AU2008299604A1 - Piperidine derivatives as agonists of muscarinic receptors - Google Patents

Info

Publication number

AU2008299604A1

AU2008299604A1 AU2008299604A AU2008299604A AU2008299604A1 AU 2008299604 A1 AU2008299604 A1 AU 2008299604A1 AU 2008299604 A AU2008299604 A AU 2008299604A AU 2008299604 A AU2008299604 A AU 2008299604A AU 2008299604 A1 AU2008299604 A1 AU 2008299604A1

Authority

AU

Australia

Prior art keywords

alkyl

piperidyl

alkoxy

methyl

hexahydro

Prior art date

2007-09-11

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 title description 24
• 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 title description 24
• 239000000556 agonist Substances 0.000 title description 14
• 150000003053 piperidines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 192
• 125000000217 alkyl group Chemical group 0.000 claims description 96
• -1 C 2 -6alkynyloxy Chemical group 0.000 claims description 90
• 239000000203 mixture Substances 0.000 claims description 80
• 125000003545 alkoxy group Chemical group 0.000 claims description 64
• 238000002560 therapeutic procedure Methods 0.000 claims description 38
• 238000000034 method Methods 0.000 claims description 33
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 22
• NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 claims description 20
• 208000002193 Pain Diseases 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
• 241001465754 Metazoa Species 0.000 claims description 17
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
• 239000003814 drug Substances 0.000 claims description 14
• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 239000001257 hydrogen Substances 0.000 claims description 14
• 125000005936 piperidyl group Chemical group 0.000 claims description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 12
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 12
• 238000004519 manufacturing process Methods 0.000 claims description 12
• 230000036407 pain Effects 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 238000011282 treatment Methods 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• LJENYWOZYGSALB-NBJLRHFZSA-N ethyl 3-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 LJENYWOZYGSALB-NBJLRHFZSA-N 0.000 claims description 7
• RWIIUBCMPVZLBA-UHFFFAOYSA-N 1,3,3a,4,5,6,7,7a-octahydrobenzimidazol-2-one Chemical compound C1CCCC2NC(=O)NC21 RWIIUBCMPVZLBA-UHFFFAOYSA-N 0.000 claims description 6
• 201000000980 schizophrenia Diseases 0.000 claims description 6
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 4
• CCHCOSYSXRNJPP-NBJLRHFZSA-N 2-fluoroethyl 3-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1CC(N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C1(C)CCN(C(=O)OCCF)C1 CCHCOSYSXRNJPP-NBJLRHFZSA-N 0.000 claims description 4
• 241001510512 Chlamydia phage 2 Species 0.000 claims description 4
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
• ZXKUTOMRBVXFKV-OALUTQOASA-N propan-2-yl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 ZXKUTOMRBVXFKV-OALUTQOASA-N 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
• GFOOVKOSROWXAZ-UHFFFAOYSA-N 1,3,3a,4,5,6,7,7a-octahydroindol-2-one Chemical compound C1CCCC2NC(=O)CC21 GFOOVKOSROWXAZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 3
• VIRFRHVDXNAETH-UHFFFAOYSA-N 4-methylpiperidine-1-carboxylic acid Chemical compound CC1CCN(C(O)=O)CC1 VIRFRHVDXNAETH-UHFFFAOYSA-N 0.000 claims description 3
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
• 208000019901 Anxiety disease Diseases 0.000 claims description 3
• 125000002393 azetidinyl group Chemical group 0.000 claims description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• LJENYWOZYGSALB-LGJCEAAXSA-N ethyl 3-[4-[(3ar,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1(C)N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 LJENYWOZYGSALB-LGJCEAAXSA-N 0.000 claims description 3
• IVJDEIANCSDDAO-ROUUACIJSA-N ethyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 IVJDEIANCSDDAO-ROUUACIJSA-N 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• NNBXAFHPUMFFFB-RTBURBONSA-N (3ar,7ar)-3-[1-[1-(cyclopropanecarbonyl)-4-methylpiperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(C)(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CCN1C(=O)C1CC1 NNBXAFHPUMFFFB-RTBURBONSA-N 0.000 claims description 2
• NNBXAFHPUMFFFB-OALUTQOASA-N (3as,7as)-3-[1-[1-(cyclopropanecarbonyl)-4-methylpiperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(C)(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1CC1 NNBXAFHPUMFFFB-OALUTQOASA-N 0.000 claims description 2
• BILIYBGFXJGAPT-UHFFFAOYSA-N 3-methylpyrrolidine-1-carboxylic acid Chemical compound CC1CCN(C(O)=O)C1 BILIYBGFXJGAPT-UHFFFAOYSA-N 0.000 claims description 2
• 230000036506 anxiety Effects 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• QZHXKFXCKFGNJH-NVPCEHRXSA-N but-2-ynyl 3-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC#CC)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 QZHXKFXCKFGNJH-NVPCEHRXSA-N 0.000 claims description 2
• SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 claims description 2
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• IVJDEIANCSDDAO-QZTJIDSGSA-N ethyl 4-[4-[(3ar,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(C)N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 IVJDEIANCSDDAO-QZTJIDSGSA-N 0.000 claims description 2
• IVJDEIANCSDDAO-MSOLQXFVSA-N ethyl 4-[4-[(3ar,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(C)N1CCC(N2C(N[C@@H]3CCCC[C@@H]32)=O)CC1 IVJDEIANCSDDAO-MSOLQXFVSA-N 0.000 claims description 2
• FBMWQXFLRCKPIQ-OALUTQOASA-N ethyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-ethylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(CC)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 FBMWQXFLRCKPIQ-OALUTQOASA-N 0.000 claims description 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• AQNYLONDPBAVGN-GAOSQQNJSA-N prop-2-ynyl 3-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1CC(N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C1(C)CCN(C(=O)OCC#C)C1 AQNYLONDPBAVGN-GAOSQQNJSA-N 0.000 claims description 2
• IXBYUAVOBQEXJC-QUCCMNQESA-N propan-2-yl 4-[4-[(3ar,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-indol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1(C)N1CCC(N2C(C[C@H]3CCCC[C@@H]32)=O)CC1 IXBYUAVOBQEXJC-QUCCMNQESA-N 0.000 claims description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• FOLNBRUMVDDPBA-RTBURBONSA-N tert-butyl 4-[4-[(3ar,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 FOLNBRUMVDDPBA-RTBURBONSA-N 0.000 claims description 2
• FOLNBRUMVDDPBA-OALUTQOASA-N tert-butyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 FOLNBRUMVDDPBA-OALUTQOASA-N 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 15
• 150000002431 hydrogen Chemical class 0.000 claims 11
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 10
• 125000005133 alkynyloxy group Chemical group 0.000 claims 3
• 208000020401 Depressive disease Diseases 0.000 claims 1
• XXXPJMMKHPCKGA-PMACEKPBSA-N but-2-ynyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC#CC)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 XXXPJMMKHPCKGA-PMACEKPBSA-N 0.000 claims 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• PTNFPCNYGTUQIT-OALUTQOASA-N prop-2-ynyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CC(N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C1(C)CCN(C(=O)OCC#C)CC1 PTNFPCNYGTUQIT-OALUTQOASA-N 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 207
• 239000000243 solution Substances 0.000 description 68
• 238000002360 preparation method Methods 0.000 description 48
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 38
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 30
• 238000005481 NMR spectroscopy Methods 0.000 description 29
• 238000000746 purification Methods 0.000 description 26
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• 239000007787 solid Substances 0.000 description 24
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 23
• 239000012267 brine Substances 0.000 description 22
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 21
• 241000700159 Rattus Species 0.000 description 19
• 239000012074 organic phase Substances 0.000 description 19
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 229910052757 nitrogen Inorganic materials 0.000 description 18
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 17
• 229920006395 saturated elastomer Polymers 0.000 description 17
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
• 229960005181 morphine Drugs 0.000 description 15
• 239000011734 sodium Substances 0.000 description 15
• 239000008346 aqueous phase Substances 0.000 description 14
• 239000002207 metabolite Substances 0.000 description 14
• 239000012071 phase Substances 0.000 description 14
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
• 238000006243 chemical reaction Methods 0.000 description 13
• 125000000623 heterocyclic group Chemical group 0.000 description 13
• 238000012360 testing method Methods 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
• 239000003480 eluent Substances 0.000 description 12
• 208000004296 neuralgia Diseases 0.000 description 12
• 208000021722 neuropathic pain Diseases 0.000 description 12
• 238000003556 assay Methods 0.000 description 10
• 238000002474 experimental method Methods 0.000 description 10
• 239000012299 nitrogen atmosphere Substances 0.000 description 10
• 208000004454 Hyperalgesia Diseases 0.000 description 9
• 230000027455 binding Effects 0.000 description 9
• 125000000753 cycloalkyl group Chemical group 0.000 description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
• 235000019439 ethyl acetate Nutrition 0.000 description 9
• 102000005962 receptors Human genes 0.000 description 9
• 108020003175 receptors Proteins 0.000 description 9
• 239000002904 solvent Substances 0.000 description 9
• 208000035154 Hyperesthesia Diseases 0.000 description 8
• 239000012528 membrane Substances 0.000 description 8
• 239000007821 HATU Substances 0.000 description 7
• 238000007792 addition Methods 0.000 description 7
• 125000003118 aryl group Chemical group 0.000 description 7
• 210000004978 chinese hamster ovary cell Anatomy 0.000 description 7
