NZ566508A - Benzimidazole derivatives which have activity at M1 receptor and their uses in medicine - Google Patents

Info

Publication number

NZ566508A

NZ566508A NZ566508A NZ56650806A NZ566508A NZ 566508 A NZ566508 A NZ 566508A NZ 566508 A NZ566508 A NZ 566508A NZ 56650806 A NZ56650806 A NZ 56650806A NZ 566508 A NZ566508 A NZ 566508A

Authority

NZ

New Zealand

Prior art keywords

group

compound

formula

fluoro

disorder

Prior art date

2005-09-30

Links

• Espacenet
• Global Dossier
• Discuss

• 239000003814 drug Substances 0.000 title claims description 44
• 230000000694 effects Effects 0.000 title claims description 37
• 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title abstract 2
• 102000017927 CHRM1 Human genes 0.000 title description 3
• 101150073075 Chrm1 gene Proteins 0.000 title description 3
• 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 235
• 208000028017 Psychotic disease Diseases 0.000 claims abstract description 57
• 208000010877 cognitive disease Diseases 0.000 claims abstract description 20
• 208000028698 Cognitive impairment Diseases 0.000 claims abstract description 15
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 106
• 239000000203 mixture Substances 0.000 claims description 94
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 67
• 238000000034 method Methods 0.000 claims description 61
• -1 HCI salt Chemical class 0.000 claims description 58
• 150000003839 salts Chemical class 0.000 claims description 57
• 238000011282 treatment Methods 0.000 claims description 53
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
• 239000012453 solvate Substances 0.000 claims description 47
• 125000001153 fluoro group Chemical group F* 0.000 claims description 43
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 239000001257 hydrogen Substances 0.000 claims description 36
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
• 238000006243 chemical reaction Methods 0.000 claims description 30
• 230000008569 process Effects 0.000 claims description 30
• 125000003545 alkoxy group Chemical group 0.000 claims description 26
• 238000005160 1H NMR spectroscopy Methods 0.000 claims description 23
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
• 238000004519 manufacturing process Methods 0.000 claims description 16
• 238000004587 chromatography analysis Methods 0.000 claims description 15
• 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 15
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 12
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
• 239000003153 chemical reaction reagent Substances 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 238000005932 reductive alkylation reaction Methods 0.000 claims description 10
• 238000002560 therapeutic procedure Methods 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 230000008878 coupling Effects 0.000 claims description 8
• 238000010168 coupling process Methods 0.000 claims description 8
• 238000005859 coupling reaction Methods 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 150000002367 halogens Chemical group 0.000 claims description 8
• 238000010438 heat treatment Methods 0.000 claims description 8
• 239000012442 inert solvent Substances 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 230000003551 muscarinic effect Effects 0.000 claims description 8
• 229910052763 palladium Inorganic materials 0.000 claims description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
• 230000008484 agonism Effects 0.000 claims description 7
• 125000001246 bromo group Chemical group Br* 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 230000009467 reduction Effects 0.000 claims description 7
• 238000006722 reduction reaction Methods 0.000 claims description 7
• 239000012044 organic layer Substances 0.000 claims description 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
• 238000006969 Curtius rearrangement reaction Methods 0.000 claims description 5
• 239000003054 catalyst Substances 0.000 claims description 5
• 239000010949 copper Substances 0.000 claims description 5
• 229910052802 copper Inorganic materials 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 239000000377 silicon dioxide Substances 0.000 claims description 5
• 238000001228 spectrum Methods 0.000 claims description 5
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
• 238000005804 alkylation reaction Methods 0.000 claims description 4
• MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
• OHXYISPGUNPNIT-UHFFFAOYSA-N 4-[4-(4,5-difluoro-6-methyl-2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]oxane-4-carbonitrile Chemical compound O=C1NC=2C(F)=C(F)C(C)=CC=2N1C(CC1)CCN1C1(C#N)CCOCC1 OHXYISPGUNPNIT-UHFFFAOYSA-N 0.000 claims description 3
• DSUMPQPZYPXTND-UHFFFAOYSA-N 5-chloro-7-fluoro-3-[1-(oxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC=2C(F)=CC(Cl)=CC=2N1C(CC1)CCN1C1CCOCC1 DSUMPQPZYPXTND-UHFFFAOYSA-N 0.000 claims description 3
• 239000007818 Grignard reagent Substances 0.000 claims description 3
• 238000006751 Mitsunobu reaction Methods 0.000 claims description 3
• 230000029936 alkylation Effects 0.000 claims description 3
• 125000006239 protecting group Chemical group 0.000 claims description 3
• 229920006395 saturated elastomer Polymers 0.000 claims description 3
• KQYDZKAMMFFLSN-UHFFFAOYSA-N 6,7-difluoro-5-methyl-3-[1-(4-methyloxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC=2C(F)=C(F)C(C)=CC=2N1C(CC1)CCN1C1(C)CCOCC1 KQYDZKAMMFFLSN-UHFFFAOYSA-N 0.000 claims description 2
• NCIMFRCDQMTAFP-UHFFFAOYSA-N 7-fluoro-5-methoxy-3-[1-(oxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C12=CC(OC)=CC(F)=C2NC(=O)N1C(CC1)CCN1C1CCOCC1 NCIMFRCDQMTAFP-UHFFFAOYSA-N 0.000 claims description 2
• KRRSQJOVDWYKHH-UHFFFAOYSA-N 7-fluoro-5-methyl-3-[1-(oxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C12=CC(C)=CC(F)=C2NC(=O)N1C(CC1)CCN1C1CCOCC1 KRRSQJOVDWYKHH-UHFFFAOYSA-N 0.000 claims description 2
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
• 229910021529 ammonia Inorganic materials 0.000 claims description 2
• 239000008096 xylene Substances 0.000 claims description 2
• QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
• 238000003747 Grignard reaction Methods 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• 229940125846 compound 25 Drugs 0.000 claims 1
• NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims 1
• LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 claims 1
• 235000011006 sodium potassium tartrate Nutrition 0.000 claims 1
• 125000001424 substituent group Chemical group 0.000 abstract description 4
• 229940122547 Muscarinic M1 receptor agonist Drugs 0.000 abstract 1
• 239000000359 muscarinic M1 receptor agonist Substances 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 77
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 71
• 230000001225 therapeutic effect Effects 0.000 description 51
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 48
• 239000000164 antipsychotic agent Substances 0.000 description 33
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
• 239000007787 solid Substances 0.000 description 30
• 239000002904 solvent Substances 0.000 description 30
• 150000001412 amines Chemical class 0.000 description 29
• 239000002249 anxiolytic agent Substances 0.000 description 29
• 230000000949 anxiolytic effect Effects 0.000 description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 29
• 235000019439 ethyl acetate Nutrition 0.000 description 26
• 239000000243 solution Substances 0.000 description 26
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
• 229940079593 drug Drugs 0.000 description 24
• 239000004480 active ingredient Substances 0.000 description 23
• 239000000935 antidepressant agent Substances 0.000 description 23
• 208000035475 disorder Diseases 0.000 description 23
• 239000000543 intermediate Substances 0.000 description 23
• 229940127237 mood stabilizer Drugs 0.000 description 23
• 229940005513 antidepressants Drugs 0.000 description 22
• 239000002475 cognitive enhancer Substances 0.000 description 22
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
• 230000001430 anti-depressive effect Effects 0.000 description 20
• 239000004050 mood stabilizer Substances 0.000 description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
• 230000035987 intoxication Effects 0.000 description 15
• 231100000566 intoxication Toxicity 0.000 description 15
• 208000019901 Anxiety disease Diseases 0.000 description 13
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
• 239000005557 antagonist Substances 0.000 description 13
• 102000005962 receptors Human genes 0.000 description 13
• 108020003175 receptors Proteins 0.000 description 13
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 13
• 206010012218 Delirium Diseases 0.000 description 12
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
• 208000019116 sleep disease Diseases 0.000 description 12
• 208000019022 Mood disease Diseases 0.000 description 11
• 239000012458 free base Substances 0.000 description 11
• 239000011541 reaction mixture Substances 0.000 description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• 210000004027 cell Anatomy 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 239000000047 product Substances 0.000 description 10
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• 229910052786 argon Inorganic materials 0.000 description 9
• 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 9
• 150000002513 isocyanates Chemical class 0.000 description 9
• 239000010410 layer Substances 0.000 description 9
• 238000002360 preparation method Methods 0.000 description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
• 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 8
• 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 8
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 8
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
