WO1995005812A1 - Anthelmintic formulations - Google Patents

Anthelmintic formulations Download PDF

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Publication number
WO1995005812A1
WO1995005812A1 PCT/NZ1994/000084 NZ9400084W WO9505812A1 WO 1995005812 A1 WO1995005812 A1 WO 1995005812A1 NZ 9400084 W NZ9400084 W NZ 9400084W WO 9505812 A1 WO9505812 A1 WO 9505812A1
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WO
WIPO (PCT)
Prior art keywords
anthelmintic
composition
closantel
glycol
milbemycins
Prior art date
Application number
PCT/NZ1994/000084
Other languages
French (fr)
Inventor
Colin Manson Harvey
Original Assignee
Ashmont Holdings Limited
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 Ashmont Holdings Limited filed Critical Ashmont Holdings Limited
Priority to EP94924428A priority Critical patent/EP0724437A4/en
Priority to AU74694/94A priority patent/AU695582B2/en
Publication of WO1995005812A1 publication Critical patent/WO1995005812A1/en

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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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—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
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones

Definitions

  • This invention relates to veterinary compositions for the treatment of helminthiasis in warm-blooded animals, more particularly cattle, sheep, goats, and other domesticated herbivores.
  • Helminthiasis is a widely occurring disease in farmed animals. It commonly causes clinical disease and has significant adverse economic effects on farming economies j r j when present at subclinical levels. Over the past twenty-five years a number of initially successful anthelmmtic agents, with relatively specific effects on the metabolism of smaller or larger groups of endoparasites have been discovered, trialled, and used successfully to control helminthiasis on farms. Various groups of compounds have a greater or lesser spectrum of activity - that is to say they are able to destroy a wider or smaller range of parasite.
  • ivermectin is active against parasitic roundworms and also against some ectoparasites, yet it is inactive against tapeworms because of a difference ih their biochemical constitution.
  • Tericlabendazole is active only against the liver fluke Fasciola hepatica.
  • the drug closantel is a useful anthelmintic active agent that gives control over a range 25 of internal parasites including liverfluke in cattle and sheep. For this reason it has been used in aqueous suspension in combination with other anthelmintics such as albendazole and mebendazole.
  • This invention is based on the surprising discovery that an anthelmintic solution can be prepared from a combination of closantel and an avermectin or milbemycin like
  • anthelmintic for example ivermectin, moxidectin and doramectin.
  • ivermectin for example ivermectin, moxidectin and doramectin.
  • Glycol based solvents such as polyethylene glycol and propylene glycol are able to dissolve both compounds to produce a stable formulation.
  • Such formulations may also be dispersed in water.
  • the milbemycins are described in the 11th Edition of the Merck index as a family of novel macrolide antibiotics with Milbemycin D in particular being used as an anthelmintic.
  • the avermectins are described in the 11th Edition of the Merck index as a group of broad-spectrum antiparasitic compounds which are derivatives of pentacyclic 16-membered lactones related to the milbemycins.
  • the most well known of these avermectins is ivermectin which is a semi-synthetic derivative of abamectin (one of the avermectins).
  • the invention comprises a composition including an effective amount of the anthelmintic closantel together with a glycol based solvent and an effective amount of at least one other anthelmintic.
  • the invention provides a method for treating helminthiasis in animals with compositions comprising an effective amount of the anthelmintic closantel together with a glycol based solvent and an effective amount of at least one other anthelmintic.
  • the other anthelmintic is chosen from the group comprising the avermectins or milbemycins.
  • avermectins or milbemycins Such a group includes moxidectin, ivermectin, doramectin, Milbemycin D, as well as other milbemycins.
  • compositions of the present invention are used by injection. They may also include trace elements and/or vitamins.
  • the closantel and other anthelmintic may be each present at from 0.5 to 15% w/v respectively, and more preferably the closantel is present at from 1 to 2% w/v.
  • the invention provides a method of treating animals for helminthiasis by injecting a composition as previously described at the rate of lmL/50kg of the animal's live weight (different dose rates and percentages of active ingredients will become apparent from the examples).
  • the closantel and other anthelmintic is dissolved in a mixture selected from at least two of: propylene glycol, polyethylene glycol, glycerol formal and water.
  • This formulation is suitable for use as an oral drench for sheep which would offer control of parasites resistant to older anthelmintics such as the benzimidazoles and levamisole as well as controlling adult liverfluke.
  • This formulation is suitable for use as an injection for sheep and cattle. It gives the advantage of longer action of moxidectin combined with activity against liverfluke.
  • This injectable formulation can be applied to cattle at a dose rate of lmL/50kg of live weight, to provide the animal with 2.5mg/kg of closantel whilst at the same time supplying an effective dose of abamectin and a trace element such as selenium.
  • This provides another injectable formulation without the trace element by using a combination of polyethylene glycol (PEG 400) and glycerol formal.
  • Examples 5 - 7 show other injectable compositions containing different amounts of closantel to be used at a formulation dose rate of 1 mL/25kg of animal live weight.
  • compositions of this invention can contain trace elements.
  • Example 3 describes a composition containing selenium.
  • Other trace elements or vitamins may be included. Examples of trace elements include copper, cobalt, iodine, zinc or the like.
  • the vitamins may be for example vitamins A, B, D, or E.
  • compositions of this invention are stable and safe to use.
  • glycol based solvents used in this invention are non-irritant solvents and can safely be used in injectable compositions.
  • the injectable compositions are particularly suited to the control of helminthiasis in cattle.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Molecular Biology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

