Pharmaceutical composition for controlling parasites on non-human organisms

Abstract

The present invention relates to a pharmaceutical composition comprising at least one pharmaceutically active ingredient, which is completely soluble in a solvent phase, characterized in that the pharmaceutically active ingredient is in particular from the group of fluorinated heteroarylamides, and that the solvent phase is configured as a solvent mixture and comprises at least one first solvent and a second solvent different from the first solvent, wherein the first solvent comprises a C1 to C15-alcohol, wherein the second solvent comprises an organic carbonate, and also wherein the first solvent is present in a proportion from

Description

[Technical Field]

[0001] This invention relates to pharmaceutical compositions for controlling parasites on non-human organisms. Specifically, this invention relates to formulations that are dermal-applied and have improved suitability for controlling ectoparasites on mammals and livestock. [Previous Technology]

[0002] Contemporary fluorinated antiparasitic compounds, also known as fluorinated antiparasitic agents, such as fluralaner, afoxolaner, sarolaner, lotilaner, and fipronil, have been known for a considerable period of time, and the active ingredients described in WO2015 / 067646 and WO2015 / 067647 have good insecticidal and acaricidal efficacy. However, many of these compounds have very low solubility in solvents suitable for topical administration to animals. To avoid dripping of the formulation after administration or incomplete distribution on the animal's skin, the active compound should preferably be soluble in a small amount of solvent. Furthermore, the solvent must be toxicologically safe and have high skin compatibility.

[0003] WO96 / 17520 mentions formulations applied to animal skin for the control of parasitic insects having the following components: 1 to 20% by weight of an insect nicotinic acetylcholine receptor agonist or antagonist, based on the total weight of the formulation; at least 20% by weight of a benzyl alcohol family solvent or, if desired, a pyrrolidone solvent, based on the total weight of the formulation; 5.0 to 80% by weight of, if desired, other solvents from the group of cyclic carbonates or lactones, based on the total weight of the formulation; and, if desired, 0.025 to 10% by weight of, other auxiliaries from the group of thickeners, coating agents, dyes, antioxidants, foaming agents, preservatives, adhesives, and emulsifiers, based on the total weight of the formulation.

[0004] External pour-on products for combating animal parasites are known to contain isopropanol as a solvent. These include, in particular, products containing the active ingredient ivermectin, such as Baymec® pour-on, Merial® pour-on, and others. Examples of pour-on products containing isopropanol and other active ingredients include: Sebacil® Pour-on (Bayer®, active ingredient Phoxima) and Dectomax® (Elanco, active ingredient: Doramectin). [Summary of the Invention]

[0005] The object of the present invention is to provide a pharmaceutical composition for topical application to non-human organisms using a solvent, wherein a solvent, for example a fluorinated antiparasitic agent, particularly from the heteroarylamide class, has sufficiently high solubility and good applicability to animals, particularly as a drip composition.

[0006] A pharmaceutical composition is provided, the composition comprising at least one antiparasitic pharmaceutically active ingredient that is completely soluble in a solvent phase, and particularly readily applicable to animals, wherein the pharmaceutically active ingredient is specifically derived from the group of fluorinated heteroarylamides, preferably pyridinamides, and wherein the solvent phase is configured as a solvent mixture and comprises at least one first solvent and a second solvent different from the first solvent, wherein the first solvent comprises a C1 to C15-ol, wherein the second solvent comprises an organic carbonate, and wherein, based on the total amount of solvents in the solvent phase in each case, the first solvent is present in a proportion of about 50% to 95% by weight and the second solvent is present in a proportion of 5% to 50% by weight.

Implementation Method

[0007] For example, the first solvent and the second solvent, based on the total amount of solvent in the solvent phase, can be in a weight ratio of 50%:50% to 95%:5% by weight.

[0008] According to another specific example, the first solvent may comprise only one solvent or two or more solvents, preferably a combination of two C1 to C15 alcohols, wherein in this configuration, most of the C1 to C15 alcohols are present together in the aforementioned amounts and are collectively referred to as the first solvent. Therefore, in the context of this invention, a solvent is not necessarily understood to refer only to a single substance, but a solvent may also be understood to refer to a mixture of different substances. However, it is desirable that the substances forming the first solvent be all C1 to C15 alcohols.

[0009] Alternatively or additionally, the second solvent may be composed of a single substance or a combination of two or more substances, preferably two substances, wherein the substance forming the second solvent is any organic carbonate. In this configuration, the two or more organic carbonates are present together in the aforementioned amounts.

[0010] A solvent phase consisting only of the first solvent and the second solvent is also called a binary solvent phase.

[0011] The composition according to the invention can in particular provide a novel liquid medicine for topical or dermal application using a solvent, wherein fluorinated antiparasitic agents, especially those from the heteroarylamide group, have sufficiently high solubility and good applicability to animals, particularly as a drip formulation.

[0012] The pharmaceutical composition described herein also includes at least one active pharmaceutical ingredient, hereinafter also referred to as the active ingredient, which may also be referred to as an API (active pharmaceutical ingredient). Specifically, the active ingredient may be the actual active substance in the composition and thus primarily or entirely induce an antiparasitic effect, as detailed below. Therefore, the active ingredient should be effective, especially in non-human organisms.

[0013] In principle, there are no restrictions on the active pharmaceutical ingredient. However, this is provided that the active pharmaceutical ingredient is, in particular, composed of fluorinated heteroarylamides, which are described in more detail below. In principle, heteroarylamides can be pyridylamides, in which a pyridine group is bonded to an amide via an aryl group. For example, the heteroarylamide can be fluorinated.

[0014] A further prerequisite for the active pharmaceutical ingredient is that it is completely soluble in a solvent phase. This, in particular, enables favorable skin applicability, specifically possible by drip application or a solution for drip application.

[0015] Drip application, wherein a spot-on formulation can be considered as a specific example, refers specifically to a type of application in which a relatively small amount of the formulation, for example, based on the amount of the formulation applied to the body weight of the organism, up to 100 mL / 100 kg, approximately in the range of 1 mL / 100 kg to 100 mL / 100 kg, for example, approximately in the range of 1 mL / 100 kg to 20 mL / 100 kg, approximately in the range of 5 mL / 100 kg to 10 mL / 100 kg, is applied to a closed skin area, typically on the neck or back of a non-human organism. Therefore, drip formulations are understood to refer to a type of formulation suitable and desirable for drip application.

[0016] Of particular importance for such application is achieving a high degree of solubility of the active ingredient in a so-called dripping solution, so that the desired concentration of the active ingredient is present in the solution. Furthermore, good application characteristics on the skin should be achieved. Application characteristics can be understood as referring, in particular, to the distribution of the formulation on the skin. Therefore, through these application characteristics, it can be determined whether a formulation can be distributed as a solution on a living organism to the desired extent, and specifically, whether it will drip or flow out from the application site to an excessive degree, making it possible to achieve localized application without loss of the active ingredient due to flow-out after application.

[0017] In order to achieve the aforementioned properties, especially for use in casting formulations, it is desirable that the solvent phase system in the composition described herein is configured as a solvent mixture comprising a first solvent and a second solvent different from the first solvent, wherein the first solvent system comprises a C1 to C15-ol, wherein the second solvent is an organic carbonate, and wherein, based on the total amount of solvent in the solvent phase in each case, the first solvent system is present in a ratio of 50% to 95% by weight, and wherein the second solvent system is present in a ratio of 5% to 50% by weight, wherein, in a binary solvent phase, based on the total amount of solvent in the solvent phase, the first solvent and the second solvent are present in a weight ratio of 50% to 95% by weight to 5% by weight. However, it should be noted that the total proportion of the first and second solvents does not necessarily have to be as high as 100% by weight, because, for example, a ternary system with another solvent is also conceivable and may be preferred.

[0018] In one specific example, this configuration advantageously provides a sufficient concentration of the heteroarylamide active ingredient completely dissolved in the solvent phase and thus allows for advantageous coating properties during formulation and for drop application. In one specific example, the active heteroarylamide is dissolved at least 95% by weight (active). In another specific example, the active agent is dissolved at least 97% by weight (the active agent). In yet another specific example, the active agent is dissolved at 99% by weight (the active agent). In a preferred specific example, the active agent is dissolved at 100% by weight (the active agent).

[0019] Therefore, contrary to the assumptions made in the prior art, it has been shown that positive properties can be obtained from a mixture comprising C1 to C15-alcohols, especially C1 to C10-alcohols, such as C1 to C7-alcohols, and organic carbonates. For example, the solvent mixture may consist of one or more C1 to C15-alcohols and one or more organic carbonates. These combination exhibits, for example, good solubility of the active ingredient, especially active ingredients formed from the group of fluorinated heteroarylamides, and good coating properties.

[0020] C1 to C15 alcohols, in principle, refer to aliphatic or aromatic alcohols having 1 to 15 carbon atoms.

[0021] Organic carbonates also refer to acyclic or cyclic carbonates that are themselves low-volatility polar solvents, characterized by low toxicity. By technically selecting the alcohols used in ester synthesis, the physical properties of the resulting carbonates can be adjusted to the desired application area.

[0022] Therefore, with regard to coating characteristics, administration facilities and concentration of active ingredients, i.e. efficacy, the present invention provides a composition highly suitable for drip application.

[0023] Another advantage of the formulation described herein is its good compatibility and safety with the organisms being treated, such as reduced harmful effects on animals, such as skin and / or coat, such as irritation or residues in the animal body, including entry into the food chain. The ease of formulation and administration (due to its viscosity and coating, good applicability) provides excellent environmental sustainability, enabling high consumer acceptance and reducing harmful side effects. It is suitable even for livestock used in food production. Furthermore, this formulation, by increasing the concentration of dissolved components, allows the active ingredient to remain, thus providing higher efficacy in a shorter time, making it more effective and providing a sustained period of effectiveness without the need for frequent administration. Finally, the low manufacturing cost of the formulation results in ease of handling and user-friendliness. Additional advantages include good bioavailability and a wide spectrum of efficacy.

[0024] Furthermore, the composition of the present invention can be readily applied to animals, for example, in terms of viscosity and coating properties. The composition, especially the active ingredient, also has a low tendency to be washed away, for example, by rainwater. In fact, it maintains its efficacy even in the presence of wet animals or under sunlight. The composition generally exhibits high stability and reduced degradation and, for example, secondary reactions between the composition components. The preferred stability achieved by the composition described herein includes a half-life of at least 12 months at 30°C, preferably 24 months. After application, the composition dries easily, especially by adding a solvent with good evaporability, without significantly affecting the appearance of the animal.

[0025] With regard to solvents present in a solvent phase or solvent mixture, the following solvents are particularly advantageous. The first solvent is different from the second solvent. In a specific example, the first solvent, unlike the second solvent, is not a carbonate.

