WO2005004891A2 - Utilisation d’un antioxydant dans une composition a usage dermatologique et/ou cosmetique - Google Patents

Utilisation d’un antioxydant dans une composition a usage dermatologique et/ou cosmetique Download PDF

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Publication number
WO2005004891A2
WO2005004891A2 PCT/FR2004/001768 FR2004001768W WO2005004891A2 WO 2005004891 A2 WO2005004891 A2 WO 2005004891A2 FR 2004001768 W FR2004001768 W FR 2004001768W WO 2005004891 A2 WO2005004891 A2 WO 2005004891A2
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antioxidant
composition
composition according
dermatological
acne
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Ceased
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PCT/FR2004/001768
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English (en)
French (fr)
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WO2005004891A3 (fr
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Jean-Noël THOREL
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Priority to US10/562,443 priority Critical patent/US20060159714A1/en
Priority to EP04767603.6A priority patent/EP1641476B1/fr
Priority to JP2006518291A priority patent/JP2007516185A/ja
Priority to CA2531186A priority patent/CA2531186C/fr
Priority to CN2004800191677A priority patent/CN1819824B/zh
Priority to KR1020067000439A priority patent/KR101161682B1/ko
Priority to ES04767603.6T priority patent/ES2622402T3/es
Publication of WO2005004891A2 publication Critical patent/WO2005004891A2/fr
Publication of WO2005004891A3 publication Critical patent/WO2005004891A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K31/075—Ethers or acetals
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
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    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A—HUMAN NECESSITIES
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    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/201—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having one or two double bonds, e.g. oleic, linoleic acids
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    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
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    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
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    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7004—Monosaccharides having only carbon, hydrogen and oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • 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
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    • A—HUMAN NECESSITIES
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    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
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    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
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    • 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • 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
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
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    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
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    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • 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
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9771—Ginkgophyta, e.g. Ginkgoaceae [Ginkgo family]
    • 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
    • A61P17/08—Antiseborrheics
    • 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
    • A61P17/10—Anti-acne agents
    • 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
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/008—Preparations for oily skin
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    • 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
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/16—Ginkgophyta, e.g. Ginkgoaceae (Ginkgo family)

