EP1742609A1 - Formulations liquides applicables par voie dermique, utilisees pour lutter contre des arthropodes parasites chez des animaux - Google Patents

Formulations liquides applicables par voie dermique, utilisees pour lutter contre des arthropodes parasites chez des animaux

Info

Publication number
EP1742609A1
EP1742609A1 EP05730058A EP05730058A EP1742609A1 EP 1742609 A1 EP1742609 A1 EP 1742609A1 EP 05730058 A EP05730058 A EP 05730058A EP 05730058 A EP05730058 A EP 05730058A EP 1742609 A1 EP1742609 A1 EP 1742609A1
Authority
EP
European Patent Office
Prior art keywords
spp
group
animals
carbon atoms
dinotefuran
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Withdrawn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
EP05730058A
Other languages
German (de)
English (en)
Inventor
Kirkor Sirinyan
Andreas Turberg
Thomas Bach
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 Intellectual Property GmbH
Original Assignee
Bayer Healthcare 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 Healthcare AG filed Critical Bayer Healthcare AG
Publication of EP1742609A1 publication Critical patent/EP1742609A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • 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
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the present invention relates to dermal-administrable liquid formulations comprising synthetic or natural pyrethroids and halogen-free guanidines for controlling parasitic arthropods on animals.
  • topical formulations comprising the pyrethroid active ingredient permethrin ((3-phenoxyphenyl) methyl 3- (2,2-dichloroethenyl) -2,2-dimethylcyclopropanecarboxylate, CAS No. [52645-53-1]) for controlling parasitic anthropodes Animals are known (see eg WO 95/17090, JP-07 247 203, EP-A-567368, EP-A-461 962, US-5236954, US-A-5 074 252 and WO 02/087 338).
  • Halogen-free guanidines for controlling parasitic insects are also known (see US 5,434,181 and US 5,532,365). These are preferably tetrahydro-3-furanyl! ethylamino derivatives of the general formula (I)
  • X *, X ⁇ , ⁇ 3 ' 5 ⁇ 4 ⁇ ⁇ 5 ? ⁇ 6 unc j ⁇ 7 each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
  • P represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 carbon atoms, a benzyl group, an alkoxyalkyl group having 2 to 4 carbon atoms (in the whole group), an alkoxycarbonyl group having 1 to 3 • carbon atoms in the alkoxy part, a phenoxycarbonyl group, an alkylcarbonyl group having 1 to 6 carbon atoms in its alkyl part, an alkenylcarbonyl group having 2 to 3 carbon atoms in its alkenyl part, a benzoyl group substituted by 1 to 3 alkyl group (s) having 1 to 4 carbon atoms, a benzoyl group substituted by 1 to 3 halogen atom (s), a 2-furanylcarbonyi group or an N, N-dimethylcarb-.
  • R 1 represents a hydrogen atom, an amino group, a methyl group, an alkylamino group having 1 to 5 carbon atoms, a disubstituted alkylamino group having 2 to 5 carbon atoms (in the entire group), a 1-pyrrolidinyl group, an alkenylamino group having 3 carbon atoms, an alkynylamino group 3 carbon atoms, a methoxyamino group, an alkoxyalkylamino group having 2 to 4 carbon atoms (in the entire group), a methylthio group or -N (Y) ⁇ 2 (wherein
  • Y is an alkoxycarbonyl group having 1 to 3 carbon atoms in its alkoxy part, a phenoxycarbonyl group, an alkylcarbonyl group having 1 to 6 carbon atoms in its alkyl part, an alkenylcarbonyl group having 2 to 3 carbon atoms in its alkenyl part, a cycloalkylcarbonyl group having 3 to 6 carbon atoms in its cycloalkyl part a benzoyl group, a benzoyl group substituted by 1 to 3 alkyl group (s) having 1 to 4 carbon atoms, a benzoyl group substituted by 1 to 3 halogen atoms (e), a 2-furanylcarbonyl group, an N, N-dimethylcarbamoyl group, a (tetrahydro 3-furanyl) methyl group or a benzyl group and
