EP2934590A1 - Magnesiumhydroxidcarbonat als träger in pharmazeutischen zubereitungen mit verbesserter wirkstofffreisetzung - Google Patents
Magnesiumhydroxidcarbonat als träger in pharmazeutischen zubereitungen mit verbesserter wirkstofffreisetzungInfo
- Publication number
- EP2934590A1 EP2934590A1 EP13798577.6A EP13798577A EP2934590A1 EP 2934590 A1 EP2934590 A1 EP 2934590A1 EP 13798577 A EP13798577 A EP 13798577A EP 2934590 A1 EP2934590 A1 EP 2934590A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- magnesium hydroxide
- hydroxide carbonate
- release
- fenofibrate
- active ingredient
- 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- Withdrawn
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
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1611—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
-
- 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/485—Inorganic compounds
Definitions
- the present invention relates to pharmaceutical formulations of drugs poorly soluble in aqueous solutions with improved
- Drug release as well as a process for their preparation.
- Active ingredients (APIs) for use in pharmaceutical preparations must have useful processing properties for the pharmaceutical practice so that a patient-appropriate dosage form can be formulated at all.
- the active ingredients in the body must be released from these formulations again to their
- Formulations are not or only insufficiently quickly soluble, and thus in the body are not sufficiently absorbed to their
- Solution-speeding additive or by the skillful choice of a drug carrier can accelerate the drug release of such poorly soluble problem drugs.
- the object is a stable connection between a physiologically acceptable, porous IVIagnesiumhydroxidcarbonat in a mold
- the subject of the present invention are in particular
- Accelerated release formulations containing high surface area porous magnesium hydroxide carbonate as carrier material and at least one active ingredient.
- active ingredients at least one pharmaceutical active ingredient is preferably contained in the formulation according to the invention.
- Bioavailability is at least one sparingly soluble component of BCS
- the improved release of the sparingly soluble active ingredients is achieved by applying it or by applying it from a solution to the porous magnesium hydroxide carbonate as a carrier material.
- the better drug release is achieved satisfactorily when, as
- Support material magnesium hydroxide carbonate having a BET surface area of at least 20 m 2 / g, preferably of at least 30 m 2 / g and particularly preferably of at least 40 m 2 / g, is used and from it
- formulations of the invention can be prepared according to the invention in a simple process, wherein in a first step, the active ingredient or in a suitable solvent or
- Solvent mixture is (are) dissolved, wherein the porous
- the removal of the Solvent or mixtures can be made using various convection and contact drying methods.
- a particularly good connection between the magnesium hydroxide carbonate and the sparingly soluble in aqueous solutions or active ingredient (s) is obtained when the process is carried out using a fluidized bed drying, and the active ingredient solution at low temperature to a submitted in the fluidized bed porous magnesium hydroxide by spraying in intimate contact and dried.
- it has also been shown that a good connection between the carrier and the one or more sparingly soluble in aqueous solutions drug (s) is obtained when the porous magnesium hydroxide in the active ingredient-containing
- Freeze-drying process is dried. Detailed description
- Problem drug is the primary goal to increase the rate of dissolution to release an adequate amount of drug in the body and to provide for absorption. This is the only way to achieve a sufficiently high concentration of active substance at the desired site of action in the body.
- solubilizing additives because such additives often show negative physiological interactions with the body tissues.
- Magnesium hydroxide carbonates with a particularly large BET Surface and a high pore volume are particularly suitable for this, since they are considered physiologically largely harmless.
- Release medium or the physiological fluids increased. This can be done by preparing a simple physical mixture of the crystalline API with the particular magnesium hydroxide carbonate. This is for a good connection between the
- Magnesiumhydroxidcarbonattec and the crystalline APIs are important to present the latter preferably in the form of very small particles, so that by a corresponding physical interaction a
- Solvent are dissolved and this solution is then brought into intimate contact with the porous magnesium hydroxide, so that the surface and the pores of the carrier can be covered or filled with the drug solution. Subsequently, the solvent is removed. This can be achieved by drying the
- a magnesium hydroxide carbonate with a special particle morphology is particularly suitable, in particular that in WO 2011/095269 A1
- magnesium hydroxide carbonate It is characterized by a suitable particle morphology, combined with a particularly large BET surface area and a high pore volume.
