EP2155154A2 - Pharmazeutische oder kosmetische präparate zur topischen und/oder parenteralen anwendung, verfahren zu ihrer herstellung und ihre anwendung - Google Patents

Pharmazeutische oder kosmetische präparate zur topischen und/oder parenteralen anwendung, verfahren zu ihrer herstellung und ihre anwendung

Info

Publication number
EP2155154A2
EP2155154A2 EP08788213A EP08788213A EP2155154A2 EP 2155154 A2 EP2155154 A2 EP 2155154A2 EP 08788213 A EP08788213 A EP 08788213A EP 08788213 A EP08788213 A EP 08788213A EP 2155154 A2 EP2155154 A2 EP 2155154A2
Authority
EP
European Patent Office
Prior art keywords
hyaluronic acid
inhibitor
degradation
pharmaceutical
acid
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Withdrawn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
EP08788213A
Other languages
English (en)
French (fr)
Inventor
Marc Moutet
Jean-Claude Yadan
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.)
Galderma Research and Development SNC
Original Assignee
Galderma Research and Development SNC
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 Galderma Research and Development SNC filed Critical Galderma Research and Development SNC
Publication of EP2155154A2 publication Critical patent/EP2155154A2/de
Withdrawn legal-status Critical Current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
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/63—Steroids; Derivatives thereof
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • 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
    • A61Q19/08—Anti-ageing preparations

