Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Liposomes
Reexamination Certificate
1999-03-10
2001-06-19
Page, Thurman K. (Department: 1615)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Liposomes
C424S400000, C424S401000, C424S045000, C424S059000, C424S061000, C424S062000, C424S063000, C424S065000, C424S070100, C424S070270, C424S070600, C424S076100, C424S195110, C514S178000, C514S937000, C514S938000, C514S943000, C514S944000, C514S945000, C514S844000, C514S880000, C514S881000, C514S886000, C514S887000
Reexamination Certificate
active
06248352
ABSTRACT:
The invention encompasses novel lipid compounds derived from sphingoid bases, the process of preparation and their use, in particular for the treatment and care of the skin, hair, nails and eyelashes, in cosmetics or in dermatology.
Exposure of the skin to cold, to the sun or to atmospheres with a low relative humidity, repeated treatments with washing compositions or contact with organic solvents, are factors which result in a visible drying to various degrees. The skin appears drier and less supple and the skin contours appear more pronounced. Furthermore, hair which is subjected too often to certain hair treatments loses its glossy appearance and can become coarse and brittle.
The inventors have thus sought for compounds which make it possible to prevent or to correct these phenomena, which are reflected by visible drying, and which restore the skin's suppleness and the hair's gloss and softness.
In order to solve this problem, provision has already been made, in particular in French Patent 2,652,002, for the use of lipid compounds. These compounds, when used in cosmetic or dermatological compositions for the treatment and care of the skin and hair, have a moisturizing effect which makes it possible to prevent or to correct certain effects of visible drying of the skin or hair. However, it would be desirable to develop compounds which, when used in cosmetic or dermatological compositions, have a moisturizing or treating effect superior to that of the compounds of this patent.
One aspect of the invention is therefore novel lipid compounds derived from sphingoid bases corresponding to the formula:
in which
R
1
denotes a C
1
-C
31
, preferably C
9
-C
25
, hydrocarbon-comprising radical, in particular a saturated or unsaturated, linear or branched, C
1
-C
31
, preferably C
9
-C
25
, hydrocarbon radical which can be substituted by one or more optionally esterified hydroxyls; OR
2
denotes a cholesteryl radical; the said compounds being in the form of a pure enantiomer or in the form of a mixture of isomers.
Preferred compounds of formula (I), are, for example:
N-(cholesteryloxycarbonyl)-2-aminooctadecane-1,3-diol;
N-(cholesteryloxycarbonyl)-2-aminooctadecane-1,3,4-triol;
the said compounds being in the pure form or in the form of mixtures of isomers.
The lipid compounds of formula (I) above are somewhat similar in their structure to ceramides, which are the main constituents of the intercorneocytic lipids of the stratum corneum. It is generally accepted that they participate in maintaining the integrity of the cutaneous barrier. They are also found, to a lesser extent, in the hair.
The compounds of formula (I) according to the invention can therefore be of very particular advantage in the treatment and care of the skin, hair, nails and eyelashes in cosmetics or in dermatology, the moisturizing effects of which are substantially greater than those of lipid compounds derived from sphingoid bases of the prior art, in particular those in French Patent 2,652,002.
The lipid compounds of formula (I) are satisfactorily harmless with respect to the skin, hair, nails, eyelashes, eyebrows and mucous membranes. They have good emollient and softening properties. They are easily dissolved in the fatty phases of cosmetic and dermopharmaceutical preparations.
Furthermore, hair treated with these compounds of formula (I) can exhibit a glossy appearance, a softer feel and a reduced sensitivity to water, due to the contribution of lipid matter uniformly distributed over the scales of the hair. The mechanical and liveliness properties can also be improved.
The compounds according to the invention can form vesicles with other lipids.
The lipid compounds according to the invention of formula (I) above can be obtained by the condensation on the amine functional group of a sphingoid base of the following formula (II):
in which R
1
has the same meaning indicated in formula (I), with either a cholesteryl chloroformate of the following formula (III):
in which OR
2
has the same meaning indicated in the formula (I), in an appropriate organic solvent in the presence of a base; or with the cholesteryl imidazolide of following formula (IV):
in which OR
2
has the same meaning indicated in the formula (I).
The process for the preparation of the compounds of formula (I) can be represented by the following scheme:
R
1
and OR
2
having the meanings indicated above.
The compounds of formula (I) can be obtained either by reaction of the compounds of formula (II) with the chloroformate (III) in solvents, such as tert-butyl methyl ether, dimethylformamide or tetrahydrofuran (THF), in the presence of a base, such as, for example, triethylamine, pyridine, sodium bicarbonate, and the like, or by reaction of the compounds of formula (II) with the imidazolide (IV), which is isolated or prepared in situ, for example by reaction of a fatty alcohol with carbonyldiimidazole.
Cholesteryl chloroformate is a commercial product. Cholesteryl imidazolide is synthesized according to the methods described by H. A. Staab in Angew. Chem. International Edit., Vol. 1 (1962), No. 7, p. 351, the disclosure of which is specifically incorporated by reference herein.
The hydrochloride of the compound of formula (II) may also be used in the preparation of the compound of formula (I).
The compounds of formula (II) are known compounds. Their synthesis has been described in particular by D. Shapiro in “Chemistry of Sphingolipids”, Hermann, Paris (1969), the disclosure of which is specifically incorporated by reference herein.
The synthetic processes described above result in racemic mixtures. It is possible to obtain compounds in the form of pure enantiomers by carrying out a resolution of the racemate described by Shapiro in the above mentioned article on page 99. Pure enantiomers can also be synthesized directly according to the processes described by R. Schmidt in “Tetrahedron Letters”, Vol. 27, No. 4, pages 481-484 (1986), the disclosure of which is specifically incorporated by reference herein, by B. Bernet in the same journal, Vol. 24, No. 49, pages 5491-5494 (1983), the disclosure of which is specifically incorporated by reference herein, or by Makoto Kiso in “Carbohydrate Research”, 158 (1986), pages 101-111, the disclosure of which is specifically incorporated by reference herein.
The lipid compounds according to the invention of formula (I) can have various applications, in particular in cosmetic and dermatological compositions. In addition, these compounds possess the property of forming vesicles in combination with other lipids, when they are dispersed in water.
One aspect of the invention is therefore the use of the compounds of formula (I) in emulsions or dispersions or in lotions. Another aspect of the invention is the use of these compounds, in combination with other lipids, for the formation of lipid spherules.
Another aspect of the invention is compositions for cosmetic or dermatological use comprising, in a cosmetically acceptable medium, at least one of the compounds of formula (I) as defined above.
Yet another aspect of the invention is a process for the cosmetic treatment of the skin, hair, nails, eyelashes or eyebrows which comprises applying to the skin, hair, nails, eyelashes or eyebrows a sufficient amount of such a composition comprising the compounds of formula (I).
Generally, the compositions according to the invention can be in the form of emulsions (milk or cream); aqueous/alcoholic, oily or oleoalcoholic lotions; gels; dispersions or solid sticks; or an aerosol foam or sprays.
According to the invention, the compounds of formula (I) are preferably present in an amount ranging from 0.005% to 20%, more preferably from 0.01 to 10%, of the total weight of the composition.
The compositions are, for example, emollient lotions, milks or creams; milks or creams for caring for the skin or hair; make-up removal creams, lotions or milks; foundation bases; anti-sun lotions, milks or creams; artificial tanning lotions, milks or creams; shaving creams or foams; after-shave lotions; shampoos; lip rouges; mascar
Philippe Michel
Semeria Didier
Channavajjala Lakshmi
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal (S.A.)
Page Thurman K.
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