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
- Publication number
- 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
- Authority
- HR
- Croatia
- Prior art keywords
- triazin
- acetamide
- oxobenzo
- ethyl
- methoxy
- Prior art date
Links
- 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
- XSLDKBATWMJNOE-UHFFFAOYSA-N 2-(8-chloro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methoxyphenyl)ethyl]acetamide Chemical compound ClC1=CC=CC2=C1N=NN(C2=O)CC(=O)NC(C)C1=CC=C(C=C1)OC XSLDKBATWMJNOE-UHFFFAOYSA-N 0.000 claims 2
- ZXFHIAAKONRMNN-UHFFFAOYSA-N 2-(8-chloro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound ClC1=CC=CC2=C1N=NN(C2=O)CC(=O)NC(C)C1=CC=C(C=C1)C ZXFHIAAKONRMNN-UHFFFAOYSA-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
- QIXCVVSWMRNBGV-UHFFFAOYSA-N 2-(8-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methoxyphenyl)ethyl]acetamide Chemical compound FC1=CC=CC2=C1N=NN(C2=O)CC(=O)NC(C)C1=CC=C(C=C1)OC QIXCVVSWMRNBGV-UHFFFAOYSA-N 0.000 claims 2
- NFHZMSKSZWDGLN-UHFFFAOYSA-N 2-(8-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound FC1=CC=CC2=C1N=NN(C2=O)CC(=O)NC(C)C1=CC=C(C=C1)C NFHZMSKSZWDGLN-UHFFFAOYSA-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
- RZIPXHMOCWWGGT-NSHDSACASA-N 2-(8-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[4-(trifluoromethoxy)phenyl]ethyl]acetamide Chemical compound COC1=CC=CC2=C1N=NN(C2=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)OC(F)(F)F RZIPXHMOCWWGGT-NSHDSACASA-N 0.000 claims 2
- ZEFUYBHGEMUTQJ-NSHDSACASA-N 2-(8-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[4-(trifluoromethyl)phenyl]ethyl]acetamide Chemical compound COC1=CC=CC2=C1N=NN(C2=O)CC(=O)N[C@@H](C)C1=CC=C(C=C1)C(F)(F)F ZEFUYBHGEMUTQJ-NSHDSACASA-N 0.000 claims 2
- QEFZPGDVQARJQX-UHFFFAOYSA-N 2-(8-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methoxyphenyl)ethyl]acetamide Chemical compound COC1=CC=CC2=C1N=NN(C2=O)CC(=O)NC(C)C1=CC=C(C=C1)OC QEFZPGDVQARJQX-UHFFFAOYSA-N 0.000 claims 2
- QZHOUHZKMLGYJN-UHFFFAOYSA-N 2-(8-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound COC1=CC=CC2=C1N=NN(C2=O)CC(=O)NC(C)C1=CC=C(C=C1)C QZHOUHZKMLGYJN-UHFFFAOYSA-N 0.000 claims 2
- RZIPXHMOCWWGGT-UHFFFAOYSA-N 2-(8-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-[4-(trifluoromethoxy)phenyl]ethyl]acetamide Chemical compound COC1=CC=CC2=C1N=NN(C2=O)CC(=O)NC(C)C1=CC=C(C=C1)OC(F)(F)F RZIPXHMOCWWGGT-UHFFFAOYSA-N 0.000 claims 2
- ZEFUYBHGEMUTQJ-UHFFFAOYSA-N 2-(8-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-[4-(trifluoromethyl)phenyl]ethyl]acetamide Chemical compound COC1=CC=CC2=C1N=NN(C2=O)CC(=O)NC(C)C1=CC=C(C=C1)C(F)(F)F ZEFUYBHGEMUTQJ-UHFFFAOYSA-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
- UUUQJHYOVJWEKZ-UHFFFAOYSA-N 2-(8-methyl-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound CC1=CC=CC2=C1N=NN(C2=O)CC(=O)NC(C)C1=CC=C(C=C1)C UUUQJHYOVJWEKZ-UHFFFAOYSA-N 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