  • Y 1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
  • R 1 and R 1 together with the atoms to which they are attached can form a 5- to 7-membered saturated or unsaturated heterocycle containing another 1 or 2 identical or different heteroatoms or hetero groups selected from N-alkyl of 1 to 5 Carbon atoms, NH, O, and S may contain, and
  • R1 preferably represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • R 1 is preferably an alkyl group having 1 to 3 carbon atoms, the amino group (NH 2 ), a monoalkylamino group having 1 to 3 carbon atoms in the alkyl part, a disubstituted alkylamino group having 2 to 5 carbon atoms (in the whole group).
  • R * and R ⁇ together with the atoms to which they are attached form a heterocycle this is preferably a saturated 5- or 6-membered heterocycle with further 1 or 2
  • R 1 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 3 carbon atoms;
  • XX 2 , X 3 , ⁇ 4 and ⁇ 5 each represent a hydrogen atom and X and X? each represents a methyl group;
  • R * represents a hydrogen atom
  • R.2 represents a methylamino group or a dimethylamino group
  • X 1, X 2, X 3, X 4, X5, X5, and X? represent a methyl group
  • Rl represents a hydrogen atom
  • R 2 represents a methylamino group
  • Z CH-NO 2 .
  • ⁇ l, X 2 , X 3 , ⁇ , ⁇ 5 ⁇ ⁇ 6 and X ⁇ each represent a hydrogen atom or
  • ⁇ l, X 2 , X 3 , X 4 , ⁇ 5 and X> each represents a hydrogen atom and X 'represents a methyl group;
  • Rl represents a hydrogen atom
  • R 2 represents a methylamino group
  • X 3 , X ⁇ , ⁇ 5, ⁇ 6 d X? each represent a hydrogen atom or
  • X *, X 2 , X 3 , ⁇ , ⁇ 5 and X> each represents a hydrogen atom and X ⁇ represents a methyl group;
  • R 1 and ⁇ 1 simultaneously represent an alkoxycarbonyl group having 1 to 3 carbon atoms in their alkoxy part, an alkylcarbonyl group having 1 to 6 carbon atoms in their alkyl part, an alkenylcarbonyl group having 2 to 3 carbon atoms in its alkenyl part, a cycloalkylcarbonyl group having 3 to 6 carbon atoms in its cycloalkyl part, a benzoyl group, a benzoyl group substituted by 1 to 3 alkyl group (s) having 1 to 4 carbon atoms, a benzoyl group substituted by 1 to 3 halogen atom (s), a 2-furanylcarbonyl group or an N, N-dimethylcarbamoyl group,
  • Y 2 is a methyl group
  • ⁇ l, X2, X3, X4, ⁇ 5 ⁇ ⁇ 6 and X? each represent a hydrogen atom or
  • ⁇ l, X 2 , X 3 , X ⁇ , ⁇ 5 and X> each represent a hydrogen atom and X ⁇ represents a methyl group;
  • R * and ⁇ l are simultaneously an alkylcarbonyl group having 1 to 4 carbon atoms in their alkyl part or a cyclopropylcarbonyl group and Y 2 represents a methyl group;
  • ⁇ 6 and ⁇ 7 each represent a hydrogen atom or
  • ⁇ l, X 2 , X 3 , ⁇ , X ⁇ and X ⁇ each represent a hydrogen atom and X? represents a methyl group;
  • R * represents an alkylcarbonyl group having 1 to 4 carbon atoms in its alkyl portion
  • R 2 represents a dimethylamino group
  • Pyrethroids and pyrethroids for example those with common names such as fenvalerate [ ⁇ - (p-Cl-phenyl) -isovaleric acid], are to be emphasized as suitable pyrethroid active substances.
  • ⁇ -cyano-3-phenoxybenzylester flumethrin [3- [2- (4-chlorophenyl) -2-chlorovinyl] -2,2-dimethylcyclopropanecarboxylic acid ( ⁇ -cyano-4-fluoro-3-phenoxy ) benzyl ester] and its enantiomers and stereoisomers, cyfluthrin [2,2-dimethyl-3 - (2,2-dichlorovinyl) - ( ⁇ -cyano-4-fluoro-3-phenoxy) -benzyl ester], permethrin [3-Phenoxybenzylcis, trans 3- (2,2-dichloromethyl) -2,2-dimethylcyclopropane carboxylate],
  • esters such as esters of ⁇ -cyano-3-phenylbenzyl alcohols or 4-fluoro- ⁇ -cyano-3-phenoxybenzyl alcohols are particularly preferred.
