CA2595330A1

CA2595330A1 - Lacosamide pour traitement d'appoint

Lacosamide pour traitement d'appoint Download PDF

Info

Publication number: CA2595330A1
Authority: CA; Canada
Prior art keywords: alkyl; use according; aryl; day; unsubstituted
Prior art date: 2005-01-28
Legal status : Abandoned

Application number

CA002595330A

Other languages

English (en)

Inventor

Thomas Stoehr

Current Assignee

UCB Pharma GmbH

Original Assignee

Individual

Priority date

2005-01-28

Filing date

2006-01-27

Publication date

2006-08-03

2005-01-28 Priority claimed from EP05001843A external-priority patent/EP1688137A1/fr

2006-01-27 Application filed by Individual filed Critical Individual

2006-08-03 Publication of CA2595330A1 publication Critical patent/CA2595330A1/fr

Status Abandoned legal-status Critical Current

Links

201000000980 schizophrenia Diseases 0.000 title claims abstract description 71
238000002560 therapeutic procedure Methods 0.000 title claims abstract description 42
VPPJLAIAVCUEMN-GFCCVEGCSA-N lacosamide Chemical compound COC[C@@H](NC(C)=O)C(=O)NCC1=CC=CC=C1 VPPJLAIAVCUEMN-GFCCVEGCSA-N 0.000 title claims description 41
229960002623 lacosamide Drugs 0.000 title description 38
150000001875 compounds Chemical class 0.000 claims abstract description 103
208000028017 Psychotic disease Diseases 0.000 claims abstract description 96
238000011282 treatment Methods 0.000 claims abstract description 84
239000000164 antipsychotic agent Substances 0.000 claims abstract description 75
230000002265 prevention Effects 0.000 claims abstract description 54
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 40
201000010099 disease Diseases 0.000 claims abstract description 23
230000000561 anti-psychotic effect Effects 0.000 claims abstract description 22
125000000217 alkyl group Chemical group 0.000 claims description 105
-1 alkyl heterocyclic Chemical group 0.000 claims description 78
125000003118 aryl group Chemical group 0.000 claims description 57
239000001257 hydrogen Substances 0.000 claims description 54
229910052739 hydrogen Inorganic materials 0.000 claims description 54
239000000203 mixture Substances 0.000 claims description 42
125000006575 electron-withdrawing group Chemical group 0.000 claims description 40
125000004432 carbon atom Chemical group C* 0.000 claims description 39
239000008194 pharmaceutical composition Substances 0.000 claims description 37
QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 claims description 36
125000000623 heterocyclic group Chemical group 0.000 claims description 36
229960004170 clozapine Drugs 0.000 claims description 35
239000005557 antagonist Substances 0.000 claims description 31
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
125000003342 alkenyl group Chemical group 0.000 claims description 26
125000005843 halogen group Chemical group 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 25
125000000304 alkynyl group Chemical group 0.000 claims description 25
239000003814 drug Substances 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 21
229940079593 drug Drugs 0.000 claims description 19
125000000753 cycloalkyl group Chemical group 0.000 claims description 18
RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims description 18
125000003710 aryl alkyl group Chemical group 0.000 claims description 17
208000035475 disorder Diseases 0.000 claims description 17
239000003693 atypical antipsychotic agent Substances 0.000 claims description 16
KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims description 16
229960005017 olanzapine Drugs 0.000 claims description 15
229960001534 risperidone Drugs 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims description 14
208000018737 Parkinson disease Diseases 0.000 claims description 14
229960004372 aripiprazole Drugs 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
HDOZVRUNCMBHFH-UHFFFAOYSA-N zotepine Chemical compound CN(C)CCOC1=CC2=CC=CC=C2SC2=CC=C(Cl)C=C12 HDOZVRUNCMBHFH-UHFFFAOYSA-N 0.000 claims description 14
208000020925 Bipolar disease Diseases 0.000 claims description 13
NTJOBXMMWNYJFB-UHFFFAOYSA-N amisulpride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC NTJOBXMMWNYJFB-UHFFFAOYSA-N 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 claims description 13