• 238000010511 deprotection reaction Methods 0.000 description 8
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
• 238000002474 experimental method Methods 0.000 description 8
• 230000008570 general process Effects 0.000 description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
• 239000003921 oil Substances 0.000 description 8
• 235000019198 oils Nutrition 0.000 description 8
• 208000020685 sleep-wake disease Diseases 0.000 description 8
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 8
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 7
• 206010012289 Dementia Diseases 0.000 description 7
• 206010026749 Mania Diseases 0.000 description 7
• 238000005481 NMR spectroscopy Methods 0.000 description 7
• 201000001880 Sexual dysfunction Diseases 0.000 description 7
• 229940025084 amphetamine Drugs 0.000 description 7
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 7
• 239000012043 crude product Substances 0.000 description 7
• 238000001035 drying Methods 0.000 description 7
• YQZBAXDVDZTKEQ-UHFFFAOYSA-N loxapine succinate Chemical compound [H+].[H+].[O-]C(=O)CCC([O-])=O.C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 YQZBAXDVDZTKEQ-UHFFFAOYSA-N 0.000 description 7
• JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical compound O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 description 7
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 7
• 229940002612 prodrug Drugs 0.000 description 7
• 239000000651 prodrug Substances 0.000 description 7
• 231100000872 sexual dysfunction Toxicity 0.000 description 7
• 239000002002 slurry Substances 0.000 description 7
• GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 6
• DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
• PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 description 6
• RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 description 6
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• GFBKORZTTCHDGY-UWVJOHFNSA-N Thiothixene Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2\C1=C\CCN1CCN(C)CC1 GFBKORZTTCHDGY-UWVJOHFNSA-N 0.000 description 6
• 229960000583 acetic acid Drugs 0.000 description 6
• 239000000556 agonist Substances 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 239000002552 dosage form Substances 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 238000001704 evaporation Methods 0.000 description 6
• 230000008020 evaporation Effects 0.000 description 6
• 230000000147 hypnotic effect Effects 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 239000000932 sedative agent Substances 0.000 description 6
• 230000001624 sedative effect Effects 0.000 description 6
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• 239000003826 tablet Substances 0.000 description 6
• UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 6
• HMDHQYKNBZEFTH-UHFFFAOYSA-N 2,3-difluoro-4-methylaniline Chemical compound CC1=CC=C(N)C(F)=C1F HMDHQYKNBZEFTH-UHFFFAOYSA-N 0.000 description 5
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
• 206010013654 Drug abuse Diseases 0.000 description 5
• KLPWJLBORRMFGK-UHFFFAOYSA-N Molindone Chemical compound O=C1C=2C(CC)=C(C)NC=2CCC1CN1CCOCC1 KLPWJLBORRMFGK-UHFFFAOYSA-N 0.000 description 5
• 239000007868 Raney catalyst Substances 0.000 description 5
• 229910000564 Raney nickel Inorganic materials 0.000 description 5
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 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
• 239000007864 aqueous solution Substances 0.000 description 5
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 5
• 239000011575 calcium Substances 0.000 description 5
• 229910052791 calcium Inorganic materials 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• 238000006555 catalytic reaction Methods 0.000 description 5
• QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 5
• 150000004985 diamines Chemical class 0.000 description 5
• 230000009977 dual effect Effects 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 229910052751 metal Inorganic materials 0.000 description 5
• 239000002184 metal Substances 0.000 description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
• 229910052757 nitrogen Inorganic materials 0.000 description 5
• KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 5
• 239000012074 organic phase Substances 0.000 description 5
• 239000003960 organic solvent Substances 0.000 description 5
• 230000002085 persistent effect Effects 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 208000020016 psychiatric disease Diseases 0.000 description 5
• 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 5
• 239000012047 saturated solution Substances 0.000 description 5
• 208000011117 substance-related disease Diseases 0.000 description 5
• LZRDHSFPLUWYAX-UHFFFAOYSA-N tert-butyl 4-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)CC1 LZRDHSFPLUWYAX-UHFFFAOYSA-N 0.000 description 5
• 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 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
• WSPOMRSOLSGNFJ-AUWJEWJLSA-N (Z)-chlorprothixene Chemical compound C1=C(Cl)C=C2C(=C/CCN(C)C)\C3=CC=CC=C3SC2=C1 WSPOMRSOLSGNFJ-AUWJEWJLSA-N 0.000 description 4
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
• WAGLGQXOHWSQOD-UHFFFAOYSA-N 2-fluoro-6-iodo-4-methylaniline Chemical compound CC1=CC(F)=C(N)C(I)=C1 WAGLGQXOHWSQOD-UHFFFAOYSA-N 0.000 description 4
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 4
• 208000022497 Cocaine-Related disease Diseases 0.000 description 4
• UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 4
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
• GUTXTARXLVFHDK-UHFFFAOYSA-N Haloperidol decanoate Chemical compound C1CC(OC(=O)CCCCCCCCC)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 GUTXTARXLVFHDK-UHFFFAOYSA-N 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
• 208000003863 Marijuana Abuse Diseases 0.000 description 4
• 208000006262 Psychological Sexual Dysfunctions Diseases 0.000 description 4
• KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
• 241000700605 Viruses Species 0.000 description 4
• 239000002253 acid Substances 0.000 description 4
• RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
• 239000003125 aqueous solvent Substances 0.000 description 4
• 239000012300 argon atmosphere Substances 0.000 description 4
• 239000003693 atypical antipsychotic agent Substances 0.000 description 4
• 229940127236 atypical antipsychotics Drugs 0.000 description 4
• IUKQLMGVFMDQDP-UHFFFAOYSA-N azane;piperidine Chemical compound N.C1CCNCC1 IUKQLMGVFMDQDP-UHFFFAOYSA-N 0.000 description 4
• BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 4
• 239000012267 brine Substances 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 229960001076 chlorpromazine Drugs 0.000 description 4
• 229960001552 chlorprothixene Drugs 0.000 description 4
• 230000001713 cholinergic effect Effects 0.000 description 4
• 229960004170 clozapine Drugs 0.000 description 4
• NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 4
• 238000006073 displacement reaction Methods 0.000 description 4
• 229960003638 dopamine Drugs 0.000 description 4
• 229960000394 droperidol Drugs 0.000 description 4
• RMEDXOLNCUSCGS-UHFFFAOYSA-N droperidol Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CC=C(N2C(NC3=CC=CC=C32)=O)CC1 RMEDXOLNCUSCGS-UHFFFAOYSA-N 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 229960003878 haloperidol Drugs 0.000 description 4
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
• 239000012948 isocyanate Substances 0.000 description 4
• 239000007937 lozenge Substances 0.000 description 4
• 208000024714 major depressive disease Diseases 0.000 description 4
• 229960005017 olanzapine Drugs 0.000 description 4
• 208000022821 personality disease Diseases 0.000 description 4
• 239000012071 phase Substances 0.000 description 4
• JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 4
• 229950010883 phencyclidine Drugs 0.000 description 4
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 4
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
• 229960003770 reboxetine Drugs 0.000 description 4
• 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 4
• 229940044601 receptor agonist Drugs 0.000 description 4
• 239000000018 receptor agonist Substances 0.000 description 4
• 229960001534 risperidone Drugs 0.000 description 4
• 238000013341 scale-up Methods 0.000 description 4
• 201000000980 schizophrenia Diseases 0.000 description 4
• 239000003772 serotonin uptake inhibitor Substances 0.000 description 4
• 238000010898 silica gel chromatography Methods 0.000 description 4
• 239000012418 sodium perborate tetrahydrate Substances 0.000 description 4
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
• IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 4
• WHSRIIYYXHLIKU-UHFFFAOYSA-N tert-butyl 4-[(2-bromo-6-fluoro-4-methylphenyl)carbamoylamino]piperidine-1-carboxylate Chemical compound BrC1=CC(C)=CC(F)=C1NC(=O)NC1CCN(C(=O)OC(C)(C)C)CC1 WHSRIIYYXHLIKU-UHFFFAOYSA-N 0.000 description 4
• JHXBVBXTYSGILK-UHFFFAOYSA-N tert-butyl 4-[(2-fluoro-6-iodo-4-methylphenyl)carbamoylamino]piperidine-1-carboxylate Chemical compound IC1=CC(C)=CC(F)=C1NC(=O)NC1CCN(C(=O)OC(C)(C)C)CC1 JHXBVBXTYSGILK-UHFFFAOYSA-N 0.000 description 4
• 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 4
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
• MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 4
• 229960000604 valproic acid Drugs 0.000 description 4
• 229960000607 ziprasidone Drugs 0.000 description 4
• YNHSGDUOWUPKKQ-UHFFFAOYSA-N 1,3-difluoro-5-methoxy-2-nitrobenzene Chemical compound COC1=CC(F)=C([N+]([O-])=O)C(F)=C1 YNHSGDUOWUPKKQ-UHFFFAOYSA-N 0.000 description 3
• VQONOVSMIMUZCD-UHFFFAOYSA-N 1-bromo-5-chloro-3-fluoro-2-isocyanatobenzene Chemical compound FC1=CC(Cl)=CC(Br)=C1N=C=O VQONOVSMIMUZCD-UHFFFAOYSA-N 0.000 description 3
