DK2510017T3 - Oxideret derivat af hyaluronansyre, en fremgangsmåde til fremstilling deraf og en fremgangsmåde til modifikation deraf - Google Patents

Oxideret derivat af hyaluronansyre, en fremgangsmåde til fremstilling deraf og en fremgangsmåde til modifikation deraf Download PDF

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Publication number
DK2510017T3
DK2510017T3 DK10812976.8T DK10812976T DK2510017T3 DK 2510017 T3 DK2510017 T3 DK 2510017T3 DK 10812976 T DK10812976 T DK 10812976T DK 2510017 T3 DK2510017 T3 DK 2510017T3
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Denmark
Prior art keywords
hyaluronic acid
oxidized
method
acid derivative
process
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DK10812976.8T
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English (en)
Inventor
Radovan Buffa
Sofiane Kettou
Lucie Pospisilová
Miroslava Némcov
Vladimir Velebn
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Contipro Pharma A S
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Priority to CZ20090836A priority Critical patent/CZ2009836A3/cs
Application filed by Contipro Pharma A S filed Critical Contipro Pharma A S
Priority to PCT/CZ2010/000128 priority patent/WO2011069474A2/en
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Publication of DK2510017T3 publication Critical patent/DK2510017T3/da

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08BPOLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006Heteroglycans, 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
    • C08B37/0063Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
    • C08B37/0072Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates

Claims (16)

1. Hyaluronsyrederivat, oxideret ved glucosamindelens position 6 til et aldehyd ifølge formlen X, og dets hydrerede form, den såkaldte geminaldiol ifølge formlen Y:
2. Fremgangsmåde til fremstilling af hyaluronsyrederivatet ifølge krav 1, hvori hyaluronsyren reagerer med Dess-Martin periodinan (DMP) i en polær aprotisk solvent, særligt i dimethylsulfoxid.
3. Fremgangsmåde til fremstilling af hyaluronsyrederivatet ifølge krav 2, hvori hyaluronsyren er i formen af en frie syre eller et salt.
4. Fremgangsmåde til fremstilling af hyaluronsyrederivatet ifølge ethvert af kravene 2 eller 3, hvori hyaluronsyrens molekylevægt er inden for intervallet fra 1-104 til 5-106 g-mol'1.
5. Fremgangsmåde til fremstilling af hyaluronsyrederivatet ifølge ethvert af kravene 2 til 4, hvori hyaluronsyrens reaktion med Dess-Martin periodinan (DMP) udføres ved temperaturen inden for intervallet fra 10 til 50'C, fortrinsvis ved 20^, i 5 minutter til 150 timer, fortrinsvis i mindst 10 timer.
6. Fremgangsmåde til fremstilling af hyaluronsyrederivatet ifølge ethvert af kravene 2 til 5, hvori DMP er til stede i en mængde inden for intervallet fra 0,05 til 1 ækvivalent i forhold til hyaluronsyredimeren.
7. Fremgangsmåde til modifikation af hyaluronsyrederivatet fremstillet ved anvendelse af fremgangsmåden ifølge ethvert af kravene 2 til 6, hvori det oxiderede hyaluronsyrederivat reagerer med en amin med den generelle formel H2N-R eller med en hyaluronan substitueret med en -R-NH2 gruppe, hvori R er en alkyl, lineær eller forgrenet kæde Ci - C30, valgfrit indeholdende aromatiske eller heteroaromatiske grupper.
8. Fremgangsmåde til modifikation ifølge krav 7, hvori det oxiderede hyaluronansyrederivat reagerer med en aminosyre.
9. Fremgangsmåde til modifikation ifølge krav 7, hvori det oxiderede hyaluronansyrederivat reagerer med et peptid.
10. Fremgangsmåde til modifikation ifølge krav 7, hvori det oxiderede hyaluronansyrederivat reagerer med et polysaccharid indeholdende en fri aminogruppe.
11. Fremgangsmåde til modifikation ifølge ethvert af kravene 7 til 10, hvori mængden af aminen, aminosyren, peptidet eller polysaccharidet er inden for intervallet fra 0,05 til 10 ækvivalenter i forhold til hyaluronandimeren.
12. Fremgangsmåde til modifikation ifølge ethvert af kravene 7 til 11, hvori det oxiderede hyaluronsyrederivats reaktion med aminen, aminosyren, peptidet eller polysaccharidet udføres i vand eller i et vand-organisk solventsystem ved temperaturen inden for intervallet fra 0 til 80°C, fortrinsvis ved 20*Ό, i 1 minut til 24 timer, fortrinsvis i 1 time.
13. Fremgangsmåde til modifikation ifølge krav 12, hvori det oxiderede hyaluronsyrederivats reaktion med aminen, aminosyren, peptidet eller polysaccharidet udføres i tilstedeværelsen af NaBH3CN som et reduktionsmiddel, der tilsættes reaktionsblandingen i tiden 0 til 100 timer efter tilsætningen af aminen, aminosyren, peptidet eller poysaccharidet.
14. Fremgangsmåde til modifikation ifølge krav 13, hvori mængden af NaBH3CN som reduktionsmidlet er inden for intervallet fra 0 til 20 molrækvivalenter i forhold til molarmængden af aldehydet eller geminaldiolen.
15. Fremgangsmåde til modifikation ifølge ethvert af kravene 12 til 14, hvori den organiske solvent er valgt fra gruppen omfattende vandblandbare alkoholer, særligt isopropanol eller ethanol, og vandblandbare polære aprote solventer, særligt dimethylsulfoxid.
16. Fremgangsmåde til modifikation ifølge ethvert af kravene 12 til 15, hvori mængden af vand er mindst 50 % (v/v) i forhold til hele opløsningens volumen.
DK10812976.8T 2009-12-11 2010-12-10 Oxideret derivat af hyaluronansyre, en fremgangsmåde til fremstilling deraf og en fremgangsmåde til modifikation deraf DK2510017T3 (da)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CZ20090836A CZ2009836A3 (cs) 2009-12-11 2009-12-11 Derivát kyseliny hyaluronové oxidovaný v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd, zpusob jeho prípravy a zpusob jeho modifikace
PCT/CZ2010/000128 WO2011069474A2 (en) 2009-12-11 2010-12-10 Oxidized derivative of hyaluronic acid, a method of preparation thereof and a method of modification thereof

