WO2001037811A1 - Compositions permettant de liberer un ingredient actif de façon predefinie et regulee, preparation et utilisation de ces compositions - Google Patents

Compositions permettant de liberer un ingredient actif de façon predefinie et regulee, preparation et utilisation de ces compositions Download PDF

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Publication number
WO2001037811A1
WO2001037811A1 PCT/EP1999/008979 EP9908979W WO0137811A1 WO 2001037811 A1 WO2001037811 A1 WO 2001037811A1 EP 9908979 W EP9908979 W EP 9908979W WO 0137811 A1 WO0137811 A1 WO 0137811A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition according
composition
active ingredient
optionally
ivermectin
Prior art date
Application number
PCT/EP1999/008979
Other languages
English (en)
Inventor
Sébastien HURON
Eric Lacoste
Original Assignee
Akzo Nobel N.V.
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 Akzo Nobel N.V. filed Critical Akzo Nobel N.V.
Priority to AU15560/00A priority Critical patent/AU1556000A/en
Priority to PCT/EP1999/008979 priority patent/WO2001037811A1/fr
Publication of WO2001037811A1 publication Critical patent/WO2001037811A1/fr

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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
    • A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
    • A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1617—Organic compounds, e.g. phospholipids, fats
    • A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers

Definitions

  • the present invention relates to a composition, preferably to a pharmaceutical composition containing an active ingredient, such as antiparasitics, which is capable to become administered to, preferably implanted subcutaneously into an organism, such as an animal, and to release said active ingredient in a predefined and controlled manner
  • acitve ingredients to an organism are knwon, e g via the oral route (per os) through tablets, capsules, liquids (suspensions or solutions), drops, syrup and slow release bolus Tor animals the administration of liquids, powder, paste, granules via the animal feed or drinking water is often used
  • the parenteral application [e g subcutaneous (s c ), intramuscular (I m ), intraperitoneal (I p ), intraveneous (I V )] can occur e g per injection, infusion or implantation
  • the treatment of various diseases requires the maintenance of a sufficient level of pharma- ceutically active ingredients in certain body fluids over a defined period
  • One example is the control of infectious diseases with antibiotics that require a defined concentration of the antiinfective ingredient in the body fluids where the pathogen is located to kill the pathogens or control the bacteria replication
  • Another example is the control of ⁇ parasites in and on the organism
  • fomulations known as hearing aid formulations
  • practiceslow release bolus and also subcutaneous implants
  • compositions of this invention can become administered to any kind of organism, such as humans and animals, preferably mammals, the invention will be described in more detail via the treatment of animals with pharmaceutically active substances, especially antiparasitics
  • Parasites can be classified into Endoparasites and Ectoparasites Endoparasites, for example worms (nematodes), cestodes and trematodes are hosted inside (e g gastrointestinal tract, respiratory tract) the organism (human or animal). Ectoparasites, for example fleas, mites, ticks and lice are hosted on (on or in the skin) the organism (human or animal)
  • Active ingredients are known that control Endoparasites (Endoparasitics, e g Fenbendazol, Pyrantel, Praziquantel) or Ectoparasities (Ectoparasitics, e.g Deltamethrin, Fipronil, Lufenuron) and active ingredients that control both Endoparasites and Ectoparasites (Endectoparasitics, e.g Abamectin, Ivermectin, Milbemycin, Cydectin)
  • active ingredients can be adminstered in various formulation, e g as powder, spray, pour-on, bath, dip, injection, tablets, bolus or suspension
  • Another object of the present invention is an improved manufacturing process for such products minimizing or avoiding the risk of thermo-degradation of the components of such product and/or minimizing or avoiding the content of residual solvents from the manufacturing process in the product
  • Another object of the present invention is an easy to handle manufacturing process for such products using equipment that is common in the manufacturing of other parmaceutical formulations thus minimizing the cost of such manufacture
  • Still another object of the present invention is the provision of implants with dosages of active ingredients being individually adaptable to the needs of the specific prophylactic or therapeutic treatment
  • Current products use a fixed dosage in the implants Individual dosages are especially desired for animal treatment with regard to different species, body weight, breed and age
  • the present invention meets these requirements, by providing a composition, preferably a pharmaceutical composition for predefined and controlled release of an active ingredient
  • a composition allowing a predefined and controlled release of an active ingredient to an organism when administered to said organism, which composition comprises a combination A) of at least two components a) at least one active ingredient in dispersed solid form, b) at least one gelling agent, c) optionally at least one filler, and d) optionally at least one adjuvant which combination A) is in the form of discrete particles and is embedded into a matrix B) which is formed by a pore-forming agent and optionally at least one adjuvant.
  • composition of this invention can be administered to an organism in various ways known to those skilled in the art.