[0026] In one specific example, the first solvent preferably comprises a C1-C4-alkanol substituted with at least one C1-C4-alkoxy or phenyl group, wherein the hydroxyl group may, in principle, be in any alternative position. In a particular specific example, the first solvent is selected from the group consisting of ethanol, n-propanol, isopropanol, butanol, such as isobutanol or n-butanol, especially ethanol and / or isopropanol. In addition to good solubility, especially when combined with the organic carbonates, these solvents provide the additional advantage of suitable toxicity for use in non-human organisms, making it possible to administer them without adverse effects on animals.

[0027] The second solvent is preferably a hydroxyl-substituted organic aliphatic C1-C4-carbonate, if desired. In a particular specific example, the second solvent is selected from the group consisting of ethylene carbonate, propylene carbonate, and glycerol carbonate. In addition to good solubility, especially when combined with the alcohols described above, these solvents offer the additional advantage of suitable toxicity for use in non-human organisms, making it possible to administer them without adverse effects on animals.

[0028] In a particularly preferred embodiment, the first solvent is isopropanol and the second solvent is propylene carbonate. Solvent phases comprising isopropanol and propylene carbonate as solvents have been found to provide, for example, the aforementioned advantages of good solubility of the active ingredient, favorable coating properties, and low toxicity.

[0029] In another specific example, the solvent mixture is composed of a first solvent, i.e., one or more first solvents as described above, and a second solvent, i.e., one or more second solvents as described above. In other words, the aforementioned first solvent and second solvent may be sufficient as solvents on their own, wherein, in an understandable manner, one of the first solvents and one of the second solvents may be sufficient to form a solvent mixture.

[0030] In one specific example, regarding the relative ratio of the first solvent to the second solvent, the second solvent, i.e., the organic carbonate, is preferably present at a content of ≥20% to ≤45% by weight, more preferably ≥30% to ≤40% by weight, based on the total amount of solvents in the solvent mixture. In this specific example, the first solvent is present at a content of ≥55% to ≤80% by weight, more preferably ≥60% to ≤70% by weight, based on the total amount of solvents in the solvent mixture. With this configuration, the aforementioned advantages regarding the solubility of the active ingredient, along with good coating properties, can be provided particularly effectively. In other words, excellent solubility of the active ingredient can be promoted with consistent results. Therefore, favorable applicability and stable storage characteristics are jointly provided. Because of the high solubility of the active ingredient, only a relatively low amount of solvent mixture is required. Therefore, the composition can be stored.

[0031] Furthermore, in another specific example, the solvent mixture includes a third solvent, different from the first and second solvents, in addition to the first and second solvents. Therefore, the third solvent is not the first and second solvents referred to above.

[0032] By using another solvent, the solubility and / or coating properties may be further improved or at least adjusted to the desired application.

[0033] In a particular specific example, the solvent phase is configured as a mixture of at least three solvents, wherein the third solvent is neither a C1 to C15-alcohol nor an organic carbonate, but has a different definition. However, this does not preclude the first solvent and / or the second solvent and / or the third solvent from being present, for example, a binary solvent mixture in each case.

[0034] In principle, by providing a binary solvent phase, the first solvent and the second solvent can be present within the range described above, wherein the ratio of the first solvent and the second solvent may include the ratio of the third solvent. Specifically, in a particular example, the third solvent replaces the amount of the first solvent, wherein the first solvent is still present in the range of 50% to 95% by weight, based on the total amount of solvents in the solvent phase, and wherein, in each case, the second solvent is also present in the same range as described above, i.e., 5% to 50% by weight, based on the total amount of solvents in the solvent phase. The third solvent, as well as the first and second solvents, should be pharmaceutically compatible and should not adversely affect the solubility of the active ingredient. Using a solvent that promotes penetration may be useful.

[0035] Advantageous examples of a third solvent, different from the first and second solvents, are selected from the group consisting of: water, butylated hydroxytoluene, N-methylpyrrolidone, 2-pyrrolidone, dimethyl sulfoxide, triethyl phosphate, methyl benzoate, octyl dodecyl alcohol, paraffin, triglycerides, such as caprylic / capric triglycerides (e.g., Miglyol 812), propylene glycol caprylate (e.g., Miglyol 840), glycol ethers, such as diethylene glycol methyl ether, diethylene glycol monoethyl ether, dipropylene glycol monoethyl ether, diethylene glycol monobutyl ether.

[0036] In one specific example, the solvent phase may be a binary system and therefore consists of a first solvent, a second solvent, and a third solvent. In this specific example, the first solvent, the second solvent, and the third solvent are optional as defined above.

[0037] Specifically, in a concrete example of a binary system, a non-limiting example is the sum of the first and third solvents and the second solvent, which exist in a weight ratio of 50%:50% to 95%:5% based on the total amount of solvents in the solvent phase. Regarding the relative ratio of the first solvent to the second solvent, based on the total amount of solvents in the solvent mixture, the second solvent preferably exists in a content of ≥20% to ≤45% by weight, more preferably ≥30% to ≤40% by weight. Therefore, based on the total amount of solvents in the solvent mixture, the first solvent and, if necessary, the third solvent can coexist in a content of ≥55% to ≤80% by weight, more preferably ≥60% to ≤70% by weight.

[0038] Non-limiting examples of solvent mixtures may include the following: isopropanol (32.5%), ethanol (32.5%), and propylene carbonate (35%) may be used, wherein the numbers in parentheses indicate the content as a percentage by weight based on the solvent mixture. In other examples, mixtures of isopropanol (32.5%), ethanol (32.5%), and glyceryl carbonate (35), mixtures of isopropanol (65%), propylene carbonate (17.5%), and glyceryl carbonate (17.5%), or mixtures of ethanol (65%), propylene carbonate (17.5%), and glyceryl carbonate (17.5%) may be used, wherein the numbers in parentheses therefore indicate the content as a percentage by weight based on the solvent mixture.

[0039] In one specific example, a first solvent and a solvent mixture are composed of, for example, two second solvents and, if necessary, one or more third solvents are present. In another specific example, a second solvent and a solvent mixture are composed of two first solvents and, if necessary, one or more third solvents are present.

[0040] Furthermore, the components of the composition may be limited to the solvent and the active ingredient, such that the composition may include a first solvent, a second solvent, a third solvent, and the active ingredient as needed. However, it is not desirable to exclude other components and define them elsewhere.

[0041] Preferably, the fluorinated heteroarylamide is designed as described in WO 2015067646 A1 or WO 2015067647 A1. The active ingredients of this type are preferably formulated as follows and include compounds of general formula (I): (I) wherein R1 is H, or, in various cases, a substituted C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-(C1-C3)-alkyl, heteroaryl-(C1-C3)-alkyl, or, as desired, a substituted C1-C6-alkyl, preferably H or preferably C1-C2-alkyl, very preferably H or methyl, especially H, and the group system is as follows: A1 is CR2 or N, A2 is CR3 or N, A3 is CR4 or N, A4 is CR5 or N, B1 is CR6 or N, B2 is CR7 or N, B3 is CR8 or N, B4 is CR9 or N, and B5 is CR10 or N. However, no more than three of the A1 to A4 groups are N and no more than three of the B1 to B5 groups are N; R2, R3, R4, R5, R6, R7, R9 and R10 are each independently H, halogen, cyano, nitro, and, in each case, substituted C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, N-C1-C6-alkoxyimino-C1-C3-alkyl, C1-C6-alkylhydrothio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, N-C1-C6-alkylamino, N,N-di-C1-C6-alkylamino or N-C1-C3-alkoxy-C1-C4-alkylamino or 1-pyrrolidinyl; If neither A2 nor A3 is N, then R3 and R4 can together form a 5- or 6-membered ring containing 0, 1, or 2 nitrogen atoms and / or 0 or 1 oxygen atom and / or 0 or 1 sulfur atom with the carbon atom they are bonded to; or if neither A1 nor A2 is N, then R2 and R3 can together form a 6-membered ring containing 0, 1, or 2 nitrogen atoms with the carbon atom they are bonded to; R8 is halogen, cyano, nitro, or, in each case, substituted C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, N-C1-C6-alkoxyimino-C1-C3-alkyl, C1-C6-alkylhydrothio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, N-C1-C6-alkylamino, or N,N-di-C1-C6-alkylamino.W is O or S, Q is H, methyl, hydroxy, amino, or, as needed, substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-ynyl, C3-C6-cycloalkyl, C1-C5-heterocycloalkyl, C1-C4-alkoxy, C1-C6-alkyl-C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C6-,C10-C14-aryl, C1-C5-heteroaryl, C 6-,C10-,C14-aryl-(C1-C3)-alkyl, C1-C5-heteroaryl-(C1-C3)-alkyl, N-C1-C4-alkylamino, N-C1-C4-alkylcarbonylamino, or N,N-di-C1-C4-alkylamino; or an unsaturated 6-membered carbon ring requiring poly-V-substitution; or an unsaturated 4-, 5-, or 6-membered heterocycle requiring poly-V-substitution, wherein V Independently, they are halogen, cyano, nitro, and, depending on the circumstances, substituted C1-C6-alkyl, C1-C4-alkenyl, C1-C4-ynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, N-C1-C6-alkoxyimino-C1-C3-alkyl, C1-C6-alkylhydrothio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, or N,N-di-(C1-C6-alkyl)amino; T The system is a substituted 5-membered heteroaromatic system, which contains no more than two heteroatoms (one or two heteroatoms), for example, four carbon atoms and one (1) heteroatom, preferably one (1) nitrogen, one (1) oxygen, or one (1) sulfur atom, or three carbon atoms and two heteroatoms, preferably two nitrogen atoms, one (1) nitrogen and one (1) oxygen atom, or one (1) nitrogen and one (1) sulfur atom, as well as salts, N-oxides, and tautomers of compounds of formula (I).

[0042] The description refers to, for example, a compound of formula (Ia) wherein the D1 and D2 groups are each independently C-R11 or a heteroatom selected from N and O; the D3 and D4 groups are independently C or represent a heteroatom selected from N (in other words: the D3 and D4 groups independently represent C or N); wherein no more than one (1) or two groups selected from D1, D2, D3 and D4 are heteroatoms, wherein one (1) or two groups selected from D1, D2, D3 and D4 are heteroatoms in the case of D1 and D2, or N in the case of D3 and D4; is an aromatic system; and R1, A1, A2, A3, A4, B1, B2, B3, B4, B5, R2, R3, R4, R5, R 6. R7, R8, R9, R10, R11, W, Q, V and T are each defined as described herein, wherein no more than one group selected from A1, A2, A3, A4 is N and no more than one group selected from B1, B2, B3, B4 and B5 is N; or one or two groups selected from A1, A2, A3, A4 may be N and no more than one group selected from B1, B2, B3, B4 and B5 is N, as well as salts, N-oxides and tautomers of compounds of formula (I).