Definitions

  • the present invention relates to the treatment of acne and skin disorders related to the formation of comedones.
  • the comedo is the first lesion of acne vulgaris and this lesion results from the obstruction by cells of the wall of the follicle of the canal preventing the sebum produced by sebocytes (sebaceous gland cells) from reaching the surface of the skin. .
  • the mixture of sebum and cells forms a plug called a comedo, and causes in the clogged pore the proliferation of bacteria that normally live on the skin such as Propionibacterium acnes and granulosum and yeasts including Malassezia furfur. These bacteria have the particularity of metabolizing the triglycerides of sebum by releasing fatty acids which cause inflammation of the tissues.
  • the resulting seborrheic dermatitis results in an eruption of red spots or patches, covered with yellowish fatty scales, more or less itchy, predominant in areas rich in sebaceous glands.
  • the topography of the lesions is suggestive: furrow between the nose and the lips, eyebrow root, scalp, wings of the nose, folds of the pavilions, ear conches, external auditory canals.
  • the scalp frequent damage results in a more or less seborrheic dandruff condition.
  • On the trunk there are two common areas in humans: the sternum and the region between the two shoulder blades.
  • Sebum is a fatty secretion product, rich in fatty acids and in particular in squalene, an aliphatic carbide with 30 carbon atoms, precursor of cholesterol. Sebum plays an important positive role, particularly in protecting the skin, but it has also been established since 1969 (Cunliffe, WJ et al, Lancet, I, 685, 1969, The pathogenesis of acne) that there is a correlation between the rate of sebum secretion and the severity of acne.
  • compositions in order to reduce and control the excessive secretions of the sebaceous glands, in particular in order to reduce the consequences which are both unsightly such as the fatty appearance and oily of the skin and scalp, but also to reduce the formation of blackheads and resulting inflammation.
  • These compositions have significant side effects such as skin dryness, feelings of tightness or even inflammation due to the elimination of sebum which can no longer play its protective role.
  • the composition of sebum in acne patients is highly enriched in squalene.
  • the Applicant has also shown that the oxidation of the lipids constituting the sebum, resulted in an increase in the viscosity of said sebum, and an increase in the formation of comedones, the less fluid sebum being unable to flow out of the follicular canals any more. This oxidation being potentially caused by the bacterial components and the UN., Causing the formation of viscous polymers which thicken the sebum and which are very comedogenic.
  • the present invention therefore relates to compositions which improve the quality of sebum by preventing its thickening and thus reduce the induction of keratinocyte proliferation, resulting in a decrease in comedogenesis.
  • the results on acne-prone skin are obtained without modification of the sebum flow, that is to say without action on the quantity of sebum produced but by reducing its comedogenicity, correcting its quality and avoiding its thickening.
  • compositions making it possible to maintain the fluidity of sebum and more particularly to a composition for dermatological and / or cosmetic use, intended for the treatment of acne, seborrheic dermatitis and skin disorders linked to the formation of comedones, characterized in that it comprises as active principle at least one lipophilic antioxidant, chosen from the group consisting of gallates, flavonoids, butyl-hydroxytoluene (BHT), butyl-hydroxyanisole (BHA), octadecenedioic acid and hydroxydecanoic acid.
  • BHT butyl-hydroxytoluene
  • BHA butyl-hydroxyanisole
  • compositions as defined above characterized in that it also comprises at least one second active principle, a hydrophilic antioxidant chosen from the group consisting of mannitol, vitamin C, lysine azeilate, rutin , quercetin.
  • a hydrophilic antioxidant chosen from the group consisting of mannitol, vitamin C, lysine azeilate, rutin , quercetin.
  • the invention also relates to a composition in which the lipophilic antioxidant is dodecyl gallate.
  • the invention also relates to a composition in which the lipophilic antioxidant is propyl gallate
  • the invention also relates to a composition in which the lipophilic antioxidant is octyl gallate.
  • Flavonoids can for example be provided by plant extracts such as Ginkgo biloba or green tea extracts.
  • the amount of active principle that is to say hydrophilic or lipophilic antioxidant or the total amount of the two antioxidants is between 0.0001 and 20% by weight of the composition, and preferably between 0.0001 and 10 % by weight of the composition. Preferably, it is between 0.001 and 2% by weight of the composition.
  • the invention also relates to a process for fluidifying the sebum, characterized in that it comprises the application to the skin or the scalp of a composition according to the invention, as defined above.
  • This composition comprises, in a pharmacologically acceptable medium, at least one active principle, that is to say a lipophilic antioxidant.
  • the pharmacologically acceptable medium i.e. the galenic environment must be neither oxidizable nor oxidizing, i.e.
  • the excipients used must be non-oxidizable and stable under the conditions of application to the skin, nor cause oxidation.
  • the invention therefore relates to a composition as defined above, characterized in that it does not contain excipients capable of oxidizing under the conditions of use.
  • compositions according to the invention can optionally contain various non-oxidizable additives, such as suspending agents, emulsifiers, anionic, cationic, nonionic, amphoteric polymers, proteins, vitamins, surfactants, mineral oils. or vegetable, waxes, gums and / or silicone resins, thickening agents, acidifying or basifying agents, solvents, pH stabilizers, anti-UV agents, preservatives, antibacterials and antifungals, perfumes or other adjuvants usually used in cosmetics or dermatology.
  • the compositions according to the present invention are in a form suitable for administration by the topical skin route, and cover all cosmetic or dermatological forms.
  • compositions contain a cosmetically and / or dermatologically acceptable medium, that is to say compatible with the skin, hair or hair.
  • These compositions can in particular be in the form of creams, O / W emulsions, W / O or multiple emulsions, solutions, suspensions, gels, milks, lotion, sticks or powders, suitable for application to the skin, the lips and / or the hair.
  • the invention also relates to the use of at least one lipophilic antioxidant for the preparation of a dermatological and / or cosmetic composition for the treatment of acne and or skin disorders due to the formation of comedones. It relates more particularly to the use as defined above, characterized in that the lipophilic antioxidant is chosen from the group consisting of gallates and flavonoids.
  • the lipophilic antioxidant is selected from the group consisting of butyl-hydroxytoluene (BHT), butyl-hydroxyanisole (BHA), octadecenedioic acid and hydroxydecanoic acid.
  • BHT butyl-hydroxytoluene
  • BHA butyl-hydroxyanisole
  • octadecenedioic acid hydroxydecanoic acid.
  • the invention also relates to said use when the lipophilic antioxidant is dodecyl gallate.
  • the invention also relates to said use when the lipophilic antioxidant is propyl gallate
  • the invention also relates to said use when the lipophilic antioxidant is octyl gallate.
  • Flavonoids can for example be provided by plant extracts such as Ginkgo biloba or green tea extracts.
  • hydrophilic antioxidant in combination with a lipophilic antioxidant for the preparation of a dermatological and / or cosmetic composition for the treatment of acne and or skin disorders due to the formation of comedones. It also relates to a use as defined above, characterized in that the hydrophilic antioxidant is chosen from the group consisting of mannitol, vitamin C. In a variant, the hydrophilic antioxidant is chosen from the group consisting of azeilate lysine, rutin and quercetin. According to the invention the amount of hydrophilic or lipophilic antioxidant or the total amount of the two antioxidants used is between 0.0001 and 20% by weight of the composition, and preferably between 0.0001 and 10% by weight of the composition . Preferably, it is between 0.001 and 2% by weight of the composition.
  • composition according to the invention containing, as active principle, dodecyl gallate, mannitol and an extract of Ginkgo biloba was tested on a group of around thirty volunteers.
  • the subjects aged on average 23 years (18 to 34 years) present a polymorphous juvenile acne of average intensity that is to say presenting approximately 40 retentional or inflammatory lesions on average.
  • composition according to the invention was applied twice daily for 8 weeks to the face.
  • a reduction in retention lesions is noted for at least 40% of the subjects, with 20% of the subjects having a reduction of 50 to 90% of the microcysts, 15% a reduction of 50 to 90% of the comedones and 10 % a complete disappearance of blackheads.
  • compositions were obtained by simple mixing of the various components. The quantities indicated are given in percentage by weight.
  • Purifying lotion for acne-prone skin and dandruff Purifying lotion for acne-prone skin and dandruff
  • compositions according to the invention may also comprise active agents having a keratolytic activity chosen from esters of alpha-hydoxy acids and / or salicylic acid which make it possible to eliminate and prevent the formation of clusters of corneocytes which can also promote the formation of blackheads.
  • compositions according to the invention can also further comprise a zinc salt, for example zinc gluconate having a seboregulatory action, by its inactive action of 5-alpha-reductase and at a high concentration a bactericidal action on Propionibacterium acnes, the proliferation of which within comedo is characteristic of acne.
  • a zinc salt for example zinc gluconate having a seboregulatory action, by its inactive action of 5-alpha-reductase and at a high concentration a bactericidal action on Propionibacterium acnes, the proliferation of which within comedo is characteristic of acne.
  • compositions according to the invention can also comprise an anti-inflammatory or soothing active agent such as 18-beta-glycyrrhetic acid (enoxolone), the endogenous anti-inflammatory role of which is due to the inhibition of the enzyme responsible for the transformation of cortisol into cortisone or an extract of Ginkgo biloba described as an inhibitor of the inflammatory cascade.
  • an anti-inflammatory or soothing active agent such as 18-beta-glycyrrhetic acid (enoxolone)
  • enoxolone 18-beta-glycyrrhetic acid
  • the acton of these active ingredients is supplemented by a galenical base comprising glycerin and xylitol chosen for their moisturizing properties.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biotechnology (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Molecular Biology (AREA)
  • Botany (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
PCT/FR2004/001768 2003-07-07 2004-07-07 Utilisation d’un antioxydant dans une composition a usage dermatologique et/ou cosmetique Ceased WO2005004891A2 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US10/562,443 US20060159714A1 (en) 2003-07-07 2004-07-07 Use of an antioxidant in a dermatological and/or cosmetic composition
EP04767603.6A EP1641476B1 (fr) 2003-07-07 2004-07-07 Combinaison d'antioxydants dans une composition a usage dermatologique et/ou cosmetique
JP2006518291A JP2007516185A (ja) 2003-07-07 2004-07-07 皮膚科用及び／又は化粧料用組成物における酸化防止剤の使用
CA2531186A CA2531186C (fr) 2003-07-07 2004-07-07 Utilisation d'un antioxydant dans une composition a usage dermatologique et/ou cosmetique
CN2004800191677A CN1819824B (zh) 2003-07-07 2004-07-07 抗氧化剂在皮肤病和/或化妆品组合物中的用途
KR1020067000439A KR101161682B1 (ko) 2003-07-07 2004-07-07 피부용 및/또는 화장제 조성물에서 항산화제의 사용 방법
ES04767603.6T ES2622402T3 (es) 2003-07-07 2004-07-07 Combinación de antioxidantes en una composición de uso dermatológico y/o cosmético