Definitions

  • compositions for topical and / or parenteral application comprising, in a physiologically acceptable medium, at least one inhibitor of the degradation of hyaluronic acid and an oligosaccharide, processes for the production of such compositions, and their uses.
  • pharmaceutical compositions in particular of pharmaceutical or cosmetic compositions.
  • Said compositions are intended for the treatment of dermatological conditions, in particular, the filling treatment of wrinkles, fine lines, fibroblastic depletions and any scarring.
  • the aging of the skin is one of the most visible changes in the senescence process.
  • the skin is exposed to many factors that can accelerate this physiological process.
  • intrinsic aging which is easier to evaluate in areas that are normally not exposed to the sun and, on the other hand, extrinsic aging, caused by the interaction of environmental factors, in particular UV rays. These environmental factors have a much more marked effect on sun-exposed body parts, especially in light-skinned people.
  • actinic aging Other factors such as eating habits, smoking, excessive alcohol consumption, Chronic diseases and dysfunctions of the endocrine glands also contribute to this aging.
  • the stratum corneum is little modified.
  • the epidermis is atrophic and the dermal-epidermal junction is flattened, so that adhesion to the dermis is less good, facilitating the formation of bubbles.
  • the thickness of the dermis is significantly reduced; there are fewer blood vessels. There are also fewer fibroblasts and their biosynthesis and proliferation abilities are diminished.
  • the elastic fibers undergo modifications first, and then disappear.
  • Wrinkles are the most visible signs of aging. We can distinguish it from several natures, in particular superficial and deep wrinkles. Deep wrinkles may be due to dermo-hypodermic changes, while superficial wrinkles could be explained by dermal and possibly epidermal changes. Wrinkles are mainly due to the loss of elasticity of the skin. The reaching of the network elastic subepidermal gives rise to a superficial laxity of the aged skin and a fold of its surface. The destruction of elastic fibers in the reticular dermis is responsible for the loss of elasticity and the ability of the skin to regain its shape after stretching. Depending on the type, intensity and topography, a suitable treatment will be possible.
  • dermal implants that is to say as substances injected directly into the skin, in order to remedy the skin changes resulting from aging. , trauma or disease.
  • Botulinum toxin inactivated (Botox®) or the use of laser techniques. These different types of treatment are not exclusive and their combination has even been recommended.
  • collagen and hyaluronic acid are the ones that are at the origin of the majority of the products available on the market.
  • Hyaluronic acid is a ubiquitous natural polysaccharide that exists in the same form from the simplest bacterium to humans. It is a polysaccharide composed alternately of D-glucuronic acid and N- acetylglucosamine, linked together by alternating glycosidic bonds beta-1,4 and beta-1,3. According to Saari H et al. Differential effects of reactive oxygen species on a native synovial fluid and purified human umbilical cord hyaluronate.
  • the polymers of this repeating unit can have a size between 10 2 and 10 4 kDa m vivo, the hyaluronic acid taken from the umbilical cord having a weight of 2500 kDa.
  • Hyaluronic acid is a natural component of the dermis where it plays an important role in the hydration and elasticity of the skin. However, it decreases in quantity and quality with age, resulting in drying of the skin that wrinkles. It is highly water soluble and forms high viscosity solutions in water. Because of these particular properties, hyaluronic acid is one of the most widely used pharmaceutical products.
  • hyaluronic acid is very quickly eliminated from plasma by degradation. Its plasma half-life after intravenous injection is very short, between 2.5 and 5.5 minutes, while in the skin, its half-life is 0.5 to 2 days depending on its concentration. Its urogenic excretion is low, less than 1% of total clearance.
  • the rate of elimination in the skin was measured (Reed RK, Laurent UB, JR Fraser, Laurent TC.) Removal rate of [3H] hyaluronan injected subcutaneously m rabbits Am J Physiol 1990 Aug; 259 (2Pt 2): H532-5). It is non-exponential with a half-life of 0.5 to 1 day when its concentration is 5 mg / ml. The tolerance of hyaluronic acid is very good and no immunogenicity has been associated with this substance. This has a very low incidence of side effects.
  • hyaluronic acid alone or in combination
  • injectable compositions such as, for example, hyaluronic acid alone, collagen alone or the combination "hyaluronic acid and collagen" have already been used in reconstructive surgery, as part of treatment by filling wrinkles, fine lines, fibroblastic depletions and all scars.
  • hyaluronic acid because of its low bioavailability after injection and its too high injection frequency, can not be used as such.
  • compositions based on hyaluronic acid having a very good bioavailability and likely to better withstand the action of degradation enzymes. This allows, in particular, to space interventions and reduce their number.
  • compositions used as a dermal implant are all composed of stabilized hyaluronic acid and a large number of them comprise hyaluronic acid chemically modified for this purpose.
  • hyaluronic acid included in these products is predominantly of non-human origin such as for example of avian or bacterial origin.
  • compositions there are numerous hyaluronic acid derivatives chemically modified in the form, in particular of esters, of amides, as well as derivatives having "intra and / or interchain bridges".
  • a problem to be solved by the invention is to provide compositions which make it possible to provide hyaluronic acid with better bioavailability while retaining its physico-chemical characteristics and its biological properties, as well as a method of manufacturing such compositions.
  • the solution of the invention to this problem has for first object a pharmaceutical or cosmetic composition, especially for topical and / or parenteral application comprising, in a physiologically acceptable medium, as sole active ingredients:
  • this composition does not comprise retinoid nor its salts nor its derivatives.
  • Its second object is a process for producing such a composition, comprising a step of mixing at least one oligosaccharide and at least one inhibitor of the degradation of hyaluronic acid with a physiologically acceptable medium.
  • the method according to the invention also comprises a step of preparing a physiologically acceptable medium, in which the active ingredients are mixed.
