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WO 2013/150052 Al 10 October 2013 (10.10.2013) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization I International Bureau (10) International Publication Number (43) International Publication Date WO 2013/150052 Al 10 October 2013 (10.10.2013) P O P C T (51) International Patent Classification: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, A61K 9/00 (2006.01) A61K 47/12 (2006.01) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, (21) International Application Number: KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, PCT/EP2013/056987 ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (22) International Filing Date: NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, 3 April 2013 (03.04.2013) RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, (25) Filing Language: English 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, 12163198.0 4 April 2012 (04.04.2012) GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, 61/782,434 14 March 2013 (14.03.2013) UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, (71) Applicant: INTERVET INTERNATIONAL B.V. EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, [NL/NL]; Wim de Korverstraat 35, NL-583 1 AN Boxmeer MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, (NL). TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). (71) Applicant (for US only): INTERVET INC. [US/US]; 556 Morris Avenue, Summit, NJ 07901 (US). Declarations under Rule 4.17 : (72) Inventors; and — as to applicant's entitlement to apply for and be granted a (71) Applicants (for US only): ALTEHELD, Susi [DE/DE]; patent (Rule 4.1 7(H)) Zur Propstei, 55270 Schwabenheim (DE). FUCHS, Stefan — as to the applicant's entitlement to claim the priority of the [DE/DE]; Zur Propstei, 55270 Schwabenheim (DE). earlier application (Rule 4.1 7(in)) HANG, Carina [DE/DE]; Zur Propstei, 55270 Schwaben heim (DE). LUTZ, Jiirgen [DE/DE]; Zur Propstei, 55270 Published: Schwabenheim (DE). — with international search report (Art. 21(3)) (74) Agents: STUMM, K. et al; Wim de Korverstraat 35, NL- — before the expiration of the time limit for amending the 5831 AN Boxmeer (NL). claims and to be republished in the event of receipt of (81) Designated States (unless otherwise indicated, for every amendments (Rule 48.2(h)) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, o o (54) Title: SOFT CHEWABLE PHARMACEUTICAL PRODUCTS (57) Abstract: A soft chewable pharmaceutical product for delivery of a pharmaceutically acceptable active ingredient to an animal comprising pamoic acid or a pharmaceutically acceptable salt and a process for the manufacture of such soft chewable pharmaceutic - al product. Soft chewable pharmaceutical products FIELD OF THE INVENTION The invention relates to the field of orally administrable pharmaceutical dosage units such as soft chews, especially for administration to non-human animals. BACKGROUND OF THE INVENTION Chewable pharmaceutical products for drug delivery are well known. Formulation of a drug into a chewable dosage form can increase (animal) patient acceptance of the medication that tend to resist swallowing hard tablets or capsules. Texture is important for the acceptance of such oral products by (animal) patients. One of the most commonly used form for chewable pharmaceutical products is a chewable compressed tablet, whose ingredients, however, can make the tablet gritty or otherwise unappealing, especially to non-human animals. Thus, a preferred alternative dosage form for non-human animals is the "soft chew" generally a meat-like mass also widely found in consumable pet treats. Soft chews have been described in prior art. United States Patent No. 6,387,381 discloses an extrudate which is formed of a matrix having starch, sugar, fat, polyhydric alcohol and water. WO 2004/014143 relates to compositions and processes for the delivery of an additive to an organism in a form suitable for consumption, and in particular, in the form of a soft chew. US 2009/0280159 and US 201 1/0223234, relate to palatable edible soft chewable medication vehicles. The processes described herein relate to the problem that heat generated during the extrusion process causes deterioration in the stability of the active ingredient in the mixture. Machines for the high volume production of molded food patties have been described to be useful for the manufacturing of soft chews for administration to non-human animals. Such machines are molding machines developed for use in producing molded food products, for example Formax F6™ molding machine made by the Formax Corporation or the molding machines disclosed in U.S. Pat. Nos. 