  • Very particularly preferred active substances according to the invention are permethrin and flumethrin.
  • Pyrethrum extract can be used. Of these, etofenprox is particularly preferred.
  • Spot-on formulations based on halogen-free guanidines generally have good flea efficacy at higher application rates (> 15 mg active substance / kg body weight). However, they have the disadvantage that they are ineffective against ticks.
  • Synthetic pyrethroids such as e.g. Permethrin, flumethrin or deltamethrin are strongly aprotic compounds while agonists and antagonists of nicotinergic acetylcholine receptors, especially the dinotefuran analogs, are protic compounds. It is therefore not easy to find a dermal liquid formulation which contains both active ingredients and has the following properties:
  • the object of the present invention was therefore to provide a skin and environmentally friendly, user-friendly, against parasitizing arthropods, especially against ticks and fleas, effective formulation for dermal application, containing a
  • the present invention relates
  • the percentages by weight are based on the total weight.
  • dinotefuran and / or dinotefuran analogs is meant in particular the compounds of the formula (I) described above.
  • Pigthroid active ingredient are in particular the compounds mentioned above under this term.
  • compositions according to the invention additionally comprise:
  • compositions of the invention are usually liquid and are suitable for dermal application, in particular as so-called pour-on or spot-on formulations.
  • Very particularly preferred pyrethroids are permethrin or flumethrin.
  • the preferred amount of flumethrin used is in the range 0.2 to 1.0 wt .-%.
  • the permethrin levels in the composition according to the invention can be varied widely between 35 and 60% by weight. Preference is given to amounts in the range 45-60% by weight, more preferably the agent according to the invention contains permethrin in the range 47.5-55% by weight.
  • the preferred isomer mixture consists of 35-45% by weight of cis- and 55-65% by weight of trans-permethrin.
  • the particularly preferred isomer mixture consists of 37.5-42.5% by weight of cis- and 57.5-62.5% by weight of trans-permethrin.
  • dinotefuran or dinotefuran analog can be varied as broadly between 7.5 to 30 wt%, with amounts in the range 10.0 to 25.0 wt% being preferred. Particular preference is given to using dinotefuran or the dinotefuran analog in the inventive compositions in amounts in the range from 12.5 to 20% by weight.
  • formulations may contain other suitable active ingredients.
  • growth inhibiting agents and synergists e.g. Pyridoxyfen ⁇ 2- [l-methyl-2- (4-phenoxyphenoxy) -ethoxy] -pyridines CAS No .: 95737-68-1 ⁇ , methoprene [(E, E) -l-methylethyl-l-methoxy-3 , 7, ll-trimethyl-2,4-dodecadienoate CAS No .: 40596-69-8] and triflumuron ⁇ 2-chloro-N - [[[4- (trifluoromethoxy) phenyl] amino] carbonyl] benzamide CAS No .:
  • antioxidants can be varied widely in the range 0-0.5% by weight, with amounts in the range 0.05-0.25% by weight being preferred. Amounts in the range 0.05-0.15 wt .-% are particularly preferably used for the preparation of the inventive compositions. All the usual antioxidants are suitable, preferably phenolic antioxidants, e.g.
  • the amount of organic acid can be varied widely in the range 0-0.5 wt%, with amounts in the range 0.05-0.25 wt% being preferred. Quantities in the range of 0.05-0.15% by weight are used with particular preference for the preparation of the agents according to the invention.
