US 10,889,556 B2
Compositions and methods for inhibiting influenza RNA polymerase PA endonuclease
Seth M. Cohen, Carlsbad, CA (US); Cy V. Credille, San Diego, CA (US); and David T. Puerta, Fallbrook, CA (US)
Assigned to The Regents of the University of California, Oakland, CA (US)
Filed by The Regents of the University of California, Oakland, CA (US)
Filed on Sep. 7, 2018, as Appl. No. 16/125,468.
Application 16/125,468 is a continuation in part of application No. PCT/US2017/021457, filed on Mar. 8, 2017.
Claims priority of provisional application 62/305,407, filed on Mar. 8, 2016.
Claims priority of provisional application 62/608,475, filed on Dec. 20, 2017.
Prior Publication US 2019/0106398 A1, Apr. 11, 2019
Int. Cl. C07D 309/32 (2006.01); C07D 309/40 (2006.01); C07D 213/69 (2006.01); C07D 213/90 (2006.01); C07D 401/04 (2006.01); C07D 401/10 (2006.01); C07D 413/04 (2006.01); C07C 49/747 (2006.01); C07C 49/453 (2006.01); C07C 62/38 (2006.01); C07C 65/03 (2006.01); C07C 65/05 (2006.01); C07C 69/757 (2006.01); A61P 31/16 (2006.01); C07C 49/717 (2006.01); C07C 49/753 (2006.01)
CPC C07D 309/32 (2013.01) [A61P 31/16 (2018.01); C07C 49/717 (2013.01); C07C 49/747 (2013.01); C07C 49/753 (2013.01); C07C 62/38 (2013.01); C07C 65/03 (2013.01); C07C 65/05 (2013.01); C07C 69/757 (2013.01); C07D 213/69 (2013.01); C07D 213/90 (2013.01); C07D 309/40 (2013.01); C07D 401/04 (2013.01); C07D 401/10 (2013.01); C07D 413/04 (2013.01); C07C 2601/18 (2017.05)] 16 Claims
 
1. A compound having the formula:

OG Complex Work Unit Drawing
wherein,
Y is O, S, or NH;
W1 is —CH(R1)—, or —N(R1)—;
R1 is hydrogen;
W2 is —C(R2)═;
R2 is hydrogen, halogen, —CX23, —CHX22, —CH2X2, —OCX23, —OCH2X2, —OCHX22, —CN, —SOn2R2D, —SOv2NR2AR2B, —NHC(O)NR2AR2B, —N(O)m2, —NR2AR2B, —C(O)R2C, —C(O)—OR2C, —C(O)NR2AR2B, —OR2D, —NR2ASO2R2D, —NR2AC(O)R2C, —NR2AC(O)OR2C, —NR2AOR2C, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R3 is substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R4 is halogen, —CX43, —CHX42, —CH2X4, —OCX43, —OCH2X4, —OCHX42, —CN, —SOn4R4D, —SOv4NR4AR4B, —NHC(O)NR4AR4B, —N(O)m4, —NR4AR4B, —C(O)R4C, —C(O)—OR4C, —C(O)NR4AR4B, —OR4D, —NR4ASO2R4D, —NR4AC(O)R4C, —NR4AC(O)OR4C, —NR4AOR4C, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
each R2A, R2B, R2C, R2D, R4A, R4B, and R4D are independently hydrogen, —CX3, —CN, —COOH, —CONH2, —CHX2, —CH2X, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; R2A and R2B substituents bonded to the same nitrogen atom may optionally be joined to form a substituted or unsubstituted heterocycloalkyl or substituted or unsubstituted heteroaryl; R4A and R4B substituents bonded to the same nitrogen atom may optionally be joined to form a substituted or unsubstituted heterocycloalkyl or substituted or unsubstituted heteroaryl;
R1D is hydrogen;
R4C is hydrogen;
each X, X2, and X4 is independently —F, —Cl, —Br, or —I;
n2 and n4 are independently an integer from 0 to 4; and
m2, m4, v2 and v4 are independently an integer from 1 to 2.