Dermal filler compositions including antioxidants

Abstract

Dermal filler compositions presented herein can contain a vitamin that is conjugated to a hyaluronic acid.

What is claimed is: 
     
         1 . An injectable dermal filler composition comprising ascorbyl-3 aminopropyl phosphate covalently conjugated to hyaluronic acid (HA) via 1,4-butanediol diglycidyl ether (BDDE) or via amidization, wherein the HA is crosslinked. 
     
     
         2 . The composition of  claim 1 , wherein the ascorbyl-3 aminopropyl phosphate is covalently conjugated to hyaluronic acid (HA) via 1,4-butanediol diglycidyl ether (BDDE). 
     
     
         3 . The composition of  claim 1 , wherein the ascorbyl-3 aminopropyl phosphate is covalently conjugated to hyaluronic acid (HA) via amidization. 
     
     
         4 . The composition of  claim 3 , wherein the amidization is in the presence of a carbodiimide coupling agent. 
     
     
         5 . The composition of  claim 4 , wherein the amidization takes place in the presence of 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (EDC) and N-hydroxysuccinimide (NHS) and N-hydroxysulfosuccinimide (SulfoNHS). 
     
     
         6 . The composition of  claim 1 , wherein the HA is crosslinked via BDDE. 
     
     
         7 . The composition of  claim 1 , having a degree of conjugation of between about 3 mol % and about 40 mol %. 
     
     
         8 . The composition of  claim 1 , having a degree of conjugation of between about 3 mol % and about 15 mol %. 
     
     
         9 . The composition of  claim 1 , having a degree of conjugation of between about 10 mol % and about 13 mol %. 
     
     
         10 . The composition of  claim 1 , wherein the crosslinked HA comprises a combination of both high molecular weight hyaluronan polymers and low molecular weight hyaluronan polymers. 
     
     
         11 . The composition of  claim 10 , wherein the high molecular weight hyaluronan polymers have a mean molecular weight of 1,000,000 Da or greater than 1,000,000 Da. 
     
     
         12 . The composition of  claim 11 , wherein the high molecular weight hyaluronan polymers have a mean molecular weight of about 1,500,000 Da, about 2,000,000 Da, about 2,500,000 Da, about 3,000,000 Da, about 3,500,000 Da, about 4,000,000 Da, about 4,500,000 Da, or about 5,000,000 Da. 
     
     
         13 . The composition of  claim 10 , wherein the low molecular weight hyaluronan polymers have a mean molecular weight of less than 1,000,000 Da. 
     
     
         14 . The composition of  claim 13 , wherein the low molecular weight hyaluronan polymers have a mean molecular weight of about 200,000 Da, about 300,000 Da, about 400,000 Da, about 500,000 Da, about 600,000, about 700,000 Da, about 800,000 Da, or about 900,000 Da. 
     
     
         15 . The composition of  claim 10 , having a ratio of high molecular weight hyaluronan polymers to low molecular weight hyaluronan polymers of about 1:1, about 1:5, about 1:10, about 1:15, or about 1:20. 
     
     
         16 . The composition of  claim 15 , wherein the ratio of high molecular weight hyaluronan polymers to low molecular weight hyaluronan polymers is about 1:10. 
     
     
         17 . The composition of  claim 1 , wherein the crosslinked HA is present at a concentration of about 10 mg/g, about 11 mg/g, about 12 mg/g, about 13 mg/g, about 14 mg/g, about 15 mg/g, about 16 mg/g, about 17 mg/g, about 18 mg/g, about 19 mg/g or about 20 mg/g. 
     
     
         18 . The composition of  claim 17 , wherein the crosslinked HA is present at a concentration of about 20 mg/g. 
     
     
         19 . The composition of  claim 17 , wherein the crosslinked HA is present at a concentration of about 15 mg/g. 
     
     
         20 . The composition of  claim 1 , further comprising an anesthetic agent. 
     
     
         21 . The composition of  claim 20 , wherein the anesthetic agent is lidocaine or a salt thereof. 
     
     
         22 . A method of treating a soft tissue condition, the method comprising administering the composition of  claim 1  to a subject in need thereof.