EP1311491A1 - Verwendung von triazintrion-sulfonen zur bekämpfung von coccidiosen - Google Patents

Verwendung von triazintrion-sulfonen zur bekämpfung von coccidiosen

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Publication number
EP1311491A1
EP1311491A1 EP01956583A EP01956583A EP1311491A1 EP 1311491 A1 EP1311491 A1 EP 1311491A1 EP 01956583 A EP01956583 A EP 01956583A EP 01956583 A EP01956583 A EP 01956583A EP 1311491 A1 EP1311491 A1 EP 1311491A1
Authority
EP
European Patent Office
Prior art keywords
weight
concentrations
compounds
formula
particularly preferably
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01956583A
Other languages
German (de)
English (en)
French (fr)
Inventor
Gisela Greif
Iris Heep
Hans-Christian Mundt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Animal Health GmbH
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1311491A1 publication Critical patent/EP1311491A1/de
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C07D251/34—Cyanuric or isocyanuric esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis

Definitions

  • the present invention relates to the use of special derivatives of triazinetrions for combating coccidiosis in animals.
  • Coccidiosis are common infections in animals, e.g. Subclinical infections in pigs caused by protozoa of the genera Coccidia, Sarcosporidia and Toxoplasmas are common worldwide.
  • Isospora suis infections for example, have only been recognized as the cause of piglet diarrhea in recent years and have been intensively researched. As a rule, infection occurs from the
  • R 1 represents haloalkyl
  • R 2 represents alkyl, alkoxy, halogen or SO 2 N (CH 3 ) 2 , and their physiologically tolerable salts have a very good coccidiocidal activity with surprisingly low mammalian toxicity.
  • the compounds of formula (I) can be obtained by the processes known from DE-OS 27 18 799, 25 090 37, 25 323 63, 24 137 22, WO 99/62519.
  • R 1 represents C 1 -C 5 -haloalkyl having 1 to 5 halogen atoms
  • R 2 represents C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen or SO 2 N (CH 3 ) 2 , and their physiologically tolerable salts.
  • R 1 represents C 1 -C 5 -alkyl with 1 to 5 halogen atoms
  • R 2 represents -C-alkyl, and their physiologically tolerable salts.
  • R 1 represents Ci-C 4 perhaloalkyl
  • R 2 represents methyl or ethyl, and their physiologically tolerable salts.
  • the use of the compound of the formula is particularly preferred
  • the compounds of the formula (I) can optionally be present as geometric and / or optical isomers or regioisomers or their isomer mixtures in different compositions. Both the use of the pure isomers and the isomer mixtures are claimed according to the invention.
  • Preferred, particularly preferred or very particularly preferred, etc. are compounds which carry the substituents mentioned under preferred, particularly preferred or very particularly preferred, etc.
  • haloalkyl radicals given in the definition for R 1 , including those which are preferred, particularly preferred and very particularly preferred, the fluoroalkyl radicals are again preferred.
  • the compounds according to the invention can be brought into all customary formulations and administered in various application forms. Oral applications are preferred, in particular application as an oral aqueous suspension.
  • Preferred dosages are 1-500 mg of active ingredient per kg of body weight of the animal to be treated, doses of 10 to 200 mg / kg are particularly preferred and doses of 20-100 mg / kg are very particularly preferred.
  • Preparations suitable for animals are:
  • Solutions such as solutions for injection, oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pour-on formulations, gels;
  • Emulsions and semi-solid preparations for oral or cutaneous use and for injection are, for example, suspensions, pastes.
  • solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; Aerosols and inhalants.
  • Solutions for injection are administered intravenously, intramuscularly and subcutaneously.
  • Injection solutions are prepared by dissolving the active ingredient in a suitable solvent and possibly adding additives such as solubilizers, acids, bases, buffer salts, antioxidants, preservatives.
  • the solutions are sterile filtered or if necessary prepared and filled aseptically.
  • the active compounds can also be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.
  • solubilizers solvents which require the active ingredient to be dissolved in the main solvent or prevent it from precipitating.
  • solvents which require the active ingredient to be dissolved in the main solvent or prevent it from precipitating.
  • examples are polyvinyl pyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan esters.
  • Preservatives are, for example: benzyl alcohol, trichlorobutanol, p-
  • Hydroxybenzoic acid esters n-butanol, and organic acids with preserving properties such as benzoic acid, propionic acid or sorbic acid and their salts.
  • the preservatives can optionally also be used as a combination of two or more agents.
  • Oral solutions are applied directly. Concentrates are used orally after previous dilution to the application concentration. Oral solutions and concentrates are prepared as described above for the injection solutions, whereby sterile work can be dispensed with.
  • Thickeners are: inorganic thickeners such as bentonites, colloidal silica, Alumim 'ummonostearat, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates, xanthans.
