WO2012164488A2 - Nouvelle utilisation topique cosmétique ou dermopharmaceutique d'un mélange d'un tripeptide ghk et d'un tétrapeptide gqpr - Google Patents

Nouvelle utilisation topique cosmétique ou dermopharmaceutique d'un mélange d'un tripeptide ghk et d'un tétrapeptide gqpr Download PDF

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WO2012164488A2
WO2012164488A2 PCT/IB2012/052681 IB2012052681W WO2012164488A2 WO 2012164488 A2 WO2012164488 A2 WO 2012164488A2 IB 2012052681 W IB2012052681 W IB 2012052681W WO 2012164488 A2 WO2012164488 A2 WO 2012164488A2
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agents
phase
gqpr
seq
ghk
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PCT/IB2012/052681
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WO2012164488A3 (fr
Inventor
Arnaud Fournial
Philippe Mondon
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Sederma
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Priority to EP12726879.5A priority Critical patent/EP2714001A2/fr
Publication of WO2012164488A2 publication Critical patent/WO2012164488A2/fr
Publication of WO2012164488A3 publication Critical patent/WO2012164488A3/fr

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    • 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
    • A61K8/18—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
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/06—Tripeptides
    • 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
    • A61K38/07—Tetrapeptides
    • 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 present invention relates to a new topical use, cosmetic or therapeutical, of a peptidic mixture comprising a GHK type tripeptide (hereafter symbolised A-GHK-B) and a GQPR type tetrapeptide (hereafter symbolised A-GQPR-B, SEQ ID NO: 1), for the treatment of skin (including scalp skin) of human or animal mammals.
  • the invention aims for the cosmetic, hygiene and personal care, and dermopharmacy industries.
  • the GQPR Glycine-Glutamine-Proline-Arginine, SEQ ID NO: 2
  • GHK Glycine-Histidine- Lysine sequences belong to Matrikines, known to participate in the reconstruction of the extracellular matrix of the connective tissue.
  • a composition comprising a mixture of Pal-GHK tripeptide and Pal-GQPR tetrapeptide (SEQ ID NO: 3) in a physiologically acceptable excipient is marketed as anti- wrinkle active by the Applicant Sederma under the trade name MatrixylTM3000 (WO 2005/048968).
  • Dermis is composed of a part called deep reticular dermis and an upper part called papillary dermis which is in contact with the epidermis via the dermal-epidermal junction (DEJ).
  • DEJ dermal-epidermal junction
  • the fibre network of the papillary dermis is different, more fragile.
  • the proportions of collagen I and III are different and the network contains more glycoproteoglycans and glycosaminoglycans.
  • This area also contains fibroblasts that have a very important role in the formation of the epidermis.
  • the papillary dermis forms thus an important area of the skin, but fragile, especially very sensitive to UV radiations.
  • the upper part of the papillary dermis is slightly echogenic and can thus be visualized by ultrasound imaging (dermal fibers less dense returning less echos). This part is thus also called the SLEB “Sub- epidermal Low Echogenic Band” (or also called SENEB, "sub-epidermal non-echogenic band”). It has been shown that the thickness of the papillary dermis SLEB increases with time and exposure to solar radiations.
  • the present invention aims to provide a composition adapted to act specifically and efficiently on the papillary dermis, especially for the treatment of skin affected by a photo-induced and/or chronological aging.
  • B OH, OR 1; NH 2 , NHRi, NRiR 2 , Ri and R 2 being, independently of one another, selected from an alkyl, aryl, aralkyl, alkylaryl, alkoxy and aryloxy group, which may be linear, branched, cyclic, polycyclic, unsaturated, hydroxylated, carbonylated, phosphorylated and/or sulfured, said group which may have a heteroatom in its skeleton including O, S and/or N.
  • A is at the peptide N terminal end (conventionally at left).
  • papillary dermis can be reconstructed (by reducing the SLEB papillary dermis thickness and improving its density). Thanks to the invention, the papillary dermis can be rejuvenated.
  • a mixture of A-GHK-B and A-GQPR-B (SEQ ID NO: 1) peptides, or of their derivatives or analogs, can be used for preventing and/or treating aging of the papillary dermis, especially for the treatment of a skin overexposed to solar radiations (photo-induced aging).
  • the application areas are multiple, wherever necessary, damaged areas and/or areas where the dermis is particularly sensitive, for example the lips.
  • the eye contour and the neckline may be areas as well covered by the present invention uses. Uses can also be performed as a preventive measure.
