NO323329B1 - Substituerte 4-(fenyl-N-alkyl)-piperidin-forbindelser samt farmasoytiske materialer og anvendelser derav - Google Patents

Substituerte 4-(fenyl-N-alkyl)-piperidin-forbindelser samt farmasoytiske materialer og anvendelser derav Download PDF

Info

Publication number: NO323329B1
Authority: NO; Norway
Prior art keywords: accordance; treatment; pharmaceutical material; compound; group
Prior art date: 1999-12-22

Application number

NO20022879A

Other languages

English (en)

Norwegian (no)

Other versions

NO20022879D0 (no

NO20022879L (no

Inventor

Clas Ake Sonesson

Susanna Waters

Nicholas Waters

Joakim Tedroff

Bengt Andersson

Original Assignee

Carlsson A Research Ab

Priority date (The priority date 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 date listed.)

1999-12-22

Filing date

2002-06-17

Publication date

2007-03-26

2002-06-17 Application filed by Carlsson A Research Ab filed Critical Carlsson A Research Ab

2002-06-17 Publication of NO20022879D0 publication Critical patent/NO20022879D0/no

2002-08-21 Publication of NO20022879L publication Critical patent/NO20022879L/no

2007-03-26 Publication of NO323329B1 publication Critical patent/NO323329B1/no

Links

239000000463 material Substances 0.000 title claims description 30
150000001875 compounds Chemical class 0.000 claims abstract description 163
238000011282 treatment Methods 0.000 claims abstract description 37
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
-1 SO2R7 Proteins 0.000 claims abstract description 26
208000035475 disorder Diseases 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 22
229910052794 bromium Inorganic materials 0.000 claims abstract description 10
229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
229910052740 iodine Inorganic materials 0.000 claims abstract description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims abstract description 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims abstract description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
101100203602 Hypocrea jecorina (strain QM6a) sor7 gene Proteins 0.000 claims abstract 2
238000002360 preparation method Methods 0.000 claims description 43
239000000126 substance Substances 0.000 claims description 17
208000028017 Psychotic disease Diseases 0.000 claims description 13
230000000642 iatrogenic effect Effects 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 11
201000000980 schizophrenia Diseases 0.000 claims description 10
208000019022 Mood disease Diseases 0.000 claims description 9
208000019901 Anxiety disease Diseases 0.000 claims description 8
208000018737 Parkinson disease Diseases 0.000 claims description 7
208000010877 cognitive disease Diseases 0.000 claims description 7
208000010118 dystonia Diseases 0.000 claims description 7
208000012661 Dyskinesia Diseases 0.000 claims description 6
208000004547 Hallucinations Diseases 0.000 claims description 6
208000027089 Parkinsonian disease Diseases 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 6
238000002347 injection Methods 0.000 claims description 6
239000007924 injection Substances 0.000 claims description 6
208000019116 sleep disease Diseases 0.000 claims description 6
SDVLKDOEEJKGSQ-UHFFFAOYSA-N 4-[4-chloro-3-(trifluoromethyl)phenyl]-1-propylpiperidine Chemical compound C1CN(CCC)CCC1C1=CC=C(Cl)C(C(F)(F)F)=C1 SDVLKDOEEJKGSQ-UHFFFAOYSA-N 0.000 claims description 5
208000014094 Dystonic disease Diseases 0.000 claims description 5
206010034010 Parkinsonism Diseases 0.000 claims description 5
208000000323 Tourette Syndrome Diseases 0.000 claims description 5
201000009032 substance abuse Diseases 0.000 claims description 5
208000020706 Autistic disease Diseases 0.000 claims description 4
208000020925 Bipolar disease Diseases 0.000 claims description 4
208000023105 Huntington disease Diseases 0.000 claims description 4
230000000698 schizophrenic effect Effects 0.000 claims description 4
208000011117 substance-related disease Diseases 0.000 claims description 4
208000007848 Alcoholism Diseases 0.000 claims description 3
206010003805 Autism Diseases 0.000 claims description 3
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 3
206010001584 alcohol abuse Diseases 0.000 claims description 3
208000025746 alcohol use disease Diseases 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
230000036651 mood Effects 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
208000020685 sleep-wake disease Diseases 0.000 claims description 3
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 2
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 2
208000016620 Tourette disease Diseases 0.000 claims description 2
208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 2
239000002775 capsule Substances 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
208000028683 bipolar I disease Diseases 0.000 claims 3
208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
238000000034 method Methods 0.000 abstract description 74
210000003169 central nervous system Anatomy 0.000 abstract description 9
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 abstract description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
101100440695 Dictyostelium discoideum corB gene Proteins 0.000 abstract 1
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 abstract 1
239000008194 pharmaceutical composition Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 29
230000000694 effects Effects 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
241000700159 Rattus Species 0.000 description 18
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
239000003814 drug Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 15
CFFZDZCDUFSOFZ-UHFFFAOYSA-N 3,4-Dihydroxy-phenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C(O)=C1 CFFZDZCDUFSOFZ-UHFFFAOYSA-N 0.000 description 14
230000003542 behavioural effect Effects 0.000 description 14
229960003638 dopamine Drugs 0.000 description 14
108050004812 Dopamine receptor Proteins 0.000 description 13
102000015554 Dopamine receptor Human genes 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000460 chlorine Substances 0.000 description 12
238000012360 testing method Methods 0.000 description 12
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 11
210000004556 brain Anatomy 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
229940079593 drug Drugs 0.000 description 11
125000000217 alkyl group Chemical group 0.000 description 10
239000002585 base Substances 0.000 description 10
230000003291 dopaminomimetic effect Effects 0.000 description 10
239000002904 solvent Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
229960000632 dexamfetamine Drugs 0.000 description 9
239000003446 ligand Substances 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
239000013543 active substance Substances 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
230000033001 locomotion Effects 0.000 description 8
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 8
208000024891 symptom Diseases 0.000 description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
239000003210 dopamine receptor blocking agent Substances 0.000 description 7
208000013403 hyperactivity Diseases 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
210000001519 tissue Anatomy 0.000 description 7
DUUGKQCEGZLZNO-UHFFFAOYSA-N 5-hydroxyindoleacetic acid Chemical compound C1=C(O)C=C2C(CC(=O)O)=CNC2=C1 DUUGKQCEGZLZNO-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
210000001577 neostriatum Anatomy 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000006467 substitution reaction Methods 0.000 description 6
RFKKDWFWACIFDB-UHFFFAOYSA-N 1-(4-methoxy-3-methylsulfonylphenyl)piperazine Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC=C1N1CCNCC1 RFKKDWFWACIFDB-UHFFFAOYSA-N 0.000 description 5
MWSJNAFFWBQRPQ-UHFFFAOYSA-N 1-(4-methyl-3-nitrophenyl)piperazine Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1N1CCNCC1 MWSJNAFFWBQRPQ-UHFFFAOYSA-N 0.000 description 5
208000016285 Movement disease Diseases 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
206010043118 Tardive Dyskinesia Diseases 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
