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EP1318795A2 - Anthelminthiques servant a lutter contre les infections parasitaires chez l'homme et l'animal - Google Patents

Anthelminthiques servant a lutter contre les infections parasitaires chez l'homme et l'animal

Info

Publication number
EP1318795A2
EP1318795A2 EP01969321A EP01969321A EP1318795A2 EP 1318795 A2 EP1318795 A2 EP 1318795A2 EP 01969321 A EP01969321 A EP 01969321A EP 01969321 A EP01969321 A EP 01969321A EP 1318795 A2 EP1318795 A2 EP 1318795A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkenyl
alkynyl
hydrogen
formula
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Withdrawn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
EP01969321A
Other languages
German (de)
English (en)
Inventor
Achim Harder
Georg Von Samson-Himmelstjerna
Bernd-Wieland Krüger
Heinz Mehlhorn
Jürgen Schmidt
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 AG
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 EP1318795A2 publication Critical patent/EP1318795A2/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Withdrawn legal-status Critical Current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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • 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
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/221—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having an amino group, e.g. acetylcholine, acetylcarnitine
    • 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
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/223—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of alpha-aminoacids
    • 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

Definitions

  • the present invention relates to compositions comprising certain active substances suitable as repellents and their use for reducing the infection of humans or animals with the infection stages of parasitic flatworms (platinum helminths).
  • the agents are used on the skin against such stages of flatworms, so-called cercariae, which can penetrate through the skin into the host body.
  • pretreatment of the skin according to the invention with substances having an anti-inflammatory effect can protect the pathogens from penetrating.
  • Some compounds have been tested in the past for their suitability for preventing infections with such parasites.
  • the substances previously described for the purposes of the invention are toxic if they enter the body through the skin or after oral ingestion:
  • Hexachlorophene has a killing effect on cercariae from Schistosoma mansoni (Fripp, P.J. and Armstrong, F.L., The efficacy of hexachlorophene skin cleanser as a cercariae repellent. South African Med. J. 47: 1973, 526-527). Because of health risks, especially liver damage, hexachlorophene cannot be applied to the skin in humans. It is toxic at
  • 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.] Is toxicologically unsafe because it can cause inheritable genetic damage (Registry of Toxic Effects of Chemical Substances, National Institute of Occupational Safety and Health). Use on the skin when exposed to water is prohibited by its environmentally hazardous properties, since niclosamide is highly water-endangering [Federal Environment Agency (ed.) Catalog of water-endangering substances. LTwS no. May 12, 1996 with ongoing additions,
  • N, N-Diethyl-m-toluamide acts on cercariae from 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. At the. J. Trop. Med. Hyg. 58: 1998, 828-834).
  • DEET has some unfavorable properties.
  • Plathelminths especially Schistosoma haematobium, Schistosoma japonicum, Trichobilharzia spp. and Ornithobilharzia spp., but also Echinostoma spp. et al to offer.
  • the invention accordingly relates to
  • Agent for defense against helminthic parasites characterized by a content of at least one compound of the formula (I)
  • R 1 represents hydrogen or an optionally substituted alkyl, alkenyl or alkynyl radical
  • R 2 and R 5 are identical or different and stand for optionally substituted alkyl, alkenyl or alkynyl radicals and R 3 and R 5 represent hydrogen, optionally substituted alkyl, aralkyl or aryl or together with the atom to which they are attached form an optionally substituted, monocyclic ring.
  • R 1 represents hydrogen, (C r C 10 ) - alkyl, (C 2 -C 10 ) -A - kmyl,
  • R 2 and R 5 are the same or different and stand for (CI -CJO) - alkyl, (C2-C10) - alkenyl or (C -C ⁇ o) alkynyl and
  • R 3 and R 4 are hydrogen, (Cj-Cio) - alkyl, in each case in the aryl part optionally mono- to triple, identical or differently substituted aryl or aralkyl each having 6 to 10 carbon atoms in the aryl part and optionally 1 to 4 carbon atoms in the alkyl part , the aryl substituents in each case being suitable: halogen, in each case straight-chain or branched (Ci-C ⁇ alkyl, (Ci-C ⁇ haloalkyl, (-C-C4) haloalkoxy and (C 1 -C) halo - alkylthio or together with the atom to which they are attached represent cycloalkyl having 3 to 7 carbon atoms.
  • R 1 represents hydrogen, (C r C 5 ) alkyl, (C 2 -C 5 ) alkenyl or (C 2 -C 5 alkynyl,
  • R 2 represents (C r C 5 ) alkyl, (C 2 -C 5 ) alkenyl or (C 2 -C 5 ) alkynyl
  • R 3 and R 4 are hydrogen, (C 1 -C 5 ) alkyl, each in the phenyl part optionally mono- to trisubstituted, identically or differently substituted, phenyl or phenylalkyl with optionally 1 or 2 carbon atoms in the alkyl part, the following being suitable as phenyl substituents: Fluorine, chlorine, bromine, (-C-C 2 ) - alkyl, (C ⁇ -C 2 ) ⁇
  • Haloalkyl, (CC ⁇ -haloalkoxy, (Cj-C 2 ) -haloalkylthio or together with the atom to which they are attached are cycloalkyl having 3 to 6 carbon atoms and
  • R 5 is (C 1 -C 10 ) alkyl, (C 2 -C 5 ) alkenyl or (C 2 -C 5 ) alkynyl.
  • R l is hydrogen, (C r C 5 ) alkyl, (C 2 -C 5 ) alkenyl or (C 2 -C 5 ) -
  • R 2 represents (C 1 -C 5 ) alkyl, (C 2 -C 5 ) alkenyl or (C 2 -C 5 ) alkynyl,
  • R 3 and R 4 are hydrogen, (C 1 -C 5 ) -alkyl, each in the phenyl part optionally mono- to trisubstituted, identically or differently, substituted phenyl, benzyl, phenethyl, the substituents in each case being: fluorine, chlorine, bromine, methyl , Ethyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio or together with the atom to which they are attached stand for cyclopropyl, cyclopentyl, cyclohexyl and
  • R 5 represents (C r C 10 ) alkyl, (C 2 -C 5 ) alkenyl or (C 2 -C 5 ) alkynyl.
  • R 1 represents hydrogen, (C r C 5 ) -alkyl or (C 2 -C 5 ) -alkenyl
  • R 2 represents (C r C 5 ) alkyl or (C 2 -C 5 ) alkenyl
  • R 3 and R 4 represent hydrogen, (C r C 5 ) alkyl, or together with the atom to which they are attached, stand for cyclopropyl and
  • R 5 stands for (-C 5 ) alkyl or (C 2 -C 5 ) alkenyl.
  • a method of repelling helminthic parasites characterized in that compounds of the general formula (I) are used.
  • a process for the preparation of agents for defense against helminthic parasites characterized in that compounds of the general formula (I) are mixed with extenders and / or surface-active agents.
  • the compound of the formula is particularly suitable for use in the agents according to the invention.
  • the compounds of formula (I) and their preparation are known from DE OS 38 20 528.
  • the active substances contained in the agents according to the invention have already been used specifically for use as repellants on the skin against insects and ticks.
  • a major advantage of using the compounds according to the invention is their high skin, plant and environmental compatibility and the generally low toxicity of these compounds.
  • the agents according to the invention now enable simultaneous prevention against infections with platinum helminths and protection against mosquitoes with one agent. This avoids the need to use two different, possibly incompatible agents on the skin at the same time.
  • the agents according to the invention can also contain all customary auxiliaries and additives which are used in formulations for topical application.
  • the active ingredients are used directly or in the form of suitable preparations dermally or with the aid of shaped articles containing active ingredients, e.g. Strips, plates, ribbons, collars, ear tags, limb ribbons, marking devices.
  • the dermal application takes place, for example, in the form of bathing, dipping, dipping), spraying (spraying), pouring on (pour-on or spot-on), washing, shampooing, watering, powdering.
  • Suitable preparations are:
  • Emulsions and suspensions for dermal use and semi-solid preparations are Emulsions and suspensions for dermal use and semi-solid preparations
  • Solid preparations such as powders, shaped articles containing active ingredients.
  • Solutions for use on the skin are dripped on, spread on, rubbed in, sprayed on, sprayed on or applied by dipping (dipping), bathing or washing.
  • the 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.
  • solvents physiologically compatible solvents such as water, alcohols such as ethanol, butanol, benzyl alcohol, glycerol, hydrocarbons, propylene glycol, polyethylene glycols, N-methylpyrrolidone, and mixtures thereof.
  • the active ingredients can optionally also be dissolved in physiologically compatible vegetable or synthetic oils.
  • 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: benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester, n-butanol.
  • Thickeners are: inorganic thickeners such as bentonites, colloidal silica, aluminum monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.
  • Gels that are applied or spread on the skin are produced by adding enough thickening agent to solutions that have been prepared as described above to produce a clear mass with an ointment-like consistency.
  • the thickeners specified above are used as thickeners.
  • Pour-on formulations are poured or sprayed onto limited areas of the skin, the active ingredient 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, further auxiliaries such as dyes, 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, benzylbenzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol, monobutyl glycol, monobutyl glycol Methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethyl acetamide, N-methyl pyrrolidone, 2-dimethyl-4-oxy-methylene-l, 3-dioxolane. Dyes are all dyes approved for use on animals, which can be dissolved or suspended.
  • Excipients are also 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
  • Adhesives are e.g. Cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin. Emulsions are either water in oil or oil in water.
  • 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
  • Fatty acid esters such as ethyl stearate, di-n-butyryl adipate, lauric acid hexyl ester,
  • Isotridecyl alcohol 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol.
  • Fatty acids such as Oleic acid and its mixtures.
  • hydrophilic phase The following can be mentioned as the hydrophilic phase:
  • Alcohols such as e.g. Propylene glycol, glycerin, sorbitol and their mixtures.
  • nonionic surfactants e.g. polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether;
  • ampholytic surfactants such as di-Na-N-lauryl- ⁇ -iminodipropionate or lecithin;
  • anionic surfactants such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono / dialkyl polyglycol ether orthophosphoric acid ester monoemanolamine salt; cationic surfactants such as cetyltrimemylammonium chloride.
  • viscosity-increasing substances and substances stabilizing the emulsion such as carboxymethyl cellulose, methyl cellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinyl pyrrone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes , colloidal silica or mixtures of the listed substances.
  • Suspensions are prepared by adding the active ingredient in a carrier liquid, if necessary with the addition of other auxiliaries such as wetting agents, dyes, Suspending substances, preservatives, antioxidants, light stabilizers suspended.
  • the surfactants specified above may be mentioned as wetting agents (dispersants).
  • Semi-solid preparations for dermal administration differ from the suspensions and emulsions described above only in their higher viscosity.
  • 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, u-minium oxides,
  • Excipients are preservatives, antioxidants, dyes, which have already been listed above.
  • auxiliaries are lubricants and lubricants such as Magnesium stearate, stearic acid, talc, bentonite.
  • the Agents according to the invention also contain water-repellent or waterproof substances.
  • Suitable waterproof substances have previously been used in sunscreens to protect the user against the UN radiation from the sun (e.g.
  • waterproof substances can also be contained in the agent according to the invention. These can be fat-soluble, water-insoluble substances as well as compounds that increase the adhesion of the agent to the skin.
  • Skin protection products could contain, for example, 1 to 50% by weight of a polymer such as polyynylpyrrolidones, polyacrylates, silicones, etc. as water-resistant components.
  • a polymer such as polyynylpyrrolidones, polyacrylates, silicones, etc.
  • the agents for topical use can be used as a spray, solution, cream, ointment or layer- or film-forming agent, according to the methods known for the production of cosmetics (Schrader, K. (1979) basics and formulations of the cosmetics. Dr. Alfred Hüthig Verlag, Heidelberg).
  • the formulations according to the invention are applied to the skin uniformly and without gaps in a consumer-appropriate amount.
  • the agents according to the invention are of course also suitable for use on animals in order to prevent infection of the animals with parasites of these genera.
  • the funds can be used in pets, such as dogs and cats
  • Livestock such as cattle, sheep, etc.
  • 0.03 to 1 mg, preferably 0.03 to 0.1 mg and particularly preferably 0.04 to 0.06 mg of the active ingredient are generally applied per square centimeter of skin. This provides prophylactic protection against skin-penetrating worms and their pre-stages.
  • the active ingredient must be applied repeatedly during a longer stay in the water.

Landscapes

  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

La présente invention concerne des substances comprenant certains principes actifs appropriés en tant qu'agents répulsifs, et leur utilisation pour éviter à l'homme et à l'animal d'être atteints de différents stades infectieux provoqués par des vers plats parasitaires (Plathelminthes).
EP01969321A 2000-07-06 2001-06-26 Anthelminthiques servant a lutter contre les infections parasitaires chez l'homme et l'animal Withdrawn EP1318795A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10032880A DE10032880A1 (de) 2000-07-06 2000-07-06 Anthelmintika zur Verhinderung von parasitären Infektionen bei Mensch und Tier IV
DE10032880 2000-07-06
PCT/EP2001/007296 WO2002002089A2 (fr) 2000-07-06 2001-06-26 Anthelminthiques servant a lutter contre les infections parasitaires chez l'homme et l'animal

Publications (1)

Publication Number Publication Date
EP1318795A2 true EP1318795A2 (fr) 2003-06-18

Family

ID=7648014

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01969321A Withdrawn EP1318795A2 (fr) 2000-07-06 2001-06-26 Anthelminthiques servant a lutter contre les infections parasitaires chez l'homme et l'animal

Country Status (13)

Country Link
US (1) US20040006136A1 (fr)
EP (1) EP1318795A2 (fr)
JP (1) JP2004501961A (fr)
KR (1) KR20030047984A (fr)
CN (1) CN1452484A (fr)
AU (1) AU2001289612A1 (fr)
BR (1) BR0112366A (fr)
CA (1) CA2414690A1 (fr)
DE (1) DE10032880A1 (fr)
HU (1) HUP0303837A2 (fr)
PL (1) PL365638A1 (fr)
WO (1) WO2002002089A2 (fr)
ZA (1) ZA200300057B (fr)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1056132B (it) * 1974-10-02 1982-01-30 Sumitomo Chemical Co Derivati di amminoacidi sostituiti procedimento per produrli e composizioni fungicide che li contengono
DE3820528A1 (de) * 1988-06-16 1989-12-21 Bayer Ag Mittel zur insekten- und milbenabwehr
DE4341993A1 (de) * 1993-12-09 1995-06-14 Bayer Ag Endoparasitizide Mittel auf Basis von offenkettigen Octadepsipeptiden
DE4341991A1 (de) * 1993-12-09 1995-06-14 Bayer Ag Endoparasitizide Mittel auf Basis von offenkettigen Hexadepsipeptiden
DE4341992A1 (de) * 1993-12-09 1995-06-14 Bayer Ag Endoparasitizide Mittel auf Basis von offenkettigen Tetradepsipeptiden
US5621008A (en) * 1995-10-27 1997-04-15 Avon Products, Inc. N-acyl-ethylene-triacetic acids

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0202089A2 *

Also Published As

Publication number Publication date
CN1452484A (zh) 2003-10-29
WO2002002089A3 (fr) 2003-03-20
WO2002002089A2 (fr) 2002-01-10
PL365638A1 (en) 2005-01-10
CA2414690A1 (fr) 2002-01-10
KR20030047984A (ko) 2003-06-18
HUP0303837A2 (hu) 2004-03-29
JP2004501961A (ja) 2004-01-22
BR0112366A (pt) 2004-01-06
DE10032880A1 (de) 2002-01-17
ZA200300057B (en) 2004-07-05
AU2001289612A1 (en) 2002-01-14
US20040006136A1 (en) 2004-01-08

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