- GGNHXCNZBBFVSL-JTQLQIEISA-N N-[(1S)-1-(2-bromo-4-fluorophenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound BrC1=C(C=CC(=C1)F)[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O GGNHXCNZBBFVSL-JTQLQIEISA-N 0.000 claims 2
- HDUVHDCHYOJUAN-JTQLQIEISA-N N-[(1S)-1-(2-chloro-4-fluorophenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound ClC1=C(C=CC(=C1)F)[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O HDUVHDCHYOJUAN-JTQLQIEISA-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
- DBALUIBYEMXWRA-NSHDSACASA-N N-[(1S)-1-(2-fluoro-4-methylphenyl)ethyl]-2-(6-fluoro-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=C(C=C2)F)=O DBALUIBYEMXWRA-NSHDSACASA-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
- FUWMUUAHZQTWMB-NSHDSACASA-N N-[(1S)-1-(4-methoxyphenyl)ethyl]-2-[4-oxo-6-(trifluoromethyl)-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(F)(F)F)=O FUWMUUAHZQTWMB-NSHDSACASA-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
- GMLBGSJQDOOBRU-LBPRGKRZSA-N N-[(1S)-1-(4-methylphenyl)ethyl]-2-[4-oxo-6-(trifluoromethyl)-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)C(F)(F)F GMLBGSJQDOOBRU-LBPRGKRZSA-N 0.000 claims 2
- GSGHPTZMPYTVQJ-JTQLQIEISA-N N-[(1S)-1-[2-fluoro-4-(trifluoromethoxy)phenyl]ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound FC1=C(C=CC(=C1)OC(F)(F)F)[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O GSGHPTZMPYTVQJ-JTQLQIEISA-N 0.000 claims 2
- FZGJURLPBHRXHF-JTQLQIEISA-N N-[(1S)-1-[2-fluoro-4-(trifluoromethoxy)phenyl]ethyl]-2-(5-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound FC1=C(C=CC(=C1)OC(F)(F)F)[C@H](C)NC(CN1N=NC2=C(C1=O)C(=CC=C2)OC)=O FZGJURLPBHRXHF-JTQLQIEISA-N 0.000 claims 2
- KFLPUQWDEJAHHA-JTQLQIEISA-N N-[(1S)-1-[2-fluoro-4-(trifluoromethyl)phenyl]ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound FC1=C(C=CC(=C1)C(F)(F)F)[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O KFLPUQWDEJAHHA-JTQLQIEISA-N 0.000 claims 2
- BVSHTPOMWMZUCR-JTQLQIEISA-N N-[(1S)-1-[2-fluoro-4-(trifluoromethyl)phenyl]ethyl]-2-(5-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound FC1=C(C=CC(=C1)C(F)(F)F)[C@H](C)NC(CN1N=NC2=C(C1=O)C(=CC=C2)OC)=O BVSHTPOMWMZUCR-JTQLQIEISA-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
- SJQFFAMTFHKEGM-UHFFFAOYSA-N N-[1-(2,4-dimethoxyphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=C(C=CC(=C1)OC)C(C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O SJQFFAMTFHKEGM-UHFFFAOYSA-N 0.000 claims 2
- LXZGSJQRZHHQBT-UHFFFAOYSA-N N-[1-(2,4-dimethylphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound CC1=C(C=CC(=C1)C)C(C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O LXZGSJQRZHHQBT-UHFFFAOYSA-N 0.000 claims 2
- FVQNXYAXDJPHPI-UHFFFAOYSA-N N-[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(C)NC(CN1N=NC2=C(C1=O)C=C(C=C2)F)=O FVQNXYAXDJPHPI-UHFFFAOYSA-N 0.000 claims 2
- GGNHXCNZBBFVSL-UHFFFAOYSA-N N-[1-(2-bromo-4-fluorophenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound BrC1=C(C=CC(=C1)F)C(C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O GGNHXCNZBBFVSL-UHFFFAOYSA-N 0.000 claims 2
