
• 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 claims description 3
• PRCDUPVVGBJRCP-UHFFFAOYSA-N 1,1-diethyl-3-[[4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]methyl]urea Chemical compound C1=CC(CNC(=O)N(CC)CC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 PRCDUPVVGBJRCP-UHFFFAOYSA-N 0.000 claims description 3
• 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
• 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 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
• 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 claims description 3
• PDNVJFMMFLPVIM-UHFFFAOYSA-N 1-[4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]cyclopropane-1-carbonitrile Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1C1(C#N)CC1 PDNVJFMMFLPVIM-UHFFFAOYSA-N 0.000 claims description 3
• GOJSWCWEYNOFHQ-UHFFFAOYSA-N 1-[4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]cyclopropane-1-carbonitrile Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1C1(C#N)CC1 GOJSWCWEYNOFHQ-UHFFFAOYSA-N 0.000 claims description 3
• FGZRRNPUXUMCIC-UHFFFAOYSA-N 1-methyl-4-oxo-5h-thieno[2,3-c]quinoline-8-carbonitrile Chemical compound C12=CC(C#N)=CC=C2NC(=O)C2=C1C(C)=CS2 FGZRRNPUXUMCIC-UHFFFAOYSA-N 0.000 claims description 3
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 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
• ZNRSRFHENFFRKR-UHFFFAOYSA-N 2-[2-fluoro-4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CC#N)C(F)=C1 ZNRSRFHENFFRKR-UHFFFAOYSA-N 0.000 claims description 3
• IYHLHWBKYIONDN-UHFFFAOYSA-N 2-[2-fluoro-4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CC#N)C(F)=C1 IYHLHWBKYIONDN-UHFFFAOYSA-N 0.000 claims description 3
• FKVRJQMJJBRBNQ-UHFFFAOYSA-N 2-[3-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=CC(CC#N)=C1 FKVRJQMJJBRBNQ-UHFFFAOYSA-N 0.000 claims description 3
• BJUQGBGNEOJZMD-UHFFFAOYSA-N 2-[3-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=CC(CC#N)=C1 BJUQGBGNEOJZMD-UHFFFAOYSA-N 0.000 claims description 3
• MMPAUJTZOMAOHU-UHFFFAOYSA-N 2-[4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CC#N)C=C1 MMPAUJTZOMAOHU-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• AXOAFUMGENSWMZ-UHFFFAOYSA-N 2-[[4-(aminomethyl)piperidin-1-yl]methyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1CC(CN)CCN1CC1=CC(C2=CC(O)=CC=C2NC2=O)=C2S1 AXOAFUMGENSWMZ-UHFFFAOYSA-N 0.000 claims description 3
• LUQIJWBJLLLVCZ-UHFFFAOYSA-N 2-fluoro-n-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)benzenesulfonamide Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(S(=O)(=O)NCCO)C(F)=C1 LUQIJWBJLLLVCZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• XYWHLHKCETVPLT-UHFFFAOYSA-N 3-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)benzonitrile Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=CC(C#N)=C1 XYWHLHKCETVPLT-UHFFFAOYSA-N 0.000 claims description 3
• CYKQJDXXHCEMQD-UHFFFAOYSA-N 3-[3-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propanenitrile Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=CC(CCC#N)=C1 CYKQJDXXHCEMQD-UHFFFAOYSA-N 0.000 claims description 3
• GENGYDXUNLAJHA-UHFFFAOYSA-N 3-[3-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propanenitrile Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=CC(CCC#N)=C1 GENGYDXUNLAJHA-UHFFFAOYSA-N 0.000 claims description 3
• GWNNKFMWPZWVJN-UHFFFAOYSA-N 3-[4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propanenitrile Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCC#N)C=C1 GWNNKFMWPZWVJN-UHFFFAOYSA-N 0.000 claims description 3
