US20040029960A1 - Anthelminthic for the prevention of parasitic infections in human and animals - Google Patents

Anthelminthic for the prevention of parasitic infections in human and animals Download PDF

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Publication number
US20040029960A1
US20040029960A1 US10/311,418 US31141803A US2004029960A1 US 20040029960 A1 US20040029960 A1 US 20040029960A1 US 31141803 A US31141803 A US 31141803A US 2004029960 A1 US2004029960 A1 US 2004029960A1
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alkyl
optionally substituted
compounds
formula
different
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Inventor
Achim Harder
Georg Samson-Himmelstjerna
Bernd-Wieland Kruger
Heinz Mehlhorn
Jurgen Schmidt
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Saltigo GmbH
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Individual
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Assigned to BAYER AKTIENGESELLSCHAFT reassignment BAYER AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MEHLHORN, HEINZ, SCHMIDT, JURGEN, WON SAMSON-HIMMELSTJERNA, GEORG, KRUGER, BERND-WIELAND, HARDER, ACHIM
Publication of US20040029960A1 publication Critical patent/US20040029960A1/en
Assigned to SALTIGO GMBH reassignment SALTIGO GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BAYER AKTIENGESELLSCHAFT
Priority to US12/117,939 priority Critical patent/US8501775B2/en
Abandoned legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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
    • A61P33/10—Anthelmintics
    • A61P33/12—Schistosomicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/34—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms

