WO2013122554A1 - Formulations de pastilles comprenant de l'ésoméprazole - Google Patents

Formulations de pastilles comprenant de l'ésoméprazole Download PDF

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Publication number
WO2013122554A1
WO2013122554A1 PCT/TR2013/000060 TR2013000060W WO2013122554A1 WO 2013122554 A1 WO2013122554 A1 WO 2013122554A1 TR 2013000060 W TR2013000060 W TR 2013000060W WO 2013122554 A1 WO2013122554 A1 WO 2013122554A1
Authority
WO
WIPO (PCT)
Prior art keywords
active agent
esomeprazole
pellet
enterically coated
formulations
Prior art date
Application number
PCT/TR2013/000060
Other languages
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 WO2013122554A1 publication Critical patent/WO2013122554A1/fr

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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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
    • A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5015—Organic compounds, e.g. fats, sugars
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
    • A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants

Definitions

  • the present invention relates to highly stable, new esomeprazole pellet formulations.
  • the present invention further relates to enterically coated pellet formulation of esomeprazole.
  • Hydrogen potassium ATPase (H + /K + ATPase) enzymes provide stomach acidity.
  • the activity of H7K + ATPase enzymes should be blocked in order to regularize acidity in the stomach in the diseases such as dyspepsia, peptic ulcer and gastroesophageal reflux (GERD).
  • H 2 - receptor antagonists or proton pump inhibitors (PPIs) are used for this blockage.
  • H 2 - receptor antagonists prevent signal pathway activating ATPase and proton pump inhibitors block ATPase.
  • Esomeprazole one of the most used PPIs, is not durable to acidic medium and it degrades immediately. However, it is stable in alkaline mediums. Esomeprazole is indicated for treatment of gastroesophageal reflux disease (GERD), erosive reflux oesophagitis; for prevention of relapses, for long-term maintenance treatment of healed reflux oesophagitis and for symptomatic treatment of gastroesophageal reflux disease. Together with a suitable antibiotic combination, it is indicated for helicobacter pylori eradication and for treatment of helicobacter pylori induced duodenal ulcers and for prevention of relapses in helicobacter pylori induced peptic ulcers.
  • GSD gastroesophageal reflux disease
  • erosive reflux oesophagitis erosive reflux oesophagitis
  • helicobacter pylori eradication and for treatment of helicobacter pylori induced du
  • NSAIDs non-steroidal anti-inflammatory drugs
  • Dose amount of esomeprazole in a tablet or a pellet is generally in the range of 20 to 40 mg. In the case that the treatment cannot be implemented by the oral route, parenteral treatment is implemented.
  • the basic problem concerning esomeprazole is that the active agent has low stability and it is not durable to acidic mediums such as stomach.
  • the prior art suggests various methods and formulations in order to solve this problem. These are generally to use acidic enteric coatings or inert intermediate layers or to mix them with the alkaline compounds.
  • the active agent is mixed with more than one alkaline metals in order to increase stability in the patent numbered WO0078293 Al .
  • an enteric coating is not used on purpose and buffer agents are used in order to provide stability.
  • the enteric coating used in the enterically coated formulations in order for the active agent not to degrade due to gastric acid induces degradation of the active agent since it is acidic.
  • the active agent layer is general ly separated from the enteric coating by using at least one intermediate coating in the enterically coated formulations and degradation of the active agent is prevented.
  • the active agent is applied to an inert core and said core is coated with an isolating layer comprising mannitol in the patent application numbered WO2012/017074. This intermediate layer prevents degradation of the active agent due to the interaction between the agents comprised in the enteric coating.
  • the patent application numbered EP1235555 discloses pellet formulations comprising a benzimidazole (particularly omeprazole) which is susceptible to acids.
  • the pellets of the invention are composed of a) an inert core, b) a benzimidazole layer coating said core, c) one or more inert coatings and d) an enteric coating layer.
  • the benzimidazole layer (b) comprised in the formulation given in said patent comprises hydroxypropyl methylcellulose.
  • the inventors have achieved to solve this problem with the new pellet formulations and by the production method developed in the scope of the present invention.
  • the present invention relates to easily producible highly stable, new esomeprazole pellet formulations.
  • the formulations according to present invention are composed of a) an inert core, b) an active agent layer coating the core, c) an intermediate coating comprising sucrose and at least one other intermediate coating layer and d) an enteric coating layer.
  • a characteristic feature of the pellet formulations of the present invention is that said formulations comprise a) an inert core, b) an active agent layer coating the core and comprising minimum 5% mannitol by weight and at least one other excipient in addition to the active agent,
