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WO2000050009A1 - Procedes d'administration de composes a action pharmaceutique a des vertebres - Google Patents

Procedes d'administration de composes a action pharmaceutique a des vertebres Download PDF

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Publication number
WO2000050009A1
WO2000050009A1 PCT/US2000/004870 US0004870W WO0050009A1 WO 2000050009 A1 WO2000050009 A1 WO 2000050009A1 US 0004870 W US0004870 W US 0004870W WO 0050009 A1 WO0050009 A1 WO 0050009A1
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WO
WIPO (PCT)
Prior art keywords
pharmacologically active
vitamin
active compound
water
group
Prior art date
Application number
PCT/US2000/004870
Other languages
English (en)
Inventor
William R. Campbell
Douglas I. Hepler
Original Assignee
Idexx Laboratories, Inc.
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 Idexx Laboratories, Inc. filed Critical Idexx Laboratories, Inc.
Priority to AU36061/00A priority Critical patent/AU3606100A/en
Publication of WO2000050009A1 publication Critical patent/WO2000050009A1/fr

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Classifications

    • 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
    • A61K31/702—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/07—Retinol compounds, e.g. vitamin A
    • 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
    • A61K31/12—Ketones
    • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A61K31/355—Tocopherols, e.g. vitamin E
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • 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
    • A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
    • A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
    • 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
    • A61K31/65—Tetracyclines
    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents

Definitions

  • the present invention relates to methods of administering water labile, pharmacologically active compounds to vertebrates .
  • the methods may involve the administration of ivermectin-containing liposomes to the drinking water of the vertebrate to treat a parasitic infection.
  • the methods are useful for treating roundworms, cecal worms, lice, ticks, capillarial worms, and mite infections.
  • the present invention also generally relates to methods of stabilizing water-labile pharmacologically active compounds in aqueous solutions by encapsulating the drug compounds in liposomes.
  • BACKGROUND Parasitic infections are common problems in a variety of vertebrates, including cattle, horses, swine, sheep, caprines, and fowl.
  • Various parasitic infections are also problematic in companion animals such as dogs and cats.
  • Chickens and other fowl are known to suffer from a variety of parasitic infections.
  • Roundworms, cecal worms, capillarial worms, lice, and mites are among the common parasites associated with fowl and exact a substantial economic cost from the producers of fowl each year and raise health issues regarding the safety of the food supply.
  • Common methods of eliminating these parasites from fowl include the administration of piperazine to the drinking water or feed of animals.
  • the present invention provides methods of administering pharmacologically active compounds to vertebrates.
  • the methods involve encapsulating the pharmacologically active compound in liposomes to form a liposome composition and administering the liposome composition to the drinking water of the vertebrate.
  • the vertebrate may be a bovine, equine, ovine, feline, canine, porcine, a caprine, or a fowl.
  • the animal may be a fowl.
  • the pharmacologically active compound may be a parasiticide which is water labile and/or water insoluble and may be ivermectin.
  • the ivermectin may be administered to treat a parasitic infestation in the vertebrate and may be present in the liposome composition at a concentration of from about 0.01% to about 2.5% (w/v) drug in solution. In a preferred embodiment, the ivermectin may be present in the liposome composition at a concentration of from about 0.1% to about 2.0% (w/v) drug in solution.
  • the ivermectin may be present in the drinking water at a final concentration of about 10 parts per million or greater, or from about 10 ppm to about 1500 ppm. In a preferred embodiment, the ivermectin may be present in the drinking water at a final concentration of from about 10 ppm to about 500 ppm.
  • the parasites may be roundworms, mites, cecal worms, capillarial worms, lice, or ticks.
  • the pharmaceutical may be any of a wide range of antibiotics, nutrients, growth regulators, and other compounds including but not limited to, those described herein and the salts thereof.
  • the present invention also discloses a method of stabilizing a water-labile pharmacologically active compound in aqueous solutions which comprises encapsulating the water-labile pharmacologically active compound in a liposome to enhance its stability in aqueous solutions.
  • Compounds which may be stabilized by these methods include, but are not limited to, all of the compounds mentioned herein.
  • these compounds may also include nutrients and growth regulators such as vitamins, including vitamins A, E, D, and K, and steroid hormones and their derivatives, such as estrogen and estradiol .
  • the present invention also discloses a method of increasing the water solubility of a water insoluble pharmacologically active compound which comprises encapsulating the pharmacologically active compound in a liposome to increase its solubility in aqueous solutions.
  • the present invention relates to methods of administering pharmacologically active compounds to vertebrates.
  • the methods involve encapsulating the pharmacologically active compound in liposomes and administering the liposomes to the drinking water of the vertebrate .
  • the pharmacologically active compound may be a water labile compound and may be a parasiticide or an anti-parasitic agent, and the vertebrate may be a fowl.
  • the parasiticide or anti-parasitic agent may be ivermectin which may be present in the drinking water, encapsulated in liposomes, at a concentration of from about 0.01% to about 2.5% (w/v) drug in solution.
  • the ivermectin may be present in liposomes and present in the drinking water at a concentration of from about 0.1% to about 2.0% (w/v) drug in solution.
  • the ivermectin may also be present in the liposomes and present in the drinking water at a final concentration of greater than about 10 ppm (w/v) drug in solution. In preferred embodiments, the ivermectin may be present at final concentrations in the water of from about 10 ppm to about 2000 ppm drug in solution. While most of the ivermectin will be encapsulated within the liposomes, there will remain a portion of the ivermectin which is located in between liposomes and not encapsulated at all. Therefore, the concentrations cited herein relate to drug present in solution and not solely to the concentration of ivermectin in the liposomes.
  • parasiticide means any ectoparasiticide, acaricide, miticide, pediculicide, and antihelminthic .
  • anti-parasitic agent means a miticide or an antihelminthic, including but not limited to ivermectin.
  • miticide means any composition which is harmful to mites.
  • antihelminthic means any composition which is harmful to any species of helminth.
  • water labile means that the pharmacologically active compound has a tendency to lose its pharmacological effectiveness in aqueous solutions.
  • water insoluble means that the pharmacologically active compound generally shows resistance to solubilization in aqueous solutions. Compounds which are water insoluble may nevertheless still have some significant level of solubility in aqueous solutions . It is known that unmodified ivermectin cannot be efficiently administered in the drinking water because of its chemical instability and insolubility in water. Ivermectin in aqueous solutions is chemically degraded and loses its pharmacological efficacy before its therapeutic effect can be realized.
