WO2004069242A1 - Composition anthelmintique - Google Patents

Composition anthelmintique Download PDF

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Publication number
WO2004069242A1
WO2004069242A1 PCT/AU2004/000126 AU2004000126W WO2004069242A1 WO 2004069242 A1 WO2004069242 A1 WO 2004069242A1 AU 2004000126 W AU2004000126 W AU 2004000126W WO 2004069242 A1 WO2004069242 A1 WO 2004069242A1
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Prior art keywords
group
compound
composition
levamisole
amount
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PCT/AU2004/000126
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English (en)
Inventor
Kai Kin Lau
Brian Desmond Ford
John James O'brien
Marcus Holdsworth
Edward Lionel Bruce Whittem
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Jurox Pty Ltd
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Application filed by Jurox Pty Ltd filed Critical Jurox Pty Ltd
Priority to GB0516881A priority Critical patent/GB2413764B8/en
Priority to BRPI0407271A priority patent/BRPI0407271B1/pt
Priority to NZ540391A priority patent/NZ540391A/en
Priority to AU2004210461A priority patent/AU2004210461C1/en
Publication of WO2004069242A1 publication Critical patent/WO2004069242A1/fr
Priority to AU2009201942A priority patent/AU2009201942C1/en

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    • 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
    • A61K9/0017—Non-human animal skin, e.g. pour-on, spot-on
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
    • 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
    • A61K31/275—Nitriles; Isonitriles
    • A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4168—1,3-Diazoles having a nitrogen attached in position 2, e.g. clonidine
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/429—Thiazoles condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • 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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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

