WO2006041843A2 - Forme posologique pharmaceutique comprenant meloxicam - Google Patents
Forme posologique pharmaceutique comprenant meloxicam Download PDFInfo
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- WO2006041843A2 WO2006041843A2 PCT/US2005/035686 US2005035686W WO2006041843A2 WO 2006041843 A2 WO2006041843 A2 WO 2006041843A2 US 2005035686 W US2005035686 W US 2005035686W WO 2006041843 A2 WO2006041843 A2 WO 2006041843A2
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- meloxicam
- particle size
- dosage form
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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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/485—Inorganic compounds
-
- 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
- A61K9/2009—Inorganic compounds
-
- 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
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- 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
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- 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
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Definitions
- the present invention relates to solid oral pharmaceutical compositions comprising meloxicam or pharmaceutically acceptable salts, solvates, enantiomers or mixtures thereof with improved solubility and desired dissolution characteristics.
- Meloxicam is a nonsteroidal anti-inflammatory drug (NSAID) that exhibits anti-inflammatory, analgesic and antipyretic activities.
- NSAID nonsteroidal anti-inflammatory drug
- the mechanism of action of meloxicam is similar to other NSAIDs related to prostaglandin synthetase (cyclooxygenase) inhibition.
- Meloxicam an oxicam derivative, is a member of the enolic acid group of NSAIDs. It is chemically designated as 4-hydroxy-2-methyl-/V-(5-methyl-2- thiazolyl)-2H-1 ,2-benzothiazine-3-carboxamide-1 ,1 -dioxide with the structural Formula I.
- Meloxicam is the active ingredient in pharmaceutical products currently marketed using the trademark MOBIC, the tablet products containing 7.5 mg and 15 mg of meloxicam for oral administration.
- Pharmacokinetics of meloxicam have been shown to be dose proportional with single dosing within the dose range of 5 to 60 mg.
- Mean C ma ⁇ maximal plasma concentration was achieved within 4-5 hours after administration of the 7.5 mg MOBIC tablet under fasted conditions.
- U.S. Patent Nos. 6,184,220 and 6,682,747 to T ⁇ rck et al. describe an aqueous oral suspension formulation comprising particles of NSAID selected from the acid enolcarboxamides (oxicams), particularly meloxicam, having a suspendable particle size spectrum in which at least 90% of the particles are smaller than 50 ⁇ m. Preferably, at least 50% of the particles are smaller than 10 ⁇ m and most preferably about 90% of the particles are smaller than 10 ⁇ m. This can be achieved by grinding a coarser grade of the oxicam.
- oxicams acid enolcarboxamides
- the patents also compare the fine particle material suspension formulation and a capsule preparation.
- the t max time required for achieving a maximum plasma concentration of the drug
- the t max was statistically different from the t max of 5 hours (range 2 to 6 hours) for the capsule.
- U.S. Patent No. 6,284,269 to Struengmann et al. describes a pharmaceutical composition comprising meloxicam as an active ingredient, a cyclodextrin, a facultative oligosaccharide other than cyclodextrin, a facultative polysaccharide, one or more pharmaceutically acceptable additives, and facultative excipients, carriers and/or auxiliary agents, wherein the pharmaceutical composition is obtainable by co-milling, co-grinding or co-kneading meloxicam in the presence of cyclodextrin as a pharmaceutically acceptable additive.
- the composition after the grinding process in presence of cyclodextrin exhibited an improved dissolution profile compared to meloxicam ground alone under the same conditions.
- WO 2005/002542 of Elan Pharma International Ltd. discloses a nanoparticulate composition comprising meloxicam particles having an effective average particle size of less than about 2000 nm and at least one surface stabilizer.
- the nanoparticulate compositions either in the form of a colloidal dispersion or as a lyophilized wafer, have higher bioavailabilities as compared to the commercial MOB1C ® tablet.
- the rate of dissolution of a poorly-soluble drug is a rate-limiting factor in its absorption by the body.
- a reduction in the particle size can increase the dissolution rate of such compounds through an increase in the surface area of the solid phase that is in contact with the liquid medium, thereby resulting in an enhanced bioavailability of the compositions containing such compounds. It is generally not possible to predict the exact particle size and distribution required for any particular drug substance to achieve a specific dissolution profile or a specific in vivo behavior, as different drugs show differing dissolution characteristics with a reduction in the particle size.
- the problem is further complicated by the fact that the same compound may exist in more than one crystalline form, each of which could have a different dissolution profile.
