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DE4439575A1 - Pharmaceutical and cosmetic gels, emulsions, creams and films - Google Patents

Pharmaceutical and cosmetic gels, emulsions, creams and films

Info

Publication number
DE4439575A1
DE4439575A1 DE4439575A DE4439575A DE4439575A1 DE 4439575 A1 DE4439575 A1 DE 4439575A1 DE 4439575 A DE4439575 A DE 4439575A DE 4439575 A DE4439575 A DE 4439575A DE 4439575 A1 DE4439575 A1 DE 4439575A1
Authority
DE
Germany
Prior art keywords
gels
hyaluronic acid
emulsions
creams
deacylated
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
DE4439575A
Other languages
German (de)
Inventor
Guenter Prof Dr Westphal
Helgard Wasicki
Leander Schoebel
Ulrich Kluegel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
PERMSELECT GES fur ZELLSTRUKT
Original Assignee
PERMSELECT GES fur ZELLSTRUKT
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 PERMSELECT GES fur ZELLSTRUKT filed Critical PERMSELECT GES fur ZELLSTRUKT
Priority to DE4439575A priority Critical patent/DE4439575A1/en
Publication of DE4439575A1 publication Critical patent/DE4439575A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/042—Gels
    • 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
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • 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
    • 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
    • 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
    • C08J2305/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Molecular Biology (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

Novel gels are prepd. by deacylating hyaluronic acid (HA) with a base in an alcohol and taking up the prod. in purified water or a physiological buffer soln. in a concn. of 1-2 wt.%, where the HA is isolated from animal tissue or produced by biotechnology methods. Also claimed are emulsions, gels, creams or films based on deacetylated HA, where the deacetylated HA is crosslinked with itself or with other biopolymers or synthetic polymers in the presence of an activated dicarboxylic acid in water at "medium" pH values.

Description

Die Erfindung betrifft neuartig vernetzte Hyaluronsäuren nach deren Modifizierung sowie das Vermögen solcher Vernetzungs­ produkte, Fette und/oder bekannte Wirk- bzw. Füllstoffe rever­ sibel einzuschließen.The invention relates to novel cross-linked hyaluronic acids their modification and the ability of such networking products, fats and / or known active ingredients or fillers rever enclose sibel.

Hyaluronsäure (HS) mit durchschnittlichen Molekulargewichten von 5*10⁴ - 5*10⁶ D, alternierend aus Glucuronsäure- und Acetylglucos­ aminbausteinen bestehend und in dieser Reihenfolge über β-1,3 und β-1,4-Bindungen miteinander verknüpft, kann biotechnologisch her­ gestellt oder aus tierischen Geweben gewonnen werden.Hyaluronic acid (HS) with average molecular weights of 5 * 10⁴ - 5 * 10⁶ D, alternately consisting of glucuronic acid and acetylglucos amine units and linked together in this order via β-1,3 and β-1,4 bonds, can be produced biotechnologically or obtained from animal tissues.

Die Herstellung und Gewinnung der HS sind in der Literatur und im Patentschrifttum ausführlich beschrieben worden [u. a.: D. A. Swann, Biochemica et Biophysica Acta 156 (1968) 1730; E. A. Balazs, US-Pat. 4,141,973 (1979); P. Chabrecek et al., Collect. Czech. Chem. Commun. 57 (1992) 2151; A. P. Mac Lennan, J. Gen. Microbiol. 15 (1956) 485; H. Hosoy et. al., J. P. 62-257393 (1987) und 1-67196 (1989); K. K. Brown et. al., US-Pat. 5,316,926 (1994)].The manufacture and extraction of the HS are in the literature and in Patent literature has been described in detail [u. a .: D. A. Swann, Biochemica et Biophysica Acta 156 (1968) 1730; E. A. Balazs, U.S. Pat. 4,141,973 (1979); P. Chabrecek et al., Collect. Czech. Chem. Commun. 57: 2151 (1992); A.P. Mac Lennan, J. Gen. Microbiol. 15 (1956) 485; H. Hosoy et. al., J.P. 62-257393 (1987) and 1-67196 (1989); K.K. Brown et. al., U.S. Pat. 5,316,926 (1994)].

