OA11286A - 2-(4-Aryl or heteroaryl-piperazin-1-ylmethyl)-1h-indole derivatives interacting with the dopamine d4receptor. - Google Patents

2-(4-Aryl or heteroaryl-piperazin-1-ylmethyl)-1h-indole derivatives interacting with the dopamine d4receptor. Download PDF

Info

Publication number: OA11286A
Authority: OA; OAPI
Prior art keywords: disorders; fluoro; piperazin; dopamine; compound according
Prior art date: 1997-08-15

Application number

OA1200000030A

Other languages

English (en)

Inventor

Anton Franz Josef Fliri

Mark Jerome Majchrzak

Hans Rollema

Patricia Ann Seymour

Stevin Howard Zorn

Original Assignee

Pfizer Prod Inc

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.)

1997-08-15

Filing date

2000-02-08

Publication date

2003-10-22

2000-02-08 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2003-10-22 Publication of OA11286A publication Critical patent/OA11286A/en

Links

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229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
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239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
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238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
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CVVIJWRCGSYCMB-UHFFFAOYSA-N hydron;piperazine;dichloride Chemical compound Cl.Cl.C1CNCCN1 CVVIJWRCGSYCMB-UHFFFAOYSA-N 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
OWYJZQFASFWUHP-UHFFFAOYSA-N hydroxylamine;1h-indole Chemical compound ON.C1=CC=C2NC=CC2=C1 OWYJZQFASFWUHP-UHFFFAOYSA-N 0.000 description 1
230000028993 immune response Effects 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
235000015110 jellies Nutrition 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
YBXBWBBVLXZQBJ-UHFFFAOYSA-N n-[2-(5-hydroxy-2-methyl-1h-indol-3-yl)ethyl]-2-methoxyacetamide Chemical compound C1=C(O)C=C2C(CCNC(=O)COC)=C(C)NC2=C1 YBXBWBBVLXZQBJ-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000008203 oral pharmaceutical composition Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
239000002953 phosphate buffered saline Substances 0.000 description 1
239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
230000009329 sexual behaviour Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
229950001675 spiperone Drugs 0.000 description 1
108010092215 spiroperidol receptor Proteins 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
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239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

OA1200000030A 1997-08-15 2000-02-08 2-(4-Aryl or heteroaryl-piperazin-1-ylmethyl)-1h-indole derivatives interacting with the dopamine d4receptor. OA11286A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US5576497P	1997-08-15	1997-08-15

Publications (1)

Publication Number	Publication Date
OA11286A true OA11286A (en)	2003-10-22

Family

ID=22000003

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200000030A OA11286A (en)	1997-08-15	2000-02-08	2-(4-Aryl or heteroaryl-piperazin-1-ylmethyl)-1h-indole derivatives interacting with the dopamine d4receptor.

Country Status (30)

