US 12,338,232 B2
THRβ receptor agonist compound and preparation method and use thereof
Shanghai Yu, Kun Shan (CN); and Ben Li, Kun Shan (CN)
Assigned to Terns, Inc., Foster City, CA (US)
Filed by Terns, Inc., Foster City, CA (US)
Filed on May 10, 2023, as Appl. No. 18/315,291.
Application 18/315,291 is a continuation of application No. 17/951,883, filed on Sep. 23, 2022, abandoned.
Application 17/951,883 is a continuation of application No. 17/675,690, filed on Feb. 18, 2022, abandoned.
Application 17/675,690 is a continuation of application No. 17/305,302, filed on Jul. 2, 2021, abandoned.
Application 17/305,302 is a continuation of application No. 16/712,301, filed on Dec. 12, 2019, granted, now 11,084,802, issued on Aug. 10, 2021.
Claims priority of application No. 201811527414.4 (CN), filed on Dec. 13, 2018.
Prior Publication US 2023/0278988 A1, Sep. 7, 2023
Int. Cl. C07D 403/12 (2006.01)
CPC C07D 403/12 (2013.01) 25 Claims
 
1. A method of synthesizing a compound of Formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof;
wherein:
Ring A is a C5-10 aliphatic ring or a C5-10 aromatic ring, each optionally substituted with one or more substituents independently selected from the group consisting of hydrogen, halogen atoms, hydroxy, —OCF3, —NH2, —NHC1-4 alkyl, —N(C1-4alkyl)2, —CONH2, —CONHC1-4 alkyl, —CON(C1-4 alkyl)2, —NHCOC1-4 alkyl, C1-6 alkyl, C1-6 alkoxy, and C3-6 cycloalkyl, and when two substituents are contained, the two substituents can form a ring structure together with the carbon connected thereto; and the halogen atoms are selected from the group consisting of F, Cl and Br;
R2 and R3 are each independently selected from the group consisting of halogen atoms, and substituted or unsubstituted C1-6 alkyl, the substituent being selected from the group consisting of halogen atoms, hydroxy, and C1-6 alkoxy; and
R1 is selected from the group consisting of hydrogen, cyano, substituted or unsubstituted C1-6 alkyl, and substituted or unsubstituted C3-6 cycloalkyl, the substituent being selected from the group consisting of halogen atoms, hydroxy, and C1-6 alkoxy;
comprising a step of contacting a compound of Formula (I-c):

OG Complex Work Unit Chemistry
or a salt thereof, with a compound of Formula (I-d):

OG Complex Work Unit Chemistry
or a salt thereof, to produce a compound of Formula (I-e):

OG Complex Work Unit Chemistry
or a salt thereof.