EP1265619A1 - Composition a base de sphingolipide et de beta-hydroxy-acide pour les soins de la peau - Google Patents
Composition a base de sphingolipide et de beta-hydroxy-acide pour les soins de la peauInfo
- Publication number
- EP1265619A1 EP1265619A1 EP01917176A EP01917176A EP1265619A1 EP 1265619 A1 EP1265619 A1 EP 1265619A1 EP 01917176 A EP01917176 A EP 01917176A EP 01917176 A EP01917176 A EP 01917176A EP 1265619 A1 EP1265619 A1 EP 1265619A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- sphingolipid
- beta
- hydroxy acid
- acid
- composition according
- 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- Withdrawn
Links
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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/11—Encapsulated compositions
-
- 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
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic 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
- A61K8/33—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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
-
- 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
- A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
-
- 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
Definitions
- the present invention relates to a pharmaceutical and cosmetic composition, and more particularly to a composition comprising in combination at least one beta-hydroxy acid and at least one sphingolipid or a sphingolipid precursor, usable by topical administration for treatments and skin care.
- Sphingolipids are substances essentially comprising a fatty acid, a polar group and a chemical structure called sphingoid base, consisting of a long hydrocarbon chain derived from 2-amino-1,3-diol. It is known that certain sphingoid bases, in particular sphingosine and phytosphingosine, precursors of ceramides, are present in human skin, and studies have shown that these molecules have inhibitory properties of the protein inase C, and seem to be involved in differentiation. keratinocytes of the epidermis. It has also been observed that sphingosines present in the stratum corneum and other layers of the epidermis inhibit the growth of certain undesirable microorganisms.
- Sphingosine or 2-amino-4-octadecene-1,3-diol
- Phytosphingosine or 2-amino-1,3,4-octadecanetriol, is found naturally in the lipids of plants, where there are also some analogs to 16, 19 and 20 carbon atoms. According to the present invention, the names sphingosine and phytosphingosine used here also include these analogs.
- Ceramides amides of fatty acids and sphingid bases
- Ceramides are natural constituents of the surface layers of the skin, and in particular the stratum corneum, and play an essential role in the structure of the skin lipid barrier, but their content tends to decrease with age in significant proportions.
- patent applications FR-A-2,673,179 and FR-A-2,714,829 describe ceramides which can be used in cosmetic or dermatological compositions.
- Patent application FR-A-2,773,074 describes compositions based on ceramides associated with alpha-hydroxy acids, which can be used in dermatology.
- Salicylic acid is known as one of the main beta-hydroxy acids. It has keratolytic, anti-inflammatory and antibacterial properties. However, depending on the concentration, it exerts an irritant effect on the skin which limits its use to a few external treatments.
- Salicylic acid esters have been proposed in low doses, that is to say generally less than 1%, in cosmetic compositions, and for example phytosphingosine salicylate obtained by the action of methyl salicylate on phytosphingosine in the medium basic hot as in patent EP-A-919,226 or salicylates of base spheroids obtained enzymatically or chemically by means of a coupling agent such as 1 hydroxybenzotriazole in the presence of a carbodumide as in WO application. 98.40350.
- patent EP 273,202 describes the use of alpha-hydroxy acids as additives in compositions containing one or more active drug ingredients, in order to improve their activity topically.
- Patent EP 504,862 shows that certain derivatives of alpha-hydroxy acids can be used for the treatment of ment of the atrophy of the skin induced by the topical application of corticoids such as clobetasol propionate.
- Patent EP 413,528 describes compositions which can be used for the treatment of various dermatological conditions such as acne, eczema or psoriasis, containing alpha-hydroxy acids in combination with an amphoteric agent having the effect of increasing the pH of the composition.
- alpha-hydroxy acids make it possible to envisage their use in dermatology for the treatment of certain skin conditions.
- they should be used in relatively low concentrations, not exceeding 10% in free form, due to the side effects they may cause, for example increased sensitivity and skin irritation.
- the various known compositions described above which can be used for dermatological treatments are not always suitable for specific treatments such as that of acne.
- Acne is a pathological condition resulting from occlusion of the upper extremity as well as of the internal part of the pilosebaceous canal by the abnormal multiplication of keratinocytes.
- the androgenic hormonal hyperactivity generally appearing during puberty causes a significant increase in seborrhea in the sebaceous glands, and the obstruction of the pilosebaceous canal causes the formation of retentional lesions in the form of comedones or microcysts. .
