Drug – bio-affecting and body treating compositions – Topical sun or radiation screening – or tanning preparations
Reexamination Certificate
1999-11-08
2001-08-28
Dodson, Shelley A. (Department: 1616)
Drug, bio-affecting and body treating compositions
Topical sun or radiation screening, or tanning preparations
C424S060000, C424S400000, C424S401000
Reexamination Certificate
active
06280711
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to photoresponsive sunscreen compositions, and more particularly, to compositions for protecting skin or hair from sunlight comprising a carrier for topical administration and an organic sunscreen agent capable of undergoing efficient photorearrangement converting the sunscreen agent molecules from weak to strong ultraviolet-absorbing compounds.
BACKGROUND OF THE INVENTION
Overexposure to sunlight can cause premature aging of the skin and in some circumstances can lead to skin cancer. One method of preventing such skin damage is to avoid more than limited exposure to sunlight. An alternative preventive method involves the widespread use of commercially-available sunscreen compositions.
Sunscreen compositions come in a wide array of formulations including those which are preformulated to give a particular level of protection based upon an expected exposure to sunlight. The drawback with such formulations is that the user may become overexposed if the expected exposure level is underestimated.
Therefore, it is an object of this invention to provide a composition for protection from ultraviolet radiation, typically in the form of sunlight, comprising a photoresponsive element which adjusts the level of protection according to the exposure of radiation received by the user.
It is also an object of this invention to provide sunscreen compositions comprising organic molecules which undergo an efficient photoreaction, converting the molecule from a weakly-absorbing compound to a strongly-absorbing compound.
It is also an object to provide a method for obtaining protection from UV-A/B/C light through the use of compositions comprising derivatives of benzoins which undergo photolysis when exposed to UV-A/B/C light and yield benzofurans with large extinction coefficients in the UV-A/B/C region of the electromagnetic spectrum.
SUMMARY
A novel use for photoactive compounds as ingredients in a photoresponsive sunscreen composition is described herein. In particular, compositions for protecting skin or hair from ultraviolet radiation are described herein which comprise a carrier for topical administration and an organic sunscreen agent which undergoes an efficient photoreaction converting the agent from a weak ultraviolet-absorbing compound into a strong ultraviolet-absorbing compound. As demonstrated herein, one example of this type of molecule is the acetyl ester of 3′,5′-dimethoxybenzoin.
Formula 1. The Generic Structure and Numbering Scheme for 3′,5′-disubstituted Benzoin Esters.
REFERENCES:
patent: 3702854 (1972-11-01), Jurd
patent: 3901908 (1975-08-01), Fitzi et al.
patent: 4098882 (1978-07-01), Lang et al.
patent: 4469774 (1984-09-01), Lee
patent: 4522808 (1985-06-01), Jacquet et al.
patent: 4534981 (1985-08-01), Zabotto et al.
patent: 4822600 (1989-04-01), Wortzman
patent: 5118707 (1992-06-01), Chatterjee et al.
patent: 5200334 (1993-04-01), Dunn et al.
patent: 5338539 (1994-08-01), Raspanti
patent: 5468470 (1995-11-01), Raspanti
patent: 5518713 (1996-05-01), Raspanti
patent: 2 285 854 (1974-12-01), None
Baldwin, J.E., et al., “New Photolabile Phosphate Protecting Groups,” Tetrahedron, 46:(19) 6879-6884 (1990).
Cummings, R.T., et al., “Photoactivable Fluorophores. 1. Synthesis and Photoactivation of o-Nitrobenzyl-Quenched Fluorescent Carbamates,” Tetrahedron Letters, 29(1): 65-68 (1988).
Rajasekharan Pillai, V.N., “Photoremovable Protecting Groups in Organic Synthesis,” Synthesis, 1-27 (Jan. 1980).
Abstracts, Angew. Chem. Internat. Edit., 4(12) 1075-1078 (1965).
Pirrung, et al., “Dimethoxybenzoin Carbonates: Photochemically-Removable Alcohol Protecting Groups Suitable for Phosphoramidite-Based DNA Synthesis,” J. Org. Chem. 60:1116-1117 (1995).
Gurney, et al., “Light-Flash Physiology with Synthetic Photosensitive Compounds,” Physiological Reviews, 67(2):583-617 (1987).
Pillai, V.N.R., “Photoremovable Protecting Groups in Organic Synthesis,” Reviews, 1-27 (1980).
Cameron, et al., “New Photolabile Amino Protecting Groups: Photogeneration of Amines from [(3′, 5′-Dimethoxybenzoinyl) oxy]carbonyl Carbamates,” J. Chem. Commun., 923-924j(1995).
Pirrung, et al., “Photoremovable Protecting Groups for Phosphorylation of Chiral Alcohols, Asymmetric Synthesis of Phosphotriesters of (−) −3′, 5′-Dimethoxybenzoin,” J. Org. Chem., 59:3890-3897 (1994).
McCray, et al., “Properties and Uses of Photoreactive Caged Compounds,” Annu. Rev. Biophys. Chem., 18:239-270 (1989).
Cummings, et al., “Photoactivable Fluorophores. 1. Synthesis and Photoactivation of o-Nitrobenzyl-Quenched Fluorescent Carbamates,” Tetrahedron Letters, 29(1):65-68 (1988).
Mendel, et al., “Construction of a Light-Activated Protein by Unnatural Amino Acid Mutagenesis,” J. Am. Chem. Soc., 113:2578-2760 (1991).
Baldwin, et al., “New Photolabile Phosphate Protecting Groups,” Tetrahedron, 19:6879-6884 (1990_.
Corrie, et al., “Synthetic Mechanistic and Photochemical Studies of Phosphate Esters of Substituted Benzoins,” J. Chem. Soc. Perkin Trans., 1:2409-2417 (1992).
Pirrung, et al., “Photochemical Deprotection of 3′-5′-Dimethoxybenzoin (DMB) Carbamates Derived from Secondary Amines,” Tetrahedron Letters, 36(33):5883-5884 (1995).
Sheehan, et al., “The Photolysis of methoxy-Substituted Benzoin Esters. A Photosensitive Protecting Group for Carboxylic Acid,” Journal of the American Chemical Society, 93(26):7222-7228 (1971).
Krepski, et al., “Addition of Grignard Reagents to o-Trimethylsilylated Cyanohydrins: Synthesis of Acyloins,” Angew. Chem. Internat. Edition, 4(12):4075 (1965).
Rock Ronald S.
Stowell Michael H. B.
California Institute of Technology
Dodson Shelley A.
Flehr Hohbach Test Albritton & Herbert LLP
Trecartin, Esq Richard F.
LandOfFree
Photoresponsive sunscreen compositions does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Photoresponsive sunscreen compositions, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Photoresponsive sunscreen compositions will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2461314