• 239000012043 crude product Substances 0.000 description 7
• 201000010099 disease Diseases 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 229940093499 ethyl acetate Drugs 0.000 description 7
• UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• 125000004432 carbon atom Chemical group C* 0.000 description 6
• 238000003818 flash chromatography Methods 0.000 description 6
• NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 6
• DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 6
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 108090000623 proteins and genes Proteins 0.000 description 6
• 125000006413 ring segment Chemical group 0.000 description 6
• 238000004808 supercritical fluid chromatography Methods 0.000 description 6
• VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 6
• MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 6
• 229960000604 valproic acid Drugs 0.000 description 6
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
• 239000004215 Carbon black (E152) Substances 0.000 description 5
• OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 5
• 229960004373 acetylcholine Drugs 0.000 description 5
• 235000019270 ammonium chloride Nutrition 0.000 description 5
• 230000006870 function Effects 0.000 description 5
• 229930195733 hydrocarbon Natural products 0.000 description 5
• 239000003921 oil Substances 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 5
• QDPUXYAYDGHACK-UHFFFAOYSA-N tert-butyl 4-methyl-4-(4-oxopiperidin-1-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C)N1CCC(=O)CC1 QDPUXYAYDGHACK-UHFFFAOYSA-N 0.000 description 5
• GBBOZVGWCUJZSV-CVEARBPZSA-N (3as,7ar)-3-[1-(4-methylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2C(N[C@@H]3CCCC[C@@H]32)=O)CCN1C1(C)CCNCC1 GBBOZVGWCUJZSV-CVEARBPZSA-N 0.000 description 4
• 102000017927 CHRM1 Human genes 0.000 description 4
• 101150073075 Chrm1 gene Proteins 0.000 description 4
• 208000000094 Chronic Pain Diseases 0.000 description 4
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
• 230000004913 activation Effects 0.000 description 4
• 208000005298 acute pain Diseases 0.000 description 4
• 239000005557 antagonist Substances 0.000 description 4
• 239000011324 bead Substances 0.000 description 4
• FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 4
• 229960000623 carbamazepine Drugs 0.000 description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
• 210000004027 cell Anatomy 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 239000000460 chlorine Substances 0.000 description 4
• 230000001684 chronic effect Effects 0.000 description 4
• 231100000673 dose–response relationship Toxicity 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
• 125000005842 heteroatom Chemical group 0.000 description 4
• 239000003112 inhibitor Substances 0.000 description 4
• 239000010410 layer Substances 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• 230000014759 maintenance of location Effects 0.000 description 4
• 125000002950 monocyclic group Chemical group 0.000 description 4
• 230000003551 muscarinic effect Effects 0.000 description 4
• HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 4
• 239000011780 sodium chloride Substances 0.000 description 4
• AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 4
• 210000001032 spinal nerve Anatomy 0.000 description 4
• 125000001424 substituent group Chemical group 0.000 description 4
• 239000010936 titanium Substances 0.000 description 4
• UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 4
• 229940102566 valproate Drugs 0.000 description 4
• GBBOZVGWCUJZSV-HZPDHXFCSA-N (3ar,7ar)-3-[1-(4-methylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2C(N[C@@H]3CCCC[C@H]32)=O)CCN1C1(C)CCNCC1 GBBOZVGWCUJZSV-HZPDHXFCSA-N 0.000 description 3
• ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 description 3
• SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 3
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
• 206010002091 Anaesthesia Diseases 0.000 description 3
• 241000283724 Bison bonasus Species 0.000 description 3
• 206010058019 Cancer Pain Diseases 0.000 description 3
• 208000018522 Gastrointestinal disease Diseases 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
• 238000006859 Swern oxidation reaction Methods 0.000 description 3
• 206010046543 Urinary incontinence Diseases 0.000 description 3
• 239000002253 acid Substances 0.000 description 3
• 230000037005 anaesthesia Effects 0.000 description 3
• 125000004429 atom Chemical group 0.000 description 3
• 239000011575 calcium Substances 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 150000007942 carboxylates Chemical class 0.000 description 3
• NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 3
• ZOGHDTBRWUEJDP-UHFFFAOYSA-N diethylalumanylium;cyanide Chemical compound N#[C-].CC[Al+]CC ZOGHDTBRWUEJDP-UHFFFAOYSA-N 0.000 description 3
• 238000009826 distribution Methods 0.000 description 3
• 229960002866 duloxetine Drugs 0.000 description 3
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
• 239000000284 extract Substances 0.000 description 3
• 238000009472 formulation Methods 0.000 description 3
• 229960002870 gabapentin Drugs 0.000 description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
• 238000007913 intrathecal administration Methods 0.000 description 3
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
• 229960001848 lamotrigine Drugs 0.000 description 3
• PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 description 3
• 229910052744 lithium Inorganic materials 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 3
• 229960005017 olanzapine Drugs 0.000 description 3
• 239000012044 organic layer Substances 0.000 description 3
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 3
• 229960004431 quetiapine Drugs 0.000 description 3
• URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 3
• 150000003254 radicals Chemical class 0.000 description 3
• UHSKFQJFRQCDBE-UHFFFAOYSA-N ropinirole Chemical compound CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 UHSKFQJFRQCDBE-UHFFFAOYSA-N 0.000 description 3
• 239000012453 solvate Substances 0.000 description 3
• 230000000638 stimulation Effects 0.000 description 3
• 238000001356 surgical procedure Methods 0.000 description 3
• YDEDOCBRVKNDON-UHFFFAOYSA-N tert-butyl 3-methyl-3-(4-oxopiperidin-1-yl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1(C)N1CCC(=O)CC1 YDEDOCBRVKNDON-UHFFFAOYSA-N 0.000 description 3
• 239000003981 vehicle Substances 0.000 description 3
• 208000009935 visceral pain Diseases 0.000 description 3
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 3
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
• SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 description 2
• AGVOPGCXXGAGKM-BLBXNVQISA-N (3ar,7ar)-3-[1-(3-methylpyrrolidin-3-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2C(N[C@@H]3CCCC[C@H]32)=O)CCN1C1(C)CCNC1 AGVOPGCXXGAGKM-BLBXNVQISA-N 0.000 description 2
• WLVNOJPDJOADNT-WBVHZDCISA-N (3ar,7as)-1-[1-(4-methylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-3h-indol-2-one Chemical compound C1CC(N2C(C[C@H]3CCCC[C@@H]32)=O)CCN1C1(C)CCNCC1 WLVNOJPDJOADNT-WBVHZDCISA-N 0.000 description 2
• AGVOPGCXXGAGKM-GIIGEWEBSA-N (3as,7as)-3-[1-(3-methylpyrrolidin-3-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C1(C)CCNC1 AGVOPGCXXGAGKM-GIIGEWEBSA-N 0.000 description 2
• GBBOZVGWCUJZSV-HOTGVXAUSA-N (3as,7as)-3-[1-(4-methylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C1(C)CCNCC1 GBBOZVGWCUJZSV-HOTGVXAUSA-N 0.000 description 2
• GBBSUAFBMRNDJC-MRXNPFEDSA-N (5R)-zopiclone Chemical compound C1CN(C)CCN1C(=O)O[C@@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-MRXNPFEDSA-N 0.000 description 2
• VSWBSWWIRNCQIJ-GJZGRUSLSA-N (R,R)-asenapine Chemical compound O1C2=CC=CC=C2[C@@H]2CN(C)C[C@H]2C2=CC(Cl)=CC=C21 VSWBSWWIRNCQIJ-GJZGRUSLSA-N 0.000 description 2
• TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 description 2
• BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 2
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 2
• 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 2
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 2
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 2
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 2
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 2
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 2
• WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
• 238000005160 1H NMR spectroscopy Methods 0.000 description 2
• PMXMIIMHBWHSKN-UHFFFAOYSA-N 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCC(O)C4=NC=3C)=NOC2=C1 PMXMIIMHBWHSKN-UHFFFAOYSA-N 0.000 description 2
• ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 2
• XWVOEFLBOSSYGM-UHFFFAOYSA-N 4-morpholinyl-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)N2CCOCC2)=C1 XWVOEFLBOSSYGM-UHFFFAOYSA-N 0.000 description 2
• CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 description 2
• 208000008035 Back Pain Diseases 0.000 description 2
• CYGODHVAJQTCBG-UHFFFAOYSA-N Bifeprunox Chemical compound C=12OC(=O)NC2=CC=CC=1N(CC1)CCN1CC(C=1)=CC=CC=1C1=CC=CC=C1 CYGODHVAJQTCBG-UHFFFAOYSA-N 0.000 description 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
• 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 2
• 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 2
• GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 2
• PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 2
• 208000019695 Migraine disease Diseases 0.000 description 2
• 208000001294 Nociceptive Pain Diseases 0.000 description 2
• 208000008589 Obesity Diseases 0.000 description 2
• BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 description 2
• UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 description 2
• 208000018737 Parkinson disease Diseases 0.000 description 2
• PWRPUAKXMQAFCJ-UHFFFAOYSA-N Perlapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2CC2=CC=CC=C12 PWRPUAKXMQAFCJ-UHFFFAOYSA-N 0.000 description 2
• RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• ZTVQQQVZCWLTDF-UHFFFAOYSA-N Remifentanil Chemical compound C1CN(CCC(=O)OC)CCC1(C(=O)OC)N(C(=O)CC)C1=CC=CC=C1 ZTVQQQVZCWLTDF-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 description 2
