DK2552206T3 - Tricyclics AND PBK INHIBITORS CONTAINING THEM - Google Patents
Tricyclics AND PBK INHIBITORS CONTAINING THEM Download PDFInfo
- Publication number
- DK2552206T3 DK2552206T3 DK11763307.3T DK11763307T DK2552206T3 DK 2552206 T3 DK2552206 T3 DK 2552206T3 DK 11763307 T DK11763307 T DK 11763307T DK 2552206 T3 DK2552206 T3 DK 2552206T3
- Authority
- DK
- Denmark
- Prior art keywords
- quinolin
- phenyl
- thieno
- hydroxy
- hydroxythieno
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 6
- -1 hydroxyethylamino Chemical group 0.000 claims description 253
- 239000001257 hydrogen Chemical group 0.000 claims description 205
- 229910052739 hydrogen Inorganic materials 0.000 claims description 205
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 127
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 123
- 150000001875 compounds Chemical class 0.000 claims description 92
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 92
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 83
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 82
- 229910052736 halogen Inorganic materials 0.000 claims description 79
- 150000002367 halogens Chemical group 0.000 claims description 76
- 125000001424 substituent group Chemical group 0.000 claims description 75
- 150000002431 hydrogen Chemical group 0.000 claims description 66
- 125000005936 piperidyl group Chemical group 0.000 claims description 59
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 58
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 55
- 150000003839 salts Chemical class 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
- 125000003545 alkoxy group Chemical group 0.000 claims description 44
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000004193 piperazinyl group Chemical group 0.000 claims description 28
- 125000002757 morpholinyl group Chemical group 0.000 claims description 25
- 206010028980 Neoplasm Diseases 0.000 claims description 24
- 201000011510 cancer Diseases 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 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 19
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 14
- 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 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 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 10
- 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 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 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 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- YKXXFBHWNVDVJR-UHFFFAOYSA-N 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=C1 YKXXFBHWNVDVJR-UHFFFAOYSA-N 0.000 claims description 8
- 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 7
- 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 7
- 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 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- MMWJMPACIVFRFX-UHFFFAOYSA-N n-[4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)-2-methylphenyl]methanesulfonamide Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(NS(C)(=O)=O)C(C)=C1 MMWJMPACIVFRFX-UHFFFAOYSA-N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 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 6
- 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 6
- 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 6
- NPVZLKPHHQORRB-DUXPYHPUSA-N 9-[(e)-3-(3-aminopiperidin-1-yl)prop-1-enyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1C(N)CCCN1C\C=C\C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 NPVZLKPHHQORRB-DUXPYHPUSA-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