  • the topical use of the invention may be either of cosmetic or therapeutical type (dermopharmacy).
  • the present invention proposes a composition comprising a mixture of A- GHK-B tripeptide and A-GQPR-B tetrapeptide (SEQ ID NO: 1), or their derivatives or analogs, for the therapeutic treatment of the papillary dermis.
  • the invention encompasses a composition comprising a mixture of A- GHK-B tripeptide and A-GQPR-B tetrapeptide (SEQ ID NO: 1), or their derivatives or analogs, for the therapeutic treatment of a skin over-exposed to radiations, especially solar radiations.
  • the mixture of the invention will have a healing effect thanks to a papillary dermis reconstruction.
  • the peptides according to the invention may be optically pure, or consist of L or D isomers or a mixture thereof.
  • the L isomers which are those present in nature may be preferred because less expensive.
  • invention peptides may be fragments of a larger peptide, containing more amino acids than the tripeptide and tetrapeptide active "core".
  • the present invention also encompasses derivatives (with modifications and/or addition of a chemical function but no change in the carbon skeleton) and analogs (with modifications and/or addition of a chemical function but in addition a change in the skeleton carbon), complex with other species such as a metal ion (eg copper, zinc, manganese, magnesium, and others).
  • a metal ion eg copper, zinc, manganese, magnesium, and others.
  • the presence of groups other than H for A and/or other than OH or NH 2 for B on the peptides may have several purposes including: - Modifying the lipophilic character of the peptide to improve its solubility in an excipient and/or its bioavailability and its ability to penetrate skin; and/or
  • the peptide(s) is or are substituted at the N terminal end with A being an CO-Ri acyle or
  • Ri and/or R 2 is an alkyle chain, preferably comprising 1 to 24 carbon atoms, preferably a linear chain; Ri and/or R 2 are preferably lipophilic chains comprising 6 to 24 carbon atoms;
  • A is preferably an CO-Ri acyle group, in particular chosen among biotinoyl, acetyl, palmitoyl, elaidoyl, myristoyl, octanoyl, stearoyl, oleoyl and lipoyl;
  • A CO-Ri or S0 2 -Ri, Ri being a polycyclic group comprising from 2 to 6 cycles, in particular derivated from oleanolic, ursolic, boswelllic, betulinic or madecassic acid;
  • Ri comprises a sugar part.
  • a topical composition for implementing the invention comprises an effective content of A-GHK-B tripeptide and A-GQPR-B tetrapeptide (SEQ ID NO: 1), as recited above, in a physiologically acceptable medium.
  • the "effective" amount depends on various factors such as age, the state of the patient, the severity of the disorder or disease and the administration mode.
  • An effective amount means a nontoxic amount sufficient to achieve the desired effect.
  • the peptides, to be present in an effective amount are generally in proportions of between 0.000001% and 15% relative to the total weight of the composition, more preferably between 0.0001 % and 5%, depending on the destination of the composition and the desired effect more or less pronounced.
  • the peptides may be present in the compositions according to the invention in variable relative proportions, in equivalent amounts, or otherwise in different proportions.
  • Physiologically acceptable medium means according to the present invention, without limitation, an aqueous or hydroalcoholic solution, a water-in-oil emulsion, an oil-in-water emulsion, a microemulsion, an aqueous gel, an anhydrous gel, a serum, a vesicle dispersion, a powder.
  • compositions are suitable for topical or transdermal use in contact with mucous membranes, nails, scalp, hair and skin of mammals and particularly human, compositions that can be ingested or injected into the skin without risk of toxicity, incompatibility, instability, allergic response, and others.
  • This "physiologically acceptable medium” forms what is commonly called the excipient of the composition.
  • the peptide mixture according to the invention may be solubilized in a hydroalcoholic matrix, for example consisting of a water/glycerin mixture.
  • the present invention also provides a cosmetic treatment method for repairing the papillary dermis comprising applying to the skin (including lips) of a mixture of peptides A-GHK-B and A-GQPR- B (SEQ ID NO: 1), or their derivatives or analogues, as defined above.
  • the treatment of the invention may be particularly interesting on the lips where the epidermis is very thin and the dermis very thick.
  • the peptide may be combined with other active ingredients at effective concentrations that can act synergistically or in reinforcement to achieve the desired effects on the papillary dermis described for the invention, such as the following agents: radiation filters, including UVA and UVB, moisturizing, calming, myorelaxant, slimming, restructuring, firming, acting on microcirculation, acting on inflammation, on free radicals, vitamins, etc.
