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(12) Patent Application Publication (10) Pub. No.: US 2008/0306138A1 Zupan Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2008/0306138A1 Zupan Et Al US 200803 06138A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2008/0306138A1 Zupan et al. (43) Pub. Date: Dec. 11, 2008 (54) STABLE NON-AQUEOUS POUR-ON Related U.S. Application Data COMPOSITIONS (60) Provisional application No. 60/933,299, filed on Jun. (75) Inventors: Jacob Allen Zupan, Yardley, PA 5, 2007, provisional application No. 60/933,231, filed (US); Robert Bruce Albright, on Jun. 5, 2007. Chalfont, PA (US); Douglas Rugg, Lebanon, NJ (US); Izabela Publication Classification Galeska, Pennington, NJ (US); Chungjian Jerry Ong, Warren, NJ (51) Int. Cl. AOIN 43/02 (2006.01) (US) AOIN 37/52 (2006.01) Correspondence Address: AOIP 7/02 (2006.01) WYETH PATENT LAW GROUP (52) U.S. Cl. ......................................... 514/450; 514/637 5 GRALDA FARMS MADISON, NJ 07940 (US) (57) ABSTRACT The present invention relates to a stable, antiparasitic, non (73) Assignee: Wyeth, Madison, NJ (US) aqueous pour-on parasiticidal composition which comprises (21) Appl. No.: 12/133,413 an effective amount of amitraz, optionally a macrocyclic lac tone, a stabilizer and a carrier system having no active (22) Filed: Jun. 5, 2008 hydroxyl group. US 2008/0306138A1 Dec. 11, 2008 STABLE NON-AQUEOUS POUR-ON 0006. Therefore, it is an object of this invention to provide COMPOSITIONS a pour-on, parasiticidal veterinary composition containing amitraz, and at least one additional parasiticidal compound, CROSS-REFERENCE TO RELATED particularly moxidectin, which is stable, water-fast and which APPLICATIONS demonstrates a high degree of efficacy of each of the active ingredients. 0001. This application claims the benefit under 35 U.S.C. 0007. It is another object of the invention to provide a S119(e) to U.S. provisional application No. 60/933,299, filed method for the prevention, treatment and control of parasital Jun. 5, 2007, and U.S. provisional application No. 60/933, infection or infestation in a homeothermic animal. 231, filed Jun. 5, 2007, each of which is hereby incorporated 0008 A feature of this invention is that the compositions by reference in its entirety. provided offer improved efficacy over a broad spectrum of parasites for an extended period of time. BACKGROUND OF THE INVENTION 0009. Other objects and features of the invention will become more apparent from the detailed description set forth 0002. In order to control external parasites on sheep, cattle hereinbelow. and other animals including goats, pigs, horses and the like, it is a common practice to employ a localized topical applica SUMMARY OF THE INVENTION tion of a pour-on formulation containing one or more active ingredients. A pour-on formulation is typically liquid and is 0010. The present invention provides a stable antiparasitic usually applied to the exterior of an animal as a line or a spot, non-aqueous pour-on composition which comprises an effec which then acts to protect the external surface of the animal tive amount of each of amitraz and at least one additional against external parasites such as lice, keds, mites, ticks, flies parasiticidal compound and a carrier system having no active or the like. Ideally, when the pour-on formulation is applied hydroxyl group. Preferably, the additional parasiticidal com topically to a localized area, the active ingredient migrates pound is a macrocyclic lactone, more particularly, moxidec over the surface of the animal to protect its whole external tin. In a more particular embodiment, the composition com Surface area. prises a stabilizer. 0011. Also provided is a method for the treatment and 0003) Active ingredients generally employed in pour-on control of parasitic infection and infestation and a process for compositions include ectoparaciticides such as ixodicides. the preparation of a veterinary parasiticidal pour-on compo Amitraz, a valuable veterinary product, is effective against sition. strains of ticks resistant to other chemical classes of ixodi cides. Amitraz also possesses Sufficient persistence on hair 0012. Other objects, features and advantages of the and wool to control all stages of parasitic ticks. The unique present invention will become apparent from the following expellant action of amitraz causes ticks to withdraw mouth detailed description. It should be understood, however, that parts rapidly from, and fall off, the host animal. Effective tick the detailed description and the specific examples, while indi control in conjunction with effective ecto or endoparasiticidal cating preferred embodiments of the invention, are given by control is highly desirable in the raising, breeding and hous way of illustration only, since various changes and modifica ing of healthy agronomic and domestic animals. However, tions within the spirit and scope of the invention will become amitraz is, unfortunately, chemically unstable in the presence apparent to those skilled in the art from this detailed descrip of carriers having a reactive hydroxyl group Such as alcohols, tion. glycols, water and the like. This characteristic has limited the