WO1992018106A1 - Method of manufacturing solid dispersion - Google Patents
Method of manufacturing solid dispersion Download PDFInfo
- Publication number
- WO1992018106A1 WO1992018106A1 PCT/JP1992/000470 JP9200470W WO9218106A1 WO 1992018106 A1 WO1992018106 A1 WO 1992018106A1 JP 9200470 W JP9200470 W JP 9200470W WO 9218106 A1 WO9218106 A1 WO 9218106A1
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- WO
- WIPO (PCT)
- Prior art keywords
- hydrochloride
- ray diffraction
- solid dispersion
- powder
- test
- Prior art date
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Classifications
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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
- A61K9/1682—Processes
- A61K9/1694—Processes resulting in granules or microspheres of the matrix type containing more than 5% of excipient
-
- 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
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
Definitions
- the present invention translates into a method for producing a planar dispersion. More specifically, the present invention relates to a method for producing a solid dispersion using a twin-screw extruder, and can be mainly used in the field of pharmaceutical production.
- the term “hedron-body” refers to one of drug substance-containing drug substance powders in which a drug is dissolved or dispersed in a polymer carrier.
- Solid dispersions are very useful for increasing the solubility of a drug, controlling the release rate of a drug from a drug product, improving bioavailability, etc. The need is great.
- Conventional methods for producing a solid dispersion include a melting method in which a drug and a polymer carrier are heated and melted and then cooled, and a method in which the drug and the polymer carrier are dissolved in an appropriate solvent, There is a solvent method characterized by the removal of water, a melt-solvent method combining both features, and the like.
- the fusion method has a drawback that it is decomposed by heat or is likely to be decomposed or cannot be used for molecular support.
- the solvent method does not have the drawbacks of the above-described melting method, but has the following drawbacks because an organic solvent such as an alcohol-chlorine solvent is used.
- An object of the present invention is to establish a method for producing an excellent facet fraction overcoming the above-mentioned drawbacks inherent in the fusion method and the solvent method.
- the gist of the present invention resides in that a mixture of a drug, a polymer carrier, and the like, which are components of a facepiece, is treated with a two-glaze extruder.
- 2 tt type extruder is a type of front-discharge extrusion granulator characterized by having two screws, and is a single-shaft extruder having only one screw. It has a different structure from a truder.
- the 2-axis ETAS trusser is a metering machine, barrel (cylinder), screw, paddle, screw pot, barrel heating / cooling device, exit die (cooling die, heating die, molding die), It is a device that can change the pressing force and kneading temperature during the kneading process by changing the screen type, rotation speed, and the combination of the screw elements on the glaze.
- the barrel can be used in combination of length and type depending on the application, and temperature control is possible if necessary.
- twin-screw extruder requires only two screws. Material can be processed and the screw elements on the shaft can be rearranged, etc., so it has superior features that are incomparable to single-screw extruders, for example: .
- the screws do not interfere with each other, and the raw materials do not rotate together with the screws. Therefore, the characteristics of the processing raw materials are not so affected. Therefore, the 2 ⁇ type extruder can process even high oil content and long-lasting raw materials that cannot be processed by the 1 shaft type extruder.
- twin-screw extruder is superior to the 1tt-type etrus extruder in terms of shearing force, mixer, and transport capacity. Therefore, for example, when processing a protein, organization of the protein, which is not possible with a single-axis extruder, is possible with a two-axis extruder.
- the two-wheel extruder has a low frictional heat with the barrel, so it is easy to control the temperature. Therefore, the 2suke type extruder is advantageous for pharmaceuticals and the like that do not like commercial temperature.
- the macromolecular carrier used in the present invention is a natural or synthetic high molecular compound that can be generally used as a raw material for pharmaceutical preparations, and loses its function when discharged from the pores of the die of the biaxial Etastruder. There is no particular limitation as long as the substance is not used.
- Examples of such a ⁇ ⁇ molecular carrier include ⁇ -dependent polymer carriers, ⁇ independent ⁇ molecular carriers, and water-soluble polymer carriers, and examples thereof include the following polymer compounds.
