CA2321830A1 - Derives de benzylpiperazinyl et piperidinyl ethanone, preparation, et utilisation comme antagonistes des recepteurs d4 de la dopamine - Google Patents

Derives de benzylpiperazinyl et piperidinyl ethanone, preparation, et utilisation comme antagonistes des recepteurs d4 de la dopamine Download PDF

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Publication number
CA2321830A1
CA2321830A1 CA002321830A CA2321830A CA2321830A1 CA 2321830 A1 CA2321830 A1 CA 2321830A1 CA 002321830 A CA002321830 A CA 002321830A CA 2321830 A CA2321830 A CA 2321830A CA 2321830 A1 CA2321830 A1 CA 2321830A1
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CA
Canada
Prior art keywords
compound according
hydrogen
alkyl
formula
piperazinyl
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.)
Abandoned
Application number
CA002321830A
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English (en)
Inventor
Renata X. Kover
Silva Terdjanian
Jennifer Tran
Andrew Thurkauf
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Neurogen Corp
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Individual
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Filing date
Publication date
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Publication of CA2321830A1 publication Critical patent/CA2321830A1/fr
Abandoned legal-status Critical Current

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    • 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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • 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
    • C07D209/54—Spiro-condensed
    • 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
    • C07D215/04—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/08—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/16—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • 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

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical 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)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Addiction (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Indole Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne des composés représentés par la formule (I) ou certains de leurs sels d'addition pharmaceutiquement acceptables. Dans ladite formule, Y représente oxygène ou soufre: Z représente azote ou CH; R¿1?, R¿2? et R¿3? représentent hydrogène, halogène, hydroxy, alcoxy, alkyle, trifluorométhyle ou trifluorométhoxy; R¿4? et R¿4?' représentent hydrogène, alkyle ou forment un noyau avec l'atome auquel ils sont fixés; R¿5? représente hydrogène, alkyle, alcoxy ou alkylthio et R¿6? représente hydrogène ou alkyle; R¿5? et R¿6? peuvent aussi former un noyau avec les atomes auxquels ils sont fixés; R¿7?, R¿8?, R¿10? et R¿11? représentent hydrogène ou alkyle. Lesdits composés sont utiles pour le traitement et/ou la prévention de troubles neuropsychologiques, parmi lesquels la schizophrénie, la manie, la démence, la dépression, l'anxiété, les comportements compulsifs, les abus d'intoxicants, les troubles moteurs du type Parkinson et les troubles du mouvement associés à la consommation de neuroleptiques. L'invention concerne également des intermédiaires représentés par les formules (VII-a) et (VII-b), dans lesquelles X représente oxygène, soufre ou CH¿2?, m représente 0 ou un entier de 1 à 4, et L représente un groupe partant.
CA002321830A 1998-02-26 1999-02-26 Derives de benzylpiperazinyl et piperidinyl ethanone, preparation, et utilisation comme antagonistes des recepteurs d4 de la dopamine Abandoned CA2321830A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US3098798A 1998-02-26 1998-02-26
US09/030,987 1998-02-26
PCT/US1999/004309 WO1999043670A1 (fr) 1998-02-26 1999-02-26 Derives de benzylpiperazinyl et piperidinyl ethanone, preparation, et utilisation comme antagonistes des recepteurs d4 de la dopamine

Publications (1)

Publication Number Publication Date
CA2321830A1 true CA2321830A1 (fr) 1999-09-02

Family

ID=21857045

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002321830A Abandoned CA2321830A1 (fr) 1998-02-26 1999-02-26 Derives de benzylpiperazinyl et piperidinyl ethanone, preparation, et utilisation comme antagonistes des recepteurs d4 de la dopamine

Country Status (11)