  • composition of the invention can be applied on the face, lips, eye contour, body, neckline, scalp, in any form or vehicles known to the skilled artisan, including in the form of a solution, dispersion, emulsion, paste or powder, individually or in pre-mixture or be conveyed individually or in pre-mixture by vectors such as macrocapsules, microcapsules or nanocapsules, macrospheres, microspheres, or nanospheres, liposomes, oleosomes or chylomicrons, macroparticles, microparticles or nanoparticles, macrosponges, microsponges or nanosponges, microemulsions or nanoemulsions, or adsorbed on powdery organic polymers, talcs, bentonites, spores or exines or any other inorganic or organic medium.
  • vectors such as macrocapsules, microcapsules or nanocapsules, macrospheres, microspheres, or nanospheres, liposomes, oleosomes or chy
  • applications can be offered for example in the ranges of facial and body skin care treatments, makeup-care products, including lip products.
  • the peptides of the present invention can be used in any form, in a bound form, incorporated or adsorbed on macro-, micro- and nano-particles, or on macro-, micro- and nano- capsules for the treatment of textiles, natural or synthetic fibers, wools, and all materials intended to come into contact with skin and that can be used in clothing, day and night underwears, handkerchiefs, or textiles, in order to exert its cosmetic or therapeutic effect via this contact skin/textile and allow continuous topical delivery.
  • a composition according to the invention may further contain other ingredients that can enhance the appearance and feel touch of the skin.
  • ingredients classes include, but are not limited to: healing agents, skin anti-aging agents, anti- wrinkle agents, anti-atrophy agents, skin moisturizing agents, skin smoothing agents, antibacterial agents, anti-parasitic agents, antifungal agents, fungicidal agents, fungistatic agents, bactericidal agents, bacteriostatic agents, antimicrobial agents, anti-inflammatory agents, anti-pruriginous agents, anesthetic agents, antiviral agents, keratolytic agents, free radicals scavengers, anti- seborrhea agents, antidandruff agents, the agents modulating differentiation, proliferation or pigmentation of the skin, penetration accelerating agents, desquamating agents, melanin synthesis stimulating or inhibiting agents, whitening, depigmenting or lightening agents, pro-pigmenting agents, self-tanning agents, NO-synthase inhibiting agents, antioxidants, free radical scavengers and/or agents against atmospheric pollution, reactive carbonyl species scavengers
  • triethanolamine triethanolamine
  • propellants reducing agents, sequestrants, decoloring and/or lightening agents
  • skin-conditioning agents e.g., humectants, including miscellaneous and occlusive
  • moisture retaining agents alphahydroxyacids, betahydroxyacids, moisturizers, epidermal hydrolytic enzymes, healing and/or calming agents
  • skin treating agents anti-wrinkle agents, agents that reduce or treat bags under the eyes, exfoliating agents, thickeners, softening agents, gelling polymers, vitamins and their derivatives, wetting agents, peeling agents, soothing agents, curative agents of the skin, lignans, preservatives (i.e.
  • phenoxyethanol and parabens include anti UV, cytotoxic agents, anti-neoplastics, viscosity modifiers, non-volatile solvents, pearling agents, anti-perspirant agents, depilatories, vaccine, perfumed water, skin restructuring agent (i.e.
