Cyclopropyl-(hetero)aryl-substituted ethylsulphonyl-pyridine derivatives

Patent metadata

Field	Value
Publication number	US-12435083-B2
Application number	US-202217930882-A
Country	US
Kind code	B2
Filing date	Sep 9, 2022
Priority date	Sep 13, 2021
Publication date	Oct 7, 2025
Grant date	Oct 7, 2025

Abstract

The present invention relates to cyclopropyl-(hetero)aryl substituted ethylsulphonyl-pyridine derivatives of formula (1)

wherein the variables are as defined in the description and in the claims, which can be used as antiparasitic agents for the treatment, prevention and/or control of parasitic infections and/or infestations in animals.

First claim

The invention claimed is:

1. A compound of formula (I)

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;

is attached to a C atom;
R, R1a, R1b, R2a, R2b, R3 are each independently hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C3-C8-cycloalkyl, aryl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, S(O) r —(C 1 -C 6 -alkyl), S(O) s —(C 1 -C 6 -haloalkyl), S(O) t —R w , S(O) 2 —N(R x )(R y ), or S(O)—(R w )=N—R z ; 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, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, aryl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, OH, CN, C(O)OR x , S(O) r —(C 1 -C 6 -alkyl), and S(O) s —(C 1 -C 6 -haloalkyl);
Q is selected from the group consisting of:

wherein:
R4 is selected from the group consisting of C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 1 -C 6 -haloalkoxy, S(O) p —(C 1 -C 6 -alkyl), S(O) q —(C 1 -C 6 -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, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-alkyl, C 3 -C 8 -cycloalkyl substituted with one or more haloalkyl, C 3 -C 8 -cycloalkyl substituted with one or more halogens, C(O)—(C 1 -C 6 -alkyl), heterocyclyl, S(O) p —(C 1 -C 6 -alkyl), and S(O) q —(C 1 -C 6 -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;
R v , R w , R x , R y , R z in each occurrence are independently selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl, and C 1 -C 6 -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 ( ) signifies a single or double bond;

or a pharmaceutically acceptable salt thereof.

2. The compound according to claim 1 , wherein:
W1, W2, W3, W4, W5 are independently C or C—H;
or a pharmaceutically acceptable salt thereof.

3. The compound according to claim 1 , wherein:
W1 is an N atom, and
W2, W3, W4, W5 are independently C or C—H;
or a pharmaceutically acceptable salt thereof.

4. The compound according to claim 1 , wherein:
W2 is an N atom, and
W1, W3, W4, W5 are independently C or C—H;
or a pharmaceutically acceptable salt thereof.

5. The compound according to claim 1 , wherein:
W3 is an N atom, and
W1, W2, W4, W5 are independently C or C—H;
or a pharmaceutically acceptable salt thereof.

6. The compound according to claim 1 , wherein:
W1, W3 are both N atoms, and
W2, W4, W5 are independently C or C—H;
or a pharmaceutically acceptable salt thereof.

7. The compound according to claim 1 , wherein: W1, W5 are both N atoms, and
W2, W3, W4 are independently C or C—H;
or a pharmaceutically acceptable salt thereof.

8. The compound according to claim 1 , wherein:
W2, W3 are both N atoms, and
W1, W4, W5 are independently C or C—H;
or a pharmaceutically acceptable salt thereof.

9. The compound according to claim 1 , wherein:
W2, W4 are both N atoms, and
W1, W3, W5 are independently C or C—H;
or a pharmaceutically acceptable salt thereof.

10. The compound according to claim 1 , wherein:
W1, W2 are both N atoms, and
W3, W4, W5 are independently C or C—H;
or a pharmaceutically acceptable salt thereof.

11. The compound according to claim 1 , wherein:
W1, W2, W4 are all N atoms, and
W3, W5 are independently C or C—H;
or a pharmaceutically acceptable salt thereof.

12. The compound according to claim 1 , wherein:
W1, W2, W5 are all N atoms, and
W3, W4 are independently C or C—H;
or a pharmaceutically acceptable salt thereof.

13. The compound according to claim 1 , wherein:

is attached to W3, wherein W3 is a C atom;
or a pharmaceutically acceptable salt thereof.

14. The compound according to claim 1 , wherein;

is attached to W2, wherein W2 is a C atom;
or a pharmaceutically acceptable salt thereof.

15. The compound according to claim 1 , wherein:

is attached to W4, wherein W4 is a C atom;
or a pharmaceutically acceptable salt thereof.

16. The compound according to claim 1 , wherein:

is attached to W1, wherein W1 is a C atom;
or a pharmaceutically acceptable salt thereof.

17. The compound according to claim 1 , wherein:

is attached to W5, wherein W5 is a C atom;
or a pharmaceutically acceptable salt thereof.

18. The compound according to claim 1 , wherein:
n is 0 or 1;
or a pharmaceutically acceptable salt thereof.

19. The compound according to claim 1 , wherein:
m is 1 or 2;
or a pharmaceutically acceptable salt thereof.

20. A compound selected from the group consisting of:

Assignees

• Boehringer Ingelheim Vetmedica Gmbh
• Nihon Nohyaku Co Ltd

Inventors

• Herlé Bart
• Koolman Hannes Fiepko
• Long Alan
• Meier Robin
• Yonemura Ikki
• Gagnepain Julien

Classifications

• C07D513/04

  Ortho-condensed systems · CPC title

• C07D498/04

  Ortho-condensed systems · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title

• C07D417/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title