  • Suitable for use in the compositions of the invention are all pharmaceutically acceptable organic acids, in particular carboxylic acids, such as citric acid, tartaric acid, lactic acid, succinic acid and malic acid. Most preferably, the organic acids are citric acid and malic acid. Most preferred is citric acid.
  • Their amount can be varied in particular in the range 0.05 to 0.25 wt .-% wide. The amounts in the range from 0.075 to 0.15% by weight are again particularly preferred.
  • the amounts of di- or triglycerides can be varied widely in the range 2.5-10% by weight, amounts in the range 2.0-10% by weight being preferred. Amounts in the range 2.5 to 7.5 wt .-% are particularly preferably used in the inventive compositions.
  • Preferred solvents are organic solvents having a boiling point> 80 ° C and a flame point> 75 ° C into consideration. Preference is given to the solvents which have a spreading effect.
  • higher-boiling aromatic alcohols such as benzyl alcohol, N-methylpyrrolidone, 2-pyrrolidone, n-octylpyrrolidone, aromatic esters, such as
  • ethers or polyethers are suitable, for example, from the series of diethylene glycol monoethyl ether, dipropylene glycol monomethyl ether, tetrahydrofurfuryl alcohol and tetrahydrofurfuryl ethoxylate, the latter two being particularly preferred.
  • N-methylpyrrolidone benzyl alcohol, tetrahydrofurfuryl alcohol and mixtures thereof are preferably used to prepare the agents according to the invention.
  • the spreading agents used are in particular fatty acid esters and triglycerides.
  • fatty acid esters and triglycerides isopropyl myristate, Miglyol 810, Miglyol 812, Miglyol 818, Miglyol 829, Miglyol 840 and Miglyol 8810 (for the definition of
  • Miglyols see, for example, H.P. Fiedler Lexicon of adjuvants for pharmacy, cosmetics and adjacent areas, pages 1008-1009, Vol. 2, Edito Cantor Verlag Aulendorf (1996)).
  • compositions of the invention may contain other conventional pharmaceutically acceptable excipients. Examples which may be mentioned as such are: spreading agents and surfactants.
  • Spreading agents are, for example, spreading oils such as adipic acid di-2-ethylhexyl ester, isopropyl myristate, dipropylene glycol pelargonate, cyclic and acyclic silicone oils such as Dimetikone and also their co- and terpolymers with ethylene oxide, propylene oxide and formalin, fatty acid esters, triglycerides, fatty alcohols.
  • spreading oils such as adipic acid di-2-ethylhexyl ester, isopropyl myristate, dipropylene glycol pelargonate, cyclic and acyclic silicone oils such as Dimetikone and also their co- and terpolymers with ethylene oxide, propylene oxide and formalin, fatty acid esters, triglycerides, fatty alcohols.
  • said formulations can be modified with surfactants in a manner known per se.
  • nonionic surfactants e.g. polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ethers;
  • ampholytic surfactants such as di-Na-N-lauryl- ⁇ -iminodipropionate or lecithin;
  • anionic surfactants such as Na lauryl sulfate, fatty alcohol ether sulfates, mono / dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt;
  • cationic surfactants such as cetyltrimethylammonium chloride.
  • compositions of the invention can be prepared by conventional methods, for example by mixing the active ingredients with stirring with the other ingredients and preparing a solution. This can optionally be filtered.
  • plastic tubes are suitable for filling.
  • the ectoparasiticidal activity of the agents according to the invention containing pyrethroids in combination with dinotefuran or a dinotefuran analogue is surprisingly higher than expected from the effects of the individual components.
  • the application rates of active ingredient can be reduced and the long-term effect can be increased. Their application therefore brings economic and environmental benefits.