• RJCAGQWAPIQFON-UHFFFAOYSA-N 3-[4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]-3-oxopropanenitrile Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(=O)CC#N)C=C1 RJCAGQWAPIQFON-UHFFFAOYSA-N 0.000 claims description 3
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
• KWWDFDWRLJWEMC-UHFFFAOYSA-N 4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 KWWDFDWRLJWEMC-UHFFFAOYSA-N 0.000 claims description 3
• CMRJVQPBTWNUIT-UHFFFAOYSA-N 4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)-n-(3-methylbutyl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCC(C)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 CMRJVQPBTWNUIT-UHFFFAOYSA-N 0.000 claims description 3
• VOLQCHAQJFJZFL-UHFFFAOYSA-N 4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 VOLQCHAQJFJZFL-UHFFFAOYSA-N 0.000 claims description 3
• SKFYJZPHCZZCCE-UHFFFAOYSA-N 4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 SKFYJZPHCZZCCE-UHFFFAOYSA-N 0.000 claims description 3
• KCFYWMBKFIZTLB-UHFFFAOYSA-N 4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)benzonitrile Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C#N)C=C1 KCFYWMBKFIZTLB-UHFFFAOYSA-N 0.000 claims description 3
• FWDWSJYBSMLVRN-UHFFFAOYSA-N 4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)-n,n-dimethylbenzenesulfonamide Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(S(=O)(=O)N(C)C)C=C1 FWDWSJYBSMLVRN-UHFFFAOYSA-N 0.000 claims description 3
• ZGESPOGZTOQCFO-UHFFFAOYSA-N 4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)-n-propylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 ZGESPOGZTOQCFO-UHFFFAOYSA-N 0.000 claims description 3
• OYOXGRMMUWXDQR-UHFFFAOYSA-N 4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)benzonitrile Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C#N)C=C1 OYOXGRMMUWXDQR-UHFFFAOYSA-N 0.000 claims description 3
• SNKSXKDXKTXYQP-UHFFFAOYSA-N 4-oxo-5h-thieno[2,3-c]quinoline-8-carbonitrile Chemical compound O=C1NC2=CC=C(C#N)C=C2C2=C1SC=C2 SNKSXKDXKTXYQP-UHFFFAOYSA-N 0.000 claims description 3
• GICXEWLNDUOZDJ-UHFFFAOYSA-N 5-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)-3h-1,3-benzoxazol-2-one Chemical compound C1=C2OC(=O)NC2=CC(C2=C3C=4C=CSC=4C(=O)NC3=CC=C2O)=C1 GICXEWLNDUOZDJ-UHFFFAOYSA-N 0.000 claims description 3
• QOCKYTNDOPCORF-UHFFFAOYSA-N 6-chloro-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=C(Cl)C2=C1C(C=CS1)=C1C(=O)N2 QOCKYTNDOPCORF-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• OLYOORKNESCLTH-UHFFFAOYSA-N 7,8,9-trihydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C(O)=C(O)C(O)=CC=2NC(=O)C2=C1C=CS2 OLYOORKNESCLTH-UHFFFAOYSA-N 0.000 claims description 3
• YKLBSLRCVXWLCU-UHFFFAOYSA-N 7,8,9-trimethoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=2C(OC)=C(OC)C(OC)=CC=2NC(=O)C2=C1C=CS2 YKLBSLRCVXWLCU-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
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• OIOUIPSTQHPGEN-UHFFFAOYSA-N 9-[4-[2-(dimethylamino)ethyl]phenyl]-6-fluoro-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(F)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCN(C)C)C=C1 OIOUIPSTQHPGEN-UHFFFAOYSA-N 0.000 claims description 3
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• ALRVNRWMUOBFGI-UHFFFAOYSA-N 9-[4-[2-(ethylamino)ethoxy]phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(OCCNCC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 ALRVNRWMUOBFGI-UHFFFAOYSA-N 0.000 claims description 3
