US2016355540A1PendingUtilityA1

5-position modified pyrimidines and their use

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Assignee: SOMALOGIC INCPriority: Apr 12, 2010Filed: Apr 4, 2016Published: Dec 8, 2016
Est. expiryApr 12, 2030(~3.7 yrs left)· nominal 20-yr term from priority
Inventors:John C. RohloffNebojsa JanjicJeffrey D. CarterCatherine Fowler
A61P 37/00A61P 43/00A61P 37/08A61P 17/00A61P 17/04C12N 15/115C07H 19/06C12N 2310/335C07H 19/067C07H 19/173C07H 19/10C12N 2310/16C07H 21/04C07H 19/073C07H 19/167A61K 31/7088C07H 19/00
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Claims

Abstract

The present disclosure relates to the field of nucleic acid chemistry, specifically to 5-position modified uridines as well as phosphoramidite and triphosphate derivatives thereof. The present disclosure also relates to methods of making and using the same.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . A C-5 modified aminocarbonylpyrimidine having the following structure: 
       
         
           
           
               
               
           
         
         wherein 
         R′ is selected from the group consisting of —H, —Ac, —Bz, —CH 2 CH 2 OCH 3 , —C(O)CH 2 OCH 3  and —SiMe 2 tBu; 
         R″ is selected from the group consisting of H, DMT and triphosphate (—P(O)(OH)—O—P(O)(OH)—O—P(O)(OH) 2 ) or a salt thereof; 
         X is selected from the group consisting of —H, —OH, —OMe, —O-allyl, —F, —OEt, —OPr, —OCH 2 CH 2 OCH 3  and -azido, 
         R is selected from the group consisting of —(CH 2 ) n —R X1 ; 
         R X1  is selected from the group consisting of: 
       
       
         
           
           
               
               
           
         
         R X4  is selected from the group consisting of a Cl and a nitrile (CN); and 
         n=0-10. 
       
     
     
         2 . A 3′-phosporamidite of a C-5 modified aminocarbonylpyrimidine having the following structure: 
       
         
           
           
               
               
           
         
         wherein 
         R″ is selected from the group consisting of H, DMT and triphosphate (—P(O)(OH)—O—P(O)(OH)—O—P(O)(OH) 2 ) or a salt thereof; 
         X is selected from the group consisting of —H, —OH, —OMe, —O-allyl, —F, —OEt, —OPr, —OCH 2 CH 2 OCH 3  and -azido, 
         R is selected from the group consisting of —(CH 2 ) n —R X1 ; 
         R X1  is selected from the group consisting of: 
       
       
         
           
           
               
               
           
         
         R X4  selected from the group consisting of a Cl and a nitrile (CN); and 
         n=0-10. 
       
     
     
         3 . A 5′-triphosphate of a C-5 modified aminocarbonylpyrimidine having the following structure: 
       
         
           
           
               
               
           
         
         wherein 
         R′ is selected from the group consisting of —H, —Ac, —Bz, —CH 2 CH 2 OCH 3 , —C(O)CH 2 OCH 3  and —SiMe 2 tBu; 
         X is selected from the group consisting of —H, —OH, —OMe, —O-allyl, —F, —OEt, —OPr, —OCH 2 CH 2 OCH 3  and -azido, 
         R is selected from the group consisting of —(CH 2 ) n —R X1 ; 
         R X1  is selected from the group consisting of: 
       
       
         
           
           
               
               
           
         
         R X4  selected from the group consisting of a Cl and a nitrile (CN); and 
         n=0-10.

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