KR20160129386A - Composition of solid pharmaceutical preparation containing piroxicam-loaded nanospheres prepared by elctrospraying - Google Patents
Composition of solid pharmaceutical preparation containing piroxicam-loaded nanospheres prepared by elctrospraying Download PDFInfo
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- KR20160129386A KR20160129386A KR1020150061455A KR20150061455A KR20160129386A KR 20160129386 A KR20160129386 A KR 20160129386A KR 1020150061455 A KR1020150061455 A KR 1020150061455A KR 20150061455 A KR20150061455 A KR 20150061455A KR 20160129386 A KR20160129386 A KR 20160129386A
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- 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
- A61K9/1629—Organic macromolecular compounds
- A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
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- 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
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- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
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- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
Abstract
The present invention relates to a nano particle containing a Piroxocam using an electrospray technique and a solid preparation composition for oral use containing the same.
Description
The present invention relates to a nano particle containing a Piroxocam using an electrospray technique and a solid preparation composition for oral use containing the same.
Piroxocam is a non-steroidal anti-inflammatory drug (NSAID), widely used for rheumatoid arthritis, osteoarthritis, musculoskeletal disorders, post-surgical or post-traumatic pain. PYROXYCAM is a class II drug according to the Biopharmaceutical classification systems (BCS) and has very low solubility in water. Due to these properties, PYROCYCAM exhibits a low dissolution profile in gastrointestinal fluids, making it difficult to predict bioavailability. Thus, there is a need for a new formulation that improves the dissolution rate and dissolution profile of the drug over currently available Plexiglas solid formulations.
On the other hand, the spray drying method is a method which is already used for the formulation of a large number of medicines by spraying the liquid sample continuously while spraying it to make fine drops of water droplets and instantaneously drying with hot air. The spray drying method has an advantage in that it can make an appropriate sized powder for transporting medicines in the drug delivery through the inhalation or the pore, but the problem is that the shape of the particles is uneven and the size is uneven.
Accordingly, the present invention provides a nano-particle containing a Piroxocam prepared by applying an electrospray technique to a mixture of Piroxycam and polyvinylpyrrolidone, and an oral solid preparation containing the same.
For example, the present invention includes the steps of dissolving PYROXYCAM and polyvinylpyrrolidone in ethanol in a weight ratio of 1: 9 to 3: 7, and spinning the dissolved solution under applied voltage Containing nanocomposite nanocomposite nanocomposite nanoparticles.
As another example, the present invention provides a pyroxycam-containing nanoparticle prepared by the above method.
In another example, the present invention provides an oral solid pharmaceutical composition comprising a pyroxycam-containing nanoparticle prepared by the above method.
As another example, the present invention provides a pyroxycam-containing nanoparticle prepared by an electrospray method, which comprises a pyroxycam and polyvinylpyrrolidone in a weight ratio of 1: 9 to 3: 7.
As another example, the present invention relates to an oral solid pharmaceutical composition comprising a pyroxycam and polyvinylpyrrolidone in a weight ratio of 1: 9 to 3: 7 and comprising a pyroxycam containing nanoparticles prepared by electrospray .
The present invention provides a picoxycam-containing nanoparticle improved in physico-chemical properties and oral bioavailability compared to conventional Pycnospore powders.
In one embodiment, the present invention is directed to a method for preparing a pharmaceutical composition comprising the steps of dissolving pyroxycam and polyvinylpyrrolidone in ethanol in a weight ratio of 1: 9 to 3: 7, and spinning the dissolved solution under applied voltage To a process for producing a polycarboxylic acid-containing nanoparticle.
In another embodiment, the present invention relates to a pyroxycam-containing nanoparticle prepared by the above method.
In another aspect, the present invention relates to an oral solid pharmaceutical composition comprising a pyroxycam-containing nanoparticle prepared by the above method.
In another aspect, the present invention relates to a pyroxycam-containing nanoparticle prepared by electrospinning, which comprises a mixture of pycoxycam and polyvinylpyrrolidone in a weight ratio of 1: 9 to 3: 7.
In another embodiment, the present invention relates to a pharmaceutical composition for oral solid preparation comprising a pycoxycam and polyvinylpyrrolidone in a weight ratio of 1: 9 to 3: 7, ≪ / RTI >
In the present invention, PYROCYCAM is a concept including pYROXYCAM, racemates, enantiomers, polymorphs, hydrates, solvates and pharmaceutically acceptable salts thereof.