230000006399 behavior Effects 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
239000003136 dopamine receptor stimulating agent Substances 0.000 description 5
235000019439 ethyl acetate Nutrition 0.000 description 5
230000006870 function Effects 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 5
230000006742 locomotor activity Effects 0.000 description 5
150000004885 piperazines Chemical class 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
230000001225 therapeutic effect Effects 0.000 description 5
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 5
DDWYBHPNFVYDDC-UHFFFAOYSA-N 1-[3-chloro-5-(trifluoromethyl)phenyl]piperazine Chemical compound FC(F)(F)C1=CC(Cl)=CC(N2CCNCC2)=C1 DDWYBHPNFVYDDC-UHFFFAOYSA-N 0.000 description 4
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 4
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 4
XDYBLYXOINDZAL-UHFFFAOYSA-N 1-propyl-4-[3-(trifluoromethyl)phenyl]piperazine Chemical compound C1CN(CCC)CCN1C1=CC=CC(C(F)(F)F)=C1 XDYBLYXOINDZAL-UHFFFAOYSA-N 0.000 description 4
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 4
XGOCKBMEZPNDPJ-UHFFFAOYSA-N 4-bromo-1-chloro-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Br)=CC=C1Cl XGOCKBMEZPNDPJ-UHFFFAOYSA-N 0.000 description 4
208000026331 Disruptive, Impulse Control, and Conduct disease Diseases 0.000 description 4
229940121891 Dopamine receptor antagonist Drugs 0.000 description 4
208000030814 Eating disease Diseases 0.000 description 4
208000019454 Feeding and Eating disease Diseases 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
206010019233 Headaches Diseases 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
206010044565 Tremor Diseases 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
238000003818 flash chromatography Methods 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
231100000869 headache Toxicity 0.000 description 4
QRMZSPFSDQBLIX-UHFFFAOYSA-N homovanillic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1O QRMZSPFSDQBLIX-UHFFFAOYSA-N 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
230000003340 mental effect Effects 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
208000020016 psychiatric disease Diseases 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
230000000862 serotonergic effect Effects 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
239000011734 sodium Substances 0.000 description 4
208000011580 syndromic disease Diseases 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
ZMWYXHKBARSVBJ-UHFFFAOYSA-N 1-(4-chloro-3-nitrophenyl)-4-propylpiperazine Chemical compound C1CN(CCC)CCN1C1=CC=C(Cl)C([N+]([O-])=O)=C1 ZMWYXHKBARSVBJ-UHFFFAOYSA-N 0.000 description 3
YGDZKYYCJUNORF-UHFFFAOYSA-N 1-propylpiperidin-4-one Chemical compound CCCN1CCC(=O)CC1 YGDZKYYCJUNORF-UHFFFAOYSA-N 0.000 description 3
OUKOAOJXXYENGL-UHFFFAOYSA-N 4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-propylpiperidine Chemical compound C1CN(CCC)CCC1C1=CC=C(F)C(C(F)(F)F)=C1 OUKOAOJXXYENGL-UHFFFAOYSA-N 0.000 description 3
239000003310 5-hydroxyindoleacetic acid Substances 0.000 description 3
RVWZUOPFHTYIEO-UHFFFAOYSA-N 5-hydroxyindoleacetic acid Natural products C1=C(O)C=C2C(C(=O)O)=CNC2=C1 RVWZUOPFHTYIEO-UHFFFAOYSA-N 0.000 description 3
208000027448 Attention Deficit and Disruptive Behavior disease Diseases 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
208000019888 Circadian rhythm sleep disease Diseases 0.000 description 3
206010012218 Delirium Diseases 0.000 description 3
206010012239 Delusion Diseases 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
208000001089 Multiple system atrophy Diseases 0.000 description 3
208000012902 Nervous system disease Diseases 0.000 description 3
208000025966 Neurological disease Diseases 0.000 description 3
208000008589 Obesity Diseases 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
230000008485 antagonism Effects 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000001149 cognitive effect Effects 0.000 description 3
231100000868 delusion Toxicity 0.000 description 3
238000011161 development Methods 0.000 description 3
230000018109 developmental process Effects 0.000 description 3
235000014632 disordered eating Nutrition 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 3
239000003176 neuroleptic agent Substances 0.000 description 3
230000000701 neuroleptic effect Effects 0.000 description 3
230000000926 neurological effect Effects 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
235000020824 obesity Nutrition 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
230000036961 partial effect Effects 0.000 description 3
230000001575 pathological effect Effects 0.000 description 3
230000002085 persistent effect Effects 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000010561 standard procedure Methods 0.000 description 3
230000005062 synaptic transmission Effects 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
229910052723 transition metal Inorganic materials 0.000 description 3
150000003624 transition metals Chemical class 0.000 description 3
125000005270 trialkylamine group Chemical group 0.000 description 3
230000002792 vascular Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 3
TYTITCUEUIIXNP-DTORHVGOSA-N (2r,6s)-2,6-dimethyl-1-propylpiperazine Chemical compound CCCN1[C@@H](C)CNC[C@H]1C TYTITCUEUIIXNP-DTORHVGOSA-N 0.000 description 2
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 2
DIVQKHQLANKJQO-UHFFFAOYSA-N 3-methoxytyramine Chemical compound COC1=CC(CCN)=CC=C1O DIVQKHQLANKJQO-UHFFFAOYSA-N 0.000 description 2
CECGTSSOVAKSAO-UHFFFAOYSA-N 4-[4-chloro-3-(trifluoromethyl)phenyl]piperidine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C2CCNCC2)=C1 CECGTSSOVAKSAO-UHFFFAOYSA-N 0.000 description 2
VPYXKYIZKISJTF-UHFFFAOYSA-N 4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-propyl-3,6-dihydro-2h-pyridine Chemical compound C1N(CCC)CCC(C=2C=C(C(F)=CC=2)C(F)(F)F)=C1 VPYXKYIZKISJTF-UHFFFAOYSA-N 0.000 description 2
CFPZDVAZISWERM-UHFFFAOYSA-N 4-bromo-1,2-dichlorobenzene Chemical compound ClC1=CC=C(Br)C=C1Cl CFPZDVAZISWERM-UHFFFAOYSA-N 0.000 description 2
AJLIJYGWAXPEOK-UHFFFAOYSA-N 4-bromo-1-fluoro-2-(trifluoromethyl)benzene Chemical compound FC1=CC=C(Br)C=C1C(F)(F)F AJLIJYGWAXPEOK-UHFFFAOYSA-N 0.000 description 2
XMGUUWRHYPQTHF-UHFFFAOYSA-N 4-bromo-1-methoxy-2-methylsulfonylbenzene Chemical compound COC1=CC=C(Br)C=C1S(C)(=O)=O XMGUUWRHYPQTHF-UHFFFAOYSA-N 0.000 description 2
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 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
229920000945 Amylopectin Polymers 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000010248 Cerebrovascular Trauma Diseases 0.000 description 2
206010008748 Chorea Diseases 0.000 description 2
240000007154 Coffea arabica Species 0.000 description 2
208000027691 Conduct disease Diseases 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
206010012289 Dementia Diseases 0.000 description 2
208000012239 Developmental disease Diseases 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
102000004980 Dopamine D2 Receptors Human genes 0.000 description 2
108090001111 Dopamine D2 Receptors Proteins 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
206010020852 Hypertonia Diseases 0.000 description 2
208000004356 Hysteria Diseases 0.000 description 2
208000030990 Impulse-control disease Diseases 0.000 description 2
208000001456 Jet Lag Syndrome Diseases 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
208000019695 Migraine disease Diseases 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
206010061296 Motor dysfunction Diseases 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
244000061176 Nicotiana tabacum Species 0.000 description 2
235000002637 Nicotiana tabacum Nutrition 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
208000005793 Restless legs syndrome Diseases 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
208000003028 Stuttering Diseases 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
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 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
244000269722 Thea sinensis Species 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
208000030886 Traumatic Brain injury Diseases 0.000 description 2
