WO1997025976A1 - Anthelminthische paste - Google Patents

Anthelminthische paste Download PDF

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Publication number
WO1997025976A1
WO1997025976A1 PCT/EP1997/000006 EP9700006W WO9725976A1 WO 1997025976 A1 WO1997025976 A1 WO 1997025976A1 EP 9700006 W EP9700006 W EP 9700006W WO 9725976 A1 WO9725976 A1 WO 9725976A1
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WO
WIPO (PCT)
Prior art keywords
spp
pastes
anthelmintic
corn starch
horses
Prior art date
Application number
PCT/EP1997/000006
Other languages
English (en)
French (fr)
Inventor
Jochen Kalbe
Helmut Schnabel
Original Assignee
Bayer Aktiengesellschaft
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 Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to NZ325850A priority Critical patent/NZ325850A/xx
Priority to CA002242972A priority patent/CA2242972C/en
Priority to DK97900555T priority patent/DK0877598T3/da
Priority to US09/101,931 priority patent/US6025357A/en
Priority to JP52563797A priority patent/JP4143121B2/ja
Priority to HU9901023A priority patent/HU227817B1/hu
Priority to DE59703789T priority patent/DE59703789D1/de
Priority to AT97900555T priority patent/ATE201979T1/de
Priority to EP97900555A priority patent/EP0877598B1/de
Priority to BR9706976-0A priority patent/BR9706976A/pt
Priority to AU13093/97A priority patent/AU703567B2/en
Priority to KR10-1998-0704695A priority patent/KR100451857B1/ko
Publication of WO1997025976A1 publication Critical patent/WO1997025976A1/de

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Classifications

    • 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
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
    • 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
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • 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
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin

Definitions

  • the present invention relates to anthelmintic pastes for horses, dogs and cats based on hexahydropyrazino derivatives.
  • Pastes containing praziquantel are known from EP-A 279 343.
  • a disadvantage of these pastes is their high water content.
  • the pastes must therefore be protected against attack by pathogenic bacteria with preservatives. Even the homogeneous mixing in of the poorly water-soluble active ingredients often presents difficulties.
  • the present invention relates to anthelmintic pastes for horses, dogs and cats based on hexahydropyrazino derivatives which are characterized in that, in addition to the active ingredient, they contain corn starch and glycerol as auxiliaries for paste formation.
  • Mixtures according to the invention which contain praziquantel and epsiprantel as hexahydropyrazine derivatives are preferred.
  • Praziquantel is particularly preferred.
  • the active substance is contained in the formulations according to the invention in weight concentrations of 5 to 30%, preferably 10 to 20%.
  • Corn starch is contained in the formulations according to the invention in weight concentrations of 10 to 30%, preferably 15 to 25%.
  • Glycerin is contained in the formulations according to the invention in weight concentrations of 40 to 80%, preferably 55 to 75%.
  • the individual components are 100% complementary.
  • the ratio of corn starch to glycerin is chosen so that an easy-to-process, packable and usable formulation is created.
  • the formulations according to the invention can also contain further active ingredients. These include phenylguanidines, benzimidazoles or tetrahydropyrimidines.
  • Phenylguanidines which may be mentioned are those of the formula (I):
  • R 1 represents hydrogen, optionally substituted alkyl, cycloalkyl, alkoxy, aryl or amino,
  • R 2 represents hydrogen, optionally substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, alkoxy, alkenoxy,
  • R 3 represents hydrogen, optionally substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl,
  • R 4 represents alkyl, alkoxy, phenoxy, alkylthio, phenylthio, phenylsulfinyl, phenylsulfonyl, benzoyl, which are optionally substituted by halogen, alkoxy, alkylthio, haloalkoxy, haloalkylthio.
  • R 3 and R 4 have the meaning given for the compounds of the formula (I).
  • Tetrahydropynmidines which may be mentioned are those of the formula (III):
  • R 5 represents hydrogen or alkyl
  • R 6 represents optionally substituted phenyl or thienyl
  • Phenylguanidines include e.g. Febantel, Netobimin.
  • the benzimidazoles include e.g. Febendazole, albendazole, oxibendazole, oxfendazole, mebendazole, flubendazole, parbendazole, luxabendazole.
  • Tetrahydropyrimidines include e.g. Pyrantel, Morantel, Oxantel.
  • the pastes according to the invention are suitable with favorable warm-blood toxicity for combating pathogenic endoparasites in horses in animal husbandry and
  • Pathogenic endoparasites include cestodes, trematodes, nematodes, acantocephals, in particular: From the order of the Pseudophyllidea, for example: Diphyllobothrium spp., Spiiometra spp., Schistocephalus spp ..
  • Cyclophyllidea for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Taenia spp., Echinococcus spp., Hydatigera spp., Diorchis spp., Dipylidium spp., Joyeuxyrella spp. .
  • Stronylus spp. Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Poteriostomum spp., Cyclicocyclus spp., Stephanurus spp., Ancyclostoma spp., Uncinaria spp., Cyathostom spp.
  • Metastrongylus spp. Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Filaroides spp., Parafilaroides spp., Marshallaganpp., Marshallagia spp., Craterostomum spp., Cyclicodontophorus spp., Hyalocephalus spp., Cylindropharynx spp., Caballonema spp., Elaeophorus spp., Dirofilaria spp., Onchocerca spp., Setaria spp ..
  • Oxyurida From the order of the Oxyurida, for example: Oxyuris spp., Enterobius spp ..
  • Ascaridia e.g. Ascaris spp., Toxascaris spp., Toxocara spp., Parascaris spp., Probstmangria spp ..
  • the application can be prophylactic as well as therapeutic.
  • the preferred use concentration of the mixture according to the invention is 1 to 300 mg, preferably 5 to 50 mg, of hexahydropyrazine per kg of live weight.
  • anthelmintic active ingredients can be added in an application amount per kg of 0.1 to 20 mg, preferably 1 to 10 mg, particularly preferably approx. 5 mg.
  • the components are stirred together. A paste is formed which can be filled into appropriate applicators.

