Novel amino acid compounds and photoprotecting compositions comprised thereof

Abstract

Amino acid compounds having the formula (I): are well suited for the UV-photoprotection of human skin and/or hair, as well as for the UV-photoprotection of a wide variety of photosensitive industrial materials/substrates, e.g., plastics, glasses, textiles, etc.

What is claimed is:  
     
         1 . An amino acid compound having the following structural formula (I):  
       
         
           
           
               
               
           
         
       
       in which  n  is an integer ranging from 1 to 4; and R 1  is one of the following radicals of formula (1), (2), (3), (4), (5), (6) or (7):  
       
         
           
           
               
               
           
         
       
       in which  p  is an integer ranging from 1 to 3; R 2  is a hydrogen atom, a C 1 -C 8  alkyl radical, a C 1 -C 8 O-alkyl radical or a C 1 -C 8  O-acyl radical; R 3  and R 4 , which may be identical or different, are each a hydrogen or halogen atom, or C 1 -C 8  alkyl or alkoxy, or a radical of the following formula (8):  
       
         
           
           
               
               
           
         
       
       R 5  is a hydrogen or halogen atom, a C 1 -C 8  alkyl or alkoxy radical, or a divalent radical:  
       
         
           
           
               
               
           
         
       
       R 6  is a hydrogen atom, a C 1 -C 8  alkyl radical, or a divalent radical:  
       
         
           
           
               
               
           
         
       
       with the proviso that at least one of the two substituents R 5  and R 6  is the divalent radical:  
       
         
           
           
               
               
           
         
       
       R 7  is a C 1 -C 8  alkyl radical; and the acid or base salts thereof; said amino acid compound being in the form of a mixture of isomers or a pure isomer, and also being other than N ε -cinnamoyl-L-lysine and other than 
 3[(1-oxo-3-phenyl-2-propenyl)amino]-L-alanine and the monohydrochloride thereof.  
 
     
     
         2 . An amino acid compound as defined by  claim 1 , wherein formula (I),  n =3 (ornithine compound) or  n =4 (lysine compound).  
     
     
         3 . An amino acid compound as defined by  claim 1 , being 
 N ε -(4-methoxycinnamoyl)-L-lysine, or    N ε -[4-(4,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-ylidenemethyl) benzenesulfonyl]-L-lysine.    
     
     
         4 . An amino acid compound as defined by  claim 1 , wherein formula (I), R 1  is a radical of formula (1).  
     
     
         5 . An amino acid compound as defined by  claim 1 , wherein formula (I), R 1  is a radical of formula (2).  
     
     
         6 . An amino acid compound as defined by  claim 1 , wherein formula (I), R 1  is a radical of formula (3).  
     
     
         7 . An amino acid compound as defined by  claim 1 , wherein formula (I), R 1  is a radical of formula (4).  
     
     
         8 . An amino acid compound as defined by  claim 1 , wherein formula (I), R 1  is a radical of formula (5).  
     
     
         9 . An amino acid compound as defined by  claim 1 , wherein formula (I), R 1  is a radical of formula (6).  
     
     
         10 . An amino acid compound as defined by  claim 1 , wherein formula (I), R 1  is a radical of formula (7).  
     
     
         11 . Particulates of an amino acid compound as defined by  claim 1 , the mean particle size of which being less than 50 μm.  
     
     
         12 . The particulates as defined by  claim 11 , the mean particle size of which ranging from about 0.01 μm to about 20 μm.  
     
     
         13 . A process for the preparation of an amino acid compound of formula (1) as defined in  claim 1 , comprising (a) first complexing the NH 2 —CH(COOH)— moiety of an amino acid monohydrochloride having the following formula (II):  
       
         
           
           
               
               
           
         
       
       with copper sulfate in a basic medium in the presence of a polar solvent; (b) next reacting, in the presence of a polar organic solvent, the copper complex thus prepared with an acid chloride R 1 COCl or a sulfonyl chloride R 1 SO 2 Cl; (c) then recovering, by filtration, the precipitate obtained in step (b); and (d) decomplexing the product thus obtained with a sequestering agent.  
     
     
         14 . A photoprotective cosmetic composition suited for the UV-photoprotection of human skin and/or hair, comprising an effective UV-photoprotective amount of at least one amino acid compound having the structural formula (I):  
       
         
           
           
               
               
           
         
       
       in which  n  is an integer ranging from 1 to 4; and R 1  is one of the following radicals of formula (1), (2), (3), (4), (5), (6) or (7):  
       
         
           
           
               
               
           
         
       
       in which p is an integer ranging from 1 to 3; R 2  is a hydrogen atom, a C 1 -C 8  alkyl radical, a C 1 -C 8  O-alkyl radical, or a C 1 -C 8  O-acyl radical; R 3  and R 4 , which may be identical or different, are each a hydrogen or halogen atom, or C 1 -C 8  alkyl or alkoxy, or a radical of the following formula (8):  
       
         
           
           
               
               
           
         
       
       R 5  is a hydrogen or halogen atom, a C 1 -C 8  alkyl or alkoxy radical, or a divalent radical:  
       
         
           
           
               
               
           
         
       
       R 6  is a hydrogen atom, a C 1 -C 8  alkyl radical, or a divalent radical:  
       
         
           
           
               
               
           
         
       
       with the proviso that at least one of the two substituents R 5  and R 6  is the divalent radical:  
       
         
           
           
               
               
           
         
       
       R 7  is a C 1 -C 8  alkyl radical; or an acid or base salt thereof, formulated into a topically applicable, cosmetically acceptable vehicle, diluent or carrier therefor.  
     
