WO2001035925A1 - Produit alimentaire comprenant des medicaments encapsules - Google Patents

Produit alimentaire comprenant des medicaments encapsules Download PDF

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Publication number
WO2001035925A1
WO2001035925A1 PCT/GB2000/004405 GB0004405W WO0135925A1 WO 2001035925 A1 WO2001035925 A1 WO 2001035925A1 GB 0004405 W GB0004405 W GB 0004405W WO 0135925 A1 WO0135925 A1 WO 0135925A1
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WIPO (PCT)
Prior art keywords
food product
food
product according
agent
particles
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Application number
PCT/GB2000/004405
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English (en)
Inventor
Ian Andrew Lilley
Philip Martin Mcgenity
Original Assignee
Mars U.K. 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 Mars U.K. Limited filed Critical Mars U.K. Limited
Priority to AU14066/01A priority Critical patent/AU1406601A/en
Publication of WO2001035925A1 publication Critical patent/WO2001035925A1/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
    • A61K9/20—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
    • A61K9/2081—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets with microcapsules or coated microparticles according to A61K9/50
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • 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
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system

Definitions

  • the present invention relates to food products that contain a pharmaceutical agent dispersed within a palatable food matrix.
  • the products are designed so that the unpleasant taste of the pharmaceutical agent is disguised. Additionally, the pharmaceutical agent is not susceptible to modification or degradation as a result of contacting compounds contained within the food matrix. This guarantees the safety of the product.
  • one or more pharmaceutical agents are dispersed within a matrix of substantially inert materials and formed into a tablet or lozenge. Inert materials are used to prevent reaction of the pharmaceutical agent with compounds contained within the food.
  • inert materials are generally selected from a range of such materials that are specified in approved Pharmaceutical monographs, such as the European Pharmacopoeia. Such collections of monographs tend to exclude many of the materials which are most palatable to many animals, such as meat products and complex proteins, at least partly because their complexity makes it almost impossible to define a very precise specification for such materials. This makes it difficult to design medicinal food products that are palatable to the animal.
  • Palatability is of great significance, particularly for fastidious companion animals such as cats, since oral administration of an unpalatable tablet can be very difficult and on occasions even impossible, particularly when the agents to be administered are especially unpalatable to the animal.
  • Palatability is also important when baiting wild animals, for example, for the delivery of vaccines or other pharmaceutical formulations. In this instance, it is of the utmost importance to ensure that the active agents are successfully ingested by the wild animal, since it will be desirable for as many animals as possible to receive the intended treatment.
  • the problem of the oral administration of unpalatable medicine to animals has been recognised in the art, and a number of solutions have been proposed.
  • One approach is to create a product, using pharmaceutical agents that are relatively stable chemically, that consists of one or more pharmaceutical agents dispersed within a palatable matrix of pet food materials. Analytical methods are then employed to validate that, within the resolution of such methods, the pharmaceutical agents are not degraded, either during processing, or simply through being in contact with food materials.
  • Such a product known as "Esy-Dose", is currently sold in Australia.
  • a related concern is that the complexity and variability of materials such as meat products, that could well be present in such a palatable matrix, may be such that the occasional batch of such a material might be exceptionally more chemically reactive towards the pharmaceutical agent. Because this event is only very occasional, this possibility may not be apparent during the validation procedures.
  • EP 0 574 301 (Sogeval SA) teaches an alternative solution, namely that of using a matrix of palatable food material which contains a "recess" within which a pill can be placed.
  • a similar principle is described in International patent application WO95/20942 (Atali & Vuagnoux).
  • WO95/20942 (Atali & Vuagnoux)
  • Another approach is to disperse the pharmaceutical active within a core and to apply an outer coating layer, which includes palatable substances, as is described in US 5,683,722 (Derrieu et al.).
  • Yet another approach is to disperse the active in an inert matrix of materials taken from a relatively restricted range of those which have pharmacopoeia monographs and to create a granule, which may then be added to a feed.
  • Such an approach is taught in US 4,597,969 (Merck, Sharp & Dohme), where the granule is formed from alginates and magnesium hydroxide.
  • the ability of many animals to "sift out" particles of unpalatable material from others which are more palatable presents a significant drawback to this approach.