- CUQGMLWXJHUOGX-UHFFFAOYSA-N 9-[4-(2-aminoethyl)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=C1 CUQGMLWXJHUOGX-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- SRZXAPKPOAKZSD-UHFFFAOYSA-N 9-[4-[(dimethylamino)methyl]phenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CN(C)C)C=C1 SRZXAPKPOAKZSD-UHFFFAOYSA-N 0.000 claims description 6
- LERUBGGDUUBJFL-UHFFFAOYSA-N 9-[4-[1-(dimethylamino)ethyl]phenyl]-6,7-difluoro-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=C(F)C(F)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)N(C)C)C=C1 LERUBGGDUUBJFL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 6
- 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 5
- MMHDVVJAYIEIGD-UHFFFAOYSA-N 9-(4-amino-3-methoxyphenyl)-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(N)C(OC)=C1 MMHDVVJAYIEIGD-UHFFFAOYSA-N 0.000 claims description 5
- JATXSNBXAAURSW-GQCTYLIASA-N 9-[(e)-3-[3-(dimethylamino)piperidin-1-yl]prop-1-enyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1C(N(C)C)CCCN1C\C=C\C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 JATXSNBXAAURSW-GQCTYLIASA-N 0.000 claims description 5
- DIHXWSTUEKATGV-UHFFFAOYSA-N 9-[3-fluoro-4-[(3-hydroxypyrrolidin-1-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=C1F)=CC=C1CN1CCC(O)C1 DIHXWSTUEKATGV-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- BFIYZNDEFMHINH-UHFFFAOYSA-N 9-[4-(1-aminopropyl)phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(C(N)CC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 BFIYZNDEFMHINH-UHFFFAOYSA-N 0.000 claims description 5
- QJZQFKUMJMSYPB-UHFFFAOYSA-N 9-[4-(3-aminopropyl)phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCCN)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 QJZQFKUMJMSYPB-UHFFFAOYSA-N 0.000 claims description 5
- XIQBLIXWNGDLID-UHFFFAOYSA-N 9-[4-(diethylaminomethyl)phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CN(CC)CC)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 XIQBLIXWNGDLID-UHFFFAOYSA-N 0.000 claims description 5
- SKFADHGIHJUPNL-UHFFFAOYSA-N 9-[4-(diethylaminomethyl)phenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CN(CC)CC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 SKFADHGIHJUPNL-UHFFFAOYSA-N 0.000 claims description 5
- PZEQOFCNWJMLFQ-UHFFFAOYSA-N 9-[4-(ethylaminomethyl)phenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CNCC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 PZEQOFCNWJMLFQ-UHFFFAOYSA-N 0.000 claims description 5
- OJPDNHCQSDWYCT-JTQLQIEISA-N 9-[4-[(1s)-1-aminoethyl]phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC([C@@H](N)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 OJPDNHCQSDWYCT-JTQLQIEISA-N 0.000 claims description 5
- RFVFHKLYSVILJI-NSHDSACASA-N 9-[4-[(1s)-1-aminoethyl]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@H](C)N)C=C1 RFVFHKLYSVILJI-NSHDSACASA-N 0.000 claims description 5
- GKJCNYKGKAQOMV-LBPRGKRZSA-N 9-[4-[(2r)-1-aminopropan-2-yl]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@@H](C)CN)C=C1 GKJCNYKGKAQOMV-LBPRGKRZSA-N 0.000 claims description 5
- 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 5
- JYQDSHIEJSGQNK-UHFFFAOYSA-N 9-[4-[(dimethylamino)methyl]phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 JYQDSHIEJSGQNK-UHFFFAOYSA-N 0.000 claims description 5
- ITRCQSYUXJOIHS-UHFFFAOYSA-N 9-[4-[1-(cyclopentylamino)ethyl]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(C)NC1CCCC1 ITRCQSYUXJOIHS-UHFFFAOYSA-N 0.000 claims description 5
- NBBMWGADQAERGA-UHFFFAOYSA-N 9-[4-[2-(dimethylamino)ethyl]phenyl]-8-hydroxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(CCN(C)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 NBBMWGADQAERGA-UHFFFAOYSA-N 0.000 claims description 5
