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WO2000000489A3 - 6-(4-arylalkylpiperazin-1-yl)benzodioxane and 6-(4-arylalkylpiperazin-1-yl)chromane derivatives: dopamine receptor subtype specific ligands - Google Patents

6-(4-arylalkylpiperazin-1-yl)benzodioxane and 6-(4-arylalkylpiperazin-1-yl)chromane derivatives: dopamine receptor subtype specific ligands Download PDF

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Publication number
WO2000000489A3
WO2000000489A3 PCT/US1999/014426 US9914426W WO0000489A3 WO 2000000489 A3 WO2000000489 A3 WO 2000000489A3 US 9914426 W US9914426 W US 9914426W WO 0000489 A3 WO0000489 A3 WO 0000489A3
Authority
WO
WIPO (PCT)
Prior art keywords
arylalkylpiperazin
benzodioxane
dopamine receptor
receptor subtype
specific ligands
Prior art date
Application number
PCT/US1999/014426
Other languages
French (fr)
Other versions
WO2000000489A2 (en
Inventor
Jennifer N Tran
Andrew Thurkauf
Original Assignee
Neurogen Corp
Jennifer N Tran
Andrew Thurkauf
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.)
Filing date
Publication date
Application filed by Neurogen Corp, Jennifer N Tran, Andrew Thurkauf filed Critical Neurogen Corp
Priority to AU47204/99A priority Critical patent/AU4720499A/en
Priority to EP99930727A priority patent/EP1091949A2/en
Priority to CA002336089A priority patent/CA2336089A1/en
Priority to JP2000557250A priority patent/JP2002519350A/en
Publication of WO2000000489A2 publication Critical patent/WO2000000489A2/en
Publication of WO2000000489A3 publication Critical patent/WO2000000489A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
    • 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
    • A61P25/22—Anxiolytics
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/02—Seven-membered rings
    • C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
    • C07D313/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • C07D321/02—Seven-membered rings
    • C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Addiction (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Furan Compounds (AREA)
  • Pyrane Compounds (AREA)

Abstract

Disclosed are compounds of formula (I) or the pharmaceutically acceptable acid addition salts thereof, wherein: R1, R2, R3, R4 and R5 are the same or different and represent hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C4 alkylthio, hydroxy, amino, mono- or di(C1-C6)alkylamino, cyano, nitro, trifluoromethyl or trifluoromethoxy; and X is oxygen, a bond, C1-C2 alkylene or methyleneoxy, which compounds are useful for the treatment and/or prevention of neuropsychological disorders including, but not limited to, schizophrenia, mania, dementia, depression, anxiety, compulsive behavior, substance abuse, Parkinson-like motor disorders and motion disorders related to the use of neuroleptic agents.
PCT/US1999/014426 1998-06-30 1999-06-25 6-(4-arylalkylpiperazin-1-yl)benzodioxane and 6-(4-arylalkylpiperazin-1-yl)chromane derivatives: dopamine receptor subtype specific ligands WO2000000489A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU47204/99A AU4720499A (en) 1998-06-30 1999-06-25 6-(4-arylalkylpiperazin-1-yl)benzodioxane and 6-(4-arylalkylpiperazin-1-yl)chromane derivatives: dopamine receptor subtype specific ligands
EP99930727A EP1091949A2 (en) 1998-06-30 1999-06-25 6-(4-arylalkylpiperazin-1-yl)benzodioxane and 6-(4-arylalkylpiperazin-1-yl)chromane derivatives: dopamine receptor subtype specific ligands
CA002336089A CA2336089A1 (en) 1998-06-30 1999-06-25 6-(4-arylalkylpiperazin-1-yl)benzodioxane and 6-(4-arylalkylpiperazin-1-yl)chromane derivatives: dopamine receptor subtype specific ligands
JP2000557250A JP2002519350A (en) 1998-06-30 1999-06-25 6- (4-arylalkylpiperazin-1-yl) benzodioxane and 6- (4-arylalkylpiperazin-1-yl) chroman derivatives: dopamine receptor subtype specific ligands

