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US 6,884,425 B2Granted
Cosmetic or dermatological composition comprising an association between a compound of the N-acylaminoamide family and at least one matrix metalloproteinase inhibitor
AssigneeL'oreal
InventorsLionel Breton, Yann Mahe
Life of this patent
Estimating the term…
Abstract
A cosmetic or dermatological composition characterized in that it comprises an association between an elastase inhibitor compound of the N-acylaminoamide family and at least one metalloproteinase inhibiting compound.
Claims20
A composition comprising an N-acylaminoamide elastase inhibitor and at least one metalloproteinase inhibitor, wherein the elastase inhibitor is a compound of the formula (I):
- where
- the Y radical represents O or S,
- the R1 radical represents
- (i) a hydrogen atom,
- (ii) a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical having 1 to 18 carbon atoms,
- optionally substituted by 1 to 5 groups, either identical or different, selected from the group consisting of —OH;
- —OR;
- —O—COR;
- —SH;
- —SR;
- —S—COR;
- —NH2;
- —NHR;
- —NRR′;
- —NH—COR;
- halogen;
- —CN;
- COOR;
- —COR;
- —P(O)—(OR)2;
- —SO2—OR;
- with R and R′ representing, independently from each other, a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical having 1 to 6 carbon atoms, optionally being halogenated;
- said R and R′ radicals being able to form together with N a carbon ring with 5 to 6 ring members optionally further comprising at least one heteroatom being selected from the group consisting of O, N and S in the ring and/or optionally substituted by 1 to 5 groups, identical or different, selected from the group consisting of —OH;
- —OR″;
- —O—COR″;
- —SH;
- —SR″;
- —S—COR″;
- —NH2;
- —NHR″;
- —NH—COR″;
- halogen;
- —CN;
- —COOR″;
- and —COR″;
- with R″ representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical, having 1 to 6 carbon atoms, optionally being halogenated;
- (iii) a radical selected from the group consisting of —OR;
- —NH2;
- —NHR;
- —NRR′;
- —NH—COR;
- —COOR;
- —COR;
- with R and R′ representing, independently from each other, a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical having 1 to 6 carbon atoms, optionally being halogenated;
- said R and R′ radicals being able to form together with N a carbon ring with 5 to 6 ring members optionally comprising, additionally, at least one heteroatom selected from the group consisting of O, N and S in the ring and/or optionally substituted by 1 to 5 groups, identical or different, selected from the group consisting of —OH;
- —OR″;
- —O—COR″;
- —SH;
- —SR″;
- —S—COR″;
- —NH2;
- —NHR″;
- —NH—COR″;
- halogen;
- —CN;
- —COOR″;
- and —COR″;
- with R″ representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical having 1 to 6 carbon atoms, optionally being halogenated;
- the R2 radical represents a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical, with 1 to 18 carbon atoms, optionally substituted by 1 to 5 groups, either identical or different, selected from the group consisting of —OH;
- —OR;
- —O—COR;
- —SH;
- —SR;
- —S—COR;
- —NH2;
- —NHR;
- —NRR′;
- —NH—COR;
- halogen;
- —CN;
- —COOR;
- and —COR;
- with R and R′ representing, independently from each other, a hydrocarbon, linear, branched or cyclic, saturated or unsaturated radical, with 1 to 6 carbon atoms, optionally halogenated;
- said R and R′ radicals able to form together with N a carbon cycle with 5 to 6 chains optionally comprising, additionally, at least one heteroatom selected from the group consisting of O, N and S in the ring and/or optionally substituted by 1 to 5 groups, identical or different, selected from the group consisting of —OH;
- —OR″;
- —O—COR″;
- —SH;
- —SR″;
- —S—COR″;
- —NH2;
- —NHR″;
- —NH—COR″;
- halogen;
- —CN;
- —COOR″;
- and —COR″;
- with R″ representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical, with 1 to 6 carbon atoms, optionally halogenated
- the R3 radical represents a radical selected from formulae (II) or (III)
- -A-C6H(5-y)—By (II)
- —C6H(5-y′)—By′ (III)
- where
- y is an integer between 0 and 5 inclusive, and y′ is an integer between 1 and 5 inclusive;
- A is a linear or branched, saturated or unsaturated hydrocarbon divalent radical, with 1 to 18 carbon atoms, optionally being substituted by 1 to 5 groups, either identical or different, selected from the group consisting of —OH;
- —OR;
- —O—COR;
- —SH;
- —SR;
- —S—COR;
- —NH2;
- —NHR;
- —NRR′;
- —NH—COR;
- halogen;
- —CN;
- —COOR;
- —COR;
- —NO2;
- and —SO2OR;
- with R and R′ representing, independently from each other, a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical, with 1 to 6 carbon atoms, optionally being halogenated;
- said R and R′ radicals being able to form together with N a carbon ring with 5 to 6 ring members optionally comprising further at least one heteroatom selected from the group consisting of O, N and S in the ring and/or optionally substituted by 1 to 5 groups, identical or different, selected from the group consisting of —OH;
- —OR″;
- —O—COR″;
- —SH;
- —SR″;
- —S—COR″;
- —NH2;
- —NHR″;
- —NH—COR″;
- halogen;
- —CN;
- —COOR″;
- and —COR″;
- with R″ representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical having 1 to 6 carbon atoms, optionally being halogenated;
- B is a linear or branched, saturated or unsaturated hydrocarbon radical having 1 to 18 carbon atoms, optionally substituted by 1 to 5 groups, either identical or different, selected from the group consisting of —OH;
- —OR;
- —O—COR;
- —SH;
- —SR;
- —S—COR;
- —NH2;
- —NHR;
- —NRR′;
- —NH—COR;
- halogen;
- —CN;
- —COOR;
- —COR;
- —NO2;
- and —SO2OR;
