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WO2009044019A9 - Dérivés de 1-oxo-isoindoline-4-carboxamides et de 1-oxo-1,2,3,4-tetrahydroisoquinoleine-5-carboxamides, leur préparation et leur application en thérapeutique - Google Patents

Dérivés de 1-oxo-isoindoline-4-carboxamides et de 1-oxo-1,2,3,4-tetrahydroisoquinoleine-5-carboxamides, leur préparation et leur application en thérapeutique Download PDF

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Publication number
WO2009044019A9
WO2009044019A9 PCT/FR2008/001110 FR2008001110W WO2009044019A9 WO 2009044019 A9 WO2009044019 A9 WO 2009044019A9 FR 2008001110 W FR2008001110 W FR 2008001110W WO 2009044019 A9 WO2009044019 A9 WO 2009044019A9
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
oxo
carboxamide
cycloalkyl
nr7r8
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/FR2008/001110
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English (en)
Other versions
WO2009044019A3 (fr
WO2009044019A2 (fr
Inventor
Bernard Baudoin
Michel Evers
Arielle Genevois-Borella
Andreas Karlsson
Jean-Luc Malleron
Magali Mathieu
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 JP2010517453A priority Critical patent/JP5412428B2/ja
Priority to BRPI0813624A priority patent/BRPI0813624A2/pt
Priority to NZ582873A priority patent/NZ582873A/en
Priority to CN2008801045290A priority patent/CN101790514B/zh
Priority to HK10109764.3A priority patent/HK1143163B/xx
Priority to EP08835551A priority patent/EP2185511A2/fr
Priority to AU2008306763A priority patent/AU2008306763B2/en
Priority to EA201070197A priority patent/EA201070197A1/ru
Priority to MX2010001079A priority patent/MX2010001079A/es
Application filed by Sanofi Aventis France filed Critical Sanofi Aventis France
Priority to CA2694322A priority patent/CA2694322A1/fr
Publication of WO2009044019A2 publication Critical patent/WO2009044019A2/fr
Publication of WO2009044019A3 publication Critical patent/WO2009044019A3/fr
Priority to ZA2010/00582A priority patent/ZA201000582B/en
Priority to US12/693,597 priority patent/US8372864B2/en
Anticipated expiration legal-status Critical
Priority to MA32652A priority patent/MA31635B1/fr
Publication of WO2009044019A9 publication Critical patent/WO2009044019A9/fr
Ceased legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44Iso-indoles; Hydrogenated iso-indoles
    • C07D209/46Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/02Drugs for disorders of the nervous system for peripheral neuropathies
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/06Antimigraine agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/22Anxiolytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D217/00Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22Heterocyclic 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
    • C07D217/24Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (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)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

L'invention concerne les dérivés de 1-oxo-isoindoline-4-carboxamides et de 1-oxo- 1,2,3,4-tétrahydroisoquinoléine-5-carboxamides, de formule générale (I) dans laquelle R1 représente un atome d'hydrogène, un groupe (C1-C6)alkyle, (C3-C7)cycloalkyle (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 u groupe COOR, S(O)mR, un aryle ou un aralkyle; R2 représente un ou plusieurs groupe 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)alky!e, dans lequel Z représente un hétéroatome choisi parmi O, N et S(O)m, ou bien R2 représente u 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 d l'autre, un atome d'hydrogène, ou bien R4 et R5 forment avec l'atome de carbone qui le 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 u 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 group NR7R8, COOR, un groupe NR7(SO2)R8, CONR7R8, un groupe aryle ou hétérocycle; représente un groupe (C1-C2)alkylène; m représente un nombre entier compris entre O et 2 n représente un nombre entier compris entre 1 et 6. L'invention a également trait à leur procédé de préparation et leur application e thérapeutique comme inhibiteurs de β-secrétase pour traiter les trouble neurodégénératifs tels qu'Alzheimer. I
PCT/FR2008/001110 2007-07-27 2008-07-25 Dérivés de 1-oxo-isoindoline-4-carboxamides et de 1-oxo-1,2,3,4-tetrahydroisoquinoleine-5-carboxamides, leur préparation et leur application en thérapeutique Ceased WO2009044019A2 (fr)

