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
• • 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
  • A61P17/18—Antioxidants, e.g. antiradicals
• • 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
• • 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
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/52—Stabilizers
  • A61K2800/522—Antioxidants; Radical scavengers

Definitions

• the invention concerns the cosmetic use of thiazolidine derivatives, particularly in the domain of skin protection and more especially in the struggle against oxidative stress and its cutaneous consequences.
• ROS reactive oxygen species
• ROS reactive oxygen species
• This overproduction of ROS is then responsible for biological constituent alterations of skin, in particular of those met in the cutaneous cells (DNA, proteins, lipids, glucides).
• the formation of by-products issued from degradation of these biological molecules, and in particular of those issued from the peroxidised membrane phospholipids by the ROS, is also harmful to skin.
• exposure of a skin to an overproduction of ROS also initiates complex biochemical reactions, which are at the origin of pro-inflammatory cytokine production, mutagen metabolites, and the death of cutaneous cells (Briganti S, and al., J. Eur. Acad. Dermatol. Venereol. (2003), vol. 17, pp. 663-669).
• first generation ROS an efficient protection against these so-called first generation ROS is shown for a number of antioxidant or antiradical molecules belonging to the state of the technique.
• first generation ROS it is to necessary to understand the species derived from molecular oxygen reduction (O 2 o ⁇ , H 2 O 2 , 1 O 2 , OH o , ONOO ⁇ , etc).
• second generation products toxic aldehydes, final products issued from the lipid peroxidation, etc
• the present invention has been developed in this context to satisfy this request for products or preparations able to oppose the destructive effects of oxidative stress and its toxic by-products as efficiently as possible, notably in the deep skin layers.
• the 2-oxo-1,3-thiazolidine compound is not a new product.
• it is to raise its synthesis from aminoethanethiol and diphenyl carbonates according to a process and particular conditions which usually grant a phosgene-type chemical reactivity to various cyclic polycarbonates issued from plastic retreatment (Hata S. and al., J. Appl. Polym. Sci. (2003), vol. 90, pp. 2959-2968).
• the invention has for object the use of a derivative of general formula (I) as active ingredient in a cosmetic composition
• X represents an atom of oxygen or sulphur
• the said derivative or the said composition being intended for skin protection against any stress generating free radicals or reactive oxygen species.
• the preferred compound of above formula (I) is such that X represents an atom of oxygen.
• the above-mentioned use is preferentially maintained against a stress with an origin chosen among atmospheric pollution, contact with chemical xenobiotics or smoky atmospheres, and more specifically ultraviolet radiation.
• the present invention aims to forestall and to fight against cutaneous signs resulting from such stress, notably against varied events connected to skin ageing. It especially applies to the domain of sun protection, with regard to:
• the present invention also spreads to a cosmetic composition
• a cosmetic composition comprising, in association with any physiologically compatible excipient with skin, and as main active ingredient, the derivative of formula (I) such as defined previously, the said composition being intended for protecting skin against any stress generating free radicals or reactive oxygen species.
• composition is intended for protecting skin against a “UV-induced” stress
• derivative of general formula (I) is such that X represents an atom of oxygen.
• the quantity of the said derivative of formula (I) in the above-mentioned composition comprises between 0.01 and 10% in weight in relation to total weight of the composition, preferably between 0.05 and 5% in weight, even better between 0.5 and 5% in weight.
• physiologically compatible excipient with skin is a surfactant, a preservative, body fat, a colorant, an emulsifier, a gelling agent, an emollient, a moisturizer, a pigment, or all other adjuvants usually used in cosmetics.
• the said composition is susceptible to comprise, furthermore, another active element chosen among antioxidant, antiradical and/or anti-pollution agents found on the market, in such a way that the intrinsically attached effect to the compositions according to the invention is not altered by the considered addition.
• antioxidant, antiradical or anti-pollution agents commonly found on the market can be:
• the above-mentioned composition can also associate a UV-A or B sunscreen, or their mixture, of organic (benzophenone derivatives) or inorganic (metallic oxides) nature, or even a cosmetic active ingredient with a secondary effect, such as a moisturizing agent, a smoothing agent, a pigmenting agent, an agent stimulating the synthesis of epidermic and dermic macromolecules, and this, whilst maintaining that the said cosmetic active ingredient and its quantity are present in a way that properties of the composition according to the invention are not altered by the considered addition.
• a UV-A or B sunscreen or their mixture, of organic (benzophenone derivatives) or inorganic (metallic oxides) nature
• a cosmetic active ingredient with a secondary effect, such as a moisturizing agent, a smoothing agent, a pigmenting agent, an agent stimulating the synthesis of epidermic and dermic macromolecules, and this, whilst maintaining that the said cosmetic active ingredient and its quantity are present in a way that properties of the composition according to the invention are
• compositions according to the invention are adapted to a topical cutaneous administration and presented under all typical forms used for such an administration.
