WO2004052400A1 - Pharmaceutical formulation and a method of making same - Google Patents
Pharmaceutical formulation and a method of making same Download PDFInfo
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- WO2004052400A1 WO2004052400A1 PCT/NZ2003/000272 NZ0300272W WO2004052400A1 WO 2004052400 A1 WO2004052400 A1 WO 2004052400A1 NZ 0300272 W NZ0300272 W NZ 0300272W WO 2004052400 A1 WO2004052400 A1 WO 2004052400A1
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- formulation
- active
- liquid
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- salts
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Classifications
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- 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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
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- 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
- A61K31/365—Lactones
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- 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
- A61K31/70—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
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/04—Sulfur, selenium or tellurium; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/18—Iodine; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/30—Zinc; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/34—Copper; Compounds thereof
-
- 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
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/143—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with inorganic compounds
-
- 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 pharmaceutical formulations, their preparation and their use in veterinary applications.
- the present invention relates to methods of making multi-active formulations which are capable of stably integrating multiple actives.
- a mixture may be required for effective management of a condition, or the combination may give an advantageous result over the administration of a single active.
- the actives to be co-administered will have overlapping formulation requirements and should to co-exist stably in the formulation.
- the actives to be co-administered will have conflicting formulation requirements or may actively degrade each other.
- levamisole is soluble in water-based formulations and requires an acidic pH for stability.
- avermectins are substantially insoluble in water. If formulated in water based formulation avermectins require a neutral pH for stability. In the acid pH required by levamisole the avermectins will degrade.
- the formulation must be practical to use. That is, it must be able to be stored for say up to a year without significant physical or chemical changes taking place.
- the relative proportions of the components should not change significantly over time. In addition, while some sedimentation is to be expected, the sediment should be easily re-dispersed on shaking. The formulation should not cause excessive side effects in the animal. The formulation should be relatively easy to administer and it is of suitable flowability to allow delivery by injection and drench.
- New Zealand Patent Application No. 336139 involves a storage stable veterinary composition comprising a levamisole containing aqueous phase and an anthelmintic containing organic phase wherein the composition having at least most of the first active in the organic phase is emulsified in the second liquid phase which includes the second active agent when present.
- this suspo-emulsion method tends to result in a formulation that is highly viscous and flows poorly. As such, it is difficult to administer.
- the invention comprises a method of manufacturing a pharmaceutical formulation comprising the steps:
- the active is a lipophilic active.
- the lipophilic active is selected from the group including the avermectins and the milbemycins.
- the liquid is an aqueous vehicle.
- the solvent is selected from oils and organic solvents.
- the solvent is selected from medium chain mono-/di-glycerides (Capmul MCM) in the range of 0.1-10% preferably between 2-4%.
- Capmul MCM medium chain mono-/di-glycerides
- the liquid optionally includes one or more medicaments selected from the group including vitamins, minerals, anthelmintics or antigens.
- the minerals are selected from selenium salts, cobalt slats, copper salts, zinc salts and iodine salts and their chelates.
- the minerals are sodium selenate and cobalt EDTA.
- the anthelmintics are selected from the group including thiazole derivatives such as a levamisole salt and benzimidazole derivates such as albendazole, oxfendazole, fenbendazole, mebendazole and acylated quinoline such as praziquantel and benzenesulphamide such as clorsulon and closantel.
- thiazole derivatives such as a levamisole salt and benzimidazole derivates
- albendazole oxfendazole, fenbendazole, mebendazole and acylated quinoline such as praziquantel and benzenesulphamide such as clorsulon and closantel.
- the sorbing medium is selected from magnesium aluminometasilicate, cellulose, microcrystalline cellulose, diatomaceous earth, montmorillonite, betonite, titanium dioxide, amorphous silicon dioxide, colloidal silicon dioxide, calcium carbonate, talc (SiO2+MgO), attapulgite (silicon, aluminium and iron oxides clay), kaolin (aluminium silicate) preferably colloidal silicon dioxide (Aerosil) more preferably Aerosil R972.