The pharmaceutically acceptable salts of the Piroxycam may refer to both organic or inorganic addition salts of Piroxycam which are relatively non-toxic and harmless to the patient and which do not impair the beneficial effects of the base compounds of Piroxycam, , Organic acids, or salts derived from bases. Suitable acids include, for example, hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, perchloric acid, fumaric acid, maleic acid, phosphoric acid, glycolic acid, lactic acid, salicylic acid, succinic acid, toluene-p-sulfonic acid, tartaric acid, acetic acid, , Benzoic acid, malonic acid, naphthalene-2-sulfonic acid, and benzenesulfonic acid. Salts derived from suitable bases may include alkali metals such as sodium and potassium, alkaline earth metals such as magnesium, and ammonium. The preparation of the above composition can be initiated using a salt of picoxycam combined with a pharmaceutically acceptable salt thereof. The salt may be added dropwise in the course of dissolving the picoxycam in a solvent, To form a salt of the Piroxycam.
Polyvinylpyrrolidone (PVP, or povidone) is a polymer made from the monomer N-vinylpyrrolidone. In one embodiment, the polyvinylpyrrolidone used in the present invention may be a water soluble polymer having an average molecular weight of greater than or equal to 2,000 daltons (g / mol), preferably greater than or equal to 20,000 daltons, and less than or equal to 2,500,000 daltons, preferably less than or equal to 1,500,000 daltons have. Polyvinylpyrrolidone can be synthesized or commercially available. For example, polyvinyl pyrrolidone is commercially available from BASF (Ludwigshafen, Germany) under the trade name kollidon or from ISP Technologies (Wayne, New Jersey, USA) . Examples of the polyvinyl pyrrolidone include
Herein, pyroxycam and polyvinylpyrrolidone are dissolved in ethanol at a weight ratio of 1: 9 to 3: 7, and then sprayed through an electrospray so that nanoparticles containing picoxam can be produced.
In one embodiment, the blending ratio of pycoxam and polyvinylpyrrolidone may be 1: 9 to 3: 7 by weight and may be, for example, 1: 9, 2: 8 or 3: 7. When the blending ratio of PYROXYCAM and polyvinylpyrrolidone is less than 1: 9 to 3: 7, since the drug has to be administered orally to many nanoparticles in order to exhibit the drug efficacy, the dose is too much, If it exceeds the above range, nanoparticles may not be produced but nanofibers may be produced.
The pyrroxycam and polyvinylpyrrolidone may be dissolved in ethanol. The content of ethanol depends on the weight percentage of the pycoxycam. When 3 ml or more of ethanol is added to the weight of 1 g of the pycoxycam, the pycoxycam and the polyvinylpyrrolidone can be sufficiently dissolved. When the amount of ethanol is less than 3 ml based on the weight of 1 g of the PYROXYCAM, the PYROXYCAM and the polyvinylpyrrolidone are not dissolved and it is impossible to prepare the nanoparticles.
In the present invention, in the production of the nano-particles containing the pigments by spray drying, a voltage is applied to form an electric field, and the balance between the electrostatic force, which is the force pulling the liquid by the electric field and the surface tension of the liquid, The surface is broken to generate a large number of minute particles (fine droplets) of a very fine shape from the liquid, thereby obtaining a pigment-containing nanoparticle having a uniform particle shape and size.
Electrospray conditions for producing the nano-particles containing the PYROCYCAM are such that the injection rate (or the rate at which the solution is pushed) is 0.07 to 0.10 ml / hr, the applied voltage is 11 to 13 kV, and the injection distance (for example, And the collector plate) may be between 5 and 20 cm. The nanoparticles of the present invention can be easily formulated with nanoparticles having improved physico-chemical properties and oral bioavailability within the above range within the above-mentioned range. .
The nanoparticles of the present invention are prepared through electrospray and have a smaller particle size than particles prepared by spray drying. More specifically, the average particle size of the pycoxycam-containing nanoparticles according to the present invention may be 500 to 1,000 nm. In addition, charges on the surface of the particles are charged, so that aggregation between the particles can be reduced.
In the present invention, the sub-micron sized pycoxycam-containing nanoparticles prepared by the electrospray method have a smaller particle size and uniformity than conventional pycoxycam powder, improved solubility and dissolution characteristics of the drug, higher bioavailability , The drug in the nanoparticle stably exists in an amorphous form.
