US 12,030,875 B2
EIF4E inhibitors and uses thereof
Ashis Saha, Arlington, MA (US)
Assigned to PIC THERAPEUTICS, INC., Natick, MA (US)
Appl. No. 17/273,878
Filed by PIC Therapeutics, Inc., Natick, MA (US)
PCT Filed Sep. 6, 2019, PCT No. PCT/US2019/049903
§ 371(c)(1), (2) Date Mar. 5, 2021,
PCT Pub. No. WO2020/051424, PCT Pub. Date Mar. 12, 2020.
Claims priority of provisional application 62/728,372, filed on Sep. 7, 2018.
Prior Publication US 2022/0089587 A1, Mar. 24, 2022
Int. Cl. C07D 417/04 (2006.01); A61P 35/00 (2006.01); C07D 277/30 (2006.01); C07D 277/42 (2006.01); C07D 417/10 (2006.01); C07D 417/14 (2006.01)
CPC C07D 417/04 (2013.01) [A61P 35/00 (2018.01); C07D 277/30 (2013.01); C07D 277/42 (2013.01); C07D 417/10 (2013.01); C07D 417/14 (2013.01)] 19 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
L1 is a bond, O, or S;
R1 is phenyl substituted with 1-4 substituents independently selected from —CN, halogen, —OH, unsubstituted —C1-6alkyl, unsubstituted —O—C1-6alkyl, and an unsubstituted 3-8 membered monocyclic saturated or partially unsaturated heterocyclic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur;
L2 is a C1-8 bivalent straight or branched hydrocarbon chain, wherein 1, 2, or 3 methylene units of the hydrocarbon chain are optionally and independently replaced with —N(R)— or —Cy—;
each R is independently selected from hydrogen or optionally substituted —C1-6 aliphatic;
each —Cy— is independently an optionally substituted bivalent ring selected from a 3-6 membered monocyclic, saturated or partially unsaturated, carbocyclic ring, or a 3-6 membered monocyclic, saturated or partially unsaturated, heterocyclic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur;
R2 is —COOR; and
R3 is optionally substituted —C1-6 aliphatic, halogen, or an optionally substituted ring selected from phenyl, an 8-10 membered bicyclic aromatic carbocyclic ring, a 5-6 membered monocyclic heteroaromatic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur, or an 8-10 membered bicyclic heteroaromatic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, and sulfur.