US20030059447A1 - Compositions comprising a combination of a free sphingoid base and a ceramide and uses thereof - Google Patents

Compositions comprising a combination of a free sphingoid base and a ceramide and uses thereof Download PDF

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Publication number
US20030059447A1
US20030059447A1 US09/367,033 US36703399A US2003059447A1 US 20030059447 A1 US20030059447 A1 US 20030059447A1 US 36703399 A US36703399 A US 36703399A US 2003059447 A1 US2003059447 A1 US 2003059447A1
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Prior art keywords
ceramide
composition
skin
carbon atoms
group
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Abandoned
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US09/367,033
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English (en)
Inventor
Johannes Wilhelmus J Lambers
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Cosmoferm BV
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Individual
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Assigned to DSM N.V. reassignment DSM N.V. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LAMBERS, JOHANNES WILHELMUS JACOBUS
Assigned to COSMOFERM B.V. reassignment COSMOFERM B.V. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DSM N.V.
Assigned to COSMOFERM B.V. reassignment COSMOFERM B.V. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: DSM GIST B.V.
Publication of US20030059447A1 publication Critical patent/US20030059447A1/en
Priority to US10/463,277 priority Critical patent/US7597899B2/en
Abandoned legal-status Critical Current

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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
    • A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • 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
    • 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
    • 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
    • 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
    • A61Q19/007—Preparations for dry skin

