Use of cannabinoid compounds for stimulating melanogenesis
The invention relates to the nontherapeutic cosmetic use of at least one cannabinoid compound chosen from the compounds corresponding to general formula (I): and also the geometric isomers and optical isomers thereof, the cosmetically acceptable acid or base salts thereof, and the hydrates thereof; in which compounds of formula (I): R 1 represents a hydrogen atom or a C 1 -C 30 alkyl group; it being possible for said alkyl group to be optionally substituted with a hydroxyl (OH) group; R 2 represents a halogen atom or a group chosen from hydroxyl, thiol (SH), and amino optionally substituted with one or two C 1 -C 6 alkyl groups; R 3 and R 4 form, together with the carbon atom which bears them, an oxo group or else R 3 and R 4 represent a hydrogen atom; R 5 represents a hydrogen atom or a C 1 -C 6 alkyl group; X represents a heteroatom chosen from oxygen and sulfur atoms and the divalent group —N(R 6 )—, with R 6 representing a hydrogen atom or a C 1 -C 6 alkyl group; represents a single or double bond; n is 1, 2 or 3, preferentially 1 or 2; it being understood that, when R 3 and R 4 together form an oxo group with the carbon atom which bears them and X represents an oxygen atom, then R 1 cannot represent a hydroxymethyl group, as an agent for coloring keratin materials. It also relates to one of these specific cannabinoid compounds for use thereof in the treatment of vitiligo or pityriasis versicolor , to nontherapeutic cosmetic processes for coloring the skin or for treating canities, comprising the topical application to the skin and/or head hair, or the oral administration, of a composition comprising, in a physiologically acceptable medium, one of these cannabinoid compounds, and to a process for selecting an active agent which promotes the pigmentation of keratin materials.
1. A process for coloring a keratin material comprising:
treating a keratin material in need of coloring with a composition comprising a coloring effective amount of at least one cannabinoid compound selected from the group consisting of a compound of formula (I):
a geometric isomer thereof, an optical isomer thereof, a cosmetically acceptable acid or base salt thereof, and a hydrate thereof;
wherein:
R 1 represents a hydrogen atom, or a C 1 -C 30 alkyl group, which is optionally substituted with a hydroxyl (OH) group;
R 2 represents a halogen atom or a group selected from the group consisting of a hydroxyl group, a thiol (SH) group, and an amino group optionally substituted with one or two C 1 -C 6 alkyl groups;
R 3 and R 4 form an oxo group via carbon atoms of R 3 and R 4 or else R 3 and R 4 represent a hydrogen atom;
R 5 represents a hydrogen atom or a C 1 -C 6 alkyl group;
X represents a heteroatom selected from the group consisting of oxygen and sulfur, and a divalent group of —N(R 6 )—, with R 6 representing a hydrogen atom or a C 1 -C 6 alkyl group;
represents a single or double bond; and
n is 1, 2 or 3;
with the proviso that, when R 3 and R 4 form an oxo group via carbon atoms of R 3 and R 4 and X represents an oxygen atom, R 1 is not a hydroxymethyl group.
2. The process of claim 1 , wherein the cannabinoid compound is selected from the group consisting of anandamide, methanandamide, arachidonyl-2′-chloroethylamide, linoleyl ethanolamide, docosatetraenyl ethanolamide and 2-arachidonyl glyceryl ether.
3. The process of claim 1 , wherein the cannabinoid compound is an agent for increasing pigmentation of the skin and/or body hair and/or head hair.
4. The process of claim 1 , wherein the cannabinoid compound is a skin-browning agent.
5. The process of claim 1 , wherein the cannabinoid compound is an agent for slowing natural whitening of head hair.
6. The process of claim 1 , wherein the cannabinoid compound is an agent for stimulating melanogenesis.
7. A cannabinoid compound, which is a compound of formula (I):
a geometric isomer thereof, an optical isomer thereof, a cosmetically acceptable acid or base salt thereof, or a hydrate thereof,
wherein
R 1 represents a hydrogen atom, or a C 1 -C 30 alkyl group, which is optionally substituted with a hydroxyl (OH) group;
R 2 represents a halogen atom or a group selected from the group consisting of a hydroxyl group, a thiol (SH) group, and an amino group optionally substituted with one or two C 1 -C 6 alkyl groups;
R 3 and R 4 form an oxo group via carbon atoms of R 3 and R 4 or else R 3 and R 4 represent a hydrogen atom;
R 5 represents a hydrogen atom or a C 1 -C 6 alkyl group;
X represents a heteroatom selected from the group consisting of oxygen and sulfur, and a divalent group of —N(R 6 )—, with R 6 representing a hydrogen atom or a C 1 -C 6 alkyl group;
represents a single or double bond;
n is 1, 2 or 3; and
with the proviso that, when R 3 and R 4 form an oxo group via carbon atoms of R 3 and R 4 and X represents an oxygen atom, R 1 is not a hydroxymethyl group.
