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WO2007086012A1 - Préparation de cefpodoxime, d'acide clavulanique et de linezolide - Google Patents

Préparation de cefpodoxime, d'acide clavulanique et de linezolide Download PDF

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Publication number
WO2007086012A1
WO2007086012A1 PCT/IB2007/050244 IB2007050244W WO2007086012A1 WO 2007086012 A1 WO2007086012 A1 WO 2007086012A1 IB 2007050244 W IB2007050244 W IB 2007050244W WO 2007086012 A1 WO2007086012 A1 WO 2007086012A1
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WO
WIPO (PCT)
Prior art keywords
pharmaceutical composition
cefpodoxime
enhance
antimicrobial activity
linezolid
Prior art date
Application number
PCT/IB2007/050244
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English (en)
Inventor
Jegannathan Srinivas
Original Assignee
Jegannathan Srinivas
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 Jegannathan Srinivas filed Critical Jegannathan Srinivas
Publication of WO2007086012A1 publication Critical patent/WO2007086012A1/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
    • A61K31/42—Oxazoles
    • A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
    • 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
    • A61K31/42—Oxazoles
    • A61K31/424—Oxazoles condensed with heterocyclic ring systems, e.g. clavulanic 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
    • A61K31/54—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 sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/542—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 sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
    • A61K31/546—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine containing further heterocyclic rings, e.g. cephalothin