Definitions

  • the present invention relates to the field of topical use of compositions comprising a selected combination of sphingolipids.
  • the human skin forms a structural and adapted barrier to the environment. It further plays an important physiological role since it provides not only protection and thermoregulation, but also has a metabolic and sensorial function and storage capacity.
  • the lipid composition of the epidermal cells within the skin changes considerably when the cells migrate to the outer surface and differentiate.
  • the cells in the basal layer contain a complex lipid composition, with phospholipids as the major constituent.
  • the phospholipid content is diminished while the amount of cerebrosides (glycosylceramides), ceramides, cholesterol and cholesterol sulphate is increased as result of de novo synthesis and storage into the so-called lamellar bodies.
  • the stratum corneum horny layer
  • the most abundant lipids in this layer are ceramides, which mainly have been formed by enzymatic deglycosylation of cerebrosides.
  • the barrier function of the skin mainly is provided by the stratum corneum.
  • the stratum corneum consists of corneocytes embedded in an extracellular matrix of multiple bilayers of lipids.
  • the intercellular lipid phase of the stratum corneum has roughly the following composition: 40% ceramides, 25% cholesterol, 10% cholesteryl sulphate and 25% free fatty acids.
  • the skin is provided with both a perfect protective layer and a filter-active permeability layer.
  • Emollient creams and lotions may relieve part of the symptoms, but often only temporarily.
  • Conventional antiimflammatory creams, of which corticosteroid creams form the main part are more effective for the treatment of certain disorders but continued use may reduce the effectiveness of the treatment and/or may give side reactions.
  • conventional antiinflammatory as well as antimicrobial creams typically are not adapted to restore an impaired barrier function.
  • Ceramides are generally applied in cosmetics because of their moisture-retaining properties (see for instance Japanese patent application J61-260008).
  • lipid mixtures should be applied for an optimal treatment of skin disorders associated with a disrupted epidermal barrier.
  • Said lipid mixtures comprise lipids selected from the three major classes of naturally-occurring epidermal lipids, i.e. the classes of ceramides, cholesterol and free fatty acids.
  • these formulations have to be applied together with conventionally used therapeutic agents.
  • topical compositions comprising a combination of a free sphingoid base and a ceramide have a beneficial effect when applied on skin conditions associated with an impaired barrier function, and especially when applied on skin conditions further associated with a deranged regulation of cell growth and differentiation, inflammatory and/or infectious phenomena.
  • compositions suitable for topical use comprising a combination of a free sphingoid base and a ceramide.
  • the topical compositions of the invention can be cosmetic as well as dermatologic compositions.
  • topical compositions comprising a combination of a free sphingoid base and a ceramide have a positive and beneficial effect on skin conditions associated with an impaired lipid barrier function.
  • the synergistic effects of the combination of a free sphingoid base and a ceramide become even more apparent when the compositions according to the invention are used for the treatment of skin conditions wherein an impaired lipid barrier function further is associated with a deranged regulation of cell growth and differentiation, an imflammatory condition and/or an infectious state.
  • Said deranged regulation of cell growth and differentiation is characterized by conditions like hyperproliferation of keratinocytes, decreased differentiation of keratinocytes and/or decreased desquamation of corneocytes.
  • the present invention shows that the presence of a free sphingoid base especially improves the efficacy of the composition of the invention with regard to its antiinflammatory and/or its antimicrobial activity. It is shown that this efficacy improvement is due to, in particular, an antimicrobial and antiinflammatory activity of the free sphingoid base.
  • the free sphingoid base present in the composition according to the invention has a general structure according to Formula 1:
  • A is CH 2 —CH 2 , CH ⁇ CH or C(H)OH—CH 2 , and
  • R is a straight chain or branched alkyl group having 10 to 22 carbon atoms which may optionally contain one or more double bonds and/or may optionally be substituted with one or more hydroxyl groups, preferably is a straight chain alkyl group having 12 to 18 carbon atoms, more preferably is a straight chain alkyl group having 13 carbon atoms.
  • the ceramide present in the composition according to the invention has a general structure according to Formula 2:
  • a and R are defined as above, and
  • R′ is a straight chain or branched alkyl group having 13 to 55 carbon atoms, preferably 15 to 50 carbon atoms, more preferably 17 to 44 carbon atoms; the alkyl chain may optionally be interrupted by an oxygen atom or by an internal ester group; may optionally contain one or more double bonds; and may optionally be substituted with one or more hydroxyl groups.
  • the free sphingoid base which is present in the composition of the invention preferably is a sphingosine, a sphinganine or a phytosphingosine. More preferably, the free sphingoid base is a phytosphingosine obtainable by deacetylation of tetraacetylphytosphingosine obtainable by fermentation of the yeast Pichia ciferri.
  • the ceramide which is present in the composition of the invention can be extracted from a natural source, for instance a mammalian source, or can be obtained via synthetic means.
  • a suitable chemical synthesis method is the acylation of a free sphingoid base with a suitable fatty acid, for instance via the acylation method as disclosed in international patent application WO93/20038.
  • the ceramide present in the composition of the invention is a ceramide which corresponds in stereochemical configuration to a ceramide isolatable from mammalian skin.