In a preferred embodiment, in the examples herein, PYROXYCAM and polyvinylpyrrolidone (PVP) are completely dissolved in ethanol in a weight ratio of 1: 9 to 3: 7 and sprayed in an electrospray apparatus , Injection rate 0.09 ml / hr, bolt amount 11-13 kV, and distance from the
The pyroxycam-containing nanoparticles prepared by the present invention can be prepared in pharmaceutical form together with pharmaceutically acceptable additives. The additive can improve the preparation, compressibility, appearance and taste of the preparation and can be used as a stabilizer, a surfactant, a lubricant, a solubilizer, a buffer, a sweetener, a base, an adsorbent, a mating agent, a binder, a suspending agent, A thickening agent, an antistatic agent, a colorant, a sugar, an isotonic agent, a softening agent, an emulsifying agent, a pressure-sensitive adhesive, a thickening agent, a foaming agent, a thickening agent, , a pH adjusting agent, an excipient, a dispersing agent, a disintegrant, a waterproofing agent, an antiseptic, a preservative, a solubilizer, a solvent, a fluidizing agent and the like may be added as required. Other conventional excipients known in the art may also be included .
The solid preparation in the present invention may be exemplified by tablets, powders, granules or capsules. The shape of the tablet is not particularly limited, and it may be an uncoated tablet having a shape such as a circle, an ellipse, a rectangle, and a coated tablet of the above-mentioned shape. In addition, the solid preparation of the present invention may be a multi-layer tablet, a press-coated tablet or a press-coated tablet such as a group tablet, a two-layer tablet and a three-layer tablet prepared by mixing two or more kinds of granules.
The present invention improves the solubility and dissolution characteristics of PYROXYCAM to increase the bioavailability of PYROXYCAM and speeds up the expression time, thereby solving the problems of poor drug efficacy as well as inconvenience of use in existing oral solid preparations .
FIG. 1 shows a single nozzle spinning spraying apparatus used in this embodiment.
Fig. 2 shows the solubility of the drug in the Pycoxycamnoparticles and the powder particles (the mean ± SD, n = 3). S1 is a nanoparticle in which piroxycam and povidone are blended in a weight ratio of 1: 9, S2 is a nanoparticle blended with piroxycam and povidone in a weight ratio of 2: 8, S3 is a piroxicam Cam and povidone in a weight ratio of 3: 7.
Figure 3 shows the elution profiles of the Pycoxycamnon particles and the powder particles (the mean ± SD, n = 6). S1 is a nanoparticle in which piroxycam and povidone are blended in a weight ratio of 1: 9, S2 is a nanoparticle blended with piroxycam and povidone in a weight ratio of 2: 8, S3 is a piroxicam Cam and povidone in a weight ratio of 3: 7.
4 shows the particle size and particle distribution of the Pycoxycamnon particles and the powder particles. Piroxicam represents the Piroxocam nanoparticles, and S2 represents the nanoparticles blended with Piroxycam and Povidone in a weight ratio of 2: 8.
FIG. 5 is a scanning electron micrograph (SEM) photograph of the PXC powder and the PXC nanoparticle. FIG.
Figure 6 shows differential scanning calorimetry (DSC) patterns of (A) PYLOCYCAM POWDER, (B) PYVIDONE, (C) physical compounds of PYROXYCAM and povidone, and (D) .
FIG. 7 is a graph showing X-ray diffraction (PXRD) analysis of the physical compounds of (A) PYXYCAM POWDER, (B) Povidone, (C) PYROXYCAM and povidone, and (D) Pattern.
Figure 8 shows the time-to-blood concentration profile of oral carcinoma nanoparticles and powder particles in rats (the mean ± SD, n = 6). * ≪ / RTI > indicates P < 0.05 as compared with the Plioxycam powder.
Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.
Example One. Pirocci Kam Manufacture of nanoparticles
1-1. Experimental material
Piroxycam was received from Hanyin Pharmaceutical Co., Ltd. (Suwon, Korea), and naproxen was received from Hanmi Pharmaceutical Co., Ltd. (Hwasung, Korea). Polyvinylpyrrolidone (PVP, K30) was purchased from BASF (Ludwigshafen, Germany). Other compounds were HPLC grade, purified or used without purification.
