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WO 2016/207234 Al 29 December 2016 (29.12.2016) P O P C T

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WO 2016/207234 Al 29 December 2016 (29.12.2016) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2016/207234 Al 29 December 2016 (29.12.2016) P O P C T (51) International Patent Classification: AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, A61K 31/42 (2006.01) A61P 33/00 (2006.01) BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (21) International Application Number: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, PCT/EP20 16/064449 KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, (22) International Filing Date: MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, 22 June 2016 (22.06.2016) PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, (25) Filing Language: English TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (26) Publication Language: English (84) Designated States (unless otherwise indicated, for every (30) Priority Data: kind of regional protection available): ARIPO (BW, GH, 15 173454.8 23 June 2015 (23.06.2015) EP GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, (71) Applicant: INTERVET INTERNATIONAL B.V. TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, [NL/NL]; Wim de Korverstraat 35, 583 1 AN Boxmeer DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (NL). LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, (71) Applicant (for US only): INTERVET INC. [US/US]; 2 GW, KM, ML, MR, NE, SN, TD, TG). Giralda Farms, Madison, NJ New Jersey 07940 (US). Declarations under Rule 4.17: (72) Inventors: FLOCHLAY-SIGOGNAULT, Annie; 2 Gir alda Farms, Madison, New Jersey 07940 (US). LEHAY, — as to applicant's entitlement to apply for and be granted a Anne; 7 rue Olivier de Serres Angers Technopole, 49071 patent (Rule 4.1 7(H)) Beaucouze Cedex (FR). — as to the applicant's entitlement to claim the priority of the (74) Agent: INTERVET INTERNATIONAL BV ASS. NO. earlier application (Rule 4.1 7(in)) 666; Wim de Korverstraat 35, 583 1 AN Boxmeer (NL). Published: (81) Designated States (unless otherwise indicated, for every — with international search report (Art. 21(3)) kind of national protection available): AE, AG, AL, AM, l o (54) Title: ISOXAZOLINE SOLUTION CONTAINING VITAMIN E FOR USE WITH SANITIZED DRINKING WATER (57) Abstract: For the prevention of parasite infestation of animals, an isoxazoline can be administered by drinking water route. v However the inventors have found that when the drinking water is sanitized, for instance by using hypochlorite, the isoxazoline be - o comes degraded. Surprisingly, the isoxazoline can be protected from degradation by the use of a vitamin E. A pharmaceutical com position can now be prepared containing a concentrated solution of the isoxazoline in a solvent and co-solvent, with vitamin E. The composition can be diluted in drinking water, even when sanitized, to prepare medicated drinking water for animals. This way an an o ti-parasitic treatment can be mass-administered, leading to a highly effective reduction of the parasite infestation of an animal, and its surroundings. ISOXAZOLINE SOLUTION CONTAINING VITAMIN E FOR USE WITH SANITIZED DRINKING WATER The present invention relates to the fields of veterinary parasitology and -pharmacology, specifically to the treatment or prevention of parasite infestation of non-human animals. In particular the invention relates to a pharmaceutical composition comprising an isoxazoline, a solvent and a co-solvent; to medicated drinking water comprising this pharmaceutical composition; to methods for the preparation of the pharmaceutical composition and of the medicated drinking water; to (medical) uses of the pharmaceutical composition and of the medicated drinking water; to the stabilisation of an isoxazoline in medicated drinking water comprising a water sanitizer; to a container comprising the pharmaceutical composition; and to a kit comprising the container. Isoxazoline substituted benzamide derivatives were first described in WO 2005/08521 6 (Nissan Chem. Ind. Ltd.), as pesticides with potential for veterinary insecticidal- and acaricidal use, and subsequently their use as parasiticides has been further developed. These hydrophobic compounds contain a 5 membered isoxazole ring structure, which is covalently bound to other aryl or heteroaryl systems in position 3 and 5 , and which can each contain further substituents or more or less extensive side chains. The isoxazolines possess at least one chiral centre at position 5 of the isoxazoline ring. While the S- enantiomer seems to provide the parasiticidal activity, but often a racemic mixture is used. Meanwhile many variants of isoxazoline pesticides have been described, for example in: WO 2007/0791 62, WO 2008/1 22375, WO 2009/002809, WO 2009/02454 1, WO 2009/080250, WO 