WO2011069475A2 - Procédé d'élaboration de dérivé oxydé d'acide hyaluronique et procédé de modification - Google Patents

Procédé d'élaboration de dérivé oxydé d'acide hyaluronique et procédé de modification Download PDF

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Publication number
WO2011069475A2
WO2011069475A2 PCT/CZ2010/000129 CZ2010000129W WO2011069475A2 WO 2011069475 A2 WO2011069475 A2 WO 2011069475A2 CZ 2010000129 W CZ2010000129 W CZ 2010000129W WO 2011069475 A2 WO2011069475 A2 WO 2011069475A2
Authority
WO
WIPO (PCT)
Prior art keywords
hyaluronic acid
water
hyaluronan
oxidized
tempo
Prior art date
Application number
PCT/CZ2010/000129
Other languages
English (en)
Other versions
WO2011069475A3 (fr
Inventor
Radovan Buffa
Sofiane Kettou
Lucie POSPIŠILOVÁ
Gloria Huerta-Angeles
Drahomira CHLÁDKOVÁ
Vladimir Velebny
Original Assignee
Contipro C A.S.
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 Contipro C A.S. filed Critical Contipro C A.S.
Priority to BR112012013955A priority Critical patent/BR112012013955B1/pt
Priority to US13/512,484 priority patent/US9434791B2/en
Priority to EP10812840.6A priority patent/EP2510016B1/fr
Priority to DK10812840.6T priority patent/DK2510016T3/en
Priority to KR1020127017887A priority patent/KR101766693B1/ko
Priority to RU2012125154/05A priority patent/RU2559447C2/ru
Priority to JP2012542356A priority patent/JP5886754B2/ja
Publication of WO2011069475A2 publication Critical patent/WO2011069475A2/fr
Publication of WO2011069475A3 publication Critical patent/WO2011069475A3/fr

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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
    • 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
    • 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
    • A61K31/728—Hyaluronic 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof

