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WO2003072112A1 - Composition antiparasitaire injectable a action prolongee - Google Patents

Composition antiparasitaire injectable a action prolongee Download PDF

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Publication number
WO2003072112A1
WO2003072112A1 PCT/GB2003/000535 GB0300535W WO03072112A1 WO 2003072112 A1 WO2003072112 A1 WO 2003072112A1 GB 0300535 W GB0300535 W GB 0300535W WO 03072112 A1 WO03072112 A1 WO 03072112A1
Authority
WO
WIPO (PCT)
Prior art keywords
closantel
composition according
amount
composition
ivermectin
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.)
Ceased
Application number
PCT/GB2003/000535
Other languages
English (en)
Inventor
William Blakely
Lillian Cromie
Sean Duffy
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.)
Norbrook Laboratories Ltd
Original Assignee
Norbrook Laboratories Ltd
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 Norbrook Laboratories Ltd filed Critical Norbrook Laboratories Ltd
Priority to AU2003205858A priority Critical patent/AU2003205858A1/en
Publication of WO2003072112A1 publication Critical patent/WO2003072112A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • A61K31/16—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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides

Definitions

  • This invention relates to injectable parasiticidal compositions, especially combination products for veterinary use, based on for example an avermectin or milbemycin together with another parasiticidal agent.
  • Such combination products exhibit efficacy across a broader spectrum of parasites than is observed with the use of a single parasiticidal agent alone.
  • Oral drenches, pastes, boluses, tablets, and granules for incorporating into feed mixes are known methods capable of being used by the animal husbandrymen, but other methods which are intended to avoid use of the gastrointestinal route are typically administered by qualified practitioners. Such other methods include use of aerosols, and parenteral drug compositions which are selectively prepared as solution or suspension or micronised powder formulations intended for subcutaneous, intracutaneous, and intramuscular injection according to the intended delivery regime. These last methods require special care in formulation to avoid irritation at the site of injection or possible adverse allergic or pyrogenic reactions.
  • Injectable formulations are typically prepared using aqueous or non- aqueous (“solvent”) vehicles.
  • solvent aqueous or non- aqueous
  • the latter class may comprise physiologically tolerable alcohols, glycols, esters, a limited range of organic aromatic solvents, and vegetable oils and extracts or modified forms thereof.
  • solvent aqueous or non- aqueous
  • the skilled person has to consider a number of issues including, solubility of the intended active ingredient(s), the affinity of the drug to certain vehicles, whether it will affect any essential auxiliaries, pH, stability over time, viscosity, and naturally the risk of any toxic effect upon the animal to be treated. Therefore, formulation of a parasiticide is a complex task.
  • Traditional parasiticides include chemical agents such as the benzimidazoles, and carbamates, and plant extracts such as the pyrethroids, which tend to be used to combat ectoparasites such as ticks and mites.
  • the avermectins are very potent antiparasitic agents which are useful against a broad spectrum of endoparasites and ectoparasites in mammals as well as having agricultural uses against various parasites found in and on crops and soil.
  • the basic avermectin compounds are isolated from the fermentation broth of the soil micro-organism Streptomyces avermitilis and these compounds are described in US patent US 4310 519. Furthermore, derivatives of these basic avermectin compounds have been prepared by a variety of chemical means.
  • avermectin group of compounds contain a 22, 23-double bond and others contain a disaccharide at the 13-position which consists of ⁇ -L- oleandrosyl- ⁇ -L-oleandrosyl group.
  • One or both saccharide units can be removed forming a monosaccharide or an aglycone (where both saccharides are removed) as described in US patent US 4206205.
  • the aglycone derivatives possess a hydroxy group at the 13 position which may be removed to form the 13-deoxy compound as described in the patents US 4 171 314 and US 4 173 571. Acylation of hydroxy groups on the avermectin compounds and derivatives can be carried out as described in US 4 201 861.
  • milbemycin series of compounds disclosed in US 3 950 360, are structurally similar to the avermectin family in that they contain the sixteen membered macrocyclic ring. However, they do not contain the disaccharide sub- unit and there are differences in the substituent groups.
  • Ivermectin disclosed in US 4 199 569, is prepared by the selective reduction of the 22, 23 double bond of the avermectin compounds.
  • Ivermectin is a mixture of 22, 23-dihydro Avermectin B1 a and B1 b in a ratio of at least 80:20.
  • Ivermectin is an especially preferred active component in pesticidal compositions, and there is extensive literature on its activity, demonstrating its efficacy against internal and external parasites, and its ability to interfere in the life cycle of certain parasites.
  • ivermectin for the purposes of delivery in a variety of presentations, e.g. as an oral drench, pour-on, parenteral formulations, granules for adding to feed, and syringeable pastes, has proved highly challenging and numerous patents have been published on its use.
  • Ivermectin exhibits a lipophilic character but it can be solvated in aqueous systems, and various patents describe special solvent systems for use in its formulation. Thus reference may be made at least to EP 0 045 655, and EP 0 146 414 for example.
  • ivermectin is surprisingly effective, and has enjoyed a long period of commercial success, there remains a keen interest in exploiting ivermectin against a wider range of parasites and in overcoming tolerance by some parasites which demands higher amounts of ivermectin to be delivered. Taking into account the fact that a significant volume of use of ivermectin is in protecting and treating animals intended for human consumption, there are constraints on the residual amount of ivermectin in the carcass of such an animal. Therefore, high loadings of ivermectin, even if technically feasible, in a delivery system are not necessarily the optimum solution.
  • Combination formulations are also desirable taking account of acquired tolerance or resistance in pests to prolonged usage of other more traditional parasiticidal agents. This phenomenon is well documented, e.g. in relation to worming compositions. Synergistic effects or complementary effects of combined parasiticidal agents have been observed as a route to combating the aforesaid tolerance problem. Synergistic anthelmintic compositions are discussed in WO 94/28887, which focuses on substituted mono- and bisphenols, salicylanilides, benzene sulphonamides, halogenated benzimidazoles, benzimidazoles, and benzimidazole carbamates.