- XQWGKASWNUVUQU-UHFFFAOYSA-N 9-[4-[3-[2-(diethylamino)ethylamino]propoxy]phenyl]-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=CC(OCCCNCCN(CC)CC)=CC=C1C1=C(OC)C=CC2=C1C(C=CS1)=C1C(=O)N2 XQWGKASWNUVUQU-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 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 5
- OBUZUDQXWGKOIL-UHFFFAOYSA-N n-(2-fluoroethyl)-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)NCCF)C=C1 OBUZUDQXWGKOIL-UHFFFAOYSA-N 0.000 claims description 5
- YONLPQHQBZGSMF-UHFFFAOYSA-N 2-[4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]-2-(oxetan-3-yl)acetonitrile Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1C(C#N)C1COC1 YONLPQHQBZGSMF-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 4
- 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 4
- 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 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
- 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 4
- 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 4
- BHNWJNLCLSOBRU-UHFFFAOYSA-N 8-methoxy-9-[4-[(propan-2-ylamino)methyl]phenyl]-5h-thieno[2,3-c]quinolin-4-one Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CNC(C)C)C=C1 BHNWJNLCLSOBRU-UHFFFAOYSA-N 0.000 claims description 4
- PRHCZAVMCGKYNN-UHFFFAOYSA-N 9-(2,3-dihydro-1h-indol-5-yl)-8-methoxy-5h-thieno[2,3-c]quinolin-4-one Chemical compound C1=C2NCCC2=CC(C2=C3C=4C=CSC=4C(=O)NC3=CC=C2OC)=C1 PRHCZAVMCGKYNN-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
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- 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
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- 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
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- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- 102220545870 Vacuolar protein sorting-associated protein 41 homolog_R74A_mutation Human genes 0.000 claims description 2
- 102220545880 Vacuolar protein sorting-associated protein 41 homolog_R75A_mutation Human genes 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
- 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
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- QCSRVODTOZIYRM-LLVKDONJSA-N n-[(1r)-1-[4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]ethyl]methanesulfonamide Chemical compound C1=CC([C@H](NS(C)(=O)=O)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 QCSRVODTOZIYRM-LLVKDONJSA-N 0.000 claims description 2
- RHBAZLSIAUXEGX-LBPRGKRZSA-N n-[(2r)-2-[2-fluoro-4-(8-hydroxy-6-methyl-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propyl]methanesulfonamide Chemical compound C1=C(F)C([C@H](CNS(C)(=O)=O)C)=CC=C1C1=C(O)C=C(C)C2=C1C(C=CS1)=C1C(=O)N2 RHBAZLSIAUXEGX-LBPRGKRZSA-N 0.000 claims description 2
- SDBKKQOUJXIHJN-ZDUSSCGKSA-N n-[(2r)-2-[2-fluoro-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(F)=C1 SDBKKQOUJXIHJN-ZDUSSCGKSA-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
- 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
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
- DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 7
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 5
- 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 5
- 125000005999 2-bromoethyl group Chemical group 0.000 claims 4
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 3
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- CKWJIFNNVRMXFW-UHFFFAOYSA-N tert-butyl n-[2-(4-bromophenyl)propan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)(C)C1=CC=C(Br)C=C1 CKWJIFNNVRMXFW-UHFFFAOYSA-N 0.000 description 1
- BWNIERMOMIYCBU-UHFFFAOYSA-N tert-butyl n-[2-[2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate Chemical compound C1=C(Cl)C(CCNC(=O)OC(C)(C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 BWNIERMOMIYCBU-UHFFFAOYSA-N 0.000 description 1
