IP Library › Granted Patent US 12,559,503

Granted Patent B2

US 12,559,503 · App. 18/150,992 · Granted Feb 24, 2026

Anthelmintic aza-benzothiophene and aza-benzofuran compounds

Inventors: Alan Long (Warthausen, DE); Hannes Fiepko Koolman (Biberach an der Riss, DE); Hyoung Ik Lee (Alpharetta, GA)

C07D495/04 A61P33/10 C07D307/85 C07D407/12 C07D409/12 C07D413/14 C07D519/00 A61K45/06

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 12,559,503
App. No.: 18/150,992
Granted: Feb 24, 2026
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

This invention provides for compounds of the formula: wherein the variables are defined herein, or a stereoisomer, tautomer, N-oxide, hydrate, solvate, or salt thereof, compositions comprising these compounds, and method for the treatment, control or prevention of a parasitic infestation or infection in an animal in need thereof by administering an effective amount of these compounds to said animal.

Claims (127)

1 . A compound of Formula I:

or salt thereof,

wherein:

L is L1 or L2:

R 1 is optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted cycloalkyloxy, optionally substituted heterocyclyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, —SO p (optionally substituted alkyl) or —SO p (optionally substituted haloalkyl), —SF 5 , or —NR a R b wherein R a and R b are independently H or optionally substituted alkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;

R 2 is hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl;

R 2′ is optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl;

R 3 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, —S(O) p (optionally substituted alkyl), —SF 5 , optionally substituted heterocyclyl, optionally substituted 6- to 10-membered aryl, optionally substituted 5- to 10-membered heteroaryl, a spirocyclic heterocyclyl-carbocyclyl group, a spirocyclic heterocyclyl-heterocyclyl group, a spirocyclic carbocyclyl-carbocyclyl group, a spirocyclic carbocycylyl-heterocyclyl group, or —NR a R b wherein R a and R b are independently H or optionally substituted alkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;

R 4 is independently in each occurrence hydrogen, cyano, halogen, hydroxyl, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl; optionally substituted aryloxy, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted cycloalkyloxy, optionally substituted heterocyclyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, —SO p (optionally substituted alkyl) or —SO p (optionally substituted haloalkyl), —SF 5 , or —NR a R b wherein R a and R b are independently H or optionally substituted alkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;

R 5 and R 5′ are independently in each occurrence, hydrogen, halogen, cyano, nitro, hydroxyl, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted cycloalkyl, optionally substituted cycloalkyloxy, optionally substituted aryl, optionally substituted heteroaryl, —SF 5 , —SO p (optionally substituted alkyl) or —SO p (optionally substituted haloalkyl), or —NR c R d wherein R c and R d are independently H or optionally substituted alkyl; or R c and R d may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;

R 10 is hydrogen, halogen, alkyl, haloalkyl, cycloalkyl, alkenyl or alkynyl;

X is O or S;

Q is O, S or NR 2′ ;

Y 1 is N; Y 2 is N or —CR 4 ; and Y 3 is N or —CR 4 ; or

Y 1 is —CR 4 ; Y 2 is N; and Y 3 is N or —CR 4 ;

Y 1′ and Y 6′ are each independently N, C, or —CR 5 —;

Y 2′ , Y 3′ , Y 4′ , Y 5′ are each independently N, NR 2 , S, O, —CR 5 — or CR 5 R 5′ ;

W is CR 6 R 7 , O, S, or N—R 8 ,

Z is CR 6 R 7 , O, S, or N—R 8 ,

wherein

R 6 and R 7 are independently in each occurrence hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy or C 3 -C 8 -cycloalkoxy;

R 8 is hydrogen or C 1 -C 4 -alkyl;

and

wherein at most three of Y 1′ , Y 2′ , Y 3′ , Y 4′ , Y 5′ and Y 6′ are heteroatoms;

a is 0 or 1;

q is 0 or 1;

p is independently in each occurrence is 0, 1, or 2; and

the dashed bonds signify a single or double bond.