• BWMNOFXLNWSOMU-UHFFFAOYSA-N 1-fluoro-3-iodo-2-isocyanato-5-methylbenzene Chemical compound CC1=CC(F)=C(N=C=O)C(I)=C1 BWMNOFXLNWSOMU-UHFFFAOYSA-N 0.000 description 3
• QVECFWRRZNGQDO-UHFFFAOYSA-N 2-bromo-6-fluoro-4-methylaniline Chemical compound CC1=CC(F)=C(N)C(Br)=C1 QVECFWRRZNGQDO-UHFFFAOYSA-N 0.000 description 3
• MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 3
• DDNBXAHODWXJKM-UHFFFAOYSA-N 3,5-difluoro-4-nitrophenol Chemical compound OC1=CC(F)=C([N+]([O-])=O)C(F)=C1 DDNBXAHODWXJKM-UHFFFAOYSA-N 0.000 description 3
• ABAGKHWCTWMUDH-UHFFFAOYSA-N 5-bromo-1,3-difluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=C(F)C=C(Br)C=C1F ABAGKHWCTWMUDH-UHFFFAOYSA-N 0.000 description 3
• IRGBOMFFIWQHOO-UHFFFAOYSA-N 5-cyclopropyl-1,3-difluoro-2-nitrobenzene Chemical compound C1=C(F)C([N+](=O)[O-])=C(F)C=C1C1CC1 IRGBOMFFIWQHOO-UHFFFAOYSA-N 0.000 description 3
• YQPPCQAVVPGPCD-UHFFFAOYSA-N 6,7-difluoro-5-methyl-3-[1-(4-methyloxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one;hydrochloride Chemical compound Cl.O=C1NC=2C(F)=C(F)C(C)=CC=2N1C(CC1)CCN1C1(C)CCOCC1 YQPPCQAVVPGPCD-UHFFFAOYSA-N 0.000 description 3
• JCNSWCZJWGOGNR-UHFFFAOYSA-N 6,7-difluoro-5-methyl-3-piperidin-4-yl-1h-benzimidazol-2-one;hydrochloride Chemical compound Cl.O=C1NC=2C(F)=C(F)C(C)=CC=2N1C1CCNCC1 JCNSWCZJWGOGNR-UHFFFAOYSA-N 0.000 description 3
• 208000024827 Alzheimer disease Diseases 0.000 description 3
• 208000031091 Amnestic disease Diseases 0.000 description 3
• 208000029197 Amphetamine-Related disease Diseases 0.000 description 3
• 208000020925 Bipolar disease Diseases 0.000 description 3
• 206010012239 Delusion Diseases 0.000 description 3
• 229940121891 Dopamine receptor antagonist Drugs 0.000 description 3
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
• 208000004230 Gender Dysphoria Diseases 0.000 description 3
• 208000004547 Hallucinations Diseases 0.000 description 3
• 241000124008 Mammalia Species 0.000 description 3
• 208000026139 Memory disease Diseases 0.000 description 3
• 208000026251 Opioid-Related disease Diseases 0.000 description 3
• 208000006199 Parasomnias Diseases 0.000 description 3
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
• ZGUGWUXLJSTTMA-UHFFFAOYSA-N Promazinum Chemical compound C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZGUGWUXLJSTTMA-UHFFFAOYSA-N 0.000 description 3
• 241000700159 Rattus Species 0.000 description 3
• 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 229960000276 acetophenazine Drugs 0.000 description 3
• 239000000443 aerosol Substances 0.000 description 3
• 229960003036 amisulpride Drugs 0.000 description 3
• NTJOBXMMWNYJFB-UHFFFAOYSA-N amisulpride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC NTJOBXMMWNYJFB-UHFFFAOYSA-N 0.000 description 3
• 229940005530 anxiolytics Drugs 0.000 description 3
• QUNGXSCIAYPUKE-UHFFFAOYSA-N benzimidazol-2-one;hydrochloride Chemical compound Cl.C1=CC=CC2=NC(=O)N=C21 QUNGXSCIAYPUKE-UHFFFAOYSA-N 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• 239000004202 carbamide Substances 0.000 description 3
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 230000007278 cognition impairment Effects 0.000 description 3
• 230000006999 cognitive decline Effects 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 238000007405 data analysis Methods 0.000 description 3
• 231100000868 delusion Toxicity 0.000 description 3
• 230000003001 depressive effect Effects 0.000 description 3
• HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 3
• 235000014632 disordered eating Nutrition 0.000 description 3
• 239000003210 dopamine receptor blocking agent Substances 0.000 description 3
• 206010013663 drug dependence Diseases 0.000 description 3
• 229960002690 fluphenazine Drugs 0.000 description 3
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
• 238000005984 hydrogenation reaction Methods 0.000 description 3
• 206010020765 hypersomnia Diseases 0.000 description 3
• 206010022437 insomnia Diseases 0.000 description 3
• 229910052740 iodine Inorganic materials 0.000 description 3
• 125000002346 iodo group Chemical group I* 0.000 description 3
• 150000002576 ketones Chemical class 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
• 229960000423 loxapine Drugs 0.000 description 3
• 229940089527 loxitane Drugs 0.000 description 3
• 229960004938 molindone Drugs 0.000 description 3
• 239000002767 noradrenalin uptake inhibitor Substances 0.000 description 3
• 208000019906 panic disease Diseases 0.000 description 3
• 230000037361 pathway Effects 0.000 description 3
• 230000002093 peripheral effect Effects 0.000 description 3
• 229960000762 perphenazine Drugs 0.000 description 3
• 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 3
• 229960003634 pimozide Drugs 0.000 description 3
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 3
• 239000011591 potassium Substances 0.000 description 3
• 229910052700 potassium Inorganic materials 0.000 description 3
• WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 3
• 229960003111 prochlorperazine Drugs 0.000 description 3
• 238000000746 purification Methods 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
• 230000002829 reductive effect Effects 0.000 description 3
• 230000004044 response Effects 0.000 description 3
• 239000000741 silica gel Substances 0.000 description 3
• 229910002027 silica gel Inorganic materials 0.000 description 3
• 229960001866 silicon dioxide Drugs 0.000 description 3
• 235000017557 sodium bicarbonate Nutrition 0.000 description 3
• 229910052938 sodium sulfate Inorganic materials 0.000 description 3
• 235000011152 sodium sulphate Nutrition 0.000 description 3
• 239000007858 starting material Substances 0.000 description 3
• 239000000829 suppository Substances 0.000 description 3
• 208000024891 symptom Diseases 0.000 description 3
• YZBQMSPKOMUXBY-UHFFFAOYSA-N tert-butyl 4-(2-amino-5-cyclopropyl-3-fluoroanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC(C2CC2)=CC(F)=C1N YZBQMSPKOMUXBY-UHFFFAOYSA-N 0.000 description 3
• ZVHOWAPFATVRBO-UHFFFAOYSA-N tert-butyl 4-(4-fluoro-6-methyl-2-oxo-3h-benzimidazol-1-yl)piperidine-1-carboxylate Chemical compound C12=CC(C)=CC(F)=C2NC(=O)N1C1CCN(C(=O)OC(C)(C)C)CC1 ZVHOWAPFATVRBO-UHFFFAOYSA-N 0.000 description 3
• XGYUUVSXTLOGJO-UHFFFAOYSA-N tert-butyl 4-(5-cyclopropyl-3-fluoro-2-nitroanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC(C2CC2)=CC(F)=C1[N+]([O-])=O XGYUUVSXTLOGJO-UHFFFAOYSA-N 0.000 description 3
• SLBZPKSUFGWJSZ-UHFFFAOYSA-N tert-butyl 4-[(2-bromo-4-chloro-6-fluorophenyl)carbamoylamino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC(=O)NC1=C(F)C=C(Cl)C=C1Br SLBZPKSUFGWJSZ-UHFFFAOYSA-N 0.000 description 3
• 229960002784 thioridazine Drugs 0.000 description 3
• 229960002324 trifluoperazine Drugs 0.000 description 3
• 238000003828 vacuum filtration Methods 0.000 description 3
• 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 2
• GJJFMKBJSRMPLA-HIFRSBDPSA-N (1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenyl-1-cyclopropanecarboxamide Chemical compound C=1C=CC=CC=1[C@@]1(C(=O)N(CC)CC)C[C@@H]1CN GJJFMKBJSRMPLA-HIFRSBDPSA-N 0.000 description 2
• IGLYMJRIWWIQQE-QUOODJBBSA-N (1S,2R)-2-phenylcyclopropan-1-amine (1R,2S)-2-phenylcyclopropan-1-amine Chemical compound N[C@H]1C[C@@H]1C1=CC=CC=C1.N[C@@H]1C[C@H]1C1=CC=CC=C1 IGLYMJRIWWIQQE-QUOODJBBSA-N 0.000 description 2
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
• 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 2
• 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 2
• 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 2
• 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 2
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• ODMLBEQUDLHJMW-UHFFFAOYSA-N 1,2-difluoro-3-methyl-4-nitrobenzene Chemical compound CC1=C(F)C(F)=CC=C1[N+]([O-])=O ODMLBEQUDLHJMW-UHFFFAOYSA-N 0.000 description 2
• RCDKCOBKMXBXAU-UHFFFAOYSA-N 1,3-difluoro-5-methyl-2-nitrobenzene Chemical compound CC1=CC(F)=C([N+]([O-])=O)C(F)=C1 RCDKCOBKMXBXAU-UHFFFAOYSA-N 0.000 description 2
• BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 2
• PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical group [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 2
• DQKUCXAFYAIKFJ-UHFFFAOYSA-N 2,3-difluoro-1-methyl-4-nitrobenzene Chemical compound CC1=CC=C([N+]([O-])=O)C(F)=C1F DQKUCXAFYAIKFJ-UHFFFAOYSA-N 0.000 description 2
• ZAJBUIBKJUTUIT-UHFFFAOYSA-N 2,3-difluoro-6-iodo-4-methylaniline Chemical compound CC1=CC(I)=C(N)C(F)=C1F ZAJBUIBKJUTUIT-UHFFFAOYSA-N 0.000 description 2
• JDQKXSGSNQPPJG-UHFFFAOYSA-N 2-(2,3-difluoro-4-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C([N+]([O-])=O)C(F)=C1F JDQKXSGSNQPPJG-UHFFFAOYSA-N 0.000 description 2
• KZNVCGPCWKYPKD-UHFFFAOYSA-N 2-(2,3-difluoro-6-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=C(F)C(F)=CC=C1[N+]([O-])=O KZNVCGPCWKYPKD-UHFFFAOYSA-N 0.000 description 2
• XGLFBUVWWKDQKP-UHFFFAOYSA-N 2-(3,5-difluoro-4-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC(F)=C([N+]([O-])=O)C(F)=C1 XGLFBUVWWKDQKP-UHFFFAOYSA-N 0.000 description 2
• BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 2
• ZQEXBVHABAJPHJ-UHFFFAOYSA-N 2-fluoro-4-methylaniline Chemical compound CC1=CC=C(N)C(F)=C1 ZQEXBVHABAJPHJ-UHFFFAOYSA-N 0.000 description 2
• MGOCSCHYSUUUMG-UHFFFAOYSA-N 3,4-difluoro-1-iodo-2-isocyanato-5-methylbenzene Chemical compound CC1=CC(I)=C(N=C=O)C(F)=C1F MGOCSCHYSUUUMG-UHFFFAOYSA-N 0.000 description 2
• FEBOTPHFXYHVPL-UHFFFAOYSA-N 3-[1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidinyl]-1H-benzimidazol-2-one Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 FEBOTPHFXYHVPL-UHFFFAOYSA-N 0.000 description 2
• BIAVGWDGIJKWRM-FQEVSTJZSA-N 3-hydroxy-2-phenyl-n-[(1s)-1-phenylpropyl]quinoline-4-carboxamide Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(O)C=1C1=CC=CC=C1 BIAVGWDGIJKWRM-FQEVSTJZSA-N 0.000 description 2
