Gamma-diketones for treatment and prevention of aging skin and wrinkles
The present disclosure relates to compounds, cosmetic or dermopharmaceutical compositions comprising the same, and methods for using the compounds or compositions for treating, protecting, and/or improving the condition and/or aesthetic appearance of skin, for example, treating, preventing, ameliorating, reducing and/or eliminating fine lines and/or wrinkles of skin, or improving the appearance of fine lines and/or or wrinkles of skin comprising application of the compounds or compositions disclosed. In some embodiments, the compounds useful in the methods described herein include compounds of Formula I: or a dermatologically acceptable salt thereof.
1. A method for improving the aesthetic appearance of a subject's skin, the method comprising administering to the subject an effective amount of a compound of Formula I, or a dermatologically acceptable salt thereof:
wherein:
Ring A is a 7-12 membered heteroaryl, with the proviso that a carbon atom on the ring is attached to the carbonyl carbon;
Ring B is phenyl;
R 1 is a substituent attached to Ring A and is independently selected at each occurrence from the group consisting of unsubstituted —C 1-6 alkyl, —C 1-3 haloalkyl, halide, —OR 3 , and CN;
R 2 is a substituent attached to Ring B and is independently selected at each occurrence from the group consisting of unsubstituted —C 1-6 alkyl, —CH 2 OH, —CH 2 N(R 3b ) 2 , —C 1-3 haloalkyl, halide, —OR 3 , and CN;
each R 3 is independently selected from the group consisting of H, unsubstituted —C 1-6 alkyl, and —C 1-3 haloalkyl;
each R 3b is independently selected from the group consisting of H and unsubstituted —C 1-3 alkyl;
each n is 0 to 10; and
each m is 0 to 5.
2. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
3. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
4. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
5. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
6. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
7. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
8. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
9. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
10. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
11. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
12. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
13. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
14. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
15. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
16. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
17. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
18. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
19. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
20. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
21. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
22. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
23. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
24. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
25. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
26. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
27. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
28. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
29. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
30. The method of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
or a dermatologically acceptable salt thereof.
31. A method for improving the aesthetic appearance of a subject's skin, the method comprising administering to skin an effective amount of a cosmetic or dermopharmaceutical composition comprising a compound according to Formula I, or a dermatologically acceptable salt thereof:
wherein:
Ring A is a 7-12 membered heteroaryl, with the proviso that a carbon atom on the ring is attached to the carbonyl carbon;
Ring B is phenyl;
R 1 is a substituent attached to Ring A and is independently selected at each occurrence from the group consisting of unsubstituted —C 1-6 alkyl, —C 1-3 haloalkyl, halide, —OR 3 , and CN;
R 2 is a substituent attached to Ring B and is independently selected at each occurrence from the group consisting of unsubstituted —C 1-6 alkyl, —CH 2 OH, —CH 2 N(R 3b ) 2 , —C 1-3 haloalkyl, halide, —OR 3 , and CN;
each R 3 is independently selected from the group consisting of H, unsubstituted —C 1-6 alkyl, and —C 1-3 haloalkyl;
each R 3b is independently selected from the group consisting of H and unsubstituted —C 1-3 alkyl;
each n is 0 to 10; and
each m is 0 to 5.
32. The method of claim 1 , wherein the improvement in aesthetic appearance is improvement in one or more of skin tone, radiance, clarity, tautness, skin firmness, plumpness, suppleness, softness, skin texture, skin texturization and moisturization, appearance of skin contours, appearance of hollow cheeks, appearance of sunken, baggy, or dark circles under eyes, skin luster, brightness, skin thickness, and skin elasticity and/or resiliency.
33. The method of claim 1 , wherein the improvement in aesthetic appearance is the reduction of fine lines or wrinkles.
34. The method of claim 1 , wherein the improvement in aesthetic appearance is the improvement in procollagen and/or collagen production.
35. The method of claim 1 , wherein the improvement in aesthetic appearance is the reduction of discoloration of skin.
36. The method of the claim 1 , wherein the compound is administered as a cosmetic or dermopharmaceutical composition.
37. The method according to claim 36 , wherein the cosmetic or dermopharmaceutical composition is a topical composition.
38. The method according to claim 36 , wherein the cosmetic composition is intended for use as a non-therapeutic treatment.