US 12,065,429 B2
Small molecule modulators of IL-17
Mark Andrews, Ballerup (DK); Mogens Larsen, Ballerup (DK); Alan Jessiman, Ballerup (DK); Patrick Johnson, Valby (DK); and Kevin Neil Dack, Ballerup (DK)
Assigned to Leo Pharma A/S, Ballerup (DK)
Filed by LEO Pharma A/S, Ballerup (DK)
Filed on Dec. 1, 2023, as Appl. No. 18/526,149.
Claims priority of application No. 22211150 (EP), filed on Dec. 2, 2022; application No. 22216032 (EP), filed on Dec. 22, 2022; and application No. 23151131 (EP), filed on Jan. 11, 2023.
Prior Publication US 2024/0208938 A1, Jun. 27, 2024
Int. Cl. C07D 401/14 (2006.01)
CPC C07D 401/14 (2013.01) 20 Claims
 
1. A compound according to formula (I)

OG Complex Work Unit Chemistry
wherein X is fluoro or chloro;
R1 is selected from

OG Complex Work Unit Chemistry
wherein R5 is independently selected from (C1-C4)alkyl, (C3-C4)cycloalkyl, and —CH2—(C3-C4)cycloalkyl, wherein said (C1-C4)alkyl, (C3-C4)cycloalkyl, and —CH2—(C3-C4)cycloalkyl are optionally substituted with substituents independently selected from one hydroxy group and 1, 2, or 3 fluoro;
R2 is selected from hydrogen, (C1-C3)alkyl, cyclopropyl, and chloro, wherein said (C1-C3)alkyl is optionally substituted with one or more fluoro;
R3 is selected from hydrogen, (C1-C3)alkyl, cyclopropyl, and chloro, wherein said (C1-C3)alkyl is optionally substituted with one or more fluoro; and
R4 is selected from hydrogen, (C1-C3)alkyl, cyclopropyl, (C1-C2)alkoxy, cyano, methylsulfone, fluoro, and chloro; wherein said (C1-C3)alkyl and (C1-C2)alkoxy are optionally substituted with one or more fluoro;
provided that at least one of R2 and R3 is not hydrogen;
or pharmaceutically acceptable salts thereof.