JP2018511587A5 - - Google Patents
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- JP2018511587A5 JP2018511587A5 JP2017548261A JP2017548261A JP2018511587A5 JP 2018511587 A5 JP2018511587 A5 JP 2018511587A5 JP 2017548261 A JP2017548261 A JP 2017548261A JP 2017548261 A JP2017548261 A JP 2017548261A JP 2018511587 A5 JP2018511587 A5 JP 2018511587A5
- Authority
- JP
- Japan
- Prior art keywords
- indol
- fluoro
- methyl
- dioxide
- dihydrobenzo
- 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.)
- Granted
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- -1 (-)-Methyl Chemical group 0.000 claims 130
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000004043 oxo group Chemical group O=* 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- CJMWCVHRDNPWIE-UHFFFAOYSA-N 3-[5-(6-fluoro-1H-indol-3-yl)-3-(hydroxymethyl)-1,1-dioxo-3H-1,2-benzothiazol-2-yl]propane-1,2-diol Chemical compound OC(CN1S(C2=C(C1CO)C=C(C=C2)C1=CNC2=CC(=CC=C12)F)(=O)=O)CO CJMWCVHRDNPWIE-UHFFFAOYSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- YTBRDCJCTHUZLT-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-3-methyl-2-(2-methylsulfinylethyl)-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(N(S2(=O)=O)CCS(=O)C)C)C=1 YTBRDCJCTHUZLT-UHFFFAOYSA-N 0.000 claims 3
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- VEVPOVSPCMGGON-SBXXRYSUSA-N (2R)-3-[5-(6-fluoro-1H-indol-3-yl)-3-methyl-1,1-dioxo-3H-1,2-benzothiazol-2-yl]propane-1,2-diol Chemical compound O[C@H](CN1S(C2=C(C1C)C=C(C=C2)C1=CNC2=CC(=CC=C12)F)(=O)=O)CO VEVPOVSPCMGGON-SBXXRYSUSA-N 0.000 claims 2
- VEVPOVSPCMGGON-IAXJKZSUSA-N (2S)-3-[5-(6-fluoro-1H-indol-3-yl)-3-methyl-1,1-dioxo-3H-1,2-benzothiazol-2-yl]propane-1,2-diol Chemical compound O[C@@H](CN1S(C2=C(C1C)C=C(C=C2)C1=CNC2=CC(=CC=C12)F)(=O)=O)CO VEVPOVSPCMGGON-IAXJKZSUSA-N 0.000 claims 2
- IXSJHACANDXCDX-UHFFFAOYSA-N 1-[5-(6-fluoro-1H-indol-3-yl)-1,1-dioxo-2,3-dihydro-1,2-benzothiazol-3-yl]-N,N-dimethylmethanamine Chemical compound CN(C)CC1NS(=O)(=O)C2=C1C=C(C=C2)C1=CNC2=CC(F)=CC=C12 IXSJHACANDXCDX-UHFFFAOYSA-N 0.000 claims 2
- KFMKCVDVXIMKLQ-UHFFFAOYSA-N 1-[5-(6-fluoro-1H-indol-3-yl)-1,1-dioxo-2,3-dihydro-1,2-benzothiazol-3-yl]-N-methylmethanamine Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(NS2(=O)=O)CNC)C=1 KFMKCVDVXIMKLQ-UHFFFAOYSA-N 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- OVOIQZIQNPJJQN-UHFFFAOYSA-N 2-(azetidin-3-yl)-5-(6-fluoro-1H-indol-3-yl)-3-methyl-3H-1,2-benzothiazole 1,1-dioxide Chemical compound N1CC(C1)N1S(C2=C(C1C)C=C(C=C2)C1=CNC2=CC(=CC=C12)F)(=O)=O OVOIQZIQNPJJQN-UHFFFAOYSA-N 0.000 claims 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 2
- KKBGUNRNQNHDIB-UHFFFAOYSA-N 2-[5-(6-fluoro-1H-indol-3-yl)-1,1-dioxo-2,3-dihydro-1,2-benzothiazol-3-yl]ethanol Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(NS2(=O)=O)CCO)C=1 KKBGUNRNQNHDIB-UHFFFAOYSA-N 0.000 claims 2
- PPXQYVWTQJWWQN-UHFFFAOYSA-N 2-[5-(6-fluoro-1H-indol-3-yl)-3-(hydroxymethyl)-1,1-dioxo-3H-1,2-benzothiazol-2-yl]ethanol Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(N(S2(=O)=O)CCO)CO)C=1 PPXQYVWTQJWWQN-UHFFFAOYSA-N 0.000 claims 2
