ES2333918T3 - Derivados de pirrolidina que tiene la actividad en el transportador glyt1. - Google Patents
Derivados de pirrolidina que tiene la actividad en el transportador glyt1. Download PDFInfo
- Publication number
- ES2333918T3 ES2333918T3 ES07786764T ES07786764T ES2333918T3 ES 2333918 T3 ES2333918 T3 ES 2333918T3 ES 07786764 T ES07786764 T ES 07786764T ES 07786764 T ES07786764 T ES 07786764T ES 2333918 T3 ES2333918 T3 ES 2333918T3
- Authority
- ES
- Spain
- Prior art keywords
- pyrrolidinyl
- methyl
- phenyl
- propyl
- trifluoromethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title description 18
- 230000000694 effects Effects 0.000 title description 7
- 102100022622 Alpha-1,3-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferase Human genes 0.000 title 1
- 101000972916 Homo sapiens Alpha-1,3-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferase Proteins 0.000 title 1
- NGWVYOWTXSIDQF-UHFFFAOYSA-N 2-methoxy-n-(2-methyl-1-phenyl-2-pyrrolidin-1-ylpropyl)-4,6-bis(trifluoromethyl)benzamide Chemical compound COC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC(C(C)(C)N1CCCC1)C1=CC=CC=C1 NGWVYOWTXSIDQF-UHFFFAOYSA-N 0.000 claims abstract description 94
- 239000012453 solvate Substances 0.000 claims abstract description 86
- 150000001875 compounds Chemical class 0.000 claims description 82
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 76
- 208000035475 disorder Diseases 0.000 claims description 69
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 63
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 62
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 61
- 208000028017 Psychotic disease Diseases 0.000 claims description 42
- PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 claims description 42
- 238000011282 treatment Methods 0.000 claims description 41
- 239000003814 drug Substances 0.000 claims description 32
- 229950005216 napadisilate Drugs 0.000 claims description 29
- 101710083171 Sodium- and chloride-dependent glycine transporter 1 Proteins 0.000 claims description 27
- 102100023145 Sodium- and chloride-dependent glycine transporter 1 Human genes 0.000 claims description 22
- 230000001225 therapeutic effect Effects 0.000 claims description 22
- 229940079593 drug Drugs 0.000 claims description 20
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 206010012289 Dementia Diseases 0.000 claims description 15
- 230000001404 mediated effect Effects 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 201000000980 schizophrenia Diseases 0.000 claims description 13
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 12
- 239000005557 antagonist Substances 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 7
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 239000000935 antidepressant agent Substances 0.000 claims description 5
- 229940125681 anticonvulsant agent Drugs 0.000 claims description 4
- 239000001961 anticonvulsive agent Substances 0.000 claims description 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 3
- 229940123445 Tricyclic antidepressant Drugs 0.000 claims description 3
- 239000000556 agonist Substances 0.000 claims description 3
- 229940005513 antidepressants Drugs 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000006735 deficit Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 3
- 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 claims description 3
- 239000000952 serotonin receptor agonist Substances 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 239000003029 tricyclic antidepressant agent Substances 0.000 claims description 3
- 101000783611 Takifugu rubripes 5-hydroxytryptamine receptor 1D Proteins 0.000 claims description 2
- 239000002475 cognitive enhancer Substances 0.000 claims description 2
- 230000003291 dopaminomimetic effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229940076279 serotonin Drugs 0.000 claims description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims 1
- 239000003693 atypical antipsychotic agent Substances 0.000 claims 1
- 229940127236 atypical antipsychotics Drugs 0.000 claims 1
- 229960002748 norepinephrine Drugs 0.000 claims 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 86
- 239000000243 solution Substances 0.000 description 72
- 239000000203 mixture Chemical class 0.000 description 64
- 239000007787 solid Substances 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 235000019439 ethyl acetate Nutrition 0.000 description 39
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 239000002253 acid Substances 0.000 description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 29
- 239000002904 solvent Substances 0.000 description 28
- 238000003756 stirring Methods 0.000 description 26
- 150000003839 salts Chemical class 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000000725 suspension Substances 0.000 description 23
- GEPUTQMHNJGKLT-UHFFFAOYSA-N 2-methyl-1-phenyl-2-pyrrolidin-1-ylpropan-1-amine Chemical compound C1CCCN1C(C)(C)C(N)C1=CC=CC=C1 GEPUTQMHNJGKLT-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 17
- -1 monosuccinate salt Chemical class 0.000 description 17
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 17
- 239000003176 neuroleptic agent Substances 0.000 description 16
- 208000019116 sleep disease Diseases 0.000 description 16