- This phenomenon triggers an inflammatory reaction of the skin, which may be in the form of papules or pustules
- papulopustular acne particularly common in adolescents. These lesions are generally located in the superficial dermis. In some cases there is a intense inflammatory reaction accompanying deep lesions reaching the deep dermis, forming nodules and macrocysts (nodulocystic acne) requiring appropriate treatment.
- the work undertaken by the applicant has made it possible to show that the combined use of certain beta-hydroxy acids with certain sphingolipids or sphingolipid precursors, such as sphingosine and phytosphingosine, makes it possible to restore the natural defenses of the skin, and effectively fight against certain skin conditions, more particularly in the case of acne, thus offering an alternative to treatment with antibiotics such as erythromycin.
- the present invention relates to a composition based on beta-hydroxy acid and sphingolipid or sphingolipid precursor, such as sphingosine, sphinganine and phytosphingosine, usable in therapy and in cosmetics by topical application.
- the subject of the invention is also a composition comprising at least one beta-hydroxy acid in combination with a sphingolipid or a sphingolipid precursor, such as sphingosine, sphinganine and phytosphingosine, as well as excipients suitable for application by topically, for the treatment of various dermatological conditions, and more particularly for the treatment of acne.
- a sphingolipid or a sphingolipid precursor such as sphingosine, sphinganine and phytosphingosine
- the composition according to the present invention comprises, in combination, at least one beta-hydroxy acid, or one of its salts and esters, and at least one sphingolipid.
- the sphingolipid or sphingolipid precursor used in the compositions according to the present invention can be chosen more particularly from sphmgosine, hydroxyphosphmgosme, sphinganine, N, N-dimethylsphingosme, oleoyl-sphingosme and phytosphingosine.
- beta-hydroxy acid of the invention and its salts and esters can be represented by the general formulas (I) or (I ') below:
- R x and R 2 identical or different, represent a hydrogen atom or a linear or branched alkyl group comprising 1 to 5 carbon atoms, or a phenyl group, or
- Ri and R 2 together form a 5- or 6-membered ring
- R is a hydrogen atom, an alkyl group of 1 to 12 carbon atoms, an alkyl-silyl group, an ammonium group or an alkali or alkalo- earthy.
- the beta-hydroxy acid used in the invention has keratolytic and antiseptic properties.
- the beta-hydroxy acid is salicylic acid, or an alkyl or alkali metal salicylate, for example isodecyl salicylate or tnmethylsilyl salicylate, or alternatively acid beta-hydroxybutyric.
- the compositions according to the present invention may also contain one or more alpha-hydroxy acids as well as their salts and esters, represented by the following general formula (II):
- R 3 and R 4 identical or different, represent a hydrogen atom, a linear or branched alkyl group comprising 1 to 5 carbon atoms optionally substituted by a carboxyl group, or a phenyl group, and R 5 is an atom hydrogen, an alkyl group, an ammonium group or an alkali or alkaline earth metal.
- R 3 is preferably a methyl or ethyl group and R is a hydrogen atom, or R 3 and R 4 both represent a group -CH 2 COOH.
- R 5 is preferably a hydrogen atom, an ammonium group or a sodium, magnesium, potassium or calcium ion.
- R 5 is an alkyl group in formula (II), this group may contain 1 to 15 carbon atoms, and may for example be an octyl, decyl or dodecyl group.
- formula (II) represents an alpha-hydroxy acid which may preferably be glycolic acid, lactic acid, malic acid, ascorbic acid, acid mandelic, citric acid or 2-hydroxybutanoic acid.
- the salts and esters represented by the general formula (II) where R 5 is an ammonium group or an alkali or alkaline earth metal atom can be obtained by a simple acid-base reaction, by reacting the acid represented by same formula (II) where R 5 is a hydrogen atom, with a base constituted for example by a hydroxide, such as 1 magnesium or calcium hydroxide, or an alkali or alkaline earth metal hydroxide.
- a base constituted for example by a hydroxide, such as 1 magnesium or calcium hydroxide, or an alkali or alkaline earth metal hydroxide.
- an alpha-hydroxy acid ester is used represented by the general formula (II) where R5 is an alkyl group such as an ethyl, propyl, butyl, octyl, decyl group. or dodecyl, and more preferably ethyl lactate, tri-C ⁇ 2 C ⁇ 3 -alkyl citrate, C ⁇ 2 -C ⁇ 3 alkyl lactate, bis (trimethylsilyl) glycolate.