  • the agents according to the invention are outstandingly suitable for use in parasite control.
  • Anoplura e.g. Haematopinus spp., Linognathus spp., Solenopotes spp., Pediculus spp., Pthirus spp .;
  • Haematobia spp. Stomoxys spp., Fannia spp., Glossina spp., Lucilia spp., Calliphora spp., Auchmeromyia spp., Cordylobia spp., Cochliomyia spp., Chrysomyia spp., Sarcophaga spp., Wohlfartia spp., Gasterophilus spp , Oesteromyia spp., Oedemagena spp., Hypoderma spp., Oestrus spp., Rhinoestrus spp., Melophagus spp., Hippobosca spp.
  • siphonaptera e.g. Ctenocephalides spp., Echidnophaga spp., Ceratophyllus spp., Pulex spp.
  • mesostigmata e.g. Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp.
  • astigmata e.g. Acarus spp., Myocoptes spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Neoknemidocoptes spp.
  • compositions of the invention are particularly suitable for controlling ectoparasites, usually arthropods, z. Insects or arachnids (such as mites or ticks), preferably of ticks and / or fleas, on animals, preferably warm-blooded animals, in particular mammals.
  • the agents according to the invention are preferably used in small animals.
  • Small animals are understood to mean, in particular, dogs, cats and other warm-blooded animals that are no larger than dogs; i.e. they have a body weight of usually not more than 90 kg, preferably not more than 50 kg.
  • the agents according to the invention were particularly preferably used in dogs and cats, in particular in dogs.
  • the effect of the agents according to the invention optionally not only directly on the animal but also in a corresponding extent in their environment.
  • liquid formulations according to the invention are distinguished by their excellent storage stability of at least three years in all climatic zones. Because of the very good
  • Application volumes are 0.1-0.35 ml / 1.0 kg [body weight of the animal to be treated], preferably 0.15-0.25 ml / 1.0 kg [body weight of the animal to be treated].
  • compositions according to the invention are furthermore excellently tolerated by the skin and have a low toxicity.
  • a homogeneous spot-on solution consisting of 45 g of permethrin with 40% cis and 60% trans isomer 24 g of dinotefuran
  • a homogeneous spot-on solution consisting of 45 g of permethrin with 40% cis and 60% trans isomer content 20 g of dinotefuran 124.8 g of N-methylpyrrolidone 0.1 g of citric acid 0.1 g of BHT (butylhydroxytoluene) 10.0 g Miglyol 812 from the company Sasol Germany GmbH, D-58453 Witten
  • the animals After counting the fleas, the animals are treated. The dogs of the control group are not treated.
  • the drugs to be tested are dermal administered to the animals as spot-on at an application level of 0.2 ml / kg body weight. The application takes place once on
  • a formulation is considered to be highly effective if, on day 1 and on the second day after reinfestation, an efficacy> 95% is established and this effect persists for at least 3-4 weeks.
  • control group BG treatment group
  • the animals After counting the ticks, the animals are treated. The dogs of the control group are not treated.
  • the drugs to be tested are dermal administered to the animals as spot-on. The application takes place once on day 0. Only clinically healthy animals are used.
  • Results are recorded in the raw data. On day 2, all live and dead ticks are removed from the dog.
  • a formulation is considered to be highly effective if efficacy> 90% is determined on day 2 and on the second day after reinfestation and this effect persists for at least 3 weeks.
  • control group BG treatment group