- RINMMXGBZVCUDN-UHFFFAOYSA-N tert-butyl n-[2-[2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl]carbamate Chemical compound C1=C(Cl)C(C(CNC(=O)OC(C)(C)C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 RINMMXGBZVCUDN-UHFFFAOYSA-N 0.000 description 1
- ATHQUAUVXVFXJX-UHFFFAOYSA-N tert-butyl n-[2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate Chemical compound C1=C(F)C(CCNC(=O)OC(C)(C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 ATHQUAUVXVFXJX-UHFFFAOYSA-N 0.000 description 1
- YSWGHDMGGXFIDV-UHFFFAOYSA-N tert-butyl n-[2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl]carbamate Chemical compound C1=C(F)C(C(CNC(=O)OC(C)(C)C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 YSWGHDMGGXFIDV-UHFFFAOYSA-N 0.000 description 1
- YPCNPOPHTRXFRW-UHFFFAOYSA-N tert-butyl n-[2-[2-fluoro-4-(8-methoxy-6-methyl-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]-2-methylpropyl]carbamate Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)(C)CNC(=O)OC(C)(C)C)C(F)=C1 YPCNPOPHTRXFRW-UHFFFAOYSA-N 0.000 description 1
- OOBKFZVDURJNIU-UHFFFAOYSA-N tert-butyl n-[2-[2-fluoro-4-(8-methoxy-6-methyl-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]ethyl]-n-methylcarbamate Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCN(C)C(=O)OC(C)(C)C)C(F)=C1 OOBKFZVDURJNIU-UHFFFAOYSA-N 0.000 description 1
- MGDIIQXOACAHIU-UHFFFAOYSA-N tert-butyl n-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate Chemical compound C1=CC(CCNC(=O)OC(C)(C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 MGDIIQXOACAHIU-UHFFFAOYSA-N 0.000 description 1
- KFTWYIAAHLUIBS-UHFFFAOYSA-N tert-butyl n-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl]carbamate Chemical compound C1=CC(C(CNC(=O)OC(C)(C)C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 KFTWYIAAHLUIBS-UHFFFAOYSA-N 0.000 description 1
- QJSFBNCPRBKFNS-UHFFFAOYSA-N tert-butyl n-[2-[4-(6-bromo-8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)-2-fluorophenyl]ethyl]-n-methylcarbamate Chemical compound COC1=CC(Br)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCN(C)C(=O)OC(C)(C)C)C(F)=C1 QJSFBNCPRBKFNS-UHFFFAOYSA-N 0.000 description 1
- FSDRBIKAQRWBGZ-UHFFFAOYSA-N tert-butyl n-[2-[4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]-3-methylbutyl]carbamate Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(CNC(=O)OC(C)(C)C)C(C)C)C=C1 FSDRBIKAQRWBGZ-UHFFFAOYSA-N 0.000 description 1
- WOPPNXTWWYUSFX-UHFFFAOYSA-N tert-butyl n-[2-[4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]propyl]carbamate Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(C(C)CNC(=O)OC(C)(C)C)C=C1 WOPPNXTWWYUSFX-UHFFFAOYSA-N 0.000 description 1
- GQNRLIQFMWTLPB-UHFFFAOYSA-N tert-butyl n-[2-[4-(8-methoxy-6-methyl-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]ethyl]carbamate Chemical compound COC1=CC(C)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CCNC(=O)OC(C)(C)C)C=C1 GQNRLIQFMWTLPB-UHFFFAOYSA-N 0.000 description 1
- JFIGWXGHKSPAKE-UHFFFAOYSA-N tert-butyl n-[2-[5-bromo-2-hydroxy-4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]ethyl]carbamate Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C1=CC(O)=C(CCNC(=O)OC(C)(C)C)C=C1Br JFIGWXGHKSPAKE-UHFFFAOYSA-N 0.000 description 1
- WCEITOFHCDDSET-UHFFFAOYSA-N tert-butyl n-[[1-[[4-(8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]methyl]piperidin-4-yl]methyl]carbamate Chemical compound COC1=CC=C2NC(=O)C=3SC=CC=3C2=C1C(C=C1)=CC=C1CN1CCC(CNC(=O)OC(C)(C)C)CC1 WCEITOFHCDDSET-UHFFFAOYSA-N 0.000 description 1
- CUDCEJRRWNIPDL-UHFFFAOYSA-N tert-butyl n-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OC(C)(C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 CUDCEJRRWNIPDL-UHFFFAOYSA-N 0.000 description 1
