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WO2012060785A1 - Procédé de production de formulations comprenant de la céphalosporine - Google Patents

Procédé de production de formulations comprenant de la céphalosporine Download PDF

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Publication number
WO2012060785A1
WO2012060785A1 PCT/TR2011/000250 TR2011000250W WO2012060785A1 WO 2012060785 A1 WO2012060785 A1 WO 2012060785A1 TR 2011000250 W TR2011000250 W TR 2011000250W WO 2012060785 A1 WO2012060785 A1 WO 2012060785A1
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WO
WIPO (PCT)
Prior art keywords
diluent
disintegrant
formulation according
tablet
pharmaceutical formulation
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Ceased
Application number
PCT/TR2011/000250
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English (en)
Inventor
Mahmut Bilgic
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Individual
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Individual
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Publication of WO2012060785A1 publication Critical patent/WO2012060785A1/fr
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
    • 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
    • A61K9/2072—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
    • 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

Definitions

  • the present invention relates to the process for the preparation of the pharmaceutical formulations comprising cephalosporin antibiotics.
  • Cephalosporins were first isolated in 1948 and first generation cephalosporins were produced and released in 1960.
  • Cephem derivative 7- amino-cephalosporinic acid constitutes the basic core of cephalosporins. Cephalosporins are classified into different generations according to a classification method which is chronological and practical in terms of reflecting the improvement in antibacterial spectrum.
  • the physical properties of the final product in tablet form such as hardness and dissolution time can change according to the methods used in developing the formulations.
  • Hardness of the tablets is important, if the tablet is too hard then it may be too brittle and as a result it may break into pieces while carrying them; dispersion time is important because as the dispersion time gets shorter, the onset time of the medication gets shorter as well so the medication shows its effect in a shorter time.
  • the inventors have found that the relative proportion of the excipients used while preparing the cephalosporin containing granules and while preparing a pharmaceutical formulation with the prepared granules plays an important role in the hardness and the dissolution time of the dosage forms prepared with the obtained formulations. Additionally, the compression force that is used when preparing tablet forms from the formulations according to present invention also play an important role in the dissolution and hardness properties of the dosage forms obtained with these formulations.
  • Inventors of the present invention use two portions of diluent and disintegrant compositions while preparing the formulations; one portion is used for preparing the granules comprising cephalosporin antibiotic and the other portion is used for preparing the formulation with the obtained granules.
  • the granules are mixed with the diluent and disintegrant composition, and if need be with at least one other excipients to give the formulations according to present invention
  • the first aspect of the present invention is the process for preparing the formulation comprising a cephalosporin antibiotic and other excipients wherein said formulation consists of (a) granules comprising cephalosporin antibiotic and diluent and disintegrant composition and (b) an other diluent and disintegrant composition and at least one other pharmaceutically acceptable excipient and the process is characterized in that the granules comprising cephalosporin antibiotic, diluent and disintegrant are mixed with the other diluent and disintegrant composition wherein the other diluent and disintegrant composition is in an amount of 96-100% by weight in proportion to the amount of diluent and disintegrant composition that was used for obtaining the granules and wherein a tablet compression force in the range of 5-200 kN, preferably 10-150 kN, more preferably 20-100 kN is applied.
  • the formulation prepared according to present invention consists of a mixture of (a) and (b).
  • the formulation consists of a mixture of granules comprising cephalosporin antibiotic, diluent and disintegrant composition with other diluent and disintegrant composition and at least one other excipient.
  • friability value An important parameter relating to tablet hardness is friability value.
  • the inventors have seen that when the tablet compression force having a value in the range of 5-200 kN, preferably 10-150 kN, more preferably 20-100 kN is applied, the friability value of the tablet forms is in the range of 0.01- 0.1, preferably 0.02- 0.05.
  • another aspect of the present invention is the process for preparing the tablet forms comprising cefdinir with the friability value in the range of 0.01- 0.1, preferably 0.02- 0.05.
  • cepholosporin group molecules stated in the text comprises cepholosporin group molecules such as cefpodoxime, cefditoren, cefdinir, cefixime, cefuroxime, cefaclor, ceftibuten, cefprozil, cefepime and cefetamet.
  • Cefpodoxime can be in the form of its pharmaceutically acceptable esters, solvates, hydrates, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms or free form and/or a combination thereof.
  • cefpodoxime proxetil is used.
  • Cefditoren can be in the form of its pharmaceutically acceptable esters, solvates, hydrates, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms or free form and/or a combination thereof.
  • cefditoren pivoxil is used.
  • Cefdinir can be in the form of its pharmaceutically acceptable esters, solvates, hydrates, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms or free form and/or a combination thereof.
  • Cefixime can be in the form of its pharmaceutically acceptable esters, solvates, hydrates, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms or free form and/or a combination thereof. Cefixime can be in monohydrate, dihydrate or trihydrate form before granulation. Cefuroxime can be in the form of its pharmaceutically acceptable esters, solvates, hydrates, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms or free form and/or a combination thereof. Preferably, cefuroxime axetil is used.
