CA2122599A1 - Derives ether d'alkylpiperidines et d'alkylpyrrolidines utilises comme antipsychotiques - Google Patents

Derives ether d'alkylpiperidines et d'alkylpyrrolidines utilises comme antipsychotiques

Info

Publication number: CA2122599A1
Authority: CA; Canada
Prior art keywords: compound; mammal; phenyl; inhibiting; formula
Prior art date: 1991-10-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002122599A

Other languages

English (en)

Inventor

Gary Avonn Cain

Thomas Eugene Christos

Sang William Tam

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bristol Myers Squibb Pharma Co

Original Assignee

Individual

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.)

1991-10-30

Filing date

1991-10-30

Publication date

1993-05-13

1991-10-30 Application filed by Individual filed Critical Individual

1991-10-30 Priority to CA002122599A priority Critical patent/CA2122599A1/fr

1991-10-30 Priority to PCT/US1991/007842 priority patent/WO1993009094A1/fr

1991-10-30 Priority to EP92905089A priority patent/EP0610192A1/fr

1991-10-30 Priority to JP4504730A priority patent/JPH07502008A/ja

1991-10-30 Priority claimed from PCT/US1991/007842 external-priority patent/WO1993009094A1/fr

1993-05-13 Publication of CA2122599A1 publication Critical patent/CA2122599A1/fr

Status Abandoned legal-status Critical Current

Links

239000000164 antipsychotic agent Substances 0.000 title abstract description 9
150000002170 ethers Chemical class 0.000 title abstract description 4
150000003235 pyrrolidines Chemical class 0.000 title abstract description 4
150000003053 piperidines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 84
238000000034 method Methods 0.000 claims abstract description 37
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 17
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
-1 p-F-phenyl Chemical group 0.000 claims description 40
239000002585 base Substances 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 27
230000002401 inhibitory effect Effects 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 16
239000012442 inert solvent Substances 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 15
229910052783 alkali metal Inorganic materials 0.000 claims description 14
239000003937 drug carrier Substances 0.000 claims description 13
150000001340 alkali metals Chemical class 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
125000001624 naphthyl group Chemical group 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
239000003638 chemical reducing agent Substances 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
229910000102 alkali metal hydride Inorganic materials 0.000 claims description 3
150000008046 alkali metal hydrides Chemical class 0.000 claims description 3
229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
150000001983 dialkylethers Chemical class 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
229910052782 aluminium Inorganic materials 0.000 claims description 2
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims description 2
150000008282 halocarbons Chemical class 0.000 claims description 2
125000005270 trialkylamine group Chemical group 0.000 claims description 2
208000028017 Psychotic disease Diseases 0.000 claims 23
241000124008 Mammalia Species 0.000 claims 22
150000003950 cyclic amides Chemical class 0.000 claims 2
AMRCLUNCVPHMMQ-KPKJPENVSA-N 1-benzyl-4-[[(e)-3-phenylprop-2-enoxy]methyl]piperidine Chemical compound C=1C=CC=CC=1/C=C/COCC(CC1)CCN1CC1=CC=CC=C1 AMRCLUNCVPHMMQ-KPKJPENVSA-N 0.000 claims 1
DBQIRNPOVZULRT-UHFFFAOYSA-N C1(=CC=CC=C1)C(C)N1CCC(CC1)COCC=CC1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(C)N1CCC(CC1)COCC=CC1=CC=CC=C1 DBQIRNPOVZULRT-UHFFFAOYSA-N 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 46
229910001868 water Inorganic materials 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
239000000203 mixture Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
235000019439 ethyl acetate Nutrition 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000000543 intermediate Substances 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000003921 oil Substances 0.000 description 12
239000012043 crude product Substances 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
239000012267 brine Substances 0.000 description 9
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 8
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
229960003878 haloperidol Drugs 0.000 description 7
239000012528 membrane Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
230000027455 binding Effects 0.000 description 6