• 208000027418 Wounds and injury Diseases 0.000 description 2
• JIWRDSBGQUQMBJ-MNOVXSKESA-N [(1s,2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexyl]methyl methanesulfonate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCCC[C@@H]1COS(C)(=O)=O JIWRDSBGQUQMBJ-MNOVXSKESA-N 0.000 description 2
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
• 230000001154 acute effect Effects 0.000 description 2
• 230000002411 adverse Effects 0.000 description 2
• 150000001340 alkali metals Chemical class 0.000 description 2
• 125000000304 alkynyl group Chemical group 0.000 description 2
• 229960003036 amisulpride Drugs 0.000 description 2
• NTJOBXMMWNYJFB-UHFFFAOYSA-N amisulpride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC NTJOBXMMWNYJFB-UHFFFAOYSA-N 0.000 description 2
• VIROVYVQCGLCII-UHFFFAOYSA-N amobarbital Chemical compound CC(C)CCC1(CC)C(=O)NC(=O)NC1=O VIROVYVQCGLCII-UHFFFAOYSA-N 0.000 description 2
• 238000001949 anaesthesia Methods 0.000 description 2
• 230000003444 anaesthetic effect Effects 0.000 description 2
• 230000003574 anti-allodynic effect Effects 0.000 description 2
• 230000003502 anti-nociceptive effect Effects 0.000 description 2
• 239000002249 anxiolytic agent Substances 0.000 description 2
• 230000000949 anxiolytic effect Effects 0.000 description 2
• 229940005530 anxiolytics Drugs 0.000 description 2
• 229960004372 aripiprazole Drugs 0.000 description 2
• 229960005245 asenapine Drugs 0.000 description 2
• 239000012131 assay buffer Substances 0.000 description 2
• 239000002585 base Substances 0.000 description 2
• 125000002619 bicyclic group Chemical group 0.000 description 2
• 229950009087 bifeprunox Drugs 0.000 description 2
• 239000012148 binding buffer Substances 0.000 description 2
• 230000004071 biological effect Effects 0.000 description 2
• 239000000872 buffer Substances 0.000 description 2
• RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 description 2
• 229960001736 buprenorphine Drugs 0.000 description 2
• MFKKPMUEGDJJSL-UHFFFAOYSA-N but-2-ynyl carbonochloridate Chemical compound CC#CCOC(Cl)=O MFKKPMUEGDJJSL-UHFFFAOYSA-N 0.000 description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 229910052791 calcium Inorganic materials 0.000 description 2
• 239000001768 carboxy methyl cellulose Substances 0.000 description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 2
• 229960001076 chlorpromazine Drugs 0.000 description 2
• ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 2
• 239000000064 cholinergic agonist Substances 0.000 description 2
• 229960004170 clozapine Drugs 0.000 description 2
• QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 2
• 229940110456 cocoa butter Drugs 0.000 description 2
• 235000019868 cocoa butter Nutrition 0.000 description 2
• 238000002648 combination therapy Methods 0.000 description 2
• 230000008878 coupling Effects 0.000 description 2
• 238000010168 coupling process Methods 0.000 description 2
• 238000005859 coupling reaction Methods 0.000 description 2
• YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
• 229960003461 dezocine Drugs 0.000 description 2
• VTMVHDZWSFQSQP-VBNZEHGJSA-N dezocine Chemical compound C1CCCC[C@H]2CC3=CC=C(O)C=C3[C@]1(C)[C@H]2N VTMVHDZWSFQSQP-VBNZEHGJSA-N 0.000 description 2
• 229960002069 diamorphine Drugs 0.000 description 2
• 208000035475 disorder Diseases 0.000 description 2
• ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 2
• 230000004064 dysfunction Effects 0.000 description 2
• GBBSUAFBMRNDJC-INIZCTEOSA-N eszopiclone Chemical compound C1CN(C)CCN1C(=O)O[C@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-INIZCTEOSA-N 0.000 description 2
• 229960001578 eszopiclone Drugs 0.000 description 2
• KAORKQKJTABAMV-UHFFFAOYSA-N ethyl 3-(4-hydroxypiperidin-1-yl)-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1(C)N1CCC(O)CC1 KAORKQKJTABAMV-UHFFFAOYSA-N 0.000 description 2
• VVSNTZLQTPWKEH-YGYNJSFOSA-N ethyl 3-[4-[[(1s,2s)-2-aminocyclohexyl]amino]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1(C)N1CCC(N[C@@H]2[C@H](CCCC2)N)CC1 VVSNTZLQTPWKEH-YGYNJSFOSA-N 0.000 description 2
• DITRGHJAHPIEEN-UHFFFAOYSA-N ethyl 3-cyano-3-(4-hydroxypiperidin-1-yl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1(C#N)N1CCC(O)CC1 DITRGHJAHPIEEN-UHFFFAOYSA-N 0.000 description 2
• MYZBDLHNWFCXEO-UHFFFAOYSA-N ethyl 4-cyano-4-(4-hydroxypiperidin-1-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(C#N)N1CCC(O)CC1 MYZBDLHNWFCXEO-UHFFFAOYSA-N 0.000 description 2
• ODSYNCKPTZTGIV-UHFFFAOYSA-N ethyl 4-methyl-4-(4-oxopiperidin-1-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(C)N1CCC(=O)CC1 ODSYNCKPTZTGIV-UHFFFAOYSA-N 0.000 description 2
• 238000000105 evaporative light scattering detection Methods 0.000 description 2
• 229960002428 fentanyl Drugs 0.000 description 2
• IVLVTNPOHDFFCJ-UHFFFAOYSA-N fentanyl citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 IVLVTNPOHDFFCJ-UHFFFAOYSA-N 0.000 description 2
• 239000000796 flavoring agent Substances 0.000 description 2
• 235000013355 food flavoring agent Nutrition 0.000 description 2
• 125000002541 furyl group Chemical group 0.000 description 2
• 239000011521 glass Substances 0.000 description 2
• 229960003878 haloperidol Drugs 0.000 description 2
• 238000004128 high performance liquid chromatography Methods 0.000 description 2
• 229960003162 iloperidone Drugs 0.000 description 2
• XMXHEBAFVSFQEX-UHFFFAOYSA-N iloperidone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C=2C3=CC=C(F)C=C3ON=2)CC1 XMXHEBAFVSFQEX-UHFFFAOYSA-N 0.000 description 2
• 238000003384 imaging method Methods 0.000 description 2
• 125000002883 imidazolyl group Chemical group 0.000 description 2
• 229960002725 isoflurane Drugs 0.000 description 2
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000001786 isothiazolyl group Chemical group 0.000 description 2
• 125000000842 isoxazolyl group Chemical group 0.000 description 2
• XBMIVRRWGCYBTQ-AVRDEDQJSA-N levacetylmethadol Chemical compound C=1C=CC=CC=1C(C[C@H](C)N(C)C)([C@@H](OC(C)=O)CC)C1=CC=CC=C1 XBMIVRRWGCYBTQ-AVRDEDQJSA-N 0.000 description 2
• 239000003446 ligand Substances 0.000 description 2
• 229960001078 lithium Drugs 0.000 description 2
• 229960000423 loxapine Drugs 0.000 description 2
• XJGVXQDUIWGIRW-UHFFFAOYSA-N loxapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 XJGVXQDUIWGIRW-UHFFFAOYSA-N 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 239000000463 material Substances 0.000 description 2
• 230000001404 mediated effect Effects 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• JLICHNCFTLFZJN-HNNXBMFYSA-N meptazinol Chemical compound C=1C=CC(O)=CC=1[C@@]1(CC)CCCCN(C)C1 JLICHNCFTLFZJN-HNNXBMFYSA-N 0.000 description 2
• 229960000365 meptazinol Drugs 0.000 description 2
• SLVMESMUVMCQIY-UHFFFAOYSA-N mesoridazine Chemical compound CN1CCCCC1CCN1C2=CC(S(C)=O)=CC=C2SC2=CC=CC=C21 SLVMESMUVMCQIY-UHFFFAOYSA-N 0.000 description 2
• 229960000300 mesoridazine Drugs 0.000 description 2
• DYRVQYFEYGVZSQ-NRAVZPKASA-N methyl 3-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 DYRVQYFEYGVZSQ-NRAVZPKASA-N 0.000 description 2
• 229920000609 methyl cellulose Polymers 0.000 description 2
• 239000001923 methylcellulose Substances 0.000 description 2
• 235000010981 methylcellulose Nutrition 0.000 description 2
• 206010027599 migraine Diseases 0.000 description 2
• DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
• 239000000472 muscarinic agonist Substances 0.000 description 2
• 229960002715 nicotine Drugs 0.000 description 2
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
• 230000009871 nonspecific binding Effects 0.000 description 2
• 235000020824 obesity Nutrition 0.000 description 2
• 125000002971 oxazolyl group Chemical group 0.000 description 2
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 2
• 229960002085 oxycodone Drugs 0.000 description 2
• 229960005118 oxymorphone Drugs 0.000 description 2
• 229960001057 paliperidone Drugs 0.000 description 2
• 239000002245 particle Substances 0.000 description 2
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
• WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
• 229950009253 perlapine Drugs 0.000 description 2
• 229960000762 perphenazine Drugs 0.000 description 2
• 229950000688 phenothiazine Drugs 0.000 description 2
• YVUQSNJEYSNKRX-UHFFFAOYSA-N pimozide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 YVUQSNJEYSNKRX-UHFFFAOYSA-N 0.000 description 2
• 229960003634 pimozide Drugs 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
• FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 description 2
• WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 2
• 229960003111 prochlorperazine Drugs 0.000 description 2
• ZXKUTOMRBVXFKV-MOPGFXCFSA-N propan-2-yl 4-[4-[(3ar,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1(C)N1CCC(N2C(N[C@@H]3CCCC[C@@H]32)=O)CC1 ZXKUTOMRBVXFKV-MOPGFXCFSA-N 0.000 description 2
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
• 125000003373 pyrazinyl group Chemical group 0.000 description 2
• 125000003226 pyrazolyl group Chemical group 0.000 description 2
• 125000002098 pyridazinyl group Chemical group 0.000 description 2
• 125000004076 pyridyl group Chemical group 0.000 description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 description 2
• 125000000168 pyrrolyl group Chemical group 0.000 description 2
• 230000027425 release of sequestered calcium ion into cytosol Effects 0.000 description 2
• 229960003394 remifentanil Drugs 0.000 description 2
• 230000004044 response Effects 0.000 description 2
• 229960001534 risperidone Drugs 0.000 description 2
• RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 2
• 229950003023 robalzotan Drugs 0.000 description 2
• MQTUXRKNJYPMCG-CYBMUJFWSA-N robalzotan Chemical compound C1CCC1N([C@H]1COC=2C(F)=CC=C(C=2C1)C(=O)N)C1CCC1 MQTUXRKNJYPMCG-CYBMUJFWSA-N 0.000 description 2
• 239000012047 saturated solution Substances 0.000 description 2
• 229960000652 sertindole Drugs 0.000 description 2
• GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 description 2
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
• 241000894007 species Species 0.000 description 2
• 208000011117 substance-related disease Diseases 0.000 description 2
• 229960004739 sufentanil Drugs 0.000 description 2