206010068100 Vascular parkinsonism Diseases 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
230000032683 aging Effects 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
229940025084 amphetamine Drugs 0.000 description 2
239000002830 appetite depressant Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
230000037396 body weight Effects 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
230000003925 brain function Effects 0.000 description 2
239000012267 brine Substances 0.000 description 2
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
ZPUCINDJVBIVPJ-LJISPDSOSA-N ***e Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
235000016213 coffee Nutrition 0.000 description 2
235000013353 coffee beverage Nutrition 0.000 description 2
230000003920 cognitive function Effects 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
208000012839 conversion disease Diseases 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
238000006880 cross-coupling reaction Methods 0.000 description 2
239000013058 crude material Substances 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
229940052760 dopamine agonists Drugs 0.000 description 2
230000010249 dopaminergic function Effects 0.000 description 2
239000003480 eluent Substances 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000012458 free base Substances 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
208000014674 injury Diseases 0.000 description 2
230000003993 interaction Effects 0.000 description 2
230000035987 intoxication Effects 0.000 description 2
231100000566 intoxication Toxicity 0.000 description 2
208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 description 2
210000004731 jugular vein Anatomy 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000008101 lactose Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
206010027599 migraine Diseases 0.000 description 2
230000001730 monoaminergic effect Effects 0.000 description 2
230000007659 motor function Effects 0.000 description 2
201000003631 narcolepsy Diseases 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
208000024196 oppositional defiant disease Diseases 0.000 description 2
238000006464 oxidative addition reaction Methods 0.000 description 2
230000036407 pain Effects 0.000 description 2
230000001314 paroxysmal effect Effects 0.000 description 2
208000022821 personality disease Diseases 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 2
150000003053 piperidines Chemical class 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229920001592 potato starch Polymers 0.000 description 2
230000008569 process Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
239000002516 radical scavenger Substances 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
230000009467 reduction Effects 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
230000009154 spontaneous behavior Effects 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
150000003871 sulfonates Chemical class 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000002194 synthesizing effect Effects 0.000 description 2
235000013616 tea Nutrition 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
230000008733 trauma Effects 0.000 description 2
230000009529 traumatic brain injury Effects 0.000 description 2
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
208000010926 vascular brain injury Diseases 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000003039 volatile agent Substances 0.000 description 2
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
PCMPDUPKYRRIIP-UHFFFAOYSA-N 1,3-dichloro-5-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=CC(Cl)=C1 PCMPDUPKYRRIIP-UHFFFAOYSA-N 0.000 description 1
WMKGGPCROCCUDY-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one Chemical compound C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 WMKGGPCROCCUDY-UHFFFAOYSA-N 0.000 description 1
PXFJLKKZSWWVRX-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)piperazine Chemical compound C1=C(Cl)C(Cl)=CC=C1N1CCNCC1 PXFJLKKZSWWVRX-UHFFFAOYSA-N 0.000 description 1
KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-UHFFFAOYSA-N 0.000 description 1
ILOARZGDZZZITA-UHFFFAOYSA-N 1-(4-chloro-3-methylsulfonylphenyl)piperazine Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC(N2CCNCC2)=C1 ILOARZGDZZZITA-UHFFFAOYSA-N 0.000 description 1
ASNGEUSDZWVICZ-UHFFFAOYSA-N 1-(4-chloro-3-nitrophenyl)piperazine Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(N2CCNCC2)=C1 ASNGEUSDZWVICZ-UHFFFAOYSA-N 0.000 description 1
ZXUYYZPJUGQHLQ-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-[4-(5-fluoro-2-pyrimidinyl)-1-piperazinyl]-1-butanol Chemical compound C=1C=C(F)C=CC=1C(O)CCCN(CC1)CCN1C1=NC=C(F)C=N1 ZXUYYZPJUGQHLQ-UHFFFAOYSA-N 0.000 description 1
OHNPYYXZMHFKMA-UHFFFAOYSA-N 1-(4-methoxy-3-methylsulfonylphenyl)-4-propan-2-ylpiperazine Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC=C1N1CCN(C(C)C)CC1 OHNPYYXZMHFKMA-UHFFFAOYSA-N 0.000 description 1
ISNRDQKWVRNUFV-UHFFFAOYSA-N 1-(4-methoxy-3-methylsulfonylphenyl)-4-propylpiperazine Chemical compound C1CN(CCC)CCN1C1=CC=C(OC)C(S(C)(=O)=O)=C1 ISNRDQKWVRNUFV-UHFFFAOYSA-N 0.000 description 1
PQFZQNLIVIONDY-UHFFFAOYSA-N 1-(4-methyl-3-nitrophenyl)-4-propylpiperazine Chemical compound C1CN(CCC)CCN1C1=CC=C(C)C([N+]([O-])=O)=C1 PQFZQNLIVIONDY-UHFFFAOYSA-N 0.000 description 1
YJEUNFQPKZSQEQ-UHFFFAOYSA-N 1-[2-chloro-5-(trifluoromethyl)phenyl]piperazine Chemical compound FC(F)(F)C1=CC=C(Cl)C(N2CCNCC2)=C1 YJEUNFQPKZSQEQ-UHFFFAOYSA-N 0.000 description 1
SOVLQDJRXJFKHO-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]piperazine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(N2CCNCC2)=C1 SOVLQDJRXJFKHO-UHFFFAOYSA-N 0.000 description 1
NBUGNMFCCQXVTB-UHFFFAOYSA-N 1-benzyl-4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C=2CCN(CC=3C=CC=CC=3)CC=2)=C1 NBUGNMFCCQXVTB-UHFFFAOYSA-N 0.000 description 1
LCPFPKWTMXEIBZ-UHFFFAOYSA-N 1-benzyl-4-[4-chloro-3-(trifluoromethyl)phenyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=C(C(Cl)=CC=2)C(F)(F)F)CCN1CC1=CC=CC=C1 LCPFPKWTMXEIBZ-UHFFFAOYSA-N 0.000 description 1
QGBUVOAKVFVLOZ-UHFFFAOYSA-N 1-benzyl-4-[4-chloro-3-(trifluoromethyl)phenyl]piperidine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C2CCN(CC=3C=CC=CC=3)CC2)=C1 QGBUVOAKVFVLOZ-UHFFFAOYSA-N 0.000 description 1
SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 description 1
LIGBGEJPUQBLTG-UHFFFAOYSA-N 1-bromo-3-fluoro-5-(trifluoromethyl)benzene Chemical compound FC1=CC(Br)=CC(C(F)(F)F)=C1 LIGBGEJPUQBLTG-UHFFFAOYSA-N 0.000 description 1
GCZYYAXHUMGROI-UHFFFAOYSA-N 1-butyl-4-(4-methoxy-3-methylsulfonylphenyl)piperazine Chemical compound C1CN(CCCC)CCN1C1=CC=C(OC)C(S(C)(=O)=O)=C1 GCZYYAXHUMGROI-UHFFFAOYSA-N 0.000 description 1
SSLWFPKNYZEOTH-UHFFFAOYSA-N 1-chloro-2-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C(I)=C1 SSLWFPKNYZEOTH-UHFFFAOYSA-N 0.000 description 1
VDTGOZMZOYKWCH-UHFFFAOYSA-N 1-ethyl-4-(4-methyl-3-nitrophenyl)piperazine Chemical compound C1CN(CC)CCN1C1=CC=C(C)C([N+]([O-])=O)=C1 VDTGOZMZOYKWCH-UHFFFAOYSA-N 0.000 description 1
QLEIDMAURCRVCX-UHFFFAOYSA-N 1-propylpiperazine Chemical compound CCCN1CCNCC1 QLEIDMAURCRVCX-UHFFFAOYSA-N 0.000 description 1
YITYOTNDIPUAJZ-UHFFFAOYSA-N 2,4-difluoro-n,n-dimethyl-5-pyridin-4-ylbenzenesulfonamide Chemical compound C1=C(F)C(S(=O)(=O)N(C)C)=CC(C=2C=CN=CC=2)=C1F YITYOTNDIPUAJZ-UHFFFAOYSA-N 0.000 description 1
ZAHLOZKVSJRCNA-UHFFFAOYSA-N 2-fluoro-5-(1-propylpiperidin-4-yl)benzonitrile Chemical compound C1CN(CCC)CCC1C1=CC=C(F)C(C#N)=C1 ZAHLOZKVSJRCNA-UHFFFAOYSA-N 0.000 description 1
ULJNNPVXBIJGED-UHFFFAOYSA-N 2-fluoro-5-piperazin-1-ylbenzonitrile Chemical compound C1=C(C#N)C(F)=CC=C1N1CCNCC1 ULJNNPVXBIJGED-UHFFFAOYSA-N 0.000 description 1
RUNFLPQDDQVLHF-UHFFFAOYSA-N 2-fluoro-5-pyridin-4-ylbenzonitrile Chemical compound C1=C(C#N)C(F)=CC=C1C1=CC=NC=C1 RUNFLPQDDQVLHF-UHFFFAOYSA-N 0.000 description 1
MRNQBQOWIRUROI-UHFFFAOYSA-N 2-methylsulfonyl-4-(4-propylpiperazin-1-yl)phenol Chemical compound C1CN(CCC)CCN1C1=CC=C(O)C(S(C)(=O)=O)=C1 MRNQBQOWIRUROI-UHFFFAOYSA-N 0.000 description 1
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical class C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