  • Cefaclor can be in the form of its pharmaceutically acceptable esters, solvates, hydrates, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms or free form and/or a combination thereof.
  • Ceftibuten can be in the form of its pharmaceutically acceptable esters, solvates, hydrates, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphousforms or free form and/or a combination thereof. Ceftibuten can be in monohydrate, dihydrate or trihydrate form before granulation.
  • Cefprozil can be in the form of its pharmaceutically acceptable esters, solvates, hydrates, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms or free form and/or a combination thereof.
  • Cefetamet can be in the form of its pharmaceutically acceptable esters, solvates, hydrates, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms or free form and/or a combination thereof.
  • cefetamet pivoxil is used.
  • formulations produced according to the process of the present invention comprise preferably cefdinir, cefixime, ceftibuten and cefetamet pivoxil.
  • the disintegrant that can be used in the pharmaceutical formulation prepared by the process according to the present invention can be selected from a group comprising carboxymethyl cellulose calcium, carboxymethyl cellulose sodium, microcrystalline cellulose, silicone dioxide, croscarmellose sodium, crospovidone, hydroxypropyl cellulose, methylcellulose, povidone, magnesium aluminum silicate and starch or combinations thereof.
  • Carboxymethyl cellulose calcium is preferably used as disintegrant.
  • the diluent that can be used in the pharmaceutical formulation prepared by the process according to the present invention can be selected from a group comprising calcium carbonate, calcium sulphate, dibasic calcium phosphate, tribasic calcium phosphate, calcium sulphate, microcrystalline cellulose, lactose, magnesium carbonate, magnesium oxide, maltodextrin, maltose, mannitol, sodium chloride, sorbitol, starch and xylitol or combinations thereof. Microcrystalline cellulose is preferably used as diluent.
  • the diluent and the disintegrant composition that is used for preparation of the granules (a) can be the same as or different from the other diluent and the disintegrant composition used in (b). Preferably the same disintegrant and diluent compositions are used in both steps.
  • present invention relates to a process for preparing the formulation comprising a cephalosporin antibiotic and other excipients wherein said formulation consists of (a) granules comprising cephalosporin antibiotic and microcrystalline cellulose and carboxymethyl cellulose calcium composition and (b) an other microcrystalline cellulose and carboxymethyl cellulose calcium composition and at least one other pharmaceutically acceptable excipient and the process is characterized in that the granules comprising cephalosporin antibiotic, microcrystalline cellulose and carboxymethyl cellulose calcium are mixed with the other microcrystalline cellulose and carboxymethyl cellulose calcium composition wherein the other microcrystalline cellulose and carboxymethyl cellulose calcium composition is in an amount of 96-100% by weight in proportion to the amount of microcrystalline cellulose and carboxymethyl cellulose calcium composition that was used for obtaining the granules and wherein a tablet compression force in the range of 5-200 kN, preferably 10-150 kN, more preferably 20-100 kN is applied.
  • the pharmaceutical formulation prepared by the process according to the present invention can further comprise various excipients such as binders, sweeteners, lubricants, effervescent couples, glidants along with the active agent, diluents and disintegrants.
  • excipients such as binders, sweeteners, lubricants, effervescent couples, glidants along with the active agent, diluents and disintegrants.
  • the binder that can be used in the pharmaceutical formulation prepared by the process according to the present invention can be selected from a group comprising ethyl cellulose, gelatine, hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, hypromellose, magnesium aluminum silicate, methylcellulose, polyvinylpyrrolidone.
  • the lubricant that can be used in the pharmaceutical formulation prepared by the process according to the present invention can be selected from a group comprising calcium stearate, magnesium stearate, polyethylene glycol, PEG 6000, polyvinyl alcohol, potassium benzoate and sodium benzoate.
  • the glidant that can be used in the pharmaceutical formulation prepared by the process according to the present invention can be selected from a group comprising magnesium silicate, silicone dioxide, starch, talc, tribasic calcium phosphate or the combination thereof.
  • the sweetener that can be used in the pharmaceutical formulation prepared by the process according to the present invention can be selected from a group comprising acesulfame, aspartame, dextrose, fructose, glucose, lactitol, maltitol, maltose, sorbitol, saccharine, saccharine sodium, sodium cyclamate, sucralose, sodium chloride, potassium chloride, sucrose, xylitol or combinations thereof.
  • the effervescent couple that can be used in the pharmaceutical formulation prepared by the process according to the present invention can be selected from organic acids such as citric acid, tartaric acid, malic acid, fumaric acid etc. and from basic agents such as sodium hydrogen carbonate, sodium carbonate, potassium carbonate and potassium hydrogen carbonate etc.
  • the pharmaceutical formulation prepared by the process according to the present invention can be in various dosage forms, for instance; tablet, film-coated tablet, effervescent tablet, orodispersible tablet, prolonged-release tablet, modified-release tablet.
  • these formulations comprising the granules of the present invention are in the form of tablet or film- coated tablet.
  • the pharmaceutical formulation prepared by the process according to the present invention can comprise 1-4000 mg cephalosporin or its pharmaceutically acceptable salts, hydrates, solvates or a combination thereof in an equivalent amount.
  • the pharmaceutical formulation prepared by the process according to the present invention can further comprise an active agent along with the said granules and the excipients specified above.
  • the second active substance can be selected from cephalosporins or beta-lactamases.
  • clavulanic acid is used or derivatives thereof.