229940079593 drug Drugs 0.000 description 6
239000003814 drug Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
101150041968 CDC13 gene Proteins 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000000047 product Substances 0.000 description 5
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
230000016571 aggressive behavior Effects 0.000 description 4
210000004556 brain Anatomy 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
239000003210 dopamine receptor blocking agent Substances 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
238000010992 reflux Methods 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000011282 treatment Methods 0.000 description 4
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
229940121891 Dopamine receptor antagonist Drugs 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
239000012448 Lithium borohydride Substances 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
230000000561 anti-psychotic effect Effects 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
229940073608 benzyl chloride Drugs 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
239000012230 colorless oil Substances 0.000 description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
238000010494 dissociation reaction Methods 0.000 description 3
230000005593 dissociations Effects 0.000 description 3
239000000499 gel Substances 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
230000036961 partial effect Effects 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
206010001488 Aggression Diseases 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
208000016285 Movement disease Diseases 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
229940122490 Sigma receptor antagonist Drugs 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
229930006000 Sucrose Natural products 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
208000012761 aggressive behavior Diseases 0.000 description 2
230000002152 alkylating effect Effects 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
150000001414 amino alcohols Chemical class 0.000 description 2
229940005529 antipsychotics Drugs 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
150000004657 carbamic acid derivatives Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
239000007891 compressed tablet Substances 0.000 description 2
229960003638 dopamine Drugs 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
VEIWYFRREFUNRC-UHFFFAOYSA-N hydron;piperidine;chloride Chemical class [Cl-].C1CC[NH2+]CC1 VEIWYFRREFUNRC-UHFFFAOYSA-N 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000008297 liquid dosage form Substances 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
125000005948 methanesulfonyloxy group Chemical group 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
239000003182 parenteral nutrition solution Substances 0.000 description 2
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
230000000506 psychotropic effect Effects 0.000 description 2
108010085082 sigma receptors Proteins 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
ZZJYIKPMDIWRSN-TZBSWOFLSA-N (+)-butaclamol Chemical compound C12=CC=CC=C2CCC2=CC=CC3=C2[C@@H]1CN1CC[C@@](C(C)(C)C)(O)C[C@@H]13 ZZJYIKPMDIWRSN-TZBSWOFLSA-N 0.000 description 1
FLQPYEOKVZYXRL-UHFFFAOYSA-N (1-benzylpiperidin-4-yl)methanol Chemical compound C1CC(CO)CCN1CC1=CC=CC=C1 FLQPYEOKVZYXRL-UHFFFAOYSA-N 0.000 description 1
SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 1
GEQWKFXDTNQJJN-UHFFFAOYSA-N 1-[2-(2-nitroethenyl)phenyl]propan-1-one Chemical class CCC(=O)C1=CC=CC=C1C=C[N+]([O-])=O GEQWKFXDTNQJJN-UHFFFAOYSA-N 0.000 description 1
ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 1
WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
LDSQQXKSEFZAPE-UHFFFAOYSA-N 2-piperidin-4-ylethanol Chemical compound OCCC1CCNCC1 LDSQQXKSEFZAPE-UHFFFAOYSA-N 0.000 description 1
RMPSZEZJKSUNKR-UHFFFAOYSA-N 3-chloroprop-1-ynylbenzene Chemical compound ClCC#CC1=CC=CC=C1 RMPSZEZJKSUNKR-UHFFFAOYSA-N 0.000 description 1
SDEBYHVDMCQKNZ-UHFFFAOYSA-N 4-methoxy-6-piperazin-1-ylpyrimidine;hydrochloride Chemical compound Cl.C1=NC(OC)=CC(N2CCNCC2)=N1 SDEBYHVDMCQKNZ-UHFFFAOYSA-N 0.000 description 1
WKLZNTYMDOPBSE-UHFFFAOYSA-N 823218-99-1 Chemical compound CC1=CC(C)=CC(C)=C1C1=NOC2C1C1CCC2C1 WKLZNTYMDOPBSE-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
102000015554 Dopamine receptor Human genes 0.000 description 1
108050004812 Dopamine receptor Proteins 0.000 description 1
208000012661 Dyskinesia Diseases 0.000 description 1