Definitions

  • R is hydrogen or any substitute and the co-oxidant is sodium hypochlorite (NaClO) or trichloroisocyanuric acid (TCC).
  • NaClO sodium hypochlorite
  • TCC trichloroisocyanuric acid
  • the hyaluronic acid is an important polysaccharide, composed of two repeating units of P-(l,3)-D-glucuronic acid and -(l,4)-N-acetyl-D-glucosamine.
  • the molecular weight depending on the method of isolation and on the source material, is within the range from 5.10 4 to 5.10 6 g.mol '1 .
  • the hyaluronic acid or its sodium salt hyaluronan is an essential component of connective tissues, synovial fluid of joints, and plays an important role in biological processes, such as hydratation, organization of proteoglycans, cell differentiation, proliferation and angiogenesis.
  • the hyaluronic acid is a considerably hydrophilic polysaccharide and is soluble in water in the form of a salt in the whole range of pH.
  • TEMPO is a relatively stable radical which can exist in reaction in three redox forms. Only the oxidized form of TEMPO is effective for alcohols or geminal diols oxidation.
  • a catalytic amount of TEMPO is added to the reaction and therefore, it is necessary to use a co-oxidant which restores the presence of the TEMPO oxidized form.
  • Oxidation of hyaluronan by use of TEMPO/NaClO system was described in the patent application WO 02/18448 A2. The authors also dealt with interactions of percarboxylated polysaccharides, while forming biological complexes.
  • the physico-chemical properties of the resulting hydrogels have been elucidated by instrumental analyses FT-IR, SEM (scanning electron microscopy) and rheometry. Increasing the oxidation degree of the hyaluronan lead to a corresponding increase of hydrogels compatibility and decrease of water absorption capacity. Dermal fibroblasts were used to study the cell-hydrogel interactions. Both the hydrogels and their degradation products are biocompatible, as proved by the long-term cell viability assay. When cultured with cells, the hydrogel underwent a degradation within 4 weeks, with an obvious loss of cohesiveness. The good biocompatibility and biodegradability was further demonstrated in mice subdermal implantations. Lastly, in vitro and in vivo depositions of extracellular matrix in hydrogels were demonstrated by SEM analysis.
  • the present invention relates to an improvement of a method of selective oxidation of the primary hydroxyl group of the hyaluronic acid in the position 6 of the polysaccharide glucosamine part to aldehyde.
  • the new reaction is performed using a system of 2,2,6,6- -tetramethyl-l-piperidinyloxyl radical TEMPO / co-oxidant.
  • Approaches published up to date have introduced either an aldehydic group to the position 2 and 3 of the hyaluronan glucuronic part, while opening the saccharide ring (scheme 6, structure 2), or a carboxyl group to the position 6 of the hyaluronan glucosamine part (scheme 6, structure 1).
  • the method according to the invention is more advantageous in that the respective oxidation product (structure 3, scheme 6) maintains the structure of conjugated saccharide rings. Ring opening in the product oxidized to dialdehyde (structure 2, scheme 6) gives rise to the chain linearity subreakage" and, therefore, a significant change of the polysaccharide 3- dimensional structure compared to the non-modified hyaluronan. Although in the product oxidized to a carboxylic acid (structure 1, scheme 6) the chain linearity impartbreakage" does not occur, the carboxyl group does not enable such various modification (binding) possibilities like the aldehydic group.
  • the prepared oxidized hyaluronan can be used for binding compounds containing for example an amino group.
  • the binding can be realized either in an imine form or after the reduction in an amine form (reductive amination) (scheme 7):
  • the modification of the hyaluronic acid derivative can be performed by a reaction of the oxidized derivative with an amine of the general formula H 2 N-R or with a hyaluronan substituted by an -R-NH 2 group, wherein R is an alkyl, linear or branched chain CI- C30, optionally containing aromatic or heteroaromatic groups.
  • This amine can be an alkylamine, e.g. butylamine or hexanediamine, amino acid, peptide or polysaccharide containing a free amino group.
  • cross-linked hyaluronan derivatives can be prepared.
  • the cross-linked derivatives can be prepared also by the reaction of an aldehyde with a hyaluronan substituted by an aminoalkyl group HA-alkyl-NH 2 .
  • Example 8 Oxidation of the hyaluronic acid by the TEMPO/TCC system
  • TEMPO (0.01 eq) and TCC (0.2 eq) were added to a hyaluronic acid solution (1%) (O.lg, 20 kDa) in the mixture of DMF/water 70/30. The mixture was stirred for 100 hours at the temperature of -5°C. The solution was then diluted to 0.1 % and dialyzed against the mixture (0.1% NaCl, 0.1% NaHC0 3 ) 3 x 5 liters (once per day) and against distilled water 7 x 5 liters (twice per day). The resulting solution was evaporated and analyzed.
  • the solution was then mixed with NaBH 3 CN (3 eq) in 0.5 ml of water. The mixture was stirred for 24 hours at the temperature of 20°C. The solution was then diluted to 0.1% and dialyzed against the mixture (0.1% NaCl, 0.1% NaHC0 3 ) 3 x 5 liters (once per day) and against distilled water 7 x 5 liters (twice per day). The resulting solution was evaporated and analyzed.
  • the resulting solution was diluted to 0.1% and dialyzed against the mixture (0.1% NaCI, 0.1% NaHC0 3 ) 3 x 5 liters (once per day) and against distilled water 7 x 5 liters (twice per day). The resulting solution was then evaporated and analyzed.

