EP2542222A2 - Schmelzüberzogene arzneiformen - Google Patents

Schmelzüberzogene arzneiformen

Info

Publication number
EP2542222A2
EP2542222A2 EP11705898A EP11705898A EP2542222A2 EP 2542222 A2 EP2542222 A2 EP 2542222A2 EP 11705898 A EP11705898 A EP 11705898A EP 11705898 A EP11705898 A EP 11705898A EP 2542222 A2 EP2542222 A2 EP 2542222A2
Authority
EP
European Patent Office
Prior art keywords
weight
melt
preparations according
carrier particles
preparations
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Withdrawn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
EP11705898A
Other languages
German (de)
English (en)
French (fr)
Inventor
Karl Kolter
Dejan Djuric
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to EP11705898A priority Critical patent/EP2542222A2/de
Publication of EP2542222A2 publication Critical patent/EP2542222A2/de
Withdrawn legal-status Critical Current

Links

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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/167—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface
    • A61K9/1676—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface having a drug-free core with discrete complete coating layer containing drug
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4174—Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
    • 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
    • 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
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam

Definitions

  • the present invention relates to carrier particles coated with active substance-containing coatings, wherein the sparingly water-soluble active ingredient is embedded in a coating of amphiphilic copolymers which are obtained by polymerization of vinyl acetate and N-vinyl lactams in the presence of a polyether embedded, and the coatings Form of a melt can be applied. Furthermore, the invention relates to processes for the preparation of such coated carrier particles and agglomerates of such particles and their use in pharmaceutical dosage forms.
  • the coating of particles with active substance-containing coatings is usually carried out by spraying solutions of the coating compositions
  • a disadvantage of processing from the solution is the difficult handling of organic solvents, which place high demands on the environment and equipment. Furthermore, it is often difficult to find a suitable organic solvent for poorly soluble drugs.
  • Amphiphilic copolymers such as graft polymers obtained by radical polymerization of vinyl acetate and N-vinyl lactams in the presence of a polyether are known per se.
  • WO 2007/051743 discloses the use of water-soluble or water-dispersible copolymers of N-vinyllactam, vinyl acetate and polyethers as solubilizers for pharmaceutical, cosmetic, food-processing, agrotechnical or other technical applications. This generally describes that the corresponding graft polymers can also be processed in the melt with the active ingredients.
  • melt is solvent-free.
  • solvent-free means that less than 5000 ppm of solvent are contained.
  • Suitable amphiphilic copolymers for embedding water-soluble active ingredients and their processability by melt extrusion are known, for example, from WO 2007/051743.
  • Corresponding copolymers are obtained by free-radically initiated polymerization of a mixture of i) 30 to 80% by weight of N-vinyllactam,
  • preferred copolymers obtained from: i) 30 to 70% by weight of N-vinyllactam
  • Copolymers particularly preferably used are obtainable from: i) 40 to 60% by weight of N-vinyllactam
  • Suitable N-vinyllactam are N-vinylcaprolactam or N-vinylpyrrolidone or mixtures thereof. Preference is given to using N-vinylcaprolactam.
  • an amphiphilic copolymer of N-vinylcaprolactam, vinyl acetate and a polyether is particularly preferred.
  • the graft is polyether.
  • Suitable polyethers are preferably polyalkylene glycols.
  • the polyalkylene glycols may have molecular weights of 1000 to 100000 Da [Dalton], preferably 1500 to 35000 Da, more preferably 1500 to 10000 Da. The molecular weights are determined on the basis of the measured according to DIN 53240 OH number.
  • polyalkylene glycols are polyethylene glycols. Also suitable are polypropylene glycols, polytetrahydrofurans or polybutylene glycols obtained from 2-ethyloxirane or 2,3-dimethyloxirane.
  • Suitable polyethers are also random or block copolymers of polyalkylene glycols obtained from ethylene oxide, propylene oxide and butylene oxides, such as, for example, polyethylene glycol-polypropylene glycol block copolymers.
  • the block copolymers may be of the AB or ABA type.
  • the preferred polyalkylene glycols also include those which are alkylated at one or both OH end groups.
  • Suitable alkyl radicals are branched or unbranched C to C22-alkyl radicals, preferably C 1 -C 6 -alkyl radicals, for example methyl, ethyl, n-butyl, isobutyl, pentyl, hexyl, octyl, nonyl, decyl , Dodecyl, tridecyl or octadecyl radicals.
  • amphiphilic copolymers are in particular polymers obtained by polymerization of vinyl acetate and N-vinyl lactams in the presence of a polyether used.
  • the inventive method is characterized in that carrier particles are coated with a melt.
  • the melt is composed of sparingly soluble active ingredient, solubilizing polymer and optionally further additives. After cooling and solidification of the melt results in a coating containing the active ingredient in dissolved form.
