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WO2012080984A2 - Comprimé pharmaceutique à libération contrôlée pour administration par voie orale - Google Patents

Comprimé pharmaceutique à libération contrôlée pour administration par voie orale Download PDF

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Publication number
WO2012080984A2
WO2012080984A2 PCT/IB2011/055720 IB2011055720W WO2012080984A2 WO 2012080984 A2 WO2012080984 A2 WO 2012080984A2 IB 2011055720 W IB2011055720 W IB 2011055720W WO 2012080984 A2 WO2012080984 A2 WO 2012080984A2
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WO
WIPO (PCT)
Prior art keywords
oral administration
controlled
release tablet
administration according
polymer
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/IB2011/055720
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English (en)
Spanish (es)
Other versions
WO2012080984A3 (fr
Inventor
Héctor SENOSIAIN ARROYO
María Angélica ARZOLA PANIAGUA
Gustavo BARRANCO HERNÁNDEZ
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Laboratorios Senosiain SA de CV
Original Assignee
Laboratorios Senosiain SA de CV
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Publication date
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Application filed by Laboratorios Senosiain SA de CV filed Critical Laboratorios Senosiain SA de CV
Priority to RU2013127408/15A priority Critical patent/RU2603469C2/ru
Priority to BR112013014963A priority patent/BR112013014963A2/pt
Publication of WO2012080984A2 publication Critical patent/WO2012080984A2/fr
Publication of WO2012080984A3 publication Critical patent/WO2012080984A3/fr
Priority to CR20130288A priority patent/CR20130288A/es
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61J—CONTAINERS SPECIALLY ADAPTED FOR MEDICAL OR PHARMACEUTICAL PURPOSES; DEVICES OR METHODS SPECIALLY ADAPTED FOR BRINGING PHARMACEUTICAL PRODUCTS INTO PARTICULAR PHYSICAL OR ADMINISTERING FORMS; DEVICES FOR ADMINISTERING FOOD OR MEDICINES ORALLY; BABY COMFORTERS; DEVICES FOR RECEIVING SPITTLE
    • A61J3/00—Devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms
    • A61J3/10—Devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms into the form of compressed tablets
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing
    • 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
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/282—Organic compounds, e.g. fats
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2121/00—Preparations for use in therapy