3,486,186; 3,887,964; 3,952,478; 4,054,967; 4,097,961 ; 4,182,003; 4,334,339; 4,338,702; 4,343,068; 4,356,595; 4,372,008; 4,535,505; 4,597,135; 4,608,731 ; 4,622,717; 4,697,308; 4,768,941 ; 4,780,931 ; 4,818,446; 4,821 ,376; 4,872,241 ; 4,975,039; 4,996,743; 5,021 ,025; 5,022,888; 5,655,436; and 5,980,228. Such machines are originally used to form hamburger patties from a supply of ground beef by forcing the ground beef under pressure into a multi-cavity mold plate which is rapidly shuttled on a linear slide between a fill position and a discharge position in which vertically reciprocable knock-outs push the patties from the mold cavities. For use in the manufacturing of soft chews, a dough mass is prepared with ingredients that lead to the meat-like texture of the resulting soft chew after forming and drying. For the manufacturing of a veterinary medicament on an industrial scale it is necessary to produce the soft chews by a forming machine that is able to produce high volume. However, it has been observed that some soft chew components of the dough, that is fed to the forming equipment, cause the blocking of the movable parts, especially the mold plates in the forming machine. Accordingly, the art field is in search of soft chew compositions that are easily processable in forming equipment on an industrial scale. Salts of pamoic acid are known as pamoates or embonates and are conventionally used as a counter ion of certain basic active ingredients to obtain long-acting pharmaceutical formulations. Examples of pamoate salts of active ingredients in veterinary medicine are the anthelmintic compounds pyrantel pamoate and oxantel pamoate and the antihistamine hydroxycine pamoate. A number of active ingredients used in human health are pamoate salts, e.g. as disclosed in WO 94/25460, WO 05/016261 , WO 04/017970, or WO 05/075454. The use of pamoic acid or a pharmaceutically acceptable salt thereof as excipient in soft chew formulations has not been described. It has now been found that the soft chews that comprise pamoic acid or a pharmaceutically acceptable salt thereof can be easily processed in a forming machine and that pamoic acid or a pharmaceutically acceptable salt thereof facilitates manufacturing of such soft chews on an industrial scale using a forming machine. SUMMARY OF THE INVENTION The invention provides a new soft chewable pharmaceutical product for administration to non- human animals and a process for its manufacture. Accordingly, in one embodiment the present invention relates to a soft chewable veterinary pharmaceutical product (a "soft chew") comprising as ingredients, - pamoic acid or a pharmaceutically acceptable salt thereof, provided that such pamoic acid or pharmaceutically acceptable salt thereof is not an active pharmaceutical ingredient, - one or more active pharmaceutical ingredients, - a liquid component, - a forming agent, and - optionally one or more excipients. In one embodiment the invention provides a soft chewable veterinary pharmaceutical product comprising as ingredients, - pamoic acid or a pharmaceutically acceptable salt thereof, provided that such pamoic acid or pharmaceutically acceptable salt thereof is not an active pharmaceutical ingredient, - optionally one or more active pharmaceutical ingredients, - a liquid component, - a forming agent, and - optionally one or more excipients. In a preferred embodiment the product comprises sodium pamoate. In one embodiment the amount of pamoic acid or the pharmaceutically acceptable salt thereof is between 1.5 and 30 %w/w, preferably between 2 and 5 %w/w. In another embodiment a soft chewable veterinary pharmaceutical product is provided comprising as ingredients, - a pamoate salt of an active pharmaceutical ingredient, provided that such active pharmaceutical ingredient is not pyrantel pamoate or oxantel pamoate, - optionally another active pharmaceutical ingredient, - a liquid component, - a forming agent, - optionally pamoic acid or a pharmaceutically acceptable salt thereof, and - optionally one or more excipients. In one embodiment the product as described above additionally comprise one or more of the following excipients: - a filler, - a stabilizer component, - a flavoring component, and/or - a sugar component. In one embodiment the active pharmaceutical ingredient is an isoxazoline compound of Formula (I) Formula ( I), wherein R = halogen, CF3, OCF3, CN, n = integer from 0 to 3 , preferably 1, 2 or 3 , 2 R = Ci-C 3-haloalkyl, preferably CF3 or CF2CI, T = 5- or 6-membered ring, which is optionally substituted by one or more radicals Y, Y = methyl, halomethyl, halogen
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