IP Library Granted Patent US 12,616,677
Granted Patent B2
US 12,616,677 · App. 17/606,262 · Granted May 5, 2026

Injectable pharmaceutical compositions and uses thereof

Inventors: Brenda L. Valle Colon (New Brunswick, NJ); Keith A. Freehauf (Stockton, NJ); Frank Guerino (Monroe Township, NJ); Christopher D. Kulczar (Jersey City, NJ); Brian Carrillo (Jackson, NJ)
Assignee: Intervet Inc.
A61K31/365A61K9/0019A61K9/1617A61K9/1635A61K9/1641A61K9/1652A61K9/1694A61K31/42A61K31/422A61P33/00
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,616,677
App. No.
17/606,262
Granted
May 5, 2026
Kind
B2
Abstract

An injectable pharmaceutical composition comprising an isoxazoline compound of Formula (I), or a salt or N-oxide and moxidectin microspheres and a method of preventing or treating a parasite infestation using the same.

Claims (32)

1 . An injectable veterinary composition comprising

a) moxidectin microspheres comprising from about 50% to about 99% by weight of a fat, wax or mixture thereof, and 0.01-10% by weight of an anti-oxidant; and

b) particles of an isoxazoline compound

wherein the isoxazoline compound is fluralaner

wherein the moxidectin microspheres and isoxazoline compound particles are suspended in an aqueous carrier comprising one or more suspending agents selected from sodium carboxymethylcellulose, polyvinylpyrrolidone and methylcellulose, one or more wetting agents comprising a poloxamer, and water and optionally one or more preservatives.

2 . The injectable veterinary composition of claim 1 wherein the fat, wax or mixture thereof has a melting point of higher than about 40° C.

3 . The injectable veterinary composition of claim 1 wherein the moxidectin microspheres comprise from about 75% to about 95% by weight of the fat, wax or mixture thereof.

4 . The injectable veterinary composition according to claim 1 wherein said fat, wax or mixture thereof comprises a fatty acid ester.

5 . The injectable veterinary composition according to claim 4 wherein said fatty acid ester is glyceryl tristearate.

6 . The injectable veterinary composition according to claim 1 in which the moxidectin microspheres and/or isoxazoline compound particles have a volume weighted particle size distribution D50 as measured by a static light scattering instrument of from about 25 μm to about 250 μm.

7 . The injectable veterinary composition according to claim 6 wherein the moxidectin microspheres or isoxazoline compound particles size distribution D50 is from about 75 μm to about 150 μm.

8 . The injectable veterinary composition according to claim 1 in which the isoxazoline compound particles have a thickness of greater than 10 μm but less than 100 μm, as measured by scanning electron microscopy.

9 . The injectable veterinary composition according to claim 8 wherein the isooxazoline compound particles have a thickness of greater than 30 μm but less than 80 μm.

10 . The injectable veterinary composition of claim 1 , wherein the D10 of the volume weighted particle size of the moxidectin microspheres or the isoxazoline compound particles as measured by a static light scattering instrument is about 20 to 35 μm, the D50 of the particle size is about 90 to 105 μm and the D90 of the particle size is about 155 to 175 μm.

11 . The injectable veterinary composition of claim 1 , wherein the wetting agent is a poloxamer.

12 . A kit, wherein the kit comprises:

a) a first container comprising a solid mixture of particles of isoxazoline compound wherein the isoxazoline compound is fluralaner and moxidectin microspheres comprising from about 50% to about 99% by weight of a fat, wax or mixture thereof, and 0.01-10% by weight of an anti-oxidant and;

b) a second container with an aqueous carrier comprising one or more suspending agents wherein the suspending agent is selected from sodium carboxymethylcellulose, polyvinylpyrrolidone and methylcellulose,

one or more wetting agents comprising poloxamer, and water and optionally preservatives; and

c) instructions for reconstituting moxidectin microspheres and isoxazoline compound particles with the aqueous carrier prior to subcutaneous or intramuscular injection to the animal.

13 . The kit according to claim 12 , wherein the first container comprises an effective amount of moxidectin and of the isoxazoline compound that is sufficient for treating or preventing a parasite infestation of an animal.

14 . The kit according to claim 12 , wherein the kit further comprises an apparatus for reconstituting and parenterally administering a mixture of the composition from the first and second container to an animal.

15 . The kit according to claim 14 , wherein the apparatus comprises a syringe.

