# US 10,864,195 B2 · Topical localized isoxazoline formulation

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- Number: US 10,864,195 B2
- Document ID: US10864195B2
- Status: Granted
- Kind: B2
- Application number: 15/819,523
- Filed: 2017-11-21
- Published: 2018-03-29
- Granted: 2020-12-15
- Earliest claimed: 2010-12-27
- Assignees: Intervet Inc.
- Applicants: Intervet Inc.
- Inventors: Stefan Fuchs; Anja Regina Heckeroth; Ramona Müller; Heike Williams; Hartmut Zoller
- Web page: https://patentgrep.com/patent/US10864195B2

## CPC

- A61K 31/42: Oxazoles
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)}
- A61K 9/0017: {Non-human animal skin, e.g. pour-on, spot-on}
- A61K 9/08: Solutions {(composition of solutions A61K47/00)}
- A61K 31/366: having six-membered rings, e.g. delta-lactones
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61K 47/08: containing oxygen, {e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides}
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61K 47/12: Carboxylic acids; Salts or anhydrides thereof
- A61K 47/20: containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
- A61K 47/22: Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
- A61P 33/14: Ectoparasiticides, e.g. scabicides
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

This invention provides topical localized formulations comprising an isoxazoline compound and a pharmaceutically or veterinary acceptable liquid carrier vehicle comprising N,N-diethyl-3-methylbenzamide as a solvent and an improved method for controlling, and preventing parasite infestation in animals.

## Claims

### Claim 1

A topical localized formulation for the treatment of parasite infestation in animals which comprises an effective amount of at least one isoxazoline compound of the Formula (I)
wherein
R1 is 3-CF3, and 5-C1; n is 2;
R2 is CF3;
T is
Q is X-NR3R4;
X is C(O);
R3 is -CH2-C(O)-NH-CH2-CF3;
and R4 is H
or
R1 is 3-, 4-, and 5-Cl; n is 3;
R2 is CF3;
T is
Q is X-NR3 R4;
X is C(O);
Y is methyl;
R3 is -CH2-C(O)-NH-CH2-CF3;
and R4 is H;
and a veterinary acceptable liquid carrier vehicle wherein the liquid carrier vehicle comprises N,N-diethyl-3-methylbenzamide as a solvent.

### Claim 2 (depends on 1)

The topical localized formulation according to claim 1, wherein the formulation comprises 1 to 50% N,N-diethyl-3-methylbenzamide.

### Claim 3 (depends on 1)

The topical localized formulation according to claim 1 wherein the liquid carrier vehicle comprises N,N-diethyl-3-methylbenzamide as solvent and a co-solvent selected from the group consisting of dimethyl sulfoxide, acetone, dimethylacetamide, ethyl alcohol, eucalyptol, dipropylene glycol monomethyl ether, methylethyl ketone, glycofurol, ethyl-L-lactate, and a mixture of at least two of these co-solvents.

### Claim 4 (depends on 3)

The topical localized formulation according to claim 3 wherein the liquid carrier vehicle comprises N,N-diethyl-3-methylbenzamide as solvent and a mixture of at least two of acetone, ethyl-L-lactate, dimethyl sulfoxide, dimethylacetamide and glycofurol.

### Claim 5 (depends on 3)

The topical localized formulation according to claim 3 wherein there is a weight/weight ratio of the cosolvent/solvent in the spot-on composition and the weight/weight ratio of the cosolvent/solvent is between 4/1 and 1/5.

### Claim 6 (depends on 1)

The topical localized formulation according to claim 1, wherein the formulation further comprises an effective amount of one or more compounds selected from a macrocyclic lactone compound or an insect growth regulator compound.

### Claim 7 (depends on 3)

The topical localized formulation of claim 3, wherein the formulation further comprises an effective amount of one of more compounds selected from a macrocyclic lactone compound or an insect growth regulator compound.

### Claim 8 (depends on 7)

The topical localized formulation of claim 7, wherein the macrocyclic lactone compound is selected from ivermectin, moxidectin, milbemycin, selamectin, emamectin, latidectin and lepimectin or a salt thereof and the insect growth regulator compound is selected from fenoxycarb, lufenuron, diflubenzuron, novaluron, triflumuron, fluazuron, cyromazine, methoprene and pyriproxyfen.

### Claim 9 (depends on 3)

The topical localization formulation of claim 3, wherein the veterinary acceptable liquid carrier comprises a co-solvent of at least two of ethyl-L-lactate, dimethyl sulfoxide, dimethylacetamide and glycofurol.

### Claim 10 (depends on 1)

The topical localized formulation of claim 1, wherein
R1 is 3-CF3, and 5-Cl; n is 2;
R2 is CF3;
T is
Q is X-N R3 R4;
X is C(O);
R3 is -CH2-C(O)-NH-CH2-CF3;
and R4 is H.

### Claim 11 (depends on 1)

The topical localized formulation of claim 1, wherein
R1is 3-, 4-, and 5-C1; n is 3;
R2 is CF3;
T is
Q is X-N R3 R4;
X is C(O);
Y is methyl;
R3 is -CH2-C(O)-NH-CH2-CF3;
and R4 is H.

### Claim 12 (depends on 1)

A method for treatment of parasite infestation of an animal comprising spot-on or pour-on administration of a localized topical formulation of claim 1.

### Claim 13 (depends on 12)

The method of claim 12 wherein the veterinary acceptable liquid carrier comprises a co-solvent of at least two of acetone, ethyl-L-lactate, dimethyl sulfoxide, dimethylacetamide and glycofurol.

### Claim 14 (depends on 12)

The method of claim 12 wherein the topical localized formulation comprises additionally an effective amount of a macrocyclic lactone compound and/or an insect growth regulator compound.

### Claim 15 (depends on 14)

The method of claim 14 wherein the macrocyclic lactone compound is selected from ivermectin, moxidectin, milbemycin, selamectin, emamectin, latidectin and lepimectin or a salt thereof and the insect growth regulator compound is selected from fenoxycarb, lufenuron, diflubenzuron, novaluron, triflumuron, fluazuron, cyromazine, methoprene and pyriproxyfen.