Definitions

  • the present invention relates to compositions comprising certain active compounds which are suitable as repellents, and to their use for preventing an infection of humans or of animals by the infectious stages of parasitic flatworms (platyhelminths).
  • the compositions are used on the skin against the flatworm stages which are capable of penetrating through the skin into the host organism (cercariae).
  • hexachlorophene has a lethal effect on cercariae of Schistosoma mansoni (Fripp, P. J. and Armstrong, F. I., The efficacy of hexachlorophene skin cleanser as a cercariae repellent. South African Med. J. 47: 1973, 526-527). Because of health risks, in particular liver damage, hexachlorophene cannot be used on the skin of humans. It is toxic on contact with the skin and when swallowed, may possibly cause deformities and is possibly carcinogenic [Commission of the European Community, Directive 93/72/EEC of Sep. 1, 1993, Annex Vol. I and II (EU Directive on Dangerous Substances) with amendments to 1999, Official Journal EUL258A, Volume 36, Oct. 16, 1993, Amendments to 1997].
  • Niclosamide acts against the penetration of cercariae [Bruce, J. I. et al. (1992) Efficacy of niclosamide as a potential topical antipenetrant (TAP) against cercariae of Schistosoma mansoni in monkeys. Mem. Inst. Oswaldo Cruz 87:28, 1-289.] but is toxicologically objectionable since it may possibly cause inheritable genetic damage (Registry of Toxic Effects of Chemical Substances, National Institute of Occupational Safety and Health).
  • TEP topical antipenetrant
  • N,N-Diethyl-m-toluamide acts against cercariae of Schistosoma mansoni [Salafsky, B. et al. Evaluation of N,N-diethyl-m-toluamide (DEET) as a topical agent for preventing skin penetration by cercariae of Schistosoma mansoni. Am. J. Trop. Med. Hyg. 58: 1998, 828-834).
  • DEET has some unfavourable properties.
  • compositions according to the invention are suitable for protecting humans and animals effectively against infections by platyhelminths, in particular Schistosoma haematobium, Schistosoma japonicum , Trichobilharzia spp. and Ornithobilharzia spp., but also Echinostoma spp. and others.
  • the invention relates to
  • compositions for deterring helmintic parasites characterized in that they comprise at least one compound of the formula (I)
  • Y represents hydrogen, optionally substituted alkyl or the radical O—X
  • X represents hydrogen, COR 11 , COOR 12 or R 13 ,
  • R 1 represents an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl or cycloalkenyl radical
  • R 2 , R 11 , R 12 and R 13 are identical or different and represent optionally substituted alkyl or alkenyl radicals
  • R 3 to R 10 are identical or different and represent hydrogen or represent optionally substituted alkyl radicals, where R 2 and R 3 or R 3 and R 7 or R 3 and R 5 or R 5 and R 7 together with the atoms to which they are attached may also form an optionally substituted monocyclic ring and
  • n and m are identical or different and are 0 or 1.
  • compositions for deterring helmintic parasites according to item 1, characterized in that they comprise at least one compound of the formula (I)
  • Y represents hydrogen, C 1 -C 6 -alkyl or the radical O—X
  • X represents hydrogen, COR 11 or R 13 ,
  • R 1 represents C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkenyl, C 1 -C 2 -alkyl-C 3 -C 7 -cycloalkyl, C 1 -C 2 -alkyl-C 3 -C 7 -cycloalkenyl, where the cycloalkyl or cycloalkenyl rings of the abovementioned radicals are optionally substituted up to three times by C 1 -C 6 -alkyl or by a C 1 -C 6 -dialkylene bridge, or
  • R 1 represents C 1 -C 7 -alkyl, C 2 -C 7 -alkenyl or C 2 -C 7 -alkinyl,
  • R 2 , R 11 , R 13 are identical or different and represent C-C 6 -alkyl
  • R 3 to R 8 are identical or different and represent hydrogen or C 1 -C 6 -alkyl, where R 2 and R 3 or R 3 and R 7 or R 3 and R 5 or R 5 and R 7 together with the atoms to which they are attached may also form a 5- or 6-membered monocyclic ring and
  • a method for deterring helmintic parasites characterized in that compounds of the formula (I) according to item I are applied to the skin of the organism to be protected.
  • compositions for deterring helminthic parasites characterized in that compounds of the formula (I) according to claim 1 are mixed with extenders and/or surfactants.
  • the substituent Y in the formula (I) represents hydrogen or C 1 -C 6 -alkyl, such as, for example, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl, pentyl or hexyl.
  • R 1 preferably represents C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkenyl, C 1 -C 2 -alkyl-C 3 -C 7 -cycloalkyl, C 1 -C 2 -alkyl-C 3 -C 7 -cycloalkenyl, where the cycloalkyl or cycloalkenyl rings of the abovementioned radicals are optionally substituted up to three times by C 1 -C 6 -alkyl or by a C 1 -C 6 -dialkylene bridge.
  • the compounds of the formula (I) used in the compositions according to the invention are compounds in which
  • Y represents the radical O—X
  • X represents hydrogen, COR 11 , COOR 12 or R 13 ,
  • R 1 represents optionally substituted alkyl, cycloalkyl, alkenyl or alkinyl radicals,
  • R 2 , R 11 , R 12 and R 13 are identical or different and represent optionally substituted alkyl or alkenyl radicals
  • R 3 to R 10 are identical or different and represent hydrogen or represent optionally substituted alkyl radicals, where R 2 and R 3 or R 3 and R 7 or R 3 and R 5 or R 5 and R 7 together with the atoms to which they are attached may also form an optionally substituted monocyclic ring and
  • n and m are identical or different and are 0 or 1.
  • X represents hydrogen, COR 11 or R 13 ,
  • R represents C 1 -C 7 -alkyl, C 3 -C 7 -cycloalkyl, C 2 -C 7 -alkenyl or C 2 -C 7 -alkinyl,