- the liquid optionally comprises further excipients including but not limited to preservatives, suspending agents, buffering agents, antifoaming agents and the like.
- the invention comprises a pharmaceutical formulation capable of dilution and capable (with or without dilution) of being administered to an animal, said formulation comprising:
- the active is a lipophilic active.
- the active is selected from , the group including the avermectins and the milbemycins.
- the solvent is selected from oils and organic solvents.
- the solvent is medium chain mono-/di-glycerides (Capmul MCM).
- the liquid diluent is an aqueous vehicle.
- liquid diluent optionally includes one or more additional medicaments selected from the group including vitamins, minerals, anthelmintics or antigens.
- the medicament is either soluble and/or dispersible in the liquid.
- the minerals are selected from wherein the minerals are selected from selenium salts, cobalt salts, copper salts, zinc salts and iodine salts and their chelates.
- the minerals are selected from sodium selenate and cobalt EDTA.
- the anthelmintics are selected from the group including thiazole derivatives such as a levamisole salt and benzimidazole derivates such as albendazole, oxfendazole, fenbendazole, mebendazole and acylated quinoline such as praziquantel, and benzenesulphonamide such as a clorsulon and closantel.
- thiazole derivatives such as a levamisole salt and benzimidazole derivates
- albendazole oxfendazole, fenbendazole, mebendazole and acylated quinoline such as praziquantel
- benzenesulphonamide such as a clorsulon and closantel.
- the formulation additionally includes preservatives, suspending agents, buffering agents, antifoaming agents and the like.
- the invention relates to a method of medical treatment comprising administering a formulation as described in the preceding statements to an animal.
- solvent means an oil or water immiscible liquid having good solubility for the active and being able to sorb onto the silica or other sorbing medium to physically separate the first active from the liquid.
- Active includes compounds which provide a health advantage or benefit to an animal to which the formulations referred to in the above paragraph are administered. Active includes vitamins, minerals, anthelmintics, antigens and the like.
- Liquid referred to in the preceding paragraphs comprises a liquid carrier optionally including one or more actives dissolved or suspended therein.
- the liquid may be water or oil based liquid.
- the liquid will be an aqueous vehicle, that is it will be water based and will include a water soluble active dissolved therein. It is envisaged however that the liquid may also include a further active suspended therein.
- the liquid may also include excipients including defoaming agents and buffering agents.
- the method requires the dissolving of a first active in a suitable solvent.
- This solution is sorbed onto a sorbing medium such as silica dioxide (e.g. Aerosil R972).
- a sorbing medium such as silica dioxide (e.g. Aerosil R972).
- This active loaded medium is then dispersed in a liquid.
- Suitable sorbing mediums include, by way of example, magnesium aluminometasilicate, cellulose, microcrystalline cellulose, diatomaceous earth, montmorillonite, bentonite, titanium dioxide, amorphous silicon dioxide, calcium carbonate, talc (SiO2+MgO), attapulgite (silicon, aluminium and iron oxides clay) and kaolin (aluminum silicate).
- the liquid in which the sorbing medium is to be dispersed may itself be a composition including an active.
- the liquid may comprise a water or oily based liquid and may include appropriate actives, such as levamisole, sodium selenate and the like.
- the liquid may include suspension aids/viscosity inducing agents such as sodium carboxy methylcellulose, guar gum, karaya gum or xanthan gum.
- preservatives such as methylparaben, propylparaben and their salts may be used to prevent degradation of the formulation.
- a defoamer such as a silicon emulsion can be used as a lubricant.
- suspension aids may be incorporated within the formulation.
- the formulation method may incorporate other actives including vitamins, minerals and the like as actives.
- actives including vitamins, minerals and the like as actives.
- the same actives may also be dissolved in the formulation and sorbed onto the silica or other sorbing medium to provide differential release of the active.
- avermectins or other anthelmintics may be incorporated into the formulation.
- additional actives may be incorporated in the suspension or sorbed onto the silica or other sorbing medium to provide for differential release of the active.
- the present invention relates to a method for making a formulation incorporating multiple actives.