Definitions

  • the present invention relates to modified release pharmaceutical compositions in the form of tablets for oral administration, additionally also relates to the process for the preparation of said compositions.
  • the oral administration forms are the most accepted and comfortable for administration.
  • Ciprofloxacin is a quinolone derivative that is absorbed quickly in the gastrointestinal tract, so it is desirable to have a pharmaceutical composition that allows the antibiotic to be released in a controlled manner.
  • the present invention presents a formulation and a manufacturing process of a modified release drug, with a release profile that allows its administration once a day and that contains at least one active ingredient, for example an antibiotic, such as ciprofloxacin. or other quinolone derivative, as well as its pharmaceutically acceptable salts.
  • an antibiotic such as ciprofloxacin. or other quinolone derivative, as well as its pharmaceutically acceptable salts.
  • Ciprofloxacin is a broad-spectrum antibiotic, active against Gram-positive and Gram-negative bacteria both in the rapid development phase and in the stationary phase, acting at minimum inhibitory concentrations between 0.01 and 2 mcg / mL. It is useful for treating or preventing bacterial infections of the urinary and respiratory tract, sexually transmitted diseases, septicemia, legionellosis and atypical mycobacteriosis.
  • ciprofloxacin can be administered from 500 to 1,500 mg / day, divided into two doses per day for 7 to 14 days. A single dose of 250 mg is recommended in the treatment of uncomplicated gonococcal urethritis.
  • modified release compositions of the active ingredient are known for the preparation of modified release compositions of the active ingredient. Frequently it is intended that the composition remains a prolonged time in the stomach to allow adequate absorption In other embodiments, other sections of the gastrointestinal tract may be preferred.
  • U.S. Patent Nos. 5,007,790; 5,582,837 and 5,972,389 describe sustained release dosage forms for oral administration, designed to deliver a pharmacologically active agent for a prolonged period of time.
  • the active ingredient is dispersed in a plurality of polymeric particles, which have the ability to absorb water, causing swelling.
  • the dosage form increases in size, it is prevented from passing through the pylorus into the lower gastrointestinal tract and therefore, the release of the drug takes place in the stomach and in the upper gastrointestinal tract.
  • the Mexican patent No. MX 245737 (EP1294363) of Depomed presents an oral dosage form of controlled release comprising: a matrix containing an antibiotic, the matrix has two orthogonal axes of unequal length. After immersion in water, the matrix swells along both axes. The matrix has a shape such that when it is projected on a plane it is an oval or a parallelogram. With this system swallowing of the pharmaceutical form is facilitated and the passage through the pylorus is prevented.
  • gastric retention is determined by the degree of swelling of the pharmaceutical form in contact with the aqueous medium.
  • a disadvantage of the previously described formulations is that if the pharmaceutical form is divided into two or more fragments before ingesting it, which commonly occurs when the patient finds difficulty at the moment of ingesting the complete pharmaceutical form, gastric retention It will be minimal or nil, and the release of the active ingredient will also be modified.
  • the composition of the present invention does not swell during the water immersion process.
  • the active principle release control is based on a polymeric matrix and diffusion system, independent of the tablet form.
  • Bayer patent MX 243623 offers an oral administration preparation containing a quinolone antibiotic, characterized in that it contains: a) water-swellable polymer and b) a mixture of at least two derivatives of the quinolone antibiotic, which they can be the free base and salt, for example, ciprofloxacin betaine and ciprofloxacin hydrochloride.
  • the composition is a two-layer tablet containing: a quick-release part, which may contain the salt and base mixture free of ciprofloxacin, disintegrant (eg PVP) and excipients, as well as another delayed-release part that may contain the mixture of salt and ciprofloxacin free base, retardant polymer (for example, low viscosity polymer such as HPMC (hydroxypropyl methylcellulose)), organic acid (for example, succinic acid) and excipients.
  • a quick-release part which may contain the salt and base mixture free of ciprofloxacin, disintegrant (eg PVP) and excipients, as well as another delayed-release part that may contain the mixture of salt and ciprofloxacin free base, retardant polymer (for example, low viscosity polymer such as HPMC (hydroxypropyl methylcellulose)), organic acid (for example, succinic acid) and excipients.
  • retardant polymer for example, low viscosity polymer such
  • the composition of the present invention allows to obtain a release of active ingredient both fast and modified, and the release is not affected if the pharmaceutical form is divided before ingestion.
  • Another disadvantage of the composition, MX 243623 patent is that both ciprofloxacin betaine and ciprofloxacin hydrochloride are used. It is well known that the basic form of ciprofloxacin is more unstable than salt, so that a stabilizing agent is required. In contrast, the composition of the present invention does not necessarily require a stabilizing agent, since more stable forms of the active ingredient, such as a ciprofloxacin salt, can be used. This allows to reduce operating times and costs.
  • Patent document MX / a / 2001/002634 offers an oral controlled release formulation in tablets containing an effective amount of ciprofloxacin base, and approximately 0.2% to 0.5% sodium alginate , 0.5% to 2.0% xanthan gum, 25% sodium bicarbonate as a gas generating agent and 20% of polyvinylpyrrolidone.