  • R 2 , R 11 , R 13 are identical or different and represent C 1 -C 6 -alkyl
  • R 3 -R 8 are identical or different and represent hydrogen or C 1 -C 6 -alkyl, where R 2 and R 3 or R 3 and R 7 or R 3 and R 5 or R 5 and R 7 together with the atoms to which they are attached may also form a 5- or 6-membered monocyclic ring and
  • X represents hydrogen or R 13 ,
  • R 13 represents C 1 -C 6 -alkyl
  • R 1 represents C 1 -C 7 -alkyl or C 3 -C 7 -alkenyl
  • R 4 to R 8 are identical or different and represent hydrogen or C 1 -C 6 -alkyl
  • R 2 and R 3 together with the atoms to which they are attached form a 5- or 6-membered monocyclic ring
  • n 1 and
  • compositions according to the invention are compounds of the general formula (I) in which
  • Y represents the radical O—X
  • R 1 represents C 1 -C 4 -alkyl or C 5 -C 6 -cycloalkyl
  • R 2 , R 11 and R 13 are identical or different and represent C 1 -C 6 -alkyl, R 3 to R 8 represent hydrogen and X represents hydrogen, COR 11 or R 13 , where R 11 and R 13 are as defined above.
  • the compounds of the general formula (I) are either known, or they can be prepared by generally known methods and processes (cf., for example, Cesare Ferri, Molen der organischen Synthese [Reactions of Organic Synthesis], Georg Thieme Verlag Stuttgart, 1978, p. 223 and p. 450, and also EP A 0 289 842).
  • compositions according to the invention have already been used specifically as repellents on the skin, against insects and ticks.
  • a substantial advantage of using the compounds according to the invention is their high compatibility with the skin, plants and the environment and the generally low toxicity of these compounds.
  • compositions according to the invention now allow simultaneous prevention of platyhelminth infection and protection against mosquitoes, with only one composition. Thus, the necessity for using simultaneously two different, possibly incompatible compositions on the skin is avoided.
  • compositions according to the invention may also comprise all of the customary auxiliaries and additives used in formulations for topical application.
  • the active compounds are administered, either directly or in the form of suitable preparations, dermally or with the aid of shaped articles containing the active compound, such as, for example, strips, plates, tapes, collars, ear tags, limb bands or marking devices.
  • Dermal administration is effected, for example, in the form of bathing, dipping, spraying, pouring-on or spotting-on, washing, shampooing, or powdering.
  • Suitable preparations include:
  • solutions or concentrates for administration after dilution solutions for use on the skin, pour-on formulations, gels;
  • solid preparations such as powders, shaped articles containing the active compound.
  • Solutions for use on the skin are applied drop by drop, brushed on, rubbed in, splashed on or sprayed on, or applied by dipping, bathing or washing.
  • the solutions are prepared by dissolving the active compound in a suitable solvent and adding, if appropriate, additives such as solubilizers, acids, bases, buffer salts, antioxidants, preservatives.
  • Suitable solvents include: physiologically acceptable solvents, such as water, alcohols, such as ethanol, butanol, benzyl alcohol, glycerol, hydrocarbons, propylene glycol, polyethylene glycols and N-methyl-pyrrolidone, and their mixtures.
  • physiologically acceptable solvents such as water, alcohols, such as ethanol, butanol, benzyl alcohol, glycerol, hydrocarbons, propylene glycol, polyethylene glycols and N-methyl-pyrrolidone, and their mixtures.
  • the active compounds can also be dissolved in physiologically acceptable vegetable or synthetic oils.
  • Suitable solubilizers include: solvents which facilitate the dissolution of the active compound in the main solvent or which prevent precipitation of the active compound.
  • solubilizers are polyvinylpyrrolidone, polyethoxylated castor oil and polyethoxylated sorbitan esters.
  • Suitable preservatives are: benzyl alcohol, trichlorobutanol, p-hydroxybenzoic esters or n-butanol.
  • thickeners are: inorganic thickeners, such as bentonites, colloidal silica, aluminium monostearate, or organic thickeners, such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.
  • Gels which are applied to the skin or smoothed on are prepared by adding such an amount of thickener to solutions which have been prepared as described above that a clear composition is formed which has an ointment-like consistency.
  • the thickeners used are the thickeners indicated further above.
  • pour-on and spot-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries, such as colorants, antioxidants, photostabilizers or tackifiers are added.
  • Suitable solvents include: 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 monobutyl ether, ketones, such as acetone, methyl ethyl ketone, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, N-methylpyrrolidone, 2-dimethyl-4-oxy-methylene-1,3-dioxolane.
  • aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol
  • esters such as ethyl acetate, butyl acetate
  • Colorants are all colorants which can be dissolved or suspended and which are approved for use in animals.
  • Auxiliaries include spreading oils, such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides or fatty alcohols.
  • Antioxidants are sulphites or metabisulphites, such as potassium metabisulphite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol.
  • photostabilizers are substances from the class of the benzophenones and novantisolic acid.
  • Tackifiers are, for example, cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.
  • Emulsions are either of the water-in-oil or the oil-in-water type.