This invention relates to anthelmintic compositions and has particular application to injectable compositions containing closantel together with an avermectin or milbemycin such as moxidectin, ivermectin, doramectin Milbemycin D, or other milbemycins together with a glycol based solvent such as polyethylene glycol or propylene glycol. The formulations may also include trace elements and/or vitamins.

Description

ANTHELMINTIC FORMULATIONS
5
FIELD
This invention relates to veterinary compositions for the treatment of helminthiasis in warm-blooded animals, more particularly cattle, sheep, goats, and other domesticated herbivores.
10
BACKGROUND
Helminthiasis is a widely occurring disease in farmed animals. It commonly causes clinical disease and has significant adverse economic effects on farming economies jrj when present at subclinical levels. Over the past twenty-five years a number of initially successful anthelmmtic agents, with relatively specific effects on the metabolism of smaller or larger groups of endoparasites have been discovered, trialled, and used successfully to control helminthiasis on farms. Various groups of compounds have a greater or lesser spectrum of activity - that is to say they are able to destroy a wider or smaller range of parasite. For example, the widely used "ivermectin" is active against parasitic roundworms and also against some ectoparasites, yet it is inactive against tapeworms because of a difference ih their biochemical constitution. "Triclabendazole" is active only against the liver fluke Fasciola hepatica.
The drug closantel is a useful anthelmintic active agent that gives control over a range 25 of internal parasites including liverfluke in cattle and sheep. For this reason it has been used in aqueous suspension in combination with other anthelmintics such as albendazole and mebendazole.
This invention is based on the surprising discovery that an anthelmintic solution can be prepared from a combination of closantel and an avermectin or milbemycin like
30 anthelmintic, for example ivermectin, moxidectin and doramectin. Such solutions have advantages in ease of use and may also be used by injection. Glycol based solvents such as polyethylene glycol and propylene glycol are able to dissolve both compounds to produce a stable formulation. Such formulations may also be dispersed in water.
35 The milbemycins are described in the 11th Edition of the Merck index as a family of novel macrolide antibiotics with Milbemycin D in particular being used as an anthelmintic. The avermectins are described in the 11th Edition of the Merck index as a group of broad-spectrum antiparasitic compounds which are derivatives of pentacyclic 16-membered lactones related to the milbemycins. The most well known of these avermectins is ivermectin which is a semi-synthetic derivative of abamectin (one of the avermectins).
OBJECT
It is an object of this invention to provide novel veterinary compositions having anthelmintic activity.
STATEMENT OF INVENTION
In one aspect the invention comprises a composition including an effective amount of the anthelmintic closantel together with a glycol based solvent and an effective amount of at least one other anthelmintic.
In a further aspect the invention provides a method for treating helminthiasis in animals with compositions comprising an effective amount of the anthelmintic closantel together with a glycol based solvent and an effective amount of at least one other anthelmintic.
