Use of chromen-4-one derivatives

Abstract

The invention relates to the use of chrome-4-one derivatives of the formula I where R 1 and R 2 may be identical or different and are selected from H, —C(═O)—R 7 , —C(═O)—OR 7 , alkyl groups, alkenyl groups, hydroxyalkyl groups and/or cycloalkyl groups and/or cycloalkenyl groups, R 3 is H or alkyl groups, R 4 is H or OR 8 , R 5 and R 6 are selected from —H, —OH, alkyl groups, alkenyl groups and hydroxyalkyl groups, and R 7 is H, alkyl groups, a polyhydroxyl compound, such as, preferably, an ascorbic acid radical or glycosidic radicals, and R 8 is H or alkyl groups, where at least two of the substituents R 1 , R 2 and R 4 —R 6 are different from H or at least one substituent from R 1 and R 2 is —C(═O)—R 7 or —C(═O)—OR 7 , for the care, preservation or improvement of the general state of the skin or hair.

1 . A method for caring, preserving or improving the general state of skin or hair, for prophylaxis against time- and/or light-induced ageing processes of the human skin or human hair; for prophylaxis against dry skin, wrinkle formation and/or pigment defects; or for the reduction or prevention of the harmful effects of UV rays on the skin, for prophylaxis against or reduction of skin unevenness, such as wrinkles, fine lines, rough skin or large-pored skin, for the prophylaxis and/or prevention of premature skin ageing; the prophylaxis and/or prevention of light- or ageing-induced wrinkling of the skin; for the reduction of pigmentation and keratosis actinica; or for the prophylaxis and/or treatment of a disease that is associated with normal skin ageing or light-induced ageing of the skin, for the prophylaxis and/or treatment of a skin disease that is associated with defective keratinisation relating to differentiation and cell proliferation; for the treatment of acne vulgaris, acne comedonica, polymorphic acne, acne rosaceae, nodular acne, acne conglobata, age-related acne, acne occurring as a side effect, acne solaris, medicament-related acne or acne professionalis; for the treatment of a defect of keratinisation, ichthyosis, an ichthyosiform state, Darier's disease, keratosis palmoplantaris, leukoplasia, a leukoplasiform state, skin and mucosal (buccal) eczema (lichen); for the treatment of a skin disease that is associated with defective keratinisation and has an inflammatory and/or immunoallergic component, or psoriasis relating to the skin, mucous membranes or finger- or toenails, or psoriatic rheumatism or skin atopy, eczema, or respiratory atopy, or hypertrophy of the gums, for the prophylaxis and/or treatment of a benign or malignant excrescence of the dermis or epidermis, which may be of viral origin, of verruca vulgaris, verruca plana, epidermodysplasia verruciformis, oral papillomatosis, papillomatosis florida, or an excrescence that may be caused by UV radiation, or of epithelioma baso-cellulare or epithelioma spinocellulare, comprising applying to the skin or hair at least one compound of formula I  
       
         
           
           
               
               
           
         
       
       or a salt thereof or a composition comprising at least one compound of formula I or a salt thereof, where 
 R 1  and R 2  are identical or different, and are 
 H, —C(═O)—R 7 , —C(═O)—OR 7 ,  
 a straight-chain or branched C 1 - to C 20 -alkyl group,  
 a straight-chain or branched C 3 - to C 20 -alkenyl group, or a straight-chain or branched C 1 -to C 20 -hydroxyalkyl group, where the hydroxyl group is optionally bonded to a primary or secondary carbon atom of the alkyl and wherein the alkyl is optionally interrupted by oxygen,  
 a C 3 - to C 10 -cycloalkyl group, or a C 3 - to C 12 -cycloalkenyl group, where the cyclic group is optionally bridged by —(CH 2 ) n — group, where n=1 to 3,  
 
 R 3  is H or a straight-chain or branched C 1 - to C 20 -alkyl group,  
 R 4  is H or —OR 8 ,  
 R 5  and R 6  are identical or different, and are 
 H or —OH,  
 a straight-chain or branched C 1 - to C 20 -alkyl group,  
 a straight-chain or branched C 3 - to C 20 -alkenyl group,  
 a straight-chain or branched C 1 - to C 20 -hydroxyalkyl group, where the hydroxyl group is optionally bonded to a primary or secondary carbon atom of the alkyl and wherein the alkyl is optionally interrupted by oxygen,  
 
 R 7  is H, a straight-chain or branched C 1 - to C 20 -alkyl group, or a polyhydroxyl compound, and  
 R 8  is H or a straight-chain or branched C 1 - to C 20 -alkyl group,  
 where at least two of the substituents R 1 , R 2  and R 4 —R 6  are different from H or at least one substituent from R 1  and R 2  is —C(═O)—R 7  or —C(═O)—OR 7 .  
 
