SK172799A3 - 3-benzylpiperidine derivative, process for its preparation and pharmaceutical composition containing the same - Google Patents

3-benzylpiperidine derivative, process for its preparation and pharmaceutical composition containing the same Download PDF

Info

Publication number: SK172799A3
Authority: SK; Slovakia
Prior art keywords: butyl; benzylpiperidin; formula; indole; compound
Prior art date: 1997-06-18

Application number

SK1727-99A

Other languages

English (en)

Slovak (sk)

Inventor

Henning Bottcher

Helmut Prucher

Hartmut Greiner

Christoph Seyfried

Andrew Barber

Joseph-Maria Martinez

Original Assignee

Merck Patent Gmbh

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.)

1997-06-18

Filing date

1998-06-08

Publication date

2000-06-12

1998-06-08 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2000-06-12 Publication of SK172799A3 publication Critical patent/SK172799A3/sk

Links

238000000034 method Methods 0.000 title claims description 16
239000008194 pharmaceutical composition Substances 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 6
230000008569 process Effects 0.000 title claims description 5
BKDMXVREWXKZLB-UHFFFAOYSA-N 3-benzylpiperidine Chemical class C=1C=CC=CC=1CC1CCCNC1 BKDMXVREWXKZLB-UHFFFAOYSA-N 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 89
150000003839 salts Chemical class 0.000 claims abstract description 29
238000011282 treatment Methods 0.000 claims abstract description 26
239000003814 drug Substances 0.000 claims abstract description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
208000006011 Stroke Diseases 0.000 claims abstract description 9
238000004519 manufacturing process Methods 0.000 claims abstract description 8
-1 2-indolyl Chemical group 0.000 claims description 97
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 18
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 9
WGNXJXVNAUIMFO-UHFFFAOYSA-N 3-[4-(3-benzylpiperidin-1-yl)butyl]-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CCCCN(C1)CCCC1CC1=CC=CC=C1 WGNXJXVNAUIMFO-UHFFFAOYSA-N 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
210000004556 brain Anatomy 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
206010008118 cerebral infarction Diseases 0.000 claims description 6
239000003638 chemical reducing agent Substances 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000012453 solvate Substances 0.000 claims description 6
210000000278 spinal cord Anatomy 0.000 claims description 6
201000006474 Brain Ischemia Diseases 0.000 claims description 5
206010008120 Cerebral ischaemia Diseases 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
238000011321 prophylaxis Methods 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
201000010099 disease Diseases 0.000 claims description 4
208000014674 injury Diseases 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
238000006268 reductive amination reaction Methods 0.000 claims description 4
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WVWKARDJFKCPTP-UHFFFAOYSA-N 1-(3-benzylpiperidin-1-yl)-4-(5-chloro-1h-indol-3-yl)butan-1-one Chemical compound C12=CC(Cl)=CC=C2NC=C1CCCC(=O)N(C1)CCCC1CC1=CC=CC=C1 WVWKARDJFKCPTP-UHFFFAOYSA-N 0.000 claims description 3
LHQSWVYFXNBGHA-UHFFFAOYSA-N 1-(3-benzylpiperidin-1-yl)-4-(5-fluoro-1h-indol-3-yl)butan-1-one Chemical compound C12=CC(F)=CC=C2NC=C1CCCC(=O)N(C1)CCCC1CC1=CC=CC=C1 LHQSWVYFXNBGHA-UHFFFAOYSA-N 0.000 claims description 3
BGQQJPVVCRITOF-UHFFFAOYSA-N 3-[4-(3-benzylpiperidin-1-yl)butyl]-5-chloro-1h-indole Chemical compound C12=CC(Cl)=CC=C2NC=C1CCCCN(C1)CCCC1CC1=CC=CC=C1 BGQQJPVVCRITOF-UHFFFAOYSA-N 0.000 claims description 3
CPIJNSLMQSHCKY-UHFFFAOYSA-N 3-[4-(3-benzylpiperidin-1-yl)butyl]-5-fluoro-1h-indole Chemical compound C12=CC(F)=CC=C2NC=C1CCCCN(C1)CCCC1CC1=CC=CC=C1 CPIJNSLMQSHCKY-UHFFFAOYSA-N 0.000 claims description 3
