Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07K—PEPTIDES
  • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
  • C07K7/04—Linear peptides containing only normal peptide links
  • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K38/00—Medicinal preparations containing peptides
  • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
  • A61K38/08—Peptides having 5 to 11 amino acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
  • A61K8/04—Dispersions; Emulsions
• • 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
  • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K9/00—Medicinal preparations characterised by special physical form
  • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
• • 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
  • A61K9/08—Solutions
• • 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
  • A61K9/10—Dispersions; Emulsions
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P11/00—Drugs for disorders of the respiratory system
  • A61P11/06—Antiasthmatics
• • 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
  • A61P17/06—Antipsoriatics
• • 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
  • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
• • 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
  • A61P17/16—Emollients or protectives, e.g. against radiation
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P37/00—Drugs for immunological or allergic disorders
  • A61P37/08—Antiallergic agents
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
  • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• • 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
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
  • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/10—Preparations for permanently dyeing the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q7/00—Preparations for affecting hair growth
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K38/00—Medicinal preparations containing peptides
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
  • Y02P20/00—Technologies relating to chemical industry
  • Y02P20/50—Improvements relating to the production of bulk chemicals
  • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Definitions

• the present invention relates to pseudopeptide derivatives reproducing the peripheral effects of alpha-MSH (“Melanocyte Stimulating Hormone”), their preparation and their therapeutic and cosmetic application.
• alpha-MSH Melanocyte Stimulating Hormone
• Alpha-MSH is a substance naturally produced by the human organism known to have numerous physiological activities: antipyretics, anti-inflammatories and pigments. As a mediator, alpha-MSH has specific receptors, five of which have been described and each has 7 transmembrane domains. In the skin, the above-mentioned activities involve the “melanocortin-1” receptor (MC-lr). At this level, the binding of alpha-MSH induces the activation of a G protein (having an ⁇ subunit of G ⁇ s type) which will itself stimulate adenylyl cyclase and thus produce adenosine mono phosphate cyclical (or cAMP).
• G protein having an ⁇ subunit of G ⁇ s type
• cAMP cAMP response elements
• CREB cAMP response elements
• melanins the coloring of the skin and hair is due to a common category of pigments: melanins.
• the production of these melanins in the skin is ensured by the melanocytes, cells located at the level of the basement membrane of the epidermis and in the hair follicles.
• the synthesis of melanins is controlled by the activity of an enzyme: tyrosinase. It is the production of this enzyme (as well as that of the associated enzymes: TRP-1 & TRP-2) which is stimulated by the binding of alpha-MSH to its MC-1 receptor.
• melanin The production of melanin by tyrosinase takes place within cytoplasmic organelles: the premelanosomes. Once filled with melanins, these organelles are called melanosomes and are transferred, via the dendrites of the melanocyte, to neighboring cells: keratinocytes. The melanin is thus distributed in the epidermis, ensuring its browning and its protection.
• Melanin a natural pigment known for its anti-free radical properties and absorbing solar radiation, is the physiological protective agent of the skin. There is no compound available in dermocosmetology that can stimulate the production of this pigment in humans.
• alpha-MSH by binding to the MC-1 receptor, inhibits the induction of NOSi (or NOS2), NFKB and induces the expression of mRNA followed by the production of the anti-inflammatory cytokine IL-10.
• NOSi NOS2
• NFKB NFKB
• This cytokine is opposed to the release of cytokines from inflammation like IL -1, IL6, IL-8, TNF- ⁇ , or INF ⁇ .
• the keratinocytes which constitute 95% of the cell population of the epidermis are considered to be reservoirs for IL-1 and have MC-1 receptors on their cell surface.
• IL-1 IL-1 receptors
• the binding of alpha-MSH to these receptors allows modulation of local inflammatory phenomena.
• the present invention thus aims to provide small linear pseudopeptide compounds having melanotropic and / or anti-inflammatory, anti-allergic activities. More specifically, the subject of the invention is new peptides corresponding to formula (I)
• R represents a hydrogen atom or a protective group which can be chosen from an acetyl group, a benzoyl group, a tosyl group, a benzene sulfonyl group, a benzyloxycarbonyl group or a pyridinepropionyl group.
• V represents a natural or unnatural amino acid, of configuration L, chosen from norleucine, norvaline and 2-N-Me-norleucine.
• X represents a natural or unnatural amino acid, of L or D configuration, of aromatic character chosen from phenylalanine, 1-naphthylalanine, 2-naphthylalanine, phenylglycine, benzothienylalanine, 4,4'-biphenylalanine, 3, 3-diphenylalanine, Phomophenylalanine, Pindanylglycine, 4-methylphenylalanine, thienylalanine, p-nitro-phenylalanine, halogenophenylalanine where the halogen can be a chlorine, bromine, iodine or fluorine atom in meta, ortho or para of the phenyl group.