  • ivermectin in liposomes is attributable to chemical attractions occurring within the liposome between ivermectin and the lipid members of the liposome . These chemical attractions are believed to stabilize the ivermectin molecule. While encapsulation within a liposome may provide some protection for the ivermectin molecule from water, it is believed that some water nevertheless enters and/or travels through the liposome, such that the ivermectin is still exposed to a substantial amount of water, even within the liposome. This presence of water makes the observed effect even more unexpected.
  • the present invention derived from the unexpected discovery that the encapsulation of ivermectin in liposomes results in a water-stable drug product which may be easily and conveniently administered to the drinking water of a vertebrate, and which requires no further effort thereafter to complete the therapy.
  • the present invention will make newly available a number of compounds to treat a variety of animals for a variety of illnesses or infections. These compounds formerly could not be effectively used due to their lability and/or insolubility in aqueous solutions.
  • the present invention may be applied to a wide variety of compounds, and it is especially contemplated that the present invention may be applied to various nutrients and growth promoters.
  • vitamins A, E, D, and K which are lipophilic and therefore do not dissolve readily in water
  • hormones and their analogs such as estradiol and other estrogen derivatives, or other steroid compounds, may be incorporated into liposomes and administered in the drinking water of the animal in a cost-effective manner with great ease.
  • the pharmacologically active compound of interest to be applied in the present invention be a molecule which is chemically attracted to lipids (lipophilic) , as these molecules are expected to most clearly demonstrate the benefits described herein.
  • the molecule of interest should also have some significant level of solubility in water (i.e., not be completely water insoluble) .
  • the present invention may be applied to encapsulate the following compounds in liposomes for administration in the drinking water: doramectin, avermectin, abamectin, milbe ycin, amprolium, bacitracin, chlortetracycline, erythromycin, lincomycin/spectinomycin, neomycin, oxytetracycline, piperazine, sarafloxacin, spectinomycin, sulfachloro-pyrazine, sulfadimethoxine, sulfamethazine, sulfaquinoxaline, tetracycline, and tylosin.
  • doramectin avermectin, abamectin, milbe ycin, amprolium, bacitracin, chlortetracycline, erythromycin, lincomycin/spectinomycin, neomycin, oxytetracycline,
  • the unmodified salt forms of these compounds may exhibit improved solubility, but still not be able to be administered in the drinking water due to their water lability.
  • the present invention may serve to increase the water stability of these water labile compounds and/or serve to increase the water solubility of water insoluble compounds .
  • This example illustrates how the present invention was applied to eliminate poultry roundworms (Ascaridia) in chickens.
  • Eight Silver Wyandot chickens were used in the study.
  • the liposome composition was prepared according to the methods of Mezei et al . and contained ivermectin encapsulated in liposomes such that a final concentration in the drinking water of 0.1% ivermectin (w/v) was achieved.
  • the chickens were placed into four groups of two and the composition was administered in the drinking water at concentrations of 0 ppm, 100 ppm, 250 ppm, and 500 ppm (w/v) ivermectin in the drinking water.
  • the level of infestation was determined by comparing roundworm egg counts before therapy, at 24 hours, and at 48 hours. At the end of the study a necropsy was performed and roundworms that remained in the intestine were counted. The results are summarized in Table 1.
  • This example illustrates how the present invention was used to treat northern fowl mites in chickens .
  • Eight chickens were randomly assigned to four groups, with two chickens per group.
  • the 0.1% ivermectin encapsulated in liposomes composition was administered to the drinking water of each group at dosages of 0 ppm, 100 ppm, 250 ppm, and 500 ppm (w/v) ivermectin in the drinking water (i.e., drug in solution) . It was determined that at 500 ppm (or 78.5 mg/kg of body weight/day), 0.1% ivermectin in liposomes completely eliminated fowl mites within 24 hours.
  • Example 3 This example illustrates how the present invention was applied to eliminate roundworms, cecal worms (Heterakis) , and fowl mites in 70 week+ White Leghorn hens.
  • Ivermectin encapsulated in liposomes was added to 10 liters of drinking water such that a final concentration of drug in solution ranged from 10 ppm to 200 ppm.
  • the animals were placed in a cage setting and allowed to drink ad-lib for 48 hours. The birds were heavily infested with cecal worms at the start of the study and the infestation had proved difficult to remove by currently used methods such as by using piperazine or tramisol.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Dispersion Chemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne des procédés d'administration de composés à action pharmaceutique instables et/ou insolubles dans l'eau, à des animaux vertébrés. Ces procédés comprennent les phases d'encapsulation du composé dans des liposomes et d'administration dans de l'eau des liposomes à l'animal. Le composé à action pharmaceutique peut être un antiparasitaire, tel que l'ivermectine, un antibiotique, un nutriment, un composé de contrôle de croissance, ou d'autres composés. L'invention concerne également des procédés de stabilisation de composés à action pharmaceutique instables dans l'eau et de solubilisation de composés à action pharmaceutique insolubles dans l'eau.
PCT/US2000/004870 1999-02-26 2000-02-25 Procedes d'administration de composes a action pharmaceutique a des vertebres WO2000050009A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU36061/00A AU3606100A (en) 1999-02-26 2000-02-25 Methods for administering pharmacologically active compounds to vertebrates

