HRP20212009T1 - 4-okso-3,4-dihidro-1,2,3-benzotriazini kao modulatori gpr139 - Google Patents
4-okso-3,4-dihidro-1,2,3-benzotriazini kao modulatori gpr139 Download PDFInfo
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- HRP20212009T1 HRP20212009T1 HRP20212009TT HRP20212009T HRP20212009T1 HR P20212009 T1 HRP20212009 T1 HR P20212009T1 HR P20212009T T HRP20212009T T HR P20212009TT HR P20212009 T HRP20212009 T HR P20212009T HR P20212009 T1 HRP20212009 T1 HR P20212009T1
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- Prior art keywords
- triazin
- acetamide
- oxobenzo
- ethyl
- methoxy
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- DMSSTTLDFWKBSX-UHFFFAOYSA-N 1h-1,2,3-benzotriazin-4-one Chemical class C1=CC=C2C(=O)N=NNC2=C1 DMSSTTLDFWKBSX-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims 41
- 150000001875 compounds Chemical class 0.000 claims 37
- 239000003814 drug Substances 0.000 claims 24
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- FYJKKFHJPFYDJN-UHFFFAOYSA-N 2-(4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-[4-(trifluoromethyl)phenyl]ethyl]acetamide Chemical compound O=C1C2=C(N=NN1CC(=O)NC(C)C1=CC=C(C=C1)C(F)(F)F)C=CC=C2 FYJKKFHJPFYDJN-UHFFFAOYSA-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
- POOIUAVPFUNLNL-UHFFFAOYSA-N 2-(5-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methoxyphenyl)ethyl]acetamide Chemical compound FC1=CC=CC=2N=NN(C(C=21)=O)CC(=O)NC(C)C1=CC=C(C=C1)OC POOIUAVPFUNLNL-UHFFFAOYSA-N 0.000 claims 2
- GOUPEUKVQKMWGR-UHFFFAOYSA-N 2-(5-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound FC1=CC=CC=2N=NN(C(C=21)=O)CC(=O)NC(C)C1=CC=C(C=C1)C GOUPEUKVQKMWGR-UHFFFAOYSA-N 0.000 claims 2
- 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 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
- LHFAZQQRCGGNJS-NSHDSACASA-N 2-(5-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[4-(trifluoromethoxy)phenyl]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(F)(F)F LHFAZQQRCGGNJS-NSHDSACASA-N 0.000 claims 2
- KNJBLSXPWYUHOB-UHFFFAOYSA-N 2-(5-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methoxyphenyl)ethyl]acetamide Chemical compound COC1=CC=CC=2N=NN(C(C=21)=O)CC(=O)NC(C)C1=CC=C(C=C1)OC KNJBLSXPWYUHOB-UHFFFAOYSA-N 0.000 claims 2
- KCBGXCAHBBWRNE-UHFFFAOYSA-N 2-(5-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound COC1=CC=CC=2N=NN(C(C=21)=O)CC(=O)NC(C)C1=CC=C(C=C1)C KCBGXCAHBBWRNE-UHFFFAOYSA-N 0.000 claims 2
- LHFAZQQRCGGNJS-UHFFFAOYSA-N 2-(5-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-[4-(trifluoromethoxy)phenyl]ethyl]acetamide Chemical compound COC1=CC=CC=2N=NN(C(C=21)=O)CC(=O)NC(C)C1=CC=C(C=C1)OC(F)(F)F LHFAZQQRCGGNJS-UHFFFAOYSA-N 0.000 claims 2
- TXINLWSEWPZSAH-UHFFFAOYSA-N 2-(5-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-[4-(trifluoromethyl)phenyl]ethyl]acetamide Chemical compound COC1=CC=CC=2N=NN(C(C=21)=O)CC(=O)NC(C)C1=CC=C(C=C1)C(F)(F)F TXINLWSEWPZSAH-UHFFFAOYSA-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
- OIAZRITXWWPTNH-UHFFFAOYSA-N 2-(6,8-dichloro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methoxyphenyl)ethyl]acetamide Chemical compound ClC1=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)OC)C(=C1)Cl OIAZRITXWWPTNH-UHFFFAOYSA-N 0.000 claims 2
- QDKXIUDVKUIJBT-UHFFFAOYSA-N 2-(6,8-dichloro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound ClC1=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)C)C(=C1)Cl QDKXIUDVKUIJBT-UHFFFAOYSA-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
- BHDLUINLODALAW-UHFFFAOYSA-N 2-(6,8-dimethyl-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methoxyphenyl)ethyl]acetamide Chemical compound CC1=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)OC)C(=C1)C BHDLUINLODALAW-UHFFFAOYSA-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
- IMHMUHMELFJCBS-UHFFFAOYSA-N 2-(6-chloro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methoxyphenyl)ethyl]acetamide Chemical compound ClC1=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)OC)C=C1 IMHMUHMELFJCBS-UHFFFAOYSA-N 0.000 claims 2
- QTXLUZLLRISUJM-UHFFFAOYSA-N 2-(6-chloro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound ClC1=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)C)C=C1 QTXLUZLLRISUJM-UHFFFAOYSA-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