• GGCSSNBKKAUURC-UHFFFAOYSA-N sufentanil Chemical compound C1CN(CCC=2SC=CC=2)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 GGCSSNBKKAUURC-UHFFFAOYSA-N 0.000 description 2
• 229910052717 sulfur Inorganic materials 0.000 description 2
• 229960004940 sulpiride Drugs 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• IBAUKGNDWVSETP-UHFFFAOYSA-N suproclone Chemical compound C1CN(C(=O)CC)CCN1C(=O)OC1C(SCCS2)=C2C(=O)N1C1=CC=C(C=CC(Cl)=N2)C2=N1 IBAUKGNDWVSETP-UHFFFAOYSA-N 0.000 description 2
• 229950003877 suproclone Drugs 0.000 description 2
• RMXOUBDDDQUBKD-UHFFFAOYSA-N suriclone Chemical compound C1CN(C)CCN1C(=O)OC1C(SCCS2)=C2C(=O)N1C1=CC=C(C=CC(Cl)=N2)C2=N1 RMXOUBDDDQUBKD-UHFFFAOYSA-N 0.000 description 2
• 229950006866 suriclone Drugs 0.000 description 2
• 239000000375 suspending agent Substances 0.000 description 2
• 230000002195 synergetic effect Effects 0.000 description 2
• RGEFWIJOFRCMDD-OECOBVRJSA-N tert-butyl 3-[4-[(3ar,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-indol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N2C(C[C@H]3CCCC[C@@H]32)=O)CC1 RGEFWIJOFRCMDD-OECOBVRJSA-N 0.000 description 2
• VFQYSNVJSJISED-GAOSQQNJSA-N tert-butyl 3-[4-[[(1s,2s)-2-aminocyclohexyl]amino]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N[C@@H]2[C@H](CCCC2)N)CC1 VFQYSNVJSJISED-GAOSQQNJSA-N 0.000 description 2
• HNDBOPQTJBWKMI-UHFFFAOYSA-N tert-butyl 3-cyano-3-(4-hydroxypiperidin-1-yl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1(C#N)N1CCC(O)CC1 HNDBOPQTJBWKMI-UHFFFAOYSA-N 0.000 description 2
• AIEGTZZPMNTVBM-RTBURBONSA-N tert-butyl 4-[4-[[(1r,2r)-2-aminocyclohexyl]amino]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N[C@H]2[C@@H](CCCC2)N)CC1 AIEGTZZPMNTVBM-RTBURBONSA-N 0.000 description 2
• AIEGTZZPMNTVBM-RBUKOAKNSA-N tert-butyl 4-[4-[[(1r,2s)-2-aminocyclohexyl]amino]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N[C@H]2[C@H](CCCC2)N)CC1 AIEGTZZPMNTVBM-RBUKOAKNSA-N 0.000 description 2
• BZSRLKFMVOAXPO-CTNGQTDRSA-N tert-butyl 4-[4-[[(1s,2r)-2-(cyanomethyl)cyclohexyl]amino]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N[C@@H]2[C@H](CCCC2)CC#N)CC1 BZSRLKFMVOAXPO-CTNGQTDRSA-N 0.000 description 2
• SAXCOPHNOZELEQ-UHFFFAOYSA-N tert-butyl 4-cyano-4-(4-hydroxypiperidin-1-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C#N)N1CCC(O)CC1 SAXCOPHNOZELEQ-UHFFFAOYSA-N 0.000 description 2
• IRHDDYFNNCJVSS-MNOVXSKESA-N tert-butyl n-[(1s,2r)-2-(cyanomethyl)cyclohexyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCCC[C@@H]1CC#N IRHDDYFNNCJVSS-MNOVXSKESA-N 0.000 description 2
• 125000003831 tetrazolyl group Chemical group 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• 125000000335 thiazolyl group Chemical group 0.000 description 2
• 125000001544 thienyl group Chemical group 0.000 description 2
• 229960002784 thioridazine Drugs 0.000 description 2
• 229960004380 tramadol Drugs 0.000 description 2
• TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 125000001425 triazolyl group Chemical group 0.000 description 2
• ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 2
• 229960002324 trifluoperazine Drugs 0.000 description 2
• 229950001577 trimetozine Drugs 0.000 description 2
• 239000003643 water by type Substances 0.000 description 2
• 239000011592 zinc chloride Substances 0.000 description 2
• 235000005074 zinc chloride Nutrition 0.000 description 2
• 229960000607 ziprasidone Drugs 0.000 description 2
• MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 2
• 229960000820 zopiclone Drugs 0.000 description 2
• HDOZVRUNCMBHFH-UHFFFAOYSA-N zotepine Chemical compound CN(C)CCOC1=CC2=CC=CC=C2SC2=CC=C(Cl)C=C12 HDOZVRUNCMBHFH-UHFFFAOYSA-N 0.000 description 2
• 229960004496 zotepine Drugs 0.000 description 2
• AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
• QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
• SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 1
• SSJXIUAHEKJCMH-OLQVQODUSA-N (1s,2r)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-OLQVQODUSA-N 0.000 description 1
• LHYMPSWMHXUWSK-STZFKDTASA-N (2z)-4-(3,4-dichlorophenyl)-2-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]thiomorpholin-3-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1\C=C/1C(=O)N(C=2C=C(Cl)C(Cl)=CC=2)CCS\1 LHYMPSWMHXUWSK-STZFKDTASA-N 0.000 description 1
• RTFUULRHNLQEBQ-HMZVSMPESA-N (3ar,7as)-1-[1-(3-methylpyrrolidin-3-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-3h-indol-2-one Chemical compound C1CC(N2C(C[C@H]3CCCC[C@@H]32)=O)CCN1C1(C)CCNC1 RTFUULRHNLQEBQ-HMZVSMPESA-N 0.000 description 1
• LEPSCPYTKQZCBU-QUCCMNQESA-N (3ar,7as)-1-[1-[1-(cyclopropanecarbonyl)-4-methylpiperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-3h-indol-2-one Chemical compound C1CC(C)(N2CCC(CC2)N2C(C[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1CC1 LEPSCPYTKQZCBU-QUCCMNQESA-N 0.000 description 1
• DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 description 1
• FJIKWRGCXUCUIG-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-3h-1,4-benzodiazepin-2-one Chemical compound O=C([C@H](O)N=1)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl FJIKWRGCXUCUIG-HNNXBMFYSA-N 0.000 description 1
• ICPHJSKVAZMKIV-QGZVFWFLSA-N (5r)-7,8-dimethoxy-3-methyl-5-phenyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1([C@H]2CN(C)CCC=3C=C(C(=CC=32)OC)OC)=CC=CC=C1 ICPHJSKVAZMKIV-QGZVFWFLSA-N 0.000 description 1
• WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 1
• RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 1
• ZEHYJZXQEQOSON-AATRIKPKSA-N (e)-1-chloro-3-ethylpent-1-en-4-yn-3-ol Chemical compound CCC(O)(C#C)\C=C\Cl ZEHYJZXQEQOSON-AATRIKPKSA-N 0.000 description 1
• QECAKYKTTYQVKX-RMKNXTFCSA-N (e)-3-(2,5-dihydropyrrol-1-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound COC1=C(OC)C(OC)=CC(C(=O)\C=C\N2CC=CC2)=C1 QECAKYKTTYQVKX-RMKNXTFCSA-N 0.000 description 1
• TZJUVVIWVWFLCD-UHFFFAOYSA-N 1,1-dioxo-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-1,2-benzothiazol-3-one Chemical compound O=S1(=O)C2=CC=CC=C2C(=O)N1CCCCN(CC1)CCN1C1=NC=CC=N1 TZJUVVIWVWFLCD-UHFFFAOYSA-N 0.000 description 1
• IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 description 1
• 125000005877 1,4-benzodioxanyl group Chemical group 0.000 description 1
• 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
• DWPQODZAOSWNHB-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(3-methyl-5-oxo-4H-imidazol-2-yl)urea Chemical compound CN1CC(=O)N=C1NC(=O)NC1=CC=CC(Cl)=C1 DWPQODZAOSWNHB-UHFFFAOYSA-N 0.000 description 1
• QEMSVZNTSXPFJA-HNAYVOBHSA-N 1-[(1s,2s)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]-4-phenylpiperidin-4-ol Chemical compound C1([C@H](O)[C@H](C)N2CCC(O)(CC2)C=2C=CC=CC=2)=CC=C(O)C=C1 QEMSVZNTSXPFJA-HNAYVOBHSA-N 0.000 description 1
• KYWMWUUMCDZISK-UHFFFAOYSA-N 2,2,5,5-tetrakis(trifluoromethyl)-1h-imidazol-4-amine Chemical compound NC1=NC(C(F)(F)F)(C(F)(F)F)NC1(C(F)(F)F)C(F)(F)F KYWMWUUMCDZISK-UHFFFAOYSA-N 0.000 description 1
• SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
• SFSDKRYPELHLNE-OECOBVRJSA-N 2-[(1r,2s)-2-[[1-[3-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-3-yl]piperidin-4-yl]amino]cyclohexyl]acetic acid Chemical compound C1N(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N[C@@H]2[C@H](CCCC2)CC(O)=O)CC1 SFSDKRYPELHLNE-OECOBVRJSA-N 0.000 description 1
• ZYZCHUMYNSXZQK-SFYZADRCSA-N 2-[(1r,2s)-2-aminocyclohexyl]acetonitrile Chemical compound N[C@H]1CCCC[C@@H]1CC#N ZYZCHUMYNSXZQK-SFYZADRCSA-N 0.000 description 1
• JXDXANRCLTZYDP-UHFFFAOYSA-N 2-[3-(1,4-diazepan-1-ylmethyl)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound N1(CCNCCC1)CC1=NN(C=C1C=1C=NC(=NC=1)NC1CC2=CC=CC=C2C1)CC(=O)N1CC2=C(CC1)NN=N2 JXDXANRCLTZYDP-UHFFFAOYSA-N 0.000 description 1
• SPCKHVPPRJWQRZ-UHFFFAOYSA-N 2-benzhydryloxy-n,n-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 SPCKHVPPRJWQRZ-UHFFFAOYSA-N 0.000 description 1
• 125000004918 2-methyl-2-pentyl group Chemical group CC(C)(CCC)* 0.000 description 1
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
• FXZJKVODWNYPKK-UHFFFAOYSA-N 3-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-1h-quinazoline-2,4-dione Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(C4=CC=CC=C4NC3=O)=O)CC2)=C1 FXZJKVODWNYPKK-UHFFFAOYSA-N 0.000 description 1
• 125000004919 3-methyl-2-pentyl group Chemical group CC(C(C)*)CC 0.000 description 1
• YYIXFDPFZMVJNH-UHFFFAOYSA-N 3h-indol-2-one Chemical compound C1=CC=C2[N]C(=O)CC2=C1 YYIXFDPFZMVJNH-UHFFFAOYSA-N 0.000 description 1
• PCTRYMLLRKWXGF-UHFFFAOYSA-N 4-(butylamino)-1-ethyl-6-methyl-5-pyrazolo[3,4-b]pyridinecarboxylic acid ethyl ester Chemical compound CCCCNC1=C(C(=O)OCC)C(C)=NC2=C1C=NN2CC PCTRYMLLRKWXGF-UHFFFAOYSA-N 0.000 description 1
• 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
• YOQHLBBOLXJXJH-UHFFFAOYSA-N 4-propylpiperidine-1-carboxylic acid Chemical compound CCCC1CCN(C(O)=O)CC1 YOQHLBBOLXJXJH-UHFFFAOYSA-N 0.000 description 1
• 125000005941 7-oxabicyclo[2.2.1]heptyl group Chemical group 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• QYFHCFNBYQZGKW-BDQAORGHSA-N 8-[4-[[(3s)-5-methoxy-3,4-dihydro-2h-chromen-3-yl]-propylamino]butyl]-8-azaspiro[4.5]decane-7,9-dione;hydrochloride Chemical compound Cl.CCCN([C@H]1CC2=C(OC)C=CC=C2OC1)CCCCN(C(C1)=O)C(=O)CC21CCCC2 QYFHCFNBYQZGKW-BDQAORGHSA-N 0.000 description 1
• 229940124596 AChE inhibitor Drugs 0.000 description 1
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• FDQGNLOWMMVRQL-UHFFFAOYSA-N Allobarbital Chemical compound C=CCC1(CC=C)C(=O)NC(=O)NC1=O FDQGNLOWMMVRQL-UHFFFAOYSA-N 0.000 description 1
• WKEMJKQOLOHJLZ-UHFFFAOYSA-N Almogran Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CS(=O)(=O)N1CCCC1 WKEMJKQOLOHJLZ-UHFFFAOYSA-N 0.000 description 1
• 102100028116 Amine oxidase [flavin-containing] B Human genes 0.000 description 1
• 208000000044 Amnesia Diseases 0.000 description 1
• 208000031091 Amnestic disease Diseases 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 229930003347 Atropine Natural products 0.000 description 1
• 208000023275 Autoimmune disease Diseases 0.000 description 1
• VMIYHDSEFNYJSL-UHFFFAOYSA-N Bromazepam Chemical compound C12=CC(Br)=CC=C2NC(=O)CN=C1C1=CC=CC=N1 VMIYHDSEFNYJSL-UHFFFAOYSA-N 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• UMSGKTJDUHERQW-UHFFFAOYSA-N Brotizolam Chemical compound C1=2C=C(Br)SC=2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl UMSGKTJDUHERQW-UHFFFAOYSA-N 0.000 description 1
