CA2619566C - 6-substituted-2,3,4,5-tetrahydro-1h-benzo[d]azepines as 5-ht2c receptor agonists - Google Patents

6-substituted-2,3,4,5-tetrahydro-1h-benzo[d]azepines as 5-ht2c receptor agonists Download PDF

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Publication number
CA2619566C
CA2619566C CA2619566A CA2619566A CA2619566C CA 2619566 C CA2619566 C CA 2619566C CA 2619566 A CA2619566 A CA 2619566A CA 2619566 A CA2619566 A CA 2619566A CA 2619566 C CA2619566 C CA 2619566C
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CA
Canada
Prior art keywords
alkyl
substituents
optionally substituted
cycloalkyl
fluoro substituents
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.)
Expired - Fee Related
Application number
CA2619566A
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English (en)
French (fr)
Other versions
CA2619566A1 (en
Inventor
John Gordon Allen
Karin Briner
Christopher Stanley Galka
Richard Charles Hoying
Maria Angeles Martinez-Grau
Julie Miyashiro
Matthew Robert Reinhard
Natalia Pokrovskaia
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Eli Lilly and Co
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Eli Lilly and Co
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Publication of CA2619566A1 publication Critical patent/CA2619566A1/en
Application granted granted Critical
Publication of CA2619566C publication Critical patent/CA2619566C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • 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
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • 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
    • A61P25/18—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
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D409/12—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 linked by a chain containing hetero atoms as chain links
    • 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

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Psychiatry (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Hospice & Palliative Care (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Gynecology & Obstetrics (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
CA2619566A 2005-09-01 2006-09-01 6-substituted-2,3,4,5-tetrahydro-1h-benzo[d]azepines as 5-ht2c receptor agonists Expired - Fee Related CA2619566C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US71349505P 2005-09-01 2005-09-01
US60/713,495 2005-09-01
PCT/US2006/034334 WO2007028082A1 (en) 2005-09-01 2006-09-01 6-substituted- 2,3,4,5-tetrahydro-1h-benzo[d]azepines as 5-ht2c receptor agonists

Publications (2)

Publication Number Publication Date
CA2619566A1 CA2619566A1 (en) 2007-03-08
CA2619566C true CA2619566C (en) 2013-08-13

Family

ID=37499682

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2619566A Expired - Fee Related CA2619566C (en) 2005-09-01 2006-09-01 6-substituted-2,3,4,5-tetrahydro-1h-benzo[d]azepines as 5-ht2c receptor agonists

Country Status (13)

Country Link
US (1) US7994163B2 (enExample)
EP (1) EP1924560B1 (enExample)
JP (1) JP5165568B2 (enExample)
AT (1) ATE438627T1 (enExample)
CA (1) CA2619566C (enExample)
CY (1) CY1110531T1 (enExample)
DE (1) DE602006008323D1 (enExample)
DK (1) DK1924560T3 (enExample)
ES (1) ES2328520T3 (enExample)
PL (1) PL1924560T3 (enExample)
PT (1) PT1924560E (enExample)
SI (1) SI1924560T1 (enExample)
WO (1) WO2007028082A1 (enExample)

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WO2007028132A2 (en) * 2005-09-01 2007-03-08 Eli Lilly And Company 6-N-LINKED HETEROCYCLE-SUBSTITUTED 2,3,4,5-TETRAHYDRO-1H-BENZO[d]AZEPINES AS 5-HT2C RECEPTOR AGONISTS
US8420631B2 (en) * 2005-09-01 2013-04-16 Eli Lilly And Company 6-substituted-2,3,4,5-tetrahydro-1H-benzo[d]azepines as 5-HT2C receptor agonists
JP5528699B2 (ja) 2006-05-16 2014-06-25 武田薬品工業株式会社 縮合複素環化合物およびその用途
US7897595B2 (en) 2006-05-26 2011-03-01 Forest Laboratories Holdings Limited Pyridoazepine derivatives
JP5520051B2 (ja) 2007-11-15 2014-06-11 武田薬品工業株式会社 縮合ピリジン誘導体およびその用途
EP2942346B1 (en) * 2009-02-17 2020-05-06 Syntrix Biosystems, Inc. Pyridinecarboxamides as cxcr2 modulators
AU2011293612B2 (en) 2010-08-23 2015-11-26 Syntrix Biosystems Inc. Aminopyridine- and aminopyrimidinecarboxamides as CXCR2 modulators
KR20130138768A (ko) * 2010-09-01 2013-12-19 아레나 파마슈티칼스, 인크. 5-ｈｔ2ｃ 아고니스트의 신속-용해성 투여 형태
JP2013539470A (ja) * 2010-09-01 2013-10-24 アリーナ ファーマシューティカルズ， インコーポレイテッド ロルカセリンと光学活性な酸との塩
US20130267500A1 (en) 2010-09-01 2013-10-10 Arena Pharmaceuticals, Inc. 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level
KR20130101524A (ko) * 2010-09-01 2013-09-13 아레나 파마슈티칼스, 인크. 5-ｈｔ2ｃ 아고니스트의 비-흡습성 염
US10154988B2 (en) 2012-11-14 2018-12-18 The Johns Hopkins University Methods and compositions for treating schizophrenia
WO2015066344A1 (en) 2013-11-01 2015-05-07 Arena Pharmaceuticals, Inc. 5-ht2c receptor agonists and compositions and methods of use
CN105622511B (zh) * 2014-11-03 2018-01-23 北京瑞都医药科技有限公司 一种减肥药物及其制备方法
WO2019131902A1 (ja) 2017-12-27 2019-07-04 武田薬品工業株式会社 腹圧性尿失禁および便失禁の治療薬
AU2021398540A1 (en) 2020-12-11 2023-06-22 Intervet International B.V. Anthelmintic compounds comprising a pyridine structure