  • a characteristic feature of the pellet formulations of the present invention is that said formulations are composed of a) an inert core,
  • a characteristic feature of the pellet formulations of the present invention is that said formulations are composed of a) an inert core,
  • an intermediate coating comprising sucrose and at least one other intermediate coating and d) an enteric coating layer.
  • the formulations of the present invention can preserve their stability longer than the formulations usually comprising a cellulose derivative diluent (for instance hydroxypropyl cellulose) in the prior art thanks to the use of minimum 5% mannitol by weight in the active agent layer.
  • a cellulose derivative diluent for instance hydroxypropyl cellulose
  • the fluidity characteristics of the pellets formulated this way are affected positively.
  • the final dosage form after pellet production can be easily prepared thanks to the improvement in the fluidity characteristics of the pellet formulations prepared this way.
  • a characteristic feature of the esomeprazole pellet formulations of the present invention is that said formulations can comprise a non-cellulose derivative diluent, preferably mannitol. Esomeprazole formulations of the present invention can comprise at least one other diluent in addition to mannitol.
  • the coating which covers the active agent layer and comprises sucrose has improved formulation stability in the formulations of the present invention.
  • pellet formulations according to the present invention can optionally be compressed in tablet form or can be presented after filled into capsules.
  • enterically coated esomeprazoie pellet formulations to be prepared according to the present invention comprise at least one other excipient in addition to the active agent and mannitol.
  • the pharmaceutically acceptable excipients that can be used in the enterically coated esomeprazoie pellet formulations to be prepared in accordance with the production method of the present invention can be selected from a group comprising disintegrant, diluent, lubricant, glidant, binder, colouring agent, pH regulating agent, surfactant, sweetener and/or taste regulating agent and/or flavouring agent.
  • excipients that can be comprised in the formulations of the present invention can be selected from a group comprising diluent, buffer agent, binder or combinations thereof.
  • the inert core that can be used in the formulations of the present invention is used in order to carry the active agent and it is selected from a group comprising lactose, sugar, starch, modified starch, mannitol, sorbitol, inorganic salts, microcrystalline cellulose, cellulose, calcium sulphate, xylitol and lactitol.
  • the other diluents that can be used in addition to mannitol in the enterically coated esomeprazoie pellet formulations of the present invention can be selected from a group comprising calcium carbonate, dibasic calcium phosphate, tribasic calcium phosphate, calcium sulphate, dextrose, fructose, lactitol, lactose, magnesium carbonate, magnesium oxide, mannitol, maltodextrin, maltose, simethicone, sorbitol, starch, sodium chloride, sucrose, talc.
  • the other diluent preferred is sucrose.
  • the binders that can be used in the enterically coated esomeprazoie pellet formulations of the present invention can be selected from starches such as potato starch, corn starch, wheat starch; sugars such as sucrose, glucose, dextrose, lactose, maltodextrin; natural and synthetic gums; gelatine; cellulose derivatives such as microcrystalline cellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, hydroxypropyl methyl cellulose, carboxymethyl cellulose, methyl cellulose, ethyl cellulose; polyvinylpyrrolidone (povidone); polyethylene glycol (PEG); waxes; calcium carbonate; calcium phosphate; alcohols such as dibasic calcium phosphate, sorbitol, xylitol, mannitol and water or a combination thereof.
  • starches such as potato starch, corn starch, wheat starch
  • sugars such as sucrose, glucose, dextrose, lactose, mal
  • sodium bicarbonate, potassium bicarbonate, magnesium hydroxide, magnesium lactate, magnesium glucomate, aluminium hydroxide, sodium citrate, sodium tartrate, sodium acetate, sodium carbonate, sodium polyphosphate, potassium polyphosphate, sodium pyrophosphate, potassium pyrophosphate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, trisodium phosphate, tripotassium phosphate, potassium metaphosphate, magnesium oxide, magnesium hydroxide, magnesium carbonate, magnesium silicate, calcium acetate, calcium glycerophosphate, calcium chloride, calcium carbonate, calcium hydroxide and other calcium salts or combinations thereof can be used in the enterically coated esomeprazole pellet formulations of the present invention.
  • the base coating agents that can be used in the enterically coated esomeprazole pellet formulations of the present invention are selected from a group comprising hydroxypropyl methylcellulose (HPMC), hydroxypropyl cellulose (HPC), polyvinylpyrrolidone (PVP), polyethylene glycol, methylcellulose, amylopectin or hydroxymethyl cellulose (MHC) or a combination thereof.
  • HPMC hydroxypropyl methylcellulose
  • HPC hydroxypropyl cellulose
  • PVP polyvinylpyrrolidone
  • MHC hydroxymethyl cellulose
  • the surfactants, binders and lubricants can be used in the base coating in the formulation in addition to the base coating agent.
