Anthelmintic aza-benzothiophene and aza-benzofuran compounds

Patent metadata

Field	Value
Publication number	US-12559503-B2
Application number	US-202318150992-A
Country	US
Kind code	B2
Filing date	Jan 6, 2023
Priority date	Mar 19, 2019
Publication date	Feb 24, 2026
Grant date	Feb 24, 2026

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.

First claim

What is claimed is:

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 eac

Assignees

• Boehringer Ingelheim Vetmedica Gmbh
• Boehringer Ingelheim Pharma

Inventors

• Long Alan
• Koolman Hannes Fiepko
• Lee Hyoung Ik

Classifications

• C07D519/00

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title

• C07D409/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D407/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D307/85

  attached in position 2 · CPC title