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(19) United States (12) Patent Application Publication (10) Pub US 20110281920A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0281920 A1 Holmes et al. (43) Pub. Date: Nov. 17, 2011 (54) INJECTABLE PARASITICIDAL Publication Classi?cation FORMULATIONS OF LEVAMISOLE AND MACROCYCLIC LACTONES (51) Int. Cl. A61K 31/429 (2006.01) (76) Inventors: Robert Holmes, Biirkenhead (NZ); A61P 33/10 (2006.01) Majid Razzak, The Palms (NZ); Alan Johnson, Papatoetoe (NZ); (52) US. Cl. ...................................................... .. 514/368 Jitendra GosWami, Miyapur (IN); Atul AWasthi, Manukau City (NZ) (57) ABSTRACT (21) Appl. No.: 13/106,677 The present invention provides levamisole/macrocyclic lac tone-containing inj ectable formulations that are effective (22) Filed: May 12, 2011 against animal pests, including endoparasites. The formula tions may be used for combating parasites in or on birds and Related US. Application Data mammals. The invention also provides for an improved (60) Provisional application No. 61/333,882, ?led on May method for eradicating, controlling and preventing parasite 12, 2010. infestation of birds and mammals. Patent Application Publication Nov. 17, 2011 Sheet 1 of 3 US 2011/0281920 A1 Dimethylacetamide (DMA) Add ‘ 4 . Eprinomectin V ‘ Mix until clear Add BHT Mix until clear Methylparaben 2 Mix until clear polysorbate 80 Mix until clear / Cremophor EL v DMA/Eprinomecrin/B HTAl/lelhylparaben/Pol 80mm,“ A ysorbate80 or Cremophor EL Water for Injection Add Levamisole > < Mix until clear Phosphate V Add Sol u t'onl A w“; Bulksohmon ‘H Mix~ with- silverson' 1831mm Wm] --——--~—->- Bulk Salim-On 4- Mix With Silverson V Aseptic ?ltration through 0.22 micron FIG. I Aseptic Filling Patent Application Publication Nov. 17, 2011 Sheet 2 0f 3 US 2011/0281920 A1 Levamisoile Conc in Plasma of Cattle Treated with Eprin/Levinj 1.2 E‘ 1 "" " i‘ u U3 " E 5 E16 7' rrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrr '7 .E WWBNZDS '3 £14 “?n-‘SW09 5’ £12 * "main 0 i 0 '5 l0 15 20 25 30 Time?ws} FIG. 2 Patent Application Publication Nov. 17, 2011 Sheet 3 0f3 US 2011/0281920 A1 Eprinomectin Conc in Plasma of Cattle ‘treated with Eprin/Lev inj 0.06 0.05 {mg/kg)Eprinomectinplasmacane 0.03 56 10E! 159 20G 25G 300 FIG. 3 US 2011/0281920 A1 Nov. 17, 2011 INJECTABLE PARASITICIDAL cins are described in Aoki et al., US. Pat. No. 3,950,360 as FORMULATIONS OF LEVAMISOLE AND Well as in the various references cited in “The Merck Index” MACROCYCLIC LACTONES 12”’ ed., S. Budavari, Ed., Merck & Co., Inc. Whitehouse Station, N]. (1996). Semi-synthetic derivatives of these INCORPORATION BY REFERENCE classes of compounds are Well knoWn in the art and are [0001] This application claims priority to US. provisional described, for example, in US. Pat. No. 5,077,308, US. Pat. patent application No. 61/333,882, ?led May 12, 2010. All No. 4,859,657, US. Pat. No. 4,963,582, US. Pat. No. 4,855, documents cited or referenced in the applicant cited docu 317, US. Pat. No. 4,871,719, US. Pat. No. 4,874,749, US. Pat. No. 4,427,663, US. Pat. No. 4,310,519, US. Pat. No. ments, and all documents cited or referenced herein (“herein 4,199,569, US. Pat. No. 5,055,596, US. Pat. No. 4,973,711, cited documents”), and all documents cited or referenced in US. Pat. No. 4,978,677, and US. Pat. No. 4,920,148, all herein cited documents, together With any manufacturer’s incorporated herein by reference in their entirety. A particu instructions, descriptions, product speci?cations, and product larly useful macrocyclic lactone is eprinomectin, Which is sheets for any products mentioned herein or in any document incorporated by reference herein, are hereby incorporated described in US. Pat. No. 6,174,540, US. Pat. No. 6,733,767, herein by reference, and may be employed in the practice of US. Pat. No. 5,602,107 to Merck (all incorporated by refer ence). This compound provides for a very short milk With the invention. draWal period due to it tendency to partition aWay from the milk of a lactating mammal. FIELD OF THE INVENTION [0006] To overcome the problem of resistance, various [0002] The present invention is directed to neW injectable combinations of anthelmintics have been extensively parasiticidal formulations comprising levamisole and macro researched. Unfortunately, combinations of macrocyclic lac cyclic lactones. The present invention also provides methods tone anthelmintics With anthelmintics of other families have for eradicating, controlling, and preventing parasite infesta proven di?icult to formulate at high concentration and With tion and/or infection in birds, ?sh and mammals. The formu an acceptable viscosity for injection. For example, Closamec lations of the invention may be administered to animals, tin (manufactured by Norbrook) contains iverrnectin at 0.5% particularly mammals, ?sh and birds, to prevent or treat para and closantel at 12.5% and is so viscous that the product is sitic infestation and/ or infection. supplied in a special pack that has a Warming device. The Warming device is activated 15 minutes before administration BACKGROUND OF THE