     
         15 . The photoprotective cosmetic composition as defined by  claim 14 , wherein formula (I),  n =3 (ornithine compound) or  n =4 (lysine compound).  
     
     
         16 . The photoprotective cosmetic composition as defined by  claim 15 , said amino acid compound of formula (I) being N ε -cinnamoyl-L-lysine; N ε -(4-methoxycinnamoyl)-L-lysine; or N ε -[4-(4,7,7-trimethyl-3-oxobicyclo[2.2.1] hept-2-ylidenemethyl)benzenesulfonyl]-L-lysine.  
     
     
         17 . The photoprotective cosmetic composition as defined by  claim 14 , comprising particulates of the amino acid compound of formula (I), the mean particle size of which being less than 50 μm.  
     
     
         18 . The photoprotective cosmetic composition as defined by  claim 17 , said particulates having a mean particle size ranging from about 0.01 μm to about 20 μm.  
     
     
         19 . The photoprotective cosmetic composition as defined by  claim 14 , comprising from 0.1% to 20% by weight of said at least one amino acid compound of formula (I).  
     
     
         20 . The photoprotective cosmetic composition as defined by  claim 14 , comprising an oil-in-water emulsion.  
     
     
         21 . The photoprotective cosmetic composition as defined by  claim 14 , further comprising at least one additional, hydrophilic or lipophilic, organic screening agent active in the UV-A and/or UV-B regions.  
     
     
         22 . The photoprotective cosmetic composition as defined by  claim 21 , said at least one additional organic screening agent being selected from among cinnamic derivatives, dibenzoylmethane derivatives, salicylic derivatives, camphor derivatives, triazine derivatives, benzophenone derivatives, β,β-diphenylacrylate derivatives, benzimidazole derivatives, bisbenzoazolyl derivatives, bishydroxyphenolbenzotriazole derivatives, p-aminobenzoic acid derivatives, or screening hydrocarbonaceous polymers and screening silicones.  
     
     
         23 . The photoprotective cosmetic composition as defined by  claim 14 , further comprising at least one additional UV-photoprotective agent selected from among coated or uncoated metal oxide pigments or nonopigments.  
     
     
         24 . The photoprotective cosmetic composition as defined by  claim 23 , comprising pigments or nanopigments of titanium, zinc, iron, zirconium or cerium oxides and mixtures thereof.  
     
     
         25 . The photoprotective cosmetic composition as defined by  claim 14 , further comprising at least one agent for the artificial tanning and/or browning of the skin.  
     
     
         26 . The photoprotective cosmetic composition as defined by  claim 14 , further comprising at least one adjuvant or additive selected from among fatty substances, organic solvents, thickeners, softeners, antioxidants, opacifiers, stabilizers, emollients, hydroxy acids, antifoaming agents, moisturizing agents, vitamins, fragrances, preservatives, surfactants, fillers, sequestering agents, polymers, propellants, bastifying or acidifing agents, or dyes or colorants.  
     
     
         27 . The photoprotective cosmetic composition as defined by  claim 14 , comprising a nonionic vesicular dispersion, a cream, a milk, a gel, a cream gel, a lotion, a suspension, an ointment, a dispersion, a paste, a powder, a solid, a shampoo, a foam or a spray.  
     
     
         28 . The photoprotective cosmetic composition as defined by  claim 14 , comprising a makeup for the eyelashes, eyebrows or skin.  
     
     
         29 . A regime/regimen for protecting human skin and/or hair against the deleterious effects of ultraviolet irradiation, comprising topically applying thereon an effective UV-photoprotecting amount of the photoprotecting cosmetic composition as defined by  claim 14 .  
     
     
         30 . A photostable but normally UV-photosensitive industrial material/substrate which comprises an effective UV-photoprotecting amount of at least one amino acid compound having structural formula (I):  
       
         
           
           
               
               
           
         
       
       in which  n  is an integer ranging from 1 to 4; and R 1  is one of the following radicals of formula (1), (2), (3), (4), (5), (6) or (7):  
       
         
           
           
               
               
           
         
       
       in which  p  is an integer ranging from 1 to 3; R 2  is a hydrogen atom, a C 1 -C 8  alkyl radical, a C 1 -C 8  O-alkyl radical, or a C 1 -C 8  O-acyl radical; R 3  and R 4 , which may be identical or different, are each a hydrogen or halogen atom, or C 1 -C 8  alkyl or alkoxy, or a radical of the following formula (8):  
       
         
           
           
               
               
           
         
       
       R 5  is a hydrogen or halogen atom, a C 1 -C 8  alkyl or alkoxy radical, or a divalent radical:  
       
         
           
           
               
               
           
         
       
       R 6  is a hydrogen atom, a C 1 -C 8  alkyl radical, or a divalent radical:  
       
         
           
           
               
               
           
         
       
       with the proviso that at least one of the two substituents R 5  and R 6  is the divalent radical:  
       
         
           
           
               
               
           
         
       
       R 1  is a C 1 -C 8  alkyl radical; or an acid or base salt thereof.  
     
     
         31 . The photostable but normally UV-photosensitive industrial material/substrate as defined by  claim 30 , comprising a glass, plastic, textile, paint, varnish, or foodstuff.  
     
     
         32 . The photostable but normally UV-photosensitive industrial material/substrate as defined by  claim 30 , at least one face surface thereof being coated with said at least one amino acid compound having the structural formula  
     
     
         33 . The photostable but normally UV-photosensitive industrial material/substrate as defined by  claim 30 , the composition or body thereof comprising said at least one amino acid compound having the structural formula (I).