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
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
• • 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
  • A61K31/33—Heterocyclic compounds
  • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
  • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
• • 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
  • A61K31/33—Heterocyclic compounds
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
  • A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
• • 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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/42—Amides
• • 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
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/08—Anti-ageing preparations

Definitions

• the subject of the present invention is the use of esters of N-acyl derivatives of amino acids and of isosorbide as an anti-aging agent for the skin of the human body, as well as cosmetic, pharmaceutical and dermopharmaceutical compositions for topical use comprising said esters of N-acyl derivatives of amino acids and isosorbide intended to prevent aging of the skin of the human body.
• Human skin is the first image offered in the eyes of others, and therefore, the improvement of its appearance is a subject of constant concern for human beings.
• the skin is a reflection of a state of well-being, often associated with youth, and conversely to a state of fatigue and / or aging.
• Skin aging is therefore a concern for humans and more particularly for consumers of cosmetic products who are looking for solutions to mitigate and / or prevent the visible manifestations of said aging.
• This cutaneous aging is observed at the level of the different cutaneous tissues and is characterized by metabolic, functional, cellular, architectural and tissue alterations, leading to visible external effects characterized by the appearance and increase of wrinkles, by a dull complexion. , by a lack of uniformity of the complexion (phenomenon of dyschromism), or by a modification of the texture and the properties, in particular biomechanical, of the skin of the human body.
• Skin aging results from factors that are specific to each individual (characteristics of each individual's genetic heritage) and from environmental factors.
• environmental factors that can cause skin aging include repeated and prolonged exposure to the sun, especially exposure to ultraviolet radiation, exposure to air pollution, cigarette smoke, various oxidative stress that may result among other factors previously mentioned, as well as psychological, emotional and nervous stress.
• the repeated and prolonged exposure of human skin to sunlight, and more particularly to ultraviolet radiation leads to a form of aging that is commonly called photo-aging.
• This photo-aging is well documented in the scientific literature and it causes alterations of the skin at different levels, one of the most well-known skin alterations is solar elastosis, which is characterized by profound changes in the architecture and the organization of the elastic fibers of the dermis.
• ROS reactive oxygen species
• the so-called “photodynamic” technique has been described as particularly suitable for rejuvenation (ie the reduction of wrinkles and fine lines, pigmentation spots, etc.) of the so-called “photo-exposed” skin, namely the skin exposed to solar radiation. , and more particularly to ultraviolet radiation.
• the mechanism by which this technique acts has recently been studied (4), and it turns out that its mode of action includes an increase in the fibroblastic population and an increase in the migratory capacity of said fibroblasts.
• an improvement in the migratory properties of fibroblasts of the dermis of human skin and / or an increase in the fibroblastic population are means of preventing and / or treating the aging of the skin of the human body, and more particularly to prevent and / or treat the visible effects of said aging, for example wrinkles, dullness, lack of uniformity of the complexion (dyschromia), rigidity of the skin of the human body, caused by natural aging or by exposure prolonged exposure to the sun, especially exposure to ultraviolet radiation, or exposure to oxidative stress.
• Curcumin extracts which stimulate healing when used in low doses and act on the migration of fibroblasts at higher doses (7); Pouteria Lucuma nut oils, characterized by the major presence of linoleic acid, oleic acid, palmitic acid, stearic acid and ⁇ -linolenic acid, which are described as stimulating the migration of fibroblasts and the expression of vinculin, and adapted to accelerate the healing of wounds of the skin (8); the combination of extracts of Vigna Marina, Cocos Nucifera L, Terminalia Catappa L. and Hibiscus tiliaceus L.
• cosmetic compositions to help treat wounds, improve healing, treat skin problems related to age , described in the international application published under the number WO 2010/127396 A1.
• the international application published under the number WO 2010/056908 A1 discloses the use of Pouteria lucuma extract and more particularly the oils contained in their nucleus, to improve the migration of human fibroblasts.
• the use of plant extracts, bacteria has the disadvantage of showing unreliable performance over time due to the variability of the content of the raw materials.
• synthetic cosmetic active principles for example peptides which are described as acting on the migration of fibroblasts.