  • Suitable hydrophobic phases include: paraffin oils, silicone oils, natural vegetable oils, such as sesame seed oil, almond oil, castor oil, synthetic triglycerides, such as caprylic/capric acid biglyceride, a triglyceride mixture with vegetable fatty acids of chain length C 8-12 or other specifically selected natural fatty acids, mixtures of partial glycerides of saturated or unsaturated fatty acids which may also contain hydroxyl groups, mono- and diglycerides of the C 8 /C 10 -fatty acids.
  • Fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, esters of a branched fatty acid having a medium chain length with saturated fatty alcohols of chain length C 16 -C 18 , isopropyl myristate, isopropyl palmitate, caprylic/capric esters of saturated fatty alcohols of chain length C 12 -C 18 , isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as dibutyl phthalate, diisopropyl adipate, ester mixtures related to the latter, amongst others fatty alcohols, such as isotridecyl alcohol, 2-otyldodecanol, cetylstearyl alcohol or
  • Fatty acids such as, for example oleic acid and its mixtures.
  • Suitable hydrophilic phases include:
  • Suitable emulsifiers include: nonionic surfactants, for example polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyethoxy stearate, alkylphenol polyglycol ethers;
  • ampholytic surfactants such as disodium N-lauryl-B-iminodipropionate or lecithin;
  • anionic surfactants such as sodium lauryl sulphate, fatty alcohol ether sulphates, and the monoethanolamine salt of mono/dialkylpolyglycol ether orthophosphoric ester;
  • cationic surfactants such as cetyltrimethylammonium chloride.
  • auxiliaries include: substances which increase the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, methylvinyl ether/maleic anhydride copolymers, polyethylene glycols, waxes, colloidal silica, or mixtures of the listed substances.
  • Suspensions are prepared by suspending the active compound in a liquid excipient, if appropriate with the addition of other auxiliaries, such as wetting agents, colorants, bioabsorption promoters, preservatives, antioxidants and photostabilizers.
  • auxiliaries such as wetting agents, colorants, bioabsorption promoters, preservatives, antioxidants and photostabilizers.
  • Suitable liquid excipients include all homogeneous solvents and solvent mixtures.
  • Suitable wetting agents include the surfactants indicated further above.
  • auxiliaries include those indicated further above.
  • the active compound is mixed with suitable excipients, if appropriate with the addition of auxiliaries, and the mixture is formulated as desired.
  • Suitable excipients include all physiologically acceptable solid inert substances. Suitable for this purpose are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates, such as calcium carbonate, hydrogen carbonates, aluminium oxides, silicas, clays, precipitated or colloidal silica, and phosphates.
  • Auxiliaries are preservatives, antioxidants and colorants which have already been mentioned further above.
  • auxiliaries are lubricants and glidants, such as, for example, magnesium stearate, stearic acid, talc, bentonites.
  • compositions according to the invention may additionally comprise water-repelling or water-proof substances.
  • Suitable water-proof substances are already being used in sun protection compositions which are to protect the user against the UV radiation from the sun (for example U.S. Pat. No. 5,518,712 and U.S. Pat. No. 4,810,489). Here, it is intended to maintain sun protection even after the user has been swimming, is sweating heavily, etc.
  • Sun protection compositions which comprise such water-proof or water-repelling substances and insect repellents are already known (U.S. Pat. No. 5,716,602). However, compositions which comprise anthelmintics have hitherto not been described.
  • water-proof substances may also be present in the composition according to the invention. These may be substances which are soluble in fat and insoluble in water, and compounds which improve adherence of the composition to the skin.
  • Skin protection products may comprise, as water-proof components, for example from 1 to 50% by weight of a polymer such as polyvinylpyrrolidones, polyacrylates, silicones, etc.
  • compositions for topical application can be formulated as sprays, solutions, creams, ointments or layer- or film-forming compositions, according to the known processes for manufacturing cosmetics (Schrader, K. (1979) Unen und Japaneseuren der Kosmetika [Principles of and recipes for cosmetics], Dr. Alfred Hüthig Verlag, Heidelberg).
  • formulations according to the invention are applied evenly and without any gaps onto the skin, in amounts appropriate for the user.
  • compositions according to the invention are of course also suitable for use on animals to prevent infection of the animals with parasites of these genera.
  • the compositions can be used for pets, such as, for example, dogs and cats, and for economically useful animals, for example cattle, pigs, sheep, etc.
  • compositions according to the invention in general from 0.03 to 1 mg, preferably from 0.03 to 0.1 mg and particularly preferably from 0.04 to 0.06 mg of the active compound are applied per cm 2 of skin. This results in prophylactic protection against skin-penetrating worms and juvenile stages thereof. If the user stays in the water for a longer time, the active compound has to be applied repeatedly.
  • Snails Biomphalaria glabrata
  • 8 miracidia in 10 ml of water overnight.
  • cercariae were obtained by irradiating the snails, which had been kept in darkness, with light, followed by collection of the swarming cercariae within 2 hours.