VEJMMSANEUFWJM-UHFFFAOYSA-N 4-(1-propyl-3,6-dihydro-2h-pyridin-4-yl)-2-(trifluoromethyl)aniline Chemical compound C1N(CCC)CCC(C=2C=C(C(N)=CC=2)C(F)(F)F)=C1 VEJMMSANEUFWJM-UHFFFAOYSA-N 0.000 description 1
BQQGEIGLQATVKB-UHFFFAOYSA-N 4-(4-methoxy-3-methylsulfonylphenyl)-1-propylpiperidine Chemical compound C1CN(CCC)CCC1C1=CC=C(OC)C(S(C)(=O)=O)=C1 BQQGEIGLQATVKB-UHFFFAOYSA-N 0.000 description 1
VXHLWAZJGJYUGD-UHFFFAOYSA-N 4-(4-methoxy-3-methylsulfonylphenyl)pyridine Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC=C1C1=CC=NC=C1 VXHLWAZJGJYUGD-UHFFFAOYSA-N 0.000 description 1
ITEXVBKZNBXQBP-UHFFFAOYSA-N 4-[2-chloro-5-(trifluoromethyl)phenyl]-1-propyl-3,6-dihydro-2h-pyridine Chemical compound C1N(CCC)CCC(C=2C(=CC=C(C=2)C(F)(F)F)Cl)=C1 ITEXVBKZNBXQBP-UHFFFAOYSA-N 0.000 description 1
VJKQQUIHKUVZHF-UHFFFAOYSA-N 4-[2-chloro-5-(trifluoromethyl)phenyl]-1-propylpiperidin-4-ol Chemical compound C1CN(CCC)CCC1(O)C1=CC(C(F)(F)F)=CC=C1Cl VJKQQUIHKUVZHF-UHFFFAOYSA-N 0.000 description 1
WYCNLKGYEZBUOQ-UHFFFAOYSA-N 4-[2-chloro-5-(trifluoromethyl)phenyl]-1-propylpiperidine Chemical compound C1CN(CCC)CCC1C1=CC(C(F)(F)F)=CC=C1Cl WYCNLKGYEZBUOQ-UHFFFAOYSA-N 0.000 description 1
ZLOIZBHXKDKAKE-UHFFFAOYSA-N 4-[3-fluoro-5-(trifluoromethyl)phenyl]-1-propylpiperidin-4-ol Chemical compound C1CN(CCC)CCC1(O)C1=CC(F)=CC(C(F)(F)F)=C1 ZLOIZBHXKDKAKE-UHFFFAOYSA-N 0.000 description 1
ZOUUNXKJBMITSX-UHFFFAOYSA-N 4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-propylpiperidin-4-ol Chemical compound C1CN(CCC)CCC1(O)C1=CC=C(F)C(C(F)(F)F)=C1 ZOUUNXKJBMITSX-UHFFFAOYSA-N 0.000 description 1
YHAJNZXMJKNKCN-UHFFFAOYSA-N 4-bromo-1-chloro-2-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC(Br)=CC=C1Cl YHAJNZXMJKNKCN-UHFFFAOYSA-N 0.000 description 1
PHXGKHTWEOPCEW-UHFFFAOYSA-N 4-bromo-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C(Br)C=C1C(F)(F)F PHXGKHTWEOPCEW-UHFFFAOYSA-N 0.000 description 1
UTBULQCHEUWJNV-UHFFFAOYSA-N 4-phenylpiperidine Chemical class C1CNCCC1C1=CC=CC=C1 UTBULQCHEUWJNV-UHFFFAOYSA-N 0.000 description 1
XPFLGCCWTGWXPS-UHFFFAOYSA-N 4-pyridin-4-yl-2-(trifluoromethyl)aniline Chemical compound C1=C(C(F)(F)F)C(N)=CC=C1C1=CC=NC=C1 XPFLGCCWTGWXPS-UHFFFAOYSA-N 0.000 description 1
102000056834 5-HT2 Serotonin Receptors Human genes 0.000 description 1
108091005479 5-HT2 receptors Proteins 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
GUDVQJXODNJRIJ-CALCHBBNSA-N 9-[3-[(3S,5R)-3,5-dimethyl-1-piperazinyl]propyl]carbazole Chemical compound C1[C@@H](C)N[C@@H](C)CN1CCCN1C2=CC=CC=C2C2=CC=CC=C21 GUDVQJXODNJRIJ-CALCHBBNSA-N 0.000 description 1
208000008811 Agoraphobia Diseases 0.000 description 1
208000031091 Amnestic disease Diseases 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
208000000103 Anorexia Nervosa Diseases 0.000 description 1
208000036640 Asperger disease Diseases 0.000 description 1
201000006062 Asperger syndrome Diseases 0.000 description 1
208000009017 Athetosis Diseases 0.000 description 1
102000007527 Autoreceptors Human genes 0.000 description 1
108010071131 Autoreceptors Proteins 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
206010006100 Bradykinesia Diseases 0.000 description 1
208000021500 Breathing-related sleep disease Diseases 0.000 description 1
208000021465 Brief psychotic disease Diseases 0.000 description 1
206010006550 Bulimia nervosa Diseases 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
208000009132 Catalepsy Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
208000017164 Chronobiology disease Diseases 0.000 description 1
208000011990 Corticobasal Degeneration Diseases 0.000 description 1
208000020406 Creutzfeldt Jacob disease Diseases 0.000 description 1
208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 description 1
208000010859 Creutzfeldt-Jakob disease Diseases 0.000 description 1
208000024254 Delusional disease Diseases 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
208000007590 Disorders of Excessive Somnolence Diseases 0.000 description 1
229940123603 Dopamine D2 receptor antagonist Drugs 0.000 description 1
206010013980 Dyssomnias Diseases 0.000 description 1
244000165918 Eucalyptus papuana Species 0.000 description 1
208000021584 Expressive language disease Diseases 0.000 description 1
208000018460 Feeding disease Diseases 0.000 description 1
208000001640 Fibromyalgia Diseases 0.000 description 1
208000001836 Firesetting Behavior Diseases 0.000 description 1
201000011240 Frontotemporal dementia Diseases 0.000 description 1
208000001613 Gambling Diseases 0.000 description 1
208000011688 Generalised anxiety disease Diseases 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
208000031886 HIV Infections Diseases 0.000 description 1
238000007341 Heck reaction Methods 0.000 description 1
208000002972 Hepatolenticular Degeneration Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
208000006083 Hypokinesia Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-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
208000020358 Learning disease Diseases 0.000 description 1
208000009829 Lewy Body Disease Diseases 0.000 description 1
201000002832 Lewy body dementia Diseases 0.000 description 1
206010026749 Mania Diseases 0.000 description 1
206010027387 Merycism Diseases 0.000 description 1
206010027944 Mood disorder due to a general medical condition Diseases 0.000 description 1
208000019430 Motor disease Diseases 0.000 description 1
206010028403 Mutism Diseases 0.000 description 1
201000005625 Neuroleptic malignant syndrome Diseases 0.000 description 1
206010060860 Neurological symptom Diseases 0.000 description 1
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
206010052794 Panic disorder with agoraphobia Diseases 0.000 description 1
206010033668 Panic disorder without agoraphobia Diseases 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
206010033799 Paralysis Diseases 0.000 description 1
208000012075 Paroxysmal dystonia Diseases 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
208000012202 Pervasive developmental disease Diseases 0.000 description 1
206010034912 Phobia Diseases 0.000 description 1
241001482237 Pica Species 0.000 description 1
208000000609 Pick Disease of the Brain Diseases 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
206010037180 Psychiatric symptoms Diseases 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
208000006289 Rett Syndrome Diseases 0.000 description 1
208000036353 Rett disease Diseases 0.000 description 1
241000283984 Rodentia Species 0.000 description 1
208000011390 Rumination Syndrome Diseases 0.000 description 1
208000020114 Schizophrenia and other psychotic disease Diseases 0.000 description 1
201000001880 Sexual dysfunction Diseases 0.000 description 1
208000019568 Shared Paranoid disease Diseases 0.000 description 1
208000028810 Shared psychotic disease Diseases 0.000 description 1
208000009106 Shy-Drager Syndrome Diseases 0.000 description 1
229910004298 SiO 2 Inorganic materials 0.000 description 1
229940122490 Sigma receptor antagonist Drugs 0.000 description 1
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
206010041250 Social phobia Diseases 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
208000028790 Speech Sound disease Diseases 0.000 description 1
206010042008 Stereotypy Diseases 0.000 description 1
238000006619 Stille reaction Methods 0.000 description 1
208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
208000011962 Substance-induced mood disease Diseases 0.000 description 1
231100000395 Substance-induced mood disorder Toxicity 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
238000006069 Suzuki reaction reaction Methods 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
208000008548 Tension-Type Headache Diseases 0.000 description 1
208000031674 Traumatic Acute Stress disease Diseases 0.000 description 1
208000001407 Vascular Headaches Diseases 0.000 description 1
206010047853 Waxy flexibility Diseases 0.000 description 1
208000018839 Wilson disease Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000011149 active material Substances 0.000 description 1
208000026345 acute stress disease Diseases 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000008484 agonism Effects 0.000 description 1
