IP Library Granted Patent US 10,653,675
Granted Patent B2
US 10,653,675 · App. 16/293,024 · Granted May 19, 2020

Use of isoxazoline derivatives for the treatment or prevention of arthropod infestations in poultry

Inventors: Anja Regina Heckeroth (Stadecken-Elsheim, DE); Hartmut Zoller (Hochheim, DE); Annie Flochlay-Sigognault (Angers, FR); Bruno Huyghe (St Martin du Fouilloux, FR)
Assignee: Intervet Inc.
A61K31/42A01N43/80A01N43/90A61K9/0053A61K9/08A61K31/422A61K31/437A61K47/10A61K47/26
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Quick Facts
Patent No.
US 10,653,675
App. No.
16/293,024
Granted
May 19, 2020
Kind
B2
Abstract

The present invention relates to methods of treating or preventing arthropod infestations of poultry animals and methods of controlling arthropod infestations in poultry animal's environment by administering an isoxazoline compound of formula (I) via drinking water.

Claims (86)

1. A method of preventing or treating an infestations of a laying hen by a temporary parasitic arthropod comprising administering via the drinking water an effective amount of an isoxazoline compound of formula (I)

Wherein

R 1 =halogen, CF 3 , OCF 3 , CN,

n=integer from 0 to 3

R 2 =C 1 -C 3 -haloalkyl

T=5- or 6-membered ring, which is optionally substituted by one or more radicals Y,

or is selected from

wherein in T-1, T-3 and T-4 the radical Y is hydrogen, halogen, methyl, halomethyl, ethyl, haloethyl;

Y=methyl, halomethyl, halogen, CN, NO 2 , NH 2 —C═S, or two adjacent radicals Y form together a chain;

Q=X—NR 3 R 4 or a 5-membered N-heteroaryl ring, which is optionally substituted by one or more radicals;

X=CH 2 , CH(CH 3 ), CH(CN), CO, CS,

R 3 =hydrogen, methyl, haloethyl, halopropyl, halobutyl, methoxymethyl,methoxyethyl, halomethoxymethyl, ethoxymethyl, haloethoxymethyl, propoxymethyl, ethylaminocarbonylmethyl, ethylaminocarbonylethyl, dimethoxyethyl, propynylaminocarbonylmethyl, N-phenyl-N-methyl-amino, haloethylaminocarbonylmethyl, haloethylaminocarbonylethyl, tetrahydrofuryl, methylaminocarbonylmethyl, (N,N-dimethylamino)-carbonylmethyl, propylaminocarbonylmethyl, cyclopropylaminocarbonylmethyl, propenylaminocarbonylmethyl, haloethylaminocarbonylcyclopropyl,

wherein Z A =hydrogen, halogen, cyano, halomethyl (CF 3 );

R 4 =hydrogen, ethyl, methoxymethyl, halomethoxymethyl, ethoxymethyl, haloethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, propylcarbonyl, cyclopropylcarbonyl, methoxycarbonyl, methoxymethylcarbonyl, aminocarbonyl, ethylaminocarbonylmethyl, ethylaminocarbonylethyl, dimethoxyethyl, propynylaminocarbonylmethyl, haloethylaminocarbonylmethyl, cyanomethylaminocarbonylmethyl, or haloethylaminocarbonylethyl;

or R 3 and R 4 together form a substituent selected from the group consisting of:

or a salt or solvate thereof;

wherein the effective dose of the isoxazoline compound is administered via the drinking water in two or three separate dosages approximately 7 days apart;

wherein the temporary parasitic arthropod infestation is an infestation by Dermanyssus spp. and/or Ornithonyssus spp. mites; and

wherein the effective amount is between 0.1 and 10 mg/kg body weight of animals treated.

2. The method according to claim 1 wherein the isoxazoline compound is afoxolaner or lotilaner.

3. The method of claim 1 wherein the temporary parasitic arthropod infestation is an infestation by Dermanyssus gallinae.

4. The method according to claim 1 wherein the isoxazoline compound is administered in two separate dosages approximately 7 days apart.

5. The method according to claim 1 wherein the isoxazoline compound is administered in three separate dosages approximately 7 days apart.