- Hydroxypropyl methylcellulose phthalate 220824 ( ⁇ 50), hydroxyb D virmethylcell orifice 220731 ( ⁇ 55), Hydroxypropyl methylcellulose acetate succinate (A-coat), carboxymethylethylcellulose (CI BC), tungstic acid fluoric acid cell ⁇ -source (CAP), methacrylic acid cobolimer LD (L30D55) , Meta Ryo Co-Po Limer S (S-100), Amino Alkyl Meta!
- Rate copolymer E gastric solubility
- polybutylacetal getylaminobutyrate ABA
- polybulpyridone K-25, 30, 90; PVP
- ethylcellulose BC
- Meta-acrylic acid copolymer Polymer RS (RS 30D), polybutyl alcohol (PVA), methyl cellulose (MC), hydroxypropyl cellulose (HPC), hydroxymethyl bil methylcell ⁇ -source 2208 (metrose 90SH), Hydroxylab mouth virumethylcellulose 2906 (Methorose 65SH), Hydrodipsiprovir methylcelluose mouth 2910 ⁇ Methorose 60SH), carboxymethylcellulose sodium (sodium fiber glycolate sodium), Dexto Lin, burlan, arabia gum, tragacanth, sodium luginate, propylene glycol alginate, carten , Gelatin, 3 ⁇ 4 flour, pressurized E ⁇ , Li phospholipids (lecithin), Darko mannan like.
- Each of the above polymer carriers can be used alone, or two or more of them can be used as a mixture, if necessary.
- the size of the particle SE of the molecular ft should be a particle diameter that can be put into the machine body from the hopper of the twin-screw extruder. ⁇ It is below. Even larger particles of a polymer carrier can be used by coarse grinding in advance.
- Pressure, temperature, feed rate, water or plasticizer in the production method of the present invention The setting conditions such as the amount of added and the supply rate vary depending on the drug used, the molecular carrier, the type of biaxial extruder, and other conditions. It is important to combine them, and it is necessary to change them according to the desired product characteristics.
- the ratio of mixing the drug and the molecular carrier depends on the type, purpose, spreading properties, etc. of the drug and molecular carrier, but the ratio of the polymer carrier to the drug 1 is 0.1 to 999, preferably 0.1 to 999. 5 to 500, more preferably 1 to 50 is suitable.
- an aqueous solution or a separating solution of the plasticizer can be added before or during the application to the twin-screw type Etrusstruder.
- the degree of transition of the polymer carrier can be reduced, so that the molding temperature can be set below the decomposition temperature of the drug and the quotient molecular carrier, and the decomposition of the drug or polymer carrier by heat can be performed. Can be prevented.
- an aqueous solution or dispersion of a plasticizer can be similarly added to a system containing no heat-labile drug or polymer carrier.
- a plasticizer for lowering the transition temperature of the molecular carrier a compound or the like used as a plasticizer for a film coating agent in the pharmaceutical field can be used.
- the following compounds can be mentioned.
- Cetanol medium chain fatty acid triglyceride, polyoxyethylene—polyoxypropylene glycol (bull nick), macrogol (200, 300, 400, 600, 1000, 1500, 1540, 4000. 6000, 20000). Tritin-cetin, triethyl citrate (citroflex), etc.
- the plasticizer that can be used in the present invention is not limited to these, and any compound that has an effect of reducing the degree of tillering S of the polymer carrier can be used.
- the amount of the plasticizer to be added varies depending on the drug used, the quotient carrier, etc., but 1 to 80% is appropriate for the polymer carrier, and preferably 5 to 50% is quick. .
- the method of addition may be directly from the beginning to the mixture system of the polymer carrier and the drug, or may be one that is permanently dissolved or dispersed during molding. As described above, the method of adding the plastic is not particularly limited.
- the drug that can be used in the present invention is not particularly limited, but a drug that is stable to temperature, particularly a drug that does not decompose at 50T or less is preferable.
- examples of such drugs include the following.
