IP Library Granted Patent US 12,012,416
Granted Patent B2
US 12,012,416 · App. 17/728,876 · Granted Jun 18, 2024

Compositions and methods for treating atopic dermatitis

Inventor: Ratan K Chaudhuri (Lincoln Park, NJ)
Assignee: Sytheon Ltd
C07D493/04A61K8/4973A61K9/0014A61K9/0053A61K31/34A61K45/06A61Q17/04A61Q19/007A61Q19/08A61K2800/74
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Quick Facts
Patent No.
US 12,012,416
App. No.
17/728,876
Granted
Jun 18, 2024
Kind
B2
Abstract

A method of improving skin health and condition comprising the application of select isohexides to the skin.

Claims (31)

1. A method of improving, repairing and/or rejuvenating barrier function in the skin comprising applying an efficacious amount of a topical skin treatment composition to those areas of the skin for which such improvement, repair and/or rejuvenation is desired, said topical skin treatment composition comprising:

a) an isohexide according to Structure 1

wherein R 1 and R 2 , which are the same or different, are independently selected from H and a C 15 to C 19 unsaturated n-alkyl carboxylate group, provided that both R 1 and R 2 are not hydrogen, alone or in combination with

b) one or more additional isohexides according to Structure 1 wherein R 1 and R 2 which are the same or different, are independently selected from H and a C 15 to C 19 saturated or unsaturated n-alkyl carboxylate group, provided that both R 1 and R 2 are not hydrogen and the isohexide is a different isomer from that of isohexide (a) or at least one of R 1 and R 2 , is different from the R 1 and R 2 of isohexide (a), or both, or in combination with

c) one or more isohexides corresponding to Structure 5

wherein R 4 and R 5 are the same or different and are independently selected from H and saturated or unsaturated n-alkyl carboxylate groups provided that the saturated and/or unsaturated n-alkyl carboxylate groups are other than saturated and/or unsaturated n-alkyl carboxylate groups of 15 to 19 carbon atoms and provided that both R 4 and R 5 are not H, or in combination with

d) both (b) and (c); provided that when isohexide (c) is present at least 50 mole % of the isohexides are according to Structure 1: the carbon number for the saturated and/or unsaturated n-alkyl carboxylate groups referring the number of carbon atoms of the group excluding the carboxylate carbon.

2. The method of claim 1 wherein one of R 1 and R 2 of isohexide (a) is H.

3. The method of claim 1 wherein neither R 1 nor R 2 of isohexide (a) is H.

4. The method of claim 1 wherein R 1 and R 2 of isohexide (a) are the same and are selected from unsaturated n-alkyl groups having from 16 to 19 carbon atoms.

5. The method of claim 1 wherein at least one of R 1 and R 2 of isohexide (a) is an unsaturated n-alkyl carboxylate group of 17 carbon atoms.

6. The method of claim 1 wherein at least one of R 1 and R 2 of isohexide (a) is a mono-unsaturated n-alkyl carboxylate group.

7. The method of claim 1 wherein at least one of R 1 and R 2 of isohexide (a) is a poly-unsaturated n-alkyl carboxylate group.

8. The method of claim 1 wherein at least one isohexide (b) is present.

9. The method of claim 8 wherein the isohexides (a) and (b) are isosorbides, isomannides or isoiodides or a combination of any two or all three.

10. The method of claim 9 wherein at least 50 mole % of the isohexides are isosorbides.

11. The method of claim 8 wherein a plurality of different R 1 and/or R 2 groups are present.

12. The method of claim 8 wherein the R 1 and R 2 groups of isohexide (a) are different from the R 1 and R 2 groups of the isohexide(s) (b).

13. The method of claim 11 wherein at least 40 mole % of the R 1 and R 2 groups are unsaturated n-alky carboxylate groups and are the same.

14. The method of claim 1 wherein at least one isohexide according to Structure 5, isohexide (c), is present.

15. The method of claim 14 wherein the saturated and/or unsaturated n-alkyl group(s) R 4 and R 5 of Structure 5 have from 1 to 10 carbon atoms.

16. The method of claim 15 wherein R 4 and R 5 are saturated n-alkyl group(s).

17. The method of claim 1 wherein a plurality of isohexides (a) and (b) are present and are the reaction product of a dianhydrohexitol and a natural oil containing a plurality of fatty acids having from 16 to 20 carbon atoms and/or the triglyceride precursor of said fatty acids.

18. The method of claim 17 wherein the natural oil contains a combination of saturated and/or unsaturated fatty acids of from 16 to: 20 carbon atoms.

19. The method of claim 17 wherein the natural oil contains a combination of mono- and/or poly-unsaturated fatty acids of 16 to 20 carbon atoms.

20. The method of claim 17 wherein the natural oil is selected from the group consisting of oils isolated from safflower, grape seed, silybum marianum , hemp, sunflower, wheat germ, pumpkin seed, sesame, rice bran, almond, rapeseed, peanut, olive, and coconut.

21. The method of claim 20 wherein the natural oil is sunflower oil.

22. The method of claim 1 wherein the R 1 and R 2 groups of isohexides (a) and (b), if present, are selected from oleate, linoleate, and linolenate and mixtures of any two or all three.

23. The method of claim 1 wherein at least 40 mole % of the R 1 and R 2 groups are linoleate.

24. The method of claim 1 wherein the topical skin treatment composition includes a dermatologically acceptable carrier and the isohexide(s) amount to from 0.5 to 30 weight percent of the topical composition.

25. The method of claim 1 wherein the method is employed to treat atopic dermatitis.