  • the coating of the carrier particles with a melt can be carried out in conventional fluidized bed apparatuses.
  • the melt is sprayed onto a fluidized bed of carrier particles.
  • the melt is advantageously provided even before the actual spraying in a tempered storage vessel.
  • the melt consisting of polymer, active ingredient and optionally further additives, can then be sprayed by means of nozzles with the aid of a likewise tempered melt pump.
  • Single-fluid nozzles or multi-fluid nozzles can be used as nozzles.
  • two-component nozzles are suitable as multi-substance nozzles.
  • the supply air temperatures are usually between 30 and 200 ° C, preferably between 40 and 120 ° C.
  • the product temperatures are generally between 20 and 100, preferably between 30 and 80 ° C.
  • the melt can also be applied without sputtering, for example by pouring in a thin stream.
  • the melt is solvent-free.
  • the total content of solvents customarily used for such purposes such as alkanols, for example ethanol, methanol or isopropanol, furthermore acetone, ethyl acetate, dichloromethane, chloroform, dimethylformamide and / or methyl ethyl ketone, should be less than 5000 ppm.
  • the content of alkanols should preferably be less than 10 ppm.
  • carrier particles are spherical or at least approximately spherical particles, so-called “nonpareils.”
  • the nonpareils are pure, ie 100% by weight, of pharmaceutical auxiliaries.
  • Carrageenan, starch or microcrystalline cellulose are available in different sizes (100 - 2000 ⁇ ) . Usually the particle sizes are 700-1000 M.
  • Carrier particles may also be tablets or granules.
  • the weight ratio of active ingredient to amphiphilic copolymer in the coating is between 1:99 and 80:20, preferably between 10:90 and 60:40.
  • active agent concentrations of from 1 to 80% by weight, based on the total mass, result.
  • such granules or powders may also contain one or more active substances.
  • the layer thickness of the active substance-containing coatings of amphiphilic copolymer may be 5 to 1000, preferably 10 to 700 ⁇ .
  • the term "sparingly soluble in water” also encompasses practically insoluble substances and means that a solution of the substance in water requires at least 30 to 100 g of water per g of substance at 20 ° C. In the case of practically insoluble substances, at least 10,000 g of water per
  • substances which are sparingly soluble in water are preferably understood to mean biologically active substances such as pharmaceutical active substances for humans and animals, cosmetic or agrochemical active substances or nutritional supplements or dietetic active substances or organic pigments.
  • Suitable biologically active substances according to the invention are in principle all solid active compounds which have a melting point which is below the decomposition point below the melting conditions of the coating mixture.
  • the copolymers can generally be processed at temperatures up to 260 ° C.
  • the lower temperature limit depends on the composition of the mixtures to be melted and the sparingly soluble substances to be processed in each case.
  • the minimum temperature limit can be 30 ° C.
  • the lower temperature limit depends on the viscosity of the melt, which must be low enough to be sprayed. Furthermore, the nozzle shapes and diameters are of importance for the melt viscosity to be adjusted over the temperature.
  • the pharmaceutical active ingredients used are water-insoluble to sparingly soluble substances. According to DAB 9 (German Pharmacopoeia), the classification of the solubility of active pharmaceutical ingredients is as follows: sparingly soluble (soluble in 30 to 100 parts of solvent); poorly soluble (soluble in 100 to 1000 parts of solvent); practically insoluble (soluble in more than 10,000 parts solvent).
  • the active ingredients can come from any indication.
  • Examples include benzodiazepines, antihypertensives, vitamins, cytostatic drugs - especially taxol, anesthetics, neuroleptics, antidepressants, antiviral agents such as anti-HIV agents, antibiotics, antimycotics, anti-dementia, fungicides, chemotherapeutics, urologics, antiplatelet agents, sulfonamides, anticonvulsants, Hormones, immunoglobulins, serums, thyroid therapeutics, psychotropic drugs, Parkinson's and other antihyperkinetics, ophthalmics, neuropathy preparations, calcium metabolism regulators, muscle relaxants, anesthetics, lipid lowering agents, liver therapeutics, coronary agents, cardiakats, immunotherapeutics, regulatory peptides and their inhibitors, hypnotics, sedatives, gynecologics, gout, fibrinolytics , Enzyme preparations and transport proteins, Enzyme inhibitors, Emetics, Medication
  • solubilizer according to the invention in the pharmaceutical preparation is, depending on the active ingredient, in the range of 20 to 99 wt .-%.
  • further pharmaceutically customary excipients may be added to the formulation according to the invention, such as further solubilizers, polymers, dyes, inorganic carriers, disintegrants, gelling agents, slow-release agents, antioxidants, flavoring agents, plasticizers, buffer substances.
  • enteric polymers or retardation polymers the release of the active ingredient can be controlled in a targeted manner.
  • crystallization-inhibiting substances such as Kollidon 30 can increase the stability of the solid solutions.