  • the clavulanic acid that can be used optionally in the pharmaceutical formulation prepared by the process can be in the form of its solvates, hydrates, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms or in free form and/or the combination thereof.
  • potassium clavulanate is used.
  • said formulation prepared by the process can comprise clavulanic acid in the range of 50-500 mg or its pharmaceutically acceptable salts, hydrates, solvates or a combination thereof in an equivalent amount.
  • Clavulanic acid and its derivatives e.g. potassium clavulanate
  • potassium clavulanate is preferably used with a humectant in the ratio of 1 :1 in the pharmaceutical formulation prepared by the process of the present invention.
  • colloidal silica for instance colloidal silica anhydrous, for instance silicondioxide, magnesium trisilicate, cellulose powder, fumed silicamagnesium oxide, calcium silicate, amorphous silica, starch, microcrystalline cellulose, talc can be used as the humectant.
  • potassium clavulanate is preferably used with amorphous silica in the ratio of 1 : 1.
  • the pharmaceutical formulation prepared by the process according to the present invention comprises 50-75% of cephalosporin or its pharmaceutically acceptable solvates, hydrates, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms, and 2-8% binder; 2-8% lubricant; 1-4% sweetener; 2-20% diluent; 8-14% disintegrant; 0-85% effervescent couple; 2-4% glidant; 0-90% clavulanic acid or an equivalent amount of its pharmaceutically acceptable salts, hydrates, solvates or the combination thereof in proportion to the total weight of unit dose amount.
  • the process pertaining to the present invention is composed of the following steps;
  • Granulation solution is prepared by dissolving the binder in water
  • Cephalosporin, diluent and disintegrant are granulated with the granulation solution prepared
  • step III Granules obtained in step III are sieved
  • Granules are blended with diluent, disintegrant, glidant and optionally the second active agent and effervescent couple,
  • the pharmaceutical composition obtained is stored in a required dosage form. It is compressed in tablet form and optionally packed with commercially available coating agents by using the techniques in the prior art.
  • the granules are sieved with a sieve, mesh size of which is in the range of 0,5-5 mm, preferably in the range of 1-3 mm.
  • the pharmaceutical composition prepared by the process according to the present invention can be used in treatment of upper respiratory infections, such as otorhinolaryngological infections, otitis media, sinusitis, tonsillitis, pharyngitis; lower respiratory tract infections, such as pneumonia, acute bronchitis and acute exacerbation of acute bronchitis; genitourinary infections, such as pyelonephritis, cystitis, urethritis; skin and soft tissue infections, such as furuncle, pyoderma, impetigo; and such diseases as community-acquired pneumonia, acute maxillary sinus infection.
  • upper respiratory infections such as otorhinolaryngological infections, otitis media, sinusitis, tonsillitis, pharyngitis
  • lower respiratory tract infections such as pneumonia, acute bron
  • Example 1 Formulation and process for preparation of film-coated tablet comprising cefdinir.
  • Cefdinir is mixed with a part of the diluent and a part of the disintegrant and granulated with the granulation solution composed of aqueous solution of the binder. Obtained granules are dried at 40 °C and sieved with a 1-3 mm mesh sieve. Said granules are mixed withglidant, and the diluent and disintegrant composition which is 96-100% by weight in proportion to the amount of diluent and disintegrant used for obtaining granules,. Then lubricant is added and the mixture is mixed again. Obtained mixture is loaded into tablet compression machine and then tablets are coated with an appropriate coating agent.
  • Example 2 Formulation and process for preparation of tablet comprising cefdinir and potassium clavulanate.
  • Cefdinir is mixed with a part of the diluent and a part of the disintegrant and granulated with the granulation solution composed of aqueous solution of the binder. Obtained granules are dried at 40 °C and sieved with a 1-3 mm mesh sieve. Said granules are mixed with glidant, the diluent and disintegrant composition which is 96-100% by weight in proportion to the amount of diluent and disintegrant used for obtaining granules. Then lubricant is added and the mixture is mixed again. Obtained mixture is loaded into tablet compression machine and then tablets are coated with the coating agent.
  • Example 3 Formulation and process for preparation of tablet comprising cefixime.
  • Cefixime is mixed with a part of the diluent and a part of the disintegrant and granulated with the granulation solution composed of aqueous solution of the binder. Obtained granules are dried at 40 °C and sieved with a 1-3 mm mesh sieve. Said granules are mixed with glidant and the diluent and disintegrant composition which is 96-100% by weight in proportion to the amount of diluent and disintegrant used for obtaining granules. Then lubricant is added and the mixture is mixed again. Obtained mixture is loaded into tablet compression machine and and pressed to form tablets.
  • Example 4 Formulation and process for preparation of tablet comprising ceftibuten.
  • Ceftibuten is mixed with a part of the diluent and a part of the disintegrant and granulated with the granulation solution composed of aqueous solution of the binder. Obtained granules are dried at 40 °C and sieved with a 1-3 mm mesh sieve. Said granules are mixed with glidant, sweetenerand the diluent and disintegrant composition which is 96-100% by weight in proportion to the amount of diluent and disintegrant used for obtaining granules. Then lubricant is added and the mixture is mixed again. Obtained mixture is loaded into tablet compression machine and and pressed to form tablets.
  • Example 5 Formulation and process for preparation of tablet comprising cefetamet pivoxil.
  • Cefetamet pivoxil is mixed with a part of the diluent and a part of the disintegrant and granulated with the granulation solution composed of aqueous solution of the binder. Obtained granules are dried at 40 °C and sieved with a 1-3 mm mesh sieve. Said granules are mixed with glidant, sweetenerand the diluent and disintegrant composition which is 96-100% by weight in proportion to the amount of diluent and disintegrant used for obtaining granules. Then lubricant is added and the mixture is mixed again. Obtained mixture is loaded into tablet compression machine and pressed to form tablets.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

