IP Library Patent Application 16570633
Patent Application
App. No. 16/570,633

ISOXAZOLINE COMPOSITIONS AND USE THEREOF IN THE PREVENTION OR TREATMENT OF PARASITE INFESTATIONS IN ANIMALS

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Patent No.
US None
App. No.
16/570,633
Abstract

This invention is directed to a pharmaceutical composition for drinking water administration comprising isoxazoline compounds of formula (I) and a polysorbate surfactant and diethylene glycol monoethyl ether (transcutol); and the use of the composition to treat or prevent parasite infestations of animals.

Claims (49)

1 . A method of preventing or treating parasite infestations in animals by administering to such animal in its drinking water Use-f a pharmaceutical composition comprising 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,

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, and a pharmaceutically acceptable carrier comprising diethylene glycol monoethyl ether and a polysorbate surfactant.

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

3 . The method according to claim 2 comprising between 1.5 mg/ml and 100 mg/ml of the isoxazoline compound.

4 . The method according to claim 1 wherein the ratio of diethylene glycol monoethyl ether to polysorbate surfactant is <50:50% w/w.

5 . The use method according to claim 1 wherein the composition further comprises ethyl lactate.

6 - 7 . (canceled)

8 . The method according to claim 1 wherein the animals are selected from pigs and poultry.

9 . The method according to claim 8 wherein the animals are laying hens.

10 . The method according to claim 1 wherein the parasite infestation is a mite infestation.

11 . The method according to claim 10 wherein the mite infestation is an infestation with Dermanyssus sp. or Ornithonyssus sp.

12 . A Medicated drinking water comprising a mixture of a pharmaceutical composition comprising 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,

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, and a pharmaceutically acceptable carrier comprising diethylene glycol monoethyl ether and a polysorbate surfactant and water.

13 . The Medicated drinking water according to claim 12 wherein the amount of the isoxazoline compound is between 0.001 and 100 mg/ml.

14 . (canceled)

15 . A Method for preparing medicated drinking water according to claim 12 wherein the pharmaceutical composition is diluted by injecting through a dosing pump system in a water system or by mixing with water in a medication tank.

16 . The medicated drinking water according to claim 12 wherein the isoxazoline compound is afoxolaner, sarolaner or lotilaner.

17 . The medicated drinking water according to claim 12 wherein the composition further comprises ethyl lactate.

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

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

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

21 . The medicated drinking water according to claim 12 , wherein n is 1, 2 or 3.

22 . The medicated drinking water according to claim 12 , wherein R 2 is CF 3 or CF 2 Cl.

23 . The medicated drinking water according to claim 12 , wherein two adjacent radicals Y form together a three or four member chain.

24 . The method according to claim 12 wherein the ratio of diethylene glycol monoethyl ether to polysorbate surfactant is <50:50% w/w.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2019
From: LEHAY, ANNE; FLOCHLAY-SIGOGNAULT, ANNIE
To: INTERVET INC.
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