- the present invention relates to solid oral pharmaceutical compositions of meloxicam or pharmaceutically acceptable salts, solvates, enantiomers or mixtures thereof of a defined particle size and distribution and processes for preparing the same.
- the invention also relates to solid oral pharmaceutical compositions comprising meloxicam having a defined particle size wherein a plurality of meloxicam particles have a mean particle size of about 2 ⁇ m to about 25 ⁇ m, or about 2 ⁇ m to about 10 ⁇ m, or about 2 ⁇ m to about 5 ⁇ m.
- the particles have a size distribution of Di 0 about 2 ⁇ m or less, D 50 about 5 ⁇ m or less, and D 90 about 15 ⁇ m or less.
- the solid oral pharmaceutical composition is a dosage form such as a tablet or capsule.
- the invention further relates to processes for preparing the pharmaceutical compositions using meloxicam of defined particle size and distribution as defined above.
- An embodiment of the process comprises: a. forming a mixture of the meloxicam particles and at least one pharmaceutically acceptable excipient; b. optionally granulating the mixture, optionally using an aqueous or organic solvent, with or without a binder, and removing solvent to form a granulate; and -A-
- the invention also includes therapeutic uses and methods of treatment employing the composition comprising meloxicam of defined particle size and distribution or such pharmaceutical dosage forms, medicaments or products.
- the present invention relates to solid oral pharmaceutical compositions of meloxicam of defined particle sizes and distribution and processes for preparing the same.
- a particle size distribution of D 50 as used herein is defined as the distribution where 50 volume-% of the particles are smaller than that size given
- a particle size distribution of Dio as used herein is defined as the distribution where 10 volume-% of the particles are smaller than that size given
- a particle size distribution of Dgo as used herein is defined as the distribution where 90 volume-% of the particles are smaller than that size given.
- the D 50 value is considered to be a "mean particle size.”
- the drug meloxicam as used herein includes without any limitation pharmaceutically acceptable salts, solvates, enantiomers, other polymorphic or crystalline forms or mixtures thereof.
- meloxicam with a defined particle size and distribution which enables the preparation of pharmaceutical dosage forms with a better control on the in vitro and in vivo behavior.
- the meloxicam of the invention comprises a plurality of meloxicam particles having a mean particle size (D 50 ) of about 2 ⁇ m to about 25 ⁇ m, or about 2 ⁇ m to about 10 ⁇ m, or about 2 ⁇ m to about 5 ⁇ m.
- feedstock used comprises but is not limited to crystals, powder aggregates, and coarse powders of either crystalline or amorphous meloxicam, and the like.
- the most widely practiced methods of sorting by particle size involve passing the milled material through a stack of sieves, each having openings of different sizes.
- the sieves are arranged so that the material encounters the sieve having the largest openings first, and those particles that pass through the first sieve encounter a second sieve with smaller openings. Particles that pass through the second sieve may encounter a third sieve, and so forth.
- Meloxicam particles can also be separated by particle size using various techniques such as cyclonic techniques, centrifugation techniques, and the like.
- a fluid energy mill or "micronizer” is found to be useful for its ability to produce particles of small sizes in a narrow size distribution.
- Micronizers use the kinetic energy of collisions between particles suspended in a rapidly moving fluid (typically air or an inert gas) stream to cleave the particles.
- an air jet mill is found to be useful as an example of a fluid energy mill.
- the suspended particles are injected under pressure into a recirculating particle stream, typically in a manner to intersect with the recirculating stream at an oblique angle.
- Smaller particles are carried aloft inside the mill and swept into a vent connected to a particle size classifier such as a cyclone separator.
- the feedstock used will usually first be milled to have a mean particle size about 150 to 850 ⁇ m, or smaller.
- the size distribution of meloxicam particles of the present invention can be determined by techniques such as, for example, laser diffraction, Coulter counter measurement, or microscopy. Other techniques for the measurement of particle size are also acceptable.
- meloxicam particles and the distributions reported herein were determined using a Malvern MastersizerTM laser diffraction instrument (Malvern Instruments Ltd., Worcestershire, UK). Samples of the meloxicam were suspended in hexane containing the surfactant, 1% polyoxyethylene sorbitan monooleate. The suspensions were mixed and then sonicated for 1-5 minutes to thoroughly disperse the meloxicam particles. The dispersion was then circulated in the flow cell of the Malvern MastersizerTM for about two minutes before particle size measurements were taken.