- the magnesium hydroxide carbonate described herein is easily soluble in an acidic and aqueous environment such as gastric juice due to its porous structure and releases CO2 gas. Depending on the size of one out of this
- Magnesium hydroxide carbonate manufactured tablet can this
- Magnesium hydroxide carbonate as a carrier material or filler in
- Medicament preparations are used, which disintegrate rapidly after oral intake or for the production of medicated effervescent drinks.
- Magnesiumhydroxidcarbonate receives the formulator in the pharmaceutical industry, the ability to bring even problematic drugs in a fast drug release form.
- Particularly interesting is the possibility of influencing the dissolution rate and the solubility (also as supersaturation) and, consequently, influencing the bioavailability of poorly soluble and / or poorly absorbable APIs. It is particularly advantageous that it is at
- Magnesium hydroxide carbonate as a carrier is a substance listed in all pharmacopoeias, so that no problems can arise from the registration for the approval of the drugs.
- Test systems diagnostics, for the release of agricultural active substances, in veterinary medicine or in body implants.
- a sparingly soluble API such as fenofibrate
- a suitable solvent such as fenofibrate
- Magnesium hydroxide is not or only slightly soluble.
- This solution is intimately mixed with a magnesium hydroxide carbonate having a particularly large BET surface area and a large pore volume. Thereafter, the solvent is removed, for example, by evaporation in vacuo, optionally with gentle heating or by freeze-drying.
- the resulting drug-magnesium hydroxide carbonate conglomerate has, as the further studies have shown, an improved in vitro release behavior, especially when it is further processed into formulations in tablet form.
- This type of formulation of poorly soluble active ingredients is particularly advantageous when particularly low-dose preparations of the active ingredient have to be prepared. Due to the firm binding of the active ingredient to the surface of the carrier material, a free-flowing powder is obtained, which, if desired, can be compressed into tablets in which a consistent active ingredient concentration can be reliably guaranteed. The same applies, however, to active substances which are to be administered in low doses and administered in powder form. Since the drug is firmly attached to the carrier, no separation of powdered carrier and drug can take place.
- Nutritional supplements but also cosmetics,
- Plant treatment agents such as herbicides or fungicides, reagents, diagnostics and feed and also as dyes, minerals or catalysts are suitable. These include, for example, tablets of any shape, capsules, pellets or granules and powder mixtures.
- auxiliaries may be present in the active substance-containing solid formulations in addition to the active ingredient and the porous magnesium hydroxide carbonate as carrier according to the invention. These may include, but are not limited to flavor enhancers, tableting aids such as lubricants, and the like. Possible additives are, for example, thermoplastic polymers, lipids, sugar alcohols,
- thermoplastic polymers are, for example
- Polyvinylpyrrolidone (PVP), copolymers of N-vinylpyrrolidone and
- Crotonic acid partially saponified polyvinyl acetate, polyvinyl alcohol,
- Methylcellulose and ethylcellulose Hydroxyalkylcetlured, in particular hydroxypropylcellulose (HPC), hydroxyalkyl-alkylcelluloses, in particular hydroxypropylmethylcellulose (HPMC), cellulose esters such
- Cellulose phthalates in particular cellulose acetate phthalate,
- HPMCAS Hydroxypropylmethylcellulose acetate succinate
- sugars such as sucrose, glucose, maltose, xylose, fructose,
- Ribose arabinose, galactose, trehalose, but also sugar alcohols.
- Suitable sugar alcohols are sorbitol, xylitol, mannitol, maltitol; a suitable one
- Sugar alcohol derivative is also isomalt. Also suitable may be urea, nicotinamide, amino acids or cyclodextrins. These additives can be obtained commercially in various grades under different trade names.
- Suitable lipids are fatty acids, such as stearic acid; Fatty alcohols, such as cetyl or stearyl alcohol; Fats, such as animal or vegetable fats; Waxes, such as carnauba wax; or mono- and / or diglycerides or phosphatides, especially lecithin.