1-2. Pirocci Kam Manufacture of nanoparticles
Pirocci cam nanoparticles were prepared using a single-nozzle electrospraying setup to form particles in a single jet (ES-100 Nano NC Seoul, Korea) (FIG. 1). The electrospray system consists of a voltage power source with a high voltage output, a mechanical syringe pump with high accuracy at an adjustable injection speed, and a 21 gauge stainless steel nozzle. Povidone (Povidone, polyvinylpyrrolidone, PVP) was dissolved in 0.1 M NaOH (pH 5) in a weight ratio of 1: 9 (denoted as S1), 2: 8 (denoted as S2) and 3: Completely dissolved in ethanol, placed in a 1 ml syringe and placed on the pump. Next, the mechanical pump was pushed into the stainless steel nozzle with the solution filled in the syringe. The voltage was applied and the jet was fired at the tip of the nozzle. In all of the three solutions (S1, S2, S3), the spraying conditions were an injection speed of 0.09 ml / hr, an applied voltage (bolt amount) of 11-13 kV and a distance from the nozzle tip of 20 cm. Pycoxycam nanoparticles were collected on an aluminum foil sheet, and the produced Pycoxycamnano particles were produced in a spherical shape with a yield of 90% or more.
Example 2. Solubility test
To determine the solubility of the Pycoxycamnano-particles, excess Pycoxycam powder and Pycoxycamnoparticles were added to 2 ml microtube (Axygen MCT-200) containing 1 ml of water and diluted in water bath at 25 占 폚 For 3 days. The solution was centrifuged at 3000 g for 10 minutes and then filtered through a membrane filter. The filtrate (50 μl) was subjected to HPLC (Agilent 1220 Infinity; Agilent Technologies, Santa Clara, Calif., USA, an Inertsil ODS-3 C18 column The mobile phase was 0.1 M sodium acetate-acetonitrile-triethylamine (61: 39: 0.05, v / v) with a flow rate of 1.5 mL / min and a UV absorption value of 330 nm.
As a result, the PXC nanoparticles S1, S2 and S3 both increased the solubility significantly compared to the PXC powder, and the nanoparticles S2 and S3 similarly increased the solubility and increased the solubility more than S1. In particular, S2 had a solubility of 3313.67 ± 88.7981 μg / ml and increased the solubility (5.68 ± 0.0619 μg / ml) of the Plexoxime powder by about 600 times (Figure 2).
Example 3. Dissolution test
(
As a result, the PXC nanoparticles S1, S2, and S3 significantly increased drug elution than the PXC powder. When the dissolution rate of the drug after 5 minutes was compared, the Pycoxycamnoparticles S2 and S3 increased dissolution similarly, and the dissolution was further increased than that of S1. In addition, S2 had a drug dissolution rate of about 50% by weight at 60 minutes, and increased the dissolution rate (about 3% by weight) of the Plioxicam powder by about 16 times (FIG. 3).
Example 4. Pirocci Kam Evaluation of morphology, crystal form and size of nanoparticles
The morphology and surface of the Pycoxycamnano particles were examined using a scanning electron microscope (S-4800, Hitachi; Tokyo, Japan). S2 was used as the polycrystalline nanoparticle. The crystal form was evaluated using a differential scanning calorimeter (DSC Q200; TA Instruments, New Castle, DE, USA) and X-ray powder diffraction (D / MAX-2500 PC, Rigaku Corporation; Tokyo, Japan). Particle size and particle distribution were also evaluated using a particle size analyzer (H1918; Sympatec GmbH, System-Partikle-Technik, Clausthal-Zellerfeld Saxony, Germany).
As a result, the Pycoxycarbon nanoparticles showed a smaller particle size distribution and a uniform particle size distribution compared to the Pycoxiocin powder (about 20 μm), and about 70% or more of the nanoparticles were 500-1000 nm in size 4).
In addition, SEM photographs of the Plioxycam powder and the Pycoxycam nanoparticles showed that the Plioxicam powder was heterogeneous hexagonal crystal (FIG. 5A) while the nanoparticles had a smooth and spherical surface (FIG. 5B).
