EP2313373A1 - Derives heterocycliques utiles dans le traitement de maladies neurodegeneratives - Google Patents

Derives heterocycliques utiles dans le traitement de maladies neurodegeneratives

Info

Publication number
EP2313373A1
EP2313373A1 EP09780818A EP09780818A EP2313373A1 EP 2313373 A1 EP2313373 A1 EP 2313373A1 EP 09780818 A EP09780818 A EP 09780818A EP 09780818 A EP09780818 A EP 09780818A EP 2313373 A1 EP2313373 A1 EP 2313373A1
Authority
EP
European Patent Office
Prior art keywords
compound
group
formula
hétar
hydrogen atom
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.)
Withdrawn
Application number
EP09780818A
Other languages
German (de)
English (en)
French (fr)
Inventor
Fanny Schmidt
Bruno Figadere
Rita Sylvia Vozari
Pierre Champy
Xavier Franck
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.)
Centre National de la Recherche Scientifique CNRS
Original Assignee
Centre National de la Recherche Scientifique CNRS
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 Centre National de la Recherche Scientifique CNRS filed Critical Centre National de la Recherche Scientifique CNRS
Publication of EP2313373A1 publication Critical patent/EP2313373A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • 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
    • A61P25/28—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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring

Definitions

  • R 3 represents a hydrogen atom and R 4 represents a (C 1 -C 6) alkyl or aryl group, advantageously a (C 1 -C 6) alkyl group.
  • the compounds of the invention can be used at doses of between 0.01 mg and 1000 mg per day, given in a single dose once a day or administered in several doses throughout the day, for example twice per day. day in equal doses.
  • the dose administered per day is advantageously between 5 mg and 500 mg, more advantageously between 10 mg and 200 mg. It may be necessary to use doses out of these ranges which the skilled person can realize himself.
  • IR cm- 1 573, 650, 726, 822, 859, 904, 1077, 1136, 1236, 1352, 1465, 1518, 1622,
  • the wells are then washed twice with PBS and then 500 ⁇ l of distilled water are added.
  • the cells are scraped and the liquid transferred into scintillation vials containing 7mL of scintillation fluid (Biodegradable Counting Scintillant-liquid scintillation spectroscopy, BCS), that well per well.
  • BCS Biodegradable Counting Scintillant-liquid scintillation spectroscopy
  • the neuroprotective effect of the compounds of the invention was evaluated by counts of dopaminergic neurons (TH + ) labeled immunohistochemistry tyrosine hydroxylase (TH) after 8 days of culture. Thus the compounds were evaluated at InM, 10nM, 10OnM and 1 ⁇ M and compared to the activity of cyclic dibutyryl-AMP (dbc-).

Landscapes

  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)
EP09780818A 2008-07-18 2009-07-20 Derives heterocycliques utiles dans le traitement de maladies neurodegeneratives Withdrawn EP2313373A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0854921A FR2933977B1 (fr) 2008-07-18 2008-07-18 Derives heterocycliques utiles dans le traitement des maladies neurodegeneratives
PCT/EP2009/059285 WO2010007179A1 (fr) 2008-07-18 2009-07-20 Derives heterocycliques utiles dans le traitement de maladies neurodegeneratives

Publications (1)

Publication Number Publication Date
EP2313373A1 true EP2313373A1 (fr) 2011-04-27

Family

ID=40379618

Family Applications (1)

Application Number Title Priority Date Filing Date
EP09780818A Withdrawn EP2313373A1 (fr) 2008-07-18 2009-07-20 Derives heterocycliques utiles dans le traitement de maladies neurodegeneratives

Country Status (7)

Country Link
US (1) US8445511B2 (ja)
EP (1) EP2313373A1 (ja)
JP (1) JP2011528335A (ja)
CN (1) CN102099338A (ja)
CA (1) CA2730331A1 (ja)
FR (2) FR2933977B1 (ja)
WO (1) WO2010007179A1 (ja)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2973373A1 (fr) * 2011-03-30 2012-10-05 Centre Nat Rech Scient Derives amino-quinoxalines pour le traitement de maladies neurodegeneratives
US9604930B2 (en) * 2012-12-21 2017-03-28 Epizyme, Inc. Tetrahydro- and dihydro-isoquinoline PRMT5 inhibitors and uses thereof
FR3042191B1 (fr) 2015-10-09 2020-01-17 Institut Du Cerveau Et De La Moelle Epiniere Derives 1,4,8-triazaphenanthrene pour le traitement de maladies neurodegeneratives
CA3111627A1 (en) * 2018-09-26 2020-04-02 The Trustees Of The University Of Pennsylvania Compositions and methods for inhibiting acss2

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR781812A (fr) * 1933-09-14 1935-05-22 Ig Farbenindustrie Ag Production de nouvelles combinaisons azotées quaternaires
WO2002057238A1 (fr) * 2001-01-17 2002-07-25 Institut De Recherche Pour Le Developpement (Ird) Quinoleines substituees pour le traitement de co-infections a protozoaires et a retrovirus

Family Cites Families (17)

