US 2003/0113284 A1Published application

Use of DHEA derivatives on keratinous substances

AssigneeL'oreal

InventorsMaria Dalko, Alexandre Cavezza

Life of this patent

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Abstract

Methods of improving the appearance of keratinous substances using at least one DHEA derivative such as the skin, hair, eyelashes and/or nails, in particular for preventing or treating cutaneous signs of ageing and/or a faded complexion and/or disorders of pigmentation of the skin or hair and/or drying of the skin and/or hyperseborrhoea and/or imperfections relating to hyperseborrhoea and/or sensitive skin and/or dandruff and/or hair loss and/or canities.

Claims31

Dependent claims

A method for improving the appearance of a keratinous substance comprising applying to said keratinous substance at least one DHEA derivative of the following formula (I):

6
in which:
R1 is selected from the group consisting of
(a) a hydrogen atom;
(b) a saturated or unsaturated, linear or branched, or cyclic, which can optionally comprise one or more heteroatoms, alkyl group which is optionally substituted by one or more groups selected from the grop consisting of —OR′, —SR′, —COOR′, —NR′R′, halogen, perfluoroalkyl, sulphate, phosphate, aryl, heterocycle, and mixtures thereof;
(c) an alkylcarbonyl group, the alkyl part of which is saturated or unsaturated, linear, branched or cyclic, and optionally substituted by one or more groups selected from the group consisting of —OR′, —SR′, —COOR′, —NR′R′, halogen, perfluoroalkyl, sulphate, or phosphate, aryl, heterocycle, and mixtures thereof;
(d) a phenyl group, optionally substituted by one or more groups selected from the group consisting of —OR′, —SR′, —COOR′, —NR′R′, halogen, perfluoroalkyl, sulphate, phosphate, aryl, heterocycle groups, and mixtures thereof;
(e) a benzyl group, optionally substituted by —OR′, —SR′, —COOR′, —NR′R′, halogen, perfluoroalkyl, sulphate, phosphate, aryl, heterocycle groups, and mixtures thereof;
(f) an arylcarbonyl group or an arylalkylcarbonyl group optionally substituted by one or more groups selected from the group consisting of —OR′, —SR′, —COOR′, —NR′R′, halogen, perfluoroalkyl, sulphate, phosphate, aryl, heterocycle groups, and mixtures thereof;
(g) an O═P(OH)OR′ group;
(h) an (O)2SOR′ group;
(i) an (O)2SR′ group;
(j) a trialkylsilyl group (SiR13) in which the R′ groups may be identical or different;
(k) an alkyloxycarbonyl group (R′OCO);
(l) an alkylaminocarbonyl group (R′NR′′′CO);
and
(m) a carbohydrate comprising 3 to 100 carbon atoms;
R4 and R5:
(a) together represent a group selected from the group consisting of
(1) a keto group (═O);
(2) a=CHR′ group;
(3) an=NR′ group;
and
(4) a=NCOR′ group;
(b) each represent an identical —OR″ group;