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000002249 anxiolytic agent Substances 0.000 description 15
- 230000000949 anxiolytic effect Effects 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- 230000000147 hypnotic effect Effects 0.000 description 15
- 239000000932 sedative agent Substances 0.000 description 15
- 208000019901 Anxiety disease Diseases 0.000 description 14
- 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 14
- 238000009472 formulation Methods 0.000 description 14
- 230000001624 sedative effect Effects 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 12
- 229950010883 phencyclidine Drugs 0.000 description 12
- 239000004471 Glycine Substances 0.000 description 11
- 208000019022 Mood disease Diseases 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 206010012218 Delirium Diseases 0.000 description 10
- 208000005374 Poisoning Diseases 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 231100000572 poisoning Toxicity 0.000 description 10
- 230000000607 poisoning effect Effects 0.000 description 10
- 208000020685 sleep-wake disease Diseases 0.000 description 10
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 9
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 9
- 201000001880 Sexual dysfunction Diseases 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 230000002085 persistent effect Effects 0.000 description 9
- 231100000872 sexual dysfunction Toxicity 0.000 description 9
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 8
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
- 229940025084 amphetamine Drugs 0.000 description 8
- 208000010877 cognitive disease Diseases 0.000 description 8
- 230000014509 gene expression Effects 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 208000020016 psychiatric disease Diseases 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000001384 succinic acid Substances 0.000 description 8
- 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 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 229960003920 cocaine Drugs 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 239000000380 hallucinogen Substances 0.000 description 7
- 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 7
- 239000000126 substance Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- 208000020706 Autistic disease Diseases 0.000 description 5
- 241000218236 Cannabis Species 0.000 description 5
- 208000028698 Cognitive impairment Diseases 0.000 description 5
- 206010013654 Drug abuse Diseases 0.000 description 5
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 5
- 102100028886 Sodium- and chloride-dependent glycine transporter 2 Human genes 0.000 description 5
- 101710083167 Sodium- and chloride-dependent glycine transporter 2 Proteins 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 229960001948 caffeine Drugs 0.000 description 5
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 208000013403 hyperactivity Diseases 0.000 description 5
- 230000035987 intoxication Effects 0.000 description 5
- 231100000566 intoxication Toxicity 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 208000024714 major depressive disease Diseases 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- GUGMWCUXIGSRJX-UHFFFAOYSA-N 2-methyl-2-pyrrolidin-1-ylpropanenitrile Chemical compound N#CC(C)(C)N1CCCC1 GUGMWCUXIGSRJX-UHFFFAOYSA-N 0.000 description 4
- 208000020925 Bipolar disease Diseases 0.000 description 4
- 208000022497 Cocaine-Related disease Diseases 0.000 description 4
- DIWVBIXQCNRCFE-UHFFFAOYSA-N DL-alpha-Methoxyphenylacetic acid Chemical compound COC(C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-UHFFFAOYSA-N 0.000 description 4
- 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 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 206010026749 Mania Diseases 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000007832 Na2SO4 Substances 0.000 description 4
- 208000026251 Opioid-Related disease Diseases 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 208000006011 Stroke Diseases 0.000 description 4
- 230000004075 alteration Effects 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000000228 antimanic agent Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000019771 cognition Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000004050 mood stabilizer Substances 0.000 description 4
- 229940127237 mood stabilizer Drugs 0.000 description 4
- 230000001575 pathological effect Effects 0.000 description 4
- 208000022821 personality disease Diseases 0.000 description 4
- 238000002603 single-photon emission computed tomography Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 208000011117 substance-related disease Diseases 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 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 4
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
- UGPLARWZFAOTLM-UHFFFAOYSA-N 2-methoxy-n-(2-methyl-1-phenyl-2-pyrrolidin-1-ylpropyl)-4,6-bis(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.COC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC(C(C)(C)N1CCCC1)C1=CC=CC=C1 UGPLARWZFAOTLM-UHFFFAOYSA-N 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 206010003805 Autism Diseases 0.000 description 3
- 244000110556 Cyclopia subternata Species 0.000 description 3
