US 11,963,963 B2
6-heterocyclyl-4-morpholin-4-ylpyridine-2-one compounds useful for the treatment of cancer and diabetes
Jessica Martinsson, Huddinge (SE); Martin Andersson, Huddinge (SE); Johan Lindström, Huddinge (SE); Rickard Forsblom, Huddinge (SE); Fredrik Rahm, Huddinge (SE); Tobias Ginman, Huddinge (SE); and Jenny Viklund, Huddinge (SE)
Assigned to Sprint Bioscience AB, Huddinge (SE)
Filed by Sprint Bioscience AB, Huddinge (SE)
Filed on Oct. 14, 2021, as Appl. No. 17/501,407.
Application 17/501,407 is a continuation of application No. 15/999,432, granted, now 11,179,399, previously published as PCT/EP2017/053614, filed on Feb. 17, 2017.
Claims priority of application No. 16156533 (EP), filed on Feb. 19, 2016.
Prior Publication US 2022/0175788 A1, Jun. 9, 2022
Int. Cl. A61K 31/5377 (2006.01); A61K 31/4745 (2006.01); A61K 31/5386 (2006.01); A61K 31/541 (2006.01); A61K 33/243 (2019.01); A61K 45/06 (2006.01); A61P 35/00 (2006.01); C07D 401/04 (2006.01); C07D 413/14 (2006.01); C07D 417/14 (2006.01)
CPC A61K 31/5377 (2013.01) [A61K 31/4745 (2013.01); A61K 31/5386 (2013.01); A61K 31/541 (2013.01); A61K 33/243 (2019.01); A61K 45/06 (2013.01); A61P 35/00 (2018.01); C07D 401/04 (2013.01); C07D 413/14 (2013.01); C07D 417/14 (2013.01)] 20 Claims
 
1. A process for preparing a compound represented by Formula (I):

OG Complex Work Unit Chemistry
wherein
R1, R2 and R3 are independently selected from the group consisting of hydrogen, C1-C3haloalkyl and C1-C3alkyl;
A represents

OG Complex Work Unit Chemistry
wherein
X is selected from the group consisting of CH2, S, SO, SO2, NR5, NCOR5, NCOR9, NCOCH2R9, and a bond;
Y is selected from the group consisting of N, CH and C;
n is selected from the group consisting of 1, 2, 3 and 4;
R4 is selected from the group consisting of hydrogen, halogen, COR6, C1-C6alkyl, C1-C3alkoxyC1-C3alkyl, C1-C6alkoxy, C3-C6cycloalkyl, C3-C6heterocyclyl, C1-C3cyanoalkyl, C1-C3haloalkyl, aryl and heteroaryl, wherein said aryl and said heteroaryl are optionally substituted with one or more R7;
R5 is selected from the group consisting of hydrogen, C1-C3fluoroalkyl, C1-C3alkyl, C1-C3alkoxyC1-C3alkyl and C3-C6cycloalkyl;
R6 is selected from the group consisting of C1-C3alkoxy, N—C1-C3alkylamino, N,N-diC1-C3alkylamino, 1-pyrrolidinyl, 1-piperidinyl and 1-azetidinyl;
R7 is selected from the group consisting of C1-C6alkyl, C3-C6cycloalkyl, C1-C3alkoxyC1-C3alkyl, C1-C3haloalkyl, halogen, N—C1-C3alkylamino, N,N-diC1-C3alkylamino, C1-C3haloalkoxy and C1-C3alkoxy;
R9 is selected from the group consisting of C1-C3alkyl, C1-C3alkoxy, C3-C6cycloalkyl, heterocyclyl, phenyl and a monocyclic heteroaryl, wherein said heterocyclyl, said phenyl and said monocyclic heteroaryl are optionally substituted with one or two R8; and
R8 is selected from the group consisting of halogen, C1-C3haloalkyl and C1-C3alkyl;
and pharmaceutically acceptable salts, stereoisomers and tautomers thereof;
the process comprising:
(i) providing a compound represented by Formula (III):

OG Complex Work Unit Chemistry
wherein
R1, R2, R3, and A are as defined as above;
R10 is selected from the group consisting of F, OCH3, OC(CH3)3, and OSiR′R″R′″; and
R′, R″, and R′″ are each independently aryl or alkyl; and
(ii) converting the compound represented by Formula (III) into the compound represented by Formula (I).