- RXHUKMCACHRXDL-VIFPVBQESA-N 2-(6-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[2-fluoro-4-(trifluoromethoxy)phenyl]ethyl]acetamide Chemical compound FC1=C(C=CC(=C1)OC(F)(F)F)[C@H](C)NC(CN1N=NC2=C(C1=O)C=C(C=C2)F)=O RXHUKMCACHRXDL-VIFPVBQESA-N 0.000 claims 2
- BDMKAHJBUJKFSQ-JTQLQIEISA-N 2-(6-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[4-(trifluoromethoxy)phenyl]ethyl]acetamide Chemical compound FC1=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)OC(F)(F)F)C=C1 BDMKAHJBUJKFSQ-JTQLQIEISA-N 0.000 claims 2
- SEVBEOMRNZHSKQ-JTQLQIEISA-N 2-(6-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[4-(trifluoromethyl)phenyl]ethyl]acetamide Chemical compound FC1=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)C(F)(F)F)C=C1 SEVBEOMRNZHSKQ-JTQLQIEISA-N 0.000 claims 2
- POUOYHMMTHSEKJ-UHFFFAOYSA-N 2-(6-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methoxyphenyl)ethyl]acetamide Chemical compound FC1=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)OC)C=C1 POUOYHMMTHSEKJ-UHFFFAOYSA-N 0.000 claims 2
- JQVQDOAWGVPICK-UHFFFAOYSA-N 2-(6-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound FC1=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)C)C=C1 JQVQDOAWGVPICK-UHFFFAOYSA-N 0.000 claims 2
- RXHUKMCACHRXDL-UHFFFAOYSA-N 2-(6-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-[2-fluoro-4-(trifluoromethoxy)phenyl]ethyl]acetamide Chemical compound FC1=C(C=CC(=C1)OC(F)(F)F)C(C)NC(CN1N=NC2=C(C1=O)C=C(C=C2)F)=O RXHUKMCACHRXDL-UHFFFAOYSA-N 0.000 claims 2
- BDMKAHJBUJKFSQ-UHFFFAOYSA-N 2-(6-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-[4-(trifluoromethoxy)phenyl]ethyl]acetamide Chemical compound FC1=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)OC(F)(F)F)C=C1 BDMKAHJBUJKFSQ-UHFFFAOYSA-N 0.000 claims 2
- SEVBEOMRNZHSKQ-UHFFFAOYSA-N 2-(6-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-[4-(trifluoromethyl)phenyl]ethyl]acetamide Chemical compound FC1=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)C(F)(F)F)C=C1 SEVBEOMRNZHSKQ-UHFFFAOYSA-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
- LXOIGFCFUKXFFP-NSHDSACASA-N 2-(6-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[4-(trifluoromethoxy)phenyl]ethyl]acetamide Chemical compound COC1=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)OC(F)(F)F)C=C1 LXOIGFCFUKXFFP-NSHDSACASA-N 0.000 claims 2
- ZIDDEVMTDGRYBN-NSHDSACASA-N 2-(6-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[4-(trifluoromethyl)phenyl]ethyl]acetamide Chemical compound COC1=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)C(F)(F)F)C=C1 ZIDDEVMTDGRYBN-NSHDSACASA-N 0.000 claims 2
- MPFIBOVPLHCEFO-UHFFFAOYSA-N 2-(6-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound COC1=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)C)C=C1 MPFIBOVPLHCEFO-UHFFFAOYSA-N 0.000 claims 2
- LXOIGFCFUKXFFP-UHFFFAOYSA-N 2-(6-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-[4-(trifluoromethoxy)phenyl]ethyl]acetamide Chemical compound COC1=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)OC(F)(F)F)C=C1 LXOIGFCFUKXFFP-UHFFFAOYSA-N 0.000 claims 2
- ZIDDEVMTDGRYBN-UHFFFAOYSA-N 2-(6-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-[4-(trifluoromethyl)phenyl]ethyl]acetamide Chemical compound COC1=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)C(F)(F)F)C=C1 ZIDDEVMTDGRYBN-UHFFFAOYSA-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
- MLWZRROZCADIQQ-UHFFFAOYSA-N 2-(6-methyl-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound CC1=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)C)C=C1 MLWZRROZCADIQQ-UHFFFAOYSA-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
- REOWSJCKCYOYLG-UHFFFAOYSA-N 2-(7-chloro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound ClC=1C=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)C)C=1 REOWSJCKCYOYLG-UHFFFAOYSA-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
- LSUBHVFYZXMIAC-NSHDSACASA-N 2-(7-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[4-(trifluoromethoxy)phenyl]ethyl]acetamide Chemical compound COC=1C=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)OC(F)(F)F)C=1 LSUBHVFYZXMIAC-NSHDSACASA-N 0.000 claims 2