- DVGUHHIULIPPKB-UHFFFAOYSA-N N-[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(C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O DVGUHHIULIPPKB-UHFFFAOYSA-N 0.000 claims 2
- DBALUIBYEMXWRA-UHFFFAOYSA-N N-[1-(2-fluoro-4-methylphenyl)ethyl]-2-(6-fluoro-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound FC1=C(C=CC(=C1)C)C(C)NC(CN1N=NC2=C(C1=O)C=C(C=C2)F)=O DBALUIBYEMXWRA-UHFFFAOYSA-N 0.000 claims 2
- FHQBSRAOVCISAR-UHFFFAOYSA-N N-[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(C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O FHQBSRAOVCISAR-UHFFFAOYSA-N 0.000 claims 2
- AOPMTWFMINSQGV-UHFFFAOYSA-N N-[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(C)NC(C(C)N1N=NC2=C(C1=O)C=CC=C2)=O AOPMTWFMINSQGV-UHFFFAOYSA-N 0.000 claims 2
- CWATUEVSJUJDCD-UHFFFAOYSA-N N-[1-(4-ethoxyphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound C(C)OC1=CC=C(C=C1)C(C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O CWATUEVSJUJDCD-UHFFFAOYSA-N 0.000 claims 2
- MROVHIZKKLRMMY-UHFFFAOYSA-N N-[1-(4-methoxyphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)C(C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O MROVHIZKKLRMMY-UHFFFAOYSA-N 0.000 claims 2
- RBQKTEXHVZWNOM-UHFFFAOYSA-N N-[1-(4-methoxyphenyl)ethyl]-2-(5-methyl-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)C(C)NC(CN1N=NC2=C(C1=O)C(=CC=C2)C)=O RBQKTEXHVZWNOM-UHFFFAOYSA-N 0.000 claims 2
- OOURTFAADXDITC-UHFFFAOYSA-N N-[1-(4-methoxyphenyl)ethyl]-2-(6-methyl-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)C(C)NC(CN1N=NC2=C(C1=O)C=C(C=C2)C)=O OOURTFAADXDITC-UHFFFAOYSA-N 0.000 claims 2
- FNEAIYYXBKHWMI-UHFFFAOYSA-N N-[1-(4-methoxyphenyl)ethyl]-2-(7-methyl-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)C(C)NC(CN1N=NC2=C(C1=O)C=CC(=C2)C)=O FNEAIYYXBKHWMI-UHFFFAOYSA-N 0.000 claims 2
- SPIRXYAZOIUKLW-UHFFFAOYSA-N N-[1-(4-methoxyphenyl)ethyl]-2-(8-methyl-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)C(C)NC(CN1N=NC2=C(C1=O)C=CC=C2C)=O SPIRXYAZOIUKLW-UHFFFAOYSA-N 0.000 claims 2
- FUWMUUAHZQTWMB-UHFFFAOYSA-N N-[1-(4-methoxyphenyl)ethyl]-2-[4-oxo-6-(trifluoromethyl)-1,2,3-benzotriazin-3-yl]acetamide Chemical compound COC1=CC=C(C=C1)C(C)NC(CN1N=NC2=C(C1=O)C=C(C=C2)C(F)(F)F)=O FUWMUUAHZQTWMB-UHFFFAOYSA-N 0.000 claims 2
- AMRDWWMUNNALHK-UHFFFAOYSA-N N-[1-(4-methylphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound O=C1C2=C(N=NN1CC(=O)NC(C)C1=CC=C(C=C1)C)C=CC=C2 AMRDWWMUNNALHK-UHFFFAOYSA-N 0.000 claims 2
- GMLBGSJQDOOBRU-UHFFFAOYSA-N N-[1-(4-methylphenyl)ethyl]-2-[4-oxo-6-(trifluoromethyl)-1,2,3-benzotriazin-3-yl]acetamide Chemical compound O=C1C2=C(N=NN1CC(=O)NC(C)C1=CC=C(C=C1)C)C=CC(=C2)C(F)(F)F GMLBGSJQDOOBRU-UHFFFAOYSA-N 0.000 claims 2
- GSGHPTZMPYTVQJ-UHFFFAOYSA-N N-[1-[2-fluoro-4-(trifluoromethoxy)phenyl]ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound FC1=C(C=CC(=C1)OC(F)(F)F)C(C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O GSGHPTZMPYTVQJ-UHFFFAOYSA-N 0.000 claims 2