6. A method for the prevention or treatment of parasitic arthropod infestations of laying hens during the laying period comprising administering via drinking water an effective amount of an isoxazoline compound of formula (I)

Wherein

R 1 =halogen, CF 3 , OCF 3 , CN,

n=integer from 0 to 3,

R 2 =C 1 -C 3 -haloalkyl,

T=5- or 6-membered ring, which is optionally substituted by one or more radicals Y,

or is selected from

wherein in T-1, T-3 and T-4 the radical Y is hydrogen, halogen, methyl, halomethyl, ethyl, haloethyl;

Y=methyl, halomethyl, halogen, CN, NO 2 , NH 2 —C═S, or two adjacent radicals Y form together a chain;

Q=X—NR 3 R 4 or a 5-membered N-heteroaryl ring, which is optionally substituted by one or more radicals;

X=CH 2 , CH(CH 3 ), CH(CN), CO, CS,

R 3 =hydrogen, methyl, haloethyl, halopropyl, halobutyl, methoxymethyl,methoxyethyl, halomethoxymethyl, ethoxymethyl, haloethoxymethyl, propoxymethyl, ethylaminocarbonylmethyl, ethylaminocarbonyl ethyl, dimethoxyethyl, propynylaminocarbonylmethyl, N-phenyl-N-methyl-amino, haloethyl aminocarbonylmethyl, haloethylaminocarbonylethyl, tetrahydrofuryl, methylaminocarbonylmethyl, (N,N-dimethylamino)-carbonylmethyl, propylaminocarbonylmethyl, cyclopropylaminocarbonylmethyl, propenylaminocarbonylmethyl, haloethylaminocarbonylcyclopropyl,

wherein Z A =hydrogen, halogen, cyano, halomethyl (CF 3 );

R 4 =hydrogen, ethyl, methoxymethyl, halomethoxymethyl, ethoxymethyl, haloethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, propyl carbonyl, cyclopropylcarbonyl, methoxycarbonyl, methoxymethylcarbonyl, aminocarbonyl, ethylaminocarbonylmethyl, ethylaminocarbonylethyl, dimethoxyethyl, propynylaminocarbonylmethyl, haloethylaminocarbonylmethyl, cyanomethylaminocarbonylmethyl, or haloethylaminocarbonyl ethyl;

or R 3 and R 4 together form a substituent selected from the group consisting of:

or a salt or solvate thereof, and a pharmaceutically acceptable carrier;

wherein the effective dose of the isoxazoline compound is administered via the drinking water in two or three separate dosages approximately 7 days apart;

wherein the temporary parasitic arthropod infestation is an infestation by Dermanyssus spp. and/or Ornithonyssus spp. mites; and

wherein the effective amount is between 0.1 and 10 mg/kg body weight of animals treated.

7. A Method of controlling darkling beetles in the environment of poultry animals comprising administering to the poultry animal via drinking water an effective amount of an isoxazoline compound of formula (I)

Wherein

R 1 =halogen, CF 3 , OCF 3 , CN,

n=integer from 0 to 3,

R 2 =C 1 -C 3 -haloalkyl,

T=5- or 6-membered ring, which is optionally substituted by one or more radicals Y,

or is selected from

wherein in T-1, T-3 and T-4 the radical Y is hydrogen, halogen, methyl, halomethyl, ethyl, haloethyl;

Y=methyl, halomethyl, halogen, CN, NO 2 , NH 2 —C═S, or two adjacent radicals Y form together a chain;

Q=X—NR 3 R 4 or a 5-membered N-heteroaryl ring, which is optionally substituted by one or more radicals;

X=CH 2 , CH(CH 3 ), CH(CN), CO, CS,

R 3 =hydrogen, methyl, haloethyl, halopropyl, halobutyl, methoxymethyl,methoxyethyl, halomethoxymethyl, ethoxymethyl, haloethoxymethyl, propoxymethyl, ethylaminocarbonylmethyl, ethylaminocarbonyl ethyl, dimethoxyethyl, propynylaminocarbonylmethyl, N-phenyl-N-methyl-amino, haloethyl aminocarbonylmethyl, haloethylaminocarbonylethyl, tetrahydrofuryl, methylaminocarbonylmethyl, (N,N-dimethylamino)-carbonylmethyl, propylaminocarbonylmethyl, cyclopropylaminocarbonylmethyl, propenylaminocarbonylmethyl, haloethylaminocarbonylcyclopropyl,

wherein Z A =hydrogen, halogen, cyano, halomethyl (CF 3 );