  • Ceramides as isolated from mammalian skin typically can be subdivided in six heterogeneous classes of compounds, ceramide 1, 2, 3, 4, 5, 6I and 6II.
  • these ceramides consist of a free sphingoid base in amide linkage with a nonhydroxy or an ⁇ -hydroxy fatty acid, or an ⁇ -hydroxy fatty acid esterified with an additional fatty acid.
  • a ceramide which corresponds in stereochemical configuration to a mammalian skin ceramide may for instance be obtained by acylation of Pichia ciferri -derived phytosphingosine.
  • Examples of such ceramides are the ceramides disclosed in international patent applications WO93/20038, WO95/11881, WO95/25716 and WO96/10557.
  • an individual ceramide as well as a mixture of two or more different ceramides can be applied in a topical composition.
  • said mixture of two or more different ceramides may include various ceramide combinations, the choice of a specific combination depending among others on the desired application.
  • a combination of two or more representatives of each ceramide class may for instance be applied, since said combination may lead to an increased ceramide solubility in the composition according to the invention.
  • Individual ceramides may tend to crystallize and consequently become inert and unfunctional.
  • a further option is a combination of, on the one hand, a sphinganine- and/or sphingosine-containing ceramide and, on the other hand, a phytosphingosine-containing ceramide (e.g. ceramide 1 and/or 2 and/or 4/5 with ceramide 3 and/or Ceramide 6).
  • a phytosphingosine-containing ceramide e.g. ceramide 1 and/or 2 and/or 4/5 with ceramide 3 and/or Ceramide 6.
  • Such a combination consists of two types of ceramides having a head group which differs in hydrophilicity and this may increase barrier enhancing properties of the same.
  • ceramide containing an ⁇ -hydroxy fatty acid with a ceramide containing a non-hydroxylated fatty acid (e.g. ceramide 1 and/or ceramide 2 and/or ceramide 3 with ceramide 4/5 and/or ceramide 6).
  • composition of the invention optionally may comprise one or more additional skin lipid compounds, such as cholesterol, cholesterol esters like cholesteryl sulphate, free fatty acids like palmitic, stearic, behenic, oleic and/or linoleic acid and/or other sphingolipids like glycoceramides.
  • the composition of the invention may further comprise ceramide compounds having a short-chain acyl group, said short chain acyl group optionally being ⁇ -hydroxylated (so-called short-chain ceramides).
  • a cerebroside is understood to be a glycoceramide wherein a monosaccharide, mostly glucose or galactose, is attached to the oxygen of the —CH 2 OH group of the ceramide according to Formula 2.
  • gangliosides oligosaccharides, frequently including sialic acid, are attached to the same.
  • a short chain acyl group is meant to comprise acyl groups having 2 to 14 carbon atoms.
  • a preferred ceramide with a short-chain acyl group is acetylphytosphingosine.
  • Examples of ceramides having a short-chain ⁇ -hydroxyacyl group are disclosed in international patent application WO95/29151.
  • a composition comprising a free sphingoid base and a ceramide may contain as the sole type of ceramide compound a glycoceramide or a short-chain ceramide.
  • the ceramide compound in the composition of the invention may be a mixture of a glycoceramide and a short-chain ceramide.
  • the combination of a free sphingoid base and a ceramide may advantageously be applied in combination with a conventional antiinflammatory and/or antimicrobial agent, where said conventional antiinflammatory and/or antimicrobial agent may be applied in substantially lower concentrations than typically used, because of the activity of the free sphingoid base.
  • An example of a conventionally used antiinflammatory agent is a corticosteroid.
  • compositions according to the invention are agents which have an effect on skin appearance.
  • yeast ⁇ -glucan may be applied in the composition according to the invention to reduce UV-induced erythema.
  • Skin-peeling agents like ⁇ -hydroxyacids, urea, salicylic acid or proteases, may be applied in the composition according to the invention to improve desquamation and/or decrease roughness of the skin.
  • Retinoids may be applied in the composition according to the invention to stimulate the mitotic and metabolic activity of epidermal cells.
  • Vitamin C and/or E may be applied in the composition of the invention for their antioxidant activity on skin components, which favours their application as, for instance, antiageing agents.
  • the free sphingoid base as well as the ceramide may be present in the composition according to the invention in a concentration of 0.001 to 10%, preferably in a concentration of 0.005 to 5%, more preferably in a concentration of 0.01-2%, most preferably in a concentration of 0.02-1.0%.
  • the ratio of free sphingoid base to ceramide in the composition according to the invention may lie within a range of 1 to 10 to 10 to 1.
  • said ratio may vary from about 1 to 5 to about 5 to 1. More preferably, said ratio may vary from about 1 to 5 to about 1 to 1.
  • topical preparations of the invention further include the usual components.
  • the composition comprises a vehicle to enable the active ingredients to be conveyed to the skin.
  • the vehicle enables proper application on skin and/or hair, to provide both a dermatological as well as a cosmetic treatment.
  • the composition may comprise a solid, semi-solid or liquid cosmetically and/or physiologically acceptable vehicle.
  • vehicle will depend upon the method chosen for topical administration of the composition.
  • Vehicles other than water can include liquid or solid emollients, solvents, humectants, thickeners, powders, surfactants, which are also sometimes designated as emulsifiers, solubilizers, propellants and other active ingredients.
  • Emollients can be classified under such general chemical categories as (fatty acid) esters, fatty acids, (fatty) alcohols, polyols, (natural) waxes, natural oils, silicone oils, both volatile and non-volatile and hydrocarbons such as mineral oil, petroleum jelly, vaseline, squalens and (iso)paraffin.