  • Closantel is described in US 4 005 218 and in the literature, e.g. J.Guerrero et al, J.Parasitol.68,616, (1983); H.Van den Bossche et al, Arch. Int. Physiol.Biochim, 87, 851 (1979); H.J.Kane et al, Mol.Biochem.Parasitol.1 , 347(1980).
  • Formulations of the pour-on and injectable type are discussed in WO 01/60380, which comprise use of a pyrrolidone solvent and a bridging solvent such as a xylene, optionally including a further solubility agent such as propylene glycol caprylic acids and esters or peanut oil.
  • a pyrrolidone solvent and a bridging solvent such as a xylene, optionally including a further solubility agent such as propylene glycol caprylic acids and esters or peanut oil.
  • a further solubility agent such as propylene glycol caprylic acids and esters or peanut oil.
  • Salicylanilide derivatives such as closantel provide useful control over a range of parasites and are especially useful against liver fluke.
  • the avermectin group of anti-parasitic compounds of which ivermectin is the best known example, provide complementary protection against many other parasites such as roundworms. Therefore, there are advantages to be gained if a combination of these drugs could be provided in a form that can be conveniently administered to livestock and which will provide effective control of parasitic infection.
  • the established dose rate for injection of livestock is of the order of 200 ⁇ g/kg (ivermectin) and 2.5mg/kg (closantel).
  • Ivermectin can be prepared in non-aqueous or low water content systems that are suitable for injection.
  • Glycerol formal, propylene glycol, polyethylene glycol, pyrrolidone, and related solvents have been used in various formulations, singly or in combination.
  • Patent publication WO 95/05812 discloses closantel and ivermectin solutions for injection using some of the solvents established as suitable for ivermectin (glycerol formal, polyethylene glycol, propylene glycol and water).
  • the effectiveness of the formulations, in terms of bioavailability of the active parasiticidal agents, described in that patent application were not disclosed.
  • Objects of the Invention Accordingly, it is an object of the present invention to provide improved veterinary pharmaceutical preparations.
  • preparations which are suitable for administration by injection It is a further object of this invention to provide preparations which are suitable for administration by injection.
  • a still further object of the invention is to provide a veterinary pharmaceutical product combining ivermectin and closantel in an effective formulation enabling enhanced bioavailability of closantel in excess of the observed prior art levels.
  • PVP polyvinylpyrrolidone
  • the invention enables the provision of injectable parasiticidal compositions, especially combination products, based on for example an avermectin or milbemycin together with another parasiticidal agent of the salicylanilide type with effective bioavailability of the parasiticidal agents.
  • an injectable parasiticidal composition prepared for treating animals comprises a first parasiticidal agent selected from amongst the avermectins and the milbemycins, typically in an amount of from 0.1 to 10% (w/v), together with another parasiticidal agent selected from the salicylanilides in an amount such that the injectable composition delivers at least about 2.5 mg salicylanilide per kilogram live weight of the animal to be treated, in a physiologically tolerable solvent system suitable for injection, characterised in that the composition comprises an amount of a polymeric species that is effective to improve bioavailability of the salicylanilide parasiticidal agent over a period of treatment.
  • a preferred injectable composition comprises ivermectin in an amount of from 0.1 to 10%(w/v), along with closantel in an amount sufficient to provide the required dosage amount.
  • the polymeric species is selected from a polyvinylpyrrolidone (PVP) or a polyoxypropylene/polyoxyethylene block copolymer, the former being especially preferred.
  • PVP polyvinylpyrrolidone
  • Polyoxypropylene/polyoxyethylene block copolymer the former being especially preferred.
  • Polyvinylpyrrolidone is available in powder form of various molecular weights (M w circa 10,000 up to 55,000, and above : Aldrich Catalogue 2000-2001) for pharmaceutical use and is generally adopted as a dispersing and suspending agent (Merck Index).
  • M w circa 10,000 up to 55,000 and above : Aldrich Catalogue 2000-2001
  • Merck Index dispersing and suspending agent
  • PVP is surprisingly found to be effective in the manufacture of an injectable parasiticidal composition comprising closantel having long acting efficacy, such that the amount of PVP used enables the desired period of efficacy to be designed into the formulation to provide a controllable period of effective treatment with a predictable depletion period permitting slaughter for human consumption of the treated animal if required.
  • a suitable solvent system comprises glycerol formal (GF), or a mixture of propylene glycol (PG) and GF, or a mixture of a polyethylene glycol (PEG) and GF.
  • GF glycerol formal
  • PG propylene glycol
  • PEG polyethylene glycol
  • a range of PEG solvents according to molecular weight is commercially available, and any of those, or others that may yet be made available, may be chosen for convenience provided that the PEG is presented or rendered available as a liquid during formulation.
  • PEG 200 to 1500 are readily to hand from commercial sources, and thus can be used for the purposes herein, but PEG 200 to PEG 600 are usefully employed in this invention.
  • a preferred solvent system consists of PEG 200 with GF.
  • an avermectin preferably ivermectin
  • a salicylanilide preferably closantel
  • the potential ranges of the preferred parasiticidal agents useful in such formulations are: Ivermectin - from 0.1 to 10% w/v, preferably 1 to 5 % w/v;
  • the quantity of polymeric species, especially polyvinylpyrrolidone, required to be effective depends on the desired salicylanilide activity of the mixture but typically at least 11 % PVP is required to permit the higher effective amounts of e.g. closantel desired to be achieved, and good results are demonstrated at levels of 15% or more.
  • PVP polyvinylpyrrolidone
  • Glycerol Formal q.s. ad 100%v/v C In the preparation of a 0.5%w/v ivermectin parenteral solution the composition was as follows:
  • Performance Examples 1 to 7 describe the trials of prior art proposals in comparison with formulations according to the invention.
  • the invention will be usefully applied in the field of veterinary medicine in particular for combating endoparasites and ectoparasites typically afflicting livestock such as bovines, equines, ovines and caprines.