Um die ohnehin vorhandenen vorteilhaften physiologischen Eigenschaften der HS weiter zu optimieren und die Einsatzfelder zu erweitern, wurde das Polysaccharid mit sich selbst oder anderen Biopolymeren oder bekannten synthetischen Polymeren vernetzt. Als Vernetzungsreagenzien werden u. a. erfolgreich Divinylsulfon, Epoxide, Halogenhydrine, Isocyanate, Carbodiimide etc. eingesetzt. [T. C. Laurent et. al., Acta Chem. Scand. 18 (1984) 274; J. Zoki, Japan J. Artificial Organs 12 (1983) 327; E. A. Balazs, US-Pat. 4,636, 524 (1987) und 4,582,865 (1986) sowie DE 35 20 008 C2 (1991); T. Mälson, US-Pat. 4, 716,154 (1987); F. della Valle, US-Pat. 4,957,744 (1990); M. Tsunenaga, US-Pat. 5,137,875 (1992); S. Suzuki, US-Pat. 5,087,446 (1992)].To the already existing advantageous physiological Further optimize the properties of the HS and the fields of application expand, the polysaccharide was with itself or others Crosslinked biopolymers or known synthetic polymers. As Cross-linking reagents are u. a. successful divinyl sulfone, Epoxides, halohydrins, isocyanates, carbodiimides etc. are used. [T. C. Laurent et. al., Acta Chem. Scand. 18 (1984) 274; J. Zoki, Japan J. Artificial Organs 12 (1983) 327; E. A. Balazs, U.S. Pat. 4,636, 524 (1987) and 4,582,865 (1986) and DE 35 20 008 C2 (1991); T. Mälson, U.S. Pat. 4, 716, 154 (1987); F. della Valle, U.S. Pat. 4,957,744 (1990); M. Tsunenaga, U.S. Pat. 5,137,875 (1992); S. Suzuki, U.S. Pat. 5,087,446 (1992)].

Die Erfindung stellt sich die Aufgabe, neue Emulsionen, wasserlös­ liche Cremes, Gele und filmartige Produkte auf Basis modifizierter HS zur Verfügung zu stellen.The invention has as its object new water-soluble emulsions Liche creams, gels and film-like products based on modified To provide HS.

Diese Aufgabe wird gelöst, indem HS zunächst deacetyliert und dann mit sich selbst oder anderen Polymeren in Gegenwart aktivierter Dicarbonsäuren vernetzt wird. In die Netzstruktur der so gebildeten Matrices können Fette, bevorzugt mit öliger Konsistenz über physikalische und/oder chemische Wechselwirkungen einge­ schlossen werden.This problem is solved by first deacetylating HS and then activated with itself or other polymers in the presence Dicarboxylic acids are crosslinked. In the network structure of the sun Formed matrices can be fats, preferably with an oily consistency about physical and / or chemical interactions be closed.

Erfindungsgemäß werden Gele hoher Viskosität nach Deacylierung natürlicher HS zur Verfügung gestellt. Ferner werden Produkte mit unterschiedlichen Fließeigenschaften und differenter Plastizität bereitgestellt, die durch Vernetzung deacetylierter HS mit sich selbst oder anderen Biopolymeren oder synthetischen Polymeren in Gegenwart von aktivierten Dicarbonsäuren, bevorzugt Malein- oder Bernsteinsäureanhydrid entstehen. According to the invention, gels become high viscosity after deacylation natural HS provided. Furthermore, products with different flow properties and different plasticity provided by crosslinking deacetylated HS with itself itself or other biopolymers or synthetic polymers in Presence of activated dicarboxylic acids, preferably maleic or Succinic anhydride.  

Schließlich werden mit der Erfindung Emulsionen, Cremes, Gele und filmartige Produkte zur Verfügung gestellt, dadurch gekenn­ zeichnet, daß in die polymeren Matrices Fette von Raublattge­ wächsen, Ölweiden, Samen von Schwarzen Johannisbeeren, Borretsch und/oder Nachtkerzen, besonders Sanddornbeeren eingeschlossen werden. In die zuletzt genannten Stoffkombinationen gehen die Fette als Rohöl, entsäuerte und entlecithinierte Öle durch Um­ setzung mit deacylierter, vernetzter HS in Wasser- bzw. Puffer­ lösungen oder in siedendem phosphat-, soda- bzw. acetatgesättigtem Alkohol ein. Die Verknüpfung der hydrophilen und hydrophoben Komponenten in den Proportionen 5 : 1 bis 1 : 2, vorzugsweise 1 : 1 (w/w) erfolgt auch in Gegenwart von Emulgatoren auf Naturstoff­ basis.Finally, emulsions, creams, gels and provided film-like products, thereby characterized records that in the polymer matrices fats from Raublattge waxes, olive willows, black currant seeds, borage and / or evening primrose, especially sea buckthorn berries will. They go into the last-mentioned combinations Fats as crude oil, deacidified and de-lecithinized oils by Um Settling with deacylated, cross-linked HS in water or buffer solutions or in boiling phosphate, soda or acetate saturated Alcohol. Linking the hydrophilic and hydrophobic Components in the proportions 5: 1 to 1: 2, preferably 1: 1 (f / f) also takes place in the presence of emulsifiers on natural product Base.

