Resorcinol derivatives for cosmetic use thereof

Patent metadata

Field	Value
Publication number	US-10457619-B2
Application number	US-201616061913-A
Country	US
Kind code	B2
Filing date	Dec 8, 2016
Priority date	Dec 16, 2015
Publication date	Oct 29, 2019
Grant date	Oct 29, 2019

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 R 1 and R 2 , which may be identical or different, denote hydrogen, or a COR5 radical in which R5 denotes a linear C 1 -C 10 or branched C 3 -C 10 alkyl radical, preferably a linear C 1 -C 6 or branched C 3 -C 6 alkyl radical, more preferentially a linear C 1 -C 4 alkyl radical, R 3 denotes a linear C 1 -C 6 or branched C 3 -C 6 alkyl radical, preferably a linear C 1 -C 4 or branched C 3 -C 4 alkyl radical, and R 4 denotes H, a linear C 1 -C 6 or branched C 3 -C 6 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).

First claim

The invention claimed is:

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

wherein:
R 1 and R 2 , which may be identical or different, are chosen from:
a) hydrogen, or
b) a radical COR 5 , wherein R 5 is chosen from a linear C 1 -C 10 or branched C 3 -C 10 alkyl radical;
R 3 is chosen from a linear C 1 -C 6 or branched C 3 -C 6 alkyl radical; and
R 4 is chosen from:
a) hydrogen,
b) a linear C 1 -C 6 or branched C 3 -C 6 alkyl radical, or
c) a radical COR 5 ,
or a salt thereof, a solvate thereof, an optical isomer thereof, a racemate thereof, or a mixture thereof.

2. The compound according to claim 1 , wherein:
R 1 and R 2 , which may be identical or different, are chosen from a radical COR 5 , wherein R 5 is chosen from a linear C 1 -C 6 or branched C 3 -C 6 alkyl radical; and
R 3 is chosen from a linear C 1 -C 4 or branched C 3 -C 4 alkyl radical.

3. The compound according to claim 1 , wherein R 1 and R 2 , which may be identical or different, are chosen from a radical COR 5 , wherein R 5 is chosen from a linear C 1 -C 4 alkyl radical.

4. The compound according to claim 1 , wherein R 4 is chosen from hydrogen, a linear C 1 -C 4 alkyl radical, a branched C 3 -C 4 alkyl radical, or a radical COR 5 .

5. The compound according to claim 1 , wherein R 4 is chosen from hydrogen or a radical COR 5 .

6. The compound according to claim 1 , wherein:
R 1 and R 2 , which may be identical or different, are chosen from hydrogen or a COCH 3 radical;
R 3 is chosen from methyl, ethyl or isopropyl; and
R 4 is chosen from hydrogen or a COCH 3 radical,
or a salt thereof, a solvate thereof, an optical isomer thereof, a racemate thereof.

7. The compound according to claim 1 , wherein:
R 1 and R 2 , which may be identical or different, are chosen from hydrogen or a COCH 3 radical;
R 3 is methyl; and
R 4 is chosen from hydrogen or a COCH 3 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:

Compound

Structure
No.
Chemical name

1
4-(3-hydroxy-1- methylpropyl) benzene-1,3-diol

2
4-[4-(acetyloxy)but- 2-yl]benzene-1,3- diyl diacetate

3
3-(2,4- dihydroxyphenyl) butyl acetate

or salts thereof, solvates thereof, optical isomers thereof, racemates thereof, or mixtures thereof.

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

wherein:
R 1 and R 2 , which may be identical or different, are chosen from:
a) hydrogen, or
b) a radical COR 5 , wherein R 5 is chosen from a linear C 1 -C 10 or branched C 3 -C 10 alkyl radical;
R 3 is chosen from a linear C 1 -C 6 or branched C 3 -C 6 alkyl radical; and
R 4 is chosen from
a) hydrogen,
b) a linear C 1 -C 6 or branched C 3 -C 6 alkyl radical, or
c) a radical COR 5 ,
or a salt thereof, a solvate thereof, an optical isomer thereof, a racemate thereof, or a mixture thereof.

10. The composition according to claim 9 , wherein:
R 1 and R 2 , which may be identical or different, are chosen from hydrogen or a radical COR 5 , wherein R 5 is chosen from a linear C 1 -C 6 or branched C 3 -C 6 alkyl radical; and
R 3 is chosen from a linear C 1 -C 4 or branched C 3 -C 4 alkyl radical.

11. The composition according to claim 9 , wherein R 1 and R 2 , which may be identical or different, are chosen from a radical COR 5 , wherein R 5 is chosen from a linear C 1 -C 4 alkyl radical.

12. The composition according to claim 9 , wherein R 4 is chosen from hydrogen, a linear C 1 -C 4 alkyl radical, a branched C 3 -C 4 alkyl radical, or a radical COR 5 .

13. The composition according to claim 9 , wherein R 4 is chosen from hydrogen or a radical COR 5 .

14. The composition according to claim 9 , comprising at least one compound according to formula (I) wherein:
R 1 and R 2 , which may be identical or different, are chosen from hydrogen or a COCH 3 radical;
R 3 is chosen from methyl, ethyl or isopropyl; and
R 4 is chosen from hydrogen or a COCH 3 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:
R 1 and R 2 , which may be identical or different, are chosen from hydrogen or a COCH 3 radical;
R 3 is methyl; and
R 4 is chosen from hydrogen or a COCH 3 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:

Compound

Structure
No.
Chemical name

1
4-(3-hydroxy-1- methylpropyl) benzene-1,3-diol

Assignees

• Oreal

Inventors

• Marat Xavier
• Gueguiniat Amélie

Classifications

• A61P17/00

  Drugs for dermatological disorders · CPC title

• A61K8/375

  the alcohol moiety containing more than one hydroxy group · CPC title

• A61K8/347

  Phenols · CPC title

• C07C39/11 Primary

  Alkylated hydroxy benzenes containing also acyclically bound hydroxy groups, e.g. saligenol · CPC title

• A61Q19/02

  for chemically bleaching or whitening the skin · CPC title