Dithiazocane compounds for the cosmetic use thereof

Patent metadata

Field	Value
Publication number	US-2021000727-A1
Application number	US-201816955745-A
Country	US
Kind code	A1
Filing date	Dec 18, 2018
Priority date	Dec 21, 2017
Publication date	Jan 7, 2021
Grant date	—

Abstract

The invention relates to the non-therapeutic cosmetic use of at least one compound of formula (I) as defined below, as an agent for bleaching, lightening and/or depigmenting keratin materials, especially the skin. The invention also relates to a non-therapeutic cosmetic process for depigmenting, lightening and/or bleaching keratin materials, especially the skin, using these compounds (I).

First claim

1 .- 17 . (canceled)

18 . A method for bleaching, lightening, and/or depigmenting a keratin material, comprising applying to the keratin material a composition comprising at least one compound of formula (I),

salts thereof, solvates thereof, optical and/or geometrical isomers thereof, including enantiomers and diastereoisomers thereof, racemates thereof, or mixtures thereof:
wherein in formula (I):
R is chosen from a radical OR′ or NR a R b ;
R 1 is chosen from a hydrogen atom or a (C 1 -C 18 )alkyl group;
R′ is chosen from:
i) a hydrogen atom;
ii) a (C 1 -C 18 )alkyl group, wherein:
a) the (C 1 -C 18 )alkyl group is optionally substituted with at least one identical or different radical chosen from:
 hydroxyl;
 (hetero)cycloalkyl, optionally substituted with at least one identical or different radical chosen from hydroxyl, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, or C 1 -C 4 alkoxy, and/or at least one of ring members of the (hetero)cycloalkyl denoting a ketone (—CO—); or
 aryl, optionally substituted with at least one identical or different radical chosen from C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or hydroxyl; and/or
b) the (C 1 -C 18 )alkyl group is optionally interrupted with at least one heteroatom;

iii) a (C 2 -C 18 )alkenyl group, wherein:
a) the (C 2 -C 18 )alkenyl group is optionally substituted with at least one identical or different radical chosen from:
 hydroxyl; or
 aryl, optionally substituted with at least one identical or different radical chosen from C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or hydroxyl; and/or
b) the (C 2 -C 18 )alkenyl group is optionally interrupted with at least one heteroatom; or

iv) an optionally substituted aryl or heteroaryl radical;

R a and R b are independently chosen from:
i) a hydrogen atom;
ii) a (C 1 -C 18 )alkyl group, wherein:
a) the (C 1 -C 18 )alkyl group is optionally substituted with at least one identical or different radical chosen from:
 hydroxyl;
 carboxy;
 (C 1 -C 6 )alkyloxycarbonyl; or
 aryl, optionally substituted with at least one identical or different radical chosen from C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or hydroxyl; and/or
b) the (C 1 -C 18 )alkyl group is optionally interrupted with at least one heteroatom;

iii) a (C 2 -C 18 )alkenyl group, wherein:
a) the (C 2 -C 18 )alkenyl group is optionally substituted with at least one identical or different radical chosen from:
 hydroxyl;
 carboxy;
 (C 1 -C 6 )alkyloxycarbonyl; or
 aryl; optionally substituted with at least one identical or different radical chosen from C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or hydroxyl; and/or
b) the (C 2 -C 18 )alkenyl group is optionally interrupted with at least one heteroatom;

iv) an aryl or heteroaryl radical, optionally substituted with at least one identical or different radical chosen from C 1 -C 4 alkyl, hydroxyl, or C 1 -C 4 alkoxy; or
v) a heterocycloalkyl radical, optionally substituted with at least one identical or different radical chosen from hydroxyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkyl, or C 1 -C 4 alkoxy, and/or at least one of ring members of the heterocycloalkyl radical denoting a ketone (—CO—); or

R a and R b form, together with the nitrogen atom to which R a and R b are attached, an optionally substituted heterocycloalkyl.

19 . The method of claim 18 , wherein the at least one compound of formula (I) is of R configuration.

20 . The method of claim 18 , wherein in formula (I), R 1 is chosen from a (C 1 -C 6 )alkyl group or a hydrogen atom.