  • its third object is the use of at least one inhibitor of the degradation of hyaluronic acid and of at least one oligosaccharide chosen from oligomers of hyaluronic acid, or a composition according to the invention. , for the manufacture of a medicament for the treatment and / or prevention of dermatological conditions.
  • a composition according to the invention significantly increases the bioavailability of a hyaluronic acid, which is furthermore included in said composition, or which is administered separately.
  • the composition according to the invention makes it possible to space the applications of hyaluronic acid and to reduce the number thereof and it has a significant effectiveness in the filling of wrinkles, fine lines, fibroblastic depletions and all scars.
  • the Applicant has also demonstrated a decrease in catabolism of hyaluronic acid in vivo human keratinocytes to which hyaluronic acid, an oligosaccharide and an inhibitor of the degradation of hyaluronic acid are applied, in the absence of rétmoide.
  • the absence of retinoid in a composition comprising an oligosaccharide and an inhibitor of the degradation of hyaluronic acid gives the hyaluronic acid also applied a better stability, a better bioavailability.
  • compositions of the prior art are therefore more effective than the compositions of the prior art, and in particular compositions comprising retinoids, in the filling of wrinkles, fine lines, fibroblastic depletions and all scars, as well as in the hydration of the skin.
  • Figure 1 shows in a semi-logarithmic the results of a study to assess the inhibitory effect of glycyrrhizin on bovine hyaluronidase activity.
  • composition according to the invention comprises, in a physiologically acceptable medium, at least one oligosaccharide, and at least one inhibitor of the degradation of hyaluronic acid.
  • a physiologically acceptable medium at least one oligosaccharide, and at least one inhibitor of the degradation of hyaluronic acid.
  • it does not include retinoid nor its salts or drifts.
  • composition according to the invention may further comprise hyaluronic acid.
  • the composition according to the invention may be administered to a subject to whom hyaluronic acid is independently administered.
  • the hyaluronic acid may be included in a separate composition, which may be administered simultaneously or in a different time from that of the administration of the composition according to the invention.
  • the distinct composition comprising hyaluronic acid can be administered topically, orally or parenterally, for example by injection.
  • Physiologically acceptable medium means a medium compatible with the skin and optionally with its integuments (eyelashes, nails, hair) and / or mucous membranes.
  • compositions according to the invention the oligosaccharide and the inhibitor of the degradation of hyaluronic acid and, where appropriate, hyaluronic acid, are present in proportions ranging from 0.0000001% to 10%, preferably from 0.00001% to 1% by weight, relative to the total weight of the composition. In the present description, and unless otherwise specified, it is understood that when concentration ranges are given, they include the upper and lower limits of said range.
  • the compositions according to the invention may comprise hyaluronic acid.
  • hyaluronic acid is meant a ubiquitous natural polysaccharide existing in the same form from the simplest bacterium to humans. It is a polysaccharide composed alternately of D-glucuronic acid and N-acetylglucosamine, linked together by alternating glycoside bonds beta-1,4 and beta-1,3. According to Saari H et al. Differential effects of reactive oxygen species on a native synovial fluid and pu ⁇ fied human umbilical cord hyaluronate.
  • the polymers of this repeating unit can have a size between 10 2 and 10 4 kDa in vivo, the hyaluronic acid taken from the umbilical cord having a weight of 2500 kDa.
  • hyaluronic acid is natural.
  • hyaluronic acid By natural hyaluronic acid is meant a non-stabilized hyaluronic acid, not chemically modified in the form, especially of esters, amides, or in the form of derivatives having "intra and / or interchain bridges" (cross linked), such modifications affecting the physico-chemical characteristics and the biological properties of said hyaluronic acid, as well as its fate after administration.
  • compositions according to the invention comprise an oligosaccharide.
  • oligosaccharide polymers formed of a number n (with n less than or equal to 100) of monosaccharides by glycosidic bonding, in particular any oligosaccharide limiting the penetration of hyaluronic acid into the cells of the skin, in particular keratinocytes and fibroblasts.
  • the oligomers of hyaluronic acid preferentially the di-dodecamers of hyaluronic acid, will be chosen, said dimer comprising a disaccharide unit. component of hyaluronic acid, and the dodecamere comprising six of these disaccharide units, more preferably the tetra- to hexamers of hyaluronic acid, more preferably the pentamere of hyaluronic acid.
  • the molecular weight of a disaccharide unit of hyaluronic acid is about 400 Da.
  • An oligomer of one to six disaccharide units of hyaluronic acid therefore has a molecular weight of between 400 and 2400 Da.
  • Oligomer means, according to IUPAC in Pure Appl. Chem., Vol. 68, No.12, pp. 2287-2311, 1996, a molecule of intermediate molecular weight, the structure of which comprises a small amount of molecules having a lower molecular weight.
  • a molecule having an intermediate molecular mass we will speak of a molecule having an intermediate molecular mass, when the removal of one or a few constituent units will significantly modify the properties of the molecule.
  • the oligosaccharides used in the compositions according to the invention are compounds that exist naturally in the human body.
  • one oligosaccharide is used at concentrations of between 10 -9 M and 10 -3 M, preferably between 10 -8 M and 10 -5 M.
  • compositions according to the invention comprise an inhibitor of the degradation of hyaluronic acid.
  • inhibitor of the degradation of hyaluronic acid is meant a compound capable of reducing, or even blocking, the catabolism either extracellular or intracellular of hyaluronic acid, preferably a compound capable of reducing or even blocking the extracellular catabolism of hyaluronic acid, more preferably a compound capable of inhibiting extracellular hyaluronidase present in the skin.
  • 1,2,3,4,6-penta-O-galloylglucose will be chosen in particular.
  • the inhibitors of the degradation of hyaluronic acid used in the compositions according to the invention are natural.
  • the inhibitor is used at concentrations of between 10 -9 M and 10 -2 M, preferentially between 10 -6 M and 10 -3 M.
  • derivatives of glycyrrhizin or glycyrrhetinic acid is meant in particular salts, substituted derivatives, enantiomers and racemates of said compounds.
