Moisture curable materials for delivery of agents, methods, and medical devices

Abstract

The present invention provides curable materials, medical devices incorporating such materials, wherein the curable materials are capable of releasing hydrolyzable leaving agents upon hydrolysis that can form agents (e.g., pharmaceutically active agents), and methods of making and using such materials and devices.

1 . A curable material comprising a prepolymer comprising at least one silicon atom and at least one hydrolyzable leaving group bonded to at least one silicon atom, wherein the hydrolyzable leaving group forms a pharmaceutically active agent upon hydrolysis of the prepolymer and release of the hydrolyzable leaving group. 
     
     
         2 . The material of  claim 1  wherein the prepolymer comprises a monomer, an oligomer, a polymer, or mixtures thereof. 
     
     
         3 . The material of  claim 1  wherein the pharmaceutically active agent includes one or more active hydrogen atoms. 
     
     
         4 . The material of  claim 3  wherein the pharmaceutically active agent comprises one or more hydroxyl groups, carboxylic acid groups, amine groups, amide groups, urea groups, carbamate groups, urethane groups, hemiketal groups, hemiacetal groups, or combinations thereof. 
     
     
         5 . The material of  claim 4  wherein the pharmaceutically active agent is selected from the group consisting of salicylic acid, fenbufen, cortisone, ibuprofen, diflunisal, sulindac, difluprednate, prednisone, medrysone, acematacin, indomethacin, meloxicam, camptothecin, benoxinate, benzocaine, procaine, ciprofloxacin, norfloxacin, clofoctol, and combinations thereof. 
     
     
         6 . The material of  claim 1  wherein a curable intermediate is formed upon hydrolysis of the prepolymer and release of the hydrolyzable leaving group. 
     
     
         7 . The material of  claim 6  wherein the curable intermediate forms a biocompatible polymer upon condensation. 
     
     
         8 . The material of  claim 6  wherein the curable intermediate comprises at least two silanol groups. 
     
     
         9 . The material of  claim 1  wherein the prepolymer is a polymer and further comprises a poly(alkylene oxide) segment, a polysiloxane segment, a polyester segment, a poly(vinyl pyrrolidone) segment, a polyacrylate segment, a polymethacrylate segment, a polycarbonate segment, a hydrocarbon segment, a polycarbosilane segment, a fluoropolymeric segment, a polyoxazoline segment, or mixtures or copolymers thereof. 
     
     
         10 . The material of  claim 1  wherein the prepolymer comprises one or more silicon atoms per one hydrolyzable group. 
     
     
         11 . The material of  claim 10  wherein the hydrolyzable group is a terminal group bonded to the silicon atom. 
     
     
         12 . The material of  claim 1  wherein the prepolymer comprises one silicon atom per one or two hydrolyzable groups. 
     
     
         13 . The material of  claim 1  wherein the prepolymer comprises one silicon atom per one to three hydrolyzable groups. 
     
     
         14 . The material of  claim 1  wherein the prepolymer comprises two silicon atoms per one hydrolyzable group. 
     
     
         15 . The material of  claim 14  wherein the hydrolyzable group is bonded to the two silicon atoms to form a linear polymer. 
     
     
         16 . The material of  claim 14  wherein the hydrolyzable group is attached to the two silicon atoms to form a ring. 
     
     
         17 . The material of  claim 1  wherein the prepolymer comprises one or more silicon-bonded hydrolyzable leaving groups pendant from a polymeric chain. 
     
     
         18 . The material of  claim 1  further comprising particulate material. 
     
     
         19 . The material of  claim 1  wherein the prepolymer is formed by polymerizing a polymerizable monomer comprising at least one silicon atom and at least one hydrolyzable leaving group bonded to at least one silicon atom. 
     
     
         20 . The material of  claim 1  wherein the prepolymer is biocompatible. 
     
     
         21 . The material of  claim 19  wherein the polymerizable monomer is formed by reacting a pharmaceutically active agent and a silicon-containing starting material of the formula SiX x R y  wherein:
 each X is independently a halogen, pseudohalogen, alkoxy, or acetoxy;   each R is independently hydrogen or an organic group; and   x=0-4, y=0-4, and x+y=4.   
     
     
         22 . The material of  claim 19  wherein the polymerizing reaction is a hydrosilylation reaction. 
     
     
         23 . The material of  claim 19  wherein the polymerizing reaction is an alkene metathesis reaction. 
     
     
         24 . The material of  claim 19  wherein the prepolymer is formed by reacting a pharmaceutically active agent and a silicon-containing starting material of the formula X x′ R y′ Si—R 1 —SiX x′ R y′  wherein:
 each X is independently a halogen or pseudohalogen;   each R is independently hydrogen or an organic group; and   R 1  is an alkylene, a divalent siloxane, a divalent oligo- or poly-alkylene oxide, a divalent carbosilane; and   x′=0-3, y′=0-3, and x′+y′=3.   
     
     
         25 . The material of  claim 1  wherein the prepolymer is formed by reacting a pharmaceutically active agent and a silicon-containing polymer.