Sunscreen compositions and compounds for use therein

Details Sunscreen compositions and compounds for use therein Sunscreen compositions and compounds for use therein

1988-05-26

1991-03-19

Ore, Dale R.

Drug, bio-affecting and body treating compositions

Topical sun or radiation screening, or tanning preparations

424 47, 424 60, 514844, 514847, 514873, 514937, 514938, 514939, 514944, 514948, 514969, 514973, 546 15, A61K 740, A61K 742, A61K 744, A61K 748

Patent

active

050009460

DESCRIPTION:

BRIEF SUMMARY
The invention relates to sunscreen compositions comprising ultra-violet radiation absorbing compounds to methods of preparing such compositions, and to UV-absorbing compounds of particular use in preparing such compositions.
Sunscreen compositions may be used to form a coating for protecting substrates from harmful effects of ultraviolet radiation such as in solar radiation. For example, sunscreen compositions are probably best known for use in the protection of skin against severe erythra edema which can be caused by exposure to sunlight.
Common commercially available UV-agents include, for example, para-aminobenzoic acid derivatives, benzotriazoles, benzophenones, methoxycinnamates and salicylates. It has been proposed, for example in U.K. Pat. application No. 2,120,549A and French Pat. application No. 8301391, that certain specific classes of vinylagous amide compounds (enaminoketones) may also be used as UV-absorbing sunscreen agents.
We have observed that certain mycosporine amino acids which exist in the living tissue of the Pacific staghorn coral Acropora formosa are functional UV-absorbing agents (.lambda.max 310-332 nm) in corals inhabiting the shallow-water, tropical coral reef environment. While these naturally occurring enaminoketone compounds appear to be potentially attractive as commercial UV-agents, their utility is questionable because of the difficulty of isolating them from their biological source and because of their lack of adequate chemical stability. We have proposed that certain synthetic vinylagous amide analogues of those natural products can be prepared which preserves their characteristic UV-absorbing chromophore within a chemically more stable structure and which typically have UV-absorption maxima (.lambda.max) in the wavelength region 288-340 nanometers (P.C.T. Pat. application No. PCT/AU85/00242) These synthetic analogues, however, proved to be chemically unstable during prolonged period of formulation and storage.
We have now found that a select group of cyclic vinylogous amide compounds which comprise a tetrahydropyridine moiety are particularly suitable for use in sunscreen compositions.
Accordingly we provide a sunscreen composition comprising as an effective component thereof at least one compound of formula I ##STR2## wherein: R.sup.1 is selected from the group consisting of: C.sub.1 to C.sub.18 alkyl; C.sub.1 to C.sub.9 alkyl substituted with a substituent selected from the group of hydroxy, amino, C.sub.1 to C.sub.9 alkoxy, C.sub.2 to C.sub.9 alkenyloxy, C.sub.1 to C.sub.9 alkanoyl, (C.sub.1 to C.sub.9 alkoxy)carbonyl, carbamoyl, (C.sub.1 to C.sub.6 alkyl)carbamoyl and phenyl; C.sub.2 to C.sub.18 alkenyl; C.sub.2 to C.sub.9 alkenyl substituted with a substituent selected from the group consisting of hydroxy, amino, C.sub.1 to C.sub.9 alkoxy, C.sub.2 to C.sub.9 alkenyloxy, C.sub.1 to C.sub.9 alkanoyl, carbamoyl, (C.sub.1 to C.sub.6 alkyl)carbamoyl, and phenyl; C.sub.2 to C.sub.18 alkynyl; phenyl; the groups phenyl and benzyl said groups being substituted in the benzene ring with a substituent is selected from the group of C.sub.1 C.sub.12 alkyl, C.sub.1 to C.sub.12 alkoxy, C.sub.2 to C.sub.12 alkenyloxy, C.sub.1 to C.sub.12 alkylamino, N,N-di(C.sub.1 to C.sub.6 alkyl)amino, (C.sub.1 to C.sub.12 alkoxy)carbonyl and C.sub.1 to C.sub.12 alkanoyl; C.sub.5 to C.sub.7 cycloalkyl; C.sub.5 to C.sub.7 cycloalkenyl; the groups substituted C.sub.5 to C.sub.7 cycloalkyl and substituted C.sub.5 to C.sub.7 cycloalkenyl wherein the substituent is selected from the group of hydroxy, amino, C.sub.1 to C.sub.9 alkyl, C.sub.1 to C.sub.9 alkoxy, and C.sub.2 to C.sub.9 alkenyloxy; polymers of one or more of the monomers selected from ethylene glycol, propylene glycol, styrene and C.sub.2 to C.sub.4 alkenes, and derivatives of said polymers; and wherein R.sup.1 may optionally link together with R.sup.2 via a bridging group of formula --(R.sup.7 R.sup.8 C).sub.m -- wherein m is 2 or 3 and R.sup.7 (which may be the same or different) and R.sup.8 (which may be the same or different) are indep

REFERENCES:
patent: 3479327 (1969-11-01), Merijan
patent: 3873537 (1975-03-01), Parker et al.
UK Patent Appln. No. 2120549.
International Patent Appln. PCT/AU85/00242.
Schreiber, Tetrahedron Letters, 21, 1027-1030 (1980).
Greenhill, J. Chem. Soc. (c), 2699-2702 (1977).

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