- the fats preferably have a melting point of at least 50 ° C.
- Preferred are triglycerides of the Ci 2 , C 4 , Cie and C-is fatty acids.
- galenic adjuvants whose total amount may be up to 20% by weight, preferably less than 10% by weight, in particular less than 5% by weight, based on the dosage form, can be used. Which includes:
- Extenders or fillers such as lactose, cellulose, silicates, phosphates or silica;
- Lubricants such as magnesium and calcium stearate, sodium stearyl fumarate; plasticizers;
- Dyes such as azo dyes, organic or inorganic pigments or dyes of natural origin
- Stabilizers such as antioxidants, light stabilizers, hydroperoxide killers, radical scavengers, preservatives and microbial attack stabilizers;
- active substances are to be understood as meaning all substances having a desired physiological action on the human or animal body or plants. These are in particular pharmaceutical active ingredients. The amount of active ingredient per dose can vary within wide limits. It is usually chosen so that it is sufficient to achieve the desired effect. Also drug combinations can be used. Active substances within the meaning of the invention are also vitamins and minerals as well as peptide therapeutics and proteins.
- sparingly soluble substances in the context of the invention are substances whose saturation solubility at room temperature (20 ° C) in at least one of the following media is less than 1 wt .-%: water, 0.1 molar aqueous hydrochloric acid, aqueous phosphate buffer pH 7, 2, 0.9% by weight aqueous sodium chloride solution.
- the sparingly soluble substances are a large number of active substances and effect substances, in particular pharmaceutical or cosmetic active ingredients, active ingredients for dietary supplements or dietary agents or food additives.
- Sparingly soluble substances according to the invention are, for example: piroxicam, clotrimazole, carbamazepine, 17-beta-estradiol, sulfathiazole, fenofibrate, benzocaine, lidocaine, dimethindene, biperiden, bisacodyl,
- Refocoxib Oxaprozin, Leflunomide, Diclofenac, Nabumetone, Flurbiprofen, Tetrahydrocannabinol, Capsaicin, Ketorolac, Albendazole, Ivermectin,
- Amiodarone zileuton, zafirlukast, albuterol, montelukast, azithromycin, ciprofloxacin, clarithromycin, dirithromycin, rifabutin, rifapentin,
- Trovafloxacin ritanovir, saquinavir, nelfinavir, efavirenz,
- Paroxetine sertraline, venlafaxine, bupropion, clomipramine, miglitol,
- Repaglinide glimepiride, pioglitazone, rosiglitazone, troglitazone, glyburide, glipizide, glibenclamide, fosphenytione, tiagabine, topiramate, lamotrigine, vigabatrin, amphotericin B, butenafine, terbinafine, itraconazole, flucanazole,
- mice Miconazole, ketoconazole, metronidazole, griseofulvin, nitrofurantoin, lisinopril, benezepril, nifedipine, nisolidipine, telmisartan, irbesartan, eposartan,
- Valsartan candesartan, minoxidil, terazosin, halofantrine, mefloquine, dihydroergotamine, ergotamine, frovatriptan, pizotifen, sumatriptan,
- Tacrolimus sirolimus, tamoxifen, camptothecan, topotecan, nilutamide, bicalutanide, toremifene, atovaquone, metronidazole, furazolidone, paricalcitol, benzonatate, midazolam, zolpidem, gabapentin, zopiclone, digoxin,
- Fenofibrate probucol, gemfibrozil, cerivistatin, pravastatin, simvastatin, fluvastatin, atorvastatin, tizanidine, dantrolene, isosorbide dinitrate,
- Dihydrotachysterol essential fatty acids, codeine, fentanyl, methadone, nalbuphine, pentazocine, clomiphene, danazol, dihydroepiandrosterone,
- Medroxyprogesterone progesterone, rimexolone, megestrol acetate, oestradiol, finasteride, mefepristone, L-thyroxine, tamsulosin, methoxsalen, tacrine, donepezil, raloxifene, vertoporfin, sibutramine, pyridostigmine, and theirs Isomers, derivatives, salts or mixtures or other active substances which fulfill the abovementioned definition.