208000027776 Extrapyramidal disease Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
JSSIAXXILAGJKE-FOWTUZBSSA-N Mahanimbinol Chemical compound N1C2=CC=CC=C2C2=C1C(C/C=C(C)/CCC=C(C)C)=C(O)C(C)=C2 JSSIAXXILAGJKE-FOWTUZBSSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Chemical class 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
206010043118 Tardive Dyskinesia Diseases 0.000 description 1
ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
IWTYTFSSTWXZFU-QPJJXVBHSA-N [(e)-3-chloroprop-1-enyl]benzene Chemical compound ClC\C=C\C1=CC=CC=C1 IWTYTFSSTWXZFU-QPJJXVBHSA-N 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000005233 alkylalcohol group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
230000003374 anti-dyskinetic effect Effects 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003064 anti-oxidating effect Effects 0.000 description 1
239000000729 antidote Substances 0.000 description 1
229940075522 antidotes Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
239000012148 binding buffer Substances 0.000 description 1
AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical class CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical class CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000001913 cellulose Chemical class 0.000 description 1
229920002678 cellulose Chemical class 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
229960001076 chlorpromazine Drugs 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000003255 drug test Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000006274 endogenous ligand Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
ASQCOPJFYLJCGD-UHFFFAOYSA-N ethyl 1-benzylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1=CC=CC=C1 ASQCOPJFYLJCGD-UHFFFAOYSA-N 0.000 description 1
RUJPPJYDHHAEEK-UHFFFAOYSA-N ethyl piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCNCC1 RUJPPJYDHHAEEK-UHFFFAOYSA-N 0.000 description 1
125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
230000003400 hallucinatory effect Effects 0.000 description 1
238000011597 hartley guinea pig Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000003446 ligand Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
MLSKXPOBNQFGHW-UHFFFAOYSA-N methoxy(dioxido)borane Chemical compound COB([O-])[O-] MLSKXPOBNQFGHW-UHFFFAOYSA-N 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
230000001095 motoneuron effect Effects 0.000 description 1
210000001577 neostriatum Anatomy 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229950010883 phencyclidine Drugs 0.000 description 1
150000002990 phenothiazines Chemical class 0.000 description 1
VUNPWIPIOOMCPT-UHFFFAOYSA-N piperidin-3-ylmethanol Chemical compound OCC1CCCNC1 VUNPWIPIOOMCPT-UHFFFAOYSA-N 0.000 description 1
XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
AMLFJZRZIOZGPW-UHFFFAOYSA-N prop-1-en-1-amine Chemical class CC=CN AMLFJZRZIOZGPW-UHFFFAOYSA-N 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
239000003196 psychodysleptic agent Substances 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
239000002287 radioligand Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
239000008107 starch Chemical class 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
YBNJZIDYXCGAPX-UHFFFAOYSA-N tert-butyl 4-(2-hydroxyethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CCO)CC1 YBNJZIDYXCGAPX-UHFFFAOYSA-N 0.000 description 1
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- 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
- 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
- C07D211/20—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 with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Psychiatry (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Hydrogenated Pyridines (AREA)
Pyrrole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA002122599A 1991-10-30 1991-10-30 Derives ether d'alkylpiperidines et d'alkylpyrrolidines utilises comme antipsychotiques Abandoned CA2122599A1 (fr)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
CA002122599A CA2122599A1 (fr)	1991-10-30	1991-10-30	Derives ether d'alkylpiperidines et d'alkylpyrrolidines utilises comme antipsychotiques
PCT/US1991/007842 WO1993009094A1 (fr)	1991-10-30	1991-10-30	Derives ethers de pyrrolidines et de piperidines d'alkyle utilises en tant qu'agents antipsychotiques
EP92905089A EP0610192A1 (fr)	1991-10-30	1991-10-30	Derives ethers de pyrrolidines et de piperidines d'alkyle utilises en tant qu'agents antipsychotiques
JP4504730A JPH07502008A (ja)	1991-10-30	1991-10-30	抗精神病薬としてのアルキルピペリジンおよびピロリジンのエーテル誘導体