RUTBXWVIBMTOBA-FQEVSTJZSA-N 7-[4-[(3s)-3-benzylpiperidin-1-yl]butyl]-5h-[1,3]dioxolo[4,5-f]indole Chemical compound C([C@@H]1CCCN(C1)CCCCC=1C2=CC=3OCOC=3C=C2NC=1)C1=CC=CC=C1 RUTBXWVIBMTOBA-FQEVSTJZSA-N 0.000 claims description 3
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 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
VMCHPKQLZLOOJG-UHFFFAOYSA-N methyl 3-[4-(3-benzylpiperidin-1-yl)butyl]-1h-indole-5-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2NC=C1CCCCN(C1)CCCC1CC1=CC=CC=C1 VMCHPKQLZLOOJG-UHFFFAOYSA-N 0.000 claims description 3
KSOOJJUNZORSAM-UHFFFAOYSA-N 1-[4-(1h-indol-3-yl)butyl]-2,3-diphenylpiperidin-2-ol Chemical compound C1CCN(CCCCC=2C3=CC=CC=C3NC=2)C(O)(C=2C=CC=CC=2)C1C1=CC=CC=C1 KSOOJJUNZORSAM-UHFFFAOYSA-N 0.000 claims description 2
LKPSJYQVHOILLW-UHFFFAOYSA-N 3-[4-(3-benzylpiperidin-1-yl)butyl]-1h-indole-5-carboxylic acid Chemical compound C12=CC(C(=O)O)=CC=C2NC=C1CCCCN(C1)CCCC1CC1=CC=CC=C1 LKPSJYQVHOILLW-UHFFFAOYSA-N 0.000 claims description 2
FLXQRWYZBBBJNH-UHFFFAOYSA-N 3-[4-(3-benzylpiperidin-1-yl)butyl]-5-methoxy-1h-indole Chemical compound C12=CC(OC)=CC=C2NC=C1CCCCN(C1)CCCC1CC1=CC=CC=C1 FLXQRWYZBBBJNH-UHFFFAOYSA-N 0.000 claims description 2
IKIYHGLNEPJBKD-JOCHJYFZSA-N 3-[4-[(3r)-3-benzylpiperidin-1-yl]butyl]-1h-indole-5-carbonitrile Chemical compound C([C@H]1CCCN(C1)CCCCC1=CNC2=CC=C(C=C21)C#N)C1=CC=CC=C1 IKIYHGLNEPJBKD-JOCHJYFZSA-N 0.000 claims description 2
CPIJNSLMQSHCKY-HXUWFJFHSA-N 3-[4-[(3r)-3-benzylpiperidin-1-yl]butyl]-5-fluoro-1h-indole Chemical compound C([C@H]1CCCN(C1)CCCCC1=CNC2=CC=C(C=C21)F)C1=CC=CC=C1 CPIJNSLMQSHCKY-HXUWFJFHSA-N 0.000 claims description 2
IKIYHGLNEPJBKD-QFIPXVFZSA-N 3-[4-[(3s)-3-benzylpiperidin-1-yl]butyl]-1h-indole-5-carbonitrile Chemical compound C([C@@H]1CCCN(C1)CCCCC1=CNC2=CC=C(C=C21)C#N)C1=CC=CC=C1 IKIYHGLNEPJBKD-QFIPXVFZSA-N 0.000 claims description 2
UDWUJTZEVHYIMD-UHFFFAOYSA-N 3-[4-[3-[(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]butyl]-1h-indole-5-carbonitrile Chemical compound C1CCN(CCCCC=2C3=CC(=CC=C3NC=2)C#N)CC1C(O)C1=CC=C(F)C=C1 UDWUJTZEVHYIMD-UHFFFAOYSA-N 0.000 claims description 2
LGBHVQXDSNYGPR-UHFFFAOYSA-N 5-fluoro-3-[4-[3-[(4-fluorophenyl)methyl]piperidin-1-yl]butyl]-1h-indole Chemical compound C1=CC(F)=CC=C1CC1CN(CCCCC=2C3=CC(F)=CC=C3NC=2)CCC1 LGBHVQXDSNYGPR-UHFFFAOYSA-N 0.000 claims description 2
241000972349 Ocoa Species 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
239000002552 dosage form Substances 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
CPIJNSLMQSHCKY-FQEVSTJZSA-N 3-[4-[(3s)-3-benzylpiperidin-1-yl]butyl]-5-fluoro-1h-indole Chemical compound C([C@@H]1CCCN(C1)CCCCC1=CNC2=CC=C(C=C21)F)C1=CC=CC=C1 CPIJNSLMQSHCKY-FQEVSTJZSA-N 0.000 claims 1
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DRYBMFJLYYEOBZ-UHFFFAOYSA-N methyl 1h-indole-5-carboxylate Chemical compound COC(=O)C1=CC=C2NC=CC2=C1 DRYBMFJLYYEOBZ-UHFFFAOYSA-N 0.000 claims 1
208000035475 disorder Diseases 0.000 abstract description 6
230000003389 potentiating effect Effects 0.000 abstract description 5
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150000003053 piperidines Chemical class 0.000 abstract description 3
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QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000002636 symptomatic treatment Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000002435 venom Substances 0.000 description 1
210000001048 venom Anatomy 0.000 description 1
231100000611 venom Toxicity 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Indole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK1727-99A 1997-06-18 1998-06-08 3-benzylpiperidine derivative, process for its preparation and pharmaceutical composition containing the same SK172799A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19725664A DE19725664A1 (de)	1997-06-18	1997-06-18	3-Benzylpiperidine
PCT/EP1998/003429 WO1998057953A1 (de)	1997-06-18	1998-06-08	3-benzylpiperidine