L'invention concerne un procédé de préparation de formulations pharmaceutiques comprenant un antibiotique du type céphalosporine en tant que principe actif.
PCT/TR2011/000250 2010-11-05 2011-11-03 Procédé de production de formulations comprenant de la céphalosporine Ceased WO2012060785A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR2010/09167 2010-11-05
TR2010/09167A TR201009167A2 (tr) 2010-11-05 2010-11-05 Sefalosporin içeren farmasötik granüller.

Publications (1)

Publication Number Publication Date
WO2012060785A1 true WO2012060785A1 (fr) 2012-05-10

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Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/TR2011/000253 Ceased WO2012060788A1 (fr) 2010-11-05 2011-11-03 Formulations de céphalosporines avec teneur en humidité contrôlée
PCT/TR2011/000250 Ceased WO2012060785A1 (fr) 2010-11-05 2011-11-03 Procédé de production de formulations comprenant de la céphalosporine

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Application Number Title Priority Date Filing Date
PCT/TR2011/000253 Ceased WO2012060788A1 (fr) 2010-11-05 2011-11-03 Formulations de céphalosporines avec teneur en humidité contrôlée

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TR (1) TR201009167A2 (fr)
WO (2) WO2012060788A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013109227A1 (fr) * 2012-01-18 2013-07-25 Mahmut Bilgic Compositions pharmaceutiques contenant du ceftibutène
WO2013109203A1 (fr) * 2012-01-18 2013-07-25 Mahmut Bilgic Formulations en comprimés comprenant du cefditoren pivoxil
CN105168147A (zh) * 2015-09-11 2015-12-23 青岛蓝盛洋医药生物科技有限责任公司 一种治疗细菌感染的药物盐酸头孢他美酯组合物颗粒剂
WO2018071810A1 (fr) * 2016-10-13 2018-04-19 RhinoNase, Inc. Compositions antibiotiques pour irrigation nasale et procédés
CN108743548A (zh) * 2018-06-28 2018-11-06 苏州中联化学制药有限公司 一种头孢丙烯颗粒剂及其制备方法
US10624899B2 (en) 2016-07-14 2020-04-21 Achaogen, Inc. Combination products for the treatment of bacterial infections and methods of producing or dosing of same