Die erfindungsgemäß benannten Produkte sind in die Herstellung von Pharmaka und Kosmetika einzubeziehen.The products named according to the invention are in the manufacture of Include pharmaceuticals and cosmetics.

Im folgenden wird die Erfindung anhand einiger Beispiele näher erläutert:In the following, the invention is illustrated by some examples explains:

Beispiel 1example 1

In 100 ml 1%iger wäßriger Hyaluronsäurelösung trägt man 10 ml einer 25%igen Ammoniaklösung, zuvor vermischt mit 30 ml Methanol, ein. Nach 150 Minuten versetzt man die entstandene viskose Lösung mit acetatgesättigtem Ethanol und trennt den entstandenen Nieder­ schlag ab.10 ml is carried in 100 ml of 1% aqueous hyaluronic acid solution a 25% ammonia solution, previously mixed with 30 ml of methanol, on. After 150 minutes, the resulting viscous solution is added with acetate-saturated ethanol and separates the resulting low tee off.

Beispiel 2Example 2

Man verrührt 15 ml einer 1%igen deacetylierten Hyaluronsäure mit 240 mg Xanthan. In die klare Lösung werden 80 mg Maleinsäure­ anhydrid eingetragen. Nach wenigen Minuten erstarrt das Reaktions­ gemisch zu einer zusammenhängenden hochviskosen Masse.15 ml of a 1% deacetylated hyaluronic acid are mixed with 240 mg xanthan. 80 mg of maleic acid are added to the clear solution anhydride registered. The reaction freezes after a few minutes mix to form a coherent, highly viscous mass.

Beispiel 3Example 3

Analog Beispiel 2 unter Verwendung von Carboxymethylcellulose.Analogously to Example 2 using carboxymethyl cellulose.

Beispiel 4Example 4

Das nach Beispiel 3 gewonnene Produkt wird im Verhältnis 2 : 1 (w/w) mit entsäuertem und entlecithiniertem Sanddornöl zur Reaktion ge­ bracht. Nach 60 Minuten (bei 4g-Ansätzen) entsteht bei Raumtempe­ ratur unter Rühren eine gelblich gefärbte Creme, die nach dem Auf­ tragen auf die Oberhaut schnell von der Haut aufgenommen wird.The product obtained according to Example 3 is in a ratio of 2: 1 (w / w) reaction with deacidified and declecithinated sea buckthorn oil brings. After 60 minutes (with 4g batches) is created at room temperature a yellowish cream with stirring, which after opening wear on the epidermis is quickly absorbed by the skin.

Claims (6)

