IP Library Granted Patent US 7,144,570
Granted Patent B2
US 7,144,570 · App. 10/444,356 · Granted Dec 5, 2006

Sunscreen compositions and methods of use thereof

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,144,570
App. No.
10/444,356
Granted
Dec 5, 2006
Kind
B2
Abstract

Disclosed herein are novel methods for reducing or preventing the harmful effects of solar radiation on skin. Also disclosed are novel sunscreen compositions comprising thaizolium, thiadiazolium or triazolium compounds or derivatives and analogs thereof for reducing or preventing the harmful effects of solar radiation on skin. Sunscreen active agents that provide UV-A and UV-B filters are also included. The invention further discloses additional sunscreen active agents, emollients, humectants, dry-feel modifiers, waterproofing agents, insect repellants, antimicrobial preservatives, antioxidants, chelating agents, fragrances and moisturizers, suitable carriers for topical application and emulsions.

Claims (41)

1. A method of reducing or preventing harmful effects of solar radiation on skin comprising, applying a composition, the composition comprising:

one or more agents that provide a UV-B filter; and,

an effective amount of a compound of formula I:

wherein

R 1 and R 2 are, independently, hydrogen, an alkyl group, or, taken together, NR 1 R 2 comprise a heterocyclic ring;

R 3 and R 4 are, independently, selected from hydrogen and pi electron donating groups;

R b and R c are, independently, hydrogen, hydroxy(lower)alkyl, (lower)alkanoyl(lower)alkyl, (lower)alkyl, (lower)alkoxycarbonyl(lower)alkyl, (lower)alkenyl, carboxy(lower)alkyl, carboxy(lower)alkyloxyimino, alkoxycarbonyl, (C 6 or C 10 ) aryl, (C 5 or C 9 ) heteroaryl, wherein the heteroaryl group contains one oxygen, one sulfur or one nitrogen, or Ar(lower)alkyl;

Y is S, O, or N—R′ where R′ is aryl, heteroaryl or lower alkyl;

Z is N or C—R b ; and

X- is a pharmaceutically acceptable anion;

wherein the compound of the formula I is not a 3-[2-(4-diethylaminophenyl)-2-oxoethy]thiazolium salt.

2. The method of claim 1 , wherein the effective amount of the compound of the formula I is between about 0.5% and about 10% by weight of the composition.

3. The method of claim 1 , wherein at least one of R 3 or R 4 is a halogen.

4. The method of claim 1 , wherein at least one of R 3 or R 4 is OH.

5. The method of claim 1 , wherein R 1 and R 2 are, independently, hydrogen or a lower alkyl group.

6. The method of claim 1 , wherein the composition further comprises a suitable carrier for topical application to human skin.

7. The method of claim 1 , wherein the one or more agents that provide a UV-B filter are selected from the group consisting of paramethoxycinnamic acid esters and octyl salicylate.

8. The method of claim 1 , wherein the composition further comprises one or more agents that provide a UV-A filter.

9. The method of claim 8 , wherein the UV-A filter is selected from the group consisting of dibenzoylmethane derivatives, 4-(1,1-dimethylethyl)-4′-methoxydibenzoylmethane, and 4-isopropyl dibenzoylmethane.

10. A sunscreen composition for the reduction or prevention of harmful effects of solar radiation on skin comprising:

one or more agents that provide a UV-B filter; and,

an effective amount of a compound of the formula I:

wherein

R 1 and R 2 are, independently, hydrogen, an alkyl group, or, taken together, NR 1 R 2 comprise a heterocyclic ring;

R 3 and R 4 are, independently, selected from hydrogen and pi electron donating groups;

R b and R c are, independently, hydrogen, hydroxy(lower)alkyl, (lower)alkanoyl(lower)alkyl, (lower)alkyl, (lower)alkoxycarbonyl(lower)alkyl, (lower)alkenyl, carboxy(lower)alkyl, carboxy(lower)alkyloxyimino, alkoxycarbonyl, (C 6 or C 10 ) aryl, (C 5 or C 9 ) heteroaryl, wherein the heteroaryl group comprises one heteroatom, selected from oxygen, sulfur or nitrogen, or Ar(lower)alkyl;

Y is S, O or N—R′ where R′ is aryl, heteroaryl or lower alkyl;

Z is N or C—R b ;

X- is a pharmaceutically acceptable anion;

wherein the compound of the formula I is not a 3-[2-(4-diethylaminophenyl)-2-oxoethyl]thiazolium salt; and,

a suitable carrier for application to the skin.

11. The composition of claim 10 , wherein the effective amount of the compound of the formula I is between about 0.5% and about 10% by weight of the composition.

12. The composition of claim 10 , wherein the one or more agents that provide a UV-B filter are selected from the group consisting of paramethoxycinnamic acid esters and octyl salicylate.

13. The composition of claim 10 , wherein the composition further comprises one or more agents that provide a UV-A filter.

14. The method of claim 13 , wherein the UV-A filter is selected from the group consisting of dibenzoylmethane derivatives, 4-(1,1-dimethylethyl)-4′-methoxydibenzoylmethane, and 4-isopropyl dibenzoylmethane.

15. The composition of claim 10 , wherein the composition further comprises one or more sunscreen active agents.

16. The method of claim 15 , wherein the one or more sunscreen active agents are selected from the group consisting of para aminobenzoic acid, avobenzone, cinoxate, dioxybenzone, homosalate, menthyl anthranilate, octocrylene, octyl methoxycinnamate, oxybenzone, padimate O, phenylbenzimidazole sulfonic acid, sulisobenzone, trolamine salicylate, titanium dioxide, zinc oxide, diethanolamine methoxycinnamate, digalloy trioleate, ethyl dihydroxypropyl PABA, glyceryl aminobenzoate, lawsone with dihydroxyacetone, red petrolatum, homomenthyl salicylate, Benzophenone-3, Uvinul MS-40, Uvasorb MET/C, and Neo Heliopan 303 or mixtures thereof.

17. The composition of claim 10 , wherein the composition further comprises one or more components selected from the group consisting of emollients, humectants, dry-feel modifiers, waterproofing agents, insect repellants, antimicrobial preservatives, antioxidants, chelating agents, fragrances and moisturizers.

18. The composition of claim 10 , wherein the composition is in the form of an emulsion.

19. The emulsion of claim 18 , further comprising a hydrophobic component that imparts film-forming and waterproofing characteristics to the emulsion.

20. The emulsion of claim 19 , wherein the hydrophobic component is a polymer selected from the group consisting of a copolymer comprising octadecene-1 and maleic anhydride monomers, polyanhydride resin, and a copolymer comprising vinyl pyrollidone and eicosene monomers.

Assignments (3)
RELEASE OF SECURITY INTEREST (REEL/FRAME 018746/0676) Recorded Aug 7, 2007
From: BAKER BROS ADVISORS, LLC
To: SYNVISTA THERAPEUTICS, INC.
Reel/Frame 019658/0176 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Jan 12, 2007
From: ALTEON INC., A DELAWARE CORPORATION
To: BAKER BROS ADVISORS, LLC, AS COLLATERAL AGENT FOR THE SECURED PARTIES
Reel/Frame 018746/0676 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2004
From: GALL, MARTIN; PAGAN, MIGUEL
To: ALTEON INC.
Reel/Frame 014909/0933 →