EP2575757A1 - Formulation hydrosoluble stable - Google Patents

Formulation hydrosoluble stable

Info

Publication number
EP2575757A1
EP2575757A1 EP11745588.1A EP11745588A EP2575757A1 EP 2575757 A1 EP2575757 A1 EP 2575757A1 EP 11745588 A EP11745588 A EP 11745588A EP 2575757 A1 EP2575757 A1 EP 2575757A1
Authority
EP
European Patent Office
Prior art keywords
pharmaceutical composition
composition according
amlodipine
effervescent
acid
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.)
Withdrawn
Application number
EP11745588.1A
Other languages
German (de)
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 EP2575757A1 publication Critical patent/EP2575757A1/fr
Withdrawn legal-status Critical Current

Links

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
    • A61K31/33—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
    • 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
    • A61K31/4422—1,4-Dihydropyridines, e.g. nifedipine, nicardipine
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • 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

Definitions

  • the present invention relates to novel, stable and easily produceable water soluble pharmaceutical compositions of a combination of a calcium channel blocker and a 3-hydroxy- 3-methylglutaryl-coenzyme A reductase inhibitor.
  • Amlodipine (Formula I), chemical name of which is 3-ethyl 5-methyl (+/-)-2-[(2- aminoethoxy)methyl] -4-(o-chlorophenyl)- 1 ,4-dihydropyridine-6-methyl-3 ,5 - pyridinedicarboxylate, was disclosed in the patent numbered EP 0089167 in detail.
  • HMG-CoA reductase inhibitors competitively inhibit the activation of the enzyme named HMG-CoA reductase.
  • This enzyme is in HMG-CoA reductase pathway where it is used for cholesterol synthesis of the body.
  • Rosuvastatin, atorvastatin, cerivastatin, lovastatin, fluvastatin, mevastatin, pravastatin and pitavastatin are HMG-CoA reductase inhibitors, in other terms, statin group compounds.
  • Rosuvastatin having the chemical name (3i?,5S,6E)-7-[4-(4-fluorophenyl)-6-(l-methylethyl)- 2[methyl(methylsulphonyl)amino]-5-pyrimidinyl]-3,5-dihydroxy-6-heptenoic acid is a HMG CoA enzyme inhibitor which was first disclosed in the patent numbered US 5260440 is displayed in formula (II):
  • rosuvastatin inhibits the activation of the enzyme named HMG-CoA reductase that is responsible for cholesterol synthesis in the body and prevents cholesterol formation and it is effective in the treatment of cardiovascular diseases such as hypercholesterolemia, hyperlipoproteinemia and atherosclerosis.
  • Atorvastatin ⁇ Formula III which has the chemical name ( R, (Si?,)-2-(4-fluorophenyl)- ⁇ , ⁇ - dihydroxy-5 -( 1 -methylethyl)-3 -phenyl-4- [(phenylamino)carbanoyl] - 1 H-pyrrol- 1 -heptanoic acid is a HMG CoA reductase inhibitor.
  • Atorvastatin was first disclosed in the patent numbered EP 409281. There exist processes for preparation of atorvastatin and its use as cholesterol biosynthesis inhibitor in said patent.
  • Atorvastatin is a hypolipidemic drug which is a selective competitive inhibitor of HMG CoA reductase enzyme. It has the indication of lowering increased LDL cholesterol and triglyceride levels.
  • the product marketed under the trademark CADUET® comprises the combination of atorvastatin and amlodipine.
  • the product in tablet form is formulated in 5/10 mg, 5/20 mg, 10/10 mg and 10/20 mg doses of amlodipine/atorvastatin.
  • Rosuvastatin on the other hand, is marketed under the trademark Crestor®. Rosuvastatin in the composition formulated as film tablet is in calcium salt form.
  • formulations comprising amlodipine and statins separately or in combination are formulated in tablet form which is a solid dosage form.
  • one of the disadvantages of tablet dosage forms that they have lower bioavailability compared with suspension dosage forms.
  • the highest bioavailability can be obtained from oral solutions among all dosage forms.
  • dosage forms such as tablet and capsule leads to swallowing difficulties for some patients, especially for elderly and physically handicapped patients as they are difficult to be swallowed and have unpleasant taste even taken with liquids. In parallel with this, the patients do not take the drugs regularly and this substantially affects the efficiency of the treatment.
  • Use of solid dosage forms such as tablet or capsule poses problems in pediatric and geriatric patients, people having swallowing difficulties.
  • suspension forms may not be preferred since they have the possibility of high and/or uncontrolled dose intake; high manufacture costs; problems in physical and chemical stability; problems in use and carrying.
  • suspension forms have higher bioavailability values compared with solid dosage forms, they are more inconvenient in comparison to solid dosage forms in terms of stability and shelf life.
  • the inventors have surprisingly found new, user-friendly, therapeutically advantageous and stable water soluble powder, tablet and granule formulations comprising amlodipine and a statin group compound.
  • the characteristic feature of the present invention is that water soluble powder, tablet and granule formulations carry the advantages of both tablet and suspension forms together and eliminate the problems observed in these dosage forms.
  • the present invention relates to pharmaceutical formulations comprising therapeutically effective amounts of amlodipine and a statin group compound.
  • amlodipine can be in free form, in the form of a pharmaceutically acceptable salt, crystalline form, amorphous form, enantiomer, racemate, solvate, hydrate thereof.
  • amlodipine is in the form of a pharmaceutically acceptable salt thereof; preferably in besylate, mesylate or maleate salts form, more preferably in besylate salt form.
  • the statin group compound can be in free form, in the form of a pharmaceutically acceptable salt, crystalline form, amorphous form, enantiomer, racemates, solvate, hydrate thereof.