- INNZJFMCCWHXDL-UHFFFAOYSA-N 2-[5-(6-fluoro-1H-indol-3-yl)-3-methyl-1,1-dioxo-3H-1,2-benzothiazol-2-yl]ethanol Chemical compound CC1N(CCO)S(=O)(=O)C2=C1C=C(C=C2)C1=CNC2=CC(F)=CC=C12 INNZJFMCCWHXDL-UHFFFAOYSA-N 0.000 claims 2
- AVRSXTDANSQCNG-UHFFFAOYSA-N 3-cyclopropyl-5-(6-fluoro-1H-indol-3-yl)-2,3-dihydro-1,2-benzothiazole 1,1-dioxide Chemical compound C1(CC1)C1NS(C2=C1C=C(C=C2)C1=CNC2=CC(=CC=C12)F)(=O)=O AVRSXTDANSQCNG-UHFFFAOYSA-N 0.000 claims 2
- UDMPUXUCELVCTO-UHFFFAOYSA-N 3-ethyl-5-(6-fluoro-1H-indol-3-yl)-2,3-dihydro-1,2-benzothiazole 1,1-dioxide Chemical compound C(C)C1NS(C2=C1C=C(C=C2)C1=CNC2=CC(=CC=C12)F)(=O)=O UDMPUXUCELVCTO-UHFFFAOYSA-N 0.000 claims 2
- BHSNBOZVMIRRMP-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-1,1-dioxo-2,3-dihydro-1,2-benzothiazole-3-carboxamide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(NS2(=O)=O)C(=O)N)C=1 BHSNBOZVMIRRMP-UHFFFAOYSA-N 0.000 claims 2
- ZMCRNPLKPSLLOS-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-3-methyl-2,3-dihydro-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(NS2(=O)=O)C)C=1 ZMCRNPLKPSLLOS-UHFFFAOYSA-N 0.000 claims 2
- WGMSRXJXUFKLJT-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-3-methyl-2-(2-methylsulfonylethyl)-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(N(S2(=O)=O)CCS(=O)(=O)C)C)C=1 WGMSRXJXUFKLJT-UHFFFAOYSA-N 0.000 claims 2
- AKNKCTPWZVPPOD-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-3-methyl-2-(2-morpholin-4-ylethyl)-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(N(S2(=O)=O)CCN2CCOCC2)C)C=1 AKNKCTPWZVPPOD-UHFFFAOYSA-N 0.000 claims 2
- IANSEGCGGREKGE-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-3-methyl-2-(piperidin-4-ylmethyl)-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(N(S2(=O)=O)CC2CCNCC2)C)C=1 IANSEGCGGREKGE-UHFFFAOYSA-N 0.000 claims 2
- YZDVOQUALAJWPU-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-3-methyl-2-[(1-methyl-1,2,4-triazol-3-yl)methyl]-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(N(S2(=O)=O)CC2=NN(C=N2)C)C)C=1 YZDVOQUALAJWPU-UHFFFAOYSA-N 0.000 claims 2
- DUVOUPARCSJAMO-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-3-methyl-2-piperidin-4-yl-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(N(S2(=O)=O)C2CCNCC2)C)C=1 DUVOUPARCSJAMO-UHFFFAOYSA-N 0.000 claims 2
- RMVZJAAFRKPMCT-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-3-propan-2-yl-2,3-dihydro-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(NS2(=O)=O)C(C)C)C=1 RMVZJAAFRKPMCT-UHFFFAOYSA-N 0.000 claims 2
- VVVMDJMOERMJPW-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-3-propyl-2,3-dihydro-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(NS2(=O)=O)CCC)C=1 VVVMDJMOERMJPW-UHFFFAOYSA-N 0.000 claims 2
- SCRMJNXZQNDGNI-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-N-methyl-1,1-dioxo-2,3-dihydro-1,2-benzothiazole-3-carboxamide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(NS2(=O)=O)C(=O)NC)C=1 SCRMJNXZQNDGNI-UHFFFAOYSA-N 0.000 claims 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- ZWVBNIKEVVRPBQ-UHFFFAOYSA-N [5-(6-fluoro-1H-indol-3-yl)-1,1-dioxo-2,3-dihydro-1,2-benzothiazol-3-yl]methanamine Chemical compound NCC1NS(C2=C1C=C(C=C2)C1=CNC2=CC(=CC=C12)F)(=O)=O ZWVBNIKEVVRPBQ-UHFFFAOYSA-N 0.000 claims 2
