Polymers

Abstract

A polymer having a plurality of 5-6 membered unsaturated rings which may be the same or different, linked together by way of linker chains to form a backbone, at least some of said 5-6 membered unsaturated rings carrying a ligand. Polymers of this nature can act as DNA mimics and as supports for use in oligonucleotide production.

1 - 18 . (canceled)  
   
   
       19 . A process for preparing a polymer having a plurality of 5-6 membered unsaturated rings which may be the same or different, linked together by way of linker chains to form a backbone, at least some of said 5-6 membered unsaturated rings carrying a ligand, which process comprises consecutively adding appropriately substituted monomers to a chain.  
   
   
       20 . A process according to  claim 19  in which the polymer comprises a compound of general formula (I)  
     
       
         
         
             
             
         
       
     
     where n is an integer in excess of 1, each A is the same or different and is a 5 or 6 membered unsaturated ring, each R 1  is the same or different to any other such group and is selected from hydrogen or a ligand group, each R 2  is an optionally substituted linker group which may be the same or different to any other such group, R 3  is hydrogen or a blocking group, R 4  is at least a part of a linker group, p is 0 or 1, and R 5  is a leaving group or a blocked derivative thereof.  
   
   
       21 . A process according to  claim 20  which comprises the following steps: 
 (a) reacting a compound of formula (III)                          in which A is a 5 or 6 membered unsaturated ring, R 4  is at least a part of a linker group, R 5  is a leaving group or a blocked derivative thereof, p is 0 or 1, R 1′  is selected from hydrogen or a ligand group or a protected derivative thereof; R 2′  is an optionally substituted linker group or a protected form thereof where p is 0, or R 2′  is a precursor group, such that an optionally substituted linker group or a protected form thereof is formed by —R 2′ —R 4 — where p is 1, and    R 14  is a protecting group,    with a compound of formula (IV);    where A is a 5 or 6 membered unsaturated ring, R 2  is an optionally substituted linker group which may be the same or different to any other such group, R 4  is at least a part of a linker group, p is 0 or 1, q is 0 or 1 and R 1′  and R 2′  are as defined above in relation to formula (III), and all of these may be the same or different to the corresponding moieties in the compound of formula (III), where R 15  is a protecting group    then    (b) removing a protecting group R 14  and reacting the product with a further compound of formula (III); or                          (c) where q is 1, removing a protecting group R 15  and reacting the product with a further compound of formula (III); and    (d) repeating step (b) and/or (c) until the desired polymer is obtained;    (e) removing any protecting groups on R 1′  and/or R 2′ ;    and thereafter if desired or necessary, removing any remaining protecting groups R 14  or R 15  and/or introducing a blocking group R 3 .    
   
   
       22 . A process according to  claim 19  which is carried out in an automated fashion.  
   
   
       23 . A process according to  claim 20  which is carried out in an automated fashion.  
   
   
       24 . A process according to  claim 20  wherein the rings A are aromatic rings.  
   
   
       25 . A process according to  claim 20  wherein the rings A are of sub-formula (i)  
     
       
         
         
             
             
         
       
     
     where X 1 , X 2  and X 3  are independently selected from C or N.  
   
   
       26 . A process according to  claim 25  wherein at least some of the groups or sub-formula (i) are triazine groups.  
   
   
       27 . A process according to  claim 20  wherein linker groups R 2  are independently selected from a chain of from 2-8 atoms or a ring of from 3-8 atoms, selected from carbon atoms or heteroatoms which may be optionally substituted.  
   
   
       28 . A process according to  claim 27  wherein at least some linking groups R 2  are groups of sub-formula (ii) or (iii)  
       —Y 1 —(CR 6 R 7 ) m —Y 2 —  (ii)  —(CR 8 R 9 ) s —Y 3 —(CR 10 R 11 ) t —  (iii)  
     where m, s and t are independently selected from integers of from 1-6, and Y 1  and Y 2  are independently selected from a bond, O, S, NR 12 , —C(O)O—, —OC(O)—, —NR 12 C(O)—, —C(O)NR 12 —, or —NR 12 C(O)NR 13  where R 12  and R 13  are independently selected from hydrogen or C 1-4 alkyl, and Y 3  is a group which is formed by joining two moieties together, such as esters and amides of formulae —C(O)O—, —OC(O)—, —NR 12 C(O)—, —C(O)NR 12 —, or —NR 12 C(O)NR 13  where R 12  and R 13  are as defined above; and each R 6 , R 7 , R 8 , R 9 , R 10  and R 11  is independently selected from hydrogen, alkyl, hydroxy, hydroxyalkyl, alkoxy, alkanoyl, carboxy or salts or esters thereof, carboxyalkyl or salts or esters thereof, nitro, nitroalkyl, cyano, cyanoalkyl, amino, mono- or di-alkyl amino, aminoalkyl phosphate, alkyl phosphate, sulphate, alkyl sulphate, mercapto, alkylthio, alkylsulphonyl, or a reporter molecule or tag.  
   
   
       29 . A process according to  claim 28  wherein at least some linking groups R 2  are groups of formula —NHCH 2 CH 2 NH—.  
   
   
       30 . A process according to  claim 19  wherein the ligand is selected from nucleobases, nucleobase binding groups or DNA intercalators, where the nucleobases, nucleobase binding groups or DNA intercalators may be bonded directly to the ring or may have a C 1-4 alkylene chain interposed therebetween.  
   
   
       31 . A process according to  claim 30  wherein at least some groups R 1  are naturally occurring nucleobases.  
   
   
       32 . A process according to  claim 20 , wherein the polymer is a compound of formula (II)  
     
       
         
         
             
             
         
       
     
     where R 2 , R 3 , R 5  and n are as defined in claim  2 , each R 1  is the same or different and is as defined in  claim 20 , and X 1 , X 2  and X 3  are independently selected from C or N.  
   
   
       33 . A compound of formula (III) as defined in  claim 21 .  
   
   
       34 . A compound of formula (IV) as defined in  claim 21 .  
   
   
       35 . A compound of formula (VI)  
     
       
         
         
             
             
         
       
     
     where R 2  and R 14  are as defined in  claim 20  and R 17  and R 19  are leaving groups.  
   
   
       36 . A method of preparing a compound of formula (X)  
     
       
         
         
             
             
         
       
     
     where R 2  is as defined in relation to formula (I) and R 14  is as defined in relation to formula (III), by reacting a cyanuric chloride with a compound of formula (XI)  
       H—R 2 —R 14    (XI)  
     where R 2  and R 14  are as defined above, at a temperature below 10° C.