  • a food product for the oral delivery of a pharmaceutical agent to a non-human animal comprising particles of said agent dispersed substantially uniformly within a palatable food matrix, wherein each of said particles is encapsulated within a substantially inert coating.
  • the food products of the invention have the advantage that they greatly increase the ease and chance of success of oral administration, by suppressing the unpalatable taste of the medicament, whilst minimising the risks associated with bringing pharmaceutical agents directly into contact with food components.
  • the pharmaceutical agent is isolated from the food material by virtue of the inert coating surrounding the agent, meaning that no undesirable reactions can occur between the pharmaceutical agent and the other ingredients of the food product. This greatly increases the range of pharmaceutical agents that may be included in food products.
  • a large selection of food ingredients may be used to ensure that the product exhibits the desired degree of palatability to the target animal, since the selection is not limited to the substantially inert materials that are generally approved for contact with pharmaceutical agents.
  • a further advantage of the food products of the invention is that they provide an excellent mechanism by which to control the dosage of medicament that is applied to the animal.
  • a certain product type, designed for a particular application to a specific target animal will therefore contain a controlled amount of medicament. This amount should correspond to the desired dosage for a particular unit weight of animal, for example, a 10kg unit weight.
  • the owner or carer of the animal can in this way administer the required dosage simply by reference to the weight of the animal. In this example, a 30kg animal would be given three food products.
  • the food products of the invention may be liquid, semi-solid or solid in form.
  • Solid food products may be formed into lozenges or tablets that contain a particular unit dose of pharmaceutical agent. Strips or chews may also be used.
  • Semi-solid products may take the form of a porridge or broth.
  • Liquid food products may be packaged into cans or tins, preferably in amounts corresponding to a particular unit dose.
  • the food matrix may be any material that is palatable, non-toxic, and easily ingestable, including solid, semi-solid and liquid materials.
  • the matrix is easily digestible by the animal. Suitable food materials may be selected from those used conventionally in pet foods and livestock feed, as the skilled reader will appreciate.
  • the matrix will contain flours and starches and other materials necessary to aid processing, impart colour, act as preservatives, impart texture and so on.
  • poultry meal protein source, palitant
  • soya bean oil fat, aid to processing
  • poultry liver powder protein, palitant
  • sugar flavour, humectant
  • glycerol softener, humectant
  • water texture former, aid to processing
  • maltose glucose syrup flavour, humectant
  • salt flavour, humectant
  • dark malt flour starch, colorant
  • red iron oxide mineral
  • turkey flavour flavour, palitant
  • roche D20 antioxidant
  • meat and fish-based materials may also be used in the food matrix. These materials are generally derived from dried meat and fish products that are then formed into powders for incorporation into food materials.
  • Milk is particularly suitable as a food matrix for a liquid food product, since it is highly palatable, allows homogenous dispersion of the encapsulated particles of pharmaceutical agent and may be easily packaged and stored without risk of degradation.
  • the products may optionally be divided into fractions to allow precise administration of the correct dose to an animal that falls between two weight groupings.
  • a product in the form of a lozenge, tablet, strip or chew may be marked into segments (for example, into quarters).
  • the products of the invention may be administered directly to the animal, for example, by hand.
  • the products may be mixed into the animal's food.
  • solid food products such as lozenges or tablets may be broken into small portions, once the correct number of units has been measured out.
  • a large range of pharmaceutical agents may be included in the food products of the invention, as will be clear to the skilled reader.
  • a course of medicaments may be prescribed.
  • agents to treat or prevent parasite infestation such as anti-worming agents, agents directed against stiffness or arthritis, components of vaccines, anti-flatulence agents, antibiotics, agents for the treatment of obesity, agents for the treatment of motor disorders, agents for the treatment of senility, agents for the treatment of elevated blood pressure, anti-inflammatory agents, oral rehydration agents, hormones, diuretics, cardiovascular and respiratory preparations, products to thin the blood or enhance circulation and agents directed against unpleasant breath odour.
  • Suitable examples of pharmaceutical agents include anti-worming compounds such as dichlorophen, febantel, fenbendazole, mebendazole, nitroscannate, piperazine, praziquantel, pyrantel, and oxantel.
  • Medicament may also be applied to livestock, such as horses, cattle, sheep, pigs and goats.
  • suitable agents include albendazole and oxfendazole.
  • the agents may be combined into one product type to give a combined medicament.
  • each agent may be individually encapsulated and mixed into the food matrix separately.
  • individually encapsulated pharmaceutical agents may be agglomerated into combined particles and further encapsulated.
  • wild animals susceptible to disease may be treated using bait laced with the food products of the invention.
  • a vaccine such as, for example, an anti-rabies vaccine
  • Animals such as deer may be treated with anti-tick vaccines.
  • poisons may also be delivered using the food products of the invention, for example, to limit a pest population.
  • the pharmaceutical agent should be dispersed throughout the food matrix as small encapsulated particles.
  • the size of these particles may vary between certain limits, depending on various factors such as the nature of the medicament, the method of processing, the target animal species, the cost of production and the intended sales value of the food products.
  • the particle size should be small enough that the integrity of the encapsulated pharmaceutical is retained through the manufacturing process; if the particles are too large, there is a risk that during mixing of the particles within the food matrix, the particles will become broken by shearing forces. Furthermore, a large particle size increases the chance that the particles may become broken during chewing of the food by the animal, meaning that the unpalatable pharmaceutical agent will be tasted and the food rejected.
  • the particles will be between lOOnm and 1mm in diameter, preferably between 1 and 500 ⁇ m diameter, more preferably between 150 and 500 ⁇ m diameter.
  • the thickness of the encapsulating coating may also be varied, depending on the particular requirements of each system.
  • the coating must be sufficiently mechanically robust to withstand the high shearing forces encountered during the production and molding process, but must not be so thick that the particles pass through the digestive system without being ingested. An additional factor is that as more coating material is used in the production process, the cost of materials increases.
  • the coating should be thick enough to prevent it degrading until the food has passed out of the buccal cavity into the lower regions of the oesophagus, where the palatability of the food is no longer of concern.
  • a preferred range for the thickness of the coating is between lnm and lOO ⁇ m, more preferably, between 20nm and lOOnm.
  • the ratios of coating to core may vary between around 1:20, to around 1: 1, depending upon the particular requirements and properties desired of the food product.
  • encapsulating agents will be known to those of skill in the art.
  • inert encapsulating materials include ethylcellulose, gelatine and gum arabic.
  • substantially inert is meant that the material is non-reactive chemically under conditions of normal temperature and pressure with food matrix materials and with pharmaceutical agents.
  • the encapsulating coating should not itself be a recognised pharmaceutical agent and should be safe to eat.
  • any method of generation and encapsulation of small particles will be suitable for use in the present invention, as the skilled reader will appreciate. In general, there are three main methods by which encapsulated particles may be most easily generated.
  • a co-assivation technique may be applied for pharmaceutical agents that are soluble in organic solvents, and that are insoluble in water.
  • a particulate suspension of the agent is prepared, for example, in a solution of ethylcellulose in cyclohexane. This solution is then stirred vigorously. The particles will in this manner gradually become encased within an ethylcellulose coating.
  • the size of the particles can be controlled by the speed of stirring the solution; faster stirring will result in a smaller particle size.
  • the thickness of the coating may be controlled by altering the amount of encapsulating agent that is present in the solvent. A larger amount of encapsulating agent will increase the thickness of the coating layer.
  • a second method also suitable for use with water-insoluble pharmaceutical agents, involves spraying a solution of the pharmaceutical agent into a bath of calcium chloride.
  • the pharmaceutical agent may be dissolved in a sodium alginate solution and then sprayed into the bath, thus creating an atomised aerosol that forms encapsulated particles.
  • the force with which the liquid is sprayed controls the particle size; the faster spraying is operated, the smaller will be the resulting particle size.
  • the thickness of the coating can be controlled by varying the content of encapsulating material.
  • a third method utilises co-assivation of a gelatine/gum arabic mixture in an aqueous solution, within which the pharmaceutical agent is dispersed.
  • the suspension is stirred until the particles reach the desired size, then the pH is adjusted, forcing the gelatine/gum arabic mixture back out of solution to form deposits on the surface of each particle.
  • the thickness of the encapsulated layer can be controlled by varying the content of the gelatine/gum arabic material.
  • the particles of encapsulated pharmaceutical are mixed into the food matrix to form a homogenous mixture, in which the particles are mixed substantially uniformly.
  • substantially uniformly is meant that the particles are dispersed throughout the food matrix and do not agglomerate together in lumps.
  • the food matrix must be mixed with the particles for a sufficient time.
  • the mixing period will differ for different particle sizes and for different food matrix materials. If necessary, samples can be taken at time points during the mixing process and analysed to assess the degree to which mixing has occurred. The most effective way to ensure that complete mixing has occurred is to blend the mixture for an extended period of time.
