CZ2012537A3 - Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití - Google Patents

Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití

Info

Publication number
CZ2012537A3
CZ2012537A3 CZ2012-537A CZ2012537A CZ2012537A3 CZ 2012537 A3 CZ2012537 A3 CZ 2012537A3 CZ 2012537 A CZ2012537 A CZ 2012537A CZ 2012537 A3 CZ2012537 A3 CZ 2012537A3
Authority
CZ
Czechia
Prior art keywords
hyaluronan
aldehyde
amino
compounds
preparation
Prior art date
Application number
CZ2012-537A
Other languages
English (en)
Other versions
CZ304512B6 (cs
Inventor
Radovan Buffa
Petra Šedová
Lucie Wolfová
Ivana Basarabová
Robert Pospíšil
Martina Hašová
Kristina Nešporová
Vladimír Velebný
Original Assignee
Contipro Biotech S.R.O.
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 Biotech S.R.O. filed Critical Contipro Biotech S.R.O.
Priority to CZ2012-537A priority Critical patent/CZ304512B6/cs
Priority to KR1020157005050A priority patent/KR102060026B1/ko
Priority to JP2015525734A priority patent/JP2015525820A/ja
Priority to US14/420,012 priority patent/US9522966B2/en
Priority to EP13762380.7A priority patent/EP2882779B1/en
Priority to PCT/CZ2013/000091 priority patent/WO2014023272A1/en
Priority to RU2015107312A priority patent/RU2647859C2/ru
Priority to ES13762380.7T priority patent/ES2595755T3/es
Priority to DK13762380.7T priority patent/DK2882779T3/en
Priority to PL13762380T priority patent/PL2882779T3/pl
Priority to BR112015002755-5A priority patent/BR112015002755B1/pt
Priority to HUE13762380A priority patent/HUE031496T2/en
Publication of CZ2012537A3 publication Critical patent/CZ2012537A3/cs
Publication of CZ304512B6 publication Critical patent/CZ304512B6/cs

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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
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • 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
    • A61K47/56—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 macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/61—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 macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K17/00—Carrier-bound or immobilised peptides; Preparation thereof
    • C07K17/02—Peptides being immobilised on, or in, an organic carrier
    • C07K17/10—Peptides being immobilised on, or in, an organic carrier the carrier being a carbohydrate
    • 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
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
    • C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
    • C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C08J3/075—Macromolecular gels
    • 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
    • A61K31/28—Compounds containing heavy metals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Dispersion Chemistry (AREA)
  • Materials Engineering (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Inorganic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Cosmetics (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)

Abstract

Řešení se týká přípravy a použití .alfa.,.beta.-nenasyceného aldehydu hyaluronanu s dvojnou vazbou v polohách 4 a 5 a aldehydickou skupinou v poloze 6 glukosaminové části polysacharidu podle strukturního vzorce X nebo jeho hydratované formy podle strukturního vzorce Y. Způsob přípravy je založen na dehydrataci hyaluronanu s aldehydickou skupinou v poloze 6 glukosaminové části polysacharidu. Byly popsány dvě metody, a to dehydratace v roztoku, anebo zahřátí v suchém stavu bez přítomnosti rozpouštědel, bázi nebo jiných aditiv. Tento derivát umožňuje stabilizovat konjugáty hyaluronanu s aminosloučeninami pomocí násobné vazby ze strany aldehydu, takže na takto modifikovaný hyaluronan je možné efektivně imobilizovat ve fyziologických podmínkách prakticky jakoukoliv sloučeninu obsahující amino skupinu. V případě použití diaminu nebo sloučenin případně polymerů s obsahem tří nebo víc aminoskupin, je možné připravit síťované deriváty hyaluronanu. Popsané řešení dává významnou výhodu nejenom v oblasti nosičů biologicky aktivních látek, ale také ve tkáňovém inženýrství, kde je síťování s biologicky akceptovatelnými amino sloučeninami ve fyziologických podmínkách velmi žádané.
CZ2012-537A 2012-08-08 2012-08-08 Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití CZ304512B6 (cs)

Priority Applications (12)