• QORQZMBCPRBCAB-UHFFFAOYSA-M Butabarbital sodium Chemical compound [Na+].CCC(C)C1(CC)C(=O)NC([O-])=NC1=O QORQZMBCPRBCAB-UHFFFAOYSA-M 0.000 description 1
• RZZPDXZPRHQOCG-OJAKKHQRSA-M CDP-choline(1-) Chemical compound O[C@@H]1[C@H](O)[C@@H](COP([O-])(=O)OP([O-])(=O)OCC[N+](C)(C)C)O[C@H]1N1C(=O)N=C(N)C=C1 RZZPDXZPRHQOCG-OJAKKHQRSA-M 0.000 description 1
• 102000017926 CHRM2 Human genes 0.000 description 1
• 102000017924 CHRM4 Human genes 0.000 description 1
• KORNTPPJEAJQIU-KJXAQDMKSA-N Cabaser Chemical compound C1=CC([C@H]2C[C@H](CN(CC=C)[C@@H]2C2)C(=O)N(CCCN(C)C)C(=O)NCC)=C3C2=CNC3=C1 KORNTPPJEAJQIU-KJXAQDMKSA-N 0.000 description 1
• 208000024172 Cardiovascular disease Diseases 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 102000009660 Cholinergic Receptors Human genes 0.000 description 1
• 108010009685 Cholinergic Receptors Proteins 0.000 description 1
• 101150012960 Chrm2 gene Proteins 0.000 description 1
• 208000017667 Chronic Disease Diseases 0.000 description 1
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 description 1
• GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
• 208000027932 Collagen disease Diseases 0.000 description 1
• 206010010774 Constipation Diseases 0.000 description 1
• 206010011224 Cough Diseases 0.000 description 1
• LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
• KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 1
• HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
• 108010057987 Desmodus rotundus salivary plasminogen activator alpha 1 Proteins 0.000 description 1
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 1
• 239000004375 Dextrin Substances 0.000 description 1
• 229920001353 Dextrin Polymers 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 206010012735 Diarrhoea Diseases 0.000 description 1
• XIQVNETUBQGFHX-UHFFFAOYSA-N Ditropan Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCN(CC)CC)C1CCCCC1 XIQVNETUBQGFHX-UHFFFAOYSA-N 0.000 description 1
• 206010013654 Drug abuse Diseases 0.000 description 1
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
• 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
• 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
• 208000011688 Generalised anxiety disease Diseases 0.000 description 1
• 208000010412 Glaucoma Diseases 0.000 description 1
• JMBQKKAJIKAWKF-UHFFFAOYSA-N Glutethimide Chemical compound C=1C=CC=CC=1C1(CC)CCC(=O)NC1=O JMBQKKAJIKAWKF-UHFFFAOYSA-N 0.000 description 1
• WYCLKVQLVUQKNZ-UHFFFAOYSA-N Halazepam Chemical compound N=1CC(=O)N(CC(F)(F)F)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 WYCLKVQLVUQKNZ-UHFFFAOYSA-N 0.000 description 1
• 239000012981 Hank's balanced salt solution Substances 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101000768078 Homo sapiens Amine oxidase [flavin-containing] B Proteins 0.000 description 1
• 208000023105 Huntington disease Diseases 0.000 description 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
• 206010020751 Hypersensitivity Diseases 0.000 description 1
• 206010020772 Hypertension Diseases 0.000 description 1
• 206010020853 Hypertonic bladder Diseases 0.000 description 1
• 206010021118 Hypotonia Diseases 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• 206010061216 Infarction Diseases 0.000 description 1
• WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
• WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
• YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 1
• NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• JEYCTXHKTXCGPB-UHFFFAOYSA-N Methaqualone Chemical compound CC1=CC=CC=C1N1C(=O)C2=CC=CC=C2N=C1C JEYCTXHKTXCGPB-UHFFFAOYSA-N 0.000 description 1
• 208000019430 Motor disease Diseases 0.000 description 1
• UQOFGTXDASPNLL-XHNCKOQMSA-N Muscarine Chemical compound C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O UQOFGTXDASPNLL-XHNCKOQMSA-N 0.000 description 1
• 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
• QOSSAOTZNIDXMA-UHFFFAOYSA-N N,N′-Dicyclohexylcarbodiimide Substances C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
• HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
• 206010028980 Neoplasm Diseases 0.000 description 1
• 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 1
• 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 1
• 102000006538 Nitric Oxide Synthase Type I Human genes 0.000 description 1
• 108010008858 Nitric Oxide Synthase Type I Proteins 0.000 description 1
• PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 description 1
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
• 206010030113 Oedema Diseases 0.000 description 1
• 208000009722 Overactive Urinary Bladder Diseases 0.000 description 1
• RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
• RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 1
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
• 229920005372 Plexiglas® Polymers 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• MWQCHHACWWAQLJ-UHFFFAOYSA-N Prazepam Chemical compound O=C1CN=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N1CC1CC1 MWQCHHACWWAQLJ-UHFFFAOYSA-N 0.000 description 1
• 208000023146 Pre-existing disease Diseases 0.000 description 1
• QPCVHQBVMYCJOM-UHFFFAOYSA-N Propiverine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCC)C(=O)OC1CCN(C)CC1 QPCVHQBVMYCJOM-UHFFFAOYSA-N 0.000 description 1
• IKMPWMZBZSAONZ-UHFFFAOYSA-N Quazepam Chemical compound FC1=CC=CC=C1C1=NCC(=S)N(CC(F)(F)F)C2=CC=C(Cl)C=C12 IKMPWMZBZSAONZ-UHFFFAOYSA-N 0.000 description 1
• BKRGVLQUQGGVSM-KBXCAEBGSA-N Revanil Chemical compound C1=CC(C=2[C@H](N(C)C[C@H](C=2)NC(=O)N(CC)CC)C2)=C3C2=CNC3=C1 BKRGVLQUQGGVSM-KBXCAEBGSA-N 0.000 description 1
• PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 description 1
• QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
• 206010039424 Salivary hypersecretion Diseases 0.000 description 1
• ZRIHAIZYIMGOAB-UHFFFAOYSA-N Secbutobarbitone Natural products CCC(C)C1(CC)C(=O)NC(=O)NC1=O ZRIHAIZYIMGOAB-UHFFFAOYSA-N 0.000 description 1
• 206010039897 Sedation Diseases 0.000 description 1
• 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
• 206010041250 Social phobia Diseases 0.000 description 1
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
• 208000020339 Spinal injury Diseases 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 208000006011 Stroke Diseases 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• SEQDDYPDSLOBDC-UHFFFAOYSA-N Temazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 SEQDDYPDSLOBDC-UHFFFAOYSA-N 0.000 description 1
• 108090000373 Tissue Plasminogen Activator Proteins 0.000 description 1
• 102000003978 Tissue Plasminogen Activator Human genes 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 208000030886 Traumatic Brain injury Diseases 0.000 description 1
• YYQRGCZGSFRBAM-UHFFFAOYSA-N Triclofos Chemical compound OP(O)(=O)OCC(Cl)(Cl)Cl YYQRGCZGSFRBAM-UHFFFAOYSA-N 0.000 description 1
• 101100107916 Xenopus laevis chrm4 gene Proteins 0.000 description 1
• GDSCFOSHSOWNDL-UHFFFAOYSA-N Zolasepam Chemical compound N=1CC(=O)N(C)C(N(N=C2C)C)=C2C=1C1=CC=CC=C1F GDSCFOSHSOWNDL-UHFFFAOYSA-N 0.000 description 1
• WXIONIWNXBAHRU-UHFFFAOYSA-N [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylidene]-dimethylazanium Chemical compound C1=CN=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 WXIONIWNXBAHRU-UHFFFAOYSA-N 0.000 description 1
• 229960000446 abciximab Drugs 0.000 description 1
• QOMNQGZXFYNBNG-UHFFFAOYSA-N acetyloxymethyl 2-[2-[2-[5-[3-(acetyloxymethoxy)-2,7-difluoro-6-oxoxanthen-9-yl]-2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]phenoxy]ethoxy]-n-[2-(acetyloxymethoxy)-2-oxoethyl]-4-methylanilino]acetate Chemical compound CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)C1=CC=C(C)C=C1OCCOC1=CC(C2=C3C=C(F)C(=O)C=C3OC3=CC(OCOC(C)=O)=C(F)C=C32)=CC=C1N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O QOMNQGZXFYNBNG-UHFFFAOYSA-N 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
• 229940099983 activase Drugs 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 229960003148 adinazolam Drugs 0.000 description 1
• GJSLOMWRLALDCT-UHFFFAOYSA-N adinazolam Chemical compound C12=CC(Cl)=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1 GJSLOMWRLALDCT-UHFFFAOYSA-N 0.000 description 1
• OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical compound C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 150000001336 alkenes Chemical class 0.000 description 1
• 150000004703 alkoxides Chemical class 0.000 description 1
• 150000003973 alkyl amines Chemical class 0.000 description 1
• 230000007815 allergy Effects 0.000 description 1
• 229960000880 allobarbital Drugs 0.000 description 1
• 125000005336 allyloxy group Chemical group 0.000 description 1
• 229960002133 almotriptan Drugs 0.000 description 1
• 229950000420 alnespirone Drugs 0.000 description 1
• 229950003674 alonimid Drugs 0.000 description 1
• 229960004538 alprazolam Drugs 0.000 description 1
• VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
• 229960003805 amantadine Drugs 0.000 description 1
• DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 229960000836 amitriptyline Drugs 0.000 description 1
• KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
• 230000006986 amnesia Effects 0.000 description 1
• 229960001301 amobarbital Drugs 0.000 description 1
• 229960002519 amoxapine Drugs 0.000 description 1
• QWGDMFLQWFTERH-UHFFFAOYSA-N amoxapine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2N=C1N1CCNCC1 QWGDMFLQWFTERH-UHFFFAOYSA-N 0.000 description 1
• 229940124326 anaesthetic agent Drugs 0.000 description 1
• 230000036592 analgesia Effects 0.000 description 1
• 230000000202 analgesic effect Effects 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 150000001450 anions Chemical class 0.000 description 1
• 239000000730 antalgic agent Substances 0.000 description 1
• 230000000259 anti-tumor effect Effects 0.000 description 1
• 229940125681 anticonvulsant agent Drugs 0.000 description 1
• 239000001961 anticonvulsive agent Substances 0.000 description 1
• 239000000935 antidepressant agent Substances 0.000 description 1
• 229940005513 antidepressants Drugs 0.000 description 1
• 239000000164 antipsychotic agent Substances 0.000 description 1