  • the mixture of food matrix and encapsulated pharmaceutical particles that results at the end of the mixing process may then be molded into the desired shape.
  • These products may be any shape, but will normally be spherical, square, rectangular, cylindrical or pill-shaped. However, to increase their consumer appeal, the products may be formed into attractive shapes such as, for example, the shape of a bone. As discussed above, molded products may include indentations that mark out fractions of the product, so allowing the product to be broken into segments to facilitate the correct dosing. Finally, the products will be packaged for sale. Packages that contain one or more food products as described above are included as part of the present invention.
  • a process for the production of a food product containing a pharmaceutical agent suitable for administration to a non-human animal comprising the step of dispersing particles of said agent substantially uniformly within a palatable food matrix, wherein each of said particles is encapsulated within a substantially inert coating.
  • a food product for use in therapy of a non-human animal.
  • the invention also provides the use of particles of a pharmaceutical agent encapsulated within a substantially inert coating and dispersed within a palatable food matrix, in the manufacture of a medicament for the treatment or prevention of a disease in a non-human animal.
  • a still further aspect of the invention provides a method of treating a disease, or of preventing incidence of a disease in a non-human animal, comprising administering to said animal, a food product according to any one of the aspects of the invention described above.
  • Gelatine (10 g) and acacia (10 g) were dissolved separately in water at 40°C.
  • Fenbendazole (20 g) was added to the gelatine solution and the resulting suspension homogenised using a high shear Silverson mixer.
  • the acacia solution was added, the suspension re-homogenised and then diluted to a concentration of 1.5% (w/v) based on the individual colloids.
  • the pH of the suspension was adjusted to 4.5 over 1 hour by the addition of 10% acetic acid in water, held for 1 hour at 40°C then cooled to 15°C over 2 hours.
  • the solution was diluted with isopropanol (200 ml), filtered then dried to give free flowing particles.
  • Sodium Alginate (8.4 g) was dissolved in hot water (700 g) with vigorous stirring.
  • Praziquantel (5.2 g) was added and the resulting suspension homogenised using a high shear Silverson mixer.
  • Calcium chloride (11.2 g) was dissolved in water (800 g) and agitated in a large diameter bowl.
  • the praziquantel-alginate suspension was sprayed into the calcium chloride solution, setting the alginate, and generating a slurry of praziquantel entrained in alginate gel.
  • the slurry was filtered and the resultant high moisture content solid analysed for free Praziquantel according to the standard test conditions.
  • Methanol - DMSO (9: 1) was demonstrated as a suitable solvent for the free active while having the potential to leave the encapsulating materials intact over a short time period (Based on data obtained from The Merck Index (1 1th Edition), Merck and Co, 1989).
  • the sample was diluted with solvent in a 50 ml volumetric flask, shaken for 2 minutes to dissolve free active then sample.
  • the sample was analysed by HPLC against an external standard (C18 column, eluant 70 : 30 MeOH : H 2 O, flow rate 1.5ml.min, detection at 290 nm) to give a To value for free active.
  • the solution was samples over the course of 2 hours to give an indication of the degradation rate of the wall and the leach rate from the capsule.
  • the capsules were ground with methanol - DMSO (9: 1) in order to mechanically disrupt the capsule walls, sonicated for 15 minutes to ensure full dissolution of the released active, then analysed by HPLC.
  • Example 4 Microencapsulation to Enhance Palatability.
  • Praziquantel was encapsulated in calcium gelled alginate as previously described.
  • the resultant colourless powder was dispersed in a powder premix and the bonding agent added.
  • the resultant dough was maintained at 60°C in order to keep it workable, while being formed into 2.5g treats.
  • the product was fed to cats in three separate trials and acceptance of the product compared against a control product.
  • the final trial tested whether aversion to the treat was introduced when the product was repeat fed.
  • a feeding trial was carried out using non- encapsulated material. The results are summarised below.
  • a slight deterioration in performance is observed after feeding the treat on successive days, however the feeding pattern for worming treats is a once a month occasion.
  • a further improvement in performance can be expected through an improvement in the palatability of the base recipe .
  • Example 5 Microencapsulation to Enhance Stability.
  • Step Two Preparation of Bonding Agent
  • Gelatin was added to boiling water, stirred to dissolve, then sucrose added. On dissolution of the sucrose, glycerol was added followed by potassium sorbate, and the solution homogenised. The resultant solution was then allowed to cool to solidify.
  • Powdered placebo (874.7g) and Oral Insecticide (20. Og) were mixed thoroughly to ensure complete homogeneity.
  • Solid bonding agent (105.2g) was cut into small ( ⁇ 5mm 3 ) cubes, added to the powder premix and mixed thoroughly. The raw material was then heated to 40°C in a stirred mixer to give workable dough that was moulded by hand.

