JP2017535559A5 - - Google Patents
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- Publication number
- JP2017535559A5 JP2017535559A5 JP2017526844A JP2017526844A JP2017535559A5 JP 2017535559 A5 JP2017535559 A5 JP 2017535559A5 JP 2017526844 A JP2017526844 A JP 2017526844A JP 2017526844 A JP2017526844 A JP 2017526844A JP 2017535559 A5 JP2017535559 A5 JP 2017535559A5
- Authority
- JP
- Japan
- Prior art keywords
- oxobenzo
- triazin
- acetamide
- ethyl
- methoxy
- 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 hydroxy, amino Chemical group 0.000 claims 194
- 150000001875 compounds Chemical class 0.000 claims 50
- 150000003839 salts Chemical class 0.000 claims 40
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 16
- 239000003814 drug Substances 0.000 claims 16
- RRXSYZFVDIRTFB-UHFFFAOYSA-N C[CH]C1=CC=C(OC)C=C1 Chemical group C[CH]C1=CC=C(OC)C=C1 RRXSYZFVDIRTFB-UHFFFAOYSA-N 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- GZSKABYYCABBFU-UHFFFAOYSA-N n-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound C1=CC=C2C(=O)N(NC(=O)C)N=NC2=C1 GZSKABYYCABBFU-UHFFFAOYSA-N 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 3
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 208000011117 substance-related disease Diseases 0.000 claims 3
- AOPMTWFMINSQGV-UONOGXRCSA-N (2R)-N-[(1S)-1-(2-methoxy-4-methylphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)propanamide Chemical compound COC1=C(C=CC(=C1)C)[C@H](C)NC([C@@H](C)N1N=NC2=C(C1=O)C=CC=C2)=O AOPMTWFMINSQGV-UONOGXRCSA-N 0.000 claims 2
- NHHIFMSLOXYVBO-ZDUSSCGKSA-N 2-(4-oxo-1,2,3-benzotriazin-3-yl)-n-[(2r)-2-phenylpropyl]acetamide Chemical compound C1([C@H](CNC(=O)CN2C(C3=CC=CC=C3N=N2)=O)C)=CC=CC=C1 NHHIFMSLOXYVBO-ZDUSSCGKSA-N 0.000 claims 2
- NHHIFMSLOXYVBO-CYBMUJFWSA-N 2-(4-oxo-1,2,3-benzotriazin-3-yl)-n-[(2s)-2-phenylpropyl]acetamide Chemical compound C1([C@@H](CNC(=O)CN2C(C3=CC=CC=C3N=N2)=O)C)=CC=CC=C1 NHHIFMSLOXYVBO-CYBMUJFWSA-N 0.000 claims 2
- POOIUAVPFUNLNL-NSHDSACASA-N 2-(5-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methoxyphenyl)ethyl]acetamide Chemical compound FC1=CC=CC=2N=NN(C(C=21)=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)OC POOIUAVPFUNLNL-NSHDSACASA-N 0.000 claims 2
- KCBGXCAHBBWRNE-ZDUSSCGKSA-N 2-(5-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound COC1=CC=CC=2N=NN(C(C=21)=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)C KCBGXCAHBBWRNE-ZDUSSCGKSA-N 0.000 claims 2
- OIAZRITXWWPTNH-JTQLQIEISA-N 2-(6,8-dichloro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methoxyphenyl)ethyl]acetamide Chemical compound ClC1=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)OC)C(=C1)Cl OIAZRITXWWPTNH-JTQLQIEISA-N 0.000 claims 2
- QDKXIUDVKUIJBT-NSHDSACASA-N 2-(6,8-dichloro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound ClC1=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)C)C(=C1)Cl QDKXIUDVKUIJBT-NSHDSACASA-N 0.000 claims 2
- BHDLUINLODALAW-AWEZNQCLSA-N 2-(6,8-dimethyl-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methoxyphenyl)ethyl]acetamide Chemical compound CC1=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)OC)C(=C1)C BHDLUINLODALAW-AWEZNQCLSA-N 0.000 claims 2
- IMHMUHMELFJCBS-NSHDSACASA-N 2-(6-chloro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methoxyphenyl)ethyl]acetamide Chemical compound ClC1=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)OC)C=C1 IMHMUHMELFJCBS-NSHDSACASA-N 0.000 claims 2