- the formulation and method are advantageous as they allow the stable integration of actives, which have different formulation requirements, in the same formulation.
- the present invention is advantageous in that it allows the incorporation in a single formulation of multiple actives, which may be incompatible in that they have different solubility characteristics or requirements or they degrade the other.
- the active and solvent sorbed on to the sorbing medium should be incompatible with the liquid in which the active loaded sorbing medium is dispersed.
- a lipophilic active such as an avermectin
- a lipophilic solvent such as Capmul MCM and loaded onto Aerosil
- the liquid should be an aqueous based.
- An important factor in determining suitable active and solvent combinations for loading onto the Aerosil is the amount of active needed to provide effective treatment. Accordingly active which provide good efficacy at relatively low dose rates are more suitable for sorption onto the Aerosil than are actives which require administration of a relatively large dose for efficacy.
- the constraint is a physical one, the inclusion of a larger amount of Aerosil or other sorbing medium into a formulation can lead to difficulties in flowability.
- the present invention provides an improved veterinary composition including two or more actives together with a method of manufacturing the same.
- the initial trial included silicon dioxide (brand name Aerosil R972) and polyoxyl 40 hydrogenated castor oil.
- the formulation comprising:
- Carboxymethyl cellulose sodium is dissolved in 150ml of water.
- 500mg Ivermectin is dissolved in 25ml of medium chain mono-/di-glycerides (Capmul MCM.)
- Oxfendazole is dispersed into the formulation resulting from step 4 under stirring.
- the ivermectin-loaded silicon dioxide (brand name Aerosil R972) is dispersed into the formulation of step 5 under stirring.
- Step 1 The formulation of Step 1 is added to that from step 7 under stirring.
- the pH is adjusted to below 4, preferably 3.84 using 20%w/v citric acid solution.
- volume is made up to 500ml using purified water.
- silicon dioxide brand name Aerosil 200
- polyoxyl 40 hydrogenated castor oil was used in combination with polyoxyl 40 hydrogenated castor oil.
- the medium chain mono-/di-glycerides containing ivermectin are sorbed on silicon dioxide (brand name Aerosil 200) instead of silicon dioxide (brand name Aerosil R972), and
- the resulting formulation was chemically stable; however it exhibited a non-homogeneous sedimentation. Accordingly it was decided to discontinue this formulation.
- the flow time for this formulation was 28 seconds.
- the resulting formulation was surfactant free and chemically stable. This confirmed the formulation of example 3 was viable. However, it exhibited a flow time of 30 seconds.
- the formula in this example uses silicon dioxide (brand name Aerosil R972) alone and 0.5% carboxymethyl cellulose sodium to improve the flow time.
- Ivermectin is dissolved in 50ml of medium chain mono-/di-glycerides (Capmul MCM.) 3. 1.8mg Sodium methyl paraben and 200mg sodium propyl paraben are dissolved in
- the ivermectin-loaded silicon dioxide (brand name Aerosil R972) is dispersed into the formulation of step 5 under stirring.
- Step 1 The formulation of Step 1 is added to that from step 7 under stirring.
- the pH is adjusted to below 4, preferably 3.84 using 20%w/v citric acid solution.
- volume is made up to IL using purified water.
- step 10 the pH is set at 3.79 instead of 3.84 and 30%w/v citric acid solution is used instead of 20%w/v in example 6.
- step 11 the volume is made up to 1000ml using purified water. Testing of this formulation revealed a flow rate of 16 seconds confirming the defoamer had no effect on the flow rate.
- the following trial included ivermectin and xanthan gum.
- formulation components and methods comprised:
- the medium chain mono-/di-glycerides containing ivermectin was sorbed onto 90g silicon dioxide (brand name Aerosil R972) using mortar and pestle.
- Ivermectin loaded silicon dioxide (brand name Aerosil R972) was dispersed into the formulation from step 5 under stirring.
- step 8 50ml of purified water was used to rinse the beaker. This was then added to the formulation of step 8.