In addition, the DSC pattern of the Plioxycam powder and the Plioxycamp nanoparticle showed that the Plioxicam powder had a peak estimated at about 190 ° C as a melting point, indicating that the pure drug was in a crystalline state (FIG. 6A). Povidone did not show a specific peak and showed a low endothermic peak at 100 DEG C due to its glass transition temperature (Fig. 6B). In addition, the physical mixture prepared by simply mixing povidone and pyrroxycam in a weight ratio of 1: 1 slightly showed a specific peak of the pinkoxam powder (FIG. 6C), but the pinkoxil nanoparticles showed a specific peak of the pinkoxam powder , Indicating that the drug has been converted to amorphous form in the formulation (Figure 6D).
In addition, at the X-ray peak, the PXC powder exhibited a regular crystal pattern showing several distinct peaks at a specific diffraction angle (Fig. 7A), and povidone and plexoxymia were mixed in a ratio of 1: 1 This pattern was also observed in the prepared physical mixture (Fig. 7C). Since the picoxican nanoparticles did not show such a specific peak, it was judged that the pycoxycam powder in the nanoparticles changed into a crystalline form and became amorphous (Fig. 7D).
Example 5. Pirocci Kam In vivo dynamics of nanoparticles
Animal experiments were conducted in accordance with the NIH Policy and Animal Welfare Act with the approval of Hanyang University's Institutional Animal Care and Use Committee (IACUC).
Twelve Sprague-Dawley male rats (280 ± 20 g, 6-8 weeks of age) (Nara Biotech, Seoul, Korea) were fasted for 12 hours prior to the experiment and divided into two groups. Approximately 10 mg / kg of Plexoxymes powder or Plexoxamine nanoparticles S2 were administered per group, respectively. Anesthetized rats were cannulated into the femoral artery by cannulation of the polyethylene tube, and the pyloxicam powder or nanoparticles filled with very small capsules (# 9, Suheung capsule Co .; Seoul, Korea) ) Were orally administered, 0.3 ml of blood was collected from the femoral artery at a constant time, and centrifuged at 6,000 g for 10 minutes (Eppendorf, USA). 0.01 ml of naproxen (50 μg / ml in methanol) and 0.2 ml of acetonitrile were added to plasma (0.16 ml) and centrifuged at 6,000 g for 10 minutes. The concentration of the drug in the plasma was measured by the above quantitative method with 50 μl of this solution.
As a result, the plasma concentration of the pycoxycam in the whole Pycoxiocin nanoparticles was higher than that of the Pycoxycam powder, and the initial plasma concentration was significantly increased up to 5 hours as compared with the Pycoxycam powder (P < 0.05, FIG. 8). This increase in initial blood concentration is thought to be due to the increase in solubility and dissolution of the drug by the nanoparticles. In addition, the PXC nanoparticles significantly increased area under the concentration-time curve (AUC) and maximum plasma concentration (P <0.05, Table 1) as compared with the PXC powder, Indicating a threefold increase in utilization. Thus, it can be seen that the Pycoxycamnano particles are oral preparations having increased absorption than the Pycoxycam powder.
* P <0.05 compared with Piroxicam powder
Claims (6)
And spraying the dissolved solution with a voltage applied thereto.
A method for producing nano particles containing a pyroxican.
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KR101892731B1 (en) | 2017-08-07 | 2018-08-29 | 한국기계연구원 | Spherical ceramic granules and manufacturing method thereof |
US11801222B2 (en) | 2017-04-14 | 2023-10-31 | Korea Institute Of Materials Science | Manufacturing method for granule |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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KR930021176A (en) | 1992-04-28 | 1993-11-22 | 타이도 나오카타 | Pyroxycam tablets and preparation method thereof |
KR20120109549A (en) | 2009-12-15 | 2012-10-08 | 데이고꾸세이약꾸가부시끼가이샤 | Piroxicam-containing endermic preparation |
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KR930021176A (en) | 1992-04-28 | 1993-11-22 | 타이도 나오카타 | Pyroxycam tablets and preparation method thereof |
KR20120109549A (en) | 2009-12-15 | 2012-10-08 | 데이고꾸세이약꾸가부시끼가이샤 | Piroxicam-containing endermic preparation |
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US11801222B2 (en) | 2017-04-14 | 2023-10-31 | Korea Institute Of Materials Science | Manufacturing method for granule |
KR101892731B1 (en) | 2017-08-07 | 2018-08-29 | 한국기계연구원 | Spherical ceramic granules and manufacturing method thereof |
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