Retinyl carbonate derivatives, preparation process and uses

Details Retinyl carbonate derivatives, preparation process and uses Retinyl carbonate derivatives, preparation process and uses

2000-05-30

2001-12-18

Badio, Barbara P. (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Cyclopentanohydrophenanthrene ring system doai

C514S512000, C552S544000, C558S277000

Reexamination Certificate

active

06331535

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel retinyl carbonate derivatives. The invention also relates to the use of these compounds in or for the preparation of compositions intended in particular for preventing or combating acne and/or chronological or actinic ageing of the skin.
2. Discussion of the Background
Retinoid-based cosmetic and/or dermatological compositions have undergone considerable development in recent years. The reason for this is that it has been found that certain compounds of the retinoid family, derived from retinoic acid, are advantageous in skin care, in particular in the treatment of acne and for limiting, or even eliminating altogether, the effects of ageing on the skin such as wrinkles, a weathered appearance, yellowing, loss of elasticity, a ruddy complexion and dryness of the skin, as well as the appearance of blemishes.
These signs of ageing are all the more accentuated when the skin is frequently exposed to sunlight or is particularly sensitive to exposure to UV radiation. Thus, the effects of intrinsic ageing of the skin (age-related) and of light-induced ageing (due to exposure to sunlight) can be cumulative. The manifestations of ageing usually appear at an advanced age; however, their prevention should be undertaken from the start of adult life by suitable care treatments.
Treatment of the skin with compounds of the retinoid family forms part of these preventive or curative care treatments for the signs of ageing.
Among the compounds of the retinoid family, retinol, also known as vitamin A, is most particularly advantageous. The reason for this is that retinol is a natural endogenous constituent of the human body. It is also well tolerated when applied to the skin up to levels that are considerably higher than those for retinoic acid.
However, when it is introduced into a cosmetic composition intended for topical application, retinol degrades rapidly under the effects of light, oxygen, metal ions, oxidizing agents, water or, in particular, under the effect of elevated temperature. There is thus a need for compounds with retinoid-type activity which are more stable than retinol.
WO 95/16659 discloses conjugate compounds obtained from the reaction of retinoids with organic acids or derivatives of these acids. The retinoid, which may be retinol, retinal, retinoic acid or dehydroretinol, is conjugated to the acid derivative, which may be an aldehyde, a ketone, an alcohol, an ester, etc. via an ester, reverse ester, amide or ether bond. Among the very great number of compounds corresponding to this definition, only the ether obtained by reaction of retinol with the hydroxyl function of glycolic acid is described. In particular, no mention is made of retinyl carbonate derivatives.
Moreover, the publications from Svishchuk et al., “Preparation of &agr;-tocopherol (Vitamin E) Ethers”,
Farm. Zh
., 29(6), 36-8 (1974) and from Protopova et al., “Insecticidal Action of 6-hydroxychroman derivatives”,
Fiziol, Akt. Veshchestva
, 7, 142-4 (1975) describe, respectively, a tocopheryl retinyl carbonate and an analogous compound in which the side chain of the tocopheryl radical is slightly modified. However, these compounds are not intended for cosmetic use.
SUMMARY OF THE INVENTION
Accordingly, it has now been found that the above-described problems associated with conventional compounds have been solved by the present invention, the first embodiment of which provides a retinol derivative corresponding to formula (I):
in which R is selected from the group including:
(a) a linear, cyclic or branched, saturated or unsaturated C
1
—C
18
hydrocarbon-based radical, which is unsubstituted or substituted with one or more groups —OH, —OR′, —NHCOR, —SH, —SR′, —COOH, —CONHR′, —COOR′, —CN or —CF
3
, in which R′is a C
1
-C
4
alkyl radical; with a halogen atom; or with:
(i) one or more saturated or unsaturated, substituted or unsubstituted C
3
-C
7
aliphatic rings, or
(ii) one or more substituted or unsubstituted aromatic rings, or
(iii) one or more saturated or unsaturated, substituted or unsubstituted C
3
-C
7
heterocycles, or
(iv) one or more amino acid or peptide residues;
(b) a radical of cyclopentanephenanthrene structure, which is at least partially hydrogenated and/or substituted,
(c) an aryl radical optionally substituted with one or more groups —OH, —NH
2
, —SH, —COOH, —CONHR′, —NHCOR, —COOR′, —OR′, —SR′, —CN or —CF
3
, in which R′is a C
1
-C
4
alkyl; with a halogen atom; or with:
(i) one or more saturated or unsaturated, substituted or unsubstituted C
3
-C
7
aliphatic rings, or
(ii) one or more substituted or unsubstituted aromatic rings, or
(iii) one or more saturated or unsaturated, substituted or unsubstituted C
3
-C
7
heterocycles,
wherein substituted chroman groups are excluded;
(d) a group derived from ceramide, sphingosine or sphinganine;
(e) an amino acid or peptide residue bearing a free hydroxyl group; and
(f) a carbohydrate residue.
Another embodiment of the invention provides a composition, which includes:
the retinol derivative described above; and
a physiologically acceptable medium.
Another embodiment of the invention provides a process for preparing the retinol derivative described above, including reacting a chloroformate with retinol.
Another embodiment of the invention provides a process for preparing the retinol derivative described above, including reacting two equivalents of retinol with one equivalent of carbonyldiimidazole.
Another embodiment of the invention provides a method of using the composition described above for the cosmetic treatment of the skin.
Another embodiment of the invention provides a method of using the composition described above for the cosmetic treatment of the scalp.
Another embodiment of the invention provides a method of using retinol derivative described above to prepare a composition intended for the cosmetic treatment of the skin.
Another embodiment of the invention provides a method of using the retinol derivative described above to prepare a composition intended to combat at least one condition selected from the group including acne, chronological aging of the skin, actinic ageing of the skin, and combinations thereof.
Another embodiment of the invention provides a method of using the retinol derivative described above to prepare a composition intended to combat at least one condition selected from the group including the greasy appearance of the hair and hair loss.
Another embodiment of the invention provides a method of combating or treating at least one condition selected from the group including acne, chronological aging of the skin, actinic ageing of the skin, greasy appearance of the hair, hair loss, and combinations thereof, that includes applying to the skin or scalp the retinol derivative described above.
Another embodiment of the invention provides a method of combating or treating at least one condition selected from the group including acne, chronological aging of the skin, actinic ageing of the skin, greasy appearance of the hair, hair loss, and combinations thereof, that includes applying to the skin or scalp the composition described above.
DETAILED DESCRIPTION OF THE INVENTION
Various other objects, features and attendant advantages of the present invention will be more fully appreciated as the same becomes better understood from the following detailed description of the preferred embodiments of the invention.
Preferably, the derivatives of formula (I) can be defined as the products of condensation of retinol with other compounds bearing an alcohol function, via a carbonate bond.
Preferable linear hydrocarbon-based radicals containing from 1 to 18 carbon atoms include methyl, ethyl, propyl, butyl, hexyl, octyl, decyl, dodecyl, hexadecyl and octadecyl radicals.
Preferable branched hydrocarbon-based radicals containing from 1 to 18 carbon atoms include 2-ethylhexyl, 2-butyloctyl and 2-hexyldecyl radicals.
The unsaturated hydrocarbon-based radicals are preferably radicals containi

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