- the invention also relates to solid oral pharmaceutical compositions comprising meloxicam having a defined particle size wherein a plurality of meloxicam particles have a mean particle size (D 5 o) about 2 ⁇ m to about 25 ⁇ m, or about 2 ⁇ m to about 10 ⁇ m, or about 2 ⁇ m to about 5 ⁇ m, with a desired in vitro and in vivo behavior.
- meloxicam having a defined particle size wherein a plurality of meloxicam particles have a mean particle size (D 5 o) about 2 ⁇ m to about 25 ⁇ m, or about 2 ⁇ m to about 10 ⁇ m, or about 2 ⁇ m to about 5 ⁇ m, with a desired in vitro and in vivo behavior.
- Meloxicam with a defined particle size and distribution as described herein is useful for preparing pharmaceutical compositions and encapsulated free flowing and compressed solid dosage forms such as tablets, caplets, capsules, troches, lozenges and the like.
- the meloxicam is also useful for preparing solid dosage forms such as powders, including granulated powders.
- the meloxicam with a particle size and distribution as defined herein is useful in the preparation of tablet formulations which have in vitro and in vivo behavior comparable to that of a commercially available product, MOBIC.
- pharmaceutical composition means a solid dosage form (medicament) for use in treating a mammal that includes meloxicam of a defined particle size distribution and is prepared in a manner that is appropriate for administration to a mammal, preferably a human.
- a pharmaceutical composition contains one or more pharmaceutically acceptable excipients that are non-toxic to the mammal intended to be treated when the composition is administered in an amount effective to treat the mammal.
- compositions are well known in the art and perform various functions. They add bulk or act as diluents, improve bulk-handling properties or aid in dissolution or disintegration of the final oral solid dosage form.
- a person skilled in the art of development and manufacture of pharmaceutical solid oral dosage forms is aware of the factors involved in making a choice of different excipients.
- a given pharmaceutically acceptable excipient may have more than one of the foregoing characteristics or properties and classification of excipients according to function is therefore somewhat arbitrary.
- compositions of the present invention can contain one or more diluents added to make the tablet or capsule mass and hence easier for the formulator, patient and caregiver to handle.
- diluents are, but are not limited to, microcrystalline cellulose, powdered cellulose, lactose, starch, pregelatinized starch, calcium carbonate, calcium sulfate, sugar, dextrates, dextrin, dextrose, dibasic calcium phosphate dihydrate, tribasic calcium phosphate, kaolin, magnesium carbonate, magnesium oxide, maltodextrin, mannitol, and the like.
- Binders can also be included in the pharmaceutical compositions of the present invention to help hold granules or tablets together.
- Some typical binders are: gums like acacia, alginic acid, sodium alginate, gelatin, guar gum; starch; pregelatinized starch; carbomer (e.g. carbopol); povidone (e.g. Kollidon®, Plasdone®); celluloses like carboxy methylcellulose sodium, methylcellulose, ethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose (e.g. Klucel®), hydroxypropyl methyl cellulose (e.g.
- Methocel® liquid glucose; magnesium aluminum silicate (VeegumTM); dextrin; maltodextrin; polymethacrylates; and the like.
- Useful organic alkalizers or inorganic salts for pH adjustment include but are not limited to sodium or potassium carbonate; sodium or potassium citrate; sodium or potassium acetate, and basic amines such as arginine, tromethamine and meglumine.
- the pharmaceutical compositions to be made into tablets or capsules can further include a disintegrant to accelerate disintegration of the tablet or capsule in the patient's digestive system.
- a disintegrant to accelerate disintegration of the tablet or capsule in the patient's digestive system.
- Useful disintegrants include alginic acid, carboxymethyl cellulose calcium, carboxymethyl cellulose sodium (e.g. Ac-Di- Sol®, Primellose®), colloidal silicon dioxide, crospovidone (e.g. Kollidon®, Polyplasdone®), guar gum, magnesium aluminum silicate, microcrystalline cellulose, polacrilin potassium, powdered cellulose, pregelatinized starch, sodium alginate, sodium starch glycolate (e.g. Explotab®), starch, and the like.
- compositions for tableting and encapsulation may further include glidants, lubricants, flavoring agents, colorants and other commonly used excipients, as will be readily appreciated by a person skilled in the art.