Landscapes

  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Zoology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Processing Of Solid Wastes (AREA)
  • Fertilizers (AREA)

Abstract

Die vorliegende Erfindung betrifft anthelminthische Pasten für Pferde, Hunde und Katzen auf der Basis von Hexahydropyrazinoderivaten, die dadurch gekennzeichnet sind, daß sie neben dem Wirkstoff Maisstärke und Glycerin enthalten.

Description

Antheimintische Paste
Die vorliegende Erfindung betrifft anthelmintische Pasten für Pferde, Hunde und Katzen auf Basis von Hexahydropyrazinoderivaten.
Praziquantel-haltige Pasten sind bekannt aus EP-A 279 343. Nachteilig bei diesen Pasten ist jedoch ihr hoher Wassergehalt. Die Pasten müssen daher vor Befall durch pathogene Bakterien durch Konservierungsmittel geschützt werden. Auch das homogene Einmischen der schwer wasserlöslichen Wirkstoffe bereitet oft Schwierigkeiten.
Die vorliegende Erfindung betrifft anthelmintische Pasten für Pferde, Hunde und Katzen auf der Basis von Hexahydropyrazinoderivaten, die dadurch gekennzeich¬ net sind, daß sie neben dem Wirkstoff als Hilfsstoffe zur Pastenbildung Maisstärke und Glycerin enthalten.
Es handelt sich um eine Formulierung die
1. nur aus wenigen Komponenten aufgebaut ist,
2. aus preiswerten Komponenten aufgebaut ist,
3. ohne besondere Konservierungsmittel auskommt,
4. einfach herzustellen ist.
Bevorzugt sind erfindungsgemäße Mischungen, die als Hexahydropyrazinderivate Praziquantel und Epsiprantel enthalten. Besonders bevorzugt ist Praziquantel.
Der Wirkstoff ist in den erfindungsgemäßen Formulierungen in Gewichtskonzen¬ trationen von 5 bis 30 %, bevorzugt von 10 bis 20 % enthalten.
Maisstärke ist in den erfindungsgemäßen Formulierungen in Gewichtskonzentra- tionen von 10 bis 30 %, bevorzugt von 15 bis 25 % enthalten. Glycerin ist in den erfindungsgemäßen Formulierungen in Gewichtskonzentra¬ tionen von 40 bis 80 %, bevorzugt von 55 bis 75 % enthalten. Die Einzelkompo¬ nenten ergänzen sich zu 100 %. Das Verhältnis Maisstärke zu Glycerin wird so gewählt, daß eine leicht verarbeitbare, verpackbare und anwendungsfähige Formu- lierung entsteht.
Die erfindungsgemäßen Formulierungen können neben den Hexahydropyrazinonen noch weitere Wirkstoffe enthalten. Dazu zählen Phenylguanidine, Benzimidazole oder Tetrahydropyrimidine.
Als Phenylguanidine seien solche der Formel (I) genannt:
Figure imgf000004_0001
in welcher
R1 für Wasserstoff, gegebenenfalls substituiertes Alkyl, Cycloalkyl, Alkoxy, Aryl oder Amino steht,
R2 für Wasserstoff, gegebenenfalls substituiertes Alkyl, Cycloalkyl, Alkenyl, Alkinyl, Aryl, Alkoxy, Alkenoxy, steht,
R3 für Wasserstoff, gegebenenfalls substituiertes Alkyl, Cycloalkyl, Alkenyl, Alkinyl, Aryl, steht,
R4 für Alkyl, Alkoxy, Phenoxy, Alkylthio, Phenylthio, Phenylsulfinyl, Phenyl- sulfonyl, Benzoyl steht, die gegebenenfalls substituiert sind durch Halogen, Alkoxy, Alkylthio, Halogenalkoxy, Halogenalkylthio.
Als Benzimidazole seien solche der Formel (II) genannt:
Figure imgf000005_0001
in welcher