  • the statin group compound is preferably used in the form of a pharmaceutically salt thereof, more preferably in calcium salt form.
  • the characteristic feature of the formulation of the present invention is that said formulation is in powder, tablet or granule form.
  • water soluble powder, tablet and granule refers to effervescent tablets, effervescent granules, effervescent powders, water soluble powders, water soluble tablets, water soluble granules and sachet forms. It has been observed that the composition of the present invention provides a more effective use when said composition is formulated as effervescent formulations in the form of effervescent tablet, effervescent granule or effervescent powder. Medicament compositions comprising effervescent formulations suitable for single dose use provide ease of use for patients requiring special consideration.
  • Effervescent formulations disperse very fast; they rapidly and simultaneously release the active agent/agents into the aqueous liquid. At this point, effervescent tablet forms are more advantageous than solid dosage forms.
  • the time passing between the addition of the formulation into water and swallowing the obtained solution is relatively short. Consumption of the formulation in a short time impedes the degradation of the active agent with water.
  • pharmaceutical formulations in effervescent form are particularly preferred by patients in terms of ease of use and carrying.
  • the formulation disperses in aqueous liquid rapidly and it can be administered by the oral route, with a spoon or as a drop when necessary. Such formulations are more advantageous especially for elderly and physically handicapped patients.
  • the formulations of the present invention comprise amlodipine in a therapeutically effective amount, a statin group compound in a therapeutically effective amount and at least one excipient.
  • a solution which can easily be taken even by patients with swallowing difficulties is produced, owing to the fact that the composition of the present invention comprises an effervescent couple. Dissolution of the active agent rapidly and being taken as a solution enables to obtain the effect of the medicament relatively fast.
  • the term "effervescent couple” refers to use of an acidic agent and a basic agent together.
  • Said basic agent can be alkaline earth carbonate or alkaline earth bicarbonate. Earth alkaline carbonate/bicarbonate in the effervescent couple provides C0 2 production in the pharmaceutical composition.
  • Said acidic agent can be selected from organic and/or inorganic acids such as acetic acid, citric acid, lactic acid, malic acid, phosphoric acid, fumaric acid, propionic acid, tartaric acid; or their pharmaceutically acceptable salts, hydrates, anhydrates or a combination thereof.
  • the pharmaceutical composition is produced by dry granulation method.
  • amlodipine which is one of the active agents composing the composition of the present invention, is a quite hygroscopic compound. There observed degradation as it absorbs the humidity in its environment.
  • composition of the present invention comprises the following steps:
  • Step 1
  • statin group compound is subjected to wet granulation in the presence of at least one effervescent base.
  • statin granules obtained are dried such that their moisture rate is 5% and they are sieved.
  • the active agent amlodipine is treated with at least one effervescent acid in non-aqueous environment.
  • the mixtures obtained in the second and the third steps are mixed until the required homogeneity is attained to.
  • the final mixture is prepared ready for tablet compression optionally after the other pharmaceutically acceptable excipients are added. Tablets are coated as required.
  • the problems experienced in water soluble powder, tablet and granule formulations are overcome and a far more stable product is obtained in comparison with the compositions produced by conventional methods since the pharmaceutical composition comprising amlodipine and a statin group compound is subjected to the production method according to the present invention.
  • statin group compound By subjecting the statin group compound to wet granulation in the presence of the effervescent base; fluidity, dispersion and solubility characteristics of said compound is provided to be as required.
  • the amount of the active agent in the pharmaceutical formulation of the present invention can vary in the range of 0.5% to 95%, preferably in the range of 1% to 90% according to total amount of substance in the pharmaceutical formulation. Dosage of the active agent in the pharmaceutical formulation may change according to the route of administration; users' age and state of health.
  • the pharmaceutical formulation comprising the present invention can comprise 1-40 mg amlodipine and 0,1-160 mg statin group compound in one dose.
  • Statin group compounds can be selected from the group comprising rosuvastatin, atorvastatin, cerivastatin, lovastatin, fluvastatin, mevastatin, pravastatin and pitavastatin.
  • compositions are obtained in the treatment of the disease by formulating amlodipine in combination with rosuvastatin or atorvastatin.
  • compositions comprising the present invention are indicated in diseases comprising dyslipidemia, hypercholesterolemia, hyperlipoproteinemia, hypertriglyceridemia, angina, variant angina, prophylaxis of myocardial infarction, prophylaxis of stroke, atherosclerosis and hypertension.
  • the pharmaceutical formulations of the present invention are administered by the oral route.
  • the pharmaceutical formulation comprising the use of amlodipine and a statin group compound in combination can also optionally comprise excipients such as effervescent couple, binder, sweetener, flavoring agent, diluent, lubricant, taste regulating agent, viscosity enhancing components, surfactants, filling materials, drying agents, glidants, anti-foam agents, wetting agents.
