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WO2013095313A1 - Formulations pharmaceutiques comprenant du cefdinir - Google Patents

Formulations pharmaceutiques comprenant du cefdinir Download PDF

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Publication number
WO2013095313A1
WO2013095313A1 PCT/TR2012/000217 TR2012000217W WO2013095313A1 WO 2013095313 A1 WO2013095313 A1 WO 2013095313A1 TR 2012000217 W TR2012000217 W TR 2012000217W WO 2013095313 A1 WO2013095313 A1 WO 2013095313A1
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WO
WIPO (PCT)
Prior art keywords
cefdinir
granules
excipient
active agent
optionally
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/TR2012/000217
Other languages
English (en)
Inventor
Mahmut Bilgic
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of WO2013095313A1 publication Critical patent/WO2013095313A1/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
    • A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
    • A61K9/0007—Effervescent
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1611—Inorganic compounds
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1617—Organic compounds, e.g. phospholipids, fats
    • 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
    • A61K9/2009—Inorganic compounds
    • 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

Definitions

  • the present invention relates to pharmaceutical formulations comprising cefdinir so as to be used in treatment of a number of diseases caused by gram positive and gram negative bacteria.
  • Cefdinir was first disclosed in the application numbered BE897864. It has been disclosed in said document that cefdinir is effective in treatment of a number of diseases caused by gram positive and gram negative bacteria.
  • Cefdinir is found in capsule and suspension form on the market.
  • formulation composition does not have a proper flow due to the reasons that free flow of the obtained granules cannot be enabled and/or friction between granule particles cannot be reduced; therefore, homogeneity cannot be provided in the obtained pharmaceutical composition and the composition loses its homogeneity during the processes. Therefore, during the conversion of formulations into any solid dosage form, said issues cause changes in weight of the final product and increase in relative standard deviation values. Weight and content uniformity in the final product cannot be ensured due to the deviations observed in the weight of final product and failure to provide homogeneity of the formulation. Thus, said points pose problems to producers in production and quality control processes and at the same time, patients cannot take same amounts of drug during the treatment because of weight and content uniformity loss observed in the dosage forms obtained; therefore, efficiency of the treatment decreases.
  • the present invention relates to pharmaceutical formulations comprising cefdinir and methods for preparation of said formulations.
  • formulations in which the average particle size of the granules comprising cefdinir, at least one excipient and optionally a second active agent is in the range of 300-2500 ⁇ , preferably in the range of 350-2000 ⁇ , more preferably in the range of 500-1750 ⁇ are converted into any solid dosage form; it has surprisingly been observed that relative standard deviation value remains low; a homogeneous pharmaceutical composition is obtained; weight and content uniformity are ensured by preventing the changes in weight.
  • average particle size of the granules comprising cefdinir, at least one excipient and optionally a second active agent is in the range of 300-2500 ⁇ , preferably in the range of 350-2000 ⁇ , more preferably in the range of 500-1750 ⁇ during the preparation of formulations comprising cefdinir.
  • average particle size refers to volumetric average particle diameter and is indicated by d 50 in short.
  • d 50 means that half of the said substance by volume has a particle size above the value stated with d 50 and the other half has a particle size below the value stated with d 5 o.
  • D 50 value can be measured by one of the known measurement devices such as a device measuring the particle distribution with laser diffraction (for example; Malvern Mastersizer etc).
  • the present invention relates to a process that will be used in production of granules having an average particle size in the range of 300-2500 ⁇ , preferably in the range of 350-2000 ⁇ , more preferably in the range of 500-1750 ⁇ which comprise cefdinir, at least one excipient and optionally a second active agent characterized in that said granules having an average particle size in the range of 300-2500 ⁇ , preferably in the range of 350- 2000 ⁇ , more preferably in the range of 500-1750 ⁇ are obtained by;
  • Grinding process is performed by the effect of rolling blades within the device in the case that blade mill is used.
  • Grinding process is performed by the effect of rolling hammers within the device in the case that impact mill is used.
  • Grinding process is performed by making the particles collide with each other with the help of compressed and high speed air stream in the case that jet mill is used.
  • composition of the invention can be obtained by a method comprising the steps of;
  • the inventors have observed the relative standard deviation of the weight by changing the average particle size values of the granules in order to find out the effect of the average particle size values of the granules sieved after the granulation and drying processes on weight changes of the solid dosage form obtained and therefore their effect on weight uniformity. Accordingly, average particle size values of the granules obtained after the sieving process and therefore their relative standard deviation values (RSD %) are given in Table 1. As seen in the table, it is observed that RSD % values of the obtained granules are about 2% or below in the case that their average particle sizes are in the range of 300-2500 ⁇ , preferably in the range of 500-2000 ⁇ .