16 . The kit according to claim 12 wherein in the first container the isoxazoline compound and/or the moxidectin microspheres have a volume weighted particle size distribution D50 of about 25 microns to about 250 microns as measured by a static light scattering instrument.

17 . The kit according to claim 12 wherein in the first container the D10 of the particle size of the isoxazoline compound is about 20 to 35 μm, the D50 of the particle size is about 90 to 105 μm and the D90 of the particle size is about 155 to 175 μm.

18 . A method of treating or preventing a parasite infestation in an animal comprising administering to the animal in need thereof the injectable veterinary composition of claim 1 .

19 . A method of producing the injectable veterinary composition according to claim 1 comprising the steps of:

a) Preparing isoxazolines particles;

b) Preparing the moxidectin microspheres by melting the fat, wax or mixture thereof and adding the moxidectin and optionally an antioxidant and preparing the microspheres through spinning disk atomization and sieving;

c) filling the moxidectin microspheres obtained by step b) together with the isoxazoline particles obtained by step a) in a first container;

d) preparing the aqueous carrier by dissolving the excipients including the suspending agents, wetting agents and/or preservatives in water and filling into a second container;

e) reconstituting the solids by transferring the aqueous carrier from the second container d) to the first container c) and shake to form a ready-to-use suspension.

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 Oct 25, 2021
From: VALLE COLON, BRENDA L.; FREEHAUF, KEITH A.; GUERINO, FRANK; KULCZAR, CHRISTOPHER D.; CARRILLO, BRIAN
To: INTERVET INC.
Reel/Frame 057904/0662 →
Continuity (2)
Provisional Application 62842709 · May 3, 2019
Related Publication 20220296564A1 · Sep 22, 2022
References Cited (30)
US 11497732B2 · Le Hir De Fallois et al. · 2022 [cited by applicant]
US 20110059988A1 · Heckeroth · 2011 [cited by applicant]
US 20110152312A1 · Le Hir de Fallois et al. · 2011 [cited by applicant]
US 20130143956A1 · Cady et al. · 2013 [cited by applicant]
US 20160235720A1 · Foster et al. · 2016 [cited by applicant]
US 20160256442A1 · Cady et al. · 2016 [cited by applicant]
US 20170239218A1 · Le Hir De Fallois et al. · 2017 [cited by applicant]
US 20180177730A1 · Corace et al. · 2018 [cited by applicant]
US 20200022959A1 · Cady et al. · 2020 [cited by applicant]
US 20210177808A1 · Freehauf et al. · 2021 [cited by applicant]
US 20210299104A1 · Cady et al. · 2021 [cited by applicant]
EP 0525307A1 · 1993 [cited by applicant]
EP 1197207B1 · 2008 [cited by applicant]
EP 2308857A1 · 2011 [cited by applicant]
WO 2009024541A2 · 2009 [cited by applicant]
WO 2012089623A1 · 2012 [cited by applicant]
WO 2012089622A2 · 2012 [cited by applicant]
WO 2013150052A1 · 2013 [cited by applicant]
WO 2016138339A1 · 2016 [cited by applicant]
WO 2016164487A1 · 2016 [cited by applicant]
WO 2017108954A1 · 2017 [cited by applicant]
WO 2017147352A1 · 2017 [cited by applicant]
WO 2018039508A1 · 2018 [cited by applicant]
WO 2019091936A1 · 2019 [cited by applicant]
WO 2019091940A1 · 2019 [cited by applicant]
Mashkovsky, M.D., Medicines, M.: Novaya Volna, Aug. 2012, 12+13, 16th Edition, English translation. [cited by applicant]
Mashkovsky, M.D., Medicines, M.: Novaya Volna, Aug. 2012, 12+13, 16th Edition. [cited by applicant]
Belikov, V.G., Pharmaceutical Chemistry, Moscow MEDpress-inform, 4th Edition, 27-29, 2007. [cited by applicant]
Pertsev, I.M. et al., Pharmaceutical and Biomedical Aspects of Drugs, Kharkov Publishing House UkrFA, Chapter 11, 253-254, 1999. [cited by applicant]
Rohdich, Nadja et al., Field effectiveness and safety of fluralaner plus moxidectin (Bravecto® Plus) against ticks and fleas: a European randomized, blinded, multicenter field study in naturally-infested client-owned ca… [cited by applicant]