  • Suitable plasticizers are, for example, triacetin, triethyl citrate, glycerol monostearate, polyethylene glycols or poloxamers.
  • HLB value hydrophilic lipophilic balance
  • ethoxylated hydrogenated castor oil Cremophor® RH 40
  • ethoxylated castor oil Cremophor EL
  • Dyes are e.g. Iron oxides, titanium dioxide, triphenylmethane dyes, azo dyes, quinoline dyes, indigotine dyes, carotenoids to dye the dosage forms, opacifying agents such as titanium dioxide or talc to increase the light transmission and to save dyes.
  • the preparations according to the invention are also suitable for use in the food industry, for example for the incorporation of poorly water-soluble or water-insoluble nutrients, auxiliaries or additives, such. fat-soluble vitamins or carotenoids.
  • the application of the preparations according to the invention in agrochemistry can u. a.
  • Formulations include pesticides, herbicides, fungicides or insecticides, especially those preparations of pesticides used as spray or casting broths.
  • the coated carrier particles obtained according to the invention can be used as capsule fillings or in sachets.
  • coated carrier particles in the form of pellets or granules can also be pressed into tablets.
  • other common Tabllettentosscher as fillers, binders, disintegrants and flow and release agents are used.
  • active substance-containing coatings on carrier particles can be obtained as so-called solid solutions with sparingly soluble substances.
  • Solid solutions according to the invention are systems in which no crystalline components of the sparingly soluble substance are observed.
  • the preparations obtained by the process according to the invention are amorphous, which means that the crystalline proportions of the biologically active substance are less than 5% by weight.
  • the amorphous state is checked by DSC or XRD. Such an amorphous state may also be referred to as an amorphous state.
  • the process of the invention allows the production of stable preparations with high drug loading and good stability with respect to the amorphous state of the sparingly soluble substance.
  • the peculiarity of this method is that an amphiphilic polymer is used together with sparingly soluble active ingredient in the form of a solvent-free melt.
  • the amphiphilic polymer is able to melt or dissolve the active ingredient below its melting point.
  • the coating is thus not a conventional pellet or tablet coating, but a coating that holds poorly soluble drug in dissolved form.
  • the solid solution formed can also serve as a binder bridge between carrier particles and thus as a granulation aid.
  • the advantage of solid solutions is that sparingly soluble drugs can be made more bioavailable.
  • the active ingredients may be contained in the coating or binder layer in amorphous or molecularly dissolved form.
  • the polymer Due to the amphiphilic polymer structure, the polymer is ideally suited as a basis for solid solutions.
  • solid solutions can be achieved via a melt extrusion process.
  • An elegant alternative method is the formation of the solid solution as a coating on solid dosage forms such as pellets, granules, powders or even tablets.
  • the use of common fluidized bed systems makes this process all the more interesting.
  • the freedom of solvent of the melt has a positive effect on the properties of the coatings. These are less porous, but smoother and more homogeneous.
  • Another advantage of this processing method is that solid solutions of sparingly soluble drugs can be made into multiparticulate solid dosage forms. NEN. These multiparticulate dosage forms can be filled, for example, into hard gelatin capsules or even pressed into tablets.
  • amphiphilic copolymer was a graft polymer of 13 wt .-% polyethylene glycol. MG 6000, 57% by weight of N-vinylcaprolactam and 30% by weight of vinyl acetate having an average molecular weight of 44,000 daltons.
  • the processing took place in a fluidized-bed granulator from Glatt Glatt (GPCG 3.1).
  • the spraying was carried out with a two-fluid nozzle, diameter 4 mm.
  • the coatings prepared were examined for crystallinity and morphogenicity using XRD and DSC using the following equipment and conditions:
  • Measuring instrument Diffractometer D 8 Advance with 9-fold sample changer (Fa.Bruker / AXS)
  • Example 1 In the examples below, different carrier particles were provided with active substance-containing coatings.
  • Example 1 Example 1 :
  • the release of the active ingredient from 400 mg pellets was carried out in a USP apparatus 2 in 700 ml of 0.1 normal HCL. After 60 minutes, 90% of the drug was released.
  • the release of the active ingredient from 400 mg pellets was carried out in a USP apparatus 2 in 700 ml of 0.1 normal HCL. After 40 minutes, 100% of the drug was released.
  • the release of the active ingredient from 300 mg pellets was carried out in a USP apparatus 2 in 700 ml of 0.1 normal HCL. After 30 minutes, 100% of the drug was released.
  • the release of the active ingredient from 600 mg pellets was carried out in a USP apparatus 2 in 700 ml of 0.1 normal HCL. After 60 minutes, 100% of the drug was released.
  • the release of the active ingredient from 400 mg of granules was carried out in a USP apparatus 2 700 ml of 0.1 normal HCL. After 60 minutes, 85% of the drug was released.