- FZGJURLPBHRXHF-UHFFFAOYSA-N N-[1-[2-fluoro-4-(trifluoromethoxy)phenyl]ethyl]-2-(5-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound FC1=C(C=CC(=C1)OC(F)(F)F)C(C)NC(CN1N=NC2=C(C1=O)C(=CC=C2)OC)=O FZGJURLPBHRXHF-UHFFFAOYSA-N 0.000 claims 2
- KFLPUQWDEJAHHA-UHFFFAOYSA-N N-[1-[2-fluoro-4-(trifluoromethyl)phenyl]ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound FC1=C(C=CC(=C1)C(F)(F)F)C(C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O KFLPUQWDEJAHHA-UHFFFAOYSA-N 0.000 claims 2
- BVSHTPOMWMZUCR-UHFFFAOYSA-N N-[1-[2-fluoro-4-(trifluoromethyl)phenyl]ethyl]-2-(5-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound FC1=C(C=CC(=C1)C(F)(F)F)C(C)NC(CN1N=NC2=C(C1=O)C(=CC=C2)OC)=O BVSHTPOMWMZUCR-UHFFFAOYSA-N 0.000 claims 2
- WCYBVBQGXJOEJY-UHFFFAOYSA-N N-[1-[4-(difluoromethoxy)phenyl]ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound FC(OC1=CC=C(C=C1)C(C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O)F WCYBVBQGXJOEJY-UHFFFAOYSA-N 0.000 claims 2
- CBWQJOMWISNROA-UHFFFAOYSA-N N-[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(C)NC(CN1N=NC2=C(C1=O)C(=CC=C2)OC)=O)F CBWQJOMWISNROA-UHFFFAOYSA-N 0.000 claims 2
- NVBVBYBGSGRJPA-UHFFFAOYSA-N N-[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(C)NC(CN1N=NC2=C(C1=O)C=C(C=C2)F)=O)F NVBVBYBGSGRJPA-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 208000029560 autism spectrum disease Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 2
- -1 hydroxy, amino Chemical group 0.000 claims 2
- YNTGGPUBNFJFLL-UHFFFAOYSA-N n-[1-(4-bromophenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound N1=NC2=CC=CC=C2C(=O)N1CC(=O)NC(C)C1=CC=C(Br)C=C1 YNTGGPUBNFJFLL-UHFFFAOYSA-N 0.000 claims 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- JZGLECLGVQRPPI-NSHDSACASA-N 2-(4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[4-(trifluoromethoxy)phenyl]ethyl]acetamide Chemical compound O=C1C2=C(N=NN1CC(=O)N[C@@H](C)C1=CC=C(C=C1)OC(F)(F)F)C=CC=C2 JZGLECLGVQRPPI-NSHDSACASA-N 0.000 claims 1
- 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
- FYJKKFHJPFYDJN-NSHDSACASA-N 2-(4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[4-(trifluoromethyl)phenyl]ethyl]acetamide Chemical compound O=C1C2=C(N=NN1CC(=O)N[C@@H](C)C1=CC=C(C=C1)C(F)(F)F)C=CC=C2 FYJKKFHJPFYDJN-NSHDSACASA-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
- PGSIBSVOWOZOCM-UHFFFAOYSA-N 2-(4-oxo-1,2,3-benzotriazin-3-yl)-n-(1-phenylethyl)acetamide Chemical compound N1=NC2=CC=CC=C2C(=O)N1CC(=O)NC(C)C1=CC=CC=C1 PGSIBSVOWOZOCM-UHFFFAOYSA-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
- 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 1
- 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 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
- TXINLWSEWPZSAH-NSHDSACASA-N 2-(5-methoxy-4-oxo-1,2,3-benzotriazin-3-yl)-N-[(1S)-1-[4-(trifluoromethyl)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)C(F)(F)F TXINLWSEWPZSAH-NSHDSACASA-N 0.000 claims 1