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US25981299A 1999-02-26 1999-02-26
US09/259,812 1999-02-26

Publications (1)

Publication Number Publication Date
WO2000050009A1 true WO2000050009A1 (fr) 2000-08-31

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ID=22986499

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PCT/US2000/004870 WO2000050009A1 (fr) 1999-02-26 2000-02-25 Procedes d'administration de composes a action pharmaceutique a des vertebres

Country Status (2)

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AU (1) AU3606100A (fr)
WO (1) WO2000050009A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007053902A1 (fr) * 2005-11-10 2007-05-18 Bomac Animal Health Pty Limited Méthode pour traiter des parasites
US8777134B2 (en) 2006-06-14 2014-07-15 Intervet International B.V. Suspension comprising benzimidazole carbamate and a polysorbate
EP2861218A4 (fr) * 2012-06-18 2015-12-16 Lipotec Lab Llc Formulations de liposome
CN107496436A (zh) * 2017-10-19 2017-12-22 洛阳瑞华动物保健品有限公司 一种酒石酸泰乐菌素磺胺二甲嘧啶缓释微丸及其制备方法
US11077134B1 (en) * 2020-11-10 2021-08-03 Mountain Valley Md Inc Water dissolvable macrocyclic lactone cyclodextrin complexes

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990006747A1 (fr) * 1988-12-20 1990-06-28 Micro Vesicular Systems, Inc. Mise en capsules de parasiticides
US5023086A (en) * 1987-03-13 1991-06-11 Micro-Pak, Inc. Encapsulated ionophore growth factors
WO1991016068A1 (fr) * 1990-04-26 1991-10-31 Haynes Duncan H Microcristaux recouverts de phospholipides: formulations injectables de medicaments insolubles dans l'eau
DE19529861A1 (de) * 1995-08-14 1997-02-20 Berg & Schmidt Gmbh & Co Lipidhaltiges Konzentrat
US5851578A (en) * 1997-02-21 1998-12-22 Soma Technologies Clear or translucent liquid beverage with souluble fiber and nutrients

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5023086A (en) * 1987-03-13 1991-06-11 Micro-Pak, Inc. Encapsulated ionophore growth factors
WO1990006747A1 (fr) * 1988-12-20 1990-06-28 Micro Vesicular Systems, Inc. Mise en capsules de parasiticides
WO1991016068A1 (fr) * 1990-04-26 1991-10-31 Haynes Duncan H Microcristaux recouverts de phospholipides: formulations injectables de medicaments insolubles dans l'eau
DE19529861A1 (de) * 1995-08-14 1997-02-20 Berg & Schmidt Gmbh & Co Lipidhaltiges Konzentrat
US5851578A (en) * 1997-02-21 1998-12-22 Soma Technologies Clear or translucent liquid beverage with souluble fiber and nutrients

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007053902A1 (fr) * 2005-11-10 2007-05-18 Bomac Animal Health Pty Limited Méthode pour traiter des parasites
US8777134B2 (en) 2006-06-14 2014-07-15 Intervet International B.V. Suspension comprising benzimidazole carbamate and a polysorbate
EP2861218A4 (fr) * 2012-06-18 2015-12-16 Lipotec Lab Llc Formulations de liposome
CN107496436A (zh) * 2017-10-19 2017-12-22 洛阳瑞华动物保健品有限公司 一种酒石酸泰乐菌素磺胺二甲嘧啶缓释微丸及其制备方法
US11077134B1 (en) * 2020-11-10 2021-08-03 Mountain Valley Md Inc Water dissolvable macrocyclic lactone cyclodextrin complexes

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Publication number Publication date
AU3606100A (en) 2000-09-14

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