Granted Patent B2

US 12,221,453 · App. 17/806,893 · Granted Feb 11, 2025

Inventors: Craig E. Masse (Cambridge, MA); Jeremy Robert Greenwood (Brooklyn, NY); Sayan Mondal (New York, NY)

Assignee: Takeda Pharmaceutical Company Limited

C07D519/00C07D487/04

Abstract

Claims (27)

1. A compound of Formula I′:

or a pharmaceutically acceptable salt or stereoisomer thereof, wherein:

R 1 is -L 1 -R 1A ;

L 1 is a covalent bond;

R 1A is an 8- to 10-membered heteroaryl ring;

wherein the heteroaryl ring is bicyclic;

wherein the heteroaryl ring has 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;

wherein the heteroaryl ring is optionally substituted with one or more substituents independently selected from the group consisting of halogen, CN, C 1-6 aliphatic, C(O)NRR, OR, a 3- to 7-membered carbocyclic ring, and a 4- to 7-membered heterocyclic ring;

wherein each 3- to 7-membered carbocyclic ring and 4- to 7-membered heterocyclic ring substituent is independently saturated or partially unsaturated;

wherein each 4- to 7-membered heterocyclic ring substituent has 1 or 2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; and

wherein each 3- to 7-membered carbocyclic ring and 4- to 7-membered heterocyclic ring substituent is optionally and independently substituted with one or more OH substituents;

each R is independently H, C 1-6 aliphatic, a 3- to 7-membered heterocyclic ring, phenyl, or a 5- or 6-membered heteroaryl ring;

wherein each heterocyclic ring is independently saturated or partially unsaturated;

wherein each heterocyclic ring independently has 1 or 2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; and

wherein each heteroaryl ring independently has 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; or

any two geminal R substituents, taken together with the nitrogen atom to which they are attached, independently form a 4- to 7-membered heterocyclic ring or a 5- or 6-membered heteroaryl ring;

wherein each heterocyclic ring is independently saturated or partially unsaturated; and

wherein each heterocyclic ring and heteroaryl ring independently has 0, 1, 2, or 3 additional heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;

R 2 is C(O)NHR 2A ;

R 2A is a 3- to 7-membered saturated carbocyclic ring;

wherein the carbocyclic ring is saturated; and

wherein the carbocyclic ring is substituted with n independently selected R 2C substituents;

each R 2C is independently halogen or OH; and

n is 0, 1, or 2.

2. The compound of claim 1 , or a stereoisomer thereof, wherein the compound, or stereoisomer thereof, is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

3. A pharmaceutical composition comprising a pharmaceutically acceptable carrier, adjuvant, or vehicle and a compound of claim 1 , or a pharmaceutically acceptable salt or stereoisomer thereof.

Assignments (7)

Continuity (5)

References Cited (131)