Publications (1)

Publication Number	Publication Date
SK172799A3 true SK172799A3 (en)	2000-06-12

Family

ID=7832780

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1727-99A SK172799A3 (en)	1997-06-18	1998-06-08	3-benzylpiperidine derivative, process for its preparation and pharmaceutical composition containing the same

Country Status (19)

Country	Link
US (1)	US6333339B1 (es)
EP (1)	EP0993458B1 (es)
JP (1)	JP2002511082A (es)
KR (1)	KR20010013750A (es)
CN (1)	CN1260791A (es)
AR (1)	AR011483A1 (es)
AT (1)	ATE236897T1 (es)
AU (1)	AU8214598A (es)
BR (1)	BR9810622A (es)
CA (1)	CA2294379A1 (es)
DE (2)	DE19725664A1 (es)
HU (1)	HUP0003997A3 (es)
NO (1)	NO996290D0 (es)
PL (1)	PL337229A1 (es)
RU (1)	RU2194047C2 (es)
SK (1)	SK172799A3 (es)
TW (1)	TW487706B (es)
WO (1)	WO1998057953A1 (es)
ZA (1)	ZA985254B (es)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1249051C (zh)	2000-04-28	2006-04-05	阿卡蒂亚药品公司	毒蕈碱性激动剂
DE10050236A1 (de) *	2000-10-11	2002-04-25	Merck Patent Gmbh	Verwendung bestimmter Substanzen, die an den Sigma-Rezeptor binden, zur Behandlung von Sarkomen und Karzinomen
US6713479B2 (en) *	2001-03-02	2004-03-30	Sepracor Inc.	Piperidine-piperazine ligands for neurotransmitter receptors
DE10305739A1 (de)	2003-02-11	2004-08-19	Merck Patent Gmbh	Benzofuranderivate
ATE414078T1 (de) *	2005-07-21	2008-11-15	Hoffmann La Roche	Indol-3-ylcarbonylpiperidinbenzimidazolderivate als v1a-rezeptorantagonisten
RU2329044C1 (ru) *	2006-11-16	2008-07-20	Андрей Александрович Иващенко	Лиганды 5-ht6 рецепторов, фармацевтическая композиция, способ ее получения и лекарственное средство
TWI410420B (zh) *	2008-02-05	2013-10-01	Dainippon Sumitomo Pharma Co	苄基哌啶化合物
US9533973B2 (en)	2011-12-08	2017-01-03	The Board Of Regents Of The University Of Texas System	Allosteric modulators of 5-hydroxytryptamine 2C receptor (5-HT2CR)
KR102508562B1 (ko)	2017-01-10	2023-03-10	석 영 정	직무능력 예측을 포함하는 직무 자동매칭 서비스 및 그를 이용하는 컴퓨팅 장치

