Liposomogenic UV absorbers

Details Liposomogenic UV absorbers Liposomogenic UV absorbers

1997-09-15

2000-01-18

Nutter, Nathan M.

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Liposomes

424 59, 424 60, 424 709, C07C21910, C07C 69734, C07C22912, C07D25154

Patent

active

060155752

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to liposomogenic UV absorbers, the preparation of these compounds, and their use as sunscreen agents in cosmetic preparations.
It is known that UV rays having a wavelength of 285 to 400 nm can cause or accelerate, in man, skin damage of many different kinds, such as erythemas, accelerated skin ageing, phototoxic and photoallergic reactions etc. For the topical protection of the human skin, chemical compounds in the form of cosmetic preparations are therefore recommended, which are able to prevent the said harmful actions of the UV radiation.
It is furthermore known that the chemical UV absorbers provided in the cosmetic preparations for UV protection themselves only adhere inadequately to or in the skin. It was therefore attempted to eliminate this deficiency by the development of suitable formulations, such as emulsions, gels or oils. Such formulations should permit a longer residence of the UV protective substances on, or in, the outer skin layer. A further, improved possibility of permitting a high penetration of UV absorbers into the stratum corneum and simultaneously a longer residence time of these compounds there consists in applying the corresponding UV absorbers to the skin in liposomal packaging. Such processes are disclosed, for example in WO-92.05761 and WO-93.02659.
Surprisingly, it has now been found that compounds which contain a UV chromophore having an absorption in the range from 285 to 400 nm and specific chemical structural elements which make these compounds capable of self-organization in bimolecular layers, penetrate into the stratum corneum to a high extent and behave there in an extremely wash-resistant manner.
The present invention therefore relates to liposomogenic UV absorbers which comprise a hydrophilic head group (.dbd.Z), a spacer (.dbd.W), a UV chromophore (Q) having an absorption in the range from 285 to 400 nm and at least one hydrophobic tail group (.dbd.A) of the formula ##STR2## in which A.sub.1 and A.sub.2, independently of one another, are a hydrophobic radical, radical, 4, n.sub.1 =n.sub.2 =0 not being additionally included,
The compounds according to the invention are synthetic amphiphilic compounds which are able to organize themselves, i.e. in water they spontaneously form a two-dimensional bilayer.
The hydrophobic radicals A.sub.1 and A.sub.2 are an alkyl, alkoxy, acyl or alkylamino radical, the chains having at least 8 carbon atoms. As alkoxy radicals, A.sub.1 and A.sub.2 are advantageously the radical of an unsaturated or, preferably, saturated aliphatic monoalcohol having 8 to 22 carbon atoms. The hydrocarbon radical can be branched or preferably straight-chain. A.sub.1 and A.sub.2 preferably are an alkyl or alkenyl radical having 10 to 14 carbon atoms.
Suitable aliphatic saturated monoalcohols can be natural alcohols, such as lauryl alcohol, myristyl alcohol, cetyl alcohol or stearyl alcohol, and also synthetic alcohols, such as decyl alcohol, C.sub.10 -C.sub.13 oxoalcohol, tridecyl alcohol, isotridecyl alcohol or linear primary alcohols (Alfols) having 10 to 22 carbon atoms. Some representatives of these Alfols are Alfol (10-14), Alfol (12-13) or Alfol (16-18). ("Alfol" is a registered trademark).
Unsaturated aliphatic monoalcohols are, for example, dodecenyl alcohol, hexadecenyl alcohol or oleyl alcohol.
The alcohol radicals can be present individually or in the form of mixtures, such as mixtures of alkyl and/or alkenyl groups which are derived from soya fatty acids, palm kernel fatty acids or tallow oils, of two or more components, preferably individually.
If the radicals A.sub.1 and A.sub.2 are an alkylamino radical, this is derived from primary or preferably secondary C.sub.12 -C.sub.22 fatty amines. These amines can be obtained from the corresponding fatty acids by dehydration and subsequent dehydrogenation. Preferably, A.sub.1 and A.sub.2 as an alkylamino radical are the di-C.sub.12 -C.sub.18 alkylamino radical.
A suitable acyl radical is preferably C.sub.8 -C.sub.22 alkylcarbonyl; for example octyl-, decyl-, dodecyl-, tr

REFERENCES:
patent: 5605704 (1997-02-01), Finel et al.
J. Am. Chem. Soc. (1993), 115(10), 4387-8, XP002007895.
Angewandte Chemie International Ed., vol. 31, 1992, pp. 709-726.
Koch et al. "Photodimerization and photopolymerization of amphiphilic cinnamic acid derivatives in oriented monolayers, vesicles and solution" Makrol. Chem. 187, 1843-1853 (1986).
Watanabe et al, "Studies of Hypolipidemic Agents, I. Synthesis and Hypolipidemic Activities of Alkoxycinnamic Acid Derivatives" J. Med. Chem. 1980, 23, 50-59, 1980.
Chemical Abstracts 85:192401F, Kiguchi et al "p-Alkoxy-.alpha.-methylcinnamate esters." 1976.

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