  • This controlled release formulation is swollen by the effect of sodium bicarbonate and sodium alginate. Upon swelling, the tablet is retained in the lower part of the stomach and before passing through the pylorus, thereby achieving a controlled release of ciprofloxacin at the site of absorption.
  • Patent document MX / a / 2002/008568 offers an oral formulation of controlled release in tablets for administration once a day, which contains an effective amount of ciprofloxacin base and a viscolizing agent (also called viscous agent) ), a carboxylic or cellulose gum, gelling agent (also called gelling agent) sodium alginate, gas generating agent (carbonate or sodium bicarbonate) and a swelling agent (crosslinked polyvinyl pyrrolidone).
  • a viscolizing agent also called viscous agent
  • carboxylic or cellulose gum also called gelling agent
  • gelling agent also called gelling agent
  • gas generating agent carbonate or sodium bicarbonate
  • swelling agent crosslinked polyvinyl pyrrolidone
  • the present invention presents a modified release formulation comprising an active ingredient, but not limited to, a derivative of Quinolone as ciprofloxacin hydrochloride, without the inclusion of gas-generating agents or gelling networks, which makes it not an inflatable formulation. Instead, there is a polymeric matrix system for diffusion of the active substance, which complies with a release profile for administration once a day. For this, excipients are used that delay the release of the active ingredient, coated by a matrix polymeric that in contact with the gastric medium is eroded to form a plurality of channels through which the active substance is released by diffusion.
  • the present invention relates to a modified release composition, which represents an advantage at the time of administration since greater adherence to the treatment regimen is achieved, the administration of the medicament being once a day for the required period. JUSTIFICATION OF THE INVENTION.
  • compositions that offer controlled release formulations of active ingredient, however, all of them are obtained through processes made with the use of a large number of excipients.
  • the present invention offers a combination of systems that allow obtaining a composition that allows to achieve a controlled release profile, and that in a preferred embodiment the release is modified tangentially, using a smaller amount of excipients and using a smaller amount of inputs, time and labor during the preparation of the composition.
  • Another innovation of the composition is the use of a barrier-diffuser matrix with a double function: taste masking and diffusion barrier.
  • Figure 1 shows the plasma level curves against the absorption time of the formulation of the present invention (Graph with white circuits) compared to a reference formulation (commercial product, Bayer's Cipro XR®, inflatable tablet) (Graph with black circuits).
  • the challenge faced by the development of the present invention is to obtain an oral pharmaceutical composition, which complies with the required release profile of the active ingredient and that in a preferred embodiment the release is modified tangentially, for administration once daily, where the resulting composition is stable, safe and with therapeutic efficacy.
  • composition of the present invention offers a combination of systems that makes it possible to obtain modified tangential release of the active ingredient, using a smaller amount of excipients and using a smaller amount of inputs, time and labor during the preparation of the composition.
  • a polymeric matrix release system that doses the active ingredient in two continuous phases at two different rates in the same dose unit.
  • This system consists of an internal part of delayed release, and an external part of rapid release.
  • the delayed-release part contains the active substance and excipients that give it protection and allow it to delay the release of ciprofloxacin abroad.
  • it is exposed to the active principle by a two-way controlled release: diffusion through a polymeric matrix and release through the channels formed by erosion of a polymeric matrix.
  • the combination of these release processes results in an active principle release process in a modified and controlled manner.
  • composition within the organism exhibits a release suitable for oral administration once a day by combining diffusion and erosion systems.
  • compositions of easy swallowing and with modified release systems wherein the active ingredient is included in amounts equal to or greater than 500mg.
  • a such a high amount of active ingredient would imply the use of a large number of excipients.
  • a tablet is obtained that allows it to be more accepted by the patient who has swallowing problems, stable, safe, which allows masking the unpleasant taste of ciprofloxacin.
  • the active ingredient comprises about 80% by weight of the formulation and the excipients about 20%.
  • the components of the formulation are:
  • Active ingredient the active substance is selected from any drug that is required to be administered in a modified and / or delayed manner, this may be a quinolone derivative such as ciprofloxacin or pharmaceutically acceptable salts thereof.
  • Binder diluent it can be selected from microcrystalline cellulose, polivilpyrrolidone, hydroxypropyl methylcellulose, lactose, starch, calcium dibasic phosphate, mixture thereof or other equivalent excipient. Microcrystalline cellulose is preferred. This excipient is in the formulation in a range of 10% to 20% by weight and in a preferred embodiment is between 10% to 15% by weight.
