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WO2009044018A9 - Dérivés de 1-0x0-1,2-dihydroisoquinoleine-5-carboxamides et de 4-oxo-3,4-dihydroquinazoline-8-carboxamides, leur préparation et leur application en thérapeutique - Google Patents

Dérivés de 1-0x0-1,2-dihydroisoquinoleine-5-carboxamides et de 4-oxo-3,4-dihydroquinazoline-8-carboxamides, leur préparation et leur application en thérapeutique Download PDF

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Publication number
WO2009044018A9
WO2009044018A9 PCT/FR2008/001109 FR2008001109W WO2009044018A9 WO 2009044018 A9 WO2009044018 A9 WO 2009044018A9 FR 2008001109 W FR2008001109 W FR 2008001109W WO 2009044018 A9 WO2009044018 A9 WO 2009044018A9
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WO
WIPO (PCT)
Prior art keywords
alkyl
group
carboxamides
oxo
cycloalkyl
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.)
Ceased
Application number
PCT/FR2008/001109
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English (en)
Other versions
WO2009044018A2 (fr
WO2009044018A3 (fr
Inventor
Michel Evers
Arielle Genevois-Borella
Andreas Karlsson
Jean-Luc Malleron
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.)
Sanofi Aventis France
Original Assignee
Sanofi Aventis France
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
Priority to AU2008306762A priority Critical patent/AU2008306762A1/en
Priority to CA2694313A priority patent/CA2694313A1/fr
Priority to NZ582995A priority patent/NZ582995A/en
Priority to CN200880104537A priority patent/CN101790518A/zh
Priority to EA201070196A priority patent/EA201070196A1/ru
Priority to BRPI0814177-0A2A priority patent/BRPI0814177A2/pt
Priority to JP2010517452A priority patent/JP2010534640A/ja
Priority to MX2010001081A priority patent/MX2010001081A/es
Priority to EP08835688A priority patent/EP2185523A2/fr
Application filed by Sanofi Aventis France filed Critical Sanofi Aventis France
Publication of WO2009044018A2 publication Critical patent/WO2009044018A2/fr
Publication of WO2009044018A3 publication Critical patent/WO2009044018A3/fr
Priority to US12/693,598 priority patent/US8030320B2/en
Priority to ZA2010/00583A priority patent/ZA201000583B/en
Anticipated expiration legal-status Critical
Publication of WO2009044018A9 publication Critical patent/WO2009044018A9/fr
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 nitrogen-containing ring
    • C07D217/24—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/22—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
    • A61P35/00—Antineoplastic 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
    • 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
    • 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
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/88—Oxygen atoms

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

Abstract

L'invention concerne les dérivés de 1 -oxo-1,2-dihydroisoquinoléine-5-carboxamides et de 4-oxo-3,4-dihydroquinazoline-8-carboxamides, de formule générale (I) dans laquelle R1 représente un atome d'hydrogène, un groupe (C1-C10)alkyle, (C3-C7)cycloalkyle,l (CH2)n-(C1-C6)alcényle, (CH2)n-(C1-C6)alcynyle, (C1-C6)alkyle-Z-(C1-C6)alkyle, dans lequel Z représente un hétéroatome choisi parmi O, N et S(O)m, ou bien R1 représente uni groupe COOR, S(O)mR, un aryle ou un aralkyle; R2 représente un ou plusieurs groupes 1, choisis parmi un atome d'hydrogène, un atome d'halogène, un groupe (C1-C6)alkyle, (C3-C7)cycloalkyle, (C1-C6)alcényle, (C1-C6) alcynyle, (C1-C6)alkyle-Z-(C1-C6)alkyle, dans lequel Z représente un hétéroatome choisi parmi O, N et S(O)m, ou bien R2 représente un groupe halo(C1-C6)alkyle, halo(C1-C6)alcoxy, hydroxy, (C1-C6)alcoxy, nitro, cyano, amino, un groupe NR7R8, COOR, CONR7R8, OCO(C1-C6)alkyle, S(O)mNR7R8, un groupe aryle; R3 représente un groupe trifluorométhyle; R4 et R5 représentent, indépendamment l'un de l'autre, un atome d'hydrogène, ou bien R4 et R5 forment avec l'atome de carbone qui les porte un cycle saturé contenant de 3 à 6 atomes de carbone et contenant éventuellement de O à 1 hétéroatome choisis parmi O, N ou S; R6 représente un groupe choisi parmi un atome d'hydrogène, un atome d'halogène, un groupe (C1-C6)alkyle, (C3-C7)cycloalkyle, (C3-C7)cycloalkyle(C1-C6)alkyle, un groupe halo(C1-C6)alkyle, nitro, amino, un groupe NR7R8, COOR, un groupe NR7(SO2)R8, CONR7R8, un groupe aryle; X représente un atome de carbone ou un atome d'azote; m représente un nombre entier compris entre O et 2 et n représente un nombre entier compris entre 1 et 6. L'invention a également trait à leur procédé de préparation et leur application en thérapeutique comme inhibiteurs de β-secrétase pour traiter les troubles neurodégénératifs tels qu'Alzheimer.
PCT/FR2008/001109 2007-07-27 2008-07-25 Dérivés de 1-0x0-1,2-dihydroisoquinoleine-5-carboxamides et de 4-oxo-3,4-dihydroquinazoline-8-carboxamides, leur préparation et leur application en thérapeutique Ceased WO2009044018A2 (fr)

