WO1998040054A1 - Forme posologique orale a enrobage gastro-resistant contenant de l'amoxicilline de sodium - Google Patents

Forme posologique orale a enrobage gastro-resistant contenant de l'amoxicilline de sodium Download PDF

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Publication number
WO1998040054A1
WO1998040054A1 PCT/SE1998/000356 SE9800356W WO9840054A1 WO 1998040054 A1 WO1998040054 A1 WO 1998040054A1 SE 9800356 W SE9800356 W SE 9800356W WO 9840054 A1 WO9840054 A1 WO 9840054A1
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WO
WIPO (PCT)
Prior art keywords
dosage form
enteric coated
sodium amoxycillin
amoxycillin
sodium
Prior art date
Application number
PCT/SE1998/000356
Other languages
English (en)
Inventor
Stig WENDSJÖ
Original Assignee
Astra Aktiebolag (Publ)
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 Astra Aktiebolag (Publ) filed Critical Astra Aktiebolag (Publ)
Priority to JP53949898A priority Critical patent/JP2001515489A/ja
Priority to EP98909899A priority patent/EP0981335A1/fr
Priority to AU64268/98A priority patent/AU6426898A/en
Publication of WO1998040054A1 publication Critical patent/WO1998040054A1/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
    • A61K31/33—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
    • A61K31/429—Thiazoles condensed with heterocyclic ring systems
    • A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
    • 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
    • A61K9/2886—Dragees; Coated pills or tablets, e.g. with film or compression coating having two or more different drug-free coatings; Tablets of the type inert core-drug layer-inactive layer
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
    • A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
    • A61K9/2081—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets with microcapsules or coated microparticles according to A61K9/50

