# US 2014/0193348 A1 · Molecules, compositions, and methods for light absorption

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- Number: US 2014/0193348 A1
- Document ID: US20140193348A1
- Status: Published application
- Kind: A1
- Application number: 13/878,947
- Filed: 2012-02-23
- Published: 2014-07-10
- Earliest claimed: 2012-02-23
- Assignees: Empire Technology Development LLC
- Inventors: Jinye Wang
- Web page: https://patentgrep.com/patent/US20140193348A1

## CPC

- A61K 8/63: Steroids; Derivatives thereof
- A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- C07D 213/04: having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07J 41/0055: {the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives}
- C07J 43/003: {not condensed}
- C07J 9/00: Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07J: STEROIDS (seco-steroids C07C)

## Abstract

Embodiments provided herein relate to molecules, compositions, and methods for light absorption. In some embodiments, the molecules and/or compositions can be used to absorb ultraviolet light. In some embodiments, the ultraviolet light absorption compound can be used in a sunscreen composition. In some embodiments, the compound includes an azobenzene group for the absorption of ultraviolet light.

## Claims

### Claim 1

A molecule comprising an azobenzene group attached to a heterocycle group and a cholesterol group.

### Claim 2 (depends on 1)

The molecule of claim 1, wherein the azobenzene group has the formula of Formula I:
wherein R1 comprises a heterocycle group or a substituted variant thereof and wherein R2 comprises a cholesterol group or a substituted variant thereof.

### Claim 3 (depends on 2)

The molecule of claim 2, wherein the heterocycle group comprises a 5 or 6 membered heterocycle.

### Claim 4 (depends on 3)

The molecule of claim 3, wherein the heterocycle group is selected from Formula VI, VII, VIII, or IX.

### Claim 5 (depends on 4)

The molecule of claim 4, wherein the heterocycle is connected to the structure of Formula I via an alkoxy member.

### Claim 6 (depends on 5)

The molecule of claim 5, wherein the alkoxy member comprises 1, 2, 3, 4, 5, 6, 7, or 8 carbons.

### Claim 7 (depends on 6)

The molecule of claim 6, wherein the heterocycle group comprises the structure shown in Formula II:
wherein n=1 or 2, and wherein R3 is either no substitution or a phenyl group.

### Claim 8 (depends on 7)

The molecule of claim 7, wherein R3 can be in the ortho-position or meso-position to the nitrogen.

### Claim 9 (depends on 2)

The molecule of claim 2, wherein the cholesterol group is selected from the group consisting of:

### Claim 10 (depends on 8)

The molecule of claim 8, wherein the cholesterol group comprises the structure of Formula III:

### Claim 11 (depends on 1)

The molecule of claim 1, wherein the molecule comprises the structure of Formula IV:
wherein n=1 or 2 and wherein R3 is either no substitution or a phenyl group.

### Claim 12 (depends on 1)

The molecule of claim 1, wherein the molecule comprises the structure of Formula V:
wherein n=1 or 2, and wherein R3 is either no substitution or a phenyl group, and wherein when the when R3 is a phenyl group, the phenyl is in the ortho or meso-position to the nitrogen in the heterocycle.

### Claim 13

A sunscreen composition comprising an azobenzene, wherein the azobenzene is present in an amount that is sufficient to serve as a sunscreen at an SPF of at least 15.

### Claim 14 (depends on 13)

The sunscreen composition of claim 13, further comprising a heterocycle group attached to the azobenzene group.

### Claim 15 (depends on 13)

The sunscreen composition of claim 13, further comprising a cholesterol group attached to the azobenzene group.

### Claim 16 (depends on 15)

The sunscreen composition of claim 15, wherein the azobenzene group has the formula of Formula I:
wherein R1 comprises a heterocycle group or substituted variant thereof and wherein R2 comprises a cholesterol group or substituted variants thereof.

### Claim 17 (depends on 13)

The sunscreen composition of claim 13, further comprising at least one ingredient selected from the group consisting of: p-Aminobenzoic acid, Padimate O, Phenylbenzimidazole sulfonic acid, Cinoxate, Dioxybenzone, Oxybenzone, Homosalate, Menthyl anthranilate, Octocrylene, Octyl methoxycinnamate, Octyl salicylate, Sulisobenzone, Trolamine salicylate, Avobenzone, Ecamsule, Titanium dioxide, Zinc oxide, Cinnamates (octyl methoxycinnamate (OMC), Ethylhexyl p-Methoxycinnamate, Ensulizole, Octinoxate, Octyl dimethyl paba, and any combination thereof.

### Claim 18 (depends on 13)

The sunscreen composition of claim 13, further comprising at least one ingredient selected from the group consisting of: Avobenzone, Parsol 1789, Dioxybenzone (UVB, UVAII), Ecamsule, Menthyl Anthranilate, Meradimate, Oxybenzone (benzophenone, benzophenone-3), Sulisobenzone (UVB, UVAII), and any combination thereof.

### Claim 19 (depends on 13)

The sunscreen composition of claim 13, wherein the composition does not include a photostabilizer.

### Claim 20 (depends on 13)

The sunscreen composition of claim 13, wherein the sunscreen composition is a sun block.

### Claim 21 (depends on 13)

The sunscreen composition of claim 13, wherein the sunscreen composition is a sun tanner.

### Claim 22 (depends on 13)

The sunscreen composition of claim 13, further comprising water.

### Claim 23 (depends on 13)

The sunscreen composition of claim 13, wherein the composition is formulated as an oil, cream, lotion, spray, lipstick, ointment, wax, or gel.

### Claim 24 (depends on 1)

A pharmaceutical composition comprising the molecule of claim 1.

### Claim 25

A sunscreen composition comprising an azobenzene attached to at least one of the following: a heterocycle group, a cholesterol group, or both a heterocycle group and a cholesterol group.

### Claim 26

(canceled)

### Claim 27

(canceled)

### Claim 28

(canceled)

### Claim 29

(canceled)

### Claim 30

(canceled)

### Claim 31

(canceled)

### Claim 32

(canceled)

### Claim 33

(canceled)

### Claim 34

(canceled)

### Claim 35

(canceled)

### Claim 36

(canceled)

### Claim 37

(canceled)

### Claim 38

A method of reactivating a sunscreen, the method comprising:
providing a sunscreen comprising a trans azobenzene;
exposing the trans azobenzene to ultraviolet light for a first period of time, thereby converting the trans azobenzene to a cis azobenzene; and
allowing the cis azobenzene to return to the trans azobenzene to form reactivated trans azobenzene, thereby reactivating the sunscreen.

### Claim 39 (depends on 38)

The method of claim 38, further comprising exposing the reactivated trans azobenzene to ultraviolet light for a second period of time.

### Claim 40

A sunscreen comprising a trans form of azobenzene in an amount that is sufficient to serve as the active ingredient in the sunscreen.

### Claim 41

A method of making a UV absorbing agent, the method comprising:
providing an azo compound; and
attaching a cholesterol group to the azo compound.

### Claim 42 (depends on 41)

The method of claim 41, wherein the cholesterol group is attached to the azo compound by an esterification reaction.

### Claim 43 (depends on 42)

The method of claim 42, wherein the azo compound is provided by a diazo reaction.