- 206010012239 Delusion Diseases 0.000 description 3
- 208000030814 Eating disease Diseases 0.000 description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 description 3
- 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 3
- 208000004230 Gender Dysphoria Diseases 0.000 description 3
- 208000003863 Marijuana Abuse Diseases 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- KLPWJLBORRMFGK-UHFFFAOYSA-N Molindone Chemical compound O=C1C=2C(CC)=C(C)NC=2CCC1CN1CCOCC1 KLPWJLBORRMFGK-UHFFFAOYSA-N 0.000 description 3
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 3
- RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-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
- 208000006262 Psychological Sexual Dysfunctions Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 3
- KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 description 3
- 229960000276 acetophenazine Drugs 0.000 description 3
- 230000003109 amnesic effect Effects 0.000 description 3
- 239000000164 antipsychotic agent Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000012131 assay buffer Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 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 3
- 229960001076 chlorpromazine Drugs 0.000 description 3
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 231100000868 delusion Toxicity 0.000 description 3
- 230000001066 destructive effect Effects 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 235000014632 disordered eating Nutrition 0.000 description 3
- 229960000394 droperidol Drugs 0.000 description 3
- 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 3
- 206010013663 drug dependence Diseases 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 229960003878 haloperidol Drugs 0.000 description 3
- 206010020765 hypersomnia Diseases 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 208000014674 injury Diseases 0.000 description 3
- 206010022437 insomnia Diseases 0.000 description 3
- XJGVXQDUIWGIRW-UHFFFAOYSA-N loxapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 XJGVXQDUIWGIRW-UHFFFAOYSA-N 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 230000036651 mood Effects 0.000 description 3
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 3
- 229960002715 nicotine Drugs 0.000 description 3
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 3
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 3
- 208000019906 panic disease Diseases 0.000 description 3
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 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 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 201000009032 substance abuse Diseases 0.000 description 3
- 230000005062 synaptic transmission Effects 0.000 description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- 230000008673 vomiting Effects 0.000 description 3
- 229960000607 ziprasidone Drugs 0.000 description 3
- 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 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- QMOSZSHTSOWPRX-UHFFFAOYSA-N 2-bromo-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(Br)C(=O)C1=CC=CC=C1 QMOSZSHTSOWPRX-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
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 2
- 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 2
- 206010000117 Abnormal behaviour Diseases 0.000 description 2
- 244000215068 Acacia senegal Species 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
- 208000031091 Amnestic disease Diseases 0.000 description 2
- 208000029197 Amphetamine-Related disease Diseases 0.000 description 2
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 108010078791 Carrier Proteins Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 208000017781 Cocaine intoxication Diseases 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 description 2
- 208000029810 Gender identity disease Diseases 0.000 description 2
- 229940123454 Glucose transporter 1 inhibitor Drugs 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 description 2
- 108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 description 2
- 102000011714 Glycine Receptors Human genes 0.000 description 2
- 108010076533 Glycine Receptors Proteins 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- 208000004547 Hallucinations Diseases 0.000 description 2
- 208000023105 Huntington disease Diseases 0.000 description 2
- 208000020358 Learning disease Diseases 0.000 description 2
- 208000026139 Memory disease Diseases 0.000 description 2
- 206010061285 Mental disorder due to a general medical condition Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 208000005314 Multi-Infarct Dementia Diseases 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 208000012902 Nervous system disease Diseases 0.000 description 2
- 208000025966 Neurological disease Diseases 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 206010033888 Paraphilia Diseases 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- 208000030988 Schizoid Personality disease Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000011963 Substance-induced psychotic disease Diseases 0.000 description 2
- 231100000393 Substance-induced psychotic disorder Toxicity 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000012317 TBTU Substances 0.000 description 2
