Photostabilizing compounds, compositions, and methods

Patent metadata

Field	Value
Publication number	US-11484485-B2
Application number	US-201917254231-A
Country	US
Kind code	B2
Filing date	Jun 13, 2019
Priority date	Jun 18, 2018
Publication date	Nov 1, 2022
Grant date	Nov 1, 2022

Abstract

Photostabilizing compounds are provided. In particular, the photostabilizing compounds may be heterocyclic or homocyclic. Topical compositions comprising these compounds are also provided. In particular, these topical compositions may further comprise photoactive compounds. Methods for stabilizing photoactive compounds are also provided. These methods comprise mixing the photoactive compounds with photostabilizing compounds.

First claim

The invention claimed is:

1. A photostabilizing compound having a structure according to the formula selected from the group consisting of:

wherein each A is independently selected from the group consisting of CR 1 and N;
wherein R 1 is selected from the group consisting of H, OH, a straight or branched chain alkyl group having from about 1 to about 20 carbon atoms, an alkoxy group having from about 1 to about 20 carbon atoms, an alkenyl group having from about 2 to about 20 carbon atoms, an alkynyl group having from about 2 to about 20 carbon atoms, and an aryl group having from about 6 to about 20 carbon atoms;
wherein no more than four As are N;
wherein each of B 1 and B 2 is independently selected from the group consisting of CN, C(═O)OR 2 , with the proviso that B 1 and B 2 are not both CN;
wherein R 2 is selected from the group consisting of H, an alkyl group having from about 1 to about 20 carbon atoms, an alkenyl group having from about 2 to about 20 carbon atoms, an alkynyl group having from about 2 to about 20 carbon atoms, and an aryl group having from about 6 to about 20 carbon atoms.

2. The photostabilizing compound of claim 1 , wherein the photostabilizing compound is heterocyclic.

3. The photostabilizing compound of claim 1 , wherein the photostabilizing compound is homocyclic.

4. The photostabilizing compound of claim 1 , wherein the photostabilizing compound having a structure according to Formula I.

5. The photostabilizing compound of claim 1 , wherein the photostabilizing compound having a structure according to Formula II.

6. The photostabilizing compound of claim 1 , wherein the compound having a structure according to Formula III.

7. The photostabilizing compound of claim 1 , wherein the photostabilizing compound having a structure according to Formula IV.

8. The photostabilizing compound of claim 1 , wherein R 1 is selected from the group consisting of H, a straight or branched chain alkyl group having from about 1 to about 20 carbon atoms, and an alkoxy group having from about 1 to about 20 carbon atoms.

9. The photostabilizing compound of claim 1 , wherein R 1 is selected from the group consisting of H, and a straight or branched chain alkyl selected from the group consisting of methyl, ethyl, propyl, butyl, 2-methyl-1-propyl, 2-methyl-2-propyl, pentyl, 2-methyl-2-butyl, hexyl, heptyl, octyl, decyl, or dodecyl.

10. The photostabilizing compound of claim 1 , wherein R 2 is a straight or branched chain alkyl group having from about 1 to about 20 carbon atoms.

11. The photostabilizing compound of claim 10 , wherein R 2 is a straight or branched chain alkyl group having at least 8, no more than 12 carbon atoms.

12. The photostabilizing compound of claim 11 , wherein R 2 is a straight or branched chain alkyl group having 8 carbon atoms.

13. The photostabilizing compound of claim 1 , wherein the photostabilizing compound is selected from the group consisting of:

14. A composition comprising at least one photostabilizing compound having the structure according to the formula selected from the group consisting of:

wherein each A is independently selected from the group consisting of CR 1 and N;
wherein R 1 is selected from the group consisting of H, OH, a straight or branched chain alkyl group having from about 1 to about 20 carbon atoms, an alkoxy group having from about 1 to about 20 carbon atoms, an alkenyl group having from about 2 to about 20 carbon atoms, an alkynyl group having from about 2 to about 20 carbon atoms, and an aryl group having from about 6 to about 20 carbon atoms;
wherein no more than four As are N;
Wherein each of B 1 and B 2 is independently selected from the group consisting of CN, C(═O)OR 2 , with the proviso that B 1 and B 2 are not both CN;
wherein R 2 is selected from the group consisting of H, an alkyl group having from about 1 to about 20 carbon atoms, an alkenyl group having from about 2 to about 20 carbon atoms, an alkynyl group having from about 2 to about 20 carbon atoms, and an aryl group having from about 6 to about 20 carbon atoms.

15. The composition of claim 14 , wherein the photostabilizing compound is present in amount ranging from 0.01 to 25% by weight of the total composition.

16. The composition of claim 14 , further comprising at least one photoactive compound.

17. The composition of claim 16 , wherein the photoactive compound is selected from the group consisting of a retinoid, a sunscreen, or mixture thereof.

18. The composition of claim 17 , wherein the photoactive compound is a retinoid.

19. The composition of claim 18 , wherein the retinoid is present in amount ranging from about 0.0001 to about 20% by weight of the total composition.

20. The composition of claim 17 , wherein the photoactive compound is a sunscreen.

21. The composition of claim 20 , wherein the sunscreen is selected from the group consisting of a UVA chemical sunscreen, a UVB chemical sunscreen, a physical sunscreen, and mixture thereof.

22. The composition of claim 21 , wherein the sunscreen is a UVA chemical sunscreen.

23. The composition of claim 22 , wherein the UVA chemical sunscreen is present in amount ranging from about 0.001 to about 20% by weight of the total composition.

24. The composition of claim 21 , wherein the sunscreen is a UVB chemical sunscreen.

25. The composition of claim 24 , wherein the UVB chemical sunscreen is present in amount ranging from about 0.001 to about 45% by weight of the total composition.

26. The composition of claim 16 , further comprising at least one ingredient selected from the group consisting of oils, surfactants, humectants, botanical extracts, particulate materials, antioxidants, and other vitamins.

Assignees

• Elc Man Llc

Inventors

• Bonda Craig Alan

Classifications

• A61Q19/08

  Anti-ageing preparations · CPC title

• A61K8/41 Primary

  Amines · CPC title

• A61K8/671

  Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal · CPC title

• C07D471/14

  Ortho-condensed systems · CPC title

• A61K2800/522

  Antioxidants; Radical scavengers · CPC title