Country	Link
EP (1)	EP1003739A2 (is)
JP (1)	JP2002536291A (is)
KR (1)	KR20010022507A (is)
CN (1)	CN1265660A (is)
AP (1)	AP9801321A0 (is)
AR (1)	AR017019A1 (is)
AU (1)	AU8457298A (is)
BG (1)	BG104069A (is)
BR (1)	BR9811557A (is)
CA (1)	CA2297486C (is)
CO (1)	CO4960656A1 (is)
DZ (1)	DZ2583A1 (is)
EA (1)	EA200000023A1 (is)
HR (1)	HRP980441A2 (is)
HU (1)	HUP0003425A3 (is)
ID (1)	ID23803A (is)
IL (1)	IL133960A0 (is)
IS (1)	IS5336A (is)
MA (1)	MA24632A1 (is)
NO (1)	NO20000722D0 (is)
OA (1)	OA11286A (is)
PA (1)	PA8457001A1 (is)
PE (1)	PE106299A1 (is)
PL (1)	PL338947A1 (is)
SK (1)	SK1352000A3 (is)
TN (1)	TNSN98151A1 (is)
TR (1)	TR200000414T2 (is)
UY (1)	UY25144A1 (is)
WO (1)	WO1999009025A2 (is)
ZA (1)	ZA987304B (is)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4570773B2 (ja) *	1997-10-27	2010-10-27	ニューロサーチ、アクティーゼルスカブ	ニコチン性アセチルコリンレセプターに於けるコリン作動性リガンドとしてのヘテロアリールジアザシクロアルカン
EP0953567A3 (en) *	1998-04-29	2003-04-02	Pfizer Products Inc.	Bicyclic substituted piperazine-, piperidine- and tetrahydropyridine derivatives, their preparation and their use as agents with central dopaminergic (dopamine D4 receptor) activity
DE60011817T2 (de) *	1999-12-30	2005-07-14	H. Lundbeck A/S	4-phenyl-1-piperazinyl, -piperidinyl und -tetrahydropyridyl-derivate
GB0017952D0 (en) *	2000-07-22	2000-09-13	Univ Manchester	Treatment of dyskinesia
EP1177792A3 (en)	2000-07-27	2002-10-23	Pfizer Products Inc.	Dopamine D4 Ligands for the treatment of novelty-seeking disorders
US6803362B2 (en)	2001-03-09	2004-10-12	Ortho-Mcneil Pharmaceutical Inc.	Heterocyclic compounds
PL377087A1 (pl)	2002-09-06	2006-01-23	Janssen Pharmaceutica, N.V.	Związki heterocykliczne
WO2004108671A1 (en) *	2003-06-06	2004-12-16	Suven Life Sciences Limited	Substituted indoles with serotonin receptor affinity, process for their preparation and pharmaceutical compositions containing them
EP1731505B1 (en)	2004-03-30	2015-01-14	Takeda Pharmaceutical Company Limited	Alkoxyphenylpropanoic acid derivatives
US7572805B2 (en)	2004-07-14	2009-08-11	Bristol-Myers Squibb Company	Pyrrolo(oxo)isoquinolines as 5HT ligands
US7618980B2 (en)	2004-07-14	2009-11-17	Bristol-Myers Squibb Company	Pyrrolo(oxo)quinolines as 5HT ligands
JO2769B1 (en) *	2005-10-26	2014-03-15	جانسين فارماسوتيكا ان. في	Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor
JO2642B1 (en)	2006-12-08	2012-06-17	جانسين فارماسوتيكا ان. في	Dopamine 2 receptor antagonists are rapidly hydrolyzed
JO2849B1 (en) *	2007-02-13	2015-03-15	جانسين فارماسوتيكا ان. في	Dopamine 2 receptor antagonists are rapidly hydrolyzed
CA2683111A1 (en)	2007-04-23	2008-10-30	Janssen Pharmaceutica N.V.	4-alkoxypyridazine derivatives as fast dissociating dopamine 2 receptor antagonists
MX2009011416A (es)	2007-04-23	2009-11-05	Janssen Pharmaceutica Nv	Tia(di)azoles como antagonistas del receptor de dopamina 2 de disociacion rapida.
JP5417439B2 (ja)	2008-07-03	2014-02-12	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	５−ｈｔ６受容体アンタゴニストとしての置換された６−（１−ピペラジニル）−ピリダジン類
CN102171189B (zh)	2008-07-31	2013-11-20	詹森药业有限公司	作为快速解离多巴胺2受体拮抗剂的哌嗪-1-基-三氟甲基取代的吡啶
WO2019057123A1 (zh) *	2017-09-20	2019-03-28	杭州英创医药科技有限公司	作为ido抑制剂和/或ido-hdac双重抑制剂的多环化合物
WO2021216665A1 (en) *	2020-04-22	2021-10-28	Anima Biotech Inc.	Collagen 1 translation inhibitors and methods of use thereof

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB944443A (is) *	1959-09-25	1900-01-01
ES2097341T3 (es) *	1991-07-03	1997-04-01	Upjohn Co	Indoles sustituidos como farmacos para el tratamiento del sida.
JPH05255089A (ja) *	1991-12-18	1993-10-05	Sanwa Kagaku Kenkyusho Co Ltd	抗ウイルス剤
CA2146018A1 (en) *	1992-10-23	1994-05-11	Paul David Leeson	Dopamine receptor subtype ligands
GB9305644D0 (en) *	1993-03-18	1993-05-05	Merck Sharp & Dohme	Therapeutic agents
AU6215594A (en) *	1993-03-18	1994-10-11	Merck Sharp & Dohme Limited	Indole derivatives as dopamine d4 antagonists
WO1994024105A1 (en) *	1993-04-15	1994-10-27	Merck Sharp & Dohme Limited	Indole derivatives as dopamine d4 antagonists
DE4414113A1 (de) *	1994-04-22	1995-10-26	Merck Patent Gmbh	3-Indolylpiperidine
TW406075B (en) *	1994-12-13	2000-09-21	Upjohn Co	Alkyl substituted piperidinyl and piperazinyl anti-AIDS compounds
ZA968661B (en) *	1995-11-17	1998-04-14	Upjohn Co	Oxazolidinone antibacterial agent with tricyclic substituents.
TW504510B (en) *	1996-05-10	2002-10-01	Janssen Pharmaceutica Nv	2,4-diaminopyrimidine derivatives