229960000607 ziprasidone Drugs 0.000 claims description 13
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 claims description 13
229960004496 zotepine Drugs 0.000 claims description 13
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 12
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 12
206010003805 Autism Diseases 0.000 claims description 12
208000020706 Autistic disease Diseases 0.000 claims description 12
229960003036 amisulpride Drugs 0.000 claims description 12
208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 12
229960004431 quetiapine Drugs 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 12
208000024827 Alzheimer disease Diseases 0.000 claims description 10
BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 claims description 9
230000001154 acute effect Effects 0.000 claims description 9
239000003210 dopamine receptor blocking agent Substances 0.000 claims description 9
229960004940 sulpiride Drugs 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 8
208000007848 Alcoholism Diseases 0.000 claims description 7
206010012289 Dementia Diseases 0.000 claims description 7
208000012661 Dyskinesia Diseases 0.000 claims description 7
208000023105 Huntington disease Diseases 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
206010021036 Hyponatraemia Diseases 0.000 claims description 7
206010026749 Mania Diseases 0.000 claims description 7
208000036626 Mental retardation Diseases 0.000 claims description 7
208000019022 Mood disease Diseases 0.000 claims description 7
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 7
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 7
208000016620 Tourette disease Diseases 0.000 claims description 7
206010001584 alcohol abuse Diseases 0.000 claims description 7
208000025746 alcohol use disease Diseases 0.000 claims description 7
230000003291 dopaminomimetic effect Effects 0.000 claims description 7
230000036033 hyponatraemia Effects 0.000 claims description 7
206010022437 insomnia Diseases 0.000 claims description 7
208000022821 personality disease Diseases 0.000 claims description 7
206010036067 polydipsia Diseases 0.000 claims description 7
PXUIZULXJVRBPC-UHFFFAOYSA-N 1'-[3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl]hexahydro-2H-spiro[imidazo[1,2-a]pyridine-3,4'-piperidin]-2-one Chemical compound C12=CC(Cl)=CC=C2CCC2=CC=CC=C2N1CCCN1CCC2(C(NC3CCCCN32)=O)CC1 PXUIZULXJVRBPC-UHFFFAOYSA-N 0.000 claims description 6
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
229960003894 mosapramine Drugs 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 5
238000001990 intravenous administration Methods 0.000 claims description 5
229950004193 perospirone Drugs 0.000 claims description 5
GTAIPSDXDDTGBZ-OYRHEFFESA-N perospirone Chemical compound C1=CC=C2C(N3CCN(CC3)CCCCN3C(=O)[C@@H]4CCCC[C@@H]4C3=O)=NSCC2=C1 GTAIPSDXDDTGBZ-OYRHEFFESA-N 0.000 claims description 5
125000003373 pyrazinyl group Chemical group 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
229960005197 quetiapine fumarate Drugs 0.000 claims description 5
GMDCDXMAFMEDAG-CHHFXETESA-N (S,S)-asenapine maleate Chemical compound OC(=O)\C=C/C(O)=O.O1C2=CC=CC=C2[C@H]2CN(C)C[C@@H]2C2=CC(Cl)=CC=C21 GMDCDXMAFMEDAG-CHHFXETESA-N 0.000 claims description 4
BTFMCMVEUCGQDX-UHFFFAOYSA-N 1-[10-[3-[4-(2-hydroxyethyl)-1-piperidinyl]propyl]-2-phenothiazinyl]ethanone Chemical compound C12=CC(C(=O)C)=CC=C2SC2=CC=CC=C2N1CCCN1CCC(CCO)CC1 BTFMCMVEUCGQDX-UHFFFAOYSA-N 0.000 claims description 4
ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 claims description 4
GUJRSXAPGDDABA-NSHDSACASA-N 3-bromo-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2,6-dimethoxybenzamide Chemical compound CCN1CCC[C@H]1CNC(=O)C1=C(OC)C=CC(Br)=C1OC GUJRSXAPGDDABA-NSHDSACASA-N 0.000 claims description 4
ICAXEUYZCLRXKY-UHFFFAOYSA-N 7-[3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propoxy]-3-(hydroxymethyl)chromen-4-one Chemical compound FC1=CC=C2C(C3CCN(CC3)CCCOC=3C=C4OC=C(C(C4=CC=3)=O)CO)=NOC2=C1 ICAXEUYZCLRXKY-UHFFFAOYSA-N 0.000 claims description 4
QOYHHIBFXOOADH-UHFFFAOYSA-N 8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 QOYHHIBFXOOADH-UHFFFAOYSA-N 0.000 claims description 4
ANDGGVOPIJEHOF-UHFFFAOYSA-N CX-516 Chemical compound C=1C=C2N=CC=NC2=CC=1C(=O)N1CCCCC1 ANDGGVOPIJEHOF-UHFFFAOYSA-N 0.000 claims description 4