Definitions

  • This invention relates to new formulations of sodium amoxycillin, in particular enteric coated oral dosage formulations of sodium amoxycillin, processes for their manufacture and their use in the treatment of Helicobacter pylori infections.
  • each single active substance is administered separately in different dosage forms.
  • administration of two or more different tablets is not typically seen as convenient or satisfactory by the patient and therefore such therapy has the disadvantage of poor patient compliance and therefore poor results.
  • the antibacterial agent amoxycillin has been known for many years to be useful in the treatment of wide variety of infections, ranging from bronchitis to urinary-tract infections.
  • amoxycillin has been indicated as being a preferred antibacterial agent.
  • combination therapies comprising coadministration of omeprazole and amoxycillin have been approved by regulatory authorities in e.g. the United Kingdom and Sweden.
  • Amoxycillin is typically administered in two forms, amoxycillin trihydrate which is typically admimstered orally and sodium amoxycillin which is typically administered by injection.
  • a tablet formulation typically comprises amoxycillin trihydrate and the injection is a solution of sodium amoxicyllin.
  • Enteric coated formulations comprising sodium amoxycillin are not previously known at the knowledge of the Applicant. We have found that, in the treatment of H. pylori infections, the above problems may be solved by providing an enteric coated formulation of sodium amoxycillin which may be used as a single therapy or in a combination therapy.
  • enteric coated oral dosage forms comprising sodium amoxycillin (hereinafter referred to as "the dosage forms according to the invention").
  • Enteric coatings are well known in the art of drug formulation as an effective method of preventing the release of pharmaceutically active agents in the stomach, but which will dissolve and release drug in the small intestine. They are typically used to prevent the release of drugs which are inactivated by the stomach's contents (e.g. pancreatin and erythromycin) or which irritate the gastric mucosa (e.g. aspirin, i.e. acetyl salicylic acid).
  • drugs which are inactivated by the stomach's contents (e.g. pancreatin and erythromycin) or which irritate the gastric mucosa (e.g. aspirin, i.e. acetyl salicylic acid).
  • sodium amoxycillin exhibits a surprisingly high dissolution rate at p ⁇ values typically experienced in the small intestine when compared to amoxycillin trihydrate and that the dosage forms according to the invention comprising exhibit significantly higher maximum serum concentrations.
  • H. pylori when compared with conventional formulations of amoxycillin trihydrate, are experienced with an enteric coated formulation of sodium amoxycillin.
  • the present invention relates to an enteric coated oral dosage form providing a fast release of sodium amoxicillin after passage of the stomach and thus a high plasma concentration of amoxicillin and which dosage form in combination with a proton pump inhibitor provides an enhanched eradication of H. pylori.
  • Figure 1 shows the result of in vitro dissolution test of tablets.
  • the dosage forms according to the invention may be formulated as a single unit or as a multiple unit tableted dosage form.
  • single unit denotes that the tablet matrix contains the active substance homogenously distributed beneath the surface area and the term “multiple unit” denotes that the active substance is present in the tablet in several units (of which each one may have its own protective surface layer). In both cases the tablet may contain either one single active substance or one or more additional active substances.
  • sodium amoxycillin may be formulated as a solid granulation along with inactive excipients and compressed into a single unit tablet, prior to application of the enteric coating.
  • inactive excipients examples include diluents, binders, lubricants and, if necessary, wetting agents.
  • Suitable diluents include lactose, sucrose, dextrose, starches (e.g. sodium starch glycolate, corn starch) cellulose derivatives (e.g. low substituted hydroxypropyl cellulose, microcrystalline cellulose), mannitol, crosslinked polyvinyl pyrrolidone, microcrystalline and colloidal anhydrous silicon dioxide (Aerosii ).
  • the dry mixture of sodium amoxycillin may subsequently be mixed with a binder, for example polyvinyl pyrrolidone, hydroxypropyl cellulose, sorbitol and gelatin.
  • a binder for example polyvinyl pyrrolidone, hydroxypropyl cellulose, sorbitol and gelatin.
  • Suitable lubricants which may be employed for the tableting process include for example sodium stearyl fumarate, magnesium stearate and talc.
  • Suitable wetting agents include for instance sodium lauryl sulphate dissolved in distilled water.
  • Sodium amoxycillin may be dry mixed with the appropriate excipients and then tableted, or the mixture may be wet massed with a granulation liquid. The wet mass is dried, preferably to a loss on drying of less than 3% by weight. Thereafter the dry mass is milled to a suitable size for tableting. The tablets are enteric coated in a suitable equipment.
  • the enteric coated pellets, or granules, comprising sodium amoxycillin are prepared as hereinbefore described for tablets.
  • the enteric coated pellets are mixed with tablet excipients such as fillers, binders, disintegrants and lubricants, and the dry mixture is then compressed into a multiple unit tableted dosage form.
  • the solid tableted granulation or the prepared pellets may optionally be coated with at least one separating layer before application of the enteric coating.
  • Examples of materials which may be used as a separating layer include pharmaceutically acceptable compounds such as sugar, polyethylene glycol, polyvinylpyrrolidine, polyvinyl alcohol, polyvinyl acetate, hydroxypropyl cellulose, methylcellulose, ethylcellulose, hydroxypropyl methylcellulose, carboxymethylcellulose sodium, water soluble salts of enteric coating polymers or mixtures thereof.