- Dibrofilin Salbutamol triureate, Chlorbrenaline citrate, Formoterol fumarate, Orcibrenaline sulphate, Bilbuterol citrate, Hexobrenalin sulphate, Vitortel succinate, Sigma-cletol hydrochloride, Sulfuric acid hydrochloride, Sulfuric acid Terbutaline, mabuterol hydrochloride, pentoterol hydrobromide, methoxyphenamine hydrochloride.
- Bottle mouth brobranol hydrochloride ⁇ -yl, carteol hydrochloride, methotrolone tartrate, labetalol hydrochloride, oxourenol hydrochloride, acebutol hydrochloride, bufenrolol hydrochloride, alpreno hydrochloride Chinolol, oxalate chinolol, oxprenolol hydrochloride, nadolol.
- Bucumolol hydrochloride indenol hydrochloride, timolol maleate, difunolol hydrochloride, carteolol hydrochloride, bupranolol hydrochloride. 1 7.
- Antiarrhythmic agent ⁇ -yl, carteol hydrochloride, methotrolone tartrate, labetalol hydrochloride, oxourenol hydrochloride, acebutol hydrochloride, bufenrolo
- Feline toine sodium palproate, metal bital, rubbamazevin.
- N-phenylaminate maleate clemastine fumarate, mequitazine, alimemazine tartrate, butadiene cyclate.
- Vitamin Bl Vitamin B2, Vitamin B6, Vitamin B12, Vitamin, Vegetable acid.
- Enalapril maleate, alasepril, delapril hydrochloride Enalapril maleate, alasepril, delapril hydrochloride.
- the solid dispersion obtained according to the present invention can easily obtain solid dispersion particles having an arbitrary particle system by being crushed using an appropriate crusher, and is used as it is as a powder or granule. You can also.
- tablets, granules, fine granules, capsules, or capsules filled with a half-sided dispersion, capsules filled with an oily substance, or the like can be prepared using the pulverized fine particles. It can also be used as a mouth preparation.
- the technology described in the above-mentioned document is a technology that applies a 1 ⁇ -type extruder, which is extremely inferior to a 2-axis extruder, as described above. It is different from the solid dispersion produced. Further, the above-mentioned technology is intended to produce a sustained-release agent, and the greed and sustained-release agent is produced at a high temperature.
- the above technique is different from the present invention, which is a method for producing a face dispersion, which overcomes the disadvantages of the melting method and the solvent method, and has different objects, configurations, and effects.
- a solid dispersion can be obtained without placing a drug and a polymer carrier in a high temperature state and without using any organic solvent.
- a facepiece dispersion body can be formed and taken out independently, and a facepiece dispersion having an arbitrary size or an arbitrary shape can be manufactured by changing the discharge hole diameter ⁇ of the die. .
- Example 1 Compound A (Compound name; Methyl 2,6-dimethyl-14- (2-2-trifluorophenyl) -1-5- (2-oxo-1,3,2-Dioxaphosphorinan-2-yl) 1-1,4-Dihydro 500 g of powdered powder (average particle size: 60 jm) containing powdered viridine-3-carboxylate (hereinafter the same applies) is added to hydroxy ⁇ -hydroxypropyl methylcellulose acetate acetate (trade name: ⁇ Coat) , AS-MP, manufactured by Shin-Etsu Chemical Co., Ltd. The same applies hereinafter.
- This compact is finely pulverized using a sample mill (type: AP-S, manufactured by Hosokawa Iron Works, the same applies hereinafter), and the obtained fine particles are eluted with a test sample (65 to 100 mesh), powder X-rays. Samples were used for diffraction (250 mesh through) and solubility measurement (65 to 100 mesh).
- 500 g of indomethacin was mixed with 2500 g of virmethylcellulose phthalate (trade name; HPMCP, HP-55P grade, manufactured by Shin-Etsu Chemical Co., Ltd .; the same applies hereinafter) to 500 g of indomethacin. While adding a 50% (w / w) aqueous solution of reticle, the molded product was formed by a biaxial extruder equipped with a 4 ⁇ 0X2 die at a barrel temperature of 80t and an extrusion speed of 200rpm. (Solid dispersion) was obtained.