- KYRYLJFKAQHXHY-UHFFFAOYSA-N tert-butyl n-[[4-(6-chloro-8-methoxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]methyl]carbamate Chemical compound COC1=CC(Cl)=C2NC(=O)C=3SC=CC=3C2=C1C1=CC=C(CNC(=O)OC(C)(C)C)C=C1 KYRYLJFKAQHXHY-UHFFFAOYSA-N 0.000 description 1
- TYYYKVWXLYNXSH-UHFFFAOYSA-N tert-butyl n-[[4-(8-hydroxy-4-oxo-5h-thieno[2,3-c]quinolin-9-yl)phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OC(C)(C)C)=CC=C1C1=C(O)C=CC2=C1C(C=CS1)=C1C(=O)N2 TYYYKVWXLYNXSH-UHFFFAOYSA-N 0.000 description 1
- YRSBMLYBZHELAV-UHFFFAOYSA-N tert-butyl n-ethyl-n-[1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate Chemical compound C1=CC(C(C)N(CC)C(=O)OC(C)(C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 YRSBMLYBZHELAV-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 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
- 125000005942 tetrahydropyridyl group Chemical group 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
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/02—Ergot alkaloids of the cyclic peptide type
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
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|---|---|---|---|
| US31860610P | 2010-03-29 | 2010-03-29 | |
| PCT/US2011/030278 WO2011123419A1 (en) | 2010-03-29 | 2011-03-29 | Trycyclic compounds and pbk inhibitors containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2552206T3 true DK2552206T3 (en) | 2015-09-28 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK11763307.3T DK2552206T3 (en) | 2010-03-29 | 2011-03-29 | Tricyclics AND PBK INHIBITORS CONTAINING THEM |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US8962648B2 (enExample) |
| EP (1) | EP2552206B1 (enExample) |
| JP (1) | JP5849302B2 (enExample) |
| KR (1) | KR101757502B1 (enExample) |
| CN (1) | CN102917590B (enExample) |
| AU (1) | AU2011235319B2 (enExample) |
| BR (1) | BR112012023836B1 (enExample) |
| CA (1) | CA2792941C (enExample) |
| DK (1) | DK2552206T3 (enExample) |
| ES (1) | ES2547571T3 (enExample) |
| IL (1) | IL222080B (enExample) |
| MX (1) | MX2012011412A (enExample) |
| SG (1) | SG184376A1 (enExample) |
| TW (1) | TWI503323B (enExample) |
| WO (1) | WO2011123419A1 (enExample) |
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| HRP20181849T1 (hr) * | 2013-12-24 | 2018-12-28 | Bristol-Myers Squibb Company | Triciklični spojevi kao antikancerogeni agensi |
| TWI557011B (zh) | 2015-05-25 | 2016-11-11 | 可影像處理的自行車錶裝置 | |
| AU2016275764B8 (en) | 2015-06-11 | 2021-03-04 | Basilea Pharmaceutica International AG | Efflux-pump inhibitors and therapeutic uses thereof |
| GB201617758D0 (en) | 2016-10-20 | 2016-12-07 | Almac Discovery Limited | Pharmaceutical compounds |
| CN108341774B (zh) * | 2017-01-25 | 2022-07-19 | 首药控股(北京)股份有限公司 | 取代的喹啉酮类抑制剂 |
| PH12019502314A1 (en) | 2017-04-10 | 2020-10-26 | Bayer Ag | Substituted n-arylethyl-2-arylquinoline-4-carboxamides and use thereof |
| US12024715B2 (en) | 2017-11-07 | 2024-07-02 | Temple University-Of The Commonwealth System Of Higher Education | Compositions and methods for improved T cells |
| CN111099941B (zh) * | 2018-10-26 | 2022-10-18 | 中国科学院上海有机化学研究所 | 一种烷基腈类化合物的制备方法 |
| TW202300150A (zh) * | 2021-03-18 | 2023-01-01 | 美商薛定諤公司 | 環狀化合物及其使用方法 |
| WO2024008113A1 (zh) * | 2022-07-07 | 2024-01-11 | 深圳微芯生物科技股份有限公司 | 一种甲酰胺取代的杂三环类衍生物、其制备方法及其应用 |
| WO2024097228A1 (en) * | 2022-10-31 | 2024-05-10 | Meliora Therapeutics, Inc. | Compounds targeting cdk11 and methods of using the same |
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| JPS5377096A (en) * | 1976-12-17 | 1978-07-08 | Teijin Ltd | Preparation of thieno 2,3-c quinolin-4(5h)-one-7-acetic acids |
