DK2682409T3 - Hyaluronsyrederivat modificeret med aminocarboxylsyre - Google Patents

Hyaluronsyrederivat modificeret med aminocarboxylsyre Download PDF

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Publication number
DK2682409T3
DK2682409T3 DK12752403.1T DK12752403T DK2682409T3 DK 2682409 T3 DK2682409 T3 DK 2682409T3 DK 12752403 T DK12752403 T DK 12752403T DK 2682409 T3 DK2682409 T3 DK 2682409T3
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Denmark
Prior art keywords
hyaluronic acid
acid derivative
hydrogen atom
ppm
shows
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DK12752403.1T
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English (en)
Inventor
Tomoko Yasugi
Yoshihiro Tampo
Kenji Yasugi
Tai Hirakura
Tsuyoshi Shimoboji
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Chugai Pharmaceutical Co Ltd
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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
    • 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
    • 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Dermatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Preparation (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Materials For Medical Uses (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

Claims (8)

1. Hyaluronsyrederivat omfattende disaccharidenheder gengivet ved formlen (I):
hvor R1, R2, R3 og R4 hver især er uafhængigt udvalgt blandt et hydrogenatom, Ci-6-alkyl, formyl og Ci-e-alkylcarbonyl; R8 er et hydrogenatom, formyl eller Ci-6-alkylcarbonyl; X er gengivet ved følgende formler:
hvor "*" betegner et bindingssted til carboxygruppen i hyaluronsyrederivatet, hvor andelen af disaccharidenheder med formlen (1) ud af disaccharidgentagelsesenhe- derne, der er til stede i hyaluronsyrederivatet, andrager mindst 70 %.
2. Hyaluronsyrederivat ifølge krav 1, yderligere omfattende disaccharidenheder gengivet ved formlen (II):
hvor Rla, R2a, R3a og R4a hver især er uafhængigt udvalgt blandt et hydrogenatom, Ci-6-alkyl, formyl og Ci-e-alkylcarbonyl; R8a er et hydrogenatom, formyl eller Ci-6-alkylcarbonyl; Xa er udvalgt blandt hydroxy og -0"Q+, hvor Q+ står for en modkation.
3. Hyaluronsyrederivat ifølge et hvilket som helst af kravene 1 eller 2, yderligere omfattende disaccharidenheder gengivet ved formlen (III):
hvor Rlb, R2b, R3b, og R4b hver især er uafhængigt udvalgt blandt et hydrogenatom, Ci-6-alkyl, formyl og Ci-6-alkylcarbonyl; R8b er et hydrogenatom, formyl eller Ci-6-alkylcarbonyl; Xb er en gruppe gengivet ved -NRe-Yb-Rd; hvor Re er et hydrogenatom eller Ci-6-alkyl; Rd er et hydrogenatom, Ci-e-alkyl, -CO-C(R7)=CH2, eller -C0-G4-Xc; R7 er et hydrogenatom eller methyl; G4 er udvalgt blandt phenylen, C3-8-cykloalkylen og -G5-(Ci io-alkylen)-G6-, hvor Ci-io-alkylen-delen kan have en til tre phenylener eller C3-8-cy kloa I ky lener indsat i sig; G5 og G6 hver især er uafhængigt udvalgt blandt en direkte binding, phenylen, eller C3-8-cykloalkylen; Xc er mercapto, et halogenatom eller en gruppe gengivet ved formlen: £ 3 Yb er -CH2-(CHR5)i-2-CH2-NH-, -CH2-(CHR6)p.2-CH2-0-, -(CH2)rS-, eller -(CH2)a-(Y1-(CH2)b)c-G-; 1, p, og j er hver især uafhængigt et heltal udvalgt blandt 2 til 10, R5 og R6 er hver især uafhængigt et hydrogenatom eller hydroxy; a er et heltal udvalgt blandt 2 til 10; hvert enkelt b er uafhængigt et heltal udvalgt blandt 2 til 10; c er et heltal udvalgt blandt 1 til 200; Y1 er et oxygenatom eller -NRn-; G er et oxygenatom, et svovlatom eller -NH-; Rn er et hydrogenatom, Ci-e-alkyl, -CO-(CH2)d-R°, -(CH2)e-Rp eller -(CH2)f-(Y2-(CH2)g)h-Rq; hvert enkelt g er uafhængigt et heltal udvalgt blandt 2 til 10; d, e, f og h er hver især uafhængigt et heltal udvalgt blandt 2 til 10; R°, Rp og Rq er hver især uafhængigt et hydrogenatom, hydroxy, carboxy eller -NHRr; Y2 er et oxygenatom eller -NH-; og Rr er et hydrogenatom, formyl eller Ci-6-alkylcarbonyl.
4. Hyaluronsyrederivat ifølge et hvilket som helst af kravene 1 til 3, som er fremstillet under anvendelse af hyaluronsyre, der udelukkende er sammensat af disaccharidenhederne, som hver især er gengivet ved formel (II) som anført i krav 2, hvor vægtmiddelmolekylvægten er i området 20-120 kilodalton, når Rla, R2a, R3a og R4a alle er hydrogenatomer, R8a er acetyl, og Xa er -0'Na+.
5. Hyaluronsyrederivat ifølge et hvilket som helst af kravene 1 til 4, hvor en uafledt hyaluronsyre svarende til hyaluronsyrederivatet med hensyn til skeletstrukturen har en vægtmiddelmolekylvægt på 20-120 kilodalton, hvor den uafledte hyaluronsyre er hyaluronsyre sammensat udelukkende af disaccharidenheder med formlen (II) som anført i krav 2, hvor Rla, R2a, R3a og R4a er hydrogenatomer, R8a er acetyl, og Xa er -0'Na+.
6 Farmaceutisk sammensætning omfattende hyaluronsyrederivatet ifølge et hvilket som helst af kravene 1 til 5 som bæremiddel.
7. Hyaluronsyrederivat/lægemiddel-konjugat, hvor et eller flere lægemidler er konjugeret til hyaluronsyrederivatet ifølge et hvilket som helst af kravene 1 til 5.
8. Bionedbrydeligt lægemiddelbæremiddel omfattende hyaluronsyrederivatet ifølge et hvilket som helst af kravene 1 til 5.
DK12752403.1T 2011-03-03 2012-03-02 Hyaluronsyrederivat modificeret med aminocarboxylsyre DK2682409T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011046749 2011-03-03
PCT/JP2012/055421 WO2012118189A1 (ja) 2011-03-03 2012-03-02 アミノ－カルボン酸により修飾されたヒアルロン酸誘導体