• Y represents a natural amino acid of configuration L, of basic character chosen from arginine, lysine or ornithine.
• amino acids Ala, His and Trp respectively at positions 2, 3 and 6 in the peptide of formula (I) are of configuration L.
• the peptides of formula (I) may contain one or more asymmetric carbon atoms. They can exist in the form of enantiomers or diastereoisomers. These enantiomers, diastereoisomers, as well as their mixtures, including racemic mixtures are part of the invention.
• these new peptides have an activity for stimulating pigmentation and / or limiting local inflammatory phenomena in the skin or mucous membranes.
• the peptides according to the invention are useful in the prevention and / or treatment of pathologies such as atopic dermatitis, psoriasis, vitiligo, erythema, inflammatory alopecia, eczema or asthma, which are initiated at the cellular level and can be attenuated by the direct intervention of compounds which mimic natural mediators.
• the peptides which are the subject of the present invention therefore constitute a spectacular innovation in skin care.
• the present invention thus also relates to the use of one or more peptides of formula (I) for the manufacture of a medicament having an anti-inflammatory and / or anti-allergic effect as well as the use of one or more peptides of formula (I) for the manufacture of a cosmetic product having a melanotropic activity.
• R represents a protective group which can be chosen from an acetyl group, a benzene sulfonyl group, a tosyl group or a pyridinepropionyl group
• V represents a natural amino acid or not chosen from norleucine and 2-
• N-Me-norleucine of configuration L.
• X represents a natural or non-aromatic amino acid chosen from phenylalanine, 2-naphthylalanine, homophenylalanine, thienylalanine or p-nitro-phenylalanine, of configuration D or L.
• Y represents a natural amino acid of configuration L , of a basic character chosen from arginine or lysine.
• the compounds of general formula (I) can be prepared according to various methods known to a person skilled in the art, in particular by chemical synthesis processes in solution or on solid support. Synthesis on a support with resin is particularly suitable.
• the resins which can be used mention may be made of the resin of the Rink amide type (or 4- (2 ′, 4′-dimethoxyphenyl-fmoc-aminomethyl) - ⁇ henoxy resin) (H. Rink, Tetrahedron Let., 1987 , 28, 3787) and the MBHA resin (or 4-methyl-benzhydrylamine resin) (GR Matsueda et al. Peptides, 1981, 2, 45).
• the starting materials are protected amino acids.
• the protective groups can be an acetyl group (Ac) or a 9-fluorenylmethoxycarbonyl group (Fmoc) on the main amine function, a tert-butyloxycarbonyl group (Boc), a Trityl group (Trt), a group 2,2, 5,7,8- pentamethylchroman-6-sulfonyl (Pmc) on the functions of the side chains. Washing, coupling and deprotection techniques are well known to those skilled in the art.
• Example 1 Compound No. 1 in the Table
• This peptide is synthesized by synthesis on a solid support with a resin of the Rink amide type, the functionalization of which is between 0.3 and 0.6 mmol / g of resin.
• the Rink amide resin is firstly prepared, by washing with DMF (2 washes), then deprotection is carried out as described below. For each amino acid to be coupled, the steps of coupling the amino acid, washing the resin, deprotecting the amino function of the main chain of the amino acid, and again washing the resin are repeated. Coupling: 2 equivalents of BOP (or HBTU), 2 equivalents of DIEA (or NMM) and 2 equivalents of Fmoc-AA-OH for 2 hours in DMF.
• the peptide is cleaved from the resin using a TFA / dichloromethane 50/50 mixture with 2% ethanediol for 1 h 30 min.
• the dichloromethane and the TFA are evaporated under nitrogen flow, then precipitated with diethyl ether and purified on preparative liquid chromatography, with a C1 reverse phase column.
• BOP Benzotriazole-l-yl-oxy-tris (dimemylamino) phosphonium hexafluorophosphate
• This peptide is synthesized by synthesis on a solid support with a resin of the Rink amide type, the functionalization of which is between 0.3 and 0.6 mmol / g of resin.
• HPLC High Performance Liquid Chromatography
• the purities are expressed as a relative percentage relative to the surface of the peaks of the crude product before purification and the retention times (TR) are expressed in minutes.
• TR retention times
• - PyrProp represents a pyridinepropionyl group
• DHomoPhe homophenylalanine of configuration D
• Nap represents the 2-naphthylalanine of configuration L
• - DPhe represents the phenylalanine of configuration D
• - NMe-Nle represents 2-N-Me-Norleucine of configuration L.
