WO2000049000A1 - Dopamine d1 receptor agonist compounds - Google Patents

Dopamine d1 receptor agonist compounds 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)
French (fr)
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 IL14481000A priority Critical patent/IL144810A0/xx
Priority to AU25632/00A priority patent/AU767332B2/en
Priority to EA200100783A priority patent/EA004745B1/ru
Priority to KR1020017010418A priority patent/KR20010108228A/ko
Priority to CA002363695A priority patent/CA2363695A1/en
Priority to MXPA01008294A priority patent/MXPA01008294A/es
Priority to EP00903881A priority patent/EP1157009A1/en
Priority to JP2000599740A priority patent/JP2002537288A/ja
Priority to BR0008329-1A priority patent/BR0008329A/pt
Publication of WO2000049000A1 publication Critical patent/WO2000049000A1/en
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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
PCT/GB2000/000570 1999-02-17 2000-02-17 Dopamine d1 receptor agonist compounds WO2000049000A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
IL14481000A IL144810A0 (en) 1999-02-17 2000-02-17 Dopamine d1 receptor agonist compounds
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
CA002363695A CA2363695A1 (en) 1999-02-17 2000-02-17 Dopamine d1 receptor agonist compounds
MXPA01008294A MXPA01008294A (es) 1999-02-17 2000-02-17 Compuestos agonistas del receptor de dopamina d1.
EP00903881A EP1157009A1 (en) 1999-02-17 2000-02-17 Dopamine d1 receptor agonist compounds
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
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 (en) 2000-08-24

Family

ID=10847990

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2000/000570 WO2000049000A1 (en) 1999-02-17 2000-02-17 Dopamine d1 receptor agonist compounds

Country Status (17)

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

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003053936A1 (en) * 2001-12-20 2003-07-03 Shire Pharmaceutical Development Ltd Dopamine d1 receptor agonist pro-drug compounds & derivatives
WO2007019266A3 (en) * 2005-08-03 2007-05-18 Mineuet Therapeutics Ltd Killing human lymphoma and leukemia cancer cells and tcr-activated normal human cells by dopamine d1r agonists
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 (en) * 1985-12-20 1987-08-05 Smithkline Beecham Corporation 1-Phenyl-3-benzazepines
EP0380355A2 (en) * 1989-01-27 1990-08-01 Smithkline Beecham Corporation Carbamates of 6-chloro-7,8-dihydroxy-1-(4'-Hydroxyphenyl)-2,3,4,5-tetra-hydro-1H-3-benzazepine as prodrugs

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 (en) * 1985-12-20 1987-08-05 Smithkline Beecham Corporation 1-Phenyl-3-benzazepines
EP0380355A2 (en) * 1989-01-27 1990-08-01 Smithkline Beecham Corporation Carbamates of 6-chloro-7,8-dihydroxy-1-(4'-Hydroxyphenyl)-2,3,4,5-tetra-hydro-1H-3-benzazepine as prodrugs

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 (en) * 2001-12-20 2003-07-03 Shire Pharmaceutical Development Ltd Dopamine d1 receptor agonist pro-drug compounds & derivatives
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 (en) * 2005-08-03 2007-05-18 Mineuet Therapeutics Ltd Killing human lymphoma and leukemia cancer cells and tcr-activated normal human cells by dopamine d1r agonists
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
NO20013978D0 (no) 2001-08-15
IL144810A0 (en) 2002-06-30
CZ20012973A3 (cs) 2002-01-16
KR20010108228A (ko) 2001-12-07
NO20013978L (no) 2001-08-15
BR0008329A (pt) 2002-01-29
EA004745B1 (ru) 2004-08-26
GB9903671D0 (en) 1999-04-14
CN1341102A (zh) 2002-03-20
AU2563200A (en) 2000-09-04
EP1157009A1 (en) 2001-11-28
HUP0200057A3 (en) 2004-03-29
ZA200106478B (en) 2002-02-07
PL349838A1 (en) 2002-09-23
CA2363695A1 (en) 2000-08-24
HUP0200057A2 (en) 2002-08-28
EA200100783A1 (ru) 2002-02-28
JP2002537288A (ja) 2002-11-05
MXPA01008294A (es) 2002-07-02
AU767332B2 (en) 2003-11-06
CN1142916C (zh) 2004-03-24

