Photostabilizing compounds, compositions, and methods

Patent metadata

Field	Value
Publication number	US-2021115041-A1
Application number	US-201917254182-A
Country	US
Kind code	A1
Filing date	Jun 13, 2019
Priority date	Jun 18, 2018
Publication date	Apr 22, 2021
Grant date	—

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

1 . A heterocyclic compound having a 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, and 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 B 1 and B 2 is independently selected from the group consisting of carbonyl or C═C(R 1 )R 2 ;
wherein each of R 1 and R 2 is independently selected from the group consisting of CN, C(═O)OR 4 , with the proviso that R 1 and R 2 are not both CN;
wherein R 4 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 heterocyclic compound of claim 1 , wherein R 3 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.

3 . The heterocyclic compound of claim 2 , wherein R 3 is selected from the group consisting of H, and a straight or branched chain alkyl group having from about 1 to about 20 carbon atoms.

4 . The heterocyclic compound of claim 1 , wherein R 3 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.

5 . The heterocyclic compound of claim 1 , wherein each of R 1 and R 2 is independently selected from the group consisting of CN and C(═O)OR 4 .

6 . The heterocyclic compound of claim 5 , wherein one of R 1 and R 2 is CN.

7 . The heterocyclic compound of claim 5 , wherein R 4 is a straight or branched chain alkyl group having from about 1 to about 20 carbon atoms.

8 . The heterocyclic compound of claim 5 , wherein R 4 is a straight or branched chain alkyl group having at least 8, no more than 12 carbon atoms.

9 . The heterocyclic compound of claim 5 , wherein R 4 is a straight or branched chain alkyl group having 8 carbon atoms.

10 . The heterocyclic compound of claim 1 , wherein the heterocyclic compound is selected from the group consisting of:

11 . A composition comprising 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, and 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 B 1 and B 2 is independently selected from the group consisting of carbonyl or C═C(R 1 )R 2 ;
wherein each of R 1 and R 2 is independently selected from the group consisting of CN, C(═O)OR 4 , with the proviso that R 1 and R 2 are not both CN;
wherein R 4 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.

12 . The composition of claim 11 , wherein the heterocyclic compound is present in amount ranging from 0.01 to 25% by weight of the total composition.

13 . The composition of claim 11 , further comprising at least one photoactive compound.

14 . The composition of claim 13 , wherein the photoactive compound is selected from the group consisting of a retinoid, a sunscreen, or mixture thereof.

15 . The composition of claim 14 , wherein the photoactive compound is a retinoid.

16 . The composition of claim 15 , wherein the retinoid is present in amount ranging from about 0.0001 to about 20% by weight of the total composition.

17 . The composition of claim 14 , wherein the photoactive compound is a sunscreen.

18 . The composition of claim 17 , wherein the sunscreen is selected from the group consisting of a UVA chemical sunscreen, a UVB chemical sunscreen, a physical sunscreen, and mixture thereof.

19 . The composition of claim 18 , wherein the sunscreen is a UVA chemical sunscreen.

20 . The composition of claim 19 , wherein the UVA chemical sunscreen is present in amount ranging from about 0.001 to about 20% by weight of the total composition.

21 . The composition of claim 18 , wherein the sunscreen is a UVB chemical sunscreen.

22 . The composition of claim 21 , wherein the UVB chemical sunscreen is present in amount ranging from about 0.001 to about 45% by weight of the total composition.

23 . The composition of claim 13 , 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

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• A61Q17/04

  Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations · CPC title

• A61K2800/52

  Stabilizers · CPC title

• A61K8/671

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

• A61K8/494 Primary

  with more than one nitrogen as the only hetero atom · CPC title