EP2167061A1 - Compositions depigmentantes dermatologiques et cosmetiques, leurs procedes de preparation, et leurs utilisations - Google Patents

Compositions depigmentantes dermatologiques et cosmetiques, leurs procedes de preparation, et leurs utilisations

Info

Publication number
EP2167061A1
EP2167061A1 EP08805686A EP08805686A EP2167061A1 EP 2167061 A1 EP2167061 A1 EP 2167061A1 EP 08805686 A EP08805686 A EP 08805686A EP 08805686 A EP08805686 A EP 08805686A EP 2167061 A1 EP2167061 A1 EP 2167061A1
Authority
EP
European Patent Office
Prior art keywords
retinoid
composition according
rucinol
weight
salts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP08805686A
Other languages
German (de)
English (en)
French (fr)
Inventor
Isabelle Pelisson
Itaru Suziki
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Galderma Research and Development SNC
Original Assignee
Galderma Research and Development SNC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Galderma Research and Development SNC filed Critical Galderma Research and Development SNC
Publication of EP2167061A1 publication Critical patent/EP2167061A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/185—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
    • A61K31/203—Retinoic acids ; Salts thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82B—NANOSTRUCTURES FORMED BY MANIPULATION OF INDIVIDUAL ATOMS, MOLECULES, OR LIMITED COLLECTIONS OF ATOMS OR MOLECULES AS DISCRETE UNITS; MANUFACTURE OR TREATMENT THEREOF
    • B82B3/00—Manufacture or treatment of nanostructures by manipulation of individual atoms or molecules, or limited collections of atoms or molecules as discrete units
    • 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
    • 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
    • A61K31/07—Retinol compounds, e.g. vitamin A
    • 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
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • 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
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • 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
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • 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
    • A61P17/16—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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening 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
    • A61Q19/08—Anti-ageing preparations
    • C—CHEMISTRY; METALLURGY
    • C30—CRYSTAL GROWTH
    • C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
    • C30B23/00—Single-crystal growth by condensing evaporated or sublimed materials
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/92—Oral administration

