WO2015022559A1 - Composition pharmaceutique contenant de la rosuvastatine et du ramipril - Google Patents

Composition pharmaceutique contenant de la rosuvastatine et du ramipril Download PDF

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Publication number
WO2015022559A1
WO2015022559A1 PCT/HU2014/000071 HU2014000071W WO2015022559A1 WO 2015022559 A1 WO2015022559 A1 WO 2015022559A1 HU 2014000071 W HU2014000071 W HU 2014000071W WO 2015022559 A1 WO2015022559 A1 WO 2015022559A1
Authority
WO
WIPO (PCT)
Prior art keywords
ramipril
pharmaceutical composition
ram
rosuvastatin
granulate
Prior art date
Application number
PCT/HU2014/000071
Other languages
English (en)
Inventor
Katalin Baranek
György UJFALUSSY
András FEHÉR
Zsolt Zsigmond
Ádám ORBÁN
Original Assignee
Egis Gyógyszergyár Zrt.
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 Egis Gyógyszergyár Zrt. filed Critical Egis Gyógyszergyár Zrt.
Publication of WO2015022559A1 publication Critical patent/WO2015022559A1/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
    • A61K9/20—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
    • A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
    • A61K9/209—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat containing drug in at least two layers or in the core and in at least one outer layer
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4808—Preparations in capsules, e.g. of gelatin, of chocolate characterised by the form of the capsule or the structure of the filling; Capsules containing small tablets; Capsules with outer layer for immediate drug release
    • 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
    • A61K9/5047—Cellulose ethers containing no ester groups, e.g. hydroxypropyl methylcellulose
    • 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
    • A61K9/5084—Mixtures of one or more drugs in different galenical forms, at least one of which being granules, microcapsules or (coated) microparticles according to A61K9/16 or A61K9/50, e.g. for obtaining a specific release pattern or for combining different drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives

Definitions

  • the invention concerns a wide range of pharmaceutical compositions.
  • the technical field of the invention is the combination composition containing several active ingredient in one dosage form.
  • the invention can be grouped into the combination compositions containing ramipril.
  • Ramipril, (2S, 3aS, 6aS) -1 [ (S) -N- [ (S) -l-carboxy-3- phenylpropyl ] -alanyl-octahydrocyclopenta- [b] pyrrole-2-carboxylic acid-ethlyester, is a known drug active ingredient, which is used in the therapy to treat hypertension, heart failure, nephropathy, to promote revascularisation, to decrease the risk of cardiovascular diseases and events, especially stroke and myocardial infarction, and to decrease cardiovascular mortality.
  • the active ingredient ramipril is sensitive to heat and moisture and decomposes easily. During the decomposition the hydrolysis of the ester groups occurs, which results the impurity corresponding to the active metabolite, that is the ramiprilate (European Pharmacopoeia: Impurity E) .
  • the concentration of the decomposition product diketopiperazine in the product can reach 22.8%, in case of ramipril capsules filled with powder mixture containing 2.5 mg of active ingredient can reach 6.4%, respectively.
  • the oxidative decomposition of ramipril in the presence of air can result in undesired discoloration.
  • Rosuvastatin is the selective and competitive inhibitor of
  • Rosuvastatin is used for medical purposes in the form of its pharmaceutically acceptable salts, primarily as the calcium salt or as the zinc salt. Rosuvastatin is an active ingredient of Class III of the Biopharmaceutics Classification System (BCS) , which has a high solubility in water and in body fluids.
  • BCS Biopharmaceutics Classification System
  • Amlodipine is hard to tablet and easily decomposes. Amlodipine is used in pharmaceutical compositions in the form of benzenesulfonic acid salt, i.e. amlodipine besylate. It is known from the international publication No. WO2010038091 that in combination compositions amlodipine easily interacts undesirably with the second active ingredient, which leads to decomposition reactions. Due to the hydrolysis of amlodipine besylate in the presence of moisture it is expected that mixing it directly with ramipril the fast decomposition of ramipril will occur in the resulting acidic medium.
  • Chinese patent application No. CN101658675 describes several combination compositions, however, does not describe the stability and release features of the compositions. Furthermore, the patent application neither describes the drug formulation containing ramipril and rosuvastatin simultaneously.
  • the object of our invention is therefore to develop a drug formulation containing ramipril, which applied in a unit dose combination eliminates the incompatibility occurring between ramipril and rosuvastatin described above.
  • the mixture of 10 - 50 m/m% of ramipril and 50 - 90 m/m% of the diluent calculated to the weight of the coated granules is dry compacted during the dry granulation.
  • the step of the wet granulation fluidization granulation or vortex granulation can preferably be used.
  • 1 - 10 m/m% binder is used calculated to the weight of the coated granules.
  • ramipril granules according to the invention are produced according to the following process:
  • the diluent is preferably crospovidone
  • the binder is preferably hypromellose .
  • a further object of the invention is the ramipril granule prepared by any of the above described processes.
  • the ramipril granule according to the invention preferably contains crosslinked PVP and/or HPMC.
  • a further object of the invention is a pharmaceutical composition containing ramipril granules according to the invention .
  • a further object of the invention is a pharmaceutical composition containing ramipril granules according to the invention and rosuvastatin .
  • the pharmaceutical composition according to the invention contains also amlodipine.
  • a further object of the present invention is the pharmaceutical use of the pharmaceutical composition of the invention, especially for the treatment of hypertension and to decrease high cholesterol level.
  • the active ingredients remain stable during manufacture and storage, i.e. in the composition, or the level of impurities formed during the manufacture does not exceed the level of the approved impurities relating to the given active ingredient of the mono-composition,
  • bioavailability of the combination composition shall be similar or identical to the one, if two or three mono- compositions are administered together, which correspond to the active ingredient content of the combination composition,
  • the aimed compositions with similar effect and that are preferably bioequivalent are suitable for - in case of already treated patients - switching without risk the simultaneous administration of two or three compositions to the combination composition.
  • This has a particular importance in the treatment of patients with hypertension, because setting the blood pressure by using different active ingredients generally needs longer time, and there is a risk that the effect of the new combination does not reach the required level.
  • the drug search- setting process can last for even months, while the side effects (dizziness, headache, etc.) caused by the hypertension significantly decrease the life quality of the patient, and formation and/or progression of the accompanying diseases are not inhibited.
  • the combination composition is bioequivalent, than the long process of the setting and the risks can be avoided.
  • release profiles do not change during storage time, as a composition with altered release profile can not exert the same effect. Namely, if the release profile of any of the active ingredients changes, the bioavailability can also deviate, and the composition will not be suitable either to replace the corresponding mono-compositions or to use it as a drug.
  • Our invention is therefore a solid combination pharmaceutical composition containing ramipril and rosuvastatin and optionally amlodipine or pharmaceutically acceptable salts or complexes thereof.
  • the coated ramipril containing granulate by the following method:
  • disintegrant is preferably crosslinked polyvinylpyrrolidone (e.g. polyplasdone XL 10) is dry-compacted, and compacts are regranulated and coated by 5-10%, preferably 5-8% aqueous solution of 1-15 m/m%, preferably 1-10 m/m%, more preferably 2-6 m/m% HPMC calculated to the weight of the coated granule.
  • crosslinked polyvinylpyrrolidone e.g. polyplasdone XL 10
  • compacts are regranulated and coated by 5-10%, preferably 5-8% aqueous solution of 1-15 m/m%, preferably 1-10 m/m%, more preferably 2-6 m/m% HPMC calculated to the weight of the coated granule.
  • ramipril and crosslinked polyvinylpyrrolidone (PVP), preferably polyplasdon XL 10
  • PVP polyvinylpyrrolidone
  • the obtained compact is subjected to regranulation on a sieve of 0.6 mm, than on 0.5 mm hole size and afterwards homogenized.
  • the obtained homogenized granulate is coated with an aqueous solution of 6 m/m% HPMC in a fluidization granulation apparatus.
  • the resulting coated granules are optionally homogenized with part of the microcrystalline cellulose used for the outer phase, and afterwards the rest of the microcrystalline cellulose and aerosil R972 is added to the obtained mixture.
  • compritol 888 glyceryl behenate
  • Amlodipine besylate (AMD 12 VT) 13.900 mg
  • Preparation of the granulate is made by a two-step granulation, first dry granulation (compaction) , than wet granulation occurs.
  • first dry granulation (compaction)
  • wet granulation occurs.
  • the necessary amount of active ingredient and additive is mixed, sieved, homogenized followed by compaction by a dry granulation apparatus, than regranulation and homogenization occurs, and the further granulation follows in a fluidization granulation apparatus by spraying the granulation solution.
  • the material with an appropriate drying loss is preferably homogenized after regranulation .
  • the active ingredient rosuvastatin is sensitive to light, therefore the strong lighting during the whole manufacturing process shall be avoided.
  • the preferably sieved magnesium stearate of vegetable origin is added during the manufacturing process to materials of the prehomogenized internal phase (Rosuvastatin Ca compact and Prosolv HD 90) , than the press-ready end-homogenizate is prepared by end-homogenization, which can preferably be tableted in a rotary tablet press.
  • the flow diagram of the preparation of the combination composition is the following:
  • Preparation of the amlodipine compact occurs preferably by multiple steps of mixing, sieving, regranulation and homogenization of amlodipine besylate (AMD 12 VT) and Vivapur 200
  • amlodipine is used in the combination composition, than preferably the prepared amlodipine granulate is mixed with the Ramipril granulate and further agents (Aerosil R 972, Vivapur 200), homogenized, and after the addition of Compritol 888 the end-homogenizate is prepared by homogenization.
  • the end- homogenizate containing the Ramipril and optionally Amlodipine is filled into the capsule shells, and as the second step Rosuvastatin Ca tbl 20 mg (0.02 M) is filled onto the homogenizate .

