Photostabilizing compounds, compositions, and methods

Patent metadata

Field	Value
Publication number	US-11655215-B2
Application number	US-201917253612-A
Country	US
Kind code	B2
Filing date	Jun 13, 2019
Priority date	Jun 18, 2018
Publication date	May 23, 2023
Grant date	May 23, 2023

Abstract

Heterocyclic compounds are provided. In particular, the heteroatom of the heterocyclic compound may be nitrogen. The heterocyclic compounds may demonstrate capacity of stabilizing photoactive compounds. Topical compositions comprising these heterocyclic compounds are also provided. In particular, these topical compositions further comprise photoactive compounds. Methods for stabilizing photoactive compounds are also provided. These methods comprise mixing the photoactive compounds with photostabilizing heterocyclic compounds.

First claim

The invention claimed is:

1. A composition comprising at least one photoactive compound and at least one heterocyclic compound having the structure according to Formula I:

Wherein each of A1, A2, A3, A4, A5, A6, A7, and A8 is independently selected from the group consisting of CR 3 and N;
wherein R 3 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, an aryl group having from about 6 to about 20 carbon atoms;
wherein at least one of A1, A2, A3, A4, A5, A6, A7, and A8 is N;
wherein no more than four of A1, A2, A3, A4, A5, A6, A7, and A8 are N;
wherein each of R 1 and R 2 is independently selected from the group consisting of CN, C(═O)OR 4 , C(═O)R 4 , F, CF 3 , with the proviso that R 1 and R 2 are not both CN.
wherein R 4 is selected from the group consisting of H, a straight or branched chain 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, an aryl group having from about 6 to about 20 carbon atoms.

2. The composition of claim 1 , wherein the heterocyclic compounds are present in amount ranging from 0.01 to 25% by weight of the total composition.

3. The composition of claim 1 , wherein the photoactive compound is selected from the group consisting of a retinoid, a sunscreen, or mixture thereof.

4. The composition of claim 3 , wherein the photoactive compound is a retinoid.

5. The composition of claim 4 , wherein the retinoid is present in amount ranging from about 0.0001 to about 20% by weight of the total composition.

6. The composition of claim 3 , wherein the photoactive compound is a sunscreen.

7. The composition of claim 6 , wherein the sunscreen is selected from the group consisting of a UVA chemical sunscreen, a UVB chemical sunscreen, a physical sunscreen, and mixture thereof.

8. The composition of claim 7 , wherein the sunscreen is a UVA chemical sunscreen.

9. The composition of claim 8 , wherein the UVA chemical sunscreen is present in amount ranging from about 0.001 to about 20% by weight of the total composition.

10. The composition of claim 7 , wherein the sunscreen is a UVB chemical sunscreen.

11. The composition of claim 10 , wherein the UVB chemical sunscreen is present in amount ranging from about 0.001 to about 45% by weight of the total composition.

12. The composition of claim 1 , wherein the at least one heterocyclic compound is selected from:

13. A method for stabilizing a photoactive compound, comprising mixing a least one photoactive compound with at least one heterocyclic compound having the structure according to Formula I:

Wherein each of A1, A2, A3, A4, A5, A6, A7, and A8 is independently selected from the group consisting of CR 3 and N;
wherein R 3 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, an aryl group having from about 6 to about 20 carbon atoms;
wherein at least one of A1, A2, A3, A4, A5, A6, A7, and A8 is N;
wherein no more than four of A1, A2, A3, A4, A5, A6, A7, and A8 are N;
wherein each of R 1 and R 2 is independently selected from the group consisting of CN, C(═O)OR 4 , C(═O)R 4 , F, CF 3 , with the proviso that R 1 and R 2 are not both CN.
wherein R 4 is selected from the group consisting of H, a straight or branched chain 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, an aryl group having from about 6 to about 20 carbon atoms.

Assignees

• Elc Man Llc

Inventors

• Bonda Craig Alan

Classifications

• A61K8/4926 Primary

  having six membered rings · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title

• A61Q19/08

  Anti-ageing preparations · CPC title

• A61K8/4953 Primary

  containing pyrimidine ring derivatives, e.g. minoxidil · CPC title

• A61K8/671

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