Priority Applications (13)

Application Number Priority Date Filing Date Title
MX2010001079A MX2010001079A (es) 2007-07-27 2008-07-25 Derivados de 1-oxo-isoindolina-4-carboxamidas y de 1-oxo-1,2,3,4-tetrahidroisoquinoleina-5-carboxamidas, su preparacion y su aplicacion en terapeutica.
NZ582873A NZ582873A (en) 2007-07-27 2008-07-25 1-oxo-isoindoline-4-carboxamide and 1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxamide derivatives, preparation and therapeutic use thereof
CA2694322A CA2694322A1 (fr) 2007-07-27 2008-07-25 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
HK10109764.3A HK1143163B (en) 2007-07-27 2008-07-25 1-oxo-isoindoline-4-carboxamide and 1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxamide derivatives, preparation and therapeutic use thereof
EP08835551A EP2185511A2 (fr) 2007-07-27 2008-07-25 Dérivés de 1-oxo-isoindoline-4-carboxamides et de 1-oxo-1,2,3,4-tetrahydroisoquinoleine-5-carboxamides, leur préparation et leur application en thérapeutique
AU2008306763A AU2008306763B2 (en) 2007-07-27 2008-07-25 1-oxo-isoindoline-4-carboxamide and 1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxamide derivatives, preparation and therapeutic use thereof
EA201070197A EA201070197A1 (ru) 2007-07-27 2008-07-25 Производные 1-оксо-изоиндолин-4-карбоксамидов и 1-оксо-1,2,3,4-тетрагидроизохинолин-5-карбоксамидов, способ их получения и применение в терапии
JP2010517453A JP5412428B2 (ja) 2007-07-27 2008-07-25 1−オキソ−イソインドリン−4−カルボキサミドおよび1−オキソ−1,2,3,4−テトラヒドロイソキノリン−5−カルボキサミド誘導体、それらの調製および治療上の使用
CN2008801045290A CN101790514B (zh) 2007-07-27 2008-07-25 1-氧代-异二氢吲哚-4-甲酰胺和1-氧代-1,2,3,4-四氢异喹啉-5-甲酰胺衍生物、其制备和治疗用途
BRPI0813624A BRPI0813624A2 (pt) 2007-07-27 2008-07-25 derivados de 1-oxo-isoindolina-4-carboxamidas e de 1-oxo-1,2,3,4-tetra-hidroisoquinoleína-5-carboxamidas, o respectivo preparo e a respectiva aplicação em terapêutica.
ZA2010/00582A ZA201000582B (en) 2007-07-27 2010-01-26 1-oxo-isoindoline-4-carboxamide and 1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxamide derivatives,preparation and therapeutic use thereof
US12/693,597 US8372864B2 (en) 2007-07-27 2010-01-26 1-oxo-isoindoline-4-carboxamide and 1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxamide derivatives, preparation and therapeutic use thereof
MA32652A MA31635B1 (fr) 2007-07-27 2010-02-24 Dérivés de 1-oxo-isoindoline-4-carboxamides et de 1-oxo-1,2,3,4-tetrahydroisoquinoleine-5-carboxamides, leur préparation et leur application en thérapeutique

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0705499 2007-07-27
FR0705499A FR2919285B1 (fr) 2007-07-27 2007-07-27 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.

