ES2734735T3 - Derivados de 4-oxo-3,4-dihidro-1,2,3,-benzotriazina como moduladores de GPR139 - Google Patents

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Publication number

ES2734735T3

ES2734735T3 ES15816275T ES15816275T ES2734735T3 ES 2734735 T3 ES2734735 T3 ES 2734735T3 ES 15816275 T ES15816275 T ES 15816275T ES 15816275 T ES15816275 T ES 15816275T ES 2734735 T3 ES2734735 T3 ES 2734735T3

Authority

ES

Spain

Prior art keywords

oxobenzo

acetamide

triazin

ethyl

fluoro

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 45
• 102100033836 Probable G-protein coupled receptor 139 Human genes 0.000 title description 43
• 150000001875 compounds Chemical class 0.000 claims abstract description 277
• -1 hydroxy, amino Chemical group 0.000 claims abstract description 177
• 150000003839 salts Chemical class 0.000 claims abstract description 55
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 50
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 49
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 41
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 39
• 125000005843 halogen group Chemical group 0.000 claims abstract description 33
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 31
• 239000001257 hydrogen Substances 0.000 claims abstract description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 26
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 10
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 6
• 239000000460 chlorine Substances 0.000 claims abstract description 5
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
• CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims abstract description 3
• IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims abstract description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 196
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 56
• 239000003814 drug Substances 0.000 claims description 49
• 208000035475 disorder Diseases 0.000 claims description 35
• 238000011282 treatment Methods 0.000 claims description 25
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 23
• 201000010099 disease Diseases 0.000 claims description 21
• OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 20
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 19
• 229940055764 triaz Drugs 0.000 claims description 18
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 17
• 201000000980 schizophrenia Diseases 0.000 claims description 16
• RRXSYZFVDIRTFB-UHFFFAOYSA-N C[CH]C1=CC=C(OC)C=C1 Chemical group C[CH]C1=CC=C(OC)C=C1 RRXSYZFVDIRTFB-UHFFFAOYSA-N 0.000 claims description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
• 208000010877 cognitive disease Diseases 0.000 claims description 7
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 208000011117 substance-related disease Diseases 0.000 claims description 7
• 208000029560 autism spectrum disease Diseases 0.000 claims description 6
• 208000020925 Bipolar disease Diseases 0.000 claims description 5
• 208000028698 Cognitive impairment Diseases 0.000 claims description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 230000006735 deficit Effects 0.000 claims description 5
• 206010013663 drug dependence Diseases 0.000 claims description 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• 208000019901 Anxiety disease Diseases 0.000 claims description 4
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
• 208000002193 Pain Diseases 0.000 claims description 4
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
• 206010003805 Autism Diseases 0.000 claims description 3
• 208000020706 Autistic disease Diseases 0.000 claims description 3
• 208000030814 Eating disease Diseases 0.000 claims description 3
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
• 208000001640 Fibromyalgia Diseases 0.000 claims description 3
• 239000013543 active substance Substances 0.000 claims description 3
• 235000014632 disordered eating Nutrition 0.000 claims description 3
• 208000028173 post-traumatic stress disease Diseases 0.000 claims description 3
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 2
• 208000019116 sleep disease Diseases 0.000 claims description 2
• 238000001228 spectrum Methods 0.000 claims description 2
• 201000009032 substance abuse Diseases 0.000 claims description 2
• 231100000736 substance abuse Toxicity 0.000 claims description 2
• 125000005605 benzo group Chemical group 0.000 claims 6
• NHHIFMSLOXYVBO-ZDUSSCGKSA-N 2-(4-oxo-1,2,3-benzotriazin-3-yl)-n-[(2r)-2-phenylpropyl]acetamide Chemical compound C1([C@H](CNC(=O)CN2C(C3=CC=CC=C3N=N2)=O)C)=CC=CC=C1 NHHIFMSLOXYVBO-ZDUSSCGKSA-N 0.000 claims 2
• VDXSDOHBTDMGFG-CYBMUJFWSA-N N-[(2R)-1-(4-methoxyphenyl)propan-2-yl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)C[C@@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O VDXSDOHBTDMGFG-CYBMUJFWSA-N 0.000 claims 2
• VDXSDOHBTDMGFG-ZDUSSCGKSA-N N-[(2S)-1-(4-methoxyphenyl)propan-2-yl]-2-(4-oxo-1,2,3-benzotriazin-3-yl)acetamide Chemical compound COC1=CC=C(C=C1)C[C@H](C)NC(CN1N=NC2=C(C1=O)C=CC=C2)=O VDXSDOHBTDMGFG-ZDUSSCGKSA-N 0.000 claims 2
• 125000003545 alkoxy group Chemical group 0.000 claims 2
• XAGZJIQIVXSURR-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]piperidin-2-one Chemical group C1=CC(C(F)(F)F)=CC=C1N1C(=O)CCCC1 XAGZJIQIVXSURR-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
• 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
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• MEYRABVEYCFHHB-UHFFFAOYSA-N 2-bromo-4-fluorophenol Chemical compound OC1=CC=C(F)C=C1Br MEYRABVEYCFHHB-UHFFFAOYSA-N 0.000 claims 1
• IGYXYGDEYHNFFT-UHFFFAOYSA-N 2-chloro-4-fluorophenol Chemical compound OC1=CC=C(F)C=C1Cl IGYXYGDEYHNFFT-UHFFFAOYSA-N 0.000 claims 1
• RCLQFKLASUKMCG-UHFFFAOYSA-N 6-fluoro-1h-1,2,3-benzotriazin-4-one Chemical compound N1=NNC(=O)C2=CC(F)=CC=C21 RCLQFKLASUKMCG-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 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
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims 1
• 208000013403 hyperactivity Diseases 0.000 claims 1
• ORSHURWNDMDTSA-UHFFFAOYSA-N n-[1-(4-methylphenyl)ethyl]acetamide Chemical compound CC(=O)NC(C)C1=CC=C(C)C=C1 ORSHURWNDMDTSA-UHFFFAOYSA-N 0.000 claims 1
• 239000007787 solid Substances 0.000 description 59
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• 238000002360 preparation method Methods 0.000 description 47
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• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 27
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
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