Ceramide compounds, process of preparation and use

Details Ceramide compounds, process of preparation and use Ceramide compounds, process of preparation and use

1999-12-21

2001-03-20

Kumar, Shailendra (Department: 1621)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Cosmetic, antiperspirant, dentifrice

C424S059000, C424S070100, C424S405000, C514S827000, C514S828000, C514S880000, C514S588000, C556S009000, C556S012000, C560S169000, C560S170000, C564S060000

Reexamination Certificate

active

06203808

ABSTRACT:

The present invention relates to novel compounds of ceramide type, their process of preparation and their use, in particular for the treatment and care of the skin, hair, nails and eyelashes, in cosmetics or in pharmaceuticals.
Exposure of the skin to the 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.
Provision has in particular been made to use ceramides in order to solve these problems. This is because it is known that these compounds are the major constituents of the intercorneocytic lipids of the stratum corneum and participate in maintaining the integrity of the cutaneous barrier.
The ceramides used in cosmetics are generally natural extracts derived in particular from pigskin, ox brain, eggs, blood cells, plants, such as wheat, and the like (See Japanese Patent Applications J86/260008 and J87/120308). Such ceramides have also been provided for the protection of hair (See EP 0,278,505).
They are therefore always mixtures with a greater or lesser content of ceramides, the composition of which is difficult to monitor. In addition, these mixtures are subject to bacterial contamination. It is thus difficult to control or preserve them. When they are of animal origin, there is in addition a risk of contamination by the agent responsible for BSE (bovine spongiform encephalopathy).
Provision has been made, in order to overcome these disadvantages, for synthetic ceramides, in particular in European Patent Applications EP 500,437 and EP 647,617. These compounds, 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.
Provision has also been made, in European Patent Application EP 420,722, for lipid ceramide derivatives corresponding to the formula:
R
1
—CH(OH)—CH(CH
2
OH)—NH—COOR
2
in which R
1
denotes a C
11
to C
21
alkyl or alkenyl radical and R
2
denotes a C
8
to C
30
hydrocarbon-comprising radical. In this document, provision has been made to modify the amide junction of the ceramides by replacing it by a urethane junction. The compounds thus obtained are of particular advantage in the treatment of the skin or hair and also make it possible to prevent or to correct certain effects of drying. Furthermore, they exhibit a weak aggressive nature with respect to the skin or ocular mucous membranes and good emollient and softening properties.
However, the need still remains to have available compounds which have an improved moisturizing and/or treating effect with respect to the compounds of the prior art, while being capable of application in the cosmetic and/or dermatological fields, in particular.
The inventors have thus sought compounds which make it possible to prevent or to correct phenomenons which are reflected by a visible drying and which restore the skin's suppleness and the hair's gloss and softness.
The subject-matter of the present invention is thus compounds corresponding to the formula (I):
R
1
—CH(OH)—CH(CH
2
OH)—NH—CO—NR
2
R
3
in which:
R
1
denotes a saturated or unsaturated, linear or branched, C
9
to C
23
alkyl radical which may be optionally hydroxylated,
R
2
denotes hydrogen or a saturated or unsaturated, linear or branched, C
1
to C
8
alkyl radical,
R
3
denotes a saturated or unsaturated, linear or branched, C
1
to C
32
alkyl radical which may be optionally hydroxylated, it being possible for the hydroxyl radical itself to be substituted by a saturated or unsaturated, linear or branched, C
1
to C
24
acyl radical; the R
3
group can optionally be interrupted by 1 to 7 heteroatoms.
Another subject of the invention is a process for the preparation of the above compounds, in which an aminodiol of formula:
R
1
—CH(OH)—CH(NH
2
)—CH
2
OH
is reacted with an azolide derivative in an inert solvent, so as to obtain the desired compound.
Another subject of the invention is an aqueous dispersion of lipid spherules composed of organized molecular layers enclosing an encapsulated aqueous phase, the layers being composed of at least one compound of formula (I) above in combination with at least one other lipid compound.
Another subject of the invention is a composition, in particular for cosmetic or pharmaceutical use, comprising, in a cosmetically or pharmaceutically acceptable medium, at least one compound of formula (I) and/or one aqueous dispersion of lipid spherules as above.
Another subject of the invention is the use of a compound of formula (I) or of an aqueous dispersion of lipid spherules comprising it as moisturizing, emollient and/or softening agent.
Yet another subject of the invention is the use, in cosmetics or in pharmaceuticals, of a compound of formula (I) or of an aqueous dispersion of lipid spherules comprising it for treating and/or caring for the skin and/or keratinous substances, in particular for treating and/or caring for damaged and/or aged skin and/or of damaged hair and/or nails.
It has been found that these novel compounds exhibit a very good moisturizing power for the skin and/or keratinous substances (hair, eyelashes, eyebrows and nails). They can be used with very particular advantage when an effect in combating drying of the skin and/or of the hair is sought in cosmetics or in pharmaceuticals.
These novel compounds have the advantage of improving and/or of reestablishing the barrier function when they are applied to the skin. Furthermore, these compounds exhibit a weak aggressive nature with respect to the skin or ocular mucous membranes and good tolerance with respect to cell membranes, such as those of erythrocytes.
These novel compounds exhibit emollient and softening properties, in particular for the skin and hair. In addition, they can be easily dissolved in the fatty phases of cosmetic or pharmaceutical compositions.
The compounds according to the invention can be used to treat damaged and/or aged skin and damaged hair or nails in the cosmetic or pharmaceutical field.
Hair treated with these compounds of formula (I) exhibits 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 (i.e., body) properties are also improved.
The compounds according to the invention thus correspond to the following formula:
R
1
—CHOH—CH(CH
2
OH)—NH—CO—NR
2
R
3
where
R
1
preferably denotes an optionally hydroxylated, saturated or unsaturated, linear C
11
to C
19
alkyl radical,
R
2
preferably denotes hydrogen, and
R
3
preferably denotes a saturated or unsaturated, linear or branched, C
4
to C
18
alkyl radical which can be interrupted by 1 to 5 heteroatoms.
Mention may be made, among heteroatoms, of oxygen, nitrogen and/or silicon.
The compounds according to the invention can be used in the form of a pure isomer or of mixtures of isomers.
The preferred compounds according to the invention are:
2-(N-hexadecylureido)octadecane-1,3-diol,
2-(N-ethyloxycarbonylmethylureido)octadecane-1,3-diol,
2-(N-oleylureido)octadecane-1,3-diol,
N-(2-aminooctadecane-1,3-diol)carboxy-N′-aminopropylsiloxane, and
2-(N-dodecylureido)octadecane-1,3-diol.
The compounds according to the invention can be easily prepared by a person skilled in the art, in particular using the process which is the subject-matter of the invention. This process comprises reacting an aminodiol of formula:
R
1
—CH(OH)—CH(NH
2
)—CH
2
OH
with an azolide derivative in an inert solvent, so to obtain the desired compound.
Use is preferably made of an imidazolide derivative, such as an imidazolidide.
The two starting constituents are preferably added in equimolar amounts.
The reaction is preferably

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