R 4 =hydrogen, ethyl, methoxymethyl, halomethoxymethyl, ethoxymethyl, haloethoxym ethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, propyl carbonyl, cyclopropylcarbonyl, methoxycarbonyl, methoxymethylcarbonyl, aminocarbonyl, ethylaminocarbonylmethyl, ethylaminocarbonylethyl, dimethoxyethyl, propynylaminocarbonylmethyl, haloethylaminocarb onylm ethyl, cyanomethylaminocarbonylmethyl, or haloethylaminocarb onyl ethyl;

or R 3 and R 4 together form a substituent selected from the group consisting of:

or a salt or solvate thereof;

wherein the effective dose of the isoxazoline compound is administered via the drinking water in two or three separate dosages approximately 7 days apart; and

wherein the effective amount is between 0.1 and 10 mg/kg body weight of animals treated.

8. The method according to claim 7 wherein the isoxazoline compound is afoxolaner or lotilaner.

9. The method according to claim 6 wherein the isoxazoline compound is afoxolaner or lotilaner.

10. The method of claim 1 , wherein n is 1, 2 or 3.

11. The method of claim 1 , wherein R 2 is CF 3 or CF 2 Cl.

12. The method of claim 1 , wherein two adjacent radicals Y form together a three or four member chain.

13. The method according to claim 6 , wherein n is 1, 2 or 3.

14. The method according to claim 6 , wherein R 2 is CF 3 or CF 2 Cl.

15. The method according to claim 6 , wherein two adjacent radicals Y form together a three or four member chain.

16. The method according to claim 7 , wherein n is 1, 2 or 3.

17. The method according to claim 7 , wherein R 2 is CF 3 or CF 2 Cl.

18. The method according to claim 7 , wherein two adjacent radicals Y form together a three or four member chain.

19. A method of preventing or treating an infestations of a laying hen by a temporary parasitic arthropod comprising administering via the drinking water an effective amount of an isoxazoline compound, wherein the isoxazoline compound is sarolaner or a salt or solvate thereof;

wherein the effective dose of the isoxazoline compound is administered via the drinking water in two separate dosages approximately 7 days apart;

wherein the temporary parasitic arthropod infestation is an infestation by Dermanyssus spp. and/or Ornithonyssus spp. mites; and

wherein the effective amount is between 0.1 and 10 mg/kg body weight of animals treated.

20. A method for the prevention or treatment of parasitic arthropod infestations of laying hens during the laying period comprising administering via drinking water an effective amount of an isoxazoline compound, wherein the isoxazoline compound is sarolaner or a salt or solvate thereof;

wherein the effective dose of the isoxazoline compound is administered via the drinking water in two separate dosages approximately 7 days apart;

wherein the temporary parasitic arthropod infestation is an infestation by Dermanyssus spp. and/or Ornithonyssus spp. mites; and

wherein the effective amount is between 0.1 and 10 mg/kg body weight of animals treated.

21. A Method of controlling darkling beetles in the environment of poultry animals comprising administering to the poultry animal via drinking water an effective amount of an isoxazoline compound, wherein the isoxazoline compound is sarolaner or a salt or solvate thereof;

wherein the effective dose of the isoxazoline compound is administered via the drinking water in two separate dosages approximately 7 days apart;

wherein the effective amount is between 0.1 and 10 mg/kg body weight of animals treated.

22. The method according to claim 6 wherein the isoxazoline compound is administered in two separate dosages approximately 7 days apart.

23. The method according to claim 6 wherein the isoxazoline compound is administered in three separate dosages approximately 7 days apart.

24. The method according to claim 7 wherein the isoxazoline compound is administered in two separate dosages approximately 7 days apart.

25. The method according to claim 7 wherein the isoxazoline compound is administered in three separate dosages approximately 7 days apart.

Assignments (2)
CHANGE OF ADDRESS Recorded Sep 26, 2023
From: INTERVET INC.
To: INTERVET INC.
Reel/Frame 065028/0818 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 20, 2020
From: HECKEROTH, ANJA REGINA; ZOLLER, HARTMUT; FLOCHLAY-SIGOGNAULT, ANNIE; HUYGHE, BRUNO
To: INTERVET INC.
Reel/Frame 051878/0681 →
Priority Claims (1)
EP 13199007 · Dec 20, 2013 · regional
Continuity (2)
Continuation 15105197
Related Publication 20190192486A1 · Jun 27, 2019
Cited By (3)
US 12,304,903 US 12,544,336 US 12,655,138