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  • Tropical Medicine & Parasitology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Helmets And Other Head Coverings (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Compounds Of Unknown Constitution (AREA)
US10/311,418 2000-07-06 2001-06-25 Anthelminthic for the prevention of parasitic infections in human and animals Abandoned US20040029960A1 (en)

Priority Applications (1)

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Applications Claiming Priority (3)

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DE10032878.4 2000-07-06
DE10032878A DE10032878A1 (de) 2000-07-06 2000-07-06 Anthelmintika zur Verhinderung von parasitären Infektionen bei Mensch und Tier
PCT/EP2001/007201 WO2002002115A2 (de) 2000-07-06 2001-06-25 Anthelmintika zur verhinderung von parasitären infektionen bei mensch und tier

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US12/117,939 Expired - Fee Related US8501775B2 (en) 2000-07-06 2008-05-09 Anthelmintics for preventing parasitic infections in humans and animals

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US (2) US20040029960A1 (ko)
EP (1) EP1301185B1 (ko)
JP (2) JP2004501972A (ko)
KR (1) KR100927845B1 (ko)
CN (1) CN1283251C (ko)
AT (1) ATE446755T1 (ko)
AU (2) AU6908801A (ko)
BR (1) BR0112230A (ko)
CA (1) CA2414670C (ko)
DE (2) DE10032878A1 (ko)
DK (1) DK1301185T3 (ko)
ES (1) ES2332990T3 (ko)
HK (1) HK1058481A1 (ko)
HU (1) HUP0301579A3 (ko)
NZ (1) NZ523421A (ko)
PL (1) PL205722B1 (ko)
WO (1) WO2002002115A2 (ko)
ZA (1) ZA200210352B (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060182805A1 (en) * 2005-02-15 2006-08-17 Jazz Pharmaceuticals Dosage form and method for sustained release of substituted pyrazine compound