- the magnesium hydroxide carbonate of sample A differs from the other investigated magnesium hydroxide carbonate grades (samples B and C), in particular in the BET surface area.
- the magnesium hydroxide carbonate of the sample B shows a BET surface area of only about 11.5 m 2 / g, that of the sample C at least about 31.6 m 2 / g, but the invention
- Magnesium hydroxide carbonate of sample A has a BET surface area of 44 ) has 4m 2 / g.
- the 31.6m 2 / g BET surface area of sample C does not appear to be sufficient for a significant improvement in drug release. The data show that such formulations have a faster and more
- Dispersant R1 1,330; Pump Speed: 2000 rpm; Stirrer Speed: 2000 rpm;
- Ultrasonic Duration 1 sec; Ultrasonic Level: 100%; Tray Type: General Purpose; Background Time: 7500 msec; Measure Time: 7500 msec; Obscuration limits: 10.0-20.0%;
- composition (% by weight) of the release medium with 0.5% SDS:
- composition (in% by weight) of the release medium with 1% SDS:
- Sample B NutriMag MC DC magnesium carbonate heavy, pharm., Gran.
- Fenofibrate> 99% powder, Sigma Aldrich, Buchs (Switzerland), Pcode 101050968, F6020, LOT BCBG3328V
- Acetone used to dissolve the fenofibrate acetone suitable for use as excipient EMPROVE exp Ph Eur, BP, NF, Merck KGaA, Darmstadt (Germany), Art. No .: 100013, lot: K42947013
- Hydrochloric acid c (HCI) 1 mol / l (1N) TitriPUR, Merck KGaA, Darmstadt
- Hard capsules used Capsugel Gr.OO, Product CD: X01E0009, Capsugel Order no. 2159658-1-1, Lot no. 33045581
- Aim The aim of the experiments is to differentiate the in vitro release behavior of poorly soluble drugs, such as To elucidate fenofibrate from formulations based on different types of magnesium hydroxide carbonate. For this purpose, three different free-flowing and
- Magnesiumhydroxidcarbonatmuster A-C are mixed with 5.0g fenofibrate, mixed and then each 500mg +/- 2mg of these mixtures by hand in hard capsules filled (each 12 capsules per
- Fig. 1 It is the Fenofibratzysprofile the mechanical
- Magnesiumhydroxidcarbonatmuster A-C are mixed with 50.0g of fenofibrate (dissolved in acetone), intimately mixed, the solvent removed and then each 500mg +/- 2mg of these conglomerates by hand in hard capsules filled (12 capsules per production). Each 6 of these capsules are tested in the paddle apparatus of Erweka in both media (with 1% SDS or with 0.5% SDS) on the rate and extent of fenofibrate release.
- the measurements in the two release media with different amounts of SDS detergent serve to better discriminate the different fenofibrate release behavior based on the three different magnesium hydroxide carbonates.
- FIG. 3 The release profiles of fenofibrate [% by weight] in FIG.
- Table 10 Results of fenofibrate release from the hard capsules in the release medium with 0.5% SDS / sodium dodecyl sulfate (In% by weight of the amount of fenofibrate released relative to a total expected amount of 50 mg fenofibrate / capsule, measurement of 6 capsules per example)
- FIG. 4 The release profiles of fenofibrate [% by weight] in FIG.
- Magnesium hydroxide carbonate sample A according to Example 4 exhibits significantly faster and greater drug release both in speed and in extent (after 120 minutes) than the fenofibrate grown on the magnesium hydroxide carbonate samples B and C (Examples 5 and 6).
- Fig. 5 The release profiles of fenofibrate after being grown on different magnesium hydroxide carbonates compared to the profiles of the mechanical mixtures in the presence of 1% SDS are shown;
- Example 4 In the release medium with 1% SDS as detergent, the fenofibrate formulation of Example 4 (fenofibrate grown on the magnesium hydroxide carbonate sample A) shows the fastest as well as the most quantitative release of the active ingredient. Examples 5 and 6
- Fig. 6 The release profiles of fenofibrate after mounting on various magnesium hydroxide carbonates compared to the profiles of the mechanical mixtures in the presence of 0.5% SDS are shown; Examples 4-6 compared with Examples 1-3.