  • pharmaceutically acceptable compounds such as sugar, polyethylene glycol, polyvinylpyrrolidine, polyvinyl alcohol, polyvinyl acetate, hydroxypropyl cellulose, methylcellulose, ethylcellulose, hydroxypropyl methylcellulose, carboxymethylcellulose sodium, water soluble salts of enteric coating polymers or mixtures thereof.
  • the separating layer may further comprise additives such as plasticizers, colorants, pigments, fillers anti-tacking and anti-static agents, such as magnesium stearate, titanium dioxide, talc.or mixtures thereof.
  • additives such as plasticizers, colorants, pigments, fillers anti-tacking and anti-static agents, such as magnesium stearate, titanium dioxide, talc.or mixtures thereof.
  • Separating layers may be applied to the prepared tablets or pellets by coating or layering procedures in suitable equipment, such as coating pan, coating granulator or in a fluidized bed apparatus using water and/or organic solvents for the coating process.
  • the separating layers may be applied to the tablets or pellets by using a powder coating technique.
  • the separating layer when applied, may be of a variable thickness.
  • the maximum thickness of the separating layer is normally only limited by processing conditions.
  • the separating layer may further serve as a diffusion barrier and may act as a pH-buffering zone.
  • the pH-buffering properties of the separating layer may be further strengthened by introducing into the layer one or more substances chosen from a group of compounds often used in antacid formulations, for example magnesium oxide, hydroxide or carbonate, aluminium or calcium hydroxide, carbonate or silicate; composite aluminium magnesium compounds (e.g.
  • Talc or other compounds may be added to increase the thickness of the layer and thereby strengthen the diffusion barrier.
  • the separating layer may alternatively be formed in situ, for example by reaction of an enteric coating polymer layer with an alkaline reacting compound contained in the tablets or pellets, upon application of the enteric coating onto the tablets or pellets.
  • Enteric coatings which may be employed include those known to those skilled in the art, for example cellulose acetate phthalate, acrylate polymers (e.g. acrylic resins such as Eudragit L and Eudragit S), hydroxypropyl methylcellulose phthalate, polyvinyl acetate phthalate, methacrylic acid copolymers, hydroxypropyl methylcellulose acetate succinate, polyvinyl acetate phthalate, cellulose acetate trimellitate, carboxymethylethylcellulose, shellac or combinations thereof.
  • cellulose acetate phthalate e.g. acrylic resins such as Eudragit L and Eudragit S
  • hydroxypropyl methylcellulose phthalate e.g. acrylic resins such as Eudragit L and Eudragit S
  • polyvinyl acetate phthalate e.g. acrylic resins such as Eudragit L and Eudragit S
  • methacrylic acid copolymers hydroxypropyl methylcellulose acetate succinate
  • the enteric coating layers may also contain appropriate quantities of pharmaceutically acceptable plasticizers in order to obtain the desired mechanical properties (e.g. flexibility and hardness).
  • suitable plasticizers include triacetin, citric acid esters, phthalic acid esters, dibutyl sebacate, cetyl alcohol, polyethylene glycols, polysorbates or combinations thereof.
  • plasticizer will depend upon the nature of the constituents of the enteric coating layer formula and how much of the said formula is to be applied to the pellets. Ideally the mechanical properties should be adjusted so that the acid resistance of the enteric coated pellets does not significantly alter during compression of pellets into tablets. Typical amounts of plasticizer are above 10% by weight of the enteric coating layer polymer(s), preferably 15 - 50% and more preferably 20 - 50%.
  • Further additives which may be employed in the enteric coating layer include dispersants, colorants, pigments, polymers e.g. poly(ethylacrylate or -methylmethacrylate), anti-tacking and anti- foaming agents. Other compounds may be added to increase film thickness of the enteric coating layer.
  • the film thickness of the enteric coating layer is preferably at least 10 ⁇ m, preferably more than 20 ⁇ m.
  • Enteric coated pellets may be coated further with one or more over-coating layers in order to prevent agglomeration of pellets and to protect the enteric coating layer from cracking during the compaction process, i.e. the compression of the pellets into a tablet.
  • the over-coating layers may be applied to the enteric coated pellets by coating or layering procedures using suitable equipment such as a coating pan, a coating granulator or in a fluidized bed apparatus, using water and/or organic solvents for the coating or layering process.
  • suitable materials for use as the over-coating layers include sugar, polyethylene glycol, polyvinylpyrrolidine, polyvinyl alcohol, polyvinyl acetate, hydroxypropyl cellulose, methylcellulose, ethylcellulose, hydroxypropyl methylcellulose, carboxymethylcellulose sodium or combinations thereof.
  • the overcoating layer may further comprise additives such as plasticizers, colorants, pigments, fillers, anti-tacking and anti-static agents, such as for instance magnesium stearate, titamum dioxide, talc and other additives may also be included in the over-coating layer.
  • additives such as plasticizers, colorants, pigments, fillers, anti-tacking and anti-static agents, such as for instance magnesium stearate, titamum dioxide, talc and other additives may also be included in the over-coating layer.
  • additives such as plasticizers, colorants, pigments, fillers, anti-tacking and anti-static agents, such as for instance magnesium stearate, titamum dioxide, talc and other additives may also be included in the over-coating layer.
  • the maximum thickness of the applied over-coating layer(s) is normally only limited by processing conditions.
  • the prepared single unit tablet or compressed multiple unit tablet is optionally covered with at least one film-forming agent in order that the tablets obtains a smooth surface and to further enhance the stability of the tablets during packaging and transport.
