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FR2964660B1 - NOVEL BIOTINYL POLYSACCHARIDES WITH ANTITHROMBOTIC ACTIVITY AND IMPROVED METABOLIC STABILITY - Google Patents

NOVEL BIOTINYL POLYSACCHARIDES WITH ANTITHROMBOTIC ACTIVITY AND IMPROVED METABOLIC STABILITY

Info

Publication number
FR2964660B1
FR2964660B1 FR1057194A FR1057194A FR2964660B1 FR 2964660 B1 FR2964660 B1 FR 2964660B1 FR 1057194 A FR1057194 A FR 1057194A FR 1057194 A FR1057194 A FR 1057194A FR 2964660 B1 FR2964660 B1 FR 2964660B1
Authority
FR
France
Prior art keywords
group
alpha
methyl
covalent bond
polysaccharides
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.)
Expired - Fee Related
Application number
FR1057194A
Other languages
French (fr)
Other versions
FR2964660A1 (en
Inventor
Marc Bianciotto
Alexandre Driguez
Philippe Duchaussoy
Gilbert Lassalle
Dref Pierrick Le
Jean Christophe Thiery
Patrick Trouilleux
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
Application filed by Sanofi Aventis France filed Critical Sanofi Aventis France
Priority to FR1057194A priority Critical patent/FR2964660B1/en
Priority to JP2013527656A priority patent/JP2013537181A/en
Priority to PCT/FR2011/000498 priority patent/WO2012042123A1/en
Priority to EP11761652.4A priority patent/EP2614089A1/en
Publication of FR2964660A1 publication Critical patent/FR2964660A1/en
Application granted granted Critical
Publication of FR2964660B1 publication Critical patent/FR2964660B1/en
Priority to US13/790,681 priority patent/US20130190268A1/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
    • C08B37/0075—Heparin; Heparan sulfate; Derivatives thereof, e.g. heparosan; Purification or extraction methods thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/74—Synthetic polymeric materials
    • A61K31/795—Polymers containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biochemistry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Cardiology (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

Synthetic polysaccharides (A) comprising at least one covalent bond with biotin or its derivative, is new, where the covalent bond is resistant to cleavage and comprises a metabolic linking group X comprising -O-, amine group (a1), amide group (a2) and diamide group (a3). Synthetic polysaccharides (A) comprising at least one covalent bond with biotin or its derivative, is new, where the covalent bond is resistant to cleavage and comprises a metabolic linking group X comprising -O-, amine group of formula (-N(R)-) (a1), amide group of formula (-N(R)-CO-) (a2) and diamide group of formula (-N(R)-CO-NR1a) (a3). R, R1a : alkyl group. - ACTIVITY : Anticoagulant; Thrombolytic. - MECHANISM OF ACTION : Factor Xa inhibitor. The ability of (A) to inhibit Factor Xa was tested using an in vitro model of inhibition of factor Xa of coagulation. The result showed that methyl (2-deoxy-3,4-di-O-methyl-2 -{[5-[({4-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl] butyl}carbamoyl)amino]pentanoyl}amino)-6-O-sulfonato-alpha -D-glucopyranosyl)-(1-4)-(2,3-di-O-methyl-beta -D-glucopyranosyluronate]-(1-4)-(2,3,6-tri-O-sulfonato-alpha -D-glucopyranosyl)-(1-4)-(2,3-di-O-methyl-alpha -L-iodopyranosyluronate)-(1-4)-2,3,6-tri-O-sulfonato-alpha -D-glucopyranoside exhibited an IC 5 0value of 17.1 ng/ml.
FR1057194A 2010-09-10 2010-09-10 NOVEL BIOTINYL POLYSACCHARIDES WITH ANTITHROMBOTIC ACTIVITY AND IMPROVED METABOLIC STABILITY Expired - Fee Related FR2964660B1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
FR1057194A FR2964660B1 (en) 2010-09-10 2010-09-10 NOVEL BIOTINYL POLYSACCHARIDES WITH ANTITHROMBOTIC ACTIVITY AND IMPROVED METABOLIC STABILITY
JP2013527656A JP2013537181A (en) 2010-09-10 2011-09-09 Biotinylated polysaccharides with antithrombotic activity and improved metabolic stability
PCT/FR2011/000498 WO2012042123A1 (en) 2010-09-10 2011-09-09 Biotinylated polysaccharides having an antithrombotic activity and improved metabolic stability
EP11761652.4A EP2614089A1 (en) 2010-09-10 2011-09-09 Biotinylated polysaccharides having an antithrombotic activity and improved metabolic stability
US13/790,681 US20130190268A1 (en) 2010-09-10 2013-03-08 Biotinylated polysaccharides having an antithrombotic activity and improved metabolic stability

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1057194A FR2964660B1 (en) 2010-09-10 2010-09-10 NOVEL BIOTINYL POLYSACCHARIDES WITH ANTITHROMBOTIC ACTIVITY AND IMPROVED METABOLIC STABILITY

Publications (2)

Publication Number Publication Date
FR2964660A1 FR2964660A1 (en) 2012-03-16
FR2964660B1 true FR2964660B1 (en) 2012-09-28

Family

ID=43827300

Family Applications (1)

Application Number Title Priority Date Filing Date
FR1057194A Expired - Fee Related FR2964660B1 (en) 2010-09-10 2010-09-10 NOVEL BIOTINYL POLYSACCHARIDES WITH ANTITHROMBOTIC ACTIVITY AND IMPROVED METABOLIC STABILITY

Country Status (1)

Country Link
FR (1) FR2964660B1 (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2814463B1 (en) * 2000-09-22 2002-11-15 Sanofi Synthelabo NOVEL POLYSACCHARIDES WITH ANTITHROMBOTIC ACTIVITY COMPRISING AT LEAST ONE COVALENT BINDING WITH BIOTIN OR A BIOTINE DERIVATIVE

Also Published As

Publication number Publication date
FR2964660A1 (en) 2012-03-16

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