  • Surfactants including emulsifiers may be cationic, nonionic, anionic or amphoteric in nature. A single type of surfactant and/or combinations of surfactants may be employed.
  • nonionic surfactants are alkoxylated compounds based upon fatty alcohols, fatty acids and sorbitan.
  • Anionic-type surfactants may include fatty acid soaps, lauryl sulphate salts, lauryl ether sulphate salts, alkyl benzene sulphonates, alkyl acid phosphates.
  • Amphoteric surfactants include materials as dialkylamine oxide and various types of betaines, such as cocoamido propyl betaine.
  • Cationic surfactants comprise quaternary ammonium compounds (Quats) such as cetyl trimethyl ammonium chloride or bromide.
  • a special class of surfactants are silicone surfactants, which are high molecular weight polymers of dimethyl polysiloxane with polyoxyethylene and/or polyoxypropylene side chains having a molecular weight of 10,000 to 50,000 D.
  • surfactants used for the preparation of emulsions include emulsifiers comprising compounds having a HLB (hydrophilic/lipophilic balance) value which is in the lower as well as in the higher ranges, i.e. compounds which are able to form a water-in-oil as well as compounds which are able to form an oil-in-water emulsion, respectively.
  • HLB hydrophilic/lipophilic balance
  • the HLB value of the emulsifier or mixture of emulsifiers varies between about 1 and 7.
  • said HLB value is higher than about 7.
  • Specific emulsifiers comprise emulsifiers which are able to form a lamellar phase (liquid crystalline or gel phase). Lamellar phases are formed at the oil-water interphase of an oil-in-water emulsion and directly incorporate the free sphingoid base and the ceramide. Examples of such specific emulsifiers are:
  • polyglyceryl-2 isostearate (or resp. di/tri/tetra isostearate)
  • sucrose esters (laurate/palmitate/stearate/oleate/isostearate)
  • Propellants include propane, butane, isobutane, dimethyl ether, chlorofluoroalkanes, carbon dioxide, nitrous oxide.
  • Solvents include ethyl alcohol, methylene chloride, isopropanol, ethyl ethers such as ethoxyethanol and butoxyethanol, acetone, tetrahydrofuran, dimethyl formamide, DMSO, propylene glycol, butylene glycol.
  • Humectants include proteins and protein hydrolysates, amino acids, sorbitol, glycerin, sorbitol, glycols preferably PEG 200-4000 and other polyols.
  • Thickeners include cross linked polyacrylates, silicone gums and polysaccharide gums such as xanthan, carrageenan, gelatin, pection and locust beans gum, hyaluronic acid and carboxylic group-containing polymers
  • Powders include chalk, talc, starch, kaolin, clays, silicates, carboxyvinyl polymers.
  • anti-oxidants like butyl hydroxy toluene, ascorbic acid and salts, EDTA, hydroquinone, tocopherols, gallates;
  • preservatives like para-hydroxy benzoate esters, sorbic acid, EDTA, quaterniums, benzoic acid, imidazolidinyl urea, (benzyl)alcohol;
  • enzyme regulators like vitamins and other co-factors
  • penetration enhancers like mono- or di-esters of C2 to C10 alcohols and C8 to C18 fatty acids, propanols, urea, sugar esters, POE esters or ethers of fatty acids and/or alcohols, butan-1,4 diol, tetrahydrofuran, salicylate salts, pyrrolidones, N-alkyl-aza-cycloheptanones, oleic acid, linoleic acid;
  • sunscreens blocking UV light, like PABA's, cinnamate and salicylate derivatives
  • the combination of the said components can account for 5 to 99% of the composition.
  • compositions according to the invention on affected skin areas are various and are summarized as follows: a reduction of redness, dryness, roughness and/or scaling of the skin, a reduction of pruritis, a reduction of skin lesions, an improvement in healing of small wounds, a decrease of inflammatory symptoms in affected areas, a decrease of an infectious state of the skin in affected areas.
  • Examples of skin conditions which benefit from topical application of a composition according to the invention are psoriasis, atopic dermatitis, irritant and allergic contact dermatitis, seborrheic and sebostatic dermatitis, photodermatitis (UV-induced erythema), acne, ichthyosis, xerosis, aged skin.
  • the skin infections which benefit from topical application of the compositions of the invention include bacterial, fungal, yeast and viral infections. For example dandruff, impetigo, Pityriasis vesicolor, Tinea corporis, Rosacea, Herpes, venereal diseases.
  • ceramides with a short-chain acyl group may be advantageous. These short-chain ceramides will have the additional effect that they are cell-permeable and known to reduce proliferation, increase differentiation and increase desquamation.
  • the present invention is exemplified by several formulations and by an efficacy study using test persons with different skin disorders. Furthermore, the antiimflammatory activity of a free sphingoid base is demonstrated.
  • ceramides and the free sphingoid base used in these formulations are the following:
  • Ceramide IIIB N-oleoyl-phytosphingosine
  • Phytoceramide I N-stearoyloxyheptacosanoyl-phytosphingosine Waterless Barrier Cream I comprising Ceramide III, Ceramide VI and Phytosphingosine INCI-name Trade name Percentage (% w/w) Hydrogenated lecithin 4.0 Glycerin 48.0 Butylene glycol 18.0 Jojoba oil 5.0 Propylene glycol Miglyol 840 (Huls) 10.0 dicaprylate/dicaprate Isocetyl alcohol Eutanol G16 (Henkel) 3.0 Tocopheryl acetate 5.0 Dimethicone copolyol 5.0 eicosonate Ceramide 3 Ceramide III 0.5 (Cosmoferm) Ceramide IIIB 0.5 (Cosmoferm) Ceramide 6 Ceramide VI 0.5 (Cosmoferm) Phytosphingosine Phytosphingosine 0.5 (Cosmoferm) Waterless Barrier Creams II and
  • barrier cream I was applied daily by several test persons suffering from various skin disorders. The results are indicated in Table 1. It is clear that the use of a barrier cream according to the invention results in a significant improvement of the affected skin areas.
  • test product resp. 0% (Placebo), 0.2 and 0.5% phytosphingosine (PS) in Propylene glycol:Ethanol (60:40).
  • PS phytosphingosine
  • IL-1 ⁇ secretion was measured in the incubation medium of the skin explants, using a standard ELISA technique.

