US 12,134,600 B2
Method for producing a vadadustat intermediate
Koji Machida, Takasago (JP); Hiroaki Yasukouchi, Takasago (JP); and Akira Nishiyama, Takasago (JP)
Assigned to KANEKA CORPORATION, Osaka (JP)
Appl. No. 17/605,408
Filed by KANEKA CORPORATION, Osaka (JP)
PCT Filed Mar. 5, 2020, PCT No. PCT/JP2020/009453
§ 371(c)(1), (2) Date Oct. 21, 2021,
PCT Pub. No. WO2020/217733, PCT Pub. Date Oct. 29, 2020.
Claims priority of application No. 2019-086759 (JP), filed on Apr. 26, 2019.
Prior Publication US 2022/0204451 A1, Jun. 30, 2022
Int. Cl. C07D 213/81 (2006.01)
CPC C07D 213/81 (2013.01) 9 Claims
 
1. A method for producing a first vadadustat intermediate comprising:
reacting a compound represented by the following formula (1):

OG Complex Work Unit Chemistry
wherein X represents a chlorine atom, a hydroxy group, or OP1; and P1 represents an oxygen protecting group,
with glycine or a glycine derivative represented by the following formula (2):

OG Complex Work Unit Chemistry
wherein R1 represents a hydroxy group, OR2, or NR3R4; R2, R3, and R4 independently represent an alkyl group having 1 to 20 carbon atoms and optionally having a substituent, an aryl group having 6 to 20 carbon atoms and optionally having a substituent, or an aralkyl group having 7 to 20 carbon atoms and optionally having a substituent; and R3 and R4 may join together to form a ring, or a salt of the glycine or the glycine derivative in the presence of carbon monoxide to produce the first vadadustat intermediate represented by the following formula (3):

OG Complex Work Unit Chemistry
wherein R1 and X are the same as the above.