  • Gels are applied to or spread on the skin or placed in body cavities. Gels are made by adding enough thickening agent to solutions that have been prepared as described for the injection solutions to form a clear mass with an ointment-like consistency.
  • the thickeners specified above are used as thickeners.
  • Pour-on formulations are poured onto or sprayed onto limited areas of the skin, the active ingredient either penetrating the skin and acting systemically or being distributed over the surface of the body.
  • pour-on formulations are prepared by dissolving, suspending or emulsifying the active ingredient in suitable skin-compatible solvents or solvent mixtures. If necessary, other auxiliaries such as dyes, absorption-promoting substances, antioxidants, light stabilizers and adhesives are added.
  • solvents water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate;
  • Ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol kononobutyl ether, ketones such as acetone, methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, N-methylpyrrolidone, 2,2-dimethyl-4-hydroxy-methyl-l 3-dioxolane. Dyes are all dyes approved for use on animals, which can be dissolved or suspended.
  • Absorbing substances are DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides, fatty alcohols.
  • Antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylated hydroxytoluene, butylated hydroxyanisole, tocopherol.
  • Light stabilizers are e.g. Substances from the class of benzophenones or novantisolic acid.
  • Adhesives are e.g. Cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.
  • Emulsions can be used orally, cutaneously or as an injection.
  • Emulsions are either water in oil or oil in water.
  • emulsifiers emulsifiers
  • auxiliary substances such as dyes, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-increasing substances, homogenized.
  • hydrophobic phase paraffin oils, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic / capric acid biglyceride, triglyceride mixture with vegetable fatty acids of chain length C 8 . 12 or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated, possibly also hydroxyl-containing fatty acids, mono- and diglycerides of C 8 / C 10 fatty acids.
  • Fatty acid esters such as ethyl stearate, di-n-butyryl adipate, lauric acid hexyl ester, dipropylene glycol pelargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C; [6-C ⁇ g, isopropyl myristate, isopropyl pahnitat, caprylic / capric alcoholic esters the chain length C 12 - C 18 , isopropyl stearate, oleic acid oleyl ester, oleic acid decyl ester, ethyl oleate, lactic acid ethyl ester, waxy fatty acid esters such as artificial duckling gland fat, dibutyl phthalate, adipic acid diisopropyl ester, the latter related ester mixtures and others
  • Fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol.
  • Fatty acids such as Oleic acid and its mixtures.
  • hydrophilic phase water, alcohols, e.g. Propylene glycol, glycerin, sorbitol and their mixtures.
  • emulsifiers surfactants (contains emulsifiers and wetting agents), such as
  • non-ionic e.g. polyoxyethylated castor oil, polyoxyethylene sorbitan monooleate, sorbitan monostearate, ethyl alcohol, glycerol monostearate, polyoxyethyl stearate, alkylphenol polylglycol ether,
  • ampholytic such as di-Na-N-lauryl- ⁇ -iminodipropionate or lecithin,
  • anionic such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono / dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt,
  • cationic such as Cetylljrimemylammoniumchlorid.
  • Viscosity-increasing and emulsion-stabilizing substances such as carboxymethyl cellulose, methyl cellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinyl pyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, or colloidal silica Mixtures of the listed substances.
  • Suspensions can be administered orally, cutaneously or as an injection. They are produced by adding the active ingredient in a carrier liquid, optionally with the addition of other auxiliaries such as wetting agents, defoamers, dyes, absorption-promoting substances, suspension stabilizers, preservatives, antioxidants,
  • suspension stabilizers such as e.g. Bentonites and / or xanthans in concentrations of from 0.01 to 5% by weight, particularly preferably from 0.05 to 1% by weight.
  • G optionally acidic or basic substances in the concentrations required to adjust the pH.
  • solvents and homogeneous solvent mixtures listed further above may be mentioned as carrier liquids, provided that they are pharmaceutically acceptable and the active substance or substances are not or only to a small extent therein
  • Loosen dimensions Water is preferably used.
  • Surfactants such as. Can be mentioned as wetting agents (dispersants) for the orally administrable suspensions
  • anionic such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono / dialkyl polyglycol ether orthophosphate monoethanolamine salt, lignin sulfonates or dioctyl sulfosuccinate,
  • cationic such as cetytrimethylammonium chloride
  • ampholytic such as di-Na-N-lauryl- ⁇ -iminodipropionate or lecithin,
  • non-ionic e.g. polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, ethyl alcohol, glycerol monostearate,
  • Defoamers are those based on silicone, for example dimethicone or simethicone.
  • the viscosity-increasing substances listed above can be used, for example, as suspension stabilizers.
  • humectants examples include: propylene glycol, glycerol, sugar alcohols such as sorbitol, sugars such as cane sugar.
  • Suitable preservatives are known to the person skilled in the art; Examples have already been mentioned above.
  • Organic acids with preserving properties are preferably used, such as. B. benzoic acid, propionic acid or