• Pentapeptides of Lys-Thr-Thr-Lys-X formula can thus be mentioned, where X represents any natural amino acid, but preferentially serine, and of which a fatty acid chain (C2 to C22) is grafted on the N-terminal amine. and / or its esterified carboxyl group, described in the French patent application published under the number FR 2 783 169.
• pentapeptides are incorporated in cosmetic or pharmaceutical compositions to cause the increase of the synthesis of collagen and glycosaminoglycans (by radioactivity ) on cutaneous explants and the increase of the proliferation of normal human fibroblasts in culture, and consequently to improve the appearance of the skin in the case of its natural aging; of its drying up, of its cicatrization.
• WO 97/17835 discloses peptides containing at least one sequence of three amino acids (Lys-Lys-Gly, Gly-His-Lys or Glu-His-Lys) conjugated to a mono or dicarboxylic acid, incorporated in cosmetic or pharmaceutical compositions as a healing and anti-wrinkle agent, showing an effect on the synthesis of collagen I by fibroblasts.
• N-acylated amino acid derivatives are chemical ingredients widely used for the preparation of cosmetic, dermo-cosmetic, dermopharmaceutical and pharmaceutical compositions, because of their different active properties.
• JP 2002-179518 discloses N-acyl derivatives of glutamic acid and aspartic acid and their salts, characterized by acyl chains having from 6 to 24 carbon atoms, used to be incorporated in the preparation of cosmetic compositions for sensitive, dry and atopic skin. None of his documents describes the use of N-acylated amino acid derivatives to enhance the migratory properties of dermal fibroblasts in human skin and / or an increase in of the fibroblastic population so as to prevent and / or treat the aging of the skin of the human body
• EP 1 471 881 discloses that N-acylated derivatives of ⁇ -amino acids and in particular N-undecylenoyl phenylalanine have an affinity for the specific melanocyte Hormone receptor (a- MSH) and thus induce the lightening of the skin according to the following biochemical mechanism: the competition between the ⁇ -MSH hormone and the molecule having affinity towards the ⁇ -MSH receptor, results in a lower rate of fixation of said hormone on cellular receptors; this competition results in an inhibition of the activity of the adenylate cyclase which causes a less transformation of ⁇ in intracellular cyclic AMP; the decrease of cyclic AMP results in an inhibition of Protein Kinase A (PKA) enzyme; the inhibition of Protein Kinase A induces a lower activation of tyrosinase due to the lesser transformation of tyrosinase into phosphorylated tyrosinase; this less activation of
• PKA Protein Kinas
• Japanese Patent Application No. 2000-229121 discloses the use of N-acylamino acid ester polyols as high performance surfactants.
• any changes in the external appearance of the skin or the lips due to aging is chronobiological and / or photo- induced and / or resulting from exposure to environmental stresses (air pollution, contact with dangerous substances), for example wrinkles and fine lines, alteration of the microrelief, lack of elasticity and / or tone of the skin, the lack of density and / or firmness of the human skin or lips, but also any internal changes in the skin that do not systematically result in a modified external appearance, for example any internal damage to the skin resulting from exposure to the skin. ultraviolet radiation.
• the subject of the invention is the use of a compound of formula (I):
• R 'and R " which are identical or different, represent either a hydrogen atom or a monovalent radical of formula (IIa):
• R3 represents a hydrogen atom
• R2 represents a radical chosen from methyl, isopropyl, isobutyl or 1-methylpropyl radicals
• the subject of the present invention is the use as described above of a compound of formula (I) or of a composition (Ci) as defined above for which the compound of formula (I), the compound of formula (Ia) and the compound of formula (Ib) are chosen from isosorbide esters of N-octanoyl alanine, N-octanoyl valine, N-octanoyl leucine of N-octanoyl isoleucine, ⁇ - ( ⁇ -undecylenoyl) alanine, N- (i-undecylenoyl) valine, N- (i-undecylenoyl) leucine of ⁇ - ( ⁇ -undecylenoyl) isoleucine, N-dodecanoyl alanine, N- dodecanoyl valine, N-dodecanoyl leucine N-do
• N-cocoyl alanine N-cocoyl valine, N-cocoyl leucine or N-cocoyl isoleucine
• the subject of the present invention is the use as previously described of a compound of formula (Ia), as previously defi ned, chosen from isosorbide N-octanoyl alaninate, isosorbide N-hexadecanoyl valinate, isosorbide N-octanoyl isoleucinate, or the mixture of isosorbide N-cocoyl isoleucinate.