• DASKXADFUYTWTK-UHFFFAOYSA-N 5-chloro-7-fluoro-3-piperidin-4-yl-1h-benzimidazol-2-one;hydrochloride Chemical compound Cl.O=C1NC=2C(F)=CC(Cl)=CC=2N1C1CCNCC1 DASKXADFUYTWTK-UHFFFAOYSA-N 0.000 description 2
• XKFPYPQQHFEXRZ-UHFFFAOYSA-N 5-methyl-N'-(phenylmethyl)-3-isoxazolecarbohydrazide Chemical compound O1C(C)=CC(C(=O)NNCC=2C=CC=CC=2)=N1 XKFPYPQQHFEXRZ-UHFFFAOYSA-N 0.000 description 2
• UJCASPHRCDNOAI-UHFFFAOYSA-N 6,7-difluoro-5-methyl-3-[1-(oxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one;hydrochloride Chemical compound Cl.O=C1NC=2C(F)=C(F)C(C)=CC=2N1C(CC1)CCN1C1CCOCC1 UJCASPHRCDNOAI-UHFFFAOYSA-N 0.000 description 2
• FJYKBJUHMMQVPU-UHFFFAOYSA-N 7-fluoro-5-methoxy-3-[1-(oxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one;hydrochloride Chemical compound Cl.C12=CC(OC)=CC(F)=C2NC(=O)N1C(CC1)CCN1C1CCOCC1 FJYKBJUHMMQVPU-UHFFFAOYSA-N 0.000 description 2
• DQSNUMFLMIZQFH-UHFFFAOYSA-N 7-fluoro-5-methyl-3-[1-(oxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C12=CC(C)=CC(F)=C2NC(=O)N1C(CC1)CCN1C1CCOCC1 DQSNUMFLMIZQFH-UHFFFAOYSA-N 0.000 description 2
• KJCKZWGVZMJOCI-UHFFFAOYSA-N 7-fluoro-5-methyl-3-[1-(oxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.C12=CC(C)=CC(F)=C2NC(=O)N1C(CC1)CCN1C1CCOCC1 KJCKZWGVZMJOCI-UHFFFAOYSA-N 0.000 description 2
• KWBOEFVUJIZJDY-UHFFFAOYSA-N 7-fluoro-5-methyl-3-piperidin-4-yl-1h-benzimidazol-2-one;hydrochloride Chemical compound Cl.C12=CC(C)=CC(F)=C2NC(=O)N1C1CCNCC1 KWBOEFVUJIZJDY-UHFFFAOYSA-N 0.000 description 2
• 206010000117 Abnormal behaviour Diseases 0.000 description 2
• 208000008811 Agoraphobia Diseases 0.000 description 2
• 206010001605 Alcohol poisoning Diseases 0.000 description 2
• 208000007848 Alcoholism Diseases 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• 208000020706 Autistic disease Diseases 0.000 description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
• 102000017926 CHRM2 Human genes 0.000 description 2
• 102000017925 CHRM3 Human genes 0.000 description 2
• 101150060249 CHRM3 gene Proteins 0.000 description 2
• 241000218236 Cannabis Species 0.000 description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
• 101150012960 Chrm2 gene Proteins 0.000 description 2
• 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 2
• 208000017781 Cocaine intoxication Diseases 0.000 description 2
• 208000024254 Delusional disease Diseases 0.000 description 2
• 208000020401 Depressive disease Diseases 0.000 description 2
• 208000007590 Disorders of Excessive Somnolence Diseases 0.000 description 2
• 206010013980 Dyssomnias Diseases 0.000 description 2
• 208000030814 Eating disease Diseases 0.000 description 2
• 208000019454 Feeding and Eating disease Diseases 0.000 description 2
• 206010016754 Flashback Diseases 0.000 description 2
• 208000029810 Gender identity disease Diseases 0.000 description 2
• 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 2
• QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 2
• LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 description 2
• 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 2
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
• GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
• PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 description 2
• 206010033888 Paraphilia Diseases 0.000 description 2
• AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 2
• RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 239000002202 Polyethylene glycol Substances 0.000 description 2
• 208000020186 Schizophreniform disease Diseases 0.000 description 2
• 206010041250 Social phobia Diseases 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• 208000006011 Stroke Diseases 0.000 description 2
• 208000011962 Substance-induced mood disease Diseases 0.000 description 2
• 231100000395 Substance-induced mood disorder Toxicity 0.000 description 2
• 208000011963 Substance-induced psychotic disease Diseases 0.000 description 2
• 231100000393 Substance-induced psychotic disorder Toxicity 0.000 description 2
• 206010043118 Tardive Dyskinesia Diseases 0.000 description 2
• KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 description 2
• 229940123445 Tricyclic antidepressant Drugs 0.000 description 2
• BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 description 2
• WNTYBHLDCKXEOT-UHFFFAOYSA-N acetophenazine Chemical compound C12=CC(C(=O)C)=CC=C2SC2=CC=CC=C2N1CCCN1CCN(CCO)CC1 WNTYBHLDCKXEOT-UHFFFAOYSA-N 0.000 description 2
• 239000004479 aerosol dispenser Substances 0.000 description 2
• 208000028505 alcohol-related disease Diseases 0.000 description 2
• 229960004538 alprazolam Drugs 0.000 description 2
• VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 2
• 229960000959 amineptine Drugs 0.000 description 2
• VDPUXONTAVMIKZ-UHFFFAOYSA-N amineptine hydrochloride Chemical compound [Cl-].C1CC2=CC=CC=C2C([NH2+]CCCCCCC(=O)O)C2=CC=CC=C21 VDPUXONTAVMIKZ-UHFFFAOYSA-N 0.000 description 2
• 229960000836 amitriptyline Drugs 0.000 description 2
• KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 2
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• 230000008485 antagonism Effects 0.000 description 2
• 230000000561 anti-psychotic effect Effects 0.000 description 2
• 239000008346 aqueous phase Substances 0.000 description 2
• 239000007900 aqueous suspension Substances 0.000 description 2
• 229960004372 aripiprazole Drugs 0.000 description 2
• 239000012131 assay buffer Substances 0.000 description 2
• 239000002585 base Substances 0.000 description 2
• 229960002507 benperidol Drugs 0.000 description 2
• 229940049706 benzodiazepine Drugs 0.000 description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
• 229960001058 bupropion Drugs 0.000 description 2
• SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 2
• 229960001948 caffeine Drugs 0.000 description 2
• VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 2
• 201000001843 cannabis dependence Diseases 0.000 description 2
• 229960000623 carbamazepine Drugs 0.000 description 2
• FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 235000010980 cellulose Nutrition 0.000 description 2
• 229920002678 cellulose Polymers 0.000 description 2
• 210000003169 central nervous system Anatomy 0.000 description 2
• 210000004978 chinese hamster ovary cell Anatomy 0.000 description 2
• 239000000460 chlorine Substances 0.000 description 2
• 229910052801 chlorine Inorganic materials 0.000 description 2
• 239000000544 cholinesterase inhibitor Substances 0.000 description 2
• 229960001653 citalopram Drugs 0.000 description 2
• 229960004606 clomipramine Drugs 0.000 description 2
• ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
• 230000019771 cognition Effects 0.000 description 2
• 230000001149 cognitive effect Effects 0.000 description 2
• 238000002648 combination therapy Methods 0.000 description 2
• 238000009833 condensation Methods 0.000 description 2
• 230000005494 condensation Effects 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 125000000753 cycloalkyl group Chemical group 0.000 description 2
• 238000013461 design Methods 0.000 description 2
• SEESNIHRBOITKW-UHFFFAOYSA-N diethyl 2-(2,3-difluoro-4-nitrophenyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C1=CC=C([N+]([O-])=O)C(F)=C1F SEESNIHRBOITKW-UHFFFAOYSA-N 0.000 description 2
• MSOQCNAFADYWFJ-UHFFFAOYSA-N diethyl 2-(2,3-difluoro-6-nitrophenyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C1=C(F)C(F)=CC=C1[N+]([O-])=O MSOQCNAFADYWFJ-UHFFFAOYSA-N 0.000 description 2
• 239000006185 dispersion Substances 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
• 230000003291 dopaminomimetic effect Effects 0.000 description 2
• 229960002866 duloxetine Drugs 0.000 description 2
• 229960004341 escitalopram Drugs 0.000 description 2
• 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 2
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
• 229950003930 femoxetine Drugs 0.000 description 2
• OJSFTALXCYKKFQ-YLJYHZDGSA-N femoxetine Chemical compound C1=CC(OC)=CC=C1OC[C@@H]1[C@@H](C=2C=CC=CC=2)CCN(C)C1 OJSFTALXCYKKFQ-YLJYHZDGSA-N 0.000 description 2
• 229960002464 fluoxetine Drugs 0.000 description 2
• VIQCGTZFEYDQMR-UHFFFAOYSA-N fluphenazine decanoate Chemical compound C1CN(CCOC(=O)CCCCCCCCC)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 VIQCGTZFEYDQMR-UHFFFAOYSA-N 0.000 description 2
• 229960001374 fluphenazine decanoate Drugs 0.000 description 2
• 229960004038 fluvoxamine Drugs 0.000 description 2
• 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 2
• 150000004675 formic acid derivatives Chemical class 0.000 description 2
• 229960002870 gabapentin Drugs 0.000 description 2
• ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 description 2
• 239000000499 gel Substances 0.000 description 2
• 239000007903 gelatin capsule Substances 0.000 description 2
• 239000012362 glacial acetic acid Substances 0.000 description 2
• 235000011187 glycerol Nutrition 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 229940095895 haldol Drugs 0.000 description 2
• 239000000380 hallucinogen Substances 0.000 description 2
• 208000011331 hallucinogen-persisting perception disease Diseases 0.000 description 2
• 229960005007 haloperidol decanoate Drugs 0.000 description 2
• 230000002209 hydrophobic effect Effects 0.000 description 2
• 229960004801 imipramine Drugs 0.000 description 2
• BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 2
• 229950002473 indalpine Drugs 0.000 description 2
• SADQVAVFGNTEOD-UHFFFAOYSA-N indalpine Chemical compound C=1NC2=CC=CC=C2C=1CCC1CCNCC1 SADQVAVFGNTEOD-UHFFFAOYSA-N 0.000 description 2
• 239000003112 inhibitor Substances 0.000 description 2
• 208000014674 injury Diseases 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• 229960002672 isocarboxazid Drugs 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
• 229960004391 lorazepam Drugs 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
• 235000019341 magnesium sulphate Nutrition 0.000 description 2