Definitions

  • the present invention belongs to the field of pharmaceutical technology. More particularly the invention principally relates to a pharmaceutical composition of normal and modified release fixed dose formulations comprising a betalactam antibiotic, Cefpodoxime proxetil or its pharmaceutically acceptable hydrates, salts or esters as the active ingredient, and complexated in Betacyclodextrin or similar bioavailability enhancer.
  • the invention relates to pharmaceutical composition of Cefpodoxime fortified with Clavulanic acid and Linezolid.
  • the invention relates to pharmaceutical composition of normal and modified release fixed dose formulations in which the active material is selected from Cefpodoxime, or its pharmaceutically acceptable hydrates, salts or esters. Inclusion of Clavulanic Acid enables enhanced antimicrobial activity and potentiation of Cefpodoxime, while combination with Linezolid enhances the spectrum of activity.
  • Betalactamases which hydrolyze Betalactam antibiotics such as penicillins, cephalosporins and carbapenems. These enzymes catalyze the hydrolysis of the Betalactam ring to effectively destroy the antibiotic's activity.
  • Enzyme Inhibitors such as Clavulanic Acid have been proved to be extremely useful in overcoming the bacterial resistance by inhibiting the betalactamase enzyme.
  • the enzyme inhibitors have a limited or nil action against the bacteria that produce Extended Spectrum Betalactamases (ESBL) such as Pseudomonas spp. Nevertheless, combining Clavulanic Acid has been found to substantially enhance the antibacterial activity even between second-generation cephalosporins, such as Cefaclor and Cefprozil (U.S. Patent Application No. 20030109503 of GSK).
  • the objectives during antimicrobial therapy are to maximize blood concentration; preferably several fold higher than the minimum inhibitory concentration (MIC) for the particular agent, but to minimize both the risk of toxicity to the patient and of promoting microbial resistance.
  • MIC minimum inhibitory concentration
  • oral administration will be the preferred route, in the case of antibiotics this route is frequently unattractive because of their low or variable oral bioavailability.
  • While many compounds are known to be useful as pharmacologically active substances, some of them have relatively short biological half-life and need to be administered several times a day in order to achieve desired therapeutic effect. However, a decrease in the frequency of administration will not only reduce the burden on the patient but will also increase compliance and thus provide greater therapeutic effect. It can be achieved by controlling the release of active ingredients or by reducing the elimination of the active ingredient from the body, so that the effective level is maintained in the blood for a prolonged period of time.
  • hydrophilic polymers to produce, sustained or modified release pharmaceutical compositions.
  • release of the drug is controlled primarily by diffusion of the drug, or by surface erosion of the hydrophilic polymers into the surrounding medium, or by a combination of the two processes. Control of the rate of release can produce constant blood levels of the active ingredient that may result in reducing the frequency of administration, thereby improving patient compliance to the dosage regimen.
  • United States Patent No. 4,250,166 discloses a long-acting Cephalexin preparation comprising of normal quick-releasing Cephalexin and particulate Cephalexin coated with a copolymer of methylmethacrylate and methacrylic acid, which dissolves at a pH from 5. 5 to 6.5 and the potency ratio of the normal Cephalexin to coated cephalexin is between 40: 60 and 25: 75.
  • United States Patent No. 5,948,440 discloses a controlled release tablet of an active ingredient comprising of cefaclor, cephalexin, or their pharmaceutically acceptable hydrates, salts, or esters as active ingredient, and a mixture of hydrophilic polymers selected from the group consisting of at least one hydroxypropyl methylcellulose and at least one hydroxypropylcellulose.
  • the composition optionally also contains one or more of a water-soluble or water dispersible diluent.
  • the quantities of the hydrophilic polymers and water- soluble or water-dispersible diluents are such that the therapeutically effective active ingredient is released at a rate suitable for twice daily administration of the pharmaceutical composition.
  • U.S Patent Application No. 20040126429 discloses a modified release preparation of the Fixed Dose Combination of Amoxycillin plus Clavulanic Acid with a claim of both immediate and sustained action in the NDDS.
  • Japanese Patent JP 57165392A discloses a long-acting cephalexin tablet comprising cephalexin mixed with 210% w/w oils and fats (e. g. higher fatty acid, higher alcohol, alcohol ester, etc.) and with a vehicle such as microcrystalline cellulose and a lubricant such as magnesium stearate, and the mixture is pressed, formed to granules passing through a 20 mesh sieve, and subjected to the slug-forming process to obtain a high-quality long-acting tablet.
  • the rate of dissolution of cephalexin can be controlled by selecting the kind of oils and fats and the number of the times of slug formation process.
  • the object of the present invention is to provide an immediate as well as long acting pharmaceutical composition of a betalactam antibiotic such as Cefpodoxime, or its pharmaceutically acceptable hydrates, salts or esters in a modified release matrix formulation.
  • the objective of the present invention is to provide a pharmaceutical composition that provides Cefpodoxime with an enhanced activity in combination with Clavulanic Acid.
  • Another objective of the present invention is to provide an extended spectrum of activity by combining Cefpodoxime with Linezolid, an Oxazolidinone, a new class of antibiotic.
  • the combination provides exceptional advantage of coverage against MRSA/VRSA and some important anaerobes
  • Another objective of the present invention is to provide a pharmaceutical composition that provides a more bioavailable preparation with an absorption enhancer such as Betacyclodextrin
  • a further objective of the present invention is to provide a pharmaceutical composition that provides a conventional dosage form of the Fixed Dose Combination