R3 und R4 die bei den Verbindungen der Formel (I) angegebene Bedeutung haben.
Als Tetrahydropynmidine seien solche der Formel (III) genannt:
Figure imgf000005_0002
X in welcher
R5 für Wasserstoff oder Alkyl steht,
R6 für gegebenenfalls substituiertes Phenyl oder Thienyl steht,
X für -(CH2)2_3-, -CH=CH- steht.
Zu den Phenylguanidinen gehören z.B. Febantel, Netobimin.
Zu den Benzimidazolen gehören z.B. Febendazol, Albendazol, Oxibendazol, Oxfendazol, Mebendazol, Flubendazol, Parbendazol, Luxabendazol.
Zu den Tetrahydropyrimidinen gehören z.B. Pyrantel, Morantel, Oxantel.
Die erfindungsgemäßen Pasten eignen sich bei günstiger Warmblütertoxizität zur Bekämpfung von pathogenen Endoparasiten die bei Pferden in der Tierhaltung und
Tierzucht vorkommen. Sie sind dabei gegen alle oder einzelne Entwicklungs¬ stadien der Schädlinge sowie gegen resistente und normal sensible Arten wirksam. Zu den pathogenen Endoparasiten zählen Cestoden, Trematoden, Nematoden, Acantocephalen, insbesondere: Aus der Ordnung der Pseudophyllidea z.B.: Diphyllobothrium spp., Spiiometra spp., Schistocephalus spp..
Aus der Ordnung der Cyclophyllidea z.B.: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Taenia spp., Echinococcus spp., Hydatigera spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Spyrometra spp..
Aus der Unterklasse der Digenea z.B.: Schistosoma spp., Fasciola spp., Dicro- coelium spp., Opisthorchis spp..
Aus der Ordnung der Enoplida z.B.: Trichuris spp., Capillaria spp., Trichinella spp..
Aus der Ordnung der Rhabditia z.B.: Micronema spp., Strongyloides spp..
Aus der Ordnung der Strongylida z.B.: Stronylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Poteriostomum spp., Cyclicocyclus spp., Stephanurus spp., Ancyclostoma spp., Uncinaria spp., Cyathostomum spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Filaroides spp., Parafilaroides spp., Marshallagia spp., Hyostrongylus spp., Ollulanus spp., Craterostomum spp., Cyclicodontophorus spp., Hyalocephalus spp., Cylindropharynx spp., Caballonema spp., Elaeophorus spp., Dirofilaria spp., Onchocerca spp., Setaria spp..
Aus der Ordnung der Oxyurida z.B.: Oxyuris spp., Enterobius spp..
Aus der Ordnung der Ascaridia z.B. Ascaris spp., Toxascaris spp., Toxocara spp., Parascaris spp., Probstmangria spp..
Aus der Ordnung der Spirurida z.B.: Thelazia spp., Habronema spp., Draschia spp., Dracunculus spp..
Die Anwendung kann sowohl prophylaktisch als auch therapeutisch erfolgen. Die bevorzugte Anwendungskonzentration der erfindungsgemäßen Mischung liegt pro kg Lebendgewicht bei 1 bis 300 mg, bevorzugt bei 5 bis 50 mg Hexahydro- pyrazin.
Weitere anthelminthische Wirkstoffe können zur Anwendung in einer Aufwand¬ menge pro kg von 0,1 bis 20 mg, bevorzugt 1 bis 10 mg, besonders bevorzugt ca. 5 mg, zugesetzt werden.
Beispiel 1
Paste zur oralen Applikation oder zum Mischen unter das Futter
Zu sammensetzu ng :
Praziquantel 20,0 g Maisstärke 15,0 g
Glycerin 65,0 g
Herstellung:
Die Komponenten werden zusammengerührt. Es entsteht eine Paste die in ent¬ sprechende Applikatoren gefüllt werden kann.

