US 12,377,084 B2
ERAP1 modulators
Martin Quibell, Oxford (GB); Michael Sparenberg, Oxford (GB); and Jason John Shiers, Oxford (GB)
Assigned to Grey Wolf Therapeutics Limited, Abingdon (GB)
Appl. No. 17/774,239
Filed by GREY WOLF THERAPEUTICS LIMITED, Abingdon (GB)
PCT Filed Nov. 12, 2020, PCT No. PCT/GB2020/052886
§ 371(c)(1), (2) Date May 4, 2022,
PCT Pub. No. WO2021/094763, PCT Pub. Date May 20, 2021.
Claims priority of application No. 1916597 (GB), filed on Nov. 14, 2019; and application No. 2007717 (GB), filed on May 22, 2020.
Prior Publication US 2023/0000851 A1, Jan. 5, 2023
Int. Cl. A61K 31/196 (2006.01); A61K 31/277 (2006.01); A61K 31/40 (2006.01); A61K 31/41 (2006.01); A61K 31/451 (2006.01); A61K 31/454 (2006.01); A61K 35/15 (2025.01); A61K 39/00 (2006.01); A61K 39/395 (2006.01); C07C 311/21 (2006.01); C07C 317/34 (2006.01); C07D 207/09 (2006.01); C07D 211/28 (2006.01); C07D 211/34 (2006.01); C07D 257/04 (2006.01); C07D 401/10 (2006.01); C07D 417/10 (2006.01)
CPC A61K 31/451 (2013.01) [A61K 31/196 (2013.01); A61K 31/277 (2013.01); A61K 31/40 (2013.01); A61K 31/41 (2013.01); A61K 31/454 (2013.01); A61K 35/15 (2013.01); A61K 39/0011 (2013.01); A61K 39/3955 (2013.01); C07C 311/21 (2013.01); C07C 317/34 (2013.01); C07D 207/09 (2013.01); C07D 211/28 (2013.01); C07D 211/34 (2013.01); C07D 257/04 (2013.01); C07D 401/10 (2013.01); C07D 417/10 (2013.01); A61K 2039/507 (2013.01); A61K 2039/572 (2013.01); A61K 2039/585 (2013.01); C07C 2601/02 (2017.05); C07C 2601/14 (2017.05)] 20 Claims
 
1. A compound of formula (I), or a pharmaceutically acceptable salt or hydrate thereof,

OG Complex Work Unit Chemistry
wherein:
Z is a group of formula:

OG Complex Work Unit Chemistry
wherein P and Q are each independently CR12R13; or
one of P and Q is NR14 and the other is CR12R13;
the group X—Y is —NHSO2— or —SO2NH—;
R1 is H, CN or alkyl;
R2 is selected from COOH and a tetrazolyl group;
R3 is selected from H, CI and alkyl;
R4 is selected from H and halo;
R5 is selected from H, alkyl, haloalkyl, SO2-alkyl, CI, alkoxy, OH, CN, hydroxyalkyl, alkylthio, heteroaryl, cycloalkyl, heterocycloalkyl and haloalkoxy;
R6 is H;
R7 is selected from H, CN, haloalkyl, halo, SO2-alkyl, heteroaryl, SO2NR16R17, CONR10R11 and alkyl, wherein said heteroaryl group is optionally substituted by one or more substituents selected from alkyl, halo, alkoxy, CN, haloalkyl and OH;
R8 is selected from H, alkyl, haloalkyl and halo;
R9 is H or halo; and
R10, R11, R12, R13, R14, R16 and R17 are each independently H or alkyl;
R15 is selected from alkyl, halo, alkoxy, CN, haloalkyl and OH; and
m and n are each independently 0, 1, 2 or 3.