INVENTION and the pack requires periodic shaking throughout this time to [0003] Animals, such as mammals, ?sh and birds are often ensure temperature reduces the viscosity suf?ciently for susceptible to parasite infestation and/or infection. These acceptable administration. parasites may be ectoparasites, such as insects and acarine [0007] Another example, Which has been the subject of species, and endoparasites such as ?lariae and other Worms. considerable research, is combining a macrocyclic lactone Endoparasites pose a signi?cant problem to those Who raise (ML) With levamisole. The di?iculties of combining these production animals such as bovines, ovines, and porcines. tWo actives lies in the stability of each being incompatible in Thus, there is an ongoing need to develop active pesticidal the environment in Which the other is stable. and parasiticidal compounds to protect animals against attack [0008] Levamisole is stable in acid conditions usually a pH or infestation/infection by pests. of about 4 or beloW, While macrocyclic lactones are unstable [0004] Many endoparasiticides or anthelmintics exist in the in conditions Where the pH is acidic. Both levamisole and art for treating internal parasites and other animal pests. macrocyclic lactones are Well knoWn in the art. In particular, These endoparasiticides vary in cost as Well as their effective levamisole has been used as an anthelmintic to treat nema ness to a particular parasite. HoWever, the results of treatment todes and respiratory Worm infestations in both humans and With these pesticides are not alWays satisfactory because of animals. Levamisole may be combined With other actives, continued development of resistance by the parasite to the although often With signi?cant dif?culty, as is described in available therapeutic agents. Thus, there is a need in the art for various patents and applications. For example, US 2009/ more effective parasiticidal agents for treatment and protec 0075918 A1 to Neto et al. appears to contemplate adding tion of animals, eg mammals, ?sh and birds from infestation various organic salts of levamisole to macrocyclic lactones, by animal parasites. but provides no Working examples. Other applications that [0005] The averrnectin and milbemycin series of com mention levamisole in combination With macrocyclic lac pounds are potent anthelmintic and antiparasitic agents tones include WO 00/061068, Which describes non-aqueous against a Wide range of internal and external parasites. The pour-on formulations that further contain triclabendaZole, compounds Which belong to this series are either natural and WO 04/009080, Which describes stable pyrrolidone products or are semi-synthetic derivatives thereof. The struc based formulations of averrnectins or milbemycins combined ture of these tWo series of compounds are closely related and With levamisole. Even more recently, WO2010021555 (to they both share a complex 16-membered macrocyclic lactone Intervet) has described oral drenches containing levamisole ring; hoWever, the milbemycins do not contain the disaccha and a macrocyclic lactone, Where the macrocyclic lactone is ride substituent in the 13-position of the lactone ring. The apparently stabiliZed via the inclusion of a protective agent, natural product averrnectins are disclosed in US. Pat. No. namely hydroxypropyl starch phosphate. Since this type of 4,310,519 to Albers-Schonberg, et al., and the 22,23-dihydro “protective agent” also serves as a thickener and emulsion averrnectin compounds are disclosed in Chabala, et al., US. stabiliZer, this particular approach to stabiliZing the macro Pat. No. 4,199,569. For a general discussion of averrnectins, cyclic lactone component may be ill-suited to developing Which include a discussion of their uses in humans and ani injectable formulations. Hydroxypropyl starch phosphate mals, see “Ivermectin and Abamectin,” W. C. Campbell, ed., (HP starch) is typically used for creams & lotions, founda Springer-Verlag, NY. (1989). Naturally occurring milbemy tions, mascara, color cosmetics, liquid make-up, liquid talc, US 2011/0281920 A1 Nov. 17, 2011 conditioners, shampoos, sunscreen products, and antiperspi that the Applicants reserve the right to this invention and rants. Finally, AU200310102 (to Nufarm and Novar‘tis) hereby disclose a disclaimer of any previously knoWn prod describes formulations having levamisole, avermectins, and uct, process, or method. benZimidaZole, said formulations appearing to make use of a [0014] It is noted that in this disclosure and particularly in biphasic solvent system, in an attempt to overcome the prob the claims and/or paragraphs, terms such as “comprises”, lematic instability of formulations Which comprise levami “comprised”, “comprising” and the like can have the meaning sole and macrocyclic lactones. Several patents describe long acting injectable combination formulations comprising attributed to it in US. patent laW; e.g., they can mean macrocyclic lactones and other actives, for example US “includes”, “included”, “including”, and the like; and that patent numbers US.
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