Priority Applications (11)

Application Number Priority Date Filing Date Title
EP08835688A EP2185523A2 (fr) 2007-07-27 2008-07-25 Dérivés de 1-0x0-1,2-dihydroisoquinoleine-5-carboxamides et de 4-oxo-3,4-dihydroquinazoline-8-carboxamides, leur préparation et leur application en thérapeutique
NZ582995A NZ582995A (en) 2007-07-27 2008-07-25 Derivatives of 1-oxo-1,2-dihydroisoquinoline-5-carboxamides and of 4-oxo-3,4-dihydroquinazoline-8-carboxamides, preparation thereof and application thereof in therapeutics
CN200880104537A CN101790518A (zh) 2007-07-27 2008-07-25 1-氧代-1,2-二氢异喹啉-5-甲酰胺的衍生物和4-氧代-3,4-二氢喹唑啉-8-甲酰胺的衍生物,其制备和其治疗学应用
EA201070196A EA201070196A1 (ru) 2007-07-27 2008-07-25 Производные 1-оксо-1,2-дигидроизохинолин-5-карбоксамидов и 4-оксо-3,4-дигидрохиназолин-8-карбоксамидов, их получение и их применение в терапии
BRPI0814177-0A2A BRPI0814177A2 (pt) 2007-07-27 2008-07-25 Derivados de 1-oxo-1,2-di-hidroisoquinoleína-5-carboxamidas e de 4-oxo-3,4-di-hidroquinazolina-8-carboxamidas, sua preparação e sua aplicação em terapêutica
JP2010517452A JP2010534640A (ja) 2007-07-27 2008-07-25 １−オキソ−１，２−ジヒドロイソキノリン−５−カルボキサミドおよび４−オキソ−３，４−ジヒドロキナゾリン−８−カルボキサミド誘導体、その調製およびその治療における適用
MX2010001081A MX2010001081A (es) 2007-07-27 2008-07-25 Derivados de 1-oxo-1,2-dihidroisoquinolina-5-carboxamidas y de 4-oxo-3,4-dihidroquinazolina-8-carboxamidas, su preparacion y su uso terapeutico.
AU2008306762A AU2008306762A1 (en) 2007-07-27 2008-07-25 Derivatives of 1-oxo-1,2-dihydroisoquinoline-5-carboxamides and of 4-oxo-3,4-dihydroquinazoline-8-carboxamides, preparation thereof and application thereof in therapeutics
CA2694313A CA2694313A1 (fr) 2007-07-27 2008-07-25 Derives de 1-oxo-1,2-dihydroisoquinoleine-5-carboxamides et de 4-oxo-3,4-dihydroquinazoline-8-carboxamides, leur preparation et leur application en therapeutique
US12/693,598 US8030320B2 (en) 2007-07-27 2010-01-26 Derivatives of 1-OXO-1,2-dihydroisoquinoline-5-carboxamides and of 4-OXO-3,4-dihydroquinazoline-8-carboxamides, preparation thereof and application thereof in therapeutics
ZA2010/00583A ZA201000583B (en) 2007-07-27 2010-01-26 Derivatives of 1-oxo-1,2-dihydroisoquinoline-5-carboxamides and of 4-oxo-3,4-dihydroquinazoline-8-carboxamides,preparation thereof and application thereof in therapeutics

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0705500A FR2919286A1 (fr) 2007-07-27 2007-07-27 Derives de derives de 1-oxo-1,2-dihydroisoquinoleine-5- carboxamides et de 4-oxo-3,4-dihydroquinazoline-8- carboxamides,leur preparation et leur application en therapeutique.
FR0705500 2007-07-27

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/693,598 Continuation US8030320B2 (en) 2007-07-27 2010-01-26 Derivatives of 1-OXO-1,2-dihydroisoquinoline-5-carboxamides and of 4-OXO-3,4-dihydroquinazoline-8-carboxamides, preparation thereof and application thereof in therapeutics

Publications (3)

