US 11,970,469 B2
Compounds useful in the treatment of disorders associated with mutant RAS
Terrence Rabbitts, Headington (GB); Camilo Quevedo, Headington (GB); and Carole Bataille, Oxford (GB)
Assigned to THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL, London (GB)
Appl. No. 15/734,244
Filed by Oxford University Innovation Limited, Oxford (GB)
PCT Filed Jun. 3, 2019, PCT No. PCT/GB2019/051536
§ 371(c)(1), (2) Date Dec. 2, 2020,
PCT Pub. No. WO2019/234405, PCT Pub. Date Dec. 12, 2019.
Claims priority of application No. 1809102 (GB), filed on Jun. 4, 2018.
Prior Publication US 2021/0214322 A1, Jul. 15, 2021
Int. Cl. C07D 265/30 (2006.01); A61K 45/06 (2006.01); C07C 217/92 (2006.01); C07C 237/30 (2006.01); C07D 213/74 (2006.01)
CPC C07D 265/30 (2013.01) [A61K 45/06 (2013.01); C07C 217/92 (2013.01); C07C 237/30 (2013.01); C07D 213/74 (2013.01)] 10 Claims
 
1. A compound of Formula Ih, Ii, Ij or Ik, or a salt or solvate thereof:

OG Complex Work Unit Chemistry
wherein,
R1 is selected from C1-6 alkoxy and NRpRq, wherein Rp and Rq are independently selected from hydrogen, C1-6 alkyl and C(O)C1-3alkyl;
R2 and R3 are independently selected from the group consisting of hydrogen, hydroxyl, halogen, CN, C1-6 haloalkyl, C1-6 haloalkoxy, O—C1-6 alkyl and C1-6 alkyl;
R4 is selected from hydrogen and C1-3 alkyl;
R5 is selected from the group consisting of hydrogen, hydroxyl, ═O, halogen, CN, C1-6 haloalkyl, C1-6 haloalkoxy, O—C1-6 alkyl, C1-6 alkyl and NRpRq;
R6 is selected from the group consisting of hydrogen, hydroxyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, O—C1-6 alkyl, C1-6 alkyl and NRpRq;
R7a and R7b are independently selected from hydrogen, hydroxyl, halogen, C1-6 haloalkyl, C1-6 haloalkoxy, O—C1-6 alkyl and C1-6 alkyl;
R8 is selected from selected from the group consisting of hydrogen and C1-6 alkyl; and
R9 is selected from C1-6 alkyl, optionally substituted with one or more groups of HNMe or NMe2; or
R9 is —(CH2)1-6-heterocycle, wherein said heterocycle is or morpholine optionally substituted with one or more C1-6 alkyl; or
R9 if —C(O)NH(CH2)1-4-heterocycle, wherein said heterocycle is piperidine substituted by Rk; wherein Rk is selected from the group consisting of hydrogen, C1-6 alkyl optionally substituted with phenyl, —C(O)OH, and —C(O)OC1-6 alkyl.