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WO2006008640A1 - Suspension non aqueuse contenant un medicament a gout desagreable - Google Patents

Suspension non aqueuse contenant un medicament a gout desagreable Download PDF

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Publication number
WO2006008640A1
WO2006008640A1 PCT/IB2005/002122 IB2005002122W WO2006008640A1 WO 2006008640 A1 WO2006008640 A1 WO 2006008640A1 IB 2005002122 W IB2005002122 W IB 2005002122W WO 2006008640 A1 WO2006008640 A1 WO 2006008640A1
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WO
WIPO (PCT)
Prior art keywords
oil
composition according
drug
particle size
oils
Prior art date
Application number
PCT/IB2005/002122
Other languages
English (en)
Inventor
Lorraine Elisabeth Pena
Original Assignee
Pharmacia & Upjohn Company Llc
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 Pharmacia & Upjohn Company Llc filed Critical Pharmacia & Upjohn Company Llc
Publication of WO2006008640A1 publication Critical patent/WO2006008640A1/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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • 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

Definitions

  • the compositions contain an oil or fat and an antacid.
  • the antacid may be either a fatty amine, which can also serve as the fat component, a fatty amine salt, or conventional antacids such as calcium carbonate, magnesium carbonate, magnesium trisilicate, magnesium hydroxide, and similar compounds.
  • a flavoring agent such as peppermint oil.
  • US Patent 4,865,851 relates to cefuroxime axetil in particulate form coated with an integral coating of a lipid or mixture of lipids which serves to mask the bitter taste of cefuroxime axetil but disperses or dissolves on contact with gastrointestinal fluid.
  • the compositions may include thickeners, sweeteners, and flavoring agents.
  • WO 92/04893 relates to liquid oral compositions comprising a histamine H 2 - antagonist, such as cimetidine, in an edible oily vehicle.
  • the compositions may contain flavoring agents, sweeteners, preservatives, emulsifiers, and thickening agents.
  • WO 03/039460 relates to quinazoline compounds that are useful for treating cellular proliferative diseases.
  • the compounds may be formulated in an oily suspension in vegetable or mineral oil.
  • the formulations may contain thickeners, flavoring agents, sweetening agents and preservatives.
  • a composition comprising: a surfactant, an edible oil, and a drug of low oil solubility having reduced particle size, selected from the group consisting of oxazolidinone antibiotics and pregabalin is disclosed.
  • the present invention provides an oil suspension for oral use of a drug of low oil solubility.
  • Pregabalin and oxazolidinone antibiotics may be used in the composition of the present invention. Both pregabalin and oxazolidinone antibiotics are known to have an unpleasant taste, and it is an object of the present invention to provide a formulation in which the unpleasant taste of the drug is masked.
  • the oil suspension formulation comprises the drug, having a reduced particle size, and a surfactant in an edible oil base.
  • the formulation may further comprise preservatives, thickeners, sweeteners, flavor enhancers, creaminess enhancers, saltiness enhancers, and flavoring agents.
  • oxazolidinones are a well known group of antibiotics that have been described in many patents and patent publications.
  • International Patent Publication No. WO 03/063862 relates to a wide variety of oxazolidinones that may be used in combination with B vitamins in the treatment of bacterial infections.
  • US Patent 6,239,152 relates to oxazolidinones and methods for their synthesis.
  • US Patent No 6,605,609 relates to a thiazine oxazolidinone useful as an antimicrobial agent and a new antimicrobial combination therapy for infective diseases.
  • US Patent No 5,700,799 relates to oxazolidinone derivatives possessing a substituted diazine moiety bonded to an N-aryl ring.
  • US Patent No 6,605,609 relates to thiopyran oxazolidinones useful as antimicrobial agents.
  • US Patent No. 5,880,118 relates to substituted oxazine and thiazine oxazolidinone antimicrobials.
  • US Patent No. 6,968,962 relates to phenyloxazolidinones having a C-C bond to 4-8 membered heterocyclic rings.
  • US Patent No. 5,981,528 relates to antibiotic oxazolidinone derivatives.