- QTXLUZLLRISUJM-LBPRGKRZSA-N 2-(6-chloro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound ClC1=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)C)C=C1 QTXLUZLLRISUJM-LBPRGKRZSA-N 0.000 claims 2
- POUOYHMMTHSEKJ-NSHDSACASA-N 2-(6-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methoxyphenyl)ethyl]acetamide Chemical compound FC1=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)OC)C=C1 POUOYHMMTHSEKJ-NSHDSACASA-N 0.000 claims 2
- JQVQDOAWGVPICK-LBPRGKRZSA-N 2-(6-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound FC1=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)C)C=C1 JQVQDOAWGVPICK-LBPRGKRZSA-N 0.000 claims 2
- MPFIBOVPLHCEFO-ZDUSSCGKSA-N 2-(6-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound COC1=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)C)C=C1 MPFIBOVPLHCEFO-ZDUSSCGKSA-N 0.000 claims 2
- MLWZRROZCADIQQ-AWEZNQCLSA-N 2-(6-methyl-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound CC1=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)C)C=C1 MLWZRROZCADIQQ-AWEZNQCLSA-N 0.000 claims 2
- REOWSJCKCYOYLG-LBPRGKRZSA-N 2-(7-chloro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound ClC=1C=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)C)C=1 REOWSJCKCYOYLG-LBPRGKRZSA-N 0.000 claims 2
- KZGCQSLARYWBID-LBPRGKRZSA-N 2-(7-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methoxyphenyl)ethyl]acetamide Chemical compound COC=1C=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)OC)C=1 KZGCQSLARYWBID-LBPRGKRZSA-N 0.000 claims 2
- BFLNIJPZEKHHMD-ZDUSSCGKSA-N 2-(7-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound COC=1C=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)C)C=1 BFLNIJPZEKHHMD-ZDUSSCGKSA-N 0.000 claims 2
- UOFXNHJSTFHCTF-AWEZNQCLSA-N 2-(7-methyl-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound CC=1C=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)C)C=1 UOFXNHJSTFHCTF-AWEZNQCLSA-N 0.000 claims 2
- XSLDKBATWMJNOE-NSHDSACASA-N 2-(8-chloro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methoxyphenyl)ethyl]acetamide Chemical compound ClC1=CC=CC2=C1N=NN(C2=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)OC XSLDKBATWMJNOE-NSHDSACASA-N 0.000 claims 2
- ZXFHIAAKONRMNN-LBPRGKRZSA-N 2-(8-chloro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound ClC1=CC=CC2=C1N=NN(C2=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)C ZXFHIAAKONRMNN-LBPRGKRZSA-N 0.000 claims 2
- QIXCVVSWMRNBGV-NSHDSACASA-N 2-(8-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methoxyphenyl)ethyl]acetamide Chemical compound FC1=CC=CC2=C1N=NN(C2=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)OC QIXCVVSWMRNBGV-NSHDSACASA-N 0.000 claims 2
- NFHZMSKSZWDGLN-LBPRGKRZSA-N 2-(8-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound FC1=CC=CC2=C1N=NN(C2=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)C NFHZMSKSZWDGLN-LBPRGKRZSA-N 0.000 claims 2
- BFNPBDJFKSZLHJ-ZDUSSCGKSA-N 2-(8-fluoro-6-methyl-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound FC1=CC(=CC2=C1N=NN(C2=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)C)C BFNPBDJFKSZLHJ-ZDUSSCGKSA-N 0.000 claims 2
- QEFZPGDVQARJQX-LBPRGKRZSA-N 2-(8-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methoxyphenyl)ethyl]acetamide Chemical compound COC1=CC=CC2=C1N=NN(C2=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)OC QEFZPGDVQARJQX-LBPRGKRZSA-N 0.000 claims 2
