JP2013525438A5 - - Google Patents
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- Publication number
- JP2013525438A5 JP2013525438A5 JP2013508139A JP2013508139A JP2013525438A5 JP 2013525438 A5 JP2013525438 A5 JP 2013525438A5 JP 2013508139 A JP2013508139 A JP 2013508139A JP 2013508139 A JP2013508139 A JP 2013508139A JP 2013525438 A5 JP2013525438 A5 JP 2013525438A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- sulfonamide
- tetrahydroquinoline
- alkyl
- dimethylphenyl
- Prior art date
- 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.)
- Pending
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- -1 3,4-dihydroquinolin-2 (1H) -onyl Chemical group 0.000 claims 36
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 23
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- 125000004122 cyclic group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000005157 alkyl carboxy group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- XESJSVKSJFRHPE-UHFFFAOYSA-N 1-acetyl-n-(3,4-dimethylphenyl)-2,3-dihydroindole-5-sulfonamide Chemical compound C=1C=C2N(C(=O)C)CCC2=CC=1S(=O)(=O)NC1=CC=C(C)C(C)=C1 XESJSVKSJFRHPE-UHFFFAOYSA-N 0.000 claims 1
- KUMQIRFCKBSETE-UHFFFAOYSA-N 1-acetyl-n-(3,4-dimethylphenyl)-2-methyl-2,3-dihydroindole-5-sulfonamide Chemical compound C=1C=C2N(C(C)=O)C(C)CC2=CC=1S(=O)(=O)NC1=CC=C(C)C(C)=C1 KUMQIRFCKBSETE-UHFFFAOYSA-N 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- WVMOGAPSTDCYRO-UHFFFAOYSA-N 2-oxo-n-(3-phenylphenyl)-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1S(=O)(=O)NC(C=1)=CC=CC=1C1=CC=CC=C1 WVMOGAPSTDCYRO-UHFFFAOYSA-N 0.000 claims 1
- WQRPZEZBGHLTAC-UHFFFAOYSA-N 2-oxo-n-[3-(trifluoromethyl)phenyl]-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound FC(F)(F)C1=CC=CC(NS(=O)(=O)C=2C=C3CCC(=O)NC3=CC=2)=C1 WQRPZEZBGHLTAC-UHFFFAOYSA-N 0.000 claims 1
- DWLBYLGNERHAIR-UHFFFAOYSA-N 2-oxo-n-pyridin-3-yl-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1S(=O)(=O)NC1=CC=CN=C1 DWLBYLGNERHAIR-UHFFFAOYSA-N 0.000 claims 1
- ICWKDRRYYPUARX-UHFFFAOYSA-N 3,3-dichloro-n-(3,4-dimethylphenyl)-2-oxo-1h-indole-5-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)C2(Cl)Cl)C2=C1 ICWKDRRYYPUARX-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- PNUCPERAJKCNDW-UHFFFAOYSA-N 6-(dimethylamino)-n-(3,4-dimethylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-7-sulfonamide Chemical compound CN(C)C1=CC=2CCC(=O)NC=2C=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 PNUCPERAJKCNDW-UHFFFAOYSA-N 0.000 claims 1
- UKDWCJDLGFLUDX-UHFFFAOYSA-N 6-bromo-N-(3,4-dimethylphenyl)-3-oxo-4H-1,4-benzoxazine-7-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)Br)=CC2=C1NC(=O)CO2 UKDWCJDLGFLUDX-UHFFFAOYSA-N 0.000 claims 1
- NLCUMMKSKTZTBQ-UHFFFAOYSA-N 6-chloro-N-(3,4-dimethylphenyl)-3-oxo-4H-1,4-benzoxazine-7-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)Cl)=CC2=C1NC(=O)CO2 NLCUMMKSKTZTBQ-UHFFFAOYSA-N 0.000 claims 1
- XRRWVAJHXHPVMF-UHFFFAOYSA-N 6-chloro-n-(3,4-dimethylphenyl)-2-oxo-1,3-dihydroindole-5-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)Cl)=CC2=C1NC(=O)C2 XRRWVAJHXHPVMF-UHFFFAOYSA-N 0.000 claims 1
- YGLBSBMBNJMIQH-UHFFFAOYSA-N 6-chloro-n-(3,4-dimethylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-7-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)Cl)=CC2=C1CCC(=O)N2 YGLBSBMBNJMIQH-UHFFFAOYSA-N 0.000 claims 1