- the fenofibrate formulation of Example 4 (fenofibrate grown on the magnesium hydroxide carbonate sample A) also shows the fastest as well as the most quantitative release of the active ingredient.
- Magnesium hydroxide carbonate carrier is superior to a simple mechanical mixture of the components in terms of release rate and release amount of the drug.
- Pattern A differs from Patterns B and C especially in the BET surface area; Pattern C shows a BET surface area of only about 1; 5 m 2 / g, pattern B of at least about 31, 6m 2 / g and of sample A 44,4m 2 / g.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13798577.6A EP2934590A1 (de) | 2012-12-21 | 2013-11-22 | Magnesiumhydroxidcarbonat als träger in pharmazeutischen zubereitungen mit verbesserter wirkstofffreisetzung |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12008593 | 2012-12-21 | ||
EP13000573 | 2013-02-05 | ||
EP13798577.6A EP2934590A1 (de) | 2012-12-21 | 2013-11-22 | Magnesiumhydroxidcarbonat als träger in pharmazeutischen zubereitungen mit verbesserter wirkstofffreisetzung |
PCT/EP2013/003537 WO2014094956A1 (de) | 2012-12-21 | 2013-11-22 | Magnesiumhydroxidcarbonat als träger in pharmazeutischen zubereitungen mit verbesserter wirkstofffreisetzung |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2934590A1 true EP2934590A1 (de) | 2015-10-28 |
Family
ID=49680975
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP13798577.6A Withdrawn EP2934590A1 (de) | 2012-12-21 | 2013-11-22 | Magnesiumhydroxidcarbonat als träger in pharmazeutischen zubereitungen mit verbesserter wirkstofffreisetzung |
Country Status (10)
Country | Link |
---|---|
US (1) | US20150328316A1 (zh) |
EP (1) | EP2934590A1 (zh) |
JP (2) | JP6498607B2 (zh) |
KR (1) | KR20150100826A (zh) |
CN (1) | CN104870018A (zh) |
AU (1) | AU2013362269A1 (zh) |
BR (1) | BR112015014739A2 (zh) |
CA (1) | CA2895827A1 (zh) |
IL (1) | IL239393A0 (zh) |
WO (1) | WO2014094956A1 (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107951841B (zh) * | 2017-12-21 | 2021-04-06 | 聊城大学 | 一种尼莫地平固体分散体及其片剂制备方法 |
WO2021110545A1 (en) * | 2019-12-02 | 2021-06-10 | Merck Patent Gmbh | Deposition of nanosuspensions of active pharmaceutical ingredients on carriers |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
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US460923A (en) * | 1891-10-06 | Eighths to wm | ||
JPH04369375A (ja) * | 1991-06-17 | 1992-12-22 | Matsushita Refrig Co Ltd | 冷蔵庫 |
US6630192B2 (en) * | 1995-04-07 | 2003-10-07 | Brandeis University | Increasing the HDL level and the HDL/LDL ratio in human serum by balancing saturated and polyunsaturated dietary fatty acids |
GB0016452D0 (en) * | 2000-07-04 | 2000-08-23 | Kilgowan Limited | Vitamin K and essential fatty acids |
JP2003342894A (ja) * | 2002-05-24 | 2003-12-03 | Nittetsu Mining Co Ltd | 低密度紙用填料、低密度紙及びその製造方法 |
JP3910503B2 (ja) * | 2002-07-30 | 2007-04-25 | 日鉄鉱業株式会社 | 塩基性炭酸マグネシウムの製造方法 |
EP1475351B1 (en) * | 2002-02-13 | 2018-05-23 | Nittetsu Mining Co., Ltd. | Basic magnesium carbonate, process for producing the same and utilization thereof |