Application Number Priority Date Filing Date Title
CZ2012-537A CZ304512B6 (cs) 2012-08-08 2012-08-08 Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití
KR1020157005050A KR102060026B1 (ko) 2012-08-08 2013-08-05 히알루론산 유도체, 이의 제조 방법, 이의 변형 방법, 및 이의 용도
JP2015525734A JP2015525820A (ja) 2012-08-08 2013-08-05 ヒアルロン酸誘導体，その調製方法，修飾方法及び使用
US14/420,012 US9522966B2 (en) 2012-08-08 2013-08-05 Hyaluronic acid derivative, method of preparation thereof, method of modification thereof and use thereof
EP13762380.7A EP2882779B1 (en) 2012-08-08 2013-08-05 Hyaluronic acid derivative, method of preparation thereof, method of modification thereof and use thereof
PCT/CZ2013/000091 WO2014023272A1 (en) 2012-08-08 2013-08-05 Hyaluronic acid derivative, method of preparation thereof, method of modification thereof and use thereof
RU2015107312A RU2647859C2 (ru) 2012-08-08 2013-08-05 Производное гиалуроновой кислоты, способ его получения, способ его модификации и его применение
ES13762380.7T ES2595755T3 (es) 2012-08-08 2013-08-05 Derivado de ácido hialurónico, método de preparación del mismo, método de modificación del mismo y utilización del mismo
DK13762380.7T DK2882779T3 (en) 2012-08-08 2013-08-05 Hyaluronic Acid Derivative, Process for Preparation thereof, Process for Modification and Use thereof
PL13762380T PL2882779T3 (pl) 2012-08-08 2013-08-05 Pochodna kwasu hialuronowego, sposób jej wytwarzania, sposób jej modyfikacji i jej zastosowanie
BR112015002755-5A BR112015002755B1 (pt) 2012-08-08 2013-08-05 Derivado de ácido hialurônico, método de preparação de derivado de ácido hialurônico e uso de derivados
HUE13762380A HUE031496T2 (en) 2012-08-08 2013-08-05 Hyaluronic acid derivative, a process for its preparation, a method for its modification and its use

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CZ2012-537A CZ304512B6 (cs) 2012-08-08 2012-08-08 Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití

Publications (2)

Publication Number Publication Date
CZ2012537A3 true CZ2012537A3 (cs) 2014-03-19
CZ304512B6 CZ304512B6 (cs) 2014-06-11

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CZ2012-537A CZ304512B6 (cs) 2012-08-08 2012-08-08 Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití

Country Status (12)

Country Link
US (1) US9522966B2 (cs)
EP (1) EP2882779B1 (cs)
JP (1) JP2015525820A (cs)
KR (1) KR102060026B1 (cs)
BR (1) BR112015002755B1 (cs)
CZ (1) CZ304512B6 (cs)
DK (1) DK2882779T3 (cs)
ES (1) ES2595755T3 (cs)
HU (1) HUE031496T2 (cs)
PL (1) PL2882779T3 (cs)
RU (1) RU2647859C2 (cs)
WO (1) WO2014023272A1 (cs)

Cited By (10)

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Publication number Priority date Publication date Assignee Title
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
US9522966B2 (en) 2012-08-08 2016-12-20 Contipro Biotech S.R.O. Hyaluronic acid derivative, method of preparation thereof, method of modification thereof and use thereof
US9999678B2 (en) 2012-11-27 2018-06-19 Contipro A.S. C6-C18-acylated derivative of hyaluronic acid and method of preparation thereof
US10414832B2 (en) 2015-06-26 2019-09-17 Contipro A.S Derivatives of sulfated polysaccharides, method of preparation, modification and use thereof
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
US10759878B2 (en) 2015-06-15 2020-09-01 Contipro A.S. Method of crosslinking of polysaccharides using photoremovable protecting groups

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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
FI3623390T3 (fi) * 2015-12-29 2023-10-30 Galderma Holding SA Hiilihydraattisilloittaja
AU2018240375C1 (en) 2017-03-22 2024-02-01 Ascendis Pharma A/S Hydrogel cross-linked hyaluronic acid prodrug compositions and methods
DE102018124022A1 (de) 2018-09-28 2020-04-02 Rheinisch-Westfälische Technische Hochschule (Rwth) Aachen Hyaluronsäurestabilisator
KR102225971B1 (ko) * 2020-05-19 2021-03-10 주식회사 차메디텍 펩타이드 가교제를 이용한 히알루론산 기반의 하이드로겔 및 이의 제조 방법
CN112030566B (zh) * 2020-09-30 2022-10-21 山东华熙海御生物医药有限公司 一种依克多因缓释微囊及其制备方法和应用
CN112851966A (zh) * 2020-12-31 2021-05-28 深圳市光韵达增材制造研究院 双改性化合物及其制备方法、生物胶水及其制备方法
CN113087819A (zh) * 2021-03-12 2021-07-09 深圳市光韵达增材制造研究院 一种双改性化合物及其制备方法和应用
CN115636884B (zh) * 2022-12-23 2023-03-28 北京格林意锐医药科技有限责任公司 一种透明质酸钠衍生物制备方法及交联透明质酸钠和用途
CN117304368B (zh) * 2023-11-29 2024-03-01 杭州湃肽生化科技有限公司 一种透明质酸钠与胶原五肽的组合物及其应用

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