Use of unsymmetrically substituted triazine derivatives in...

Details Use of unsymmetrically substituted triazine derivatives in... Use of unsymmetrically substituted triazine derivatives in...

2001-01-18

2002-04-16

Dodson, Shelley A. (Department: 1616)

Drug, bio-affecting and body treating compositions

Topical sun or radiation screening, or tanning preparations

C424S060000, C424S400000, C424S401000, C514S241000

Reexamination Certificate

active

06372199

ABSTRACT:

The present invention relates to cosmetic and dermatological preparations containing unsymmetrically substituted triazine derivatives. In further embodiments, the present invention relates to preparations for protecting the skin against UV radiation. The invention further relates to dermatological preparations which maintain and improve the immune status of human skin.
Skin care primarily means the strengthening or rebuilding of the natural function of the skin as a barrier against environmental influences (e.g. dirt, chemicals, microorganisms) and against the loss of endogenous bodily substances (e.g. water, natural fats, electrolytes).
If this function is impaired, increased resorption of toxic or allergenic substances or attack by microorganisms can occur, leading to toxic or allergic skin reactions.
The main aim of skincare is also to compensate for the loss of sebum and water from the skin caused by daily washing. This is particularly important when the natural regeneration ability is inadequate. Furthermore, skincare products should protect against environmental influences, in particular against sun and wind, and delay the signs of skin ageing.
cis-Urocanic acid (also called cis-urocaninic acid or cis-4-imidazolylacrylic acid) is characterized by the following structural formula:
It has the empirical formula C
6
H
6
N
2
O
2
and the molecular mass 138.12. cis-Urocanic acid is formed, for example, by UV irradiation of the trans isomer, which occurs in human skin and also in perspiration.
trans-Urocanic acid is characterized by the following structural formula:
trans-Urocanic acid likewise has the empirical formula C
6
H
6
N
2
O
2
and the molecular mass 138.12 and occurs in human skin and also in perspiration.
If, within the scope of the disclosure presented herein, the term “urocanic acid” is used without an indication of the isomer concerned, then both th cis and also the trans isomer and any mixtures of the two isomers are covered.
DE-A 41 21 030 shows that urocanic acid has an antiphlogistic effect, alleviates the effects of allergic reactions and prevents allergic reactions to a high degree.
Because of its antiphlogistic and antiallergic potency, urocanic acid is effective against psoriasis, neurodermatitis and contact dermatitis and autoimmune diseases, such as, for example, vitiligo, pruritus, Alopecia areata, ichthyosis and atopy, for which the activity mechanism is similar.
Traditional preparations have been unable to prevent endogenous skin urocanic acid from being washed out or washed off upon contact with water and/or surfactants or during perspiration. Even conventional preparations containing urocanic acid were at best able to freshen up the urocanic acid status of the skin a little, but no longer able to achieve the original state itself. It has hitherto only been possible to achieve this after the individual regeneration time of the skin in question.
Skincare preparations are mostly in the form of creams, lotions, milks, ointments, ointment bases, oils, tinctures, sticks, spray formulations and the like.
Customary cosmetic preparations are, for example, sunscreens. The use of trans-urocanic acid as a sunscreen is likewise known.
The harmful effect of the ultraviolet part of solar radiation on the skin is generally known. Whereas rays with a wavelength less than 290 nm (the UVC region), are absorbed by the ozone layer in the earth's atmosphere, rays in the range between 290 nm and 320 nm, the UVB region, cause an erythema, simple sunburn or even burns to the skin of greater or lesser severity.
A maximum erythema activity of sunlight is given as the narrower region around 308 nm.
Numerous compounds are known for protecting against UVB radiation; these are mostly derivatives of 3-benzylidenecamphor, of 4-aminobenzoic acid, of cinnamic acid, of salicylic acid, of benzophenone and also of 2-phenylbenzimidazole.
Also for the wavelength range between about 320 and 400 nm, the UVA region, UV filter substances are important since such rays can also cause damage. For example, it has been proven that UVA radiation leads to damage of the elastic and collagenous fibres of connective tissue, which causes the skin to age prematurely, and is to be regarded as a cause of numerous phototoxic and photoallergic reactions. The harmful effect of UVB radiation can be intensified by UVA radiation.
UV radiation can, however, also lead to photochemical reactions, in which case the photochemical reaction products intervene in the skin and cell metabolism.
Such photochemical reaction products are predominantly free-radical compounds, e.g. hydroxyl radicals, hydroperoxy radicals and superoxide ions. Undefined free-radical photoproducts which form in the skin itself can also display uncontrolled secondary reactions because of their high reactivity. However, singlet oxygen, a non-free-radical excited state of the oxygen molecule, can also be formed during UV irradiation, as can short-lived epoxides and many others. Singlet oxygen, for example, differs from normal triplet oxygen (free-radical ground state) by virtue of its increased reactivity. However, excited, reactive (free-radical) triplet states of the oxygen molecule also exist.
In order to prevent these reactions, antioxidants and/or free-radical scavengers can be additionally incorporated into the cosmetic or dermatological formulations.
Most of the inorganic pigments which are known for use in cosmetics to protect the skin against UV rays are UV absorbers or UV reflectors. These are oxides of titanium, zinc, iron, zirconium, silicon, manganese, aluminium, cerium and mixtures thereof, and modifications.
Although there are entirely advantageous cosmetic or dermatological preparations for protecting the skin against the harmful consequences of the effect of UV light, one disadvantage which is often observed is that the preparations are not water-resistant or are insufficiently water-resistant.
Sunscreen preparations are particularly frequently required and used on beaches and in open-air swimming pools. It is therefore desirable for the sunscreen formulation to be largely water-resistant so that it is not washed off from the skin or is washed off only to a small extent.
Relatively high sunscreen factors, namely, for example, those above SPF 15, can generally only be achieved using large amounts of UV filter substances. If a sunscreen product is still to have a high sunscreen factor after bathing, the UV filter substance in particular must be retained on the skin.
It is inconvenient if the sunscreen product has to be reapplied after bathing. During bathing itself, the use of a sunscreen formulation which can be washed off may, under certain circumstances, even be reckless and harmful to the skin since water does not absorb light in the UVA and UVB region very well, and consequently represents no noteworthy UV protection, not even for submerged areas of skin.
For water-resistant sunscreen formulations, the prior art usually uses non-water-soluble UV filter substances, water-repellent raw materials (e.g. silicone oils in high concentrations) and/or film formers, in particular high molecular weight compounds (e.g. PVP/hexadecene copolymers). Here, barriers are built up between the UV filter substances on the skin and the water.
A disadvantage here is that although diffusion of the filter substances into water can be delayed, it cannot be prevented completely. For this reason, such products can lose their protective effect to a considerable extent during relatively long bathing periods. However, the sun protection can be significantly diminished even as a result of the normal development of perspiration or the wiping off of this perspiration and the sunscreen substances dissolved or partially dissolved therein, in particular the endogenous skin urocanic acid, but also the artificially applied urocanic acid.
Even simple bathing in water without the addition of surfactants will initially cause the horny layer of the skin to swell, the degree of this swelling depending, for example, on the bathing time and temperature. Along with w

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