Publication Number Publication Date
WO2009044018A2 WO2009044018A2 (fr) 2009-04-09
WO2009044018A3 WO2009044018A3 (fr) 2009-06-18
WO2009044018A9 true WO2009044018A9 (fr) 2010-10-14

Family

ID=39106736

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2008/001109 Ceased WO2009044018A2 (fr) 2007-07-27 2008-07-25 Dérivés de 1-0x0-1,2-dihydroisoquinoleine-5-carboxamides et de 4-oxo-3,4-dihydroquinazoline-8-carboxamides, leur préparation et leur application en thérapeutique

Country Status (16)

Country Link
US (1) US8030320B2 (fr)
EP (1) EP2185523A2 (fr)
JP (1) JP2010534640A (fr)
KR (1) KR20100047294A (fr)
CN (1) CN101790518A (fr)
AU (1) AU2008306762A1 (fr)
BR (1) BRPI0814177A2 (fr)
CA (1) CA2694313A1 (fr)
CO (1) CO6290668A2 (fr)
EA (1) EA201070196A1 (fr)
FR (1) FR2919286A1 (fr)
MA (1) MA31629B1 (fr)
MX (1) MX2010001081A (fr)
NZ (1) NZ582995A (fr)
WO (1) WO2009044018A2 (fr)
ZA (1) ZA201000583B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2687750C (fr) * 2007-07-06 2016-10-18 Boehringer Ingelheim International Gmbh Amino-quinazolinones derivees, medicaments comprenant ledit compose, leur utilisation et leur procede de fabrication
FR2919285B1 (fr) * 2007-07-27 2012-08-31 Sanofi Aventis Derives de 1-oxo-isoindoline-4-carboxamides et de 1-oxo- 1,2,3,4-tetrahydroisoquinoleine-5-carboxamides, leur preparation et leur application en therapeutique.
EP2822656B1 (fr) 2012-03-07 2016-10-19 Institute of Cancer Research: Royal Cancer Hospital (The) Composés 3-aryl -5-substitué-isoquinolin -1-one et leur utilisation thérapeutique
CN103087047B (zh) * 2012-12-10 2016-12-21 南京农业大学 一种含二氢异喹啉基团的吡咯烷‑2,4‑二酮类化合物、制备方法及其应用
AU2014320149A1 (en) 2013-09-11 2016-04-07 Institute Of Cancer Research: Royal Cancer Hospital (The) 3-aryl-5-substituted-isoquinolin-1-one compounds and their therapeutic use
TWI770527B (zh) 2019-06-14 2022-07-11 美商基利科學股份有限公司 Cot 調節劑及其使用方法
CA3175541A1 (fr) 2020-03-30 2021-10-07 Gilead Sciences, Inc. Formes solides de (s)-6-(((1-(bicyclo[1.1.1]pentan-1-yl)-1h-1,2,3-triazol-4-yl)-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)methyl)))amino)8-chloro-(neopentylamino)quinoline-3-carb onitrile un compose inhibiteur de cot
EP4613745A3 (fr) * 2020-04-02 2025-11-26 Gilead Sciences, Inc. Procédé de préparation d'un composé inhibiteur de cot

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL161881A0 (en) * 2001-11-08 2005-11-20 Upjohn Co N,N'-substituted-1,3-diamino-2-hydroxypropane derivatives
US20050171094A1 (en) 2002-02-22 2005-08-04 Kenichiro Kataoka Pyrrolopyrimidine derivatives
GB0309221D0 (en) 2003-04-23 2003-06-04 Glaxo Group Ltd Novel compounds
GB0328900D0 (en) 2003-12-12 2004-01-14 Glaxo Group Ltd Novel compounds
US7745470B2 (en) 2005-03-10 2010-06-29 Bristol-Myers Squibb Company Isophthalates as beta-secretase inhibitors
GB0506562D0 (en) 2005-03-31 2005-05-04 Glaxo Group Ltd Novel compounds

Also Published As

Publication number Publication date
KR20100047294A (ko) 2010-05-07
JP2010534640A (ja) 2010-11-11
ZA201000583B (en) 2011-04-28
CO6290668A2 (es) 2011-06-20
US8030320B2 (en) 2011-10-04
EP2185523A2 (fr) 2010-05-19
WO2009044018A2 (fr) 2009-04-09
CN101790518A (zh) 2010-07-28
FR2919286A1 (fr) 2009-01-30
NZ582995A (en) 2012-04-27
EA201070196A1 (ru) 2010-08-30
US20100197706A1 (en) 2010-08-05
BRPI0814177A2 (pt) 2015-01-20
AU2008306762A1 (en) 2009-04-09
MA31629B1 (fr) 2010-08-02
MX2010001081A (es) 2010-03-24
CA2694313A1 (fr) 2009-04-09
WO2009044018A3 (fr) 2009-06-18

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