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

Abstract

L'invention concerne un nouveau procédé d'élaboration d'un dérivé hyaluronane à groupe adhéhydique en position (6) de la partie glucosamine de polysaccharide. L'oxydation de l'acide hyaluronique peut s'effectuer au moyen de systèmes TEMPO/NaCIO or TEMPO/TCC dans un environnement protique, avec ou sans la présence de sels anorganiques. L'aldhéhyde ainsi élaboré peut être utilisé pour la liaison d'amines, de diamines, d'acides aminés, de peptides et d'autres composés contenant un groupe amino, par exemple au moyen de l'amination réductive avec NaBH3CN dans l'eau ou dans un système eau-solvant organique. Lorsque diamine ou des composés contenant trois ou plus de trois groupes aminés sont utilisés, il est possible d'élaborer des dérivés hyaluronane réticulés. Des dérivés réticulés peuvent aussi être élaborés par la réaction de l'aldéhyde avec un hyaluronane substitué par un groupe amino-alkyle HA-alkyl-NH2.
PCT/CZ2010/000129 2009-12-11 2010-12-10 Procédé d'élaboration de dérivé oxydé d'acide hyaluronique et procédé de modification WO2011069475A2 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
BR112012013955A BR112012013955B1 (pt) 2009-12-11 2010-12-10 método de preparação do derivado de ácido hialurônico seletivamente oxidado na posição (6) da parte glucosamina do polissacarídeo ao aldeído e método de modificação do derivado de ácido hialurônico
US13/512,484 US9434791B2 (en) 2009-12-11 2010-12-10 Method of preparation of an oxidized derivative of hyaluronic acid and a method of modification thereof
EP10812840.6A EP2510016B1 (fr) 2009-12-11 2010-12-10 Procédé d'élaboration de dérivé oxydé d'acide hyaluronique et procédé de modification
DK10812840.6T DK2510016T3 (en) 2009-12-11 2010-12-10 A process for preparing an oxidized derivative of hyaluronic acid and a process for modifying it
KR1020127017887A KR101766693B1 (ko) 2009-12-11 2010-12-10 히알루론산의 산화된 유도체의 제조 방법 및 이의 변형 방법
RU2012125154/05A RU2559447C2 (ru) 2009-12-11 2010-12-10 Способ получения окисленного производного гиалуроновой кислоты и способ его модификации
JP2012542356A JP5886754B2 (ja) 2009-12-11 2010-12-10 ヒアルロン酸の酸化誘導体の調製方法及びその修飾方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CZPV2009-835 2009-12-11
CZ20090835A CZ2009835A3 (cs) 2009-12-11 2009-12-11 Zpusob prípravy derivátu kyseliny hyaluronové oxidovaného v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd a zpusob jeho modifikace

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WO2011069475A2 true WO2011069475A2 (fr) 2011-06-16
WO2011069475A3 WO2011069475A3 (fr) 2011-08-11

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US (1) US9434791B2 (fr)
EP (1) EP2510016B1 (fr)
JP (1) JP5886754B2 (fr)
KR (1) KR101766693B1 (fr)
BR (1) BR112012013955B1 (fr)
CZ (1) CZ2009835A3 (fr)
DK (1) DK2510016T3 (fr)
HU (1) HUE031497T2 (fr)
PL (1) PL2510016T3 (fr)
RU (1) RU2559447C2 (fr)
WO (1) WO2011069475A2 (fr)

Cited By (18)