239000000556 agonist Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
229940125709 anorectic agent Drugs 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000000561 anti-psychotic effect Effects 0.000 description 1
239000000939 antiparkinson agent Substances 0.000 description 1
229940125688 antiparkinson agent Drugs 0.000 description 1
239000000164 antipsychotic agent Substances 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
150000001502 aryl halides Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
208000029560 autism spectrum disease Diseases 0.000 description 1
230000002567 autonomic effect Effects 0.000 description 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
238000013542 behavioral therapy Methods 0.000 description 1
238000009227 behaviour therapy Methods 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
208000027757 bipolar ll disease Diseases 0.000 description 1
230000036760 body temperature Effects 0.000 description 1
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
230000006931 brain damage Effects 0.000 description 1
231100000874 brain damage Toxicity 0.000 description 1
208000029028 brain injury Diseases 0.000 description 1
244000309464 bull Species 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000006315 carbonylation Effects 0.000 description 1
238000005810 carbonylation reaction Methods 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
239000000969 carrier Substances 0.000 description 1
206010007776 catatonia Diseases 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
208000015114 central nervous system disease Diseases 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
208000024825 childhood disintegrative disease Diseases 0.000 description 1
QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
208000012601 choreatic disease Diseases 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
230000027288 circadian rhythm Effects 0.000 description 1
229960003920 ***e Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
208000030251 communication disease Diseases 0.000 description 1
239000000039 congener Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000007333 cyanation reaction Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
208000026725 cyclothymic disease Diseases 0.000 description 1
238000006900 dealkylation reaction Methods 0.000 description 1
230000034994 death Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000003001 depressive effect Effects 0.000 description 1
ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
208000035548 disruptive behavior disease Diseases 0.000 description 1
208000009985 drug-induced dyskinesia Diseases 0.000 description 1
208000024732 dysthymic disease Diseases 0.000 description 1
238000000835 electrochemical detection Methods 0.000 description 1
230000004970 emotional disturbance Effects 0.000 description 1
230000002996 emotional effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
230000037406 food intake Effects 0.000 description 1
235000012631 food intake Nutrition 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
210000005153 frontal cortex Anatomy 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
230000008570 general process Effects 0.000 description 1
208000029364 generalized anxiety disease Diseases 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
239000000380 hallucinogen Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004447 heteroarylalkenyl group Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
206010020765 hypersomnia Diseases 0.000 description 1
239000003326 hypnotic agent Substances 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
206010022437 insomnia Diseases 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229960003299 ketamine Drugs 0.000 description 1
206010023461 kleptomania Diseases 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000010410 layer Substances 0.000 description 1
201000003723 learning disability Diseases 0.000 description 1
230000002197 limbic effect Effects 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
208000024714 major depressive disease Diseases 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
230000007257 malfunction Effects 0.000 description 1
210000005171 mammalian brain Anatomy 0.000 description 1
240000004308 marijuana Species 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
238000002483 medication Methods 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000000897 modulatory effect Effects 0.000 description 1
230000004899 motility Effects 0.000 description 1
230000037023 motor activity Effects 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000001722 neurochemical effect Effects 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
208000037860 neuroleptic-induced Akathisia Diseases 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
208000031237 olivopontocerebellar atrophy Diseases 0.000 description 1
229940005483 opioid analgesics Drugs 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000002746 orthostatic effect Effects 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
208000021090 palsy Diseases 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
208000002851 paranoid schizophrenia Diseases 0.000 description 1
208000020861 perceptual disease Diseases 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
238000001050 pharmacotherapy Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
229950010883 phencyclidine Drugs 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
208000028173 post-traumatic stress disease Diseases 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
201000002212 progressive supranuclear palsy Diseases 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
210000004129 prosencephalon Anatomy 0.000 description 1
238000000746 purification Methods 0.000 description 1
QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
201000004645 pyromania Diseases 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000003893 regulation of appetite Effects 0.000 description 1
229950004933 rimcazole Drugs 0.000 description 1
208000015212 rumination disease Diseases 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
238000005070 sampling Methods 0.000 description 1
208000022610 schizoaffective disease Diseases 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
230000001953 sensory effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000000952 serotonin receptor agonist Substances 0.000 description 1
230000013275 serotonin uptake Effects 0.000 description 1
208000012201 sexual and gender identity disease Diseases 0.000 description 1
208000015891 sexual disease Diseases 0.000 description 1
231100000872 sexual dysfunction Toxicity 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
230000036299 sexual function Effects 0.000 description 1
239000003982 sigma receptor ligand Substances 0.000 description 1
230000007958 sleep Effects 0.000 description 1
208000022925 sleep disturbance Diseases 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
239000012439 solid excipient Substances 0.000 description 1
201000001716 specific phobia Diseases 0.000 description 1
208000027765 speech disease Diseases 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
208000013623 stereotypic movement disease Diseases 0.000 description 1
230000035882 stress Effects 0.000 description 1
208000003755 striatonigral degeneration Diseases 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
208000016686 tic disease Diseases 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
230000007704 transition Effects 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tri(ortho-tolyl)phosphine Substances CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
208000002271 trichotillomania Diseases 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
230000006441 vascular event Effects 0.000 description 1
230000001755 vocal effect Effects 0.000 description 1
239000001993 wax Substances 0.000 description 1
208000016153 withdrawal disease Diseases 0.000 description 1
239000012991 xanthate Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/06—Antimigraine agents
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