- R5 is an alkyl group such as an ethyl, propyl, butyl, octyl, decyl group. or dodecyl, and more preferably ethyl lactate, tri-C ⁇ 2 C ⁇ 3 -alkyl citrate, C ⁇ 2 -C ⁇ 3 alkyl lactate, bis (trimethylsilyl) glycolate.
- This alpha-hydroxy acid ester is used in conjunction with beta-hydroxy acid and the sphingolipid or shmgolipid precursor, these three components can themselves be supplemented with excipients and carriers usually used in cosmetic and pharmaceutical compositions.
- excipients and carriers usually used in cosmetic and pharmaceutical compositions.
- a composition comprising an ethyl lactate or glycolate, a sphingolipid, a beta-hydroxy acid and one or two alpha-hydroxy acids chosen from glycolic acid, acid mandelic and malic acid.
- the tests carried out have shown that the combined presence of an ammonium salt and one or more hydroxy acids potentiates the effects of the ammonium salt by improving the absorption and the persistence.
- compositions according to the invention may also contain an alpha-acetoxylated acid such as alpha-acetylmandelic acid, alpha-acetylbenzylic acid, alpha-acetylglycolic acid and alpha-acetyl-lactic acid, or alternatively an alpha -aceto-acid such as pyruvic acid or gluconolactone.
- an alpha-acetoxylated acid such as alpha-acetylmandelic acid, alpha-acetylbenzylic acid, alpha-acetylglycolic acid and alpha-acetyl-lactic acid
- an alpha -aceto-acid such as pyruvic acid or gluconolactone.
- compositions according to the invention preferably comprise between 0.1% and 15% by weight of beta-hydroxy acid and between 0.01% and 6% by weight of sphingolipid or shmgolipid precursor relative to the total weight of the composition.
- the compositions comprise one or more beta-hydroxy acids in a proportion of 0.2% to 10%, one or more alpha-hydroxy acids in a proportion of 0.5% to 30% in total, and a sphingolipid is 0.01% to 5% by weight.
- a preferred composition according to the invention comprises between 0.1% and 6% by weight of beta-hydroxy acid, between 0.5% and 15% of alpha-hydroxy acid, between 5 and 20% of ester of alpha-hydroxy acid and between 0.01% and 1% of sphingolipid, relative to the total weight of the composition.
- compositions in accordance with the present invention are intended to be administered topically and therefore comprise, in addition to the essential components indicated below, usual excipients, additives and carriers acceptable on the market. pharmaceutical and cosmetic.
- emulsifiers, preservatives, thickeners, colorants, antioxidants, moisturizers, perfumes and various additives intended to improve the properties of the composition can be used.
- encapsulation systems for example by means of liposomes or microcapsules consisting for example of gelatin and of polyaminoelectrolyte.
- 10 sphingolipids or sphingolipid precursors used in the invention for example phytosphingosine.
- compositions may be in the form of creams, milks, gels, lotions, masks or ointments, and preferably in an anhydrous form, for example an alcoholic gel.
- They can be used in particular for the treatment of dermatological conditions such as acne, but also certain keratmisation disorders such as atopic dermatitis, xerosis, psoriasis, and pityriasis of the leather.
- the present invention also relates to a method of cosmetic treatment of the skin, consisting in applying to the skin at least one beta-hydroxy acid, or one of its acceptable salts and esters, and at least one
- Sphingolipid or a sphingolipid precursor as well as the use of a beta-hydroxy acid, or a pharmaceutically acceptable salt and ester thereof, in combination with a sphingolipid or a sphingolipid precursor, for the preparation of a composition dermatological for
- compositions of the invention have significant antimicrobial activity on different types of bacteria, and in particular
- a gel (lotion) having the following weight composition is prepared:
- Ethanol q.s.p. 100.00
- the gel the composition of which is given above, can be applied to the areas to be treated once or twice a day.
- a gel having the above composition can be obtained by operating according to the method indicated below, without this being limiting: the phytosphingosine salicylic acid and the alpha-hydroxy- are first solubilized acids in ethanol, then ethyl lactate, cyclopentasiloxane and transcutol, and finally hydroxypropylcellulose, are added thereto, operating at room temperature.