- Pharmaceutical compositions are prepared using process known to those skilled in the art, such as direct compression, dry granulation, compaction granulation, or wet granulation. Powder blends or granules are further mixed with other excipients and either filled into capsules or compressed as tablet. These and other excipients may all be used without limitation to provide a pharmaceutical composition containing meloxicam with the above described particle size characteristics of the invention.
- the meloxicam compositions of the present invention can be administered to a mammal via the oral route.
- a mammal is used to define a human or a non-human.
- patient and mammal may be used interchangeably.
- the present invention provides a method of rapidly increasing the plasma levels of meloxicam in a patient. Such a method comprises administering to a mammal an effective amount of a composition comprising meloxicam particles having a mean particle sizes (D 5 o) of about 2 ⁇ m to about 25 ⁇ m, or about 2 ⁇ m to about 10 ⁇ m, or about 2 ⁇ m to about 5 ⁇ m.
- D 5 o mean particle sizes
- compositions of the invention are useful in treating or preventing disorders or conditions such as arthritic disorders, gastrointestinal conditions, inflammatory conditions, pulmonary inflammation, ophthalmic diseases, central nervous system disorders, pain, fever, inflammation related cardiovascular disorders, disorders of female reproductive system such as endometriosis, osteoporosis, dysmenorrhea, and fibromyalgia syndrome, infectious arthritis, psoriatic arthritis, osteoarthritis, rheumatoid arthritis, and the like.
- disorders or conditions such as arthritic disorders, gastrointestinal conditions, inflammatory conditions, pulmonary inflammation, ophthalmic diseases, central nervous system disorders, pain, fever, inflammation related cardiovascular disorders, disorders of female reproductive system such as endometriosis, osteoporosis, dysmenorrhea, and fibromyalgia syndrome, infectious arthritis, psoriatic arthritis, osteoarthritis, rheumatoid arthritis, and the like.
- An orally administered tablet or capsule according to the invention can contain one or more NSAIDs as a pharmaceutically active substance in addition to meloxicam particles having a mean particle size (D 50 ) of about 2 ⁇ m to about 25 ⁇ m.
- the classic active substance acetylsalicylic acid and the following active substances of the following categories are examples of these NSAIDs: propionic acid derivatives such as but not limited to ibuprofen, naproxen, flurbiprofen, fenoprofen, fenbufen, ketoprofen, indoprofen, pirprofen, carprofen, oxaprozin, pranoprofen, miroprofen, tioxaprofen, suprofen, alminoprofen, tiaprofenic acid, fluprofen, and the pharmaceutically acceptable salts and derivatives thereof; acetic acid derivatives such as but not limited to indomethacin, sulindac
- fenamic acid derivatives such as but not limited to, mefenamic acid, meclofenamic acid, flufenamic acid, nifluminic acid, tolfenamic acid and the pharmaceutically acceptable salts thereof
- biphenylcarboxylic acid derivatives such as but not limited to, diflunisal, flufenisal, and the pharmaceutically acceptable salts thereof
- acid enolcarboxamides oxicams
- diaryl heterocycles with methylsulphonyl or aminosulphonyl substitutes, acid sulphonamides such as but not limited to nimesulide; and the like.
- the dose of meloxicam in a pharmaceutical composition according to the instant invention can range from about 1 to about 20 milligrams, or from about 5 to about 15 milligrams.
- meloxicam with a mean particle size in the range of about 2 to about 25 ⁇ m, or about 2 to about 10 ⁇ m, or about 2 to about 5 ⁇ m is suitable for purposes of the invention.
- Useful meloxicam average particle sizes for compositions of the invention include about 2 ⁇ m, or about 3 ⁇ m, or about 4 ⁇ m, and the particles will typically have bulk densities about 0.2 to about 0.3 g/ml, with tapped bulk densities about 0.4 to about 0.6 g/ml, as determined using the standard method of Test 611 (Bulk Density and Tapped Density) of United States Pharmacopeia 24, The United States Pharmacopeial Convention, Inc., Rockville, Maryland, 1999.
- meloxicam particles have a particle size distribution of Di 0 about 2 ⁇ m or less, D 50 about 5 ⁇ m or less, and Dg 0 about 15 ⁇ m or less.
- a process for the manufacture of the meloxicam composition of the invention comprising:
- Useful solvents for granulating the dry mixture containing meloxicam of desired particle sizes include, without limitation thereto, water, isopropyl alcohol, acetone, dichloromethane, methanol, ethanol, chloroform and the like. Combinations of one or more solvents for use in granulation also falls within the scope of invention.