NO20022879A 1999-12-22 2002-06-17 Substituerte 4-(fenyl-N-alkyl)-piperidin-forbindelser samt farmasoytiske materialer og anvendelser derav NO323329B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE9904723A SE9904723D0 (sv)	1999-12-22	1999-12-22	New modulators of dopamine neurotransmission II
PCT/SE2000/002675 WO2001046146A1 (en)	1999-12-22	2000-12-22	New modulators of dopamine neurotransmission

Publications (3)

Publication Number	Publication Date
NO20022879D0 NO20022879D0 (no)	2002-06-17
NO20022879L NO20022879L (no)	2002-08-21
NO323329B1 true NO323329B1 (no)	2007-03-26

Family

ID=20418252

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20022879A NO323329B1 (no)	1999-12-22	2002-06-17	Substituerte 4-(fenyl-N-alkyl)-piperidin-forbindelser samt farmasoytiske materialer og anvendelser derav

Country Status (30)

Country	Link
US (2)	US6924374B2 (da)
EP (2)	EP1240143A1 (da)
JP (1)	JP5096654B2 (da)
KR (1)	KR100771287B1 (da)
CN (1)	CN1196680C (da)
AT (1)	ATE397446T1 (da)
AU (1)	AU778183B2 (da)
BG (1)	BG65698B1 (da)
BR (1)	BR0016635A (da)
CA (1)	CA2394606C (da)
CZ (1)	CZ302907B6 (da)
DE (1)	DE60039131D1 (da)
DK (1)	DK1419773T3 (da)
EE (1)	EE05083B1 (da)
ES (1)	ES2307861T3 (da)
HK (1)	HK1054228B (da)
HR (1)	HRP20020539B1 (da)
HU (1)	HUP0203874A3 (da)
IL (2)	IL150350A0 (da)
MX (1)	MXPA02006317A (da)
NO (1)	NO323329B1 (da)
NZ (2)	NZ519566A (da)
PL (1)	PL205092B1 (da)
PT (1)	PT1419773E (da)
RU (1)	RU2262504C2 (da)
SE (1)	SE9904723D0 (da)
SK (1)	SK287366B6 (da)
UA (1)	UA73337C2 (da)
WO (1)	WO2001046146A1 (da)
ZA (1)	ZA200204813B (da)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE9904724D0 (sv) *	1999-12-22	1999-12-22	Carlsson A Research Ab	New modulators of dopamine neurotransmission I
USRE46117E1 (en)	1999-12-22	2016-08-23	Teva Pharmaceuticals International Gmbh	Modulators of dopamine neurotransmission
SE9904723D0 (sv)	1999-12-22	1999-12-22	Carlsson A Research Ab	New modulators of dopamine neurotransmission II
US20070021404A1 (en) *	2003-06-24	2007-01-25	Dan Peters	Novel aza-ring derivatives and their use as monoamine neurotransmitter re-uptake inhibitors
DE10361259A1 (de) *	2003-12-24	2005-07-28	Schwarz Pharma Ag	Verwendung von Rotigotine in einem Frühstadium von Morbus Parkinson zur Prävention des weiteren Neuronenverlustes
MXPA06013945A (es) *	2004-06-08	2007-10-08	Neurosearch Sweden Ab	Piperidinas sustituidas, novedosas, como moduladores de la neurotransmision de dopamina.
SE0401464D0 (sv) *	2004-06-08	2004-06-08	Carlsson A Research Ab	New disubstituted phenylpiperidines/piperazines as modulators of dopamine neurotransmission
US7851629B2 (en)	2004-06-08	2010-12-14	Nsab, Filial Af Neurosearch Sweden Ab, Sverige	Disubstituted phenylpiperidines as modulators of dopamine and serotonin neurotransmission
DE602005017784D1 (de) *	2004-06-08	2009-12-31	Nsab, Filial Af Neurosearch Sweden Ab	Neue disubstituierte phenylpiperidine als modulatoren der dopamin- und serotoninneurotransmission
JP4937124B2 (ja) *	2004-06-08	2012-05-23	エヌエスエービー，フィリアルアフニューロサーチスウェーデンアクチボラゲット，スヴェリエ	ドーパミン神経伝達のモジュレーターとしての新規に提供されるフェニルピペリジン／ピペラジン
SE0401465D0 (sv) *	2004-06-08	2004-06-08	Carlsson A Research Ab	New substituted piperdines as modulators of dopamine neurotransmission
MXPA06014213A (es) *	2004-06-18	2007-03-12	Neurosearch As	Novedosos derivados de piperazina sustituidos por alquilo y su uso como inhibidores de la recaptacion del neurotransmisor monoamina.
CN101056854B (zh)	2004-10-13	2013-06-05	Nsab神经研究瑞典公司分公司	合成4-(3-甲磺酰基苯基)-1-n-丙基-哌啶的方法
AU2005293755A1 (en) *	2004-10-13	2006-04-20	Nsab, Filial Af Neurosearch Sweden Ab, Sverige	Process for the synthesis of 4-(3-sulfonylphenyl)-piperidines
ITMI20051193A1 (it) *	2005-06-24	2006-12-25	Acraf	Uso farmaceutico di una 1-3-clorofenil-3-alchilpiperazina
SE529246C2 (sv) *	2005-10-13	2007-06-12	Neurosearch Sweden Ab	Nya disubstituerade fenyl-piperidiner som modulatorer för dopaminneurotransmission
WO2007065655A1 (en) *	2005-12-07	2007-06-14	Neurosearch Sweden Ab	Disubstituted phenylpiperidines as modulators of cortical catecholaminergic neurotransmission
AU2008239841B2 (en) *	2007-04-12	2013-07-18	Teva Pharmaceuticals International Gmbh	N-oxide and/or di-N-oxide derivatives of dopamine receptor stabilizers/modulators displaying improved cardiovascular side-effects profiles
MX2009012716A (es)	2007-06-05	2009-12-14	Nsab Af Neurosearch Sweden Ab	Nuevas fenilpirrolidinas disustituidas como moduladores de la neurotransmision catecolaminergica cortical.
NZ581364A (en)	2007-06-05	2011-10-28	Nsab Af Neurosearch Sweden Ab	Disubstituted phenylpyrrolidines as modulators of cortical catecholaminergic neurotransmission
JP2011519839A (ja) *	2008-04-29	2011-07-14	エヌエスエイビー、フィリアルアヴノイロサーチスウェーデンエービー、スヴェーリエ	ドーパミン神経伝達のモジュレーター
US8492372B2 (en) *	2008-04-29	2013-07-23	Integrated Research Laboratories Sweden Ab	Modulators of dopamine neurotransmission
MX2010011724A (es) *	2008-04-29	2010-11-30	Nsab Af Neurosearch Sweden Ab	Moduladores de neurotransmision de dopamina.
WO2011107583A1 (en)	2010-03-04	2011-09-09	Nsab, Filial Af Neurosearch Sweden Ab, Sverige	Substituted 4-phenyl-n-alkyl-piperidines for preventing onset or slowing progression of neurodegenerative disorders
US20130197031A1 (en)	2010-09-03	2013-08-01	IVAX International GmbH	Deuterated analogs of pridopidine useful as dopaminergic stabilizers
JP6189299B2 (ja)	2011-09-07	2017-08-30	テバ・ファーマシューティカルズ・インターナショナル・ゲーエムベーハー	プリドピジン塩酸塩の新規な多形形態
US9012476B2 (en)	2011-12-08	2015-04-21	IVAX International GmbH	Hydrobromide salt of pridopidine
CN104470585A (zh)	2012-04-04	2015-03-25	爱华克斯国际有限公司	用于联合疗法的药物组合物
AR105434A1 (es)	2015-07-22	2017-10-04	Teva Pharmaceuticals Int Gmbh	Proceso para preparar pridopidina

