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WO2000018767A3 - 2-piperazino alkylamino benzoazole derivatives: dopamine receptor subtype specific ligands - Google Patents

2-piperazino alkylamino benzoazole derivatives: dopamine receptor subtype specific ligands Download PDF

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Publication number
WO2000018767A3
WO2000018767A3 PCT/US1999/022791 US9922791W WO0018767A3 WO 2000018767 A3 WO2000018767 A3 WO 2000018767A3 US 9922791 W US9922791 W US 9922791W WO 0018767 A3 WO0018767 A3 WO 0018767A3
Authority
WO
WIPO (PCT)
Prior art keywords
piperazino
alkylamino
dopamine receptor
receptor subtype
specific ligands
Prior art date
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.)
Ceased
Application number
PCT/US1999/022791
Other languages
French (fr)
Other versions
WO2000018767A9 (en
WO2000018767A2 (en
Inventor
Xiao-Shu He
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.)
Filing date
Publication date
Application filed by Neurogen Corp filed Critical Neurogen Corp
Priority to CA002345944A priority Critical patent/CA2345944A1/en
Priority to JP2000572226A priority patent/JP2002525373A/en
Priority to EP99950068A priority patent/EP1117663A2/en
Priority to HK02100301.2A priority patent/HK1038749A1/en
Priority to AU62801/99A priority patent/AU6280199A/en
Publication of WO2000018767A2 publication Critical patent/WO2000018767A2/en
Publication of WO2000018767A3 publication Critical patent/WO2000018767A3/en
Anticipated expiration legal-status Critical
Publication of WO2000018767A9 publication Critical patent/WO2000018767A9/en
Ceased legal-status Critical Current

Links

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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/30—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/82—Nitrogen 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

Disclosed are compounds of formula (I) or pharmaceutically acceptable salts thereof, wherein: A is (un)substituted alkylene; R1 and R2 are the same or different and represent hydrogen, halogen, alkyl, alkoxy, alkylthio, hydroxy, (un)substituted amino, cyano, nitro, sulfonamide, trifluoromethyl or trifluoromethoxy; R3, R4, R5, R6 and R8 are independently hydrogen or alkyl; and X is sulfur, oxygen or NR7 where R8 is defined herein; m is an integer chosen from 0, 1 or 2; and Ar is an aryl or heteroaryl group as further defined herein, 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/US1999/022791 1998-09-30 1999-09-30 2-piperazino alkylamino benzoazole derivatives: dopamine receptor subtype specific ligands Ceased WO2000018767A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CA002345944A CA2345944A1 (en) 1998-09-30 1999-09-30 2-piperazino alkylamino benzoazole derivatives: dopamine receptor subtype specific ligands
JP2000572226A JP2002525373A (en) 1998-09-30 1999-09-30 2-piperazinoalkylaminobenzoazole derivatives: dopamine receptor subtype special ligand
EP99950068A EP1117663A2 (en) 1998-09-30 1999-09-30 2-piperazino alkylamino benzoazole derivatives: dopamine receptor subtype specific ligands
HK02100301.2A HK1038749A1 (en) 1998-09-30 1999-09-30 2-piperazino alkylamino benzoazole derivatives: dopamine receptor subtype specific ligands
AU62801/99A AU6280199A (en) 1998-09-30 1999-09-30 2-piperazino alkylamino benzoazole derivatives: dopamine receptor subtype specific ligands

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US16357398A 1998-09-30 1998-09-30
US09/163,573 1998-09-30

Publications (3)

Publication Number Publication Date
WO2000018767A2 WO2000018767A2 (en) 2000-04-06
WO2000018767A3 true WO2000018767A3 (en) 2000-07-27
WO2000018767A9 WO2000018767A9 (en) 2001-04-19

Family

ID=22590612

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/022791 Ceased WO2000018767A2 (en) 1998-09-30 1999-09-30 2-piperazino alkylamino benzoazole derivatives: dopamine receptor subtype specific ligands

Country Status (7)