  • Retardant polymer selected from ethyl cellulose, oleic oil, derivatives of the copolymer of methacrylic acid, cellulose acetate, methyl cellulose. This excipient is found in the formulation in a range of 0.5 to 6% by weight and in a preferred embodiment is between 3% to 6% by weight.
  • Matrix forming polymer selected from HPMC (hydroxypropyl methylcellulose or hypromellose), hydroxyethylcellulose, hydroxymethylcellulose, methylcellulose, derived from methacrylate acid copolymers. This component is in the formulation in a range of 0.5 to 10% by weight and in a preferred embodiment is between 5% to 10% by weight.
  • Diluent or diluent agent can be selected from: lactose monohydrate, microcrystalline cellulose, dextrose, sucralose or sucrose and / or mannitol.
  • Sliding is selected from magnesium stearate, magnesium phosphate, stearic acid, glyceryl stearate, polyethylene glycol, sodium lauryl sulfate, sodium stearyl fumarate, talc, mixture thereof or other equivalent excipient.
  • Coating polymer can be selected from cellulose and methacrylate derivatives, polyvinylpyrrolidone, polyvinyl alcohol, hydroxypropyl methylcellulose, carrageenan or any other equivalent excipient.
  • Table 1 illustrates three examples of formulations obtained during the development of the present invention. TABLE 1
  • HPMC is hydroxypropyl methylcellulose and PM means molecular weight
  • Critical excipients in the present formulation are the "retarding polymer” and the "matrix forming polymer.”
  • HPMC high molecular weight polymers are recommended by manufacturers of excipients for modified release, however, it was observed that when using these high molecular weight polymers as matrix formers in With ciprofloxacin formulations, a considerable delay of the release is obtained and therefore the active principle is not released in the times to comply with the specification.
  • HPMC 5 of very low molecular weight does allow the release at specified times.
  • Tablet formulations in the form of coated tablets were evaluated with stability studies to verify that they are robust and compliant formulations and They retain their stability.
  • Table 3 shows the results of a stability test for formulation 3, which shows that under different conditions it retains the characteristics of being an oblong, homogeneous and smooth tablet.
  • Table 4 shows the general tablet formulation in the form of tablets, according to formulation 3.
  • a preferred formulation without limiting the scope of the present invention is that which contains from 250 mg to 1500 mg of active ingredient.
  • Tablet formulations in the form of coated tablets can be made without limiting the scope of the present invention in presentations containing from 250mg, 500mg, 750mg, lOOOmg and up to 1500mg of ciprofloxacin, some examples are shown in Table 5.
  • excipients used do not represent more than 20% of the weight of the formulation. Through a careful selection of excipients a formulation was achieved that allows using the least amount of them. This is because the matrix forming polymer and the retarding polymer have a double function. The matrix forming polymer is also a taste masking. The polymer that delays the release of the active ingredient also acts as a lubricant with good flow properties, which obviously results in a reduction in operating times and material supply costs.
  • Granular hypromellose, the active substance and water (granulate 2).
  • the obtained tablet is placed in the coater where it is sprayed with the final protective cover.
  • the finished product is conditioned.
  • the formulations obtained do not limit the content of the active ingredients to the formulations presented as examples, since they can be presented with any other active ingredient capable of being integrated into the formulation.
  • the active ingredients used are derivatives of quinolones selected from enoxacin, ofloxacin, norfloxacin, ciprofloxacin, levofloxacin, fleroxacin, perfloxacin, trovafloxacin and their pharmaceutically acceptable salts or hydrates.
  • the present invention provides oral pharmaceutical compositions comprising an active ingredient, such as a quinolone derivative, or its pharmaceutically acceptable salts or hydrates, from 500 mg to 1000 mg even up to 1,500 mg in one same dose unit, without compromising the controlled release of the composition.
  • an active ingredient such as a quinolone derivative, or its pharmaceutically acceptable salts or hydrates
  • a Bioequivalence Study of the composition was carried out to know the concentration, time of release of the active substance ciprofloxacin or its acceptable pharmaceutical salts, in its healthy etho-volunteers.
  • a cross-sectional study was carried out two sequences, two periods (2x2) at a therapeutic dose of 1 g of ciprofloxacin contained in a dose unit (tablet).
  • Plasma samples were processed through the liquid-liquid extraction technique and ciprofloxacin concentrations were determined by the High Resolution Liquid Chromatography Method.
  • Figure 1 shows the plasma level curves of the formulation of the present invention (white circles) and a reference formulation (black circles). This figure shows that the formulation of the present invention meets the required characteristics such as a release greater than 40% in the first hour and greater than 80% after 4 hours.
  • composition of the present invention once-daily extended-release tablet, is bioequivalent with the reference formulation, but the advantage that only one ciprofloxacin derivative is used and that the release of the active substance is independent of the swelling of the pharmaceutical form.
  • composition of the present invention is that it is effective and safe in its administration.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Communicable Diseases (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biophysics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Oncology (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

