DK2510016T3 - En fremgangsmåde til fremstilling af et oxideret derivat af hyaluronsyre og en fremgangsmåde til modifikation deraf - Google Patents
En fremgangsmåde til fremstilling af et oxideret derivat af hyaluronsyre og en fremgangsmåde til modifikation deraf Download PDFInfo
- Publication number
- DK2510016T3 DK2510016T3 DK10812840.6T DK10812840T DK2510016T3 DK 2510016 T3 DK2510016 T3 DK 2510016T3 DK 10812840 T DK10812840 T DK 10812840T DK 2510016 T3 DK2510016 T3 DK 2510016T3
- Authority
- DK
- Denmark
- Prior art keywords
- hyaluronic acid
- oxidized
- hyaluronan
- water
- mixture
- Prior art date
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Classifications
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- 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
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- 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
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- 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
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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)
Claims (15)
1. Fremgangsmåde til fremstilling af et derivat af hyaluronsyre oxideret i positionen 6 i glucosamindelen af polysaccharidet selektivt til aldehyd, hvori hyaluronsyren reagerer med 4-R-TEMPO, hvor R er en lineær eller forgrenet kæde med 1 til 50 atomer, valgfrit indeholdende aromatiske eller heteroaromatiske grupper, 4-R-TEMPO er til stede i en mængde indenfor intervallet fra 0,005 til 0,5 ækvivalenter i forhold til hyaluronandimeren, og en co-oxidant er til stede i en mængde indenfor intervallet fra 0,05 til 1 ækvivalent i forhold til hyaluronandimeren, hvor fremstillingen er ved temperaturen indenfor intervallet fra -10 til 20 'O i 5 minutter til 24 timer i et protisk opløsningsmiddel, der indbefatter vand og vandige opløsninger af salte med en generel formel MX, hvor M er et alkalimetal og X er valgt fra gruppen indbefattende HC03", C032", PO43", HPO42', H2PO4" og halogener, hvori koncentrationen af de vandige saltopløsninger er 0 til 15 vægt-%.
2. Fremgangsmåde til fremstilling ifølge krav 1, hvori co-oxidanten indbefatter natriumhypochlorit.
3. Fremgangsmåde til fremstilling ifølge krav 1, hvori hyaluronsyren er i form af en fri syre eller et salt.
4. Fremgangsmåde til fremstilling ifølge ethvert af kravene 1 til 3, hvori hyaluronsyremolekylvægten er indenfor intervallet fra T104 til 5-106 g.mol'1.
5. Fremgangsmåde til fremstilling ifølge ethvert af kravene 1 til 4, hvori reaktion af hyaluronsyren, 4-R-TEMPO og co-oxidanten udføres ved temperaturen 0 °C i 10 timer.
6. Fremgangsmåde til modifikation af hyaluronsyrederivatet fremstillet med fremgangsmåden ifølge ethvert af kravene 1 til 5, hvori det oxiderede hyaluronsyrederivat reagerer med en amin med den generelle formel H2N-R eller med en hyaluronan substitueret med en -R-NH2 gruppe, hvor R er en alkyl, lineær eller forgrenet C1 - C30, valgfrit indeholdende aromatiske eller heteroaromatiske grupper.
7. Fremgangsmåde til modifikation ifølge krav 6, hvori det oxiderede hyaluronsyrederivat reagerer med en aminosyre.
8. Fremgangsmåde til modifikation ifølge krav 6, hvor det oxiderede hyaluronsyrederivat reagerer med et peptid.
9. Fremgangsmåde til modifikation ifølge krav 6, hvori det oxiderede hyaluronsyrederivat reagerer med et polysaccharid indeholdende en fri aminogruppe.
10. Fremgangsmåde til modifikation ifølge ethvert af kravene 6 til 9, hvori mængden af aminen, aminosyren, peptidet eller polysaccharidet er indenfor intervallet fra 0,05 til 10 ækvivalenter i forhold til hyaluronandimeren.
11. Fremgangsmåde til modifikation ifølge ethvert af kravene 6 til 10, hvori reaktionen af det oxiderede hyaluronsyrederivat med aminen, aminosyren, peptidet eller polysaccharidet udføres i vand eller i et system af vand-organisk opløsningsmiddel ved temperaturen indenfor intervallet fra 0 til 80 °C, fortrinsvis ved 20 °C, i 1 minut til 24 timer, fortrinsvis i 1 time.
12. Fremgangsmåde til modifikation ifølge krav 11, hvori reaktionen af det oxiderede hyaluronsyrederivat med aminen, aminosyren, peptidet eller polysaccharidet udføres i nærværelse af NaBH3CN som et reduktionsmiddel, der sættes til reaktionsblandingen på tiden 0 til 100 timer efter tilsætningen af aminen, aminosyren, peptidet eller polysaccharidet.
13. Fremgangsmåde til modifikation ifølge krav 12, hvori mængden af NaBH3CN som et reduktionsmiddel er indenfor intervallet fra 0 til 20 molækvivalenter i forhold til molmængden af aldehydet eller geminaldiolen.