  • granules which are obtained by drying the granules at a temperature in the range of 10-120°C, preferably in the range of 20-100°C and more preferably in the range of 25-70°C according to the process of the invention have proper flow characteristics and the solid forms prepared from said granules have the desired hardness and brittleness.
  • the present invention relates to drying the granules comprising cefdinir, at least one excipient and optionally a second active agent at a temperature in the range of 10-120°C, preferably in the range of 20-100°C and more preferably in the range of 25-70°C during the preparation of formulations comprising cefdinir.
  • the present invention relates to drying the granules comprising cefdinir, at least one excipient and optionally a second active agent such that they have a moisture content less than 1%, preferably in the range of 0.1 to 0.9% during the preparation of formulations comprising cefdinir.
  • Cefdinir comprised in the pharmaceutical formulations prepared according to the process of the present invention can be in form of its pharmaceutically acceptable salts, hydrates, solvates, esters, enantiomers, diastereomers or combinations thereof in terms of chemical structure.
  • polymorphic structure it can be in amorphous or crystalline form or a combination thereof.
  • compositions comprising cefdinir and prepared according to the process of the present invention can be prepared in any solid dosage form such as tablet, effervescent tablet, effervescent granule, effervescent dry powder, film coated tablet, enterically coated tablet, dry powder, granule, capsule, prolonged release tablet, modified release tablet, delayed release tablet.
  • solid dosage form such as tablet, effervescent tablet, effervescent granule, effervescent dry powder, film coated tablet, enterically coated tablet, dry powder, granule, capsule, prolonged release tablet, modified release tablet, delayed release tablet.
  • compositions comprising cefdinir and prepared according to the process of the present invention are preferably in water-soluble powder, tablet and granule form, more preferably in effervescent tablet, effervescent granule or effervescent dry powder form.
  • Pharmaceutical formulation obtained according to the invention can be prepared in any dosage form mentioned above. In the case that it is in tablet form, obtained tablets can be treated with film coating agents such as sugar-based coating agents, water-soluble film coating agents, enteric coating agents, delayed release coating agents or coating compositions comprising a combination thereof.
  • saccharose can be used alone or optionally together with any of the agents such as talc, calcium carbonate, calcium phosphate, calcium sulphate, gelatine, gum arabic, polyvinylpyrrolidone and pullulan or any combination thereof.
  • agents such as talc, calcium carbonate, calcium phosphate, calcium sulphate, gelatine, gum arabic, polyvinylpyrrolidone and pullulan or any combination thereof.
  • Water-soluble film coating agent can be selected from cellulose derivatives such as hydroxypropyl cellulose, hydroxypropyl methyl cellulose, hydroxyethyl cellulose, methyl hydroxyethyl cellulose and sodium carboxymethyl cellulose; synthetic polymers such as polyvinyl acetal diethyl amino acetate, aminoalkyl methacrylate copolymers and polyvinylpyrrolidone; and polysaccharides such as pullulan or combinations thereof.
  • cellulose derivatives such as hydroxypropyl cellulose, hydroxypropyl methyl cellulose, hydroxyethyl cellulose, methyl hydroxyethyl cellulose and sodium carboxymethyl cellulose
  • synthetic polymers such as polyvinyl acetal diethyl amino acetate, aminoalkyl methacrylate copolymers and polyvinylpyrrolidone
  • polysaccharides such as pullulan or combinations thereof.
  • Enteric-coating agents can be selected from cellulose derivatives such as hydroxypropyl methyl cellulose ftalat, hydroxypropyl methyl cellulose acetate succinate, carboxymethyl ethyl cellulose, cellulose acetate ftalat; acrylic acid derivatives such as methacrylic acid copolymer L, methacrylic acid copolymer LD and methacrylic acid copolymer S; and natural substances such as shellac or combinations thereof.
  • cellulose derivatives such as hydroxypropyl methyl cellulose ftalat, hydroxypropyl methyl cellulose acetate succinate, carboxymethyl ethyl cellulose, cellulose acetate ftalat
  • acrylic acid derivatives such as methacrylic acid copolymer L, methacrylic acid copolymer LD and methacrylic acid copolymer S
  • natural substances such as shellac or combinations thereof.
  • Delayed release coating agents can be selected from cellulose derivatives such as ethyl cellulose; acrylic acid derivatives such as aminoalkyl methacrylate copolymer RS, ethyl acrylate-methyl methacrylate copolymer emulsion or combinations thereof.
  • compositions comprising cefdinir and prepared according to the process of the present invention can comprise various excipients together with the active agent cefdinir.
  • excipient selected from a group comprising disintegrant, diluent, lubricant, glidant, binder, effervescent couple comprising at least one acidic and one basic agent, colouring agent, pH regulating agent, surfactant, stabilizing agent, sweetener and/or taste regulating agent, flavouring agent in addition to the active agent cefdinir.
  • the disintegrant that can be used in pharmaceutical formulations comprising cefdinir and prepared according to the process of the invention can be selected from a group comprising carboxymethyl cellulose, carboxymethyl cellulose calcium, carboxymethyl cellulose sodium, croscarmellose sodium, crospovidone, hydroxypropyl cellulose, microcrystalline cellulose, methyl cellulose, chitosan, starch, sodium starch glycolate.