- with R and R′ representing, independently from each other, a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical having 1 to 6 carbon atoms, optionally being halogenated;
- said R and R′ radicals being able to form together with N a carbon ring with 5 to 6 ring members optionally comprising further at least one heteroatom selected from the group consisting of O, N and S in the ring and/or optionally substituted by 1 to 5 groups, identical or different, selected from the group consisting of —OH;
- —OR″;
- —O—COR″;
- —SH;
- —SR″;
- —S—COR″;
- —NH2;
- —NHR″;
- —NH—COR″;
- halogen;
- —CN;
- —COOR″;
- and —COR″;
- with R″ representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon having 1 to 6 carbon atoms, optionally being halogenated;
- the X radical is a radical selected from the group consisting of —OH;
- —OR4;
- —NH2;
- —NHR4;
- —NR4R5;
- —SR4;
- —COOR4;
- and —COR4;
- with R4 and R5 representing, independently from each other, a linear, cyclic or branched, saturated or unsaturated hydrocarbon radical having 1 to 6 carbon atoms, optionally substituted by 1 to 5 groups, identical or different, selected from the group consisting of —OH;
- —OR;
- —O—COR;
- —SH;
- —SR;
- —S—COR;
- —NH2;
- —NHR;
- —NH—COR;
- halogen;
- —CN;
- —COOR;
- —COR;
- with R and R′ representing, independently from each other, a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical having 1 to 6 carbon atoms, optionally being halogenated;
- said R and R′ radicals being able to form together with N a carbon ring with 5 to 6 ring members optionally comprising further at least one heteroatom selected from the group consisting of O, N and S in the ring and/or optionally substituted by 1 to 5 groups, identical or different, selected from the group consisting of —OH;
- —OR″;
- —O—COR″;
- —SH;
- —SR″;
- —S—COR″;
- —NH2;
- —NHR″;
- —NH—COR″;
- halogen;
- —CN;
- —COOR″;
- and —COR″;
- with R″ representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical having 1 to 6 carbon atoms, optionally being halogenated;
- said R4 and R5 radicals being able to form together with N a carbon ring with 5 to 6 ring members optionally comprising further at least one heteroatom selected from the group consisting of O, N and S in the ring and/or optionally substituted by 1 to 5 groups, identical or different, selected from the group consisting of —OH;
- —OR″;
- —O—COR″;
- —SH;
- —SR″;
- —S—COR″;
- —NH2;
- —NHR″;
- —NH—COR″;
- halogen;
- —CN;
- —COOR″;
- and —COR″;
- with R″ representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical having 1 to 6 carbon atoms, optionally being halogenated the mineral or organic acid salts thereof, the optical isomers thereof, in an isolated form or as a racemic mixture.
201 more elements
A composition comprising an N-acylaminoamide elastase inhibitor and at least one metalloproteinase inhibitor, wherein the N-acylaminoamide elastase inhibitor is a compound of the formula (I):
- where
- the Y radical represents oxygen,
- the R1 radical represents hydrogen or a linear or branched, saturated or unsaturated hydrocarbon radical having 1 to 12, optionally substituted,
- the R1 substituents being selected from the group consisting of —OH;
- —OR;
- and —P(O)—(OR)2 with R representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical having 1 to 6 carbon atoms, optionally being halogenated;
- the R2 radical represents a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical having 1 to 12 carbon atoms, optionally substituted,
- the R2 substituents being —OH or —OR with R representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical having 1 to 6 carbon atoms, optionally being halogenated;
- the R3 radical represents a radical of the formula —C6H(5-y′)—By′ where y′=1, 2 or 3;
- or a radical of the formula -A-C6H(5-y)-By where y=0, 1 or 2;
- the A radical of R3 is a linear or branched, saturated or unsaturated hydrocarbon divalent radical having 1 to 12 carbon atoms, optionally substituted;
- the B radical of R3 is a linear or branched, saturated or unsaturated hydrocarbon radical having 1 to 12 carbon atoms, optionally substituted;
- A and/or for B are selected from the group consisting of -halogen;
- —CN;
- —COOR;
- —NO2;
- and —SO2—OR;
- with R representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon radical having 1 to 6 carbon atoms, optionally being halogenated, and/or
- the X radical represents —OH or —OR4 with R4 representing a linear, cyclic or branched, saturated or unsaturated hydrocarbon radical having 1 to 6 carbon atoms, optionally substituted, and
- R4 of X is —OH or —OR with R representing a linear, cyclic or branched, saturated or unsaturated hydrocarbon radical having 1 to 6 carbon atoms, optionally being substituted.
17 more elements
A composition comprising an N-acylaminoamide elastase inhibitor and at least one metalloproteinase inhibitor, wherein the N-acylaminoamide elastase inhibitor is a compound of the formula (I):
- where
- the R1 radical represents a methyl, ethyl, propyl or isopropyl radical, optionally substituted by a —OH or —P(O)—(OR)2 group with R representing methyl, ethyl, propyl or isopropyl;
- the R2 radical represents a methyl, ethyl, propyl, isopropyl, n-butyl, ter-butyl or isobutyl radical;
- the R3 radical represents a group of one of the following formulae:
- where the divalent A radical is a methylene, ethylene, propylene and/or the B radical is a methyl, ethyl, propyl or isopropyl radical, substituted by one or more halogens, and
- the X radical represents a radical selected from the group consisting of —OH, —OCH3, —OC2H5, —O—C3H7 and —OC4H9.
3 more elements
Dependencies are inferred from the claim text.