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0007399B1 (de)	1978-06-24	1982-01-20	MERCK PATENT GmbH	Indolalkylamine, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung
US5256673A (en)	1983-11-25	1993-10-26	Merck Patent Gesellschaft Mit Beschrankter Haftung	Indole-3-yl-A-tetrahydropyridyl or piperidyl compounds
US5116846A (en) *	1990-03-28	1992-05-26	Du Pont Merck Pharmaceutical Company	N-aralkyl piperidine derivatives as psychotropic drugs
NZ243065A (en) *	1991-06-13	1995-07-26	Lundbeck & Co As H	Piperidine derivatives and pharmaceutical compositions
US5814644A (en)	1993-04-15	1998-09-29	Merck Sharp & Dohme, Ltd.	Indole derivatives as dopamine D4 antagonists
GB9314758D0 (en)	1993-07-16	1993-08-25	Wyeth John & Brother Ltd	Heterocyclic derivatives
GB9411099D0 (en)	1994-06-03	1994-07-27	Wyeth John & Brother Ltd	Piperazine derivatives
JP2002515891A (ja) *	1997-12-19	2002-05-28	スミスクライン・ビーチャム・コーポレイション	新規なピペリジン含有化合物

1997
- 1997-06-18 DE DE19725664A patent/DE19725664A1/de not_active Withdrawn
1998
- 1998-05-14 TW TW087107480A patent/TW487706B/zh active
- 1998-06-08 CA CA002294379A patent/CA2294379A1/en not_active Abandoned
- 1998-06-08 AU AU82145/98A patent/AU8214598A/en not_active Abandoned
- 1998-06-08 CN CN98806187A patent/CN1260791A/zh active Pending
- 1998-06-08 HU HU0003997A patent/HUP0003997A3/hu unknown
- 1998-06-08 JP JP50367999A patent/JP2002511082A/ja active Pending
- 1998-06-08 KR KR1019997011765A patent/KR20010013750A/ko not_active Withdrawn
- 1998-06-08 AT AT98932135T patent/ATE236897T1/de not_active IP Right Cessation
- 1998-06-08 PL PL98337229A patent/PL337229A1/xx unknown
- 1998-06-08 BR BR9810622-8A patent/BR9810622A/pt not_active IP Right Cessation
- 1998-06-08 RU RU2000101294/04A patent/RU2194047C2/ru not_active IP Right Cessation
- 1998-06-08 US US09/445,587 patent/US6333339B1/en not_active Expired - Fee Related
- 1998-06-08 SK SK1727-99A patent/SK172799A3/sk unknown
- 1998-06-08 DE DE59807879T patent/DE59807879D1/de not_active Expired - Fee Related
- 1998-06-08 EP EP98932135A patent/EP0993458B1/de not_active Expired - Lifetime
- 1998-06-08 WO PCT/EP1998/003429 patent/WO1998057953A1/de not_active Ceased
- 1998-06-17 AR ARP980102877A patent/AR011483A1/es not_active Application Discontinuation
- 1998-06-17 ZA ZA985254A patent/ZA985254B/xx unknown
1999
- 1999-12-17 NO NO996290A patent/NO996290D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
EP0993458B1 (de)	2003-04-09
ZA985254B (en)	1999-04-13
US6333339B1 (en)	2001-12-25
ATE236897T1 (de)	2003-04-15
PL337229A1 (en)	2000-08-14
WO1998057953A1 (de)	1998-12-23
CN1260791A (zh)	2000-07-19
KR20010013750A (ko)	2001-02-26
AR011483A1 (es)	2000-08-16
AU8214598A (en)	1999-01-04
DE19725664A1 (de)	1998-12-24
CA2294379A1 (en)	1998-12-23
NO996290L (no)	1999-12-17
NO996290D0 (no)	1999-12-17
BR9810622A (pt)	2000-10-03
TW487706B (en)	2002-05-21
HUP0003997A3 (en)	2001-04-28
JP2002511082A (ja)	2002-04-09
EP0993458A1 (de)	2000-04-19
DE59807879D1 (de)	2003-05-15
HUP0003997A2 (en)	2001-03-28
RU2194047C2 (ru)	2002-12-10

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