Dermal filler compositions including antioxidants

Abstract

Provided are injectable, hyaluronic acid-based hydrogel compositions including conjugated vitamins.

What is claimed is: 
     
         1 . An injectable dermal filler comprising:
 hyaluronic acid; and   a vitamin C derivative covalently conjugated to the hyaluronic acid;
 wherein a degree of conjugation is between about 3 mol % and about 40 mol %. 
   
     
     
         2 . The dermal filler of  claim 1  wherein the hylauronic acid is crosslinked with Star-PEG epoxide. 
     
     
         3 . The dermal filler of  claim 1  wherein the hyaluronic acid is crosslinked with Star-PEG amine. 
     
     
         4 . The dermal filler of  claim 1  wherein the hyaluronic acid is crosslinked with BDDE. 
     
     
         5 . The dermal filler of  claim 4  wherein and the degree of conjugation is between about 3 mol % and about 15 mol %. 
     
     
         6 . The dermal filler of  claim 1  wherein vitamin C derivative is AA2G. 
     
     
         7 . The dermal filler of  claim 1  wherein the vitamin C derivative is Vitagen. 
     
     
         8 . The dermal filler of  claim 1  wherein the vitamin C derivative is AA2P. 
     
     
         9 . The dermal filler of  claim 1  used in treating a skin defect wherein, when introduced into the skin of a human being, releases ascorbic acid into the human being for at least about 1 month and up to about 20 months. 
     
     
         10 . An injectable dermal filler comprising:
 hyaluronic acid crosslinked with Star PEG amine and having a degree of conjugation of between about 3 mol % and about 40 mol %; and   AA2P covalently conjugated to the hyaluronic acid
 wherein the dermal filler, when introduced into the skin of a human being, releases ascorbic acid into the human being for at least about 1 months and up to about 20 months. 
   
     
     
         11 . A method of making a dermal filler comprising the steps of:
 providing hyaluronic acid;   reacting a crosslinking agent with a Vitamin C derivative;   adding the reacted crosslinking agent and Vitamin C derivative to the hyaluronic acid to form a crosslinked hyaluronic acid composition including covalently conjugated Vitamin C; and   homogenizing and neutralizing the crosslinked hyaluronic acid composition to obtain an injectable gel having a conjugation degree of between about 3 mol % and about 40 mol %.   
     
     
         12 . The method of  claim 11  wherein the step of reacting comprises pre-reacting vitamin C derivatives with crosslinker to achieve a composition containing Vitamin C derivative capped by crosslinker, unreacted crosslinker and free AA2G. 
     
     
         13 . The method of  claim 12  wherein the crosslinker is BDDE and vitamin C derivative is AA2G, vitagen, and SAP. 
     
     
         14 . The method of  claim 12  wherein the crosslinker is 4-arm epoxide and vitamin C derivative is AA2G, vitagen, and SAP. 
     
     
         15 . The method of  claim 11  wherein the crosslinking agent is Star-PEG epoxide. 
     
     
         16 . The method of  claim 11  wherein the crosslinking agent is Star-PEG amine. 
     
     
         17 . The method of  claim 11  wherein vitamin C derivative is AA2G. 
     
     
         18 . The method of  claim 11  wherein the vitamin C derivative is Vitagen. 
     
     
         19 . The method of  claim 11  wherein the vitamin C derivative is AA2P. 
     
     
         20 . A method of treating a skin condition comprising introducing the dermal filler of  claim 1  into a patient.