- the following examples will further illustrate certain aspects of the invention in greater detail and are not intended to limit the scope of the invention.
- a coarse meloxicam powder was subjected to size reduction by jet milling, using air as the fluid at pressures about 4-6 bar, in an Alpine jet micronizer manufactured by Hosokawa Alpine AG, of Augsburg, Germany.
- Particle size distributions of the feed material and two batches of micronized products were determined using a Malvern Mastersizer instrument.
- the feed material and micronized products were also characterized according to Test 611 (Bulk Density and Tapped Density) of United States Pharmacopeia 24, The United States Pharmacopeial Convention, Inc., Rockville, Maryland, 1999, using tapping Method II, and the following results were obtained:
- Samples of meloxicam having different particle size distribution profiles were filled into gelatin capsules, for dissolution testing.
- the samples were characterized, as follows:
- Capsules containing 15 mg of drug were tested according to Test 711 (Dissolution) of United States Pharmacopeia 24, The United States Pharmacopeial Convention, Inc., Rockville, Maryland, 1999, using Apparatus 2, a stirring rate of 75 rpm, and 900 ml of a pH 7.5 phosphate buffer.
- PVP K-30 was weighed and dissolved in about 0.5 ml of water
- step 1 The dry mixture of step 1 was granulated using solutions of steps 2 and 3;
- step 7 the mixture of step 7 was compressed into tablets using a rotary tablet compression machine.
- the tablets were manufactured using the procedure of Example 2.
- Tablet formulations 1 , 2, and 3 were prepared as described in Example 3, except for the presence or absence of the sodium citrate dihydrate component, and the particle size distribution of the meloxicam.
- Formulation 1 was made using coarse meloxicam (D 50 « 79 ⁇ m), and without the sodium citrate dihydrate.
- Formulation 2 was made using coarse meloxicam (D 50 « 79 ⁇ m) and with the sodium citrate dihydrate.
- Formulation 3 was made using fine meloxicam (D 50 ⁇ 4 ⁇ m) and with the sodium citrate dihydrate.
- tablet formulation 3 comprising meloxicam of a mean particle size about 4 ⁇ m exhibits a higher rate and extent of drug dissolution, when compared to the formulations 1 and 2 with a mean meloxicam particle size of about 79 ⁇ m, either with or without sodium citrate dihydrate.
- compositions prepared according to Example 3 and comprising meloxicam having a mean particle size about 2 ⁇ m were tested for bioequivalence to the commercially available meloxicam 15 mg tablets (MOBIC ® ).
- An open label single dose crossover study was carried out using thirteen healthy human male volunteers in the fed state. The results of the study are tabulated below:
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Abstract
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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IN1023CH2004 | 2004-10-04 | ||
IN1023/CHE/2004 | 2004-10-04 |
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WO2006041843A2 true WO2006041843A2 (fr) | 2006-04-20 |
WO2006041843A3 WO2006041843A3 (fr) | 2006-08-24 |
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
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EP2015632A2 (fr) * | 2006-04-19 | 2009-01-21 | Novadel Pharma Inc. | Formulations hydroalcooliques stables à pulvériser dans la cavité buccale et procédés associés |
WO2010121325A1 (fr) * | 2009-04-24 | 2010-10-28 | Iceutica Pty Ltd | Nouvelle formulation de méloxicam |
WO2010121323A1 (fr) * | 2009-04-24 | 2010-10-28 | Iceutica Pty Ltd | Procédé destiné à la production de poudres de nanoparticules et de microparticules à usage commercial |
WO2011026080A1 (fr) * | 2009-08-31 | 2011-03-03 | Wilmington Pharmaceuticals, Llc | Compositions à désintégration rapide de méloxicame, procédés pour sa fabrication et utilisation pour traiter l'arthrite et/ou la douleur |
RU2465892C1 (ru) * | 2011-09-21 | 2012-11-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Новосибирский национальный исследовательский государственный университет (НГУ)" | Способ получения высокодисперсного мелоксикама |