  • Yet another objective of the present invention is to provide a pharmaceutical composition that provides a modified release dosage form of the Fixed Dose Combination to enhance patient compliance Summary:
  • composition of this invention is in the form of a matrix tablet comprising the active ingredient, w-hydrophilic polymers, water-soluble and/or water dispersible diluents, pharmaceutically acceptable tablet excipients, and antibiotic adjuvant if any, for controlling the release of active ingredients.
  • the active ingredient is a betalactam antibiotic such as Cefpodoxime, or its pharmaceutically acceptable hydrates, salts or esters in a controlled release matrix.
  • the Cefpodoxime, or its pharmaceutically acceptable hydrates, salts or esters may be present in an amount from about 100 mg to about 400 mg by weight of the controlled release matrix.
  • Cefpodoxime or its pharmaceutically acceptable hydrates, salts or esters may be present in an amount from 50 mg to 200 mg in the conventional dosage form.
  • cephalosporin antibiotics examples include all other I Generation Cephalosporins and, pharmaceutically acceptable hydrates, salts or esters thereof.
  • the Clavulanic Acid is used in combination with Cefpodoxime in a ratio of 2.5:1 or 2.5:2, based on the requirement for enhanced antimicrobial activity. It is an antibiotic adjuvant for reducing the elimination rate and increasing the half-life of the therapeutically active ingredient. Inclusion of Clavulanic Acid allows reduction in the amount of active incorporated in the hydrophilic polymer matrix but still provides the desired once a day profile.
  • the pharmaceutical composition is complexated in Betacyclodextrin or any other absorption enhancer that enhances the absorption of the fixed dose combination of the antibiotic.
  • the pharmaceutical composition of the present invention may be prepared by procedures well known to formulation chemists.
  • the method of manufacturing can affect the release characteristics of the composition. The method is as follows:
  • This invention relates to pharmaceutical formulations, in particular to novel formulations for the treatment of bacterial infections.
  • This invention relates to pharmaceutical composition
  • pharmaceutical composition comprising fixed dose combination of Cefpodoxime with Clavulanate and Linezolid, and an absorption enhancer
  • Linezolid is an Oxazolidinone, a new class of antibiotic, which is less prone to bacterial resistance compared to the earlier antibiotics. Linezolid has an exceptionally good activity against MRSA, VRSA, E.faecalis and Bacteroides
  • Clavulanic acid in the form of its derivatives (hereinafter termed "clavulanate”), particularly its salts, are consequently used in formulations in combination with antibiotics to suppress the activity of beta.- lactamase enzymes which mediate bacterial resistance to betalactam antibiotics.
  • This type of microorganisms includes penicillin- resistant organisms such as Streptococcus spp., e.g. S. pneumoniae, Haemophilus spp., e.g. H. influenzae, Staphylococcus spp., E.coli, Proteus spp. and
  • clavulanate together with betalactam antibiotics is believed to be novel per se, and therefore in a further aspect of this invention there is provided a pharmaceutical formulation comprising in combination clavulanate together with a cephalosporin antibiotic selected from the cephalosporins, Cefpodoxime.
  • betalactam antibiotics referred to herein may be in the form of the free acids or pharmaceutically acceptable salts or in-vivo hydrolysable esters.
  • the clavulanate and any other antibacterial agent such as the penicillin or cephalosporin antibiotics, as used in this invention, whether in the form of the free acids, salts, esters or derivatives thereof are preferably each in a substantially pure form, e.g. at least 60% pure, more suitably at least 75% pure, preferably at least 85% especially at least 98% pure on a weight basis.
  • the formulation may be formulated for administration by any route, such as oral, topical or parenteral.
  • the route of choice may for example be determined by the route of choice for the antibacterial agent used in combination with the clavulanate.
  • the formulation may be in the form of tablets, capsules, powders, granules, lozenges, creams or liquid preparations, such as oral or sterile parenteral solutions or suspensions.
  • the topical formulations of the present invention may be presented as, for instance, ointments, creams or lotions, eye ointments and eye or ear drops, impregnated dressings and aerosols, and may contain appropriate conventional additives such as preservatives, solvents to assist drug penetration and emollients in ointments and creams.
  • the formulations may also contain compatible conventional carriers, such as cream or ointment bases and ethanol or oleyl alcohol for lotions. Such carriers may be present at from about 1 % up to about 98% of the formulation. More usually they will form up to about
  • Tablets and capsules for oral administration may be in unit dose presentation form, and may contain conventional excipients such as binding agents, for example syrup, acacia, gelatin, sorbitol, tragacanth, or polyvinylpyrollidone; fillers, for example lactose, sugar, maize-starch, calcium phosphate, sorbitol or glycine; tabletting lubricants, for example magnesium stearate, talc, polyethylene glycol or silica; disintegrants, for example potato starch; or acceptable wetting agents such as sodium lauryl sulphate.
  • binding agents for example syrup, acacia, gelatin, sorbitol, tragacanth, or polyvinylpyrollidone
  • fillers for example lactose, sugar, maize-starch, calcium phosphate, sorbitol or glycine
  • tabletting lubricants for example magnesium stearate, talc, polyethylene glycol or silica
  • Such tablets may also include an effervescent couple of generally known type, e.g a solid carboxylic acid and an alkali metal carbonate or bicarbonate.
  • Such tablets may also include a chewable base such as mannitol, sorbitol or lactose, optionally together with an effervescent couple.
  • Such tablets and solid dosage forms may be made by any of the generally known methods for such dosage forms, and may be coated according to methods well known in normal pharmaceutical practice.
