Ceramide-like function imparting agent

Patent metadata

Field	Value
Publication number	US-10143667-B2
Application number	US-201414775043-A
Country	US
Kind code	B2
Filing date	Mar 11, 2014
Priority date	Mar 12, 2013
Publication date	Dec 4, 2018
Grant date	Dec 4, 2018

Abstract

Provided are an agent for imparting ceramide-like function,
an agent for reinforcing skin barrier function, a moisturizing agent and a skin drug for external use.
The agent for imparting ceramide-like function comprises as an effective ingredient a derivative of succinic acid diamide represented by the following formula (1):

[wherein R 1 and R 2 each independently represents a hydroxyalkyl group of from 1 to 6 carbon atoms, R 3 represents a group: —CH 2 CH 2 CH 2 CH 2 —R 4 or a group: —CH 2 CH═CHCH 2 —R 4 (wherein R 4 represents an alkyl group of from 8 to 26 carbon atoms)].

First claim

The invention claimed is:

1. A method for treating dry skin, irritated skin, atopic dermatitis, senile xerosis, and/or psoriasis, comprising administering an effective amount of a derivative of succinic acid diamide to a subject in need thereof,
wherein the derivative of succinic acid diamide is represented by formula (1):

wherein
R 1 and R 2 each independently represents a hydroxyalkyl group of from 2 to 4 carbon atoms and from 1 to 3 hydroxyl groups, and
R 3 represents a group: —CH 2 CH 2 CH 2 CH 2 —R 4 or a group: —CH 2 CH═CHCH 2 —R 4 , with R 4 representing an alkyl group of 8 to 26 carbon atoms.

2. The method of claim 1 , wherein said administering comprises reinforcing skin barrier function.

3. The method of claim 1 , wherein said administering comprises moisturizing skin.

4. The method according to claim 1 , wherein R 1 and R 2 each independently is a monohydroxyalkyl group of from 2 to 4 carbon atoms.

5. The method according to claim 1 , wherein R 1 and R 2 are independently selected from the group consisting of a 2-hydroxyethyl group; a 3-hydroxypropyl group; a 1-hydroxypropan-2-yl group; a 4-hydroxybutyl group; a 1,3-dihydroxy-2-methylpropan-2-yl group; a 1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl group; a 1,2-dihydroxypropan-3-yl group; and a 1-hydroxy-2-(hydroxymethyl)propan-3-yl group.

6. The method according to claim 1 , wherein R 4 represents an alkyl group of from 12 to 26 carbon atoms.

7. The method according to claim 1 , wherein R 4 represents an alkyl group of from 16 to 20 carbon atoms.

8. The method according to claim 2 , wherein R 1 and R 2 each independently is a monohydroxyalkyl group of from 2 to 4 carbon atoms.

9. The method according to claim 2 , wherein R 1 and R 2 are independently selected from the group consisting of a 2-hydroxyethyl group; a 3-hydroxypropyl group; a 1-hydroxypropan-2-yl group; a 4-hydroxybutyl group; a 1,3-dihydroxy-2-methylpropan-2-yl group; a 1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl group; a 1,2-dihydroxypropan-3-yl group; and a 1-hydroxy-2-(hydroxymethyl)propan-3-yl group.

10. The method according to claim 2 , wherein R 4 represents an alkyl group of from 12 to 26 carbon atoms.

11. The method according to claim 2 , wherein R 4 represents an alkyl group of from 16 to 20 carbon atoms.

12. The method according to claim 3 , wherein R 1 and R 2 each independently is a monohydroxyalkyl group of from 2 to 4 carbon atoms.

13. The method according to claim 3 , wherein R 1 and R 2 are independently selected from the group consisting of a 2-hydroxyethyl group; a 3-hydroxypropyl group; a 1-hydroxypropan-2-yl group; a 4-hydroxybutyl group; a 1,3-dihydroxy-2-methylpropan-2-yl group; a 1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl group; a 1,2-dihydroxypropan-3-yl group; and a 1-hydroxy-2-(hydroxymethyl)propan-3-yl group.

14. The method according to claim 3 , wherein R 4 represents an alkyl group of from 12 to 26 carbon atoms.

15. The method according to claim 3 , wherein R 4 represents an alkyl group of from 16 to 20 carbon atoms.

16. The method according to claim 1 , wherein said administering comprises applying an effective amount of the derivative of succinic acid diamide of the formula (1) to the human body for the purpose of reinforcing and returning to health of skin barrier functions or improvement in water-retention ability of skin.

17. The method according to claim 16 , wherein said applying comprises contacting, directly or indirectly, a skin surface of a human body with the derivative of succinic acid diamide of the formula (1), to deliver an effective amount of the derivative of succinic acid diamide to at least one of the epidermis and dermis of the skin.

18. The method according to claim 16 , wherein the effective amount of the derivative of succinic acid diamide of the formula (1) is from 0.01 to 5% by mass.

19. The method according to claim 17 , wherein the effective amount of the derivative of succinic acid diamide of the formula (1) is from 0.01 to 5% by mass.

20. The method according to claim 2 , wherein said administering comprises applying an effective amount of the derivative of succinic acid diamide of the formula (1) to the human body for the purpose of reinforcing and returning to health of skin barrier functions or improvement in water-retention ability of skin.

21. The method according to claim 20 , wherein said applying comprises contacting, directly or indirectly, a skin surface of a human body with a derivative of succinic acid diamide of the formula (1), to deliver an effective amount of the derivative of succinic acid diamide to at least one of the epidermis and dermis of the skin.

22. The method according to claim 20 , wherein the effective amount of the derivative of succinic acid diamide of the formula (1) is from 0.01 to 5% by mass.

23. The method according to claim 21 , wherein the effective amount of the derivative of succinic acid diamide of the formula (1) is from 0.01 to 5% by mass.

24. The method according to claim 3 , wherein said administering comprises applying an effective amount of the derivative of succinic acid diamide of the formula (1) to the human body for the purpose of reinforcing and returning to health of skin barrier functions or improvement in water-retention ability of skin.

25. The method according to claim 24 , wherein said applying comprises contacting, directly or indirectly, a skin surface of a human body with a derivative of succinic acid diamide of the formula (1), to deliver an effective amount of the derivative of succinic acid diamide to at least one of the epidermis and dermis of the skin.

26. The method according to claim 24 , wherein the effective amount of the derivative of succinic acid diamide of the formula (1) is from 0.01 to 5% by mass.

27. The method according to claim 25 , wherein the effective amount of the derivative of succinic acid diamide of the formula (1) is from 0.01 to 5% by mass.

28. A method for treating atopic dermatitis, senile xerosis, and/or psoriasis, comprising administering an effective amount of a derivative of succinic acid diamide to a subject in need thereof,
wherein the derivative of succinic acid diamide is represented by formula (1):

wherein
R 1 and R 2 each independently represents a hydroxyalkyl group of from 2 to 4 carbon atoms and from 1 to 3 hydroxyl groups, and
R 3 represents a group: —CH 2 CH 2 CH 2 CH 2 —R 4 or a group: —CH 2 CH═CHCH 2 —R 4 , with R 4 representing an alkyl group of 8 to 26 carbon atoms.

Assignees

• Kao Corp

Inventors

• Sugai Yoshiya
• Aosaki Taisuke

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61K8/42

  Amides · CPC title

• C07C233/20

  having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton · CPC title

• A61K31/164 Primary

  of a carboxylic acid with an aminoalcohol, e.g. ceramides · CPC title

• A61Q17/00

  Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings · CPC title