2 . The compound of Formula (I) of claim 1 , or salt thereof,

wherein:

R 1 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, hydroxy-C 1 -C 6 -alkyl, hydroxy-C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, amino-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, optionally substituted phenyl, optionally substituted phenyloxy, optionally substituted heteroaryl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted C 3 -C 8 -cycloalkyloxy, optionally substituted 3- to 7-membered heterocyclyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -haloalkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -haloalkylaminocarbonyl, —SF 5 , —SO p (optionally substituted C 1 -C 6 -alkyl) or —SO p (C 1 -C 6 -haloalkyl), or —NR a R b wherein R a and R b are independently H or optionally substituted C 1 -C 6 -alkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;

R 2 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl;

R 2′ is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, optionally substituted C 3 -C 8 -cycloalkyl, or optionally substituted phenyl;

R 3 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, optionally substituted C 3 -C 8 -cycloalkyl, —SF 5 , optionally substituted 3- to 7-membered heterocyclyl containing from one to three heteroatoms selected from the group consisting of N, O and S; optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, a 5- to 11-membered spirocyclic heterocyclyl-carbocyclyl group, a 5- to 11-membered spirocyclic heterocyclyl-heterocyclyl group, a 5- to 11-membered spirocyclic carbocyclyl-carbocyclyl group, a 5- to 11-membered spirocyclic carbocyclyl-heterocyclyl group, or —NR a R b wherein R a and R b are independently H, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;

R 4 is independently in each occurrence hydrogen, cyano, halogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, optionally substituted phenyl; optionally substituted phenyloxy, optionally substituted 5- or 6-membered heteroaryl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted C 3 -C 8 -cycloalkyloxy, optionally substituted 3- to 7-membered heterocyclyl containing from one to three heteroatoms selected from the group consisting of N, O and S, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -haloalkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -haloalkylaminocarbonyl, —SO p (optionally substituted C 1 -C 6 -alkyl) or —SO p (optionally substituted C 1 -C 6 -haloalkyl), SF 5 , or —NR a R b wherein R a and R b are independently H, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;

R 5 and R 5′ are independently in each occurrence, hydrogen, halogen, cyano, nitro, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted C 3 -C 8 -cycloalkyloxy, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, —SF 5 , —SO p (optionally substituted C 1 -C 6 -alkyl) or —SO p (optionally substituted C 1 -C 6 -haloalkyl), or —NR c R d wherein Re and R d are independently H, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; or R c and R d may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted; and

R 10 is hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl.

3 . The compound of Formula (I), or salt thereof, according to claim 1 , wherein

R 1 is optionally substituted C 1 -C 4 -alkyl, optionally substituted C 1 -C 4 -alkoxy, optionally substituted C 2 -C 4 -alkenyl, optionally substituted C 2 -C 4 -alkynyl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted, saturated or unsaturated 5-, 6-, or 7-membered heterocycle, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, optionally substituted phenyloxy, —SO p (optionally substituted C 1 -C 4 -alkyl), SO p (optionally substituted C 1 -C 4 -haloalkyl), amino, —NH-optionally substituted C 1 -C 4 -alkyl, or —NR a R b wherein R a and R b are independently optionally substituted C 1 -C 4 -alkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-5-, 6-, 7-, or 8-membered-heterocyclyl group, which may be optionally substituted;

R 2 is hydrogen or C 1 -C 4 -alkyl;

R 3 is C 1 -C 4 -alkyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, optionally substituted C 3 -C 8 -cycloalkyl, a 5- to 11-membered spirocyclic heterocyclyl-carbocyclyl group, a 5- to 11-membered spirocyclic heterocyclyl-heterocyclyl group, a 5- to 11-membered spirocyclic carbocyclyl-carbocyclyl group, or a 5- to 11-membered spirocyclic carbocyclyl-heterocyclyl group, each of which may be optionally substituted with 1, 2, or 3 substituents;

R 4 is independently hydrogen, halogen, cyano, hydroxyl, optionally substituted C 1 -C 4 -alkyl, optionally substituted C 1 -C 4 -alkoxy, optionally substituted C 3 -C 8 -cycloalkyl, amino, NH-optionally substituted C 1 -C 4 -alkyl, —SF 5 , —SO p (optionally substituted C 1 -C 4 -alkyl), —SO p (optionally substituted C 1 -C 4 -haloalkyl), or —NR a R b wherein R a and R b are independently optionally substituted C 1 -C 4 -alkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3, 4, 5, 6, 7, or 8 membered-heterocyclyl group, which may be optionally substituted; and