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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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US09/367,033 1997-12-05 1998-12-07 Compositions comprising a combination of a free sphingoid base and a ceramide and uses thereof Abandoned US20030059447A1 (en)

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US10/463,277 US7597899B2 (en) 1997-12-05 2003-06-17 Compositions comprising a combination of a free sphingoid base and ceramide and uses thereof

Applications Claiming Priority (2)

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EP203824.4 1997-12-05
EP97203824 1997-12-05

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PCT/EP1998/008121 A-371-Of-International WO1999029293A1 (en) 1997-12-05 1998-12-07 Compositions comprising a combination of a free sphingoid base and a ceramide and uses thereof

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US (2) US20030059447A1 (ko)
EP (1) EP0975325B1 (ko)
JP (1) JP2001510487A (ko)
KR (1) KR100639531B1 (ko)
CN (1) CN1112916C (ko)
BR (1) BRPI9807124B8 (ko)
DE (1) DE69818242T2 (ko)
ES (1) ES2207023T3 (ko)
WO (1) WO1999029293A1 (ko)

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FR2855047A1 (fr) * 2003-05-19 2004-11-26 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
US20060194881A1 (en) * 2001-12-27 2006-08-31 Philippe Msika Composition comprising at least one alkanolamide to inhibit megration of langerhans cells and uses therof
US20080103207A1 (en) * 2006-08-09 2008-05-01 Takasago International Corp. (Usa) Topical ceramide compositions and methods of use
US20090062247A1 (en) * 2007-08-27 2009-03-05 Shuan Shian Huang METHODS FOR INHIBITING TGF-beta
US20100075923A1 (en) * 2008-09-16 2010-03-25 Jung San Huang Method of enhancing tgf-beta signalling
US20150126624A1 (en) * 2012-05-16 2015-05-07 Archer Daniels Midland Company Emulsifier for solubilizing polar solvents in oils and polyols
US20150351439A1 (en) * 2013-01-24 2015-12-10 Danstar Ferment A.G. Yeast cell walls comprising vitamin d2, uses thereof and method of producing the same
US9511144B2 (en) 2013-03-14 2016-12-06 The Proctor & Gamble Company Cosmetic compositions and methods providing enhanced penetration of skin care actives
CN110742842A (zh) * 2019-11-12 2020-02-04 医美生物科技(上海)有限公司 一种延缓皮肤老化的精华组合物及其制备方法
WO2021188326A1 (en) * 2020-03-17 2021-09-23 Enzo Biochem, Inc. Sphingosine pathway modulating compounds for the treatment of coronavirus infection
US20220047491A1 (en) * 2018-12-18 2022-02-17 Genuine R&D Co., Ltd. Ceramide dispersion composition
CN116261445A (zh) * 2020-10-09 2023-06-13 赢创运营有限公司 包含神经酰胺、聚甘油羧酸酯和胆甾醇的组合物

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JP4391668B2 (ja) * 2000-06-06 2009-12-24 高砂香料工業株式会社 液晶構造を有する脂質組成物
JP4619489B2 (ja) * 2000-06-13 2011-01-26 花王株式会社 抗かゆみ皮膚外用剤
US7419958B2 (en) 2001-03-26 2008-09-02 Dana-Farber Cancer Institute, Inc. Method of attenuating reactions to skin irritants
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JP2003155231A (ja) * 2001-11-20 2003-05-27 Kikkoman Corp 医薬及び抗アレルギー剤
EP1462081B1 (en) * 2001-12-10 2012-08-08 Kao Corporation Production of ceramide emulsions
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