  • Oral liquid preparations may be in the form of, for example, aqueous or oily suspensions, solutions, emulsions, syrups or elixirs, or may be presented as a dry product for reconstitution with water or other suitable vehicle before use.
  • Such liquid preparations may contain conventional additives, such as suspending agents, for example sorbitol, methyl cellulose, glucose syrup, gelatin, hydroxyethyl cellulose, carboxymethyl cellulose, aluminium stearate gel or hydrogenated edible fats, emulsifying agents, for example lecithin, sorbitan monooleate, or acacia; nonaqueous vehicles (which may include edible oils), for example almond oil, oily esters such as glycerine, propylene glycol, or ethyl alcohol; preservatives, for example methyl or propyl p-hydroxybenzoate or sorbic acid, and, if desired, conventional flavouring or colouring agents.
  • suspending agents for example sorbitol, methyl cellulose, glucose syrup, gelatin, hydroxyethyl cellulose, carboxymethyl cellulose, aluminium stearate gel or hydrogenated edible fats, emulsifying agents, for example lecithin, sorbitan monooleate, or
  • Suppositories will contain conventional suppository bases, e.g. cocoa-butter or other glyceride.
  • fluid unit dosage forms are prepared utilizing clavulanate and any antibacterial agent and a sterile vehicle, water being preferred. These active compounds, depending on the vehicle and concentration used, can be either suspended or dissolved in the vehicle. In preparing solutions the active compounds can be dissolved in water for injection and filter sterilised before filling into a suitable vial or ampoule and sealing.
  • agents such as a local anaesthetic, preservative and buffering agents can be dissolved in the vehicle.
  • the formulation can be frozen after filling into the vial and the water removed under vacuum.
  • the dry lyophilized powder is then sealed in the vial and an accompanying vial of water for injection may be supplied to reconstitute the liquid prior to use.
  • Parenteral suspensions are prepared in substantially the same manner except that the ingredients of the suspension are suspended in the vehicle instead of being dissolved and sterilization cannot be accomplished by filtration.
  • the formulation can be sterilised by exposure of its dry constituents to ethylene oxide before suspending in the sterile vehicle.
  • a surfactant or wetting agent is included in the formulation to facilitate uniform distribution of the active compounds. 18.
  • Aqueous solution and suspension formulations of this invention can only be provided in the form of dry solids for make up into aqueous solution or suspension shortly prior to use, for example
  • aqueous suspensions or solutions insofar as they contain clavulanate must be provided as dry solids for reconstitution with water shortly before administration.
  • a formulation according to the invention may be in unit dosage form, for example unit dosage form for oral or parenteral administration, which latter will primarily include administration by injection or infusion, especially intramuscular and intravenous administration.
  • the above-mentioned formulations may contain 0.1- 90% by weight, preferably from 10-60% by weight of the active materials, depending on the method of administration.
  • the clavulanate may suitably be administered to the patient at a daily dosage of from 0.3 to 15 mg/kg, preferably from 0.7 to 10 mg/kg, for example from 0.7 to 7 mg/kg, of body weight.
  • for an adult human (of approximately 70 kg body weight) from 25 to 1000 mg, preferably from 50 to 500 mg, of clavulanate expressed as its free acid equivalent may be administered daily, suitably in from 2.5:1 to 2.5:2, separate doses. Higher or lower dosages may, however, be used in accordance with clinical practice.
  • each unit dose may suitably comprise from 12.5 to 1000 mg, preferably from 12.5 to 250 mg, of clavulanate.
  • Each unit dose may, for example, be 12.5, 25, 37.5, 50, 62.5, 75, 87.5, 100, 125, 150, 200, or 250 mg of clavulanate.
  • the ratio of the amount of the clavulanate used according to the invention to the amount of any antibacterial agent present may vary within a wide range.
  • the said ratio may, for example, be from 1 :1 to 1 :30; more particularly, it may, for example, be from 1 :1 to 1 :12, for example 1 :2, 1 :3, 1 :4, 1 :5, 1 :6, 1 :7, 1 :8, or 1 :9 by weight, suitably within a variance of +-.10%.
  • Suitable unit dosages and maximum daily dosages of any antibacterial agent used in combination with clavulanate in this invention may for example be determined according to the unit dosages and maximum daily dosages of the agent used conventionally.
  • amoxycillin is generally provided in unit dosages of 125 to 1000 mg, administered from 2 to 4 times daily to a typical daily dosage of 125 to 3000 mg per day.
  • amoxycillin is generally provided in unit dosages of 125 to 1000 mg, administered from 2 to 4 times daily to a typical daily dosage of 125 to 3000 mg per day.
  • Cefpodoxime is generally provided in unit dosages of 125 and 1000 mg, and may be dosed up to a maximum daily dosage of 4000 mg per day.
  • a preferred combination of this invention is clavulanate with amoxycillin, in a ratio clavulanate:amoxycillin in the range 1 :1 to 1 :12, for example together in a formulation.
  • An example of a suitable formulation according to the invention for oral administration is one comprising from 125 to 3000 mg, preferably from 500 to 1000 mg, of amoxycillin trihydrate, in admixture or conjunction with from 12.5 to 250 mg, preferably from 25 to 125 mg, of potassium clavulanate per unit dose.
  • a further example of a suitable formulation according to this invention for parenteral administration is one comprising from 125 to 3000 mg of sodium amoxycillin, in admixture or conjunction with from 12.5 to 250 mg, preferably from 25 to 125 mg, of potassium clavulanate.
  • An example of a unit dosage form of a formulation of this invention comprises 12.5 to 1000 mg of potassium clavulanate and 125 to 1000 mg of Cefpodoxime - both in the conventional form as well as modified release form.
  • a further example of this formulation is the addition of an absorption enhancer, such as Betacyclodextrin to enhance the bioavailibility

