WO2013095315A1 - Préparations comprenant du dexkétoprofène (taille de particules 300-2500 micromètres) - Google Patents

Préparations comprenant du dexkétoprofène (taille de particules 300-2500 micromètres) Download PDF

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Publication number
WO2013095315A1
WO2013095315A1 PCT/TR2012/000219 TR2012000219W WO2013095315A1 WO 2013095315 A1 WO2013095315 A1 WO 2013095315A1 TR 2012000219 W TR2012000219 W TR 2012000219W WO 2013095315 A1 WO2013095315 A1 WO 2013095315A1
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WO
WIPO (PCT)
Prior art keywords
dexketoprofen
granules
active agent
excipient
optionally
Prior art date
Application number
PCT/TR2012/000219
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English (en)
Inventor
Mahmut Bilgic
Original Assignee
Mahmut Bilgic
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 Mahmut Bilgic filed Critical Mahmut Bilgic
Publication of WO2013095315A1 publication Critical patent/WO2013095315A1/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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • 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
    • A61K9/0002—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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • the present invention relates to pharmaceutical formulations comprising dexketoprofen that shall be used as antipyretic, analgesic, anti-inflammatory in treatment of mild and moderate pains such as toothache, menstrual pain, post-surgical pain, musculoskeletal pain.
  • dexketoprofen was first disclosed in the application numbered EP0668851. In said document, it has been disclosed that dexketoprofen is effective when used as antipyretic, analgesic, antiinflammatory in treatment of mild and moderate pain such as toothache, menstrual pain, postsurgical pain, musculoskeletal pain.
  • Dexketoprofen is available in forms of 50 mg/2ml solution for injection, 25 mg film coated tablet and 25 mg effervescent tablet on the market.
  • the present invention relates to pharmaceutical formulations comprising dexketoprofen and methods for preparation of these formulations.
  • the formulations which comprise granules comprising dexketoprofen, at least one excipient and optionally a second active agent and 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 formed into any solid dosage form; relative standard deviation remains low, a homogeneous pharmaceutical composition is obtained, weight and content uniformity are provided by preventing weight changes.
  • the subject of the present invention is the granules which comprise dexketoprofen, at least one excipient and optionally a second active agent and have 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 ⁇ during preparation of formulations comprising dexketoprofen.
  • average particle size refers to volumetric average particle size and it is also shown with d 50 in short.
  • d 50 signifies that half of the said substance by volume has a particle size over the value stated with d 5 o and the other half of the substance by volume has a particle size below the value stated with d 50 .
  • D 0 value can be measured with one of the known measuring devices, for instance with a device which measures particle distribution by laser diffraction (for instance, Malvern Mastersizer etc.).
  • the present invention relates to a process that shall be used in production of the granules which have 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 ⁇ and comprise dexketoprofen, at least one excipient and optionally a second active agent characterized in that the 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
  • the pharmaceutical formulation of the present invention can be obtained by a method comprising:
  • the pharmaceutical formulation is formulated in effervescent tablet form, it is obtained by a method comprising the following steps:
  • a granulation solution is prepared with binder, deionized water and ethyl alcohol, II.
  • Effervescent acid is mixed with the effervescent base, binder and the sweetener, III.
  • the mixture obtained in step II is firstly granulated with the granulation solution obtained in step I and then with ethyl alcohol,
  • step III The granules obtained in step III are dried and an amount in the range of 1-15% of said dried granules is set apart,
  • step V The active agent dexketoprofen is added into the remaining dry granules obtained in step IV and mixed, and then the dry granules set apart are added into this mixture,
  • step V when the active agent dexketoprofen is added into the remaining amount of the granules obtained in step IV and 1-15% of the dried granules is added into this mixture, the inventors have observed that a more homogeneous mixture is obtained and the obtained effervescent formulations can disperse more rapidly.
  • the present invention relates to a process that the active agent dexketoprofen is added into the remaining amount of the granules obtained in step IV and then 1-15% of the dried granules, which is set apart, is added into this mixture in step V.