  • Such additional active ingredient/compound can be selected from the group consisting of: sugar amines, glucosamine, D-glucosamine, N-acetyl glucosamine, N-acetyl-D-glucosamine, mannosamine, N-acetyl mannosamine, galactosamine, N-acetyl galactosamine, B3 vitamin and its derivatives, niacinamide, sodium dehydroacetate, dehydroacetic acid and its salts, phytosterols, salicylic acid compounds, hexamidines, dialkanoyl hydroxyproline compounds, soy extracts and derivatives, equol, isoflavones, flavonoids, phytantriol, farnesol, geraniol, bisabolol, peptides and their derivatives, di-, tri-, terra-, penta-, and hexapeptides and their derivatives, KTTKS (SEQ ID NO: 11), Pal-KTTKS
  • betain betain, glycerol, Actimoist Bio 2TM (Active organics), AquaCacteenTM (Mibelle AG Cosmetics), AquaphylineTM (Silab), AquaregulKTM (Solabia), CarcilineTM (Greentech), CodiavelaneTM (Biotech Marine), DermafluxTM (Arch Chemicals, Inc), Hydra'FlowTM (Sochibo), Hydromoist LTM (Symrise), RenovHyalTM (Soliance), SeamossTM (Biotech Marine), EssenskinTM (Sederma), Moist 24TM (Sederma), ArgirelineTM (trade name of the acetyl hexapeptide-3 of Lipotec), spilanthol or an extract of Acmella oleracea known under the name Gatuline ExpressionTM, an extract of Boswellia serrata known under the name BoswellinTM, Deepaline PVBTM (Seppic), PhytoCellTecTMArgan (
  • extracts of Ivy in particular English Ivy (Hedera Helix), of Bupleurum chinensis, of Bupleurum Falcatum, of arnica ⁇ Arnica Montana L), of rosemary ⁇ Rosmarinus officinalis N), of marigold ⁇ Calendula officinalis), of sage ⁇ Salvia officinalis L), of ginseng ⁇ Panax ginseng), of ginko biloba, of St.-John's-Wort ⁇ Hyperycum Perforatum), of butcher's- broom ⁇ Ruscus aculeatus L), of European meadowsweet ⁇ Filipendula ulmaria L), of big- flowered Jarva tea ⁇ Orthosiphon Stamincus Benth), of algae ⁇ Fucus Vesiculosus), of birch ⁇ Betula alba
  • C. blumei, C esquirolii, C scutellaroides, C xanthantus and C Barbatus such as the extract of root of Coleus barbatus, extracts of Ballote, of Guioa, of Davallia, of Terminalia, of Barringtonia, of Trema, of antirobia, cecropia, argania, dioscoreae such as Dioscorea opposita or Mexican, extracts of Ammi visnaga, of Siegesbeckia, in particular Siegesbeckia orientalis, vegetable extracts of the family of Ericaceae, in particular bilberry extracts (Vaccinium angustifollium) or Arctostaphylos uva ursi, aloe vera, plant containing sterols (e.g., phytosterol), Manjistha (extracted from plants of the genus Rubia, particularly Rubia Cordifolia), and Guggal (extracted from plants of
  • compositions of the present invention may include other peptides, including, without limitation, the di-, tri-, terra-, penta-and hexapeptides and their derivatives.
  • concentration of the additional peptide, in the composition ranges from lxl0 "7 and 20%, preferably from lxl0 ⁇ 6 % and 10%, preferably between lxl0 "5 % and 5% by weight.
  • peptide refers to peptides containing 10 amino acids or less, their derivatives, isomers and complexes with other species such as a metallic ion (e.g. copper, zinc, manganese, magnesium, and others).
  • peptides refers to both natural peptides and synthetic peptides. It also refers to compositions that contain peptides which are found in nature, and/or that are commercially available.
  • Suitable dipeptides for use herein include but are not limited to carnosine (beta- AH), YR, VW, NF, DF, KT, KC, CK, KP, KK or TT.
  • Suitable tripeptides for use herein include, but are not limited to RKR, HGG, GKH, GGH, GHG, KFK, KPK, KMOK, KM0 2 K or KAvaK.
  • Suitable tetrapeptides for use herein include but are not limited to RSRK (SEQ ID NO: 13) or KTFK (SEQ ID NO: 14).
  • Non limitative suitable examples of pentapeptide include the KTTKS (SEQ ID NO: 11) and of hexapeptides the GKTTKS (SEQ ID NO: 15) and VGVAPG (SEQ ID NO: 16).
  • Suitable peptides for use herein include, but are not limited to: lipophilic derivatives of peptides, preferably palmitoyl derivatives, and metal complexes as aforementioned (e.g. copper complex of the tripeptide HGG).
  • Preferred dipeptide derivatives include Pal-beta-AH, Ac-YR- hexadecylester (CalmosensineTM, IdealiftTM from Sederma), Pal-KT, Pal-RT (Sederma).
  • Preferred tripeptide derivatives include the copper derivative of HGG (LaminTM from Sigma), Lipospondin (Ela-KFK) and its analogs of conservative substitution, Ac-RKR-NH 2 (Peptide CK+), Pal-KM0 2 K (Sederma) and derivatives thereof.
  • a suitable tetrapeptide derivative for use according to the present invention includes, but not limited to, Ela-KTFK (SEQ ID NO: 17), (from Sederma), suitable pentapeptide derivatives for use herein include, but are not limited to, Pal-KTTKS (MATRIXYLTM, SEQ ID NO: 12), Pal-YGGFX (SEQ ID NO: 18) with X being Met(M) or Leu(L) or mixtures thereof.
  • Suitable hexapeptide derivatives for use herein include, but are not limited to, Pal-VGVAPG (SEQ ID NO: 19), Pal-GKTTKS (SEQ ID NO: 20) and derivatives thereof.