  • WO 01/34128 A2 relates to admixture of linezolid and other antibacterial agents.
  • International Patent Publication No. WO 03/093247 A relates to oxazolidinone derivatives for treating or preventing infectious disorders caused by bacteria in human or animal.
  • International Patent Publication No. WO 03/0007870 A2 relates to certain substituted phenyl oxazolidinones and processes for the synthesis of the same.
  • US Patent 5,688,792 relates to linezolid
  • US Patent 6,559,305 relates to linezolid
  • US Patent 6,559,305 relates to a particular crystal form of linezolid.
  • US Patent 6,197,819 relates to 3(S)-3aminomethyl-5-methyl-hexanoic acid (pregabalin), and similar compounds. The use of these compounds in treating seizure disorders is described.
  • US Patent 6,242,488 relates to the use of GABA analogs to prevent and treat gastrointestinal damage and ethanol withdrawal syndrome. The preferred GABA analogs were gabapentin and pregabalin.
  • Linezolid and pregabalin are the preferred drugs for use in the formulations of the present invention.
  • the drug particles have a reduced particle size, that is, a volume median diameter ("particle size") of not more than 10 ⁇ m.
  • the minimum particle size is not critical, but should not be so small as to cause problems in the manufacture of the formulation. Particle sizes as low as 0.5 ⁇ m would be satisfactory.
  • the particle size of the bulk drug is greater than 10 ⁇ m, it may be reduced in particle size by any conventional means, but is preferably milled using a pulverizing rotary mill or air jet micronizer.
  • the reduced size of the drug particles is desirable because it provides a smooth feeling when the formulation is taken into the mouth.
  • drug of reduced particle size is more readily suspendable in oil than larger particles would be.
  • particle size the physical and chemical characteristics of the milled drug are the same as the unmilled drug.
  • Other solid components of the formulation, such as solid sweeteners should also be reduced in particle size.
  • the formulations of the present invention are suspensions of the drug of low oil solubility in oil. The lower the oil solubility of the drug, the better the oil can serve to mask the unpleasant taste of the drug. Ideally, the drug should be practically insoluble in oil. In practice, the purposes of the present invention may be achieved if the drug has low oil solubility. In this case, low oil solubility means a solubility of the drug in the edible oil of 0 to 1 mg/ml at a temperature of 20 to 25° C.
  • the edible oils that may be used in the formulation include animal oils, fish oils, vegetable oils, hydrogenated vegetable oils and C 6 to Ci 6 fatty acid diglycerides and triglycerides.
  • Oils of animal origin include lard and beef tallow.
  • Fish oils include cod liver oil and menhaden oil. Since oils of animal and fish origin generally have stronger flavors, they are not preferred for use in the present invention.
  • Vegetable oils include oils such as avocado oil, cannola oil, coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, and soybean oil.
  • the fatty acids suitable for the diglycerides and triglycerides include caproic, caprylic, capric, lauric, myristic, palmitic, stearic, oleic, linoleic, linolenic acid and the like.
  • C 8 to Ci 2 saturated fatty acid triglycerides obtained from natural oils, such as coconut oil, and palm kernel oil, are useful, including those sold under the brand Miglyol ® from Sasol, and bearing trade designations 810, 812, 829 and 840.
  • Miglyol ® 812, a mixture of C 8 and Ci 0 triglycerides is a preferred oil.
  • cocoa butter, or hydrogenated vegetable oils may be used as the oil in the formulation.
  • Suitable hardened oils which may be used in the formulation are Witepsol ® H15, Witepsol ® H32, Softisan ® 100 and Softisan ® 378 from Sasol, which are triglycerides based on C 8 to Ci 8 saturated fatty acids. Other similar food grade triglycerides may also be used. For example, Sasol supplies a number of such products.
  • the formulation contains a nonionic surfactant.
  • the surfactant helps the edible oil to wet the powdered oxazolidinone antibiotic.
  • Suitable nonionic surfactants include lecithin, polysorbate 60, polysorbate 80, glycerol mono and di-esters with fatty acids, propylene glycol monofatty acid esters, sorbitan esters with fatty esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene fatty acid esters, and glycerides of citric acid. McCutcheon's Emulsifiers and Detergents (1987 edition) provides a list of surfactants suitable for food or pharmaceutical usage.
