Cosmetic use of N-substituted sulfonyloxybenzylamines and related compounds
View Patent ↗Cosmetic compositions comprising N-substituted sulfonyloxybenzylamines and methods of using such compositions to impart anti-aging benefits to the skin are disclosed. The N-substituted sulfonyloxybenzylamines are believed to have modulatory activity against one or more biochemical pathways implicated in skin aging.
1. A method for improving the aesthetic appearance of human skin comprising topically applying to an area of the skin in need thereof an effective amount of an N-substituted sulfonyloxybenzylamine or a cosmetically acceptable salt thereof in a cosmetically acceptable vehicle.
2. The method according to claim 1 wherein said N-substituted sulfonyloxybenzylamine has the structure of formula I:
where:
W 1 and W 2 are independently CO, CO 2 , CONH, SO 2 or PO 3 ;
R 1 , R 2 and R 3 are independently C 1-20 hydrocarbons, each independently selected from alkyl, cycloalkyl, haloalkyl, alkoxyalkyl, heteroalkyl, heteroaryl, aryl, arylalkyl, alkylaryl, heteroaryl, heteroarylalkyl, and alkylheteroaryl, each being optionally substituted with C and/or 1-6 heteroatoms, including halogen, O, N and S;
X, Y each independently represent H or an optionally substituted alkyl, haloalkyl, alkoxy, amino, aminoalkyl, haloalkoxy, alkenyl, and where adjacent X, Y taken together can form a 5, 6, or 7 member ring;
and wherein the —O—W 2 —R 1 group is attached to the phenyl ring at the 3- or 4-position.
3. The method according to claim 2 , where R 1 is a C 1-4 alkyl group.
4. The method according to claim 3 , where R 1 is —CH 3 or —CH 2 CH 3 .
5. The method according to claim 2 , where R 2 is selected from the group consisting of i-butyl, sec-butyl, methoxyethyl and CH 2 -2-furanyl.
6. The method according to claim 5 , where R 2 is a group i-butyl.
7. The method according to claim 2 , where W 1 and W 2 are independently selected from the group consisting of CO, CONH, and SO 2 .
8. The method according to claim 7 , where W 1 is a group —SO 2 or a group —CONH, and W 2 is a group —SO 2 .
9. The method according to claim 2 , where R 3 is alkyl, cycloalkyl or aryl.
10. The method according to claim 9 , where R 3 is phenyl.
11. The method according to claim 1 , wherein said aesthetic improvement of said human skin is selected from the group consisting of:
(a) treatment and/or reduction of fine lines or wrinkles,
(b) reduction of skin pore size,
(c) improvement in skin thickness, plumpness, and/or tautness;
(d) improvement in skin suppleness and/or softness;
(e) improvement in skin tone, radiance, and/or clarity;
(f) improvement in procollagen and/or collagen production;
(g) improvement in maintenance and remodeling of elastin;
(h) improvement in skin texture and/or promotion of retexturization;
(i) improvement in skin barrier repair and/or function;
(j) improvement in appearance of skin contours;
(k) restoration of skin luster and/or brightness;
(l) replenishment of essential nutrients and/or constituents in the skin;
(m) improvement of skin appearance decreased by menopause;
(n) improvement in skin moisturization;
(o) increase in skin elasticity and/or resiliency;
(p) treatment and/or reduction of skin sagging; and
(q) reduction of pigment spots.
12. The method according to claim 11 , wherein said aesthetic improvement of said skin is the treatment and/or reduction of: fine lines and/or wrinkles, skin sagging, loss of elasticity and mottled skin appearance.
13. The method according to claim 2 , wherein said N-substituted sulfonyloxybenzylamine has the structure:
or a cosmetically acceptable salt thereof,
where:
X and Y are H;
R 1 is a C 1-8 alkyl group, a phenyl group or benzyl group, each being optionally substituted with C and/or 1-6 heteroatoms, including halogen, O, N and S;
R 2 is alkyl, aryl, alkylaryl or heteroaryl, each being optionally substituted with C and/or 1-6 heteroatoms, including halogen, O, N and S; and
R 3 is alkyl or aryl, each being optionally substituted with C and/or 1-6 heteroatoms, including halogen, O, N and S.
14. The method according to claim 2 , wherein said N-substituted sulfonyloxybenzylamine has the structure:
or a cosmetically acceptable salt thereof,
where
X and Y are H;
R 1 is a C 1-8 alkyl group, a phenyl group or benzyl group, each being optionally substituted with C and/or 1-6 heteroatoms, including halogen, O, N and S;
R 2 is alkyl, aryl, alkylaryl or heteroaryl each being optionally substituted with C and/or 1-6 heteroatoms, including halogen, O, N and S; and
R 3 is alkyl or aryl each being optionally substituted with C and/or 1-6 heteroatoms, including halogen, O, N and S; and
wherein said —O—SO 2 —R 1 group is attached to the phenyl ring at the 3- or 4-position.
15. The method according to claim 2 , wherein said N-substituted sulfonyloxybenzylamine has the structure:
where:
X and Y are H;
R 1 is a C 1-8 alkyl group, a phenyl group or benzyl group, each being optionally substituted with C and/or 1-6 heteroatoms, including halogen, O, N and S;
R 2 is alkyl, aryl, alkylaryl or heteroaryl, each being optionally substituted with C and/or 1-6 heteroatoms, including halogen, O, N and S; and
R 3 is alkyl or aryl, each being optionally substituted with C and/or 1-6 heteroatoms, including halogen, O, N and S.
16. A method for treating wrinkles and/or fine lines comprising topically applying to said wrinkle and/or fine line on the skin of an individual in need thereof an effective amount of a N-substituted sulfonyloxybenzylamine or a cosmetically acceptable salt thereof in a cosmetically acceptable vehicle for a time sufficient to reduce the severity of said wrinkles or fine lines.
17. The method according to claim 16 , wherein said N-substituted sulfonyloxybenzylamine or a cosmetically acceptable salt thereof is applied to said skin at least once daily for a period of at least four weeks.
18. The method according to claim 15 , wherein said N-substituted sulfonyloxybenzylamine has the structure:
or a cosmetically acceptable salt thereof.
19. The method according to claim 16 wherein said N-substituted sulfonyloxybenzylamine has the structure of formula I:
where:
W 1 and W 2 are independently CO, CO 2 , CONH, SO 2 or PO 3 ;
R 1 , R 2 and R 3 are independently C 1-20 hydrocarbons, each independently selected from alkyl, cycloalkyl, haloalkyl, alkoxyalkyl, heteroalkyl, heteroaryl, aryl, arylalkyl, alkylaryl, heteroaryl, heteroarylalkyl, and alkylheteroaryl, each being optionally substituted with C and/or 1-6 heteroatoms, including halogen, O, N and S;
X, Y each independently represent H or an optionally substituted alkyl, haloalkyl, alkoxy, amino, aminoalkyl, haloalkoxy, alkenyl, and where adjacent X, Y taken together can form a 5, 6, or 7 member ring;
and wherein the —O—W 2 —R 1 group is attached to the phenyl ring at the 3- or 4-position.