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

Abstract

La présente invention concerne une composition pharmaceutique de Cefpodoxime et d'acide clavulanique associés en dose fixe à du linezolide et à un activateur de biodisponibilité. Dans le cas présent, le clavulanate de potassium agit comme un inhibiteur enzymatique accentuant l'activité antibactérienne. Les principes actifs, qui sont issus fondamentalement du cefpodoxime, sont soumis à une réaction avec le clavulanate de potassium. De plus, la composition contenant du cefpodoxime et du clavulanate est complexée avec un accentuateur d'absorption tel que la bêtacyclodextrine et un autre médicament, le linezolide, un oxazolidinnone faisant partie d'une ouvelle classe d'antibactériens exceptionnellement efficaces contre MRSA, VRSA, E.faecalis et les bactéroïdes. Cette composition peut se présenter sous forme pharmaceutique à libération normale et modifiée ainsi qu'en dose injectable.
PCT/IB2007/050244 2006-01-25 2007-01-24 Préparation de cefpodoxime, d'acide clavulanique et de linezolide WO2007086012A1 (fr)

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IN121CH2006 2006-01-25
IN121/CHE/2006 2006-01-25

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011078820A1 (fr) * 2009-12-25 2011-06-30 Mahmut Bilgic Formulations pharmaceutiques comprenant une céphalosporine de troisième génération et de l'acide clavulanique
WO2011142730A1 (fr) * 2010-05-14 2011-11-17 Mahmut Bilgic Composition pharmaceutique comprenant la céfixime et un composé dérivé de l'acide clavulanique
WO2011152806A1 (fr) * 2010-06-03 2011-12-08 Mahmut Bilgic Méthode de production de formulation effervescente comprenant du céphalosporine et du clavulanate de potassium
WO2011152807A1 (fr) * 2010-06-03 2011-12-08 Bilgic Mahmut Préparations pharmaceutiques comprenant du cefpodoxime proxetil et de l'acide clavulanique
WO2011093826A3 (fr) * 2010-01-29 2011-12-15 Mahmut Bilgic Formulations effervescentes comprenant du céfaclor et de l'acide clavulanique comme principes actifs
US8614315B2 (en) 2009-12-25 2013-12-24 Mahmut Bilgic Cefdinir and cefixime formulations and uses thereof
WO2014170683A1 (fr) * 2013-04-17 2014-10-23 Blueberry Therapeutics Limited Compositions et procédés pour lutter contre des bactéries résistantes à un antibactérien