- 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 1
- BFNPBDJFKSZLHJ-UHFFFAOYSA-N 2-(8-fluoro-6-methyl-4-oxo-1,2,3-benzotriazin-3-yl)-N-[1-(4-methylphenyl)ethyl]acetamide Chemical compound FC1=CC(=CC2=C1N=NN(C2=O)CC(=O)NC(C)C1=CC=C(C=C1)C)C BFNPBDJFKSZLHJ-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 208000001640 Fibromyalgia Diseases 0.000 claims 1
- ZKALVEIABNRJPU-ZDUSSCGKSA-N N-[(1S)-1-(2-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=C(C=CC=C1)C)C=CC=C2 ZKALVEIABNRJPU-ZDUSSCGKSA-N 0.000 claims 1
- 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 1
- FULFLROHKPSFAY-LBPRGKRZSA-N N-[(2S)-1-(4-chloro-2-methoxyphenyl)propan-2-yl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound ClC1=CC(=C(C=C1)C[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O)OC FULFLROHKPSFAY-LBPRGKRZSA-N 0.000 claims 1
- 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 1
- HDUVHDCHYOJUAN-UHFFFAOYSA-N N-[1-(2-chloro-4-fluorophenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound ClC1=C(C=CC(=C1)F)C(C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O HDUVHDCHYOJUAN-UHFFFAOYSA-N 0.000 claims 1
- NCYGXXHWJXKIOW-UHFFFAOYSA-N N-[2-(2-chloro-4-methoxyphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound ClC1=C(CCNC(CN2N=NC3=C(C2=O)C=CC=C3)=O)C=CC(=C1)OC NCYGXXHWJXKIOW-UHFFFAOYSA-N 0.000 claims 1
- RTUBUXQAHORXQB-UHFFFAOYSA-N N-[2-(4-hydroxyphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound OC1=CC=C(C=C1)CCNC(CN1N=NC2=C(C1=O)C=CC=C2)=O RTUBUXQAHORXQB-UHFFFAOYSA-N 0.000 claims 1
- ZGZJPRGEZGGMOK-UHFFFAOYSA-N N-[2-(4-methoxyphenyl)ethyl]-N-methyl-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)CCN(C(CN1N=NC2=C(C1=O)C=CC=C2)=O)C ZGZJPRGEZGGMOK-UHFFFAOYSA-N 0.000 claims 1
- 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
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- BRVHTHJIFYTNJL-NSHDSACASA-N n-[(1s)-1-(4-chlorophenyl)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(Cl)C=C1 BRVHTHJIFYTNJL-NSHDSACASA-N 0.000 claims 1
- 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
- ZKALVEIABNRJPU-UHFFFAOYSA-N n-[1-(2-methylphenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound N1=NC2=CC=CC=C2C(=O)N1CC(=O)NC(C)C1=CC=CC=C1C ZKALVEIABNRJPU-UHFFFAOYSA-N 0.000 claims 1
- BRVHTHJIFYTNJL-UHFFFAOYSA-N n-[1-(4-chlorophenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound N1=NC2=CC=CC=C2C(=O)N1CC(=O)NC(C)C1=CC=C(Cl)C=C1 BRVHTHJIFYTNJL-UHFFFAOYSA-N 0.000 claims 1
- IKWQWSKSKJKRIZ-UHFFFAOYSA-N n-[1-(4-fluorophenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound N1=NC2=CC=CC=C2C(=O)N1CC(=O)NC(C)C1=CC=C(F)C=C1 IKWQWSKSKJKRIZ-UHFFFAOYSA-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
- GASJSONKGOIOOV-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound C1=CC(Cl)=CC=C1CCNC(=O)CN1C(=O)C2=CC=CC=C2N=N1 GASJSONKGOIOOV-UHFFFAOYSA-N 0.000 claims 1
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 201000009032 substance abuse Diseases 0.000 claims 1