R 5 is independently hydrogen, halogen, cyano, nitro, hydroxyl, optionally substituted C 1 -C 4 -alkyl, optionally substituted C 1 -C 4 -alkoxy, optionally substituted C 3 -C 8 -cycloalkyl, —SF 5 , SO p (optionally substituted C 1 -C 4 -alkyl), SO p (optionally substituted C 1 -C 4 -haloalkyl), or —NR c R d wherein Re and R d are independently hydrogen or optionally substituted C 1 -C 4 -alkyl; or R c and R d may form, with the nitrogen to which they are attached, a 3, 4, 5, 6, 7, or 8 membered-heterocyclyl group, which may be optionally substituted.

4 . The compound of Formula (I), or salt thereof, according to claim 1 , wherein X is S.

5 . The compound of Formula (I), or salt thereof, according to claim 1 , wherein X is O.

6 . The compound of Formula (I), or salt thereof, according to claim 1 , wherein a is 1 and q is 1.

7 . The compound of Formula (I), or salt thereof, according to claim 1 , wherein a is 0 and q is 0.

8 . The compound of Formula (I), or salt thereof, according to claim 1 , wherein a is 1 and q is 0.

9 . The compound of Formula (I), or salt thereof, according to claim 1 , wherein:

L is L1;

R 1 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, hydroxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -haloalkyl, alkoxy-C 1 -C 4 -alkyl, alkoxy-C 1 -C 4 -haloalkyl, C 3 -C 8 -cycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, optionally substituted 5- or 6-membered heteroaryl or optionally substituted 5- or 6-membered heterocyclyl containing 1 to 3 N, S or O heteroatoms or —NR a R b wherein R a and R b are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5- or 6-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;

R 2 is hydrogen or C 1 -C 4 -alkyl;

R 3 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted 3- to 7-membered heterocyclyl containing from one to three heteroatoms selected from the group consisting of N, O and S; optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl; or —NR a R b wherein R a and R b are independently H, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;

R 4 is independently in each occurrence hydrogen, halogen, —SF 5 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, optionally substituted C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, aminocarbonyl, C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -haloalkylaminocarbonyl, di-C 1 -C 4 -alkylaminocarbonyl, di-C 1 -C 4 -haloalkylaminocarbonyl, —SO p (optionally substituted C 1 -C 4 -alkyl) or —SO p (optionally substituted C 1 -C 4 -haloalkyl), or —NR a R b wherein R a and R b are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;

R 5 is independently in each occurrence, hydrogen, halogen, —SF 5 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, —SO p (optionally substituted C 1 -C 4 -alkyl) or —SO p (optionally substituted C 1 -C 4 -haloalkyl), or —NR c R d wherein R c and R d are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;

R 10 is hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;

Q is O or S;

Z is CR 6 R 7 or O; and

W is CR 6 R 7 .

10 . The compound of Formula (I), or salt thereof, according to claim 9 wherein a is 1 and q is 1.

11 . The compound of Formula (I), or salt thereof, according to claim 9 , wherein a is 0 or 1 and q is 0.

12 . The compound of Formula (I), or salt thereof, according to claim 9 , which is represented by the following structure of Formula (IC):

wherein

R 9 is independently halogen, cyano, nitro, C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -halocycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, or —NR a R b wherein R a and R b are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;

R 1 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, hydroxy-C 1 -C 4 -alkyl, alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, optionally substituted 5- or 6-membered heterocyclyl containing 1 to 3 N, S or O heteroatoms or —NR a R b wherein R a and R b are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5- or 6-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;

R 4 is in each occurrence independently hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, or —NR a R b wherein R a and R b are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;

R 5 is hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, or —NR c R d wherein R c and R d are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;

W is CR 6 R 7 ;

R 2 is hydrogen or C 1 -C 3 -alkyl;

o is 0, 1 or 2; and

m is 0, 1, 2, or 3.

