WO2010052430A2 - Composition injectable a base d'acide hyaluronique ou l'un de ses sels, de polyols et de lidocaïne, sterilisee a la chaleur - Google Patents
Composition injectable a base d'acide hyaluronique ou l'un de ses sels, de polyols et de lidocaïne, sterilisee a la chaleur Download PDFInfo
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- WO2010052430A2 WO2010052430A2 PCT/FR2009/052134 FR2009052134W WO2010052430A2 WO 2010052430 A2 WO2010052430 A2 WO 2010052430A2 FR 2009052134 W FR2009052134 W FR 2009052134W WO 2010052430 A2 WO2010052430 A2 WO 2010052430A2
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- gel
- hyaluronic acid
- composition according
- aqueous composition
- lidocaine
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- 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
- A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
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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
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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
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
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- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
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- 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
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- 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
- A61L27/54—Biologically active materials, e.g. therapeutic substances
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- A—HUMAN NECESSITIES
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- 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
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- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0034—Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
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- A61K9/0048—Eye, e.g. artificial tears
- A61K9/0051—Ocular inserts, ocular implants
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
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- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/06—Flowable or injectable implant compositions
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- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/02—Materials or treatment for tissue regeneration for reconstruction of bones; weight-bearing implants
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- A—HUMAN NECESSITIES
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- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/16—Materials or treatment for tissue regeneration for reconstruction of eye parts, e.g. intraocular lens, cornea
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- A61L2430/00—Materials or treatment for tissue regeneration
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- 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
- A61L2430/00—Materials or treatment for tissue regeneration
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- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/34—Materials or treatment for tissue regeneration for soft tissue reconstruction
Definitions
- Injectable composition based on hvaluronic acid or one of its salts, polvols and lidocaine, heat sterilized
- the present invention relates to an injectable aqueous composition in the form of a gel based on hyaluronic acid or a salt thereof, one or more polyol (s) and lidocaine, a heat-sterilized composition having rheological properties of viscoelasticity. improved and long in vivo persistence, for use for aesthetic purposes or for therapeutic purposes.
- Injectable gels based on hyaluronic acid have been used for many years for aesthetic purposes for filling or replacing biological tissues (filling wrinkles, remodeling the face, increasing the volume of the lips, etc.) as well as in the treatment of rehydration of the skin by mesotherapy.
- Injectable gels based on hyaluronic acid are also used in many therapeutic applications. For example,
- WO 2005/012364 discloses polysaccharide-based gels, including hyaluronic acid, crosslinked and grafted, having a better remanence than uncrosslinked and / or ungrafted products.
- WO 2004/092222 discloses polysaccharide-based gels, including hyaluronic acid, comprising at least one low molecular weight polysaccharide and at least one high molecular weight polysaccharide, gels having a higher remanence than products which do not possess mixing of molecular masses.
- - WO 2005/085329 describes a manufacturing process for obtaining polydensified cross-linked hyaluronic acid gels, gels having a long remanence in vivo.
- WO 2000/0046252 describes gels based on hyaluronic acid with a high "biostability" having a high degree of crosslinking by virtue of a process for double crosslinking of hyaluronic acid.
- the polyols belong to a family of molecules of chemical formula C x HyOz which have at least two alcohol groups. Because of their strong ability to adjust osmolarity, one skilled in the art knows that it can introduce polyols into an injectable aqueous formulation to obtain an iso-osmolar composition.
- Lidocaine (or lidocaine hydrochloride) is a local anesthetic commonly used in the aesthetic and medical fields. This molecule has been used for many years in aesthetic products such as wrinkle fillers to limit pain during and after injection (case of Zyderm® product containing collagen and 0.3% lidocaine).
- hyaluronic acid gels which may contain a polyol and / or lidocaine are described.
- WO 2007/077399 describes gels based on hyaluronic acid and a viscous biocompatible alcohol whose sterilization increases the viscosity.
- WO 2004/032943 describes gels based on hyaluronic acid containing local anesthetics including lidocaine.
- WO 98/41171 discloses an injectable composition in the form of a gel based on hyaluronic acid, mannitol and lidocaine.
- WO 2008/068297 describes the use of an injectable implant subcutaneously or intradermally in the form of hyaluronic acid hydrogel. It also discloses the use of mannitol as an antioxidant.
- the viscoelastic properties of a gel based on hyaluronic acid with polyol and lidocaine are identical to those of a hyaluronic acid gel without polyol and without lidocaine.
