EP1611160A2 - Vernetzung von polysacchariden mit niedrigem und hohem molekulargewicht, verfahren zur herstellung von injizierbaren einphasigen hydrogelen, sowie so erhaltene polysaccharide und hydrogele - Google Patents

Vernetzung von polysacchariden mit niedrigem und hohem molekulargewicht, verfahren zur herstellung von injizierbaren einphasigen hydrogelen, sowie so erhaltene polysaccharide und hydrogele

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Publication number
EP1611160A2
EP1611160A2 EP04742458A EP04742458A EP1611160A2 EP 1611160 A2 EP1611160 A2 EP 1611160A2 EP 04742458 A EP04742458 A EP 04742458A EP 04742458 A EP04742458 A EP 04742458A EP 1611160 A2 EP1611160 A2 EP 1611160A2
Authority
EP
European Patent Office
Prior art keywords
advantageously
polymer
molecular weight
crosslinking
salt
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.)
Ceased
Application number
EP04742458A
Other languages
English (en)
French (fr)
Inventor
Pierre Lebreton
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.)
Allergan Industrie SAS
Original Assignee
Corneal Industrie SA
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=33186443&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP1611160(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Corneal Industrie SA filed Critical Corneal Industrie SA
Priority to EP20100181594 priority Critical patent/EP2289945B1/de
Priority to EP20140200048 priority patent/EP2868669A1/de
Publication of EP1611160A2 publication Critical patent/EP1611160A2/de
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/738—Cross-linked polysaccharides
    • 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
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14—Macromolecular materials
    • A61L27/20—Polysaccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/52—Hydrogels or hydrocolloids
    • 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
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • 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

