Pyrrolopyrimidine nucleosides and analogs thereof

Inventors: John Henry Bougher, III (Durham, NC); Ramamurty V S Changalvala (Morrisville, NC); John C. Drach (Ann Arbor, MI); Ernest Randall Lanier, Jr. (Chapel Hill, NC); Andrew Louis McIver (Durham, NC); Bradley David Robertson (Durham, NC); Dean Wallace Selleseth (Cary, NC); Phiroze Behram Sethna (Durham, NC); Leroy Townsend (Ann Arbor, MI); Roy W. Ware (Raleigh, NC)

Assignees: Chimerix, Inc.; The Regents of the University of Michigan

C07H19/14 A61K31/706 A61K31/7052 A61K31/7064

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Quick Facts

Patent No.: US 9,701,706
App. No.: 15/358,938
Granted: Jul 11, 2017
Kind: B2

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Abstract

The present disclosure provides pyrrolopyrimidine nucleoside analogs of the Formula I, Formula IA, Formula IB, or Formula II and phospholipid conjugates and pharmaceutical compositions thereof wherein R c and A are defined herein. Also presented are methods of treating and/or preventing viral infection and/or viral infection-associated disease or disorder with one or more compounds of Formula I, Formula IA, Formula IB, or Formula II.

Claims (59)

1. A compound of Formula II:

or a pharmaceutically acceptable salt, solvate, enantiomer, diastereomer, racemate or mixture thereof, wherein:

Y is —C(O)—, or

wherein X 1 is independently O, NH, or S, X 2 is independently a bond, —O—, —S—, or —NH—, and X 3 is independently —OR, —NHR II , or —SR II ;

each R is independently —H, —C 1 -C 20 alkyl, —C 2 -C 20 alkenyl, —C 2 -C 20 alkynyl, —C 3 -C 8 cycloalkyl, —C 4 -C 8 cycloalkenyl, aryl, heteroaryl, or heterocyclyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, or heterocyclyl is optionally substituted with one or more halogen, oxo, R 1 , —OR 1 , —NR 1 R 2 , —SR 1 , —OC(O)R 1 , —C(O)OR 1 , —NHC(O)OR 1 , or —NHC(O)R 1 ;

R a and R b are each independently, at each occurrence, —H, —C 1 -C 20 alkyl, —C 2 -C 20 alkenyl, —C 2 -C 20 alkynyl, —C 3 -C 8 cycloalkyl, —C 4 -C 8 cycloalkenyl, aryl, heteroaryl, or heterocyclyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, or heterocyclyl is optionally substituted with one or more halogen, oxo —OR 1 , —NR 1 R 2 , —SR 1 , —OC(O)R 1 , —C(O)OR 1 —NHC(O)OR 1 , or —NHC(O)R 1 ;

R 1 and R 2 are each independently, at each occurrence, —H, —C 1 -C 20 alkyl, —C 2 -C 20 alkenyl, —C 2 -C 20 alkynyl, —C 3 -C 8 cycloalkyl, —C 4 -C 8 cycloalkenyl, aryl, heteroaryl, or heterocyclyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, or heterocyclyl is optionally substituted with one or more halogen, oxo, —R 3 , —R 4 , —OR 3 , —NR 3 R 4 , —SR 3 , —OC(O)R 3 , —C(O)OR 3 , —NHC(O)OR 3 , or —NHC(O)R 3 ;

R 3 and R 4 are each independently, at each occurrence, —H, —C 1 -C 20 alkyl, —C 2 -C 20 alkenyl, —C 2 -C 20 alkynyl, —C 3 -C 8 cycloalkyl, —C 4 -C 8 cycloalkenyl, aryl, heteroaryl, or heterocyclyl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, or heterocyclyl is optionally substituted with one or more halogen, oxo, aryl, heteroaryl, —OH, —NH 2 , —SH, —OC(O)H, —C(O)OH, —NHC(O)OH, or —NHC(O)H;

R c is independently —H or -D; and

n is independently 0, 1, 2 or 3.

2. The compound of claim 1 , wherein R a is —H.

3. The compound of claim 1 , wherein R b is —H.

4. The compound of claim 1 , wherein R c is —H.

5. The compound of claim 1 , wherein n is 0.

6. The compound of claim 1 , wherein R a , R b and R c are —H.

7. The compound of claim 1 , wherein R a , R b and R c are —H and n is 0.

8. The compound of claim 1 , wherein the compound is: