GB2342357A - Amphiphilic polysaccharide derivatives - Google Patents

Amphiphilic polysaccharide derivatives

Info

Publication number
GB2342357A
GB2342357A GB0001794A GB0001794A GB2342357A GB 2342357 A GB2342357 A GB 2342357A GB 0001794 A GB0001794 A GB 0001794A GB 0001794 A GB0001794 A GB 0001794A GB 2342357 A GB2342357 A GB 2342357A
Authority
GB
United Kingdom
Prior art keywords
heparin
heparin derivatives
derivatives
water
devices
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.)
Granted
Application number
GB0001794A
Other versions
GB0001794D0 (en
GB2342357B (en
Inventor
Youngro Byun
Yong Kyu Lee
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.)
Mediplex Corp Korea
Original Assignee
Mediplex Corp Korea
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 claimed from KR1019990014003A external-priority patent/KR100314496B1/en
Application filed by Mediplex Corp Korea filed Critical Mediplex Corp Korea
Publication of GB0001794D0 publication Critical patent/GB0001794D0/en
Publication of GB2342357A publication Critical patent/GB2342357A/en
Application granted granted Critical
Publication of GB2342357B publication Critical patent/GB2342357B/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
    • A61K31/727—Heparin; Heparan
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/542—Carboxylic acids, e.g. a fatty acid or an amino acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/554—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound the modifying agent being a steroid plant sterol, glycyrrhetic acid, enoxolone or bile acid
    • 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
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • 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

Landscapes

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

Abstract

Polysaccharides, which are widely used as anticoagulation drugs, especially heparin, are clinically administered only by intravenous or subcutaneous injection because of their strong hydrophilicity and high negative charge. Amphiphilic heparin derivatives were synthesized by conjugate to bile acids, sterols, and alkanoic acids, respectively. The hydrophobicity of the heparin derivatives depended on the feed mole ratio of heparin to hydrophobic agent. The heparin derivatives were slightly hydrophobic and exhibited good solubility in a water-acetone solvent, as well as water. The heparin derivatives have a high anticoagulant activity. These slightly hydrophobic heparin derivatives can be absorbed in gastric intestinal tract and can be used as oral dosage form. Also, the heparin derivatives can be used for the surface modification to prevent coagulation for medical devices such as extracorporeal devices and implanted devices.
GB0001794A 1998-05-28 1999-05-14 Amphiphilic heparin derivatives Expired - Fee Related GB2342357B (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR19980019469 1998-05-28
KR1019990014003A KR100314496B1 (en) 1998-05-28 1999-04-20 Non-thrombogenic heparin derivatives, process for preparation and use thereof
US09/300,173 US6245753B1 (en) 1998-05-28 1999-04-27 Amphiphilic polysaccharide derivatives
PCT/KR1999/000242 WO1999061481A1 (en) 1998-05-28 1999-05-14 Amphiphilic polysaccharide derivatives

Publications (3)

Publication Number Publication Date
GB0001794D0 GB0001794D0 (en) 2000-03-22
GB2342357A true GB2342357A (en) 2000-04-12
GB2342357B GB2342357B (en) 2002-03-27

Family

ID=27349744

Family Applications (1)

Application Number Title Priority Date Filing Date
GB0001794A Expired - Fee Related GB2342357B (en) 1998-05-28 1999-05-14 Amphiphilic heparin derivatives

Country Status (5)

Country Link
JP (1) JP3541007B2 (en)
AU (1) AU3735899A (en)
DE (1) DE19981169B4 (en)
GB (1) GB2342357B (en)
WO (1) WO1999061481A1 (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6656922B2 (en) * 1998-05-28 2003-12-02 Mediplex Corporation, Korea Oral delivery of macromolecules
US7303768B2 (en) 1998-07-24 2007-12-04 Seo Hong Yoo Preparation of aqueous clear solution dosage forms with bile acids
US7772220B2 (en) 2004-10-15 2010-08-10 Seo Hong Yoo Methods and compositions for reducing toxicity of a pharmaceutical compound
KR100378109B1 (en) * 2000-10-24 2003-03-29 주식회사 메디프렉스 Hydrophobic multicomponant heparin conjugates, a preparing method and a use thereof
JP4084199B2 (en) * 2001-05-09 2008-04-30 メディプレックス コーポレーション Process for increasing mucosal absorption of amphiphilic heparin derivatives
US7145125B2 (en) 2003-06-23 2006-12-05 Advanced Optical Technologies, Llc Integrating chamber cone light using LED sources
FR2864091B1 (en) * 2003-12-19 2006-04-07 Ethypharm Sa AMPHIPHILE HEPARIN DERIVATIVE FORMED BY COUPLING HEPARIN WITH A BILARY ACID
US8173627B2 (en) 2004-08-30 2012-05-08 Seo Hong Yoo Neuroprotective effect of solubilized UDCA in focal ischemic model
ATE506955T1 (en) 2004-10-15 2011-05-15 Seo Hong Yoo COMPOSITIONS FOR REDUCING THE TOXICITY OF CISPLATIN, CARBOPLATIN AND OXALIPLATIN
US20110046050A1 (en) 2007-02-08 2011-02-24 Emisphere Technologies, Inc. Phenylalkylcarboxylic acid delivery agents
EP2222753A4 (en) * 2007-12-05 2011-07-06 Xiao-Xia Zhu Amphiphilic polymers having a cholane core
US8759322B2 (en) 2008-11-05 2014-06-24 National University Corporation Tokyo Medical And Dental University Hyaluronic acid derivative and pharmaceutical composition thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB891554A (en) * 1959-10-19 1962-03-14 Applic Chimiques D Etudes Et D Galenic suppository containing salts of heparin
GB1157754A (en) * 1966-06-29 1969-07-09 Canada Packers Ltd Orally Active Heparin and method of making and using same
WO1995012620A1 (en) * 1993-11-01 1995-05-11 Alpha-Beta Technology, Inc. Derivatized polysaccharide bile acid sequestrant for reducing cholesterol

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07206903A (en) * 1994-01-24 1995-08-08 Takeda Chem Ind Ltd Aggregate of super molecule structure type

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB891554A (en) * 1959-10-19 1962-03-14 Applic Chimiques D Etudes Et D Galenic suppository containing salts of heparin
GB1157754A (en) * 1966-06-29 1969-07-09 Canada Packers Ltd Orally Active Heparin and method of making and using same
WO1995012620A1 (en) * 1993-11-01 1995-05-11 Alpha-Beta Technology, Inc. Derivatized polysaccharide bile acid sequestrant for reducing cholesterol

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"New approaches for the preparation of hydrophobic heparin derivatives", *
Database WPIL on EPO,week 95-40,London:Derwent Publications Ltd,AN95-309101,JP07-206903A, 8/8/1995 *
Journal of Pharmaceutical Sciences, Vol 83, No 7, July 1994 Pages 1034-1039,J.LIU et al.: *

Also Published As

Publication number Publication date
WO1999061481A1 (en) 1999-12-02
JP2002516355A (en) 2002-06-04
GB0001794D0 (en) 2000-03-22
AU3735899A (en) 1999-12-13
GB2342357B (en) 2002-03-27
DE19981169B4 (en) 2007-09-13
JP3541007B2 (en) 2004-07-07
DE19981169T1 (en) 2000-11-16

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Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee

Effective date: 20110514