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FR0308288A FR2857266B1 (fr) 2003-07-07 2003-07-07 Composition a usage dermatologique et/ou cosmetique, comprenant a titre de principe actif au moins un antioxydant lipophile
FR03/08288 2003-07-07

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EP2583662A1 (fr) 2011-10-18 2013-04-24 Thorel, Jean-Noël Composition à base de meroterpene destinée aux peaux grasses, à tendance acneique ou atteintes d'acne
US9918916B2 (en) 2014-07-25 2018-03-20 Sederma Active ingredient comprising a mixture of unsaturated dicarboxylic fatty acids, compositions comprising said ingredient and cosmetic or dermatological uses

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FR2857266B1 (fr) 2007-09-21
EP1641476B1 (fr) 2017-03-29
CA2531186A1 (fr) 2005-01-20
WO2005004891A3 (fr) 2005-06-09
KR101161682B1 (ko) 2012-07-02
EP1641476A2 (fr) 2006-04-05
CN1819824A (zh) 2006-08-16
KR20060028744A (ko) 2006-03-31
JP2007516185A (ja) 2007-06-21
CA2531186C (fr) 2013-04-09
FR2857266A1 (fr) 2005-01-14
US20060159714A1 (en) 2006-07-20
CN1819824B (zh) 2010-05-12
ES2622402T3 (es) 2017-07-06

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