- 208000030886 Traumatic Brain injury Diseases 0.000 description 2
- 201000004810 Vascular dementia Diseases 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 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
- 230000004913 activation Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 201000007930 alcohol dependence Diseases 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229940005529 antipsychotics Drugs 0.000 description 2
- 229940005530 anxiolytics Drugs 0.000 description 2
- 229960004372 aripiprazole Drugs 0.000 description 2
- 230000003542 behavioural effect Effects 0.000 description 2
- 229960002507 benperidol Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 208000028683 bipolar I disease Diseases 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 201000001843 cannabis dependence Diseases 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 2
- 229960001552 chlorprothixene Drugs 0.000 description 2
- 230000002566 clonic effect Effects 0.000 description 2
- 229960004170 clozapine Drugs 0.000 description 2
- 230000001149 cognitive effect Effects 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 230000003001 depressive effect Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 201000002545 drug psychosis Diseases 0.000 description 2
- 230000002996 emotional effect Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 206010016531 fetishism Diseases 0.000 description 2
- 229960002690 fluphenazine Drugs 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000003400 hallucinatory effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000011872 intimate mixture Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 201000003723 learning disability Diseases 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229960000423 loxapine Drugs 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 206010027175 memory impairment Diseases 0.000 description 2
- 229960004503 metoclopramide 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
- 238000010369 molecular cloning Methods 0.000 description 2
- 229960004938 molindone Drugs 0.000 description 2
- 208000004296 neuralgia Diseases 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- 230000000926 neurological effect Effects 0.000 description 2
- 210000002569 neuron Anatomy 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 229960005017 olanzapine Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 208000024309 orgasm disease Diseases 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 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
- 230000008447 perception Effects 0.000 description 2
- 229960000762 perphenazine Drugs 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 2
- 229960003111 prochlorperazine Drugs 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229960001534 risperidone Drugs 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 208000022610 schizoaffective disease Diseases 0.000 description 2
- 238000000527 sonication Methods 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- 229960002784 thioridazine Drugs 0.000 description 2
- 230000001256 tonic effect Effects 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- 238000011269 treatment regimen Methods 0.000 description 2
- ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 2
- 229960002324 trifluoperazine Drugs 0.000 description 2
- BXDAOUXDMHXPDI-UHFFFAOYSA-N trifluoperazine hydrochloride Chemical compound [H+].[H+].[Cl-].[Cl-].C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 BXDAOUXDMHXPDI-UHFFFAOYSA-N 0.000 description 2
- 210000004916 vomit Anatomy 0.000 description 2
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
- DIWVBIXQCNRCFE-MRVPVSSYSA-N (2r)-2-methoxy-2-phenylacetic acid Chemical compound CO[C@@H](C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-MRVPVSSYSA-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
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 1
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 1
- WXUAQHNMJWJLTG-VKHMYHEASA-N (S)-methylsuccinic acid Chemical compound OC(=O)[C@@H](C)CC(O)=O WXUAQHNMJWJLTG-VKHMYHEASA-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
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical class C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-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
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-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
- IIWWKGJYKXFWRG-UHFFFAOYSA-N 2-methoxy-4,6-bis(trifluoromethyl)benzoic acid Chemical compound COC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(O)=O IIWWKGJYKXFWRG-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- AVMIBSYQKBTNOW-UHFFFAOYSA-N 4-methylperoxy-4-oxobutanoic acid Chemical compound COOC(=O)CCC(O)=O AVMIBSYQKBTNOW-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 206010065040 AIDS dementia complex Diseases 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
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 208000021465 Brief psychotic disease Diseases 0.000 description 1
- 206010006550 Bulimia nervosa Diseases 0.000 description 1
- 206010008027 Cerebellar atrophy Diseases 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
- GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 description 1