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• XNDBJBUGRRJFNM-UHFFFAOYSA-N 9-[4-[3-(diethylamino)propoxy]phenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(OCCCN(CC)CC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 XNDBJBUGRRJFNM-UHFFFAOYSA-N 0.000 claims description 3
• AYJAYTPLNHSBDD-UHFFFAOYSA-N 9-[4-[3-(dimethylamino)propoxy]phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(OCCCN(C)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 AYJAYTPLNHSBDD-UHFFFAOYSA-N 0.000 claims description 3
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• IYAYIGCVDVSWQN-UHFFFAOYSA-N 9-[4-[[4-(aminomethyl)piperidin-1-yl]methyl]-3-fluorophenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1CC(CN)CCN1CC1=CC=C(C=2C=3C=4C=CSC=4C(=O)NC=3C=CC=2O)C=C1F IYAYIGCVDVSWQN-UHFFFAOYSA-N 0.000 claims description 3
• PWQCQEBKZGEMDY-UHFFFAOYSA-N 9-[4-[[4-(aminomethyl)piperidin-1-yl]methyl]-3-fluorophenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1F)=CC=C1CN1CCC(CN)CC1 PWQCQEBKZGEMDY-UHFFFAOYSA-N 0.000 claims description 3
• KGKCMRVFOHCEQP-UHFFFAOYSA-N 9-[5-(aminomethyl)furan-2-yl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound O1C(CN)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 KGKCMRVFOHCEQP-UHFFFAOYSA-N 0.000 claims description 3
• YJLUSYSZDWUAAU-UHFFFAOYSA-N 9-[5-(aminomethyl)thiophen-2-yl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound S1C(CN)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 YJLUSYSZDWUAAU-UHFFFAOYSA-N 0.000 claims description 3
• FBWSMWOFHUEWQP-UHFFFAOYSA-N 9-amino-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C12=C(N)C(OC)=CC=C2NC(=O)C2=C1C=CS2 FBWSMWOFHUEWQP-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• INHRRNJRNMXUJX-UHFFFAOYSA-N 9-cyclopropyl-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1CC1 INHRRNJRNMXUJX-UHFFFAOYSA-N 0.000 claims description 3
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
• POEVDNZCHFYKGG-UHFFFAOYSA-N [9-[3-fluoro-4-[2-(methanesulfonamido)ethyl]phenyl]-4-oxo-5h-thieno[2,3-c]quinolin-8-yl] methanesulfonate Chemical compound C1=C(F)C(CCNS(=O)(=O)C)=CC=C1C1=C(OS(C)(=O)=O)C=CC2=C1C(C=CS1)=C1C(=O)N2 POEVDNZCHFYKGG-UHFFFAOYSA-N 0.000 claims description 3
• KPJVZNKGCLOUFX-UHFFFAOYSA-N [9-[4-(aminomethyl)phenyl]-4-oxo-5h-thieno[2,3-c]quinolin-8-yl] trifluoromethanesulfonate Chemical compound C1=CC(CN)=CC=C1C1=C(OS(=O)(=O)C(F)(F)F)C=CC2=C1C(C=CS1)=C1C(=O)N2 KPJVZNKGCLOUFX-UHFFFAOYSA-N 0.000 claims description 3
• FYLQFGXOSFOXRG-GFCCVEGCSA-N [9-[4-[(1r)-1-(methanesulfonamido)ethyl]phenyl]-4-oxo-5h-thieno[2,3-c]quinolin-8-yl] methanesulfonate Chemical compound C1=CC([C@H](NS(C)(=O)=O)C)=CC=C1C1=C(OS(C)(=O)=O)C=CC2=C1C(C=CS1)=C1C(=O)N2 FYLQFGXOSFOXRG-GFCCVEGCSA-N 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
• QRYMVHRIIQATTI-UHFFFAOYSA-N n-(2-bromoethyl)-2-fluoro-4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)benzenesulfonamide Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(S(=O)(=O)NCCBr)C(F)=C1 QRYMVHRIIQATTI-UHFFFAOYSA-N 0.000 claims description 3
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• 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
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• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
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• 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 claims description 2
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• 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 claims description 2
• OWAVZGAOAYALIT-UHFFFAOYSA-N 9-[4-[3-(dimethylamino)-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)C)C=C1 OWAVZGAOAYALIT-UHFFFAOYSA-N 0.000 claims description 2