Similar Documents

Publication Publication Date Title
US6225312B1 (en) Piperazine and piperidine compounds
JP2634190B2 (ja) 新環状アミン誘導体及びこれらの化合物を含む薬学的組成物
EP0628030A1 (en) 2,3,4,5-TETRAHYDRO-1H --3-BENZAZEPINES HAVING ANTI-PSYCHOTIC ACTIVITY, AND SYNTHESIS OF $g(a)-SUBSTITUTED-ARYLACETAMIDES
KR20010101606A (ko) 피페리딘, 테트라히드로피리딘 및 피페라진 유도체,그들의 제조 방법 및 용도
DK3107900T3 (en) 5-BENZYLISOQUINOLINE DERIVATIVES FOR TREATING CARDIOVASCULAR DISEASES
US20040034219A1 (en) Benzothiophene derivative compounds process of preparation and use thereof
JP2008542365A (ja) 新規なｍｃｈｒ１アンタゴニスト並びにｍｃｈｒ１媒介状態及び障害の処置のためのそれらの使用
US4727086A (en) Certain anti-hypertensive 2,3-dihydrobenzofuran compounds
JPH03120218A (ja) 痛みおよび／または中枢神経系障害の新規治療用医薬およびそれに用いる複素環式化合物
AU767332B2 (en) Dopamine D1 receptor agonist compounds
JP3779319B2 (ja) 複素環式化合物、それらの使用および製法
CA1079639A (en) 3-benzazepine derivatives
CN106883141B (zh) 一种丹皮酚肟醚类化合物、其制备方法及医药用途
IE61006B1 (en) New tricyclic amines derived from 2,3,5,6,7,8-hexahydronaphto (2,3-b) furan and from 2,3,6,7,8,9-hexahydro-5H-benzocyclohepta (2,3-b) furan, the processes for preparing them and the pharmaceutical compositions which contain them
US5298503A (en) N-(isoquinolin-5-ylsulphonyl) azacycloalkanes
AU778796B2 (en) Novel fluorinated imidazoline benzodioxane, preparation and therapeutic uses thereof
NO318113B1 (no) Nye heterocykliske forbindelser, farmasoytiske sammensetninger inneholdende disse, samt anvendelse av forbindelsene
US5053430A (en) Use of 2,7-diamino-1,2,3,4-tetrahydronaphthalenes as medicaments, new 2,7-diamino-1,2,3,4-tetrahydronaphthalenes and processes for their preparation
JP5635905B2 (ja) ミルタザピンの調製方法
PL168815B1 (pl) Sposób wytwarzania pochodnych N-2-chlorobenzylo-2-okso i N-2-chlorobenzylo-2,2-diokso-1,2,3-oksatiazolidyny PL PL PL
KR100472522B1 (ko) 스피로 이미다졸린 화합물, 이것의 제조방법 및 이것을 함유하는 약제학적 조성물
WO2003053936A1 (en) Dopamine d1 receptor agonist pro-drug compounds & derivatives
CA2021154A1 (en) Optically active naphthylethanol derivative
KR850000383B1 (ko) 2-(4-하이드록시알킬-1-퍼페라지닐)-2,4,6-사이클로헵타트리엔-1-온 유도체의 제조방법
KR20000005412A (ko) 피페라진 및 피페리딘 화합물

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 00803947.X

Country of ref document: CN

AK Designated states

Kind code of ref document: A1

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

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN 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)
WWE Wipo information: entry into national phase

Ref document number: 2001/06478

Country of ref document: ZA

Ref document number: 200106478

Country of ref document: ZA

WWE Wipo information: entry into national phase

Ref document number: 144810

Country of ref document: IL

Ref document number: 2000903881

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: IN/PCT/2001/1130/CHE

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 513552

Country of ref document: NZ

ENP Entry into the national phase

Ref document number: 2363695

Country of ref document: CA

Ref document number: 2363695

Country of ref document: CA

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: PV2001-2973

Country of ref document: CZ

ENP Entry into the national phase

Ref document number: 2000 599740

Country of ref document: JP

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: PA/a/2001/008294

Country of ref document: MX

Ref document number: 1020017010418

Country of ref document: KR

Ref document number: 200100783

Country of ref document: EA

WWE Wipo information: entry into national phase

Ref document number: 25632/00

Country of ref document: AU

WWP Wipo information: published in national office

Ref document number: 2000903881

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1020017010418

Country of ref document: KR

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWP Wipo information: published in national office

Ref document number: PV2001-2973

Country of ref document: CZ

WWG Wipo information: grant in national office

Ref document number: 25632/00

Country of ref document: AU

WWW Wipo information: withdrawn in national office

Ref document number: 2000903881

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1020017010418

Country of ref document: KR

WWR Wipo information: refused in national office

Ref document number: PV2001-2973

Country of ref document: CZ