Cosmetic use of substituted amino heterocylic carbamoyl analogs and related compounds
View Patent ↗Cosmetic compositions comprising substituted amino heterocyclic carbamoyl analogs and methods of using such compositions to impart anti-aging benefits to the skin are disclosed. The substituted amino heterocyclic carbamoyl analogs 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, a composition comprising a cosmetically acceptable vehicle and an effective amount of a collagen-stimulating compound having the structure:
where:
X is selected from O, S, or NR N ; and
R 2 is selected from the group consisting of hydrogen and C 1-6 alkyl;
R 4 is selected from hydrogen, C 1-6 alkyl, or a group:
wherein R 5 -R 9 are independently selected from the group consisting of hydrogen; F, Cl, Br, I; —OH; —NH 2 ; —NR N R N ; —SH; —CN; oxo; —CHO; —CO 2 H; —O—(C═O)—H; —O—(C═O)—C 1-10 alkyl; —O—(C═O)—Ar; —(C═O)—O—C 1-10 alkyl; —(C═O)—O—Ar; —(C═O)—NR N R N ; —O—C 1-10 alkyl; —O—Ar; —S—C 1-10 alkyl; —S—Ar; —Ar; —C 1-10 alkyl; —NR N —CHO; —NR N —(C═O)—C 1-10 alkyl; —C 1-10 alkyl-O—C 1-10 alkyl; perfluoroalkyl; epoxy; azido; thiocyanate; —SO 2 —R N ; nitro; and C 1-6 alkyl, alkenyl, alkynyl, and aryl, wherein each of said C 1-6 alkyl, alkenyl, alkynyl, and aryl could be optionally further substituted with one or more groups R a ;
wherein R a is independently, at each occurrence, selected from hydrogen, halogen (F, Cl, Br, or I); —OH; —NH 2 ; —NR N R N ; —SH; —CN; oxo; —CHO; —CO 2 H; —O—(C═O)—H; —O—(C═O)—C 1-10 alkyl; —O—(C═O)—Ar; —(C═O)—O—C 1-10 alkyl; —(C═O)—O—Ar; —(C═O)—NR N R N ; —O—C 1-10 alkyl; —O—Ar; —S—C 1-10 alkyl; —S—Ar; —Ar; —C 1-10 alkyl; —NR N —CHO; —NR N —(C═O)—C 1-10 alkyl; —C 1-10 alkyl-O—C 1-10 alkyl; perfluoroalkyl; epoxy; azido; thiocyanate; —SO 2 —R N ; or nitro;
wherein R N is independently selected, at each occurrence, from hydrogen or a C 1-16 hydrocarbon radical, optionally substituted with halogen (F, Cl, Br, or I); —OH; —NH 2 ; —NR*R*; —SH; —CN; oxo; —CHO; —CO 2 H; —O—(C═O)—H; —O—(C═O)—C 1-10 alkyl; —O—(C═O)—Ar; —(C═O)—O—C 1-10 alkyl; —(C═O)—O—Ar; —(C═O)—NR*R*; —O—C 1-10 alkyl; —O—Ar; —S—C 1-10 alkyl; —S—Ar; —Ar; —C 1-10 alkyl; —NR*—CHO; —NR*—(C═O)—C 1-10 alkyl; —C 1-10 alkyl-O—C 1-10 alkyl; perfluoroalkyl; epoxy; azido; thiocyanate; —SO 2 —R*; or nitro; wherein R* is independently hydrogen or a C 1-16 hydrocarbon radical;
where any two adjacent groups R N may together form a 5 or 6 membered ring;
“m” is independently selected, at each occurrence, from an integer from 1 to 6, and “n” is independently selected, at each occurrence, from an integer from 0 to 4;
or a cosmetically acceptable salt thereof;
and wherein said compound comprises from about 0.00001% to about 0.5% by weight of the composition.
2. The method according to claim 1 , wherein R 4 is:
where,
X is selected from O or S; and R 2 is H
or a cosmetically acceptable salt thereof.
3. The method according to claim 2 , wherein said compound has the structure:
or a cosmetically acceptable salt thereof.
4. The method according to claim 3 , wherein said compound has the structure:
or a cosmetically acceptable salt thereof.
5. The method according to claim 3 , wherein said compound has the structure:
or a cosmetically acceptable salt thereof.
6. The method according to claim 1 , wherein said aesthetic improvement of said skin is selected from the group consisting of:
(a) treatment, reduction, and/or prevention of fine lines or wrinkles;
(b) reduction of skin pore size;
(c) improvement in skin thickness, plumpness, and/or tautness;
(d) improvement in skin smoothness, 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) decreased by aging and/or menopause;
(n) improvement in skin moisturization;
(o) increase in skin elasticity and/or resiliency;
(p) treatment, reduction, and/or prevention of skin sagging;
(q) improvement in skin firmness;
(r) reduction of pigment spots and/or mottled skin;
(s) improving the appearance of acne scars or marks;
(t) improving the appearance of stretch marks; and/or
(u) improvement in the appearance of cellulite.
7. The method according to claim 6 , wherein said aesthetic improvement of said skin is the treatment, reduction, and/or prevention of: fine lines and/or wrinkles, skin sagging, or loss of elasticity.
8. The method according to claim 7 , wherein said aesthetic improvement of said skin is the treatment of wrinkles and/or fine lines on the skin, and wherein said method comprises topically applying an effective amount of a collagen-stimulating compound of formula I or a cosmetically acceptable salt thereof in a cosmetically acceptable vehicle to affected skin of an individual in need thereof, for a time sufficient to reduce the severity of said wrinkles or fine lines.
9. The method according to claim 8 , wherein said collagen-stimulating compound of formula I or a cosmetically acceptable salt thereof is applied to said skin at least once daily for a period of at least four weeks.