  • Sorbic acid and its salts can also be used as a combination of two or more agents, a preferred example being a combination of sodium propionate and sodium benzoate.
  • customary pharmaceutically acceptable acids, bases and buffers are suitable as acidic or basic substances for adjusting the pH.
  • acids which may be mentioned are: hydrochloric acid, citric acid and tartaric acid.
  • bases which may be mentioned are: alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; Alkali and alkaline earth carbonates such as sodium carbonate and amines, for example mono-, di- or triethanolamine.
  • buffer systems which can be used are those based on phosphate.
  • the pH is preferably in the range from 2 to 10, in particular 3 to 7.
  • the active ingredient is preferably used in the suspensions in micronized form, usually in particle size distributions of 0.1 to 100 ⁇ m, preferably 1 to 50 ⁇ m.
  • the active ingredient is present in a grain size of 10-10 mm and a maximum grain size of 50-10 ⁇ m in a concentration of 0.1-20% by weight,
  • polyacrylic acids with an acrylic acid content of 56 to 68% by weight and a molecular weight of approx. 3-l06, which are neutralized with alkali or alkaline earth bases, are present in a concentration of 0.1-5% by weight,
  • humectants are present in a concentration of 5 to 30% by weight
  • the active ingredient is present in the pastes mentioned preferably in weight concentrations of 5% by weight to 20% by weight, particularly preferably from 10% by weight to 15% by weight.
  • polyacrylic acids used in the pastes mentioned are preferably neutralized with alkali hydroxide or carbonate.
  • Polyacrylic acids are preferred in the formulation according to the invention in weight concentrations of 0.2% to 1% of 0.5% included. These are commercially available and are known in pharmacopoeias, for example under the trade name Carbomer 934 P.
  • the preservatives used in the pastes mentioned are preferably para-hydroxybenzoic acid esters (parabens) such as methyl 4-hydroxybenzoate, ethyl 4-hydroxybenzoate or propyl 4-hydroxybenzoate.
  • parabens such as methyl 4-hydroxybenzoate, ethyl 4-hydroxybenzoate or propyl 4-hydroxybenzoate.
  • the preservatives can be used individually or in combination for adequate preservation. They are usually contained in concentrations of 0.01-0.5% by weight.
  • the pastes mentioned can also contain moisture-retaining agents, e.g. Glycerin or 1,2-propylene glycol.
  • Moisture-retaining agents are used in weight concentrations of 5% to 30%, preferably from 10% to 20%.
  • the active ingredient is present in the pastes mentioned in a grain size of 1 to 10-10 "6 m, preferably from 1 to 5-10" ⁇ m.
  • the maximum grain size is'
  • the paste is obtained by mixing the individual components together.
  • the consistency of the paste can be increased or decreased A pasty consistency is desired, which allows the agent to be administered orally using suitable applicators such as syringes, tubes, spatulas, etc.
  • the active ingredient is mixed with suitable carriers, if appropriate with the addition of auxiliaries, and brought into the desired shape.
  • Inorganic and organic substances serve as such.
  • Inorganic substances are e.g. Common salt, carbonates such as calcium carbonate, hydrogen carbonates, aluminum oxides,
  • Silicas, clays, precipitated or colloidal silicon dioxide, phosphates are, for example, sugar, cellulose, food and feed such as milk powder, animal meal, cereal meal and meal, starches.
  • Excipients are preservatives, antioxidants, dyes, which have already been listed above.
  • auxiliaries are lubricants and lubricants such as Magnesium stearate, stearic acid, talc, bentonite, decomposition substances such as starch or cross-linked polyvinylpyrrolidone, binders such as e.g. Starch, gelatin or linear polyvinylpyrrolidone and dry binders such as microcrystalline cellulose.
  • lubricants and lubricants such as Magnesium stearate, stearic acid, talc, bentonite, decomposition substances such as starch or cross-linked polyvinylpyrrolidone, binders such as e.g. Starch, gelatin or linear polyvinylpyrrolidone and dry binders such as microcrystalline cellulose.
  • the active compounds can also be encapsulated in the form of their solid or liquid formulation ranges mentioned above.
  • the active ingredients can also be used in the form of an aerosol.
  • the active ingredient in a suitable formulation is finely distributed under pressure.
  • the active ingredients are preferably administered together with the feed and / or the drinking water.
  • the feed includes single feed of vegetable origin such as hay, beets, cereals, grain by-products, single feed of animal origin such as meat, fats, milk products, bone meal, fish products, as well as the single feed such as vitamins, proteins, amino acids, e.g. DL-methionine, salts such as lime and table salt.
  • the feed also includes supplementary, finished and compound feed. These contain
  • Feed materials in a composition that ensures a balanced diet visibly ensures the energy and protein supply as well as the supply of vitamins, mineral salts and trace elements.
  • the concentration of the active substances in the feed is normally about 0.01 to 500 ppm, preferably 0.1 to 50 ppm.
  • the active ingredients can be added to the feed as such or in the form of premixes or feed concentrates.
  • Premixes and feed concentrates are mixtures of the active ingredient with a suitable carrier.
  • the carrier substances include feed materials or mixtures thereof.