Publications (1)

Publication Number Publication Date
DK2510017T3 true DK2510017T3 (da) 2015-03-23

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US (1) US9403918B2 (da)
EP (1) EP2510017B1 (da)
JP (1) JP5945504B2 (da)
KR (1) KR101710432B1 (da)
BR (1) BR112012013954A2 (da)
CZ (1) CZ2009836A3 (da)
DK (1) DK2510017T3 (da)
ES (1) ES2531292T3 (da)
RU (1) RU2550602C2 (da)
WO (1) WO2011069474A2 (da)

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CZ2009836A3 (cs) 2009-12-11 2011-06-22 Contipro C A.S. Derivát kyseliny hyaluronové oxidovaný v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd, zpusob jeho prípravy a zpusob jeho modifikace
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CZ2012843A3 (cs) * 2012-11-27 2014-02-05 Contipro Biotech S.R.O. Nekonečná vlákna na bázi hyaluronanu, selektivně oxidovaného v poloze 6 N-acetyl-D-glukosaminové části, jejich příprava, použití, nitě, střiže, příze, textilie a způsob jejich úpravy
CZ2012842A3 (cs) 2012-11-27 2014-08-20 Contipro Biotech S.R.O. Nanomicelární kompozice na bázi C6-C18-acylovaného hyaluronanu, způsob přípravy C6-C18-acylovaného hyaluronanu, způsob přípravy nanomicelární kompozice a stabilizované nanomicelární kompozice a použití
KR101664444B1 (ko) 2013-12-13 2016-10-12 재단법인 유타 인하 디디에스 및 신의료기술개발 공동연구소 생분해성 의료용 접착제 또는 실란트 조성물
CZ305153B6 (cs) * 2014-03-11 2015-05-20 Contipro Biotech S.R.O. Konjugáty oligomeru kyseliny hyaluronové nebo její soli, způsob jejich přípravy a použití
CZ2015398A3 (cs) 2015-06-15 2017-02-08 Contipro A.S. Způsob síťování polysacharidů s využitím fotolabilních chránicích skupin
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US9403918B2 (en) 2016-08-02
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ES2531292T3 (es) 2015-03-12
WO2011069474A3 (en) 2013-03-14
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