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10924298A 1998-06-30 1998-06-30
US09/109,242 1998-06-30

Publications (2)

Publication Number Publication Date
WO2000000489A2 WO2000000489A2 (en) 2000-01-06
WO2000000489A3 true WO2000000489A3 (en) 2000-02-10

Family

ID=22326595

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/014426 WO2000000489A2 (en) 1998-06-30 1999-06-25 6-(4-arylalkylpiperazin-1-yl)benzodioxane and 6-(4-arylalkylpiperazin-1-yl)chromane derivatives: dopamine receptor subtype specific ligands

Country Status (5)

Country Link
EP (1) EP1091949A2 (en)
JP (1) JP2002519350A (en)
AU (1) AU4720499A (en)
CA (1) CA2336089A1 (en)
WO (1) WO2000000489A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2009259494A1 (en) 2008-06-16 2009-12-23 F. Hoffmann-La Roche Ag Heteroaromatic monoamides as orexinin receptor antagonists

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5550129A (en) * 1992-10-08 1996-08-27 Willmar Schwabe Gmbh & Co. Benzopyranones, processes for their preparation and their use
WO1997041108A1 (en) * 1996-04-30 1997-11-06 Warner-Lambert Company Substituted piperazines and piperidines as central nervous system agents
WO1997044334A2 (en) * 1996-05-17 1997-11-27 EGIS Gyógyszergyár Rt. Novel piperazine or homopiperazine derivatives, pharmaceutical compositions containing the same and a process for their preparation
WO1997045419A1 (en) * 1996-05-29 1997-12-04 Warner-Lambert Company Benzoxazinone dopamine d4 receptor antagonists
WO1998033784A1 (en) * 1997-01-30 1998-08-06 Neurogen Corporation 1-phenyl-4-benzylpiperazines: dopamine receptor subtype specific ligands (d4)

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5550129A (en) * 1992-10-08 1996-08-27 Willmar Schwabe Gmbh & Co. Benzopyranones, processes for their preparation and their use
WO1997041108A1 (en) * 1996-04-30 1997-11-06 Warner-Lambert Company Substituted piperazines and piperidines as central nervous system agents
WO1997044334A2 (en) * 1996-05-17 1997-11-27 EGIS Gyógyszergyár Rt. Novel piperazine or homopiperazine derivatives, pharmaceutical compositions containing the same and a process for their preparation
WO1997045419A1 (en) * 1996-05-29 1997-12-04 Warner-Lambert Company Benzoxazinone dopamine d4 receptor antagonists
WO1998033784A1 (en) * 1997-01-30 1998-08-06 Neurogen Corporation 1-phenyl-4-benzylpiperazines: dopamine receptor subtype specific ligands (d4)

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
ALLEN B. REITZ ET AL.: "n-aryl-n'-benzylpiperazines as potential antipsychotic agents", J. MED. CHEM., vol. 38, no. 21, 1995, columbus ohio, pages 4211 - 4222, XP002065378 *
IZZY BOYFIELD ET AL.: "n-(substituted-phenyl)piperazines: Antagonists with high binding and functional selectivity for dopamine d4 receptors", BIOORGANIC &MEDICINAL CHEMISTRY LETTERS, vol. 6, no. 11, 1996, great britain, pages 1227 - 1232, XP002065936 *
MICHAEL S. HADLEY: "d4 Receptors and their Antagonists", MEDICINAL RESEARCH REVIEWS, vol. 16, no. 6, 1996, pages 507-526, XP000654693 *
S. SARATI ET AL.: "kinetics of piribedil and effects on dopamine metabolism: hepatic biotransformation is not a determinant of its dopaminergic action in rats", PSYCHOPHARMACOLOGY, vol. 105, 1991, pages 541 - 545, XP002065935 *

Also Published As

Publication number Publication date
WO2000000489A2 (en) 2000-01-06
EP1091949A2 (en) 2001-04-18
AU4720499A (en) 2000-01-17
JP2002519350A (en) 2002-07-02
CA2336089A1 (en) 2000-01-06

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