Preferably the other anthelmintic is chosen from the group comprising the avermectins or milbemycins. Such a group includes moxidectin, ivermectin, doramectin, Milbemycin D, as well as other milbemycins.
Preferably the compositions of the present invention are used by injection. They may also include trace elements and/or vitamins.
Preferably the closantel and other anthelmintic may be each present at from 0.5 to 15% w/v respectively, and more preferably the closantel is present at from 1 to 2% w/v.
In another aspect the invention provides a method of treating animals for helminthiasis by injecting a composition as previously described at the rate of lmL/50kg of the animal's live weight (different dose rates and percentages of active ingredients will become apparent from the examples).
Preferably the closantel and other anthelmintic is dissolved in a mixture selected from at least two of: propylene glycol, polyethylene glycol, glycerol formal and water.
EXAMPLES These and other aspects of the invention will be apparent from the following description, which is given by way of example only.
Figure imgf000005_0001
This formulation is suitable for use as an oral drench for sheep which would offer control of parasites resistant to older anthelmintics such as the benzimidazoles and levamisole as well as controlling adult liverfluke.
Figure imgf000005_0002
This formulation is suitable for use as an injection for sheep and cattle. It gives the advantage of longer action of moxidectin combined with activity against liverfluke.
Figure imgf000005_0003
This is an injectable composition containing selenium.
Preparation Example To a clean dry mixing vessel, add the glycerol formal (i) and Tween 80. With stirring, add the abamectin and sodium closantel, and heat to about 60" - 70* C with continued stirring until dissolved. Dissolve the sodium selenate in water and add to the batch while stirring. Allow to cool to room temperature and add the benzyl alcohol, stirring well to disperse. Make up to 100% volume with glycerol formal (ii).
Trial solutions of Example 3 were found to be stable overnight at 2*C, 21*C and 37°C with the active ingredients remaining soluble at all temperatures.
Use
This injectable formulation can be applied to cattle at a dose rate of lmL/50kg of live weight, to provide the animal with 2.5mg/kg of closantel whilst at the same time supplying an effective dose of abamectin and a trace element such as selenium.
Example 4:
Dose rate lml/50kg
Figure imgf000006_0001
This provides another injectable formulation without the trace element by using a combination of polyethylene glycol (PEG 400) and glycerol formal.
Examples 5 - 7 show other injectable compositions containing different amounts of closantel to be used at a formulation dose rate of 1 mL/25kg of animal live weight.
Figure imgf000007_0001
Dose rate lml/25kg
Figure imgf000007_0002
In addition to the combination of closantel and an avermectin or milbemycin the compositions of this invention can contain trace elements. Example 3 describes a composition containing selenium. Other trace elements or vitamins may be included. Examples of trace elements include copper, cobalt, iodine, zinc or the like. The vitamins may be for example vitamins A, B, D, or E.
ADVANTAGES
The compositions of this invention are stable and safe to use. The glycol based solvents used in this invention are non-irritant solvents and can safely be used in injectable compositions. The injectable compositions are particularly suited to the control of helminthiasis in cattle.

