EP0500437B1
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EP
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Ceramides, method for their preparation and their application in cosmetics and dermopharmacy
Assignee: L'Oréal SA
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Filing: 1992-02-17
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Granted: 1995-07-26
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Expires: 2012-02-17
Abstract
Abstract The invention relates to ceramides of formula: <IMAGE> where R1 denotes a C11 to C21 alkyl or alkenyl radical and R2 denotes a linear C11-C19 hydrocarbon radical which carries one or more ethylenic unsaturations, and especially one or two, or a mixture of linear C11-C19 hydrocarbon radicals which are saturated or carry one or more ethylenic unsaturations, and especially one or two, in which the proportion of saturated radicals must not exceed 35%, these compounds being in the form of a racemic mixture of the erythro and threo diasteroisomers in the proportions erythro:threo of 85:15 to 60:40. The invention likewise relates to the process for preparing the compounds as well as their application in cosmetics and dermopharmacy.
Inventors
- 👤 Alexandre Zysman
- 👤 Guy Vanlerberghe
- 👤 Didier Semeria
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-01 14:33
CPC Classifications
C; C07; C07C; C07C233/00; C07C233/01; C07C233/16; C07C233/17; C07C233/20; A; A61; A61K; A61K8/00; A61K8/02; A61K8/14; A61K8/18; A61K8/30; A61K8/68; A61K9/00; A61K9/10; A61K9/127; A61K9/1271; A61K9/1272; A61Q; A61Q19/00; A61Q5/00; B; B82; B82Y; B82Y5/00; A61Q1/00; A61Q1/02; A61Q1/04; A61Q1/06; A61Q1/10; A61Q5/02; A61Q5/06
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
107 words
Synthetic ceramide comprising a compound of formula: in which: . R₁ denotes a C₁₁ to C₂₁ alkyl or alkenyl radical; . R₂ denotes a C₁₁-C₁₉ hydrocarbon radical, which is linear and carries one or more ethylenic unsaturations, and in particular one or two, or a mixture of compounds of formula (I) and of formula: in which R₁ is defined as above and R₂ is a saturated linear C₁₁-C₁₉ hydrocarbon radical, the proportion of compounds of formula (Ia) in the mixture not exceeding 35%, this ceramide being in the form of a racemic mixture of the erythro and threo diastereoisomers in the erythro:threo proportions of 85:15 to 60:40.
Claim 2
Dependent Claim
19 words
Synthetic ceramide according to Claim 1, characterised in that R₁ is a C₁₅ radical derived from sphingosine or dihydrosphingosine.
Claim 3
Dependent Claim
23 words
Synthetic ceramide according to either of Claims 1 and 2, characterised in that R₂ is a radical derived from oleic or linoleic acid.
Claim 4
Dependent Claim
21 words
Synthetic ceramide according to any one of Claims 1 to 3, characterised in that it is chosen from 2-oleoylamino-1,3-octadecanediol and 2-linoleoylamino-1,3-octadecanediol.
Claim 5
Dependent Claim
115 words
Process for preparing a ceramide according to any one of Claims 1 to 4, characterised in that it consists in acylating an amine functional group of a sphingosine or a dihydrosphingosine of the following formula (II) in which R₁ denotes a C₁₁ to C₂₁ alkyl or alkenyl radical, this compound being in the form of a racemic mixture of the erythro and threo diastereoisomers in the erythro: threo proportions of 85:15 to 60:40, with an acid chloride, with an anhydride, with a paranitrophenol ester, with a succinimide ester, with a dicyclohexylcarbodiimide ester, with a lower alkyl ester or with an azolide, in an anhydrous medium or in solvents such as tetrahydrofuran, pyridine, dimethylformamide and dichloromethane.
Claim 6
Dependent Claim
48 words
Process for preparing a ceramide according to Claim 5; characterised in that the anhydride is a mixed anhydride of formula R₂COOCOOC₂H₅, R₂ having the meaning given in Claim 1, the lower alkyl ester is a methyl or ethyl ester and the azolide is an imidazolide or a pyrazolide.
Claim 7
Dependent Claim
63 words
Composition for cosmetic or dermopharmaceutical use, characterised in that it contains 0.05 to 20% by weight, preferably 0.1 to 10% by weight, of at least one ceramide according to any one of Claims 1 to 4, in the presence of an adjuvant chosen from fatty substances, solvents, water, thickeners, emulsifiers, moisturising products, demulcents, sunscreen agents, germicides, colorants, preservatives, perfumes, propellants and surface-active agents.