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

Abstract

L'invention concerne une composition injectable destinée à traiter des animaux souffrant de parasites, ces parasites étant sensibles aux avermectines, aux milbémycines et/ou aux salicylanilides. Par exemple, ladite composition comprend de l'ivermectine dans une proportion comprise entre 0,1 et 10 % (poids/volume), un solvant choisi dans le groupe constitué par le glycérol formal, le propylène glycol, le polyéthylène glycol et des combinaisons correspondantes, ainsi qu'un salicylanilide, tel que le closantel, dans une proportion suffisante pour que la composition injectable diffuse environ 2,5 mg de closantel par kilogramme de poids vif de l'animal à traiter. Cette composition comprend en outre une espèce polymère choisie dans le groupe constitué par une polyvinylpyrrolidone et des copolymères blocs de polyoxypropylène/polyoxyéthylène, ladite espèce polymère améliorant la biodisponibilité du salicylanilide, et notamment du closantel.
PCT/GB2003/000535 2002-02-28 2003-02-12 Composition antiparasitaire injectable a action prolongee Ceased WO2003072112A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003205858A AU2003205858A1 (en) 2002-02-28 2003-02-12 "long"-"acting" injectable parasiticidal composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0204713A GB2386067A (en) 2002-02-28 2002-02-28 Long-acting parasiticidal composition with improved bioavailability comprising an avermectin or milbemycin, plus a salicylanilide & a polymeric species
GB0204713.2 2002-02-28

Publications (1)

Publication Number Publication Date
WO2003072112A1 true WO2003072112A1 (fr) 2003-09-04

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2003/000535 Ceased WO2003072112A1 (fr) 2002-02-28 2003-02-12 Composition antiparasitaire injectable a action prolongee

