Nothing Special   »   [go: up one dir, main page]

WO2003028728A8 - 4-(4-substituted piperazinyl-1yl)-butylcarboxamides as d3 dopamine subtype selective ligands - Google Patents

4-(4-substituted piperazinyl-1yl)-butylcarboxamides as d3 dopamine subtype selective ligands

Info

Publication number
WO2003028728A8
WO2003028728A8 PCT/HU2002/000095 HU0200095W WO03028728A8 WO 2003028728 A8 WO2003028728 A8 WO 2003028728A8 HU 0200095 W HU0200095 W HU 0200095W WO 03028728 A8 WO03028728 A8 WO 03028728A8
Authority
WO
WIPO (PCT)
Prior art keywords
optionally substituted
6alkoxy
selective ligands
butylcarboxamides
subtype selective
Prior art date
Application number
PCT/HU2002/000095
Other languages
French (fr)
Other versions
WO2003028728A1 (en
Inventor
Katalin Nogradi
Janos Galambos
Tibor Acs
Istvan Borza
Attila Bielik
Gyoergy Domany
Bela Kiss
Istvan Gyertyan
Istvan Laszlovszky
Attila Horvath
Original Assignee
Richter Gedeon Vegyeszet
Katalin Nogradi
Janos Galambos
Tibor Acs
Istvan Borza
Attila Bielik
Gyoergy Domany
Bela Kiss
Istvan Gyertyan
Istvan Laszlovszky
Attila Horvath
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 Richter Gedeon Vegyeszet, Katalin Nogradi, Janos Galambos, Tibor Acs, Istvan Borza, Attila Bielik, Gyoergy Domany, Bela Kiss, Istvan Gyertyan, Istvan Laszlovszky, Attila Horvath filed Critical Richter Gedeon Vegyeszet
Publication of WO2003028728A1 publication Critical patent/WO2003028728A1/en
Publication of WO2003028728A8 publication Critical patent/WO2003028728A8/en

Links

Classifications

    • 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
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • 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
    • 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
    • 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • 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
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
    • 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
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • 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
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
    • C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention relates to new D3 dopamine receptor subtype selective ligands of Formula (I), wherein R1, R2 and R3 independently represent substituents selected from hydrogen, halogen, C1-6alkyl, C1-6alkoxy, cyano, hydroxy, trifluoromethyl, C1-6alkylsulfonyloxy, trifluoromethanesulfonyloxy, optionally substituted C1-6alkanoyloxy, amino, aminoalkyl, carboxy, aminocarbonyl, N-hydroxycarbamimidoyl, carbamimidoyl, hydroxycarbamoyl, thiocarbamoyl, sulfamoyl, optionally substituted phenyl or naphthyl, optionally substituted mono or bicyclic heterocyclic group, two adjacent groups of R1, R2 and R3 may combine to form an optionally substituted fused mono or bicyclic heterocyclic group, with the exception of compounds wherein a) R1= R2 = R3 = H, b) R1 = R2= H and R3 = C1-6alkoxy in the position 2 or R3 is in the position 4 of the piperazinylphenyl moiety, c) R1 = H and R2 = R3 = C1-6alkoxy; Q represents an optionally substituted C1-6alkyl, C1-6alkenyl, phenyl or heteroaryl group.
PCT/HU2002/000095 2001-09-28 2002-09-25 4-(4-substituted piperazinyl-1yl)-butylcarboxamides as d3 dopamine subtype selective ligands WO2003028728A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HUP0103987 2001-09-28
HU0103987A HUP0103987A3 (en) 2001-09-28 2001-09-28 Phenylpiperazinylalkyl carboxylic acid amid derivatives, process for their preparation, pharmaceutical compositions containing them and their intermediates

Publications (2)

Publication Number Publication Date
WO2003028728A1 WO2003028728A1 (en) 2003-04-10
WO2003028728A8 true WO2003028728A8 (en) 2005-04-07

Family

ID=89979731

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/HU2002/000095 WO2003028728A1 (en) 2001-09-28 2002-09-25 4-(4-substituted piperazinyl-1yl)-butylcarboxamides as d3 dopamine subtype selective ligands

Country Status (2)

