CA2495248A1 - Anabaseine derivatives useful in the treatment of neurodegenerative diseases - Google Patents

Anabaseine derivatives useful in the treatment of neurodegenerative diseases Download PDF

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Publication number
CA2495248A1
CA2495248A1 CA002495248A CA2495248A CA2495248A1 CA 2495248 A1 CA2495248 A1 CA 2495248A1 CA 002495248 A CA002495248 A CA 002495248A CA 2495248 A CA2495248 A CA 2495248A CA 2495248 A1 CA2495248 A1 CA 2495248A1
Authority
CA
Canada
Prior art keywords
bipyridinyl
tetrahydro
ylmethylene
carbon atoms
alkyl
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
CA002495248A
Other languages
English (en)
French (fr)
Inventor
Brian Herbert
Truc Minh Nguyen
Ashok Tehim
Allen T. Hopper
Wenge Xie
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Memory Pharmaceuticals Corp
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2495248A1 publication Critical patent/CA2495248A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • 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
    • C07D401/14—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 three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • 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
    • 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
    • A61P25/24—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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32—Alcohol-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D405/14—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 three or more hetero rings
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07D417/14—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 three or more hetero rings
    • 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
    • C07D487/08—Bridged systems

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Diabetes (AREA)
  • Psychiatry (AREA)
  • Addiction (AREA)
  • Psychology (AREA)
  • Obesity (AREA)
  • Pain & Pain Management (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Emergency Medicine (AREA)
  • Rheumatology (AREA)
  • Hospice & Palliative Care (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)
CA002495248A 2002-08-30 2003-08-29 Anabaseine derivatives useful in the treatment of neurodegenerative diseases Abandoned CA2495248A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US40698102P 2002-08-30 2002-08-30
US60/406,981 2002-08-30
PCT/US2003/027164 WO2004019943A1 (en) 2002-08-30 2003-08-29 Anabaseine derivatives useful in the treatment of neurodegenerative diseases

Publications (1)

Publication Number Publication Date
CA2495248A1 true CA2495248A1 (en) 2004-03-11

Family

ID=31978399

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002495248A Abandoned CA2495248A1 (en) 2002-08-30 2003-08-29 Anabaseine derivatives useful in the treatment of neurodegenerative diseases

Country Status (6)

Country Link
US (3) US7244745B2 (enExample)
EP (4) EP1531820A1 (enExample)
JP (2) JP2006501246A (enExample)
AU (1) AU2003265842A1 (enExample)
CA (1) CA2495248A1 (enExample)
WO (1) WO2004019943A1 (enExample)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1891036A4 (en) 2005-06-07 2010-08-04 Univ Florida SELECTIVE LIGANDS FOR ALPHA-7 NICOTINE RECEPTORS
US7662965B2 (en) 2006-01-26 2010-02-16 Cornerstone Therapeutics, Inc. Anabaseine derivatives, pharmaceutical compositions and method of use thereof
SA08290475B1 (ar) 2007-08-02 2013-06-22 Targacept Inc (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه
US9463190B2 (en) * 2008-03-31 2016-10-11 University Of South Florida Methods of treating disease-induced ataxia and non-ataxic imbalance
TW201031664A (en) 2009-01-26 2010-09-01 Targacept Inc Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide
US20120157464A1 (en) * 2009-07-23 2012-06-21 Novartis Ag Use of azabicycloalkyl derivatives or pyrrolidine-2-one derivatives for the treatment or prevention of ataxia
JO3250B1 (ar) 2009-09-22 2018-09-16 Novartis Ag إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7
JP5749797B2 (ja) 2010-05-17 2015-07-15 フォルム ファーマシューティカルズ、インコーポレイテッド （ｒ）−７−クロロ−ｎ−（キヌクリジン−３−イル）ベンゾ［ｂ］チオフェン−２−カルボキサミド塩酸塩一水和物の結晶形
JP2015504861A (ja) * 2011-12-12 2015-02-16 ユニバーシティ オブ フロリダ リサーチ ファウンデーション ニコチン性受容体標的化合物および組成物
CA2872005A1 (en) 2012-05-08 2013-11-14 Forum Pharmaceuticals, Inc. Methods of maintaining, treating or improving cognitive function
KR102472011B1 (ko) * 2016-05-12 2022-11-28 버크 인스티튜트 포 리서치 온 에이징 App 의 정상 가공을 촉진하는 화합물
CN111808907B (zh) * 2019-10-09 2021-07-09 北京原基华毅生物科技有限公司 调整觉醒的物质及方法