• the subject of the present invention is the use as described above of a compound of formula (Ib) as defined above, chosen from bis (N-octanoyl alaninate) of isosorbide.
• the compound of formula (I) as defined above may be prepared according to a preparation process comprising:
• the compounds of formulas (Nia) and (IIIb) are known or are synthesizable by N-acylation of the corresponding ⁇ -amino acids according to methods known to those skilled in the art.
• the molar ratio of compound of formula (Nia) or of formula (IIIb) on isosorbide of formula (IV) is generally between 3/1 and 1/5, more particularly between 1/1 and 1/5, and even more particularly between 1/1 and 1/3.
• step b) of separation of the compounds of formula (Ia) and of formula (Ib) is carried out by the conventional separation methods known to those skilled in the art.
• the compound of formula (I) as defined above may also be prepared according to a preparation process comprising:
• R5 represents a linear aliphatic radical having 1 to 4 carbon atoms, to form either a compound of formula (Via):
• R1, R4 and R5 are as previously defined;
• step b The implementation of step b).
• step a1) is generally carried out at a temperature of about 60 ° C to 120 ° C, under an inert gas, and in the presence of an acidic catalyst system.
• acidic catalytic system are meant strong acids such as sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, hypophosphorous acid, methanesulfonic acid, para-toluene sulfonic acid, trifluoromethanesulfonic acid, or acidic ion exchange resins.
• step a1) of the process as described above the molar ratio of compound of formula (Nia) or compound of formula (IIIb) on alcohol of formula (V) is generally between 1/1 and 1/10, more particularly between 1/1 and 1/8, and even more particularly between 1/2 and 1/8.
• step a2) of trans-esterification of the ester of formula (Via) or of formula (VIb) obtained in step a1) is generally carried out at a temperature of about between 80 ° C and 180 ° C, more particularly between 100 ° C and 150 ° C, even more particularly between 120 ° C and 150 ° C under an inert gas, and in the presence of an acid catalyst system such as previously described, and with vacuum distillation of the alcohol of formula (V) formed in-situ.
• step a2) of the process as described above the molar ratio of compound of formula (V) to isosorbide of formula (V) is between 3/1 and 1/5, more particularly between 1/1 and 1 / 5, and even more particularly between 1/1 and 1/3.
• composition (C1) as defined above can be prepared by various routes.
• a first route of preparation of the composition (C1), implemented in the use object of the invention, consists in mixing in the mass proportions. desired, the compound of formula (la) as defined above, with the compound of formula (Ib) as defined above.
• a second route of preparation of the composition (C1), implemented in the use object of the invention, consists in implementing the process for preparing the compound of formula (I) as described above, by reacting in the desired proportions, the isosorbide of formula (IV) with the compound of formula (Nia) and / or this compound of formula (IIIb).
• a third route of preparation of the composition (C1), implemented in the use that is the subject of the invention, consists in implementing the variant of the process for preparing the compound of formula (I) as described above, by react in the desired proportions, the compound of formula (Nia) or the compound (IIIb) with the alcohol of formula (V), then the isosorbide of formula (IV).
• the invention also relates to a method for the purpose of preventing or slowing the appearance of wrinkles, fine lines, an alteration of the microrelief, lack of elasticity and / or tone, lack of density and or of firmness or of eliminating them, comprising at least one step of application to human skin or to the lips, of a cosmetic formulation for topical use comprising at least one cosmetically acceptable excipient and an effective amount of at least a compound of formula (I) or a composition (C1) as defined above.
• the cosmetic formulation for topical use is spread on the surface of the skin to be treated, then the skin is massaged a few moments.
• the expression "for topical use” used in the definition of the cosmetic formulation used in the cosmetic process that is the subject of the present invention means that said formulation is implemented by application to the skin, whether a direct application in the case of a cosmetic formulation or an indirect application when the cosmetic formulation according to the invention is impregnated on a support intended to be put in contact with the skin (paper, wipe, textile, transdermal device, etc.).