- QZHOUHZKMLGYJN-ZDUSSCGKSA-N 2-(8-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound COC1=CC=CC2=C1N=NN(C2=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)C QZHOUHZKMLGYJN-ZDUSSCGKSA-N 0.000 claims 2
- UUUQJHYOVJWEKZ-AWEZNQCLSA-N 2-(8-methyl-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound CC1=CC=CC2=C1N=NN(C2=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)C UUUQJHYOVJWEKZ-AWEZNQCLSA-N 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- AMRDWWMUNNALHK-CYBMUJFWSA-N N-[(1R)-1-(4-methylphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound O=C1C2=C(N=NN1CC(=O)N[C@H](C)C1=CC=C(C=C1)C)C=CC=C2 AMRDWWMUNNALHK-CYBMUJFWSA-N 0.000 claims 2
- SJQFFAMTFHKEGM-LBPRGKRZSA-N N-[(1S)-1-(2,4-dimethoxyphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=C(C=CC(=C1)OC)[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O SJQFFAMTFHKEGM-LBPRGKRZSA-N 0.000 claims 2
- LXZGSJQRZHHQBT-AWEZNQCLSA-N N-[(1S)-1-(2,4-dimethylphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound CC1=C(C=CC(=C1)C)[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O LXZGSJQRZHHQBT-AWEZNQCLSA-N 0.000 claims 2
- FVQNXYAXDJPHPI-ZDUSSCGKSA-N N-[(1S)-1-(2,4-dimethylphenyl)ethyl]-2-(6-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound CC1=C(C=CC(=C1)C)[C@H](C)NC(CN1N=NC2=C(C1=O)C=C(C=C2)F)=O FVQNXYAXDJPHPI-ZDUSSCGKSA-N 0.000 claims 2
- DVGUHHIULIPPKB-LBPRGKRZSA-N N-[(1S)-1-(2-fluoro-4-methylphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound FC1=C(C=CC(=C1)C)[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O DVGUHHIULIPPKB-LBPRGKRZSA-N 0.000 claims 2
- FHQBSRAOVCISAR-ZDUSSCGKSA-N N-[(1S)-1-(2-methoxy-4-methylphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=C(C=CC(=C1)C)[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O FHQBSRAOVCISAR-ZDUSSCGKSA-N 0.000 claims 2
- YNTGGPUBNFJFLL-NSHDSACASA-N N-[(1S)-1-(4-bromophenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound BrC1=CC=C(C=C1)[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O YNTGGPUBNFJFLL-NSHDSACASA-N 0.000 claims 2
- CWATUEVSJUJDCD-ZDUSSCGKSA-N N-[(1S)-1-(4-ethoxyphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound C(C)OC1=CC=C(C=C1)[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O CWATUEVSJUJDCD-ZDUSSCGKSA-N 0.000 claims 2
- MROVHIZKKLRMMY-LBPRGKRZSA-N N-[(1S)-1-(4-methoxyphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O MROVHIZKKLRMMY-LBPRGKRZSA-N 0.000 claims 2
- RBQKTEXHVZWNOM-ZDUSSCGKSA-N N-[(1S)-1-(4-methoxyphenyl)ethyl]-2-(5-methyl-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)[C@H](C)NC(CN1N=NC2=C(C1=O)C(=CC=C2)C)=O RBQKTEXHVZWNOM-ZDUSSCGKSA-N 0.000 claims 2
- OOURTFAADXDITC-ZDUSSCGKSA-N N-[(1S)-1-(4-methoxyphenyl)ethyl]-2-(6-methyl-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)[C@H](C)NC(CN1N=NC2=C(C1=O)C=C(C=C2)C)=O OOURTFAADXDITC-ZDUSSCGKSA-N 0.000 claims 2
- FNEAIYYXBKHWMI-ZDUSSCGKSA-N N-[(1S)-1-(4-methoxyphenyl)ethyl]-2-(7-methyl-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC(=C2)C)=O FNEAIYYXBKHWMI-ZDUSSCGKSA-N 0.000 claims 2
- SPIRXYAZOIUKLW-ZDUSSCGKSA-N N-[(1S)-1-(4-methoxyphenyl)ethyl]-2-(8-methyl-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2C)=O SPIRXYAZOIUKLW-ZDUSSCGKSA-N 0.000 claims 2
- AMRDWWMUNNALHK-ZDUSSCGKSA-N N-[(1S)-1-(4-methylphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound O=C1C2=C(N=NN1CC(=O)N[C@@H](C)C1=CC=C(C=C1)C)C=CC=C2 AMRDWWMUNNALHK-ZDUSSCGKSA-N 0.000 claims 2
