WO2000049000A1 - Composes agonistes du recepteur d1 de dopamine - Google Patents

Composes agonistes du recepteur d1 de dopamine Download PDF

Info

Publication number
WO2000049000A1
WO2000049000A1 PCT/GB2000/000570 GB0000570W WO0049000A1 WO 2000049000 A1 WO2000049000 A1 WO 2000049000A1 GB 0000570 W GB0000570 W GB 0000570W WO 0049000 A1 WO0049000 A1 WO 0049000A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrogen
tetrahydro
dopamine
chloro
halogen
Prior art date
Application number
PCT/GB2000/000570
Other languages
English (en)
Inventor
Gary Tilbrook
Original Assignee
Cenes Limited
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 Cenes Limited filed Critical Cenes Limited
Priority to EP00903881A priority Critical patent/EP1157009A1/fr
Priority to MXPA01008294A priority patent/MXPA01008294A/es
Priority to AU25632/00A priority patent/AU767332B2/en
Priority to EA200100783A priority patent/EA004745B1/ru
Priority to KR1020017010418A priority patent/KR20010108228A/ko
Priority to JP2000599740A priority patent/JP2002537288A/ja
Priority to BR0008329-1A priority patent/BR0008329A/pt
Priority to IL14481000A priority patent/IL144810A0/xx
Priority to CA002363695A priority patent/CA2363695A1/fr
Publication of WO2000049000A1 publication Critical patent/WO2000049000A1/fr
Priority to NO20013978A priority patent/NO20013978L/no

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/16—Benzazepines; Hydrogenated benzazepines
    • 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
    • A61P25/28—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • GB 1 599 705 discloses 1-thienyl and l-furyl-2,3,4,5-tetrahydro-lH-3-benzazepines having utility as cardiovascular agents.
  • Some benzazepines as Dopamine Dl receptor agonists have been described.
  • l-phenyl-3 -benzazepines are disclosed in EP 0 230 755-A and carbamates of6-chloro-7,8-dihydroxy-l (4'-hydroxyphenyl)-2,3,4,5-tetrahydro-lH-3- benzazepine are disclosed in EP 0 380 355-A.
  • l-Indan-5-yl-6-chloro-7,8-dimethoxy-3-methyl-2,3,4,5-tetrahydro-lH-3-benzazepine (1.03 g, 2.77 mmol) was dissolved in anhydrous dichloromethane (15 ml), which was cooled to -78°C. To this solution was added dropwise BBr 3 (1.0 M solution in dichloromethane, 13.8 ml, 13.8 mmol) over 25 min. The reaction mixture was stirred at -78°C for 1 h, at 0°C for 3 h and at r.t for further 1 h.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Neurosurgery (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne des 2,3,4,5-tétrahydro-1H-3-benzazépines de formule (I) dans laquelle R1 est un groupe hydrogène, halogène, C¿1?-C4 alkyle, ou CF3, R?2¿ est un groupe hydrogène, méthyle, ou un alcényle inférieur à 3-5 atomes de carbone, R3 et R4 forment ensemble un noyau furane, dihydrofurane, thiophène, dihydrothiophène, cyclopentane ou cyclohexane et R5 est un groupe hydrogène ou R4 et R5 forment ensemble un noyau furane, dihydrofurane, thiophène, dihydrothiophène, cyclopentane ou cyclohexane et R3 est un groupe hydrogène, R6 est un groupe hydrogène, halogène, CF¿3?, CN, NO2 ou NH2, R?7¿ est un groupe hydrogène, halogène, CF¿3?, CN, NO2 ou NH2. La combinaison spécifique de substituants R1 = H, R2 = H et R4 et R5 formant ensemble un noyau cyclohexane est exclue, notamment le 1-(5,6,7,8-tétrahydronaphthalène-2-yl)-2,3,4,5-tétrahydro-1H-benzol[d]azépine-7,8-diol. Les composés de l'invention permettent d'obtenir des agents thérapeutiques qui interagissent sélectivement avec les récepteurs D1 postsynaptiques de dopamine dans le striatum, directement ou indirectement (appelés agonistes D1 de dopamine) et sont particulièrement utiles comme anti-Parkinsoniens.
PCT/GB2000/000570 1999-02-17 2000-02-17 Composes agonistes du recepteur d1 de dopamine WO2000049000A1 (fr)