     
     
         2 . A method according to  claim 1 , wherein the method is for prophylaxis against time- and/or light-induced ageing processes of the human skin or human hair; for prophylaxis against dry skin, wrinkle formation and/or pigment defects; or for the reduction or prevention of the harmful effects of UV rays on the skin.  
     
     
         3 . A method according to  Claim 1 , wherein the method is for prophylaxis against or reduction of skin unevenness, such as wrinkles, fine lines, rough skin or large-pored skin.  
     
     
         4 . A method according to  claim 1 , wherein the method is for the prophylaxis and/or prevention of premature skin ageing; the prophylaxis and/or prevention of light- or ageing-induced wrinkling of the skin; for the reduction of pigmentation and keratosis actinica; or for the prophylaxis and/or treatment of a disease that is associated with normal skin ageing or light-induced ageing of the skin.  
     
     
         5 . A method according to  claim 1 , wherein the method is for the prophylaxis and/or treatment of a skin disease that is associated with defective keratinisation relating to differentiation and cell proliferation; for the treatment of acne vulgaris, acne comedonica, polymorphic acne, acne rosaceae, nodular acne, acne conglobata, age-related acne, acne occurring as a side effect, acne solaris, medicament-related acne or acne professionalis; for the treatment of a defect of keratinisation, ichthyosis, an ichthyosiform state, Darier's disease, keratosis palmoplantaris, leukoplasia, a leukoplasiform state, skin and mucosal (buccal) eczema (lichen); for the treatment of a skin disease that is associated with defective keratinisation and has an inflammatory and/or immunoallergic component, or psoriasis relating to the skin, mucous membranes or finger- or toenails, or psoriatic rheumatism or skin atopy, eczema, or respiratory atopy, or hypertrophy of the gums.  
     
     
         6 . A method according to  claim 1 , wherein the method is for the prophylaxis and/or treatment of a benign or malignant excrescence of the dermis or epidermis, which may be of viral origin, of verruca vulgaris, verruca plana, epidermodysplasia verruciformis, oral papillomatosis, papillomatosis florida, or an excrescence that may be caused by UV radiation, or of epithelioma baso-cellulare or epithelioma spinocellulare.  
     
     
         7 . A method according to  claim 1 , wherein R 3  is H, and R 4  is OH.  
     
     
         8 . A method according to  claim 1 , wherein R 5  and R 6  are H.  
     
     
         9 . A method according to  claim 1 , wherein one of the radicals R 1  and R 2  is H and the other radical of R 1  and R 2  is —C(═O)—R 7 , —C(═O)OR 7  or a straight-chain or branched C 1 - to C 20 -alkyl group.  
     
     
         10 . A method according to  claim 1 , wherein the compound of formula I is a compound of one of the formulae Ia-In:  
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         11 . A composition comprising at least one compound of formula I  
       
         
           
           
               
               
           
         
       
       or a salt thereof or a composition comprising at least one compound of formula I or a salt thereof, where 
 R 1  and R 2  are identical or different, and are 
 H, —C(═O)—R 7 , —C(═O)—OR 7 ,  
 a straight-chain or branched C 1 - to C 20 -alkyl group,  
 a straight-chain or branched C 3 - to C 20 -alkenyl group, or a straight-chain or branched C 1 - to C 20 -hydroxyalkyl group, where the hydroxyl group is optionally bonded to a primary or secondary carbon atom of the alkyl and wherein the alkyl is optionally interrupted by oxygen,  
 a C 3 - to C 10 -cycloalkyl group, or a C 3 - to C 12 -cycloalkenyl group, where the cyclic group is optionally bridged by —(CH 2 ) n — group, where n=1 to 3,  
 
 R 3  is H or a straight-chain or branched C 1 - to C 20 -alkyl group,  
 R 4  is H or OR 8 ,  
 R 5  and R 6  are identical or different, and are 
 H or —OH,  
 a straight-chain or branched C 1 - to C 20 -alkyl group,  
 a straight-chain or branched C 3 - to C 20 -alkenyl group,  
 a straight-chain or branched C 1 - to C 20 -hydroxyalkyl group, where the hydroxyl group is optionally bonded to a primary or secondary carbon atom of the alkyl and wherein the alkyl is optionally interrupted by oxygen,  
 
 R 7  is H, a straight-chain or branched C 1 - to C 20 -alkyl group, or a polyhydroxyl compound, and  
 R 8  is H or a straight-chain or branched C 1 - to C 20 -alkyl group,  
 where at least two of the substituents R 1 , R 2  and R 4 —R 6  are different from H or at least one substituent from R 1  and R 2  is —C(═O)—R 7  or —C(═O)—OR 7 ,  
 and at least one skin-care ingredient other than a compound of formula I, and at least one carrier that is suitable for topical application or is a food-suitable carrier.  
 