• 229940005529 antipsychotics Drugs 0.000 description 1
• 239000003443 antiviral agent Substances 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 239000007900 aqueous suspension Substances 0.000 description 1
• 230000037007 arousal Effects 0.000 description 1
• 206010003246 arthritis Diseases 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• 238000011914 asymmetric synthesis Methods 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
• 229960000396 atropine Drugs 0.000 description 1
• 239000003693 atypical antipsychotic agent Substances 0.000 description 1
• 229940127236 atypical antipsychotics Drugs 0.000 description 1
• 125000004069 aziridinyl group Chemical group 0.000 description 1
• 229940125717 barbiturate Drugs 0.000 description 1
• 150000007514 bases Chemical class 0.000 description 1
• 230000006399 behavior Effects 0.000 description 1
• 230000003542 behavioural effect Effects 0.000 description 1
• 229950001957 bentazepam Drugs 0.000 description 1
• AIZFEOPQVZBNGH-UHFFFAOYSA-N bentazepam Chemical compound C1=2C=3CCCCC=3SC=2NC(=O)CN=C1C1=CC=CC=C1 AIZFEOPQVZBNGH-UHFFFAOYSA-N 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• GNRXCIONJWKSEA-UHFFFAOYSA-N benzoctamine Chemical compound C12=CC=CC=C2C2(CNC)C3=CC=CC=C3C1CC2 GNRXCIONJWKSEA-UHFFFAOYSA-N 0.000 description 1
• 229960001303 benzoctamine Drugs 0.000 description 1
• 229940049706 benzodiazepine Drugs 0.000 description 1
• 150000001557 benzodiazepines Chemical class 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 238000012925 biological evaluation Methods 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• IEPBPSSCIZTJIF-UHFFFAOYSA-N bis(2,2,2-trichloroethyl) carbonate Chemical compound ClC(Cl)(Cl)COC(=O)OCC(Cl)(Cl)Cl IEPBPSSCIZTJIF-UHFFFAOYSA-N 0.000 description 1
• 230000036471 bradycardia Effects 0.000 description 1
• 208000006218 bradycardia Diseases 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• 229960002729 bromazepam Drugs 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 229960002802 bromocriptine Drugs 0.000 description 1
• OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
• 229960003051 brotizolam Drugs 0.000 description 1
• 229960001058 bupropion Drugs 0.000 description 1
• SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 1
• 229960002495 buspirone Drugs 0.000 description 1
• QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 description 1
• 229940015694 butabarbital Drugs 0.000 description 1
• UZVHFVZFNXBMQJ-UHFFFAOYSA-N butalbital Chemical compound CC(C)CC1(CC=C)C(=O)NC(=O)NC1=O UZVHFVZFNXBMQJ-UHFFFAOYSA-N 0.000 description 1
• 229960002546 butalbital Drugs 0.000 description 1
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
• 229960004596 cabergoline Drugs 0.000 description 1
• 150000001669 calcium Chemical class 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• HLSLSXBFTXUKCY-UHFFFAOYSA-N capuride Chemical compound CCC(C)C(CC)C(=O)NC(N)=O HLSLSXBFTXUKCY-UHFFFAOYSA-N 0.000 description 1
• 229950003152 capuride Drugs 0.000 description 1
• AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
• 229960004484 carbachol Drugs 0.000 description 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• 125000004623 carbolinyl group Chemical group 0.000 description 1
• 229910052799 carbon Inorganic materials 0.000 description 1
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
• 230000000747 cardiac effect Effects 0.000 description 1
• 230000005961 cardioprotection Effects 0.000 description 1
• 229960000590 celecoxib Drugs 0.000 description 1
• RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 1
• 239000006143 cell culture medium Substances 0.000 description 1
• 210000000170 cell membrane Anatomy 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 238000012512 characterization method Methods 0.000 description 1
• UKFDTMNJMKWWNK-UHFFFAOYSA-N chembl2104165 Chemical compound C12=CC(Cl)=CC=C2N\C(=N\CC2CC2)C[N+]([O-])=C1C1=CC=CC=C1 UKFDTMNJMKWWNK-UHFFFAOYSA-N 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 239000003638 chemical reducing agent Substances 0.000 description 1
• 229960004782 chlordiazepoxide Drugs 0.000 description 1
• ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
• 229960001231 choline Drugs 0.000 description 1
• 230000001713 cholinergic effect Effects 0.000 description 1
• 239000000544 cholinesterase inhibitor Substances 0.000 description 1
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
• 238000013375 chromatographic separation Methods 0.000 description 1
• 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 229960001653 citalopram Drugs 0.000 description 1
• 229960001284 citicoline Drugs 0.000 description 1
• 229960004606 clomipramine Drugs 0.000 description 1
• 229960003120 clonazepam Drugs 0.000 description 1
• DGBIGWXXNGSACT-UHFFFAOYSA-N clonazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl DGBIGWXXNGSACT-UHFFFAOYSA-N 0.000 description 1
• 229960002896 clonidine Drugs 0.000 description 1
• 229950000551 cloperidone Drugs 0.000 description 1
• 229960004362 clorazepate Drugs 0.000 description 1
• XDDJGVMJFWAHJX-UHFFFAOYSA-N clorazepic acid Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(C(=O)O)N=C1C1=CC=CC=C1 XDDJGVMJFWAHJX-UHFFFAOYSA-N 0.000 description 1
• 230000019771 cognition Effects 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 239000012230 colorless oil Substances 0.000 description 1
• 229940000425 combination drug Drugs 0.000 description 1
• 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
• ILVITZMPXQQPBD-OFAXGOBFSA-N crobenetine Chemical compound O([C@H](CN1[C@@H]2CC3=CC=CC=C3[C@@H](C2(C)C)CC1)C)CC1=CC=CC=C1 ILVITZMPXQQPBD-OFAXGOBFSA-N 0.000 description 1
• 229950005056 crobenetine Drugs 0.000 description 1
• 125000004122 cyclic group Chemical group 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 1
• 229950010040 cyprazepam Drugs 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• 230000007850 degeneration Effects 0.000 description 1
• 229960003914 desipramine Drugs 0.000 description 1
• 229950001282 desmoteplase Drugs 0.000 description 1
• UPMOVJBGNREKJV-CQOQZXRMSA-N dexclamol Chemical compound C12=CC=CC=C2CCC2=CC=CC3=C2[C@@H]1CN1CC[C@@](C(C)C)(O)C[C@@H]13 UPMOVJBGNREKJV-CQOQZXRMSA-N 0.000 description 1
• 229950005215 dexclamol Drugs 0.000 description 1
• 235000019425 dextrin Nutrition 0.000 description 1
• 229960003529 diazepam Drugs 0.000 description 1
• AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
• ATKXDQOHNICLQW-UHFFFAOYSA-N dichloralphenazone Chemical compound OC(O)C(Cl)(Cl)Cl.OC(O)C(Cl)(Cl)Cl.CN1C(C)=CC(=O)N1C1=CC=CC=C1 ATKXDQOHNICLQW-UHFFFAOYSA-N 0.000 description 1
• 229960005422 dichloralphenazone Drugs 0.000 description 1
• DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
• 229960001259 diclofenac Drugs 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• 125000000532 dioxanyl group Chemical group 0.000 description 1
• 125000005879 dioxolanyl group Chemical group 0.000 description 1
• 229960000520 diphenhydramine Drugs 0.000 description 1
• XLZOVRYBVCMCGL-BPNVQINPSA-L disodium;4-[(z)-[tert-butyl(oxido)azaniumylidene]methyl]benzene-1,3-disulfonate Chemical compound [Na+].[Na+].CC(C)(C)[N+](\[O-])=C\C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O XLZOVRYBVCMCGL-BPNVQINPSA-L 0.000 description 1
• 229960003530 donepezil Drugs 0.000 description 1
• 229940052760 dopamine agonists Drugs 0.000 description 1
• 239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
• 239000000221 dopamine uptake inhibitor Substances 0.000 description 1
• 229960005426 doxepin Drugs 0.000 description 1
• ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
• 238000001647 drug administration Methods 0.000 description 1
• 206010013663 drug dependence Diseases 0.000 description 1
• 201000006549 dyspepsia Diseases 0.000 description 1
• 229960002472 eletriptan Drugs 0.000 description 1
• OTLDLQZJRFYOJR-LJQANCHMSA-N eletriptan Chemical compound CN1CCC[C@@H]1CC1=CN=C2[C]1C=C(CCS(=O)(=O)C=1C=CC=CC=1)C=C2 OTLDLQZJRFYOJR-LJQANCHMSA-N 0.000 description 1
• 229950007566 elzasonan Drugs 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 238000005516 engineering process Methods 0.000 description 1
• 229960004341 escitalopram Drugs 0.000 description 1
• WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 description 1
• CDCHDCWJMGXXRH-UHFFFAOYSA-N estazolam Chemical compound C=1C(Cl)=CC=C(N2C=NN=C2CN=2)C=1C=2C1=CC=CC=C1 CDCHDCWJMGXXRH-UHFFFAOYSA-N 0.000 description 1
• 229960002336 estazolam Drugs 0.000 description 1
• 229960004447 ethchlorvynol Drugs 0.000 description 1
• HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
• FSRWEZFSESZVCX-JUAJCIKASA-N ethyl 3-[4-[(3ar,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-indol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1(C)N1CCC(N2C(C[C@H]3CCCC[C@@H]32)=O)CC1 FSRWEZFSESZVCX-JUAJCIKASA-N 0.000 description 1
• JVYQKKGONMWXNA-UHFFFAOYSA-N ethyl 3-methyl-3-(4-oxopiperidin-1-yl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC1(C)N1CCC(=O)CC1 JVYQKKGONMWXNA-UHFFFAOYSA-N 0.000 description 1
• DQYGBMLEVQLDQC-UHFFFAOYSA-N ethyl 3-oxopyrrolidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(=O)C1 DQYGBMLEVQLDQC-UHFFFAOYSA-N 0.000 description 1
• IDECSARNUYYRQF-UHFFFAOYSA-N ethyl 4-(4-hydroxypiperidin-1-yl)-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(C)N1CCC(O)CC1 IDECSARNUYYRQF-UHFFFAOYSA-N 0.000 description 1
• KPVQSGDOQBFPQP-ROUUACIJSA-N ethyl 4-[4-[[(1s,2s)-2-aminocyclohexyl]amino]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(C)N1CCC(N[C@@H]2[C@H](CCCC2)N)CC1 KPVQSGDOQBFPQP-ROUUACIJSA-N 0.000 description 1
• LUBGFMZTGFXIIN-UHFFFAOYSA-N ethyl 4-oxopiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(=O)CC1 LUBGFMZTGFXIIN-UHFFFAOYSA-N 0.000 description 1
• 229960001690 etomidate Drugs 0.000 description 1
• NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
• 229960004945 etoricoxib Drugs 0.000 description 1
• MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 description 1
• 230000002964 excitative effect Effects 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 229950002489 fenobam Drugs 0.000 description 1
• 229960002200 flunitrazepam Drugs 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 229960002464 fluoxetine Drugs 0.000 description 1