  • Preferred is the form of an implant, preferably a subcutaneous implant.
  • composition of this invention preferably contains, as an active ingredient, an endectocide in the form of subcutaneous implants, constituted by one or more tablets that release the active ingredient in a predetermined and controlled manner during a period quite longer as known formulations allow, of up to about 1 year, preferably of about 4 months, thus reducing the labor costs, the movement of the animals, the losses of body weight and of production of milk due to such movements, besides protecting the animals and their hide against the attack of the parasites.
  • an endectocide in the form of subcutaneous implants constituted by one or more tablets that release the active ingredient in a predetermined and controlled manner during a period quite longer as known formulations allow, of up to about 1 year, preferably of about 4 months, thus reducing the labor costs, the movement of the animals, the losses of body weight and of production of milk due to such movements, besides protecting the animals and their hide against the attack of the parasites.
  • the duration of the action of the composition of the invention can be easily controlled by manipulating the concentration of the active principle and of the excipients.
  • an active ingredient a) in dispersed solid form any active substance can be used that is desired to become released when administered to an organism.
  • Active ingredients can be all types of biologically active substances, preferably pharmaceutically active substances.
  • biologically active substances are antibiotics, antiparasitics, hormones, growth promotors. anti-cancer drugs, vitamines and vaccines.
  • More specific examples of pharmaceutically active substances are BST, trenbolone, zeranol, ivermectin, abamectin, doramectin, moxidectin, selamectin and other systemical compounds
  • More than one active ingredient can be used, for example a synergistic combination of two pharmaceutically active ingredients.
  • composition according to the present invention can also additionally contain other biologically active agents used in human or veterinary medicine such as, for example, vaccines, antibiotics, growth promoters, agents that potentialize the antiparasite effect of the active ingredient or that improve or avoid its side effects
  • the active ingredient is an endectocide, especially preferred an avermectin or a milbemicin and most especially preferred ivermectin and abamectin.
  • the active ingredient is solid and is applied in dispersed form, for example in the form of powder or preferred in the form of granules.
  • Solid shall mean solid at 25°C
  • the gelling agent b) can be of any kind as long as this agent is physiologically acceptable and forms together a gel or a shapable mass with component a), with optional components c) and d) and with a liquid, for example water or body fluids
  • gelling agents are organic or inorganic gelling agents, such as modified cellulose, modified starch, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylates, polymethacrylates, or dispersed silica
  • modified cellulose preferably alkylated cellulose, most preferred ethylcellulose
  • the filler c) can be of any kind as long as this is a pharmacologically inactive substance
  • examples of filler c) are carbohydrates and silica, preferably a disaccharide, and most preferred lactose
  • the matrix material B) embedding shaped particles from components a), b), optionally c) and optionally d) is a pore-forming agent
  • This agent is soluble in body fluids and after being administered to the organism this agent dissolves thereby forming pores in the matrix
  • this agent dissolves thereby forming pores in the matrix
  • the body fluids become access to the combination A) comprising components a), b) and optionally c) and d) and the active ingredient is released in a predetermined and controlled manner
  • pore-forming agents are polyalkylene ethers, polyvinyl alcohol, sugar and sugar alcohols
  • sugars are lactose, glucose and preferred saccarose
  • sugar alcohols are mannitol and sorbitol
  • Preferred as pore-forming agents are polyalkylene ethers or polyvinyl alcohol.
  • Said polyalkylene ethers or polyvinylalcohols are available in different aggregate forms, depending on their molecular weight, as liquids or solids at 25°C.
  • the polyalkylene ethers and the polyvinylalcohols should be matrix-forming and shapable via compression methods
  • the molecular weight of the pore-forming agent should be selected adequately to allow pore-forming effects in contact with body fluids
  • polyalkylene ethers examples include polybutylene ethers, polypropylene ethers or especially polyethylene ethers
  • a nonionic polymer of polyethylene oxide, a polyethylene glycol, a polyethyleneglycol alkyl ether or combinations thereof are used Said matrix material B) in addition can contain one or more adjuvants d)
  • a material forming matrix B) is a a nonionic polymer of polyethylene oxide possessing a molecular weight (weight average) between 3M and 10 M, whereby M stands for a million
  • a very preferred matrix material B) for use in the instant invention is the excipient Polyox ⁇ from Union Carbide Corporation, this being a nonionic polymer of polyethylene oxide with specifications of USP-NF 1990 In this respect reference is made to the leaflet of Union Carbide Corporation published in the USA in 1994 under the title "POLYOXYO
  • the molecular weight of Polyox used in the implants of the present invention is of 4 M, 5 M and 7 M, where M stands for 1 million
  • compositions of the present invention one can use all the forms of Polyox mentioned in said leaflet as well as othei different forms of excipients that can be used for the same purpose as Polyox such as polyethylene glycol, polyethylene glycol alkyl ether, polyvinyl alcohol other derivatives of polyoxyethylene and other polymers usable for the same purpose