  • This invention relates to the treatment of anthelmintic infections in animals, and more particularly to compositions that are effective against parasites that are resistant to a wide variety of drug treatments, particularly in non-human animals..
  • Farm animals such as lambs, weaners and sheep may typically be infected by a wide variety of parasites.
  • parasites include Haemonconchus spp., Ostertagia spp., Trichostrongylus spp., Cooperia spp., Nematodirus spp., Chabertia spp., Oesophagostomum spp., Trichuris spp., Strongyloides spp., Bunostomum spp., Oestrus spp., Dictyocaulus spp., Fasciola spp. and Monezia spp. Specific examples of these parasites are set out in Table 1.
  • the present invention provides in a first aspect, a synergistic anthelmintically effective composition consisting of at least one compound selected from each of the following groups: macrocylic lactones, benzimidazoles, salicylanilides and imidazothiazoles and a therapeutically acceptable carrier.
  • the present invention provides a method for treating parasitic infections in an animal, comprising administering to the animal, a synergistic anthelmintically effective amount of a composition which consists of at least one compound selected from each of the following groups: macrocylic lactones, benzimidazoles, salicylanilides and imidazothiazoles and a therapeutically acceptable carrier.
  • the present invention further provides the use of a synergistic anthelmintically effective amount of a composition which consists of at least one compound selected from each of the following groups: macrocylic lactones, benzimidazoles, salicylanilides and imidazothiazoles and a therapeutically acceptable carrier in the treatment of a parasitic infection in an animal.
  • the aforementioned treatments may be desirably administered to animals prior to introduction to a land area so as to prevent the land area from becoming infested with parasites which may or may not be resistant to one or more compounds selected from the groups consisting of macrocylic lactones, benzimidazoles, salicylanilides and imidazothiazoles.
  • animals such as sheep, will be isolated for at least 2 days after treatment before being placed on pasture.
  • animals may be treated at any time, as appropriate, particularly when it is suspected that the animal may be carrying at least one parasite which is resistant to at least one of the groups macrocylic lactones, benzimidazoles, salicylanilides and imidazothiazoles.
  • compositions of this invention have application where the parasites are resistant to known drug treatments.
  • the compositions are effective in situations where parasites are resistant to at least one of each of the groups macrocylic lactones, benzimidazoles, salicylanilides and imidazothiazoles.
  • the compositions are effective in situations where parasites are resistant to at least two of each of the groups macrocylic lactones, benzimidazoles, salicylanilides and imidazothiazoles.
  • the compositions are effective in situations where parasites are resistant to at least three of each of the groups macrocylic lactones, benzimidazoles, salicylanilides and imidazothiazoles.
  • the compositions are effective in situations where parasites are resistant to all of the groups macrocylic lactones, benzimidazoles, salicylanilides and imidazothiazoles.
  • a preferred indication is the treatment of stock to eliminate adult gastro- intestinal worms and liver fluke.
  • treatment results in the clearance of >95% of total worm count including worms resistant to at least one of each of the groups macrocylic lactones, benzimidazoles, salicylanilides and imidazothiazoles.
  • Compositions of this invention include at least one compound selected from each of the groups: macrocylic lactones, benzimidazoles, salicylanilides and imidazothiazoles.
  • the therapeutically active compounds used in the invention are preferably incorporated into formulations in the range of concentrations as follows (g/L)
  • macrocylic lactones 0.1-20.0 g/L, preferably 0.5-1.5 g/L benzimidazoles: 1-100 g/L, preferably 18-30 g/L salicylanilides: 1-100 g/L, preferably 30-50 g/L imidazothiazoles: 1 -100 g L, preferably 30-50 g L
  • drenches are preferred dosage forms for the compositions of this invention, a number of alternative compositions may be used. These pour-on transdermals, slow release boluses for rumenal deposition and injectable formulations. Each dosage form requires a therapeutically effective carrier.
  • a formulation will include a solvent system for the macrocylic lactones, one or more dispersing and suspending agents for the benzimidazoles and salicylanilides , one or more surfactants, one or more preservatives, a buffering system and water as a carrier.
  • the solvent system for the macrocyclic lactones includes at least one solvent selected from the group consisting of: polyethylene glycol, tetraglycol, ethanol, benzyl alcohol and propylene glycol.
  • the dispersing and suspending agents for the benzimidazoles and salicylanilides include at least one selected from the group consissting of: glyceryl palmitostearate, bentonite, colloidal silica, xanthan gum and polymeric pyrrolidones.
  • Surfactants that may be used include polysorbate 80 and ethoxylated castor oil.
  • buffer systems may be used, particularly phosphate buffers based on combinations of varying amounts of monobasic and dibasic sodium phosphate to achieve the desired pH.
  • compositions of the invention are effective when used in a variety of animals.
  • animals For example, sheep, goats, ruminants (including cattle) and camelids.
  • Example 4 was prepared as follows:
  • step 1. Add polysorbate 80 to step 1. 3. Add water to the solution from step 2 and mix until homogeneous.
  • Trial RD0201-H002 A critical pen sacrifice study evaluating the therapeutic efficacy of a combination abamectin. levamisole hvdrochloride, albendazole and closantel anthelmintic formulation against resistant strains of Haemonchus contortus, Trichostrongylus colubriformis and Teladorsasia circumcincta in sheep.
  • faecal samples were collected from each trial animal to confirm individual zero faecal egg counts. Later that day trial sheep were infected with approximately 5000 Haemonchus contortus (macrocyclic lactone and closantel resistant strains), 6000 Trichostrongylus colubriformis (levamisole hydrochloride and albendazole resistant strains) and 5000 Osteratagia circumcincta (macrocyclic and albendazole resistant strains) infective larvae. Faecal samples were collected from each sheep on 14 th June 2002 (Day -3) and individual faecal egg counts were conducted.
  • Animals were ranked on the basis of decreasing faecal egg counts and blocked into eight blocks each of two animals and randomly allocated to the treatment groups from these blocks. The 16 animals with the highest counts were selected for inclusion in the trial and the two animals with the lowest faecaLegg counts were selected as spare animals.
  • the 18 trial sheep (including the 2 spare animals) were sacrificed on 27 th June 2002 (Day 10) for collection of faecal samples, abomasal and small intestine contents. Individual faecal egg counts, treatment group coprocultures and total worm counts were conducted for calculation of treatment efficacies.
  • Drenchrites (CSIRO Research - Horizon Technology 1996) was performed between the 10 th July and the 23 rd August 2002 to clarify that strains of Trichostrongylus colubriformis used were resistant to levamisole hydrochloride and albendazole and, Osteratagia circumcincta were resistant to albendazole.
  • Example 4 abamectin / closantel /albendazole /levamisole hydrochloride
  • Table 10 Larval differentiation results followin rou bulk co roculture- Larvae as a % of the total number counted.
  • Example 4 Excellent control (>99.9% reduction) was achieved by the Example 4 formulation against the major nematodes, macrocyclic lactone and closantel resistant strains of Haemonchus spp. (adult and immature stages - geometric means), macrocyclic and albendazole resistant strains Ostertagia spp. (adult, immature and L4 stages - geometric means) and levamisole hydrochloride and albendazole resistant strains of Trichostrongylus spp (adult and immature stages - geometric means) as assessed by geometric total worm counts.