• 229960003528 flurazepam Drugs 0.000 description 1
• SAADBVWGJQAEFS-UHFFFAOYSA-N flurazepam Chemical compound N=1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F SAADBVWGJQAEFS-UHFFFAOYSA-N 0.000 description 1
• 229960004038 fluvoxamine Drugs 0.000 description 1
• CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• JMYCGCXYZZHWMO-UHFFFAOYSA-N fosazepam Chemical compound N=1CC(=O)N(CP(C)(=O)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 JMYCGCXYZZHWMO-UHFFFAOYSA-N 0.000 description 1
• 229950006306 fosazepam Drugs 0.000 description 1
• 229960002284 frovatriptan Drugs 0.000 description 1
• SIBNYOSJIXCDRI-SECBINFHSA-N frovatriptan Chemical compound C1=C(C(N)=O)[CH]C2=C(C[C@H](NC)CC3)C3=NC2=C1 SIBNYOSJIXCDRI-SECBINFHSA-N 0.000 description 1
• 125000003838 furazanyl group Chemical group 0.000 description 1
• 230000004927 fusion Effects 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 230000005176 gastrointestinal motility Effects 0.000 description 1
• 208000029364 generalized anxiety disease Diseases 0.000 description 1
• 229960000647 gepirone Drugs 0.000 description 1
• QOIGKGMMAGJZNZ-UHFFFAOYSA-N gepirone Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 QOIGKGMMAGJZNZ-UHFFFAOYSA-N 0.000 description 1
• 230000000762 glandular Effects 0.000 description 1
• 229960002972 glutethimide Drugs 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 229960002158 halazepam Drugs 0.000 description 1
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
• 125000006038 hexenyl group Chemical group 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 239000008240 homogeneous mixture Substances 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• 150000003840 hydrochlorides Chemical class 0.000 description 1
• 229960000930 hydroxyzine Drugs 0.000 description 1
• ZQDWXGKKHFNSQK-UHFFFAOYSA-N hydroxyzine Chemical compound C1CN(CCOCCO)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZQDWXGKKHFNSQK-UHFFFAOYSA-N 0.000 description 1
• 230000000917 hyperalgesic effect Effects 0.000 description 1
• 239000003326 hypnotic agent Substances 0.000 description 1
• 230000000147 hypnotic effect Effects 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• 229960004801 imipramine Drugs 0.000 description 1
• BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
• 239000002955 immunomodulating agent Substances 0.000 description 1
• 229940121354 immunomodulator Drugs 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 230000007574 infarction Effects 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 230000000977 initiatory effect Effects 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 208000014674 injury Diseases 0.000 description 1
• 206010022437 insomnia Diseases 0.000 description 1
• 230000003834 intracellular effect Effects 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 230000001057 ionotropic effect Effects 0.000 description 1
• 229950003599 ipsapirone Drugs 0.000 description 1
• 208000002551 irritable bowel syndrome Diseases 0.000 description 1
• 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
• 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 description 1
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 229940060977 lidoderm Drugs 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 229960003587 lisuride Drugs 0.000 description 1
• 238000011068 loading method Methods 0.000 description 1
• 229960004391 lorazepam Drugs 0.000 description 1
• 229960004033 lormetazepam Drugs 0.000 description 1
• 229960002373 loxoprofen Drugs 0.000 description 1
• BAZQYVYVKYOAGO-UHFFFAOYSA-M loxoprofen sodium hydrate Chemical compound O.O.[Na+].C1=CC(C(C([O-])=O)C)=CC=C1CC1C(=O)CCC1 BAZQYVYVKYOAGO-UHFFFAOYSA-M 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 210000002988 lumbosacral plexus Anatomy 0.000 description 1
• 229960000994 lumiracoxib Drugs 0.000 description 1
• KHPKQFYUPIUARC-UHFFFAOYSA-N lumiracoxib Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=CC=C1Cl KHPKQFYUPIUARC-UHFFFAOYSA-N 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
• 239000001095 magnesium carbonate Substances 0.000 description 1
• 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 229960004090 maprotiline Drugs 0.000 description 1
• QSLMDECMDJKHMQ-GSXCWMCISA-N maprotiline Chemical compound C12=CC=CC=C2[C@@]2(CCCNC)C3=CC=CC=C3[C@@H]1CC2 QSLMDECMDJKHMQ-GSXCWMCISA-N 0.000 description 1
• 229950007403 mecloqualone Drugs 0.000 description 1
• SFITWQDBYUMAPS-UHFFFAOYSA-N mecloqualone Chemical compound CC1=NC2=CC=CC=C2C(=O)N1C1=CC=CC=C1Cl SFITWQDBYUMAPS-UHFFFAOYSA-N 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 229960003194 meglumine Drugs 0.000 description 1
• 229960003987 melatonin Drugs 0.000 description 1
• DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 1
• BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 description 1
• 229960004640 memantine Drugs 0.000 description 1
• ALARQZQTBTVLJV-UHFFFAOYSA-N mephobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)N(C)C1=O ALARQZQTBTVLJV-UHFFFAOYSA-N 0.000 description 1
• 229960004815 meprobamate Drugs 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• 229960002803 methaqualone Drugs 0.000 description 1
• NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
• YKFLJYAKACCWMH-UHFFFAOYSA-N methyl piperidine-1-carboxylate Chemical compound COC(=O)N1CCCCC1 YKFLJYAKACCWMH-UHFFFAOYSA-N 0.000 description 1
• UWHWNFVVODLFIQ-UHFFFAOYSA-N methyl pyrrolidine-1-carboxylate Chemical compound COC(=O)N1CCCC1 UWHWNFVVODLFIQ-UHFFFAOYSA-N 0.000 description 1
• 229960001703 methylphenobarbital Drugs 0.000 description 1
• 229950010642 midaflur Drugs 0.000 description 1
• 229960003793 midazolam Drugs 0.000 description 1
• DDLIGBOFAVUZHB-UHFFFAOYSA-N midazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NC=C2CN=C1C1=CC=CC=C1F DDLIGBOFAVUZHB-UHFFFAOYSA-N 0.000 description 1
• 229940101972 mirapex Drugs 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 239000003068 molecular probe Substances 0.000 description 1
• 239000004050 mood stabilizer Substances 0.000 description 1
• 229940127237 mood stabilizer Drugs 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• 239000003149 muscarinic antagonist Substances 0.000 description 1
• 210000003205 muscle Anatomy 0.000 description 1
• 230000036640 muscle relaxation Effects 0.000 description 1
• NDVZIUGCCMZHLG-UHFFFAOYSA-N n-methyl-3-(2-methylsulfanylphenoxy)-3-phenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1SC NDVZIUGCCMZHLG-UHFFFAOYSA-N 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
• 229960002009 naproxen Drugs 0.000 description 1
• 229960005254 naratriptan Drugs 0.000 description 1
• UNHGSHHVDNGCFN-UHFFFAOYSA-N naratriptan Chemical compound C=12[CH]C(CCS(=O)(=O)NC)=CC=C2N=CC=1C1CCN(C)CC1 UNHGSHHVDNGCFN-UHFFFAOYSA-N 0.000 description 1
• 229960001800 nefazodone Drugs 0.000 description 1
• VRBKIVRKKCLPHA-UHFFFAOYSA-N nefazodone Chemical compound O=C1N(CCOC=2C=CC=CC=2)C(CC)=NN1CCCN(CC1)CCN1C1=CC=CC(Cl)=C1 VRBKIVRKKCLPHA-UHFFFAOYSA-N 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 210000005036 nerve Anatomy 0.000 description 1
• 230000009907 neuroendocrine response Effects 0.000 description 1
• 239000000842 neuromuscular blocking agent Substances 0.000 description 1
• 239000002858 neurotransmitter agent Substances 0.000 description 1
• 229950008643 nisobamate Drugs 0.000 description 1
• CBDPCXYQNVDTMW-UHFFFAOYSA-N nisobamate Chemical compound NC(=O)OCC(C)(C(C)CC)COC(=O)NC(C)C CBDPCXYQNVDTMW-UHFFFAOYSA-N 0.000 description 1
• 229960001454 nitrazepam Drugs 0.000 description 1
• KJONHKAYOJNZEC-UHFFFAOYSA-N nitrazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1 KJONHKAYOJNZEC-UHFFFAOYSA-N 0.000 description 1
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• 229960001158 nortriptyline Drugs 0.000 description 1
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229940005483 opioid analgesics Drugs 0.000 description 1
• 210000000056 organ Anatomy 0.000 description 1
• 208000020629 overactive bladder Diseases 0.000 description 1
• 229960004535 oxazepam Drugs 0.000 description 1
• ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 1
• 125000003566 oxetanyl group Chemical group 0.000 description 1
• 125000000466 oxiranyl group Chemical group 0.000 description 1
• 229960005434 oxybutynin Drugs 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• 239000001301 oxygen Chemical group 0.000 description 1
• 208000019906 panic disease Diseases 0.000 description 1
• 229960005489 paracetamol Drugs 0.000 description 1
• 210000001002 parasympathetic nervous system Anatomy 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 229960002296 paroxetine Drugs 0.000 description 1
• 239000001814 pectin Substances 0.000 description 1
• 235000010987 pectin Nutrition 0.000 description 1
• 229920001277 pectin Polymers 0.000 description 1
• 229960001412 pentobarbital Drugs 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 229960004851 pergolide Drugs 0.000 description 1
• YEHCICAEULNIGD-MZMPZRCHSA-N pergolide Chemical compound C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 YEHCICAEULNIGD-MZMPZRCHSA-N 0.000 description 1
• 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
• 230000002093 peripheral effect Effects 0.000 description 1
• 239000002831 pharmacologic agent Substances 0.000 description 1
• 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
• 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
• 229960000964 phenelzine Drugs 0.000 description 1
• 229960002695 phenobarbital Drugs 0.000 description 1
• DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
• 125000005954 phenoxathiinyl group Chemical group 0.000 description 1
• 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 229960001416 pilocarpine Drugs 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 229920001983 poloxamer Polymers 0.000 description 1
• 125000003367 polycyclic group Chemical group 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 239000004926 polymethyl methacrylate Substances 0.000 description 1
• 238000002600 positron emission tomography Methods 0.000 description 1
• 208000028173 post-traumatic stress disease Diseases 0.000 description 1
• 230000002980 postoperative effect Effects 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229960003089 pramipexole Drugs 0.000 description 1