- 208000018652 Closed Head injury Diseases 0.000 description 1
- 206010012225 Delirium tremens Diseases 0.000 description 1
- 208000024254 Delusional disease Diseases 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- 206010054089 Depressive symptom Diseases 0.000 description 1
- 201000010374 Down Syndrome Diseases 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 208000004483 Dyspareunia Diseases 0.000 description 1
- 208000010228 Erectile Dysfunction Diseases 0.000 description 1
- 108700024394 Exon Proteins 0.000 description 1
- 208000021663 Female sexual arousal disease Diseases 0.000 description 1
- 208000001640 Fibromyalgia Diseases 0.000 description 1
- 201000011240 Frontotemporal dementia Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 208000011688 Generalised anxiety disease Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229940088352 Glycine transporter inhibitor Drugs 0.000 description 1
- 239000007821 HATU Substances 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
- 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
- ZCYVEMRRCGMTRW-AHCXROLUSA-N Iodine-123 Chemical compound [123I] ZCYVEMRRCGMTRW-AHCXROLUSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 206010024419 Libido decreased Diseases 0.000 description 1
- 208000008930 Low Back Pain Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010026864 Masochism Diseases 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 208000027120 Narcissistic personality disease Diseases 0.000 description 1
- 206010028980 Neoplasm 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
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-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
- 208000006199 Parasomnias Diseases 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
- 208000032769 Pedophilia Diseases 0.000 description 1
- 206010034759 Petit mal epilepsy Diseases 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 206010034912 Phobia Diseases 0.000 description 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 description 1
- 208000034592 Polysubstance dependence Diseases 0.000 description 1
- 206010036376 Postherpetic Neuralgia Diseases 0.000 description 1
- 206010039367 Sadism Diseases 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 208000020186 Schizophreniform disease Diseases 0.000 description 1
- 208000024791 Schizotypal Personality disease Diseases 0.000 description 1
- 229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 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
- 206010041250 Social phobia Diseases 0.000 description 1
- 208000027520 Somatoform disease Diseases 0.000 description 1
- 206010041347 Somnambulism Diseases 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
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 1
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- 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 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
- 206010070863 Toxicity to various agents 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
- 208000012886 Vertigo Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 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 1
- KRHYYFGTRYWZRS-BJUDXGSMSA-N ac1l2y5h Chemical compound [18FH] KRHYYFGTRYWZRS-BJUDXGSMSA-N 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 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
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000026345 acute stress disease Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000009098 adjuvant therapy Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000007000 age related cognitive decline Effects 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 208000029650 alcohol withdrawal Diseases 0.000 description 1
- 208000006246 alcohol withdrawal delirium Diseases 0.000 description 1
- 208000028505 alcohol-related disease Diseases 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 230000006986 amnesia Effects 0.000 description 1
- 201000002472 amphetamine abuse Diseases 0.000 description 1
- 238000002266 amputation Methods 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 239000003263 anabolic agent Substances 0.000 description 1
- 229940070021 anabolic steroids Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 208000024823 antisocial personality disease Diseases 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000011230 binding agent Substances 0.000 description 1
- 208000014679 binge eating disease Diseases 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 208000022257 bipolar II disease Diseases 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 208000030963 borderline personality disease Diseases 0.000 description 1
- 210000000133 brain stem Anatomy 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical class CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 201000009322 cannabis abuse Diseases 0.000 description 1
- 229960000623 carbamazepine Drugs 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-BJUDXGSMSA-N carbon-11 Chemical compound [11C] OKTJSMMVPCPJKN-BJUDXGSMSA-N 0.000 description 1
- 206010007776 catatonia Diseases 0.000 description 1
- 239000006143 cell culture medium Substances 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000027288 circadian rhythm Effects 0.000 description 1