Claims

Patentansprüche
1. Anthelminthische Pasten für Pferde, Hunde und Katzen auf der Basis von Hexahydropyrazinoderivaten, die dadurch gekennzeichnet sind, daß sie neben dem Wirkstoff als Hilfsstoffe zur Pastenbildung Maisstärke und Glycerin enthalten.
2. Anthelminthische Pasten für Pferde, Hunde und Katzen gemäß Anspruch 1, dadurch gekennzeichnet, daß der Wirkstoff in Gewichtskonzentrationen von 5 bis 30 % enthalten ist, Maisstärke in Gewichtskonzentrationen von 10 bis 30 % enthalten ist, Glycerin in Gewichtskonzentrationen von 40 bis 80 % enthalten ist.
PCT/EP1997/000006 1996-01-16 1997-01-03 Anthelminthische paste WO1997025976A1 (de)

Priority Applications (12)

Application Number Priority Date Filing Date Title
NZ325850A NZ325850A (en) 1996-01-16 1997-01-03 Anthelmintic paste for horses, dogs and cats
CA002242972A CA2242972C (en) 1996-01-16 1997-01-03 Anthelmintic paste
DK97900555T DK0877598T3 (da) 1996-01-16 1997-01-03 Anthelmintisk pasta
US09/101,931 US6025357A (en) 1996-01-16 1997-01-03 Anthelmintic paste
JP52563797A JP4143121B2 (ja) 1996-01-16 1997-01-03 駆虫ペースト
HU9901023A HU227817B1 (en) 1996-01-16 1997-01-03 Anthelmintic paste
DE59703789T DE59703789D1 (en) 1996-01-16 1997-01-03 Anthelminthische paste
AT97900555T ATE201979T1 (de) 1996-01-16 1997-01-03 Anthelminthische paste
EP97900555A EP0877598B1 (de) 1996-01-16 1997-01-03 Anthelminthische paste
BR9706976-0A BR9706976A (pt) 1996-01-16 1997-01-03 Pasta anti-helmìntica
AU13093/97A AU703567B2 (en) 1996-01-16 1997-01-03 Anthelmintic paste
KR10-1998-0704695A KR100451857B1 (ko) 1996-01-16 1997-01-03 구충제페이스트