Family Cites Families (60)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2027703A (en) *	1934-06-21	1936-01-14	Ribar Peter	Shoe jack
DE1019308B (de) *	1954-07-19	1957-11-14	Hoechst Ag	Verfahren zur Herstellung gegen Bilharzia-Infektionen wirksamer 4-Phenyl-piperazine
GB850662A (en)	1956-10-22	1960-10-05	Parke Davis & Co	Substituted piperazines and processes for their production
BE662455A (da)	1964-04-14
GB1060160A (en)	1964-08-05	1967-03-01	Allen & Hanburys Ltd	4-phenylpiperidine derivatives
NL6607959A (da) *	1965-06-10	1966-12-12
US3539573A (en)	1967-03-22	1970-11-10	Jean Schmutz	11-basic substituted dibenzodiazepines and dibenzothiazepines
CA1061356A (en) *	1975-10-03	1979-08-28	Dieter H. Klaubert	2-cyano-3- or 4-(substituted amino) oxanilic acid derivatives
GB1560271A (en)	1977-01-14	1980-02-06	Joullie International Sa	Therapeutically useful m-trifluoromethylphenylpiperazine derivatives
US4202898A (en) *	1978-06-05	1980-05-13	Synthelabo	Method of treating anxiety and depression
FR2459797A2 (fr) *	1978-08-01	1981-01-16	Synthelabo	Derives de phenyl-1 piperazine et leur application en therapeutique
US4267328A (en)	1978-08-01	1981-05-12	Synthelabo	1-Phenylpiperazines
US4333942A (en)	1979-08-03	1982-06-08	Byk Gulden Lomberg Chemische Fabrik Gmbh	Anti-depressant and analgesic 4-phenoxypiperidines
US4518712A (en)	1980-06-30	1985-05-21	Taiho Pharmaceutical Company Limited	Piperazine derivative and analgesic composition containing the same
JPS5714585A (en) *	1980-06-30	1982-01-25	Taiho Yakuhin Kogyo Kk	1-cycloalkylmethylpiperazine derivative
GB2083476B (en)	1980-09-12	1984-02-08	Wyeth John & Brother Ltd	Heterocyclic compounds
FR2501506A1 (fr)	1981-03-11	1982-09-17	Sanofi Sa	Compositions pharmaceutiques a action anorexigene contenant des derives de la tetrahydropyridine
JPS5815979A (ja) *	1981-07-11	1983-01-29	Kyowa Hakko Kogyo Co Ltd	新規なピペリジン誘導体およびその製造法
US4415736A (en)	1981-12-28	1983-11-15	E. I. Du Pont De Nemours & Co.	Certain tetrahydropyridine intermediates
EP0094159B1 (en)	1982-05-10	1990-03-14	Takeda Chemical Industries, Ltd.	Dihydropyridine derivatives, their production and use
US4504660A (en) *	1982-07-06	1985-03-12	American Home Products Corporation	Process for the production of 2,6-diaminobenzonitrile derivatives
ES8602674A1 (es) *	1985-02-07	1985-12-01	Inst Investigacion Desarrollo	Un nuevo procedimiento de obtencion de derivados del acido quinolincarboxilico
US4892975A (en)	1987-09-28	1990-01-09	President And Fellows Of Harvard College	Diethynyl monomers and polymers thereof
HU198454B (en)	1987-12-14	1989-10-30	Richter Gedeon Vegyeszet	Process for production of new derivatives of tetrahydrospiridin and medical compositions containing these compounds
FR2639226B1 (fr)	1988-11-18	1993-11-05	Sanofi	Utilisation de trifluoromethylphenyltetrahydropyridines pour la preparation de medicaments destines a combattre les troubles anxio-depressifs
WO1991009594A1 (en) *	1989-12-28	1991-07-11	Virginia Commonwealth University	Sigma receptor ligands and the use thereof
JP3176063B2 (ja)	1991-04-17	2001-06-11	ファルマシア・アンド・アップジョン・カンパニー	新規中枢神経作用性置換フェニルアザシクロアルカン類
EP0591426A4 (en)	1991-06-27	1996-08-21	Univ Virginia Commonwealth	Sigma receptor ligands and the use thereof
NZ240863A (en)	1991-09-11	1995-04-27	Mcneilab Inc	Substituted 4-aryl piperidine and 4-aryl piperazine derivatives, preparation and pharmaceutical compositions thereof
ATE204262T1 (de)	1991-09-18	2001-09-15	Glaxo Group Ltd	Benzanilidderivate als 5-ht1d-antagonisten
GB9119932D0 (en)	1991-09-18	1991-10-30	Glaxo Group Ltd	Chemical compounds
GB9119920D0 (en) *	1991-09-18	1991-10-30	Glaxo Group Ltd	Chemical compounds
TW240217B (da) *	1992-12-30	1995-02-11	Glaxo Group Ltd
GB2276160A (en) *	1993-03-17	1994-09-21	Glaxo Group Ltd	Ethanone compounds.
US5502050A (en) *	1993-11-29	1996-03-26	Cornell Research Foundation, Inc.	Blocking utilization of tetrahydrobiopterin to block induction of nitric oxide synthesis
EP0659743A1 (en)	1993-12-27	1995-06-28	Hoechst Aktiengesellschaft	Piperidine derivatives as inhibitors of platelet aggregation and their preparation
CA2144669A1 (en)	1994-03-29	1995-09-30	Kozo Akasaka	Biphenyl derivatives
US5571822A (en) *	1994-09-30	1996-11-05	The University Of North Carolina At Chapel Hill	Antitumor compounds
WO1997003986A1 (fr)	1995-07-19	1997-02-06	Yoshitomi Pharmaceutical Industries, Ltd.	Composes fusionnes de triazole
FR2740134B1 (fr) *	1995-10-18	1998-01-09	Pf Medicament	Derives d'amines cycliques d'aryl-piperazines, leur preparation et les compositions pharmaceutiques les contenant
US5892041A (en)	1996-08-12	1999-04-06	Neurogen Corporation	Fused indolecarboxamides: dopamine receptor subtype specific ligands
DE19637237A1 (de) *	1996-09-13	1998-03-19	Merck Patent Gmbh	Piperazin-Derivate
DZ2376A1 (fr) *	1996-12-19	2002-12-28	Smithkline Beecham Plc	Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant.
US6232326B1 (en)	1998-07-14	2001-05-15	Jodi A. Nelson	Treatment for schizophrenia and other dopamine system dysfunctions
JP2000086603A (ja)	1998-07-15	2000-03-28	Yoshitomi Pharmaceut Ind Ltd	桂皮酸アミド誘導体および３―フェニルプロピオン酸アミド誘導体
WO2000078728A1 (en)	1999-06-22	2000-12-28	Neurosearch A/S	Novel benzimidazole derivatives and pharmaceutical compositions comprising these compounds
SE9904724D0 (sv)	1999-12-22	1999-12-22	Carlsson A Research Ab	New modulators of dopamine neurotransmission I
SE9904723D0 (sv)	1999-12-22	1999-12-22	Carlsson A Research Ab	New modulators of dopamine neurotransmission II
US6906120B1 (en)	2000-06-20	2005-06-14	General Electric	Poly(arylene ether) adhesive compositions
EP1313477A4 (en) *	2000-07-15	2004-03-03	Smithkline Beecham Corp	COMPILATIONS AND METHODS
US7186715B2 (en)	2001-01-08	2007-03-06	Eli Lilly And Company	Piperazine- and piperidine-derivatives as melanocortin receptor agonists
US6663587B2 (en) *	2001-06-22	2003-12-16	Medela Holding Ag	Breastshield with multi-pressure and expansible chamber construction, related breastpump and method
US20050004164A1 (en)	2003-04-30	2005-01-06	Caggiano Thomas J.	2-Cyanopropanoic acid amide and ester derivatives and methods of their use
US7160888B2 (en)	2003-08-22	2007-01-09	Warner Lambert Company Llc	[1,8]naphthyridin-2-ones and related compounds for the treatment of schizophrenia
DE602005017784D1 (de)	2004-06-08	2009-12-31	Nsab, Filial Af Neurosearch Sweden Ab	Neue disubstituierte phenylpiperidine als modulatoren der dopamin- und serotoninneurotransmission
SE0401465D0 (sv)	2004-06-08	2004-06-08	Carlsson A Research Ab	New substituted piperdines as modulators of dopamine neurotransmission
JP4937124B2 (ja)	2004-06-08	2012-05-23	エヌエスエービー，フィリアルアフニューロサーチスウェーデンアクチボラゲット，スヴェリエ	ドーパミン神経伝達のモジュレーターとしての新規に提供されるフェニルピペリジン／ピペラジン
US7851629B2 (en)	2004-06-08	2010-12-14	Nsab, Filial Af Neurosearch Sweden Ab, Sverige	Disubstituted phenylpiperidines as modulators of dopamine and serotonin neurotransmission
SE529246C2 (sv)	2005-10-13	2007-06-12	Neurosearch Sweden Ab	Nya disubstituerade fenyl-piperidiner som modulatorer för dopaminneurotransmission
WO2007065655A1 (en)	2005-12-07	2007-06-14	Neurosearch Sweden Ab	Disubstituted phenylpiperidines as modulators of cortical catecholaminergic neurotransmission