  • compositions commercially available containing a tripeptide or a derivative include MaxilipTM, BiobustylTM and MatrixylTMsynthe'6TM of Sederma.
  • compositions commercially available preferred sources of tetrapeptides include RiginTM, EyelissTM, MatrixylTM Reloaded and Matrixyl 3000TM proposed by Sederma.
  • peptides can be mentioned as well as additional active ingredients: VialoxTM, Syn-akeTM or Syn-CollTM (Pentapharm), Hydroxyprolisilane CNTM (Exsymol), ArgirelineTM, LeuphasylTM, AldenineTM, TrylgenTM, EyeserylTM, SerilesineTM or DecorinylTM (Lipotec), CollaxylTM or QuintescineTM (Vincience), BONT-L-PeptideTM (lnfinitec Activos), CytokinolTMLS (Laboratoires Serobi GmbH/Cognis), KollarenTM, IP2000TM or MelipreneTM (lnstitut Europeen de Biologie Cellulaire), NeutrazenTM (Innovations), ECM-ProtectTM (Atrium Innovations), Timp-PeptideTM, ECM ModulineTM (lnfinitec Activos).
  • the present invention also proposes a cosmetic treatment method to improve the general appearance of the skin, thanks to a reconstruction of the papillary dermis, comprising the application to the skin of an effective amount of a composition according to the invention as recited above.
  • composition according to the invention may be applied locally onto targeted areas.
  • One of the major advantages of the present invention resides in the ability whenever necessary or desirable to be able to apply local selective "gentle" treatments through this topical, non-invasive method of application.
  • the application can be carried out very locally using a liner, a pencil, a roll-on applicator, a brush, a micro-cannula, applicators which are well known to the skilled person.
  • topical cosmetic treatment method according to the invention can be combined with one or several other treatment methods targeting the skin such as luminotherapy, heat or aromatherapy treatments.
  • devices with several compartments or kits may be proposed to apply the method described above which may include for example and non-restrictively, a first compartment containing a composition comprising one of the peptide of the invention, and in a second compartment a composition containing the other peptide and/or excipient, the compositions contained in the said first and second compartments in this case being considered to be a combination composition for simultaneous, separate or stepwise use in time, particularly in one of the treatment methods recited above.
  • the treatment method of the invention is more particularly adapted to the treatment of photodamaged skin.
  • galenic formulas are given below containing the Pal-GHK-OH peptide and the Pal-GQPR-OH peptide (SEQ ID NO: 3) according to the invention as active ingredient.
  • These formulas can also incorporate additional active ingredients, the latter coming if appropriate to support and/or in addition to the activity of the active ingredient of the invention.
  • These ingredients can be of any class according to their(s) function(s), the application site (body, face, hands, etc.), the desired final effect and the target consumer.
  • MATRIXYL® 3000 comprising:
  • Excipient glycerin, eau, butylen glycol, carbomer and polysorbate.
  • MATRIXYL® 3000 Lipo comprising:
  • Excipient Alkylated benzoate, sorbitan laurate, tristearin and acetylated glycol stearate.
  • RIGINTM comprising:
  • Excipient glycerin, eau, polyethoxylated alcohol.
  • BIOPEPTIDE CLTM comprising:
  • Palmitoyl Tetrapeptide-7 Procedure weigh phase A and melt around 90°C. Mix phase B and then add it to phase A. Add phase C extemporaneously. Melt Phase D and add it to phase A+B+C. Homogenize. Pour into molds. Cool to room temperature.
  • RENO V AGETM global anti-ageing active ingredient marketed by SEDERMA (WO2006/020646). 3% by weight of this ingredient can be for example added to the formulation in phase D.
  • SUBLISKINTM active ingredient marketed by SEDERMA (WO2009/055663) which hydrates and smoothes the skin while allowing it to resist to external aggression. 3% by weight of this ingredient may for example be added to the formulation in the phase G.
  • DERM AX YLTM anti-aging active ingredient marketed by SEDERMA (WO2004/101609) which smoothes wrinkles and repairs the skin barrier. 3% by weight of the ingredient may for example be added to phase G.
  • Niacinamide (B3vitamine), retinol, resveratrol, DHEA : anti-aging actives, in particular anti- wrinkles.
  • 0,5 % by weight of retinol, of resveratrol or DHEA may be added to phase G.
  • 10% in weight of niacinamide at 10% in water can be for example added to phase G.
  • Hexamidine antibacterial active that may be added to phase G of the formulation at 0.5% by weight.
