Granted Patent B2

US 9,044,408 · App. 13/285,458 · Granted Jun 2, 2015

Abstract

Claims (71)

1. A cosmetic composition for topical application to human skin comprising a cosmetically acceptable vehicle and a dermatologically effective amount of a N— heteroarylbisamide of Formula IA:

where:

R 2 , R 2′ , R 6 , and R 7 are independently H, C 1 -C 8 alkyl, heteroalkyl, alkoxyalkyl, heteroalkoxyalkyl, C 3 -C 8 cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkyl-aryl, heteroalkyl-aryl, aryl-alkyl, and/or heteroaryl-alkyl;

R 1 and R 5 are independently H, C 1 -C 8 alkyl, heteroalkyl, alkoxyalkyl, heteroalkoxyalkyl, C 3 -C 8 cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkyl-aryl, heteroalkyl-aryl, aryl-alkyl, and/or heteroaryl-alkyl or WR wherein W is CO, CO 2 , CONH, SO 2 , PO 3 , or CH(Oalkyl) 2 ; and

n is 1-4.

2. The cosmetic composition of claim 1 , wherein R 7 is H, halogen, or C 1 -C 4 alkyl or alkoxy.

3. The cosmetic composition of claim 2 , wherein R 7 is chlorine or methyl.

4. The cosmetic composition of claim 1 , wherein R 2 is C 1 -C 6 alkyl, or a C 6 aromatic hydrocarbon radical.

5. The cosmetic composition of claim 4 , wherein R 2 is methyl or tert-butyl.

6. The cosmetic composition of claim 1 , wherein R 2′ is H or phenyl.

7. The cosmetic composition of claim 1 , wherein R 6 is propyl, substituted propyl, or substituted phenyl.

8. The composition of claim 1 , wherein R 1 and R 5 are independently H, or lower alkyl.

9. The composition of claim 1 , wherein n is 3.

10. The cosmetic composition of claim 1 , wherein said N-heteroarylbisamide has the structure:

11. A method for improving the aesthetic appearance of human skin comprising topically applying to an area of the skin in need thereof an amount of the cosmetic composition of claim 1 to enhance the skin.

12. The method according to claim 11 , wherein the skin enhancement is an increase in the production of procollagen or collagen, and the aesthetic improvement is selected from the group consisting of:

(a) treatment and/or reduction of the appearance of fine lines or wrinkles,

(b) improvement of the skin's thickness, plumpness, and/or tautness;

(c) improvement in skin barrier repair and/or function;

(d) improvement in appearance of skin contours;

(e) increase in skin elasticity and/or resiliency;

(f) treatment and/or reduction of skin sagging;

(g) smooth scars and stretch marks; and/or

(h) reduction in pore size.

13. The method according to claim 11 , wherein the skin enhancement is an increase in the production of hyaluronic acid and the aesthetic improvement is selected from the group consisting of:

(a) improvement in the skin's suppleness, softness, tone, radiance, and/or clarity;

(b) improvement in skin texture and/or promotion of retexturization;

(c) restoration of skin luster and/or brightness;

(d) replenishment of essential nutrients and/or constituents in the skin; and/or

(e) improvement of skin moisturization and/or complexion.

14. The method according to claim 11 , wherein the skin enhancement is the modulation of fibroblasts and the aesthetic improvement is selected from the group consisting of:

(a) increase in the production of structural proteins and glucosaminoglycans;

(b) improvement in the structure of collagen;

(c) homoeostasis of structural protein and glucosaminoglycans;

(d) down-regulation of cytokine production;

(e) increased activation of fibroblasts to fibrocytes;

(f) increase in the viability and/or function of fibroblasts;

(g) improvement in maintenance and remodeling of elastin; and/or

(h) improvement in skin barrier repair and/or function.

15. The method according to claim 11 , wherein the skin enhancement is the modulation of kertinocytes and the aesthetic improvement is selected from the group consisting of:

(a) improve the viability and/or function of the keratinocytes

(b) down-regulate the production of inflammatory factors and/or cytokines;

(c) improve skin barrier repair and/or function;

(d) improve thickness of the epidermis;

(e) improve uniformity of epidermal cells;

(f) improvement in pigmentation; and/or

(g) smooth scars and stretch marks.

16. The method of claim 11 , wherein the skin enhancement is improving and maintaining the quality and viability of the extracellular matrix and the aesthetic improvements is selected from the group consisting of:

(a) treatment and/or reduction of the appearance of fine lines or wrinkles;

(b) improvement in the skin's thickness, plumpness, and/or tautness;

(c) improvement in skin barrier repair and/or function;

(d) improvement in appearance of skin contours;

(e) increased skin elasticity and/or resiliency;

(f) treatment and/or reduction of skin sagging;

(g) smoothing scars and stretch marks;

(h) reduction of pore size;

(i) improvement in the skin's suppleness, softness, tone, radiance, and/or clarity;

(j) improvement in the skin texture and/or promotion of its retexturization;

(k) restoration of skin luster and/or brightness;

(k) replenishment of essential nutrients and/or constituents in the skin; and/or

(l) improvement in skin moisturization and/or type.

17. The method according to claim 11 , wherein the skin enhancement is improving and maintaining the quality and viability of the epidermis and the aesthetic improvement is selected from the group consisting of:

(a) improvement in skin barrier repair and/or function;

(b) improvement of thickness of the epidermis;

(c) improvement in uniformity of epidermal cells;

(d) improvement in pigmentation; and/or

(e) smoothing scars and stretch marks.

18. The method of claim 11 wherein the dermatologically effective amount of the cosmetic composition is applied to the area of skin in need thereof for a time sufficient to improve the area of skin's aesthetic appearance.

19. The method according to claim 18 , wherein the composition is applied to said skin at least once daily for a period of at least four weeks.

20. The cosmetic composition of claim 1 , further comprising from about 0.0001% to about 25% by weight of the N-heteroarylbisamide of Formula I.

21. The cosmetic composition according to claim 1 , wherein said cosmetically acceptable vehicle comprises a water-in-oil or oil-in-water emulsion.

Assignments (8)