13 . The compound of Formula (I), or salt thereof, according to claim 9 , which is represented by the following structure:

wherein:

R 4 is independently in each occurrence hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, or —NR a R b wherein R a and R b are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;

R 5 and R 5′ are independently in each occurrence hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, or —NR c R d wherein R c and R d are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;

R 2 is hydrogen or C 1 -C 3 -alkyl;

R 10 is hydrogen;

Z is CR 6 R 7 or O;

Y 1′ and Y 6′ are each independently C, N or CR 5 ;

Y 3′ , Y 4′ , Y 5′ are independently CR 5 , CR 5 R 5′ , N, NR 2 , O or S;

the dashed bonds signify a single or double bond;

a is 0 or 1; and

m is 0, 1, 2, or 3.

14 . The compound according to claim 13 , or salt thereof, wherein Y 1′ and Y 6′ are each C;

Y 3′ and Y 4′ are independently CR 5 ; and

Y 5′ is S.

15 . The compound according to claim 13 , or salt thereof, wherein Y 3′ and Y 6′ are N;

Y 1′ is C; and

Y 4′ and Y 5′ are independently CR 5 .

16 . The compound according to claim 13 , or salt thereof, wherein Y 1′ and Y 5′ are N;

Y 6′ is C; and

Y 3′ and Y 4′ are independently CR 5 .

17 . The compound according to claim 9 , or salt thereof, which is represented by the following structure:

wherein

R 9 is independently halogen, cyano, C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -halocycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, or —NR a R b wherein R a and R b are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;

R 5 is hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, or —NR c R d wherein R c and R d are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;

R 2 is hydrogen or C 1 -C 3 -alkyl;

R 10 is hydrogen;

D is —N— or —CH—,

D 1 is —NH—, —O—, —CH 2 —;

m is 0, 1, 2, or 3; and

b is 0 or 1.

18 . The compound according to claim 12 , or salt thereof, wherein

R 1 C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 3 -C 6 -cycloalkyl, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl) amino, morpholino, pyranyl, tetrahydropyranyl, or dihydropyranyl;

R 4 is independently in each occurrence hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 4 haloalkyl; and

R 5 is independently in each occurrence a halogen, C 1 -C 4 -alkyl, or C 1 -C 4 haloalkyl.

19 . The compound according to claim 13 , or salt thereof, wherein

R 1 C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 3 -C 6 -cycloalkyl, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl) amino, morpholino, pyranyl, tetrahydropyranyl, or dihydropyranyl;

R 4 is independently in each occurrence hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 4 haloalkyl; and

R 5 is independently in each occurrence hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 4 haloalkyl.

20 . The compound according to claim 17 , or salt thereof, wherein

R 1 C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 3 -C 6 -cycloalkyl, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl) amino, morpholino, pyranyl, tetrahydropyranyl, or dihydropyranyl;

R 4 is independently in each occurrence hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 4 haloalkyl; and

R 5 is independently in each occurrence hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 4 haloalkyl.

21 . The compound of claim 1 , or salt thereof, wherein Y 1 is N; and Y 2 and Y 3 are —C—R 4 .

22 . The compound of claim 1 , or salt thereof, wherein Y 2 is N; and Y 1 and Y 3 are —CR 4 .

23 . The compound of claim 1 , or salt thereof, wherein Y 1 and Y 3 are N; and Y 2 is —CR 4 .

24 . The compound of claim 1 , or salt thereof, wherein Y 1 and Y 2 are N; and Y 3 is —CR 4 .

25 . A veterinary composition comprising the compound of claim 1 or a pharmaceutically or a veterinarily acceptable salt thereof and a veterinarily acceptable carrier.

26 . A veterinary composition comprising the compound of claim 1 or a pharmaceutically or a veterinarily acceptable salt thereof, one or more additional active agent(s), and a veterinarily acceptable carrier.

27 . A method for the treatment, control or prevention of a parasitic infection in an animal in need thereof, which comprises administering to said animal an effective amount of the compound of claim 1 , or a pharmaceutically or a veterinarily acceptable salt thereof.

28 . A method for the treatment, control or prevention of a parasitic infection in an animal in need thereof, which comprises administering to said animal an effective amount of the compound of claim 12 , or a pharmaceutically or a veterinarily acceptable salt thereof.

29 . A method for the treatment, control or prevention of a parasitic infection in an animal in need thereof, which comprises administering to said animal an effective amount of the compound of claim 13 , or a pharmaceutically or a veterinarily acceptable salt thereof.

30 . A compound, or a salt thereof, selected from the group consisting of:

Assignments (4)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 29, 2025

From: BOEHRINGER INGELHEIM PHARMA GMBH & CO KG

To: BOEHRINGER INGELHEIM VETMEDICA GMBH

Reel/Frame 070970/0752 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 5, 2023

From: LONG, ALAN; LEE, HYOUNG IK

To: BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC.

Reel/Frame 063549/0952 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 5, 2023

From: KOOLMAN, HANNES FIEPKO

To: BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG

Reel/Frame 063550/0005 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 5, 2023

From: BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC.

To: BOEHRINGER INGELHEIM VETMEDICA GMBH

Reel/Frame 063550/0197 →

Continuity (3)

Continuation 16823138 · Mar 18, 2020

Provisional Application 62820352 · Mar 19, 2019

Related Publication 20230219974A1 · Jul 13, 2023

References Cited (134)

US 4464372A · Bristol et al. · 1984 [cited by applicant]

US 5434150A · Austel et al. · 1995 [cited by applicant]

US 6900208B2 · Salvati et al. · 2005 [cited by applicant]

US 6911543B2 · Walker et al. · 2005 [cited by applicant]

US 7030112B2 · Salvati et al. · 2006 [cited by applicant]

US 7153854B2 · Abe et al. · 2006 [cited by applicant]

US 7300932B2 · Fox et al. · 2007 [cited by applicant]

US 7306631B2 · Glenn, Jr. et al. · 2007 [cited by applicant]

US 7420056B2 · Kuehnert et al. · 2008 [cited by applicant]

US 7456192B2 · Imbert et al. · 2008 [cited by applicant]

US 7476685B2 · Araki et al. · 2009 [cited by applicant]

US 7723336B2 · Vaccaro et al. · 2010 [cited by applicant]

US 7893085B2 · Savy et al. · 2011 [cited by applicant]

US 7919628B2 · Hachtel et al. · 2011 [cited by applicant]

US 7956068B2 · Carson et al. · 2011 [cited by applicant]

US 7964204B2 · Lahm et al. · 2011 [cited by applicant]

US 8030327B2 · Sato et al. · 2011 [cited by applicant]

US 8252795B2 · Fink et al. · 2012 [cited by applicant]

US 8431593B2 · Hutchison et al. · 2013 [cited by applicant]

US 8450354B2 · Mjalli et al. · 2013 [cited by applicant]

US 8772301B2 · Hardy et al. · 2014 [cited by applicant]

US 9023850B2 · Lahm et al. · 2015 [cited by applicant]

US 9556169B2 · Chatterjee et al. · 2017 [cited by applicant]

US 9718816B2 · Chesworth et al. · 2017 [cited by applicant]

US 9802961B2 · Clark et al. · 2017 [cited by applicant]

US 9868749B2 · Alexander et al. · 2018 [cited by applicant]

US 9873703B2 · Ali et al. · 2018 [cited by applicant]

US 10138248B2 · Buesking et al. · 2018 [cited by applicant]

US 11560388B2 · Long · 2023 [cited by examiner]

US 20040242587A1 · Fu · 2004 [cited by applicant]

US 20060074102A1 · Cusack et al. · 2006 [cited by applicant]

US 20070027093A1 · Ogawa et al. · 2007 [cited by applicant]

US 20070275962A1 · Koul et al. · 2007 [cited by applicant]

US 20110105457A1 · Taniyama et al. · 2011 [cited by applicant]

US 20110195933A1 · Katz et al. · 2011 [cited by applicant]

US 20110206607A1 · Olsson et al. · 2011 [cited by applicant]

US 20110245274A1 · Nanchen et al. · 2011 [cited by applicant]

US 20120015943A1 · Blackburn et al. · 2012 [cited by applicant]

US 20120065200A1 · Barbosa et al. · 2012 [cited by applicant]

US 20120083476A1 · Breitenbucher et al. · 2012 [cited by applicant]

US 20120219500A1 · Sakurai et al. · 2012 [cited by applicant]

US 20130071415A1 · Babu et al. · 2013 [cited by applicant]

US 20130203692A1 · Soll et al. · 2013 [cited by applicant]