| FR2636063B1 (fr) * | 1988-09-05 | 1993-04-30 | Centre Nat Rech Scient | Composes phenylpyrroliques utiles en tant que medicaments, leur preparation et leur application |
| DE19806348A1 (de) * | 1998-02-12 | 1999-08-19 | Schering Ag | 3,4-Dihydrochinolin-Derivate und ihre Verwendung in Arzneimitteln |
| US6506769B2 (en) * | 1999-10-06 | 2003-01-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | Heterocyclic compounds useful as inhibitors of tyrosine kinases |
| JP2003519127A (ja) * | 1999-12-29 | 2003-06-17 | ワイス | 三環系タンパクキナーゼ阻害薬 |
| US6638929B2 (en) * | 1999-12-29 | 2003-10-28 | Wyeth | Tricyclic protein kinase inhibitors |
| DE10242106A1 (de) | 2002-09-11 | 2004-04-15 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Phosphorgruppenhaltige Carbonsäurederivate mit organisch polymerisierbaren Gruppen |
| MXPA05002007A (es) * | 2002-09-17 | 2005-04-28 | Warner Lambert Co | Piperazinas heterociclicas sustituidas para el tratamiento de la esquizofrenia. |
| WO2004035577A2 (en) * | 2002-10-16 | 2004-04-29 | Gilead Sciences, Inc. | Pre-organized tricyclic integrase inhibitor compounds |
| GB0501999D0 (en) * | 2005-02-01 | 2005-03-09 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| JP5399905B2 (ja) | 2006-09-01 | 2014-01-29 | センワ バイオサイエンシズ インコーポレイテッド | セリン−トレオニンタンパク質キナーゼおよびparp調節因子 |
| AU2008277377B2 (en) * | 2007-07-19 | 2013-08-01 | Msd Italia S.R.L. | Macrocyclic compounds as antiviral agents |
| AU2009219154A1 (en) * | 2008-02-29 | 2009-09-03 | Cylene Pharmaceuticals, Inc. | Protein kinase modulators |
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2011
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- 2011-03-29 JP JP2013502740A patent/JP5849302B2/ja active Active
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- 2011-03-29 ES ES11763307.3T patent/ES2547571T3/es active Active
- 2011-03-29 US US13/202,544 patent/US8962648B2/en active Active
- 2011-03-29 CA CA2792941A patent/CA2792941C/en active Active
- 2011-03-29 KR KR1020127027125A patent/KR101757502B1/ko not_active Expired - Fee Related
- 2011-03-29 EP EP11763307.3A patent/EP2552206B1/en active Active
- 2011-03-29 BR BR112012023836-1A patent/BR112012023836B1/pt not_active IP Right Cessation
- 2011-03-29 AU AU2011235319A patent/AU2011235319B2/en not_active Ceased
- 2011-03-29 SG SG2012072807A patent/SG184376A1/en unknown
- 2011-03-29 DK DK11763307.3T patent/DK2552206T3/en active
- 2011-03-29 WO PCT/US2011/030278 patent/WO2011123419A1/en not_active Ceased
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2012
- 2012-09-23 IL IL222080A patent/IL222080B/en active IP Right Grant
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2014
- 2014-12-09 US US14/565,047 patent/US9453025B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| TW201136939A (en) | 2011-11-01 |
| CA2792941C (en) | 2017-09-12 |
| KR20130020666A (ko) | 2013-02-27 |
| US20150183799A1 (en) | 2015-07-02 |
| KR101757502B1 (ko) | 2017-07-12 |
| ES2547571T3 (es) | 2015-10-07 |
| HK1179114A1 (en) | 2013-09-27 |
| BR112012023836B1 (pt) | 2022-02-01 |
| SG184376A1 (en) | 2012-11-29 |
| CN102917590A (zh) | 2013-02-06 |
| JP5849302B2 (ja) | 2016-01-27 |
| WO2011123419A1 (en) | 2011-10-06 |
| US9453025B2 (en) | 2016-09-27 |
| CN102917590B (zh) | 2016-02-17 |
| AU2011235319B2 (en) | 2016-07-14 |
| BR112012023836A2 (pt) | 2015-09-22 |
| CA2792941A1 (en) | 2011-10-06 |
| JP2013523749A (ja) | 2013-06-17 |
| IL222080B (en) | 2018-05-31 |
| US8962648B2 (en) | 2015-02-24 |
| AU2011235319A1 (en) | 2012-10-11 |
| RU2012145855A (ru) | 2014-05-10 |
| US20130178459A1 (en) | 2013-07-11 |
| MX2012011412A (es) | 2013-02-07 |
| TWI503323B (zh) | 2015-10-11 |
| EP2552206A1 (en) | 2013-02-06 |
| EP2552206A4 (en) | 2013-08-14 |
| EP2552206B1 (en) | 2015-07-22 |
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