Resorcinol derivatives for cosmetic use thereof

• US 10,457,619 B2
• Filed: 12/08/2016
• Issued: 10/29/2019
• Est. Priority Date: 12/16/2015
• Status: Active Grant

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Marat, Xavier, Gueguiniat, Amelie
• Primary Examiner(s): Keys, Rosalynd A
• Application Number:
  US16/061,913
• Publication Number:
  US 20180370886A1
• Time in Patent Office: 1,055 Days
• CPC Class Codes: A61K 8/347 Phenols
• CPC Class Codes: A61K 8/375 the alcohol moiety containing more than one hydroxy group
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61Q 19/02 for chemically bleaching or whitening the skin
• CPC Class Codes: C07C 39/11 Alkylated hydroxy benzenes containing also acyclically bound hydroxy groups, e.g. saligenol
• CPC Class Codes: C07C 69/18 of trihydroxylic compounds

Abstract

The present invention relates to a compound of formula (I), in particular for the use thereof for depigmenting, lightering and/or bleaching the skin. (I) In which R₁ and R₂, which may be identical or different, denote hydrogen, or a COR5 radical in which R5 denotes a linear C₁-C₁₀ or branched C₃-C₁₀ alkyl radical, preferably a linear C₁-C₆ or branched C₃-C₆ alkyl radical, more preferentially a linear C₁-C₄ alkyl radical, R₃ denotes a linear C₁-C₆ or branched C₃-C₆ alkyl radical, preferably a linear C₁-C₄ or branched C₃-C₄ alkyl radical, and R₄ denotes H, a linear C₁-C₆ or branched C₃-C₆ alkyl radical, or a COR5 radical, and also the salts thereof, the solvates thereof and the optical isomers thereof, and the racemic mixtures thereof, alone or as a mixture. The present invention also relates to the novel compounds (I) and also to the process for preparing same and to a cosmetic process for depigmenting the skin using such compounds (I).

Claims

1. A compound for depigmenting, lightening, and/or bleaching the skin, according to formula (I) below:

2. The compound according to claim 1, wherein:

R₁ and R₂, which may be identical or different, are chosen from a radical COR₅, wherein R₅ is chosen from a linear C₁-C₆ or branched C₃-C₆ alkyl radical; and

R₃ is chosen from a linear C₁-C₄ or branched C₃-C₄ alkyl radical.

3. The compound according to claim 1, wherein R₁ and R₂, which may be identical or different, are chosen from a radical COR₅, wherein R₅ is chosen from a linear C₁-C₄ alkyl radical.

4. The compound according to claim 1, wherein R₄ is chosen from hydrogen, a linear C₁-C₄ alkyl radical, a branched C₃-C₄ alkyl radical, or a radical COR₅.

5. The compound according to claim 1, wherein R₄ is chosen from hydrogen or a radical COR₅.

6. The compound according to claim 1, wherein:

R₁ and R₂, which may be identical or different, are chosen from hydrogen or a COCH₃ radical;

R₃ is chosen from methyl, ethyl or isopropyl; and

R₄ is chosen from hydrogen or a COCH₃ radical,

or a salt thereof, a solvate thereof, an optical isomer thereof, a racemate thereof.

7. The compound according to claim 1, wherein:

R₁ and R₂, which may be identical or different, are chosen from hydrogen or a COCH₃ radical;

R₃ is methyl; and

R₄ is chosen from hydrogen or a COCH₃ radical,

or a salt thereof, a solvate thereof, an optical isomer thereof, or a racemate thereof.

8. The compound according to claim 1, wherein the compound is chosen from:

9. A cosmetic composition comprising, in a physiologically acceptable medium, at least one compound according to formula (I) below:

10. The composition according to claim 9, wherein:

R₁ and R₂, which may be identical or different, are chosen from hydrogen or a radical COR₅, wherein R₅ is chosen from a linear C₁-C₆ or branched C₃-C₆ alkyl radical; and

R₃ is chosen from a linear C₁-C₄ or branched C₃-C₄ alkyl radical.

11. The composition according to claim 9, wherein R₁ and R₂, which may be identical or different, are chosen from a radical COR₅, wherein R₅ is chosen from a linear C₁-C₄ alkyl radical.

12. The composition according to claim 9, wherein R₄ is chosen from hydrogen, a linear C₁-C₄ alkyl radical, a branched C₃-C₄ alkyl radical, or a radical COR₅.

13. The composition according to claim 9, wherein R₄ is chosen from hydrogen or a radical COR₅.

14. The composition according to claim 9, comprising at least one compound according to formula (I) wherein:

R₁ and R₂, which may be identical or different, are chosen from hydrogen or a COCH₃ radical;

R₃ is chosen from methyl, ethyl or isopropyl; and

R₄ is chosen from hydrogen or a COCH₃ radical,

or a salt thereof, a solvate thereof, an optical isomer thereof, a racemate thereof, or a mixture thereof.

15. The composition according to claim 9, comprising at least one compound according to formula (I) wherein:

R₁ and R₂, which may be identical or different, are chosen from hydrogen or a COCH₃ radical;

R₃ is methyl; and

R₄ is chosen from hydrogen or a COCH₃ radical,

or a salt thereof, a solvate thereof, an optical isomer thereof, a racemate thereof, or a mixture thereof.

16. The composition according to claim 9, wherein the composition comprises at least one compound chosen from:

17. The composition according to claim 9, wherein the at least one compound according to formula (I) is present in an amount ranging from about 0.01% to about 10% by weight, relative to the total weight of the composition.

18. The composition according to claim 9, wherein the at least one compound according to formula (I) is present in an amount ranging from about 0.1% to about 5% by weight, relative to the total weight of the composition.

19. The composition according to claim 9, wherein the at least one compound according to formula (I) is present in an amount ranging from about 0.5% to about 3% by weight, relative to the total weight of the composition.

20. A nontherapeutic cosmetic process for depigmenting, lightening and/or bleaching keratin materials, wherein the method comprises applying to the keratin materials a cosmetic composition, the cosmetic composition comprising, in a physiologically acceptable medium, at least one compound according to formula (I) below: