# US 2014/0193349 A1 · Use of cannabinoid compounds for stimulating melanogenesis > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0193349 A1 - Document ID: US20140193349A1 - Status: Published application - Kind: A1 - Application number: 14/237,015 - Filed: 2012-08-03 - Published: 2014-07-10 - Earliest claimed: 2011-08-05 - Assignees: L'oreal - Inventors: Michela Zuccolo; Roland Jourdain; Lionel Breton; Mauro Maccarrone - Web page: https://patentgrep.com/patent/US20140193349A1 ## CPC - A61K 8/42: Amides - A61K 31/16: Amides, e.g. hydroxamic acids - A61K 31/164: of a carboxylic acid with an aminoalcohol, e.g. ceramides - A61P 17/00: Drugs for dermatological disorders - A61Q 5/00: Preparations for care of the hair - A61Q 5/10: Preparations for permanently dyeing the hair - A61Q 19/00: Preparations for care of the skin - A61Q 19/04: for chemically tanning the skin (topical sun or radiation screening or tanning preparations A61Q17/04) - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS ## 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): R1 represents a hydrogen atom or a C1-C30 alkyl group; it being possible for said alkyl group to be optionally substituted with a hydroxyl (OH) group; R2 represents a halogen atom or a group chosen from hydroxyl, thiol (SH), and amino optionally substituted with one or two C1-C6 alkyl groups; R3 and R4 form, together with the carbon atom which bears them, an oxo group or else R3 and R4 represent a hydrogen atom; R5 represents a hydrogen atom or a C1-C6 alkyl group; X represents a heteroatom chosen from oxygen and sulfur atoms and the divalent group —N(R6)—, with R6 representing a hydrogen atom or a C1-C6 alkyl group; represents a single or double bond; n is 1, 2 or 3, preferentially 1 or 2; it being understood that, when R3 and R4 together form an oxo group with the carbon atom which bears them and X represents an oxygen atom, then R1 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. ## Claims ### Claim 1 A nontherapeutic cosmetic use of process for coloring a keratin material, the process comprising: treating the keratin material with 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: R1 represents a hydrogen atom, or a C1-C30 alkyl group, which is optionally substituted with a hydroxyl (OH) group; R2 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 C1-C6 alkyl groups; R3 and R4 form an oxo group via carbon atoms of R3 and R4 or else R3 and R4 represent a hydrogen atom; R5 represents a hydrogen atom or a C1-C6 alkyl group; X represents a heteroatom selected from the group consisting of oxygen and sulfur, and a divalent group of —N(R6)—, with R6 representing a hydrogen atom or a C1-C6 alkyl group; represents a single or double bond; and n is 1, 2 or 3; with the proviso that, when R3 and R4 form an oxo group via carbon atoms of R3 and R4 and X represents an oxygen atom, R1 is not a hydroxymethyl group. ### Claim 2 (depends on 1) 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. ### Claim 3 (depends on 1) 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. ### Claim 4 (depends on 1) The process of claim 1, wherein the cannabinoid compound is a skin-browning agent. ### Claim 5 (depends on 1) The process of claim 1, wherein the cannabinoid compound is an agent for slowing natural whitening of head hair. ### Claim 6 (depends on 1) The process of claim 1, wherein the cannabinoid compound is an agent for stimulating melanogenesis. ### Claim 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 R1 represents a hydrogen atom, or a C1-C30 alkyl group, which is optionally substituted with a hydroxyl (OH) group; R2 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 C1-C6 alkyl groups; R3 and R4 form an oxo group via carbon atoms of R3 and R4 or else R3 and R4 represent a hydrogen atom; R5 represents a hydrogen atom or a C1-C6 alkyl group; X represents a heteroatom selected from the group consisting of oxygen and sulfur, and a divalent group of —N(R6)—, with R6 representing a hydrogen atom or a C1-C6 alkyl group; represents a single or double bond; n is 1, 2 or 3; and with the proviso that, when R3 and R4 form an oxo group via carbon atoms of R3 and R4 and X represents an oxygen atom, R1 is not a hydroxymethyl group. ### Claim 8 (depends on 7) A nontherapeutic cosmetic process for coloring skin, the process comprising: topically applying to the skin, or orally administering a composition comprising, in a physiologically acceptable medium, the cannabinoid compound of claim 7. ### Claim 9 (depends on 7) A nontherapeutic cosmetic process for treating natural whitening of head hair, the process comprising: topically applying to head hair, or orally administering, a composition comprising, in a physiologically acceptable medium, the cannabinoid compound of claim 7. ### Claim 10 (depends on 8) 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. ### Claim 11 (depends on 8) 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. ### Claim 12 (depends on 9) 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. ### Claim 13 (depends on 9) 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. ### Claim 14 (depends on 7) A process for treating vitiligo or pityriasis versicolor, the process comprising: applying the cannabinoid compound of claim 7 to a patient in need thereof. ### Claim 15 (depends on 14) 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.