  • salts of said compounds there may be mentioned the salts obtained by adding said compounds with a base inorganic, chosen in particular from hydroxides of sodium, lithium, calcium, potassium, magnesium, ammonium or zinc, alkali or alkaline earth metal carbonates such as sodium carbonates, sodium bicarbonates, calcium, potassium, magnesium, ammonium or zinc, or with an organic base, chosen in particular from methylamine, propylamine, trimethylamine, diethylamine, triethylamine, N, N-dimethylethanolamine, tris ( hydroxymethyl) ammomethane, ethanolamine, pyrimidine, picolme, dicyclohexylamine, morpholine, process, lysine, arginine, histidine, N-methylglucamine or phosphonium salts such as alkylphosphonium, arylphosphonium salts, alkylarylphosphonium salts, alkenylarylphosphonium salts or quaternary ammonium salts such as tetra-
  • Such salts are in particular the potassium salt of glycyrrhetinic acid, the sodium salt of glycyrrhetinic acid, or the monoammonium salt of glycyrrhetinic acid (ammonium glycyrrhetmate).
  • analogue is intended to mean, in particular, the enzymatic or biomimetic analogs of said compounds, capable of binding to the catalytic or non-catalytic site of hyaluronidases and of thus inhibiting their activation.
  • Such analogs can be selected in vitro by hyaluronidase binding or inhibition tests according to conventionally used techniques.
  • the derivatives and / or analogues must be of natural origin.
  • the compounds and their derivatives and / or analogues of natural origin are compounds in the pure state or in solution at different concentrations, obtained by various processes for extracting or hydrolyzing biological material of natural origin.
  • compositions according to the invention may also contain the usual adjuvants well known to those skilled in the art.
  • compositions according to the invention are preferably formulated for topical and / or parenteral application.
  • topical means an external application on the skin or mucous membranes.
  • compositions may be in any of the galenic forms normally used for topical administration.
  • topical compositions mention may be made of compositions in liquid, pasty or solid form and, more particularly, in the form of ointments, aqueous, hydroalcoholic or oily solutions, and optionally two-phase lotion-type dispersions.
  • serum, aqueous, anhydrous or lipophilic gels powders, soaked swabs, syndets, wipes, sprays, foams, sticks, shampoos, compresses, washing bases, emulsions of liquid consistency or semi-liquid of the milk type, obtained by dispersion of a fatty phase in an aqueous phase (O / W) or conversely (W / O), a microemulsion, suspensions or emulsions of soft consistency, semi-liquid liquid or solid white or colored cream, gel or ointment, suspensions of microspheres or nanospheres or lipid or polymeric vesicles, or microcapsules, microparticles or nanoparticles or polymeric or gelled patches for controlled release.
  • compositions according to the invention can be applied subcutaneously or intradermally.
  • parenteral compositions mention may be made of compositions in the form of solutions or suspensions for infusion or injection.
  • hyaluronic acid may be administered in the form of an injectable aqueous solution, the pentamere of acid hyaluronic acid and glycyrrhizin being administered in the form of a cream.
  • the administration frequencies may be identical or different.
  • the frequency of administration of hyaluronic acid injected in the form of an aqueous solution for injection may vary from 4 to 24 months, preferably from 4 to 16 months, while those of composition according to the invention, administered topically, for example in cream form, can vary from 1 to 7 days, preferably from 1 to 3 days.
  • the process for manufacturing a composition comprises the steps of preparing a physiologically acceptable medium and mixing an effective amount of pentamer of hyaluronic acid, and glycyrrhizin and / or its derivatives and / or analogues.
  • the invention also relates to the use of at least one inhibitor of the degradation of hyaluronic acid, and of at least one oligosaccharide chosen from oligomers of hyaluronic acid, or of a composition as described previously for the manufacture of a medicament for the treatment, improvement and / or prevention of dermatological conditions.
  • the invention relates to the use of at least one inhibitor of the degradation of hyaluronic acid, and of at least one oligosaccharide chosen from oligomers of hyaluronic acid, or of a composition such as as described above, for the manufacture of a cosmetic or pharmaceutical composition for the treatment, improvement and / or prevention of skin aging.
  • Skin aging is understood to mean wrinkles, fine lines, fibroblastic depletions and scars.
  • Such a composition is adapted to the treatment of wrinkled and / or aged skin, and is intended in particular to prevent and / or reduce the effects thereof.
  • the treatment of wrinkles, fine lines, Fibroblastic depletions and all scarring is done by filling.
  • composition according to the invention can be applied to the areas of the face or forehead marked by expression lines.
  • the invention also relates to the use of at least one inhibitor of the degradation of hyaluronic acid, and of at least one oligosaccharide chosen from oligomers of hyaluronic acid, or of a composition as described previously, for the manufacture of a cosmetic or pharmaceutical composition for use in reconstructive surgery.
  • GLZ at different concentrations, is pre-incubated or not for 20 minutes at 37 ° C in the presence of the enzyme.
  • the enzymatic reaction is triggered by adding the hyaluronic acid solution (TO time). After 20 minutes of incubation, the unhydrolysed hyaluronic acid is precipitated by addition of the acid solution of bovine albumin.
  • TO time the time of incubation
  • bovine albumin the acid solution of bovine albumin
  • the turbidimetry of the solutions is determined on a spectrophotometer at a wavelength of 600 nm.
  • the optical density (OD) of these solutions is deduced from the OD of a control solution of hyaluronic acid (of the same concentration) not hydrolyzed by the enzyme. This difference in OD, which is inversely proportional to the concentration of hyaluronic acid, is used to measure the activity of hyaluronidase.
  • Example 2 Inhibitory effect of pentameric bindmg (NAC-Glucuronic acid) on the CD44 receptor of hyaluronic acid
  • hyaluronic acid labeled with fluoresceinamine (according to DeBelder et al., 1975, Carbohydrate Res., 44, 251-257) and then increasing concentrations of pentamer (NAC-Glucuronic acid) 5.
  • the measurement of the displacement of fluorescent hyaluronic acid by the pentamer (NAC-Glucuronic acid) is carried out.
  • composition is prepared in a conventional manner for the person skilled in the art:
  • Example 4 Composition No. 2