• cosmetic formulation for topical use, used in the cosmetic process that is the subject of the present invention, means according to the Council Directive 76/768 / EEC of 27 July 1976 as amended by Directive 93/35 / EEC of 14 June 1993, that the said formulation includes any substance or preparation intended to be placed in contact with the various parts of the human body (epidermis, hair and hair system, nails, lips and genitals) or with the teeth and oral mucosa in view, exclusively and mainly, to clean, perfume, modify the appearance and / or correct body odor and / or protect or maintain it in good condition.
• effective amount of the compound of formula (I) or of the composition (C1) as defined previously present in the cosmetic formulation for topical use implemented in the process as defined above is meant for 100% of the mass. of said cosmetic formulation for topical use, the amount of between 0.1% and 5% by weight, more particularly between 0.1% and 3% by weight, and even more particularly between 0.5% and 2% by weight of compound of formula (I) or the composition (C1).
• the cosmetic formulations for topical use implemented in the cosmetic process as defined above are generally in the form of aqueous or hydro-alcoholic or hydro-glycolic solutions, in the form of a suspension, an emulsion, a microemulsion or a nanoemulsion, whether of water-in-oil, oil-in-water, water-in-oil-in-water or oil-in-water-in-oil type, or in the form of a powder.
• topical cosmetic formulations used in the cosmetic process which is the subject of the present invention may be packaged in a bottle, in a device of the pump “bottle” type, in pressurized form in an aerosol device, in a device provided with a perforated wall such as a grid or in a device provided with a ball applicator (called “roll-on").
• the compound of formula (I) or the composition (C1), present in cosmetic formulations for topical use implemented in the cosmetic process that is the subject of the present invention is associated with chemical additives that are usually used.
• chemical additives that are usually used. in the field of formulations for topical use, such as foaming and / or detergent surfactants, thickening and / or gelling surfactants, thickening and / or gelling agents, stabilizing agents, film-forming compounds, solvents and co-solvents, hydrotropic agents, thermal or mineral waters, plasticizers, emulsifiers and co-emulsifiers, opacifying agents, pearlescent agents, superfatting agents, sequestering agents, chelating agents, oils, waxes, antioxidants, perfumes, essential oils, preservatives, conditioners, deodorants, bleaching agents hair and skin discoloration, the active ingredients intended to provide a treating and / or protective action with respect to the skin or the hair, sunscreens, mineral fillers or pigments, particles providing a visual effect
• foaming and / or detergent surfactants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, it is possible to mention may be made of foaming surfactants and / or anionic, cationic, amphoteric or nonionic detergents.
• foaming and / or detergent anionic surfactants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, it is mention may be made of alkali metal, alkaline earth metal, ammonium, amine, or aminoalcohol, alkyl ether sulphate, alkyl sulphate, alkylamidoether sulphate, alkylaryl polyether sulphate, monoglyceride sulphate or alpha salts.
• olefinsulfonates paraffin sulfonates, alkylphosphates, alkyletherphosphates, alkylsulfonates, alkylamidesulfonates, alkylarylsulfonates, alkylcarboxylates, alkylsulfosuccinates, alkylethersulfosuccinates, alkylamidesulfosuccinates, alkylsulfoacetates, alkylsarcosinates, acylisethionates, N-acyltaurates, acyllactylates, N-acyl derivatives of amino acids, N-acyl derivatives of peptides, N-acyl derivatives of proteins or N-acyl derivatives of fatty acids.
• foaming and / or detergent amphoteric surfactants which can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, it is possible to mention may be made of alkylbetaines, alkylamidobetaines, sultaines, alkylamidoalkylsulfobetaines, imidazoline derivatives, phosphobetaines, amphopolyacetates and amphopropionates.
• foaming and / or detergent cationic surfactants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, it is mention may be made especially of quaternary ammonium derivatives.
