Drug – bio-affecting and body treating compositions – Cosmetic – facial
Patent
1996-05-30
1997-12-02
Mosley, Terressa M.
Drug, bio-affecting and body treating compositions
Cosmetic, facial
424401, 514847, A61K 600
Patent
active
056936770
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to new physiologically active ceramide derivatives. Specifically, the invention relates to new ceramide 3 derivatives based on monounsaturated fatty acids. These ceramide 3 derivatives are soluble in normally employed ceramide solvents and have a relatively high oxidation stability. The bioavailability is increased and the ceramide is used for maintaining the epidermal water permeability barrier of the skin.
BACKGROUND OF THE INVENTION
It is generally understood that ceramides present within the intercellular lipid lamellae of the stratum corneum have an important structural function in the water permeability barrier of the skin. The ceramides are considered essential in structuring and maintaining said barrier. It is believed that one of the causes of dry skin is a reduction in the amount of ceramides within these intercellular lipid lamellae. It is therefore desirable to be able to successfully replace these depleted lipida via the topical route.
Downing et al. (Arch. Dermatol. Res. 277, 284-287, 1985; J. Invest. Derm. 84, 410-412, 1985; J. Lipid Res. 24, 759-765, 1983) identified the six predominant existing types of ceramides in the stratum corneum. It is observed that in surfactant-induced dry skin there exists a relative deficiency of a ceramide with phytosphingosine as a backbone (A. W. Fulmer et al. J. Invest. Derm. 86, 598-602, 1985). This ceramide was identified by Downing as ceramide 3. Ceramide 3 is a mixture of different molecules, characterized by the general name N-acylphytosphingosine, wherein the acyl group is saturated and has a chain length of 14 to 30 carbon atoms.
Ceramides must be able to penetrate the stratum corneum in order to reach the lipid lamellae of the permeability barrier. One of the unsolved problems with the topical application of skin products is to find a suitable way to deliver the active ingredient in sufficient amounts to the place where it must exert its biological activity. The penetration of the ceramides in the skin is highly dependent on their solubility in a cosmetic formulation.
KAO has disclosed in the European Patent Applications, EP 227994 and EP 282816 that surfactants such as glycerylethers assist in penetration of ceramides into the stratum corneum. However, these kind of surfactants tend to permanently disrupt the stratum corneum so that afterwards the penetrated ceramide leaks out of the stratum corneum again.
A class of compounds with well known surfactant properties are fatty acids via acylation coupled with the aminoalcohol diethanolamine. It is observed that the surfactant properties of these compounds improve with increasing degree of unsaturation of the fatty acyl group. (H .S. Vedanayagam et al., J. Oil Technol. Assoc. India, 15, 68-71, 1984).
In ceramide 3, a saturated fatty acid (C.sub.14 -C.sub.30) is coupled via acylation with phytosphingosine. Although phytosphingosine also is an aminoalcohol, it is structurally very different from diethanolamine. In contrast to diethanolamine, phytosphingosine already contains an alkyl chain (having a length of 14 carbon atoms in ceramide 3). The influence of the presence of this phytosphingosine alkyl chain on modifications in the acyl group of ceramide 3 therefore cannot be predicted.
SUMMARY OF THE INVENTION
The invention provides novel compounds having the following formula: ##STR1## wherein R is a straight chain or branched alkyl group containing one double bona and having up to 55 carbon atoms, preferably 10 to 50 carbon atoms, more preferably 14 to 48 carbon atoms, and X is an integer from 11 to 21, inclusive, preferably 13.
A preferred compound of the present invention is N-oleoyl phytosphingosine.
The invention further provides a method for preparing a monounsaturated derivative of ceramide 3 by the acylation of phytosphingosine with monounsaturated fatty acids.
The compounds of the present invention are soluble in fatty alcohol containing solvents, their solubility being higher than that of corresponding ceramide 3 derivatives containing saturat
REFERENCES:
patent: 5368857 (1994-11-01), Corcoran et al.
Fulmer, A.W., et al., J. of Investigative Dermatology, Inc., (1986) 86:598-602.
Kraus, R. et al., Liebigs Ann. Chem., (1991) 1991:125-128.
Long, S.A., et al., Arch Dermatol Res., (1985) 277:284-287.
Wertz, P.W., et al., J. or Investigative Dermatology, (1985) 84:410-412.
Wertz, P.W. et al., J. of Lipid Res., (1983) 24:759-765.
Derwent WPI, Derwent Abstract No. AN 93-070179 (Kao Corp.) (1993).
Vedanayagam, H.S., et al., "Preparation, characterization and surfactant properties of fatty acid diethanolamides" J. Oil Technol. Assoc. of India (1984) 15:68-71.
Lambers Johannes Wilhelmus Jacobus
Verweij Jan
Gist-Brocades N.V.
Mosley Terressa M.
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