Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
2000-10-13
2002-12-24
Hartley, Michael G. (Department: 1617)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C554S069000, C514S171000
Reexamination Certificate
active
06497888
ABSTRACT:
The present invention relates generally to a process for limiting the penetration into the skin and/or the keratinous fibres of at least one cosmetically and/or pharmaceutically active agent present in a base cosmetic and/or pharmaceutical composition for topical application and in particular for reducing the rate of penetration into the skin and/or the keratinous fibres of the active agent(s).
Numerous families of compounds are known which have the property of activating the penetration into the skin or the keratinous fibres of an active agent present in a cosmetic and/or pharmaceutical composition. Thus, U.S. Pat. No. 4,960,771 discloses the use, in cosmetic or pharmaceutical compositions, of oxazolidinone derivatives for increasing the penetration of active agents in the broadest sense. The use of amides for increasing this penetration is disclosed in U.S. Pat. No. 5,162,315.
U.S. Pat. Nos. 4,837,026, 4,876,249 and 5,030,629 disclose cyclic derivatives which promote the penetration of active agents.
On the other hand, very few families of compounds are known which possess the reverse activity, that is to say effectively reducing the penetration of an active agent of a cosmetic and/or pharmaceutical composition into the skin and/or the keratinous fibres.
However, some oxazolidinone derivatives exhibit this property.
It would be desirable to have available compounds or formulations having properties of reducing the penetration into the skin and/or the keratinous fibres of active agents of cosmetic and/or pharmaceutical compositions.
This is because, for certain cosmetic and/or pharmaceutical formulations for application to the skin and/or the keratinous fibres, it is highly desirable to reduce, slow down or indeed even eliminate the penetration of an active agent of the formulation into the substrate, skin or keratinous fibres to which the cosmetic and/or pharmaceutical formulation is applied, either for reasons of safety or for reasons of effectiveness.
Thus, for reasons of effectiveness, it may be important to reduce the penetration of dyes or of sunscreens into the keratinous fibres and/or the skin.
In the case of sunscreens, the protective effect of which on the skin decreases according to their penetration into the skin, it is desirable to slow down, indeed optionally even eliminate, their penetration into the skin in order to increase the effectiveness thereof.
It would thus be desirable to have available an agent which, used with a base cosmetic and/or pharmaceutical composition comprising at least one cosmetically and/or therapeutically active agent, reduces, indeed even eliminates, the penetration into the skin and/or the keratinous fibres of the cosmetically and/or therapeutically active agent.
The above aim is achieved according to the invention by the joint use, with a base cosmetic and/or pharmaceutical composition comprising at least one cosmetically and/or pharmaceutically active agent, of an effective amount of a dispersion of vesicles in a medium, the vesicles comprising at least one ceramide of formula (I):
in which R
1
is chosen from saturated and unsaturated, linear and branched C
1
-C
32
, preferably C
9
-C
25
, alkyl groups optionally substituted by at least one hydroxyl group, wherein the at least one hydroxyl group is optionally esterified by a group chosen from C
1
-C
35
, preferably C
8
-C
28
, acyl groups, and R
2
is chosen from saturated and unsaturated, linear and branched C
1
-C
50
, preferably C
6
-C
35
, alkyl groups optionally substituted by at least one hydroxyl group, and wherein the at least one hydroxyl group is optionally esterified by a group chosen from C
1
-C
30
, preferably C
6
-C
24
, acyl groups.
The medium in which the vesicles are dispersed is essentially an aqueous medium. This means that the medium is sufficiently aqueous so that the vesicles can be dispersed therein.
A subject-matter of the invention is therefore a process for limiting, indeed even eliminating, the penetration into the skin and/or the keratinous fibres of at least one cosmetically and/or pharmaceutically active agent present in a base cosmetic and/or dermal pharmaceutical composition, characterized in that it consists in using, jointly with the base composition, an effective amount of the dispersion of vesicles defined above.
The term “joint use of the base composition and of the dispersion of vesicles” is understood to mean either the addition of the effective amount of the dispersion of vesicles directly to the base composition before use, such as by application in the form of a film on the skin and/or the keratinous fibres, or the successive application to the skin and/or to the keratinous fibres, in the form of films, of an effective amount of the dispersion of vesicles, followed by the base composition.
The term “effective amount of the dispersion of vesicles” is understood to mean an amount of the dispersion sufficient to produce a significant effect in limiting the penetration, in particular the rate of penetration, of the active agent or agents of the base composition.
Another subject-matter of the present invention is a cosmetic or pharmaceutical composition which includes at least one cosmetically or pharmaceutically active agent, characterized in that it additionally comprises a dispersion of vesicles as defined above in an amount which is effective in limiting the penetration of the active agent or agents into the skin and/or the keratinous fibres.
The at least one ceramide of the formula (I) is chosen from known compounds. These ceramides and their processes of preparation are disclosed, inter alia, in European Patents EP-500,437, EP-647,617 and EP-790,053, the disclosures of which are specifically incorporated by reference herein.
The dispersion of vesicles can also comprise a mixture of ceramides of formula (I) and/or a stereoisomeric mixture of ceramides of formula (I).
Mention may be made, among the preferred ceramides of formula (I), of
2-(oleoylamino)octadecane-1,3-diol, 2-(lineoylamino)octadecane-1,3-diol,
2-[(2′-hydroxyhexadecanoyl)amino]octadecane-1,3-diol,
2-[(2′-hydroxydecosanoyl)amino]octadecane-1,3-diol,
2-[(D,L-mandeloyl)amino]octadecane-1,3-diol and oleyl chloride.
The particularly preferred ceramide is
2-[(2′-hydroxyhexadecanoyl)amino]octadecane-1,3-diol.
The dispersion of vesicles can comprise at least one second lipids other than the at least one ceramide of formula (I).
The at least one second lipid used in combination with the at least one ceramide of formula (I) in the dispersion of vesicles can be any lipid, other than the at least one ceramide of formula (I) of the dispersion, which makes possible the formation of vesicles and which does not harm the property of limiting penetration of the cosmetically and/or pharmaceutically active agent or agents of the dispersion.
A representative at least one second lipid capable of being used in combination with the at least one ceramide of formula (I), is chosen from alcohols and diols with a chain comprising 8-32 carbon atoms, preferably 12-30 carbon atoms, steroids, such as cholesterol, phospholipids, cholesteryl sulphate and phosphate, amines with a chain comprising 8-32 carbon atoms, preferably 12-30 carbon atoms, and their quaternary ammonium derivatives, dihydroxyalkylamines, polyoxyethylenated amines with a chain comprising 8-32 carbon atoms, preferably 12-30 carbon atoms, esters of aminoalcohols with a chain comprising 8-32 carbon atoms, preferably 12-30 carbon atoms, their salts and quaternary ammonium derivatives, phosphoric esters of alcohols with a chain comprising 8-32 carbon atoms, preferably 12-30 carbon atoms, such as dicetyl hydrogen phosphate and its sodium salt, alkyl sulphates, such as sodium cetyl sulphate, acids with a chain comprising 8-32 carbon atoms, preferably 12-30 carbon atoms, in the form of salts, and lipids of the type of those disclosed in Patents FR-2,315,991, 1,477,048 and 2,091,516 or in International Patent Application WO 93/01571, the disclosures of all of which are specifically incorpora
Morancais Jean-Luc
Philippe Michel
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
Hartley Michael G.
L'Oreal (S.A.)
Willis Michael A.
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