• a synthesis on a support can be carried out with a resin of the Rink amide type as described in Example 1.
• amino acids are introduced in protected form onto the side chains if necessary, the main function being protected by an Fmoc group.
• the molecules used for these syntheses are according to the position:
• Trp 6 Fmoc-Trp (Boc) -OH
• Y 5 Fmoc-Arg (Pmc) -OH, Fmoc-Lys (Boc) -OH
• Ala 2 Fmoc-Ala-OH
• Ala 1 Ac-Nle-OH, Fmoc-Nle-OH in the case of terminal protection other than acetyl protection.
• the terminal protections (R) will be introduced, after a deprotection step, by coupling, using the following reagents: benzene sulfonyl chloride, pyridine propionyl chloride and tosyl chloride.
• the peptides of the invention have been the subject of pharmacological tests making it possible to determine their effects after their safety has been confirmed by the appropriate toxicity and tolerance tests.
• peptide No. 1 and alpha-MSH The action of peptide No. 1 and alpha-MSH on the production of tyrosinase has been demonstrated in vitro on maintained human melanocytes.
• the production of tyrosinase was monitored on the M4Be line by western-blotting using an anti-human tyrosinase antibody. After 24 hours of culture, the cells are added with alpha-MSH or peptide No. 1 at a concentration of 10 " M final.
• the cells are peeled off and lysed in NaH 2 PO 4 50mM buffer pH 6.8 + 1% Triton XI 00 + ImM PMSF
• the protein level of the various samples is determined by assay with bicinconinic acid and 100 ⁇ g of sample is deposited per well of 15% electrophoresis gel d 'acrylamide / bisacrylamide.
• the samples are migrated for 3 hours at 70 mA. Transfer to a nitrocellulose membrane (Schleicher & Schuell, ref Protari) is carried out overnight at 10 V.
• the membrane is blocked with buffer at pH 7, 6 (200mM Tris; 1.37 M NaCl; 1M HC1) + 0.1% Tween + 5% BSA, for 1 hour at 37 ° C.
• the revelation is carried out firstly by a goat anti-tyrosinase antibody human (Santa Cruz, ref SC-7833) diluted to 1 / 1000th at 4 ° C overnight, then incubated with an anticor ps goat anti-immunoglobulin coupled with peroxidase (Sigma, ref A8919) diluted to 1/10000 at room temperature for 1 hour.
• the presence of tyrosinase is visualized by chemiluminescence using an ECL detection kit (Amersham Pharmacia Biotech, ref. RPN2109) which prints a photographic film (Amersham Pharmacia Biotech, ref. RPN2103K) reported in Figure 1/1.
• the ultra structural analysis of melanocytes and melanosomes was carried out by electron microscopy.
• the fine sections were subjected to a double contrast technique and then observed at magnifications of up to x 12,000 (Jeol 1200EX).
• peptide No. 1 in the table induces a statistically significant increase in skin browning (tanning) by 54% (p ⁇ 0.05, Student's t test). Clinical observation of the treated areas did not show any sign of intolerance. Compared to placebo, peptide No. 1 in the table induces a statistically significant increase (+ 68%, p ⁇ 0.01) in the quantity of melanin in the epidermis of the volunteers. The analysis of variance according to the Fisher test reveals a very significant product effect with a risk of less than 1%.
• the ultra-structural analysis of the melanocytes reveals an important influence of the treatment with large cells, a developed nucleus with little heterochromatin, very abundant cellular organelles and dendrites loaded with eumelanosomes. All these signs testify to an intense activity of biosynthesis of melanin, perfectly physiological.
• melanosomes in keratinocytes show that they naturally accumulate at the apical level of the cell nucleus constituting a typical "nuclear parasol".
• Peptide No. 1 in the table applied topically has been shown to be able to significantly stimulate skin melanogenesis in humans. It is also perfectly tolerated locally.
• Anti-inflammatory activity has been demonstrated as follows: In the skin, irritants such as surfactants are responsible for inflammatory reactions characterized by the extracellular expression of cytokines such as interleukin-1 alpha (IL- la). The keratinocyte model in SDS-stimulated culture was used to assess the anti-inflammatory potential of peptide # 1 in the table.
• irritants such as surfactants are responsible for inflammatory reactions characterized by the extracellular expression of cytokines such as interleukin-1 alpha ( IL- la).
• IL- la interleukin-1 alpha
• NCTC 2544 human keratinocytes are cultured with peptide No. 1 in the table at a concentration of 10 ⁇ 6 M for 72 hours. After rinsing, the SDS is introduced at a concentration of 85 mg / 1 and left in contact for 24 hours.
