Compositions and methods for stimulating collagen synthesis in the skin
View Patent ↗Cosmetic compositions comprising substituted carbamoyl heterocyclic analogs and methods of using such compositions to impart anti-aging benefits to the skin are disclosed. The substituted carbamoyl heterocyclic analogs are believed to have modulatory activity against one or more biochemical pathways implicated in skin aging.
1. A method of stimulating collagen synthesis in human skin comprising topically applying to an area of the skin in need thereof, in a cosmetically acceptable vehicle, an effective amount of a collagen-stimulating compound having the formula I:
where:
R 1 is selected from the group consisting of H, or a C 1-6 alkyl, alkenyl, alkynyl, aryl, or heteroaryl group optionally substituted with one or more C 1-6 alkyl, alkenyl, alkynyl, aryl, or R a groups;
R 4 -R 8 are independently selected from the group consisting of R a , C 1-6 alkyl, alkenyl, alkynyl, and aryl, each of which could be optionally further substituted with one or more groups R a ;
wherein R a is independently, at each occurrence, selected from 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 ; or nitro;
wherein R N is independently selected, at each occurrence, from hydrogen or a C 1-16 hydrocarbon radical, optionally substituted with a group R a ; and where any two adjacent groups R N may together form a 5, 6, or 7 membered ring;
or a cosmetically acceptable salt thereof.
2. The method according to claim 1 wherein R 4 to R 8 are independently hydrogen, methyl, ethyl, propyl, chloro, or bromo, with at least two of R 4 to R 8 being hydrogen.
3. The method according to claim 1 , wherein R a is hydrogen, methyl, ethyl, propyl, and R 1 is hydrogen, methyl, ethyl, or propyl.
4. The method according to claim 1 , wherein R a is methyl, ethyl, propyl, and R 1 is hydrogen, methyl, ethyl, or propyl.
5. The method according to claim 1 , 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.
6. The method according to claim 1 , wherein the compound has the structure:
and wherein R b , R a , R 1 , and Q are as set forth below:
R b
R a
R 1
H
H
H