5-position modified pyrimidines and their use

Patent metadata

Field	Value
Publication number	US-9163056-B2
Application number	US-201314069798-A
Country	US
Kind code	B2
Filing date	Nov 1, 2013
Priority date	Apr 12, 2010
Publication date	Oct 20, 2015
Grant date	Oct 20, 2015

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.

First claim

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 fo 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; 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 — X1 ;
R X1 is selected from the group consisting of:

R X4 is; 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 is; and n=0−10.

Assignees

• Somalogic Inc

Inventors

• ROHLOFF John
• Janjic Nebojsa
• Carter Jeffrey D
• Fowler Catherine

Classifications

• A61P37/08

  Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14) · CPC title

• A61P37/00

  Drugs for immunological or allergic disorders · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P17/04

  Antipruritics · CPC title

• A61P17/00

  Drugs for dermatological disorders · CPC title