Landscapes

  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Emergency Medicine (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
EP11705898A 2010-03-05 2011-03-01 Schmelzüberzogene arzneiformen Withdrawn EP2542222A2 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP11705898A EP2542222A2 (de) 2010-03-05 2011-03-01 Schmelzüberzogene arzneiformen

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP10155640 2010-03-05
EP11705898A EP2542222A2 (de) 2010-03-05 2011-03-01 Schmelzüberzogene arzneiformen
PCT/EP2011/053012 WO2011107466A2 (de) 2010-03-05 2011-03-01 Schmelzüberzogene arzneiformen

Publications (1)

Publication Number Publication Date
EP2542222A2 true EP2542222A2 (de) 2013-01-09

Family

ID=43901590

Family Applications (1)

Application Number Title Priority Date Filing Date
EP11705898A Withdrawn EP2542222A2 (de) 2010-03-05 2011-03-01 Schmelzüberzogene arzneiformen

Country Status (4)

Country Link
EP (1) EP2542222A2 (ja)
JP (1) JP2013521249A (ja)
CN (1) CN102781429A (ja)
WO (1) WO2011107466A2 (ja)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2157731B1 (es) * 1998-07-21 2002-05-01 Liconsa Liberacion Controlada Preparacion farmaceutica oral de un compuesto de actividad antifungica y procedimiento para su preparacion.
BRPI0415121A (pt) 2003-10-10 2006-11-28 Lifecycle Pharma As material particulado, forma de dosagem sólida, método para fabricar a mesma, e, uso de um material particulado ou de uma forma de dosagem sólida
CA2582403A1 (en) * 2004-10-01 2006-04-13 Lifecycle Pharma A/S Pharmaceutical compositions comprising fenofibrate and atorvastatin
DE102005053066A1 (de) * 2005-11-04 2007-05-10 Basf Ag Verwendung von Copolymeren als Solubilisatoren für in Wasser schwerlöslichen Verbindungen
WO2009013202A1 (de) * 2007-07-26 2009-01-29 Basf Se Verfahren zur herstellung von durch pfropfpolymerisation in lösung erhaltenen copolymeren auf basis von polyethern in fester form
WO2010017918A2 (de) * 2008-08-11 2010-02-18 Ratiopharm Gmbh Amorphes ambrisentan

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2011107466A2 *

Also Published As

Publication number Publication date
WO2011107466A2 (de) 2011-09-09
WO2011107466A3 (de) 2011-12-15
CN102781429A (zh) 2012-11-14
JP2013521249A (ja) 2013-06-10

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