  • excipients such as effervescent couple, binder, sweetener, flavoring agent, diluent, lubricant, taste regulating agent, viscosity enhancing components, surfactants, filling materials, drying agents, glidants, anti-foam agents, wetting agents.
  • the pharmaceutically acceptable effervescent couple of the present invention is composed of the combination of an acidic agent and a basic agent.
  • the acidic agent comprises organic and/or inorganic acids; the basic agent can be alkaline earth carbonate or alkaline earth bicarbonate.
  • the pharmaceutically acceptable acidic agent of the present invention can be selected from, but not limited to, a group comprising acetic acid, citric acid, lactic acid, malic acid, phosphoric acid, fumaric acid, propionic acid, tartaric acid and/or pharmaceutically acceptable salts, hydrates, anhydrates or preferably a combination thereof.
  • the pharmaceutically acceptable basic agent of the present invention can be selected from, but not limited to, the group comprising potassium carbonate, potassium bicarbonate, sodium carbonate, sodium hydrogen carbonate or combinations thereof.
  • the pharmaceutically acceptable binder of the present invention can be selected from, but not limited to, a group comprising ethyl cellulose, hydroxyethyl cellulose, methyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, gelatin, hypromellose, magnesium aluminum silicate, maltodextrin, polyethylene oxide, povidone, polyvinylpyrrolidone, sorbitol and water or combinations thereof.
  • stability characteristic of the pharmaceutical formulation is positively affected when the binder is polyvinylpyrrolidone.
  • the pharmaceutically acceptable sweetener of the present invention can be selected from, but not limited to, a group comprising aspartame, acesulfame, acesulfame potassium, fructose, dextrose, glucose, lactitol, maltitol, xylitol, sorbitol, maltose, saccharine, saccharine sodium, sodium cyclamate, sucralose, sucrose or combinations thereof.
  • the pharmaceutically acceptable flavoring agent of the present invention can be selected from, but not limited to, the group comprising sour cherry flavor, blackberry flavor, grapefruit flavor, grape flavor, pear flavor, orange flavor, apricot flavor or combinations thereof.
  • the pharmaceutically acceptable diluent of the present invention can be selected from, but not limited to, the group comprising lactose, dry lactose, lactose monohydrate, directly compressed lactose (lactose D.C.), starch, hydrolyzed starch, mannitol, sorbitol, xylitol, dextrose, dextrose monohydrate, dibasic calcium phosphate dihydrate, monobasic calcium, sulfate monohydrate, calcium sulfate dihydrate, amylose, calcium carbonate, glycine, bentonite.
  • the pharmaceutically acceptable lubricant of the present invention can be selected from, but not limited to, the group comprising metallic stearates (e.g. magnesium stearate, calcium stearate, aluminum stearate), fatty acid esters (e.g. sodium stearil fumarate), fatty acids (e.g. stearic acid), fatty alcohols, polyethylene glycol, glyceryl behenate, mineral oil, paraffines, hydrogenated vegetable oil, leucine, polyethylene glycols (PEG), metallic lauryl sulfates (e.g. sodium lauryl sulfate, magnesium lauryl sulfate), sodium chloride, sodium benzoate, sodium acetate and talc.
  • metallic stearates e.g. magnesium stearate, calcium stearate, aluminum stearate
  • fatty acid esters e.g. sodium stearil fumarate
  • fatty acids e.g. stearic acid
  • the pharmaceutically acceptable surfactant can be selected from, but not limited to, the group comprising sodium lauryl sulfate, polyoxyethylene sorbitan fatty acid esters (polysorbates), polyoxyethylene alkyl ethers, sorbitan fatty acid esters, polyethylene glycols, polyoxyethylene castor oil derivatives, docusate sodium, quaternary ammonium compounds, sugar esters of fatty acids and glycerides of fatty acids.
  • the pharmaceutically acceptable glidant of the present invention can be selected from, but not limited to, the group comprising talc, silicone dioxide, magnesium trisilicate, cellulose powder, starch, tribasic calcium phosphate, metallic stearates, calcium silicate and metallic lauryl sulfate.
  • Atorvastatin is subjected to wet granulation in the presence of at least one effervescent base.
  • the granules obtained are dried such that their moisture rate is maximum 5%, then they are sieved.
  • Amlodipine is mixed with at least one effervescent acid and the binder in nonaqueous environment. Then, the mixtures belonging to the active agents atorvastatin and amlodipine are mixed until the required homogeneity is attained to.
  • the mixture is prepared ready for tablet compression after the other pharmaceutically acceptable excipient are added. Said mixture is shaped.
  • Rosuvastatin is subjected to wet granulation in the presence of at least one effervescent base.
  • the granules obtained are dried such that their moisture rate is maximum 5%, then they are sieved.
  • Amlodipine is mixed with at least one effervescent acid and the binder in nonaqueous environment. Then, the mixtures belonging to the active agents atorvastatin and amlodipine are mixed until the required homogeneity is attained to.
  • the mixture is prepared ready for tablet compression after other pharmaceutically acceptable excipient are added. Said mixture is shaped.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne des nouvelles compositions pharmaceutiques hydrosolubles stables et faciles à produire, comprenant une combinaison d'un inhibiteur calcique et d'un inhibiteur de la 3-hydroxy-3-méthylglutaryl-coenzyme A réductase.
EP11745588.1A 2010-06-03 2011-06-02 Formulation hydrosoluble stable Withdrawn EP2575757A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR201004458 2010-06-03
PCT/TR2011/000140 WO2011152803A1 (fr) 2010-06-03 2011-06-02 Formulation hydrosoluble stable