Definitions

  • Crosslinking of low and high molecular weight polysaccharides preparation of injectable monophasic hydroqels; polysaccharides and hydro ⁇ els obtained.
  • the subject of the present invention is:
  • hydrogels in question based on said crosslinked polymers, have numerous outlets, in particular as filling material in restorative, aesthetic, dental surgeries, in ophthalmology, in orthopedics ... as a product preventing tissue adhesions, in general surgery, urology ... Said hydrogels are particularly suitable for repairing the vocal cords.
  • outlets indicated above, in a nonlimiting manner, for this type of product, are familiar to those skilled in the art.
  • the invention results from a real effort to optimize the implementation of the crosslinking of the polymers in question, with a view to obtaining injectable monophasic hydrogels, which are particularly advantageous with reference to the compromise below: mechanical properties and persistence, on the one hand, injectability (with injection forces and acceptable injection needle diameters), on the other hand.
  • the injectable qualifier used in the present text means manually injectable by means of syringes fitted with conventional needles (of a diameter between 0.1 and 0.5 mm).
  • hydrogels injectable through hypodermic needles of 30 G 1. , 27 G 1 /., 26 G 1 /., 25 G.
  • compositions With reference to the specific problem of injectability, two-phase compositions have been proposed, the continuous phase of which in particular is based on such hydrogels. Said continuous phase serves as a plasticizer, as an injection vehicle for a dispersed phase. This dispersed phase is more or less solid, more or less differentiated from the continuous phase. So :
  • the biphasic compositions described consist of two phases - continuous, dispersed - bioresorbable and are in the form of sludge. Said two phases are advantageously prepared from Hylan fibers (natural hyaluronic acid chemically modified in situ in order to facilitate its extraction from the tissues), - in application WO-A-96 337 51, the biphasic compositions described also have two bioresorbable phases, better separated, the dispersed phase consisting of insoluble fragments of a polymer hydrogel (chosen from hyaluronic acid and its salts), highly crosslinked; - In application WO-A-00 014 28, the biphasic compositions described contain a dispersed phase, not bioresorbable (particles of at least one hydrogel of a (co) polymer obtained by polymerization and crosslinking of acrylic acid and / or methacrylic acid and / or at least one derivative of said acids), in suspension in an aqueous solution
  • the product in question is not an injectable hydrogel but a product of solid consistency.
  • eye implants are in fact described, used to temporarily fill a vacuum created surgically.
  • the hydrogel produced is proposed as a substitute for the vitreous body.
  • the polymer in question sodium hyaluronate
  • the monophasic hydrogel described is charged with an antiseptic, effective to protect it, after implantation, against free radicals.
  • WO-A-02 063 50 a process is described, capable of generating this type of hydrogel, very homogeneous in its mass.
  • All these monophasic hydrogels were obtained from polymers of high molecular mass, crosslinked with the intervention of an effective and not excessive amount of at least one crosslinking agent, in aqueous solvent.
  • the inventors wished to improve the efficiency of the crosslinking of the polymer in question so as in particular to improve the resistance to degradation (the persistence) of the implanted hydrogel, while retaining the possibility of injecting said hydrogel under acceptable conditions.
  • the inventors first thought of involving more crosslinking agent. This approach was quickly discarded insofar as it inevitably leads to denaturation of the polymer in question and chemical pollution of the crosslinked product obtained. Said inventors then thought of increasing the concentration of polymer in the reaction mixture.
  • the inventors have surprisingly established that by combining low molecular weight polymer (s) and high molecular weight polymer (s), an excellent compromise is obtained, namely the possibility of generating, for a non-excessive crosslinking rate (equivalent to that of the prior art) a monophasic, injectable hydrogel with improved mechanical properties and remanence.
  • This low mass / high mass association makes it possible to obtain a hydrogel which more than satisfactorily meets the following specifications: - monophasic,
  • the key factor of the crosslinking process of the invention therefore resides in the concentration of the reagents (which is increased compared to that of the reaction mixtures of the prior art, due to the intervention of low molecular weight polymer (s). ), the crosslinking of said concentrated reagents being however "controlled” by the intervention of polymer (s) of high molecular weight, which guarantee the homogeneity of the crosslinked product and then of the hydrogel obtained.
  • the present invention therefore relates to a process for crosslinking at least one polymer chosen from polysaccharides and their derivatives, used in aqueous solvent by action of an effective and not excessive amount of at least one crosslinking agent, improved in that it is used on a mixture containing at least one low molecular weight polymer and at least one high molecular weight polymer.
  • Said mixture naturally includes the said (s) polymer (s) of low molecular weight in sufficient quantity to guarantee a relatively high concentration of the reaction medium in polymer (s) and the said (s) polymer (s) ) of high molecular mass in an amount sufficient to guarantee a homogeneous consistency to said crosslinked polymer obtained.
  • the crosslinking method of the invention is a method of crosslinking polymers chosen from polysaccharides and their derivatives.
  • the polymer (s) in question can therefore not be natural or synthetic.
  • natural polymers are hyaluronic acid and its salts, other glycosaminoglycans, such as chondroitin sulfates, keratan sulfate, heparin, heparan sulfate, alginic acid and its biologically acceptable salts, starch, amylose, dextran, xanthan, pullulan ...
  • Examples of synthetic derivatives of natural polysaccharides are carboxyoixose, carboxymethylcellutose, alkylcelluloses, such as hydroxyethylcellulose, hydroxypropylmethylcellulose (HPMC) , oxidized starch ...
  • the process of the invention is likely to be suitable for the crosslinking of any one of these polymers, insofar as said polymer intervenes at low (s) and high (s) molecular weights.
