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WO2006117696A3 - Diastereoisomeres de of 4-hydroxyisoleucine et utilisations associees - Google Patents

Diastereoisomeres de of 4-hydroxyisoleucine et utilisations associees Download PDF

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Publication number
WO2006117696A3
WO2006117696A3 PCT/IB2006/001758 IB2006001758W WO2006117696A3 WO 2006117696 A3 WO2006117696 A3 WO 2006117696A3 IB 2006001758 W IB2006001758 W IB 2006001758W WO 2006117696 A3 WO2006117696 A3 WO 2006117696A3
Authority
WO
WIPO (PCT)
Prior art keywords
hydroxyisoleucine
diabetes
type
isomers
diastereoisomers
Prior art date
Application number
PCT/IB2006/001758
Other languages
English (en)
Other versions
WO2006117696A2 (fr
Inventor
Claude Coquelet
Charles Mioskowski
Alain Wagner
Original Assignee
Innodia Inc
Centre Nat Rech Scient
Univ Pasteur
Claude Coquelet
Charles Mioskowski
Alain Wagner
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 Innodia Inc, Centre Nat Rech Scient, Univ Pasteur, Claude Coquelet, Charles Mioskowski, Alain Wagner filed Critical Innodia Inc
Priority to AU2006242851A priority Critical patent/AU2006242851A1/en
Priority to BRPI0607140-6A priority patent/BRPI0607140A2/pt
Priority to CA002598491A priority patent/CA2598491A1/fr
Priority to MX2007009985A priority patent/MX2007009985A/es
Priority to EP06765601A priority patent/EP1853552A2/fr
Priority to JP2007555732A priority patent/JP2008530198A/ja
Publication of WO2006117696A2 publication Critical patent/WO2006117696A2/fr
Publication of WO2006117696A3 publication Critical patent/WO2006117696A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • 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
    • A61P3/08—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des isomères configurationnels 4-hydroxyisoleucine, ainsi que des lactones, des sels pharmaceutiquement acceptables, des promédicaments associés, des procédés de préparation et des compositions pharmaceutiques les contenant. Les isomères de l'invention possèdent une activité insulinotropique et peuvent donc être utiles à la prévention et au traitement de troubles du métabolisme des glucides ou des lipides, y compris le diabète sucré (diabètes de type 1 et de type 2), le prédiabète, et le syndrome métabolique.
PCT/IB2006/001758 2005-02-18 2006-02-17 Diastereoisomeres de of 4-hydroxyisoleucine et utilisations associees WO2006117696A2 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU2006242851A AU2006242851A1 (en) 2005-02-18 2006-02-17 Diastereoisomers of 4-hydroxyisoleucine and uses thereof
BRPI0607140-6A BRPI0607140A2 (pt) 2005-02-18 2006-02-17 composto, uso do composto e/ou uso de um sal, lactona ou pró-medicamento farmaceuticamente aceitável do dito composto, composição farmacêutica, kit farmacêutico, método para estimular a captação de glicose pelas células musculares e/ou células de adipócito, método para estimular a secreção de insulina pelas células pancreáticas células-(beta) e método para o tratamento de um mamìfero que tem um distúrbio do metabolismo de carboidratos ou de lipìdios
CA002598491A CA2598491A1 (fr) 2005-02-18 2006-02-17 Diastereoisomeres de of 4-hydroxyisoleucine et utilisations associees
MX2007009985A MX2007009985A (es) 2005-02-18 2006-02-17 Diastereoisomeros de 4-hidroxiisoleucina y usos de los mismos.
EP06765601A EP1853552A2 (fr) 2005-02-18 2006-02-17 Diastereoisomeres de of 4-hydroxyisoleucine et utilisations associees
JP2007555732A JP2008530198A (ja) 2005-02-18 2006-02-17 ４−ヒドロキシイソロイシンのジアステレオ異性体及びこれらの使用

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US65441305P 2005-02-18 2005-02-18
US60/654,413 2005-02-18

Publications (2)

Publication Number Publication Date
WO2006117696A2 WO2006117696A2 (fr) 2006-11-09
WO2006117696A3 true WO2006117696A3 (fr) 2007-01-25

Family

ID=37086084

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2006/001758 WO2006117696A2 (fr) 2005-02-18 2006-02-17 Diastereoisomeres de of 4-hydroxyisoleucine et utilisations associees

Country Status (8)