• 229960004090 maprotiline Drugs 0.000 description 2
• 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 2
• 239000000463 material Substances 0.000 description 2
• 206010027175 memory impairment Diseases 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
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 229940042053 methotrimeprazine Drugs 0.000 description 2
• TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 2
• 229960004503 metoclopramide Drugs 0.000 description 2
• 229960003955 mianserin Drugs 0.000 description 2
• 229960000600 milnacipran Drugs 0.000 description 2
• 229960001785 mirtazapine Drugs 0.000 description 2
• RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 description 2
• 238000002156 mixing Methods 0.000 description 2
• 229940028394 moban Drugs 0.000 description 2
• YHXISWVBGDMDLQ-UHFFFAOYSA-N moclobemide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCCN1CCOCC1 YHXISWVBGDMDLQ-UHFFFAOYSA-N 0.000 description 2
• 229960004644 moclobemide Drugs 0.000 description 2
• 239000002899 monoamine oxidase inhibitor Substances 0.000 description 2
• 229960001800 nefazodone Drugs 0.000 description 2
• 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 2
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
• 229960001158 nortriptyline Drugs 0.000 description 2
• 125000002524 organometallic group Chemical group 0.000 description 2
• 229950009875 osanetant Drugs 0.000 description 2
• DZOJBGLFWINFBF-UMSFTDKQSA-N osanetant Chemical compound C([C@](C1)(CCCN2CCC(CC2)(N(C(C)=O)C)C=2C=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)C1=CC=CC=C1 DZOJBGLFWINFBF-UMSFTDKQSA-N 0.000 description 2
• 229960001816 oxcarbazepine Drugs 0.000 description 2
• CTRLABGOLIVAIY-UHFFFAOYSA-N oxcarbazepine Chemical compound C1C(=O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 CTRLABGOLIVAIY-UHFFFAOYSA-N 0.000 description 2
• 208000002851 paranoid schizophrenia Diseases 0.000 description 2
• 239000003182 parenteral nutrition solution Substances 0.000 description 2
• 229960002296 paroxetine Drugs 0.000 description 2
• 239000004031 partial agonist Substances 0.000 description 2
• WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 description 2
• 208000007100 phencyclidine abuse Diseases 0.000 description 2
• 229960000964 phenelzine Drugs 0.000 description 2
• AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
• 229960005235 piperonyl butoxide Drugs 0.000 description 2
• 229920001223 polyethylene glycol Polymers 0.000 description 2
• NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• 239000003380 propellant Substances 0.000 description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 238000010926 purge Methods 0.000 description 2
• 229950010561 radafaxine Drugs 0.000 description 2
• RCOBKSKAZMVBHT-TVQRCGJNSA-N radafaxine Chemical compound C[C@@H]1NC(C)(C)CO[C@@]1(O)C1=CC=CC(Cl)=C1 RCOBKSKAZMVBHT-TVQRCGJNSA-N 0.000 description 2
• BLGXFZZNTVWLAY-DIRVCLHFSA-N rauwolscine Chemical compound C1=CC=C2C(CCN3C[C@H]4CC[C@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-DIRVCLHFSA-N 0.000 description 2
• 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 2
• 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 2
• 229940076279 serotonin Drugs 0.000 description 2
• 239000000952 serotonin receptor agonist Substances 0.000 description 2
• 229940126570 serotonin reuptake inhibitor 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
• 229960002073 sertraline Drugs 0.000 description 2
• 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 2
• 230000001568 sexual effect Effects 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 235000017281 sodium acetate Nutrition 0.000 description 2
• 229940087562 sodium acetate trihydrate Drugs 0.000 description 2
• JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
• 239000012312 sodium hydride Substances 0.000 description 2
• 229910000104 sodium hydride Inorganic materials 0.000 description 2
• 235000010265 sodium sulphite Nutrition 0.000 description 2
• AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 2
• 229940084026 sodium valproate Drugs 0.000 description 2
• 230000010473 stable expression Effects 0.000 description 2
• 230000000638 stimulation Effects 0.000 description 2
• 201000009032 substance abuse Diseases 0.000 description 2
• 238000006467 substitution reaction Methods 0.000 description 2
• 229950011332 talnetant Drugs 0.000 description 2
• OHLUOLTYTMEECV-UHFFFAOYSA-N tert-butyl 2-(3,5-difluoro-4-nitrophenyl)acetate Chemical compound CC(C)(C)OC(=O)CC1=CC(F)=C([N+]([O-])=O)C(F)=C1 OHLUOLTYTMEECV-UHFFFAOYSA-N 0.000 description 2
• VPWMYWZWIPSPIZ-UHFFFAOYSA-N tert-butyl 4-(2-amino-3-fluoro-5-methoxyanilino)piperidine-1-carboxylate Chemical compound COC1=CC(F)=C(N)C(NC2CCN(CC2)C(=O)OC(C)(C)C)=C1 VPWMYWZWIPSPIZ-UHFFFAOYSA-N 0.000 description 2
• WPGVDMMFDHNCKL-UHFFFAOYSA-N tert-butyl 4-(3-fluoro-5-methoxy-2-nitroanilino)piperidine-1-carboxylate Chemical compound COC1=CC(F)=C([N+]([O-])=O)C(NC2CCN(CC2)C(=O)OC(C)(C)C)=C1 WPGVDMMFDHNCKL-UHFFFAOYSA-N 0.000 description 2
• URZMJJACYUGKRT-UHFFFAOYSA-N tert-butyl 4-(4,5-difluoro-6-methyl-2-oxo-3h-benzimidazol-1-yl)piperidine-1-carboxylate Chemical compound O=C1NC=2C(F)=C(F)C(C)=CC=2N1C1CCN(C(=O)OC(C)(C)C)CC1 URZMJJACYUGKRT-UHFFFAOYSA-N 0.000 description 2
• SKGBPPYCDJEMIE-UHFFFAOYSA-N tert-butyl 4-[(2,3-difluoro-6-iodo-4-methylphenyl)carbamoylamino]piperidine-1-carboxylate Chemical compound FC1=C(F)C(C)=CC(I)=C1NC(=O)NC1CCN(C(=O)OC(C)(C)C)CC1 SKGBPPYCDJEMIE-UHFFFAOYSA-N 0.000 description 2
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
• DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 2
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
• PBJUNZJWGZTSKL-MRXNPFEDSA-N tiagabine Chemical compound C1=CSC(C(=CCCN2C[C@@H](CCC2)C(O)=O)C2=C(C=CS2)C)=C1C PBJUNZJWGZTSKL-MRXNPFEDSA-N 0.000 description 2
• 229960001918 tiagabine Drugs 0.000 description 2
• 229960005013 tiotixene Drugs 0.000 description 2
• 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 2
• 229960004394 topiramate Drugs 0.000 description 2
• 229960003741 tranylcypromine Drugs 0.000 description 2
• 229960003991 trazodone Drugs 0.000 description 2
• PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 description 2
• 239000003029 tricyclic antidepressant agent Substances 0.000 description 2
• 229960002431 trimipramine Drugs 0.000 description 2
• 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 2
• 229960004688 venlafaxine Drugs 0.000 description 2
• PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 2
• JOLJIIDDOBNFHW-UHFFFAOYSA-N xanomeline Chemical compound CCCCCCOC1=NSN=C1C1=CCCN(C)C1 JOLJIIDDOBNFHW-UHFFFAOYSA-N 0.000 description 2
• 229950006755 xanomeline Drugs 0.000 description 2
• BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 2
• 229960000317 yohimbine Drugs 0.000 description 2
• AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 2
• 229960002791 zimeldine Drugs 0.000 description 2
• OYPPVKRFBIWMSX-SXGWCWSVSA-N zimeldine Chemical compound C=1C=CN=CC=1C(=C/CN(C)C)\C1=CC=C(Br)C=C1 OYPPVKRFBIWMSX-SXGWCWSVSA-N 0.000 description 2
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
• SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
• RTGAJOPJZJDWAX-XVGSOSPHSA-N (1e,4e)-1,5-bis(3,5-dimethoxyphenyl)penta-1,4-dien-3-one;palladium Chemical compound [Pd].COC1=CC(OC)=CC(\C=C\C(=O)\C=C\C=2C=C(OC)C=C(OC)C=2)=C1.COC1=CC(OC)=CC(\C=C\C(=O)\C=C\C=2C=C(OC)C=C(OC)C=2)=C1 RTGAJOPJZJDWAX-XVGSOSPHSA-N 0.000 description 1
• WYDUSKDSKCASEF-LJQANCHMSA-N (1s)-1-cyclohexyl-1-phenyl-3-pyrrolidin-1-ylpropan-1-ol Chemical compound C([C@](O)(C1CCCCC1)C=1C=CC=CC=1)CN1CCCC1 WYDUSKDSKCASEF-LJQANCHMSA-N 0.000 description 1
• ZERWDZDNDJBYKA-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)ON1C(=O)CCC1=O ZERWDZDNDJBYKA-UHFFFAOYSA-N 0.000 description 1
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
• FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 description 1
• MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 description 1
• IFLZPECPTYCEBR-VIEYUMQNSA-N (z)-but-2-enedioic acid;(2r)-3-(2-methoxyphenothiazin-10-yl)-n,n,2-trimethylpropan-1-amine Chemical compound OC(=O)\C=C/C(O)=O.C1=CC=C2N(C[C@H](C)CN(C)C)C3=CC(OC)=CC=C3SC2=C1 IFLZPECPTYCEBR-VIEYUMQNSA-N 0.000 description 1
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
• ARCACZWMYGILNI-UHFFFAOYSA-N 1,2,3-trifluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(F)=C1F ARCACZWMYGILNI-UHFFFAOYSA-N 0.000 description 1
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
• SSNCMIDZGFCTST-UHFFFAOYSA-N 1,3-difluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=C(F)C=CC=C1F SSNCMIDZGFCTST-UHFFFAOYSA-N 0.000 description 1
• SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 1
• WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
• DKMFBWQBDIGMHM-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-(4-methyl-1-piperidinyl)-1-butanone Chemical compound C1CC(C)CCN1CCCC(=O)C1=CC=C(F)C=C1 DKMFBWQBDIGMHM-UHFFFAOYSA-N 0.000 description 1
• MQHYXXIJLKFQGY-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-(4-methylpiperidin-1-ium-1-yl)butan-1-one;chloride Chemical compound [Cl-].C1CC(C)CC[NH+]1CCCC(=O)C1=CC=C(F)C=C1 MQHYXXIJLKFQGY-UHFFFAOYSA-N 0.000 description 1
• AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
• SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
• LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
• BKYUJVHOWQZPQD-UHFFFAOYSA-N 2-[4-[3-(2-chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethanol;3-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylidene)-n,n-dimethylpropan-1-amine;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21.C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 BKYUJVHOWQZPQD-UHFFFAOYSA-N 0.000 description 1
• HBHBARSMRVAINH-UHFFFAOYSA-N 2-bromo-4-chloro-6-fluoroaniline Chemical compound NC1=C(F)C=C(Cl)C=C1Br HBHBARSMRVAINH-UHFFFAOYSA-N 0.000 description 1
• ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 description 1
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
• HJSSBIMVTMYKPD-UHFFFAOYSA-N 3,5-difluorophenol Chemical compound OC1=CC(F)=CC(F)=C1 HJSSBIMVTMYKPD-UHFFFAOYSA-N 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• BVUSNQJCSYDJJG-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one;2-hydroxypropanoic acid Chemical compound CC(O)C(O)=O.C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 BVUSNQJCSYDJJG-UHFFFAOYSA-N 0.000 description 1
• NQNQKLBWDARKDG-UHFFFAOYSA-N 4-amino-1-piperidinecarboxylic acid Chemical compound NC1CCN(C(O)=O)CC1 NQNQKLBWDARKDG-UHFFFAOYSA-N 0.000 description 1
• BFQSQUAVMNHOEF-UHFFFAOYSA-N 4-bromo-2,6-difluoroaniline Chemical compound NC1=C(F)C=C(Br)C=C1F BFQSQUAVMNHOEF-UHFFFAOYSA-N 0.000 description 1
• 229940127239 5 Hydroxytryptamine receptor antagonist Drugs 0.000 description 1
• AXXFKJZRMQNHPU-UHFFFAOYSA-N 5-chloro-7-fluoro-3-[1-(oxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one;hydrochloride Chemical compound Cl.O=C1NC=2C(F)=CC(Cl)=CC=2N1C(CC1)CCN1C1CCOCC1 AXXFKJZRMQNHPU-UHFFFAOYSA-N 0.000 description 1
• UHCMVLUHZXKNJQ-UHFFFAOYSA-N 6,7-difluoro-5-methyl-3-[1-(oxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC=2C(F)=C(F)C(C)=CC=2N1C(CC1)CCN1C1CCOCC1 UHCMVLUHZXKNJQ-UHFFFAOYSA-N 0.000 description 1
• FDACQSJDRGVKFF-UHFFFAOYSA-N 7-fluoro-5-methyl-3-[1-(oxan-4-yl)piperidin-4-yl]-1h-benzimidazol-2-one;hydrochloride Chemical compound Cl.C12=CC(C)=CC(F)=C2NC(=O)N1C(CC1)CCN1C1CCOCC1 FDACQSJDRGVKFF-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• JSXBVMKACNEMKY-UHFFFAOYSA-N 8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzoxazepine;hydron;chloride Chemical compound Cl.C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 JSXBVMKACNEMKY-UHFFFAOYSA-N 0.000 description 1
• 206010065040 AIDS dementia complex Diseases 0.000 description 1
• 206010001596 Alcohol induced persisting dementia Diseases 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• 208000000044 Amnesia Diseases 0.000 description 1
• 208000000103 Anorexia Nervosa Diseases 0.000 description 1
• 206010002859 Anxiety disorder due to a general medical condition Diseases 0.000 description 1
• 235000003911 Arachis Nutrition 0.000 description 1
• 244000105624 Arachis hypogaea Species 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 208000027448 Attention Deficit and Disruptive Behavior disease Diseases 0.000 description 1
• 206010003805 Autism Diseases 0.000 description 1
• 206010004716 Binge eating Diseases 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• 208000021500 Breathing-related sleep disease Diseases 0.000 description 1
• 208000021465 Brief psychotic disease Diseases 0.000 description 1
• 208000032841 Bulimia Diseases 0.000 description 1
• 206010006550 Bulimia nervosa Diseases 0.000 description 1
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
• 102000017924 CHRM4 Human genes 0.000 description 1
• 102000017923 CHRM5 Human genes 0.000 description 1
• 101150064612 CHRM5 gene Proteins 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• 101000957724 Catostomus commersonii Corticoliberin-1 Proteins 0.000 description 1
• 241000282693 Cercopithecidae Species 0.000 description 1
• 206010008027 Cerebellar atrophy Diseases 0.000 description 1
• 108091006146 Channels Proteins 0.000 description 1
• JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
• 208000019888 Circadian rhythm sleep 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
• 208000027691 Conduct disease Diseases 0.000 description 1
• 241001480079 Corymbia calophylla Species 0.000 description 1
• 206010012225 Delirium tremens Diseases 0.000 description 1
• OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
• 201000010374 Down Syndrome Diseases 0.000 description 1
• 208000004483 Dyspareunia Diseases 0.000 description 1
• 208000010228 Erectile Dysfunction Diseases 0.000 description 1
• 208000026097 Factitious disease Diseases 0.000 description 1
• 208000021663 Female sexual arousal disease Diseases 0.000 description 1
• LRWSFOSWNAQHHW-UHFFFAOYSA-N Fluphenazine enanthate Chemical compound C1CN(CCOC(=O)CCCCCC)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 LRWSFOSWNAQHHW-UHFFFAOYSA-N 0.000 description 1
• 208000010235 Food Addiction Diseases 0.000 description 1
• 206010017389 Frotteurism Diseases 0.000 description 1
• 108091006027 G proteins Proteins 0.000 description 1
• 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
• 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
• 230000005526 G1 to G0 transition Effects 0.000 description 1
• 102000030782 GTP binding Human genes 0.000 description 1
• 108091000058 GTP-Binding Proteins 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• 208000011688 Generalised anxiety disease Diseases 0.000 description 1
• 102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 description 1
• 108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 description 1
• 206010019196 Head injury Diseases 0.000 description 1
• 208000016619 Histrionic personality disease Diseases 0.000 description 1
• 241000282412 Homo Species 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
• KRDOFMHJLWKXIU-UHFFFAOYSA-N ID11614 Chemical class C1CNCCN1C1=NSC2=CC=CC=C12 KRDOFMHJLWKXIU-UHFFFAOYSA-N 0.000 description 1
• 208000016588 Idiopathic hypersomnia Diseases 0.000 description 1
• 208000001271 Inhalant Abuse Diseases 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
• 208000020358 Learning disease Diseases 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• 206010024419 Libido decreased Diseases 0.000 description 1
• 235000006552 Liquidambar styraciflua Nutrition 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 208000030431 Male orgasmic disease Diseases 0.000 description 1
• 206010026864 Masochism Diseases 0.000 description 1
• 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 description 1
• 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• GQWNECFJGBQMBO-UHFFFAOYSA-N Molindone hydrochloride Chemical compound Cl.O=C1C=2C(CC)=C(C)NC=2CCC1CN1CCOCC1 GQWNECFJGBQMBO-UHFFFAOYSA-N 0.000 description 1
• 206010027944 Mood disorder due to a general medical condition Diseases 0.000 description 1
• 208000005314 Multi-Infarct Dementia Diseases 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• 102000007207 Muscarinic M1 Receptor Human genes 0.000 description 1
• 108010008406 Muscarinic M1 Receptor Proteins 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• 208000027120 Narcissistic personality disease Diseases 0.000 description 1
• 206010028813 Nausea Diseases 0.000 description 1
• 208000009668 Neurobehavioral Manifestations Diseases 0.000 description 1
• 206010057852 Nicotine dependence Diseases 0.000 description 1
• 208000000224 Night Terrors Diseases 0.000 description 1
• 206010029412 Nightmare Diseases 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 208000008589 Obesity Diseases 0.000 description 1
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
• 206010033664 Panic attack Diseases 0.000 description 1
• 208000027099 Paranoid disease Diseases 0.000 description 1
• 208000018737 Parkinson disease Diseases 0.000 description 1
• 208000027089 Parkinsonian disease Diseases 0.000 description 1
• 206010034010 Parkinsonism Diseases 0.000 description 1
• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
• 208000032769 Pedophilia Diseases 0.000 description 1
• 244000025272 Persea americana Species 0.000 description 1
• 235000008673 Persea americana Nutrition 0.000 description 1
• 206010034912 Phobia Diseases 0.000 description 1
• 208000034592 Polysubstance dependence Diseases 0.000 description 1
• 102000007568 Proto-Oncogene Proteins c-fos Human genes 0.000 description 1
• 108010071563 Proto-Oncogene Proteins c-fos Proteins 0.000 description 1
• 206010052276 Pseudodementia Diseases 0.000 description 1
• 206010061921 Psychotic disorder due to a general medical condition Diseases 0.000 description 1
• 206010038743 Restlessness Diseases 0.000 description 1
• XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 description 1
• 206010039367 Sadism Diseases 0.000 description 1
• 208000030988 Schizoid Personality disease Diseases 0.000 description 1
• 208000024791 Schizotypal Personality disease Diseases 0.000 description 1
• 208000029901 Sexual arousal disease Diseases 0.000 description 1
• 208000029899 Sexual aversion disease Diseases 0.000 description 1
• 208000030047 Sexual desire disease Diseases 0.000 description 1
• 208000019568 Shared Paranoid disease Diseases 0.000 description 1
• 208000028810 Shared psychotic disease Diseases 0.000 description 1
• 206010063910 Sleep disorder due to a general medical condition Diseases 0.000 description 1
• 102100023145 Sodium- and chloride-dependent glycine transporter 1 Human genes 0.000 description 1
• 101710083171 Sodium- and chloride-dependent glycine transporter 1 Proteins 0.000 description 1
• 208000027520 Somatoform disease Diseases 0.000 description 1
• 206010041347 Somnambulism Diseases 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
• 231100000643 Substance intoxication Toxicity 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 206010042635 Suspiciousness Diseases 0.000 description 1
• 208000025569 Tobacco Use disease Diseases 0.000 description 1
• 208000000323 Tourette Syndrome Diseases 0.000 description 1
• 208000016620 Tourette disease Diseases 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 208000005386 Transient Global Amnesia Diseases 0.000 description 1
• 208000031674 Traumatic Acute Stress disease Diseases 0.000 description 1
• 206010044565 Tremor Diseases 0.000 description 1
• HWHLPVGTWGOCJO-UHFFFAOYSA-N Trihexyphenidyl Chemical group C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 HWHLPVGTWGOCJO-UHFFFAOYSA-N 0.000 description 1
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