  • the enteric coating agents can be selected from cellulose derivatives such as hydroxypropyl methyl cellulose phthalate, hydroxypropyl methylcellulose 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 a combination thereof.
  • the enteric coating used in the formulation can comprise at least one other pharmaceutically acceptable excipient such as surfactants, plasticisers, emulsion agents, colouring agents, binders, disintegrants, lubricants, solvents in addition to the enteric coating agent.
  • excipients that can be comprised in the active agent layer of the enterically coated esomeprazole pellet formulations according to the present invention can preferably be at least one buffer agent, at least one diluent and at least one binder selected from the groups given above in addition to active agent and minimum 5% mannitol by weight.
  • pellet formulations of the present invention are preferably produced by the method given below: I. esomeprazole, mannitol and at least one other excipient are mixed (active agent mixture), II. the inert cores are wetted with the granulation solution,
  • the active agent mixture is added to wet inert cores in parts; it is continued to wet the mixture with the granulation solution during the adding process,
  • the pellets prepared are coated firstly with the base coating and then with the enteric coating layer.
  • the formulations of the present invention can optionally be used with another active agent or agents in combined form.
  • the dosage forms can be can be administered separately, together or sequentially; though they can also be taken by combining esomeprazole with the other active agent or agents in a single dosage form for combined therapy.
  • the other active agent or agents can be selected from dopamine antagonists such as acepromazine, amisulpride, amoxapine, azaperone, benperidol, bromopride, butaclamol, clomipramine, chlorpromazine, chlorprothixene, clopenthixol, domperidone, droperidol, eticlopride, flupentixol, fluspirilene, haloperidol, iodine benzamide, loxapine, mesoridazine, levomepromazine, metoclopramide, nafadotride, nemonapride, penfluridol, perazine, perphenazine, pimozide, prochlorperazine, promazine, raclopride, remoxipride, risperidone, spiperone, spiroxatrine, stepholidine, sulpride, sultop
  • One or two of the other active agents can be combined with esomeprazole in combined treatment.
  • the present invention comprises the binary and ternary combinations of esomeprazole with the other abovementioned active agents.
  • the other active agent or agents that can be used in combined treatment can be produced with esomeprazole by using the same production method while they can also be in a treatment package form prepared by formulating the active agent formulations separately, storing them in different dosage forms and combining the dosage forms prepared in a single dosage form.
  • the second active agent that can be used in the pellet formulations comprising esomeprazole to be used in treatment of gastroesophageal reflux disease (GERD), erosive reflux oesophagitis; for prevention of relapses, for long-term maintenance treatment of healed reflux oesophagitis and for symptomatic treatment of gastroesophageal reflux disease (GERD) and erosive reflux oesophagitis is preferably domperidone in the scope of the present invention.
  • the enterically coated pellet formulations of the present invention comprising the proton pump inhibitor esomeprozole are indicated for treatment of gastroesophageal reflux disease (GERD), erosive reflux oesophagitis; for prevention of relapses, for long-term maintenance treatment of healed reflux oesophagitis and for symptomatic treatment of gastroesophageal reflux disease.
  • GUD gastroesophageal reflux disease
  • erosive reflux oesophagitis for prevention of relapses, for long-term maintenance treatment of healed reflux oesophagitis and for symptomatic treatment of gastroesophageal reflux disease.
  • parenteral treatment is implemented.
  • helicobacter pylori eradication and for treatment of helicobacter pylori induced duodenal ulcers and for prevention of relapses in helicobacter pylori induced peptic ulcers.
  • NSAIDs non-steroidal anti-inflammatory drugs
  • Esomeprazole is used for treatment of gastro-intestinal ulcer and duodenal ulcer in Chorn disease.
  • Esomeparazole, mannitol and at least one other excipient are mixed (active agent mixture), b) The inert core is wetted with the granulation solution, c) The active agent mixture is added to wet inert cores in parts; it is continued to wet the mixture with the granulation solution during the adding process, d) After all the active agent mixture is added, the mixture is coated with sucrose and pelleting process is completed, e) The pellets prepared are coated firstly with the base coating and then the enteric coating layer.
  • Esomeprazole, mannitol and at least one other excipient are mixed (active agent mixture), b) The inert core is wetted with the granulation solution, c) The active agent mixture is added to wet inert cores in parts; it is continued to wet the mixture with the granulation solution during the adding process, d) After all the active agent mixture is added, the mixture prepared is coated with sucrose and pelleting process is completed, e) The pellets prepared are coated firstly with the base coating and then with the enteric coating layer.