• LSGYTCQLRWZANP-UHFFFAOYSA-N 9-[4-[3-[(dimethylamino)methyl]pentan-3-yl]phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(CC)(CN(C)C)CC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 LSGYTCQLRWZANP-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims description 2
• XQKCBCNBBQNINY-UHFFFAOYSA-N 9-[4-[hydroxy(1,3-thiazol-2-yl)methyl]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(O)C1=NC=CS1 XQKCBCNBBQNINY-UHFFFAOYSA-N 0.000 claims description 2
• CMFINBSDVRVIIK-UHFFFAOYSA-N 9-[6-(1-aminoethyl)pyridin-3-yl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=NC(C(N)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 CMFINBSDVRVIIK-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
• 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 claims description 2
• 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 description 2
• 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 claims description 2
• 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 claims description 2
• KHGKKDFYIKDLHS-UHFFFAOYSA-N 9-[6-[1-(diethylamino)ethyl]pyridin-3-yl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=NC(C(C)N(CC)CC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 KHGKKDFYIKDLHS-UHFFFAOYSA-N 0.000 claims description 2
• XNSVFQVGYJPAJE-UHFFFAOYSA-N 9-[6-[1-(dimethylamino)ethyl]pyridin-3-yl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=NC(C(N(C)C)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 XNSVFQVGYJPAJE-UHFFFAOYSA-N 0.000 claims description 2
• OKZKYXGEWXHJIO-UHFFFAOYSA-N 9-[6-[1-(dimethylamino)ethyl]pyridin-3-yl]-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)N(C)C)N=C1 OKZKYXGEWXHJIO-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
• YQQPDMVUECEAJK-UHFFFAOYSA-N N-(8-methoxy-4-oxo-5H-thieno[2,3-c]quinolin-9-yl)benzenesulfonamide Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC=1C=2C3=C(C(NC=2C=CC=1OC)=O)SC=C3 YQQPDMVUECEAJK-UHFFFAOYSA-N 0.000 claims description 2
• FAZHHNSKKXZUDQ-UHFFFAOYSA-N N-[4-(8-methoxy-4-oxo-5H-thieno[2,3-c]quinolin-9-yl)phenyl]ethanesulfonamide Chemical compound C(C)S(=O)(=O)NC1=CC=C(C=C1)C=1C=2C3=C(C(NC=2C=CC=1OC)=O)SC=C3 FAZHHNSKKXZUDQ-UHFFFAOYSA-N 0.000 claims description 2
• IRDQECODCUWLBM-UHFFFAOYSA-N [9-[4-(1-aminoethyl)phenyl]-4-oxo-5h-thieno[2,3-c]quinolin-8-yl] acetate Chemical compound C1=CC(C(N)C)=CC=C1C1=C(OC(C)=O)C=CC2=C1C(C=CS1)=C1C(=O)N2 IRDQECODCUWLBM-UHFFFAOYSA-N 0.000 claims description 2
• GVSDRBPZWPFCSC-UHFFFAOYSA-N [9-[4-(1-aminoethyl)phenyl]-4-oxo-5h-thieno[2,3-c]quinolin-8-yl] morpholine-4-carboxylate Chemical compound C1=CC(C(N)C)=CC=C1C(C=1C=2C=CSC=2C(=O)NC=1C=C1)=C1OC(=O)N1CCOCC1 GVSDRBPZWPFCSC-UHFFFAOYSA-N 0.000 claims description 2
• HNPRTOCSHLUJHQ-UHFFFAOYSA-N [9-[4-(1-aminoethyl)phenyl]-4-oxo-5h-thieno[2,3-c]quinolin-8-yl] n,n-diethylcarbamate Chemical compound CCN(CC)C(=O)OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)N)C=C1 HNPRTOCSHLUJHQ-UHFFFAOYSA-N 0.000 claims description 2
• HOAOAQXDGNZWDO-UHFFFAOYSA-N [9-[4-(1-aminoethyl)phenyl]-4-oxo-5h-thieno[2,3-c]quinolin-8-yl] n,n-dimethylcarbamate Chemical compound C1=CC(C(N)C)=CC=C1C1=C(OC(=O)N(C)C)C=CC2=C1C(C=CS1)=C1C(=O)N2 HOAOAQXDGNZWDO-UHFFFAOYSA-N 0.000 claims description 2
• APIJSFSFSPDPLN-UHFFFAOYSA-N [9-[4-(1-aminoethyl)phenyl]-4-oxo-5h-thieno[2,3-c]quinolin-8-yl] propan-2-yl carbonate Chemical compound CC(C)OC(=O)OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)N)C=C1 APIJSFSFSPDPLN-UHFFFAOYSA-N 0.000 claims description 2