- XRNQVMXHJDERIT-UHFFFAOYSA-N 6-chloro-n-(3-chloro-2-methylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-7-sulfonamide Chemical compound CC1=C(Cl)C=CC=C1NS(=O)(=O)C(C(=C1)Cl)=CC2=C1CCC(=O)N2 XRNQVMXHJDERIT-UHFFFAOYSA-N 0.000 claims 1
- RFVFXQILUXVPQU-UHFFFAOYSA-N 6-chloro-n-(3-chloro-4-methylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-7-sulfonamide Chemical compound C1=C(Cl)C(C)=CC=C1NS(=O)(=O)C(C(=C1)Cl)=CC2=C1CCC(=O)N2 RFVFXQILUXVPQU-UHFFFAOYSA-N 0.000 claims 1
- KEEWNCGXRMKJTQ-UHFFFAOYSA-N 6-chloro-n-(5-chloro-2-methylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-7-sulfonamide Chemical compound CC1=CC=C(Cl)C=C1NS(=O)(=O)C(C(=C1)Cl)=CC2=C1CCC(=O)N2 KEEWNCGXRMKJTQ-UHFFFAOYSA-N 0.000 claims 1
- CPCRMUCDKAAXGT-UHFFFAOYSA-N 7-(diethylamino)-n-(3,4-dimethylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound CCN(CC)C1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 CPCRMUCDKAAXGT-UHFFFAOYSA-N 0.000 claims 1
- JTMUYMFTDPYETO-UHFFFAOYSA-N 7-(dimethylamino)-n-(3,4-dimethylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound CN(C)C1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 JTMUYMFTDPYETO-UHFFFAOYSA-N 0.000 claims 1
- AOEUWFASGTXXAQ-UHFFFAOYSA-N 7-[2-(dimethylamino)ethyl-methylamino]-n-(3,4-dimethylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound CN(C)CCN(C)C1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 AOEUWFASGTXXAQ-UHFFFAOYSA-N 0.000 claims 1
- NFXGFWJXAFTFGK-UHFFFAOYSA-N 7-[3-(dimethylamino)pyrrolidin-1-yl]-n-(3,4-dimethylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1C(N(C)C)CCN1C(C(=C1)S(=O)(=O)NC=2C=C(C)C(C)=CC=2)=CC2=C1CCC(=O)N2 NFXGFWJXAFTFGK-UHFFFAOYSA-N 0.000 claims 1
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical group OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 claims 1
- JPRSMOUDRVVIHR-UHFFFAOYSA-N N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxo-3,4-dihydro-1H-quinoline-6-sulfonamide Chemical compound O1CCOC2=CC(NS(=O)(=O)C=3C=C4CCC(NC4=CC=3)=O)=CC=C21 JPRSMOUDRVVIHR-UHFFFAOYSA-N 0.000 claims 1
- KQHKZXBKJWOHHU-UHFFFAOYSA-N N-(3-chlorophenyl)-2-oxo-3,4-dihydro-1H-quinoline-6-sulfonamide Chemical compound ClC1=CC=CC(NS(=O)(=O)C=2C=C3CCC(=O)NC3=CC=2)=C1 KQHKZXBKJWOHHU-UHFFFAOYSA-N 0.000 claims 1
- GTFOCOKDGPLBEK-UHFFFAOYSA-N N-(4-chloro-3-methylphenyl)-2-oxo-3,4-dihydro-1H-quinoline-6-sulfonamide Chemical compound C1=C(Cl)C(C)=CC(NS(=O)(=O)C=2C=C3CCC(=O)NC3=CC=2)=C1 GTFOCOKDGPLBEK-UHFFFAOYSA-N 0.000 claims 1
- BANOCBYMYBHZCK-UHFFFAOYSA-N N-(4-fluorophenyl)-2-oxo-3,4-dihydro-1H-quinoline-6-sulfonamide Chemical compound C1=CC(F)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CC2)C2=C1 BANOCBYMYBHZCK-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- AIEOBFOLWRLWFY-UHFFFAOYSA-N [3-[(2-oxo-3,4-dihydro-1h-quinolin-6-yl)sulfonylamino]phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(NS(=O)(=O)C=2C=C3CCC(=O)NC3=CC=2)=C1 AIEOBFOLWRLWFY-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- FXULHVBWXADQIT-UHFFFAOYSA-N n-(2-fluorophenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound FC1=CC=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CC2)C2=C1 FXULHVBWXADQIT-UHFFFAOYSA-N 0.000 claims 1
- HPTNHSMTBSTARS-UHFFFAOYSA-N n-(2-methoxyphenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound COC1=CC=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CC2)C2=C1 HPTNHSMTBSTARS-UHFFFAOYSA-N 0.000 claims 1