150000001204 N-oxides Chemical class 0.000 claims description 4
ZZQNEJILGNNOEP-UHFFFAOYSA-N Ocaperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC3=C(C)N=C4N(C3=O)C=CC=C4C)=NOC2=C1 ZZQNEJILGNNOEP-UHFFFAOYSA-N 0.000 claims description 4
229950007013 abaperidone Drugs 0.000 claims description 4
229960001615 asenapine maleate Drugs 0.000 claims description 4
229960003532 fluspirilene Drugs 0.000 claims description 4
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 claims description 4
229960003162 iloperidone Drugs 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
CVCDAZZJQWLXHM-UHFFFAOYSA-N mosapramine dihydrochloride Chemical compound Cl.Cl.C12=CC(Cl)=CC=C2CCC2=CC=CC=C2N1CCCN1CCC2(C(NC3CCCCN32)=O)CC1 CVCDAZZJQWLXHM-UHFFFAOYSA-N 0.000 claims description 4
229950010634 ocaperidone Drugs 0.000 claims description 4
WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 claims description 4
229960002195 perazine Drugs 0.000 claims description 4
229960004265 piperacetazine Drugs 0.000 claims description 4
230000036470 plasma concentration Effects 0.000 claims description 4
125000002098 pyridazinyl group Chemical group 0.000 claims description 4
229960003448 remoxipride Drugs 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
229960003474 ziprasidone hydrochloride Drugs 0.000 claims description 4
XCWPUUGSGHNIDZ-UHFFFAOYSA-N Oxypertine Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(C)=C1CCN(CC1)CCN1C1=CC=CC=C1 XCWPUUGSGHNIDZ-UHFFFAOYSA-N 0.000 claims description 3
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000001041 indolyl group Chemical group 0.000 claims description 3
125000002757 morpholinyl group Chemical group 0.000 claims description 3
229960002841 oxypertine Drugs 0.000 claims description 3
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 claims description 3
229960000652 sertindole Drugs 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
XCVDGQBGMARFRY-GFCCVEGCSA-N (2r)-2-acetamido-n-[(3-fluorophenyl)methyl]-3-methoxypropanamide Chemical compound COC[C@@H](NC(C)=O)C(=O)NCC1=CC=CC(F)=C1 XCVDGQBGMARFRY-GFCCVEGCSA-N 0.000 claims description 2
VEEHBRVUEHYHQQ-CYBMUJFWSA-N (2r)-2-acetamido-n-benzyl-3-ethoxypropanamide Chemical compound CCOC[C@@H](NC(C)=O)C(=O)NCC1=CC=CC=C1 VEEHBRVUEHYHQQ-CYBMUJFWSA-N 0.000 claims description 2
239000004593 Epoxy Chemical group 0.000 claims description 2
101100134927 Gallus gallus COR8 gene Proteins 0.000 claims description 2
125000002393 azetidinyl group Chemical group 0.000 claims description 2
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
125000003838 furazanyl group Chemical group 0.000 claims description 2
125000002636 imidazolinyl group Chemical group 0.000 claims description 2
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
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125000005956 isoquinolyl group Chemical group 0.000 claims description 2
125000001786 isothiazolyl group Chemical group 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
125000003566 oxetanyl group Chemical group 0.000 claims description 2
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125000005936 piperidyl group Chemical group 0.000 claims description 2
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
125000003226 pyrazolyl group Chemical group 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
125000001422 pyrrolinyl group Chemical group 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims description 2
125000005493 quinolyl group Chemical group 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
125000003831 tetrazolyl group Chemical group 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000001425 triazolyl group Chemical group 0.000 claims description 2
ZCBZSCBNOOIHFP-UHFFFAOYSA-N ziprasidone hydrochloride hydrate Chemical compound [H+].O.[Cl-].C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 ZCBZSCBNOOIHFP-UHFFFAOYSA-N 0.000 claims 2
PVNGTPGYSFGJIH-GFCCVEGCSA-N (2r)-2-acetamido-n-[(4-fluorophenyl)methyl]-3-methoxypropanamide Chemical compound COC[C@@H](NC(C)=O)C(=O)NCC1=CC=C(F)C=C1 PVNGTPGYSFGJIH-GFCCVEGCSA-N 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
125000000842 isoxazolyl group Chemical group 0.000 claims 1
