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 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,
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.