- MUYZCDJFMYXXLU-UHFFFAOYSA-N [5-(6-fluoro-1H-indol-3-yl)-1,1-dioxo-2,3-dihydro-1,2-benzothiazol-3-yl]methanol Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(NS2(=O)=O)CO)C=1 MUYZCDJFMYXXLU-UHFFFAOYSA-N 0.000 claims 2
- PSSSKDUJDVBKPP-UHFFFAOYSA-N [5-(6-fluoro-1H-indol-3-yl)-2-[(1-methyl-1,2,4-triazol-3-yl)methyl]-1,1-dioxo-3H-1,2-benzothiazol-3-yl]methanol Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(N(S2(=O)=O)CC2=NN(C=N2)C)CO)C=1 PSSSKDUJDVBKPP-UHFFFAOYSA-N 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
- BRYVWWIWOBEVKY-AWEZNQCLSA-N (2S)-3-[5-(6-fluoro-1H-indol-3-yl)-1,1-dioxo-3H-1,2-benzothiazol-2-yl]propane-1,2-diol Chemical compound O[C@@H](CN1S(C2=C(C1)C=C(C=C2)C1=CNC2=CC(=CC=C12)F)(=O)=O)CO BRYVWWIWOBEVKY-AWEZNQCLSA-N 0.000 claims 1
- YNVGNSUTDNJJNH-CQSZACIVSA-N (3R)-5-(6-fluoro-1H-indol-3-yl)-3-methyl-2-(pyridin-2-ylmethyl)-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C([C@H](N(S2(=O)=O)CC2=NC=CC=C2)C)C=1 YNVGNSUTDNJJNH-CQSZACIVSA-N 0.000 claims 1
- GZACIBROAWWMDJ-OAHLLOKOSA-N (3R)-5-(6-fluoro-1H-indol-3-yl)-3-methyl-2-[(6-methylpyridin-2-yl)methyl]-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C([C@H](N(S2(=O)=O)CC2=NC(=CC=C2)C)C)C=1 GZACIBROAWWMDJ-OAHLLOKOSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- GZNZXLRJPJOBAY-UHFFFAOYSA-N 2-(azetidin-3-yl)-5-(6-fluoro-1H-indol-3-yl)-3H-1,2-benzothiazole 1,1-dioxide Chemical compound N1CC(C1)N1S(C2=C(C1)C=C(C=C2)C1=CNC2=CC(=CC=C12)F)(=O)=O GZNZXLRJPJOBAY-UHFFFAOYSA-N 0.000 claims 1
- QCIJWHDJHWUKCI-UHFFFAOYSA-N 2-[5-(6-fluoro-1H-indol-3-yl)-1,1-dioxo-3H-1,2-benzothiazol-2-yl]-N,N-dimethylethanamine Chemical compound CN(CCN1S(C2=C(C1)C=C(C=C2)C1=CNC2=CC(=CC=C12)F)(=O)=O)C QCIJWHDJHWUKCI-UHFFFAOYSA-N 0.000 claims 1
- ZKBOYHOLKWEZTJ-UHFFFAOYSA-N 2-[5-(6-fluoro-1H-indol-3-yl)-1,1-dioxo-3H-1,2-benzothiazol-2-yl]ethanamine Chemical compound NCCN1S(C2=C(C1)C=C(C=C2)C1=CNC2=CC(=CC=C12)F)(=O)=O ZKBOYHOLKWEZTJ-UHFFFAOYSA-N 0.000 claims 1
- CRIMTKLPICUTMT-UHFFFAOYSA-N 2-[5-(6-fluoro-1H-indol-3-yl)-1,1-dioxo-3H-1,2-benzothiazol-2-yl]ethanol Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(CN(S2(=O)=O)CCO)C=1 CRIMTKLPICUTMT-UHFFFAOYSA-N 0.000 claims 1
- VFYDGJNCGAVMBU-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-2-(1-methylazetidin-3-yl)-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(CN(S2(=O)=O)C2CN(C2)C)C=1 VFYDGJNCGAVMBU-UHFFFAOYSA-N 0.000 claims 1
- ITQMDQPZQGQNHV-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-2-(1-methylpiperidin-4-yl)-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(CN(S2(=O)=O)C2CCN(CC2)C)C=1 ITQMDQPZQGQNHV-UHFFFAOYSA-N 0.000 claims 1
- PFODQNCZTNXHQC-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-2-(2-methylsulfinylethyl)-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(CN(S2(=O)=O)CCS(=O)C)C=1 PFODQNCZTNXHQC-UHFFFAOYSA-N 0.000 claims 1
- WUYBEIGQZMXBMJ-OAHLLOKOSA-N 5-(6-fluoro-1H-indol-3-yl)-2-[(3R)-oxolan-3-yl]-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(CN(S2(=O)=O)[C@H]2COCC2)C=1 WUYBEIGQZMXBMJ-OAHLLOKOSA-N 0.000 claims 1
- WUYBEIGQZMXBMJ-HNNXBMFYSA-N 5-(6-fluoro-1H-indol-3-yl)-2-[(3S)-oxolan-3-yl]-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(CN(S2(=O)=O)[C@@H]2COCC2)C=1 WUYBEIGQZMXBMJ-HNNXBMFYSA-N 0.000 claims 1
- YULQEZKKXGNCKE-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-2-piperidin-4-yl-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(CN(S2(=O)=O)C2CCNCC2)C=1 YULQEZKKXGNCKE-UHFFFAOYSA-N 0.000 claims 1
- OWTRVSZKMCEMPJ-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-3,3-dimethyl-2H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(NS2(=O)=O)(C)C)C=1 OWTRVSZKMCEMPJ-UHFFFAOYSA-N 0.000 claims 1
- GWMPFYQTAPDESW-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-3-methyl-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(=NS2(=O)=O)C)C=1 GWMPFYQTAPDESW-UHFFFAOYSA-N 0.000 claims 1
- YNVGNSUTDNJJNH-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-3-methyl-2-(pyridin-2-ylmethyl)-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(N(S2(=O)=O)CC2=NC=CC=C2)C)C=1 YNVGNSUTDNJJNH-UHFFFAOYSA-N 0.000 claims 1
- GZACIBROAWWMDJ-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)-3-methyl-2-[(6-methylpyridin-2-yl)methyl]-3H-1,2-benzothiazole 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(N(S2(=O)=O)CC2=NC(=CC=C2)C)C)C=1 GZACIBROAWWMDJ-UHFFFAOYSA-N 0.000 claims 1
- BMJVEMOJJOLGAB-UHFFFAOYSA-N 5-(6-fluoro-1H-indol-3-yl)spiro[2H-1,2-benzothiazole-3,1'-cyclopropane] 1,1-dioxide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C=1)C1(CC1)NS2(=O)=O BMJVEMOJJOLGAB-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- WYKSGEFWOINIQZ-UHFFFAOYSA-N FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(N(S2(=O)=O)CCN2N=C(C=C2O)C)C)C=1 Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC2=C(C(N(S2(=O)=O)CCN2N=C(C=C2O)C)C)C=1 WYKSGEFWOINIQZ-UHFFFAOYSA-N 0.000 claims 1
- 101000892398 Homo sapiens Tryptophan 2,3-dioxygenase Proteins 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010027406 Mesothelioma Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
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-
2016
- 2016-03-17 CN CN201680028408.7A patent/CN107635990A/zh active Pending
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- 2016-03-17 HK HK18103418.8A patent/HK1243999A1/zh unknown
- 2016-03-17 WO PCT/IB2016/051509 patent/WO2016147144A1/en not_active Ceased
- 2016-03-17 SG SG11201706992TA patent/SG11201706992TA/en unknown
- 2016-03-17 AU AU2016231832A patent/AU2016231832B2/en not_active Ceased
- 2016-03-17 MX MX2017011951A patent/MX2017011951A/es unknown
- 2016-03-17 RU RU2017130845A patent/RU2672252C1/ru not_active IP Right Cessation
- 2016-03-17 BR BR112017019699-9A patent/BR112017019699A2/pt not_active Application Discontinuation
- 2016-03-17 JP JP2017548261A patent/JP6775516B2/ja not_active Expired - Fee Related
- 2016-03-17 KR KR1020177029203A patent/KR102013512B1/ko not_active Expired - Fee Related
- 2016-03-17 EP EP16711022.0A patent/EP3271354A1/en not_active Withdrawn
- 2016-03-17 US US15/072,534 patent/US9873690B2/en not_active Expired - Fee Related
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2017
- 2017-08-23 IL IL254124A patent/IL254124A0/en unknown
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