- the pH was adjusted to below 4 preferably 3.71 using 30%w/v citric acid solution.
- the volume was made up to 3000ml using purified water.
- step 7 the abamectin loaded silicon dioxide (brand name Aerosil R972) is dispersed into the formulation of step 5.
- example 10 was used to give a reduced quantity of medium chain mono-/di-glycerides, silicon dioxide (brand name Aerosil R972) and xanthan gum.
- the sodium benzoate was omitted.
- ivermectin is dissolved in 10ml medium chain mono-/di-glycerides instead of 15ml as in example 14.
- example 12 was the best formulation on the basis it stably integrated two pharmaceutical actives in the formulation.
- the suspension was surfactant free and had a low sedimentation rate resulting in a formulation that can be stored without significant physical change.
- the formulation also had a reduced flow rate of around 15 seconds through a Ford No. 4 cup to allow for easy and effective administration of the formulation to animals.
- a lipophilic active ivermectin is firstly solubilised and then sorbed on a hydrophobic grade of silica.
- the surrounding aqueous solution contains levamisole, an active more stable at low pH.
- Levamisole salts (Levamisole HC1) are easily soluble in water.
- This method provides a physical and chemical separation between the sorbed ivermectin/silica and the surrounding solution or suspension containing the second or more active ingredients. It is envisaged that other materials may also be used as the sorbing medium. It will be appreciated that other combinations of actives may be used
- Cobalt EDTA 6.284gm Capmul MCM 15ml Aerosil R972 9gms Xanthan gum 1.250gms Nipagin Sod. 900mg Nipasol Sod. lOOmg Defoamer lOgms
- step 6 Disperse Adsorbed abamectin in step 4 under stirring.
- step 8 Add step 1 to step 7 under stirring.
- step 8 Add step 1 to step 7 under stirring.
- step 9 Add citric acid anhydrous to step 8 and check the pH.
- 3 -way and 4-way drench formulations are suspension type of dosage forms. Some sediment formed upon standing at room temperature. The sedimented portion was easily redispersed upon shaking. There was no sign of cake formation.
- the preferred formulations have also been shown to be highly efficacious in field use.
- the formulations were administered to animals as a drench at a rate of 1 ml per 5 kg animal weight.
- Tables 1 and 2 below show the arithmetic and geometric mean total worm counts respectively for groups of sheep treated with the 3 and 4 active drenches.
- Tables 3 and 4 show the efficacies of each of the treatments relative to the controls using arithmetic and geometric means respectively.
- Results demonstrate that both the 3 and 4 active drenches were highly effective against all species present in the trial. Efficacies of >99.9% were achieved against all parasites that were present. Worm numbers in the control animals were high for all species that were present demonstrating that the animals were exposed to a very high parasite challenge.
- Table 1 Arithmetic mean total worm counts for control and treated groups
- Trichostrongylus spp 26983 (mature)
- Trichostrongylus spp 75 (immature)
- Trichostrongylus spp 20254 a (mature)
- Trichuris 15 a 0 b 0" a means with different superscripts within the same row are statistically different from each other.
- Table 3 Treatment efficacies based on group arithmetic mean total worm counts.
- Table 4 Treatment efficacies based on group geometric mean total worm counts.
- the methods of the present invention and the formulations made from those methods allow the stable integration of multiple actives within a single formulation.
- the solubilisation of the active in a solvent and the subsequent adsorption onto a sorbing medium provide effective protection for the active from any adverse conditions within the liquid in which the active-loaded sorbing medium is dispersed.
- the liquid can be formulated to suit the requirements of the actives that may include therein.
- the actives may be stably integrated within the formulation. This allows the co-administration of the actives and the resultant benefits in terms of cost savings and convenience to be enjoyed.