Definitions

  • the invention relates to depigmenting compositions, methods for preparing such compositions, and their uses.
  • the hyperpigmentation of the skin is a common disorder manifested by the appearance of brown or colored spots of the skin due to the accumulation of melanin, and conferring on the skin a heterogeneity. Pigmented spots can appear on all parts of the body, especially on the backs of hands, on the face, beaulleté and skull of men.
  • age spots or solar lentigines are a common form of hyperpigmentation. They are due to sun damage, and usually appear on the back of the hands and arms, on the neckline or at the level of the face. These spots are darker than freckles or ephelides, and persist in winter. Therefore, there is a real need for an effective and safe treatment of the symptoms of photoaging, especially hyperpigmentary tasks induced by exposure to ultraviolet light.
  • Melasma or chloasma lesions are more extensive than age spots and localized on the face. They are most often due to hormonal changes. Pregnancy, for example, can trigger the overproduction of melanin that causes the "pregnancy mask".
  • Skin color changes can result from external causes, such as skin diseases such as acne, or skin lesions. Freckles are also small brown spots that can appear anywhere on the body, but are the most common on the face and arms. Freckles are an inherited feature.
  • Post-inflammatory hyperpigmentation is also a disorder of frequent pigmentation that may be the consequence of various skin disorders as well as therapeutic interventions. This excess skin discoloration may be due to infections, allergic reactions, trauma such as abrasion, scarring, burning, drug reactions, phototoxic eruptions, and also following inflammatory diseases such as acne, eczema, psoriasis, lichen planus, lupus erythematosus, atopic dermatitis, or cutaneous lymphoma.
  • PIHP is more common in dark phototypes such as non-Caucasian skin, especially Asian, black, or mixed skin
  • Depigmenting agents or bleaching agents currently used in the form of topical compositions make it possible to reduce the density of melanin in the epidermis. These agents are usually absorbed through the lower layers of the epidermis and slow down the formation of melanin.
  • Hydroquinone is a depigmenting agent, as well as its derivatives, such as benzyl-oxy-phenol and hydroquinone monobenzylether.
  • these agents have several drawbacks: the hydroquinone is unstable in an alkaline medium and is oxidized in the form of quinone, which gives a brownish color to the compositions comprising it; hydroquinone is irritating; it can also induce hypersensitivity reactions and in rare cases ochronoses; hydroquinone is also suspected to be carcinogenic; hydroquinone monobenzylether is not metabolized properly when absorbed through the skin and causes irreversible depigmentation.
  • Methoxyphenol, a hydroquinone ether which has the disadvantage of being poorly soluble in water and difficult to incorporate in cosmetic or dermatological formulations, is also known.
  • depigmenting composition comprising (US Pat. No. 3,856,934) hydroquinone, retinoic acid and dexamethasone, but this composition is also irritating and can cause itching in the most extreme cases.
  • Various vitamin C-type products, fruit acids, and sunscreens have been developed to treat these pigmentation problems, but most of them contain unstable mixtures and are not very active.
  • the pallor or whiteness of the Asian face is obtained with molecules, such as arbutin, kojic acid, or ascorbic acid, which may be poorly tolerated or irritating.
  • compositions having a depigmenting or lightening activity and which are well tolerated by the skin especially for non-Caucasian skin, such as Hispanic, Indian, black, Asian or mixed skin.
  • Rucinol or lucinol, or 4-butyl-resorcinol, is marketed as a lightening agent for brown spots related to pigmentation disorders.
  • a problem to be solved by the invention is to provide a composition which shows an improved efficiency in the cosmetic and / or dermatological treatment of pigmentation, without the disadvantages of the compositions of the prior art.
  • the invention firstly relates to a composition, preferably dermatological or cosmetic, characterized in that it comprises, in a medium physiologically acceptable, (i) at least one compound selected from rucinol and its salts and (ii) at least one retinoid (hereinafter referred to as "active (i) and (ii)").
  • dermatological composition is meant a composition for treating and / or preventing skin pigment disorders.
  • cosmetic composition is meant a composition intended to beautify the skin and / or improve its physical appearance.
  • physiologically acceptable medium is meant a medium compatible with the skin, mucous membranes and / or integuments.
  • It has the second object the use of at least one compound selected from rucinol and its salts, and at least one retinoid, to prepare a drug for the treatment and / or prevention of disorders of pigmentation. It also relates to the use of a composition comprising, in a physiologically acceptable medium, at least one compound chosen from rucinol and its salts, and at least one retinoid, for preparing a medicinal product intended for treatment and / or for prevention of disorders of pigmentation.
  • Its third object is the use of a cosmetic composition
  • a cosmetic composition comprising, in a physiologically acceptable medium, at least one compound chosen from rucinol and its salts, and further comprising a retinoid, for the prevention and / or cosmetic treatment of skin pigmentation.
  • It also relates to a method for dermatological or cosmetic treatment of cutaneous pigmentation, comprising the administration of a composition according to the invention to an individual to be treated.
  • Rucinol or lucmol, or 4-butyl-resorcinol, is a compound of formula:
  • rucinol salts is intended especially to mean salts formed with a pharmaceutically acceptable base, in particular a mineral base such as sodium hydroxide, potassium hydroxide and aqueous ammonia, or an organic base such as lysine, arginine, N-methyl- glucamine, but also the salts formed with fatty amines such as dioctylamine, ammomethyl propanol and stearylamine.
  • a pharmaceutically acceptable base such as sodium hydroxide, potassium hydroxide and aqueous ammonia
  • organic base such as lysine, arginine, N-methyl- glucamine
  • fatty amines such as dioctylamine, ammomethyl propanol and stearylamine.
  • rucinol will be used.
  • the Applicant has demonstrated a significant improvement in the depigmenting activity of rucinol when it is in combination with a retinoid and, in particular, a faster depigmentation than the compositions of the prior art and that rucinol alone .
  • an effective amount of retinoid acts in synergy with an effective amount of rucinol for the depigmenting effect of the skin and can significantly reduce side effects such as irritation.
  • Retinoids find various applications in dermatology. However, it is known that these compounds have significant undesirable side effects, whether used systemically or topically. They cause in particular strong irritations. These disadvantages of retinoids did not allow to expect the advantageous effects of the compositions according to the invention.