1999
- 1999-12-22 SE SE9904723A patent/SE9904723D0/xx unknown
2000
- 2000-12-22 PT PT03027034T patent/PT1419773E/pt unknown
- 2000-12-22 WO PCT/SE2000/002675 patent/WO2001046146A1/en not_active Application Discontinuation
- 2000-12-22 EP EP00989163A patent/EP1240143A1/en not_active Withdrawn
- 2000-12-22 JP JP2001547057A patent/JP5096654B2/ja not_active Expired - Fee Related
- 2000-12-22 NZ NZ519566A patent/NZ519566A/en unknown
- 2000-12-22 AT AT03027034T patent/ATE397446T1/de active
- 2000-12-22 ES ES03027034T patent/ES2307861T3/es not_active Expired - Lifetime
- 2000-12-22 DK DK03027034T patent/DK1419773T3/da active
- 2000-12-22 US US10/168,019 patent/US6924374B2/en not_active Ceased
- 2000-12-22 BR BR0016635-9A patent/BR0016635A/pt not_active IP Right Cessation
- 2000-12-22 EE EEP200200345A patent/EE05083B1/xx not_active IP Right Cessation
- 2000-12-22 DE DE60039131T patent/DE60039131D1/de not_active Expired - Lifetime
- 2000-12-22 NZ NZ531643A patent/NZ531643A/en not_active IP Right Cessation
- 2000-12-22 SK SK866-2002A patent/SK287366B6/sk not_active IP Right Cessation
- 2000-12-22 MX MXPA02006317A patent/MXPA02006317A/es active IP Right Grant
- 2000-12-22 CA CA002394606A patent/CA2394606C/en not_active Expired - Fee Related
- 2000-12-22 EP EP03027034A patent/EP1419773B1/en not_active Expired - Lifetime
- 2000-12-22 RU RU2002119417/04A patent/RU2262504C2/ru not_active IP Right Cessation
- 2000-12-22 CZ CZ20022074A patent/CZ302907B6/cs not_active IP Right Cessation
- 2000-12-22 PL PL362251A patent/PL205092B1/pl not_active IP Right Cessation
- 2000-12-22 US US11/904,013 patent/USRE41315E1/en not_active Expired - Lifetime
- 2000-12-22 AU AU25706/01A patent/AU778183B2/en not_active Ceased
- 2000-12-22 KR KR1020027008066A patent/KR100771287B1/ko not_active IP Right Cessation
- 2000-12-22 IL IL15035000A patent/IL150350A0/xx unknown
- 2000-12-22 CN CNB008182582A patent/CN1196680C/zh not_active Expired - Fee Related
- 2000-12-22 UA UA2002076054A patent/UA73337C2/uk unknown
- 2000-12-22 HU HU0203874A patent/HUP0203874A3/hu unknown
2002
- 2002-06-14 ZA ZA200204813A patent/ZA200204813B/xx unknown
- 2002-06-17 NO NO20022879A patent/NO323329B1/no not_active IP Right Cessation
- 2002-06-19 BG BG106845A patent/BG65698B1/bg unknown
- 2002-06-20 IL IL150350A patent/IL150350A/en not_active IP Right Cessation
- 2002-06-20 HR HR20020539A patent/HRP20020539B1/xx not_active IP Right Cessation
2003
- 2003-09-09 HK HK03106410.6A patent/HK1054228B/zh not_active IP Right Cessation

Also Published As

Publication number	Publication date
RU2002119417A (ru)	2004-01-10
CA2394606A1 (en)	2001-06-28
BG65698B1 (bg)	2009-07-31
CA2394606C (en)	2009-06-02
HUP0203874A2 (hu)	2003-03-28
SK287366B6 (sk)	2010-08-09
IL150350A (en)	2010-05-31
EP1419773A3 (en)	2004-05-26
CZ302907B6 (cs)	2012-01-18
SE9904723D0 (sv)	1999-12-22
USRE41315E1 (en)	2010-05-04
PL362251A1 (en)	2004-10-18
HRP20020539A2 (en)	2004-08-31
JP2003518096A (ja)	2003-06-03
MXPA02006317A (es)	2004-05-14
CZ20022074A3 (cs)	2002-10-16
EE05083B1 (et)	2008-10-15
KR100771287B1 (ko)	2007-10-29
PT1419773E (pt)	2008-07-01
AU778183B2 (en)	2004-11-18
UA73337C2 (en)	2005-07-15
NO20022879D0 (no)	2002-06-17
BG106845A (en)	2003-04-30
DK1419773T3 (da)	2008-09-22
DE60039131D1 (de)	2008-07-17
ES2307861T3 (es)	2008-12-01
BR0016635A (pt)	2002-10-15
HK1054228B (zh)	2005-09-16
ZA200204813B (en)	2003-08-27
NO20022879L (no)	2002-08-21
RU2262504C2 (ru)	2005-10-20
KR20020067565A (ko)	2002-08-22
WO2001046146A1 (en)	2001-06-28
EP1419773B1 (en)	2008-06-04
CN1420870A (zh)	2003-05-28
US20030004169A1 (en)	2003-01-02
US6924374B2 (en)	2005-08-02
NZ519566A (en)	2004-05-28
EP1419773A2 (en)	2004-05-19
HRP20020539B1 (en)	2009-06-30
IL150350A0 (en)	2002-12-01
NZ531643A (en)	2005-03-24
EE200200345A (et)	2003-06-16
HK1054228A1 (en)	2003-11-21
ATE397446T1 (de)	2008-06-15
CN1196680C (zh)	2005-04-13
JP5096654B2 (ja)	2012-12-12
HUP0203874A3 (en)	2005-03-29
EP1240143A1 (en)	2002-09-18
PL205092B1 (pl)	2010-03-31
SK8662002A3 (en)	2003-02-04
AU2570601A (en)	2001-07-03

Legal Events

Date	Code	Title	Description
2014-07-21	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO323329B1 (no)	2007-03-26	Substituerte 4-(fenyl-N-alkyl)-piperidin-forbindelser samt farmasoytiske materialer og anvendelser derav
CA2394602C (en)	2009-03-10	New modulators of dopamine neurotransmission
USRE46117E1 (en)	2016-08-23	Modulators of dopamine neurotransmission
AU2005200729B2 (en)	2006-11-16	New modulators of dopamine neurotransmission