Country Link
HU (1) HUP0103987A3 (en)
WO (1) WO2003028728A1 (en)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10232020A1 (en) * 2002-07-04 2004-02-26 Friedrich-Alexander-Universität Erlangen-Nürnberg Neuroreceptor-active heteroarenecarboxamides
CA2489396A1 (en) * 2002-07-04 2004-01-15 Schwarz Pharma Ag Utilization of heteroarene carboxamide as dopamine-d3 ligands for the treatment of cns diseases
CA2528538A1 (en) * 2003-06-19 2004-12-29 Psychiatric Genomics, Inc. Dual function compounds and uses thereof
KR20070047763A (en) * 2004-07-20 2007-05-07 시에나 바이오테크 에스.피.에이. Modulators of alpha7 nicotinic acetylcholine receptors and therapeutic uses thereof
DE502005003491D1 (en) * 2004-08-02 2008-05-08 Sanol Arznei Schwarz Gmbh CARBOXAMIDE OF INDOLICINE AND ITS AZA AND DIAZADERIVATES
DE102004054634A1 (en) * 2004-11-12 2006-05-18 Schwarz Pharma Ag Azaindolcarboxamide
DE102004063797A1 (en) * 2004-12-30 2006-07-13 Schwarz Pharma Ag Oxygenated fused phenylpiperazine and phenyldiazepane carboxamides
WO2006072608A2 (en) * 2005-01-03 2006-07-13 Universitá Degli Studi Di Siena Aryl piperazine derivatives for the treatment of neuropsychiatric disorders
EP1683790A1 (en) * 2005-01-24 2006-07-26 Institut National De La Sante Et De La Recherche Medicale (Inserm) 3,4-dihydro-2-naphthamide derivatives as selective dopamine D3 ligands
HUP0500170A3 (en) 2005-02-03 2007-11-28 Richter Gedeon Nyrt Piperazine derivatives, process for producing them and pharmaceutical compositions containing them
EP1909910A1 (en) 2005-08-04 2008-04-16 Sirtris Pharmaceuticals, Inc. Benzimidazole derivatives as sirtuin modulators
JPWO2007099828A1 (en) * 2006-02-23 2009-07-16 塩野義製薬株式会社 Nitrogen-containing heterocyclic derivatives substituted with cyclic groups
FR2903986A1 (en) * 2006-07-21 2008-01-25 Pierre Fabre Medicament Sa NOVEL CHROMENES OR THIOCHROMENES CARBOXAMIDE DERIVATIVES, PROCESS FOR PREPARING THEM AND THERAPEUTIC APPLICATIONS THEREOF
EP2081907B1 (en) * 2006-10-13 2011-01-26 Universita Degli Studi di Siena Aryl piperazine derivatives useful for the treatment of neuropsychiatry disorders
CN1948298B (en) * 2006-11-09 2010-09-01 东南大学 Dopamine D3 acceptor portion agonist and its application
TW200901974A (en) 2007-01-16 2009-01-16 Wyeth Corp Compounds, compositions, and methods of making and using them
CL2008001821A1 (en) 2007-06-20 2009-03-13 Sirtris Pharmaceuticals Inc Imidazo [2,1-b] -thiazole derived compounds; pharmaceutical composition comprising said compound; and use of the compound for the treatment of diabetes, metabolic syndrome, insulin resistance, among others.
US20110085978A1 (en) * 2008-03-14 2011-04-14 Neurosearch A/S Novel quinolinylamide derivatives useful as modulators of dopamine and serotonin receptors
WO2010038948A2 (en) * 2008-10-02 2010-04-08 Green Cross Corporation Arylpiperazine-containing pyrrole 3-carboxamide derivatives for treating depressive disorders
US9227944B2 (en) 2008-10-10 2016-01-05 Institute Of Pharmacology And Toxicology Academy Of Military Science P.L.A. China Dopamine D3 receptor ligands and preparation and medical uses of the same
EP2354136B1 (en) * 2008-10-10 2016-02-24 Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. China Novel dopamine d3 receptor ligands and preparation and medical uses of the same
CA2885476A1 (en) 2012-10-11 2014-04-17 Southern Research Institute Urea and amide derivatives of aminoalkylpiperazines and use thereof
US9828352B2 (en) 2013-07-18 2017-11-28 Fondazione Istituto Italiano Di Tecnologia Phenyl carbamates and their use as inhibitors of the fatty acid amide hydrolase (FAAH) enzyme and modulators of the D3 dopamine receptor (D3DR)
CN104672135A (en) * 2014-12-22 2015-06-03 中国人民解放军成都军区总医院 Novel quinoline-4-carboxamide derivative, preparation method thereof, pharmaceutical composition containing novel quinoline-4-carboxamide derivative, and medical application of novel quinoline-4-carboxamide derivative
US10392378B2 (en) * 2014-12-23 2019-08-27 Proteostasis Therapeutics, Inc. Derivatives of 5-phenyl- or 5-heteroarylathiazol-2-carboxylic amide useful for the treatment of inter alia cystic fibrosis
EP3736272A1 (en) * 2015-09-14 2020-11-11 The National Institute for Biotechnology in the Negev Ltd. Novel piperazine and piperidine derivatives, their synthesis and use thereof in inhibiting vdac oligomerization, apoptosis and mitochondria dysfunction
US10434099B2 (en) * 2016-09-22 2019-10-08 The National Institute for Biotechnology in the Negev Ltd. Methods for treating central nervous system disorders using VDAC inhibitors
US10787423B2 (en) 2015-09-14 2020-09-29 The National Institute For Biotechnolgy In The Negev Ltd. Piperazine and piperidine derivatives, their synthesis and use thereof in inhibiting VDAC oligomerization, apoptosis and mitochondria dysfunction
US11299476B2 (en) 2016-03-14 2022-04-12 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Dopamine D3 receptor selective antagonists/partial agonists; method of making; and use thereof
EP3429993B1 (en) * 2016-03-14 2021-05-26 The United States of America, as represented by the Secretary, Department of Health and Human Services Dopamine d3 receptor selective antagonists/partial agonists; method of making; and use thereof
EP3587398A1 (en) * 2017-02-24 2020-01-01 Shenzhen Linglan Bio-pharmaceutical Technology Co., Ltd Novel selective ligand for dopamine d3 receptor, preparation method therefor, and pharmaceutical application thereof
CN106966953A (en) * 2017-03-07 2017-07-21 深圳市老年医学研究所 A kind of preparation method and applications of novel dopamine D3 receptor selective ligands
EP3849963A1 (en) 2018-09-11 2021-07-21 The United States of America, as Represented By the Secretary, Department of Health and Human Services Dopamine d3 receptor selective antagonists/partial agonists and uses thereof

