US 11,964,943 B2
3,5-diarylidenyl-n-substituted-piperid-4-one-derived inhibitors of Stat3 pathway activity and uses thereof
Konstantinos Kiakos, Vienna (AT); John A. Hartley, London (GB); and Moses Namfong Lee, Vancouver, WA (US)
Filed by Konstantinos Kiakos, Vienna (AT); John A. Hartley, London (GB); and Moses Namfong Lee, Vancouver, WA (US)
Filed on May 19, 2020, as Appl. No. 15/929,736.
Application 15/929,736 is a continuation of application No. PCT/EP2018/081905, filed on Nov. 20, 2018.
Claims priority of provisional application 62/588,678, filed on Nov. 20, 2017.
Prior Publication US 2020/0399220 A1, Dec. 24, 2020
Int. Cl. C07D 211/74 (2006.01); A61K 31/282 (2006.01); A61K 31/45 (2006.01); A61K 31/555 (2006.01); A61K 33/243 (2019.01); A61K 45/06 (2006.01); A61P 35/00 (2006.01); C07D 213/68 (2006.01); G01N 33/58 (2006.01); A61K 31/337 (2006.01)
CPC C07D 213/68 (2013.01) [G01N 33/582 (2013.01); A61K 31/282 (2013.01); A61K 31/337 (2013.01); A61K 33/243 (2019.01); A61K 45/06 (2013.01)] 18 Claims
 
1. A compound, comprising Formula I:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, solvate, radiolabeled form, stereoisomeric form, racemic mixture, geometric isomer, and/or tautomer thereof, wherein:
R is —(C6-C14)aryl, which is unsubstituted or substituted with 1, 2, 3, 4, or 5 independently selected R6 groups;
R6 is selected from:
(a) —H, —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, —(C1-C6)alkoxy, and —(C3-C5)cycloalkyl; and
(b) -halo, —C(halo)3, —CH(halo)2, —CH2(halo), —CN, —NO, —NO2, —N3, —OH, —SH, —N(R7)2, —NH(OH), —C(═O)R7, —C(═O)OR7, —OC(═O)R7, —C(═O)N(R7)2, —N(R7)C(═O)R7, —N(R7)C(═O)N(R7)2, —OC(═O)N(R7)2, and —N(R7)C(═O)OR7;
R1, R2, R4, and R5 are independently selected from:
(a) —H, —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, and —(C1-C6)alkoxy; and
(b) -halo, —C(halo)3, —CH(halo)2, —CH2(halo), —CN, —NO, —NO2, —N3, —OH, —SH, —N(R7)2, —NH(OH), —C(═O)R7, —C(═O)OR7, —OC(═O)R7, —C(═O)N(R7)2, —N(R7)C(═O)R7, —N(R7)C(═O)N(R7)2, —OC(═O)N(R7)2, and —N(R7)C(═O)OR7;
R3 is selected from the group consisting of:
(a) —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, and —(C1-C6)alkoxy; and
(b) -halo, —C(halo)3, —CH(halo)2, —CH2(halo), —CN, —NO, —NO2, —N3, —OH, —SH, —N(R7)2, —NH(OH), —C(═O)R7, —C(═O)OR7, —OC(═O)R7, —C(═O)N(R7)2, —N(R7)C(═O)R7, —N(R7)C(═O)N(R7)2, —OC(═O)N(R7)2, and —N(R7)C(═O)OR7;
each R7 is independently selected from the group consisting of —H, —(C1-C6)alkyl, —(C2-C6)alkenyl, and —(C2-C6)alkynyl; and
each halo is independently —F, —Cl, —Br, or —I.