  • the formulation may further comprise a sweetening agent.
  • the sweetening agent may include one or more individual sweeteners.
  • the sweeteners may be sugars, sugar derivatives, natural products, such as honey, or artificial sweeteners.
  • Sugars, and sugar derivatives include glucose, fructose, sucrose, maltose, lactose, glycyrrhizin, sorbitol, mannitol, and xylitol.
  • Artificial sweeteners include saccharin, cyclamate, aspartame, acesulfame-K, and sucralose.
  • the sweetener may include two types of sweetening agents. One type of sweetening agent provides immediate sweetness.
  • Such sweeteners include glucose, fructose, sucrose, and acesulfame-K. Other sweeteners that may be included provide a long lasting sweetness. Such sweeteners include sucralose, saccharin, and glycyrrhizin.
  • the sweetening agent may include components that provide a cooling sensation, such as sorbitol, mannitol, and xylitol that provide a cooling sensation. Sorbitol, mannitol, and xylitol provide both a sweetening and cooling effect.
  • flavor enhancers such as Prosweet ® , available from Virginia Dare, and Sweet AM ® available from Flavors of North America
  • creaminess enhancers such as maltol and ethyl maltol
  • saltiness enhancers such as sodium chloride, potassium chloride, and monosodium glutamate.
  • the formulation may further comprise natural or artificial flavoring agents such as peppermint oil, wintergreen, oil of cloves, and plant derived essential oil, oil extracts and infusions.
  • natural or artificial flavoring agents such as peppermint oil, wintergreen, oil of cloves, and plant derived essential oil, oil extracts and infusions.
  • the formulation may further comprise thickeners.
  • thickeners include colloidal silicon dioxide, beeswax, lecithin, hydrogenated vegetable oils, and triglycerides based upon saturated fatty acids.
  • Acesulfame K Particle Size A (Sunett ® Nutrinova) 0.10 0.5
  • Magnasweet ® 100 (McAndrews & Forbes) 0.10 0.5
  • the polysorbate 80, fructose, xylitol, Prosweet ® , ethyl maltol, acesulfame K, sucralose, sodium chloride, Magnasweet ® , vanilla type flavor, and Miglyol ® 812 were weighed and placed into a suitable manufacturing vessel, and the mixture was stirred until it was uniform.
  • the linezolid was added to the vessel and the mixture was stirred until it was smooth and uniform.
  • Colloidal silicon dioxide was added and mixed at high speed. High speed mixing was continued until the colloidal silicon dioxide was wetted by the oil. The mixing speed was reduced, and mixing continued until the mixture was uniform and smooth.
  • the suspension was mixed in a homomixer for approximately 5 minutes to uniformly mix the suspension.
  • the Miglyol ® 812 was weighed and placed into a suitable manufacturing vessel. Polysorbate 80 and tutti fruiti O.S. were added and the mixture was stirred until it was uniform and clear. The powdered fructose, xylitol, Prosweet ® , and ethyl maltol were added to the mixture. The mixture was stirred until it was uniform and smooth. The linezolid was added to the vessel and the mixture was stirred until it was smooth and uniform. Colloidal silicon dioxide was added and mixed at high speed. High speed mixing was continued until the colloidal silicon dioxide was wetted by the oil. The mixing speed was reduced, and mixing continued until the mixture was uniform and smooth.
  • the Witepsol ® Hl 5 was weighed and placed into a suitable manufacturing vessel. The vessel was heated to between 42 and 45° C. This temperature was maintained throughout the mixing process. Polysorbate 80 and tutti fruiti O.S. were added and the mixture was stirred until it was uniform and clear. The powdered fructose, xylitol, Prosweet ® , and ethyl maltol were added to the mixture. The mixture was stirred until it was uniform and smooth. Linezolid was added to the vessel and the mixture was stirred until it was smooth and uniform. Colloidal silicon dioxide was added and mixed at high speed. High speed mixing was continued until the colloidal silicon dioxide was wetted by the oil. The mixing speed was reduced, and mixing continued until the mixture was uniform and smooth. The mixture was then poured into molds, and allowed to cool and solidify at room temperature.
  • Magnasweet ® 100 (McAndrews & Forbes) 0.10 0.5