- 229960001653 citalopram Drugs 0.000 description 1
- 229960004606 clomipramine Drugs 0.000 description 1
- 229940068796 clozaril Drugs 0.000 description 1
- 201000001272 cocaine abuse Diseases 0.000 description 1
- 201000006145 cocaine dependence Diseases 0.000 description 1
- 230000006999 cognitive decline Effects 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 229940088505 compazine Drugs 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 208000026725 cyclothymic disease Diseases 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 208000030964 dependent personality disease Diseases 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229960003529 diazepam Drugs 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 150000008533 dibenzodiazepines Chemical class 0.000 description 1
- 150000008509 dibenzothiazepines Chemical class 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 239000003372 dissociative anesthetic agent Substances 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000142 dyskinetic effect Effects 0.000 description 1
- 208000024732 dysthymic disease Diseases 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 208000003481 exhibitionism Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229950003930 femoxetine Drugs 0.000 description 1
- 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 1
- 230000001605 fetal effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 229960002464 fluoxetine Drugs 0.000 description 1
- 229960004038 fluvoxamine Drugs 0.000 description 1
- CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000002496 gastric effect 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
- 239000003349 gelling agent Substances 0.000 description 1
- 208000029364 generalized anxiety disease Diseases 0.000 description 1
- 229940003380 geodon Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000000848 glutamatergic effect Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002333 glycines 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
- 229940095895 haldol Drugs 0.000 description 1
- 201000002270 hallucinogen abuse Diseases 0.000 description 1
- 201000006138 hallucinogen dependence Diseases 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000037417 hyperactivation Effects 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 208000017020 hypoactive sexual desire disease Diseases 0.000 description 1
- 230000001505 hypomanic effect Effects 0.000 description 1
- 208000003532 hypothyroidism Diseases 0.000 description 1
- 230000002989 hypothyroidism Effects 0.000 description 1
- 150000008624 imidazolidinones Chemical class 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229950002473 indalpine Drugs 0.000 description 1
- SADQVAVFGNTEOD-UHFFFAOYSA-N indalpine Chemical compound C=1NC2=CC=CC=C2C=1CCC1CCNCC1 SADQVAVFGNTEOD-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229960001848 lamotrigine Drugs 0.000 description 1
- PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 description 1
- 230000008449 language Effects 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 201000010901 lateral sclerosis Diseases 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229940089527 loxitane Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 208000015421 male orgasm disease Diseases 0.000 description 1
- 210000005171 mammalian brain Anatomy 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 229960001861 melperone Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
- SLVMESMUVMCQIY-UHFFFAOYSA-N mesoridazine Chemical compound CN1CCCCC1CCN1C2=CC(S(C)=O)=CC=C2SC2=CC=CC=C21 SLVMESMUVMCQIY-UHFFFAOYSA-N 0.000 description 1
- 229960000300 mesoridazine Drugs 0.000 description 1
- 229940042053 methotrimeprazine Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 208000027061 mild cognitive impairment Diseases 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940028394 moban Drugs 0.000 description 1
- 230000001483 mobilizing effect Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 208000005264 motor neuron disease Diseases 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000002151 myoclonic effect Effects 0.000 description 1
- WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
- 210000004897 n-terminal region Anatomy 0.000 description 1
- 201000003631 narcolepsy Diseases 0.000 description 1
- 210000003061 neural cell Anatomy 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 230000016273 neuron death Effects 0.000 description 1
- 208000021722 neuropathic pain Diseases 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 239000002581 neurotoxin Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 description 1
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 description 1
- 229960001158 nortriptyline Drugs 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 229960005343 ondansetron Drugs 0.000 description 1
- 201000005040 opiate dependence Diseases 0.000 description 1
- 201000000988 opioid abuse Diseases 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 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 1
- 229950009875 osanetant Drugs 0.000 description 1
- 208000027753 pain disease Diseases 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 208000024817 paranoid personality disease Diseases 0.000 description 1
