CA2205998C - Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives; new classes of dopamine receptor subtype specific ligands - Google Patents

Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives; new classes of dopamine receptor subtype specific ligands Download PDF

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Publication number: CA2205998C
Authority: CA; Canada
Prior art keywords: methyl; phenyl; compound; imidazole; pyrimidinyl
Prior art date: 1994-11-23
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.): Expired - Fee Related

Application number

CA002205998A

Other languages

English (en)

French (fr)

Other versions

CA2205998A1 (en

Inventor

Andrew Thurkauf

Raymond F. Horvath

Jun Yuan

John M. Peterson

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

Neurogen Corp

Original Assignee

Neurogen Corp

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.)

1994-11-23

Filing date

1995-11-22

Publication date

2002-07-16

1995-03-09 Priority claimed from US08/401,201 external-priority patent/US5681956A/en

1995-11-22 Application filed by Neurogen Corp filed Critical Neurogen Corp

1996-05-30 Publication of CA2205998A1 publication Critical patent/CA2205998A1/en

2002-07-16 Application granted granted Critical

2002-07-16 Publication of CA2205998C publication Critical patent/CA2205998C/en

2015-11-22 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

-1 4-aminomethyl-2-substituted imidazole Chemical class 0.000 title claims description 155
108050004812 Dopamine receptor Proteins 0.000 title abstract description 16
102000015554 Dopamine receptor Human genes 0.000 title abstract description 16
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical class NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title description 20
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 5
239000003446 ligand Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 237
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 53
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 46
150000003839 salts Chemical class 0.000 claims abstract description 31
125000000217 alkyl group Chemical group 0.000 claims description 166
239000001257 hydrogen Substances 0.000 claims description 150
229910052739 hydrogen Inorganic materials 0.000 claims description 150
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 149
229910052736 halogen Inorganic materials 0.000 claims description 138
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 121
125000003545 alkoxy group Chemical group 0.000 claims description 110
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 90
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 claims description 69
125000000714 pyrimidinyl group Chemical group 0.000 claims description 52
125000004076 pyridyl group Chemical group 0.000 claims description 50
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
125000003884 phenylalkyl group Chemical group 0.000 claims description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
150000002460 imidazoles Chemical class 0.000 claims description 22
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
231100000252 nontoxic Toxicity 0.000 claims description 15
230000003000 nontoxic effect Effects 0.000 claims description 15
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
229910052731 fluorine Chemical group 0.000 claims description 11
239000011737 fluorine Chemical group 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 8
STHHLVCQSLRQNI-UHFFFAOYSA-N 1-azabicyclo[3.2.1]octane Chemical group C1C2CCN1CCC2 STHHLVCQSLRQNI-UHFFFAOYSA-N 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
125000004432 carbon atom Chemical class C* 0.000 abstract description 122
125000001424 substituent group Chemical group 0.000 abstract description 20
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201000000980 schizophrenia Diseases 0.000 abstract description 14
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
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KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 18
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QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 11
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VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
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IAOGWYABFHUNKI-UHFFFAOYSA-N 1h-imidazole;dihydrochloride Chemical compound Cl.[Cl-].C1=C[NH+]=CN1 IAOGWYABFHUNKI-UHFFFAOYSA-N 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
208000035475 disorder Diseases 0.000 description 8
229960003638 dopamine Drugs 0.000 description 8
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 description 6
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CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
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KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
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DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
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COHOGNZHAUOXPA-UHFFFAOYSA-N trimethyl(phenyl)stannane Chemical compound C[Sn](C)(C)C1=CC=CC=C1 COHOGNZHAUOXPA-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
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AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical class N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- 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
- 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
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
- 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
- C07D401/14—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 three or more hetero rings
- 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)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Psychology (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA002205998A 1994-11-23 1995-11-22 Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives; new classes of dopamine receptor subtype specific ligands Expired - Fee Related CA2205998C (en)

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
US34455294A	1994-11-23	1994-11-23
US34415494A	1994-11-23	1994-11-23
US08/344,154		1994-11-23
US08/344,552		1994-11-23
US08/401,201		1995-03-09
US08/401,201 US5681956A (en)	1990-12-28	1995-03-09	4-aryl substituted piperazinylmethyl phenylimidazole derivatives; a new class of dopamine receptor subtype specific ligands
PCT/US1995/015262 WO1996016040A1 (en)	1994-11-23	1995-11-22	Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives; new classes of dopamine receptor subtype specific ligands

Publications (2)

Publication Number	Publication Date
CA2205998A1 CA2205998A1 (en)	1996-05-30
CA2205998C true CA2205998C (en)	2002-07-16

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ID=27407598

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002205998A Expired - Fee Related CA2205998C (en)	1994-11-23	1995-11-22	Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives; new classes of dopamine receptor subtype specific ligands

Country Status (8)

Country	Link
EP (1)	EP0793653A1 (de)
JP (1)	JP2941950B2 (de)
CN (1)	CN1088062C (de)
AU (1)	AU4368996A (de)
BR (1)	BR9509760A (de)
CA (1)	CA2205998C (de)
MX (1)	MX9703736A (de)
WO (1)	WO1996016040A1 (de)