Claims

1. A composition including an effective amount of the anthelmintic closantel together with a glycol based solvent and an effective amount of at least one other anthelmintic.
2. A composition as claimed in claim 1 wherein the other anthelmintic is selected from the group comprising the avermectins and milbemycins.
3. A composition as claimed in claim 2 wherein the avermectins and milbemycins are selected from the group comprising abamectin, ivermectin, moxidectin, doramectin and Milbemycin D.
4. A composition as claimed in any one of claims 1-3 wherein the closantel and other anthelmintic is dissolved in a solvent selected from the group comprising: propylene glycol, polyethylene glycol, glycerol formal and water.
5. A composition as claimed in claim 4 wherein the closantel and other anthelmintic are each present at from 0.5 to 15% w/v respectively.
6. An injectable formulation comprising a composition as claimed in any one of claims 1-5.
7. An injectable formulation comprising a composition as claimed in claim 6 wherein the closantel is present at from 1 to 2% w v.
A composition as claimed in any one of claims 1 to 7 wherein the closantel and other anthelmintic is dissolved in a mixture selected from at least two of: propylene glycol, polyethylene glycol, glycerol formal and water.
A method of treating animals for helminthiasis by injecting a composition as claimed in claim 7 at the rate of lmL/25kg to lmL/50kg of the animal's live weight.
PCT/NZ1994/000084 1993-08-24 1994-08-22 Anthelmintic formulations WO1995005812A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP94924428A EP0724437A4 (en) 1993-08-24 1994-08-22 Anthelmintic formulations
AU74694/94A AU695582B2 (en) 1993-08-24 1994-08-22 Anthelmintic formulations

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NZ248486 1993-08-24
NZ248486A NZ248486A (en) 1993-08-24 1993-08-24 Stable anthelmintic formulation containing closantel and one or more avermectins or milbemycins in a glycol based solvent

Publications (1)

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WO1995005812A1 true WO1995005812A1 (en) 1995-03-02

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Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997013508A1 (en) * 1995-10-13 1997-04-17 Virbac S.A. Topical liquid composition, method for preparing same and uses thereof
AU694016B2 (en) * 1995-05-10 1998-07-09 Virbac (Australia) Pty Limited Canine anthelmintic preparation
EP0916347A1 (en) * 1997-11-18 1999-05-19 Uni-Pharma Kleon Tsetis A.B.E.E., Farmakeftika Ergastiria Pharmaceutical injectable solutions containing paracetamol and combinations of paracetamol with other active substances
US6013636A (en) * 1995-09-25 2000-01-11 Ashmont Holdings Limited Anthelmintic macrocyclic lactone compositions
WO2000004906A1 (en) * 1998-07-24 2000-02-03 Norbrook Laboratories Limited Non-aqueous anthelmintic composition
WO2000047048A1 (en) * 1999-02-08 2000-08-17 Virbac (Australia) Pty. Limited Pesticide treatment
US6193989B1 (en) * 1997-03-21 2001-02-27 Biogenesis S.A. Long acting injectable parasiticidal composition and the process for its preparation
WO2002009764A1 (en) * 2000-07-13 2002-02-07 Ashmont Holdings Limited Combination compositions
EP1215964A1 (en) * 1999-09-22 2002-06-26 Ashmont Holdings Limited Sheep pour-on
KR20020067781A (en) * 2001-02-19 2002-08-24 주식회사 엘지씨아이 Anthelmintic injectable composition containing ivermectin and process for preparation thereof
US6596714B1 (en) * 2000-05-18 2003-07-22 Phoenix Scientific, Inc. Parasiticidal formulation for animals and a method of making this formulation
WO2003072113A1 (en) * 2002-02-28 2003-09-04 Norbrook Laboratories Limited Long acting parasiticidal composition containing a salicylanilide compound, a polymeric species and at least one other anti-parasitic compound
WO2003072112A1 (en) * 2002-02-28 2003-09-04 Norbrook Laboratories Limited 'long'-'acting' injectable parasiticidal composition
FR2839614A1 (en) * 2002-05-14 2003-11-21 Virbac Sa Broad spectrum veterinary antiparasitic composition comprising macrocyclic lactone, e.g. ivermectin, and closantel, in oily vehicle
GB2403905A (en) * 2003-07-12 2005-01-19 Norbrook Lab Ltd Parasiticidal composition
WO2005074912A2 (en) * 2004-02-02 2005-08-18 Wyeth Antiparasitic composition containing an organic amine salt of closantel
WO2006061214A1 (en) * 2004-12-10 2006-06-15 Bayer Healthcare Ag Anthelmintic composition
WO2007032688A1 (en) * 2005-09-15 2007-03-22 Ashmont Holdings Limited Anthelmintic formulations
WO2007068073A2 (en) 2005-12-16 2007-06-21 Ouro Fino Participações E Empreendimentos S/A Veterinarian composition comprising an organic salt of levamisole in combination with at least one avermectine and/or milbemycine
WO2007024719A3 (en) * 2005-08-19 2007-08-09 Merial Ltd Long acting injectable parasiticidal formulations
WO2010008891A2 (en) * 2008-06-24 2010-01-21 Merial Limited Anthelminthic formulations
CN103417477A (en) * 2012-05-18 2013-12-04 中国农业科学院兰州畜牧与兽药研究所 Doramectin O/W type injection taking water as matrix and preparation method thereof

