N-acetyl aldosamines, n-acetylamino acids and related n-acetyl compounds and their topical use

A composition comprising:

• (A) a pharmaceutically acceptable vehicle for topical treatment of cosmetic conditions or dermatological disorders,
• (B) a therapeutically effective amount of at least one compound selected from the group consisting of N-acetyl aldosamines, N-acetylamino acids, and isomeric or nonisomeric, free acid, salt, lactone, amide, or ester forms thereof, wherein said N-acetyl aldosamine has the formula:
• ##STR4## wherein n is an integer;
• R.sub.1 is selected from the group consisting of CHO, CONH.sub.2, and COOR.sub.3 ;
• R.sub.2 is selected from the group consisting of H, I, F, Cl, Br, and an alkyl, alkoxyl, aralkyl or aryl group of saturated or unsaturated, straight or branched chain or cyclic form having 1 to 19 carbon atoms;
• R.sub.3 is selected from the group consisting of H and an alkyl, aralkyl, or aryl group having from 1 to 9 carbon atoms,
• wherein said N-acetylamino acid has the formula:
• ##STR5## wherein R.sub.1 is H or an alkyl or aralkyl group having 1 to 14 carbon atoms;
• n is an integer;
• R.sub.2 is OH, NH.sub.2 or OR.sub.3 ;
• and R.sub.3 is an alkyl, aralkyl or aryl group having 1 to 9 carbon atoms which may be saturated or unsaturated, straight or branched chain or cyclic form;
• H attached to a carbon atom may be substituted by I, F, Cl, Br or an alkoxyl group having 1 to 9 carbons;
• and R.sub.1 may carry OH, SH, SCH.sub.3, COOH, NH.sub.2, CONH.sub.2, guanidine or heterocyclic group,
• and wherein said N-acetylamino acid is not N-acetylcysteine or a derivative thereof, and
• (C) a cosmetic, pharmaceutical or other topical agent.

A composition comprising (A) a pharmaceutically acceptable vehicle for topical treatment of cosmetic conditions or dermatological disorders and (B) at least 1% by total weight of the composition of at least one compound selected from the group consisting of N-acetyl aldosamines, N-acetylamino acids, and isomeric or nonisomeric, free acid, salt, lactone, amide, or ester forms thereof,

• wherein said N-acetyl aldosamine has the formula:
• ##STR6## wherein n is an integer;
• R.sub.1 is selected from the group consisting of CHO, CONH.sub.2, and COOR.sub.3 ;
• R.sub.2 is selected from the group consisting of H, I, F, Cl, Br, and an alkyl, alkoxyl, aralkyl or aryl group of saturated or unsaturated, straight or branched chain or cyclic form having 1 to 19 carbon atoms;
• R.sub.3 is selected from the group consisting of H and an alkyl, aralkyl, or aryl group having from 1 to 9 carbon atoms,
• wherein said N-acetylamino acid or isomeric or nonisomeric, free acid, salt, lactone, amide, or ester form thereof is at least one member selected from the group consisting of N-acetyl-glycine, N-acetyl-alanine, N-acetyl-valine, N-acetyl-leucine, N-acetyl-isoleucine, N-acetyl-serine, N-acetyl-threonine, N-acetyl-tyrosine, N-acetyl-cysteine, N-acetyl-methionine, N-acetyl-aspartic acid, N-acetyl-asparagine, N-acetyl-glutamine, N-acetyl-arginine, N-acetyl-lysine, N-acetyl-histidine, N-acetyl-phenylalanine, N-acetyl-tyrosine, N-acetyl-tryptophan, N-acetyl-proline, N-acetyl-.beta.-alanine, N-acetyl-taurine, N-acetyl-r-aminobutanoic acid, N-acetyl-hydroxyproline, N-acetyl-canavanine, N-acetyl-hydroxylysine, N-acetyl-cycloserine, N-acetyl-homoarginine, N-acetyl-norleucine, N-acetyl-norvaline, N-acetyl-homoserine, N-acetyl-methylserine, N-acetyl-hydroxyvaline, N-acetyl-ethionine, N-acetyl-methoxinine, N-acetyl-.beta.-aminoisobutanoic acid, N-acetyl-homocysteine, N-acetyl-cysteine sulfinic acid, N-acetyl-homophenylalanine, N-acetyl-homotryptophan, N-acetyl-5-hydroxytryptamine (N-acetylserotonin), N-acetyltryptamine, N-acetyl-ornithine, N-acetyl-citrulline, N-acetyl-argininosuccinic acid, N-acetyl-dopa, N-acetyl-3-iodotyrosine, N-acetyl-3,5-diiodotyrosine, N-acetyl-3,5,3'-triiodothyronine, N-acetyl-thyroxine, N-acetyl-creatine, N-acetyl-creatinine, N-acetyl-cystine, N-acetyl-homocystine, and isomeric or nonisomeric, free acid, salt, lactone, amide, or ester forms thereof, and N-acetyl glutamic acid and isomeric or nonisomeric, free acid, lactone, amide, or ester forms thereof.