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103405387B (zh) * 2013-08-13 2015-11-04 江苏正大清江制药有限公司 一种新的头孢克肟干混悬剂及其制备方法

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EP0281200A1 (fr) * 1987-03-02 1988-09-07 Yamanouchi Europe B.V. Composition pharmaceutique, granulé pharmaceutique et leur procédé de fabrication
CA2393614A1 (fr) * 2002-07-19 2002-10-28 Abbott Laboratories Compositions antibacteriennes de clarithromycine et processus de preparation connexe
WO2004006917A1 (fr) * 2002-07-16 2004-01-22 Ranbaxy Laboratories Limited Comprimes dispersibles pour administration par voie orale
WO2005115347A1 (fr) * 2004-05-31 2005-12-08 Sam-A Pharmaceuticals Co., Ltd. Comprime dispersible comprenant des antibiotiques beta-lactame et procede de preparation dudit comprime
WO2007058397A1 (fr) * 2005-11-17 2007-05-24 Gl Pharmtech Corp. Comprime dispersible comportant le melange d'amoxicilline et d'acide clavulanique ou ses sels et son procede de preparation

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EP1883393A2 (fr) * 2005-05-05 2008-02-06 Lupin Ltd. Compositions pharmaceutiques stabilisees de cephalosporines
EP2575781A1 (fr) * 2010-06-03 2013-04-10 Mahmut Bilgic Méthode de production de formulation effervescente comprenant du céphalosporine et du clavulanate de potassium

Patent Citations (5)

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EP0281200A1 (fr) * 1987-03-02 1988-09-07 Yamanouchi Europe B.V. Composition pharmaceutique, granulé pharmaceutique et leur procédé de fabrication
WO2004006917A1 (fr) * 2002-07-16 2004-01-22 Ranbaxy Laboratories Limited Comprimes dispersibles pour administration par voie orale
CA2393614A1 (fr) * 2002-07-19 2002-10-28 Abbott Laboratories Compositions antibacteriennes de clarithromycine et processus de preparation connexe
WO2005115347A1 (fr) * 2004-05-31 2005-12-08 Sam-A Pharmaceuticals Co., Ltd. Comprime dispersible comprenant des antibiotiques beta-lactame et procede de preparation dudit comprime
WO2007058397A1 (fr) * 2005-11-17 2007-05-24 Gl Pharmtech Corp. Comprime dispersible comportant le melange d'amoxicilline et d'acide clavulanique ou ses sels et son procede de preparation

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013109227A1 (fr) * 2012-01-18 2013-07-25 Mahmut Bilgic Compositions pharmaceutiques contenant du ceftibutène
WO2013109225A1 (fr) * 2012-01-18 2013-07-25 Mahmut Bilgic Formulations pharmaceutiques en comprimés comprenant du ceftibutène
WO2013109203A1 (fr) * 2012-01-18 2013-07-25 Mahmut Bilgic Formulations en comprimés comprenant du cefditoren pivoxil
CN105168147A (zh) * 2015-09-11 2015-12-23 青岛蓝盛洋医药生物科技有限责任公司 一种治疗细菌感染的药物盐酸头孢他美酯组合物颗粒剂
US10624899B2 (en) 2016-07-14 2020-04-21 Achaogen, Inc. Combination products for the treatment of bacterial infections and methods of producing or dosing of same
WO2018071810A1 (fr) * 2016-10-13 2018-04-19 RhinoNase, Inc. Compositions antibiotiques pour irrigation nasale et procédés
US10420776B2 (en) 2016-10-13 2019-09-24 RhinoNase, Inc. Antibiotic compositions for nasal irrigation and methods
US10849909B2 (en) 2016-10-13 2020-12-01 RhinoNase, Inc. Antibiotic compositions for nasal irrigation and methods
CN108743548A (zh) * 2018-06-28 2018-11-06 苏州中联化学制药有限公司 一种头孢丙烯颗粒剂及其制备方法

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Publication number Publication date
WO2012060788A1 (fr) 2012-05-10
TR201009167A2 (tr) 2012-05-21

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