14. Fremgangsmåde til modifikation ifølge ethvert af kravene 11 til 13, hvori det organiske opløsningsmiddel er valgt fra gruppen bestående af vandblandbare alkoholer, især isopropanol eller ethanol, og vandblandbare polære aprote opløsningsmidler, især dimethylsulfoxid.
15. Fremgangsmåde til modifikation ifølge ethvert af kravene 11 til 14, hvori vandmængden er på mindst 50% (v/v) i forhold til hele opløsningens volumen.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CZ20090835A CZ302503B6 (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 |
PCT/CZ2010/000129 WO2011069475A2 (en) | 2009-12-11 | 2010-12-10 | A method of preparation of an oxidized derivative of hyaluronic acid and a method of modification thereof |
Publications (1)
Publication Number | Publication Date |
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DK2510016T3 true DK2510016T3 (da) | 2016-10-10 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DK10812840.6T DK2510016T3 (da) | 2009-12-11 | 2010-12-10 | En fremgangsmåde til fremstilling af et oxideret derivat af hyaluronsyre og en fremgangsmåde til modifikation deraf |
Country Status (11)
Country | Link |
---|---|
US (1) | US9434791B2 (da) |
EP (1) | EP2510016B1 (da) |
JP (1) | JP5886754B2 (da) |
KR (1) | KR101766693B1 (da) |
BR (1) | BR112012013955B1 (da) |
CZ (1) | CZ302503B6 (da) |
DK (1) | DK2510016T3 (da) |
HU (1) | HUE031497T2 (da) |
PL (1) | PL2510016T3 (da) |
RU (1) | RU2559447C2 (da) |
WO (1) | WO2011069475A2 (da) |
Families Citing this family (23)
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CZ302504B6 (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 |
CZ302503B6 (cs) | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Zpusob prípravy derivátu kyseliny hyaluronové oxidovaného v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd a zpusob jeho modifikace |
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 |
CZ303879B6 (cs) | 2012-02-28 | 2013-06-05 | Contipro Biotech S.R.O. | Deriváty na bázi kyseliny hyaluronové schopné tvorit hydrogely, zpusob jejich prípravy, hydrogely na bázi techto derivátu, zpusob jejich prípravy a pouzití |
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CZ304512B6 (cs) * | 2012-08-08 | 2014-06-11 | Contipro Biotech S.R.O. | Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití |
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CZ304654B6 (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 |
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 |
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CZ2014150A3 (cs) * | 2014-03-11 | 2015-05-20 | Contipro Biotech S.R.O. | Konjugáty oligomeru kyseliny hyaluronové nebo její soli, způsob jejich přípravy a použití |
CZ2014451A3 (cs) | 2014-06-30 | 2016-01-13 | Contipro Pharma A.S. | Protinádorová kompozice na bázi kyseliny hyaluronové a anorganických nanočástic, způsob její přípravy a použití |
CZ309295B6 (cs) | 2015-03-09 | 2022-08-10 | Contipro A.S. | Samonosný, biodegradabilní film na bázi hydrofobizované kyseliny hyaluronové, způsob jeho přípravy a použití |
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-
2009
- 2009-12-11 CZ CZ20090835A patent/CZ302503B6/cs unknown
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2010
- 2010-12-10 PL PL10812840T patent/PL2510016T3/pl unknown
- 2010-12-10 DK DK10812840.6T patent/DK2510016T3/da active
- 2010-12-10 WO PCT/CZ2010/000129 patent/WO2011069475A2/en active Application Filing
- 2010-12-10 BR BR112012013955A patent/BR112012013955B1/pt active IP Right Grant
- 2010-12-10 US US13/512,484 patent/US9434791B2/en active Active
- 2010-12-10 EP EP10812840.6A patent/EP2510016B1/en active Active
- 2010-12-10 JP JP2012542356A patent/JP5886754B2/ja active Active
- 2010-12-10 RU RU2012125154/05A patent/RU2559447C2/ru active
- 2010-12-10 KR KR1020127017887A patent/KR101766693B1/ko active IP Right Grant
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Also Published As
Publication number | Publication date |
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PL2510016T3 (pl) | 2017-02-28 |
RU2012125154A (ru) | 2014-01-20 |
JP2013513672A (ja) | 2013-04-22 |
US9434791B2 (en) | 2016-09-06 |
BR112012013955A2 (pt) | 2016-06-07 |
EP2510016A2 (en) | 2012-10-17 |
WO2011069475A2 (en) | 2011-06-16 |
WO2011069475A3 (en) | 2011-08-11 |
EP2510016B1 (en) | 2016-08-24 |
US20120264913A1 (en) | 2012-10-18 |
RU2559447C2 (ru) | 2015-08-10 |
KR101766693B1 (ko) | 2017-08-09 |
JP5886754B2 (ja) | 2016-03-16 |
KR20120095463A (ko) | 2012-08-28 |
HUE031497T2 (en) | 2017-07-28 |
CZ2009835A3 (cs) | 2011-06-22 |
CZ302503B6 (cs) | 2011-06-22 |
BR112012013955B1 (pt) | 2020-01-14 |
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