  • composition of this invention is in the form of a tablet
  • other forms are also applicable for example rods, capsules, microparticles and granules
  • compositions of the instant invention may contain additional adjuvants known in the art of formulations
  • adjuvants are carrier materials such as starch, starch derivatives, talc, stea ⁇ c acid or salts thereof, fats, waxes, natural or hardened oils, liquids, such as water, alcohols, e g ethanol, glycerin or polyols vegetable oils, polymers or copolymers, such as copolymers from glyco c acid and lactic acid, fillers, binders, lubricants, surfactants, stabilizers, emulsifiers, disperging agents thinners, thickening agents, solvents, preservation agents, buffer agents, salts, and antioxidants
  • carrier materials such as starch, starch derivatives, talc, stea ⁇ c acid or salts thereof, fats, waxes, natural or hardened oils, liquids, such as water, alcohols, e g ethanol, glycerin or polyols vegetable oils, polymers or copolymers
  • Such adjuvants can be contained in the component A) and/or in the component B) of the composition of this invention.
  • composition A) can generally be varied in a broad range Typical amounts of component a) are 0.01 - 98 % by weight, preferred 20 - 95 % by weight and most preferred 35 - 85 % by weight.
  • Typical amounts of component b) are 0.01 - 20 % by weight, preferred 0. 1 - 10 % by weight and most preferred 0.5 - 5 % by weight.
  • Typical amounts of component c) are 0 - 60 % by weight and preferred 1 - 40 % by weight.
  • Typical amounts of component d) are 0 - 10 % by weight and preferred 0 - 5 % by weight.
  • the indicated amounts for components a), b), c) and d) refer to the total of said components in a composition.
  • the weight proportion of combination A) and matrix material B) can also be varied in a broad range.
  • Typical amounts of matrix material B) are 2 - 50 % by weight, preferably 5 - 40 % by weight, referred to the total composition of A) and B).
  • compositions of the instant invention can be prepared by mixing components a), b), optionally c) and optionally d) in a conventional mixing equipment. This can be performed in dry form or under addition of a liquid, preferably water.
  • the mass thus formed should be shapable to form a plurality of small pieces, such as grains, of component A).
  • the formation of such small pieces can be performed by conventional shaping means, for example by pressing the obtained mass through a mesh.
  • the obtained small pieces are then combined with the matrix forming component or components. This can be performed in conventional mixing equipment.
  • this composition is given the final shape in a shaping equipment for said combination of components A) and B). Examples thereof are a pelletizer, an extruder or preferably a tablet press.
  • the instant invention also relates to a process of manufacturing the above defined composition said process encompassing the measures: i) combining components a), b), optionally c) and optionally d) in a mixing equipment, ii) mixing said components together with a liquid to form a shapable mass A) iii) shaping said mass A) into a plurality of small pieces by applying a first shaping means to said mass A) and separating said mass A) into a plurality of small pieces, iv) combining said small pieces of mass A) with a pore-forming agent B) and optionally with at least one adjuvant d), v) mixing said combination of components A) and B) to form a shapable composition; and vi shaping said composition to a desired shape by means of a second shaping means
  • a tablet press is used as a shaping means In this process the application of heat and/or organic solvents can be avoided and easily available equipment can be used
  • the shaped composition, for example tablets, obtained according to this process can be combined to form an implant.
  • implants of the present invention are packed in plastic cartridges containing a plurality of implants, which are usable for treating of several animals
  • An implant is in general constituted by a certain number of tablets, for instance 5, 10, or 15 tablets These tablets are called "pellets”.
  • a more specific formulation according to the present invention and containing the Endectoparasitics Ivermectin as an active ingredient typically contains approximately the following
  • the implant is preferably applied to the ear of the animal since this region has sufficient blood vessels, thus permitting a desired absorption of the active ingredient
  • the specific product Ivermectin after being absorbed, gets into the bloodstream deposits on the fat and is distributed by the secretions into the bloodstream, the digestive apparatus, respiratory apparatus, liver, and is eliminated by the feces and urine
  • compositions of this invention can be applied to any orgamsm where predetermined and controlled release of an active ingredient is desired, especially where individual dosage is required
  • Examples of organisms are vertebrates and non-vertebrates Preferred is the application to humans and animals
  • pellets of the compositions given below in examples 1 - 16 were obtained, that were usable to release a sufficient level of ivermectin over a certain period.
  • Example 2 Pellets containing 1428 mg of ivermectin/pellet and 10% of Polyox 301
  • Pellets containing 15.00 mg of ivermectin/pellet and 10% of Polyox 303 Pellets containing 15.00 mg of ivermectin/pellet and 10% of Polyox 303 :
  • Lactose 63. g
  • Polyox 303 20.0 g
  • Lactose 32.0 g
  • Polyox 301 57.5 g
  • Lactose 3.3 g
  • Pellets containgmg 1484 mg of ivermectin/pellet and 30% of Polyox 301