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Zoology (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne une composition comprenant un tensioactif, une huile comestible et un médicament faiblement soluble dans l'huile à granulométrie réduite sélectionné dans le groupe constitué par des antibiotiques à base d'oxazolidinone et la prégabaline.
PCT/IB2005/002122 2004-07-15 2005-07-04 Suspension non aqueuse contenant un medicament a gout desagreable WO2006008640A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US58807004P 2004-07-15 2004-07-15
US60/588,070 2004-07-15

Publications (1)

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WO2006008640A1 true WO2006008640A1 (fr) 2006-01-26

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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1210764A (en) * 1968-03-28 1970-10-28 Westinghouse Electric Corp Self-aligning hydrostatic bearing
WO2007107835A2 (fr) * 2006-03-17 2007-09-27 Aurobindo Pharma Limited Formulations liquides stables d'agents anti-epileptiques
US7417165B2 (en) 2005-04-06 2008-08-26 Teva Pharmaceutical Industries Ltd. Crystalline forms of pregabalin
US7446220B2 (en) 2005-09-19 2008-11-04 Teva Pharmaceutical Industries Ltd. Asymmetric synthesis of (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid
US7462737B2 (en) 2005-05-10 2008-12-09 Teva Pharmaceutical Industries Ltd. Pregabalin free of isobutylglutaric acid and a process for preparation thereof
US7488846B2 (en) 2005-04-11 2009-02-10 Teva Pharmaceuical Industries Ltd. Pregabalin free of lactam and a process for preparation thereof
DE102007055341A1 (de) 2007-11-19 2009-05-20 Bayer Animal Health Gmbh Stabilisierung öliger Suspensionen enthaltend hydrophobe Kieselsäuren
WO2009066325A1 (fr) * 2007-11-23 2009-05-28 Lupin Limited Compositions pharmaceutiques de prégabaline à libération contrôlée
US7619112B2 (en) 2005-05-10 2009-11-17 Teva Pharmaceutical Industries Ltd. Optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid
US7763749B2 (en) 2005-05-10 2010-07-27 Teva Pharmaceutical Industries Ltd. Method for the preparation of Pregabalin and salts thereof
WO2010094623A1 (fr) 2009-02-18 2010-08-26 Bayer Schering Pharma Aktiengesellschaft Fo0rmulation comprenant de la drospirenone pour administration souscutanee ou intramusculaire
USRE41920E1 (en) 1996-07-24 2010-11-09 Warner-Lambert Company Llc Isobutylgaba and its derivatives for the treatment of pain
WO2010150221A1 (fr) * 2009-06-25 2010-12-29 Wockhardt Research Centre Compositions pharmaceutiques de prégabaline de saveur masquée
WO2011057731A1 (fr) * 2009-11-10 2011-05-19 Cognis Ip Management Gmbh Composition comprenant un lipide approprié à la consommation humaine
US8097754B2 (en) 2007-03-22 2012-01-17 Teva Pharmaceutical Industries Ltd. Synthesis of (S)-(+)-3-(aminomethyl)-5-methyl hexanoic acid
WO2013129944A1 (fr) * 2012-02-27 2013-09-06 Bayer New Zealand Limited Compositions à libération contrôlée et leurs procédés d'utilisation
WO2014139657A1 (fr) * 2013-03-11 2014-09-18 Pharmathen S.A. Composition pharmaceutique contenant un agent antibactérien de type oxazolidinone et son procédé de préparation
EP2952207A1 (fr) * 2014-06-03 2015-12-09 Essential Pharmaceuticals Ltd Compositions pharmaceutiques pour administration orale à base d'huile
AU2015261543B2 (en) * 2012-02-27 2017-09-28 Elanco New Zealand Controlled release compositions and their methods of use