  • Trial JUA1240r A property faecal egg count reduction study evaluating the therapeutic efficacy of the Example 4 formulation against field strains of mixed nematode population of either Haemonchus contortus, Trichostrongylus colubriformis and/or Teladorsagia circumcincta in sheep.
  • the aim of this field study was to study and evaluate under field conditions, the therapeutic efficacy of Example 4 when administered to sheep that are known to be harbouring resistant strains of nematodes.
  • the selected trial site was known to harbour closantel resistant Haemonchus contortus. This however was not confirmed during the initial phase of the study as a full dose of closantel was admimstered (as stated in the protocol).
  • Standard industry practice for diagnosis of closantel resistance in the field involves either the administration of a full dose of closantel and sequential sampling of treated sheep over three to six weeks post treatment, or alternatively administration of a 1/3 dose and sampling at 10 to 14 days post treatment.
  • a second faecal egg count reduction study was conducted after consultation with the Study Sponsor to confirm the closantel resistance status at the trial site, "Kelvin East".
  • the second phase of the study involved two groups of sheep each consisting of ten animals. Ten random faecal samples were collected prior to treatment from the mob of wethers to confirm a nematode burden of greater than 400 eggs/gram, and a group coproculture that confirmed a very high percentage (91%) of Haemonchus contortus were present.
  • Treatment Day Day 0
  • individual faecal samples were collected from twenty animals as they presented in the race. These animals were weighed and weights recorded and treatments administered in accordance to the treatment regime (detailed in Table 12). Faecal samples were returned to Veterinary Health Research for individual faecal egg counts and group coprocultures. Animals were observed post treatment for adverse reactions. None were detected.
  • Table 14 Group arithmetic mean faecal egg counts and body weights at Day 0.
  • Table 15 Group arithmetic and geometric mean faecal egg counts (epg).
  • Table 16 Overall percentage efficacy calculated using arithmetic and geometric group mean faecal egg counts.
  • Table 20 Group arithmetic mean faecal egg counts and body weights at Day 0.
  • Table 21 Group arithmetic and geometric mean faecal egg counts.
  • Table 23 Nematode population % - Pre-trial, Day 0 and Day 11 (based on faecal culture and larval differentiation).
  • the second faecal egg count reduction test was to confirm the presence closantel resistant Haemonchus at the trial site. This was achieved by administering a one third dose of closantel to a group of ten (10) animals and the addition of another group often (10) animals retained as untreated controls.
  • the use of a one third dose of closantel is standard industry practice for diagnosis of closantel resistance in the field. Reduced efficacy of closantel was observed against Haemonchus, confirming. The presence of closantel resistant Haemonchus at the trial site.
  • Example 4 Excellent efficacy (> 99.0%) was attained by the Example 4 formulation against a mixed gastrointestinal population including closantel resistant Haemonchus as well as levamisole and benzimidazole resistant Trichostrongylus.
  • Trial JUA1273r A property faecal egg count reduction study evaluating the therapeutic efficacy of the Example 4 formulation against field strains of mixed nematode populations, including closantel resistant strains of Haemonchus contortus in sheep.
  • Trial sheep had already been identified Using uniquely numbered ear tags as part of standard farming practice at the trial site. From the ninety (90) potential trial sheep sixty (60) sheep were selected and allocated (according to individual strongyle faecal egg counts) to six (6) groups of ten (10) sheep each, such that each group had a similar group arithmetic mean strongyle faecal egg count and range of faecal egg counts within the group.
  • Trial sheep in Group 2 were treated according to individual body weight with the test formulation, trial sheep in Groups 3-6 were treated with the respective reference formulation and trial sheep in Group 1 were retained untreated as negative controls.
  • Groups 2, 3, 5 and 6 were treated at the recommended dose rate for each active, while sheep in Group 4 were treated at one third the normal closantel dose rate, to determine and demonstrate the presence of closantel resistance (Reference: Rolfe PF; Fourth International Congress for Sheep Veterinarians 1997, pg 55). Sheep were observed in the immediate post-treatment period for adverse reactions (none were observed). Individual strongyle faecal egg counts and group bulk coprocultures for larval differentiation were subsequently performed on the samples collected. Trial sheep were returned to the sheep yards on Day 13 of the trial (1 st October 2002) and individual faecal samples again collected. All trial sheep received a single therapeutic dose of Rycozole® 1 due to animal welfare concerns. Individual strongyle faecal egg counts and group bulk coprocultures for larval differentiation were subsequently performed on the samples collected.
  • Treatment efficacies were then calculated using group arithmetic and geometric strongyle faecal egg counts for the major strongyle species present (see figures 8 and 9 and note that the treatment "Jurox" refers to treatment with Example 4).
  • Table 26 Group arithmetic mean, maximum and minimum strongyle faecal egg counts and standard deviations following allocation.
  • Table 29 Group Arithmetic and Geometric Mean strongyle faecal egg counts during the trial (excluding Nematodirus spp.)
  • Table 30 Larval differentiation results from group bulk coprocultures.
  • Table 31 Overall treatment efficacies, against all strongyle species (apart from Nematodirus s .
  • Efficacies attained by the comparison formulations against this strain of Haemonchus contortus ranged from 85.5% for the albendazole formulation (Valbazen®) through 96.1% for the ivermectin formulation (Ivomec®) to 99.8% for the levamisole formulation (Levamisole®), based on group arithmetic mean faecal egg counts and larval differentiation. Efficacies attained against this strain based on geometric mean faecal egg counts and larval differentiation were 84.9%, 97.5% and >99.9% for these formulations respectively.
  • Treatment with a 1/3 dose of closantel resulted in a treatment efficacy of 83.0% based on arithmetic group mean faecal egg counts and a treatment efficacy of 86.8% based on geometric group mean faecal egg counts, confirming the presence of moderate closantel resistance by this Haemonchus strain.
  • Insufficient numbers of other gastrointestinal strongyles Nematodirus, Teolodorsagia and Trichostrongylus species were present to draw any conclusions about efficacy of the test formulation against these strains.
  • Trial JUA1270r A property faecal egg count reduction study evaluating the therapeutic efficacy of the Example 4 formulation against field strains of mixed nematode populations, including macrocyclic lactone resistant strains of Haemonchus contortus in sheep in sheep.
  • Treatment efficacies were then calculated using group arithmetic and geometric strongyle faecal egg counts for the major strongyle species present (see figures 11 and 12 and note that the treatment "Jurox" refers to treatment with Example 4).
  • Table 33 Treatment table.
  • Table 34 Grou arithmetic mean, maximum and minimum stron le faecal e counts and standard deviations followin allocation.
  • Table 37 Group Arithmetic and Geometric Mean strongyle faecal egg counts during the trial.
  • Haemonchus spp. Trichostrongylus spp., "Cooperia spp., Oesophagostomum spp
  • Table 39 Treatment efficacies against Haemonchus contortus.