  • They can also contain other tools, such as Substances that regulate fluidity and miscibility, e.g. Silicas, bentonites, lignin sulfonates.
  • Substances that regulate fluidity and miscibility e.g. Silicas, bentonites, lignin sulfonates.
  • antioxidants such as BHT or preservatives such as sorbic acid or calcium propionate can be added.
  • Concentrates for application via drinking water must be formulated in such a way that a clear solution or a stable, homogeneous suspension results when mixed with the drinking water.
  • Fee additives such as sugar or salts (e.g. citrates, phosphates, common salt, sodium carbonate) are therefore suitable as carriers.
  • sugar or salts e.g. citrates, phosphates, common salt, sodium carbonate
  • They can also contain antioxidants and preservatives.
  • the active substances are suitable for combating parasitic protozoa according to the invention which are used in animal husbandry and
  • Animal husbandry occurs in farm, breeding, zoo, laboratory, experimental and hobby animals. They are effective against all or individual stages of development of the pests and against resistant and normally sensitive strains. By combating the parasitic protozoa, illness, deaths and reduced performance (eg in the production of meat, milk, wool, hides, eggs, honey, etc.) are to be reduced, so that the use of the active ingredients enables more economical and easier animal husbandry is.
  • the parasitic protozoa include:
  • Mastigophora such as Trypanosomatidae e.g. Trypanosoma brucei, T. .. gambiense, T. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. si iae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, e.g. Trichomonadidae e.g. Giardia lamblia, G. canis.
  • Trypanosomatidae e.g. Trypanosoma brucei, T. .. gambiense, T. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. si iae, T. viv
  • Sarcomastigophora such as Entamoebidae e.g. Entamoeba histolytica
  • Hartmanellidae e.g. Acanthamoeba sp., Hartmanella sp.
  • Apicomplexa such as Eimeridae e.g. Eimeria acervulina, E. adenoides, E. alabahmensis, E. anatis, E. anseris, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E. canis, E. chinchillae, E. clupearum , E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E.
  • Eimeridae e.g. Eimeria acervulina, E. adenoides, E. alabahmensis, E. anatis, E. anseris, E. arloingi, E. ashata, E. auburnens
  • ovifelis S. spec, S. suihominis such as Leucozoidae such as Leucozytozoon simondi, such as Plasmodiidae such as Pasmodium berghe falciparum, P. malariae, P. ovale, P. vivax, P. spec, such as Piroplasmea, for example Babesia argentina, B. bovis, B. canis, B. spec, Theileria parva, Theileria spec, such as Adeleina, for example Hepatozoon canis, H. spec.
  • Pneumocystis carinii as well as Ciliophora (Ciliata) such as e.g. Balantidium coli, Ichthiophthirius spec., Trichodina spec., Epistylis spec.
  • the compounds according to the invention are also active against protozoa which act as
  • Parasites occur in insects. Parasites of the Microsporida strain, in particular of the genus Nosema, may be mentioned as such. Nosema apis is particularly worth mentioning for the honeybee.
  • Livestock and breeding animals include mammals such as Cattle, horses, sheep, pigs, goats, camels, water buffalos, donkeys, rabbits, fallow deer, reindeer, fur animals such as Mink, chinchilla, raccoon, birds such as Chickens, geese, turkeys,
  • Laboratory and experimental animals include mice, rats, guinea pigs, golden hamsters, dogs and cats.
  • the pets include dogs and cats.
  • the fish include utility, breeding, aquarium and ornamental fish of all ages that live in fresh and salt water.
  • Useful and farmed fish include e.g.
  • the agents according to the invention are particularly suitable for the treatment of fish fry, e.g. Carp 2 to 4 cm in length. The agents are also very suitable for eel fattening.
  • the aim of this study was to test Ponazuril for efficacy against an artificial mixed infection (Eimeria tenella, E. maxima and E. acervulina) in chickens under cage conditions.
  • the infection was moderate to massive.
  • the mortality from coccidiosis was 20% of the control treated with urine.
  • the infection was controlled with all doses and treatment schedules. The degree of control was directly dependent on the dosage and the start of treatment.
  • Starting treatment early reduced the parasitological findings significantly (oocyst excretion and number of lesions) and improved the technical parameters (body weight gain and feed turnover).
  • the highest dose (20 mg ponazuril in the feed) showed the best results. This dose corresponded approximately to a dose of 3.5 mg / kg body weight and day.
  • the aim of the experiments was to compare the effectiveness of toltrazuril and ponazuril against natural infections with pathogens of the Eimeria family.
  • the main parameters used were oocyst excretion and the consistency of the excrement.
  • the weight of the animals was also checked on occasion.
  • the infection pressure was low during the period of the examination. Both toltrazuril and ponazuril were fully effective under the test conditions.
  • suspensions specified below can be prepared by the following methods:
  • the substances are stirred together until a homogeneous suspension is formed and the pH is adjusted to a desired range.
  • the suspension stabilizer bentonite or sodium alginate is optionally used at approx.
  • the suspension can be filled into suitable containers.
  • the pH is adjusted to 3.4 to 4.2 by appropriate dosing of citric acid.
  • the bentonite is preferably first heated to 80 ° C in aqueous suspension and after swelling with the others