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NZ701697A (en) 2014-03-24 2016-05-27 Donaghys Ltd Stable veterinary anthelmintic formulations

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Cited By (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU694016B2 (en) * 1995-05-10 1998-07-09 Virbac (Australia) Pty Limited Canine anthelmintic preparation
US6013636A (en) * 1995-09-25 2000-01-11 Ashmont Holdings Limited Anthelmintic macrocyclic lactone compositions
FR2739778A1 (en) * 1995-10-13 1997-04-18 Virbac Lab TOPICAL FORMULATION FOR TREATING LIVER LIVING DISEASE IN ANIMALS
WO1997013508A1 (en) * 1995-10-13 1997-04-17 Virbac S.A. Topical liquid composition, method for preparing same and uses thereof
US6193989B1 (en) * 1997-03-21 2001-02-27 Biogenesis S.A. Long acting injectable parasiticidal composition and the process for its preparation
EP0916347A1 (en) * 1997-11-18 1999-05-19 Uni-Pharma Kleon Tsetis A.B.E.E., Farmakeftika Ergastiria Pharmaceutical injectable solutions containing paracetamol and combinations of paracetamol with other active substances
GB2339691A (en) * 1998-07-24 2000-02-09 Norbrook Lab Ltd Veterinary compositions comprising an anthelmintic agent, polyethylene glycol and glycerol formal
WO2000004906A1 (en) * 1998-07-24 2000-02-03 Norbrook Laboratories Limited Non-aqueous anthelmintic composition
WO2000047048A1 (en) * 1999-02-08 2000-08-17 Virbac (Australia) Pty. Limited Pesticide treatment
EP1215964A1 (en) * 1999-09-22 2002-06-26 Ashmont Holdings Limited Sheep pour-on
EP1215964A4 (en) * 1999-09-22 2002-11-05 Ashmont Holdings Ltd Sheep pour-on
US6858601B2 (en) 2000-05-18 2005-02-22 Phoenix Scientific, Inc. Parasiticidal formulation for animals
US6596714B1 (en) * 2000-05-18 2003-07-22 Phoenix Scientific, Inc. Parasiticidal formulation for animals and a method of making this formulation
WO2002009764A1 (en) * 2000-07-13 2002-02-07 Ashmont Holdings Limited Combination compositions
KR20020067781A (en) * 2001-02-19 2002-08-24 주식회사 엘지씨아이 Anthelmintic injectable composition containing ivermectin and process for preparation thereof
US9289380B2 (en) 2002-02-28 2016-03-22 Norbrook Laboratories Limited Long acting parasiticidal composition containing a salicylanilide compound, a polymeric species and at least one other anti-parasitic compound
GB2386066A (en) * 2002-02-28 2003-09-10 Norbrook Lab Ltd Long-acting parasiticidal composition with improved bioavailability comprising a salicylanilide, a further anti-parasitic compound & a polymeric species
GB2386067A (en) * 2002-02-28 2003-09-10 Norbrook Lab Ltd Long-acting parasiticidal composition with improved bioavailability comprising an avermectin or milbemycin, plus a salicylanilide & a polymeric species
AP1977A (en) * 2002-02-28 2009-03-19 Norbrook Lab Ltd Long acting parasiticidal composition
WO2003072112A1 (en) * 2002-02-28 2003-09-04 Norbrook Laboratories Limited 'long'-'acting' injectable parasiticidal composition