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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)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP03781126.2A EP1581258B1 (en) | 2002-12-12 | 2003-12-12 | Pharmaceutical formulation and a method of making same |
DK03781126.2T DK1581258T3 (en) | 2002-12-12 | 2003-12-12 | PHARMACEUTICAL FORMULATION AND PROCEDURE FOR PREPARING THIS |
BR0316770-4A BR0316770A (en) | 2002-12-12 | 2003-12-12 | Pharmaceutical formulation, production method and medical treatment method |
US10/542,032 US20060198850A1 (en) | 2002-12-12 | 2003-12-12 | Pharmaceutical formulation and a method of making same |
AU2003288820A AU2003288820B2 (en) | 2002-12-12 | 2003-12-12 | Pharmaceutical formulation and a method of making same |
SI200332502T SI1581258T1 (en) | 2002-12-12 | 2003-12-12 | Pharmaceutical formulation and a method of making same |
AU2008229987A AU2008229987A1 (en) | 2002-12-12 | 2008-10-17 | Pharmaceutical formulation and a method of making same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NZ523128A NZ523128A (en) | 2002-12-12 | 2002-12-12 | Anthelmintic formulations containing avermectins and or milbemycins |
NZ523128 | 2002-12-12 |
Publications (1)
Publication Number | Publication Date |
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WO2004052400A1 true WO2004052400A1 (en) | 2004-06-24 |
Family
ID=32501630
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/NZ2003/000272 WO2004052400A1 (en) | 2002-12-12 | 2003-12-12 | Pharmaceutical formulation and a method of making same |
Country Status (10)
Country | Link |
---|---|
US (1) | US20060198850A1 (en) |
EP (1) | EP1581258B1 (en) |
AU (2) | AU2003288820B2 (en) |
BR (1) | BR0316770A (en) |
DK (1) | DK1581258T3 (en) |
HU (1) | HUE031069T2 (en) |
NZ (1) | NZ523128A (en) |
SI (1) | SI1581258T1 (en) |
WO (1) | WO2004052400A1 (en) |
ZA (1) | ZA200505576B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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ES2696400A1 (en) * | 2017-08-03 | 2019-01-15 | Univ Granada | PROCEDURE FOR PREPARING A NANOSTRUCTURED MATERIAL OF PRAZIQUANTEL AND A SILICATE, MATERIAL OBTAINED AND USED AS ANTIPARASITARY (Machine-translation by Google Translate, not legally binding) |
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AU2002952597A0 (en) * | 2002-11-11 | 2002-11-28 | Schering-Plough Pty. Limited | Topical parasiticide formulations and methods of treatment |
ES2401434T3 (en) * | 2004-11-19 | 2013-04-19 | Glaxosmithkline Llc | Method for individually dispensing combination dose drug products for the individualization of therapies |
AR079409A1 (en) * | 2009-09-07 | 2012-01-25 | Mukhopadhyay Debashis | GRANULATED ANTIHELMINTIC PREPARATIONS AND SUNINISTER SYSTEMS |
WO2011075592A1 (en) | 2009-12-17 | 2011-06-23 | Merial Limited | Compositions comprising macrocyclic lactone compounds and spirodioxepinoindoles |
US20130267590A1 (en) * | 2011-09-13 | 2013-10-10 | Dr. Reddy's Laboratories Limited | Retigabine compositions |
US9770514B2 (en) * | 2013-09-03 | 2017-09-26 | ExxPharma Therapeutics LLC | Tamper-resistant pharmaceutical dosage forms |
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US4678774A (en) * | 1985-06-06 | 1987-07-07 | Merck & Co., Inc. | Novel synergistic compositions |
JPH0585902A (en) * | 1991-09-24 | 1993-04-06 | Nippon Kayaku Co Ltd | Sustained release agricultural chemical formulation containing bio-degradable polymer and its production |
WO2001060409A1 (en) * | 2000-02-16 | 2001-08-23 | Merial Limited | Improved paste formulations |