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  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La présente invention concerne une composition combinée contenant de la rosuvastatine et du ramipril, et éventuellement de l'amlodipine, et la préparation de cette composition. Les principes actifs sont séparés l'un de l'autre dans ladite composition.
PCT/HU2014/000071 2013-08-16 2014-08-15 Composition pharmaceutique contenant de la rosuvastatine et du ramipril WO2015022559A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HUP1300496 2013-08-16
HU1300496A HUP1300496A2 (hu) 2013-08-16 2013-08-16 Stabil kombinációs gyógyszerkészítmény

Publications (1)

Publication Number Publication Date
WO2015022559A1 true WO2015022559A1 (fr) 2015-02-19

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Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/HU2014/000071 WO2015022559A1 (fr) 2013-08-16 2014-08-15 Composition pharmaceutique contenant de la rosuvastatine et du ramipril
PCT/HU2014/000072 WO2015022560A1 (fr) 2013-08-16 2014-08-15 Composition pharmaceutique stable contenant du bisoprolol et du ramipril

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/HU2014/000072 WO2015022560A1 (fr) 2013-08-16 2014-08-15 Composition pharmaceutique stable contenant du bisoprolol et du ramipril

Country Status (3)

Country Link
EA (1) EA033291B1 (fr)
HU (2) HUP1300496A2 (fr)
WO (2) WO2015022559A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3501502A1 (fr) * 2017-12-20 2019-06-26 Midas Pharma GmbH Compositions pharmaceutiques dosées fixes comprenant de l'amlodipine, du ramipril et de l'atorvastatine

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021160700A1 (fr) 2020-02-10 2021-08-19 Adamed Pharma S.A. Composition comprenant du ramipril et de l'indapamide
CN115068434B (zh) * 2022-08-03 2023-05-09 昆山龙灯瑞迪制药有限公司 一种雷米普利片的制备方法

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WO2003092729A1 (fr) * 2002-05-03 2003-11-13 Hexal Ag Formulation pharmaceutique stable contenant une statine combinee avec un inhibiteur de l'ace
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WO2010038091A2 (fr) 2008-09-30 2010-04-08 Egis Gyógyszergyár Nyilvánosan Működő Részvénytársaság Composition pharmaceutique a combinaison stable
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WO2010038091A2 (fr) 2008-09-30 2010-04-08 Egis Gyógyszergyár Nyilvánosan Működő Részvénytársaság Composition pharmaceutique a combinaison stable
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WO2013121233A1 (fr) 2012-02-17 2013-08-22 Egis Gyógyszergyár Nyilvánosan Működö Részvénytársaság Formule pharmaceutique à stabilité améliorée

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3501502A1 (fr) * 2017-12-20 2019-06-26 Midas Pharma GmbH Compositions pharmaceutiques dosées fixes comprenant de l'amlodipine, du ramipril et de l'atorvastatine
WO2019121857A1 (fr) * 2017-12-20 2019-06-27 Midas Pharma GmbH Compositions pharmaceutiques à doses fixes comprenant de l'amlodipine, du ramipril et de l'atorvastatine

Also Published As

Publication number Publication date
HU231052B1 (hu) 2020-02-28
WO2015022560A1 (fr) 2015-02-19
HUP1600414A2 (hu) 2016-09-28
EA033291B1 (ru) 2019-09-30
EA201690395A1 (ru) 2016-07-29
HUP1300496A2 (hu) 2015-03-02
WO2015022560A8 (fr) 2015-05-14

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