WO2003072113A1 (en) * 2002-02-28 2003-09-04 Norbrook Laboratories Limited Long acting parasiticidal composition containing a salicylanilide compound, a polymeric species and at least one other anti-parasitic compound
FR2839614A1 (en) * 2002-05-14 2003-11-21 Virbac Sa Broad spectrum veterinary antiparasitic composition comprising macrocyclic lactone, e.g. ivermectin, and closantel, in oily vehicle
WO2003099259A1 (en) * 2002-05-14 2003-12-04 Virbac S.A. Oleaginous oral antiparasitic compositions
EA009602B1 (en) * 2003-07-12 2008-02-28 Норбрук Лэборетериз Лимитед Antiparasiticidal composition
GB2403905A (en) * 2003-07-12 2005-01-19 Norbrook Lab Ltd Parasiticidal composition
CN1822880B (en) * 2003-07-12 2012-07-11 诺布鲁克有限公司 Parasiticidal composition
AP2956A (en) * 2003-07-12 2014-08-31 Norbrook Lab Ltd Parasiticidal composition
GB2403905B (en) * 2003-07-12 2005-12-14 Norbrook Lab Ltd Parasiticidal composition
US8993546B2 (en) 2003-07-12 2015-03-31 Norbrook Laboratories Limited Parasiticidal composition
WO2005007241A1 (en) * 2003-07-12 2005-01-27 Norbrook Laboratories Limited Parasiticidal composition
EP2286876A1 (en) 2003-07-12 2011-02-23 Norbrook Laboratories Limited Parasiticidal composition
AU2004257450B2 (en) * 2003-07-12 2008-08-28 Norbrook Laboratories Limited Parasiticidal composition
WO2005074912A2 (en) * 2004-02-02 2005-08-18 Wyeth Antiparasitic composition containing an organic amine salt of closantel
EP2065042A3 (en) * 2004-02-02 2009-07-22 Wyeth Antiparasitic composition containing an organic amine salt of closantel
US7666444B2 (en) 2004-02-02 2010-02-23 Wyeth Antiparasitic composition
WO2005074912A3 (en) * 2004-02-02 2006-04-20 Wyeth Corp Antiparasitic composition containing an organic amine salt of closantel
WO2006061214A1 (en) * 2004-12-10 2006-06-15 Bayer Healthcare Ag Anthelmintic composition
WO2007024719A3 (en) * 2005-08-19 2007-08-09 Merial Ltd Long acting injectable parasiticidal formulations
US8362086B2 (en) 2005-08-19 2013-01-29 Merial Limited Long acting injectable formulations
EP3479818A1 (en) * 2005-08-19 2019-05-08 Merial, Inc. Long acting injectable parasiticidal formulations
WO2007032688A1 (en) * 2005-09-15 2007-03-22 Ashmont Holdings Limited Anthelmintic formulations
WO2007068073A2 (en) 2005-12-16 2007-06-21 Ouro Fino Participações E Empreendimentos S/A Veterinarian composition comprising an organic salt of levamisole in combination with at least one avermectine and/or milbemycine
WO2010008891A3 (en) * 2008-06-24 2011-01-20 Merial Limited Anthelminthic formulations
WO2010008891A2 (en) * 2008-06-24 2010-01-21 Merial Limited Anthelminthic formulations
CN103417477A (en) * 2012-05-18 2013-12-04 中国农业科学院兰州畜牧与兽药研究所 Doramectin O/W type injection taking water as matrix and preparation method thereof

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AU7469494A (en) 1995-03-21
EP0724437A4 (en) 1998-07-29
EP0724437A1 (en) 1996-08-07
ZA946195B (en) 1995-05-22
NZ248486A (en) 1996-07-26
AU695582B2 (en) 1998-08-13

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