• foaming and / or detergent nonionic surfactants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process, object of the present invention
• alkylpolyglycosides comprising an aliphatic radical, linear or branched, saturated or unsaturated, and comprising from 8 to 16 carbon atoms, such as octyl polyglucoside, decyl polyglucoside, undecylenyl polyglucoside, dodecyl polyglucoside, tetradecyl polyglucoside, hexadecyl polyglucoside, 1,12 dodecanediyl polyglucoside; ethoxylated hydrogenated castor oil derivatives such as the product marketed under the INCI name "Peg-40 hydrogenated castor oil”; polysorbates such as Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 70, Polysorbate 80, Polysorbates
• thickening and / or gelling surfactants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention
• polyglycoside fatty esters optionally poly (alkoxylated) such as ethoxylated methylpolyglucoside esters such as PEG 120 methyl glucose trioleate and PEG 120 methyl glucose dioleate respectively marketed under the names GLUCAMATE TM LT and GLUMATE TM DOE120; alkoxylated fatty esters such as PEG 150 pentaerythrityl tetrastearate marketed under the name CROTHIX TM DS53, PEG 55 propylene glycol oleate sold under the name ANTIL TM 141; fatty chain polyalkylene glycol carbamates such as PPG-14 laureth isophoryl dicarbamate marketed under the name ELFACOS TM T21 1, P
• thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention
• Polymers of polyelectrolytic type, linear or branched or crosslinked that can be combined with the compound of formula (I) or composition (C1) in topical cosmetic formulations used in the cosmetic process object of the present invention may be in the form of a solution, an aqueous suspension, a water-in-oil emulsion, an oil-in-water emulsion, a powder.
• Polymers of polyelectrolytic type, linear or branched or crosslinked that can be combined with the compound of formula (I) or composition (C1) in topical cosmetic formulations used in the cosmetic process object of the present invention can be selected from the products marketed under the names SIMULGEL TM EG, SIMULGEL TM EPG, SEPIGEL TM 305, SIMULGEL TM 600, SIMULGEL TM NS, SIMULGEL TM INS 100, SIMULGEL TM FL, SIMULGEL TM A, SIMULGEL TM SMS 88, SEPINOV TM EMT 10, SEPIPLUS TM 400, SEPIPLUS TM 265, SEPIPLUS TM S, SEPIMAX TM Zen, ARISTOFLEX TM AVC, ARISTOFLEX TM AVS, NOVEMER TM EC-1, NOVEMER TM EC 2, ARISTOFLEX TM HMB, COSMEDIA TM SP, FLOCARE TM AND 25, FLOCARE TM AND
• thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process
• thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention
• polysaccharides consisting of derivatives of oste, such as sulphated galactans and more particularly carrageenans and agar, uronans and more particularly alginines, alginates and pectins, heteropolymers of osteos and uronic acids and more particularly xanthan gum, gellan gum, exudates of arabic gum and karaya gum, glucosaminoglycans.
• thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention
• stabilizing agents that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of the microcrystalline waxes, and more particularly ozokerite, mineral salts such as sodium chloride or magnesium chloride, silicone polymers such as polysiloxane polyalkyl polyether copolymers.
• organic solvents such as glycerol, diglycerol, oligomers of glycerol, ethylene glycol, propylene glycol, butylene glycol, and the like. propanediol, 1,2-propanediol, hexylene glycol,
• thermal or mineral waters that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention
• thermal or mineral waters with a mineralization of at least 300 mg / l, in particular Avene water, Vittel water, Vichy basin water, Uriage water, water La Roche Posay, the water of the Bourboule, the water of Enghien-les-bains, the water of Saint-Gervais-les bains, the water of Néris-les-bains, the water of Allevard -the-baths, the water of Digne, the water of the Maizieres, the water of Neyrac-les-bains, the water of Lons le Saunier, the water of Rochefort, the water of Saint Christau, the water of the Fumades and the water of Tercis-les-bains.
• hydrotropic agents that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of the xylene sulphonates, cumene sulphonates, hexyl polyglucoside, (2-ethyl hexyl) polyglucoside, n-heptyl polyglucoside.
• emulsifying surfactants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention include nonionic surfactants, anionic surfactants, cationic surfactants.
• esters of fatty acids and of sorbitol such as the products marketed under the names MONTANE TM 40, MONTANE TM 60, MONTANE TM 70, MONTANE TM 80 and MONTANE TM 85; compositions comprising glycerol stearate and ethoxylated stearic acid between 5 moles and 150 moles of ethylene oxide, such as the composition comprising stearic acid ethoxylated with 135 moles of ethylene oxide and glycerol stearate.
• mannitan esters ethoxylated mannitan esters
• sucrose esters methylglucoside esters
• alkylpolyglycosides having a linear or branched, saturated or unsaturated aliphatic radical, and having from 14 to 36 carbon atoms, such as tetradecyl polyglucoside, hexadecyl polyglucoside, octadecyl polyglucoside, hexadecyl polyxyloside, octadecylpolyxyloside, eicosyl polyglucoside, dodecosyl polyglucoside, 2-octyldodecyl polyxyloside, 12-hydroxystearyl polyglucoside; linear or branched fatty alcohol compositions, saturated or unsaturated, and containing from 14 to 36 carbon atoms, and alkyl polyglycosides as described above.
• anionic surfactants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process, which is the subject of the present invention, mention may be made of the glyceryl stearate citrate, cetearyl sulphate, soaps such as sodium stearate or triethanolammonium stearate, N-acyl derivatives of salified amino acids for example stearoyl glutamate.
• emulsifying cationic surfactants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of the aminoxides, quaternium-82 and the surfactants described in the patent application WO96 / 00719 and mainly those whose fatty chain comprises at least 16 carbon atoms.
• opacifying and / or nacrating agents that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention
• texture agents that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention
• mention may be made of N-acylated derivatives of amino acids such as lauroyl lysine marketed under the name AMINOHOPE TM LL, octenyl starch succinate sold under the name DRYFLO TM, myristyl polyglucoside marketed under the name MONTANOV TM 14, fibers cellulose, cotton fibers, chitosan fibers, talc, sericite, mica.
• deodorant agents that can be combined with the compound of formula (I) or with the composition (C1) in the cosmetic formulations for topical use put into In the cosmetic process which is the subject of the present invention, mention may be made of alkali silicates, zinc salts such as zinc sulphate, zinc gluconate, zinc chloride and zinc lactate; quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts; glycerol derivatives such as glycerol caprate, glycerol caprylate, polyglycerol caprate; the 1, 2 decanediol; 1,3 propanediol; salicylic acid; sodium bicarbonate; cyclodextrins; metallic zeolites; TRICLOSAN TM; aluminum bromohydrate, aluminum chlorohydrates, aluminum chloride, aluminum sulphate, aluminum and zirconium hydrochlorides, aluminum and zirconium trihydrochloride, aluminum zirconium
• oils minerals such as paraffin oil, liquid petrolatum, isoparaffins or mineral white oils
• oils of animal origin such as squalene or squalane
• vegetable oils such as phytosqualane, sweet almond oil, coconut oil, castor oil, jojoba oil, olive oil, rapeseed oil, peanut oil, sunflower oil, wheat germ oil, corn germ oil, soybean oil, cottonseed oil, alfalfa oil, poppy oil, pumpkin oil, evening primrose oil, millet oil, barley oil, rye oil, Safflower oil, sayoulier oil, passionflower oil, hazelnut oil, palm oil, shea butter, apricot kernel oil, calophyllum oil, sysymbrium oil, avocado oil, calendula oil, oils derived from flowers or vegetables ethoxylated vegetable oils, such as paraffin oil, liquid petrolatum, isoparaffins or mineral white oils; oils of animal origin, such as squalene or squalane, vegetable oils, such as phytos
• waxes that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention
• waxes is meant in the present application the compounds and / or mixtures of compounds insoluble in water, having a solid appearance at a temperature greater than or equal to 45 ° C.
• vitamins and their derivatives especially their esters, such as retinol (vitamin A) and its esters (retinyl palmitate for example), ascorbic acid (vitamin C) and its esters, ascorbic acid sugar derivatives (as ascorbyl glucoside), tocopherol (vitamin E) and its esters (such as tocopherol acetate), vitamins B3 or B10 (niacinamide and its derivatives); compounds showing a lightening or depigmenting action on the skin, such as ⁇ -undecelynoyl phenylalanine marketed under the name SEPIWHITE TM MSH, SEPICALM TM VG, the mono ester and / or the glycerol diester of ⁇ -undecelynoyl phenylalanine,
• antioxidants that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention
• sunscreens that can be combined with the compound of formula (I) or with the composition (C1) in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of all those contained in Cosmetic Directive 76/768 / EEC as amended Annex VII.