  • the retinoids that can be used in the context of the invention include, in particular, all-trans retinoic acid or tretinoin, 13-cis-retinoic acid or isotretinoin acid, acitretin, arotinoic acid, retinol, and adapalene.
  • compositions according to the invention or the active agents (i) and (li) thus make it possible to reduce cutaneous pigmentation, and in particular local hyperpigmentations of the skin. In particular, when they are used topically, they produce a depigmentation of the cutaneous zone on which they are applied.
  • depigmentation is meant to obtain a discoloration of a pigmented skin area.
  • “depigmentation” is meant to obtain a discoloration of said zone until a color similar to that of the neighboring skin is obtained.
  • compositions of the invention or the active agents (i) and (ii) are particularly suitable for the treatment and / or prevention of pigmentation disorders such as: melasma or chloasma, lentigines, senile lentigo,
  • - post-inflammatory hyperpigmentations particularly due to infections, allergic reactions, traumatic injuries (such as abrasions, scars, burns), reactions to drugs, phototoxic eruptions, and also following inflammatory skin diseases (such as acne, eczema, psoriasis, rosacea, lichen planus, lupus erythematosus, atopic dermatitis, and cutaneous lymphoma);
  • compositions according to the invention or the active ingredients (i) and (ii) also find application in the cosmetic field, in particular in the protection against the harmful aspects of the sun, for preventing and / or for combating photo-induced aging. or chronological of the skin and integuments.
  • the invention also relates to a non-therapeutic cosmetic treatment method for embellishing the skin and / or improving its surface appearance, comprising applying to the skin and / or its integuments a composition comprising at least a compound selected from rucinol and its salts, and at least one retinoid.
  • the compositions according to the invention advantageously comprise between 0.0001 and 20% by weight of at least one retinoid and between 0.0001 and 20% by weight of at least one compound chosen from rucinol and its salts. , relative to the total weight of the composition.
  • they comprise between 0.001 and 10% of at least one retinoid and between 0.01 and 15% of rucinol, or its salts, and more preferentially between 0.1 and 5% by weight of at least one retinoid and between 0.1 and 5% by weight of at least one compound chosen from rucinol and its salts, relative to the total weight of the composition.
  • compositions of the invention may furthermore comprise any additive usually used in the pharmaceutical, dermatological or cosmetic field compatible with rucinol or its salts and a retinoid.
  • perfumes, essential oils, cosmetic active ingredients, moisturizers, vitamins, essential fatty acids, sphingolipids, soothing and protective agents for the skin such as allantoin, propenetrating agents, gelling agents or a mixture of those -this.
  • additives may be present in the composition in an amount of from 0 to 20% by weight relative to the total weight of the composition.
  • sequestering agents examples include ethylene diamine tetracetic acid (EDTA), as well as its derivatives or its salts, dihydroxyethylglycine, citric acid, tartaric acid, or mixtures thereof.
  • EDTA ethylene diamine tetracetic acid
  • preservatives examples include benzalkonium chloride, phenoxyethanol, benzyl alcohol, diazolidinyl urea, parabens, or mixtures thereof.
  • humectants examples include glycerin and sorbitol.
  • compositions of the invention are capable of containing one or more propenetrating agents in preferential concentrations ranging from 0 to 20% and more preferentially ranging from 0.6 to 3% by weight relative to the total weight of the composition.
  • propenetrating agents it is preferable to use, without this list being limiting, compounds such as propylene glycol, dipropylene glycol, propylene glycol dipelargonate, lauroglycol and ethoxydiglycol.
  • compositions according to the invention may also contain one or more surfactants in preferential concentrations ranging from 0 to 10% and more preferentially ranging from 0.1 to 2% by weight of the total weight.
  • Administration may be topical, enteral or oral, parenteral or ocular.
  • topical route is particularly preferred.
  • Topically we mean an application on the skin and / or the mucous membranes.
  • compositions of the present invention may be in any of the galenical forms normally used for topical application, especially in liquid, pasty or solid form, and more particularly in the form of ointments, aqueous, hydroalcoholic or oily solutions, dispersions lotion-type, aqueous, anhydrous or lipophilic gels, powders, soaked swabs, syndets, wipes, sprays, patches, foams, sticks, shampoos, compresses, washing bases, emulsions of liquid or semi-liquid consistency of the milk type, obtained by dispersion of a fatty phase in an aqueous phase (oil in water) or conversely (water in oil), or suspensions or emulsions of soft, semi-liquid or solid type cream, gel or ointment.
  • aqueous, hydroalcoholic or oily solutions dispersions lotion-type, aqueous, anhydrous or lipophilic gels, powders, soaked swabs, syndets, wipes, sprays, patches,
  • This topical composition may be in anhydrous form, in aqueous form or in the form of an emulsion or else microemulsions, microcapsules, microparticles or vesicular dispersions of ionic and / or non-ionic type. ionic.
  • the composition is in the form of an ointment, a cream, a lotion or a gel.
  • the aqueous phase of a composition according to the invention in the form of an emulsion may comprise water, a floral water such as cornflower water, or a natural thermal or mineral water, for example chosen from the water of Vittel, the waters of the Vichy basin, the water of Uriage, the water of the Roche Posay, the water of the Bourboule, the water of Enghien-les-Bains, the water of Saint Gervais-les-Bains, the water of Néris-les-Bains, the water of Allevard-les-Bains, the water of Digne, the water of Maizines, the water of Neyrac-les-Bains, the water of Lons-le-Saunier, the Good Waters, the water of Rochefort, the water of Saint Christau, the water of the Fumades and the water of Tercis-les-bains, the water of Avène or the water of Aix les Bains.
  • Said aqueous phase may be present at a content of between 10 and
  • composition according to the invention may contain a gelling agent with preferential concentrations ranging from 0.1 to 15% and, more preferably, from 0.5 to 5%.
  • gelling agents of the polyacrylamide family such as the mixture Sodium acryloyldimethyltaurate copolymer / isohexadecane / polysorbate 80 sold under the name Simulgel TM 600 by the company
  • Seppic TM the polyacrylamide / isoparaffin C13-14 / laureth-7 mixture, for example that sold under the name Sepigel 305 TM by the company Seppic TM, the family of acrylic polymers coupled to hydrophobic chains such as the
  • modified starches such as modified potato starch sold under the name Solanace TM Structure or mixtures thereof.
  • Silicone oil (“Abil 300.000 is” sold by GOLDSCHMIDT) qs 100 g