21 . The method of claim 18 , wherein in formula (I), R is an OR′ radical, in which R′ is chosen from:
A) a hydrogen atom or a (C 1 -C 4 )alkyl group;
B) a (C 1 -C 6 ) alkyl group optionally substituted with at least one identical or different radical chosen from:
hydroxyl;
heterocycloalkyl substituted with at least one identical or different radical chosen from hydroxyl, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, or C 1 -C 4 alkoxy, and/or one of the ring members of the heterocycloalkyl is a ketone (—CO—); or
phenyl, optionally substituted with at least one identical or different radical chosen from C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or hydroxyl;

C) a (C 1 -C 14 )alkyl group, the (C 1 -C 14 ) alkyl group being interrupted with at least one heteroatom;
D) a radical of formula (B′1):

wherein R h and R k are independently chosen from a hydrogen atom or a methyl radical; R l is H or OH; and y denotes an integer from 1 to 10; or

E) a (C 1 -C 6 ) alkenyl group, optionally substituted with at least one identical or different radical chosen from:
hydroxyl;
heterocycloalkyl substituted with at least one identical or different radical chosen from hydroxyl, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, or C 1 -C 4 alkoxy; and/or one of the ring members of the heterocycloalkyl is a ketone (—CO—); or
phenyl, optionally substituted with at least one identical or different radical chosen from C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or hydroxyl.

22 . The method of claim 18 , wherein in formula (I), R is an NR a R b radical, wherein:
A) R a and R b are independently chosen from a hydrogen atom or a (C 1 -C 18 )alkyl group; B) R a is a hydrogen atom and R b is chosen from a (C 1 -C 4 )alkyl group, the (C 1 -C 4 )alkyl group being optionally substituted with at least one identical or different radical chosen from:
hydroxyl,
carboxy,
(C 1 -C 6 )alkyloxycarbonyl, or
phenyl, optionally substituted with at least one identical or different radical chosen from C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or hydroxyl; or
C) R a is a hydrogen atom and R b represents a radical of the following formula B′2:

wherein:
i=0 or 1;
R 4 is chosen from a hydrogen atom or a (C 1 -C 6 )alkyl group optionally substituted with at least one group chosen from:
i) —Z—C(Z′)—Z″—R C , wherein Z, Z′, and Z″, which are identical or different, represent an oxygen atom, a sulfur atom, or N(R D ), wherein R C and R D , which are identical or different, are chosen from a hydrogen atom or a (C 1 -C 4 )alkyl group;
ii) (hetero)aryl, optionally substituted with a hydroxyl group;
iii) (di)(C 1 -C 4 )(alkyl)amino; iv) —C(Z′)—Z″—R C , wherein Z′, Z″ and R C are defined as above; or v) —Z′″—R C , wherein Z′″ is chosen from an oxygen, a sulfur atom, a selenium atom, or an NH group, and R C is as defined previously;

or, when i=0, R a and R 4 form, together with the nitrogen atom which bears R a and with the carbon atom which bears R 4 , a saturated 5- or 6-membered heterocycle;
R 6 is chosen from:
i) a hydroxyl radical —OH;
ii) a saturated or unsaturated (C 1 -C 6 )alkoxy radical; or
iii) an —NRfRg radical, wherein Rf and Rg, which are identical or different, are chosen from a hydrogen atom or a (C 1 -C 6 )alkyl group;

D) R a is a hydrogen atom and R b represents a radical of formula (B′2) as defined above, wherein in formula (B′2), R 6 is a hydroxyl radical or a saturated or unsaturated (C 1 -C 6 )alkoxy radical, and R 4 is a hydrogen atom or is chosen from radicals (a1) to (a32):

or, when i=0, R a and R 4 form, together with the nitrogen atom which bears R a and with the carbon atom which bears R 4 , a saturated 5- or 6-membered heterocycle of formula A1, A2, or A3:

Assignees

• Oreal

Inventors

• Marat Xavier
• Prevot-Gueguiniat Amélie

Classifications

• A61K8/49

  containing heterocyclic compounds · CPC title

• A61Q5/08

  Preparations for bleaching the hair · CPC title

• C07D417/12

  linked by a chain containing hetero atoms as chain links · CPC title

• A61Q19/02

  for chemically bleaching or whitening the skin · CPC title

• A61K8/602

  Glycosides, e.g. rutin · CPC title