- the viscoelastic properties of a gel based on hyaluronic acid with polyol and lidocaine are different from those of a hyaluronic acid gel without polyol and without lidocaine.
- the gel with polyol and lidocaine has a higher elasticity (higher G ') and a more elastic viscoelastic character (lower Tan ⁇ ) compared to a gel without polyol and without lidocaine.
- Heat sterilization profoundly modifies the structure of the gel and therefore the viscoelastic properties of the gel (decrease of the rheological parameters G 'and G "/ increase of the parameter Tan ⁇ ). It is found that the presence of a polyol and lidocaine in a gel based on hyaluronic acid considerably modifies the evolution of the rheological parameters during heat sterilization (limitation of the evolution of rheological parameters: decrease of G 'and G "significantly less strong / increase of Tan ⁇ significantly less strong).
- the structure of the hyaluronic acid gel with polyol and lidocaine is different from that obtained with a gel without hyaluronic acid polyol and without lidocaine.
- This structure has in particular a reinforced elastic character (better ability of the gel to create volume).
- This better resistance to thermal degradation in particular gives the gel a better stability of the product at ambient temperature over time.
- a product made according to this invention will have an expiry time that can be extended relative to a product containing no polyol and lidocaine.
- a hyaluronic acid gel with polyol and lidocaine has a better resistance to the three degradation factors of a hyaluronic acid gel in vivo compared to a gel without polyol and without lidocaine.
- lidocaine considerably increases the capacity of a polyol to be protected. a gel based on hyaluronic acid.
- the polyol (s) incorporated (s) in the hyaluronic acid-based gel can migrate out of the gel. Out of the gel, the polyol (s) will be able to diffuse into the tissues and play an important role for example in the hydration of tissues or by intervening in cellular or biochemical mechanisms.
- the injectable aqueous composition based on hyaluronic acid or one of its salts, one or more polyol (s) and lidocaine according to the invention has the following advantages for aesthetic purposes or for therapeutic purposes : - better rheological properties of gel viscoelasticity (especially better ability to create volume) because significantly less degraded to sterilization
- the invention thus provides a heat-sterilized injectable composition
- a heat-sterilized injectable composition comprising a gel based on hyaluronic acid or one of its salts, one or more polyol (s) and lidocaine.
- composition is used: - for aesthetic purposes for the filling of biological tissues or for the rehydration of the skin by mesotherapy
- the gel based on hyaluronic acid or one of its salts is uncrosslinked or crosslinked.
- the concentration of hyaluronic acid or one of its salts is between 0.01 mg / ml and 100 mg / ml and the molecular weight of hyaluronic acid or one of its salts is between 1000 Da and 10 * 10 6 Da.
- the crosslinking is carried out by bi- or poly-functional molecules chosen from epoxides, epihalohydrins and divinylsulfone, on uncrosslinked or already crosslinked hyaluronic acid with or without a or several other polysaccharides of natural origin.
- the gel may also contain other biocompatible polymers (such as polysaccharides of natural origin) and / or other active or non-active substances having a positive effect on the organism or on the skin. gel.
- biocompatible polymers such as polysaccharides of natural origin
- active or non-active substances having a positive effect on the organism or on the skin. gel.
- these gels contain one or more polyols chosen, for example, from glycerol, sorbitol, propylene glycol, xylitol, mannitol, erythritol, maltitol or lactitol.
- the concentration of polyol in the gel is between 0.0001 and 500 mg / ml and more particularly between 0.0001 and 100 mg / ml.
- the concentration of lidocaine in the gel is between 0.0001 and 500 mg / ml and more particularly between 0.001 and 50 mg / ml.
- the sterilization is carried out with dry or wet heat, preferably with moist heat.
- dry or wet heat preferably with moist heat.
- wet heat sterilization cycles may be used: 131 ° C., 1 min / 130 ° C., 3 min / 125 ° C., 7 min / 121 ° C., 20 min / 121 ° C., 10 min. / 100 0 C, 2h.
- EXAMPLES Examples are provided to illustrate the invention but are in no way limiting to said invention.
- the preparation of the crosslinked gels is carried out according to the techniques well known to those skilled in the art.
- the sodium hyaluronate used to make these gels has a molecular weight of 2.5 * 10 6 Da.
- the crosslinking agent used is butanediol diglycidyl ether (BDDE) and the definition of the degree of crosslinking used is: mass (BDDE) / mass (dry NaHA).
- the incorporation of the polyol in the gel is carried out by adding the necessary amount of polyol (% expressed by weight) in the gel and mixing with the spatula for 10 minutes (for 50 g of final gel).
- lidocaine in the gel is carried out by adding the necessary amount of lidocaine (% expressed by weight) in the gel and mixing with the spatula for 10 minutes (for 50 g of final gel).
- the crosslinked gel without polyol and without lidocaine is also mixed with the spatula for 10 minutes (for 50 g of final gel).
- the prepared gels are filled in a glass syringe and then heat-sterilized (121 ° C., 10 min).
- the rheometer used to perform the rheological characterization is an AR2000 (TA instruments) with a flat geometry of 40 mm, a gap of 1000 ⁇ m and an analysis temperature of 37 ° C.
- the gel thus obtained is divided into three fractions of equal mass (50 g).
- B be the fraction # 1.
- 1% glycerol, 1.5% sorbitol and 0.3% lidocaine are added.
- the gel is mixed with the spatula for 10 minutes.
- C be fraction No. 2.
- 1% of glycerol and 1% of sorbitol are added.
- the gel is mixed with the spatula for 10 minutes.
- D be the fraction # 3.
- a solution of NaCl of suitable concentration is added in order to have a concentration of hyaluronic acid and an osmolarity equivalent to those of the gels B and C.
- the gel is mixed with the spatula for 10 minutes.
- the gels thus obtained have a pH close to 7.00, an osmolarity close to 300 mOsm / kg and an equivalent hyaluronic acid concentration.
- a rheology measurement (frequency sweep - 0.01 to 100 Hz) is performed for each of the gels B, C and D before sterilization.
- the gels B, C and D are filled in 1 ml glass syringe and then sterilized in moist heat at 121 0 C for 10 minutes.
- a rheology measurement (frequency sweep - 0.01 to 100 Hz) is carried out for each of the gels B, C and D after sterilization.
- the presence of polyols and lidocaine greatly limited thermal degradation of the hyaluronic acid-based gel during heat sterilization.
- Example 2 Demonstration of the best resistance to enzymatic degradation of a hyaluronic acid-based gel with polyol and lidocaine.
- the resistance to enzymatic degradation of the gel B according to the invention is compared with that of the gel D (see Example 1).
- the degradation test is carried out using an AR2000 rheometer (TA instruments) with a flat geometry of 40 mm and a gap of 1000 ⁇ m.
- the degradation test is performed by adding a solution of hyaluronidases in the gel to be tested, homogenizing with a spatula for 1 minute, placing at the temperature of 37 ° C and imposing a strain of 0.3%.
- the gel according to the invention has a better resistance to enzymatic degradation.
- Example 3 Demonstration of the best resistance to radical degradation of a hyaluronic acid gel with polyol and lidocaine.
- the resistance to the radical degradation of gel B according to the invention (see Example 1), gel C (see Example 1) and gel D (see Example 1) is compared.
- the degradation test is carried out using an AR2000 rheometer (TA instruments) with a flat geometry of 40 mm and a gap of 1000 ⁇ m.
- the degradation test is carried out by adding an oxidant in the gel to be tested, homogenizing with a spatula for 1 minute, placing itself at the temperature of 37 ° C. and imposing a deformation of 0.3%.
- the gel according to the invention has a much better resistance to radical degradation.
- EXAMPLE 4 Demonstration of the Best Resistance to Thermal Degradation of a Hyaluronic Acid Gel with Polyol and Lidocaine The resistance to thermal degradation of gel B according to the invention (see Example 1) and gel D (see Example 1) is compared.
- the gel according to the invention has a better resistance to thermal degradation.
- Gel B according to the invention (see Example 1) and gel D (see Example D) were stored for 8 months at room temperature (25 ° C.).
- the gel according to the invention has a better rheological stability at ambient temperature over time.
