Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1995-12-12
1998-11-24
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
C07C23300
Patent
active
058409408
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/01069/ filed Mar. 20, 1995.
TECHNICAL FIELD
The present invention relates to a new physiologically active ceramide derivative. Specifically, the invention relates to a new linoleoylamide based ceramide. This ceramide is highly soluble in normally employed ceramide emollients. 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 maintaining said barrier. It is believed that one of the causes of a 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 lipids 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. One of these types is characterized by the presence of linoleic acid in an ester linkage (so-called ceramide 1). Several references postulate that after hydrolysis this essential fatty acid plays an important role on its own in the hydration of the stratum corneum. (P. W. Wertz et al., Biochim. Biophys. Acta 753, 350-355, 1983; P. Skolnik et al., Arch. Derm. 113, 939-941, 1977; P. Bowser et al., Biochim. Biophys. Acta 834, 429-436, 1985).
It is also 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 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 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, this 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 improve with decreasing chain length and 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. Phytosphingosine is also an aminoalcohol, but 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 cannot be predicted.
SUMMARY OF THE INVENTION
The invention provides a novel compound having the following structure: ##STR1## i.e. N-linoleoylphytosphingosine.
The invention further provides a method for preparing N-linoleoylphytosphingosine.
Compositions comprising the new compound are used for maintaining the integrity of the epidermal water permeability barrier of the skin. The compositions con
REFERENCES:
patent: 5368857 (1994-11-01), Corcoran et al.
De Pater Robertus Mattheus
Koger Hein Simon
Lambers Johannes Wilhelmus Jacobus
Verweij Jan
Carr Deborah D.
Geist Gary
Gist-Brocades B.V.
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