US 9,809,605 B1
Broad spectrum beta-lactamase inhibitors
Larry Sutton, Atchison, KS (US); and Sophia Yu, Atchison, KS (US)
Assigned to GLADIUS PHARMACEUTICALS CORPORATION, Montreal, Quebec (CA)
Filed by Gladius Pharmaceuticals Corporation, Montreal (CA)
Filed on Jul. 21, 2017, as Appl. No. 15/656,845.
Application 15/247,536 is a division of application No. 14/491,806, filed on Sep. 19, 2014, granted, now 9,453,032, issued on Sep. 27, 2016.
Application 15/656,845 is a continuation of application No. 15/247,536, filed on Aug. 25, 2016.
Application 14/491,806 is a continuation of application No. 12/248,760, filed on Oct. 9, 2008, granted, now 8,883,772, issued on Nov. 11, 2014.
Claims priority of provisional application 60/997,898, filed on Oct. 9, 2007.
Claims priority of provisional application 60/997,941, filed on Oct. 9, 2007.
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 501/24 (2006.01); C07D 501/60 (2006.01); C07D 501/22 (2006.01); A01N 43/90 (2006.01)
CPC C07D 501/24 (2013.01) [A01N 43/90 (2013.01); C07D 501/22 (2013.01); C07D 501/60 (2013.01)] 20 Claims
 
1. A compound of formula:

OG Complex Work Unit Drawing
or pharmaceutically acceptable salts thereof,wherein:
R is an acylamino group;
R1, R2, and R4 are independently selected from hydrogen, halogen, a C1-C6 alkyl group, a C1-C6 alkoxy group and —S-alkyl, where the alkyl group is a C1-C6 alkyl;
n is 1 or 2;
Y is O—C+ or OR3, where R3 is hydrogen, an alkyl group or an aryl group, each of which groups is optionally substituted, and C+ is a pharmaceutically acceptable cation;
M is selected from:

OG Complex Work Unit Drawing
where:
each R8 is independently selected from hydrogen, halogen, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C7-C19 aralkyl group, a 3-7-member ring cyclic hydrocarbon group, a 3-7 member heterocyclic group, a C6-C10 aromatic group, and a 6-10 member heterocyclic aromatic group, wherein each of said groups is optionally substituted; and
X is a leaving group;
wherein optional substitution is substitution with one or more halogen, hydroxyl, —CN, —SH, alkyl, alkenyl, alkynyl, aryl, heterocyclyl, heteroaryl, alkoxy, alkenoxy, alkynoxy, aryloxy, heteroaryloxy, heterocyclyloxy, sulfenyl, sulfonyl, sulfonate, amine, amido, aminoacyl, imine, —COR20, —COOR20, —CON(R20)2, —OCOR20, —OCN(R20)2, haloalkyl, haloalkenyl, haloaryl, —NR20COR20, —NR20COOR20, or —COO C+, where each R20 is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, heterocyclyl, and heteroaryl, and C+ is a pharmaceutically acceptable cation.