Endoparasite control agent and method for using the same

Patent metadata

Field	Value
Publication number	US-9550749-B2
Application number	US-201314424753-A
Country	US
Kind code	B2
Filing date	Aug 29, 2013
Priority date	Aug 30, 2012
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

An object of the present invention is to provide a novel endoparasite control agent as a parasiticide, an antiprotozoal or the like. Provided is an endoparasite control agent comprising a carboxamide derivative represented by the general formula (I):

or a salt thereof as an active ingredient.

First claim

The invention claimed is:

1. A method for controlling endoparasites, comprising orally or parenterally administering an effective amount of an endoparasite control composition comprising a compound of the general formula (I):

wherein each X may be the same or different, and represents a halogen atom; a cyano group; a nitro group; an amino group; a (C 1 -C 6 ) alkyl group; a halo (C 1 -C 6 ) alkyl group; a (C 1 -C 6 ) alkoxy group; a halo (C 1 -C 6 ) alkoxy group; a (C 1 -C 6 ) alkylthio group; a halo (C 1 -C 6 ) alkylthio group; a (C 1 -C 6 ) alkylsulfinyl group; a halo (C 1 -C 6 ) alkylsulfinyl group; a (C 1 -C 6 ) alkylsulfonyl group; or a halo (C 1 -C 6 ) alkylsulfonyl group,
m represents an integer of 0 to 5,
A represents a (C 2 -C 8 ) alkylene group; or a substituted (C 2 -C 8 ) alkylene group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group and a (C 3 -C 6 ) cycloalkyl group, with the proviso that the (C 2 -C 8 ) alkylene group and the substituted (C 2 -C 8 ) alkylene group may be modified by incorporation, into the carbon chain, of at least one group selected from —O—, —S—, —SO—, —SO 2 — and —N(R)—, (wherein R represents a hydrogen atom, a (C 1 -C 6 ) alkyl group, a (C 3 -C 6 ) cycloalkyl group, a (C 1 -C 6 ) alkylcarbonyl group or a (C 1 -C 6 ) alkoxycarbonyl group), and with the proviso that when the alkylene group or the substituted alkylene group having one or more substituents is a (C 3 -C 6 ) or (C 3 -C 8 ) alkylene group, or a (C 2 -C 6 ) or (C 2 -C 8 ) alkylene group modified by incorporation, into the carbon chain, of at least one group selected from —O—, —S—, —SO—, —SO 2 — and —N(R)—, or A can be cyclopropane, cyclobutane, cyclopentane or cyclohexane,
E represents a hydrogen atom; a (C 1 -C 6 ) alkyl group; a (C 3 -C 6 ) cycloalkyl group; a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; a (C 1 -C 6 ) alkylcarbonyl group; or a (C 1 -C 6 ) alkoxycarbonyl group, and
B represents any of the moieties represented by the following B5 to B8:

wherein each Y can be the same or different, and represents a halogen atom; a cyano group; a nitro group; a hydroxy group; a (C 1 -C 6 ) alkyl group; a halo (C 1 -C 6 ) alkyl group; a (C 2 -C 6 ) alkenyl group; a halo (C 2 -C 6 ) alkenyl group; a (C 2 -C 6 ) alkynyl group; a halo (C 2 -C 6 ) alkynyl group; a (C 1 -C 6 ) alkoxy group; a halo (C 1 -C 6 ) alkoxy group; a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy group; a (C 2 -C 6 ) alkenyloxy group; a halo (C 2 -C 6 ) alkenyloxy group; a (C 2 -C 6 ) alkynyloxy group; a halo (C 2 -C 6 ) alkynyloxy group; a (C 1 -C 6 ) alkylthio group; a halo (C 1 -C 6 ) alkylthio group; a (C 1 -C 6 ) alkylsulfinyl group; a halo (C 1 -C 6 ) alkylsulfinyl group; a (C 1 -C 6 ) alkylsulfonyl group; a halo (C 1 -C 6 ) alkylsulfonyl group; a (C 1 -C 6 ) alkoxycarbonyl group; a (C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group; a (C 3 -C 30 ) trialkylsilyl group; a mono (C 1 -C 6 ) alkylsulfonylamino group; a mono halo (C 1 -C 6 ) alkylsulfonylamino group; a phenyl group; a substituted phenyl group having one or more substituents selected from group Z substituents on the ring; a phenoxy group; a substituted phenoxy group having one or more substituents selected from group Z substituents on the ring; a heterocyclic group; a substituted heterocyclic group having one or more substituents selected from group Z substituents on the ring; a heterocycloxy group; or a substituted heterocycloxy group having one or more substituents selected from group Z substituents on the ring,
the group Z substituents are a halogen atom; a cyano group; a nitro group; a (C 1 -C 6 ) alkyl group; a halo (C 1 -C 6 ) alkyl group; a (C 2 -C 6 ) alkenyl group; a halo (C 2 -C 6 ) alkenyl group; a (C 2 -C 6 ) alkynyl group; a halo (C 2 -C 6 ) alkynyl group; a (C 1 -C 6 ) alkoxy group; a halo (C 1 -C 6 ) alkoxy group; a (C 2 -C 6 ) alkenyloxy group; a halo (C 2 -C 6 ) alkenyloxy group; a (C 2 -C 6 ) alkynyloxy group; a halo (C 2 -C 6 ) alkynyloxy group; a (C 1 -C 6 ) alkylthio group; a halo (C 1 -C 6 ) alkylthio group; a (C 1 -C 6 ) alkylsulfinyl group; a halo (C 1 -C 6 ) alkylsulfinyl group; a (C 1 -C 6 ) alkylsulfonyl group; a halo (C 1 -C 6 ) alkylsulfonyl group; a (C 1 -C 6 ) alkoxycarbonyl group; and a (C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group,
Y 1 represents a (C 1 -C 6 ) alkyl group,
n represents an integer of 0 to 5, with the proviso that when n is an integer of 2 to 5, two adjacent Y groups can join together to form a (C 3 -C 5 ) alkylene group; a (C 3 -C 5 ) alkenylene group; a (C 2 -C 4 ) alkyleneoxy group; a (C 1 -C 3 ) alkylene dioxy group; or a halo (C 1 -C 3 ) alkylene dioxy group, and
the numbers on each ring represent positions where the ring can be substituted by Y and the free bond extending from each ring is a bond between A and B, or

a salt thereof as an active ingredient to a non-human mammal or bird.

2. The method according to claim 1 wherein the endoparasite control composition is administered orally or parenterally to a non-human mammal.

3. The method according to claim 2 , wherein the non-human mammal is a domestic animal.

4. The method according to claim 1 , wherein A is a (C 2 -C 8 ) alkylene group; or a substituted (C 2 -C 8 ) alkylene group having a substituent(s) which may be the same or different from each other and is/are selected from a halogen atom, a (C 1 -C 6 ) alkyl group and a (C 3 -C 6 ) cycloalkyl group.

5. The method according to claim 1 , wherein B is B5.

6. The method according to claim 1 ,
wherein each X may be the same be the same or different, and is a halogen atom; a (C 1 -C 6 ) alkyl group; or a halo (C 1 -C 6 ) alkyl group,
m is 1 or 2,
A is a (C 2 -C 8 ) alkylene group; or a (C 2 -C 8 ) alkylene group substituted by a (C 1 -C 6 ) alkyl group,
E is a hydrogen atom,
B is B5,
each Y may be the same or different, and is a halogen atom; a (C 1 -C 6 ) alkyl group; a halo (C 1 -C 6 ) alkyl group; a phenyl group; a substituted phenyl group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group, a halo (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group and a halo (C 1 -C 6 ) alkoxy group on the ring; a phenoxy group; a substituted phenoxy group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group, a halo (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group and a halo (C 1 -C 6 ) alkoxy group on the ring; a pyridyl group; a substituted pyridyl group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group, a halo (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group and a halo (C 1 -C 6 ) alkoxy group on the ring; a pyridyloxy group; or a substituted pyridyloxy group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group, a halo (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group and a halo (C 1 -C 6 ) alkoxy group on the ring, and
n is an integer of 1 to 3.

Assignees

• Univ Tokyo
• Nihon Nohyaku Co Ltd

Inventors

• Kita Kiyoshi
• Suwa Akiyuki
• Oda Masatsugu
• Tanaka Koji

Classifications

• A61P33/02

  Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• A61P33/10

  Anthelmintics · CPC title

• C07D231/12

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• A61K31/415

  1,2-Diazoles · CPC title