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994016696A1 (fr) * 1993-01-22 1994-08-04 Smithkline Beecham Plc Formulations pharmaceutiques comprenant de l'acide clavulanique seul ou associe a d'autres beta-lactamines
WO2001034128A2 (fr) * 1999-11-08 2001-05-17 Pharmacia & Upjohn Company Melange de linezolid et d'autres agents antibacteriens
US20020022610A1 (en) * 2000-06-30 2002-02-21 Batts Donald H. Compositions and methods for treating bacterial infections

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994016696A1 (fr) * 1993-01-22 1994-08-04 Smithkline Beecham Plc Formulations pharmaceutiques comprenant de l'acide clavulanique seul ou associe a d'autres beta-lactamines
WO2001034128A2 (fr) * 1999-11-08 2001-05-17 Pharmacia & Upjohn Company Melange de linezolid et d'autres agents antibacteriens
US20020022610A1 (en) * 2000-06-30 2002-02-21 Batts Donald H. Compositions and methods for treating bacterial infections

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8614315B2 (en) 2009-12-25 2013-12-24 Mahmut Bilgic Cefdinir and cefixime formulations and uses thereof
WO2011078820A1 (fr) * 2009-12-25 2011-06-30 Mahmut Bilgic Formulations pharmaceutiques comprenant une céphalosporine de troisième génération et de l'acide clavulanique
US9603794B2 (en) 2010-01-29 2017-03-28 Mahmut Bilgic Preparations of effervescent formulations comprising cephalosporin and uses thereof
WO2011093826A3 (fr) * 2010-01-29 2011-12-15 Mahmut Bilgic Formulations effervescentes comprenant du céfaclor et de l'acide clavulanique comme principes actifs
WO2011093833A3 (fr) * 2010-01-29 2011-12-15 Mahmut Bilgic Formulations effervescentes contenant de la céphalosporine de deuxième génération
WO2011093823A3 (fr) * 2010-01-29 2011-12-15 Mahmut Bilgic Formulations effervescentes comprenant du céfaclor et de l'acide clavulanique
WO2011093832A3 (fr) * 2010-01-29 2011-12-15 Mahmut Bilgic Formulations effervescentes stables contenant du céfaclor
WO2011093824A3 (fr) * 2010-01-29 2011-12-22 Mahmut Bilgic Formulations effervescentes comprenant du céfaclor
US8956653B2 (en) 2010-01-29 2015-02-17 Mahmut Bilgic Preparations for effervescent formulations comprising cephalosporin and uses thereof
WO2011142730A1 (fr) * 2010-05-14 2011-11-17 Mahmut Bilgic Composition pharmaceutique comprenant la céfixime et un composé dérivé de l'acide clavulanique
WO2011152807A1 (fr) * 2010-06-03 2011-12-08 Bilgic Mahmut Préparations pharmaceutiques comprenant du cefpodoxime proxetil et de l'acide clavulanique
WO2011152805A3 (fr) * 2010-06-03 2012-04-05 Mahmut Bilgic Composition pharmaceutique comprenant de l'acide clavulanique et du cefpodoxime proxétil
WO2011152809A3 (fr) * 2010-06-03 2012-02-16 Bilgic Mahmut Formulations effervescentes comprenant de la céphalosporine et de l'acide clavulcanique
WO2011152806A1 (fr) * 2010-06-03 2011-12-08 Mahmut Bilgic Méthode de production de formulation effervescente comprenant du céphalosporine et du clavulanate de potassium
WO2014170683A1 (fr) * 2013-04-17 2014-10-23 Blueberry Therapeutics Limited Compositions et procédés pour lutter contre des bactéries résistantes à un antibactérien

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