US 12,391,641 B2
Prostaglandin EP4 receptor antagonist compounds
Miles Stuart Congreve, Cambridge (GB); Nigel Alan Swain, Cambridge (GB); and Benjamin Whitehurst, Cambridge (GB)
Assigned to Nxera Pharma UK Limitied, (GB)
Appl. No. 17/767,188
Filed by NXERA PHARMA UK LIMITED, Cambridge (GB)
PCT Filed Oct. 9, 2020, PCT No. PCT/GB2020/052530
§ 371(c)(1), (2) Date Apr. 7, 2022,
PCT Pub. No. WO2021/069927, PCT Pub. Date Apr. 15, 2021.
Claims priority of application No. 1914585 (GB), filed on Oct. 9, 2019.
Prior Publication US 2022/0411364 A1, Dec. 29, 2022
Int. Cl. C07C 233/55 (2006.01); A61K 31/165 (2006.01); A61K 31/36 (2006.01); A61K 31/437 (2006.01); A61K 31/4412 (2006.01); A61P 13/12 (2006.01); A61P 15/00 (2006.01); A61P 19/02 (2006.01); A61P 25/06 (2006.01); A61P 25/28 (2006.01); C07C 235/12 (2006.01); C07C 235/14 (2006.01); C07C 311/51 (2006.01); C07C 317/22 (2006.01); C07D 235/26 (2006.01); C07D 257/04 (2006.01); C07D 305/06 (2006.01)
CPC C07C 233/55 (2013.01) [C07C 311/51 (2013.01); C07C 317/22 (2013.01); C07D 257/04 (2013.01); C07D 305/06 (2013.01)] 27 Claims
 
1. A compound of Formula (1):

OG Complex Work Unit Chemistry
or a salt thereof, wherein;
A is selected from the group consisting of:

OG Complex Work Unit Chemistry
X is an optionally substituted phenyl ring, an optionally substituted pyridyl ring or an optionally substituted imidazopyridine ring system; R1 and R2 are independently H or a C1-3 alkyl group which is optionally substituted with one or more fluorine atoms; or R1 and R2 are joined to form a 3-6 membered carbocyclic ring which is optionally substituted with one or more fluorine atoms;
R3 is H, C1-3 alkyl or F;
R4 is H or C1-3 alkyl; R8 is C1-3 alkyl or a C3-6 cycloalkyl ring; and either R10 and R11 are both methyl or R10 and R11 are joined to form a cyclobutyl ring.