• LWZQBTRJOCZPBW-INIZCTEOSA-N [9-[4-[(1s)-1-(methanesulfonamido)propyl]phenyl]-4-oxo-5h-thieno[2,3-c]quinolin-8-yl] methanesulfonate Chemical compound C1=CC([C@@H](NS(C)(=O)=O)CC)=CC=C1C1=C(OS(C)(=O)=O)C=CC2=C1C(C=CS1)=C1C(=O)N2 LWZQBTRJOCZPBW-INIZCTEOSA-N 0.000 claims description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
• VCCBEVNXKXJYNV-UHFFFAOYSA-N n-(1-bromopropan-2-yl)-4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC(CBr)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 VCCBEVNXKXJYNV-UHFFFAOYSA-N 0.000 claims description 2
• GZPULEGLFDKNJH-UHFFFAOYSA-N n-(1-chloropropan-2-yl)-4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)benzenesulfonamide Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(S(=O)(=O)NC(C)CCl)C=C1 GZPULEGLFDKNJH-UHFFFAOYSA-N 0.000 claims description 2
• JYKNUSUQGXPXBC-UHFFFAOYSA-N n-(1-hydroxypropan-2-yl)-4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)benzenesulfonamide Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(S(=O)(=O)NC(C)CO)C=C1 JYKNUSUQGXPXBC-UHFFFAOYSA-N 0.000 claims description 2
• NJDVCWKWQCBZMB-UHFFFAOYSA-N n-(2-bromoethyl)-4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(CCBr)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 NJDVCWKWQCBZMB-UHFFFAOYSA-N 0.000 claims description 2
• LTFWPRWTXSRRMK-UHFFFAOYSA-N n-(2-chloroethyl)-4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(CCCl)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 LTFWPRWTXSRRMK-UHFFFAOYSA-N 0.000 claims description 2
• ZEZSHTDDFBMANW-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(CCO)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 ZEZSHTDDFBMANW-UHFFFAOYSA-N 0.000 claims description 2
• SSXMTGYKFZKGRH-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)-n-methylbenzenesulfonamide Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(S(=O)(=O)N(C)CCO)C=C1 SSXMTGYKFZKGRH-UHFFFAOYSA-N 0.000 claims description 2
• MFOLUDOMXRJLOM-LBPRGKRZSA-N n-[(2r)-2-[4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propyl]methanesulfonamide Chemical compound C1=CC([C@H](CNS(C)(=O)=O)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 MFOLUDOMXRJLOM-LBPRGKRZSA-N 0.000 claims description 2
• CPBALRFUCTXAKE-AWEZNQCLSA-N n-[(2r)-2-[4-(8-hydroxy-6-methyl-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propyl]-n-methylmethanesulfonamide Chemical compound C1=CC([C@H](CN(C)S(C)(=O)=O)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 CPBALRFUCTXAKE-AWEZNQCLSA-N 0.000 claims description 2
• FKEBHOXZDXPWRC-ZDUSSCGKSA-N n-[(2r)-2-[4-(8-hydroxy-6-methyl-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propyl]methanesulfonamide Chemical compound C1=CC([C@H](CNS(C)(=O)=O)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 FKEBHOXZDXPWRC-ZDUSSCGKSA-N 0.000 claims description 2
• LQUKOENHTUHNTK-ZDUSSCGKSA-N n-[(2r)-2-[4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propyl]methanesulfonamide Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C([C@@H](C)CNS(C)(=O)=O)C=C1 LQUKOENHTUHNTK-ZDUSSCGKSA-N 0.000 claims description 2
• PHWVVKIJZULAQZ-HNNXBMFYSA-N n-[(2r)-2-[4-(8-methoxy-6-methyl-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propyl]-n-methylmethanesulfonamide Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C([C@@H](C)CN(C)S(C)(=O)=O)C=C1 PHWVVKIJZULAQZ-HNNXBMFYSA-N 0.000 claims description 2
• JSSNTQQHLGNNFR-AWEZNQCLSA-N n-[(2r)-2-[4-(8-methoxy-6-methyl-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propyl]methanesulfonamide Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C([C@@H](C)CNS(C)(=O)=O)C=C1 JSSNTQQHLGNNFR-AWEZNQCLSA-N 0.000 claims description 2