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
EP08788213A 2007-05-11 2008-04-22 Pharmazeutische oder kosmetische präparate zur topischen und/oder parenteralen anwendung, verfahren zu ihrer herstellung und ihre anwendung Withdrawn EP2155154A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0755024 2007-05-11
PCT/FR2008/050725 WO2008139123A2 (fr) 2007-05-11 2008-04-22 Preparations pharmaceutiques ou cosmetiques pour application topique et/ou parenterale, leurs procedes de preparation, et leurs utilisations

Publications (1)

Publication Number Publication Date
EP2155154A2 true EP2155154A2 (de) 2010-02-24

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EP08788213A Withdrawn EP2155154A2 (de) 2007-05-11 2008-04-22 Pharmazeutische oder kosmetische präparate zur topischen und/oder parenteralen anwendung, verfahren zu ihrer herstellung und ihre anwendung

Country Status (4)

Country Link
US (1) US20110263521A1 (de)
EP (1) EP2155154A2 (de)
CA (1) CA2686931A1 (de)
WO (1) WO2008139123A2 (de)

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FR2939317B1 (fr) * 2008-12-08 2010-12-24 Oreal Systeme de delivrance trans(epi)dermique comprenant une dispersion vesiculaire, procede de traitement cosmetique et utilisation cosmetique
US20110172180A1 (en) 2010-01-13 2011-07-14 Allergan Industrie. Sas Heat stable hyaluronic acid compositions for dermatological use
KR102154944B1 (ko) 2011-06-03 2020-09-11 알러간 인더스트리 에스에이에스 항산화제를 포함하는 피부 충전제 조성물
US20130096081A1 (en) 2011-06-03 2013-04-18 Allergan, Inc. Dermal filler compositions
US9408797B2 (en) 2011-06-03 2016-08-09 Allergan, Inc. Dermal filler compositions for fine line treatment
US9393263B2 (en) 2011-06-03 2016-07-19 Allergan, Inc. Dermal filler compositions including antioxidants
PT2866804T (pt) 2012-06-27 2023-12-18 Amazentis Sa Melhoria da autofagia ou aumento da longevidade por administração de urolitinas ou seus precursores
WO2014165713A2 (en) 2013-04-03 2014-10-09 Cedars-Sinai Medical Center Treatment of inflammatory conditions by modulation of hyaluronan and hyaluronidase activity
JP7761372B2 (ja) 2017-03-08 2025-10-28 アマゼンティス エスアー 対象におけるマイトファジーを改善するための方法
DE102021114841A1 (de) * 2021-06-09 2022-12-15 Schreiner Group Gmbh & Co. Kg Folienverbund mit Schutz vor Manipulation

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FR2894827B1 (fr) * 2005-12-21 2010-10-29 Galderma Res & Dev Preparations pharmaceutiques ou cosmetiques pour application topique et/ou parenterale, leurs procedes de preparation,et leurs utilisations

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CA2686931A1 (fr) 2008-11-20
WO2008139123A3 (fr) 2009-01-08
US20110263521A1 (en) 2011-10-27
WO2008139123A2 (fr) 2008-11-20

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