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US4900834A (en) * 1987-04-28 1990-02-13 Bayer Aktiengesellschaft Substituted α,ω-aminoalcohol derivatives
US4921855A (en) * 1987-06-22 1990-05-01 Fujisawa Pharmaceutical Co., Ltd. New Histidyl amino acid derivatives, and pharmaceutical composition comprising the same
US5304650A (en) * 1991-10-10 1994-04-19 Bayer Aktiengesellschaft Process for the preparation of alkyl N-(hydroxyalkyl)-carbamates
US6147091A (en) * 1996-05-06 2000-11-14 Bayer Aktiengesellschaft Arthropod repellant

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US4810489A (en) 1986-12-04 1989-03-07 Bristol-Myers Company High oil phase pharmaceutical vehicles and sunscreen compositions having waterproof sun protection factors
US5075307A (en) * 1987-07-28 1991-12-24 Merck & Co., Inc. Paraherquamide and dihydroparaherquamide as antihelminthic agents
EP0385106B1 (en) * 1989-02-28 1994-03-23 American Cyanamid Company Sustained release bolus effective for the prolonged prevention, treatment or control of nematode, acarid and endo- and ectoparasitic infestations of ruminants
US5518712A (en) 1992-06-25 1996-05-21 Stewart; Ernest Water resistant sunscreen protection and insect repellent compound
US5716602A (en) 1996-06-26 1998-02-10 S. C. Johnson & Sons, Inc. Insect repellent sunscreen
WO1999015166A1 (en) * 1997-09-23 1999-04-01 Pfizer Limited Parasiticidal formulations
IL127852A0 (en) * 1998-01-30 1999-10-28 American Cyanamid Co Methods and compositions for protecting animals and humans against attack and infestation by arthropod and helminth parasites

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4900834A (en) * 1987-04-28 1990-02-13 Bayer Aktiengesellschaft Substituted α,ω-aminoalcohol derivatives
US4921855A (en) * 1987-06-22 1990-05-01 Fujisawa Pharmaceutical Co., Ltd. New Histidyl amino acid derivatives, and pharmaceutical composition comprising the same
US5304650A (en) * 1991-10-10 1994-04-19 Bayer Aktiengesellschaft Process for the preparation of alkyl N-(hydroxyalkyl)-carbamates
US6147091A (en) * 1996-05-06 2000-11-14 Bayer Aktiengesellschaft Arthropod repellant

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060182805A1 (en) * 2005-02-15 2006-08-17 Jazz Pharmaceuticals Dosage form and method for sustained release of substituted pyrazine compound

Also Published As

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EP1301185B1 (de) 2009-10-28
DK1301185T3 (da) 2010-03-08
AU2001269088B2 (en) 2006-04-13
JP2004501972A (ja) 2004-01-22
CN1440285A (zh) 2003-09-03
KR20030017530A (ko) 2003-03-03
CN1283251C (zh) 2006-11-08
CA2414670A1 (en) 2003-01-03
ZA200210352B (en) 2004-10-20
HK1058481A1 (en) 2004-05-21
WO2002002115A2 (de) 2002-01-10
EP1301185A2 (de) 2003-04-16
NZ523421A (en) 2005-10-28
HUP0301579A3 (en) 2004-06-28
HUP0301579A2 (hu) 2003-08-28
DE10032878A1 (de) 2002-01-17
WO2002002115A3 (de) 2002-05-23
JP2013035868A (ja) 2013-02-21
US8501775B2 (en) 2013-08-06
US20130172385A1 (en) 2013-07-04
KR100927845B1 (ko) 2009-11-23
CA2414670C (en) 2011-01-18
PL205722B1 (pl) 2010-05-31
PL359488A1 (en) 2004-08-23
ES2332990T3 (es) 2010-02-16
ATE446755T1 (de) 2009-11-15
BR0112230A (pt) 2003-05-06
AU6908801A (en) 2002-01-14
DE50115198D1 (de) 2009-12-10

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