- 231100000736 substance abuse Toxicity 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Hematology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Diabetes (AREA)
- Anesthesiology (AREA)
- Obesity (AREA)
- 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 | |
| EP19152036.0A EP3536324B1 (en) | 2014-11-20 | 2015-11-19 | 4-oxo-3,4-dihydro-1,2,3-benzotriazines as modulators of gpr139 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20212009T1 true HRP20212009T1 (hr) | 2022-04-01 |
Family
ID=55022667
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20212009TT HRP20212009T1 (hr) | 2014-11-20 | 2015-11-19 | 4-okso-3,4-dihidro-1,2,3-benzotriazini kao modulatori gpr139 |
| HRP20191003TT HRP20191003T1 (hr) | 2014-11-20 | 2015-11-19 | Derivati 4-okso-3,4-dihidro-1,2,3-benzotriazina kao modulatori gpr139 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20191003TT HRP20191003T1 (hr) | 2014-11-20 | 2015-11-19 | Derivati 4-okso-3,4-dihidro-1,2,3-benzotriazina kao modulatori gpr139 |
Country Status (40)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2021055326A1 (en) | 2019-09-16 | 2021-03-25 | 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 |
| CA3177117A1 (en) * | 2020-05-08 | 2021-11-11 | Amin Mohamed Kamel | 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 |
| 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 |
| 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 |
| 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 |
| CN120424068A (zh) * | 2024-02-02 | 2025-08-05 | 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 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3794726A (en) * | 1972-08-21 | 1974-02-26 | Uniroyal Inc | Inhibiting aggressive behavior with 1,2,3-benzotriazin-(3h)-one |
| EP0799617A3 (en) | 1986-02-24 | 1997-11-12 | Mitsui Petrochemical Industries, Ltd. | Therapeutic agent for neurological diseases |
| ATE108791T1 (de) * | 1987-11-04 | 1994-08-15 | Beecham Group Plc | Neue 4-oxobenzotriazine und 4-oxochinazoline. |
| EP1636200A2 (en) | 2003-06-09 | 2006-03-22 | Boehringer Ingelheim International GmbH | Inhibitors of papilloma virus |
| AU2004261283B2 (en) | 2003-07-31 | 2008-05-01 | Irm, Llc | Bicyclic compounds and compositions as PDF inhibitors |
| 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 |
| CN101641358A (zh) * | 2007-03-23 | 2010-02-03 | 霍夫曼-拉罗奇有限公司 | 氮杂-吡啶并嘧啶酮衍生物 |
| AU2008345225A1 (en) * | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| WO2011138265A2 (en) | 2010-05-03 | 2011-11-10 | Evotec Ag | Indole and indazole derivatives as orexin receptor antagonists |
| 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 |
-
2015
- 2015-11-18 JO JOP/2015/0282A patent/JO3719B1/ar active
- 2015-11-19 LT LTEP15816275.0T patent/LT3221298T/lt unknown
- 2015-11-19 MD MDE20170117 patent/MD3221298T2/ro unknown
- 2015-11-19 CR CR20170275A patent/CR20170275A/es unknown
- 2015-11-19 ES ES19152036T patent/ES2897545T3/es active Active
- 2015-11-19 PT PT15816275T patent/PT3221298T/pt unknown