[0043] A specific example of the present invention relates to a compound (Ia') of formula (Ia') wherein R1, R11, Q, W, A1, A2, A3, A4, B1, B2, B4 and B5 are each as defined herein, wherein no more than one group selected from A1, A2, A3, A4 is N and no more than one group selected from B1, B2, B3, B4 and B5 is N; or one or two groups selected from A1, A2, A3, A4 may be N and no more than one group selected from B1, B2, B3, B4 and B5 is N; D1 and D2 are each independently C-R11 or heteroatoms, preferably C-R11 or heteroatoms selected from N, O or S, more preferably C-R11 or heteroatoms selected from N or O; the D3 and D4 groups are independently C or heteroatoms selected from N; Not more than one (1) or two groups selected from D1, D2, D3 and D4 are heteroatoms, wherein one (1) or two groups selected from D1, D2, D3 and D4 are heteroatoms selected from N or O in the case of D1 and D2, or N in the case of D3 and D4; is an aromatic system, and the R8 system is as defined herein, preferably perfluoroC1-C4-alkyl.

[0044] Another specific example of the present invention relates to a compound of formula (Ia'') wherein D1 is C-R11 or a heteroatom selected from N or O; D2 is C-R11 or a heteroatom selected from N or O; D3 is C or N; D4 is C or N; D5 is C-R11 or N; wherein no more than one (1) or two groups selected from D1, D2, D3, D4 and D5 are heteroatoms; is an aromatic system; and R1 is H, or, in each case, a substituted C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, aryl-(C1-C3)-alkyl or heteroaryl-(C1-C3)-alkyl or, as desired, a substituted C1-C6-alkyl, preferably H; the group system is as follows: A1 is CR2 or N, A2 is CR3 or N, A3 is CR4 or N, A4 is CR5 or N, B1 is CR6 or N, B2 is CR7 or N, B3 is CR8 or N, B4 is CR9 or N, and B5 is CR10 or N, but no more than three A1 to A4 groups are N and no more than three B1 to B5 groups are N at the same time; R2, R3, R4, R5, R6, R7, R9, and R10 are each independently H, halogen, cyano, or nitro, and in each case, are substituted as needed with C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, N-C1-C6-alkoxyimino-C1-C3-alkyl, C1-C6-alkylhydrothio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, N-C1-C6-alkylamino, or N,N-di-C1-C6-alkylamino. If neither A2 nor A3 is N, then R3 and R4 can together form a 5- or 6-membered ring containing 0, 1, or 2 nitrogen atoms and / or 0 or 1 oxygen atom and / or 0 or 1 sulfur atom with the carbon atom they are bonded to; or if neither A1 nor A2 is N, then R2 and R3 can together form a 6-membered ring containing 0, 1, or 2 nitrogen atoms with the carbon atom they are bonded to; R8 is halogen, cyano, nitro, and, in each case, substituted as needed with C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, N-C1-C6-alkoxyimino-C1-C3-alkyl, C1-C6-alkylhydrothio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, N-C1-C6-alkylamino, or N,N-di-C1-C6-alkylamino. R11 can be independently H, halogen, cyano, nitro, amino, or, as desired, substituted C1-C6-alkyl, C1-C6-alkyloxy, C1-C6-alkylcarbonyl, C1-C6-alkylhydrothio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, H; preferably H.W is O or S, Q is H, methyl, hydroxy, amino, or, as needed, substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-ynyl, C3-C6-cycloalkyl, C1-C5-heterocycloalkyl, C1-C4-alkoxy, C1-C6-alkyl-C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C6-, C10-C14-aryl, C1-C5-heteroaryl. C6-, C10-, C14-aryl-(C1-C3)-alkyl, C1-C5-heteroaryl-(C1-C3)-alkyl, N-C1-C4-alkylamino, N-C1-C4-alkylcarbonylamino, or N,N-di-C1-C4-alkylamino; or an unsaturated 6-membered carbon ring requiring poly-V-substitution; or an unsaturated 4-, 5-, or 6-membered heterocycle requiring poly-V-substitution, wherein V Independently, they are halogenated, cyano, nitro, and, where necessary, substituted C1-C6-alkyl, C1-C4-alkenyl, C1-C4-ynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, N-C1-C6-alkoxyimino-C1-C3-alkyl, C1-C6-alkylhydrothio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, or N,N-di-(C1-C6-alkyl)amino; as well as salts, N-oxides, and tautomers of compounds of formula (Ia'').

[0045] Additionally suitable are compounds of formula (Ia''), wherein the compound of formula (Ia'') is a compound of formula (I-T3) (I-T3) wherein R1, A1, A2, A3, A4, R11, B1, B2, B4, B5, R8, Q and W are each as defined herein, wherein no more than one group selected from A1, A2, A3, A4 is N and no more than one group selected from B1, B2, B3, B4 and B5 is N; or one or two groups selected from A1, A2, A3, A4 may be N and no more than one group selected from B1, B2, B3, B4 and B5 is N.

[0046] Another specific example of the present invention relates to a compound of formula (Ia''), wherein the compound of formula (Ia'') is a compound of formula (I-T2) (I-T2) wherein R1, A1, A2, A3, A4, R11, B1, B2, B4, B5, R8, Q and W are each as defined herein, wherein no more than one group of A1, A2, A3, A4 is selected as N and no more than one group selected as N of B1, B2, B3, B4 and B5; or one or two groups selected as N of A1, A2, A3, A4 may be N and no more than one group selected as N of B1, B2, B3, B4 and B5.

[0047] Another specific example of the present invention relates to a compound of formula (Ia''), wherein the compound of formula (Ia'') is a compound of formula (I-T4) (I-T4) wherein R1, A1, A2, A3, A4, R11, B1, B2, B4, B5, R8, Q and W are each as defined herein, wherein no more than one group selected from A1, A2, A3, A4 is N and no more than one group selected from B1, B2, B3, B4 and B5 is N; or one or two groups selected from A1, A2, A3, A4 may be N and no more than one group selected from B1, B2, B3, B4 and B5 is N.

[0048] Additionally suitable are compounds of formula (Ia''), wherein the compound of formula (Ia'') is a compound of formula (I-T22) (IT-22) wherein R1, A1, A2, A3, A4, R11, B1, B2, B4, B5, R8, Q and W are each as defined herein, wherein no more than one group selected from A1, A2, A3, A4 is N and no more than one group selected from B1, B2, B3, B4 and B5 is N; or one or two groups selected from A1, A2, A3, A4 may be N and no more than one group selected from B1, B2, B3, B4 and B5 is N.

[0049] Additionally suitable are compounds of formula (Ia''), wherein the compound of formula (Ia'') is a compound of formula (I-T23) (I-T23) wherein R1, A1, A2, A3, A4, R11, B1, B2, B4, B5, R8, Q and W are each as defined herein, wherein no more than one group selected from A1, A2, A3, A4 is N and no more than one group selected from B1, B2, B3, B4 and B5 is N; or one or two groups selected from A1, A2, A3, A4 may be N and no more than one group selected from B1, B2, B3, B4 and B5 is N.

[0050] Also suitable are compounds according to the chemical formula and specific examples described herein, wherein R11 is H and W is O.

[0051] Also suitable are compounds according to the chemical formula and specific examples described herein, wherein R11 is H and W is O and B3 is C-R8, R8 being a halogen-substituted C1-C3-alkyl (preferably perhalogenated C1-C3-alkyl, more preferably perfluoroC1-C3-alkyl) or a halogen-substituted C1-C3-alkoxy (preferably perhalogenated C1-C3-alkoxy, more preferably perfluoroC1-C3-alkoxy).

[0052] Also suitable are compounds according to the chemical formula and specific examples described herein, wherein the groups A1 to A4 and B1 to B5 are as follows: A1 is CH, A2 is CR3 or N, A3 is CR4, A4 is CH, B1 is CR6 or N, B2 is CH, B3 is CR8, B4 is CH and B5 is CR10 or N.

[0053] Alternatively suitable are compounds based on the chemical formulas and specific examples described herein, wherein R1 is a compound of H.

[0054] Also suitable are compounds according to the chemical formula and specific examples described herein, wherein Q is a fluorinated C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl, C4-C6-heterocycloalkyl, 1-sulfoheterobutyl-3-yl, 1,1-sulfoheterobutyl-3-yl, benzyl, pyridin-2-ylmethyl, methylsulfonyl or 2-oxo-2-(2,2,2-trifluoroethylamino)ethyl.

[0055] Also suitable are chemical formulas and specific examples as described herein, wherein the R8 series represents halogens or halogen-substituted C1-C4-alkyl compounds.

[0056] Alternatively suitable are compounds based on the chemical formula and specific examples described herein, wherein R11 is a compound of H.

[0057] Also suitable are compounds according to the chemical formula and specific examples described herein, wherein R6, R7, R9 and R10 are independently H, halogen, cyano, nitro, and, in each case, substituted C1-C4-alkyl, C3-C4-cycloalkyl, C1-C4-alkoxy, N-alkoxyiminoalkyl, C1-C4-alkylhydrosulfo, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, N-C1-C4-alkylamino, N,N-di-C1-C4-alkylamino.

[0058] Also suitable are compounds according to the chemical formula and specific examples described herein, wherein R2, R3, R4 and R5 are independently H, halogen, cyano, nitro, and, in each case, substituted C1-C4-alkyl, C3-C4-cycloalkyl, C1-C4-alkoxy, N-C1-C4-alkoxyimino-C1-C4-alkyl, C1-C4-alkylhydrosulfo, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, N-C1-C4-alkylamino or N,N-di-C1-C4-alkylamino.

[0059] Also suitable are compounds according to the chemical formula and specific examples described herein, wherein the groups A1 to A4 and B1 to B5 are as follows: A1 is CH, A2 is CR3 or N, A3 is CR4, A4 is CH, B1 is CR6 or N, B2 is CH, B3 is CR8, B4 is CH and B5 is CR10 or N.

[0060] Also suitable are compounds based on the chemical formula and specific examples described herein, wherein R1 is a H.

[0061] Alternatively suitable are compounds according to the chemical formula and specific examples described herein, wherein R1 is a methyl compound.

[0062] Also suitable are compounds according to the chemical formula and specific examples described herein, wherein Q is fluorinated or fluoroamine (–C(=O)N(R)2, wherein R is independently H, C1-C3-alkyl or halogenated C1-C3-alkyl)-substituted C1-C4-alkyl, C3-C4-cycloalkyl, C4-C6-heterocycloalkyl, 1-sulfoheterobutyl-3-yl, 1,1-sulfoheterobutyl-3-yl, benzyl, pyridin-2-ylmethyl, methylsulfonylurea or 2-oxo-2-(2,2,2-trifluoroethylamino)ethyl.

[0063] Additionally suitable are compounds according to the chemical formula and specific examples described herein, wherein Q is 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 3,3,3-trifluoropropyl, cyclopropyl, cyclobutyl, 1-cyanocyclopropyl, trans-2-fluorocyclopropyl, or cis-2-fluorocyclopropyl, oxo-3-yl, thio-3-yl, 1-thiohexacyclobutyl-3-yl, 1,1-thiohexacyclobutyl-3-yl, benzyl, pyridin-2-ylmethyl, methylsulfonyl, or 2-oxo-2-(2,2,2-trifluoroethylamino)ethyl.

[0064] Alternatively suitable are compounds according to the chemical formula and specific examples described herein, wherein R8 is a halogen or a halogen-substituted C1-C4-alkyl compound.

[0065] The following compounds may be mentioned as preferred active ingredients for use in non-human organisms with antiparasitic efficacy: 2-chloro-N-cyclopropyl-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]-N-methylpyridin-3-methamide (I-1) 2-chloro-N-cyclopropyl-5-[1-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethoxy)phenyl]-1H-pyrazol-4-yl]-3-pyridinic methamide (I-2) 2-Chloro-5-[1-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-1H-pyrazole-4-yl]-N-cyclopropyl-3-pyridinecarboxamide: (I-3) 2-Chloro-5-[1-[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethoxy)phenyl]-1H-pyrazole-4-yl]-N-cyclopropylpyridine-3-carboxamide (I-4) 2-Chloro-N-cyclopropyl-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazole-4-yl]pyridine-3-carboxamide (I-5) 2-Chloro-N-cyanocyclopropyl-5-[1-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethoxy)phenyl]-1H-pyrazole-4-yl]benzamide: (II-1) 2-Chloro-5-[1-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethoxy)phenyl]pyrazole-4-yl]-N-cyclopropylbenzamide (II-2) 5-[1-[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethoxy)phenyl]pyrazole-4-yl]-2-chloro-N-cyclopropylbenzamide (II-3) 2-Chloro-5-[1-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]pyrazol-4-yl]-N-cyclopropylbenzamide (II-4) 2-Chloro-N-cyclopropyl-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]benzamide (II-5) 2-Chloro-N-cyclopropyl-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]-N-methylbenzamide (II-6) 2-Chloro-N-cyclopropyl-5-[1-[4-(1,1,1,2,3,3,3-Hepanopropyl-2-yl)-2-methyl-6-(trifluoromethyl)phenyl]-1H-pyrazole-4-yl]benzamide: (II-7) 2-Chloro-N-(1-cyanocyclopropyl)-5-[1-[4-(1,1,1,2,3,3,3-heptafluoropropyl-2-yl)-2-methyl-6-(trifluoromethyl)phenyl]-1H-pyrazole-4-yl]benzamide: (II-8) 2-Chloro-N-cyclopropyl-5-[4-[2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazole-1-yl]benzamide: (II-9) 2-Chloro-N-(1-cyanocyclopropyl)-5-[4-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-1-yl]benzylamine: (II-10) 2-Chloro-5-[3-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]isoazol-5-yl]-N-cyclopropylbenzylamine: (II-11) 2-Chloro-N-(1-cyanocyclopropyl)-5-[3-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]isoazol-5-yl]benzylamine: (II-12) 2-Chloro-N-(1-cyanocyclopropyl)-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrrolo-3-yl]benzamide: (II-13) 2-Chloro-5-[3-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]pyrrolo-1-yl]-N-cyclopropylbenzamide: (II-14)

[0066] The above-mentioned active ingredients may be part of the formulation described herein and thus have the effect of combating the parasites detailed below.

[0067] In the present invention, it is preferable to provide the active ingredients of formulas I-1 to I-5 and the active ingredients of formulas II-1 to II-6, and particularly preferably the active ingredients according to formulas I-1 to I-5.

[0068] According to a preferred embodiment, the compound according to Formula I-1 may contain an active ingredient, wherein a mixture of isopropanol (32.5), ethanol (32.5) and propylene carbonate (35) may be used as a solvent mixture or a mixture of isopropanol (32.5), ethanol (32.5) and glyceryl carbonate (35), or a mixture of isopropanol (65), propylene carbonate (17.5) and glyceryl carbonate (17.5) or a mixture of ethanol (65), propylene carbonate (17.5) and glyceryl carbonate (17.5), wherein the numbers in parentheses represent the percentage content based on the solvent mixture.

[0069] According to another preferred embodiment, the solvent mixture described above can be used for the active ingredient according to formula I-2, or formula I-3, or formula I-4, or formula I-5.

[0070] However, it is particularly preferred to give the active ingredients according to formulas I-1, I-2, I-3, I-4 and I-5 using only the first and second solvents.

[0071] In addition to the components listed above, the compositions according to the present invention may also include conventionally pharmaceutically acceptable adjuvants. Examples of such adjuvants include: coating agents, antioxidants, pH adjusters, crystallization inhibitors, surfactants, dyes, pigments, penetration enhancers, and preservatives.

[0072] Coating agents include, for example, coating oils, such as di-2-ethylhexyl adipate, isopropyl myristate, dipropylene glycol, cyclic and non-cyclic silicone oils, such as dimethicones, and copolymers and terpolymers thereof with ethylene oxide, propylene oxide and formaldehyde, fatty acid esters, triglycerides, and fatty alcohols. These may be added in a proportion of ≥1 to ≤40% w / v. According to other specific examples, the coating agent may be present in proportions of ≥0.01 to ≤1% w / v, ≥0.1 to ≤10% w / v, ≥1 to ≤20% w / v, ≥20 to ≤50% w / v, or ≥10 to ≤30% w / v.

[0073] Antioxidants include, for example, ascorbic acid, di-Na-EDTA, BHT, BHA, δ-tocopherol, and thioglycerol. They may be added in a proportion of ≥0.01-≤2% w / v. According to other specific examples, antioxidants may be present in proportions of ≥0.01-≤1% w / v, ≥0.05-≤0.5% w / v, or ≥1-≤2% w / v.

[0074] The pH adjuster is preferably an organic acid or base, such as citric acid or triethanolamine. It may be added in a proportion of ≥0.001-≤5% w / v. According to other specific examples, the pH adjuster may be present in a proportion of ≥0.01-≤1% w / v, ≥0.05-≤0.5% w / v, or ≥0.1-≤3% w / v.

[0075] Crystallization inhibitors include, for example, cellulose ethers, such as hydroxypropyl methylcellulose (HPMC); polyvinylpyrrolidone (PVP). These may be added in a proportion of ≥0.1-≤50% w / v. According to other specific examples, the crystallization inhibitor may be present in proportions of ≥1-≤30% w / v, ≥1-≤20% w / v, ≥5-≤15% w / v, ≥1-≤20% w / v, or ≥0.1-≤10% w / v.

[0076] The surfactants that may be mentioned include: nonionic surfactants, such as polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, glyceryl monostearate, polyoxyethylated stearate, and alkylphenol polyglycerol ethers; amphoteric surfactants, such as di-Na-N-lauryl β-imine dipropionate or lecithin; anionic surfactants, such as Na-lauryl sulfate, fatty alcohol ether sulfate, and mono / dialkyl polyethylene glycol ether orthophosphate monoethanolamine salt; and cationic surfactants, such as cetyltrimethylammonium chloride. These may be added in a proportion of ≥0.1-≤20% w / v. According to other specific examples, they may be present in proportions of ≥0.1-≤10% w / v, ≥0.1-≤1% w / v, ≥1-≤10% w / v, or ≥0.2-≤5% w / v.

[0077] Dyes may also be added to pharmaceutical compositions. They are soluble or suspended in the composition. Examples that may be mentioned include Brilliant Blue, D&C Violet 2, FD&C Yellow, Sunset Yellow FCF, or natural food colorings such as chlorophyll. They may be added in a proportion of ≥0.01-≤2% w / v. Depending on other specific examples, they may be present in a proportion of ≥0.01-≤1% w / v or ≥0.1-≤2% w / v.

[0078] Pharmaceutical ingredients may contain penetration enhancers, such as methanol, 1,8-cineole, and alcohol ethers (e.g., ethylene glycol methyl ether, diethylene glycol monoethyl ether, dipropylene glycol monoethyl ether, diethylene glycol monobutyl ether). These may be added in a proportion of ≥2 to ≤50% w / v. According to other specific examples, the penetration enhancer may be present in proportions of ≥1 to ≤20% w / v, ≥0.5 to ≤20% w / v, ≥0.1 to ≤10% w / v, ≥10 to ≤50% w / v, or ≥10 to ≤40% w / v.

[0079] In principle, there is no limitation on the concentration of the active ingredient, but the reality that all active ingredients should be soluble in solution should also be considered. Regarding advantageous drip application, for high efficacy, it may be preferable for the active pharmaceutical ingredient to be present in an amount greater than or equal to 0.1% by weight to less than or equal to 8% by weight, for example, greater than or equal to 0.1% by weight to less than or equal to 5% by weight. This amount, based on the pharmaceutical composition, can be equivalent to, for example, a ratio of 0.2-4 g / 100 ml, such as 1-3 g / 100 ml. Such concentrations pose no problem for the preparation of the aforementioned solvent mixtures, especially for topical drip application. In principle, concentrations of active ingredients up to 30% by weight or more are also possible without exceeding the scope of this invention.

[0080] The formulations according to the invention are therefore typically liquids and suitable for topical or skin application, especially so-called drip formulations.

[0081] The formulation according to the invention provides highly effective efficacy against ectoparasites, particularly in the case of the aforementioned drip application, wherein the formulation comprises active ingredients derived from the aforementioned group, particularly fluorinated benzoylamines. By using this formulation, the required amount of active ingredient can be reduced and the long-term efficacy increased. Therefore, its use achieves both economic and ecological benefits.

[0082] The formulations according to the present invention are excellently suited for parasite control or parasite prevention. Therefore, the pharmaceutical compositions described herein are intended for the treatment or prevention of parasitic infections, especially the treatment or prevention of ectoparasites.

[0083] The formulations according to the present invention are particularly suitable for controlling or preventing ectoparasites on non-human organisms, especially animals, particularly warm-blooded animals, preferably mammals, preferably ticks and / or mites, and / or flies or fly larvae, and / or lice.

[0084] According to a specific example, the animal may be a domesticated animal, such as a caged bird; or a mammal, such as a hamster, guinea pig, rat, mouse, chinchilla, ferret, or especially a dog or cat.

