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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238000009835 boiling Methods 0.000 description 1
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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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238000001914 filtration Methods 0.000 description 1
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235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
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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
239000000725 suspension Substances 0.000 description 1
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)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Heart & Thoracic Surgery (AREA)
Anesthesiology (AREA)
Ophthalmology & Optometry (AREA)
Addiction (AREA)
Cardiology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic 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)	NO20000722L (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
AU744539B2 (en) *	1997-10-27	2002-02-28	Neurosearch A/S	Heteroaryl diazacycloalkanes as cholinergic ligands at nicotinic acetylcholine receptors
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
EP1246817B1 (en)	1999-12-30	2004-06-23	H. Lundbeck A/S	4-phenyl-1-piperazinyl, -piperidinyl and -tetrahydropyridyl derivatives
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
AU2002336273A1 (en) *	2001-03-09	2002-09-24	Ortho-Mcneil Pharmaceutical, Inc.	Heterocyclic compounds and their use as histamine h4 ligands.
CA2497827A1 (en)	2002-09-06	2004-03-18	Janssen Pharmaceutica, N.V.	(1h-benzoimidazol-2-yl)-(piperazinyl)-methanone derivatives and related compounds as histamine h4-receptor antagonists for the treatment of inflammatory and allergic disorders
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
EP2253315A1 (en)	2004-03-30	2010-11-24	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
JP5431305B2 (ja)	2007-04-23	2014-03-05	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	高速解離性ドパミン２受容体アンタゴニストとしての４−アルコキシピリダジン誘導体
WO2008128996A1 (en)	2007-04-23	2008-10-30	Janssen Pharmaceutica N.V.	Thia(dia)zoles as fast dissociating dopamine 2 receptor antagonists
EP2310374B1 (en)	2008-07-03	2012-10-31	Janssen Pharmaceutica N.V.	Substituted 6- (1-piperazinyl) -pyridazines as 5-ht6 receptor antagonists
EP2307374B1 (en)	2008-07-31	2017-01-25	Janssen Pharmaceutica NV	Piperazin-1-yl-trifluoromethyl-substituted-pyridines as fast dissociating dopamine 2 receptor antagonists
US11266640B2 (en) *	2017-09-20	2022-03-08	Hangzhou Innogate Pharma Co., Ltd.	Polycyclic compound acting as IDO inhibitor and/or IDO-HDAC dual inhibitor
US20230150980A1 (en) *	2020-04-22	2023-05-18	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
JPH08502958A (ja) *	1992-10-23	1996-04-02	メルクシヤープエンドドームリミテツド	ドーパミンレセプターサブタイプリガンド
AU6215594A (en) *	1993-03-18	1994-10-11	Merck Sharp & Dohme Limited	Indole derivatives as dopamine d4 antagonists
GB9305644D0 (en) *	1993-03-18	1993-05-05	Merck Sharp & Dohme	Therapeutic agents
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 AU AU84572/98A patent/AU8457298A/en not_active Abandoned
- 1998-08-05 TR TR2000/00414T patent/TR200000414T2/xx unknown
- 1998-08-05 EP EP98935229A patent/EP1003739A2/en not_active Withdrawn
- 1998-08-05 CN CN98807831A patent/CN1265660A/zh active Pending
- 1998-08-05 IL IL13396098A patent/IL133960A0/xx unknown
- 1998-08-05 JP JP2000509706A patent/JP2002536291A/ja active Pending
- 1998-08-05 HU HU0003425A patent/HUP0003425A3/hu unknown
- 1998-08-05 AP APAP/P/1998/001321A patent/AP9801321A0/en unknown
- 1998-08-05 PL PL98338947A patent/PL338947A1/xx unknown
- 1998-08-05 CA CA002297486A patent/CA2297486C/en not_active Expired - Fee Related
- 1998-08-05 ID IDW20000197A patent/ID23803A/id unknown
- 1998-08-05 WO PCT/IB1998/001198 patent/WO1999009025A2/en not_active Ceased
- 1998-08-05 BR BR9811557-0A patent/BR9811557A/pt not_active IP Right Cessation
- 1998-08-05 KR KR1020007001093A patent/KR20010022507A/ko not_active Ceased
- 1998-08-05 SK SK135-2000A patent/SK1352000A3/sk unknown
- 1998-08-05 EA EA200000023A patent/EA200000023A1/ru 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 MA MA25210A patent/MA24632A1/fr unknown
- 1998-08-12 DZ DZ980193A patent/DZ2583A1/xx active
- 1998-08-12 TN TNTNSN98151A patent/TNSN98151A1/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/NO20000722L/no not_active Application Discontinuation

Also Published As

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

Publication	Publication Date	Title
WO1999009025A2 (en)	1999-02-25	2-(4-aryl or heteroaryl-piperazin-1-ylmethyl)-1h-indole derivatives interacting with the dopamine d4 receptor
US8044069B2 (en)	2011-10-25	Compounds as calcium channel blockers
EP2167083B1 (en)	2015-10-28	1- heteroaryl-3-azabicyclo[3.1.0]hexanes, methods for their preparation and their use as medicaments
US7049335B2 (en)	2006-05-23	3-azabicyclo[3.1.0]hexane derivatives
EP1909797A2 (en)	2008-04-16	Dipiperazinyl ketones and related analogues
AU2007307105A1 (en)	2008-04-17	N-substituted-azacyclylamines as histamine-3 antagonists
Andersen et al.	1992	Selective, centrally acting serotonin 5-HT2 antagonists. 2. Substituted 3-(4-fluorophenyl)-1H-indoles
US20080293771A1 (en)	2008-11-27	Azacyclylbenzamide derivatives as histamine-3 antagonists
EP1581522B1 (en)	2008-02-20	Flavaxate derivatives as muscarinic receptor antagonists
HU220070B (hu)	2001-10-28	N-szubsztituált aza-biciklo[3.2.0]heptán-származékok és ezeket a vegyületeket tartalmazó gyógyszerkészítmények
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HUP0303316A2 (hu)	2004-01-28	Aril- és amino-aril-szubsztituált szerotoninreceptor agonista és antagonista ligandumok és ezeket tartalmazó gyógyszerkészítmények
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
KR101471987B1 (ko)	2014-12-12	일정한 ｃｎｓ-관련 질환을 치료하기 위한 2-알킬-인다졸 화합물
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
CN101426778A (zh)	2009-05-06	作为组胺-3拮抗剂的n-经取代-氮杂环基胺
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
HK1123550A (en)	2009-06-19	Novel 2,3-dihydroindole compounds
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