  • a tablet coating layer may further comprise additives such as anti-tacking agents, colorants and pigments.
  • the dosage forms according to the invention are especially advantageous in the treatment of H. pylori infections. They are administered one to several times a day, preferably once or twice daily.
  • the typical daily dose of the active substances varies and depends upon various factors including the individual requirements of the patient, the mode of administration and the disease state to be treated.
  • each dosage form will comprise an amount of sodium amoxycillin corresponding to 50 mg to 2.0 g, preferably 100 mg to 1.0 g amoxycillin.
  • sodium amoxycillin in the manufacture of an enteric coated oral dosage form for use in the treatment of H. pylori infections.
  • the dosage forms according to the invention may be administered alone or in combination with proton pump inhibitors. Any compound which is known in the art and indicated as being a proton pump inhibitor may be used in conjunction with the dosage forms according to the invention.
  • Proton pump inhibitors may be used in any form (e.g. in the none-salt form or as an alkali or an alkaline earth metal salt). Examples of suitable proton pump inhibitors include those described in European Patent Applications EP 0 005 129, EP 1 174 726 and EP 1 166 287; United Kingdom Patent Application GB 2 163 747; and International Patent Applications WO 90/06925, WO 94/27988 and WO 95/01977.
  • omeprazole particularly proton pump inhibitors which may be mentioned include omeprazole, lansoprazole, pantoprazole, pariprazole (rabeprazole) and limoprazole or its single enantiomers.
  • omeprazole S-omeprazole or an alkaline salt thereof.
  • Proton pump inhibitors may be coadministered separately along with the dosage forms according to the invention.
  • the dosage form further comprises a proton pump inhibitor, i.e. that the sodium amoxycillin and proton pump inhibitor are coformulated in an enteric coated oral dosage form.
  • Coformulation of proton pump inhibitors and sodium amoxycillin into an enteric coated oral dosage form may be carried out in accordance with known techniques, such as those described hereinbefore and/or those described in International Patent Application WO 96/01623.
  • the dosage forms according to the invention may be administered in combination with another gastric acid suppressing agents, such as a H 2 -receptor antagonist, for instance ranitidine, cimetidine or famotidine.
  • the dosage forms according to the invention may further be administered in combination with other antibacterial agents.
  • Antibacterial agents which may be mentioned include for example nitroimidazole antibiotics, tetracyclines, penicillins, cephalosporins, carbopenems, aminoglycosides, macrolide antibiotics, lincosamide antibiotics, 4-quinolones, rifamycins and nitrofurantoin.
  • antibacterial compounds are: ampicillin, amoxicillin trihydrate, benzylpenicillin, phenoxymethylpenicillin, bacampicillin, pivampicillin, carbenicillin, cloxacillin, cyclacillin, dicloxacillin, methicillin, oxacillin, peperacillin, ticarcillin, flucloxacillin, cefuroxime, cefetamet, cefetrame, cefixime, cefoxitin, ceftazidime, ceftizoxime, latamoxef, cefoperazone, ceftriaxone, cefsulodin, cefotaxime, cephalexin, cefaclor, cedadroxil, cefalothin, cefazolin, cefpodoxime, ceftibuten, aztreonam, tigemonam, erythromycin, dirithromycin, roxithromycin, azithromycin, clarithromycin, clindamycin, paldimycin,
  • the dosage forms according to the invention have the advantage that they are especially advantageous in the treatment of H. pylori infections, for example as shown in the tests described below.
  • the dosage forms according to the invention may also have the advantage that they are less toxic than, are more easily prepared than, produce less side effects than, have a longer shelf-life than, increase the stability of the pharmaceutically active compound more than, or have other useful pharmacological properties over, similar dosage forms which are known in the prior art. Tests
  • Discs having a diameter of 11.3 mm were compressed of different substances in a Diaf excenter press using flat faced table punches.
  • the discs were centrically mounted on a round steel plate with hollow fitting for the discs.
  • the discs were attached to the steel plate using a water resistant tape with a circular hole of 0.50 cm 2 .
  • the steel plate and the disc were attached to a motor (IKA RW20 DZM). While rotating, the disc was lowered into 200 ml of buffer pH 5.9 thermostated at 37°C. The rotating velocity was 500 rpm.
  • the dissolution medium was analysed by continuous recirculation through the spectrophotometer using a 10 mm flow cuvette and a peristaltic pump.
  • Concentrations in the dissolution medium were determined spetrophotometrically using a Perkin Elmer Lambda 2 spectrophotometer. The pH values were measured using a Metrohm 620 pH-meter.
  • Urea breath test or Urease biopsy test were used to show activity for Helicobacter pylori.
  • the dissolution rate of amoxycillin sodium is 100 times faster than for amoxycillin trihydrate. No difference of the dissolution rate between lyophilised and crystalline amoxycillin sodium was observed.
  • Sodium amoxycillin 224 g corresponds to 200 g amoxycillin Microcrystalline cellulose 245 g Sodium starch glycolate 75 g Polyvinylpyrrolidone 38 g Magnesium stearate 8.4 g
  • Sodium amoxycillin was mixed in a planetary mixer for 5 minutes with microcrystalline cellulose and sodium starch glycolate. The resultant mixture was then moistened for 5 minutes with a solution of polyvinylpyrrolidone in isopropanol and dried. The granulate was milled through a 1.0 mm sieve and lubricated for 2 min with magnesium stearate. The granulate was compressed to tablets on a tabletting machine fitted with 12 mm punches. Each tablet contained an amount of sodium amoxicyllin corresponding to 200 mg amoxycillin.
  • the obtained tablets are covered with a separating layer and an enteric coating layer.
  • Methacrylic acid copolymer dispersion (30%) 2450 g Polyethylene glycol 400 80 g Titanium dioxide 100 g Water purified 1960 g