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Nanotechnology (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Manufacturing & Machinery (AREA)
  • Toxicology (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
EP08805686A 2007-05-04 2008-04-22 Compositions depigmentantes dermatologiques et cosmetiques, leurs procedes de preparation, et leurs utilisations Withdrawn EP2167061A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0754886A FR2915682B1 (fr) 2007-05-04 2007-05-04 Compositions depigmentantes dermatologiques et cosmetiques, leurs procedes de preparation, et leurs utilisations
PCT/FR2008/050731 WO2008148968A1 (fr) 2007-05-04 2008-04-22 Compositions depigmentantes dermatologiques et cosmetiques, leurs procedes de preparation, et leurs utilisations

Publications (1)

Publication Number Publication Date
EP2167061A1 true EP2167061A1 (fr) 2010-03-31

Family

ID=38800746

Family Applications (1)

Application Number Title Priority Date Filing Date
EP08805686A Withdrawn EP2167061A1 (fr) 2007-05-04 2008-04-22 Compositions depigmentantes dermatologiques et cosmetiques, leurs procedes de preparation, et leurs utilisations

Country Status (12)

Country Link
US (2) US20100143445A1 (es)
EP (1) EP2167061A1 (es)
JP (1) JP2010526124A (es)
KR (1) KR20100016204A (es)
CN (1) CN101674818A (es)
AU (1) AU2008259754A1 (es)
BR (1) BRPI0809880A2 (es)
CA (1) CA2685482A1 (es)
FR (1) FR2915682B1 (es)
MX (1) MX2009011743A (es)
RU (1) RU2009144988A (es)
WO (1) WO2008148968A1 (es)

