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WO2005092929A8 - Hyaluronic acid butyric esters with a low degree of substitution, procedure for their preparation and use - Google Patents

Hyaluronic acid butyric esters with a low degree of substitution, procedure for their preparation and use

Info

Publication number
WO2005092929A8
WO2005092929A8 PCT/IB2005/000780 IB2005000780W WO2005092929A8 WO 2005092929 A8 WO2005092929 A8 WO 2005092929A8 IB 2005000780 W IB2005000780 W IB 2005000780W WO 2005092929 A8 WO2005092929 A8 WO 2005092929A8
Authority
WO
WIPO (PCT)
Prior art keywords
hyaluronic acid
esters
substitution
butyric
residues
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/IB2005/000780
Other languages
French (fr)
Other versions
WO2005092929A1 (en
Inventor
Danila Coradini
Alberto Perbellini
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.)
SINTOFARM SpA
Original Assignee
SINTOFARM SpA
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 SINTOFARM SpA filed Critical SINTOFARM SpA
Priority to EP05718276A priority Critical patent/EP1781707A1/en
Publication of WO2005092929A1 publication Critical patent/WO2005092929A1/en
Publication of WO2005092929A8 publication Critical patent/WO2005092929A8/en
Anticipated expiration legal-status Critical
Ceased 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
    • C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

The invention relates to hyaluronic acid butyric esters in which the hydroxyl groups of hyaluronic acid are partially esterified with butyric residues, characterised by a degree of substitution with butyric residues (ratio of number of butyric acid residues to disaccharide units GIcNAc-GIcUA of hyaluronic acid) being equal or below 0.1. These esters with low degree of substitution are obtained by means of a process carried out in the homogeneous phase under anhydrous conditions, wherein hyaluronic acid is used in the form of a quaternary nitrogen salt. The esters of the invention have a greater antiproliferative activity than corresponding esters with higher degree of substitution, and are particularly active against primary and metastatic tumours, where said tumours are primary of hepatic origin, or are hepatic metastases. A further aspect of the invention is represented by pharmaceutical compositions, containing as active principle at least one of the esters described.
PCT/IB2005/000780 2004-03-29 2005-03-25 Hyaluronic acid butyric esters with a low degree of substitution, procedure for their preparation and use Ceased WO2005092929A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP05718276A EP1781707A1 (en) 2004-03-29 2005-03-25 Hyaluronic acid butyric esters with a low degree of substitution, procedure for their preparation and use

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI20040605 ITMI20040605A1 (en) 2004-03-29 2004-03-29 BUTYRICAL ESTERS OF HYALURONIC ACID WITH LOW DEGREE OF SUBSTITUTION PROCEDURE FOR THEIR PREPARATION AND USE
ITMI2004A000605 2004-03-29

Publications (2)

Publication Number Publication Date
WO2005092929A1 WO2005092929A1 (en) 2005-10-06
WO2005092929A8 true WO2005092929A8 (en) 2006-03-02

Family

ID=34967092

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2005/000780 Ceased WO2005092929A1 (en) 2004-03-29 2005-03-25 Hyaluronic acid butyric esters with a low degree of substitution, procedure for their preparation and use

Country Status (3)

Country Link
EP (1) EP1781707A1 (en)
IT (1) ITMI20040605A1 (en)
WO (1) WO2005092929A1 (en)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1942117A1 (en) * 2006-12-29 2008-07-09 Sigea S.R.L. Derivatives of acid polysaccharides
ITMI20072237A1 (en) * 2007-11-27 2009-05-28 Sigea Srl MIXED BUTIRRIC-FORMAL ESTERS OF ACID POLYSACCHARIDES, THEIR PREPARATION AND USE AS DERMOCOSMETICS
KR101078302B1 (en) * 2008-05-29 2011-10-31 (주)프로넥스 Drug Delivery System
ITTO20110428A1 (en) 2011-05-13 2012-11-14 Rottapharm Spa ESTERS OF HYALURONIC ACID, THEIR PREPARATION AND USE IN DERMATOLOGY
CZ2012842A3 (en) 2012-11-27 2014-08-20 Contipro Biotech S.R.O. C6-C18-acylated hyaluronate-based nanomicellar composition, process for preparing C6-C18-acylated hyaluronate, process for preparing nanomicellar composition and stabilized nanomicellar composition as well as use thereof
CZ2013914A3 (en) 2013-11-21 2015-02-25 Contipro Biotech S.R.O. Nanofibers containing photocurable ester derivative of hyaluronic acid or its salt, photocured nanofibers, method of their synthesis, preparation containing photo-hardened nanofibers and their use
CN103724455B (en) * 2013-12-11 2016-07-06 四川大学 A kind of preparation method of derivatives of hyaluronic acids and hydrogel thereof
CZ2014150A3 (en) 2014-03-11 2015-05-20 Contipro Biotech S.R.O. Conjugates of hyaluronic acid oligomer or salts thereof, process of their preparation and use
CZ2014451A3 (en) 2014-06-30 2016-01-13 Contipro Pharma A.S. Antitumor composition based on hyaluronic acid and inorganic nanoparticles, process of its preparation and use
JP6738337B2 (en) * 2015-01-13 2020-08-12 シジェア ソシエタ ア レスポンサビリタ リミタータ A method in water for the preparation of butyric acid esters of sodium hyaluronate.
CZ309295B6 (en) 2015-03-09 2022-08-10 Contipro A.S. Self-supporting, biodegradable film based on hydrophobized hyaluronic acid, method of its preparation and use
CZ2015398A3 (en) 2015-06-15 2017-02-08 Contipro A.S. A method of crosslinking polysaccharides by using photolabile protecting groups
CZ306662B6 (en) 2015-06-26 2017-04-26 Contipro A.S. Sulphated polysaccharides derivatives, the method of their preparation, the method of their modification and the use
CZ308106B6 (en) 2016-06-27 2020-01-08 Contipro A.S. Unsaturated derivatives of polysaccharides, preparing and using them
CN116444695B (en) * 2022-12-27 2024-09-06 山东丰金美业科技有限公司 Preparation method of low-cost low-molecular-weight acetylated sodium hyaluronate

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1286510B1 (en) * 1996-11-29 1998-07-15 Cooperativa Centro Ricerche Po BUTYRIC ESTERS WITH ANTI-PROLIFERATIVE ACTIVITY AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM

Also Published As

Publication number Publication date
ITMI20040605A1 (en) 2004-06-29
WO2005092929A1 (en) 2005-10-06
EP1781707A1 (en) 2007-05-09

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