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Epidemiology (AREA)
  • Hematology (AREA)
  • Nutrition Science (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Endocrinology (AREA)
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Abstract

La présente invention concerne des produits alimentaires qui contiennent des particules d'un agent pharmaceutique dispersées à l'intérieur d'une matrice alimentaire appétente. Chaque particule d'agent pharmaceutique est encapsulée dans un revêtement inerte. De cette façon, le goût déplaisant de l'agent pharmaceutique est masqué, et cet agent n'est pas sujet à modification ni à dégradation qui pourrait prendre place en cas de contact avec des composés contenus dans la matrice alimentaire.
PCT/GB2000/004405 1999-11-19 2000-11-17 Produit alimentaire comprenant des medicaments encapsules WO2001035925A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU14066/01A AU1406601A (en) 1999-11-19 2000-11-17 Food product comprising encapsulated drugs

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9927474.8 1999-11-19
GB9927474A GB2356346A (en) 1999-11-19 1999-11-19 Food product for oral delivery of a pharmaceutical agent to a non-human animal comprising encapsulated particles of said agent distributed within the product

Publications (1)

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WO2001035925A1 true WO2001035925A1 (fr) 2001-05-25

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AU (1) AU1406601A (fr)
GB (1) GB2356346A (fr)
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WO2003075895A1 (fr) * 2002-03-11 2003-09-18 Novartis Ag Compositions solides veterinaires a gout masque
EP1362583A1 (fr) * 2002-05-15 2003-11-19 CUM Taste Masking AG Procédé pour masquer le goût de substances par microencapsulation
EP1759692A2 (fr) * 2003-03-10 2007-03-07 Novartis AG Compositions solides veterinaires à goût masqué
US7348027B2 (en) * 2005-04-08 2008-03-25 Bayer Healthcare Llc Taste masked veterinary formulation
WO2009004488A2 (fr) * 2007-06-08 2009-01-08 Philip Morris Products S.A. Groupe de capsules pour une consommation par voie orale
WO2010079287A1 (fr) * 2009-01-09 2010-07-15 Vetoquinol S.A. Comprime secable comprenant des particules enrobees de s-adenosyl-methionine
WO2014136036A1 (fr) 2013-03-04 2014-09-12 Virbac Composition orale nutritionnelle et médicamenteuse a usage vétérinaire
WO2014136035A1 (fr) 2013-03-04 2014-09-12 Virbac Composition orale nutritionnelle et medicamenteuse a usage veterinaire
US9107952B2 (en) 2006-11-07 2015-08-18 Boehringer Ingelheim Vetmedica Gmbh Liquid preparation comprising pimobendan
US9463199B2 (en) 2004-03-25 2016-10-11 Boehringer Ingelheim Vetmedica Gmbh Use of PDE III inhibitors for the reduction of heart size in mammals suffering from heart failure
WO2018026810A1 (fr) * 2016-08-03 2018-02-08 Vanderbilt University Méthodes de traitement utilisant le célastrol
US10071162B2 (en) 2013-07-19 2018-09-11 Boehringer Ingelheim Vetmedica Gmbh Preserved etherified cyclodextrin derivatives containing liquid aqueous pharmaceutical composition
US10117869B2 (en) 2004-03-25 2018-11-06 Boehringer Ingelheim Vetmedica Gmbh PDE III inhibitors for treatment of asymptomatic heart failure
US10172804B2 (en) 2013-12-04 2019-01-08 Boehringer Ingelheim Vetmedica Gmbh Pharmaceutical compositions of pimobendan
WO2019161322A1 (fr) * 2018-02-19 2019-08-22 Monell Chemical Senses Center Compositions et procédés d'atténuation du caractère aversif de produits pharmaceutiques au moyen de sels
US10398705B2 (en) 2012-03-15 2019-09-03 Boehringer Ingelheim Vetmedica Gmbh Pharmaceutical tablet formulation for the veterinary medical sector, method of production and use thereof
US10537570B2 (en) 2016-04-06 2020-01-21 Boehringer Ingelheim Vetmedica Gmbh Use of pimobendan for the reduction of heart size and/or the delay of onset of clinical symptoms in patients with asymptomatic heart failure due to mitral valve disease

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US9668503B2 (en) 2007-06-08 2017-06-06 Philip Morris Usa Inc. Capsule clusters for oral consumption
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US9974325B2 (en) 2007-06-08 2018-05-22 Philip Morris Usa Inc. Capsule clusters for oral consumption
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WO2010079287A1 (fr) * 2009-01-09 2010-07-15 Vetoquinol S.A. Comprime secable comprenant des particules enrobees de s-adenosyl-methionine
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