Priority Applications (10)

Application Number Priority Date Filing Date Title
EP00903881A EP1157009A1 (fr) 1999-02-17 2000-02-17 Composes agonistes du recepteur d1 de dopamine
MXPA01008294A MXPA01008294A (es) 1999-02-17 2000-02-17 Compuestos agonistas del receptor de dopamina d1.
AU25632/00A AU767332B2 (en) 1999-02-17 2000-02-17 Dopamine D1 receptor agonist compounds
EA200100783A EA004745B1 (ru) 1999-02-17 2000-02-17 Тетрагидробензазепиновые производные в качестве агонистов дофаминовых рецепторов d1
KR1020017010418A KR20010108228A (ko) 1999-02-17 2000-02-17 도파민 ｄ1 수용체 효능제 화합물
JP2000599740A JP2002537288A (ja) 1999-02-17 2000-02-17 ドーパミンｄ１受容体アゴニスト化合物
BR0008329-1A BR0008329A (pt) 1999-02-17 2000-02-17 Compostos agonistas receptores de dopamina d1, composição farmacêutica e seu uso
IL14481000A IL144810A0 (en) 1999-02-17 2000-02-17 Dopamine d1 receptor agonist compounds
CA002363695A CA2363695A1 (fr) 1999-02-17 2000-02-17 Composes agonistes du recepteur d1 de dopamine
NO20013978A NO20013978L (no) 1999-02-17 2001-08-15 Dopamin D1 reseptor agonist forbindelser

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9903671.7 1999-02-17
GBGB9903671.7A GB9903671D0 (en) 1999-02-17 1999-02-17 Dopamine D-1 receptor agonist compounds

Publications (1)

Publication Number Publication Date
WO2000049000A1 true WO2000049000A1 (fr) 2000-08-24

Family

ID=10847990

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2000/000570 WO2000049000A1 (fr) 1999-02-17 2000-02-17 Composes agonistes du recepteur d1 de dopamine

Country Status (17)

Country Link
EP (1) EP1157009A1 (fr)
JP (1) JP2002537288A (fr)
KR (1) KR20010108228A (fr)
CN (1) CN1142916C (fr)
AU (1) AU767332B2 (fr)
BR (1) BR0008329A (fr)
CA (1) CA2363695A1 (fr)
CZ (1) CZ20012973A3 (fr)
EA (1) EA004745B1 (fr)
GB (1) GB9903671D0 (fr)
HU (1) HUP0200057A3 (fr)
IL (1) IL144810A0 (fr)
MX (1) MXPA01008294A (fr)
NO (1) NO20013978L (fr)
PL (1) PL349838A1 (fr)
WO (1) WO2000049000A1 (fr)
ZA (1) ZA200106478B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003053936A1 (fr) * 2001-12-20 2003-07-03 Shire Pharmaceutical Development Ltd Composes de pro-medicament d'agoniste du recepteur d1 de la dopamine et derives de ceux-ci
WO2007019266A3 (fr) * 2005-08-03 2007-05-18 Mineuet Therapeutics Ltd Élimination des cellules cancéreuses humaines du lymphome et de la leucémie et des cellules humaines normales activées par le tcr au moyen d'agonistes de la dopamine d1r
US8791101B2 (en) 2005-07-15 2014-07-29 Albany Molecular Research, Inc. Aryl- and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
US10696658B2 (en) 2013-06-27 2020-06-30 Pfizer Inc. Heteroaromatic compounds and their use as dopamine D1 ligands