Claim 8
Dependent Claim
88 words
Composition according to Claim 7, characterised in that it is provided in the form of an emulsion whose fatty phase, representing 5 to 60% of the total weight of the emulsion, is essentially composed of a mixture of the ceramide with at least one oil, the aqueous phase constituting 30 to 85% of the total weight of the emulsion, the emulsifying agent being present in an amount of 1 to 20% by weight, and preferably 2 to 12% by weight relative to the total weight of the emulsion.
Claim 9
Dependent Claim
38 words
Composition according to Claim 7, characterised in that it is provided in the form of an oily, oil-alcohol or dilute alcoholic lotion, in the form of a gel, a dispersion, solid sticks, a spray or an aerosol foam.
Claim 10
Dependent Claim
48 words
Composition according to Claim 7, characterised in that it is provided in the form of an aqueous dispersion of lipid spherules composed of organised molecular layers enclosing an encapsulated aqueous phase, these layers being composed of the ceramide or ceramides combined with at least one other lipid compound.
Claim 11
Dependent Claim
74 words
Composition in the form of an aqueous dispersion of lipid spherules according to Claim 10, characterised in that the other lipid compound is chosen from long chain alcohols and diols, sterols, phospholipids, glycolipids, cholesteryl sulphate and phosphate, long chain amines and quaternary ammonium derivatives thereof, dihydroxyalkylamines, polyoxyethylenated fatty amines, long chain amino alcohol esters, quaternary ammonium salts and derivatives thereof, fatty alcohol phosphoric esters, alkyl sulphates and fatty acids in the form of salts.
Claim 12
Dependent Claim
34 words
Composition in the form of an aqueous dispersion of lipid spherules according to either of Claims 10 and 11, characterised in that the spherules have a diameter of between 0.05 »m and 5 »m.
Claim 13
Dependent Claim
38 words
Composition in the form of an aqueous dispersion of lipid spherules according to either of Claims 10 and 11, characterised in that the aqueous phase encapsulated in the spherules is water or an aqueous solution of active substance.
Claim 14
Dependent Claim
94 words
Composition in the form of an aqueous dispersion of lipid spherules according to any one of Claims 10 to 13, characterised in that the aqueous phase encapsulated in the spherules contains at least one cosmetic and/or pharmaceutical, water-soluble active substance chosen from humectants, artificial tanning agents optionally combined with colorants, water-soluble sunscreen agents, antiperspiration agents, deodorants, astringents, refreshing products, tonic products, cicatrising products, keratolytic agents, depilatory products, perfumed water, plant tissue extracts, water-soluble colorants, antidandruff agents, antiseborrhoeic agents, oxidants, reducing agents, vitamins, hormones, enzymes, vaccines, anti-inflammatory agents, antibiotics, bactericides and cytotoxic or antitumour agents.
Claim 15
Dependent Claim
68 words
Composition in the form of an aqueous dispersion of lipid spherules according to any one of Claims 10 to 13, characterised in that it contains at least one fat-soluble active substance chosen from fat-soluble sunscreen agents, substances intended to improve the condition of dry or aged skin, tocopherols, vitamins E, F or A and esters thereof, retinoic acid, antioxidants, essential fatty acids, glycyrrhetinic acid, keratolytic agents and carotenoides.
Claim 16
Dependent Claim
49 words
Composition in the form of an aqueous dispersion of lipid spherules according to any one of Claims 10 to 15, characterised in that it comprises 2 to 70% by weight of a water-immiscible liquid phase chosen from oils, hydrocarbons, halogenated hydrocarbons, perfluorotributylamine, polysiloxanes, organic acid esters, ethers and polyethers.
Claim 17
Dependent Claim
39 words
Use of the ceramide according to any one of Claims 1 to 4, as a waxy constituent having emollient and demulcent properties in emulsions, dispersions, gels, solid sticks, sprays, aerosol foams or in lotions for cosmetic or dermopharmaceutical use.
Claim 18
Dependent Claim
35 words
Use of the ceramide according to any one of Claims 1 to 4 in combination with at least one other lipid compound, for the formation of dispersions of lipid spherules for cosmetic or dermopharmaceutical use.
Claim 19
Dependent Claim
44 words
Process for the cosmetic treatment of the skin, the hair or hair strands, characterised in that it consists in applying to the skin, the hair or the hair strands a sufficient amount of a composition according to any one of Claims 7 to 16.
References Cited (Backward Citations)
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