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19601263A DE19601263A1 (de) 1996-01-16 1996-01-16 Anthelmintische Paste
DE19601263.5 1996-01-16

Publications (1)

Publication Number Publication Date
WO1997025976A1 true WO1997025976A1 (de) 1997-07-24

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Application Number Title Priority Date Filing Date
PCT/EP1997/000006 WO1997025976A1 (de) 1996-01-16 1997-01-03 Anthelminthische paste

Country Status (15)

Country Link
US (1) US6025357A (de)
EP (1) EP0877598B1 (de)
JP (1) JP4143121B2 (de)
KR (1) KR100451857B1 (de)
AT (1) ATE201979T1 (de)
AU (1) AU703567B2 (de)
BR (1) BR9706976A (de)
CA (1) CA2242972C (de)
DE (2) DE19601263A1 (de)
DK (1) DK0877598T3 (de)
ES (1) ES2157551T3 (de)
HU (1) HU227817B1 (de)
NZ (1) NZ325850A (de)
PT (1) PT877598E (de)
WO (1) WO1997025976A1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7763583B2 (en) 2003-12-13 2010-07-27 Bayer Animal Health Gmbh Endoparasiticidal compositions for topical application

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6207179B1 (en) * 2000-05-18 2001-03-27 Phoenix Scientific, Inc. Parasiticidal formulation for animals and a method of making this formulation
DE102005011779A1 (de) * 2005-03-11 2006-09-14 Bayer Healthcare Ag Endoparasitizide Mittel

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4117156A (en) * 1975-07-18 1978-09-26 Ciba-Geigy Ag Anthelmintic preparations
US4447414A (en) * 1982-12-21 1984-05-08 Cutter Laboratories, Inc. Carnivore anthelmintics
EP0279343A2 (de) * 1987-02-19 1988-08-24 Bayer Ag Anthelminthische Wirkstoffkombinationen
CH685370A5 (de) * 1991-12-23 1995-06-30 Andras Selmeczi Katalin Hajdu Veterinäres Präparat.

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4675174A (en) * 1985-08-16 1987-06-23 Alza Corporation Veterinary dispenser delivering beneficial agent by gas power generated in situ
AUPM969994A0 (en) * 1994-11-28 1994-12-22 Virbac S.A. Equine anthelmintic formulations

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4117156A (en) * 1975-07-18 1978-09-26 Ciba-Geigy Ag Anthelmintic preparations
US4447414A (en) * 1982-12-21 1984-05-08 Cutter Laboratories, Inc. Carnivore anthelmintics
EP0279343A2 (de) * 1987-02-19 1988-08-24 Bayer Ag Anthelminthische Wirkstoffkombinationen
CH685370A5 (de) * 1991-12-23 1995-06-30 Andras Selmeczi Katalin Hajdu Veterinäres Präparat.

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7763583B2 (en) 2003-12-13 2010-07-27 Bayer Animal Health Gmbh Endoparasiticidal compositions for topical application

Also Published As

Publication number Publication date
CA2242972A1 (en) 1997-07-24
HUP9901023A2 (hu) 1999-07-28
HUP9901023A3 (en) 1999-11-29
EP0877598A1 (de) 1998-11-18
JP2000503306A (ja) 2000-03-21
ES2157551T3 (es) 2001-08-16
NZ325850A (en) 1999-02-25
AU703567B2 (en) 1999-03-25
AU1309397A (en) 1997-08-11
PT877598E (pt) 2001-11-30
DK0877598T3 (da) 2001-07-23
US6025357A (en) 2000-02-15
BR9706976A (pt) 2000-01-04
DE59703789D1 (en) 2001-07-19
ATE201979T1 (de) 2001-06-15
JP4143121B2 (ja) 2008-09-03
EP0877598B1 (de) 2001-06-13
KR100451857B1 (ko) 2005-07-07
CA2242972C (en) 2005-03-15
HU227817B1 (en) 2012-03-28
KR19990076602A (ko) 1999-10-15
DE19601263A1 (de) 1997-07-17

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