  • drying temperature and moisture content of the granules obtained are important for obtaining optimum values of hardness, fragility and stability of the granules obtained during preparation of the formulations comprising dexketoprofen and the end product in solid form prepared with the said granules and therefore important for preventing possible problems that can be encountered during quality control and using phases.
  • the inventors surprisingly have seen that the granules obtained according to the process of the present invention as dried at 10-120°C, preferably at 20-100°C and more preferably at 25-70°C present proper flow property and the solid forms prepared with these granules have desired hardness and fragility.
  • another aspect of the present invention relates to drying the granules comprising dexketoprofen, at least one excipient and optionally a second active agent at a temperature in the range of 10-120°C, preferably at a temperature in the range of 20-100°C and more preferably at a temperature in the range of 25-70°C in preparation of the formulations comprising dexketoprofen.
  • a second active agent at a temperature in the range of 10-120°C, preferably at a temperature in the range of 20-100°C and more preferably at a temperature in the range of 25-70°C in preparation of the formulations comprising dexketoprofen.
  • another aspect of the present invention relates to drying the granules comprising dexketoprofen, at least one excipient and optionally a second active agent in the manner that they have moisture content less than 1% by weight, preferably in the range of 0.1-0.9% by weight in preparation of the formulations comprising dexketoprofen.
  • Dexketoprofen comprised in the pharmaceutical formulations prepared according to the process of the present invention is in the form of its pharmaceutically acceptable salts, hydrates, solvates, esters, enantiomers, diastereomers or combinations thereof in terms of chemical structure; it is in amorphous form or crystalline form or a combination thereof in terms of polymorphic structure.
  • Dexketoprofen is preferably in salt form, more preferably in dexketoprofen trometamol form.
  • the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen can be prepared in any solid dosage form such as tablet, effervescent tablet, effervescent granule, effervescent dry powder, film coated tablet, enteric coated tablet, dry powder, granule, capsule, prolonged release tablet, modified release tablet, delayed release tablet.
  • the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen are preferably in powder, tablet and granule forms, more preferably in film coated tablet or effervescent tablet forms.
  • the pharmaceutical formulation obtained according to the present invention can be formed into any abovementioned dosage forms.
  • the formulation is in tablet form
  • the tablets obtained can be treated with film coating agents for instance sugar based coating agents, water soluble film coating agents, enteric coating agents, delayed release coating agents or coating compositions comprising any combination thereof.
  • Saccharose can be used singly or optionally with any of the agents such as talc, calcium carbonate, calcium phosphate, calcium sulphate, gelatine, gum arabic, polyvinylpyrrolidone and pullulan or a combination thereof as the sugar based coating agent.
  • agents such as talc, calcium carbonate, calcium phosphate, calcium sulphate, gelatine, gum arabic, polyvinylpyrrolidone and pullulan or a combination thereof as the sugar based coating agent.
  • the 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 aminoacetate, 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 aminoacetate, aminoalkyl methacrylate copolymers and polyvinylpyrrolidone and polysaccharides such as pullulan or combinations thereof.
  • the enteric coating agents can be selected from cellulose derivatives such as hydroxypropyl methyl cellulose phthalate, hydroxypropyl methyl cellulose acetate succinate, carboxymethyl ethyl cellulose, cellulose acetate phthalate; 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 phthalate, hydroxypropyl methyl cellulose acetate succinate, carboxymethyl ethyl cellulose, cellulose acetate phthalate
  • 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.
  • the delayed release coating agents can be selected from cellulose derivatives such as ethyl cellulose; acrylic acid derivatives such as aminoalkyl methacrylate copolymer RS, emulsion copolymer of ethyl acrylate-methyl methacrylate or combinations thereof.
  • compositions prepared according to the process of the present invention and comprising dexketoprofen can comprise various excipients in addition to the active agent dexketoprofen.
  • the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen comprise at least one excipient selected from a group comprising disintegrant, diluent, lubricant, glidant, binder, effervescent couple comprising at least one acidic agent and at least 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 dexketoprofen and the lubricant.
  • excipient selected from a group comprising disintegrant, diluent, lubricant, glidant, binder, effervescent couple comprising at least one acidic agent and at least 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 dexketoprofen and the lubricant.
