Granted Patent B2

US 12,521,381 · App. 18/012,768 · Granted Jan 13, 2026

Inventors: Hirokazu Fujihara (Kawachinagano, JP); Shunsuke Fuchi (Kawachinagano, JP); Yutaka Abe (Kawachinagano, JP)

Assignee: NIHON NOHYAKU CO., LTD.

A61K31/4439A61P33/02

Abstract

Claims (56)

1 . A method for coccidial control, the method comprising

administering an effective amount of a benzimidazole compound represented by General Formula (1) or (1-1) or a salt of the compound to a subject animal, General Formula (1) expressed as follows:

wherein:

R represents:

(a1) methyl or ethyl;

R 1 represents:

(b1) (C 1 -C 8 )alkyl;

(b2) halo-(C 1 -C 8 )alkyl;

(b3) (C 3 -C 8 )cycloalkyl;

(b4) (C 1 -C 8 )alkoxy(C 1 -C 8 )alkyl;

(b5) aryl; or

(b6) aryl having one to five substituents selected from, identically or differently, (a) halogen, (b) (C 1 -C 6 )alkyl, (c) halo-(C 1 -C 6 )alkyl, (d) (C 1 -C 6 )alkoxy, (e) halo-(C 1 -C 6 )alkoxy, (f) (C 1 -C 6 )alkylthio, (g) halo-(C 1 -C 6 )alkylthio, (h) (C 1 -C 6 )alkylsulfinyl, (i) halo-(C 1 -C 6 )alkylsulfinyl, (j) (C 1 -C 6 )alkylsulfonyl, (k) halo-(C 1 -C 6 )alkylsulfonyl, and (l) trimethylsilyl;

X represents O, S, SO, SO 2 , or NR 2 , where R 2 represents hydrogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkyl-carbonyl, (C 1 -C 6 )alkoxy-carbonyl, (C 1 -C 6 )alkylsulfonyl, or halo-(C 1 -C 6 )alkylsulfonyl; or

R 2 of NR 2 may combine with R 1 to form, with the nitrogen to which R 2 bonds, an unsubstituted or monosubstituted 5- to 8-membered saturated nitrogen-containing aliphatic heterocycle, where the substituent which the aliphatic heterocycle may have is ethoxycarbonyl or (C 5 -C 8 )alkylenedioxy, where two bonds of the alkylenedioxy bond to one carbon atom;

Y represents (c1) halogen;

m denotes 0 or 1;

Z represents, identically or differently in each occurrence:

(d1) halogen; or

(d2) (C 1 -C 8 )alkyl; and

n denotes 0, 1, or 2,

wherein none of the (C 1 -C 8 )alkylsulfonyl, (C 1 -C 8 )alkoxy(C 1 -C 8 )alkylsulfonyl, (C 3 -C 8 )cycloalkylsulfonyl, and halo-(C 1 -C 8 )alkylsulfonyl is present at the 2-position and the 4-position of the pyridine ring.

2 . The method according to claim 1 ,

wherein said benzimidazole compound is represented by General Formula (1) and:

R is (a1) methyl or ethyl;

R 1 is:

(b1) (C 1 -C 8 )alkyl;

(b2) halo-(C 1 -C 8 )alkyl;

(b3) (C 3 -C 8 )cycloalkyl; or

(b6) aryl having one to five substituents selected from, identically or differently, (a) halogen, (b) (C 1 -C 6 )alkyl, (c) halo-(C 1 -C 6 )alkyl, (d) (C 1 -C 6 )alkoxy, (e) halo-(C 1 -C 6 )alkoxy, (f) (C 1 -C 6 )alkylthio, (g) halo-(C 1 -C 6 )alkylthio, (h) (C 1 -C 6 )alkylsulfinyl, (i) halo-(C 1 -C 6 )alkylsulfinyl, (j) (C 1 -C 6 )alkylsulfonyl, (k) halo-(C 1 -C 6 )alkylsulfonyl, and (l) trimethylsilyl;

X is O, S, or NR 2 where R 2 is as defined above;

Y is (c1) halogen;

m is 0 or 1;

Z is, identically or differently in each occurrence:

(d1) halogen; or

(d2) (C 1 -C 8 )alkyl; and

n is 0, 1, or 2.

3 . The method according to claim 1 ,

wherein said benzimidazole compound is represented by General Formula (1) and:

R is (a1) methyl or ethyl;

R 1 is (b1) halo-(C 1 -C 8 )alkyl; and

m is 0.

4 . The method according to claim 1 ,

wherein said benzimidazole compound is represented by General Formula (1) and:

R is (a1) methyl or ethyl;

R 1 is (b1) halo-(C 1 -C 8 )alkyl;

m is 0;

Zs are, identically or differently in each occurrence:

(d1) halogen; or

(d2) (C 1 -C 8 )alkyl; and

n is 2.

5 . The method according to claim 1 ,

wherein the subject animal is an animal excluding humans.

6 . The method according to claim 1 ,

wherein the subject animal is a bird.

7 . The method according to claim 1 ,

wherein the subject animal is a chicken.

Assignments (1)

Priority Claims (2)

Continuity (1)

References Cited (22)