L'invention se rapporte à des compositions pharmaceutiques sous forme de comprimés pour l'administration par voie orale, contenant un principe actif et des excipients pharmaceutiquement acceptables. Ces comprimés sont caractérisés en ce qu'une partie du principe active est libérée immédiatement, et une autre partie du principe actif se trouve dans un système de matrice polymère de diffusion qui permet une libération retardée du principe actif.
PCT/IB2011/055720 2010-12-17 2011-12-16 Comprimé pharmaceutique à libération contrôlée pour administration par voie orale Ceased WO2012080984A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
RU2013127408/15A RU2603469C2 (ru) 2010-12-17 2011-12-16 Таблетка с контролируемым высвобождением для перорального введения и способ ее приготовления
BR112013014963A BR112013014963A2 (pt) 2010-12-17 2011-12-16 comprimido farmacêutico de liberação controlada para administração oral
CR20130288A CR20130288A (es) 2010-12-17 2013-06-13 Comprimido farmacéutico de liberación controlada para administración oral

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
MX2010014153A MX2010014153A (es) 2010-12-17 2010-12-17 Comprimido farmaceutico de liberacion controlada para administracion oral.
MXMX/A/2010/014153 2010-12-17

Publications (2)

Publication Number Publication Date
WO2012080984A2 true WO2012080984A2 (fr) 2012-06-21
WO2012080984A3 WO2012080984A3 (fr) 2012-08-16

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PCT/IB2011/055720 Ceased WO2012080984A2 (fr) 2010-12-17 2011-12-16 Comprimé pharmaceutique à libération contrôlée pour administration par voie orale

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Country Link
BR (1) BR112013014963A2 (fr)
CL (1) CL2013001707A1 (fr)
CO (1) CO6721021A2 (fr)
CR (1) CR20130288A (fr)
DO (1) DOP2013000136A (fr)
EC (1) ECSP13012766A (fr)
GT (1) GT201300154A (fr)
MX (1) MX2010014153A (fr)
PE (1) PE20140675A1 (fr)
RU (1) RU2603469C2 (fr)
WO (1) WO2012080984A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016058813A1 (fr) 2014-10-16 2016-04-21 Koninklijke Philips N.V. Alignement d'un patient à l'intérieur d'un appareil d'imagerie par résonance magnétique

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL119627A (en) * 1996-11-17 2002-03-10 Yissum Res Dev Co PHARMACEUTICAL PREPARATIONS FOR THE CONTROLLED-RELEASE OF AN ACTIVE AGENT COMPRISING AT LEAST ONE β-LACTAM ANTIBIOTIC AGENT
US6723340B2 (en) * 2001-10-25 2004-04-20 Depomed, Inc. Optimal polymer mixtures for gastric retentive tablets
US20030104052A1 (en) * 2001-10-25 2003-06-05 Bret Berner Gastric retentive oral dosage form with restricted drug release in the lower gastrointestinal tract
JP2005516020A (ja) * 2001-12-20 2005-06-02 ファルマシア・コーポレーション ゼロ次持続放出剤形およびその製造方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016058813A1 (fr) 2014-10-16 2016-04-21 Koninklijke Philips N.V. Alignement d'un patient à l'intérieur d'un appareil d'imagerie par résonance magnétique

Also Published As

Publication number Publication date
RU2603469C2 (ru) 2016-11-27
RU2013127408A (ru) 2015-01-27
DOP2013000136A (es) 2013-10-15
ECSP13012766A (es) 2013-09-30
CL2013001707A1 (es) 2014-01-10
PE20140675A1 (es) 2014-06-25
WO2012080984A3 (fr) 2012-08-16
CR20130288A (es) 2013-08-13
MX2010014153A (es) 2012-06-18
CO6721021A2 (es) 2013-07-31
BR112013014963A2 (pt) 2016-09-13
GT201300154A (es) 2014-05-07

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