(c) each represent an identical or different group selected from the group consisting of
(1) a hydrogen atom;
(2) an —NR′R′ group;
and
(3) an —NHCOR′ group;
R2 and R3 are:
(a) when R3 is a hydrogen atom, R2 is selected from the group consisting of
(1) an —OR6 group in which R6 has the same definitions as those given above for R1;
(2) an amine group —N(R7)2 in which the R7 substituents, which are identical or different, have the same definitions as those given above for R1;
(3) an N-sulphonamide group (—NR′′′SO2R′) or an N-sulphonate group (—NR′′′SO3R′);
(4) a urea group (—NR′′′CONR′R′);
(5) an alkylamide group (—NR′′′COR′);
(6) an N-carbamate group (—NR′′′COOR′);
(7) a thiol group (—SR′);
(8) a thiophenyl group (—SPh);
(9) a sulphone group (—SO2R′);
(10) a sulphoxide group (—SOR′);
(11) a halogen;
and
(12) an alkylsilane group (—SiR′3) in which the R′ groups may be identical or different;
(b) R2 and R3 together represent a group selected from the group consisting of
(1) a methylene (═CHR′);
(2) an imine (═NHR′);
(3) an oxime (═NOR′);
(4) a hydrazone (═N—NR′R′);
and
(5) a keto group (═O);
(c) R2 and R3 each represent an —OR″ group in which each of the R″ groups represents an alkyl group;
R′ is selected from the group consisting of a hydrogen atom and a saturated or unsaturated, linear or branched, or cyclic, which can optionally comprise one or more heteroatoms, alkyl group optionally substituted by one or more —OR′′′, —COOR′′′, halogen, and —NR′′′R′′′ groups;
or an aryl group, optionally substituted by one or more —OR′′′, —COOR′′′, halogen, and —NR′′′R′′′ groups;
R′′′ represents a hydrogen atom or a saturated or unsaturated and linear, branched or cyclic alkyl chain;
wherein in each of the —NR′R′ and —NR′′′R′′′ groups, the R′ and R′′′ substituents are identical or different;
with the exception of the DHEA derivatives of formula (I) for which:
(a) R2 and R3 together represent a keto group;
(b) R4 and R5 together represent a keto group;
and
(c) R1 is as defined above;
with the exception of the DHEA derivatives of formula (A)
7
in which:
R1 is selected from the group consisting of a hydrogen atom, an ester of organic acid comprising 1 to 24 carbon atoms, a sulphuric ester, a phosphoric ester, a carbonaceous ether comprising 1 to 24 carbon atoms optionally comprising nitrogen atoms, and ethers of carbohydrates comprising 3 to 100 carbon atoms and their derivatives optionally comprising nitrogen atoms;
R2 is selected from the group consisting of a hydrogen atom and an ester group of fatty acid comprising 1 to 24 carbon atoms;
R3 is selected from the group consisting of a hydrogen atom, an —OH group, —CO—R4, —CHOH—R4, ═CH—CH3, ═COH—CH3, —CHR4—CH3, and ═O, in which R4 is an alkyl group comprising from 1 to 10 carbon atoms which is optionally substituted.