Country Link
EP (1) EP1853552A2 (fr)
JP (1) JP2008530198A (fr)
CN (1) CN101128418A (fr)
AU (1) AU2006242851A1 (fr)
BR (1) BRPI0607140A2 (fr)
CA (1) CA2598491A1 (fr)
MX (1) MX2007009985A (fr)
WO (1) WO2006117696A2 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2600954A1 (fr) * 2005-03-22 2006-12-14 Innodia Inc. Composes et compositions destines a la prevention et au traitement de l'obesite et des syndromes y relatifs
WO2008154743A1 (fr) * 2007-06-19 2008-12-24 Innodia Inc. Procédés de synthèse de la 4-hydroxyisoleucine, de ses stéréoisomères et de ses analogues
WO2009085180A1 (fr) * 2007-12-20 2009-07-09 The Feinstein Institute For Medical Research Traitement de la sepsie et inhibition de mif par d-t4
LT3364958T (lt) * 2015-10-23 2023-06-12 Navitor Pharmaceuticals, Inc. Sestrin-gator2 sąveikos moduliatoriai ir jų panaudojimas
TWI776886B (zh) 2017-04-26 2022-09-11 美商奈維特製藥公司 Sestrin-gator2交互作用之調節劑及其用途
CN113164414A (zh) 2018-10-24 2021-07-23 纳维托制药有限公司 多晶型化合物和其用途
CN114786660A (zh) 2019-11-01 2022-07-22 纳维托制药有限公司 使用mtorc1调节剂的治疗方法
CN112089710B (zh) * 2020-08-07 2022-04-01 郑州大学 4-羟基异亮氨酸在制备抗肿瘤药物中的应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001015689A1 (fr) * 1999-08-27 2001-03-08 Centre National De La Recherche Scientifique (Cnrs) Utilisation d'acides amines pour la fabrication de medicaments destines au traitement des insulino-resistances
WO2005039626A2 (fr) * 2003-10-27 2005-05-06 Innodia Inc. Procedes et compositions a utiliser pour le traitement des diabetes
EP1657236A1 (fr) * 2004-11-10 2006-05-17 Centre National De La Recherche Scientifique (Cnrs) Procédé de préparation des diastéréoisomères de la 4-hydroxyisoleucine

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001015689A1 (fr) * 1999-08-27 2001-03-08 Centre National De La Recherche Scientifique (Cnrs) Utilisation d'acides amines pour la fabrication de medicaments destines au traitement des insulino-resistances
WO2005039626A2 (fr) * 2003-10-27 2005-05-06 Innodia Inc. Procedes et compositions a utiliser pour le traitement des diabetes
EP1657236A1 (fr) * 2004-11-10 2006-05-17 Centre National De La Recherche Scientifique (Cnrs) Procédé de préparation des diastéréoisomères de la 4-hydroxyisoleucine

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
BROCA C ET AL: "4-HYDROXYISOLEUCINE: EFFECTS OF SYNTHETIC AND NATURAL ANALOGUES ON INSULIN SECRETION", EUROPEAN JOURNAL OF PHARMACOLOGY, AMSTERDAM, NL, vol. 390, no. 3, March 2000 (2000-03-01), pages 339 - 345, XP000908995, ISSN: 0014-2999 *
INGHARDT T ET AL: "ORGANOALUMINIUM INDUCED RING-OPENING OF EPOXYPYRANOSIDES IV. SYNTHESIS AND STRUCTURE OF GAMMA- HYDROXY-ISOLEUCINE STEREOISOMERS AND THEIR CORRESPONDING LACTONES", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 47, no. 32, 5 August 1991 (1991-08-05), pages 6469 - 6482, XP000611434, ISSN: 0040-4020 *
JAMIESON, ANDREW G. ET AL: "The first enantioselective synthesis of the amino acid (2S,3S,4R)-.gamma.-hydroxyisoleucine using a palladium(II) catalyzed 3,3-sigmatropic rearrangement", ORGANIC & BIOMOLECULAR CHEMISTRY , 2(6), 808-809 CODEN: OBCRAK; ISSN: 1477-0520, 2004, XP002404013 *
MASHOODA HASAN: "THE DIASTEREOMERIC Y-HYDROXY-ISOLEUCINES", STUDIES IN ORGANIC CHEMISTRY, ELSEVIER, AMSTERDAM,, NL, vol. 26, 1986, pages 123 - 141, XP002020595, ISSN: 0165-3253 *
RIBES G ET AL: "Structure activity analysis of different analogues of the new insulinotropic agent 4-hydroxyisoleucine", DIABETOLOGIA, BERLIN, DE, vol. 39, no. s1, September 1996 (1996-09-01), pages A234, XP002032872, ISSN: 0012-186X *
ROLLAND-FULCRAND V ET AL: "Chemoenzymatic synthesis of enantiomerically pure (2S,3R,4S)-4-hydroxyisoleucine, an insulinotropic amino acid isolated from fenugreek seeds", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH VERLAG, WEINHEIM, DE, vol. 2004, 2004, pages 873 - 877, XP002393122, ISSN: 1434-193X *
TAMURA, OSAMU ET AL: "Syntheses of (-)-Funebrine and (-)-Funebral, Using Sequential Transesterification and Intramolecular Cycloaddition of a Chiral Nitrone", JOURNAL OF ORGANIC CHEMISTRY , 69(5), 1475-1480 CODEN: JOCEAH; ISSN: 0022-3263, 2004, XP002404012 *

Also Published As

Publication number Publication date
CA2598491A1 (fr) 2006-11-09
AU2006242851A1 (en) 2006-11-09
JP2008530198A (ja) 2008-08-07
MX2007009985A (es) 2008-03-11
CN101128418A (zh) 2008-02-20
EP1853552A2 (fr) 2007-11-14
WO2006117696A2 (fr) 2006-11-09
BRPI0607140A2 (pt) 2009-08-11

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