229940005529 antipsychotics Drugs 0.000 abstract description 13
108090000765 processed proteins & peptides Proteins 0.000 abstract description 5
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 61
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150000002431 hydrogen Chemical group 0.000 description 20
230000006977 prepulse inhibition Effects 0.000 description 20
208000024891 symptom Diseases 0.000 description 20
230000009471 action Effects 0.000 description 18
230000000694 effects Effects 0.000 description 17
239000003795 chemical substances by application Substances 0.000 description 15
239000001961 anticonvulsive agent Substances 0.000 description 13
241001465754 Metazoa Species 0.000 description 11
125000001424 substituent group Chemical group 0.000 description 11
229940125681 anticonvulsant agent Drugs 0.000 description 10
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241000699670 Mus sp. Species 0.000 description 8
210000004556 brain Anatomy 0.000 description 8
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 8
WFPIAZLQTJBIFN-DVZOWYKESA-N zuclopenthixol Chemical compound C1CN(CCO)CCN1CC\C=C\1C2=CC(Cl)=CC=C2SC2=CC=CC=C2/1 WFPIAZLQTJBIFN-DVZOWYKESA-N 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 7
238000000034 method Methods 0.000 description 7
KTOYYUONFQWSMW-UHFFFAOYSA-N pipotiazine palmitate Chemical compound C1CC(CCOC(=O)CCCCCCCCCCCCCCC)CCN1CCCN1C2=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C21 KTOYYUONFQWSMW-UHFFFAOYSA-N 0.000 description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
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 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
208000004547 Hallucinations Diseases 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
125000004414 alkyl thio group Chemical group 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
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208000002193 Pain Diseases 0.000 description 5
125000002619 bicyclic group Chemical group 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
238000011260 co-administration Methods 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
229960001848 lamotrigine Drugs 0.000 description 5
PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 description 5
230000003389 potentiating effect Effects 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 5
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KRVOJOCLBAAKSJ-RDTXWAMCSA-N (2R,3R)-nemonapride Chemical compound C1=C(Cl)C(NC)=CC(OC)=C1C(=O)N[C@H]1[C@@H](C)N(CC=2C=CC=CC=2)CC1 KRVOJOCLBAAKSJ-RDTXWAMCSA-N 0.000 description 4
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 4
RKLNONIVDFXQRX-UHFFFAOYSA-N Bromperidol Chemical compound C1CC(O)(C=2C=CC(Br)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 RKLNONIVDFXQRX-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
JTVPZMFULRWINT-UHFFFAOYSA-N N-[2-(diethylamino)ethyl]-2-methoxy-5-methylsulfonylbenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(S(C)(=O)=O)=CC=C1OC JTVPZMFULRWINT-UHFFFAOYSA-N 0.000 description 4
208000009668 Neurobehavioral Manifestations Diseases 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
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 4
125000003282 alkyl amino group Chemical group 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
229950001988 biriperone Drugs 0.000 description 4
239000002775 capsule Substances 0.000 description 4
FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 4
229960000623 carbamazepine Drugs 0.000 description 4
NWPJLRSCSQHPJV-UHFFFAOYSA-N carpipramine Chemical compound C1CN(CCCN2C3=CC=CC=C3CCC3=CC=CC=C32)CCC1(C(=O)N)N1CCCCC1 NWPJLRSCSQHPJV-UHFFFAOYSA-N 0.000 description 4
230000001684 chronic effect Effects 0.000 description 4
XRYLGRGAWQSVQW-UHFFFAOYSA-N clorotepine Chemical compound C1CN(C)CCN1C1C2=CC(Cl)=CC=C2SC2=CC=CC=C2C1 XRYLGRGAWQSVQW-UHFFFAOYSA-N 0.000 description 4
238000000576 coating method Methods 0.000 description 4
229960003878 haloperidol Drugs 0.000 description 4
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
125000002950 monocyclic group Chemical group 0.000 description 4
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 4
230000004044 response Effects 0.000 description 4
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