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Dermatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Furan Compounds (AREA)

Abstract

L'invention concerne des formulations liquides applicables par voie dermique, qui contiennent des pyréthroïdes synthétiques ou naturels et des guanidines exemptes d'halogène, qui s'utilisent pour lutter contre des arthropodes parasites chez des animaux.
EP05730058A 2004-04-28 2005-04-18 Formulations liquides applicables par voie dermique, utilisees pour lutter contre des arthropodes parasites chez des animaux Withdrawn EP1742609A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004020721A DE102004020721A1 (de) 2004-04-28 2004-04-28 Dermal applizierbare flüssige Formulierungen zur Bekämpfung von parasitierenden Insekten an Tieren
PCT/EP2005/004109 WO2005105034A1 (fr) 2004-04-28 2005-04-18 Formulations liquides applicables par voie dermique, utilisees pour lutter contre des arthropodes parasites chez des animaux

Publications (1)

Publication Number Publication Date
EP1742609A1 true EP1742609A1 (fr) 2007-01-17

Family

ID=34963670

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05730058A Withdrawn EP1742609A1 (fr) 2004-04-28 2005-04-18 Formulations liquides applicables par voie dermique, utilisees pour lutter contre des arthropodes parasites chez des animaux

Country Status (18)

Country Link
US (1) US20070259834A1 (fr)
EP (1) EP1742609A1 (fr)
JP (1) JP5523668B2 (fr)
AR (1) AR048701A1 (fr)
AU (1) AU2005237224B2 (fr)
BR (1) BRPI0510383A (fr)
CA (1) CA2564234C (fr)
DE (1) DE102004020721A1 (fr)
GT (1) GT200500094A (fr)
MX (1) MX271331B (fr)
NO (1) NO20065451L (fr)
NZ (1) NZ550834A (fr)
PE (1) PE20060025A1 (fr)
SV (1) SV2006002097A (fr)
TW (1) TW200605786A (fr)
UY (1) UY28866A1 (fr)
WO (1) WO2005105034A1 (fr)
ZA (1) ZA200608831B (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2008013846A (es) * 2006-04-28 2009-01-20 Summit Vetpharm Llc Insecticidas topicos de alta concentracion que contienen piretroides.
US8367088B2 (en) * 2009-10-08 2013-02-05 Sergeant's Pet Care Products, Inc. Liquid pest control formulation
JP2011153129A (ja) * 2009-12-28 2011-08-11 Sumitomo Chemical Co Ltd 動物外部寄生虫防除組成物
US8871806B2 (en) 2012-06-06 2014-10-28 Sergeant's Pet Care Products, Inc. Methods for preventing flea allergy dermatitis in companion animals
US9622478B2 (en) 2012-10-16 2017-04-18 Solano S.P. Ltd. Topical formulations for treating parasitic infestations
EP2967039A4 (fr) * 2013-03-14 2016-08-31 Sergeants Pet Care Prod Inc Composition antiparasitaire à application localisée ("spot-on") comprenant un néonicotinoïde et un pyréthroïde
JP5791776B1 (ja) * 2014-05-22 2015-10-07 住友商事株式会社 局所用液状殺虫剤組成物
EP3120846A1 (fr) 2015-07-24 2017-01-25 Ceva Sante Animale Compositions et leurs utilisations pour lutter contre les ectoparasites chez des mammifères non humains
WO2017187435A1 (fr) 2016-04-24 2017-11-02 Solano S.P. Ltd. Traitement liquide à base de dinotéfurane contre les puces et tiques
CN106212495A (zh) * 2016-07-26 2016-12-14 广州市白蚁防治所 农药组合物及其制备方法和应用
WO2019166649A1 (fr) * 2018-03-01 2019-09-06 Ceva Sante Animale Compositions vétérinaires pour lutter contre les moustiques
WO2021028479A1 (fr) 2019-08-14 2021-02-18 Vetoquinol S.A. Compositions comprenant du tigolaner pour lutter contre des parasites

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004064522A1 (fr) * 2003-01-17 2004-08-05 Bayer Healthcare Ag Répulsif