• they are formulated under the form for instance of emulsions, creams, milks, gels, lotions, etc.
• cosmetic composition formulation according to the invention containing the aforementioned 2-oxo-1,3-thiazolidine or 2-thiono-1,3-thiazolidine heterocycles
• the present invention concerns a cosmetic treatment process aiming to fight against the oxidative stress of skin and its consequences.
• the process is used by applying the previously defined compositions, preferentially with a composition comprising the 2-oxo-1,3-thiazolidine derivative.
• this latter can also be used with concomitance to oral supplementation of an antioxidant substance typically found on the market, for instance such as listed here-above.
• the said process can comprise also of the oral administration of an antioxidant substance to the individual person for which the cosmetic treatment is intended.
• the administration on the skin of a composition according to the invention and the oral administration of an antioxidant substance take place preferably at the same time.
• tests 1 to 6 the invention is hereafter illustrated, by the following tests described above for the invention (tests 1 to 6). It is also to signal that the first results of an in vivo study on man can illustrate the use of thiazolidine derivatives according to the present invention.
• Test 1 partition coefficient of the 2-oxo-1,3-thiazolidine compound
• n-octanol/water (Log P) partition coefficient have been experimentally obtained in accordance with the protocol described in the OECD guidelines n o 107 (adopted the 27 Jul. 1995) for tests on chemicals.
• the log P of the 2-oxo-1,3-thiazolidine compound according to the invention is compared to the one obtained for caffeine and ethanol (table 1 below).
• the 2-oxo-1,3-thiazolidine result is comparable to the one obtained for the known trans-stratum corneum permeant compound.
• Test 2 demonstration of the antioxidant effect of the 2-oxo-1,3-thiazolidine compound
• the tested substance is dissolved in a buffered medium of pH 7.4 to which is added a generating medium of OH o .
• a generating medium of OH o Following one hour of incubation at 37° C., the reaction is stopped with the help of trichloroacetic acid.
• thiobarbituric acid After addition of a calorimetric revealer, thiobarbituric acid, the absorbance is measured at 532 nm for different concentrations, then the relative Ks (OH o ) is calculated for each of the substances. The results are reported below in table 2a.
• anion O 2 o ⁇ hydrogen peroxide H 2 O 2 , and the hydroxyl radical OH o , and is expressed by following the percentage of protection of a “detecting” molecule, desoxyribose.
• the 2-oxo-1,3-thiazolidine compound according to the invention is also compared to taurine.
• the tested substance is dissolved in a buffered medium at pH 7.5, supplemented with NaCl, MgCl 2 et CaCl 2 .
• the reaction is stopped with the help of trichloroacetic acid.
• an optic density measure at 532 nm is carried out, expressed later as percentage of desoxyribose protection (following comparison with a control). Results are reported in the hereafter table 2b:
• Test 3 demonstration of the capacity of the 2-oxo-1,3-thiazolidine compound to neutralize 4-hydroxynonenal cytotoxicity
• the experimental study has been carried out on a fibroblastic line of hamster called V79, maintained in humid atmosphere at 37° C. and 5% CO 2 , then seeded in 96 wells plates at the rate of 0.5.10 4 cells per well. The cells are then submitted to a state of toxic stress, with replacement of the culture medium by a medium containing 4-hydroxynonenal (or 4-HNE) at 6 ppm concentration, medium to which is simultaneously added the 2-oxo-1,3-thiazolidine compound according to the invention.
• a medium containing 4-hydroxynonenal or 4-HNE
• the cellular viability of fibroblasts is measured by the incorporation method to the bromide of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (or MTT).
• MTT 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium
• Test 4 demonstration of the anti-clastogen effect of the 2-oxo-1,3-thiazolidine compound in presence of a genotoxic concentration of 4-hydroxynonenal.
• micronucleus cell number is counted following reading of the slides with epifluorescence microscope, on 2000 cells and after marking with orange acridine (DNA colorant).
• Test 5 “in tubo” demonstration of taurine formation when in contact with a H 2 O 2 solution.
• Test 6 demonstration of the protector effect of the 2-oxo-1,3-thiazolidine in presence of a “UVA-induced” stress
• CMDCF permeant fluorescent probe
• CMDCF cells said “positive” (cells with intracellular formation of ROS are presented below in table 6, in comparison with unirradiated cells, then with cells treated with N-acetyl-cysteine (reference molecule) and different concentrations of 2-oxo-1,3-thiazolidine compound.
• the 2-oxo-1,3-thiazolidine compound according to the invention shows a dose-dependent ability to protect cells submitted to a “UVA-induced” stress, and similar to the reference molecule.

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• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
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• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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• General Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Engineering & Computer Science (AREA)
• Biochemistry (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Cosmetics (AREA)

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• 2007
  • 2007-09-21 FR FR0706641A patent/FR2921257B1/fr not_active Expired - Fee Related
• 2008
  • 2008-09-12 DK DK08368016.5T patent/DK2039341T3/da active
  • 2008-09-12 ES ES08368016T patent/ES2378343T3/es active Active
  • 2008-09-12 AT AT08368016T patent/ATE536171T1/de active
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• 2012
  • 2012-12-07 US US13/708,462 patent/US8492417B2/en active Active

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