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101684096A (zh) * 2008-09-23 2010-03-31 中国科学院上海药物研究所 一类新型苯并氮杂卓类化合物及其制备方法和用途
CN102276531A (zh) * 2011-05-30 2011-12-14 扬子江药业集团广州海瑞药业有限公司 一种甲磺酸非诺多泮的制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2629887A1 (de) * 1975-07-02 1977-01-20 Smithkline Corp Arzneimittel mit die peripheren dopamin-rezeptoren stimulierender, die nierengefaesse erweiternder, diuretischer und das parkinsonsyndrom lindernder wirkung
US4265889A (en) * 1978-05-05 1981-05-05 Smithkline Corporation 6-Lower alkyl-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines
GB1599705A (en) * 1977-02-02 1981-10-07 Smithkline Corp Benzazepines
EP0230755A1 (fr) * 1985-12-20 1987-08-05 Smithkline Beecham Corporation 1-Phényl-3-benzazépines
EP0380355A2 (fr) * 1989-01-27 1990-08-01 Smithkline Beecham Corporation Carbamates de 6-chloro-7,8-dihydroxy-1-(4'-hydroxyphényl)-2,3,4,5-tétra-hydro-1H-3-benzazépines comme prémédicaments

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2629887A1 (de) * 1975-07-02 1977-01-20 Smithkline Corp Arzneimittel mit die peripheren dopamin-rezeptoren stimulierender, die nierengefaesse erweiternder, diuretischer und das parkinsonsyndrom lindernder wirkung
GB1599705A (en) * 1977-02-02 1981-10-07 Smithkline Corp Benzazepines
US4265889A (en) * 1978-05-05 1981-05-05 Smithkline Corporation 6-Lower alkyl-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines
EP0230755A1 (fr) * 1985-12-20 1987-08-05 Smithkline Beecham Corporation 1-Phényl-3-benzazépines
EP0380355A2 (fr) * 1989-01-27 1990-08-01 Smithkline Beecham Corporation Carbamates de 6-chloro-7,8-dihydroxy-1-(4'-hydroxyphényl)-2,3,4,5-tétra-hydro-1H-3-benzazépines comme prémédicaments

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
K. S. SUGAMORI ET AL., JOURNAL OF NEUROCHEMISTRY, vol. 71, no. 4, 1998, pages 1685 - 93, XP000864621 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003053936A1 (fr) * 2001-12-20 2003-07-03 Shire Pharmaceutical Development Ltd Composes de pro-medicament d'agoniste du recepteur d1 de la dopamine et derives de ceux-ci
US8791101B2 (en) 2005-07-15 2014-07-29 Albany Molecular Research, Inc. Aryl- and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
US9403776B2 (en) 2005-07-15 2016-08-02 Albany Molecular Research, Inc. Aryl- and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
WO2007019266A3 (fr) * 2005-08-03 2007-05-18 Mineuet Therapeutics Ltd Élimination des cellules cancéreuses humaines du lymphome et de la leucémie et des cellules humaines normales activées par le tcr au moyen d'agonistes de la dopamine d1r
US10696658B2 (en) 2013-06-27 2020-06-30 Pfizer Inc. Heteroaromatic compounds and their use as dopamine D1 ligands
US11014909B2 (en) 2013-06-27 2021-05-25 Pfizer Inc. Heteroaromatic compounds and their use as dopamine D1 ligands
US11964961B2 (en) 2013-06-27 2024-04-23 Pfizer Inc. Heteroaromatic compounds and their use as dopamine D1 ligands

Also Published As

Publication number Publication date
AU2563200A (en) 2000-09-04
ZA200106478B (en) 2002-02-07
HUP0200057A2 (en) 2002-08-28
NO20013978D0 (no) 2001-08-15
CN1341102A (zh) 2002-03-20
NO20013978L (no) 2001-08-15
BR0008329A (pt) 2002-01-29
MXPA01008294A (es) 2002-07-02
AU767332B2 (en) 2003-11-06
EP1157009A1 (fr) 2001-11-28
KR20010108228A (ko) 2001-12-07
CN1142916C (zh) 2004-03-24
CZ20012973A3 (cs) 2002-01-16
GB9903671D0 (en) 1999-04-14
IL144810A0 (en) 2002-06-30
EA004745B1 (ru) 2004-08-26
HUP0200057A3 (en) 2004-03-29
PL349838A1 (en) 2002-09-23
CA2363695A1 (fr) 2000-08-24
EA200100783A1 (ru) 2002-02-28
JP2002537288A (ja) 2002-11-05

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