US8992982B2 (en) | 2009-04-24 | 2015-03-31 | Iceutica Pty Ltd. | Formulation of indomethacin |
US9526734B2 (en) | 2014-06-09 | 2016-12-27 | Iceutica Pty Ltd. | Formulation of meloxicam |
US11103456B2 (en) | 2006-06-30 | 2021-08-31 | Iceutica Pty Ltd. | Methods for the preparation of biologically active compounds in nanoparticulate form |
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CN107970219A (zh) * | 2017-12-27 | 2018-05-01 | 佛山市南海东方澳龙制药有限公司 | 宠物用美洛昔康片及其制备方法和应用 |
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US20040229038A1 (en) * | 2003-03-03 | 2004-11-18 | Elan Pharma International Ltd. | Nanoparticulate meloxicam formulations |
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2005
- 2005-10-04 WO PCT/US2005/035686 patent/WO2006041843A2/fr active Application Filing
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US20040229038A1 (en) * | 2003-03-03 | 2004-11-18 | Elan Pharma International Ltd. | Nanoparticulate meloxicam formulations |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2015632A4 (fr) * | 2006-04-19 | 2011-03-23 | Novadel Pharma Inc | Formulations hydroalcooliques stables à pulvériser dans la cavité buccale et procédés associés |
EP2015632B1 (fr) | 2006-04-19 | 2015-12-02 | Mist Pharmaceuticals, LLC | Formulations hydroalcooliques stables à pulvériser dans la cavité buccale et procédés associés |
EP2015632A2 (fr) * | 2006-04-19 | 2009-01-21 | Novadel Pharma Inc. | Formulations hydroalcooliques stables à pulvériser dans la cavité buccale et procédés associés |
US11103456B2 (en) | 2006-06-30 | 2021-08-31 | Iceutica Pty Ltd. | Methods for the preparation of biologically active compounds in nanoparticulate form |
JP2015131811A (ja) * | 2009-04-24 | 2015-07-23 | イシューティカ ピーティーワイ リミテッド | メロキシカムの新規製剤 |
WO2010121323A1 (fr) * | 2009-04-24 | 2010-10-28 | Iceutica Pty Ltd | Procédé destiné à la production de poudres de nanoparticules et de microparticules à usage commercial |
WO2010121325A1 (fr) * | 2009-04-24 | 2010-10-28 | Iceutica Pty Ltd | Nouvelle formulation de méloxicam |
US10172828B2 (en) | 2009-04-24 | 2019-01-08 | Iceutica Pty Ltd. | Formulation of indomethacin |
AU2010239162B2 (en) * | 2009-04-24 | 2014-10-02 | Iceutica Pty Ltd | Method for the production of commercial nanoparticle and microparticle powders |
US8992982B2 (en) | 2009-04-24 | 2015-03-31 | Iceutica Pty Ltd. | Formulation of indomethacin |
US9849111B2 (en) | 2009-04-24 | 2017-12-26 | Iceutica Pty Ltd. | Formulation of indomethacin |
US9089471B2 (en) | 2009-04-24 | 2015-07-28 | Iceutica Pty Ltd. | Formulation of indomethacin |
US9095496B2 (en) | 2009-04-24 | 2015-08-04 | Iceutica Pty Ltd. | Formulation of indomethacin |
JP2012524721A (ja) * | 2009-04-24 | 2012-10-18 | イシューティカ ピーティーワイ リミテッド | メロキシカムの新規製剤 |
AP3659A (en) * | 2009-04-24 | 2016-04-08 | Iceutica Pty Ltd | A novel formulation of meloxicam |
US9522135B2 (en) | 2009-04-24 | 2016-12-20 | Iceutica Pty Ltd. | Formulation of indomethacin |
JP2017019838A (ja) * | 2009-04-24 | 2017-01-26 | イシューティカ ピーティーワイ リミテッド | メロキシカムの新規製剤 |
WO2011026080A1 (fr) * | 2009-08-31 | 2011-03-03 | Wilmington Pharmaceuticals, Llc | Compositions à désintégration rapide de méloxicame, procédés pour sa fabrication et utilisation pour traiter l'arthrite et/ou la douleur |
US8545879B2 (en) | 2009-08-31 | 2013-10-01 | Wilmington Pharmaceuticals, Llc | Fast disintegrating compositions of meloxicam |
RU2465892C1 (ru) * | 2011-09-21 | 2012-11-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Новосибирский национальный исследовательский государственный университет (НГУ)" | Способ получения высокодисперсного мелоксикама |
US9526734B2 (en) | 2014-06-09 | 2016-12-27 | Iceutica Pty Ltd. | Formulation of meloxicam |
US9649318B2 (en) | 2014-06-09 | 2017-05-16 | Iceutica Pty Ltd. | Formulation of meloxicam |
US9808468B2 (en) | 2014-06-09 | 2017-11-07 | Iceutica Pty Ltd. | Formulation of meloxicam |
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