• WOVYVRICWBCAFW-UHFFFAOYSA-N n-[2-[4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]-2-methylpropyl]methanesulfonamide Chemical compound C1=CC(C(C)(CNS(C)(=O)=O)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 WOVYVRICWBCAFW-UHFFFAOYSA-N 0.000 claims description 2
• GPKSVOKTUJSNRI-UHFFFAOYSA-N n-[4-(8-hydroxy-6-methyl-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]methanesulfonamide Chemical compound C1=2C=3C=CSC=3C(=O)NC=2C(C)=CC(O)=C1C1=CC=C(NS(C)(=O)=O)C=C1 GPKSVOKTUJSNRI-UHFFFAOYSA-N 0.000 claims description 2
• PIGSIVSWALPTRZ-UHFFFAOYSA-N n-[4-(8-methoxy-6-methyl-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]ethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1C1=C(OC)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 PIGSIVSWALPTRZ-UHFFFAOYSA-N 0.000 claims description 2
• BWMLRJHTVBEELU-UHFFFAOYSA-N n-[4-(8-methoxy-6-methyl-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]methanesulfonamide Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(NS(C)(=O)=O)C=C1 BWMLRJHTVBEELU-UHFFFAOYSA-N 0.000 claims description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 2
• 229910052739 hydrogen Inorganic materials 0.000 claims 31
• 239000001257 hydrogen Chemical group 0.000 claims 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 22
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims 16
• 125000000217 alkyl group Chemical group 0.000 claims 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 14
• 229910052736 halogen Inorganic materials 0.000 claims 13
• 150000002367 halogens Chemical group 0.000 claims 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims 11
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 9
• 150000002431 hydrogen Chemical group 0.000 claims 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims 8
• 125000003118 aryl group Chemical group 0.000 claims 6
• 125000005936 piperidyl group Chemical group 0.000 claims 6
• 125000001072 heteroaryl group Chemical group 0.000 claims 5
• 230000001419 dependent effect Effects 0.000 claims 4
• 201000010099 disease Diseases 0.000 claims 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
• 239000008194 pharmaceutical composition Substances 0.000 claims 4
• 125000001424 substituent group Chemical group 0.000 claims 4
• 125000002757 morpholinyl group Chemical group 0.000 claims 3
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 3
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims 2
• TUYAMPOPPVMZOB-UHFFFAOYSA-N 9-(3,4-difluorophenyl)-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(F)C(F)=C1 TUYAMPOPPVMZOB-UHFFFAOYSA-N 0.000 claims 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
• 125000003545 alkoxy group Chemical group 0.000 claims 2
• 229910052799 carbon Inorganic materials 0.000 claims 2
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
• NCIYEPKVXRIPMM-ZDUSSCGKSA-N 6-chloro-9-[4-[(2r)-1-(dimethylamino)propan-2-yl]phenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC(Cl)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C([C@@H](C)CN(C)C)C=C1 NCIYEPKVXRIPMM-ZDUSSCGKSA-N 0.000 claims 1
• 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 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
• QPCRNXRDNKKSFH-UHFFFAOYSA-N 9-(3,5-difluorophenyl)-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound OC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC(F)=CC(F)=C1 QPCRNXRDNKKSFH-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
• 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
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