Country Status (4)

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AR (1) AR038853A1 (fr)
AU (1) AU2003205858A1 (fr)
GB (1) GB2386067A (fr)
WO (1) WO2003072112A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007024719A3 (fr) * 2005-08-19 2007-08-09 Merial Ltd Formulations injectables a action prolongee
WO2009053466A1 (fr) * 2007-10-25 2009-04-30 Schering-Plough Limited Formulations injectables longue durée
US7666444B2 (en) 2004-02-02 2010-02-23 Wyeth Antiparasitic composition
WO2015093924A1 (fr) * 2013-12-19 2015-06-25 CASTRO ALDRETE, Jorge Issac Véhicule pour l'administration de composés pharmaceutiques
WO2019050259A1 (fr) * 2017-09-06 2019-03-14 (주)인벤티지랩 Microparticules comprenant de la moxidectine et leur procédé de préparation
CN109966438A (zh) * 2019-05-17 2019-07-05 石家庄九鼎动物药业有限公司 一种兽用抗寄生虫药物伊维菌素注射液及其制备方法
US11931461B2 (en) 2017-09-06 2024-03-19 Inventage Lab Inc. Microparticles containing moxidectin, and preparation method therefor

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0316377D0 (en) * 2003-07-12 2003-08-13 Norbrook Lab Ltd Parasiticidal composition
SG153809A1 (en) 2004-06-07 2009-07-29 Syngenta Participations Ag Methods of reducing nematode damage
BRPI0506279B1 (pt) 2005-12-16 2018-01-09 Npa - Núcleo De Pesquisas Aplicadas Ltda Composição sinergística de antihelmínticos e endectocidas

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0628302A2 (fr) * 1993-03-15 1994-12-14 Colgate-Palmolive Company Composition orale contenant un salicylanilide antibacteriel
WO1995005812A1 (fr) * 1993-08-24 1995-03-02 Ashmont Holdings Limited Formulations anti-helminthiques
US6193989B1 (en) * 1997-03-21 2001-02-27 Biogenesis S.A. Long acting injectable parasiticidal composition and the process for its preparation
WO2002009764A1 (fr) * 2000-07-13 2002-02-07 Ashmont Holdings Limited Compositions combinees

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ223200A (en) * 1988-01-15 1989-01-06 Ancare Distributors Anthelmintic compositions containing 2',5-dicloro-4'-nitrosalicylanilide and non aqueous carrier

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0628302A2 (fr) * 1993-03-15 1994-12-14 Colgate-Palmolive Company Composition orale contenant un salicylanilide antibacteriel
WO1995005812A1 (fr) * 1993-08-24 1995-03-02 Ashmont Holdings Limited Formulations anti-helminthiques
US6193989B1 (en) * 1997-03-21 2001-02-27 Biogenesis S.A. Long acting injectable parasiticidal composition and the process for its preparation
WO2002009764A1 (fr) * 2000-07-13 2002-02-07 Ashmont Holdings Limited Compositions combinees

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7666444B2 (en) 2004-02-02 2010-02-23 Wyeth Antiparasitic composition
WO2007024719A3 (fr) * 2005-08-19 2007-08-09 Merial Ltd Formulations injectables a action prolongee
US8362086B2 (en) 2005-08-19 2013-01-29 Merial Limited Long acting injectable formulations
KR101351644B1 (ko) * 2005-08-19 2014-01-14 메리얼 리미티드 지속성 주사가능 기생충구충제 제형
EP3479818A1 (fr) * 2005-08-19 2019-05-08 Merial, Inc. Formulations parasiticides injectables à action prolongée
WO2009053466A1 (fr) * 2007-10-25 2009-04-30 Schering-Plough Limited Formulations injectables longue durée
WO2015093924A1 (fr) * 2013-12-19 2015-06-25 CASTRO ALDRETE, Jorge Issac Véhicule pour l'administration de composés pharmaceutiques
WO2019050259A1 (fr) * 2017-09-06 2019-03-14 (주)인벤티지랩 Microparticules comprenant de la moxidectine et leur procédé de préparation
US11931461B2 (en) 2017-09-06 2024-03-19 Inventage Lab Inc. Microparticles containing moxidectin, and preparation method therefor
CN109966438A (zh) * 2019-05-17 2019-07-05 石家庄九鼎动物药业有限公司 一种兽用抗寄生虫药物伊维菌素注射液及其制备方法

Also Published As

Publication number Publication date
GB0204713D0 (en) 2002-04-17
GB2386067A (en) 2003-09-10
AR038853A1 (es) 2005-01-26
AU2003205858A1 (en) 2003-09-09

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