NZ336139A (en) | 1999-06-04 | 2002-07-26 | Nufarm Ltd | Pesticidal emulsion composition containing levamisole in the aqueous phase and an anthelmintic in the organic phase |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4607050A (en) * | 1981-10-19 | 1986-08-19 | Wellcome Australia Limited | Method of controlling insects and parasites with an aqueous localized pour-on formulation |
US4711774A (en) * | 1986-03-27 | 1987-12-08 | Warner-Lambert Company | Medicament adsorbates with complex magnesium aluminum silicate and their preparation |
US6165987A (en) * | 1996-07-30 | 2000-12-26 | Harvey; Colin Manson | Anthelmintic formulations |
US6248363B1 (en) * | 1999-11-23 | 2001-06-19 | Lipocine, Inc. | Solid carriers for improved delivery of active ingredients in pharmaceutical compositions |
ATE313952T1 (en) * | 1999-06-04 | 2006-01-15 | Nufarm Ltd | STABLE BIOCIDAL COMPOSITION |
AUPQ875700A0 (en) * | 2000-07-13 | 2000-08-03 | Reflex Research Limited | Combination compositions |
-
2002
- 2002-12-12 NZ NZ523128A patent/NZ523128A/en not_active IP Right Cessation
-
2003
- 2003-12-12 DK DK03781126.2T patent/DK1581258T3/en active
- 2003-12-12 US US10/542,032 patent/US20060198850A1/en not_active Abandoned
- 2003-12-12 BR BR0316770-4A patent/BR0316770A/en not_active Application Discontinuation
- 2003-12-12 SI SI200332502T patent/SI1581258T1/en unknown
- 2003-12-12 HU HUE03781126A patent/HUE031069T2/en unknown
- 2003-12-12 AU AU2003288820A patent/AU2003288820B2/en not_active Expired
- 2003-12-12 WO PCT/NZ2003/000272 patent/WO2004052400A1/en not_active Application Discontinuation
- 2003-12-12 EP EP03781126.2A patent/EP1581258B1/en not_active Expired - Lifetime
-
2005
- 2005-07-12 ZA ZA200505576A patent/ZA200505576B/en unknown
-
2008
- 2008-10-17 AU AU2008229987A patent/AU2008229987A1/en not_active Abandoned
Patent Citations (4)
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US4678774A (en) * | 1985-06-06 | 1987-07-07 | Merck & Co., Inc. | Novel synergistic compositions |
JPH0585902A (en) * | 1991-09-24 | 1993-04-06 | Nippon Kayaku Co Ltd | Sustained release agricultural chemical formulation containing bio-degradable polymer and its production |
NZ336139A (en) | 1999-06-04 | 2002-07-26 | Nufarm Ltd | Pesticidal emulsion composition containing levamisole in the aqueous phase and an anthelmintic in the organic phase |
WO2001060409A1 (en) * | 2000-02-16 | 2001-08-23 | Merial Limited | Improved paste formulations |
Non-Patent Citations (2)
Title |
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PATENT ABSTRACTS OF JAPAN * |
See also references of EP1581258A4 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2696400A1 (en) * | 2017-08-03 | 2019-01-15 | Univ Granada | PROCEDURE FOR PREPARING A NANOSTRUCTURED MATERIAL OF PRAZIQUANTEL AND A SILICATE, MATERIAL OBTAINED AND USED AS ANTIPARASITARY (Machine-translation by Google Translate, not legally binding) |
WO2020012044A1 (en) * | 2017-08-03 | 2020-01-16 | Universidad De Granada | Method for preparing a nano-structured material of praziquantel and a silicate, material obtained and use as an antiparasitic |
Also Published As
Publication number | Publication date |
---|---|
ZA200505576B (en) | 2006-06-28 |
EP1581258A1 (en) | 2005-10-05 |
DK1581258T3 (en) | 2016-12-19 |
SI1581258T1 (en) | 2018-12-31 |
AU2003288820B2 (en) | 2008-08-21 |
NZ523128A (en) | 2006-01-27 |
EP1581258B1 (en) | 2016-08-31 |
AU2003288820A1 (en) | 2004-06-30 |
BR0316770A (en) | 2005-10-25 |
AU2008229987A1 (en) | 2008-11-06 |
EP1581258A4 (en) | 2011-06-15 |
US20060198850A1 (en) | 2006-09-07 |
HUE031069T2 (en) | 2017-06-28 |
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