Dendritic and star-shaped contrast agents for medical devices and bioabsorbable radiopaque bulk material and method for producing same

Abstract

In accordance with the present invention, a high intensity radiopaque contrast agent is disclosed. The agent may be coated on or incorporated within bulk material which may then be subsequently utilized to fabricate a radiopaque medical device. Primary effects through chemistry include higher radiopaque concentrations per unit weight of the radiopaque element or agent. Secondary effects include selective placement of the radiopaque elements which may further enhance the radiopacity of the device with reduced requirements of the radiopaque agent. Such a radiopaque contrast agent may be produced in various forms such as a dendrimer and/or incorporated as the end groups of polymeric chain. In addition one can incorporate biological and/or pharmaceutical agents in combination with the present invention.

1 . A compound having the formula:  
       R—NHFmoc  wherein R is a dendritic organic moiety containing at least one halogen atom selected from the group consisting of iodine, chlorine, and bromine.    
   
   
       2 . A compound having the formula:  
       R—NH 2    wherein R is a dendritic organic moiety containing at least one halogen atom selected from the group consisting of iodine, chlorine, and bromine.    
   
   
       3 . A compound having the formula:  
       R—NH—R′ wherein R is a dendritic organic moiety containing at least one halogen atom selected from the group consisting of iodine, chlorine, and bromine, and wherein R′ is a polymer.    
   
   
       4 . A radiopaque material comprising; 
 an organic polymeric chain having a proximal end and a distal end; and    a compound having the formula:      R—NHFmoc    wherein R is a dendritic organic moiety containing at least one halogen atom selected from the group consisting of iodine, chlorine, and bromine and said compound is admixed with said organic polymeric chain.    
   
   
       5 . A radiopaque material comprising; 
 an organic polymeric chain having a proximal end and a distal end; and    a compound having the formula:      R—NH 2      wherein R is a dendritic organic moiety containing at least one halogen atom selected from the group consisting of iodine, chlorine, and bromine and said compound is covalently attached to either the proximal end or the distal end of said organic polymer chain.    
   
   
       6 . A radiopaque material comprising; 
 an organic polymeric chain having a proximal end and a distal end; and    a compound having the formula:      R—NH—R′   wherein R is a dendritic organic moiety containing at least one halogen atom selected from the group consisting of iodine, chlorine, and bromine and wherein R′ is a polymer, and said compound is admixed with said organic polymeric chain.    
   
   
       7 . The compound of any of claims  1 ,  2 , or  3  wherein R is a dendritic organic moiety containing at least three halogen atoms selected from the group consisting of iodine, chlorine, and bromine.  
   
   
       8 . The compound of any of claims  1 ,  2 , or  3  wherein R is a starshaped organic moiety containing at least three halogen atoms selected from the group consisting of iodine, chlorine, and bromine.  
   
   
       9 . A medical device fabricated from a material of any of claims  4 ,  5  or  6 .  
   
   
       10 . A medical device whose radiopacity is enhanced with a compound of any of claims  1 ,  2  or  3 .  
   
   
       11 . A medical device whose radiopacity is enhanced with a compound of  claim 7 .  
   
   
       12 . A medical device whose radiopacity is enhanced with a compound of  claim 8 .  
   
   
       13 . A medical device whose radiopacity is enhanced with a coating fabricated from a material of any of claims  4 ,  5 , or  6 .  
   
   
       14 . The compound of  claim 3  wherein said polymer is a biostable polymer.  
   
   
       15 . The compound of  claim 3  wherein said polymer is a biodegradable polymer.  
   
   
       16 . The radiopaque material of  claim 6  wherein said polymer is a biostable polymer.  
   
   
       17 . The radiopaque material of  claim 6  wherein said polymer is a biodegradable polymer.  
   
   
       18 . The medical device of  claim 9  further comprising a pharmaceutical agent.  
   
   
       19 . The medical device of  claim 10  further comprising a pharmaceutical agent.  
   
   
       20 . The medical device of  claim 11  further comprising a pharmaceutical agent.  
   
   
       21 . The medical device of  claim 12  further comprising a pharmaceutical agent.  
   
   
       22 . The medical device of  claim 13  further comprising a pharmaceutical agent.  
   
   
       23 . The radiopaque material of  claim 16  wherein said biostable polymer having polymeric chains wherein the molecular orientation of said polymeric chains are substantially aligned.  
   
   
       24 . The radiopaque material of  claim 17  wherein said biodegradable polymer having polymeric chains wherein the molecular orientation of said polymeric chains are substantially aligned.  
   
   
       25 . The medical device of  claim 18  wherein said medical device is an intraluminal medical device.  
   
   
       26 . The medical device of  claim 19  wherein said medical device is an intraluminal medical device.  
   
   
       27 . The medical device of  claim 20  wherein said medical device is an intraluminal medical device.  
   
   
       28 . The medical device of  claim 21  wherein said medical device is an intraluminal medical device.  
   
   
       29 . The medical device of  claim 22  wherein said medical device is an intraluminal medical device.