  • the process of the invention is likely to be suitable for the crosslinking of mixtures of such polymers, said mixtures containing at least one low molecular weight polymer and at least one high molecular weight mixture.
  • the reaction medium contains a single polymer, which is involved in at least two differentiated molecular weights: at least one weak and at least one strong.
  • the same polymer is preferably used at a single low molecular weight and at a single high molecular weight.
  • the polymer in question is advantageously a salt of hyaluronic acid. It is very advantageously chosen from the sodium salt, the potassium salt and their mixtures. It preferably consists of the sodium salt (NaHA).
  • crosslinking of this type of polymer a person skilled in the art understands that said crosslinking is carried out in a basic aqueous solvent. In general, said crosslinking is obviously carried out under pH conditions favorable to the dissolution of the polymer in question.
  • reaction mixture contains:
  • said reaction mixture advantageously has an intrinsic viscosity of less than 1,900 ml / g, ie
  • the reaction mixture advantageously contains more than 50%, very advantageously more than 70%, by mass of at least one salt of hyaluronic acid of low molecular mass m and therefore, logically, advantageously less than 50%, very advantageously less than 30%, by mass of at least one salt of hyaluronic acid of high molecular mass M.
  • crosslinking method of the invention is advantageously implemented with the sodium salt of hyaluronic acid, intervening at a low molecular mass m and at a high molecular mass M. We then very advantageously have: m ⁇ 3.10 5 Da and M ⁇ 3.10 6 Da.
  • crosslinking agent with all types of polymer, any agent known to crosslink polysaccharides and their derivatives can be used, via its hydroxyl functions - crosslinking agent at least bifunctional, to ensure crosslinking - and in particular an epoxy or its derivatives. We recommend the intervention of crosslinking agents, bifunctional, alone or in mixture.
  • crosslinking agent s
  • ⁇ crosslinking rate
  • ⁇ _ Total number of reactive functions of said crosslinking agent ⁇ ⁇ QQ Total number of disaccharide units of the polymer molecules between 0.5 and 70%, advantageously between 4 and 50%.
  • crosslinking process of the invention is original due to the forms of intervention of the polymers in question. Otherwise, it is implemented in a conventional manner with at least one crosslinking agent. It is noted that said crosslinking agent is generally reacted on the dissolved polymer (s). It is however in no way excluded that it intervenes on the said polymer (s) during hydration, according to the process described in WO-A-02 06 350.
  • the crosslink obtained at the end of the implementation of the crosslinking process of the invention is generally formulated to generate the desired injectable monophasic hydrogel. It is if necessary neutralized beforehand.
  • the formulation is implemented in a buffered solution at a pH compatible with the human body (since the hydrogel in question is generally intended for injection into the human body): pH between 6.5 and 7.5 advantageously between 7 and 7.4, very advantageously between 7.1 and 7.3.
  • the crosslinked polymer equilibrates. It also acquires an osmolarity compatible with that of the human body ...
  • the crosslinked polymers of the invention diluted are monophasic hydrogels.
  • an injectable hydrogel of the invention is prepared, by crosslinking a mixture of at least one polymer, salt (s) of hyaluronic acid (see above), by neutralizing the reticulate obtained, then by formulating it in a buffered solution at a pH between 7.1 and 7.3, at a concentration between 10 and 40 mg / g, advantageously between 20 and 30 mg / g.
  • the process for preparing the injectable monophasic hydrogel from the crosslinked polymer constitutes the second object of the present invention.
  • third and fourth objects consist respectively of the crosslinked polymer capable of being obtained after the implementation of the crosslinking process (first object) and the injectable monophasic hydrogel capable of being obtained by formulation. (second object) of said crosslinked polymer, as specified above.
  • Said polymer and hydrogel advantageously contain low molecular weight sodium hyaluronate and high molecular weight sodium hyaluronate; said low molecular weight sodium hyaluronate very advantageously occurring at more than 50% by mass.
  • the structure of the injectable monophasic hydrogel - fourth object of the present invention - is original. Its consistency resists degradation. This resistance of the hydrogel is much higher than that of equivalent products of the prior art.
  • hydrogels of the invention have the outlets indicated in the introduction to this text. They are particularly effective there. It is now proposed to illustrate the invention in its various aspects, by the examples below. More precisely, we have:
  • Example 1 which illustrates the prior art (crosslinking of a high molecular weight polymer)
  • Example 2 which illustrates the remarks made in the introduction to this text (crosslinking of the same low molecular weight polymer)
  • the intrinsic viscosity of sodium hyaluronate (NaHA) (in ml / g) is determined in accordance with the European Pharmacopoeia of NaHA (2.2.9), by a capillary viscometer of Ubelhode type.
  • the injectability of the NaHA-based gel is determined by measuring the force required (in Newton, N) to eject the gel contained in a standard syringe, through a 27 GVz needle, at a speed of 12.5 mm / min. The tests were carried out on a Verstatet ® traction device sold by the company Mecmésin.
  • the consistency of the gel is characterized at 25 ° C. by a rheological measurement of the elastic (G 1 ) and viscous (G ") modules as a function of the frequency (from 0.05 to 10 Hz) and in the fields of constant deformation, at using a constrained constraint rheometer (Carrimed CSL 500 from TA Instruments) and a cone / plane geometry 4 cm 2 ° This rheometer is checked and calibrated regularly
  • the gels are degraded by being brought to the temperature of 93 °. vs.
  • Macroscopic aspect flexible and continuous
  • Macroscopic aspect "puree" which fragments very easily - no cohesion of the gel nor of shooting aspect.
  • NaHA sodium hyaluronate fibers
  • the reaction lasts 2 h.
  • [NaHA] f NaHA concentration in the final hydrogel after reaction and dilution with a quantity qs of phosphate buffer
  • hydrogels of the invention (examples 3 and 4) have a rheological behavior different from that of the hydrogel of the prior art (example 1).

