US 9,809,586 B2
Inhibitors of collagen prolyl 4-hydroxylase
Ronald T. Raines, Madison, WI (US); and James Vasta, Madison, WI (US)
Assigned to Wisconsin Alumni Research Foundation, Madison, WI (US)
Filed by WISCONSIN ALUMNI RESEARCH FOUNDATION, Madison, WI (US)
Filed on Mar. 28, 2016, as Appl. No. 15/82,372.
Claims priority of provisional application 62/139,685, filed on Mar. 28, 2015.
Prior Publication US 2016/0280701 A1, Sep. 29, 2016
Int. Cl. A61K 31/4025 (2006.01); A61K 31/4155 (2006.01); A61K 31/4178 (2006.01); A61K 31/421 (2006.01); A61K 31/426 (2006.01); A61K 31/444 (2006.01); A61K 31/497 (2006.01); A61K 31/501 (2006.01); C07D 401/04 (2006.01); C07D 413/04 (2006.01); C07D 417/04 (2006.01); C07D 213/80 (2006.01)
CPC C07D 417/04 (2013.01) [C07D 213/80 (2013.01); C07D 401/04 (2013.01); C07D 413/04 (2013.01)] 21 Claims
 
1. A compound of formula:

OG Complex Work Unit Drawing
or salts thereof,
where:
X is S, O, NH, or NR,
where R is an alkyl group having 1-3 carbon atoms;
R1 and R2 independently are —OR7, or —NHSO2R8,
where R7 is selected from:
hydrogen, alkyl, alkoxyalkyl, —R′—CO—R″, —R′—CO—O—R″, —CO—R″, —R′—O—CO—R″, —R′—CO—NR″, —CO—NR″, —R′—O—CO—NR″, and
R8 is selected from hydrogen, alkyl, aryl or arylalkyl;
R3, R4 and R6 independently are hydrogen, alkyl, alkoxy, alkenyl, alkenoxy, haloalkyl, haloalkenyl, halogen, hydroxyl, hydroxyalkyl, hydroxyalkenyl, aryl, aryloxy, arylalkyl or arylalkyoxy;
R5 is hydrogen, an alkyl having 1-3 carbon atoms or an alkoxy having 1-3 carbon atoms;
—R′— is a divalent straight chain or branched alkylene, and
—R″ is an alkyl, aryl or arylalkyl.