• the extracellular IL-1 ⁇ levels in the supernatant are determined by the ELIS A method (Immunotech, ref 0755) chosen for the absence of interference with the SDS.
• Peptide No. 1 reduces by approximately 42% the expression of IL-1 ⁇ by keratinocytes in culture stressed by SDS.
• the treatment consists of a topical application on the internal face of the forearm 2 times / day for 2 weeks at a rate of 2 ⁇ l / cm 2 over 75 cm 2 .
• the arm is protected from any sun exposure.
• the solar radiation is given by a 150 W xenon arc lamp with a UVA & B spectrum ranging from 290 to 390 nm.
• Six doses of light intensity in geometric progression of 25% are applied to the treated areas through liquid light guides.
• the colorimetric measurements are made with the Chromameter TM CR 300.
• the chromaticity coordinates (L; a & b *) are determined relative to a nearby non-irradiated area.
• a differential ⁇ a *> 2.5 allows the DEM to be precisely defined 24 hours after the last treatment, the treated and control areas are irradiated with increasing doses of UV calculated to frame the DEM of each individual. After 24 h and 72 h, the irradiated area is evaluated by colorimetric measurements.
• the evaluation criterion is the D.E.M. : the lowest dose of UV A&B that causes erythema.
• peptide No. 1 in the gel table topically makes it possible to increase the resistance of the skin to the appearance of an erythema caused by excessive solar irradiation.
• peptides of the invention have anti-inflammatory, anti-allergic and melanotropic activity.
• the peptides of the invention can therefore be used for the preparation of medicaments intended for treating allergies, in particular cutaneous, inflammatory reactions and disorders of melanogenesis.
• These drugs thus find their use in therapy in particular in the prevention and / or treatment of atopic dermatitis, psoriasis, vitiligo, erythema and in particular photo-induced erythema, inflammatory alopecia, eczema and asthma.
• the present invention relates to pharmaceutical compositions containing, as active principle, a peptide according to the invention.
• These pharmaceutical compositions can in particular be adapted to a local application on the skin and the mucous membranes.
• compositions contain an effective dose of a peptide according to the invention, and one or more suitable pharmaceutical excipients.
• Said excipients are chosen according to the pharmaceutical form and the desired mode of administration.
• the active principle of formula (I) above its optional salt or hydrate can be administered in unit administration form, in mixture with conventional pharmaceutical excipients, to animals and humans for the prophylaxis or treatment of the above disorders or diseases.
• Suitable unit administration forms include oral forms such as tablets, capsules, powders, granules and oral solutions or suspensions, sublingual, buccal, intratracheal, intranasal administration forms, subcutaneous, intramuscular or intravenous administration and forms of rectal administration.
• the compounds according to the invention can be used in creams, ointments, liquid or spray aerosols (sprays), gels, lotions and patches.
• the dose of active ingredient administered per day can reach 0.5 mg / kg, in one or more doses.
• the appropriate dosage for each patient is determined by the doctor according to the method of administration, the weight and the response of said patient.
• a pharmaceutical excipient such as gelatin, starch, lactose, magnesium stearate, talc, gum arabic or the like.
• the tablets can be coated with sucrose, a cellulose derivative, or other materials.
• the tablets can be produced by different techniques, direct compression, dry granulation, wet granulation or hot melting.
• a preparation in capsules is obtained by mixing the active ingredient with a diluent and by pouring the mixture obtained into soft or hard capsules.
• aqueous suspensions, isotonic saline solutions or sterile injectable solutions which contain pharmacologically compatible dispersing agents and / or wetting agents, for example propylene glycol or butylene glycol, may be used.
• the present invention according to another of its aspects, also relates to a method of treatment of the pathologies indicated above which comprises the administration of a peptide according to the invention or one of its pharmaceutically acceptable salts.
• a cosmetic composition comprising a compound of formula (I) which can be administered by mucous or topical route also forms part of the invention as well as the use of a compound of formula (I) for the preparation of a cosmetic product having a melanotropic effect.
• the subject of the invention is dermocosmetic compositions comprising a peptide of formula (I) according to the invention for topical application which can take the form of solutions, lotions, emulsions, liquid or spray aerosols (sprays), gels or creams that can be used in particular as a skin preparation agent for sun exposure, a tanning accelerator recolouring white hair, skin soothing, anti-erythematosus.
• a peptide of formula (I) for topical application
• the pharmaceutical compositions, cosmetic products or dermocosmetic compositions which are the subject of the invention as described above containing mixtures of peptides according to the invention also form part of the invention.

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