- WDMSYXZEYIVUAV-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CC2)C2=C1 WDMSYXZEYIVUAV-UHFFFAOYSA-N 0.000 claims 1
- TVEWYQNBFLBJON-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-7-fluoro-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound FC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(Cl)C(Cl)=C1 TVEWYQNBFLBJON-UHFFFAOYSA-N 0.000 claims 1
- OZCHLLBJIJDZSV-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-1,3-dimethyl-2-oxobenzimidazole-5-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(N(C)C(=O)N2C)C2=C1 OZCHLLBJIJDZSV-UHFFFAOYSA-N 0.000 claims 1
- PQRJAXXCZAABJD-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-1-methylindole-5-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(N(C)C=C2)C2=C1 PQRJAXXCZAABJD-UHFFFAOYSA-N 0.000 claims 1
- CKACPEDULOKSHJ-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-oxo-1,3,4,5-tetrahydro-1-benzazepine-7-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CCC2)C2=C1 CKACPEDULOKSHJ-UHFFFAOYSA-N 0.000 claims 1
- BSEGVWNGGVEPQX-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-oxo-1,3-dihydrobenzimidazole-5-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)N2)C2=C1 BSEGVWNGGVEPQX-UHFFFAOYSA-N 0.000 claims 1
- XMTTXQUJUKTALG-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-oxo-1,3-dihydroindole-5-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)C2)C2=C1 XMTTXQUJUKTALG-UHFFFAOYSA-N 0.000 claims 1
- ABPIVUMUUZSCTQ-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC=C(NC(=O)CC2)C2=C1 ABPIVUMUUZSCTQ-UHFFFAOYSA-N 0.000 claims 1
- CAPFLYHFMYQPBI-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-oxo-7-(propan-2-ylamino)-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound CC(C)NC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 CAPFLYHFMYQPBI-UHFFFAOYSA-N 0.000 claims 1
- PFQAFZFSUCEPGW-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-oxo-7-piperidin-1-yl-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)N2CCCCC2)=CC2=C1NC(=O)CC2 PFQAFZFSUCEPGW-UHFFFAOYSA-N 0.000 claims 1
- ZMERFADMZRTONY-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-oxo-7-pyrrolidin-1-yl-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)N2CCCC2)=CC2=C1NC(=O)CC2 ZMERFADMZRTONY-UHFFFAOYSA-N 0.000 claims 1
- FLRPVXLMOJGRDV-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-3-oxo-4h-1,4-benzoxazine-6-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(OCC(=O)N2)C2=C1 FLRPVXLMOJGRDV-UHFFFAOYSA-N 0.000 claims 1
- LFKHSAHGVHJEPF-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-3-oxo-6-phenyl-4h-1,4-benzoxazine-7-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)C=2C=CC=CC=2)=CC2=C1NC(=O)CO2 LFKHSAHGVHJEPF-UHFFFAOYSA-N 0.000 claims 1
- CRZDZXNDKULTHH-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-4-methyl-3-oxo-1,4-benzoxazine-6-sulfonamide Chemical compound C1=C2N(C)C(=O)COC2=CC=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 CRZDZXNDKULTHH-UHFFFAOYSA-N 0.000 claims 1
- OHQSSKLYMQFLQN-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-6-methyl-3-oxo-4h-1,4-benzoxazine-7-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)C)=CC2=C1NC(=O)CO2 OHQSSKLYMQFLQN-UHFFFAOYSA-N 0.000 claims 1
- FTLNYBCPHCLODH-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-7-(1-hydroxypropan-2-ylamino)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound OCC(C)NC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 FTLNYBCPHCLODH-UHFFFAOYSA-N 0.000 claims 1
