JPH07502008A - 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 - Google Patents

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

Info

Publication number: JPH07502008A
Authority: JP; Japan
Prior art keywords: compound according; formula; psychosis; compound; phenyl
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.): Pending

Application number

JP4504730A

Other languages

English (en)

Japanese (ja)

Inventor

ケイン，ゲーリー・エイボン

クリストス，トマス・ユージーン

タム，サング・ウイリアム

Original Assignee

ザ・デュポン・メルク・ファーマシュウティカル・カンパニー

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

1995-03-02

1991-10-30 Application filed by ザ・デュポン・メルク・ファーマシュウティカル・カンパニー filed Critical ザ・デュポン・メルク・ファーマシュウティカル・カンパニー

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

1995-03-02 Publication of JPH07502008A publication Critical patent/JPH07502008A/ja

Status Pending legal-status Critical Current

Links

239000000164 antipsychotic agent Substances 0.000 title description 7
229940005529 antipsychotics Drugs 0.000 title description 4
150000002170 ethers Chemical class 0.000 title description 4
150000003235 pyrrolidines Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 91
-1 p-F-phenyl Chemical group 0.000 claims description 38
125000004432 carbon atom Chemical group C* 0.000 claims description 31
239000000203 mixture Substances 0.000 claims description 31
239000002585 base Substances 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 23
208000028017 Psychotic disease Diseases 0.000 claims description 22
238000000034 method Methods 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
239000003814 drug Substances 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 18
239000000126 substance Substances 0.000 claims description 14
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 13
229910052783 alkali metal Inorganic materials 0.000 claims description 13
239000003937 drug carrier Substances 0.000 claims description 13
239000012442 inert solvent Substances 0.000 claims description 13
150000001340 alkali metals Chemical class 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 9
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
239000003638 chemical reducing agent Substances 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
230000029936 alkylation Effects 0.000 claims description 4
238000005804 alkylation reaction Methods 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
150000003950 cyclic amides Chemical class 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000001424 substituent group Chemical group 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
229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 2
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
150000005826 halohydrocarbons Chemical class 0.000 claims description 2
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125000005270 trialkylamine group Chemical group 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims 12
241000124008 Mammalia Species 0.000 claims 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
229910000102 alkali metal hydride Inorganic materials 0.000 claims 2
150000008046 alkali metal hydrides Chemical class 0.000 claims 2
238000010511 deprotection reaction Methods 0.000 claims 2
150000001983 dialkylethers Chemical group 0.000 claims 2
201000010099 disease Diseases 0.000 claims 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
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VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
150000004820 halides Chemical group 0.000 claims 1
229910001507 metal halide Inorganic materials 0.000 claims 1
150000005309 metal halides Chemical class 0.000 claims 1
150000002829 nitrogen Chemical class 0.000 claims 1
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229940072033 potash Drugs 0.000 claims 1
235000015320 potassium carbonate Nutrition 0.000 claims 1
208000020016 psychiatric disease Diseases 0.000 claims 1
125000004665 trialkylsilyl group Chemical group 0.000 claims 1
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235000019439 ethyl acetate Nutrition 0.000 description 17
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
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239000000543 intermediate Substances 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
239000012043 crude product Substances 0.000 description 10
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 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000003480 eluent Substances 0.000 description 9
239000003921 oil Substances 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
229940079593 drug Drugs 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000012458 free base Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
102000015554 Dopamine receptor Human genes 0.000 description 6
108050004812 Dopamine receptor Proteins 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
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239000012267 brine Substances 0.000 description 6
238000005259 measurement Methods 0.000 description 6
238000002844 melting Methods 0.000 description 6
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239000012528 membrane Substances 0.000 description 6
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
238000011282 treatment Methods 0.000 description 6
229960003878 haloperidol Drugs 0.000 description 5
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
241000699670 Mus sp. Species 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
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
238000009835 boiling Methods 0.000 description 4
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NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
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241000699666 Mus <mouse, genus> Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
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210000004556 brain Anatomy 0.000 description 3
150000004657 carbamic acid derivatives Chemical class 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
238000001816 cooling Methods 0.000 description 3
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OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
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 2
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VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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239000004472 Lysine Substances 0.000 description 1
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239000012359 Methanesulfonyl chloride Substances 0.000 description 1
230000006181 N-acylation Effects 0.000 description 1
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239000002202 Polyethylene glycol Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229940122490 Sigma receptor antagonist Drugs 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229920002472 Starch Chemical class 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
241000862969 Stella Species 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
206010043118 Tardive Dyskinesia Diseases 0.000 description 1
206010044334 Trance Diseases 0.000 description 1
239000007983 Tris buffer Substances 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
239000002253 acid Substances 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000005234 alkyl aluminium group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
125000005233 alkylalcohol group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
210000003323 beak Anatomy 0.000 description 1
230000006399 behavior Effects 0.000 description 1
229960000686 benzalkonium chloride Drugs 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
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-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
239000004202 carbamide Substances 0.000 description 1
QNEFNFIKZWUAEQ-UHFFFAOYSA-N carbonic acid;potassium Chemical compound [K].OC(O)=O QNEFNFIKZWUAEQ-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 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
238000005119 centrifugation Methods 0.000 description 1
239000003795 chemical substances by application Substances 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
238000003776 cleavage reaction Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
238000003255 drug test Methods 0.000 description 1
230000002996 emotional effect Effects 0.000 description 1
239000006274 endogenous ligand Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001033 ether 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
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
230000000763 evoking effect Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
239000007789 gas Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000011597 hartley guinea pig Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
210000003127 knee Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical class [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
HTBVGZAVHBZXMS-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]alumane Chemical class [Li].[Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] HTBVGZAVHBZXMS-UHFFFAOYSA-N 0.000 description 1
230000003137 locomotive effect Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000011976 maleic acid Substances 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
238000010907 mechanical stirring Methods 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
238000012544 monitoring process Methods 0.000 description 1
230000001095 motoneuron effect Effects 0.000 description 1
210000001577 neostriatum Anatomy 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
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
229940124641 pain reliever Drugs 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000002990 phenothiazines Chemical class 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
230000003389 potentiating effect Effects 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
125000006239 protecting group Chemical group 0.000 description 1
229940001470 psychoactive drug Drugs 0.000 description 1
239000004089 psychotropic agent Substances 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
238000005476 soldering Methods 0.000 description 1
239000007909 solid dosage form Substances 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
239000005720 sucrose 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
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
235000019640 taste Nutrition 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
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
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
PIAOLBVUVDXHHL-VOTSOKGWSA-N β-nitrostyrene Chemical compound [O-][N+](=O)\C=C\C1=CC=CC=C1 PIAOLBVUVDXHHL-VOTSOKGWSA-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)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Biomedical Technology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Psychiatry (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)