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991008734A1 (fr) * 1989-06-13 1991-06-27 Abbott Laboratories Suspension liquide et anhydre a base d'huile servant a liberer un medicament
WO1992004893A1 (fr) * 1990-09-13 1992-04-02 Smithkline Beecham Corporation Suspensions orales liquides non aqueuses
US5736151A (en) * 1996-12-09 1998-04-07 Pharmacia & Upjohn Company Antibiotic oil suspensions
WO1998058641A1 (fr) * 1997-06-25 1998-12-30 Warner-Lambert Company Utilisation d'analogues de gaba, telle la gabapentine, dans la fabrication d'un medicament servant a traiter des maladies inflammatoires
WO2003084534A1 (fr) * 2002-03-29 2003-10-16 Pharmacia & Upjohn Company Llc Administration orale, parenterale ou intraveineuse d'oxazolidinones utilisees dans le traitement des infections du pied causees par le diabete

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991008734A1 (fr) * 1989-06-13 1991-06-27 Abbott Laboratories Suspension liquide et anhydre a base d'huile servant a liberer un medicament
WO1992004893A1 (fr) * 1990-09-13 1992-04-02 Smithkline Beecham Corporation Suspensions orales liquides non aqueuses
US5736151A (en) * 1996-12-09 1998-04-07 Pharmacia & Upjohn Company Antibiotic oil suspensions
WO1998058641A1 (fr) * 1997-06-25 1998-12-30 Warner-Lambert Company Utilisation d'analogues de gaba, telle la gabapentine, dans la fabrication d'un medicament servant a traiter des maladies inflammatoires
WO2003084534A1 (fr) * 2002-03-29 2003-10-16 Pharmacia & Upjohn Company Llc Administration orale, parenterale ou intraveineuse d'oxazolidinones utilisees dans le traitement des infections du pied causees par le diabete

Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1210764A (en) * 1968-03-28 1970-10-28 Westinghouse Electric Corp Self-aligning hydrostatic bearing
USRE41920E1 (en) 1996-07-24 2010-11-09 Warner-Lambert Company Llc Isobutylgaba and its derivatives for the treatment of pain
US7417165B2 (en) 2005-04-06 2008-08-26 Teva Pharmaceutical Industries Ltd. Crystalline forms of pregabalin
US7488846B2 (en) 2005-04-11 2009-02-10 Teva Pharmaceuical Industries Ltd. Pregabalin free of lactam and a process for preparation thereof
US7763749B2 (en) 2005-05-10 2010-07-27 Teva Pharmaceutical Industries Ltd. Method for the preparation of Pregabalin and salts thereof
US7462737B2 (en) 2005-05-10 2008-12-09 Teva Pharmaceutical Industries Ltd. Pregabalin free of isobutylglutaric acid and a process for preparation thereof
US7678938B2 (en) 2005-05-10 2010-03-16 Teva Pharmaceutical Industries Ltd. Optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid
US7619112B2 (en) 2005-05-10 2009-11-17 Teva Pharmaceutical Industries Ltd. Optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid
US7470812B2 (en) 2005-09-19 2008-12-30 Teva Pharmaceutical Industries Ltd. Chiral 3-carbamoylmethyl-5-methyl hexanoic acids, key intermediates for the synthesis of (S)-Pregabalin
US7851651B2 (en) 2005-09-19 2010-12-14 Teva Pharmaceutical Industries Ltd. Asymmetric synthesis of (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid
US8212071B2 (en) 2005-09-19 2012-07-03 Teva Pharmaceutical Industries Ltd. Asymmetric synthesis of (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid
US7563923B2 (en) 2005-09-19 2009-07-21 Teva Pharmaceutical Industries Ltd. Chiral 3-carbamoylmethyl-5-methyl hexanoic acids, key intermediates for the synthesis of (S)-Pregabalin
US7586005B2 (en) 2005-09-19 2009-09-08 Teva Pharmaceutical Industries Ltd. Asymmetric synthesis of (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid
US7973196B2 (en) 2005-09-19 2011-07-05 Teva Pharmaceutical Industries Ltd. Asymmetric synthesis of (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid
US7465826B2 (en) 2005-09-19 2008-12-16 Teva Pharmaceutical Industries Ltd. Chiral 3-carbamoylmethyl-5-methyl hexanoic acids, key intermediates for the synthesis of (S)-pregabalin
US7687656B2 (en) 2005-09-19 2010-03-30 Teva Pharmaceutical Industries Ltd. Asymmetric synthesis of (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid
US7446220B2 (en) 2005-09-19 2008-11-04 Teva Pharmaceutical Industries Ltd. Asymmetric synthesis of (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid
US7960583B2 (en) 2005-09-19 2011-06-14 Teva Pharmaceutical Industries Ltd. Asymmetric synthesis of (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid
US7923575B2 (en) 2005-09-19 2011-04-12 Teva Pharmaceutical Industries Limited Asymmetric synthesis of (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid
WO2007107835A3 (fr) * 2006-03-17 2008-04-17 Aurobindo Pharma Ltd Formulations liquides stables d'agents anti-epileptiques
WO2007107835A2 (fr) * 2006-03-17 2007-09-27 Aurobindo Pharma Limited Formulations liquides stables d'agents anti-epileptiques
US8097754B2 (en) 2007-03-22 2012-01-17 Teva Pharmaceutical Industries Ltd. Synthesis of (S)-(+)-3-(aminomethyl)-5-methyl hexanoic acid
DE102007055341A1 (de) 2007-11-19 2009-05-20 Bayer Animal Health Gmbh Stabilisierung öliger Suspensionen enthaltend hydrophobe Kieselsäuren
US9095511B2 (en) 2007-11-19 2015-08-04 Bayer Intellectual Property Gmbh Stabilization of oily suspensions comprising hydrophobic silicas
US9028865B2 (en) 2007-11-23 2015-05-12 Lupin Limited Controlled release pharmaceutical compositions of pregabalin
WO2009066325A1 (fr) * 2007-11-23 2009-05-28 Lupin Limited Compositions pharmaceutiques de prégabaline à libération contrôlée
US8454993B2 (en) 2007-11-23 2013-06-04 Lupin Limited Controlled release pharmaceutical compositions of pregabalin
WO2010094623A1 (fr) 2009-02-18 2010-08-26 Bayer Schering Pharma Aktiengesellschaft Fo0rmulation comprenant de la drospirenone pour administration souscutanee ou intramusculaire
WO2010150221A1 (fr) * 2009-06-25 2010-12-29 Wockhardt Research Centre Compositions pharmaceutiques de prégabaline de saveur masquée
WO2011057731A1 (fr) * 2009-11-10 2011-05-19 Cognis Ip Management Gmbh Composition comprenant un lipide approprié à la consommation humaine
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CN104244983A (zh) * 2012-02-27 2014-12-24 拜耳新西兰有限公司 控制释放组合物及其使用方法
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JP2015508098A (ja) * 2012-02-27 2015-03-16 バイエル・ニュージーランド・リミテッド 制御放出組成物およびその使用方法
WO2013129944A1 (fr) * 2012-02-27 2013-09-06 Bayer New Zealand Limited Compositions à libération contrôlée et leurs procédés d'utilisation
EP2819699A4 (fr) * 2012-02-27 2015-10-28 Bayer New Zealand Ltd Compositions à libération contrôlée et leurs procédés d'utilisation
AU2015261543C1 (en) * 2012-02-27 2022-10-13 Elanco New Zealand Controlled release compositions and their methods of use
KR20140126340A (ko) * 2012-02-27 2014-10-30 바이엘 뉴질랜드 리미티드 조절된 방출 조성물 및 이들의 사용 방법
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AU2015261543B2 (en) * 2012-02-27 2017-09-28 Elanco New Zealand Controlled release compositions and their methods of use
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WO2014139657A1 (fr) * 2013-03-11 2014-09-18 Pharmathen S.A. Composition pharmaceutique contenant un agent antibactérien de type oxazolidinone et son procédé de préparation
GB2529605A (en) * 2014-06-03 2016-03-02 Essential Pharmaceuticals Ltd Pharmaceutical composition
AU2015202991B2 (en) * 2014-06-03 2018-09-06 Essential Pharmaceuticals Ltd Pharmaceutical composition
GB2529605B (en) * 2014-06-03 2018-03-21 Essential Pharmaceuticals Ltd Pharmaceutical composition
EP2952207A1 (fr) * 2014-06-03 2015-12-09 Essential Pharmaceuticals Ltd Compositions pharmaceutiques pour administration orale à base d'huile

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