- a gel having the following composition:
- a milk having the composition by weight indicated below is prepared by a usual method: Phytosphingosine (encapsulated) 0.10
- Ammonium lactate (sol. 65% aqueous) 12.00
- a cream having the composition by weight indicated below is prepared: Phytosphingosine encapsulated 0.20
- a cream is prepared having the following composition:
- Ammonium lactate 5.00 Glyceryl stearate (and) PEG-100 stearate • i,, 20 Polymethyl methacrylate 2, 50
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0003557 | 2000-03-20 | ||
FR0003557A FR2806301B1 (fr) | 2000-03-20 | 2000-03-20 | Composition a base de sphingolipide et de beta-hydroxy-acide utilisable par voie topique pour les soins de la peau |
PCT/FR2001/000813 WO2001070235A1 (fr) | 2000-03-20 | 2001-03-19 | Composition a base de sphingolipide et de beta-hydroxy-acide pour les soins de la peau |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1265619A1 true EP1265619A1 (fr) | 2002-12-18 |
Family
ID=8848306
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP01917176A Withdrawn EP1265619A1 (fr) | 2000-03-20 | 2001-03-19 | Composition a base de sphingolipide et de beta-hydroxy-acide pour les soins de la peau |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1265619A1 (fr) |
AU (1) | AU4426801A (fr) |
FR (1) | FR2806301B1 (fr) |
WO (1) | WO2001070235A1 (fr) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1462081B1 (fr) * | 2001-12-10 | 2012-08-08 | Kao Corporation | Production d'emulsions a base de ceramides |
KR20030079231A (ko) * | 2002-04-02 | 2003-10-10 | 지앤비코스메틱 | 피부 표면에 국소 적용되는, 피부 여드름 개선용 화장료조성물 및 그의 제조방법 |
KR20030084484A (ko) * | 2002-04-27 | 2003-11-01 | 주식회사 참 존 | 여드름 피부용 화장료 조성물 |
JP2004043358A (ja) * | 2002-07-11 | 2004-02-12 | Unitika Ltd | 尋常性ざ瘡治療・予防剤 |
FR2855047B1 (fr) * | 2003-05-19 | 2007-11-30 | Oreal | Composition comprenant une base sphingoide, un activateur de la voie des 4-et/ou des 6-hydroxylases et un acide gras, utilisation pour renforcer la fonction barriere de la peau |
NL2003419C2 (en) * | 2009-09-01 | 2011-03-02 | Shieldmark Zacco | Composition for tropical application, uses thereof, applicator device and kit of parts. |
FR2972112B1 (fr) * | 2011-03-01 | 2020-11-06 | Oreal | Utilisation d'un compose pour le traitement des dermatoses inflammatoires |
FR2972110B1 (fr) * | 2011-03-01 | 2013-11-15 | Oreal | Procede de traitement cosmetique des rougeurs cutanees |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994006440A1 (fr) * | 1992-09-14 | 1994-03-31 | Smith Walter P | Composition de conditionnement de la peau, son application et sa production |
WO1995003028A1 (fr) * | 1993-07-23 | 1995-02-02 | Morris Herstein | Composition cosmetique stimulant le renouvellement de la peau, avec effet prolonge d'elimination de l'irritation |
FR2714829B1 (fr) * | 1994-01-10 | 1996-02-02 | Oreal | Composition cosmétique et/ou dermatologique pour le traitement du vieillissement contenant des céramides, son utilisation. |
US5720963A (en) * | 1994-08-26 | 1998-02-24 | Mary Kay Inc. | Barrier disruption treatments for structurally deteriorated skin |
DE69802908T2 (de) * | 1997-03-13 | 2004-05-06 | Cosmoferm B.V. | Salicylsäure - sphingoidbase derivate und ihre verwendung |
US5882665A (en) * | 1997-11-18 | 1999-03-16 | Elizabeth Arden Co., Division Of Conopco, Inc. | Phytosphingosine salicylates in cosmetic compositions |
FR2773074B1 (fr) * | 1997-12-30 | 2001-02-16 | Led Evolution Dermatolog | Composition a base d'alpha-hydroxy-acides et de ceramides utilisable par voie topique pour le traitement d'affections dermatologiques |
-
2000
- 2000-03-20 FR FR0003557A patent/FR2806301B1/fr not_active Expired - Fee Related
-
2001
- 2001-03-19 WO PCT/FR2001/000813 patent/WO2001070235A1/fr not_active Application Discontinuation
- 2001-03-19 AU AU44268/01A patent/AU4426801A/en not_active Abandoned
- 2001-03-19 EP EP01917176A patent/EP1265619A1/fr not_active Withdrawn
Non-Patent Citations (1)
Title |
---|
See references of WO0170235A1 * |
Also Published As
Publication number | Publication date |
---|---|
AU4426801A (en) | 2001-10-03 |
FR2806301A1 (fr) | 2001-09-21 |
WO2001070235A1 (fr) | 2001-09-27 |
FR2806301B1 (fr) | 2002-10-31 |
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