US 10,376,534 B2
Substituted nucleosides, nucleotides and analogs thereof
Guangyi Wang, Carlsbad, CA (US); David Bernard Smith, San Mateo, CA (US); Leonid Beigelman, San Mateo, CA (US); Jerome Deval, Pacifica, CA (US); and Marija Prhavc, Encinitas, CA (US)
Assigned to ALIOS BIOPHARMA, INC., South San Francisco, CA (US)
Filed by Alios BioPharma, Inc., South San Francisco, CA (US)
Filed on Jul. 28, 2016, as Appl. No. 15/221,961.
Application 15/221,961 is a continuation of application No. 14/386,294, granted, now 9,441,007, previously published as PCT/US2013/033018, filed on Mar. 19, 2013.
Application 14/386,294 is a continuation in part of application No. 13/721,988, filed on Dec. 20, 2012, granted, now 9,073,960, issued on Jul. 7, 2015.
Claims priority of provisional application 61/613,836, filed on Mar. 21, 2012.
Prior Publication US 2016/0331770 A1, Nov. 17, 2016
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/706 (2006.01); A61K 31/7068 (2006.01); A61K 31/7072 (2006.01); A61K 31/708 (2006.01); C07H 19/20 (2006.01); C07H 19/06 (2006.01); C07H 19/16 (2006.01); C07H 19/10 (2006.01); C07H 19/12 (2006.01); C07H 19/207 (2006.01); A61K 31/7076 (2006.01)
CPC A61K 31/708 (2013.01) [A61K 31/706 (2013.01); A61K 31/7068 (2013.01); A61K 31/7072 (2013.01); A61K 31/7076 (2013.01); C07H 19/06 (2013.01); C07H 19/10 (2013.01); C07H 19/12 (2013.01); C07H 19/16 (2013.01); C07H 19/20 (2013.01); C07H 19/207 (2013.01)] 25 Claims
 
1. A method of treating a metapneumovirus infection comprising administering to a subject infected with the metapneumovirus an effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt thereof, wherein the compound of Formula (I) has the following structure:

OG Complex Work Unit Drawing
wherein:
B1A is an optionally substituted purine-base or an optionally substituted pyrimidine-base;
R1A is selected from the group consisting of hydrogen, an optionally substituted acyl and

OG Complex Work Unit Drawing
the dashed line (------) is absent;
R2A is selected from the group consisting of an unsubstituted C1-6 alkyl, a halogen substituted C1-6 alkyl, a hydroxy substituted C1-6 alkyl, an alkoxy substituted C1-6 alkyl and a sulfenyl substituted C1-6 alkyl;
R3A is selected from the group consisting of OH and —OC(═O)R″A;
R4A is fluoro;
R5A is hydrogen;
R6A and R7A are independently absent or hydrogen; or
R6A is

OG Complex Work Unit Drawing
and R7A is absent or hydrogen;
R12A, R13A and R14A are independently absent or hydrogen;
R″A is an unsubstituted C1-6 alkyl;
m is 0 or 1; and
Z1A is O.