A composition comprising:

• (A) a pharmaceutically acceptable vehicle for topical treatment of cosmetic conditions or dermatological disorders,
• (B) at least 1% by total weight of the composition of at least one compound selected from the group consisting of N-acetyl aldosamines, N-acetylamino acids, and isomeric or nonisomeric, free acid, salt, lactone, amide, or ester forms thereof,
• wherein said N-acetyl aldosamine has the formula:
• ##STR7## wherein n is an integer;
• R.sub.1 is selected from the group consisting of CHO, CONH.sub.2, and COOR.sub.3 ;
• R.sub.2 is selected from the group consisting of H, I, F, Cl, Br, and an alkyl, alkoxyl, aralkyl or aryl group of saturated or unsaturated, straight or branched chain or cyclic form having 1 to 19 carbon atoms;
• R.sub.3 is selected from the group consisting of H and an alkyl, aralkyl, or aryl group having from 1 to 9 carbon atoms,
• wherein said N-acetylamino acid is N-acetyl-proline or has the formula:
• ##STR8## wherein R.sub.1 is H or an alkyl or aralkyl group having 1 to 14 carbon atoms;
• n is an integer;
• R.sub.2 is OH, NH.sub.2 or OR.sub.3 ;
• and R.sub.3 is an alkyl, aralkyl or aryl group having 1 to 9 carbon atoms which may be saturated or unsaturated, straight or branched chain or cyclic form;
• H attached to a carbon atom may be substituted by I, F, Cl, Br or an alkoxyl group having 1 to 9 carbons;
• and R.sub.1 may carry OH, SH, SCH.sub.3, COOH, NH.sub.2, CONH.sub.2, guanidine or heterocyclic group,
• and wherein said N-acetylamino acid is not N-acetylcysteine or a derivative thereof, and
• (C) a cosmetic, pharmaceutical or other topical agent.

A method for treating cosmetic conditions and dermatological disorders comprising topically applying a composition comprising (A) a pharmaceutically acceptable vehicle for topical treatment of cosmetic conditions or dermatological disorders and (B) a therapeutically effective amount of a composition comprising at least one compound selected from the group consisting of N-acetyl aldosamines, N-acetylamino acids and isomeric or nonisomeric, free acid, salt, lactone, amide, or ester forms thereof,

• wherein said N-acetyl aldosamine has the formula:
• ##STR9## wherein n is an integer;
• R.sub.1 is selected from the group consisting of CHO, CONH.sub.2, and COOR.sub.3 ;
• R.sub.2 is selected from the group consisting of H, I, F, Cl, Br, and an alkyl, alkoxyl, aralkyl or aryl group of saturated or unsaturated, straight or branched chain or cyclic form having 1 to 19 carbon atoms;
• R.sub.3 is selected from the group consisting of H and an alkyl, aralkyl or aryl group having from 1 to 9 carbon atoms, and
• wherein said N-acetylamino acid or isomeric or nonisomeric, free acid, salt, lactone, amide, or ester form thereof is at least one member selected from the group consisting of N-acetyl-glycine, N-acetyl-alanine, N-acetyl-valine, N-acetyl-leucine, N-acetyl-isoleucine, N-acetyl-serine, N-acetyl-threonine, N-acetyl-tyrosine, N-acetyl-cysteine, N-acetyl-methionine, N-acetyl-aspartic acid, N-acetyl-asparagine, N-acetyl-glutamine, N-acetyl-arginine, N-acetyl-lysine, N-acetyl-histidine, N-acetyl-phenylalanine, N-acetyl-tyrosine, N-acetyl-tryptophan, N-acetyl-proline, N-acetyl-.beta.-alanine, N-acetyl-taurine, N-acetyl-r-aminobutanoic acid, N-acetyl-hydroxyproline, N-acetyl-canavanine, N-acetyl-hydroxylysine, N-acetyl-cycloserine, N-acetyl-homoarginine, N-acetyl-norleucine, N-acetyl-norvaline, N-acetyl-homoserine, N-acetyl-methylserine, N-acetyl-hydroxyvaline, N-acetyl-ethionine, N-acetyl-methoxinine, N-acetyl-.beta.-aminoisobutanoic acid, N-acetyl-homocysteine, N-acetyl-cysteine sulfinic acid, N-acetyl-homophenylalanine, N-acetyl-homotryptophan, N-acetyl-5-hydroxytryptamine (N-acetylserotonin), N-acetyltryptamine, N-acetyl-ornithine, N-acetyl-citrulline, N-acetyl-argininosuccinic acid, N-acetyl-dopa, N-acetyl-3-iodotyrosine, N-acetyl-3,5-diiodotyrosine, N-acetyl-3,5,3'-triiodothyronine, N-acetyl-thyroxine, N-acetyl-creatine, N-acetyl-creatinine, N-acetyl-cystine, N-acetyl-homocystine, and isomeric or nonisomeric, free acid, salt lactone, amide, or ester forms thereof, and N-acetyl-glutamic acid and isomeric or nonisomeric, free acid, lactone, amide, or ester forms thereof.

A method for treating cosmetic conditions and dermatological disorders comprising topically applying a composition comprising:

• (A) a pharmaceutically acceptable vehicle for topical treatment of cosmetic conditions or dermatological disorders,
• (B) a therapeutically effective amount of at least one compound selected from the group consisting of N-acetyl aldosamines, N-acetylamino acids, and isomeric or nonisomeric, free acid, salt, lactone, amide, or ester forms thereof,
• wherein said N-acetyl aldosamine has the formula:
• ##STR10## wherein n is an integer;
• R.sub.1 is selected from the group consisting of CHO, CONH.sub.2, and COOR.sub.3 ;
• R.sub.2 is selected from the group consisting of H, I, F, Cl, Br, and an alkyl, alkoxyl, aralkyl or aryl group of saturated or unsaturated, straight or branched chain or cyclic form having 1 to 19 carbon atoms;
• R.sub.2 is selected from the group consisting of H and an alkyl, aralkyl, or aryl group having from 1 to 9 carbon atoms,
• wherein said N-acetylamino acid is N-acetyl-proline or has the formula:
• ##STR11## wherein R.sub.1 is H or an alkyl or aralkyl group having 1 to 14 carbon atoms;
• n is an integer;
• R.sub.2 is OH, NH.sub.2 or OR.sub.3 ;
• and R.sub.3 is an alkyl, aralkyl or aryl group having 1 to 9 carbon atoms which may be saturated or unsaturated, straight or branched chain or cyclic form;
• H attached to a carbon atom may be substituted by I, F, Cl, Br or an alkoxyl group having 1 to 9 carbons;
• and R.sub.1 may carry OH, SH, SCH.sub.3, COOH, NH.sub.2, CONH.sub.2, guanidine or heterocyclic group,
• and wherein said N-acetylamino acid is not N-acetylcysteine or a derivative thereof, and
• (C) a cosmetic, pharmaceutical or other topical agent.