- 2015-11-19 HU HUE15816275A patent/HUE044145T2/hu unknown
- 2015-11-19 UY UY0001036406A patent/UY36406A/es not_active Application Discontinuation
- 2015-11-19 PE PE2017000866A patent/PE20170899A1/es unknown
- 2015-11-19 MX MX2017006448A patent/MX378158B/es unknown
- 2015-11-19 CA CA2968242A patent/CA2968242C/en active Active
- 2015-11-19 US US14/946,194 patent/US9556130B2/en active Active
- 2015-11-19 DK DK15816275.0T patent/DK3221298T3/da active
- 2015-11-19 ES ES15816275T patent/ES2734735T3/es active Active
- 2015-11-19 SI SI201530772T patent/SI3221298T1/sl unknown
- 2015-11-19 HU HUE19152036A patent/HUE057451T2/hu unknown
- 2015-11-19 SM SM20190355T patent/SMT201900355T1/it unknown
- 2015-11-19 PT PT191520360T patent/PT3536324T/pt unknown
- 2015-11-19 TN TN2017000196A patent/TN2017000196A1/en unknown
- 2015-11-19 JP JP2017526844A patent/JP6637501B2/ja active Active
- 2015-11-19 SI SI201531729T patent/SI3536324T1/sl unknown
- 2015-11-19 SM SM20220142T patent/SMT202200142T1/it unknown
- 2015-11-19 TW TW104138295A patent/TWI684590B/zh active
- 2015-11-19 SG SG11201704002UA patent/SG11201704002UA/en unknown
- 2015-11-19 GE GEAP201814515A patent/GEAP201814515A/en unknown
- 2015-11-19 EP EP19152036.0A patent/EP3536324B1/en active Active
- 2015-11-19 UA UAA201705041A patent/UA120375C2/uk unknown
- 2015-11-19 DK DK19152036.0T patent/DK3536324T3/da active
- 2015-11-19 MY MYPI2017701778A patent/MY187423A/en unknown
- 2015-11-19 HR HRP20212009TT patent/HRP20212009T1/hr unknown
- 2015-11-19 AU AU2015349866A patent/AU2015349866B2/en active Active
- 2015-11-19 HR HRP20191003TT patent/HRP20191003T1/hr unknown
- 2015-11-19 EP EP15816275.0A patent/EP3221298B1/en active Active
- 2015-11-19 WO PCT/US2015/061607 patent/WO2016081736A1/en not_active Ceased
- 2015-11-19 PL PL15816275T patent/PL3221298T3/pl unknown
- 2015-11-19 GE GEAP201514515A patent/GEP20196961B/en unknown
- 2015-11-19 CN CN202010988947.3A patent/CN112062730B/zh active Active
- 2015-11-19 RS RS20211398A patent/RS62563B1/sr unknown
- 2015-11-19 RS RS20190776A patent/RS59078B1/sr unknown
- 2015-11-19 EA EA201791096A patent/EA033728B1/ru unknown
- 2015-11-19 NZ NZ732208A patent/NZ732208A/en unknown
- 2015-11-19 KR KR1020177016973A patent/KR102582021B1/ko active Active
- 2015-11-19 MA MA40993A patent/MA40993B1/fr unknown
- 2015-11-19 PL PL19152036T patent/PL3536324T3/pl unknown
- 2015-11-19 CN CN201580071393.8A patent/CN107108531B/zh active Active
- 2015-11-19 LT LTEP19152036.0T patent/LT3536324T/lt unknown
-
2016
- 2016-12-16 US US15/382,490 patent/US9770450B2/en active Active
-
2017
- 2017-05-12 DO DO2017000120A patent/DOP2017000120A/es unknown
- 2017-05-16 IL IL252311A patent/IL252311B/en active IP Right Grant
- 2017-05-18 PH PH12017500920A patent/PH12017500920B1/en unknown
- 2017-05-19 CL CL2017001292A patent/CL2017001292A1/es unknown
- 2017-06-16 CO CONC2017/0005959A patent/CO2017005959A2/es unknown
- 2017-06-20 EC ECIEPI201738999A patent/ECSP17038999A/es unknown
- 2017-08-22 US US15/683,589 patent/US10159677B2/en active Active