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FR2910321B1 (fr) 2006-12-21 2009-07-10 Galderma Res & Dev S N C Snc Gel creme comprenant au moins un retinoide et du peroxyde de benzole
FR2910320B1 (fr) 2006-12-21 2009-02-13 Galderma Res & Dev S N C Snc Emulsion comprenant au moins un retinoide et du peroxyde de benzole
KR20110014242A (ko) * 2008-05-30 2011-02-10 갈데르마 리써어치 앤드 디벨로프먼트 지방 상 중에 가용화 페놀성 유도체 및 레티노이드를 포함하는 무수 탈색 조성물
FR2931663B1 (fr) * 2008-05-30 2010-07-30 Galderma Res & Dev Nouvelles compositions depigmentantes anhydre comprenant un derive phenolique solubilise.
FR2931662B1 (fr) * 2008-05-30 2010-07-30 Galderma Res & Dev Nouvelles compositions depigmentantes sous forme d'une composition anhydre sans vaseline et sans elastomere comprenant un derive phenolique solubilise.
FR2931661B1 (fr) * 2008-05-30 2010-07-30 Galderma Res & Dev Nouvelles compositions depigmentantes sous forme d'une composition anhydre sans vaseline et sans elastomere comprenant un derive phenolique solubilise et un retinoide.
PT2400951T (pt) 2009-02-25 2018-11-26 Mayne Pharma Llc Composições de espuma tópica
DE102009048970A1 (de) * 2009-10-09 2011-04-14 Beiersdorf Ag Verwendung von 4-n Butylresorcin zur Herstellung einer kosmetischen oder dermatologischen Zubereitung zur Prophylaxe oder Behandlung von Augenringen die durch eine gestörte Durchblutung der Haut im Augenbereich hervorgerufen werden
CN101791282B (zh) * 2009-12-29 2013-09-25 广东药学院 一种美容换肤液及其制备方法和应用
CN101961299B (zh) * 2010-09-28 2014-04-02 清华大学 一种中草药凝胶化妆品及其制备方法
FR2969492B1 (fr) * 2010-12-23 2013-07-05 Galderma Res & Dev Mousses dermatologiques obtenues a partir d'un gel ou d'une suspension contenant de l'adapalene
FR2991175B1 (fr) * 2012-06-01 2014-12-19 Galderma Res & Dev Compositions pharmaceutiques topiques de type emulsion h/e contenant un retinoide
FR2991177B1 (fr) * 2012-06-01 2014-12-19 Galderma Res & Dev Compositions topiques, contenant un retinoide, de type emulsion huile dans eau sans emulsionnant
FR2991180B1 (fr) * 2012-06-01 2014-06-13 Galderma Res & Dev Compositions topiques de type emulsion sans emulsionnant a base de particules stabilisantes.
FR2991174B1 (fr) * 2012-06-01 2014-12-26 Galderma Res & Dev Composition dermatologique comprenant des oleosomes et des retinoides, son procede de preparation et son utilisation
FR2991176B1 (fr) * 2012-06-01 2014-12-19 Galderma Res & Dev Compositions topiques, contenant un retinoide solubilise, de type gel hydroglycolique
FR2991172A1 (fr) * 2012-06-01 2013-12-06 Galderma Res & Dev Compositions pharmaceutiques topiques comprenant des microcapsules
EA201892135A1 (ru) * 2016-05-12 2019-05-31 Юнилевер Н.В. Способ стабилизации предшественников ретиноевой кислоты и благотворно влияющая на кожу композиция, содержащая стабилизированные предшественники ретиноевой кислоты
CA3069345A1 (en) * 2017-07-12 2019-01-17 Unilever Plc Skin composition booster oil

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AU2008259754A1 (en) 2008-12-11
BRPI0809880A2 (pt) 2014-09-30
US20100143445A1 (en) 2010-06-10
FR2915682B1 (fr) 2009-07-03
WO2008148968A1 (fr) 2008-12-11
CN101674818A (zh) 2010-03-17
MX2009011743A (es) 2009-11-11
RU2009144988A (ru) 2011-06-10
CA2685482A1 (fr) 2008-12-11
US20120282314A1 (en) 2012-11-08
FR2915682A1 (fr) 2008-11-07
JP2010526124A (ja) 2010-07-29
KR20100016204A (ko) 2010-02-12

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