Publications (1)

Publication Number Publication Date
EP2575757A1 true EP2575757A1 (fr) 2013-04-10

Family

ID=44504124

Family Applications (1)

Application Number Title Priority Date Filing Date
EP11745588.1A Withdrawn EP2575757A1 (fr) 2010-06-03 2011-06-02 Formulation hydrosoluble stable

Country Status (2)

Country Link
EP (1) EP2575757A1 (fr)
WO (1) WO2011152803A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110545801A (zh) * 2017-04-26 2019-12-06 艾威群韩国股份有限公司 HMG-CoA还原酶抑制剂以及包含钙通道阻滞剂的复合制剂

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TR201009399A2 (tr) * 2010-11-11 2012-05-21 Bi̇lgi̇ç Mahmut Hızlı çözünen efervesan rosuvastatin formülasyonları.
TR201100152A2 (tr) * 2011-01-06 2012-07-23 Bi̇lgi̇ç Mahmut Amlodipin içeren efervesan bileşimler.
CN102716370B (zh) * 2012-07-04 2014-07-02 施慧达药业集团(吉林)有限公司 一种预防或治疗高血压的药物组合物
KR101910901B1 (ko) * 2013-11-29 2018-10-24 한미약품 주식회사 암로디핀, 로자탄 및 로수바스타틴을 포함하는 약제학적 복합 제제
CN109453152B (zh) * 2018-11-23 2020-10-27 西安交通大学 一种改善主动脉内皮细胞功能的药物及其应用

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FI94339C (fi) 1989-07-21 1995-08-25 Warner Lambert Co Menetelmä farmaseuttisesti käyttökelpoisen /R-(R*,R*)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110545801A (zh) * 2017-04-26 2019-12-06 艾威群韩国股份有限公司 HMG-CoA还原酶抑制剂以及包含钙通道阻滞剂的复合制剂
CN110545801B (zh) * 2017-04-26 2022-08-30 艾威群韩国股份有限公司 HMG-CoA还原酶抑制剂以及包含钙通道阻滞剂的复合制剂

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Publication number Publication date
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