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Abstract

L'invention concerne une forme posologique orale à enrobage gastro-résistant contenant de l'amoxicilline de sodium. Ladite forme posologique se présente sous la forme de comprimés à une seule unité ou à plusieurs unités. L'invention concerne également la fabrication desdites formes posologiques ainsi que l'utilisation desdites préparations dans le traitement d'infections à Helicobacter pylori.
PCT/SE1998/000356 1997-03-12 1998-02-27 Forme posologique orale a enrobage gastro-resistant contenant de l'amoxicilline de sodium WO1998040054A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP53949898A JP2001515489A (ja) 1997-03-12 1998-02-27 アモキシシリンナトリウムからなる腸溶性被覆経口剤形
EP98909899A EP0981335A1 (fr) 1997-03-12 1998-02-27 Forme posologique orale a enrobage gastro-resistant contenant de l'amoxicilline de sodium
AU64268/98A AU6426898A (en) 1997-03-12 1998-02-27 An enteric coated oral dosage form comprising sodium amoxycillin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE9700885-8 1997-03-12
SE9700885A SE9700885D0 (sv) 1997-03-12 1997-03-12 New pharmaceutical formulation

Publications (1)

Publication Number Publication Date
WO1998040054A1 true WO1998040054A1 (fr) 1998-09-17

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PCT/SE1998/000356 WO1998040054A1 (fr) 1997-03-12 1998-02-27 Forme posologique orale a enrobage gastro-resistant contenant de l'amoxicilline de sodium

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EP (1) EP0981335A1 (fr)
JP (1) JP2001515489A (fr)
AU (1) AU6426898A (fr)
SE (1) SE9700885D0 (fr)
WO (1) WO1998040054A1 (fr)

Cited By (19)