Country Link
EP (1) EP1117663A2 (en)
JP (1) JP2002525373A (en)
CN (1) CN1325397A (en)
AU (1) AU6280199A (en)
CA (1) CA2345944A1 (en)
HK (1) HK1038749A1 (en)
WO (1) WO2000018767A2 (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100526487B1 (en) 2000-06-21 2005-11-08 에프. 호프만-라 로슈 아게 Benzothiazole derivatives
US6713499B2 (en) * 2001-12-12 2004-03-30 Hoffman-La Roche Inc. 7-Amino-benzothiazole derivatives
GB0203299D0 (en) * 2002-02-12 2002-03-27 Glaxo Group Ltd Novel compounds
TW200400035A (en) 2002-03-28 2004-01-01 Glaxo Group Ltd Novel compounds
US7087761B2 (en) 2003-01-07 2006-08-08 Hoffmann-La Roche Inc. Cyclization process for substituted benzothiazole derivatives
WO2005021547A2 (en) * 2003-08-28 2005-03-10 Pharmaxis Pty Ltd. Heterocyclic cannabinoid cb2 receptor antagonists
SG131946A1 (en) * 2003-10-24 2007-05-28 Hoffmann La Roche Ccr3 receptor antagonists
WO2005116026A1 (en) 2004-05-24 2005-12-08 F. Hoffmann-La Roche Ag 4-hydroxy-4-methyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide
FR2877005A1 (en) * 2004-10-22 2006-04-28 Bioprojet Soc Civ Ile NEW ARYLPIPERAZINE DERIVATIVES
US7459563B2 (en) 2004-11-05 2008-12-02 Hoffmann-La Roche Inc. Process for the preparation of isonicotinic acid derivatives
AU2006226669B2 (en) 2005-03-23 2011-12-08 F. Hoffmann-La Roche Ag Acetylenyl-pyrazolo-pvrimidine derivatives as mGluR2 antagonists
AU2006298829B2 (en) 2005-09-27 2011-03-03 F. Hoffmann-La Roche Ag Oxadiazolyl pyrazolo-pyrimidines as mGluR2 antagonists
HRP20161612T2 (en) 2012-12-27 2017-02-24 Alzprotect Sulphate salts of n-(3-(4-(3-(diisobutylamino)propyl)piperazin-1-yl)propyl)-1h-benzo[d]imidazol-2-amine, preparation thereof and use of the same
CN105753811A (en) * 2016-03-31 2016-07-13 湖南工程学院 A kind of dopamine D4 receptor ligand and its preparation method

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994022839A1 (en) * 1993-03-30 1994-10-13 Merck Sharp & Dohme Limited Antipsychotic benzimidazole derivatives
WO1996039403A1 (en) * 1995-06-05 1996-12-12 Neurogen Corporation 1-(n'-(arylalkylaminoalkyl)) aminoisoindoles as dopamine receptor ligands
WO1997043271A1 (en) * 1996-05-10 1997-11-20 Janssen Pharmaceutica N.V. Alkylaminobenzothiazole and -benzoxazole derivatives
WO1998056786A1 (en) * 1997-06-13 1998-12-17 Neurogen Corporation 2-aminoalkylaminoquinolines as dopamine d4 ligands
WO1999023092A2 (en) * 1997-10-31 1999-05-14 Neurogen Corporation 3-aminoalkylamino-2h-1,4-benzoxa(thia-)zines and pharmaceutical compositions containing them

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994022839A1 (en) * 1993-03-30 1994-10-13 Merck Sharp & Dohme Limited Antipsychotic benzimidazole derivatives
WO1996039403A1 (en) * 1995-06-05 1996-12-12 Neurogen Corporation 1-(n'-(arylalkylaminoalkyl)) aminoisoindoles as dopamine receptor ligands
WO1997043271A1 (en) * 1996-05-10 1997-11-20 Janssen Pharmaceutica N.V. Alkylaminobenzothiazole and -benzoxazole derivatives
WO1998056786A1 (en) * 1997-06-13 1998-12-17 Neurogen Corporation 2-aminoalkylaminoquinolines as dopamine d4 ligands
WO1999023092A2 (en) * 1997-10-31 1999-05-14 Neurogen Corporation 3-aminoalkylamino-2h-1,4-benzoxa(thia-)zines and pharmaceutical compositions containing them

Also Published As

Publication number Publication date
JP2002525373A (en) 2002-08-13
AU6280199A (en) 2000-04-17
WO2000018767A9 (en) 2001-04-19
HK1038749A1 (en) 2002-03-28
CN1325397A (en) 2001-12-05
EP1117663A2 (en) 2001-07-25
WO2000018767A2 (en) 2000-04-06
CA2345944A1 (en) 2000-04-06

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