• 206010044688 Trisomy 21 Diseases 0.000 description 1
• 201000004810 Vascular dementia Diseases 0.000 description 1
• 208000027418 Wounds and injury Diseases 0.000 description 1
• 101100107916 Xenopus laevis chrm4 gene Proteins 0.000 description 1
• 150000001241 acetals Chemical class 0.000 description 1
• NUKVZKPNSKJGBK-SPIKMXEPSA-N acetophenazine dimaleate Chemical compound [H+].[H+].[H+].[H+].[O-]C(=O)\C=C/C([O-])=O.[O-]C(=O)\C=C/C([O-])=O.C12=CC(C(=O)C)=CC=C2SC2=CC=CC=C2N1CCCN1CCN(CCO)CC1 NUKVZKPNSKJGBK-SPIKMXEPSA-N 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 208000026345 acute stress disease Diseases 0.000 description 1
• 238000011360 adjunctive therapy Methods 0.000 description 1
• 230000007000 age related cognitive decline Effects 0.000 description 1
• 206010001584 alcohol abuse Diseases 0.000 description 1
• 201000007930 alcohol dependence Diseases 0.000 description 1
• 208000025746 alcohol use disease Diseases 0.000 description 1
• 208000029650 alcohol withdrawal Diseases 0.000 description 1
• 208000006246 alcohol withdrawal delirium Diseases 0.000 description 1
• 230000001476 alcoholic effect Effects 0.000 description 1
• 125000002877 alkyl aryl group Chemical group 0.000 description 1
• 150000001350 alkyl halides Chemical class 0.000 description 1
• 230000002152 alkylating effect Effects 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
• 229960003805 amantadine Drugs 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• 230000006986 amnesia Effects 0.000 description 1
• 230000003109 amnesic effect Effects 0.000 description 1
• 201000002472 amphetamine abuse Diseases 0.000 description 1
• APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 1
• 229960003942 amphotericin b Drugs 0.000 description 1
• 239000003708 ampul Substances 0.000 description 1
• 239000003263 anabolic agent Substances 0.000 description 1
• 229940070021 anabolic steroids Drugs 0.000 description 1
• 150000001448 anilines Chemical class 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 1
• 239000000739 antihistaminic agent Substances 0.000 description 1
• 229940125715 antihistaminic agent Drugs 0.000 description 1
• 229940082988 antihypertensives serotonin antagonists Drugs 0.000 description 1
• 239000003420 antiserotonin agent Substances 0.000 description 1
• 208000024823 antisocial personality disease Diseases 0.000 description 1
• 230000036506 anxiety Effects 0.000 description 1
• VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
• 229960004046 apomorphine Drugs 0.000 description 1
• 239000008365 aqueous carrier Substances 0.000 description 1
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
• 208000022804 avoidant personality disease Diseases 0.000 description 1
• 230000006399 behavior Effects 0.000 description 1
• GIJXKZJWITVLHI-PMOLBWCYSA-N benzatropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(C=1C=CC=CC=1)C1=CC=CC=C1 GIJXKZJWITVLHI-PMOLBWCYSA-N 0.000 description 1
• 229960001081 benzatropine Drugs 0.000 description 1
• 150000008316 benzisoxazoles Chemical class 0.000 description 1
• 150000001557 benzodiazepines Chemical class 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
• 208000014679 binge eating disease Diseases 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 229960003003 biperiden Drugs 0.000 description 1
• YSXKPIUOCJLQIE-UHFFFAOYSA-N biperiden Chemical compound C1C(C=C2)CC2C1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 YSXKPIUOCJLQIE-UHFFFAOYSA-N 0.000 description 1
• 208000028683 bipolar I disease Diseases 0.000 description 1
• 208000022257 bipolar II disease Diseases 0.000 description 1
• 208000030963 borderline personality disease Diseases 0.000 description 1
• 230000031709 bromination Effects 0.000 description 1
• 238000005893 bromination reaction Methods 0.000 description 1
• FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical class CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
• 230000028956 calcium-mediated signaling Effects 0.000 description 1
• 201000009322 cannabis abuse Diseases 0.000 description 1
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 206010007776 catatonia Diseases 0.000 description 1
• 239000006285 cell suspension Substances 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 230000002490 cerebral effect Effects 0.000 description 1
• WUTYZMFRCNBCHQ-PSASIEDQSA-N cevimeline Chemical compound C1S[C@H](C)O[C@]21C(CC1)CCN1C2 WUTYZMFRCNBCHQ-PSASIEDQSA-N 0.000 description 1
• 229960001314 cevimeline Drugs 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 238000005660 chlorination reaction Methods 0.000 description 1
• 239000000812 cholinergic antagonist Substances 0.000 description 1
• 210000002932 cholinergic neuron Anatomy 0.000 description 1
• NJMYODHXAKYRHW-DVZOWYKESA-N cis-flupenthixol Chemical compound C1CN(CCO)CCN1CC\C=C\1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C2/1 NJMYODHXAKYRHW-DVZOWYKESA-N 0.000 description 1
• 230000009194 climbing Effects 0.000 description 1
• 229940068796 clozaril Drugs 0.000 description 1
• 229960003920 cocaine Drugs 0.000 description 1
• 201000001272 cocaine abuse Diseases 0.000 description 1
• 201000006145 cocaine dependence Diseases 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 230000003920 cognitive function Effects 0.000 description 1
• 238000004040 coloring Methods 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 229940088505 compazine Drugs 0.000 description 1
• 230000001143 conditioned effect Effects 0.000 description 1
• 238000011340 continuous therapy Methods 0.000 description 1
• 229940111134 coxibs Drugs 0.000 description 1
• 235000019788 craving Nutrition 0.000 description 1
• 239000013058 crude material Substances 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• WLVKDFJTYKELLQ-UHFFFAOYSA-N cyclopropylboronic acid Chemical compound OB(O)C1CC1 WLVKDFJTYKELLQ-UHFFFAOYSA-N 0.000 description 1
• 208000026725 cyclothymic disease Diseases 0.000 description 1
• YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 230000006735 deficit Effects 0.000 description 1
• 230000003412 degenerative effect Effects 0.000 description 1
• 230000001419 dependent effect Effects 0.000 description 1
• 208000030964 dependent personality disease Diseases 0.000 description 1
• 239000012954 diazonium Substances 0.000 description 1
• IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
• 150000008533 dibenzodiazepines Chemical class 0.000 description 1
• 150000008509 dibenzothiazepines Chemical class 0.000 description 1
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
• 229960000520 diphenhydramine Drugs 0.000 description 1
• MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 229960003530 donepezil Drugs 0.000 description 1
• 239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
• 231100000673 dose–response relationship Toxicity 0.000 description 1
• 239000006196 drop Substances 0.000 description 1
• 238000007876 drug discovery Methods 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• 230000000142 dyskinetic effect Effects 0.000 description 1
• 208000024732 dysthymic disease Diseases 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 150000002081 enamines Chemical class 0.000 description 1
• 238000005538 encapsulation Methods 0.000 description 1
• 238000005516 engineering process Methods 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• 125000004185 ester group Chemical group 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 1
• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
• 229940103472 etrafon Drugs 0.000 description 1
• 208000003481 exhibitionism Diseases 0.000 description 1
• 210000003499 exocrine gland Anatomy 0.000 description 1
• 208000014840 female orgasmic disease Diseases 0.000 description 1
• 206010016531 fetishism Diseases 0.000 description 1
• 238000010304 firing Methods 0.000 description 1
• 238000003682 fluorination reaction Methods 0.000 description 1
• 229960002419 flupentixol Drugs 0.000 description 1
• 229960000787 fluphenazine enanthate Drugs 0.000 description 1
• 229960001258 fluphenazine hydrochloride Drugs 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 238000004108 freeze drying Methods 0.000 description 1
• 230000006870 function Effects 0.000 description 1
• 238000002825 functional assay Methods 0.000 description 1
• 229960003980 galantamine Drugs 0.000 description 1
• ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 230000005176 gastrointestinal motility Effects 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 230000014509 gene expression Effects 0.000 description 1
• 208000029364 generalized anxiety disease Diseases 0.000 description 1
• 229940003380 geodon Drugs 0.000 description 1
• 229930182470 glycoside Natural products 0.000 description 1
• 150000002338 glycosides Chemical class 0.000 description 1
• MFWNKCLOYSRHCJ-BTTYYORXSA-N granisetron Chemical compound C1=CC=C2C(C(=O)N[C@H]3C[C@H]4CCC[C@@H](C3)N4C)=NN(C)C2=C1 MFWNKCLOYSRHCJ-BTTYYORXSA-N 0.000 description 1
• 229960003727 granisetron Drugs 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 201000002270 hallucinogen abuse Diseases 0.000 description 1
• 201000006138 hallucinogen dependence Diseases 0.000 description 1
• 230000026030 halogenation Effects 0.000 description 1
• 238000005658 halogenation reaction Methods 0.000 description 1
• 229960001345 haloperidol lactate Drugs 0.000 description 1
• 235000015220 hamburgers Nutrition 0.000 description 1
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 210000001320 hippocampus Anatomy 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 150000002430 hydrocarbons Chemical group 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 208000013403 hyperactivity Diseases 0.000 description 1
• 208000017020 hypoactive sexual desire disease Diseases 0.000 description 1
• 229960003162 iloperidone Drugs 0.000 description 1