development of Veterinary compositions containing amitraz, DETAILED DESCRIPTION OF THE INVENTION and especially those containing amitraz and at least one addi 0013 Frequently, highly polar carriers containing active tional parasiticidal agent, due to the combination of the insta hydroxyl groups such as water, alcohol, glycol or the like are bility of amitraz in carriers which contain a reactive hydroxyl utilized to prepare pour-on compositions due to their compat group and the insolubility of many parasiticidal agents in ibility with animal skin, hide and/or hair, and their ability to carriers which do not contain a reactive hydroxyl group. dissolve relatively high concentrations of an active ingredi 0004 Moreover, macrocyclic lactones, particularly mox ent. Topical veterinary compositions containing amitraz as idectin is an exceptionally difficult compound to formulate. one of the active ingredients are highly desirable due to the Factors such as the size of the molecule and lack of substitu effective and persistent activity of amitraz against a wide ent Sugar moieties render the molecule lipophilic and variety of ticks, including ticks resistant to other parasiticidal insoluble in many solvents used in conventional formula actives. Heretofore, veterinary compositions containing ami tions. Accordingly, combination of two particularly difficult traz and an additional parasiticidal compound have been lim compounds in a single formulation is particularly difficult. ited by the instability of amitraz in the presence of carriers or 0005. Furthermore, acceptable topical formulations must excipients which contain an active hydroxyl group. be sufficiently easy to apply, not wash off during rainfall, 0014 When amitraz is added to a known commercial retain efficacy on wet animals, dry within a reasonable period pour-on macrocyclic lactone formulation Such as that of time without impairment of the animal's appearance, be described in U.S. Pat. No. 6,514,951 for moxidectin, the gentle on the animal's coat, non-irritating to the animal's skin resultant composition is unstable. and maintain its effectiveness on the animal through normal 0015 Surprisingly, it has now been found that amitraz and activities of the animal. Such as exposure to Sun and water. at least one additional parasiticidal compound, particularly Most desirably, the composition will provide the active ingre moxidectin, may be formulated in a stable, non-irritating dients in a formulation which will have at least a sufficient pour-on composition by employing a carrier system compris duration of activity, so as to avoid the necessity of frequent ing a non-hydroxyl-containing solvent and a stabilizer. Pref reapplications. erably the composition is substantially free of water. In a US 2008/0306138A1 Dec. 11, 2008 particular embodiment, the solvent comprises caprylic/capric 0034 (d) about 5% to about 20% w/v of an aromatic triglyceride, isopropyl myristate, mineral oil or a combina solvent; tion thereof. Accordingly, in a preferred embodiment, the 0035 (e) about 10% to about 75% w/v of caprylic/ present invention provides a topical veterinary parasiticidal capric triglyceride or mineral oil or a combination composition which comprises a carrier system as outlined thereof, and herein and an effective amount of each of amitraz and mox 0.036 (f) about 0% to about 15% w/v isopropyl idectin. myristate. 0016 Advantageously, the pour-on compositions of the 0037 More particularly, the composition comprises about present invention are well tolerated by the host animal, are not 0.01% to about 2% w/v of moxidectin. More particular still, malodorous, are capable of spreading well and rapidly over moxidectin is present at about 0.1% to about 1% w/v. Another the animal's body and are readily absorbed through the hide embodiment further comprises ivermectin. In another or skin of the treated animal. A further benefit is that the embodiment, the aromatic solvent consists essentially of compositions retain efficacy on wet skin or hide and resist C-C2 arylalkanes (e.g. toluene, xylenes, cumene, and/or wash off. pseudocumene). In another embodiment, amitraz is presentat 0017. In one embodiment, the composition is a veterinary about 1% to about 3% w/v. In another embodiment, aromatic parasiticidal composition. More particularly, the non-hy solvent is present at about 12% to about 18% w/v. In another droxyl-containing solvent comprises an aromatic solvent. embodiment, the caprylic/capric triglyceride or mineral oil or More particular still, the non-hydroxyl-containing solvent combination thereof is present at about 25% to about 65% comprises C7-Carylalkanes. In another embodiment, the w/v. In another embodiment, caprylic/capric triglyceride is non-hydroxyl-containing solvent comprises mineral oil or present at about 25% to about 65% w/v. In another embodi caprylic?capric triglyceride or a combination thereof. In ment, the isopropyl myristate is present at about 5% to about another embodiment, the non-hydroxyl-containing solvent 10% w/v. In another embodiment, the stabilizer is bis-2,6- comprises isopropyl myristate. In another embodiment, the diisopropylphenylcarbodiimide.
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