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Abstract
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Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020117010080A KR101514831B1 (ko) | 2008-11-07 | 2009-11-04 | 히알루론산 또는 그의 염 중 하나, 폴리올 및 리도카인의 가열 멸균된 주사용 조성물 |
CA2742099A CA2742099C (fr) | 2008-11-07 | 2009-11-04 | Composition injectable a base d'acide hyaluronique ou l'un de ses sels, de polyols et de lidocaine, sterilisee a la chaleur |
US13/119,787 US8455465B2 (en) | 2008-11-07 | 2009-11-04 | Heat sterilised injectable composition of hyaluronic acid or one of the salts thereof, polyols and lidocaine |
PL09768146T PL2349203T5 (pl) | 2008-11-07 | 2009-11-04 | Kompozycja iniekcyjna na bazie kwasu hialuronowego lub jednej z jego soli, polioli i lidokainy, sterylizowana cieplnie |
JP2011535154A JP5626661B2 (ja) | 2008-11-07 | 2009-11-04 | ヒアルロン酸又はその塩の1種、ポリオール及びリドカインの熱滅菌された注射用組成物 |
EP09768146.4A EP2349203B2 (fr) | 2008-11-07 | 2009-11-04 | Composition injectable a base d'acide hyaluronique ou l'un de ses sels, de polyols et de lidocaïne, sterilisée à la chaleur |
RU2011121426/15A RU2493815C2 (ru) | 2008-11-07 | 2009-11-04 | Стерилизуемая путем нагрева инъецируемая композиция, содержащая гиалуроновую кислоту или одну из ее солей, полиолы и лидокаин |
CN2009801423087A CN102196805B (zh) | 2008-11-07 | 2009-11-04 | 透明质酸或其盐之一、多元醇和利多卡因的热灭菌的注射型组合物 |
BRPI0919155A BRPI0919155B8 (pt) | 2008-11-07 | 2009-11-04 | composição aquosa injetável |
ES09768146T ES2443296T5 (es) | 2008-11-07 | 2009-11-04 | Composición inyectable a base de ácido hialurónico o una de sus sales, de polioles y de lidocaína, esterilizada con calor |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FR0857575A FR2938187B1 (fr) | 2008-11-07 | 2008-11-07 | Composition injectable a base d'acide hyaluronique ou l'un de ses sels, de polyols et de lidocaine, sterilisee a la chaleur |
FR0857575 | 2008-11-07 |
Publications (2)
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WO2010052430A2 true WO2010052430A2 (fr) | 2010-05-14 |
WO2010052430A3 WO2010052430A3 (fr) | 2010-10-07 |
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PCT/FR2009/052134 WO2010052430A2 (fr) | 2008-11-07 | 2009-11-04 | Composition injectable a base d'acide hyaluronique ou l'un de ses sels, de polyols et de lidocaïne, sterilisee a la chaleur |
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US (1) | US8455465B2 (fr) |
EP (2) | EP2349203B2 (fr) |
JP (1) | JP5626661B2 (fr) |
KR (1) | KR101514831B1 (fr) |
CN (1) | CN102196805B (fr) |
BR (1) | BRPI0919155B8 (fr) |
CA (1) | CA2742099C (fr) |
DK (1) | DK2676658T3 (fr) |
ES (2) | ES2556475T3 (fr) |
FR (1) | FR2938187B1 (fr) |
PL (2) | PL2676658T3 (fr) |
RU (1) | RU2493815C2 (fr) |
WO (1) | WO2010052430A2 (fr) |
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RU2011121426A (ru) | 2012-12-10 |
PL2349203T5 (pl) | 2021-02-08 |
KR101514831B1 (ko) | 2015-04-24 |
EP2349203A2 (fr) | 2011-08-03 |
JP2012508217A (ja) | 2012-04-05 |
EP2676658A1 (fr) | 2013-12-25 |
US20110201571A1 (en) | 2011-08-18 |
WO2010052430A3 (fr) | 2010-10-07 |
FR2938187A1 (fr) | 2010-05-14 |
FR2938187B1 (fr) | 2012-08-17 |
ES2443296T5 (es) | 2020-10-29 |
CN102196805A (zh) | 2011-09-21 |
PL2349203T3 (pl) | 2014-04-30 |
CA2742099C (fr) | 2017-08-08 |
EP2349203B1 (fr) | 2013-10-30 |
ES2443296T3 (es) | 2014-02-18 |
JP5626661B2 (ja) | 2014-11-19 |
ES2556475T3 (es) | 2016-01-18 |
DK2676658T3 (en) | 2015-12-21 |
KR20110084510A (ko) | 2011-07-25 |
PL2676658T3 (pl) | 2016-07-29 |
CN102196805B (zh) | 2013-10-16 |
EP2349203B2 (fr) | 2020-02-26 |
US8455465B2 (en) | 2013-06-04 |
CA2742099A1 (fr) | 2010-05-14 |
RU2493815C2 (ru) | 2013-09-27 |
BRPI0919155A2 (pt) | 2015-12-08 |
BRPI0919155B1 (pt) | 2019-12-10 |
EP2676658B1 (fr) | 2015-09-16 |
BRPI0919155B8 (pt) | 2021-05-25 |
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