JP4504730A 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 Pending JPH07502008A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
PCT/US1991/007842 WO1993009094A1 (en)	1991-10-30	1991-10-30	Ether derivatives of alkyl piperidines and pyrrolidines as antipsychotic agents
CA002122599A CA2122599A1 (en)	1991-10-30	1991-10-30	Ether derivatives of alkyl piperidines and pyrrolidines as antipsychotic agents

Publications (1)

Publication Number	Publication Date
JPH07502008A true JPH07502008A (ja)	1995-03-02

Family

ID=4153503

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP4504730A Pending 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

Country Status (3)

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

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

Also Published As

Publication number	Publication date
EP0610192A1 (de)	1994-08-17
CA2122599A1 (en)	1993-05-13

Publication	Publication Date	Title
US5317024A (en)	1994-05-31	Ether derivatives of alkyl piperidines and pyrrolidines as antipsychotic agents
JP2786480B2 (ja)	1998-08-13	１―インドリルアルキル―４―（置換ピリジニル）ピペラジン
US5116846A (en)	1992-05-26	N-aralkyl piperidine derivatives as psychotropic drugs
US5296479A (en)	1994-03-22	Treatment of psychosis using 1-cycloalkylpiperidines
JP4488891B2 (ja)	2010-06-23	Ｎ−［フェニル（ピペリジン−２−イル）メチル］ベンズアミド誘導体、その製造法、およびその治療用途
IE83893B1 (en)		Polycyclic amine compounds and their enantiomers, their method of preparation and pharmaceutical compositions in which they are present
SK390892A3 (en)	1995-09-13	Fluoroalkoxybenzylamino derivatives of nitrogen containing heterocycles method of their preparation, intermediates and using
CA2029275A1 (en)	1991-05-07	Aromatic amine compounds, their method of preparation and pharmaceutical compositions in which they are present
JPH0794429B2 (ja)	1995-10-11	新規なアミノピペリジン、アミノピロリジンおよびアミノパーヒドロアゼピン化合物
GB2271774A (en)	1994-04-27	Piperazine derivatives
JPH04230362A (ja)	1992-08-19	新規なピペリジン、テトラヒドロピリジンおよびピロリジン誘導体およびこれらを含有する製薬組成物
JPH0655720B2 (ja)	1994-07-27	新規化合物類
CA2542925A1 (fr)	2005-04-28	Derives de n-[phenyl(alkylpiperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique
JPH07505142A (ja)	1995-06-08	抗精神病性窒素含有二環式化合物
CA1291759C (en)	1991-11-05	Antidepressant 2-(4,5-dihydro-1h-imidazolyl)-dihydro-1h- indoles, -tetrahydroquinolines and -1h-indoles
US5554763A (en)	1996-09-10	1-azoniabicyclo[2.2.1] heptanes and pharmaceutical compositions in which they are present
KR20040007672A (ko)	2004-01-24	신규한 페닐알킬디아민 및 아미드 유사체
WO2000044376A1 (en)	2000-08-03	Antidepressant heterocyclic compounds
WO1993009094A1 (en)	1993-05-13	Ether derivatives of alkyl piperidines and pyrrolidines as antipsychotic agents
CN1041088C (zh)	1998-12-09	光学活性咪唑烷酮衍生物和抗痴呆药物组合物
US4430335A (en)	1984-02-07	Substituted 1-azaspiro[4,5]decanes and their analgesic compositions
KR100619464B1 (ko)	2006-09-05	신규한 3-테트라하이드로피리딘-4-일 인돌 화합물
JPH07502008A (ja)	1995-03-02	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
US4880822A (en)	1989-11-14	N-(pyridinyl)-1H-indol-1-amines
EP0449195A2 (de)	1991-10-02	Aminobenzolverbindungen, Herstellung und Verwendung