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicinal Preparation (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP01956583A 2000-08-17 2001-08-06 Verwendung von triazintrion-sulfonen zur bekämpfung von coccidiosen Withdrawn EP1311491A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10040174A DE10040174A1 (de) 2000-08-17 2000-08-17 Verwendung von Triazintrion-Sulfonen zur Bekämpfung von Coccidiosen
DE10040174 2000-08-17
PCT/EP2001/009060 WO2002014288A1 (de) 2000-08-17 2001-08-06 Verwendung von triazintrion-sulfonen zur bekämpfung von coccidiosen

Publications (1)

Publication Number Publication Date
EP1311491A1 true EP1311491A1 (de) 2003-05-21

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EP01956583A Withdrawn EP1311491A1 (de) 2000-08-17 2001-08-06 Verwendung von triazintrion-sulfonen zur bekämpfung von coccidiosen

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US (1) US7915257B2 (pt)
EP (1) EP1311491A1 (pt)
JP (1) JP2004506624A (pt)
KR (1) KR100803078B1 (pt)
CN (3) CN1469868A (pt)
AR (1) AR030378A1 (pt)
AU (2) AU7852201A (pt)
BR (1) BR0113268A (pt)
CA (1) CA2419471C (pt)
CZ (1) CZ300020B6 (pt)
DE (1) DE10040174A1 (pt)
HR (1) HRP20030194A2 (pt)
HU (1) HUP0303701A3 (pt)
MX (1) MXPA03001429A (pt)
MY (1) MY136518A (pt)
NO (1) NO20030585D0 (pt)
NZ (1) NZ524200A (pt)
PL (1) PL359709A1 (pt)
SK (1) SK1652003A3 (pt)
TW (1) TW200819431A (pt)
WO (1) WO2002014288A1 (pt)
YU (1) YU11703A (pt)
ZA (1) ZA200301225B (pt)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010102762A1 (de) 2009-03-10 2010-09-16 Bayer Animal Health Gmbh Zubereitung auf ölbasis enthaltend anti-protozoische triazine und anthelmintische cyclodepsipeptide

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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