     
     
         12 . A composition according to  claim 11 , wherein the composition comprises one or more compounds of formula I in an amount of 0.01 to 20% by weight based on the composition.  
     
     
         13 . A composition according to  claim 11 , wherein the at least one further skin-care ingredient is one or more antioxidants and/or vitamins.  
     
     
         14 . A composition according to  claim 11 , further comprising one or more UV filters.  
     
     
         15 . A composition according to  claim 11 , wherein the at least one further skin-care ingredient is a pyrimidinecarboxylic acid, aryl oxime, or ectoine.  
     
     
         16 . A process for preparing a composition according to  claim 11 , comprising mixing together at least one compound of formula I, at least one skin care ingredient other than a compound of formula I, and at least one carrier that is suitable for topical application.  
     
     
         17 . A method according to  claim 7 , wherein at least one of the radicals R 5  and R 6  is OH.  
     
     
         18 . A composition according to  claim 11 , wherein the composition comprises one or more compounds of formula I in an amount of 0.01 to 10% by weight based on the composition.  
     
     
         19 . A composition according to  claim 11 , wherein the at least one skin-care ingredient is vitamin C or a derivative of vitamin C, DL-α-tocopherol, tocopherol E acetate, nicontinic acid, pantothenic acid or biotin.  
     
     
         20 . A composition according to  claim 11 , wherein the composition does not contain a retinol derivative.  
     
     
         21 . A composition according to  claim 11 , further comprising 3-(4′-methylbenzylidene)-dl-camphor, 1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione, 4-isopropyldibenzoylmethane, 2-hydroxy-4-methoxybenzophenone, octyl methoxycinnamate, 3,3,5-trimethylcyclohexyl salicylate, 2-ethylhexyl 4-(dimethylamino)benzoate, 2-ethylhexyl 2-cyano-3,3-diphenylacrylate, 2-phenylbenzimidazole-5-sulfonic acid or a potassium, sodium or triethanolamine salt thereof.  
     
     
         22 . A composition according to  claim 11 , wherein the at least one carrier that is suitable for topical application is at least one carrier that is a cosmetically or dermatologically or food-suitable carrier.  
     
     
         23 . A method according to  claim 1 , wherein the method is for caring, preserving or improving the general state of skin or hair.  
     
     
         24 . A method according to  claim 1 , wherein R 7  is an ascorbic acid radical or a glycosidic radical.  
     
     
         25 . A method according to  claim 1 , wherein a composition comprising at least one compound of formula I or a salt thereof is administered and the composition contains at least one compound of formula II or a salt thereof  
       
         
           
           
               
               
           
         
       
       where R 1  to R 10  are identical or different, and are 
 H  
 OR 11    
 a straight-chain or branched C 1 - to C 20 -alkyl group,  
 a straight-chain or branched C 3 - to C 20 -alkenyl group,  
 a straight-chain or branched C 1 - to C 20 -hydroxyalkyl group, where the hydroxyl group is optionally bonded to a primary or secondary carbon atom of the alkyl and wherein the alkyl is optionally interrupted by oxygen,  
 a C 3 - to C 10 -cycloalkyl group, or a C 3 - to C 12 -cycloalkenyl group, where the cyclic group is optionally bridged by —(CH 2 ) n — group, where n=1 to 3,  
 where all OR 11  are, independently of one another, 
 OH  
 a straight-chain or branched C 1 - to C 20 -alkoxy group,  
 a straight-chain or branched C 3 - to C 20 -alkenyloxy group,  
 a straight-chain or branched C 1 - to C 20 -hydroxyalkoxy group, where the hydroxyl group(s) are optionally bonded to a primary or secondary carbon atom of the alkyl and wherein the alkyl is optionally interrupted by oxygen,  
 a C 3 - to C 10 -cycloalkoxy group, or C 3 - to C 12 -cycloalkenyloxy group, where the cyclic group is optionally bridged by —(CH 2 ) n — group, where n=1 to 3, or  
 a mono- or oligoglycosyl radical,  
 with the proviso that at least 4 radicals from R 1  to R 7  are OH and that the compound of formula II contains at least two pairs of adjacent —OH groups, or R 2 , R 5  and R 6  are OH and the radicals R 1 , R 3 , R 4  and R 7-10  are H.