US 11,981,661 B2
Heterocyclic compounds
Joerg Benz, Basel (CH); Uwe Grether, Basel (CH); Benoit Hornsperger, Basel (CH); Carsten Kroll, Basel (CH); Bernd Kuhn, Basel (CH); Rainer E. Martin, Basel (CH); Fionn O'Hara, Basel (CH); Bernd Puellmann, Basel (CH); Hans Richter, Basel (CH); and Martin Ritter, Basel (CH)
Assigned to Hoffmann-La Roche Inc., Little Falls, NJ (US)
Filed by Hoffmann-La Roche Inc., Little Falls, NJ (US)
Filed on Sep. 2, 2021, as Appl. No. 17/465,536.
Claims priority of application No. 20194318 (EP), filed on Sep. 3, 2020.
Prior Publication US 2022/0098176 A1, Mar. 31, 2022
Int. Cl. C07D 401/14 (2006.01); A61K 9/00 (2006.01); A61K 9/20 (2006.01); A61K 9/48 (2006.01); C07D 403/06 (2006.01); C07D 413/06 (2006.01); C07D 413/14 (2006.01); C07D 487/04 (2006.01)
CPC C07D 403/06 (2013.01) [A61K 9/2009 (2013.01); A61K 9/2054 (2013.01); A61K 9/2059 (2013.01); A61K 9/485 (2013.01); A61K 9/4858 (2013.01); A61K 9/4866 (2013.01); C07D 401/14 (2013.01); C07D 413/06 (2013.01); C07D 413/14 (2013.01); C07D 487/04 (2013.01)] 17 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
X is selected from O, NH, N(C1-6-alkyl), and (CH2)mCHR6;
Y is (CH2)nCHR7;
m and n are each independently an integer selected from 0 and 1;
L is selected from a covalent bond, —CHR8—, —CH2O—, SO2, —SO2NH—, —SO2NH—C1-6-alkyl-, —O—, —NH—, —CH2NH—, —CH2N(C1-6-alkyl)-, and —C≡C—;
LD is selected from a covalent bond, SO2, —O—, —NR11—, and —CH2NH—;
B is selected from:

OG Complex Work Unit Chemistry
C is selected from:

OG Complex Work Unit Chemistry
D is selected from:

OG Complex Work Unit Chemistry
RL is selected from C1-6-alkyl and a group

OG Complex Work Unit Chemistry
(i) A is

OG Complex Work Unit Chemistry
R1 is selected from halogen, SF5, sulfamoyl, C1-6-alkyl, CF3CH2—, C1-6-alkyl-SO2—, halo-C1-6-alkyl-SO2—, cyano-C1-6-alkyl-SO2—, halo-C1-6-alkoxy, and a group

OG Complex Work Unit Chemistry
 and
R2 is selected from hydrogen, C1-6-alkyl-SO2— and halogen; or
(ii) A is selected from

OG Complex Work Unit Chemistry
R1 is selected from halogen, SF5, sulfamoyl, C1-6-alkyl, halo-C1-6-alkyl, C1-6-alkyl-SO2—, halo-C1-6-alkyl-SO2—, cyano-C1-6-alkyl-SO2—, halo-C1-6-alkoxy, and a group

OG Complex Work Unit Chemistry
 and
R2 is selected from hydrogen, C1-6-alkyl-SO2— and halogen;
R3 and R7 are both hydrogen;
R4 is hydrogen or oxo;
R5 is hydrogen or C1-6-alkyl;
R6 is selected from hydrogen, halogen, hydroxy and C1-6-alkyl;
R8 is selected from hydrogen and C6-C14-aryl;
R9 is selected from hydrogen, hydroxy, oxo, halogen, cyano, carbamoyl, C1-6-alkyl, C3-C10-cycloalkyl, C1-6-alkoxy, halo-C1-6-alkyl, hydroxy-C1-6-alkyl, halo-C1-6-alkoxy, C1-6-alkyl-SO2—C1-6-alkyl-, C1-6-alkyl-SO2—, C1-6-alkoxy-carbonyl, wherein said C3-C10-cycloalkyl is optionally substituted with one halo-C1-C6-alkyl;
R10 is selected from hydrogen, halogen, hydroxy, oxo, C1-6-alkyl, and halo-C1-6-alkyl; and
R11 is selected from hydrogen, C1-6-alkyl, C1-6-alkoxy-C1-6-alkyl, C3-10-cycloalkyl-C1-6-alkyl-, and C6-C14-aryl.