US 11,905,252 B2
Compounds
Matthew Cooper, Cambridge (GB); David Miller, Cambridge (GB); Angus Macleod, Cambridge (GB); and Jonathan Shannon, Nottingham (GB)
Assigned to INFLAZOME LIMITED, Dublin (IE)
Appl. No. 16/977,241
Filed by INFLAZOME LIMITED, Dublin (IE)
PCT Filed Mar. 1, 2019, PCT No. PCT/EP2019/055127
§ 371(c)(1), (2) Date Sep. 1, 2020,
PCT Pub. No. WO2019/166619, PCT Pub. Date Sep. 6, 2019.
Claims priority of application No. 1803392 (GB), filed on Mar. 2, 2018; and application No. 1813284 (GB), filed on Aug. 15, 2018.
Prior Publication US 2021/0347737 A1, Nov. 11, 2021
Int. Cl. C07D 231/18 (2006.01); C07D 401/12 (2006.01); C07D 213/04 (2006.01); C07D 333/04 (2006.01); C07D 307/34 (2006.01)
CPC C07D 231/18 (2013.01) 22 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt or solvate thereof, wherein:
Q is selected from O or S;
V, X and Y are each independently selected from C and N, and W and Z are each independently selected from N, O, S, NH and CH, provided that at least one of V, W, X, Y and Z is N, O, S or NH;
RX and RY are each independently a halo, —OH, —NO2, —NH2, —N3, —SH, —SO2H, —SO2NH, or a saturated or unsaturated hydrocarbyl group, wherein the hydrocarbyl group may be straight-chained or branched, or be or include cyclic groups, wherein the hydrocarbyl group may optionally be substituted, and wherein the hydrocarbyl group may optionally include one or more heteroatoms N, O or S in its carbon skeleton;
optionally RX and RY together with the atoms X and Y to which they are attached may form a 4- to 12-membered saturated or unsaturated cyclic group fused to ring A, wherein the cyclic group fused to ring A may optionally be substituted;
m is 0, 1 or 2;
each R1 is independently a halo, —OH, —NO2, —NH2, —N3, —SH, —SO2H, —SO2NH, or a saturated or unsaturated hydrocarbyl group, wherein the hydrocarbyl group may be straight-chained or branched, or be or include cyclic groups, wherein the hydrocarbyl group may optionally be substituted, and wherein the hydrocarbyl group may optionally include one or more heteroatoms N, O or S in its carbon skeleton;
optionally RX and any R1 attached to W may together with the atoms W and X to which they are attached form a 4- to 12-membered saturated or unsaturated cyclic group fused to ring A, wherein the cyclic group fused to ring A may optionally be substituted;
optionally RY and any R1 attached to Z may together with the atoms Y and Z to which they are attached form a 4- to 12-membered saturated or unsaturated cyclic group fused to ring A, wherein the cyclic group fused to ring A may optionally be substituted; and
R2 is selected from:
(i) a group having the formula:

OG Complex Work Unit Chemistry
wherein R20 is a halo, —OH, —NO2, —NH2, —N3, —SH, —SO2H, —SO2NH, or a saturated or unsaturated hydrocarbyl group, wherein the hydrocarbyl group may be straight-chained or branched, or be or include cyclic groups, wherein the hydrocarbyl group may optionally be substituted, and wherein the hydrocarbyl group may optionally include one or more heteroatoms N, O or S in its carbon skeleton; or
(ii) a heteroaryl group substituted at the α and α′ positions, wherein R2 may optionally be further substituted.