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JP3157169B2 (ja)	1996-08-08	2001-04-16	シェーリングコーポレイション	アミノメチル―フェニルイミダゾールの調製
US5905152A (en) *	1996-08-08	1999-05-18	Schering Corporation	Preparation of aminomethyl-phenylimidazoles
DE19637237A1 (de)	1996-09-13	1998-03-19	Merck Patent Gmbh	Piperazin-Derivate
DE69835518T2 (de)	1997-06-12	2007-08-09	Aventis Pharma Ltd., West Malling	Imidazolyl-cyclische acetale
TW450954B (en) *	1998-05-14	2001-08-21	Pharmacia & Amp Upjohn Company	Phenylsulfonamide-phenylethylamines useful as dopamine receptors
DK1086086T3 (da) *	1998-06-12	2005-01-24	Sod Conseils Rech Applic	Imidazolylderivater og anvendelse deraf som somatostatinreceptorligander
US6288230B1 (en)	1998-09-29	2001-09-11	Neurogen Corporation	2-(2, 3-dihydrobenzofuran-5-yl)-4-aminomethylimidazoles: dopamine receptor subtype specific ligands
AU6503899A (en) *	1998-09-29	2000-04-17	Neurogen Corporation	2-(2,3-dihydrobenzofuran-5-yl)-4-aminomethylimidazoles: dopamine receptor subtype specific ligands
US6284759B1 (en)	1998-09-30	2001-09-04	Neurogen Corporation	2-piperazinoalkylaminobenzo-azole derivatives: dopamine receptor subtype specific ligands
WO2000021951A1 (en)	1998-10-08	2000-04-20	Smithkline Beecham Plc	Tetrahydrobenzazepine derivatives useful as modulators of dopamine d3 receptors (antipsychotic agents)
US6284761B1 (en)	1999-01-08	2001-09-04	Neurogen Corporation	1-phenyl-4-(1-[2-aryl]cyclopropyl)methylpiperazines: dopamine receptor ligands
HK1043360A1 (zh) *	1999-01-08	2002-09-13	Neurogen Corporation	1-苯基-4-(1-[2-芳基]环丙基)甲基哌嗉：多巴胺受体配体
TWI274750B (en) *	1999-01-12	2007-03-01	Abbott Gmbh & Co Kg	Triazole compounds showing high affinity to dopamine D3 receptor and pharmaceutical composition comprising the same
RU2380362C2 (ru) *	1999-10-11	2010-01-27	Сосьете Де Консей Де Решерш З	Производные пятичленных гетероциклов, способ их получения и их применение в качестве лекарственных средств
FR2812546B1 (fr) *	2000-08-01	2008-11-21	Sod Conseils Rech Applic	Derives d'heterocycles a 5 chainons, leur preparation et leur application a titre de medicaments
TWI283577B (en) *	1999-10-11	2007-07-11	Sod Conseils Rech Applic	Pharmaceutical composition of imidazole derivatives acting as modulators of sodium channels and the use thereof
KR100822085B1 (ko) *	1999-10-11	2008-04-15	소시에떼 드 꽁세이으 드 르세르세 에 따블리까시옹 시앙띠피끄 (에스.세.에르.아.에스.)	5-원 헤테로사이클 유도체, 이의 제조 방법 및의약으로서의 이의 용도
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1995
- 1995-11-22 EP EP95942473A patent/EP0793653A1/de not_active Withdrawn
- 1995-11-22 CN CN95197446A patent/CN1088062C/zh not_active Expired - Fee Related
- 1995-11-22 CA CA002205998A patent/CA2205998C/en not_active Expired - Fee Related
- 1995-11-22 JP JP8517074A patent/JP2941950B2/ja not_active Expired - Lifetime
- 1995-11-22 WO PCT/US1995/015262 patent/WO1996016040A1/en not_active Ceased
- 1995-11-22 BR BR9509760A patent/BR9509760A/pt not_active Application Discontinuation
- 1995-11-22 AU AU43689/96A patent/AU4368996A/en not_active Abandoned
1997
- 1997-05-21 MX MX9703736A patent/MX9703736A/es unknown

Also Published As

Publication number	Publication date
WO1996016040A1 (en)	1996-05-30
EP0793653A1 (de)	1997-09-10
MX9703736A (es)	1998-07-31
JP2941950B2 (ja)	1999-08-30
JPH10502670A (ja)	1998-03-10
CN1088062C (zh)	2002-07-24
AU4368996A (en)	1996-06-17
CA2205998A1 (en)	1996-05-30
BR9509760A (pt)	1998-06-30
CN1177349A (zh)	1998-03-25

Legal Events

Date	Code	Title	Description
1997-05-23	EEER	Examination request
2006-11-22	MKLA	Lapsed

Publication	Publication Date	Title
CA2205998C (en)	2002-07-16	Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives; new classes of dopamine receptor subtype specific ligands
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US5633376A (en)	1997-05-27	Certain aminomethyl phenylimidazole derivatives; and 4-aryl substituted piperazinyl and piperidinylmethyl phenylimidazole derivatives; a new class of dopamine receptor subtype ligands
US5159083A (en)	1992-10-27	Certain aminomethyl phenylimidazole derivatives; a class of dopamine receptor subtype specific ligands
US5017573A (en)	1991-05-21	Indazole-3-carboxylic acid derivatives
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JPH0573742B2 (de)	1993-10-15
WO1996016057A1 (en)	1996-05-30	Certain 1-substituted aminomethyl imidazole and pyrrole derivatives; novel dopamine receptor subtype specific ligands
CA2213197C (en)	2001-08-07	Certain bridged 4-phenyl-2-aminomethylimidazoles; new dopamine receptor subtype specific ligands
EP0793662A1 (de)	1997-09-10	Aminomethyl aryl verbindungen; für dopamin-unterrezeptoren spezifische liganden
US6002005A (en)	1999-12-14	Certain 1-substituted aminomethyl imidazole and pyrrole derivatives: novel dopamine receptor subtype specific ligands