Use of cannabinoid compounds for stimulating melanogenesis

Patent metadata

Field	Value
Publication number	US-9326927-B2
Application number	US-201214237015-A
Country	US
Kind code	B2
Filing date	Aug 3, 2012
Priority date	Aug 5, 2011
Publication date	May 3, 2016
Grant date	May 3, 2016

Abstract

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.

First claim

The invention claimed is:

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):

Assignees

• Zuccolo Michela
• Jourdain Roland
• Breton Lionel
• Maccarrone Mauro
• Oreal

Inventors

• Zuccolo Michela
• Jourdain Roland
• Breton Lionel
• Maccarrone Mauro

Classifications

• A61P17/00

  Drugs for dermatological disorders · CPC title

• A61Q19/04

  for chemically tanning the skin (topical sun or radiation screening or tanning preparations A61Q17/04) · CPC title

• A61Q5/00

  Preparations for care of the hair · CPC title

• A61K31/16

  Amides, e.g. hydroxamic acids · CPC title

• A61K31/164

  of a carboxylic acid with an aminoalcohol, e.g. ceramides · CPC title