1. Gele auf Basis Hyaluronsäure, dadurch gekennzeichnet, daß Hyaluronsäure, aus tierischen Geweben isoliert oder biotechno­ logisch gewonnen, mit Basen in Alkoholen deacyliert und danach in gereinigtem Wasser oder physiologischer Puffersalzlösung in einer Konzentration von 1-2% (w/w) aufgenommen werden.1. gels based on hyaluronic acid, characterized in that hyaluronic acid, isolated from animal tissues or obtained biotechnologically, deacylated with bases in alcohols and then taken up in purified water or physiological buffer salt solution in a concentration of 1-2% (w / w) . 2. Gele nach Anspruch 1, dadurch gekennzeichnet, daß die deacylierte Hyaluronsäure mit Rohölen von Raublattge­ wächsen, Ölweiden, Samen von Schwarzen Johannisbeeren, Borretsch oder Nachtkerzen verknüpft und danach mit reinem Wasser oder physiologischer Puffersalzlösung versetzt wird.2. Gels according to claim 1, characterized in that the deacylated hyaluronic acid with crude oils from Raublattge grow, olive willows, seeds of black currant, Borage or evening primrose linked and then with pure Water or physiological buffer salt solution is added. 3. Gele nach Anspruch 1, dadurch gekennzeichnet, daß die deacylierte Hyaluronsäure mit den in Anspruch 2 genannten entsäuerten und entlecithinierten Ölen in siedendem phosphat-, acetat- oder carbonatgesättigtem Alkohol umsetzt.3. Gels according to claim 1, characterized in that the deacylated hyaluronic acid with those mentioned in claim 2 deacidified and deacithinated oils in boiling phosphate, reacting alcohol saturated with acetate or carbonate. 4. Gele oder auch Emulsionen nach Anspruch 2, dadurch gekenn­ zeichnet, daß die deacetylierte Hyaluronsäure in wechselnden Mengen mit den Rohölen in Gegenwart von Emulgatoren auf Basis Milch bzw. Hefe verknüpft.4. gels or emulsions according to claim 2, characterized records that the deacetylated hyaluronic acid in changing Quantities with the crude oils in the presence of emulsifiers based Milk or yeast linked. 5. Emulsionen, Gele, Cremes oder filmartige Produkte auf Basis deacetylierter Hyaluronsäure, dadurch gekennzeichnet, daß man dieses Polysaccharid in wechselnden Mengenverhältnissen mit sich oder anderen Biopolymeren bzw. synthetischen Polymeren in Gegenwart aktivierter Dicarbonsäuren bei mittleren pH-Werten im Wasser vernetzt.5. Emulsions, gels, creams or film-like products based deacetylated hyaluronic acid, characterized in that this polysaccharide in varying proportions himself or other biopolymers or synthetic polymers in Presence of activated dicarboxylic acids at average pH values in the Networked water. 6. Emulsionen, Gele oder Cremes nach Anspruch 5, dadurch gekenn­ zeichnet, daß man die vernetzten Produkte mit den fetten Ölen aus Anspruch 2, 3 und 4 verbindet.6. emulsions, gels or creams according to claim 5, characterized records that the cross-linked products with the fatty oils from claim 2, 3 and 4 connects.
DE4439575A 1994-11-05 1994-11-05 Pharmaceutical and cosmetic gels, emulsions, creams and films Withdrawn DE4439575A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE4439575A DE4439575A1 (en) 1994-11-05 1994-11-05 Pharmaceutical and cosmetic gels, emulsions, creams and films

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE4439575A DE4439575A1 (en) 1994-11-05 1994-11-05 Pharmaceutical and cosmetic gels, emulsions, creams and films

Publications (1)

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DE4439575A1 true DE4439575A1 (en) 1996-05-09

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001085801A1 (en) * 2000-05-10 2001-11-15 Aquisitio S.P.A. Cross-linked polymers useful for the pharmaceutical, medical and cosmetic uses
EP1595528A1 (en) * 2004-05-14 2005-11-16 Fibona Health Products GmbH Hyaferm composites
US10899894B2 (en) 2015-12-29 2021-01-26 Galderma S.A Method for preparing acylated crosslinked glycosaminoglycans
US10954316B2 (en) 2016-05-31 2021-03-23 Galderma Holding SA Method for cleaving amide bonds
US11730691B2 (en) 2019-12-02 2023-08-22 Galderma Holding SA High molecular weight esthetic compositions

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001085801A1 (en) * 2000-05-10 2001-11-15 Aquisitio S.P.A. Cross-linked polymers useful for the pharmaceutical, medical and cosmetic uses
EP1595528A1 (en) * 2004-05-14 2005-11-16 Fibona Health Products GmbH Hyaferm composites
US11708461B2 (en) 2015-12-29 2023-07-25 Galderma Holding SA Method for preparing acylated crosslinked glycosaminoglycans
US11066526B2 (en) 2015-12-29 2021-07-20 Galderma Holding SA Method for cleaving amide bonds
US11198765B2 (en) 2015-12-29 2021-12-14 Galderma Holding SA Hydrolysis of ester bonds in amide crosslinked glycosaminoglycans
US11254792B2 (en) 2015-12-29 2022-02-22 Galderma Holding SA Method for deacetylation of biopolymers
US11530301B2 (en) 2015-12-29 2022-12-20 Galderma Holding SA Carbohydrate crosslinker
US11643509B2 (en) 2015-12-29 2023-05-09 Galderma Holding SA Carbohydrate crosslinker
US10899894B2 (en) 2015-12-29 2021-01-26 Galderma S.A Method for preparing acylated crosslinked glycosaminoglycans
US11780970B2 (en) 2015-12-29 2023-10-10 Galderma Holding S.A. Carbohydrate crosslinker
US11939433B2 (en) 2015-12-29 2024-03-26 Galderma Holding S.A. Method for preparing acylated crosslinked glycosaminoglycans
US10954316B2 (en) 2016-05-31 2021-03-23 Galderma Holding SA Method for cleaving amide bonds
US11730691B2 (en) 2019-12-02 2023-08-22 Galderma Holding SA High molecular weight esthetic compositions

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