8. A process for coloring skin comprising:
topically applying to the skin in need of coloring, or orally administering to a person having skin in need of coloring, a composition comprising, in a physiologically acceptable medium, a coloring effective amount of at least one cannabinoid compound of formula (I):
a geometric isomer thereof, an optical isomer thereof, a cosmetically acceptable acid or base salt thereof, or a hydrate thereof,
wherein
R 1 represents a hydrogen atom, or a C 1 -C 30 alkyl group, which is optionally substituted with a hydroxyl (OH) group;
R 2 represents a halogen atom or a group selected from the group consisting of a hydroxyl group, a thiol (SH) group, and an amino group optionally substituted with one or two C 1 -C 6 alkyl groups;
R 3 and R 4 form an oxo group via carbon atoms of R 3 and R 4 or else R 3 and R 4 represent a hydrogen atom;
R 5 represents a hydrogen atom or a C 1 -C 6 alkyl group;
X represents a heteroatom selected from the group consisting of oxygen and sulfur, and a divalent group of —N(R 6 )—, with R 6 representing a hydrogen atom or a C 1 -C 6 alkyl group;
represents a single or double bond;
n is 1, 2 or 3; and
with the proviso that, when R 3 and R 4 form an oxo group via carbon atoms of R 3 and R 4 and X represents an oxygen atom, R 1 is not a hydroxymethyl group.
9. A process for treating natural whitening of head hair comprising:
topically applying to head hair in need of coloring, or orally administering to a person having hair in need of coloring, a composition comprising, in a physiologically acceptable medium, a coloring effective amount of at least one cannabinoid compound of formula (I):
a geometric isomer thereof, an optical isomer thereof, a cosmetically acceptable acid or base salt thereof, or a hydrate thereof,
wherein
R 1 represents a hydrogen atom, or a C 1 -C 30 alkyl group, which is optionally substituted with a hydroxyl (OH) group;
R 2 represents a halogen atom or a group selected from the group consisting of a hydroxyl group, a thiol (SH) group, and an amino group optionally substituted with one or two C 1 -C 6 alkyl groups;
R 3 and R 4 form an oxo group via carbon atoms of R 3 and R 4 or else R 3 and R 4 represent a hydrogen atom;
R 5 represents a hydrogen atom or a C 1 -C 6 alkyl group;
X represents a heteroatom selected from the group consisting of oxygen and sulfur, and a divalent group of —N(R 6 )—, with R 6 representing a hydrogen atom or a C 1 -C 6 alkyl group;
represents a single or double bond;
n is 1, 2 or 3; and
with the proviso that, when R 3 and R 4 form an oxo group via carbon atoms of R 3 and R 4 and X represents an oxygen atom, R 1 is not a hydroxymethyl group.
10. The process of claim 8 , wherein the cannabinoid compound is present at a concentration of from 0.00001% to 10% by weight, relative to a total weight of the composition.
11. The process of claim 8 , wherein the cannabinoid compound is selected from the group consisting of anandamide, methanandamide, arachidonyl-2′-chloroethylamide, linoleyl ethanolamide, docosatetraenyl ethanolamide and 2-arachidonyl glyceryl ether.
12. The process of claim 9 , wherein the cannabinoid compound is present at a concentration of from 0.00001% to 10% by weight, relative to a total weight of the composition.
13. The process of claim 9 , wherein the cannabinoid compound is selected from the group consisting of anandamide, methanandamide, arachidonyl-2′-chloroethylamide, linoleyl ethanolamide, docosatetraenyl ethanolamide and 2-arachidonyl glyceryl ether.
14. A process for treating skin having vitiligo or pityriasis versicolor comprising: applying to skin in need of treatment for vitiligo or pityriasis versicolor a composition comprising a vitiligo or pityriasis versicolor treating effective amount of at least one cannabinoid compound of formula (I):
a geometric isomer thereof, an optical isomer thereof, a cosmetically acceptable acid or base salt thereof, or a hydrate thereof,
wherein
R 1 represents a hydrogen atom, or a C 1 -C 30 alkyl group, which is optionally substituted with a hydroxyl (OH) group;
R 2 represents a halogen atom or a group selected from the group consisting of a hydroxyl group, a thiol (SH) group, and an amino group optionally substituted with one or two C 1 -C 6 alkyl groups;
R 3 and R 4 form an oxo group via carbon atoms of R 3 and R 4 or else R 3 and R 4 represent a hydrogen atom;
R 5 represents a hydrogen atom or a C 1 -C 6 alkyl group;
X represents a heteroatom selected from the group consisting of oxygen and sulfur, and a divalent group of —N(R 6 )—, with R 6 representing a hydrogen atom or a C 1 -C 6 alkyl group;
represents a single or double bond;
n is 1, 2 or 3; and
with the proviso that, when R 3 and R 4 form an oxo group via carbon atoms of R 3 and R 4 and X represents an oxygen atom, R 1 is not a hydroxymethyl group to a patient in need thereof.
15. The process of claim 14 , wherein the cannabinoid compound is selected from the group consisting of anandamide, methanandamide, arachidonyl-2′-chloroethylamide, linoleyl ethanolamide, docosatetraenyl ethanolamide and 2-arachidonyl glyceryl ether.