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EP0285287A3 (en) 1987-03-23 1990-08-16 Smithkline Beecham Corporation 3-benzazepine compounds for use in treating gastrointestinal motility disorders
US4985352A (en) 1988-02-29 1991-01-15 The Trustees Of Columbia University In The City Of New York DNA encoding serotonin 1C (5HT1c) receptor, isolated 5HT1c receptor, mammalian cells expressing same and uses thereof
US5639748A (en) * 1991-08-05 1997-06-17 Smithkline Beecham Corporation 6,9-disubstituted benzazepines having α-adrenoceptor blocking activity
GB9116824D0 (en) * 1991-08-05 1991-09-18 Smithkline Beecham Corp Chemical compounds
WO1993004866A1 (fr) * 1991-09-11 1993-03-18 Canon Kabushiki Kaisha Element de nettoyage ameliore pour tete de jet d'encre et dispositif a jet d'encre equipe d'un tel element de nettoyage
GB9119467D0 (en) 1991-09-12 1991-10-23 Smithkline Beecham Corp Chemical compounds
US5698766A (en) 1995-04-05 1997-12-16 The Regents Of The University Of California Transgenic animal model for testing drugs for treating eating disorders and epilepsy
EP1213017A3 (en) 2000-12-05 2003-11-12 Akzo Nobel N.V. Use of a 5-HT2C receptor agonist for the treatment of hot flushes
JPWO2002074746A1 (ja) 2001-03-16 2004-07-08 山之内製薬株式会社 ベンゾアゼピン誘導体
BR0211140A (pt) 2001-07-13 2005-10-25 Upjohn Co Compostos e composições de indóis de hexaidroazepina (4, 5-g) e indolinas como ligantes de receptores 5-ht
JP2005535560A (ja) * 2001-11-28 2005-11-24 ファルマシア・アンド・アップジョン・カンパニー・エルエルシー 治療用の化合物
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CA2556390C (en) 2004-02-25 2012-10-02 Eli Lilly And Company 6-substituted 2,3,4,5-tetrahydro-1h-benzo[d]azepines as 5-ht2c receptor agonists
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US8420631B2 (en) * 2005-09-01 2013-04-16 Eli Lilly And Company 6-substituted-2,3,4,5-tetrahydro-1H-benzo[d]azepines as 5-HT2C receptor agonists

Also Published As

Publication number Publication date
EP1924560B1 (en) 2009-08-05
EP1924560A1 (en) 2008-05-28
PT1924560E (pt) 2009-10-23
US20080255092A1 (en) 2008-10-16
CY1110531T1 (el) 2015-04-29
ES2328520T3 (es) 2009-11-13
WO2007028082A1 (en) 2007-03-08
JP2009508818A (ja) 2009-03-05
DE602006008323D1 (de) 2009-09-17
JP5165568B2 (ja) 2013-03-21
PL1924560T3 (pl) 2009-12-31
US7994163B2 (en) 2011-08-09
ATE438627T1 (de) 2009-08-15
DK1924560T3 (da) 2009-10-19
CA2619566A1 (en) 2007-03-08
SI1924560T1 (sl) 2010-01-29

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Effective date: 20170901