US 20140045826A1 · Shakespeare et al. · 2014 [cited by applicant]

US 20140066434A1 · Shakespeare · 2014 [cited by applicant]

US 20150126523A1 · Meng · 2015 [cited by applicant]

US 20160106102A1 · Kuebbeler et al. · 2016 [cited by applicant]

US 20160333012A1 · Chatterjee et al. · 2016 [cited by applicant]

US 20170369486A1 · Acharya et al. · 2017 [cited by applicant]

US 20180230157A1 · Bacon et al. · 2018 [cited by applicant]

US 20190071447A1 · Kohler et al. · 2019 [cited by applicant]

US 20190233425A1 · Bayly et al. · 2019 [cited by applicant]

US 20190352275A1 · Meldrum et al. · 2019 [cited by applicant]

US 20200024264A1 · Hubsch et al. · 2020 [cited by applicant]

US 20200237771A1 · Hallur et al. · 2020 [cited by applicant]

US 20220047569A1 · Kazmi et al. · 2022 [cited by applicant]

CA 3117343A1 · 2020 [cited by applicant]

CL 202201662 · 2023 [cited by applicant]

CL 202201739 · 2023 [cited by applicant]

CL 202202346 · 2023 [cited by applicant]

EP 1277754B1 · 2005 [cited by applicant]

EP 3078664A1 · 2016 [cited by applicant]

EP 3643711A1 · 2020 [cited by applicant]

JP 2009203214A · 2009 [cited by applicant]

JP 2011140452A · 2011 [cited by applicant]

JP 2012012299A · 2012 [cited by applicant]

JP 2016505529A · 2016 [cited by applicant]

RU 2004136978A · 2005 [cited by applicant]

WO 2000053602A1 · 2000 [cited by applicant]

WO 2005066177A1 · 2005 [cited by applicant]

WO 2006004191A1 · 2006 [cited by applicant]

WO 2007123855A2 · 2007 [cited by applicant]

WO 2008019309A1 · 2008 [cited by applicant]

WO 2010017046A1 · 2010 [cited by applicant]

WO 2011058109A1 · 2011 [cited by applicant]

WO 2011075591A1 · 2011 [cited by applicant]

WO 2011137587A1 · 2011 [cited by applicant]

WO 2011146401A1 · 2011 [cited by applicant]

WO 2012100342A1 · 2012 [cited by applicant]

WO 2012107533A1 · 2012 [cited by applicant]

WO 2014078802A1 · 2014 [cited by applicant]

WO 2015066277A1 · 2015 [cited by applicant]

WO 2017093180A1 · 2017 [cited by applicant]

WO 2017125898A1 · 2017 [cited by applicant]

WO 2017178416A1 · 2017 [cited by applicant]

WO 2018087036A1 · 2018 [cited by applicant]

WO 2018197401A1 · 2018 [cited by applicant]

WO 2019002132A1 · 2019 [cited by applicant]

WO 2019025341A1 · 2019 [cited by applicant]

WO 2019115768A1 · 2019 [cited by applicant]

WO 2019215182A1 · 2019 [cited by applicant]

WO 2020002124A1 · 2020 [cited by applicant]

WO 2020012336A1 · 2020 [cited by applicant]

WO 2020014068A1 · 2020 [cited by applicant]

WO 2020083971A2 · 2020 [cited by applicant]

WO 2020131629A1 · 2020 [cited by applicant]

WO 2020131631A1 · 2020 [cited by applicant]

WO 2020191091A1 · 2020 [cited by applicant]

WO 2020219871A1 · 2020 [cited by applicant]

WO 2020247747A1 · 2020 [cited by applicant]

WO 2021018839A1 · 2021 [cited by applicant]

WO 2021030379A1 · 2021 [cited by applicant]

WO 2021032934A1 · 2021 [cited by applicant]

WO 2021127443A1 · 2021 [cited by applicant]

WO 2021122906A1 · 2021 [cited by applicant]

WO 2021122911A1 · 2021 [cited by applicant]

WO 2021130731A1 · 2021 [cited by applicant]

WO 2021173713A1 · 2021 [cited by applicant]

WO 2021204930A1 · 2021 [cited by applicant]

WO 2021231571A1 · 2021 [cited by applicant]