[0085] According to another preferred specific example, the animal may be agricultural livestock, including, for example, poultry, such as turkeys, ducks, geese and especially chickens; or more preferably mammals, such as sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer and especially cattle and pigs.

[0086] According to a particularly good specific example, this composition is used to control and / or prevent external parasites in cattle.

[0087] Because treated animals typically also release a certain amount of the composition used into the environment, for example by rubbing or by dispersing it as debris, the effects of the composition according to the invention may not only occur directly on the animal, but may also reach a corresponding level in its environment.

[0088] As described above, the composition described herein is preferably suitable for treating or preventing parasitic infections in non-human organisms by dripping or pouring the composition onto them, and is therefore a drip application.

[0089] The parasites that the formulation of the present invention can effectively combat include: those from the order Anoplura, such as blood-sucking lice (Haematopinus spp.), gnatous lice (Linognathus spp.), body lice (Pediculus spp.), blind lice (Solenopotes spp.), body lice (Pediculus spp.), and pubic lice (Pthirus spp.); those from the order Mallophaga, such as hairy lice (Trimenopon spp.), short-haired lice (Menopon spp.), Eomenacanthus spp., body lice (Menacanthus spp.), biting lice (Trichodectes spp.), cat lice (Felicola spp.), livestock lice (Damalinea spp.), and cattle lice (Bovicola spp.); and those from the order Diptera, such as Aedes spp. and Anopheles mosquitoes. spp.), house mosquito (Culex spp.), spinneret (Simulium spp.), winged fly (Phlebotomus spp.), yellow serpent fly (Chrysops spp.), horsefly (Tabanus spp.), housefly (Musca spp.), toothed fly (Hydrotaea spp.), carrion fly (Muscina spp.), blood-beaked fly (Haematobosca spp.), blood fly (Haematobia spp.), stinging fly (Stomoxys spp.), toilet fly (Fannia spp.), tsetse fly (Glossina spp.), green fly (Lucilia spp.), blowfly (Calliphora spp.), fire fly (Auchmeromyia spp.), lumbricoides fly (Cordylobia spp.), spiral fly (Cochliomyia spp.), golden fly (Chrysomyia The following are species of flies from the order Siphonaptera: *S. spp.*, *Sarcophaga* spp., *Wohlfahrtia* spp., *Gasterophilus* spp., *Oesteromyia* spp., *Oedemagena* spp., *Hypoderma* spp., *Oestrus* spp., *Rhinoestrus* spp., *Melophagus* spp., and *Hippobosca* spp., such as the comb-headed flea *Ctenocephalides* spp.Fleas such as *Echidnophaga* spp., *Ceratophyllus* spp., and *Pulex* spp. originate from the suborder Metastigmata, including ticks such as *Hyalomma* spp., *Rhipicephalus* (including the genus previously known as *Boophilus*), *Amblyomma* spp., *Haemophysalis* spp., *Dermacentor* spp., *Ixodes* spp., *Argas* spp., *Ornithodorus* spp., and *Otobius* spp.; and fleas from the suborder Mesostigmata, such as tussock mites *Dermanyssus* spp. and avian tussock mites *Ornithonyssus*. Mites from the suborder Prostigmata include *Cheyletiella* spp., *Psorergates* spp., *Myobia* spp., *Demodex* spp., and *Neotrombiculla* spp.; and mites from the suborder Astigmata, including *Acarus* spp., *Myocoptes* spp., *Psoroptes* spp., *Chorioptes* spp., *Otodectes* spp., *Sarcoptes* spp., *Notoedres* spp., *Knemidocoptes* spp., *Neoknemidocoptes* spp., and *Cytodites*. spp.), Laminosioptes spp. .

[0090] Hereinafter, the best specimens are from the order Diptera: Tabanus spp., Musca spp., Hydrotaea spp., Haematobia spp., Stomoxys spp., Glossina spp., Lucilia spp., Calliphora spp., Aedes spp., Anopheles spp., Culex spp., Simulium spp., and Phlebotomus spp.; and from the order Metastropha: Rhipicephalus (including the genus previously known as the bull tick), Amblyomma spp., Haemophysalis spp., and Dermacentor Species from the orders Anoplura (Hypnotus spp.), including *Ixodes spp.*, *Argas spp.*, *Ornithodorus spp.*, and *Otobius spp.*; Species from the orders Anoplura (Hypnotus spp.), including *Haematopinus spp.*, *Linognathus spp.*, and *Solenopotes spp.*; Species from the orders Mallophaga (Damalinea spp.), including *Bovicola spp.*, and *Trichodectes spp.*; Species from the orders Mesostigmata (Dermanyssus spp.) and *Ornithonyssus spp.*; Species from the orders Astigmata (Psoroptes spp.) and *Chorioptes*. spp.), ear mites (Otodectes spp.), scabies mites (Sarcoptes spp.), and scabies mites (Notoedres spp.).

[0091] Exceptional species include: Haematobia irritans irritans, Haematobia irritans exigua, Hydrotea irritans, Musca autumnalis, Culicoides spp., Stomoxys calcitrans, Glossina spp., Aedes spp., Anopheles spp., Culex spp., Damalina (Bovicola) bovis, Linognathus vituli, Haematopinus eurystemus, Solenopotes capillatus, Psoroptes bovis, Rhipicephalus (Boophilus) microplus, and Rhipicephalus circinata. Arthropods belonging to the genera *Boophilus annulatus*, *Rhipicephalus (Boophilus) decoloratus*, *Ixodes ricinus*, *Amblyomma maculatum*, *Amblyomma variegatum*, *Ixodes scapularis*, *Ixodes holocyclus*, *Haemaphysalis longicornis*, and *Otobius megnini*.

[0092] The formulation according to the present invention can be prepared by conventional methods, for example by stirring and mixing the active ingredient with other components to produce a solution. It can be filtered if necessary. For example, it is suitable for filling plastic test tubes.

[0093] The liquid formulation according to the present invention is characterized by its superior storage stability in all climate zones for at least one year, preferably at least two years, and more preferably at least three years. Due to its high efficacy, the dosage can be kept low. A preferred dosage is 0.01-1 ml / kg [body weight of the animal being treated], more preferably 0.05-0.1 ml / kg [body weight of the animal being treated].

[0094] The formulations according to the present invention also exhibit excellent skin compatibility and low toxicity. Finally, due to their biodegradability, they are environmentally friendly. Solubility test

[0095] Regarding the pharmaceutical composition according to the present invention, the solubility experiments of active ingredients I-1, I-2, I-3, and I-4 in solvents are as follows. For bioefficacy, the active ingredient should be incorporated into the formulation at a specific dose or amount, ideally as a solution in the formulation, such that the active ingredient is therefore soluble in the solvent. Because the dosage is limited, a specific minimum solubility is required in the solvent.

[0096] Table 1 shows the dissolution test results of active ingredient I-1. In this case, 10 g of a suitable solvent or solvent mixture was initially added, and the active ingredient was added as much as possible until the solution was saturated. Isopropanol (IPA) and propylene carbonate (PPC) were used as solvents. The sample was stirred for 3 days. The active ingredient should be completely dissolved before adding more active ingredient. Subsequently, the sample was stored at the appropriate temperature for another 4 days and centrifuged to remove undissolved particles. The content of active ingredient in the supernatant of each case was analyzed by HPLC-UV. Table 1: Solvent (mixture) and temperature of the solution Saturation concentration % [w / w] Isopropanol 5°C 0.98 Isopropanol 23°C 1.56 propylene carbonate 5°C 1.80 propylene carbonate 23°C 2.43 IPA / PPC 25 / 75 23°C 7.58 IPA / PPC 35 / 65 23°C 8.79 IPA / PPC 50 / 50 23°C 9.26 IPA / PPC 60 / 40 23°C 8.60 IPA / PPC 65 / 35 5°C 6.32 IPA / PPC 65 / 35 23°C 8.31 IPA / PPC 70 / 30 23°C 7.49 IPA / PPC 75 / 25 23°C 6.70 IPA / PPC 80 / 20 23°C 5.90 IPA / PPC 90 / 10 23°C 3.74

[0097] As can be seen from Table 1, the desired standard was not achieved in the single solvents of isopropanol and propylene carbonate, particularly in terms of sufficient solubility. The advantageous and preferred solubility of the active ingredient according to the invention is in the range of at least 5% m / V, where there should be a sufficient gap from saturated solubility. Surprisingly, the mixture of isopropanol and propylene carbonate showed a significant increase in solubility compared to the pure solvents, as detailed in Table 1.

[0098] Furthermore, solubility experiments were conducted in different solvents with three other active ingredients derived from fluorinated heteroarylamides, similar to the experiments described above, but only at room temperature and using a solvent mixture of isopropanol / propylene carbonate 65:35% [m / m]. The results are shown in Table 2. Table 2: Active compounds solvent Saturated solubility % [w / w] I-2 Isopropanol 6.99 I-2 propylene carbonate 5.34 I-2 Isopropanol / propylene carbonate 65 / 35 24.20 I-3 Isopropanol 4.18 I-3 propylene carbonate 4.89 I-3 Isopropanol / propylene carbonate 65 / 35 17.57 I-4 Isopropanol 13.42 I-4 propylene carbonate 11.76 I-4 Isopropanol / propylene carbonate 65 / 35 29.38

[0099] It has also been found that, for active ingredients I-2, I-3 and I-4, very good solubility of the active ingredients of the heteroarylamide family can be achieved by means of solvent mixtures or solvent phases of the compositions according to the present invention, especially for the defined structures.

[0100] It also shows that the significant increase in solubility is not limited to mixtures of isopropanol and propylene carbonate, but is also observed in other alcohols and carbonate solvents, such as the first and second solvents defined above. Table 3: Active ingredients solvent Saturated solubility % [ w / w] I-1 Isopropanol 1.56 I-1 propylene carbonate 2.43 I-1 ethanol 2.76 I-1 Glyceryl carbonate 0.15 I-1 Isopropanol / glyceryl carbonate 65:35 5.98 I-1 Ethanol / glyceryl carbonate 65:35 6.48 I-1 Ethanol / propylene carbonate 65:35 9.45

[0101] As can be clearly seen in Table 3, increased solubility can be achieved with other solvents. Therefore, the invention can be extended to other solvents within the stated scope. The examples shown herein are experiments conducted with ethanol and glyceryl carbonate, mixtures thereof, and combinations thereof with the shown solvents isopropanol and propylene carbonate.

