US 12,152,031 B2
Biodefense agents
Ashoke Bhattacharjee, Cheshire, CT (US); Erin M. Duffy, Deep River, CT (US); Trudy Grossman, New Haven, CT (US); Joseph A. Ippolito, Guilford, CT (US); and Zoltan F. Kanyo, North Haven, CT (US)
Assigned to BIOVERSYS AG, Basel (CH)
Appl. No. 16/972,775
Filed by BIOVERSYS AG, Basel (CH)
PCT Filed Jun. 6, 2019, PCT No. PCT/IB2019/000808
§ 371(c)(1), (2) Date Dec. 7, 2020,
PCT Pub. No. WO2019/234508, PCT Pub. Date Dec. 12, 2019.
Claims priority of provisional application 62/681,627, filed on Jun. 6, 2018.
Prior Publication US 2021/0253577 A1, Aug. 19, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 487/04 (2006.01); A61P 31/04 (2006.01)
CPC C07D 487/04 (2013.01) [A61P 31/04 (2018.01)] 29 Claims
 
1. A method of treating, preventing, reducing the risk of, or delaying the onset of a microbial infection in a subject, the method comprising administering to the subject a therapeutically effective amount of a compound of Formula (I):

OG Complex Work Unit Chemistry
or a tautomer thereof or a pharmaceutically acceptable salt of the compound or tautomer,
wherein:
R1 is selected from H and halo;
R2 is selected from H, halo, C1-6 alkyl, C1-4 haloalkyl, and ORa1;
R3 is selected from H, C1-6 alkyl, and C1-4 haloalkyl;
W is selected from N and CR4;
R4 is selected from H, halo, ORa2, SRa2, 5-6 membered heterocycloalkyl, S(O)2Rb2, C1-6 alkyl, C1-4 alkylthio, and C2-6 alkenyl, wherein the C1-6 alkyl is optionally substituted with a substituent selected from ORa2;
R5 is selected from H, halo, C1-6 alkyl, and C2-6 alkenyl, wherein the C1-6 alkyl is optionally substituted with a substituent selected from ORa2;
R6 is selected from H, C1-6 alkyl, and C2-6 alkenyl, wherein the C1-6 alkyl is optionally substituted with ORa3;
R7 is selected from H and C1-6 alkyl; or
R6 and R7 together with the carbon atoms to which they are attached and the nitrogen atom connecting the two carbon atoms forms a ring of the formula:

OG Complex Work Unit Chemistry
R8 is selected from H, C1-6 alkyl, and C1-4 haloalkyl;
X is selected from O and NRN;
RN is selected from H and C1-4 alkyl;
RA is H;
RB is H; or
RA and RB together with the nitrogen atom to which they are attached form a 5- to 6-membered heterocycloalkyl ring containing 1 or 2 heteroatoms selected from N, O and S, wherein the 5- to 6-membered heterocycloalkyl is optionally substituted with halo;
R9 is selected from C1-6 alkyl, C2-6 alkenyl, C3-5 cycloalkyl, wherein the C1-6 alkyl is optionally substituted with a substituent selected from ORa3 and SRa3;
R10 is selected from H, C2-4 alkenyl, C1-4haloalkyl and C1-4 alkyl optionally substituted with a substituent selected from amino, C1-4 alkoxy, C3-5 cycloalkyl, and 3- to 6-membered heterocycloalkyl;
R11 is H or C1-3 alkyl, wherein the C1-3 alkyl is optionally substituted with OH; and
each of Ra1, Ra2, Ra3, and Rb2 is independently selected from H, C1-6 alkyl and C1-4 haloalkyl;
wherein the infection is caused by or involves one or more microorganisms which are capable of being used as biological weapons or which are extremely-drug resistant Gram-positive or Gram-negative pathogens.