-
2018
- 2018-11-02 US US16/179,709 patent/US10561662B2/en active Active
-
2019
- 2019-06-20 CY CY20191100646T patent/CY1122613T1/el unknown
- 2019-12-20 JP JP2019229837A patent/JP6918088B2/ja active Active
-
2020
- 2020-01-02 US US16/732,536 patent/US11173161B2/en active Active
-
2021
- 2021-12-17 CY CY20211101111T patent/CY1124929T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20212009T1 (hr) | 4-okso-3,4-dihidro-1,2,3-benzotriazini kao modulatori gpr139 | |
| JP2017535559A5 (enExample) | ||
| HRP20120144T1 (en) | Therapeutic uses of compounds having combined sert, 5-ht3 and 5-ht1a activity | |
| PE20120413A1 (es) | ENANTIOMERO (S) DE 1'-{[5-(TRIFLUOROMETIL)FURAN-2-IL]METIL}ESPIRO[FURO[2,3-f][1,3]BENZODIOXOL-7,3'-INDOL]-2'(1'H)-ONA | |
| MX377837B (es) | Compuestos de indol carboxamida utiles como inhibidores de cinasas. | |
| MY167423A (en) | Quinoline carboxamide and quinoline carbonitrile derivatives as mglur2-negative allosteric modulators,compositions,and their use | |
| PE20152032A1 (es) | Compuestos de 3,4-dihidroisoquinolin-2(1h)-il | |
| NZ630260A (en) | Dihydrate of benzothiophene compound or of a salt thereof, and process for producing the same | |
| MX2013007295A (es) | Quinoxalinas y aza-quinoxalinas como moduladores del receptor de crth2. | |
| HRP20120558T1 (hr) | Kapa-selektivni antagonist opioidnih receptora | |
| UY32526A (es) | Aplicaciones terapéuticas de derivados de quinazolinodiona | |
| EP2604602A4 (en) | HETEROARYL PYRAZOLE DERIVATIVE | |
| RU2009103307A (ru) | ПРОИЗВОДНЫЕ ИМИДАЗО[1, 2-a]ПИРИДИН-2-КАРБОКСАМИДОВ, ИХ ПОЛУЧЕНИЕ И ПРИМЕНЕНИЕ В ТЕРАПИИ | |
| RU2016131875A (ru) | Производные n-фениллактама, способные стимулировать нейрогенез, и их применение при лечении заболеваний нервной системы | |
| CO7350619A2 (es) | Compuestos heteroaromáticos y su uso como ligandos d1 de dopamina | |
| RU2015112914A (ru) | Бензимидазолы в качестве активных агентов для центральной нервной системы | |
| MX2013002384A (es) | Compuestos quinazolina y metodos para utilizarlos. | |
| RU2016104890A (ru) | Производные 1,7-нафтиридина | |
| UY31346A1 (es) | Compuestos que tienen actividad en el receptor m1 y sus usos en medicina | |
| EP4086249A3 (en) | 6-membered aza-heterocyclic containing delta-opioid receptor modulating compounds, methods of using and making the same | |
| RU2015148927A (ru) | Производные изохинолина, стимулирующие нейрогенез | |
| MD4538B1 (ro) | 1-Piperazino-3-fenil-indani deuteraţi pentru tratamentul schizofreniei | |
| CL2007002768A1 (es) | Compuestos derivados de quinolin-amina; proceso de preparacion de dichos compuestos; medicamento; y uso para el tratamiento de enfermedades tales como depresion, trastornos de ansiedad, esquizofrenia, agorafobia, dolor, demencia y enfermedad de parki | |
| PE20140629A1 (es) | Derivados de fenil-isoxazol y procedimiento para la preparacion de los mismos | |
| HRP20170608T4 (hr) | Terapijske uporabe 1-[2-(2,4-dimetil-fenilsulfanil)fenil]piperazina |