201 0/070068, WO 201 0/079077, WO 201 1/075591 , WO 201 1/ 124998, WO 201 2/1 55352, WO 201 2/1 55676, WO 201 2/1 58396, WO 201 5/048371 , WO 201 5/066277, and EP 2865369. Several isoxazoline parasiticides were described specifically for veterinary use in the prevention or treatment of infestations by ectoparasites. Examples are: Fluralaner (CAS registry number: 864731 -61 -3), Afoxolaner (CAS RN: 1093861 -60-9), Lotilaner (CAS RN: 1369852-71 -0), and Sarolaner (CAS RN: 1398609-39-6). These isoxazolines are known to be very effective parasiticides, mainly by their effect on the nervous system by blocking of the GABA-gated chloride channel of arthropods (see Gassel et al., 201 4 , Insect Biochem. Mol. Biol., vol. 45, p. 111; and: Shoop et al. , 201 4 , Vet. Paras., vol. 201 , p. 179). Currently two formulations are commercially available: Bravecto™ (Fluralaner - Merck/MSD Animal Health), and NexGard ™ (Afoxolaner - Merial), which both have been registered specifically for oral administration to dogs for the prevention of fleas and ticks. After oral uptake via a soft-chew tablet, the active is distributed systemically, and upon a bite an ectoparasite ingests a lethal dose of the parasiticide. For animals other than dogs, the oral administration route is equally effective, however for animals which are reared in intensive farming operations such as pigs, cattle and poultry, a method of administration more suitable for mass application is preferred , such as administration by drinking water. In that respect PCT/EP201 4/078634, the content of which is hereby incorporated by reference, describes a formulation comprising an isoxazoline, a solvent and a surfactant which provides a composition that can effectively be administered via the existing drinking water system and water medication equipment, without significant segregation or sedimentation of the active compound. Patent application PCT/EP20 14/078636 the content of which is hereby incorporated by reference, describes advantageous use of such a composition for the treatment of poultry via drinking water, especially against parasitic arthropods. Many types of animal parasites are known; next to internal- or endoparasites, ectoparasites are relevant as they are more readily apparent on the affected animal, and their effects on the welfare and economic performance of animals can be considerable. Ectoparasites are very diverse, but the most relevant pests are arthropods, for example: insects like flies, fleas, lice, bugs and mosquitoes, or arachnids like ticks and mites. Many ectoparasites, in one or more stages of their development, feed on tissue, blood or other body fluids from a host. Negative effects can vary from a simple annoyance to a cause of death. This is because the parasite-host contact involves a variety of mechanical and biological interactions: the ectoparasite's piercing of the skin may cause a rash, an inflammation, or a secondary infection; the repeated blood consumption by thousands of ectoparasites over time may cause a host to become anaemic; and also the parasite may be a vector for pathogens (bacteria, Rickettsia, viruses, protozoa or helminths) that can infect the host from the parasite's mouth-parts, saliva, or its faeces. One of the advantageous uses described in PCT/EP20 14/078634 and PCT/EP20 14/078636, is the prevention or treatment of infestation of poultry with mites such as Dermanyssus gallinae (poultry red mite), Ornithonyssus sylviarum (Northern fowl mite), and O. bursa (tropical fowl mite). These live and develop in poultry houses and -farms, and at night crawl onto sitting birds (or remain stationary: O. sylviarum and O. bursa) and suck blood. Apart from a danger for transferring pathogens, a heavy infestation with mites can cause the birds to become anaemic. Not only is such an infestation a severe discomfort to the animals, it will also lead to a reduction in economic production levels, such as feed conversion, daily weight gain, and egg production, but also to increased costs for veterinary care and disinfection. In addition, heavy mite infestations will also affect persons handling the birds, as they may be bitten as well. Conventional methods of extermination of mite infestation employ synthetic organic chemicals such as pyrethroids, organophosphates, carbamates or spinosad , to decontaminate the poultry house or the birds themselves e.g. by spray, fog, or dust. However, because mites are very small and hide in cracks, such treatments have only been moderately effective. In addition, these chemical treatments are being increasingly scrutinised due to development of resistance in the parasites, as well as out of concerns over environmental- and occupational safety. Therefore an alternative, and more effective way to treat and prevent mite infestation in poultry farming is required.
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