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2261756A1 (en) * 1974-02-27 1975-09-19 Roussel Uclaf 2-Thiazole-N-(Piperazino or piperidino) alkyl carboxamides - as hypotensive and anti-hypertensive agents of low toxicity
US4778796A (en) * 1985-07-19 1988-10-18 Dainippon Pharmaceutical Co., Ltd. ω-(3-pyridyl)alkenamide derivatives and anti-allergenic pharmaceutical compositions containing same
FR2655988B1 (en) * 1989-12-20 1994-05-20 Adir Cie NOVEL DERIVATIVES OF NAPHT-1-YL PIPERAZINE, PROCESS FOR THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
SE9201138D0 (en) * 1992-04-09 1992-04-09 Astra Ab NOVEL PHTHALIMIDOALKYL PIPERAZINES
DE4425146A1 (en) * 1994-07-15 1996-01-18 Basf Ag Use of heterocyclic compounds
DE4425145A1 (en) * 1994-07-15 1996-01-18 Basf Ag Use of thiazole and thiadiazole compounds
US5659033A (en) * 1995-09-13 1997-08-19 Neurogen Corporation N-aminoalkylfluorenecarboxamides; a new class of dopamine receptor subtype specific ligands
FR2742149B1 (en) * 1995-12-11 1998-02-13 Inst Nat Sante Rech Med NOVEL 2-NAPHTAMIDE DERIVATIVES AND THEIR THERAPEUTIC APPLICATIONS
US5763609A (en) * 1996-03-21 1998-06-09 Neurogen Corporation Certain pyrrolo pyridine-3-carboxamides; a new class of gaba brain receptor ligands
US5703083A (en) * 1996-04-15 1997-12-30 Neurogen Corporation N-aminoalkyl-1-biphenylenyl-2-carboxamides; new dopamine receptor subtype specific ligands
US5703237A (en) * 1996-04-18 1997-12-30 Neurogen Corporation N-Aminoalkyl-2-anthraquinonecarboxamides; new dopamine receptor subtype specific ligands
DE19728996A1 (en) * 1997-07-07 1999-01-14 Basf Ag Triazole compounds and their use
AU8130298A (en) * 1997-07-15 1999-02-10 Sankyo Company Limited Piperazine derivatives
DE19756236A1 (en) * 1997-12-17 1999-07-01 Klinge Co Chem Pharm Fab Novel piperazinyl-substituted pyridylalkane, alkene and alkyarboxylic acid amides
DE19922443A1 (en) * 1999-05-07 2000-11-09 Basf Ag Use of dopamine D3 receptor ligands in the manufacture of drugs for the treatment of renal dysfunction
JP2004520347A (en) * 2001-01-15 2004-07-08 グラクソ　グループ　リミテッド Arylpiperidine and piperazine derivatives as inducers of LDL-receptor expression