  • the diluent that can be used in pharmaceutical formulations comprising cefdinir and prepared according to the process of the invention can be selected from a group comprising calcium carbonate, dibasic calcium phosphate, tribasic calcium phosphate, calcium sulphate, microcrystalline cellulose, dextrose, fructose, lactitol, lactose, magnesium carbonate, magnesium oxide, maltitol, maltodextrin, maltose, mannitol, simethicone, sorbitol, starch, sodium chloride, sucrose, talc, xylitol.
  • the glidant that can be used in pharmaceutical formulations comprising cefdinir and prepared according to the process of the invention can be selected from a group comprising tribasic calcium phosphate, colloidal silicone dioxide, magnesium silicate, talc.
  • the binder that can be used in pharmaceutical formulations comprising cefdinir and prepared according to the process of the invention can be selected from a group comprising carboxymethyl cellulose sodium, ethyl cellulose, gelatine, hydroxyethyl cellulose, hydroxymethyl cellulose sodium, hydroxypropyl cellulose, hypromellose, magnesium aluminium silicate, maltodextrin, methyl cellulose, povidone, starch.
  • the acidic agent constituting the effervescent couple comprising at least one acidic and one basic agent that can be used in the pharmaceutical formulations comprising cefdinir and prepared according to the process of the invention can be selected from a group comprising organic acids such as malic acid, citric acid, tartaric acid, fumaric acid; and the basic agent is selected from a group comprising agents such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate.
  • the pH regulating agent that can be used in pharmaceutical formulations comprising cefdinir and prepared according to the process of the invention can be selected from a group comprising citrate, phosphate, carbonate, tartrate, fumarate, acetate and amino acid salts.
  • the surfactant that can be used in pharmaceutical formulations comprising cefdinir and prepared according to the process of the invention can be selected from a group comprising agents such as sodium lauryl sulphate, polysorbate, polyoxyethylene, polyoxypropylene glycol and so forth.
  • the stabilizing agent that can be used in pharmaceutical formulations comprising cefdinir and prepared according to the process of the invention can be selected from a group comprising tocopherol, tetrasodium edetate, nicotinamide, cyclodextrin.
  • the sweetener and/or taste regulating agent that can be used in pharmaceutical formulations comprising cefdinir and prepared according to the process of the invention can be selected from a group comprising acesulfame, aspartame, dextrose, fructose, maltitol, maltose, mannitol, saccharine, saccharine sodium, sodium cyclamate, sorbitol, sucralose, sucrose, xylitol, sodium chloride.
  • flavouring agent that can be used in pharmaceutical formulations comprising cefdinir and prepared according to the process of the invention can be selected from flavors such as menthol, lemon, orange, vanillin, strawberry, raspberry, caramel and so forth.
  • compositions comprising cefdinir and prepared according to the process of the invention can comprise cefdinir in the range of 0.1 to 99.9%, preferably in the range of 1 to 99%, more preferably in the range of 5 to 95% by weight.
  • compositions comprising cefdinir and prepared according to the process of the invention can optionally comprise a second excipient in addition to cefdinir.
  • the second active agent can be selected from a group comprising antacid, anticholinergic, antispasmodic, antiemetic, anti-diabetic, antipropulsive, antiallergic, antidiarrheal, antiobesity, antithrombotic, antifibrinolytic, antianaemic, antihypertensive, antifungal, antipruritic, antipsoriatic, antibiotic, antiseptic, antiacne, antibacterial, antimycotic, antiviral, antineoplastic, antiaritmic, antiadrenergic, antiepileptic, anti-Parkinson, antiprotozoal, antihelminthic, anti-inflammatory, diuretic, laxative, sulphonamide, imidazole, corticosteroid, tiazolidinedion, biguanide
  • pharmaceutical formulations comprising clavulanic acid together with cefdinir and prepared according to the process of the present invention can be prepared in any solid dosage form such as tablet, effervescent tablet, effervescent granule, effervescent dry powder, film coated tablet, enterically coated tablet, dry powder, granule, capsule, prolonged release tablet, modified release tablet, delayed release tablet; in the case that the two active agents are in different formulations but in the same dosage form, said formulations can be prepared in dosage forms such as layered tablet, capsule; in the case that the two active agents are in different formulations and different dosage forms, said formulations can be prepared in form of a treatment package comprising any combination of solid dosage forms such as tablet, effervescent tablet, effervescent granule, effervescent dry powder, film coated tablet, enterically coated tablet, dry powder, granule, capsule, prolonged release tablet, modified release tablet, delayed release tablet or in form of capsule comprising micro tablet and
  • the pharmaceutical formulation of the invention can be used in treatment of a number of diseases caused by gram positive and gram negative bacteria.
  • effervescent base, effervescent acid, sweetener, binder and cefdinir are granulated with water or an aqueous solution; obtained granules are dried; sieved such that their average particle size is 700 ⁇ and following this; lubricant, colouring agent, sweetening agent and flavouring agent are added to the mixture and stirred; the mixture is compressed in tablet form.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne des formulations pharmaceutiques comprenant du cefdinir, destinées à être utilisées dans le traitement d'un certain nombre de maladies provoquées par des bactéries à Gram positif ou à Gram négatif; et les procédés de préparation desdites formulations.
PCT/TR2012/000217 2011-12-19 2012-12-17 Formulations pharmaceutiques comprenant du cefdinir Ceased WO2013095313A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR201112584 2011-12-19
TR2011/12584 2011-12-19