[0102] Experiments were also conducted using a solvent system, wherein the first solvent system comprised two alcohols. The results are shown in Table 4. Table 4: Active compounds solvent Solubility % [w / w] I-1 Isopropanol / ethanol / propylene carbonate 32.5:32.5:35 > 5 I-1 Isopropanol / ethanol / glyceryl carbonate 32.5:32.5:35 > 5 I-1 Isopropanol / propylene carbonate / glyceryl carbonate 65:17.5:17.5 > 5 I-1 Ethanol / propylene carbonate / glyceryl carbonate 65:17.5:17.5 > 5

[0103] This also demonstrates that such binary systems can achieve good solubility of the active ingredient according to Formula I-1. Examples of formulations

[0104] The following are examples of preparations of formulations having active ingredients I-1, I-2, I-3 and I-4 as defined above and additives. In all the examples described, the respective active ingredients were completely dissolved and the stability was as desired.

[0105] Table 5 here shows examples of suitable formulations with information on solvent mixtures, active ingredients, and additional additives as needed. Table 5: serial number Components quantity 1 I-1 1.5 g Butylated hydroxytoluene 0.1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 2 I-1 2 g Butylated hydroxytoluene 0.1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 3 I-1 4.5 g Butylated hydroxytoluene 0.1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 4 I-1 4.5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 5 I-1 0.5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 6 I-4 4.5 g water 1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 7 I-1 1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 8 I-1 2 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 9 I-1 4 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 10 I-1 0.25 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 11 I-4 3 g Butylated hydroxytoluene 0.1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 12 I-4 2 g Butylated hydroxytoluene 0.1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 13 I-2 3 g Butylated hydroxytoluene 0.1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 14 I-2 3 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 15 I-3 1.5 g Butylated hydroxytoluene 0.1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 16 I-3 4.5 g Butylated hydroxytoluene 0.1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 17 I-4 2 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 18 I-1 1.9 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 19 I-1 2 g ascorbic acid 0.1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 20 I-4 4.5 g Water 2 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL twenty one I-1 2 g ascorbic acid 0.5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL twenty two I-1 2 g Sodium EDTA 0.09 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL twenty three I-1 2 g Brilliant Blue 0.1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL twenty four I-1 2 g Brilliant Blue 0.0225 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 25 I-1 2 g δ-Tocopherol 0.1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 26 I-1 2 g Thioglycerin 0.5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 27 I-1 2 g Butylated hydroxytoluene 0.1 g Butylated hydroxyanisole 0.1 g Citric acid 0.3 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 28 I-1 2 g Citric acid 0.3 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 29 I-1 2 g Butylated hydroxyanisole 0.1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 30 I-1 2 g D&C Purple No. 2 0.0225 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 31 I-1 2 g water 0.2 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 32 I-1 2 g water 0.4 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 33 I-1 2 g water 2 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 34 I-1 2 g water 3 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 35 I-1 2 g Water 5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 36 I-1 2 g water 5 g Triethanolamine 0.06 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 37 I-1 2 g water 5 g Citric acid 0.00006 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 38 I-1 1.99 g Water 10 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 39 I-1 1.99 g water 5 g Isopropanol / propylene carbonate 61.3: 31.5% w / w Add to 100 mL 40 I-1 1.99 g water 0.5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 41 I-1 1.99 g water 2 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 42 I-1 1.99 g water 1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 43 I-1 2.1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 44 I-1 2 g Isopropanol / propylene carbonate 68: 32% w / w Add to 100 mL 45 I-1 1.99 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 46 I-4 4.5 g water 5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 47 I-1 4.5 g water 1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 48 I-1 4.5 g water 2 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 49 I-1 4.5 g water 5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 50 I-2 2 g Butylated hydroxytoluene 0.1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 51 I-1 2 g Ethanol / propylene carbonate 65:35% w / w Add to 100 mL 52 I-4 4.5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 53 I-1 2 g Isopropanol / propylene carbonate 62: 38% w / w Add to 100 mL 54 I-1 35 g N-methylpyrrolidone Add to 100 mL 55 I-1 2 g propylene carbonate Add to 100 mL 56 I-1 1 g Isopropanol Add to 100 mL 57 I-2 2 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 58 I-2 4.5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 59 I-1 4.5 g Isopropanol / ethanol / propylene carbonate 32.5:32.5:35% w / w Add to 100 mL 60 I-1 4.5 g Isopropanol / ethanol / glyceryl carbonate 32.5:32.5:35% w / w Add to 100 mL 61 I-1 4.5 g Isopropanol / propylene carbonate / glyceryl carbonate 65:17.5:17.5% w / w Add to 100 mL 62 I-1 4.5 g Ethanol / propylene carbonate / glyceryl carbonate 65:17.5:17.5% w / w Add to 100 mL 63 I-2 4.5 g water 1 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 64 I-2 4.5 g water 2 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 65 I-2 4.5 g water 5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL

[0106] Table 6 shows the formulations that can be prepared based on solubility experiments. Table 6: serial number Components quantity 66 I-1 1.5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 67 I-1 3 g Ethanol / propylene carbonate 65:35% w / w Add to 100 mL 68 I-1 1.99 g Ethanol / propylene carbonate 65:35% w / w Add to 100 mL 69 I-1 3 g Ethanol / glyceryl carbonate 65:35% w / w Add to 100 mL 70 I-1 1.99 g Ethanol / glyceryl carbonate 65:35% w / w Add to 100 mL 71 I-1 3 g Isopropanol / glyceryl carbonate 65: 35% w / w Add to 100 mL 72 I-1 1.99 g Isopropanol / glyceryl carbonate 65: 35% w / w Add to 100 mL 73 I-1 3 g Benzyl alcohol / glyceryl carbonate 65:35% w / w Add to 100 mL 74 I-1 1.99 g Benzyl alcohol / glyceryl carbonate 65:35% w / w Add to 100 mL 75 I-1 3 g Benzyl alcohol / propylene carbonate 65:35% w / w Add to 100 mL 76 I-1 1.99 g Benzyl alcohol / propylene carbonate 65:35% w / w Add to 100 mL 77 I-1 1.5 g 1-Methoxy-2-propanol / glyceryl carbonate 65: 35% w / w Add to 100 mL 78 I-1 4.5 g 1-Methoxy-2-propanol / propylene carbonate 65: 35% w / w Add to 100 mL 79 I-1 1.5 g 1-Methoxy-2-propanol / propylene carbonate 65: 35% w / w Add to 100 mL 80 I-2 1.5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 81 I-3 4.5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 82 I-3 1.5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 83 I-4 4.5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 84 I-4 1.5 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 85 I-1 3 g Isopropanol / propylene carbonate 25: 75% w / w Add to 100 mL 86 I-1 3 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 87 I-1 4.5 g Ethanol / propylene carbonate 65:35% w / w Add to 100 mL 88 I-1 1.5 g Ethanol / propylene carbonate 65:35% w / w Add to 100 mL 89 I-1 4.5 g Ethanol / glyceryl carbonate 65:35% w / w Add to 100 mL 90 I-1 1.5 g Ethanol / glyceryl carbonate 65:35% w / w Add to 100 mL 91 I-1 4.5 g Isopropanol / glyceryl carbonate 65: 35% w / w Add to 100 mL 92 I-1 1.5 g Isopropanol / glyceryl carbonate 65: 35% w / w Add to 100 mL 93 I-1 4.5 g Benzyl alcohol / glyceryl carbonate 65:35% w / w Add to 100 mL 94 I-1 1.5 g Benzyl alcohol / glyceryl carbonate 65:35% w / w Add to 100 mL 95 I-1 4.5 g Benzyl alcohol / propylene carbonate 65:35% w / w Add to 100 mL 96 I-1 1.5 g Benzyl alcohol / propylene carbonate 65:35% w / w Add to 100 mL 97 I-1 3 g 1-Methoxy-2-propanol / glyceryl carbonate 65: 35% w / w Add to 100 mL 98 I-1 1.99 g 1-Methoxy-2-propanol / glyceryl carbonate 65: 35% w / w Add to 100 mL 99 I-1 3 g 1-Methoxy-2-propanol / propylene carbonate 65: 35% w / w Add to 100 mL 100 I-1 1.99 g 1-Methoxy-2-propanol / propylene carbonate 65: 35% w / w Add to 100 mL 101 I-2 1.99 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 102 I-3 3 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 103 I-3 1.99 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 104 I-4 3 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 105 I-4 1.99 g Isopropanol / propylene carbonate 65: 35% w / w Add to 100 mL 106 I-1 4.5 g Isopropanol / propylene carbonate 25: 75% w / w Add to 100 mL 107 I-1 1.5 g Isopropanol / propylene carbonate 25: 75% w / w Add to 100 mL

[0107] Formulations numbered 1 to 65 were prepared and good solubility and complete dissolution of the active ingredients were observed.

[0108] Experiments numbered 66 to 107 are examples of further hypotheses, in which practical examples are prepared based on the solubility experiments conducted, and the desired solubility can be predicted based on the chemical structure of the active ingredient and the selected solvent. Examples of in vitro and in vivo tests.

[0109] Further properties and effects of the formulations according to the present invention are described below. Example 1: Determination of the application properties of the stained placebo formulation on bovine skin.

[0110] The purpose of this in vitro study was to determine the application properties of stained placebo formulations, i.e., formulations without active ingredients, on bovine skin. The results of these tests will be applicable to the application efficacy of formulations with active ingredients. The tests were conducted using a two-solvent phase composed of isopropanol (IPA) and propylene carbonate (PPC).

[0111] For this purpose, skin flakes of approximately 10 x 10 cm with the lightest possible hair color were obtained from slaughtered cattle and placed on a heating plate covered with aluminum. The heating plate was heated to 34°C + / - 0.5°C. The skin flakes with trimmed skin and natural hair length were examined. 0.025% Brilliant Blue FCF was added as a colorant. The performance of the formulation on the skin surface and the coverage area were measured within 60 minutes. The coating was also evaluated using a comparative system. In this case, such formulations are particularly advantageous and suitable for future use on animals because their coating properties are sufficiently distributed on the skin flakes within the observation period.

[0112] The results are shown in Table 7, which illustrates the coating properties of the stained placebo formulation on the skin.

[0113] Table 7 shows the area occupied by the formulation directly on the skin sample immediately after application and 1 hour later, as well as the amount of formulation applied, hair length on the skin, and skin temperature. Table 7: Mixtures (See Table 8) IPA: PPC Quantity [µl] hair length Surface temperature [°C] Area [cm²] (0 min after application) Area [cm²] (1 hour after application) i 1:0:100 250 Shaving 34 1.445 1.963 ii 2; 25: 75 250 Shaving 34 6.872 7.846 iii 3; 50:50 250 Shaving 34 12.566 12.566 iv 4; 65:35 250 Shaving 34 14.184 15.904 v 5; 75:25 250 Shaving 34 14.137 15.708 vi 6; 90:10 250 Shaving 34 12.566 19.635 vii 7; 100: 0 250 Shaving 34 7.069 15.504 i. 1:0:100 250 Unshaved 34 1.319 1.374 ii. 2; 25: 75 250 Unshaved 34 3.534 3.789 iii. 3; 50:50 250 Unshaved 34 2.827 3.471 iv. 4; 65:35 250 Unshaved 34 6.480 7.265 v. 5; 75:25 250 Unshaved 34 2.356 2.937 vi 6; 90:10 250 Unshaved 34 10.603 19.439 vii 7; 100: 0 250 Unshaved 34 3.927 4.909

[0114] It is clear from this table that this coating property is particularly advantageous. The optimal results are achieved with an isopropanol (IPA) to propylene carbonate (PPC) ratio of 65:35.