- WCYBVBQGXJOEJY-NSHDSACASA-N N-[(1S)-1-[4-(difluoromethoxy)phenyl]ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound FC(OC1=CC=C(C=C1)[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O)F WCYBVBQGXJOEJY-NSHDSACASA-N 0.000 claims 2
- CBWQJOMWISNROA-NSHDSACASA-N N-[(1S)-1-[4-(difluoromethoxy)phenyl]ethyl]-2-(5-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound FC(OC1=CC=C(C=C1)[C@H](C)NC(CN1N=NC2=C(C1=O)C(=CC=C2)OC)=O)F CBWQJOMWISNROA-NSHDSACASA-N 0.000 claims 2
- NVBVBYBGSGRJPA-JTQLQIEISA-N N-[(1S)-1-[4-(difluoromethoxy)phenyl]ethyl]-2-(6-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound FC(OC1=CC=C(C=C1)[C@H](C)NC(CN1N=NC2=C(C1=O)C=C(C=C2)F)=O)F NVBVBYBGSGRJPA-JTQLQIEISA-N 0.000 claims 2
- VDXSDOHBTDMGFG-CYBMUJFWSA-N N-[(2R)-1-(4-methoxyphenyl)propan-2-yl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)C[C@@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O VDXSDOHBTDMGFG-CYBMUJFWSA-N 0.000 claims 2
- VDXSDOHBTDMGFG-ZDUSSCGKSA-N N-[(2S)-1-(4-methoxyphenyl)propan-2-yl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)C[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O VDXSDOHBTDMGFG-ZDUSSCGKSA-N 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 208000029560 autism spectrum disease Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 206010013663 drug dependence Diseases 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- LQEAGUMJDIWZGQ-HNNXBMFYSA-N 2-(4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[4-(trifluoromethoxy)phenyl]propyl]acetamide Chemical compound O=C1C2=C(N=NN1CC(=O)N[C@@H](CC)C1=CC=C(C=C1)OC(F)(F)F)C=CC=C2 LQEAGUMJDIWZGQ-HNNXBMFYSA-N 0.000 claims 1
- IXZCMRONQCIGHM-HNNXBMFYSA-N 2-(4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[4-(trifluoromethyl)phenyl]propyl]acetamide Chemical compound O=C1C2=C(N=NN1CC(=O)N[C@@H](CC)C1=CC=C(C=C1)C(F)(F)F)C=CC=C2 IXZCMRONQCIGHM-HNNXBMFYSA-N 0.000 claims 1
- FTLWUWIALIQVHE-UHFFFAOYSA-N 2-(4-oxo-1,2,3-benzotriazin-3-yl)-n-(2-phenylethyl)acetamide Chemical compound N1=NC2=CC=CC=C2C(=O)N1CC(=O)NCCC1=CC=CC=C1 FTLWUWIALIQVHE-UHFFFAOYSA-N 0.000 claims 1
- PGSIBSVOWOZOCM-LBPRGKRZSA-N 2-(4-oxo-1,2,3-benzotriazin-3-yl)-n-[(1s)-1-phenylethyl]acetamide Chemical compound C1([C@@H](NC(=O)CN2C(C3=CC=CC=C3N=N2)=O)C)=CC=CC=C1 PGSIBSVOWOZOCM-LBPRGKRZSA-N 0.000 claims 1
- GOUPEUKVQKMWGR-LBPRGKRZSA-N 2-(5-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methylphenyl)ethyl]acetamide Chemical compound FC1=CC=CC=2N=NN(C(C=21)=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)C GOUPEUKVQKMWGR-LBPRGKRZSA-N 0.000 claims 1
- KNJBLSXPWYUHOB-LBPRGKRZSA-N 2-(5-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-(4-methoxyphenyl)ethyl]acetamide Chemical compound COC1=CC=CC=2N=NN(C(C=21)=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)OC KNJBLSXPWYUHOB-LBPRGKRZSA-N 0.000 claims 1
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- RHLQOJVKJGYHQZ-UHFFFAOYSA-N N-[2-(4-methylphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound CC1=CC=C(C=C1)CCNC(CN1N=NC2=C(C1=O)C=CC=C2)=O RHLQOJVKJGYHQZ-UHFFFAOYSA-N 0.000 claims 1
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- IKWQWSKSKJKRIZ-NSHDSACASA-N n-[(1s)-1-(4-fluorophenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound C1([C@@H](NC(=O)CN2C(C3=CC=CC=C3N=N2)=O)C)=CC=C(F)C=C1 IKWQWSKSKJKRIZ-NSHDSACASA-N 0.000 claims 1
- CPFFDGFFVKSWCC-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound ClC1=CC=CC(CCNC(=O)CN2C(C3=CC=CC=C3N=N2)=O)=C1 CPFFDGFFVKSWCC-UHFFFAOYSA-N 0.000 claims 1