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WO2013137755A1 (fr) 2012-03-14 2013-09-19 Nanovelos Sp. Z O.O. Procédé pour la préparation de nanoparticules de polysaccharide
WO2014023272A1 (fr) 2012-08-08 2014-02-13 Contipro Biotech S.R.O. Dérivé d'acide hyaluronique, procédé de préparation de celui-ci, procédé de modification de celui-ci et d'utilisation de celui-ci
WO2014082610A1 (fr) 2012-11-27 2014-06-05 Contipro Biotech S.R.O. Fibres sans fin à base d'hyaluronane sélectivement oxydé en position 6 du groupe n-acétyl-d-glucosamine, leur préparation et utilisation, filés, fibres courtes, fils et tissus constitués de celles-ci et procédé pour la modification de celles-ci
WO2015135511A1 (fr) * 2014-03-11 2015-09-17 Contipro Biotech S.R.O. Conjugués d'oligomère d'acide hyaluronique ou d'un sel de celui-ci, procédé de préparation de celui-ci et utilisation de celui-ci
US20150328328A1 (en) * 2012-12-20 2015-11-19 Pfizer Inc. Glycoconjugation process
US9403918B2 (en) 2009-12-11 2016-08-02 Contipro Pharma A.S. Oxidized derivative of hyaluronic acid, a method of preparation thereof and a method of modification thereof
US9434791B2 (en) 2009-12-11 2016-09-06 Contipro Pharma A.S. Method of preparation of an oxidized derivative of hyaluronic acid and a method of modification thereof
US9492586B2 (en) 2012-02-28 2016-11-15 Contipro Biotech S.R.O. Derivatives of hyaluronic acid capable of forming hydrogels
WO2016202314A1 (fr) 2015-06-15 2016-12-22 Contipro A.S. Procédé de réticulation de polysaccharides à l'aide de groupes protecteurs photoamovibles
WO2016206661A1 (fr) 2015-06-26 2016-12-29 Contipro A.S. Dérivés de polysaccharides sulfatés, procédé de préparation, modification et utilisation correspondants
EP3156044A1 (fr) 2015-10-16 2017-04-19 Merz Pharma GmbH & Co. KGaA Compositions de polysaccharide réticulable in situ et ses utilisations
US9999678B2 (en) 2012-11-27 2018-06-19 Contipro A.S. C6-C18-acylated derivative of hyaluronic acid and method of preparation thereof
WO2020038500A1 (fr) * 2018-08-23 2020-02-27 Contipro A.S. Dérivé chloré d'acide hyaluronique, son procédé de préparation, composition contenant le dérivé et son utilisation
US10618984B2 (en) 2016-06-27 2020-04-14 Contipro A.S. Unsaturated derivatives of polysaccharides, method of preparation thereof and use thereof
US10617711B2 (en) 2014-06-30 2020-04-14 Contipro A.S. Antitumor composition based on hyaluronic acid and inorganic nanoparticles, method of preparation thereof and use thereof
US10689464B2 (en) 2015-03-09 2020-06-23 Contipro A.S. Self-supporting, biodegradable film based on hydrophobized hyaluronic acid, method of preparation and use thereof
WO2020127407A1 (fr) 2018-12-19 2020-06-25 Merz Pharma Gmbh & Co. Kgaa Acide hyaluronique modifié par un aldéhyde, son procédé de préparation et applications associées
US11425907B2 (en) 2018-08-23 2022-08-30 Contipro A.S. Composition comprising an iodide and a derivative of hyaluronic acid with an oxidative effect, method of preparation thereof and use thereof

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CZ304072B6 (cs) * 2011-04-26 2013-09-25 Contipro Biotech S.R.O. Amfoterní materiál na bázi sítované kyseliny hyaluronové, zpusob jeho prípravy, materiály obsahující aktivní cinidla uzavrené v síti hyaluronanu, zpusob jejich prípravy a jejich pouzití
CZ201224A3 (cs) * 2012-01-16 2013-04-03 Contipro Biotech S.R.O. Kyselina hyaluronová znacená tritiem, zpusob znacení kyseliny hyaluronové tritiem a její pouzití
CZ2012844A3 (cs) * 2012-11-27 2014-02-05 Contipro Biotech S.R.O. Fotoreaktivní derivát kyseliny hyaluronové, způsob jeho přípravy, 3D síťovaný derivát kyseliny hyaluronové, způsob jeho přípravy a použití
US9751849B1 (en) 2016-12-06 2017-09-05 King Fahd University Of Petroleum And Minerals Method of producing a furanone compound
US20210008249A1 (en) 2018-03-12 2021-01-14 Merz Pharma Gmbh & Co. Kgaa Porous biomaterials for tissue regeneration

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JP2013513672A (ja) 2013-04-22
WO2011069475A3 (fr) 2011-08-11
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JP5886754B2 (ja) 2016-03-16
BR112012013955B1 (pt) 2020-01-14
US9434791B2 (en) 2016-09-06
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HUE031497T2 (en) 2017-07-28
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