- GMJKPWYOVYYMIA-NSHDSACASA-N 2-(7-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[4-(trifluoromethyl)phenyl]ethyl]acetamide Chemical compound COC=1C=CC2=C(N=NN(C2=O)CC(=O)N[C@@H](C)C2=CC=C(C=C2)C(F)(F)F)C=1 GMJKPWYOVYYMIA-NSHDSACASA-N 0.000 claims 2
- KZGCQSLARYWBID-UHFFFAOYSA-N 2-(7-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methoxyphenyl)ethyl]acetamide Chemical compound COC=1C=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)OC)C=1 KZGCQSLARYWBID-UHFFFAOYSA-N 0.000 claims 2
- BFLNIJPZEKHHMD-UHFFFAOYSA-N 2-(7-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound COC=1C=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)C)C=1 BFLNIJPZEKHHMD-UHFFFAOYSA-N 0.000 claims 2
- LSUBHVFYZXMIAC-UHFFFAOYSA-N 2-(7-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-[4-(trifluoromethoxy)phenyl]ethyl]acetamide Chemical compound COC=1C=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)OC(F)(F)F)C=1 LSUBHVFYZXMIAC-UHFFFAOYSA-N 0.000 claims 2
- GMJKPWYOVYYMIA-UHFFFAOYSA-N 2-(7-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-[4-(trifluoromethyl)phenyl]ethyl]acetamide Chemical compound COC=1C=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)C(F)(F)F)C=1 GMJKPWYOVYYMIA-UHFFFAOYSA-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
- UOFXNHJSTFHCTF-UHFFFAOYSA-N 2-(7-methyl-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound CC=1C=CC2=C(N=NN(C2=O)CC(=O)NC(C)C2=CC=C(C=C2)C)C=1 UOFXNHJSTFHCTF-UHFFFAOYSA-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
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Classifications
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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Landscapes
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- Chemical & Material Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462082539P | 2014-11-20 | 2014-11-20 | |
| US201562184729P | 2015-06-25 | 2015-06-25 | |
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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 |
| TWI873185B (zh) * | 2019-09-16 | 2025-02-21 | 日商武田藥品工業股份有限公司 | 唑稠合之嗒-3(2h)-酮衍生物 |
| WO2021127459A1 (en) * | 2019-12-20 | 2021-06-24 | Blackthorn Therapeutics, Inc. | Gpr139 receptor modulators |
| JP7697974B2 (ja) * | 2020-05-08 | 2025-06-24 | 武田薬品工業株式会社 | Ｇｐｒ１３９アゴニストの置換ベンゾトリアジノン代謝物 |
| US20230310441A1 (en) * | 2020-09-21 | 2023-10-05 | Takeda Pharmaceutical Company | Treatment for schizophrenia |
| US11760788B2 (en) | 2021-03-02 | 2023-09-19 | Pathways Neuro Pharma, Inc. | Neuroreceptor compositions and methods of use |
| CN116693536A (zh) * | 2022-03-01 | 2023-09-05 | 上海科技大学 | 吡咯并三嗪酮类化合物、含其的药物组合物、其制备方法及其应用 |
| CN116693545A (zh) * | 2022-03-01 | 2023-09-05 | 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 |
| 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 |
| CN117815217B (zh) * | 2023-12-29 | 2026-07-10 | 郑州大学第三附属医院(河南省妇幼保健院) | 一种苯甲酰胺衍生物改善认知功能障碍的用途 |
| 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 |
| CN121159462A (zh) * | 2025-11-19 | 2025-12-19 | 杭州市第七人民医院(杭州市心理危机研究与干预中心) | 喹唑啉酮类化合物及其在制备神经系统疾病药物中的应用 |
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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 |
| ATE108791T1 (de) * | 1987-11-04 | 1994-08-15 | Beecham Group Plc | Neue 4-oxobenzotriazine und 4-oxochinazoline. |
| CA2526506A1 (en) | 2003-06-09 | 2004-12-16 | Boehringer Ingelheim International Gmbh | Inhibitors of papilloma virus |
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| FR2875805B1 (fr) | 2004-09-27 | 2006-12-29 | Genfit S A | Composes derives de n-(benzyl) phenylacetamide substitues, preparation et utilisations |
| UY30048A1 (es) | 2005-12-23 | 2007-07-31 | Astrazeneca Ab | Derivados sustituidos de la n,2-(1h-benzimidazol-1-il) acetamida, composiciones farmacéuticas conteniéndolos, procesos de preparación y aplicaciones |
| TWI433839B (zh) | 2006-08-11 | 2014-04-11 | Neomed Inst | 新穎的苯并咪唑衍生物290 |
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| EP2968240A2 (en) * | 2013-03-14 | 2016-01-20 | Janssen Pharmaceutica, N.V. | 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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