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA002122599A CA2122599A1 (fr)	1991-10-30	1991-10-30	Derives ether d'alkylpiperidines et d'alkylpyrrolidines utilises comme antipsychotiques
PCT/US1991/007842 WO1993009094A1 (fr)	1991-10-30	1991-10-30	Derives ethers de pyrrolidines et de piperidines d'alkyle utilises en tant qu'agents antipsychotiques

Publications (1)

Publication Number	Publication Date
CA2122599A1 true CA2122599A1 (fr)	1993-05-13

Family

ID=4153503

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002122599A Abandoned CA2122599A1 (fr)	1991-10-30	1991-10-30	Derives ether d'alkylpiperidines et d'alkylpyrrolidines utilises comme antipsychotiques

Country Status (3)

Country	Link
EP (1)	EP0610192A1 (fr)
JP (1)	JPH07502008A (fr)
CA (1)	CA2122599A1 (fr)

1991
- 1991-10-30 JP JP4504730A patent/JPH07502008A/ja active Pending
- 1991-10-30 CA CA002122599A patent/CA2122599A1/fr not_active Abandoned
- 1991-10-30 EP EP92905089A patent/EP0610192A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
EP0610192A1 (fr)	1994-08-17
JPH07502008A (ja)	1995-03-02

Publication	Publication Date	Title
US5252586A (en)	1993-10-12	Ether derivatives of alkyl piperidines and pyrrolidines as antipsychotic agents
US7205319B2 (en)	2007-04-17	N-[phenyl (piperidin-2-yl) methyl]benzamide derivatives, preparation thereof, and use thereof in therapy
US5837707A (en)	1998-11-17	Dimeric piperidine, tetrahydropyridine and piperazine derivatives
KR100229117B1 (ko)	1999-11-01	피페리딘 유도체
US5254569A (en)	1993-10-19	(Amidomethyl)nitrogen heterocyclic analgesics
US5270328A (en)	1993-12-14	Peripherally selective piperidine opioid antagonists
AU631990B2 (en)	1992-12-10	New aminopiperidine, aminopyrrolidine and aminoperhydroazepine compounds, processes for their preparation thereof and pharmaceutical compositions containing them
CA2005919C (fr)	1997-01-07	Derives de substitution en n d'acides carboxyliques heterocycliques azotes
US5116846A (en)	1992-05-26	N-aralkyl piperidine derivatives as psychotropic drugs
US5945434A (en)	1999-08-31	Indazole derivatives having monocyclic amine
JPH09505277A (ja)	1997-05-27	４−ピペリドンのカルベン添加／アミノリシスによるスフェンタニル誘導体の製造方法
CA2135861A1 (fr)	1995-06-14	Derives de l'oxazolidine-2-one
HU206677B (en)	1992-12-28	Process for producing new 4,4-disubstituted piperidine derivatives and pharmaceutical compositions containing them
EP0029707A1 (fr)	1981-06-03	Dérivés de la pipéridine, procédé pour leur préparation et compositions pharmaceutiques les contenant
WO1993009094A1 (fr)	1993-05-13	Derives ethers de pyrrolidines et de piperidines d'alkyle utilises en tant qu'agents antipsychotiques
KR20040007672A (ko)	2004-01-24	신규한 페닐알킬디아민 및 아미드 유사체
EP0449195B1 (fr)	1996-05-08	Dérivés d'aminobenzène, préparation et application
US4430335A (en)	1984-02-07	Substituted 1-azaspiro[4,5]decanes and their analgesic compositions
CA2122599A1 (fr)	1993-05-13	Derives ether d'alkylpiperidines et d'alkylpyrrolidines utilises comme antipsychotiques
US4518713A (en)	1985-05-21	Analgesic substituted-1-aminoalkylamino-4-aryloxypiperidines
EP1032561B1 (fr)	2004-02-11	Oximes substitues en tant qu'antagonistes de neurokinine
US5856318A (en)	1999-01-05	Nitrogen-containing cyclohetero cyclo-heteroaminoaryl derivatives for CNS disorders
US4029786A (en)	1977-06-14	Morpholine derivatives for treating depression
US4329464A (en)	1982-05-11	Spiro[dihydrobenzofuran-piperidines and -pyrrolidines]
EP0141968B1 (fr)	1988-05-18	Pyrrolylaminopipéridines, procédé pour leur préparation et leur application en tant que médicaments

Legal Events

Date	Code	Title	Description
1998-10-30	FZDE	Dead