[1, 2, 4] Triazolo [1, 5-A] Pyrimidine Derivatives as Chromatographic Adsorbent for the Selective Adsorption of Igg

Abstract

The present invention relates to a chromatographic adsorbent for selectively adsorbing IgG, comprising the following formula and its corresponding enol-form, wherein X represents O, S, or NH; R 1 represents H, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl, Ar, —C(O)NHR 3 , —C(O)—R 3 or halo; R 2 represents H, C 1-3 alkyl or halo; R 3 represents H, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkyl or Ar; n represents 0, 1, 2 or 3; Y represents a carrier. The present invention also relates to a method of producing said adsorbent as well as use thereof for separating substances by affinity chromatography.

1 . A chromatographic adsorbent for selectively adsorbing IgG, comprising the following formula: 
       
         
           
           
               
               
           
         
       
       and its corresponding enol-form, 
       wherein
 X represents O, S, or NH; 
 R 1  represents H, C 1-6  alkyl, C 1-6  alkoxy, C 1-6  alkoxy-C 1-6  alkyl, Ar, —C(O)NHR 3 , —C(O)—R 3  or halo; 
 R 2  represents H, C 1-3  alkyl or halo; 
 R 3  represents H, C 1-6  alkyl, C 1-6  alkoxy, C 1-6  alkoxy-C 1-6  alkyl or Ar; 
 n represents 0, 1, 2 or 3; 
 Y represents a carrier; and 
 Ar represents a C 6-10  aryl group, which group is optionally substituted by one or more substituents selected from —OH, cyano, halo, nitro, C 1-6  alkyl and alkoxy. 
 
     
     
         2 . The chromatographic adsorbent of  claim 1 , wherein the carrier Y is selected from cellulose, starch, dextran, agar, agarose, polyacrylamide, poly(meth)acrylate, a polyvinyl hydrophilic polymer, polystyrene and polysulfone, silica, alumina, titania oxide, zirconia oxide, a polysaccharide-synthetic polymer, a polysaccharide-minral structure, or a synthetic polymer-mineral structure. 
     
     
         3 . The chromatographic adsorbent of  claim 1 , wherein R 1  represents H, n represents 0, X represents NH and Y represents agarose. 
     
     
         4 . The chromatographic adsorbent of  claim 1  further comprising a spacer molecule between X and Y. 
     
     
         5 . The chromatographic adsorbent of  claim 4  wherein R 1  represents H, n represents 0, X represents NH, Y represents HP-Sepharose, and hexamethylene diamine as the spacer molecule. 
     
     
         6 . The chromatographic adsorbent of  claim 1 , wherein the carrier material Y is in the form of beads, irregularly shaped particles, fibers, membranes, flat structure or porous mineral materials. 
     
     
         7 . A method of producing a chromatographic adsorbent comprising the following steps:
 a) providing a chromatographic carrier material Y; and   b) coupling a ligand on the surface of said carrier material,   to produce an adsorbent of the formula   
       
         
           
           
               
               
           
         
       
       and its corresponding enol-form, 
       wherein
 X represents O, S or NH; 
 R 1  represents H, C 1-6  alkyl, C 1-6  alkoxy, C 1-6  alkoxy-C 1-6  alkyl, Ar, —C(O)NHR 3 , —C(O)—R 3  or halo; 
 R 2  represents H, C 1-3  alkyl or halo; 
 R 3  represents H, C 1-6  alkyl, C 1-6  alkoxy, C 1-6  alkoxy-C 1-6  alkyl or Ar; 
 n represents 0, 1, 2 or 3; 
 Y represents the carrier; 
 Ar represents a C 6-10  aryl group, which group is optionally substituted by one or more substituents selected from —OH, cyano, halo, nitro, C 1-6  alkyl and alkoxy. 
 
     
     
         8 . The method of  claim 7 , wherein the carrier Y is an amine possessing matrix. 
     
     
         9 . The method of  claim 8 , wherein the carrier Y is epichloro hydrine activated HP-Sepharose extended with hexamethylene diamine. 
     
     
         10 - 11 . (canceled)