WO 2021242581A1 · 2021 [cited by applicant]

WO 202210646A1 · 2022 [cited by applicant]

WO 2022106469A2 · 2022 [cited by applicant]

WO 2022117783A1 · 2022 [cited by applicant]

WO 2022122987A1 · 2022 [cited by applicant]

WO 2022122988A1 · 2022 [cited by applicant]

WO 2022152918A1 · 2022 [cited by applicant]

CAS Registry Entry for Registry No. 2134947-60-5, which entered STN on Oct. 15, 2017 (Year: 2017). [cited by examiner]

CAS Registry Entry for Registry No. 1953874-77-5, which entered STN on Jul. 17, 2016 (Year: 2016). [cited by examiner]

CAS Registry Entry for Registry No. 1318005-39-8, which entered STN on Aug. 15, 2011 (Year: 2011). [cited by examiner]

CAS Registry Entry for Registry No. 1835595-45-3, which entered STN on Dec. 23, 2015 (Year: 2015). [cited by examiner]

CAS Registry Entry for Registry No. 2249355-47-1, which entered STN on Nov. 18, 2018 (Year: 2018). [cited by examiner]

CAS Registry Entry for Registry No. 1944784-28-4, which entered STN on Jul. 4, 2016 (Year: 2016). [cited by examiner]

Preston, “Low cost whole-organism screening of compounds for anthelmintic activity”, International Journal for Parasitology, vol. 45, pp. 333-343. [cited by applicant]

Koyanagi, T. & Haga, T. Bioisosterism in Agrochemicals. 15-24 (1995). [cited by applicant]

Meanwell, N. A Synopsis of Some Recent Tactical Application of Bioisosteres in Drug Design. Journal of Medicinal Chemistry, 54(8), 2529-2591. https://doi.org/10.1021/jm1013693 (Year: 2011). [cited by applicant]

Database Registry [Online], May 1, 2020 (May 1, 2020), Life Chemicals Inc.: “Imidazo[l,2-b]pyridazine-6-carboxamide, N-(1,2,3,4-tetrahydro-1-naphthalenyl)-”, XP055837558, Database accession No. 2415490-08-1 compound wit… [cited by applicant]

Database Registry (Online) Chemical Abstracts Service, Columbus, Ohio, US; Jul. 17, 2016, XP002799055, Database accession No. 1953874-77-5, 2-Benzofurancarboxamide,3,4,7-trimethyl-N-(octahydro-4-benzofuranyl)-. [cited by applicant]

Database Registry (Online) Chemical Abstracts Service, Columbus, Ohio, US; Oct. 15, 2017, XP002799056, Database accession No. 2134947-60-5, 2-Benzofurancarboxamide,3,4,7-trimethyl-N-(4,5,6,7-tetrahydro-1-methyl-1H-indaz… [cited by applicant]

Database Registry (Online) Chemical Abstracts Service, Columbus, Ohio, US; Aug. 15, 2011, XP002799057, Database accession No. 1318005-39-8, 2-Benzofurancarboxamide, N-(6-bromo-3,4-dihydro-2H-1-benzopyran-4-yl)-3,7-dimet… [cited by applicant]

Database Registry (Online) Chemical Abstracts Service, Columbus, Ohio, US; Dec. 23, 2015, XP002799058, Database accession No. 1835595-46-4, 2-Benzofurancarboxamide, N-(6-amino-1,2,3,4-tetrahydro-1-naphthalenyl)-3,4,7-tr… [cited by applicant]

Database Registry (Online) Chemical Abstracts Service, Columbus, Ohio, US; Nov. 18, 2018, XP002799059, Database accession No. 2249355-47-1, 2-Benzofurancarboxamide, N-(6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-7-yl)-3,7-dim… [cited by applicant]

Database Registry (Online) Chemical Abstracts Service, Columbus, Ohio, US; Jul. 4, 2016, XP002799060, Database accession No. 1944784-28-4, 2-Benzofurancarboxamide, 5-bromo-7-methyl-N-(4,5,6,7-tetrahydro-2-methyl-2H-inda… [cited by applicant]

Preston, “Low cost whole-organism screening of compounds for anthelmintic activity”, International Journal for Parasitology, vol. 45, pp. 333-343, 2015. [cited by applicant]