Also Published As

Publication number Publication date
HUP0103987A3 (en) 2004-11-29
HUP0103987A2 (en) 2003-05-28
WO2003028728A1 (en) 2003-04-10
HU0103987D0 (en) 2001-11-28

Similar Documents

Publication Publication Date Title
WO2003028728A8 (en) 4-(4-substituted piperazinyl-1yl)-butylcarboxamides as d3 dopamine subtype selective ligands
WO2001002400A8 (en) Fused imidazole compounds and remedies for diabetes mellitus
MXPA03006918A (en) Fused heterocyclic compounds.
MXPA02012314A (en) 1,2-dihydropyridine compounds, process for preparation of the same and use thereof.
WO2008006043A3 (en) 1,3-oxazole derivatives useful as anti-atherosclerotic, anti-dyslipidemic, anti-diabetic and anti-obesity agents
EP1180518A4 (en) 5-pyridyl-1,3-azole compounds, process for producing the same and use thereof
WO2001017972A3 (en) Novel herbicides
CA2429642A1 (en) Fused heteroaromatic glucokinase activators
WO2004014860A3 (en) Fused heterocyclic compounds as peptidase inhibitors
DE60226875D1 (en) ORTHOSUBSTITUTED ARYLAMIDES FOR COMBATING WIRELESS PESTS
WO2006123088A3 (en) 4- (thiazol-2-ylthioalkyl) -pyrazoles and their use as herbicides
NO330968B1 (en) New Process for the Synthesis of (1S) -4,5-Dimethoxy-1- (methylaminomethyl) -benzocyclobutane and Addition Salts thereof, and Use in the Synthesis of Ivabradine and Addition Salts thereof with a Pharmaceutically Acceptable Acid
EP0040639A4 (en) Isoxazole derivatives.
RS20050182A (en) Derivatives of dioxane-2-alkyl carbamates,preparation method thereof and application of same in therapeutics
WO2008093674A1 (en) Novel thiadiazole derivative having kinase inhibitory activity
WO2001062705A8 (en) Aminoalcohol derivatives
WO2003064429A1 (en) Thienopyrimidines, process for preparing the same and use thereof
WO2008136444A1 (en) Fused heterocyclic derivative
CA2341890A1 (en) Oxygen-containing heterocyclic compounds
WO1999000373A8 (en) Benzimidazole derivatives
EP1555261A4 (en) Valerolactone compounds and perfume composition
WO2004067703A3 (en) 5ht7 antagonists and inverse agonists
WO2005116023A8 (en) 3- {4- (pyridin-3-yl) phenyl} -5- (1h-1, 2, 3-triazol-1-ylmethyl) -1, 3-oxazolidin-2-ones as antibacterial agents
WO2004033456A3 (en) 1,4-diazabicyclo[3.2.2]nonanecarboxamide derivatives, preparation and therapeutic use thereof related to malfunction of nicotinic receptors
AU2003290121A1 (en) Novel process for the preparation of 2-aminomethylpyridine derivative

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BY BZ CA CH CN CO CR CU CZ DE DM DZ EC EE ES FI GB GD GE GH HR HU ID IL IN IS JP KE KG KP KR LC LK LR LS LT LU LV MA MD MG MN MW MX MZ NO NZ OM PH PL PT RU SD SE SG SI SK SL TJ TM TN TR TZ UA UG US UZ VN YU ZA ZM

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ UG ZM ZW AM AZ BY KG KZ RU TJ TM AT BE BG CH CY CZ DK EE ES FI FR GB GR IE IT LU MC PT SE SK TR BF BJ CF CG CI GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
122 Ep: pct application non-entry in european phase
CFP Corrected version of a pamphlet front page
CR1 Correction of entry in section i

Free format text: IN PCT GAZETTE 15/2003 ADD "DECLARATION UNDER RULE 4.17: - AS TO APPLICANT S ENTITLEMENT TO APPLY FOR AND BE GRANTED A PATENT (RULE 4.17(II))."

NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Country of ref document: JP