ES2897545T3 - 4-Oxo-3,4-dihidro-1,2,3-benzotriazinas como moduladores de GPR139 - Google Patents

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Publication number

ES2897545T3

ES2897545T3 ES19152036T ES19152036T ES2897545T3 ES 2897545 T3 ES2897545 T3 ES 2897545T3 ES 19152036 T ES19152036 T ES 19152036T ES 19152036 T ES19152036 T ES 19152036T ES 2897545 T3 ES2897545 T3 ES 2897545T3

Authority

ES

Spain

Prior art keywords

triazin

oxobenzo

acetamide

ethyl

methoxy

Prior art date

2014-11-20

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.)

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• 101000996780 Homo sapiens Probable G-protein coupled receptor 139 Proteins 0.000 title description 41
• 102100033836 Probable G-protein coupled receptor 139 Human genes 0.000 title description 38
• 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 description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 381
• 239000003814 drug Substances 0.000 claims abstract description 88
• 150000003839 salts Chemical class 0.000 claims abstract description 56
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 53
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 48
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 37
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 34
• 208000035475 disorder Diseases 0.000 claims abstract description 33
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 30
• -1 hydroxy, amino Chemical group 0.000 claims abstract description 30
• 239000001257 hydrogen Substances 0.000 claims abstract description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
• 238000011282 treatment Methods 0.000 claims abstract description 22
• 201000010099 disease Diseases 0.000 claims abstract description 20
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims abstract description 18
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims abstract description 17
• 201000000980 schizophrenia Diseases 0.000 claims abstract description 17
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
• 208000011117 substance-related disease Diseases 0.000 claims abstract description 9
• 208000010877 cognitive disease Diseases 0.000 claims abstract description 8
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims abstract description 6
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims abstract description 6
• 208000020925 Bipolar disease Diseases 0.000 claims abstract description 6
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims abstract description 6
• 208000019901 Anxiety disease Diseases 0.000 claims abstract description 5
• 208000028698 Cognitive impairment Diseases 0.000 claims abstract description 5
• 208000002193 Pain Diseases 0.000 claims abstract description 5
• 206010013663 drug dependence Diseases 0.000 claims abstract description 5
• 206010003805 Autism Diseases 0.000 claims abstract description 4
• 208000020706 Autistic disease Diseases 0.000 claims abstract description 4
• 208000030814 Eating disease Diseases 0.000 claims abstract description 4
• 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 4
• 208000001640 Fibromyalgia Diseases 0.000 claims abstract description 4
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 4
• 235000014632 disordered eating Nutrition 0.000 claims abstract description 4
• 208000028173 post-traumatic stress disease Diseases 0.000 claims abstract description 4
• 208000019116 sleep disease Diseases 0.000 claims abstract description 4
• 201000009032 substance abuse Diseases 0.000 claims abstract description 4
• 231100000736 substance abuse Toxicity 0.000 claims abstract description 4
• 238000001228 spectrum Methods 0.000 claims abstract description 3
• 125000001475 halogen functional group Chemical group 0.000 claims abstract 6
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 40
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 208000029560 autism spectrum disease Diseases 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
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• 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 description 3
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• 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 description 3
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• 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 description 2
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• 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 description 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 description 2
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• 239000013543 active substance Substances 0.000 claims description 2
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• 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 description 2
• 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
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• 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
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• 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
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• 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-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-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-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-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
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