• 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 1
• 238000003384 imaging method Methods 0.000 description 1
• 150000008624 imidazolidinones Chemical class 0.000 description 1
• 150000002466 imines Chemical class 0.000 description 1
• 238000011065 in-situ storage Methods 0.000 description 1
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 201000004197 inhibited female orgasm Diseases 0.000 description 1
• 201000000068 inhibited male orgasm Diseases 0.000 description 1
• 230000003834 intracellular effect Effects 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 230000008449 language Effects 0.000 description 1
• 201000010901 lateral sclerosis Diseases 0.000 description 1
• 201000003723 learning disability Diseases 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 230000003902 lesion Effects 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
• 239000012669 liquid formulation Substances 0.000 description 1
• 239000012160 loading buffer Substances 0.000 description 1
• 230000033001 locomotion Effects 0.000 description 1
• 229960004990 loxapine hydrochloride Drugs 0.000 description 1
• 229960000589 loxapine succinate Drugs 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 208000015421 male orgasm disease Diseases 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• 229960001861 melperone Drugs 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 239000002207 metabolite Substances 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• VRQVVMDWGGWHTJ-CQSZACIVSA-N methotrimeprazine Chemical compound C1=CC=C2N(C[C@H](C)CN(C)C)C3=CC(OC)=CC=C3SC2=C1 VRQVVMDWGGWHTJ-CQSZACIVSA-N 0.000 description 1
• GQJCAQADCPTHKN-UHFFFAOYSA-N methyl 2,2-difluoro-2-fluorosulfonylacetate Chemical compound COC(=O)C(F)(F)S(F)(=O)=O GQJCAQADCPTHKN-UHFFFAOYSA-N 0.000 description 1
• 208000027061 mild cognitive impairment Diseases 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 229960004684 molindone hydrochloride Drugs 0.000 description 1
• 208000005264 motor neuron disease Diseases 0.000 description 1
• 239000000472 muscarinic agonist Substances 0.000 description 1
• RLKHFSNWQCZBDC-UHFFFAOYSA-N n-(benzenesulfonyl)-n-fluorobenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(F)S(=O)(=O)C1=CC=CC=C1 RLKHFSNWQCZBDC-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
• 201000003631 narcolepsy Diseases 0.000 description 1
• 230000008693 nausea Effects 0.000 description 1
• 210000001577 neostriatum Anatomy 0.000 description 1
• 230000004770 neurodegeneration Effects 0.000 description 1
• 239000003176 neuroleptic agent Substances 0.000 description 1
• 230000000701 neuroleptic effect Effects 0.000 description 1
• 239000002581 neurotoxin Substances 0.000 description 1
• 239000002858 neurotransmitter agent Substances 0.000 description 1
• 229960002715 nicotine Drugs 0.000 description 1
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 150000005181 nitrobenzenes Chemical class 0.000 description 1
• 239000001272 nitrous oxide Substances 0.000 description 1
• 125000006574 non-aromatic ring group Chemical group 0.000 description 1
• 229940126569 noradrenaline reuptake inhibitor Drugs 0.000 description 1
• 229960002748 norepinephrine Drugs 0.000 description 1
• SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
• 230000000966 norepinephrine reuptake Effects 0.000 description 1
• 210000001009 nucleus accumben Anatomy 0.000 description 1
• 235000020824 obesity Nutrition 0.000 description 1
• 208000030459 obsessive-compulsive personality disease Diseases 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 229960005343 ondansetron Drugs 0.000 description 1
• 201000000988 opioid abuse Diseases 0.000 description 1
• 208000024196 oppositional defiant disease Diseases 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000003891 oxalate salts Chemical class 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 208000027753 pain disease Diseases 0.000 description 1
• 208000024817 paranoid personality disease Diseases 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 235000010603 pastilles Nutrition 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 229960002195 perazine Drugs 0.000 description 1
• 210000001428 peripheral nervous system Anatomy 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 229950000688 phenothiazine Drugs 0.000 description 1
• 150000002990 phenothiazines Chemical class 0.000 description 1
• 150000003014 phosphoric acid esters Chemical class 0.000 description 1
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
• JOMHSQGEWSNUKU-UHFFFAOYSA-N pipotiazine Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2N1CCCN1CCC(CCO)CC1 JOMHSQGEWSNUKU-UHFFFAOYSA-N 0.000 description 1
• 229960003252 pipotiazine Drugs 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 208000028173 post-traumatic stress disease Diseases 0.000 description 1
• 239000002243 precursor Substances 0.000 description 1
• 210000002442 prefrontal cortex Anatomy 0.000 description 1
• 206010036596 premature ejaculation Diseases 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• 238000012545 processing Methods 0.000 description 1
• DSKIOWHQLUWFLG-SPIKMXEPSA-N prochlorperazine maleate Chemical compound [H+].[H+].[H+].[H+].[O-]C(=O)\C=C/C([O-])=O.[O-]C(=O)\C=C/C([O-])=O.C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 DSKIOWHQLUWFLG-SPIKMXEPSA-N 0.000 description 1
• 229960005253 procyclidine Drugs 0.000 description 1
• 229960003598 promazine Drugs 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• 210000004129 prosencephalon Anatomy 0.000 description 1
• ZTHJULTYCAQOIJ-WXXKFALUSA-N quetiapine fumarate Chemical compound [H+].[H+].[O-]C(=O)\C=C\C([O-])=O.C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12.C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 ZTHJULTYCAQOIJ-WXXKFALUSA-N 0.000 description 1
• 229960005197 quetiapine fumarate Drugs 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 230000000306 recurrent effect Effects 0.000 description 1
• 238000009256 replacement therapy Methods 0.000 description 1
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
• 229940106887 risperdal Drugs 0.000 description 1
• 229960004136 rivastigmine Drugs 0.000 description 1
• 208000022610 schizoaffective disease Diseases 0.000 description 1
• 229940035004 seroquel Drugs 0.000 description 1
• 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 1
• 229960000652 sertindole Drugs 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 208000012201 sexual and gender identity disease Diseases 0.000 description 1
• 208000015891 sexual disease Diseases 0.000 description 1
• 201000005814 sexual masochism Diseases 0.000 description 1
• 208000027599 sexual masochism disease Diseases 0.000 description 1
• 201000005841 sexual sadism Diseases 0.000 description 1
• 208000027596 sexual sadism disease Diseases 0.000 description 1
• 150000004760 silicates Chemical class 0.000 description 1
• 238000009097 single-agent therapy Methods 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• 239000012279 sodium borohydride Substances 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000003195 sodium channel blocking agent Substances 0.000 description 1
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
• 230000000392 somatic effect Effects 0.000 description 1
• 201000001716 specific phobia Diseases 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 239000006190 sub-lingual tablet Substances 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 231100000736 substance abuse Toxicity 0.000 description 1
• 201000006152 substance dependence Diseases 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
• 150000003462 sulfoxides Chemical class 0.000 description 1
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
• 229910021653 sulphate ion Inorganic materials 0.000 description 1
• 239000002511 suppository base Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 238000002636 symptomatic treatment Methods 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 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
• KUYMVWXKHQSIAS-UHFFFAOYSA-N tert-butyl 2-chloroacetate Chemical compound CC(C)(C)OC(=O)CCl KUYMVWXKHQSIAS-UHFFFAOYSA-N 0.000 description 1
• MUNHANZLYUCPKU-UHFFFAOYSA-N tert-butyl 4-(4-fluoro-6-methoxy-2-oxo-3h-benzimidazol-1-yl)piperidine-1-carboxylate Chemical compound C12=CC(OC)=CC(F)=C2NC(=O)N1C1CCN(C(=O)OC(C)(C)C)CC1 MUNHANZLYUCPKU-UHFFFAOYSA-N 0.000 description 1
• MWRDGYGQIVGWTB-UHFFFAOYSA-N tert-butyl 4-(6-chloro-4-fluoro-2-oxo-3h-benzimidazol-1-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1C(=O)NC2=C(F)C=C(Cl)C=C21 MWRDGYGQIVGWTB-UHFFFAOYSA-N 0.000 description 1
• CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 1
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 238000010998 test method Methods 0.000 description 1
• 238000012360 testing method Methods 0.000 description 1
• 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 229960000882 thiothixene hydrochloride Drugs 0.000 description 1
• 150000005075 thioxanthenes Chemical class 0.000 description 1
• 208000016686 tic disease Diseases 0.000 description 1
• 239000010936 titanium Substances 0.000 description 1
• 238000004448 titration Methods 0.000 description 1
• 125000003944 tolyl group Chemical group 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 230000010474 transient expression Effects 0.000 description 1
• 201000005142 transvestism Diseases 0.000 description 1
• 230000008733 trauma Effects 0.000 description 1
• 229960001032 trihexyphenidyl Drugs 0.000 description 1
• 239000003174 triple reuptake inhibitor Substances 0.000 description 1
• 238000001665 trituration Methods 0.000 description 1
• 206010046947 vaginismus Diseases 0.000 description 1
• 208000008918 voyeurism Diseases 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 239000012991 xanthate Substances 0.000 description 1
• 229940039925 zyprexa Drugs 0.000 description 1