[0115] Although this experiment also showed good results with a 90:10 isopropanol (IPA) to propylene carbonate (PPC) ratio, this solvent phase has poorer solubility compared to the formulation according to the present invention. Table 8: Mixture number Brilliant Blue FCF Colorant The ratio of isopropanol (IPA): propylene carbonate (PPC) I 0.025% w / w 0:100 Ii 0.025% w / w 25:75 Iii 0.025% w / w 50:50 Iv 0.025% w / w 65:35 V 0.025% w / w 75:25 Vi 0.025% w / w 90:10 Vii 0.025% w / w 100:0 Example 2

[0116] In Example 2, the coating and run-off properties of a placebo formulation stained on bovine hide were determined. The purpose of this in vitro study was to determine the coating and run-off properties of a placebo formulation stained on bovine hide. 0.025% Brilliant Blue FCF was added as a colorant.

[0117] The formulation used is equivalent to the formulation in Table 8.

[0118] For this purpose, a piece of hide with the lightest color layer, approximately 10 x 10 cm in size, is obtained from slaughtered cattle and placed on a heating plate covered with aluminum. The heating plate is heated to 34 + / - 0.5°C. For the loss test, the heating plate is measured at an angle of 45° + / - 2°. A sheet of filter paper is fixed under the hide piece.

[0119] Record the behavior and loss rate of the formulation on the skin surface within 1 minute, and then carefully calculate using a ruler. Evaluate the coating using a rating system.

[0120] In this case, these formulations are particularly suitable for future use on animals because their loss characteristics during the observation period result in little or no staining on the filter paper. These formulations also achieve adequate distribution on the skin grafts.

[0121] The results are shown in Table 9, which measures the loss rate of the longest flow path within 1 minute after application of 750 µl of the staining placebo formulation. Table 9: IPA: PPC Mixture number Natural hair length variations Behavior The velocity of the longest flow path [mm / sec] Through filter paper Surface distribution 0:100 I medium and long Three narrow tracks left on the hair surface and flowed out. 85.0 It started dripping rapidly after 2 seconds. The application band is still narrow (<1 cm), but some of it sinks into the hair from the surface. 25:75 ii medium and long The hair sinks into the fur, forming two narrow flow tracks that are clearly visible as it flows downwards and then converges at the bottom. 10.0 It begins to drip after 40 seconds and continues to drip, with the dripping volume being less than 0:100. The application band was still narrow (<2 cm), and the fluid flowed out of the skin and did not reach the hair. 50:50 iii long It quickly sinks into the fur and a blue sheen can be seen beneath the fur - without a rapid flow path, but rather dispersed on the surface. 0.8 Nine minutes later, the filter paper showed blue droplets, but the amount was less than 25:72. The application band was still narrow (<2 cm) and flowed out of the skin, not onto the hair. 65:35 iv medium and long It sinks quickly into the coat and has a blue sheen visible beneath the outer coat - without narrow flow lines - widely distributed. 1.3 area After 7.22 seconds, small blue dots appeared on the filter paper. The application band widens (2-4 cm) and extends downwards to the skin surface. 75:25 v long The line is not wide - quite wide, with a thin downward flow trajectory. 3.3 [area] Not passing through filter paper / dripping The application zone remains narrow (<1 cm), and the flow trajectory narrows at the beginning. 90:10 vi medium and long Fast, very flat, with a flowing trajectory 1.7 area Not passing through filter paper / dripping The application band widens upwards (4 cm), and the flow path is short, flowing downwards along the skin surface. 100:0 vii long Large-area, rapid distribution with wide flow trajectories 2.7 area Not passing through filter paper / dripping It appears as a narrow application band on the surface—rapidly distributing in the skin as an area with three visible short flow tracks.

[0122] The tests, in turn, clearly showed very good results with the stated ratio of isopropanol (IPA) and propylene carbonate (PPC) because the loss characteristics during the observation period resulted in little or no filter paper staining and, in this case, adequate distribution on the leather. Example 3

[0123] In Example 3, the efficacy of the drip formulation against Haematobia irritans irritans in cattle was determined. The purpose of this study was to determine the preventive efficacy of the insecticidal formulation in cattle against experimentally generated Haematobia irritans infection.

[0124] This study was conducted as a blinded, negative-controlled, randomized parallel-group efficacy study. Each group consisted of 5 animals. Before treatment, all animals were pre-classified into descending order by hornfly counting and then divided into 4(x) groups of 5 animals each. Cattle were then randomly assigned to the groups and classified into descending order of number. Cattle were individually tethered to areas covered with mesh. Approximately 200 unfed hornflies were used to infect the animals on days -5, 1, 7, 14, 21, and 28, and in some cases, also on days 35 and 42. The number of hornflies on the cattle was measured 4 hours after infection on day 1, 24 hours after infection on day 2, and on days 8, 15, 22, and 29, and, if appropriate, on days 36, 43, 50, and 57. The efficacy against hornfly infection was determined by comparing the number of hornflies on treated cattle with the number on untreated cattle. In this case, the treatment was considered successful if the treatment group measured at least 90% efficacy compared to the control group.

[0125] The results are shown in Table 10, which verify the efficacy of the formulation according to the present invention against small hornflies (Haematobia irritans irritans) on cattle. Table 10: test Grouping Examples of blends Dosage mg / kg dpt 2 dpt 8 dpt 15 dpt 22 dpt 29 dpt 36 dpt 43 dpt 50 dpt 57 C 5 0,5 >90 >90 >90 >90 >90 >90 <90 <90 <90 C 7 1 >90 >90 >90 >90 >90 >90 >90 <90 <90 B 1 1.5 >90 >90 >90 >90 >90 >90 >90 and and C 8 2 >90 >90 >90 >90 >90 >90 >90 >90 >90 C 9 4 >90 >90 >90 >90 >90 >90 >90 >90 >90 B 3 4.5 >90 >90 >90 >90 >90 >90 >90 and and A 15 1.5 >90 >90 >90 >90 <90 <90 and na na A 16 4,5 >90 >90 >90 >90 <90 <90 na na na A 13 3 >90 >90 >90 >90 >90 <90 na na na B 11 3 >90 >90 >90 >90 >90 >90 >90 na na Dpt = Number of days after administration; na = No data.

[0126] Examples 5 and 7 in Table 10 clearly demonstrate long-lasting and effective effects even at low doses. Additionally, Examples 8, 9, 1, 3, and 11 also show long-lasting effectiveness. Example 4

[0127] In Example 4, the efficacy of the drip formulation against the tick [Rhipicephalus (Boophilus) microplus] on cattle was determined.

[0128] The purpose of this study was to determine the therapeutic and preventive efficacy of a mite-killing formulation in cattle against experimentally induced infection with *Tectus microta*.

[0129] This study was conducted as a parallel-group, unblinded, negative-controlled, randomized utility study. Each group consisted of 5 animals. Before treatment (days -14 to -2), all animals were pre-classified in descending order by sex and individual tick infection count, and then divided into groups of 5 animals each (2(x)). Cattle were randomly assigned to groups and classified in descending order of number. Each animal was infected with 3000 larvae on days -35, -33, -29, -27, -22, -20, -15, -13, -8, -6, -1, 5, 7, 12, 14, 19, 21, 26, and 28. Decreased congested female ticks were collected daily from days -14 to -2 and from days 0 to 56. Ticks were grouped from day -14 to day -2. Therapeutic efficacy was measured using ticks from day 1 to day 28, and preventative efficacy was determined using ticks from day 29 until the end of the tick descent period. Tick reproductive capacity was also determined. This was performed by hatching larvae from eggs in a mixed sample of ovipositors and congested female ticks. In this case, a hatching rate >60% was considered normal. The compounds tested in this study did not achieve significant additional efficacy.

[0130] In this case, regarding the therapeutic efficacy against existing tick infestations, a treatment is considered successful if it achieves 90% efficacy in the treatment group compared to the control group (based on the decrease in the number of congested female ticks from day 1 to day 28 after treatment). Therefore, if the efficacy is less than 90%, it is considered ineffective.

[0131] Regarding the preventive efficacy against newly emerging tick infections, a treatment is considered successful if it achieves 90% efficacy in the treatment group compared to the control group (based on the decrease in the number of congested female ticks on days 29-56 after treatment). Therefore, if the efficacy is less than 90%, it indicates insufficient efficacy.

[0132] The results are shown in Tables 11 and 12. Table 11 shows the therapeutic efficacy of the formulation according to the present invention against cattle ticks (Fernula microta) of all ages on cattle, while Table 12 shows the preventive efficacy of the formulation according to the present invention against newly emerging cattle tick (Fernula microta) infections on cattle. Table 11: Post-treatment study days Experimental grouping Examples of blends Dosage mg / kg 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 C 7 1 on on <90 <90 <90 <90 <90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 C 8 2 on on <90 <90 <90 <90 <90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 C 9 4 na na <90 <90 <90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 A 15 1.5 <90 <90 <90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 A 16 4,5 <90 <90 <90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 A 13 3 <90 <90 <90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 B 2 2 <90 <90 <90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 B 12 2 <90 <90 <90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 na = No data in Table 12: Post-treatment study days Experimental grouping Examples of blends Dosage mg / kg 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 C 7 1 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 on 100 100 on C 8 2 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 on 100 100 on C 9 4 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 na 100 100 na A 15 1.5 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 <90 <90 >90 <90 <90 na na A 16 4,5 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 and and A 13 3 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 and and B 2 2 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 <90 <90 <90 >90 >90 >90 <90 na B 12 2 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 >90 na na = No data

[0133] As can be seen in Tables 11 and 12, all the active ingredients in the formulations according to the present invention are highly effective even at low doses in terms of preventive and therapeutic efficacy against tick infection. Example 5

[0134] Following Example 5, the efficacy of the drip formulation against bovine lice (Bovicola bovis) was determined. The purpose of this study was to determine the therapeutic and preventative efficacy of the bovine insecticide formulation against naturally occurring bovine lice infestation.

