US 12,435,083 B2
Cyclopropyl-(hetero)aryl-substituted ethylsulphonyl-pyridine derivatives
Bart Herlé, Biberach an der Riss (DE); Hannes Fiepko Koolman, Biberach an der Riss (DE); Alan Long, Biberach an der Riss (DE); Robin Meier, Biberach an der Riss (DE); Ikki Yonemura, Osaka (JP); and Julien Gagnepain, Ummendorf (DE)
Assigned to Boehringer Ingelheim Vetmedica Gmbh, Ingelheim am Rhein (DE); and Nihon Nohyaku Co., Ltd., Tokyo (JP)
Filed by BOEHRINGER INGELHEIM VETMEDICA GMBH, Ingelheim am Rhein (DE); and NIHON NOHYAKU CO., LTD., Tokyo (JP)
Filed on Sep. 9, 2022, as Appl. No. 17/930,882.
Claims priority of provisional application 63/243,561, filed on Sep. 13, 2021.
Claims priority of application No. 21198461 (EP), filed on Sep. 23, 2021.
Prior Publication US 2023/0234951 A1, Jul. 27, 2023
Int. Cl. C07D 471/04 (2006.01); C07D 401/04 (2006.01); C07D 401/14 (2006.01); C07D 413/04 (2006.01); C07D 413/14 (2006.01); C07D 417/04 (2006.01); C07D 487/04 (2006.01); C07D 498/04 (2006.01); C07D 513/04 (2006.01)
CPC C07D 471/04 (2013.01) [C07D 401/04 (2013.01); C07D 401/14 (2013.01); C07D 413/04 (2013.01); C07D 413/14 (2013.01); C07D 417/04 (2013.01); C07D 487/04 (2013.01); C07D 498/04 (2013.01); C07D 513/04 (2013.01)] 32 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Chemistry
wherein:
W1, W2, W3, W4, W5 are each independently N, C or C—H, wherein at most three of W1, W2, W3, W4, W5 are N;

OG Complex Work Unit Chemistry
is attached to a C atom;
R, R1a, R1b, R2a, R2b, R3 are each independently hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, aryl, C1-C6-alkoxy, C1-C6-haloalkoxy, S(O)r—(C1-C6-alkyl), S(O)s—(C1-C6-haloalkyl), S(O)t—Rw, S(O)2—N(Rx)(Ry), or S(O)—(Rw)=N—Rz; and wherein R3, if present once or more times, in each occurrence is independently attached to a C atom; or wherein R together with R1a or R1b forms an unsubstituted or substituted carbocycle or an unsubstituted or substituted heterocycle, wherein the carbocycle or heterocycle if substituted is independently substituted with one, two or three substituents each independently selected from the group consisting of halogen, alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, aryl, C1-C6-alkoxy, C1-C6-haloalkoxy, OH, CN, C(O)ORx, S(O)r—(C1-C6-alkyl), and S(O)s—(C1-C6-haloalkyl);
Q is selected from the group consisting of:

OG Complex Work Unit Chemistry
wherein:
R4 is selected from the group consisting of C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-haloalkoxy, S(O)p—(C1-C6-alkyl), S(O)q—(C1-C6-haloalkyl), and =O, wherein, if R4 is present once or more times, in each occurrence is independently attached to a C atom;
R5, R9 are each independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-alkyl, C3-C8-cycloalkyl substituted with one or more haloalkyl, C3-C8-cycloalkyl substituted with one or more halogens, C(O)—(C1-C6-alkyl), heterocyclyl, S(O)p—(C1-C6-alkyl), and S(O)q—(C1-C6-haloalkyl);
R6, R7, R8 are each independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
m is 0, 1 or 2; and
p, q in each occurrence independently are 0, 1 or 2;
Rv, Rw, Rx, Ry, Rz in each occurrence are independently selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, and C1-C6-haloalkyl;
n is 0, 1, 2, 3, or 4;
r, s, t in each occurrence independently are 0, 1 or 2; and
the dashed bond (custom character) signifies a single or double bond;
or a pharmaceutically acceptable salt thereof.