  • CHRONODYNTM active ingredient actif marketed by SEDERMA (WO2006/075311) that tones and firms the skin, which erases signs of fatigue. 3% of this ingredient may for example be added to phase G.
  • VENUCE ANETM active ingredient marketed by SEDERMA (WO2002/066668) that prevents visible signs of photoaging (spots, wrinkles, dryness %), protects cell structures from damage caused by UV and strengthens skin integrity. 3% of this ingredient may for example be added to phase G.
  • JUVINITYTM active ingredient marketed SEDERMA that reduces signs of aging on the face and neckline, smoothes wrinkles, restructures and densifies the dermis. 2% of this ingredient may for example be added to phase G.
  • O.D.A.whiteTM active ingredient marketed by SEDERMA (WO1994/07837) which lightens the skin by reducing melanin synthesis. 1% of that ingredient may for example be added to phase G.
  • LUMISPHERETM active ingredient marketed by SEDERMA (WO04/024695). It is the combination of diacetylboldine (DAB) encapsulated in microcapsules of polymethylmethacrylate and titanium dioxide modified with manganese (Ti0 2 Mn). The Ti0 2 Mn gives the skin a unifying, mattifying and brightening effect, and DAB provides a physiological lightening. 4% of this ingredient may for example be added to the phase G of the formulation.
  • DAB diacetylboldine
  • REVIDRATTM active marketed by SEDERMA, which in particular improves the epidermis cohesion and its hydration. 2% of this ingredient may for example be added to phase G of the formulation.
  • HALOXYLTM active marketed by SEDERMA (WO2005/102266), which improves the eye contour by reducing dark circles. 3% of this ingredient may for example by added to phase G of the formulation.
  • EYELISSTM is an active marketed by SEDERMA (WO2003/068141) which helps preventing and fighting against the appearance of bags under the eyes. 3% of this ingredient may be added to phase G of the formulation.
  • HYDRERGYTM active marketed by SEDERMA (WO2003/02828692) long lasting hydratant which stimulates ATP synthesis. 3% of this ingredient may be for example added to phase G of the formulation.
  • Type and duration of study this clinical study was conducted blind using non-invasive 5 measurements on 28 volunteers who were randomised and who applied the cream according to the invention to half of their face and one of their forearms. The placebo cream was applied controlaterally. Both creams were applied twice daily, by massaging, for 2 months.
  • ultrasounds When ultrasounds hit a tissue in the human body, they are reflected and return a signal or "echo".
  • the intensity of the echoes is translated by the echograph into grey scale levels to construct a reliable anatomical indicator of the area being investigated.
  • the software in the instrument can also0 allocate colours depending on the intensity of the echoes.
  • the study was set out to assess changes in depth and density of the SLEB on a site which is not extensively exposed to sunlight (internal surface of the forearm) and on a more exposed site (external surface).
  • a Dermascan CTM (Cortex) echograph equipped with a 50 MHz frequency probe was used to5 obtain images approximately 6 mm wide and 3 mm thick with a resolution of 25 x 60 ⁇ .
  • a sequence of 100 successive images was recorded over 4 cm.
  • Five representative images were extracted and analysed by image analysis.
  • the SLEB is traced accurately over a width of 5.5 mm allowing its depth (in ⁇ ) and density (in Grey Scale Levels or GSL) to be calculated automatically.
  • the invention ⁇ 30 ⁇ 20 ⁇ 20 ⁇ 2.34 ⁇ 3.11
  • the external surface of the forearm which is exposed to sunlight deteriorates more than the internal surface, which is better protected from the sun.
  • the SLEB is thicker (195 ⁇ versus 171 ⁇ for the internal surface) and less dense (GSL of 16.2 compared to 19.7 for the internal surface).
  • VivascopeTM 1500 For this study, an instrument called VivascopeTM 1500 has been used. It comprises three laser beams (785 nm, 658 nm and 445 nm) reflected differently depending on the refractory index of the structures they hit.
  • the VivascopeTM can firstly "illuminate” a specific point in the skin (focusing illumination) and, in parallel, accurately detect the returning light (focusing detection). This device is called “confocal” for "conjugate focal planes”.
  • the main feature of the instrument is that it produces a high-definition, horizontal and vertical image in order to obtain a genuine real-time biopsy of the skin, entirely non-invasively.
  • the instrument therefore allows horizontal in situ "sections" of the skin (500 ⁇ x 500 ⁇ ) to be obtained with a horizontal resolution of 1.25 ⁇ and vertical resolution of less than 5 ⁇ .