[0135] This study was conducted as a parallel, unblinded, negative-controlled efficacy study. Each group consisted of 5 animals. The number of lice was counted on day -2 before treatment and on days 2, 14, 28, and 42. In this case, the fur of each animal was screened and counted in 10 septa. This was done by hatching larvae from eggs in a mixed sample of ovipositors and congested female ticks. A hatching rate >60% was considered normal. The compound tested in this study did not achieve significant additional efficacy. The results for each animal were averaged across groups and compared with the number of lice in the untreated control group. The actual efficacy against existing lice infestation was measured on day 2. In this case, the treatment was considered successful if at least 90% efficacy was measured in the treatment group compared to the control group. Therefore, efficacy below 90% was considered ineffective. The persistence of efficacy against existing lice infestation was measured by counts at days 14, 21, and 42.

[0136] In this case, the treatment was considered successful if the treatment group achieved 100% efficacy compared to the control group. Therefore, treatment was considered ineffective if the efficacy was below 100%. Table 13: Experimental grouping Examples of blends Dosage mg / kg dpt 2 dpt 14 dpt 28 dpt 42 B 2 2 >90 100 100 100 B 12 2 >90 100 100 100 A 16 3 <90 <100 <100 100 A 13 3 <90 <100 100 100 A 15 3 <90 <100 100 100 Dpt = Number of days after treatment

[0137] Table 13 shows the efficacy of the formulation according to the present invention against bovicola bovis.

[0138] As is evident from Table 13, Examples 2 and 16 are particularly fast and efficient when used in compositions according to the invention having a defined solvent mixture.

[0139] Therefore, the above evidence demonstrates that the pharmaceutically active ingredient according to the present invention exhibits good solubility for benzoylamine-type active ingredients, thus making it an effective active ingredient, especially for the treatment or prevention of parasitic infections, particularly in the case of non-human organisms. In this case, application by irrigation is particularly advantageous.

Claims

1. A pharmaceutical composition comprising at least one pharmaceutically active ingredient soluble in a solvent phase, wherein the pharmaceutically active ingredient is a fluorinated heteroarylamide, and wherein the solvent phase is a solvent mixture comprising at least one first solvent and a second solvent different from the first solvent, wherein the first solvent comprises a C1 to C15-ol, wherein the second solvent comprises an organic carbonate, wherein the first solvent is present in a proportion of 50% to 95% by weight, and the second solvent is present in a proportion of 5% to 50% by weight, based on the total amount of solvents in the solvent phase.

2. The pharmaceutical composition according to claim 1, wherein the first solvent is selected from C1-C4-alkanols that are substituted with at least one C1-C4-alkoxy group or phenyl group as desired, and wherein the first solvent is selected from the group consisting of ethanol, n-propanol, isopropanol, and butanol.

3. The pharmaceutical composition according to claim 1 or 2, wherein the second solvent is selected from aliphatic C1-C4-carbonates that are substituted with a hydroxyl group as desired.

4. The pharmaceutical composition according to claim 2 or 3, characterized in that the first solvent is isopropanol and the second solvent is propylene carbonate.

5. A pharmaceutical composition according to any one of claims 1 to 4, wherein the solvent mixture is composed of a first solvent and a second solvent.

6. A pharmaceutical composition according to any one of claims 1 to 4, wherein the solvent mixture further comprises, in addition to the first solvent and the second solvent, a third solvent different from the first solvent and the second solvent.

7. The pharmaceutical composition according to claim 6, wherein the third solvent is selected from the group consisting of: water, butylated hydroxytoluene, N-methylpyrrolidone, 2-pyrrolidone, dimethyl sulfoxide, triethyl phosphate, methyl benzoate, octyl dodecanol, paraffin, triglycerides, propylene glycol octanoate, and glycol ether.

8. A pharmaceutical composition according to any one of claims 1 to 7, wherein the second solvent is present in an amount of ≥20% to ≤45% by weight, based on the total amount of solvents in the solvent mixture, preferably in an amount of ≥30% to ≤40% by weight.

9. A pharmaceutical composition according to any one of claims 1 to 8, characterized in that the active ingredient is selected from compounds of general formula (I): (I) wherein R1 is H, a C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C6-alkanecarbonyl, C1-C6-alkoxycarbonyl, aryl-(C1-C3)-alkyl, heteroaryl-(C1-C3)-alkyl, or a C1-C6-alkyl that is substituted as needed, preferably H or preferably C1-C2-alkyl, very preferably H or methyl, especially H, wherein the groups are as follows: A1 is CR2 or N, A2 is CR3 or N, A3 is CR4 or N, A4 is CR5 or N, B1 is CR6 or N, B2 is CR7 or N, B3 is CR8 or N, B4 is CR9 or N, and B5 is CR10 or N. However, no more than three A1 to A4 groups are N and no more than three B1 to B5 groups are N; R2, R3, R4, R5, R6, R7, R9 and R10 are each independently H, halogen, cyano, nitro, and, in each case, substituted C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, N-C1-C6-alkoxyimino-C1-C3-alkyl, C1-C6-alkylhydrosulfo, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, N-C1-C6-alkylamino, N,N-di-C1-C6-alkylamino or N-C1-C3-alkoxy-C1-C4-alkylamino or 1-pyrrolidinyl; If neither A2 nor A3 is N, then R3 and R4 can together form a 5- or 6-membered ring containing 0, 1, or 2 nitrogen atoms and / or 0 or 1 oxygen atom and / or 0 or 1 sulfur atom with the carbon atom they are bonded to; or if neither A1 nor A2 is N, then R2 and R3 can together form a 6-membered ring containing 0, 1, or 2 nitrogen atoms with the carbon atom they are bonded to; R8 is halogen, cyano, nitro, or, in each case, a substituted C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, N-C1-C6-alkoxyimino-C1-C3-alkyl, C1-C6-alkylhydrothio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, N-C1-C6-alkylamino, or N,N-di-C1-C6-alkylamino.W is O or S, Q is H, methyl, hydroxy, amino, or, as needed, substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-ynyl, C3-C6-cycloalkyl, C1-C5-heterocycloalkyl, C1-C4-alkoxy, C1-C6-alkyl-C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C6-, C10-C14-aryl, C1-C5-heteroaryl. C6-, C10-, C14-aryl-(C1-C3)-alkyl, C1-C5-heteroaryl-(C1-C3)-alkyl, N-C1-C4-alkylamino, N-C1-C4-alkylcarbonylamino, or N,N-di-C1-C4-alkylamino; or an unsaturated 6-membered carbon ring requiring poly-V-substitution; or an unsaturated 4-, 5-, or 6-membered heterocycle requiring poly-V-substitution, wherein V Independently, they are halogen, cyano, nitro, and, depending on the circumstances, substituted C1-C6-alkyl, C1-C4-alkenyl, C1-C4-ynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, N-C1-C6-alkoxyimino-C1-C3-alkyl, C1-C6-alkylhydrothio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, or N,N-di-(C1-C6-alkyl)amino; T The system is a substituted 5-membered heteroaromatic system, which contains no more than two heteroatoms (one or two heteroatoms), for example, four carbon atoms and one (1) heteroatom, preferably one (1) nitrogen, one (1) oxygen, or one (1) sulfur atom, or three carbon atoms and two heteroatoms, preferably two nitrogen atoms, one (1) nitrogen and one (1) oxygen atom, or one (1) nitrogen and one (1) sulfur atom, as well as salts, N-oxides, and tautomers of compounds of formula (I).

10. The pharmaceutical composition according to claim 9, wherein the active ingredient is selected from the group consisting of: 2-chloro-N-cyclopropyl-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]-N-methylpyridin-3-methamide (I-1) 2-chloro-N-cyclopropyl-5-[1-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethoxy)phenyl]-1H-pyrazol-4-yl]-3-pyridinic methamide (I-2) 2-Chloro-5-[1-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-1H-pyrazole-4-yl]-N-cyclopropyl-3-pyridinecarboxamide: (I-3) 2-Chloro-5-[1-[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethoxy)phenyl]-1H-pyrazole-4-yl]-N-cyclopropylpyridine-3-carboxamide (I-4) 2-Chloro-N-cyclopropyl-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazole-4-yl]pyridine-3-carboxamide (I-5) 2-Chloro-N-cyanocyclopropyl-5-[1-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethoxy)phenyl]-1H-pyrazole-4-yl]benzamide: (II-1) 2-Chloro-5-[1-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethoxy)phenyl]pyrazole-4-yl]-N-cyclopropylbenzamide (II-2) 5-[1-[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethoxy)phenyl]pyrazole-4-yl]-2-chloro-N-cyclopropylbenzamide (II-3) 2-Chloro-5-[1-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]pyrazol-4-yl]-N-cyclopropylbenzamide (II-4) 2-Chloro-N-cyclopropyl-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]benzamide (II-5) 2-Chloro-N-cyclopropyl-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]-N-methylbenzamide (II-6) 2-Chloro-N-cyclopropyl-5-[1-[4-(1,1,1,2,3,3,3-heptafluoroprop-2-yl)-2-methyl-6-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl]benzylamine: (II-7) 2-Chloro-N-(1-cyanocyclopropyl)-5-[1-[4-(1,1,1,3-heptafluoroprop-2-yl)-2-methyl-6-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl]benzylamine2,3,3,3-Heptafluoroprop-2-yl)-2-methyl-6-(trifluoromethyl)phenyl]-1H-pyrazole-4-yl]benzamide: (II-8) 2-Chloro-N-cyclopropyl-5-[4-[2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazole-1-yl]benzamide: (II-9) 2-Chloro-N-(1-cyanocyclopropyl)-5-[4-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrazole-1-yl]benzamide: (II-10) 2-Chloro-5-[3-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]isoazol-5-yl]-N-cyclopropylbenzamide: (II-11) 2-Chloro-N-(1-cyanocyclopropyl)-5-[3-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]isoazol-5-yl]benzamide: (II-12) 2-Chloro-N-(1-cyanocyclopropyl)-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]pyrrole-3-yl]benzamide: (II-13) 2-Chloro-5-[3-[2-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]pyrrolo-1-yl]-N-cyclopropylbenzamide: (II-14).

11. A pharmaceutical composition according to any one of claims 1 to 10, wherein the active pharmaceutical ingredient is present in an amount greater than or equal to 0.1% by weight and less than or equal to 5% by weight.

12. A pharmaceutical composition according to any one of claims 1 to 11 is used for the treatment or prevention of parasitic infections.

13. The pharmaceutical composition according to claim 12 is used for the treatment or prevention of ectoparasitic infections.

14. A pharmaceutical composition according to any one of claims 1 to 13 is used for the treatment or prevention of parasitic infections in non-human organisms.

15. The pharmaceutical composition according to claim 14, which is used for the treatment or prevention of parasitic infections in non-human organisms by dripping or pouring the composition onto them.