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Abstract

La présente invention concerne le traitement d'infections anthelmintiques chez des animaux, et plus particulièrement des compositions qui sont efficaces pour lutter contre des parasites qui résistent à une large variété de traitements médicamenteux. Dans un premier aspect, l'invention concerne une composition synergique efficace d'un point de vue anthelmintique comprenant au moins un composé appartenant à l'un des groupes suivants: lactones macrocycliques, benzimidazoles, salicylanilides et imidazothiazoles, et un excipient acceptable d'un point de vue thérapeutique. Dans un second aspect, l'invention concerne un procédé pour traiter des infections parasitaires chez un animal, comprenant l'administration à l'animal d'une quantité synergique efficace d'un point de vue anthelmintique d'une composition comprenant au moins un composé appartenant à l'un des groupes suivants: lactones macrocycliques, benzimidazoles, salicylanilides et imidazothiazoles, et un excipient acceptable d'un point de vue thérapeutique. Dans un troisième aspect, l'invention concerne l'utilisation pour le traitement d'une infection parasitaire chez un animal, d'une quantité synergique efficace d'un point de vue anthelmintique d'une composition comprenant au moins un composé appartenant à l'un des groupes suivants: lactones macrocycliques, benzimidazoles, salicylanilides et imidazothiazoles, et un excipient acceptable d'un point de vue thérapeutique.
PCT/AU2004/000126 2003-02-05 2004-02-04 Composition anthelmintique WO2004069242A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
GB0516881A GB2413764B8 (en) 2003-02-05 2004-02-04 Anthelmintic compostion
BRPI0407271A BRPI0407271B1 (pt) 2003-02-05 2004-02-04 composição anti-helmíntica
NZ540391A NZ540391A (en) 2003-02-05 2004-02-04 Anthelmintic composition
AU2004210461A AU2004210461C1 (en) 2003-02-05 2004-02-04 Anthelmintic composition
AU2009201942A AU2009201942C1 (en) 2003-02-05 2009-05-15 Anthelmintic composition