  • the study examined changes in structure of the superficial dermis of the face at a depth of -70 ⁇ after applying the cream according to the invention. This level allows the observation of the extent of degradation and fragmentation of fibres depending on the person's age and ultra violet exposures Analysis of the images obtained revealed the extent of degradation and fragmentation of the papillary dermis depending on the person's age and ultra violet exposure he was subjected.
  • Cream of the invention 179.1 ⁇ 25.3 199.0 1 39.4 204.1 + 45.4 % change vs. TO 11.1% 13.9%
  • the dermal fibre structure was greatly improved in the papillary area (SLEB) with a significant increase in their circumference of +11.1% at T 1 month then +13.9% at T 2 months.
  • the placebo caused little or no change in this parameter.

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  • Bioinformatics & Cheminformatics (AREA)
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  • Proteomics, Peptides & Aminoacids (AREA)
  • Dermatology (AREA)
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Abstract

Selon l'invention, un mélange d'un tripeptide A-GHK-D et d'un tétrapeptide A-GQPR-B (SEQ ID NO: 1), ou leurs dérivés ou analogues, pour le traitement thérapeutique du derme papillaire, avec : A = H, CO-R1, SO2-R1 ; B = OH, OR1, NH2, NHR1, NR1R2 ; R1 et R2 étant, indépendamment l'un de l'autre, choisis parmi un groupe alkyle, aryle, aralkyle, alkylaryle, alcoxy et aryloxy, qui peut être linéaire, ramifié, cyclique, polycyclique, insaturé, hydroxylé, carbonylé, phosphorylé et/ou soufré, ledit groupe pouvant avoir un hétéroatome dans son squelette comprenant O, S et/ou N ; est utilisé pour empêcher un dommage au derme papillaire et/ou réparer le derme papillaire, pour empêcher et/ou traiter un vieillissement de la peau, en particulier un vieillissement de la peau photo-induit.
PCT/IB2012/052681 2011-06-01 2012-05-29 Nouvelle utilisation topique cosmétique ou dermopharmaceutique d'un mélange d'un tripeptide ghk et d'un tétrapeptide gqpr WO2012164488A2 (fr)

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CN103665102A (zh) * 2013-12-31 2014-03-26 陕西东大生化科技有限责任公司 一种ghk三肽的合成方法
WO2014209910A1 (fr) * 2013-06-24 2014-12-31 Sand Bruce J Composition transépidermique pour régénérer les peaux vieillissant prématurément
WO2014140890A3 (fr) * 2013-03-13 2015-04-09 Neocutis Sa Peptides pour le rajeunissement de la peau et leurs procédés d'utilisation
WO2019028275A1 (fr) * 2017-08-03 2019-02-07 ALASTIN Skincare, Inc. Compositions et procédés permettant d'améliorer la laxité de la peau et le contour du corps
US10286030B2 (en) 2016-02-04 2019-05-14 Alastin Skincare, Inc Compositions and methods for invasive and non-invasive procedural skincare
CN111004304A (zh) * 2019-12-31 2020-04-14 山东济肽生物科技有限公司 一种生物素三肽-1液相合成方法
DE102020201019A1 (de) 2020-01-29 2021-07-29 Beiersdorf Aktiengesellschaft Allergenschutz für die Haut
US11103455B2 (en) 2018-08-02 2021-08-31 ALASTIN Skincare, Inc. Liposomal compositions and methods of use
WO2021170754A1 (fr) 2020-02-28 2021-09-02 Sederma Micro-algues recombinantes capables de produire des peptides, des polypeptides ou des protéines kttks et leurs dérivés, et procédé et utilisations associés
WO2021185953A1 (fr) * 2020-03-20 2021-09-23 Sederma Traitement et composition cosmétique pour le traitement de l'affaissement de la peau
US20210393507A1 (en) * 2014-05-13 2021-12-23 Universkin Extemporaneous cosmetic and/or dermatological preparations
WO2022157587A1 (fr) * 2021-01-23 2022-07-28 Cellix Bio Private Limited Composition comprenant de la lidocaïne, de la l-carnosine et du dexpanthénol
US11571378B2 (en) 2021-01-22 2023-02-07 The Procter & Gamble Company Skin care composition and method of using the same
US11771637B2 (en) 2021-01-22 2023-10-03 The Procter & Gamble Company Skin care composition and method of using the same