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| JO3719B1 (ar) * | 2014-11-20 | 2021-01-31 | Takeda Pharmaceuticals Co | 4- أوكسو-4،3- داي هيدرو-3،2،1- بنزوترايازينات كمواد ضابطة لأجل gpr139 |
| US12042496B2 (en) | 2018-10-16 | 2024-07-23 | The University Of Florida Research Foundation, Incorporated | Methods related to opioid therapeutics |
| WO2020097609A1 (en) | 2018-11-09 | 2020-05-14 | Blackthorn Therapeutics, Inc. | Gpr139 receptor modulators |
| AU2020348675B2 (en) * | 2019-09-16 | 2025-11-20 | Takeda Pharmaceutical Company Limited | Azole-fused pyridazin-3(2H)-one derivatives |
| WO2021127459A1 (en) * | 2019-12-20 | 2021-06-24 | Blackthorn Therapeutics, Inc. | Gpr139 receptor modulators |
| WO2021224680A1 (en) * | 2020-05-08 | 2021-11-11 | Takeda Pharmaceutical Company Limited | Substituted benzotriazinone metabolites of a gpr139 agonist |
| TW202227087A (zh) | 2020-09-21 | 2022-07-16 | 日商武田藥品工業股份有限公司 | 精神分裂症之治療 |
| US11760788B2 (en) | 2021-03-02 | 2023-09-19 | Pathways Neuro Pharma, Inc. | Neuroreceptor compositions and methods of use |
| WO2023165262A1 (zh) * | 2022-03-01 | 2023-09-07 | 上海科技大学 | 噻吩并含氮杂环类化合物、含其的药物组合物、其制备方法及其应用 |
| US20250163065A1 (en) * | 2022-03-01 | 2025-05-22 | Shanghaitech University | Pyrrolotriazinone compound, pharmaceutical composition comprising same, preparation method therefor, and use thereof |
| CN117986183A (zh) * | 2022-10-28 | 2024-05-07 | 浙江友宁生物医药科技有限公司 | 一种gpr139受体激动剂、其制备方法及其应用 |
| WO2024102802A1 (en) * | 2022-11-11 | 2024-05-16 | Takeda Pharmaceutical Company Limited | Zelatriazin for the treatment of depression |
| WO2025119351A1 (zh) * | 2023-12-08 | 2025-06-12 | 深圳湾实验室 | Gpr139激动剂 |
| WO2025162441A1 (zh) * | 2024-02-02 | 2025-08-07 | 上海科技大学 | 稠杂环类化合物与其制备方法、药物组合物及应用 |
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| US3794726A (en) * | 1972-08-21 | 1974-02-26 | Uniroyal Inc | Inhibiting aggressive behavior with 1,2,3-benzotriazin-(3h)-one |
| EP0257102B1 (en) | 1986-02-24 | 1997-11-19 | Mitsui Petrochemical Industries, Ltd. | Agents for treating neurophathy |
| EP0315390B1 (en) * | 1987-11-04 | 1994-07-20 | Beecham Group Plc | Novel 4-oxobenzotriazines and 4-oxoquinazolines |
| PE20050630A1 (es) | 2003-06-09 | 2005-09-22 | Boehringer Ingelheim Int | Compuestos heterociclicos como inhibidores del papiloma virus |
| CN100471856C (zh) | 2003-07-31 | 2009-03-25 | Irm责任有限公司 | 作为pdf抑制剂的二环化合物和组合物 |
| FR2875805B1 (fr) | 2004-09-27 | 2006-12-29 | Genfit S A | Composes derives de n-(benzyl) phenylacetamide substitues, preparation et utilisations |
| AR058705A1 (es) | 2005-12-23 | 2008-02-20 | Astrazeneca Ab | Compuestos de bencimidazol como inhibidores del receptor vaniloide 1 (vr1) |
| TWI433839B (zh) | 2006-08-11 | 2014-04-11 | Neomed Inst | 新穎的苯并咪唑衍生物290 |
| AU2008231873B2 (en) * | 2007-03-23 | 2011-11-10 | F. Hoffmann-La Roche Ag | Aza-pyridopyrimidinone derivatives |
| EP2219646A4 (en) * | 2007-12-21 | 2010-12-22 | Univ Rochester | PROCESS FOR EXTENDING THE LIFE OF EUKARYOTIC ORGANISMS |
| WO2011138265A2 (en) | 2010-05-03 | 2011-11-10 | Evotec Ag | Indole and indazole derivatives as orexin receptor antagonists |
| US20160022636A1 (en) | 2013-03-14 | 2016-01-28 | Janssen Pharmaceutica Nv | Physiological ligands for gpr139 |
| JO3719B1 (ar) * | 2014-11-20 | 2021-01-31 | Takeda Pharmaceuticals Co | 4- أوكسو-4،3- داي هيدرو-3،2،1- بنزوترايازينات كمواد ضابطة لأجل gpr139 |
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