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EP1044680A1 (fr) * 1999-04-13 2000-10-18 Beecham Pharmaceuticals (Pte) Limited Nouvelle méthode de traitement à l'aide d'un fort régime de dosage d'Amoxycillin et de Clavulanate de Potassium
US6294199B1 (en) * 1999-04-13 2001-09-25 Beecham Pharmaceuticals (Pte) Limited Method of treating a bacterial infection comprising administering amoxycillin
WO2002049618A1 (fr) * 2000-12-21 2002-06-27 Smithkline Beecham P.L.C. Pastilles d'amoxycilline
WO2002083132A1 (fr) * 2001-04-18 2002-10-24 Orexo Ab Composition inhibant la secretion d'acides gastriques
WO2003051342A1 (fr) * 2001-12-18 2003-06-26 Laboratorios Del Dr. Esteve, S.A. Forme de dosage pharmaceutique buccal comprime a revetement enterique, contenant un compose de benzimidazole labile en milieu acide
US6726908B2 (en) 1995-09-07 2004-04-27 Smithkline Beecham P.L.C. Pharmaceutical formulation
US6746692B2 (en) 1999-04-13 2004-06-08 Beecham Pharmaceuticals (Pte) Limited Modified release pharmaceutical formulation comprising amoxycillin
US6756057B2 (en) 2000-10-12 2004-06-29 Beecham Pharmaceuticals (Pte) Limited Amoxicillin and potassium clavulanate dosage form
US6780882B2 (en) 1996-01-04 2004-08-24 The Curators Of The University Of Missouri Substituted benzimidazole dosage forms and method of using same
US7011849B2 (en) 2000-10-12 2006-03-14 Beecham Pharmaceuticals (Pte) Limited Second release phase formulation
US7217430B2 (en) 1999-04-13 2007-05-15 Beecham Pharmaceuticals (Pte) Limited Compositions and methods of treatment comprising amoxicillin and potassium clavulanate with xanthan
WO2008030141A1 (fr) * 2006-09-06 2008-03-13 Bosnalijek, Pharmaceutical And Chemical Industry, Joint Stock Company Utilisation de nifuroxazide en tant que composant d'une thérapie médicamenteuse combinée de maladies associées à une infection provoquée par helicobacter pylori et procédé de traitement destiné à éradiquer l'agent étiologique
US7771747B2 (en) 2002-10-16 2010-08-10 Orexo Ab Gastric acid secretion inhibiting composition
USRE45198E1 (en) 1996-01-04 2014-10-14 The Curators Of The University Of Missouri Omeprazole solution and method for using same
US8906940B2 (en) 2004-05-25 2014-12-09 Santarus, Inc. Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them
US8993599B2 (en) 2003-07-18 2015-03-31 Santarus, Inc. Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them
US9498445B2 (en) 2013-02-13 2016-11-22 Redhill Biopharma Ltd. Pharmaceutical compositions for the treatment of Helicobacter pylori
CN107405338A (zh) * 2015-01-09 2017-11-28 加州大学评议会 用于治疗胃肠道感染的组合物和方法
US11878011B2 (en) 2020-05-07 2024-01-23 Redhill Biopharma Ltd. Method for eradicating Helicobacter pylori infection in patients regardless of body mass index

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US8168228B2 (en) * 2003-10-17 2012-05-01 Sandoz Ag Antibiotic clarithromycin micropellet compositions

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WO1994000112A1 (fr) * 1992-06-24 1994-01-06 Astra Aktiebolag Formulation orale destinee au traitement antibacterien gastrique, procede de preparation et d'utilisation de cette formulation
WO1995025516A1 (fr) * 1994-03-24 1995-09-28 Smithkline Beecham Plc Formulations pharmaceutiques contenant des beta-lactamines ainsi que des tensioactifs a base de sulfate d'alcoyle
WO1997002020A1 (fr) * 1995-07-05 1997-01-23 Byk Gulden Lomberg Chemische Fabrik Gmbh Composition pharmaceutique administrable par voie orale contenant des agents actifs antimicrobiens et du pantoprazole a liberation differee

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
WO1994000112A1 (fr) * 1992-06-24 1994-01-06 Astra Aktiebolag Formulation orale destinee au traitement antibacterien gastrique, procede de preparation et d'utilisation de cette formulation
WO1995025516A1 (fr) * 1994-03-24 1995-09-28 Smithkline Beecham Plc Formulations pharmaceutiques contenant des beta-lactamines ainsi que des tensioactifs a base de sulfate d'alcoyle
WO1997002020A1 (fr) * 1995-07-05 1997-01-23 Byk Gulden Lomberg Chemische Fabrik Gmbh Composition pharmaceutique administrable par voie orale contenant des agents actifs antimicrobiens et du pantoprazole a liberation differee

Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6726908B2 (en) 1995-09-07 2004-04-27 Smithkline Beecham P.L.C. Pharmaceutical formulation
USRE45198E1 (en) 1996-01-04 2014-10-14 The Curators Of The University Of Missouri Omeprazole solution and method for using same
US6780882B2 (en) 1996-01-04 2004-08-24 The Curators Of The University Of Missouri Substituted benzimidazole dosage forms and method of using same
US6746692B2 (en) 1999-04-13 2004-06-08 Beecham Pharmaceuticals (Pte) Limited Modified release pharmaceutical formulation comprising amoxycillin
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JP2001515489A (ja) 2001-09-18

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