1998
- 1998-08-05 CN CN98807831A patent/CN1265660A/zh active Pending
- 1998-08-05 CA CA002297486A patent/CA2297486C/en not_active Expired - Fee Related
- 1998-08-05 JP JP2000509706A patent/JP2002536291A/ja active Pending
- 1998-08-05 ID IDW20000197A patent/ID23803A/id unknown
- 1998-08-05 KR KR1020007001093A patent/KR20010022507A/ko not_active Ceased
- 1998-08-05 SK SK135-2000A patent/SK1352000A3/sk unknown
- 1998-08-05 AU AU84572/98A patent/AU8457298A/en not_active Abandoned
- 1998-08-05 BR BR9811557-0A patent/BR9811557A/pt not_active IP Right Cessation
- 1998-08-05 HU HU0003425A patent/HUP0003425A3/hu unknown
- 1998-08-05 EA EA200000023A patent/EA200000023A1/ru unknown
- 1998-08-05 WO PCT/IB1998/001198 patent/WO1999009025A2/en not_active Ceased
- 1998-08-05 AP APAP/P/1998/001321A patent/AP9801321A0/en unknown
- 1998-08-05 TR TR2000/00414T patent/TR200000414T2/xx unknown
- 1998-08-05 EP EP98935229A patent/EP1003739A2/en not_active Withdrawn
- 1998-08-05 PL PL98338947A patent/PL338947A1/xx unknown
- 1998-08-05 IL IL13396098A patent/IL133960A0/xx unknown
- 1998-08-10 PE PE1998000717A patent/PE106299A1/es not_active Application Discontinuation
- 1998-08-10 PA PA19988457001A patent/PA8457001A1/es unknown
- 1998-08-12 DZ DZ980193A patent/DZ2583A1/xx active
- 1998-08-12 TN TNTNSN98151A patent/TNSN98151A1/fr unknown
- 1998-08-12 MA MA25210A patent/MA24632A1/fr unknown
- 1998-08-13 AR ARP980104021A patent/AR017019A1/es unknown
- 1998-08-14 HR HR60/055,764A patent/HRP980441A2/hr not_active Application Discontinuation
- 1998-08-14 ZA ZA9807304A patent/ZA987304B/xx unknown
- 1998-08-14 CO CO98046788A patent/CO4960656A1/es unknown
- 1998-08-17 UY UY25144A patent/UY25144A1/es not_active Application Discontinuation
2000
- 2000-01-10 BG BG104069A patent/BG104069A/xx unknown
- 2000-01-11 IS IS5336A patent/IS5336A/is unknown
- 2000-02-08 OA OA1200000030A patent/OA11286A/en unknown
- 2000-02-14 NO NO20000722A patent/NO20000722D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
HUP0003425A2 (hu)	2001-10-28
IS5336A (is)	2000-01-11
JP2002536291A (ja)	2002-10-29
PE106299A1 (es)	1999-11-02
HUP0003425A3 (en)	2002-02-28
EA200000023A1 (ru)	2000-08-28
TR200000414T2 (tr)	2000-08-21
AP9801321A0 (en)	2000-02-14
BR9811557A (pt)	2000-08-22
DZ2583A1 (fr)	2003-02-22
AR017019A1 (es)	2001-08-22
CA2297486C (en)	2005-05-03
PL338947A1 (en)	2000-12-04
UY25144A1 (es)	2000-12-29
CN1265660A (zh)	2000-09-06
WO1999009025A3 (en)	1999-04-15
ID23803A (id)	2000-05-11
WO1999009025A2 (en)	1999-02-25
BG104069A (en)	2001-05-31
CO4960656A1 (es)	2000-09-25
TNSN98151A1 (fr)	2005-03-15
IL133960A0 (en)	2001-04-30
NO20000722L (no)	2000-02-14
MA24632A1 (fr)	1999-04-01
HRP980441A2 (en)	1999-04-30
CA2297486A1 (en)	1999-02-25
KR20010022507A (ko)	2001-03-15
SK1352000A3 (en)	2000-08-14
EP1003739A2 (en)	2000-05-31
ZA987304B (en)	2000-02-14
AU8457298A (en)	1999-03-08
PA8457001A1 (es)	2000-09-29
NO20000722D0 (no)	2000-02-14

Publication	Publication Date	Title
OA11286A (en)	2003-10-22	2-(4-Aryl or heteroaryl-piperazin-1-ylmethyl)-1h-indole derivatives interacting with the dopamine d4receptor.
US8044069B2 (en)	2011-10-25	Compounds as calcium channel blockers
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AU2002300094B2 (en)	2007-06-14	New octahydro-2H-pyrido[1,2-alpha]pyrazine compounds, a process for their preparation and pharmaceutical compositions containing them
US20040198734A1 (en)	2004-10-07	2-(4-Aryl or heteroaryl-piperazin-1-ylmethyl)-1H-indole derivatives interacting with the dopamine
Richter et al.	2010	Discovery of potent and selective histamine H3 receptor inverse agonists based on the 3, 4-dihydro-2H-pyrazino [1, 2-a] indol-1-one scaffold
SK42299A3 (en)	1999-12-10	N-(benzothiazol-2-yl) piperidine-1-ethanamine derivatives, their preparation and application in therapeutics
US9597315B2 (en)	2017-03-21	1-heteroaryl-3-azabicyclo[3.1.0]hexanes, methods for their preparation and their use as medicaments
MXPA00001611A (en)	2001-03-05	2-(4-aryl or heteroaryl-piperazin-1-ylmethyl)-1h-indole derivatives
CZ2000307A3 (cs)	2000-08-16	Deriváty 2-(4-aryI nebo heteroarylpiperazin-1- ylmetyl)-lH-indolu
Kang et al.	2003	Preparation of Diastereomeric β-Aryloxymethylaminoalcohols Containing Nicotinic Acid Moiety and Their Binding Affinity to β 3-Adrenoreceptors
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