  • the disintegrant that can be used in the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen 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 the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen 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 the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen can be selected from a group comprising tribasic calcium phosphate, colloidal silicone dioxide, magnesium silicate, magnesium trisilicate, talc.
  • the binder that can be used in the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen can be selected from a group comprising carboxymethyl cellulose sodium, ethyl cellulose, gelatine, hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, hypromellose, magnesium aluminium silicate, maltodextrin, methyl cellulose, povidone, starch.
  • the acidic agent composing the effervescent couple comprising at least one acidic agent and at least one basic agent that can be used in the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen can be selected from a group comprising organic acids such as malic acid, citric acid, tartaric acid, fumaric acid; and the basic agent composing the effervescent couple comprising at least one acidic agent and at least one basic agent that can be used in the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen can be 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 the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen can be selected from citrate, phosphate, carbonate, tartrate, fumarate, acetate and amino acid salts.
  • the surfactant that can be used in the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen can be selected from sodium lauryl sulphate, polysorbate, polyoxyethylene, polyoxypropylene glycol and similar agents.
  • the stabilizing agent that can be used in the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen can be selected from a group comprising tocopherol, tetrasodium edetate, nicotinamide, cyclodextrin.
  • the sweetener and/or taste regulating agent that can be used in the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen 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.
  • the flavouring agent that can be used in the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen can be selected from menthol, lemon, orange, vanilla, strawberry, raspberry, caramel and similar flavours.
  • the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen can comprise dexketoprofen in the range of 0.1 to 99.9 % by weight, preferably in the range of 1 to 99% by weight, more preferably in the range of 5 to 95% by weight.
  • the pharmaceutical formulations prepared according to the process of the present invention and comprising dexketoprofen can optionally comprise a second active agent in addition to dexketoprofen.
  • the second active agent can be selected from antacid, anticholinergic, antispasmodic, antiemetic, antidiabetic, antipropulsive, antiallergic, antidiarrheal, antiobesity, antithrombotic, antifibrinolytic, antianemic, antihypertensive, antifungal, antipruritic, antipsoriatic, antibiotic, antiseptic, antiacne, antibacterial, antimycotic, antiviral, antineoplastic, antiarrhythmic, antiadrenergic, antiepileptic, anti-parkinson, antiprotozoal, anthelmintic, anti-inflammatory, diuretic, laxative, sulphonamide, imidazole, corticosteroid, thiazolidinedione, biguanide, immunosti
  • the pharmaceutical formulations prepared according to the process of the present invention and comprising a second active agent in addition to dexketoprofen 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, the pharmaceutical formulations prepared according to the process of the present invention and comprising a second active agent in addition to dexketoprofen can be prepared in dosage forms such as layered tablet, capsule; in the case that the two active agents are in different formulations and dosage forms, the pharmaceutical formulations prepared according to the process of the present invention and comprising a second active agent in addition to dexketoprofen can be prepared in treatment package form comprising a combination of solid dosage forms such as tablet, effervescent tablet,
  • the pharmaceutical formulation of the present invention can be used as antipyretic, analgesic, anti-inflammatory in treatment of mild and moderate pain such as toothache, menstrual pain, post-surgical pain, musculoskeletal pain.
  • EXAMPLE The effervescent tablets comprising dexketoprofen and preparation method thereof
  • a granulation solution is prepared by mixing ethyl alcohol, the binder and purified water.
  • the effervescent acid, the effervescent base and the taste regulating agent are mixed and granulated with the granulation solution prepared.
  • the obtained granules are dried and sieved.
  • the sweetener and dexketoprofen mixture is added into the granules dried and sieved, then the mixture is stirred.
  • the mixture obtained is mixed again after the flavouring agent and the lubricant are added and the final mixture is compressed in tablet form.