- 208000002851 paranoid schizophrenia Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960002296 paroxetine Drugs 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229960002195 perazine Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 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 1
- 229960003634 pimozide Drugs 0.000 description 1
- 229940068151 pipothiazine Drugs 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
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068917 polyethylene glycols Drugs 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 206010036596 premature ejaculation Diseases 0.000 description 1
- 230000002265 prevention Effects 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
- 229960003598 promazine Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003368 psychostimulant agent Substances 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 229960004431 quetiapine Drugs 0.000 description 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 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
- 230000005855 radiation Effects 0.000 description 1
- CBQGYUDMJHNJBX-RTBURBONSA-N reboxetine Chemical compound CCOC1=CC=CC=C1O[C@H](C=1C=CC=CC=1)[C@@H]1OCCNC1 CBQGYUDMJHNJBX-RTBURBONSA-N 0.000 description 1
- 229960003770 reboxetine Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229940106887 risperdal Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940035004 seroquel Drugs 0.000 description 1
- 229960002073 sertraline Drugs 0.000 description 1
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 208000012201 sexual and gender identity disease Diseases 0.000 description 1
- 208000015891 sexual disease Diseases 0.000 description 1
- 230000001568 sexual effect Effects 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
- 238000007493 shaping process Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 201000001716 specific phobia Diseases 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 231100000736 substance abuse Toxicity 0.000 description 1
- 201000006152 substance dependence Diseases 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 description 1
- 229960003708 sumatriptan Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- 208000016686 tic disease Diseases 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 206010046947 vaginismus Diseases 0.000 description 1
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
- 229960000604 valproic acid Drugs 0.000 description 1
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
- 229960004688 venlafaxine Drugs 0.000 description 1
- 231100000889 vertigo Toxicity 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 208000008918 voyeurism Diseases 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- 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 1
- 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 1
- 229960002791 zimeldine Drugs 0.000 description 1
- 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 1
- 229940039925 zyprexa Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/401—Proline; Derivatives thereof, e.g. captopril
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0612420.0A GB0612420D0 (en) | 2006-06-22 | 2006-06-22 | Compounds |
| GB0612420 | 2006-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2333918T3 true ES2333918T3 (es) | 2010-03-02 |
Family
ID=36803732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07786764T Active ES2333918T3 (es) | 2006-06-22 | 2007-06-20 | Derivados de pirrolidina que tiene la actividad en el transportador glyt1. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US20080070973A1 (OSRAM) |
| EP (1) | EP2041082B1 (OSRAM) |
| JP (1) | JP2009541261A (OSRAM) |
| KR (1) | KR20090019847A (OSRAM) |
| CN (1) | CN101506156A (OSRAM) |
| AR (1) | AR061554A1 (OSRAM) |
| AT (1) | ATE444288T1 (OSRAM) |
| AU (1) | AU2007263058A1 (OSRAM) |
| BR (1) | BRPI0713311A2 (OSRAM) |
| CA (1) | CA2655399A1 (OSRAM) |
| CL (1) | CL2007001808A1 (OSRAM) |
| CR (1) | CR10498A (OSRAM) |
| DE (1) | DE602007002642D1 (OSRAM) |
| EA (1) | EA200970044A1 (OSRAM) |
| ES (1) | ES2333918T3 (OSRAM) |
| GB (1) | GB0612420D0 (OSRAM) |
| IL (1) | IL195633A0 (OSRAM) |
| MA (1) | MA30522B1 (OSRAM) |
| NO (1) | NO20085412L (OSRAM) |
| PE (1) | PE20080380A1 (OSRAM) |
| TW (1) | TW200817322A (OSRAM) |
| WO (1) | WO2007147831A1 (OSRAM) |
| ZA (1) | ZA200810009B (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20061156A1 (es) | 2004-12-23 | 2006-12-16 | Glaxo Group Ltd | Derivados de benzamida como agentes inhibidores del transportador de glicina |
| WO2008155334A2 (en) * | 2007-06-20 | 2008-12-24 | Glaxo Group Limited | Improved process of amide formation |
| SG186885A1 (en) | 2010-06-04 | 2013-02-28 | Albany Molecular Res Inc | Glycine transporter-1 inhibitors, methods of making them, and uses thereof |
| US20120035156A1 (en) * | 2010-08-09 | 2012-02-09 | Daniela Alberati | Combination of glyt1 compound with antipsychotics |
| WO2019073052A1 (en) | 2017-10-13 | 2019-04-18 | Treeway Tw001 B.V. | EDARAVONE SALT |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2746959A (en) * | 1953-06-02 | 1956-05-22 | American Home Prod | Diphenylethylenediamine-penicillin salt |
| US3145209A (en) * | 1961-07-31 | 1964-08-18 | Olin Mathieson | Substituted aminophenyl-ethylamine derivatives |