65 more elements

Dependencies are inferred from the claim text.

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Abstract

A method for improving the appearance of a keratinous substance comprising applying to said keratinous substance at least one DHEA derivative of the following formula (I):

6
in which:
R1 is selected from the group consisting of
(a) a hydrogen atom;
(b) a saturated or unsaturated, linear or branched, or cyclic, which can optionally comprise one or more heteroatoms, alkyl group which is optionally substituted by one or more groups selected from the grop consisting of —OR′, —SR′, —COOR′, —NR′R′, halogen, perfluoroalkyl, sulphate, phosphate, aryl, heterocycle, and mixtures thereof;
(c) an alkylcarbonyl group, the alkyl part of which is saturated or unsaturated, linear, branched or cyclic, and optionally substituted by one or more groups selected from the group consisting of —OR′, —SR′, —COOR′, —NR′R′, halogen, perfluoroalkyl, sulphate, or phosphate, aryl, heterocycle, and mixtures thereof;
(d) a phenyl group, optionally substituted by one or more groups selected from the group consisting of —OR′, —SR′, —COOR′, —NR′R′, halogen, perfluoroalkyl, sulphate, phosphate, aryl, heterocycle groups, and mixtures thereof;
(e) a benzyl group, optionally substituted by —OR′, —SR′, —COOR′, —NR′R′, halogen, perfluoroalkyl, sulphate, phosphate, aryl, heterocycle groups, and mixtures thereof;
(f) an arylcarbonyl group or an arylalkylcarbonyl group optionally substituted by one or more groups selected from the group consisting of —OR′, —SR′, —COOR′, —NR′R′, halogen, perfluoroalkyl, sulphate, phosphate, aryl, heterocycle groups, and mixtures thereof;
(g) an O═P(OH)OR′ group;
(h) an (O)2SOR′ group;
(i) an (O)2SR′ group;
(j) a trialkylsilyl group (SiR13) in which the R′ groups may be identical or different;
(k) an alkyloxycarbonyl group (R′OCO);
(l) an alkylaminocarbonyl group (R′NR′′′CO);
and
(m) a carbohydrate comprising 3 to 100 carbon atoms;
R4 and R5:
(a) together represent a group selected from the group consisting of
(1) a keto group (═O);
(2) a=CHR′ group;
(3) an=NR′ group;
and
(4) a=NCOR′ group;
(b) each represent an identical —OR″ group;
(c) each represent an identical or different group selected from the group consisting of
(1) a hydrogen atom;
(2) an —NR′R′ group;
and
(3) an —NHCOR′ group;
R2 and R3 are:
(a) when R3 is a hydrogen atom, R2 is selected from the group consisting of
(1) an —OR6 group in which R6 has the same definitions as those given above for R1;
(2) an amine group —N(R7)2 in which the R7 substituents, which are identical or different, have the same definitions as those given above for R1;
(3) an N-sulphonamide group (—NR′′′SO2R′) or an N-sulphonate group (—NR′′′SO3R′);
(4) a urea group (—NR′′′CONR′R′);
(5) an alkylamide group (—NR′′′COR′);
(6) an N-carbamate group (—NR′′′COOR′);
(7) a thiol group (—SR′);
(8) a thiophenyl group (—SPh);
(9) a sulphone group (—SO2R′);
(10) a sulphoxide group (—SOR′);
(11) a halogen;
and
(12) an alkylsilane group (—SiR′3) in which the R′ groups may be identical or different;
(b) R2 and R3 together represent a group selected from the group consisting of
(1) a methylene (═CHR′);
(2) an imine (═NHR′);
(3) an oxime (═NOR′);
(4) a hydrazone (═N—NR′R′);
and
(5) a keto group (═O);
(c) R2 and R3 each represent an —OR″ group in which each of the R″ groups represents an alkyl group;
R′ is selected from the group consisting of a hydrogen atom and a saturated or unsaturated, linear or branched, or cyclic, which can optionally comprise one or more heteroatoms, alkyl group optionally substituted by one or more —OR′′′, —COOR′′′, halogen, and —NR′′′R′′′ groups;
or an aryl group, optionally substituted by one or more —OR′′′, —COOR′′′, halogen, and —NR′′′R′′′ groups;
R′′′ represents a hydrogen atom or a saturated or unsaturated and linear, branched or cyclic alkyl chain;
wherein in each of the —NR′R′ and —NR′′′R′′′ groups, the R′ and R′′′ substituents are identical or different;
with the exception of the DHEA derivatives of formula (I) for which:
(a) R2 and R3 together represent a keto group;
(b) R4 and R5 together represent a keto group;
and
(c) R1 is as defined above;
with the exception of the DHEA derivatives of formula (A)
7
in which:
R1 is selected from the group consisting of a hydrogen atom, an ester of organic acid comprising 1 to 24 carbon atoms, a sulphuric ester, a phosphoric ester, a carbonaceous ether comprising 1 to 24 carbon atoms optionally comprising nitrogen atoms, and ethers of carbohydrates comprising 3 to 100 carbon atoms and their derivatives optionally comprising nitrogen atoms;
R2 is selected from the group consisting of a hydrogen atom and an ester group of fatty acid comprising 1 to 24 carbon atoms;
R3 is selected from the group consisting of a hydrogen atom, an —OH group, —CO—R4, —CHOH—R4, ═CH—CH3, ═COH—CH3, —CHR4—CH3, and ═O, in which R4 is an alkyl group comprising from 1 to 10 carbon atoms which is optionally substituted.

65 more elements