- WQEYRSZNQWSCKO-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-7-(2-hydroxyethylamino)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)NCCO)=CC2=C1NC(=O)CC2 WQEYRSZNQWSCKO-UHFFFAOYSA-N 0.000 claims 1
- RDJVVXIZIXTZEL-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-7-(methylamino)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound CNC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 RDJVVXIZIXTZEL-UHFFFAOYSA-N 0.000 claims 1
- IAJXECZPLGLEKB-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-7-[(2-hydroxy-2-methylpropyl)amino]-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)NCC(C)(C)O)=CC2=C1NC(=O)CC2 IAJXECZPLGLEKB-UHFFFAOYSA-N 0.000 claims 1
- FTLNYBCPHCLODH-CQSZACIVSA-N n-(3,4-dimethylphenyl)-7-[[(2r)-1-hydroxypropan-2-yl]amino]-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound OC[C@@H](C)NC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 FTLNYBCPHCLODH-CQSZACIVSA-N 0.000 claims 1
- FTLNYBCPHCLODH-AWEZNQCLSA-N n-(3,4-dimethylphenyl)-7-[[(2s)-1-hydroxypropan-2-yl]amino]-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound OC[C@H](C)NC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 FTLNYBCPHCLODH-AWEZNQCLSA-N 0.000 claims 1
- MSHCFYZEHSRAPG-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-7-fluoro-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)F)=CC2=C1NC(=O)CC2 MSHCFYZEHSRAPG-UHFFFAOYSA-N 0.000 claims 1
- QITDSYIYIPIMLL-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-n-methyl-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1S(=O)(=O)N(C)C1=CC=C(C)C(C)=C1 QITDSYIYIPIMLL-UHFFFAOYSA-N 0.000 claims 1
- HOPSYFZHYRZZBT-UHFFFAOYSA-N n-(3-chloro-2-methylphenyl)-7-fluoro-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound CC1=C(Cl)C=CC=C1NS(=O)(=O)C(C(=C1)F)=CC2=C1NC(=O)CC2 HOPSYFZHYRZZBT-UHFFFAOYSA-N 0.000 claims 1
- CUZDABRLLGGXKI-JTQLQIEISA-N n-(3-chloro-4-fluorophenyl)-7-[[(2s)-1-hydroxypropan-2-yl]amino]-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound OC[C@H](C)NC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(F)C(Cl)=C1 CUZDABRLLGGXKI-JTQLQIEISA-N 0.000 claims 1
- NRHQXXODPRXAER-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(Cl)C(C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CC2)C2=C1 NRHQXXODPRXAER-UHFFFAOYSA-N 0.000 claims 1
- VLRYVDZPCCVRIS-LBPRGKRZSA-N n-(3-chloro-4-methylphenyl)-7-[[(2s)-1-hydroxypropan-2-yl]amino]-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound OC[C@H](C)NC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(Cl)=C1 VLRYVDZPCCVRIS-LBPRGKRZSA-N 0.000 claims 1
- HYOLJEHGMOJMNR-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-7-fluoro-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(Cl)C(C)=CC=C1NS(=O)(=O)C(C(=C1)F)=CC2=C1NC(=O)CC2 HYOLJEHGMOJMNR-UHFFFAOYSA-N 0.000 claims 1
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-
2011
- 2011-04-26 US US13/643,594 patent/US20130109672A1/en not_active Abandoned
- 2011-04-26 JP JP2013508139A patent/JP2013525438A/ja active Pending
- 2011-04-26 WO PCT/US2011/033852 patent/WO2011137089A1/en not_active Ceased
- 2011-04-26 CA CA2797694A patent/CA2797694A1/en not_active Abandoned
- 2011-04-26 AU AU2011245441A patent/AU2011245441B2/en not_active Expired - Fee Related
- 2011-04-26 EP EP11730473A patent/EP2563761A1/en not_active Withdrawn
-
2015
- 2015-03-10 US US14/643,107 patent/US9708267B2/en active Active
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