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AU2003900505A AU2003900505A0 (en) 2003-02-05 2003-02-05 Anthelmintic composition
AU2003900505 2003-02-05

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AU (3) AU2003900505A0 (fr)
BR (1) BRPI0407271B1 (fr)
GB (1) GB2413764B8 (fr)
NZ (1) NZ540391A (fr)
WO (1) WO2004069242A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2403905A (en) * 2003-07-12 2005-01-19 Norbrook Lab Ltd Parasiticidal composition
WO2009004432A1 (fr) * 2007-06-29 2009-01-08 Pfizer Inc. Combinaison anthelminthique
WO2009060063A1 (fr) * 2007-11-09 2009-05-14 Intervet International B.V. Combinaison anthelminthique
WO2011027333A1 (fr) * 2009-09-07 2011-03-10 Douglas Robert Cleverly Préparations anthelmintiques granulées
WO2011143479A1 (fr) * 2010-05-12 2011-11-17 Merial Limited Formulations parasiticides injectables de lévamisole et de lactones macrocycliques
AU2010100349B4 (en) * 2009-04-15 2012-03-29 Jurox Pty Ltd Anthelmintic formulation
WO2013030702A2 (fr) 2011-08-16 2013-03-07 Virbac Sa Formulations et traitements anthelminthiques
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RU2774960C2 (ru) * 2017-08-04 2022-06-24 Байер Энимэл Хельс ГмбХ Хинолиновые производные для лечения инфекций, вызванных гельминтами

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GB2403905B (en) * 2003-07-12 2005-12-14 Norbrook Lab Ltd Parasiticidal composition
GB2403905A (en) * 2003-07-12 2005-01-19 Norbrook Lab Ltd Parasiticidal composition
US8993546B2 (en) 2003-07-12 2015-03-31 Norbrook Laboratories Limited Parasiticidal composition
WO2009004432A1 (fr) * 2007-06-29 2009-01-08 Pfizer Inc. Combinaison anthelminthique
US8440633B2 (en) 2007-06-29 2013-05-14 Ah Usa 42 Llc Anthelmintic combination
AU2008272646B2 (en) * 2007-06-29 2013-08-22 Zoetis Services Llc Anthelmintic combination
WO2009060063A1 (fr) * 2007-11-09 2009-05-14 Intervet International B.V. Combinaison anthelminthique
AU2010100349B4 (en) * 2009-04-15 2012-03-29 Jurox Pty Ltd Anthelmintic formulation
AU2020202781B2 (en) * 2009-09-07 2021-05-13 Argenta Innovation Limited Granulated anthelmintic preparations and delivery systems
WO2011027333A1 (fr) * 2009-09-07 2011-03-10 Douglas Robert Cleverly Préparations anthelmintiques granulées
AU2022200149B2 (en) * 2009-09-07 2023-06-15 Argenta Innovation Limited Granulated anthelmintic preparations and delivery systems
US11253593B2 (en) 2009-09-07 2022-02-22 Argenta Innovation Limited Granulated anthelmintic preparations and delivery systems
AU2011252987B2 (en) * 2010-05-12 2013-05-02 Boehringer Ingelheim Animal Health USA Inc. Injectable parasiticidal formulations of levamisole and macrocyclic lactones
WO2011143479A1 (fr) * 2010-05-12 2011-11-17 Merial Limited Formulations parasiticides injectables de lévamisole et de lactones macrocycliques
US9198430B2 (en) 2011-06-23 2015-12-01 Bayer New Zealand Limited Anti-parasitic composition comprising a macrocyclic lactone and levamisole and method of treatment of parasitic infestation
EP2744495B1 (fr) 2011-08-16 2017-01-18 Virbac Composition antihelmintique et traitements
WO2013030702A2 (fr) 2011-08-16 2013-03-07 Virbac Sa Formulations et traitements anthelminthiques
WO2018038623A1 (fr) * 2016-08-23 2018-03-01 Donaghys Limited Améliorations apportées à des traitements de parasites
RU2774960C2 (ru) * 2017-08-04 2022-06-24 Байер Энимэл Хельс ГмбХ Хинолиновые производные для лечения инфекций, вызванных гельминтами

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GB2413764B8 (en) 2013-10-16
BRPI0407271B1 (pt) 2015-11-10
NZ540391A (en) 2006-12-22
GB2413764A8 (en) 2013-10-16
GB0516881D0 (en) 2005-09-28
AU2009201942B2 (en) 2012-02-16

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