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Medicinal Preparation (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)

Abstract

La présente invention concerne la réalisation de préparations pharmaceutiques contenant du dexkétoprofène qui s'utilise en tant qu'analgésique, antipyrétique ou anti-inflammatoire dans le traitement de la douleur légère ou modérée de type de mal de dents, de douleur menstruelle ou post-opératoire ou de douleur musculo-squelettique. La réalisation de préparations pharmaceutiques, de préférence d'une préparation effervescente, contenant du dexkétoprofène est caractérisée en ce que les granulés contenant du dexkétoprofène, au moins un excipient et éventuellement un deuxième agent actif sont criblés ou moulus de manière à ce avoir une taille moyenne de particules comprise entre 300 et 2500 micromètres, ces granulés étant séchés et mélangés à un excipient au moins. Une préparation préférée est une préparation effervescente de dexkétoprofène.
PCT/TR2012/000219 2011-12-19 2012-12-19 Préparations comprenant du dexkétoprofène (taille de particules 300-2500 micromètres) WO2013095315A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR2011/12581 2011-12-19
TR201112581 2011-12-19

Publications (1)

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WO2013095315A1 true WO2013095315A1 (fr) 2013-06-27

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019212426A3 (fr) * 2017-12-29 2019-11-28 Neutec Ar-Ge Sanayi Ve Ticaret Anonim Şirketi Composition de dexkétoprofène à libération retardée

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0668851A1 (fr) 1992-11-10 1995-08-30 Menarini Lab Nouveau derive arylpropionique, procede d'elaboration de ce derive et son utilisation comme agent analgesique.
WO2001041733A2 (fr) * 1999-12-09 2001-06-14 The Boots Company Plc Agents therapeutiques
CN101623280A (zh) * 2008-07-10 2010-01-13 广东肇庆星湖生物科技股份有限公司 一种镇痛的复方缓释制剂及其制备方法
US20100204259A1 (en) * 2009-02-06 2010-08-12 Egalet A/S Immediate release composition resistant to abuse by intake of alcohol
WO2012158127A2 (fr) * 2011-05-18 2012-11-22 Mahmut Bilgic Formulations solubles dans l'eau comprenant du dexketoprofène

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0668851A1 (fr) 1992-11-10 1995-08-30 Menarini Lab Nouveau derive arylpropionique, procede d'elaboration de ce derive et son utilisation comme agent analgesique.
WO2001041733A2 (fr) * 1999-12-09 2001-06-14 The Boots Company Plc Agents therapeutiques
CN101623280A (zh) * 2008-07-10 2010-01-13 广东肇庆星湖生物科技股份有限公司 一种镇痛的复方缓释制剂及其制备方法
US20100204259A1 (en) * 2009-02-06 2010-08-12 Egalet A/S Immediate release composition resistant to abuse by intake of alcohol
WO2012158127A2 (fr) * 2011-05-18 2012-11-22 Mahmut Bilgic Formulations solubles dans l'eau comprenant du dexketoprofène

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ANONYMOUS: "DEXMOL", INTERNET CITATION, 20 December 2010 (2010-12-20), XP055042987, Retrieved from the Internet <URL:http://www.iegm.gov.tr/Folders/KubKT/Yeni ilaç Sube Müdürlügü/2010.12.20_Dexmol 25 mg KUB_209e441.pdf> [retrieved on 20121102] *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019212426A3 (fr) * 2017-12-29 2019-11-28 Neutec Ar-Ge Sanayi Ve Ticaret Anonim Şirketi Composition de dexkétoprofène à libération retardée

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