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne une nouvelle composition spécialement conçue pour combattre les parasitoses internes et externes. Dans un mode de réalisation, cette composition contient, en tant qu'ingrédient actif, un endectocide, une forme d'implant sous-cutané constitué par un ou plusieurs granulés qui libèrent l'ingrédient actif de façon prédéterminée et régulée. Dans des modes de réalisation spécifiques, l'endectocide est de l'avermectine ou de la milbemycine, en particulier de l'ivermectine.
PCT/EP1999/008979 1999-11-22 1999-11-22 Compositions permettant de liberer un ingredient actif de façon predefinie et regulee, preparation et utilisation de ces compositions WO2001037811A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU15560/00A AU1556000A (en) 1999-11-22 1999-11-22 Composition allowing predefined and controlled release of active ingredient, preparation thereof and use
PCT/EP1999/008979 WO2001037811A1 (fr) 1999-11-22 1999-11-22 Compositions permettant de liberer un ingredient actif de façon predefinie et regulee, preparation et utilisation de ces compositions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP1999/008979 WO2001037811A1 (fr) 1999-11-22 1999-11-22 Compositions permettant de liberer un ingredient actif de façon predefinie et regulee, preparation et utilisation de ces compositions

Publications (1)

Publication Number Publication Date
WO2001037811A1 true WO2001037811A1 (fr) 2001-05-31

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PCT/EP1999/008979 WO2001037811A1 (fr) 1999-11-22 1999-11-22 Compositions permettant de liberer un ingredient actif de façon predefinie et regulee, preparation et utilisation de ces compositions

Country Status (2)

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AU (1) AU1556000A (fr)
WO (1) WO2001037811A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001054662A2 (fr) * 2000-01-27 2001-08-02 Ardana Bioscience Limited Microparticules comprimees pour injection seche
WO2003002102A1 (fr) * 2001-06-29 2003-01-09 Smart Drug Systems Inc Composition pharmaceutique a liberation prolongee
WO2003004059A1 (fr) * 2001-07-04 2003-01-16 Smart Drug Systems Inc Traitement de maladies parasitaires
WO2003009833A1 (fr) * 2001-06-29 2003-02-06 Smart Drug Systems Inc Systeme d'administration a liberation prolongee
WO2018189314A1 (fr) * 2017-04-13 2018-10-18 Ceva Sante Animale Composition pour le traitement d'infestations par des vers
EP2598151B1 (fr) 2010-07-30 2018-12-26 CEVA Santé Animale SA Compositions pour le traitement de ver du coeur
EP3634583A4 (fr) * 2017-06-06 2021-03-03 Merck Sharp & Dohme Corp. Implant à action prolongée pour le traitement de maladies infectieuses