WO2024092334A1 (fr) * 2022-10-31 2024-05-10 Chemyunion Ltda Composés, compositions cosmétiques, dermocosmétiques, cosméceutiques ou pharmaceutiques pour le relâchement de la musculature, y compris la musculature squelettique faciale, pour action cosmétique anti-vieillissement, pour réduction et/ou atténuation des lignes d'expression et des rides et/ou pour action anti-transpirante, utilisations et méthodes

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WO2014140890A3 (fr) * 2013-03-13 2015-04-09 Neocutis Sa Peptides pour le rajeunissement de la peau et leurs procédés d'utilisation
CN105189531A (zh) * 2013-03-13 2015-12-23 新科蒂斯公司 用于皮肤复新的肽及其使用方法
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US11331305B2 (en) 2013-03-13 2022-05-17 Anteis Sa Peptides for skin rejuvenation and methods of using the same
US10543195B2 (en) 2013-03-13 2020-01-28 Anteis Sa Peptides for skin rejuvenation and methods of using the same
WO2014209910A1 (fr) * 2013-06-24 2014-12-31 Sand Bruce J Composition transépidermique pour régénérer les peaux vieillissant prématurément
CN103665102B (zh) * 2013-12-31 2016-02-10 陕西东大生化科技有限责任公司 一种ghk三肽的合成方法
CN103665102A (zh) * 2013-12-31 2014-03-26 陕西东大生化科技有限责任公司 一种ghk三肽的合成方法
US20210393507A1 (en) * 2014-05-13 2021-12-23 Universkin Extemporaneous cosmetic and/or dermatological preparations
US10286030B2 (en) 2016-02-04 2019-05-14 Alastin Skincare, Inc Compositions and methods for invasive and non-invasive procedural skincare
US10688147B2 (en) 2016-02-04 2020-06-23 ALASTIN Skincare, Inc. Compositions and methods for invasive and non-invasive procedural skincare
US11426443B2 (en) 2016-02-04 2022-08-30 ALASTIN Skincare, Inc. Compositions and methods for invasive and non-invasive procedural skincare
US11426442B2 (en) 2016-02-04 2022-08-30 ALASTIN Skincare, Inc. Compositions and methods for invasive and non-invasive procedural skincare
US10493011B2 (en) 2017-08-03 2019-12-03 ALASTIN Skincare, Inc. Peptide compositions and methods for ameliorating skin laxity and body contour
US11052032B2 (en) 2017-08-03 2021-07-06 ALASTIN Skincare, Inc. Peptide compositions and methods for ameliorating skin laxity and body contour
US11752084B2 (en) 2017-08-03 2023-09-12 ALASTIN Skincare, Inc. Methods for fat reduction or elimination of lipid droplets
WO2019028275A1 (fr) * 2017-08-03 2019-02-07 ALASTIN Skincare, Inc. Compositions et procédés permettant d'améliorer la laxité de la peau et le contour du corps
US12053547B2 (en) 2018-08-02 2024-08-06 ALASTIN Skincare, Inc. Liposomal compositions and methods of use
US11103455B2 (en) 2018-08-02 2021-08-31 ALASTIN Skincare, Inc. Liposomal compositions and methods of use
CN111004304A (zh) * 2019-12-31 2020-04-14 山东济肽生物科技有限公司 一种生物素三肽-1液相合成方法
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WO2021151879A1 (fr) 2020-01-29 2021-08-05 Beiersdorf Ag Protection de la peau contre les allergènes
WO2021151872A1 (fr) 2020-01-29 2021-08-05 Beiersdorf Ag Protection anti-allergène contre les urushiols
DE102020201019A1 (de) 2020-01-29 2021-07-29 Beiersdorf Aktiengesellschaft Allergenschutz für die Haut
FR3107708A1 (fr) 2020-02-28 2021-09-03 Alganelle Microalgue recombinante capable de produire des peptides, polypeptides et protéines de KTTKS et leurs dérivés, et leurs procédé et utilisations associés
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FR3108258A1 (fr) * 2020-03-20 2021-09-24 Sederma Composition et traitement cosmétiques pour traiter le relâchement cutané
WO2021185953A1 (fr) * 2020-03-20 2021-09-23 Sederma Traitement et composition cosmétique pour le traitement de l'affaissement de la peau
US11571378B2 (en) 2021-01-22 2023-02-07 The Procter & Gamble Company Skin care composition and method of using the same
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WO2022157587A1 (fr) * 2021-01-23 2022-07-28 Cellix Bio Private Limited Composition comprenant de la lidocaïne, de la l-carnosine et du dexpanthénol
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EP2714001A2 (fr) 2014-04-09

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