• the family benzoic acid derivatives such as para-aminobenzoic acids (PABA), in particular the monoglycerol esters of PABA, the ethyl esters of ⁇ , ⁇ -propoxy PABA, the ethyl esters of ⁇ , ⁇ -diethoxy PABA, the ethyl esters ⁇ , ⁇ -dimethyl PABA, methyl esters of ⁇ , ⁇ -dimethyl PABA, butyl esters of ⁇ , ⁇ -dimethyl PABA; the family of anthranilic acid derivatives such as homomenthyl-N-acetyl anthranilate; the family of salicylic acid derivatives such as amyl salicylate, homomenthyl salicylate, ethylhexyl salicylate,
• PABA para-aminobenzoic acids
• anthranilic acid derivatives such as homomenthyl-N-acetyl anthranilate
• salicylic acid derivatives
• inorganic screens which can be combined with the compound of formula (I) or with the composition (C1) in the cosmetic formulations for topical use implemented in the cosmetic process object of the present invention include titanium oxides, zinc oxides, cerium oxide, zirconium oxide, iron oxides yellow, red or black, chromium oxides. These inorganic screens may or may not be micronized, have undergone or not surface treatments and may be presented in the form of aqueous or oily pre-dispersions.
• alanine ie one molar equivalent
• a hydroalcoholic mixture consisting of 1.800 grams of water and 200 grams of isopropanol at a temperature of 20 ° C.
• the pH of the medium is adjusted to 10 by addition of a 30% sodium hydroxide solution.
• 731, 7 grams of octanoyl chloride, 0.8 molar equivalent, are then gradually poured into the mixture maintained between 20 ° C and 50 ° C and at a pH between 10 and 10.5.
• the reaction medium is then stirred for two hours and then heated to 70 ° C, then added 979.6 grams of a 75% phosphoric acid solution to gradually reach a pH value of 2 , 0.
• the aqueous phase of the medium is decanted and withdrawn and the organic phase remaining in the The reactor is washed several times with brine at room temperature with stirring. After washing and then drying by vacuum distillation of the residual water, the organic phase comprising 922.3 grams of desired N-octanoyl alanine is obtained.
• Example 2 The procedure of the process described in Example 1 is carried out by replacing the molar equivalent of alanine with a molar equivalent of valine and the 0.8 molar equivalent of octanoyl chloride with 0.8 molar equivalents of chloride. of (o> - undecylenoyl) to obtain the composition (C1 B ), the analytical characteristics of which are as follows:
• Example 3 Preparation of a Composition (C1n) According to the Invention
• the procedure of the process described in Example 1 is carried out by replacing the molar equivalent of alanine with a molar equivalent of valine and the 0.8 molar equivalent of octanoyl chloride with 0.8 molar equivalents of chloride.
• of hexadecanoyie obtain the Composition (C1 c ) whose analytical characteristics are as follows:
• Example 1 The procedure of the method described in Example 1 is implemented by replacing the molar equivalent of alanine with a molar equivalent of isoleucine, to obtain the Composition (C1 D ), the analytical characteristics of which are as follows:
• Said cocoyl chloride used in the preparation of Composition (C1 E ) comprises for 100% of its mass, 8% by weight of octanoyl chloride, 8% by weight of decanoyl chloride, 50% by weight of lauroyl chloride, 17% mass of myristoyl chloride, 8% by weight of palmitoyl chloride, 3% by weight of stearoyl chloride, 4% by weight of oleoyl chloride and 2% by weight of linoleoyl chloride.
• the demonstration of anti-aging activity of the compositions according to the invention was carried out by the implementation of a study model consisting in studying the migratory capacity of normal human fibroblasts treated or not with the compositions according to the invention. and references.
• the fibroblast migration test is a test commonly used in the cosmetics and pharmacy sector and described in particular in the international application published under the number WO 2010/056908 A1. It makes it possible to reproduce in vitro the phenomenon of fibroblast migration; a decrease in the migratory capacities of fibroblasts being reported as associated with skin aging (1) (4).
• compositions (C1 A), (C1 B), (C 1 c), (C1 D) and (C1 D) with the normal human fibroblasts show a significant increase of the distance of migration of said fibroblasts, and therefore an improvement migratory properties of the dermal fibroblasts of the human skin, thus constituting an effective means of preventing and / or treating the aging of the skin of the human body and the lips.

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• 2014
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