Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1987-12-14
1994-03-29
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560 9, 560 15, 560 19, 560 21, 560 22, 560 23, 560 37, 560 38, 560 39, 560 41, 560 42, 560 43, 560 44, 560 45, 560 48, 560 49, 560 50, 562426, 562431, 562433, 562442, 562443, 562444, 562450, 562451, 562452, 562455, 564153, 564154, 564155, 564157, 564158, 564161, 564162, 564163, 564164, 564165, 564167, 564168, 564169, 564170, 564171, 564182, 564183, 564184, 564185, 564186, 564187, 5483351, 5483355, 5483361, 5483381, 5483385, 5483401, 5483415, 5483421, C07C32104, C07C22906, C07C22908, C07C22914, C07C23303, C
Patent
active
052986470
DESCRIPTION:
BRIEF SUMMARY
The present invention has for an object the synthesis and/or use of compounds capable of opposing, in the form of solar filters and if desired by induction of melanogenesis, the harmful effects of solar radiation and photosensibilization reactions induced in man, especially during use of certain medicaments or perfumes or cosmetic preparations. They are aromatic compounds absorbing UVB and/or UVA, substituted with an amide function, as well as derivative compounds obtained by introduction of an ethylenic spacer between the aromatic structure and the amide function, without modification of the spectral characteristics.
At present, a wide range of sun-blocking preparations have been developed for protecting the skin. These preparations contain as active ingredients compounds capable of selectively absorbing harmful solar radiation. But these products have the disadvantage of being difficult to apply to the surface of the skin, and of being eliminated during their use (by sweat, swimming in the ocean, . . . ) Moreover, certain among them pass through the skin and into the blood stream (D. Claus - Doctorate thesis from the University of Strasbourg, mentioned in Pharmacie 1982); they thus lose their activity and risk endangering the health of the user in case of prolonged use. Derivatives of para-methoxycinnamic acid are the most widely used sun screens in the world. To retain this type of compound on the surface of the skin, one solution consists of attaching to their chemical structure isolated amino groups (French patent No. 81.08429), or amino acids or peptides which bind to the surface of the skin. Thus, two series of amino acid compounds of para-methoxycinnamic acid and trans-urocanic acid have recently been synthesized, and their sun-blocking properties claimed (French patent No. 84.100009 and French patent No. 85.04898). For protecting against harmful solar radiation, another solution consists of stimulating the principal natural protective system of the skin, melanogenesis. At the present time, none of the products used as sunscreens claim that property.
The new compounds according to the invention have either or both of the two properties necessary to obtain maximum effectiveness in solar protection, namely prolonged absorption of harmful ultraviolet radiation by improved skin adherence of the compound, and induction of melanogenesis. The chemical structures envisioned must be able to be solubilized either in a non-aqueous or aqueous solvent; an amphoteric character will permit a disposition at the interface of the globules of an emulsion. The same compound having one or both of the photoprotective properties described above will thus exist either in the form of a liposoluble ester or will have a free carboxylic group, either in the form of an aminoalkyl chain ester, or in a hydrosoluble aminoaryl chain ester, hydrochlorides being an example of hydrosoluble amine salts, or in the form of hydrosoluble organic or inorganic salts of the free carboxylic groups. The ester function may be replaced by an amide function. All the compounds according to the invention are capable of absorbing ultraviolet radiation between 360 nm and 260 nm with a maximum which may be situated either in UVA or UVB, or conjointly in UVA and UVB. The original compounds described for the first time and for which the present invention is claimed are aromatic compounds absorbing UVB and/or UVA, substituted with an amide function, characterized in that they respond to the formulas 1 to 3, ##STR3## and in that, by introduction of an ethylenic spacer between the aromatic structure and the amide function without modification of the spectral characteristics, derivative compounds of formula 4 are obtained ##STR4## wherein R1 may be hydrogen, alkyl or aryl R2 may be a substituent of the formula: ##STR5## in which X and Y may be hydrogen, alkyl, aryl, aminoalkyl or aminoaryl; or ##STR6## in which Z may be hydrogen, alkyl, aryl, aminoalkyl or aminoaryl, X may be hydrogen, alkyl, aryl, aminoalkyl or aminoaryl and n may be an integer from 1 to 6
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Jung Louis
Robert Dominique
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