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987002240A1 (fr) * 1985-10-11 1987-04-23 Aktiebolaget Hässle Nouvelle preparation medicamenteuse a liberation controlee de l'ingredient actif, son procede de fabrication et utilisation de la nouvelle preparation
WO1989000045A1 (fr) * 1987-06-30 1989-01-12 Riker Laboratories, Incorporated Comprimes a liberation de medicaments regulee de maniere enzymatique
DE4230563A1 (de) * 1992-09-12 1994-03-17 Boehringer Ingelheim Kg Hochdosierte Kompaktgranulate und daraus hergestellte Tabletten
US5458887A (en) * 1994-03-02 1995-10-17 Andrx Pharmaceuticals, Inc. Controlled release tablet formulation
US5472708A (en) * 1992-11-27 1995-12-05 Andrx Pharmaceuticals Inc. Pulsatile particles drug delivery system
WO1999015166A1 (fr) * 1997-09-23 1999-04-01 Pfizer Limited Formulations antiparasitaires

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987002240A1 (fr) * 1985-10-11 1987-04-23 Aktiebolaget Hässle Nouvelle preparation medicamenteuse a liberation controlee de l'ingredient actif, son procede de fabrication et utilisation de la nouvelle preparation
WO1989000045A1 (fr) * 1987-06-30 1989-01-12 Riker Laboratories, Incorporated Comprimes a liberation de medicaments regulee de maniere enzymatique
DE4230563A1 (de) * 1992-09-12 1994-03-17 Boehringer Ingelheim Kg Hochdosierte Kompaktgranulate und daraus hergestellte Tabletten
US5472708A (en) * 1992-11-27 1995-12-05 Andrx Pharmaceuticals Inc. Pulsatile particles drug delivery system
US5458887A (en) * 1994-03-02 1995-10-17 Andrx Pharmaceuticals, Inc. Controlled release tablet formulation
WO1999015166A1 (fr) * 1997-09-23 1999-04-01 Pfizer Limited Formulations antiparasitaires

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6627600B2 (en) 2000-01-27 2003-09-30 Ardana Bioscience Limited Compressed microparticles for dry injection
WO2001054662A3 (fr) * 2000-01-27 2002-03-21 Asta Medica Ag Microparticules comprimees pour injection seche
WO2001054662A2 (fr) * 2000-01-27 2001-08-02 Ardana Bioscience Limited Microparticules comprimees pour injection seche
US8197839B2 (en) 2001-06-29 2012-06-12 Virbac Corporation Sustained release delivery system
JP4800570B2 (ja) * 2001-06-29 2011-10-26 バーバック コーポレイション 徐放性医薬組成物
WO2003002102A1 (fr) * 2001-06-29 2003-01-09 Smart Drug Systems Inc Composition pharmaceutique a liberation prolongee
JP2004530721A (ja) * 2001-06-29 2004-10-07 スマート ドラッグ システムズ インコーポレイティド 徐放性医薬組成物
JP2004535473A (ja) * 2001-06-29 2004-11-25 スマート ドラッグ システムズ インコーポレイティド 徐放性医薬組成物
JP4913321B2 (ja) * 2001-06-29 2012-04-11 バーバック コーポレイション 徐放性医薬組成物
WO2003009833A1 (fr) * 2001-06-29 2003-02-06 Smart Drug Systems Inc Systeme d'administration a liberation prolongee
AU2002344687B2 (en) * 2001-07-04 2008-04-10 Virbac Corporation Treatment of parasitic disease
JP2005505513A (ja) * 2001-07-04 2005-02-24 スマート ドラッグ システムズ インコーポレイティド 寄生虫病の治療
WO2003004059A1 (fr) * 2001-07-04 2003-01-16 Smart Drug Systems Inc Traitement de maladies parasitaires
EP2598151B1 (fr) 2010-07-30 2018-12-26 CEVA Santé Animale SA Compositions pour le traitement de ver du coeur
WO2018189314A1 (fr) * 2017-04-13 2018-10-18 Ceva Sante Animale Composition pour le traitement d'infestations par des vers
US11318156B2 (en) 2017-04-13 2022-05-03 Ceva Sante Animale Solid injectable veterinary implants comprising monocyclic lactone
EP3634583A4 (fr) * 2017-06-06 2021-03-03 Merck Sharp & Dohme Corp. Implant à action prolongée pour le traitement de maladies infectieuses

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Publication number Publication date
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