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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)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Transplantation (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Molecular Biology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Materials For Medical Uses (AREA)
  • Medicinal Preparation (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
EP04742458A 2003-04-10 2004-04-08 Vernetzung von polysacchariden mit niedrigem und hohem molekulargewicht, verfahren zur herstellung von injizierbaren einphasigen hydrogelen, sowie so erhaltene polysaccharide und hydrogele Ceased EP1611160A2 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP20100181594 EP2289945B1 (de) 2003-04-10 2004-04-08 Vernetzung von Natriumhyaluronaten mit niedrigem und hohem Molekulargewicht, Herstellung von einspritzbaren einzelphasigen Hydrogelen, sowie damit hergestellte vernetztes Natriumhyaluronat und Hydrogel
EP20140200048 EP2868669A1 (de) 2003-04-10 2004-04-08 Vernetztes natriumhyaluronat mit differenzierter niedriger und hoher molekularmasse und dem enthaltenden injizierbaren monophasischen hydrogel

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0304444A FR2861734B1 (fr) 2003-04-10 2003-04-10 Reticulation de polysaccharides de faible et forte masse moleculaire; preparation d'hydrogels monophasiques injectables; polysaccharides et hydrogels obtenus
PCT/FR2004/000870 WO2004092222A2 (fr) 2003-04-10 2004-04-08 Reticulation de polysaccharides de faible et forte masse moleculaire; preparation d'hydrogels monophasiques injectables; polysaccharides et hydrogels obtenus;

Related Child Applications (2)

Application Number Title Priority Date Filing Date
EP20140200048 Division EP2868669A1 (de) 2003-04-10 2004-04-08 Vernetztes natriumhyaluronat mit differenzierter niedriger und hoher molekularmasse und dem enthaltenden injizierbaren monophasischen hydrogel
EP20100181594 Division EP2289945B1 (de) 2003-04-10 2004-04-08 Vernetzung von Natriumhyaluronaten mit niedrigem und hohem Molekulargewicht, Herstellung von einspritzbaren einzelphasigen Hydrogelen, sowie damit hergestellte vernetztes Natriumhyaluronat und Hydrogel

Publications (1)

Publication Number Publication Date
EP1611160A2 true EP1611160A2 (de) 2006-01-04

Family

ID=33186443

Family Applications (3)

Application Number Title Priority Date Filing Date
EP04742458A Ceased EP1611160A2 (de) 2003-04-10 2004-04-08 Vernetzung von polysacchariden mit niedrigem und hohem molekulargewicht, verfahren zur herstellung von injizierbaren einphasigen hydrogelen, sowie so erhaltene polysaccharide und hydrogele
EP20140200048 Withdrawn EP2868669A1 (de) 2003-04-10 2004-04-08 Vernetztes natriumhyaluronat mit differenzierter niedriger und hoher molekularmasse und dem enthaltenden injizierbaren monophasischen hydrogel
EP20100181594 Revoked EP2289945B1 (de) 2003-04-10 2004-04-08 Vernetzung von Natriumhyaluronaten mit niedrigem und hohem Molekulargewicht, Herstellung von einspritzbaren einzelphasigen Hydrogelen, sowie damit hergestellte vernetztes Natriumhyaluronat und Hydrogel

Family Applications After (2)

Application Number Title Priority Date Filing Date
EP20140200048 Withdrawn EP2868669A1 (de) 2003-04-10 2004-04-08 Vernetztes natriumhyaluronat mit differenzierter niedriger und hoher molekularmasse und dem enthaltenden injizierbaren monophasischen hydrogel
EP20100181594 Revoked EP2289945B1 (de) 2003-04-10 2004-04-08 Vernetzung von Natriumhyaluronaten mit niedrigem und hohem Molekulargewicht, Herstellung von einspritzbaren einzelphasigen Hydrogelen, sowie damit hergestellte vernetztes Natriumhyaluronat und Hydrogel

Country Status (8)

Country Link
US (9) US7741476B2 (de)
EP (3) EP1611160A2 (de)
JP (1) JP4827727B2 (de)
BR (1) BRPI0409762B1 (de)
CA (1) CA2521961C (de)
ES (1) ES2536564T3 (de)
FR (1) FR2861734B1 (de)
WO (1) WO2004092222A2 (de)

Cited By (1)

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US9144631B2 (en) 2003-01-27 2015-09-29 Benedicte Asius Ceramic-based injectable implants which are used to fill wrinkles, cutaneous depressions and scars, and preparation method thereof

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US7741476B2 (en) 2010-06-22
WO2004092222A3 (fr) 2004-12-09
US20120295870A1 (en) 2012-11-22
US20190022130A1 (en) 2019-01-24
FR2861734B1 (fr) 2006-04-14
CA2521961C (en) 2013-07-23
US9062130B2 (en) 2015-06-23
US20100226988A1 (en) 2010-09-09
US8338388B2 (en) 2012-12-25
ES2536564T3 (es) 2015-05-26

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