Abstract

La présente invention se rapporte à des formulations pharmaceutiques stables comprenant de l'ésoméprazole et à leur procédé de production, ces formulations étant destinées à être utilisées dans le traitement de maladies induites par la sécrétion de l'acide gastrique.
PCT/TR2013/000060 2012-02-14 2013-02-14 Formulations de pastilles comprenant de l'ésoméprazole WO2013122554A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
TR2012/01599 2012-02-14
TR201201599 2012-02-14
TR2012/04301 2012-04-13
TR201204301 2012-04-13

Publications (1)

Publication Number Publication Date
WO2013122554A1 true WO2013122554A1 (fr) 2013-08-22

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10800738B2 (en) 2017-12-05 2020-10-13 Sunovion Pharmaceuticals Inc. Crystal forms and production methods thereof
US10874639B2 (en) 2017-12-05 2020-12-29 Sunovion Pharmaceuticals Inc. Nonracemic mixtures and uses thereof
US10946002B2 (en) * 2016-10-06 2021-03-16 Jubilant Generics Limited Pharmaceutical suspension dosage form of benzimidazole compounds and process of preparation thereof
US11160758B2 (en) 2019-06-04 2021-11-02 Sunovion Pharmaceuticals Inc. Modified release formulations and uses thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993025204A1 (fr) * 1992-06-16 1993-12-23 Ethypharm Compositions stables de microgranules d'omeprazole gastro-proteges et leur procede d'obtention
WO2000078293A1 (fr) 1999-06-22 2000-12-28 Astrazeneca Ab Nouvelle formulation
EP1235555A2 (fr) 1999-12-09 2002-09-04 Ratiopharm GmbH Preparations galeniques stables contenant un benzimidazole, et son procede de production
WO2005034924A1 (fr) * 2003-10-14 2005-04-21 Natco Pharma Limited Pastilles a enrobage enterique comprenant de l'esomeprazole, capsule de gelatine dure renfermant celles-ci et procede de preparation associe
EP1246622B1 (fr) 2000-01-11 2006-09-27 The Curators Of The University Of Missouri Nouvelles formes posologiques de benzimidazoles substitues
WO2012017074A1 (fr) 2010-08-06 2012-02-09 Valpharma S.P.A. Formulations pharmaceutiques orales d'ésoméprazole sous la forme de comprimés mups (multi unit pellets system)

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993025204A1 (fr) * 1992-06-16 1993-12-23 Ethypharm Compositions stables de microgranules d'omeprazole gastro-proteges et leur procede d'obtention
WO2000078293A1 (fr) 1999-06-22 2000-12-28 Astrazeneca Ab Nouvelle formulation
EP1235555A2 (fr) 1999-12-09 2002-09-04 Ratiopharm GmbH Preparations galeniques stables contenant un benzimidazole, et son procede de production
EP1246622B1 (fr) 2000-01-11 2006-09-27 The Curators Of The University Of Missouri Nouvelles formes posologiques de benzimidazoles substitues
WO2005034924A1 (fr) * 2003-10-14 2005-04-21 Natco Pharma Limited Pastilles a enrobage enterique comprenant de l'esomeprazole, capsule de gelatine dure renfermant celles-ci et procede de preparation associe
WO2012017074A1 (fr) 2010-08-06 2012-02-09 Valpharma S.P.A. Formulations pharmaceutiques orales d'ésoméprazole sous la forme de comprimés mups (multi unit pellets system)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10946002B2 (en) * 2016-10-06 2021-03-16 Jubilant Generics Limited Pharmaceutical suspension dosage form of benzimidazole compounds and process of preparation thereof
US10800738B2 (en) 2017-12-05 2020-10-13 Sunovion Pharmaceuticals Inc. Crystal forms and production methods thereof
US10874639B2 (en) 2017-12-05 2020-12-29 Sunovion Pharmaceuticals Inc. Nonracemic mixtures and uses thereof
US11370753B2 (en) 2017-12-05 2022-06-28 Sunovion Pharmaceuticals Inc. Crystal forms and production methods thereof
US11517558B2 (en) 2017-12-05 2022-12-06 Sunovion Pharmaceuticals Inc. Nonracemic mixtures and uses thereof
US11767293B2 (en) 2017-12-05 2023-09-26 Sunovion Pharmaceuticals Inc. Crystal forms and production methods thereof
US11160758B2 (en) 2019-06-04 2021-11-02 Sunovion Pharmaceuticals Inc. Modified release formulations and uses thereof
US11654113B2 (en) 2019-06-04 2023-05-23 Sunovion Pharmaceuticals Inc. Modified release formulations and uses thereof

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