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5074252A (en) * 1988-03-25 1991-12-24 Morgan Jr Charles Rechargeable insecticide dispenser providing controlled release of an insecticide composition
DE69126776T2 (de) * 1990-03-05 1998-01-08 Mallinckrodt Veterinary, Inc., Terre Haute, Ind. Parasitizide zusammensetzung und verfahren zu ihrer herstellung und ihre verwendung
FR2689729B1 (fr) * 1992-04-09 1994-06-03 Roussel Uclaf Nouvelles compositions pesticides renfermant un pyrethrinouide.
JP2766848B2 (ja) * 1993-10-26 1998-06-18 三井化学株式会社 フラニル系殺虫剤
US6267947B1 (en) * 1993-12-23 2001-07-31 Sun Glitz Corporation Water resistant pesticide composition
JP3580591B2 (ja) * 1995-02-17 2004-10-27 三井化学株式会社 殺虫組成物
JP4324308B2 (ja) * 2000-04-26 2009-09-02 住友化学株式会社 ハエ類の防除方法
US6660690B2 (en) * 2000-10-06 2003-12-09 Monsanto Technology, L.L.C. Seed treatment with combinations of insecticides
US20020103233A1 (en) * 2000-11-30 2002-08-01 Arther Robert G. Compositions for enhanced acaricidal activity
DE10117676A1 (de) * 2001-04-09 2002-10-10 Bayer Ag Dermal applizierbare flüssige Formulierungen zur Bekämpfung von parasitierenden Insekten an Tieren
DE10320505A1 (de) * 2003-05-08 2004-11-25 Bayer Healthcare Ag Mittel zum Bekämpfen von Parasiten an Tieren

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004064522A1 (fr) * 2003-01-17 2004-08-05 Bayer Healthcare Ag Répulsif

Also Published As

Publication number Publication date
TW200605786A (en) 2006-02-16
JP5523668B2 (ja) 2014-06-18
NO20065451L (no) 2006-11-27
NZ550834A (en) 2011-11-25
AU2005237224A1 (en) 2005-11-10
BRPI0510383A (pt) 2007-11-06
CA2564234A1 (fr) 2005-11-10
ZA200608831B (en) 2008-05-28
JP2007534714A (ja) 2007-11-29
GT200500094A (es) 2005-12-23
MXPA06012295A (es) 2007-01-31
DE102004020721A1 (de) 2005-11-24
CA2564234C (fr) 2013-03-12
AR048701A1 (es) 2006-05-17
MX271331B (es) 2009-10-29
UY28866A1 (es) 2005-11-30
WO2005105034A1 (fr) 2005-11-10
SV2006002097A (es) 2006-03-15
AU2005237224B2 (en) 2010-11-04
US20070259834A1 (en) 2007-11-08
PE20060025A1 (es) 2006-03-22

Similar Documents

Publication Publication Date Title
EP1379138B1 (fr) Formulations liquides a application cutanee pour lutter contre des insectes parasites sur des animaux
EP1742609A1 (fr) Formulations liquides applicables par voie dermique, utilisees pour lutter contre des arthropodes parasites chez des animaux
EP1587368B1 (fr) Repulsif
EP2104428B1 (fr) Produit de combinaison destiné à la lutte contre les parasites chez l'animal
EP1624756B1 (fr) Agents pour lutter contre des parasites des animaux
US20060111323A1 (en) Use of polysiloxanes having quaternary ammonium groups as formulation auxiliaries, and compositions comprising them
US11278022B2 (en) Spot-on active substance formulation
EP2725899B1 (fr) Produit de lutte antiparasitaire pour les animaux

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20061128

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR

DAX Request for extension of the european patent (deleted)
RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: BAYER ANIMAL HEALTH GMBH

17Q First examination report despatched

Effective date: 20090826

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: BAYER INTELLECTUAL PROPERTY GMBH

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: GRANT OF PATENT IS INTENDED

RIC1 Information provided on ipc code assigned before grant

Ipc: A61K 47/22 20060101ALI20170920BHEP

Ipc: A61K 47/10 20170101ALI20170920BHEP

Ipc: A61K 9/08 20060101AFI20170920BHEP

Ipc: A61K 47/12 20060101ALI20170920BHEP

INTG Intention to grant announced

Effective date: 20171020

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20180301