Drug – bio-affecting and body treating compositions – Topical sun or radiation screening – or tanning preparations
Patent
1994-01-05
1995-08-22
Gupta, Yogendra N.
Drug, bio-affecting and body treating compositions
Topical sun or radiation screening, or tanning preparations
424 60, 424401, 544296, 544330, 544331, 544332, 546225, 546264, 546266, 546287, 546304, 546307, 558393, 558394, 558395, 558398, 558400, A61K 742, C07D23942, C07D21372, C07C25509
Patent
active
054438209
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP92/01432 filed on Jun. 25, 1992.
The present invention relates to novel esters and amides of aminomethylenecyanoacetic acid of the formula I ##STR2## where R.sup.1 and R.sup.2 are each, independently of one another, phenyl, naphthyl, biphenylyl or five- or six-membered hetaryl with one, two or three nitrogens or one oxygen or one sulfur or one nitrogen and one oxygen or one nitrogen and one sulfur, which can be benzo-fused, it being possible for these radicals to be substituted by one to three C.sub.1 -C.sub.12 -alkyl groups, C.sub.1 -C.sub.12 -alkoxy groups, halogen atoms, cyano groups, hydroxyl groups or groups of the formulae COOR.sup.3, COR.sup.3, CONHR.sup.3, OCOR.sup.3 or NHCOR.sup.3, and where phenyl, oxygens, or is C.sub.4 -C.sub.12 -alkenylene or C.sub.4 -C.sub.12 -alkynylene where the unsaturated bonds are not adjacent to the ester oxygens, or is C.sub.5 -C.sub.8 -cycloalkylene or phenylene, and
The present invention also relates to a process for preparing the compounds I and to organic materials containing the compounds I and thus stabilized against the action of light, oxygen and heat, especially stabilized plastics and surface coatings, and to cosmetic preparations containing the compounds I as sunscreen agents.
Organic materials, especially plastics and surface coatings, are known to be very rapidly decomposed in particular by the action of light. This decomposition is normally manifested by yellowing, discoloration, fissuring or embrittlement of the material. No satisfactory protection against decomposition of organic material by light, oxygen and heat has been achieved with the stabilizers used to date.
Thus, for example, U.S. Pat. No. 3,079,366 recommends, inter alia, arylaminoethylenes of the formula III ##STR3## as UV absorbers for plastics. Although the compounds III have the required spectroscopic properties, they do not meet current requirements in terms of their stabilizing action. In particular, the tendency of plastics stabilized with the compounds III to be come yellow is still too great.
It is an object of the present invention to provide stabilizers which effectively protect organic material.
We have found that this object is achieved by the esters and amides of aminomethylenecyanoacetic acid I defined in the first paragraph.
Examples of suitable hetaryl radicals R.sup.1 and R.sup.2 are those derived from pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,2,3-triazine, 1,2,4-triazine, 1,2,3-triazine, furan, thiophene, oxazole, isoxazole, thiazole, indole, benzofuran, benzothiophene, benzimidazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline or phthalazine.
Suitable substituents on the ayrl or hetaryl radicals R.sup.1 and R.sup.2 are: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, but also n-pentyl, tert-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, isononyl, n-decyl, isodecyl, n-undecyl or n-dodecyl; particular, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, n-pentoxy and tert-pentoxy, but also n-hexoxy, n-heptoxy, n-octoxy, 2-ethylhexoxy, n-nonoxy, isononoxy, n-decyloxy, isodecyloxy, n-undecyloxy or n-dodecyloxy; iodine; ethoxycarbonyl, propoxycarbonyl or butoxycarbonyl; N-ethylaminocarbonyl or N-phenylaminocarbonyl; ethoxycarbonyloxy; N-propionylamino or N-benzoylamino.
In these groups, R.sup.3 is straight-chain or branched C.sub.1 -C.sub.12 -alkyl, for which the same examples as indicated above can be given, C.sub.5 -C.sub.8 -cycloalkyl such as, in particular, cyclopentyl and cyclohexyl, but also cycloheptyl, cyclooctyl, methylcyclopentyl, dimethylcyclopentyl, methylcyclohexyl or dimethylcyclohexyl, and phenyl.
The number of substituents on the aryl or hetaryl radicals R.sup.1 and R.sup.2 can be up to 3, preferably up to 2. Where there are several substituents, these can be identical or different.
In a preferred embodiment, R.sup.1 and R.sup.2 are each, independently of one another, in particular
REFERENCES:
patent: 3079366 (1963-02-01), Boyle et al.
patent: 4218515 (1980-08-01), Heckles
patent: 5155152 (1992-10-01), Wehner et al.
Aumueller Alexander
Holderbaum Martin
Trauth Hubert
BASF - Aktiengesellschaft
Gupta Yogendra N.
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