Publications (1)

Publication Number Publication Date
WO2013095313A1 true WO2013095313A1 (fr) 2013-06-27

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ID=47748743

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/TR2012/000217 Ceased WO2013095313A1 (fr) 2011-12-19 2012-12-17 Formulations pharmaceutiques comprenant du cefdinir

Country Status (1)

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WO (1) WO2013095313A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE897864A (fr) 1982-09-30 1984-03-29 Fujisawa Pharmaceutical Co Procede de production de composes de 3-vinyl-3-cephem 7-substitues et nouveaux produits ainsi obtenus
WO1998002145A2 (fr) * 1996-07-16 1998-01-22 Gist-Brocades B.V. GRANULES DE β-LACTAME SANS SOLVANTS ORGANIQUES
CN1706389A (zh) * 2005-05-26 2005-12-14 济南平志医药科技有限公司 头孢地尼泡腾制剂及其制备方法
WO2011078822A1 (fr) * 2009-12-25 2011-06-30 Mahmut Bilgic Compositions pharmaceutiques comprenant cefdinir comme principe
WO2011093821A1 (fr) * 2010-01-29 2011-08-04 Mahmut Bilgic Formulations effervescentes comprenant du cefdinir et de l'acide clavulanique
WO2012060791A2 (fr) * 2010-11-05 2012-05-10 Mahmut Bilgic Procédé de production de compositions pharmaceutiques comprenant du cefdinir

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE897864A (fr) 1982-09-30 1984-03-29 Fujisawa Pharmaceutical Co Procede de production de composes de 3-vinyl-3-cephem 7-substitues et nouveaux produits ainsi obtenus
WO1998002145A2 (fr) * 1996-07-16 1998-01-22 Gist-Brocades B.V. GRANULES DE β-LACTAME SANS SOLVANTS ORGANIQUES
CN1706389A (zh) * 2005-05-26 2005-12-14 济南平志医药科技有限公司 头孢地尼泡腾制剂及其制备方法
WO2011078822A1 (fr) * 2009-12-25 2011-06-30 Mahmut Bilgic Compositions pharmaceutiques comprenant cefdinir comme principe
WO2011093821A1 (fr) * 2010-01-29 2011-08-04 Mahmut Bilgic Formulations effervescentes comprenant du cefdinir et de l'acide clavulanique
WO2012060791A2 (fr) * 2010-11-05 2012-05-10 Mahmut Bilgic Procédé de production de compositions pharmaceutiques comprenant du cefdinir

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