JP3910495B2 (ja) * | 2002-02-13 | 2007-04-25 | 日鉄鉱業株式会社 | 塩基性炭酸マグネシウム及びその製造方法、並びに該塩基性炭酸マグネシウムを含有する組成物又は構造体 |
JP3910555B2 (ja) * | 2002-09-17 | 2007-04-25 | 日鉄鉱業株式会社 | 中空担体及び機能性粒子、並びにそれらの製造方法 |
CN1526384A (zh) * | 2003-03-05 | 2004-09-08 | 安徽省新星药物开发有限责任公司 | 非诺贝特快速崩解的口服制剂 |
EP1457206A1 (en) * | 2003-03-13 | 2004-09-15 | Fournier Laboratories Ireland Limited | Combined use of a fibrate and orlistat for the treatment of obesity |
US20090030077A1 (en) * | 2004-08-06 | 2009-01-29 | Transform Pharmaceuticals Inc. | Novel Fenofibrate Formulations and Related Methods of Treatment |
US20060068010A1 (en) * | 2004-09-30 | 2006-03-30 | Stephen Turner | Method for improving the bioavailability of orally delivered therapeutics |
WO2006085217A2 (en) * | 2005-02-08 | 2006-08-17 | Pfizer Products Inc. | Solid adsorbates of hydrophobic drugs |
IS7724A (is) * | 2005-03-02 | 2006-09-03 | Actavis Group | Samsetning á töflum með hraða sundrun sem innihalda þungt magnesíum karbónat |
ES2497574T3 (es) * | 2010-02-03 | 2014-09-23 | Merck Patent Gmbh | Hidróxido carbonato de magnesio directamente compresible |
KR101202994B1 (ko) * | 2010-04-12 | 2012-11-21 | 한미사이언스 주식회사 | 페노피브린산 및 알칼리화제를 포함하는 경구용 약학 조성물 |
EP2659882A4 (en) * | 2010-12-27 | 2014-11-12 | Tomita Pharma | DISPOSABLE CORE PARTICLES FOR PHARMACEUTICAL FORMULATION |
-
2013
- 2013-11-22 CN CN201380066746.6A patent/CN104870018A/zh active Pending
- 2013-11-22 AU AU2013362269A patent/AU2013362269A1/en not_active Abandoned
- 2013-11-22 US US14/653,507 patent/US20150328316A1/en not_active Abandoned
- 2013-11-22 WO PCT/EP2013/003537 patent/WO2014094956A1/de active Application Filing
- 2013-11-22 BR BR112015014739A patent/BR112015014739A2/pt not_active Application Discontinuation
- 2013-11-22 KR KR1020157019819A patent/KR20150100826A/ko not_active Application Discontinuation
- 2013-11-22 EP EP13798577.6A patent/EP2934590A1/de not_active Withdrawn
- 2013-11-22 JP JP2015548252A patent/JP6498607B2/ja not_active Expired - Fee Related
- 2013-11-22 CA CA2895827A patent/CA2895827A1/en not_active Abandoned
-
2015
- 2015-06-14 IL IL239393A patent/IL239393A0/en unknown
-
2018
- 2018-11-26 JP JP2018220272A patent/JP2019023246A/ja active Pending
Non-Patent Citations (1)
Title |
---|
G. AHUJA: "Porous Carriers for Controlled/Modulated Drug Delivery", INDIAN J. PHAM. SCI., vol. 71, no. 6, 1 January 2009 (2009-01-01), pages 599 - 607, XP055156183, DOI: 10.4103/0250-474X.59540 * |
Also Published As
Publication number | Publication date |
---|---|
AU2013362269A1 (en) | 2015-07-30 |
KR20150100826A (ko) | 2015-09-02 |
JP2019023246A (ja) | 2019-02-14 |
BR112015014739A2 (pt) | 2017-07-11 |
WO2014094956A1 (de) | 2014-06-26 |
IL239393A0 (en) | 2015-07-30 |
JP2016503763A (ja) | 2016-02-08 |
CN104870018A (zh) | 2015-08-26 |
US20150328316A1 (en) | 2015-11-19 |
JP6498607B2 (ja) | 2019-04-10 |
CA2895827A1 (en) | 2014-06-26 |
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