| NZ237443A (en) * | 1990-04-10 | 1993-11-25 | Asta Medica Ag | Phenalkylethylenediamine and aminomethyltetra hydroisoquinoline derivatives, platinum (ii) and (iv) complexes, methods of preparation and pharmaceutical compositions |
| GB0130696D0 (en) * | 2001-12-21 | 2002-02-06 | Smithkline Beecham Plc | Chemical Compounds |
| FR2861070B1 (fr) * | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[phenyl(pyrrolidin-2-yl)methyl]benzamide et n-[(azepan-2-yl)phenylmethyl]benzamide, leur preparation et leur application en therapeutique |
| PE20061156A1 (es) * | 2004-12-23 | 2006-12-16 | Glaxo Group Ltd | Derivados de benzamida como agentes inhibidores del transportador de glicina |
-
2006
- 2006-06-22 GB GBGB0612420.0A patent/GB0612420D0/en not_active Ceased
-
2007
- 2007-06-20 AU AU2007263058A patent/AU2007263058A1/en not_active Abandoned
- 2007-06-20 CN CNA2007800312340A patent/CN101506156A/zh active Pending
- 2007-06-20 CL CL2007001808A patent/CL2007001808A1/es unknown
- 2007-06-20 JP JP2009515863A patent/JP2009541261A/ja not_active Withdrawn
- 2007-06-20 TW TW096121972A patent/TW200817322A/zh unknown
- 2007-06-20 EA EA200970044A patent/EA200970044A1/ru unknown
- 2007-06-20 BR BRPI0713311-1A patent/BRPI0713311A2/pt not_active IP Right Cessation
- 2007-06-20 WO PCT/EP2007/056106 patent/WO2007147831A1/en not_active Ceased
- 2007-06-20 AT AT07786764T patent/ATE444288T1/de not_active IP Right Cessation
- 2007-06-20 ES ES07786764T patent/ES2333918T3/es active Active
- 2007-06-20 US US11/765,478 patent/US20080070973A1/en not_active Abandoned
- 2007-06-20 CA CA002655399A patent/CA2655399A1/en not_active Abandoned
- 2007-06-20 AR ARP070102723A patent/AR061554A1/es unknown
- 2007-06-20 KR KR1020087030915A patent/KR20090019847A/ko not_active Withdrawn
- 2007-06-20 PE PE2007000782A patent/PE20080380A1/es not_active Application Discontinuation
- 2007-06-20 EP EP07786764A patent/EP2041082B1/en active Active
- 2007-06-20 DE DE602007002642T patent/DE602007002642D1/de active Active
-
2008
- 2008-11-25 ZA ZA200810009A patent/ZA200810009B/xx unknown
- 2008-12-01 IL IL195633A patent/IL195633A0/en unknown
- 2008-12-11 CR CR10498A patent/CR10498A/es not_active Application Discontinuation
- 2008-12-19 MA MA31488A patent/MA30522B1/fr unknown
- 2008-12-30 NO NO20085412A patent/NO20085412L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20080070973A1 (en) | 2008-03-20 |
| BRPI0713311A2 (pt) | 2012-03-06 |
| GB0612420D0 (en) | 2006-08-02 |
| AU2007263058A1 (en) | 2007-12-27 |
| AR061554A1 (es) | 2008-09-03 |
| DE602007002642D1 (de) | 2009-11-12 |
| IL195633A0 (en) | 2009-09-01 |
| NO20085412L (no) | 2009-01-22 |
| ZA200810009B (en) | 2009-11-25 |
| CL2007001808A1 (es) | 2008-01-18 |
| CA2655399A1 (en) | 2007-12-27 |
| EP2041082A1 (en) | 2009-04-01 |
| WO2007147831A1 (en) | 2007-12-27 |
| MA30522B1 (fr) | 2009-06-01 |
| EA200970044A1 (ru) | 2009-04-28 |
| TW200817322A (en) | 2008-04-16 |
| EP2041082B1 (en) | 2009-09-30 |
| ATE444288T1 (de) | 2009-10-15 |
| JP2009541261A (ja) | 2009-11-26 |
| CR10498A (es) | 2009-03-20 |
| KR20090019847A (ko) | 2009-02-25 |
| PE20080380A1 (es) | 2008-05-31 |
| CN101506156A (zh) | 2009-08-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2392796T3 (es) | Moduladores de tipo indol del receptor nicotínico de acetilcolina alfa-7 | |
| ES2285227T3 (es) | Arilbenzodiazepinas sustituidas con piperazina. | |
| US20100120740A1 (en) | Prodrugs of fused heterocyclic inhibitors of d-amino acid oxidase | |
| JP4897683B2 (ja) | チエノピリジノン化合物及び治療方法 | |
| KR20100082349A (ko) | 치환된 n-페닐-비피롤리딘 우레아 및 이의 치료적 용도 | |
| ES2333918T3 (es) | Derivados de pirrolidina que tiene la actividad en el transportador glyt1. | |
| WO2005058317A1 (en) | Glycine transporter-1 inhibirors | |
| WO2005058882A1 (en) | Compounds having morpholinyl and piperidinyl groups for use as glyt1 and glyt2 inhibitors | |
| JP2010517964A (ja) | GlyT1トランスポーター阻害薬および神経学的および神経精神病学的障害の治療におけるその使用 | |
| JP2010504351A (ja) | バソプレッシン拮抗薬として使用されるスピロベンズアゼピン類 | |
| ES2237788T3 (es) | Derivados de indano para composiciones antipsicoticas. | |
| JP2008525400A (ja) | グリシン輸送阻害剤 | |
| ES2321217T3 (es) | Inhibidores del transporte de glicina. | |
| JP2008525403A (ja) | グリシントランスポーター阻害化合物としての酸素含有複素環 | |
| JP2010517963A (ja) | 神経学的および神経精神病学的障害の治療におけるGlyT1トランスポーター阻害薬としての8−オキサ−1,4−ジアザスピロ[4,5]デク−3−エン−1−イルおよび1,4,8−トリアザスピロ[4,5]デク−3−エン−1−イルアセトアミド誘導体 | |
| JP2008525398A (ja) | グリシン輸送阻害剤 | |
| JP2007533715A (ja) | GlyT1阻害剤として用いるためのモルホリニルおよびピペリジニル基を有する化合物 | |
| JP2010517959A (ja) | GlyT1トランスポーター阻害薬および神経学的および神経精神病学的障害の治療におけるその使用 | |
| JP2007533713A (ja) | N−[4−4(4−モルホリニル)フェニル]−[(4−ピペリジニル)メチル]カルボキシアミド誘導体、およびグリシントランスポーター阻害薬としてのその使用 | |
| US20100016374A1 (en) | Compounds Which Inhibit the Glycine Transporter and Uses Thereof | |
| MX2009000106A (es) | Derivados de pirrolidina que tienen actividad en el transportador glyti. | |
| US20090227629A1 (en) | Compounds having activity at the glycine transporter glyt1 and uses thereof | |
| JP2010517961A (ja) | GlyT1トランスポーター阻害薬および神経学的および神経精神病学的障害の治療におけるその使用 | |
| JP2010517962A (ja) | GlyT1トランスポーター阻害薬および神経学的および神経精神病学的障害の治療におけるその使用 | |
| JP2007533714A (ja) | N−[6−(4−モルホリニル)−3−ピリジニル]−2−(テトラヒドロ−2h−ピラン−4−イル)−n−[(1−{[フェニル]メチル}−4−ピペリジニル)メチル]アセトアミド誘導体および統合失調症などの精神病を治療するためのglyt1輸送阻害剤としての関連化合物 |