• 229960004856 prazepam Drugs 0.000 description 1
• AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 description 1
• 206010036596 premature ejaculation Diseases 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
• 230000008569 process Effects 0.000 description 1
• ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
• RAMTXCRMKBFPRG-UHFFFAOYSA-N prop-2-ynyl carbonochloridate Chemical compound ClC(=O)OCC#C RAMTXCRMKBFPRG-UHFFFAOYSA-N 0.000 description 1
• ZXKUTOMRBVXFKV-RTBURBONSA-N propan-2-yl 4-[4-[(3ar,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1(C)N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 ZXKUTOMRBVXFKV-RTBURBONSA-N 0.000 description 1
• RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
• 230000000069 prophylactic effect Effects 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• 229960003510 propiverine Drugs 0.000 description 1
• 229960004134 propofol Drugs 0.000 description 1
• OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
• 229960002601 protriptyline Drugs 0.000 description 1
• BWPIARFWQZKAIA-UHFFFAOYSA-N protriptyline Chemical compound C1=CC2=CC=CC=C2C(CCCNC)C2=CC=CC=C21 BWPIARFWQZKAIA-UHFFFAOYSA-N 0.000 description 1
• 208000020016 psychiatric disease Diseases 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000002755 pyrazolinyl group Chemical group 0.000 description 1
• 125000001422 pyrrolinyl group Chemical group 0.000 description 1
• 229960001964 quazepam Drugs 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
• RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical compound C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 description 1
• 229960000245 rasagiline Drugs 0.000 description 1
• 238000011552 rat model Methods 0.000 description 1
• 229960003770 reboxetine Drugs 0.000 description 1
• CBQGYUDMJHNJBX-RTBURBONSA-N reboxetine Chemical compound CCOC1=CC=CC=C1O[C@H](C=1C=CC=CC=1)[C@@H]1OCCNC1 CBQGYUDMJHNJBX-RTBURBONSA-N 0.000 description 1
• 239000000018 receptor agonist Substances 0.000 description 1
• 229940044601 receptor agonist Drugs 0.000 description 1
• MQGIGGJUPITZSE-UHFFFAOYSA-N reclazepam Chemical compound C12=CC(Cl)=CC=C2N(C=2OCC(=O)N=2)CCN=C1C1=CC=CC=C1Cl MQGIGGJUPITZSE-UHFFFAOYSA-N 0.000 description 1
• 229950004797 reclazepam Drugs 0.000 description 1
• 230000002829 reductive effect Effects 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• YGYBFMRFXNDIPO-QGZVFWFLSA-N repinotan Chemical compound O=S1(=O)C2=CC=CC=C2C(=O)N1CCCCNC[C@@H]1OC2=CC=CC=C2CC1 YGYBFMRFXNDIPO-QGZVFWFLSA-N 0.000 description 1
• 229950009693 repinotan Drugs 0.000 description 1
• 229940113775 requip Drugs 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 0.000 description 1
• 229960000425 rizatriptan Drugs 0.000 description 1
• TXHZXHICDBAVJW-UHFFFAOYSA-N rizatriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1CN1C=NC=N1 TXHZXHICDBAVJW-UHFFFAOYSA-N 0.000 description 1
• 229960000371 rofecoxib Drugs 0.000 description 1
• RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 1
• 229950004692 roletamide Drugs 0.000 description 1
• 229960001879 ropinirole Drugs 0.000 description 1
• 208000026451 salivation Diseases 0.000 description 1
• 229960002060 secobarbital Drugs 0.000 description 1
• KQPKPCNLIDLUMF-UHFFFAOYSA-N secobarbital Chemical compound CCCC(C)C1(CC=C)C(=O)NC(=O)NC1=O KQPKPCNLIDLUMF-UHFFFAOYSA-N 0.000 description 1
• 230000036280 sedation Effects 0.000 description 1
• MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 1
• 230000031893 sensory processing Effects 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 238000013207 serial dilution Methods 0.000 description 1
• 229960002073 sertraline Drugs 0.000 description 1
• VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
• 229960004425 sibutramine Drugs 0.000 description 1
• UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
• 239000000741 silica gel Substances 0.000 description 1
• 229910002027 silica gel Inorganic materials 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 239000012279 sodium borohydride Substances 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
• 239000007909 solid dosage form Substances 0.000 description 1
• 229960003855 solifenacin Drugs 0.000 description 1
• FBOUYBDGKBSUES-VXKWHMMOSA-N solifenacin Chemical compound C1([C@H]2C3=CC=CC=C3CCN2C(O[C@@H]2C3CCN(CC3)C2)=O)=CC=CC=C1 FBOUYBDGKBSUES-VXKWHMMOSA-N 0.000 description 1
• 210000003594 spinal ganglia Anatomy 0.000 description 1
• WZAIVXXKOAWTGQ-UHFFFAOYSA-N spiro[2,3-dihydronaphthalene-4,3'-piperidine]-1,2',6'-trione Chemical compound O=C1NC(=O)CCC11C2=CC=CC=C2C(=O)CC1 WZAIVXXKOAWTGQ-UHFFFAOYSA-N 0.000 description 1
• 238000013222 sprague-dawley male rat Methods 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 239000008223 sterile water Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 235000000346 sugar Nutrition 0.000 description 1
• 239000011593 sulfur Chemical group 0.000 description 1
• 229960003708 sumatriptan Drugs 0.000 description 1
• KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 230000035900 sweating Effects 0.000 description 1
• 210000002820 sympathetic nervous system Anatomy 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 229960001685 tacrine Drugs 0.000 description 1
• YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 229940000238 tasmar Drugs 0.000 description 1
• 229960003188 temazepam Drugs 0.000 description 1
• 235000007586 terpenes Nutrition 0.000 description 1
• YTBMRMPNNMENJQ-UHFFFAOYSA-N tert-butyl 3-(4-hydroxypiperidin-1-yl)-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1(C)N1CCC(O)CC1 YTBMRMPNNMENJQ-UHFFFAOYSA-N 0.000 description 1
• CVCMVABSSZJNFE-XWATYHNTSA-N tert-butyl 3-[4-[(3ar,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 CVCMVABSSZJNFE-XWATYHNTSA-N 0.000 description 1
• CVCMVABSSZJNFE-KJMDXERQSA-N tert-butyl 3-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 CVCMVABSSZJNFE-KJMDXERQSA-N 0.000 description 1
• CCYXPCLBIVOBSV-KPNPHKMBSA-N tert-butyl 3-[4-[[(1s,2r)-2-(cyanomethyl)cyclohexyl]amino]piperidin-1-yl]-3-methylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N[C@@H]2[C@H](CCCC2)CC#N)CC1 CCYXPCLBIVOBSV-KPNPHKMBSA-N 0.000 description 1
• JSOMVCDXPUXKIC-UHFFFAOYSA-N tert-butyl 3-oxopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)C1 JSOMVCDXPUXKIC-UHFFFAOYSA-N 0.000 description 1
• YZDIPJNYADNKAX-UHFFFAOYSA-N tert-butyl 4-(4-hydroxypiperidin-1-yl)-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C)N1CCC(O)CC1 YZDIPJNYADNKAX-UHFFFAOYSA-N 0.000 description 1
• FOLNBRUMVDDPBA-MOPGFXCFSA-N tert-butyl 4-[4-[(3ar,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N2C(N[C@@H]3CCCC[C@@H]32)=O)CC1 FOLNBRUMVDDPBA-MOPGFXCFSA-N 0.000 description 1
• XFOMOYBBCIBJQH-QUCCMNQESA-N tert-butyl 4-[4-[(3ar,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-indol-1-yl]piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C)N1CCC(N2C(C[C@H]3CCCC[C@@H]32)=O)CC1 XFOMOYBBCIBJQH-QUCCMNQESA-N 0.000 description 1
• ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
• XUFBETUUQRMWRY-ZJUUUORDSA-N tert-butyl n-[(1s,2s)-2-(hydroxymethyl)cyclohexyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCCC[C@@H]1CO XUFBETUUQRMWRY-ZJUUUORDSA-N 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
• 239000002562 thickening agent Substances 0.000 description 1
• 125000002053 thietanyl group Chemical group 0.000 description 1
• 125000001730 thiiranyl group Chemical group 0.000 description 1
• 125000005505 thiomorpholino group Chemical group 0.000 description 1
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• 239000003106 tissue adhesive Substances 0.000 description 1
• MIQPIUSUKVNLNT-UHFFFAOYSA-N tolcapone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 MIQPIUSUKVNLNT-UHFFFAOYSA-N 0.000 description 1
• 229960004045 tolterodine Drugs 0.000 description 1
• OOGJQPCLVADCPB-HXUWFJFHSA-N tolterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 OOGJQPCLVADCPB-HXUWFJFHSA-N 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
• 229950002859 tracazolate Drugs 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 230000009529 traumatic brain injury Effects 0.000 description 1
• 229950005135 traxoprodil Drugs 0.000 description 1
• 229960003991 trazodone Drugs 0.000 description 1
• PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 description 1
• 229950002464 trepipam Drugs 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• JOFWLTCLBGQGBO-UHFFFAOYSA-N triazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl JOFWLTCLBGQGBO-UHFFFAOYSA-N 0.000 description 1
• 229960003386 triazolam Drugs 0.000 description 1
• HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
• 229960001147 triclofos Drugs 0.000 description 1
• 229960002431 trimipramine Drugs 0.000 description 1
• ZSCDBOWYZJWBIY-UHFFFAOYSA-N trimipramine Chemical compound C1CC2=CC=CC=C2N(CC(CN(C)C)C)C2=CC=CC=C21 ZSCDBOWYZJWBIY-UHFFFAOYSA-N 0.000 description 1
• DTMPGSXFUXZBDK-UHFFFAOYSA-N uldazepam Chemical compound C12=CC(Cl)=CC=C2N=C(NOCC=C)CN=C1C1=CC=CC=C1Cl DTMPGSXFUXZBDK-UHFFFAOYSA-N 0.000 description 1
• 229950004526 uldazepam Drugs 0.000 description 1
• 229960002004 valdecoxib Drugs 0.000 description 1
• LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
• BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 1
• 229960004688 venlafaxine Drugs 0.000 description 1
• PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
• 229960001722 verapamil Drugs 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 239000011345 viscous material Substances 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1
• 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
• 229960004010 zaleplon Drugs 0.000 description 1
• HUNXMJYCHXQEGX-UHFFFAOYSA-N zaleplon Chemical compound CCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 HUNXMJYCHXQEGX-UHFFFAOYSA-N 0.000 description 1
• 229960001366 zolazepam Drugs 0.000 description 1
• 229960001360 zolmitriptan Drugs 0.000 description 1
• UTAZCRNOSWWEFR-ZDUSSCGKSA-N zolmitriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1C[C@H]1COC(=O)N1 UTAZCRNOSWWEFR-ZDUSSCGKSA-N 0.000 description 1
• 229960001475 zolpidem Drugs 0.000 description 1
• ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 1