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3508258A1 (de) 1985-03-08 1986-09-18 Bayer Ag, 5090 Leverkusen Ss-lactamantibiotika, verfahren zur herstellung und ihre verwendung als und in arzneimitteln
KR0175638B1 (ko) * 1991-03-01 1999-02-18 카렌 에이.홀브루크 신경계 퇴행성 질환 치료용 니코틴 아날로그의 개량된 제조방법
KR100272614B1 (ko) * 1992-08-31 2000-11-15 엠. 잭 오해니언 신경계의 퇴행성 질환의 치료에 유용한 아나바세인 유도체
US5977144A (en) * 1992-08-31 1999-11-02 University Of Florida Methods of use and compositions for benzylidene- and cinnamylidene-anabaseines
AU707748B2 (en) 1994-03-25 1999-07-22 Isotechnika Inc. Enhancement of the efficacy of drugs by deuteration
US6334997B1 (en) 1994-03-25 2002-01-01 Isotechnika, Inc. Method of using deuterated calcium channel blockers
US5510355A (en) * 1994-09-06 1996-04-23 Bencherif; Merouane Depolarizing skeletal muscle relaxants
JP3219946B2 (ja) * 1994-09-22 2001-10-15 大鵬薬品工業株式会社 新規製造中間体及びピリジン誘導体の製造方法
US20020028798A1 (en) * 1995-12-12 2002-03-07 Omeros Medical Systems Irrigation solution and method for inhibition of pain and inflammation
SE9600683D0 (sv) 1996-02-23 1996-02-23 Astra Ab Azabicyclic esters of carbamic acids useful in therapy
DE19622353A1 (de) * 1996-06-04 1997-12-11 Bayer Ag Substituierte Pyridine zur Bekämpfung tierischer Schädlinge
SK283261B6 (sk) 1996-07-18 2003-04-01 Merck Frosst Canada & Co. / Merck Frosst Canada & Cie. Substituované pyridíny, farmaceutický prostriedok s ich obsahom a ich použitie
KR100247563B1 (ko) 1997-07-16 2000-04-01 박영구 키랄3,4-에폭시부티르산및이의염의제조방법
US6277870B1 (en) 1998-05-04 2001-08-21 Astra Ab Use
ATE255888T1 (de) 1998-06-01 2003-12-15 Ortho Mcneil Pharm Inc Tetrahydronaphtalene verbindungen und deren verwendung zur behandlung von neurodegenerativen krankheiten
SE9900100D0 (sv) 1999-01-15 1999-01-15 Astra Ab New compounds
FR2788982B1 (fr) 1999-02-02 2002-08-02 Synthelabo Compositions pharmaceutiques contenant de la nicotine et leur application dans le sevrage tabagique
US6313110B1 (en) 1999-06-02 2001-11-06 Dupont Pharmaceuticals Company Substituted 2H-1,3-diazapin-2-one useful as an HIV protease inhibitor
SE9903998D0 (sv) 1999-11-03 1999-11-03 Astra Ab New compounds
SE9903997D0 (sv) 1999-11-03 1999-11-03 Astra Ab New compounds
SE9904176D0 (sv) 1999-11-18 1999-11-18 Astra Ab New use
WO2001073446A1 (en) 2000-03-29 2001-10-04 Synaptica Limited Alpha 7 nicotinic receptor screening assays
US6852741B2 (en) 2001-12-31 2005-02-08 University Of Florida Compositions and methods for treatment of neurological disorders

Also Published As

Publication number Publication date
US20040229868A1 (en) 2004-11-18
EP2305664A1 (en) 2011-04-06
WO2004019943A1 (en) 2004-03-11
US20100173891A1 (en) 2010-07-08
JP2011168617A (ja) 2011-09-01
EP2298759A1 (en) 2011-03-23
EP1531820A1 (en) 2005-05-25
US20090105215A1 (en) 2009-04-23
EP2298758A1 (en) 2011-03-23
US7994199B2 (en) 2011-08-09
JP2006501246A (ja) 2006-01-12
US7244745B2 (en) 2007-07-17
AU2003265842A1 (en) 2004-03-19
US7700630B2 (en) 2010-04-20

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FZDE Discontinued

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FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125

FZDE Discontinued

Effective date: 20130125