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/693,597 Continuation US8372864B2 (en) 2007-07-27 2010-01-26 1-oxo-isoindoline-4-carboxamide and 1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxamide derivatives, preparation and therapeutic use thereof

Publications (3)

Publication Number Publication Date
WO2009044019A2 WO2009044019A2 (fr) 2009-04-09
WO2009044019A3 WO2009044019A3 (fr) 2009-06-18
WO2009044019A9 true WO2009044019A9 (fr) 2010-10-14

Family

ID=39092246

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2008/001110 Ceased WO2009044019A2 (fr) 2007-07-27 2008-07-25 Dérivés de 1-oxo-isoindoline-4-carboxamides et de 1-oxo-1,2,3,4-tetrahydroisoquinoleine-5-carboxamides, leur préparation et leur application en thérapeutique

Country Status (18)

Country Link
US (1) US8372864B2 (fr)
EP (1) EP2185511A2 (fr)
JP (1) JP5412428B2 (fr)
KR (1) KR20100051830A (fr)
CN (1) CN101790514B (fr)
AU (1) AU2008306763B2 (fr)
BR (1) BRPI0813624A2 (fr)
CA (1) CA2694322A1 (fr)
CO (1) CO6290678A2 (fr)
EA (1) EA201070197A1 (fr)
FR (1) FR2919285B1 (fr)
MA (1) MA31635B1 (fr)
MX (1) MX2010001079A (fr)
MY (1) MY150436A (fr)
NZ (1) NZ582873A (fr)
SG (1) SG183082A1 (fr)
WO (1) WO2009044019A2 (fr)
ZA (1) ZA201000582B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014520776A (ja) 2011-07-04 2014-08-25 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー 植物における非生物的ストレスに対する活性薬剤としての置換されているイソキノリノン類、イソキノリンジオン類、イソキノリントリオン類およびジヒドロイソキノリノン類または各場合でのそれらの塩の使用
CN105254554B (zh) * 2014-07-14 2018-01-30 南开大学 一种制备异吲哚啉酮类化合物的方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0846112A1 (fr) * 1995-08-25 1998-06-10 E.I. Du Pont De Nemours And Company Herbicides bicycliques
DE10018449A1 (de) 2000-04-14 2001-11-22 Top Caredent Ag Zuerich Vorrichtung zum Darbieten von Gerätschaften der Dentalhygiene
IL161881A0 (en) * 2001-11-08 2005-11-20 Upjohn Co N,N'-substituted-1,3-diamino-2-hydroxypropane derivatives
GB0228410D0 (en) * 2002-12-05 2003-01-08 Glaxo Group Ltd Novel Compounds
GB0305918D0 (en) * 2003-03-14 2003-04-23 Glaxo Group Ltd Novel compounds
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
FR2919286A1 (fr) * 2007-07-27 2009-01-30 Sanofi Aventis Sa 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.
RS51912B (sr) * 2007-07-27 2012-02-29 Sanofi DERIVATI 1,2,3,4-TETRAHIDROPIROLO(1,2-a)PIRAZIN-6-KARBOKSAMIDA I 2,3,4,5-TETRAHIDROPIROLO(1,2-a)(1,4)-DIAZEPIN-7-KARBOKSAMIDA NJIHOVO DOBIJANJE I TERAPEUTSKA PRIMENA

Also Published As

Publication number Publication date
MY150436A (en) 2014-01-30
EP2185511A2 (fr) 2010-05-19
WO2009044019A3 (fr) 2009-06-18
AU2008306763A1 (en) 2009-04-09
CN101790514A (zh) 2010-07-28
JP5412428B2 (ja) 2014-02-12
KR20100051830A (ko) 2010-05-18
BRPI0813624A2 (pt) 2019-09-24
US20100197725A1 (en) 2010-08-05
MA31635B1 (fr) 2010-08-02
AU2008306763B2 (en) 2013-08-29
CA2694322A1 (fr) 2009-04-09
FR2919285A1 (fr) 2009-01-30
WO2009044019A2 (fr) 2009-04-09
SG183082A1 (en) 2012-08-30
HK1143163A1 (en) 2010-12-24
CO6290678A2 (es) 2011-06-20
CN101790514B (zh) 2012-12-19
NZ582873A (en) 2012-07-27
US8372864B2 (en) 2013-02-12
JP2010534641A (ja) 2010-11-11
MX2010001079A (es) 2010-03-24
EA201070197A1 (ru) 2010-08-30
ZA201000582B (en) 2011-04-28
FR2919285B1 (fr) 2012-08-31

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