Glycyrrhetinimidyl hydroxyproline alkyl esters and protected derivatives thereof
View Patent ↗The present invention is directed to glycyrrhetinimidyl hydroxyproline alkyl ester compounds and their protected derivatives and cosmetically acceptable salts thereof, methods of making the compounds, cosmetic compositions containing at least one of the compounds and methods of using the same to promote collagen production in human skin. The compounds and cosmetic compositions of the invention provide various advantageous properties to the human skin.
1. A compound of formula (I):
or a cosmetically acceptable salt thereof,
wherein R 1 is selected from the group consisting of a H— and a protecting group; and R 2 is a substituted or unsubstituted moiety selected from the group consisting C1 to C6 alkyl, C2 to C6 alkenyl, C2 to C6 alkynyl, aryl or heteroaryl.
2. The compound of claim 1 , wherein R 1 is H— and R 2 is a methyl group.
3. The compound of claim 1 , wherein R 1 is a protecting group selected from the group consisting of acetyl, benzoyl, benzyl, beta-methoxymethyl ether, methoxymethyl ether, p-methoxy benzyl ether, methylthiomethyl ether, pivaloyl, tetrahydropyranal, trityl and silyl ether.
4. The compound of claim 1 , wherein R 1 is a protecting group that is an acetyl group and R 2 is a methyl group.
5. A cosmetic composition comprising up to 75% by weight of the compound of claim 1 .
6. The cosmetic composition of claim 5 , wherein R 1 is H— and R 2 is a methyl group.
7. The cosmetic composition of claim 6 , further comprising a cosmetically acceptable carrier and wherein the compound is in an amount of about 0.001% to about 75% by weight of the composition.
8. The cosmetic composition of claim 7 , comprising a collagen release promoter.
9. A method of making a compound of formula (I):
or a cosmetically acceptable salt thereof,
wherein R 1 is selected from the group consisting of a H— and a protecting group; and
R 2 is a substituted or unsubstituted moiety selected from the group consisting C1 to C6 alkyl, C2 to C6 alkenyl, C2 to C6 alkynyl, aryl or heteroaryl, the method comprising the steps of:
protecting glycyrrhetinic acid of formula (IV):
to form protected glycyrrhetinic acid of formula (II)
where X is a protecting group; and
reacting the protected glycyrrhetinic acid of formula (II) with hydroxyproline of formula (III)
to form the protected compound of formula (I) and optionally;
deprotecting the compound of formula (I).
10. The method of claim 9 , wherein the compound of formula (I) is deprotected to form the compound wherein R 1 is H—.
11. The method of claim 10 , wherein R 2 is a methyl group.
12. A method of promoting collagen production in human skin comprising the steps of applying the compound of claim 1 to the skin of a person, and administering a collagen release promoter to the person.
13. The method of claim 12 , wherein the collagen release promoter is selected from the group consisting of Vitamin C, copper, manganese and hydroxyproline.
14. The method of claim 12 , wherein the collagen release promoter is Vitamin C.
15. The method of claim 12 , wherein the compound is in the form of a cosmetic composition.
16. The method of claim 15 , wherein the cosmetic composition comprises the compound and the collagen release promoter.