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DK2682409T3 true DK2682409T3 (da) 2017-09-11

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US (1) US9243077B2 (da)
EP (2) EP3184553B1 (da)
JP (2) JP6141180B2 (da)
DK (1) DK2682409T3 (da)
ES (1) ES2635087T3 (da)
HU (1) HUE033169T2 (da)
PL (1) PL2682409T3 (da)
SI (1) SI2682409T1 (da)
WO (1) WO2012118189A1 (da)

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EP3263604A4 (en) * 2015-02-27 2018-11-21 Josho Gakuen Educational Foundation Polysaccharide derivative having membrane-permeable peptide chain
WO2016159159A1 (ja) * 2015-03-31 2016-10-06 キユーピー株式会社 ヒアルロン酸誘導体およびその製造方法、ならびにヒアルロン酸誘導体を含む化粧料、食品組成物および医薬組成物
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EP3252080A1 (en) * 2016-05-31 2017-12-06 Galderma S.A. Method for preparing acylated crosslinked glycosaminoglycans
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Publication number Publication date
PL2682409T3 (pl) 2017-12-29
EP3184553A1 (en) 2017-06-28
JP6141180B2 (ja) 2017-06-07
JP2017179374A (ja) 2017-10-05
WO2012118189A1 (ja) 2012-09-07
EP3184553B1 (en) 2019-05-01
US20130338352A1 (en) 2013-12-19
SI2682409T1 (sl) 2017-08-31
EP2682409A1 (en) 2014-01-08
JPWO2012118189A1 (ja) 2014-07-07
US9243077B2 (en) 2016-01-26
ES2635087T3 (es) 2017-10-02
HUE033169T2 (en) 2017-11-28
EP2682409A4 (en) 2014-11-19
EP2682409B1 (en) 2017-07-05

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