Country Link
EP (1) EP1068193A1 (fr)
JP (1) JP2002504549A (fr)
KR (1) KR20010041341A (fr)
CN (1) CN1293669A (fr)
AU (1) AU2881499A (fr)
CA (1) CA2321830A1 (fr)
HU (1) HUP0100926A3 (fr)
IL (1) IL137930A0 (fr)
NO (1) NO20004271L (fr)
PL (1) PL342597A1 (fr)
WO (1) WO1999043670A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6084098A (en) 1999-02-26 2000-07-04 Neurogen Corporation Benzylpiperazinyl and piperidinyl ethanone derivatives: dopamine receptor subtype specific ligands
US6355644B1 (en) 1999-06-14 2002-03-12 Neurogen Corporation Benzylpiperazinyl-indolinylethanones
WO2000076967A1 (fr) * 1999-06-14 2000-12-21 Neurogen Corporation Benzylpiperazinyl-indolinylethanones
EP1177792A3 (fr) 2000-07-27 2002-10-23 Pfizer Products Inc. Ligands dopamine d4 destines au traitement des troubles associees a la cherche de la nouveaute
KR100394086B1 (ko) 2000-12-04 2003-08-06 한국과학기술연구원 도파민 ｄ3 및 ｄ4 수용체의 선택적 활성을 지닌 신규이소옥사졸릴알킬피페라진 유도체와, 이의 제조방법
KR100394083B1 (ko) 2000-12-04 2003-08-06 학교법인 성신학원 도파민 ｄ3 및 ｄ4 수용체의 선택적 활성을 지닌 신규4,5-디히드로이소옥사졸릴알킬피페라진 유도체와, 이의제조방법
CN1181065C (zh) * 2002-05-08 2004-12-22 上海医药工业研究院 芳烷甲酰烷基哌嗪衍生物及其作为脑神经保护剂的应用
DE102004027358A1 (de) * 2004-06-04 2005-12-29 Abbott Gmbh & Co. Kg Pyrimidinverbindungen und ihre Verwendung
GB201106817D0 (en) * 2011-04-21 2011-06-01 Astex Therapeutics Ltd New compound
RU2727169C2 (ru) 2013-11-18 2020-07-21 Форма Терапеутикс Инк. Композиции тетрагидрохинолинов в качестве ингибиторов бромодомена вет
EP3071205B1 (fr) 2013-11-18 2020-02-05 Forma Therapeutics, Inc. Compositions de benzopipérazine en tant qu'inhibiteurs de bromodomaines bet
RU2696310C1 (ru) 2013-12-20 2019-08-01 Астекс Терапьютикс Лимитед Бициклические гетероциклические соединения и их применение в терапии
CN103966340B (zh) * 2014-05-26 2015-09-16 宁波大学 一种用于辅助诊断阿尔茨海默病的检测试剂盒及其应用

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US2863752A (en) * 1953-10-30 1958-12-09 Monsanto Chemicals Herbicides
US2909523A (en) * 1957-10-11 1959-10-20 American Cyanamid Co Substituted piperazines and method of preparing the same
US3268584A (en) * 1961-08-28 1966-08-23 Monsanto Co Herbicidal alpha-haloacetanilides
NL128941C (fr) * 1964-02-19 1970-06-15
DE2604224A1 (de) * 1976-02-04 1977-08-11 Hoechst Ag Herbizide mittel
JPS5318540A (en) * 1976-08-02 1978-02-20 Nippon Nohyaku Co Ltd Alpha-chloroacetamides and their use
WO1989008654A1 (fr) * 1988-03-11 1989-09-21 Pfizer Inc. Carboxamides de pyrroloquinoline et de pyrrolophenothiazine et composes s'y rapportant
EP0934932A4 (fr) * 1996-08-22 2002-06-26 Meiji Seika Kaisha Derives quinoleine et agent psychotrope
ATE287878T1 (de) * 1996-08-23 2005-02-15 Neurosearch As Disubstituierte morpholin-, oxazepin- oder thiazepinderivate, deren herstellung und verwendung als dopamin-d4-rezeptorantagonisten
AU6256198A (en) * 1997-02-19 1998-09-09 Hoechst Marion Roussel, Inc. Benzamides having dopamine d4 receptor affinity
WO1999021848A2 (fr) * 1997-10-27 1999-05-06 Neurogen Corporation Nouveau 1-(n'-(arylalkylaminoalkyl)aminoisoquinolines; nouvelle classe de ligands specifiques de sous-type de recepteur de dopamine
JP2001521935A (ja) * 1997-10-31 2001-11-13 ニューロゲン コーポレイション ３−アミノアルキルアミノ−２ｈ−１，４−ベンゾキシアジン及び３−アミノアルキルアミノ−２ｈ−１，４−ベンゾチアジン：ドーパミン受容体サブタイプ特定の配位子

Also Published As

Publication number Publication date
AU2881499A (en) 1999-09-15
JP2002504549A (ja) 2002-02-12
KR20010041341A (ko) 2001-05-15
IL137930A0 (en) 2001-10-31
PL342597A1 (en) 2001-06-18
CN1293669A (zh) 2001-05-02
EP1068193A1 (fr) 2001-01-17
NO20004271D0 (no) 2000-08-25
HUP0100926A3 (en) 2003-03-28
WO1999043670A1 (fr) 1999-09-02
NO20004271L (no) 2000-10-25
HUP0100926A2 (hu) 2001-09-28

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Legal Events

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FZDE Discontinued