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Publication number Priority date Publication date Assignee Title
GB8726735D0 (en) * 1987-11-14 1987-12-16 Wellcome Found Pesticidal compounds
DE4217952A1 (de) * 1992-05-30 1993-12-02 Basf Ag Chinoxalin-2,3(1H,4H)-dione
JP3039750B2 (ja) * 1993-04-27 2000-05-08 キヤノン株式会社 キノキサリン化合物、これを含む液晶組成物、それを有する液晶素子、それらを用いた表示装置及び表示方法
DE69416057T2 (de) * 1993-08-31 1999-07-01 Canon Kk Mesomorphe Verbindung, eine diese enthaltene Flüssigkristallzusammensetzung, eine diese Zusammensetzung verwendende Flüssigkristallvorrichtung, Flüssigkristallapparat und Anzeigeverfahren
JPH08209135A (ja) * 1995-01-31 1996-08-13 Canon Inc 液晶組成物、それを有する液晶素子及びそれらを有する液晶装置
JPH0930960A (ja) * 1995-07-18 1997-02-04 Takasago Internatl Corp 真菌感染症治療剤
US6281216B1 (en) * 1998-02-09 2001-08-28 Duphar International Research B.V. 2-aminoquinoline derivatives having d4-agonistic activity
DK1186594T3 (da) 1999-06-11 2009-09-14 Toyama Chemical Co Ltd N-alkoxylkyl-N,N-dialkylamin-derivater eller salte deraf og midler mod neurodegenerative sygdomme, som indeholder disse
US20020052323A1 (en) * 2000-08-30 2002-05-02 Jinhai Wang Quinoline-(C=O)-(multiple amino acids)-leaving group compounds for pharmaceutical compositions and reagents
US7692011B2 (en) * 2002-10-04 2010-04-06 Prana Biotechnology Limited 8-hydroxy and 8-mercapto quinazolinones
EP1854487A3 (en) * 2003-04-11 2010-09-22 High Point Pharmaceuticals, LLC Combinations of an 11-beta-hydroxysteroid dehaydrogenase type 1 inhibitor and a glucocorticoid receptor agonist
JP2007513184A (ja) * 2003-12-04 2007-05-24 バーテックス　ファーマシューティカルズ　インコーポレイテッド プロテインキナーゼのインヒビターとして有用なキノキサリン
WO2005066132A1 (en) * 2004-01-07 2005-07-21 Astrazeneca Ab Therapeutic agents i
US7205316B2 (en) * 2004-05-12 2007-04-17 Abbott Laboratories Tri- and bi-cyclic heteroaryl histamine-3 receptor ligands
AU2006218824A1 (en) * 2005-02-28 2006-09-08 Renovis, Inc. Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
WO2006108666A1 (en) * 2005-04-13 2006-10-19 Proteosys Ag Mefloquine, nelfinavir and saquinavir as novel agents for neurodegenerative and (neuro-) inflammatory diseases
CN1966500B (zh) * 2005-11-17 2011-03-30 中国科学院上海药物研究所 一类喹喔啉类衍生物、制法及用途

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR781812A (fr) * 1933-09-14 1935-05-22 Ig Farbenindustrie Ag Production de nouvelles combinaisons azotées quaternaires
WO2002057238A1 (fr) * 2001-01-17 2002-07-25 Institut De Recherche Pour Le Developpement (Ird) Quinoleines substituees pour le traitement de co-infections a protozoaires et a retrovirus

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DURET P ET AL: "Preparative separation of quinolines by centrifugal partition chromatography with gradient elution", JOURNAL OF CHROMATOGRAPHY, ELSEVIER SCIENCE PUBLISHERS B.V, NL, vol. 1011, no. 1-2, 5 September 2003 (2003-09-05), pages 55 - 65, XP004450619, ISSN: 0021-9673, DOI: 10.1016/S0021-9673(03)01020-3 *
GARINO C ET AL: "BACE-1 inhibitory activities of new substituted phenyl-piperazine coupled to various heterocycles: Chromene, coumarin and quinoline", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, ELSEVIER SCIENCE, GB, vol. 16, no. 7, 1 April 2006 (2006-04-01), pages 1995 - 1999, XP027966383, ISSN: 0960-894X, [retrieved on 20060401] *
HEAL W ET AL: "Library Synthesis and Screening: 2,4-Diphenylthiazoles and 2,4-Diphenyloxazoles as Potential Novel Prion Disease Therapeutics", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 50, 17 February 2007 (2007-02-17), pages 1347 - 1353, XP002477267, ISSN: 0022-2623, [retrieved on 20070217], DOI: 10.1021/JM0612719 *
MOHAMMED A. FAKHFAKH ET AL: "Synthesis and biological evaluation of substituted quinolines: potential treatment of protozoal and retroviral co-infections", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 11, no. 23, 1 November 2003 (2003-11-01), pages 5013 - 5023, XP055051150, ISSN: 0968-0896, DOI: 10.1016/j.bmc.2003.09.007 *
See also references of WO2010007179A1 *

Also Published As

Publication number Publication date
CN102099338A (zh) 2011-06-15
FR2933976B1 (fr) 2013-04-26
FR2933977B1 (fr) 2013-04-26
WO2010007179A1 (fr) 2010-01-21
FR2933976A1 (fr) 2010-01-22
US8445511B2 (en) 2013-05-21
US20110118270A1 (en) 2011-05-19
FR2933977A1 (fr) 2010-01-22
CA2730331A1 (fr) 2010-01-21
JP2011528335A (ja) 2011-11-17

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