- the compact was pulverized using a sample mill, and the obtained fine particles were used as samples for a dissolution test, powder X-ray diffraction, and solubility measurement.
- Example 3 After mixing 1500 g of indomethacin with 1500 g of polyvinyl terephthalic acid acetyl acetate (trade name; AEA, manufactured by Sankyo Pharmaceutical Co., Ltd.), 50% (w / «) of triacetin was dispersed.
- the barrel temperature was set to 90 'using a twin-screw extruder equipped with a die with a mouth ⁇ X2 while adding the elongate, and the molding process was performed at an extrusion speed of 200 rpn to form a molded body (plane dispersion). Obtained.
- Compound B (Compound name: 4-Jetyl Rmino 1,1-Dimethyl-2-butynyl (Earth) 1-Cyclohexyl or -Phenyldalilate hydrate mouth chloride Monohydrate) 200 g of methacrylic acid Copolymer LD (trade name: Eudragit, Grade; L30D55, Publisher: Kokushokai Co., Ltd.) After mixing 1600 g of wheat starch and 200 g of wheat starch, a die with a diameter of 4 ⁇ 0 X 2 was added while adding (adding) water. The barrel temperature was set to 100 t using a two-mould extruder equipped with, and molding was performed at an extrusion speed of 200 rpoi to obtain a molded body (plane dispersion).
- the barrel temperature was adjusted to 100 t using a twin-screw extruder equipped with a 4 ram 0 X 2 die while adding water.
- the molding was performed at a set extrusion speed of 200 rpro to obtain a molded body (plane body separated body).
- the compact is finely pulverized using a sample mill, and the obtained particles are subjected to a dissolution test (65 to 100 mesh), powder X-ray diffraction (pass through 250 mesh), and a solubility measurement (65 to 100 mesh).
- the barrel temperature was adjusted using a twin-screw extruder equipped with a die of 2 mn 0 x 3 while adding water.
- the molding process was performed at an extrusion speed of 200 ° to obtain a molded product (solid decomposed material).
- the molded product is pulverized vigorously using a sample mill, and the obtained fine particles are subjected to a dissolution test (65 to 100 mesh), powder X bran diffraction (pass through 250 mesh), and a solubility measurement (65 to 100 mesh). ).
- the molded body is finely pulverized using a sample mill, and the obtained fine particles are subjected to a dissolution test (65 to 100 mesh), powder X-ray diffraction (250 mesh pass), and solubility measurement (65 to 100 mesh). Sample.
- the compact was finely pulverized using a sample mill, and the obtained fine particles were used as samples for a dissolution test (65 to 100 mesh) and a powder X-ray diffraction (250 mesh pass).
- Example 1 Extruder-treated product
- Comparative Example 1 the JP Pharmaceutical No. 1 solution (PH1.2), the sample solution 900 nl, the paddle method, Under the conditions of ⁇ , no elution of Compound A was observed as shown by HI.
- rapid elution was observed with the Japanese Pharmacopoeia second solution (PH6.8), test solution 900oil, paddle method, and lOOrpn.
- Example 1 and Comparative Example X-ray powder diffraction of the compact produced in Example 1 resulted in the crystal peak of Compound A observed in the raw powder and in the physical mixture of equal mixing ratio as shown in Figure 2. Had disappeared.
- Table 1 shows the results of measuring the solubility of the test sample prepared in Example 1. As shown in Fig. 1, the solubility was increased about 4 times as compared with the bulk powder. This solubility was almost similar to the solid dispersion prepared by the solvent method of Comparative Example 1. table 1
- Example 5 Weigh indomethacin 35iw equivalent of the test sample obtained in Example 5 and pour it into 900 nl of JP First Solution (PHI. 2), and perform the elution test under the conditions of paddle method and lOOrpnu measurement wavelength of 320 ⁇ >. Carried out. As a result, as shown in FIG. 5, it was confirmed that the release of indomethacin was suppressed, and the release rate was increased as compared with the amount of wheat flour added.
- PHI. 2 JP First Solution
- FIG. 1 shows the results of elution of the isomers. From the start of the test to 180 minutes after the start of the test, the elution results of the first JP (PH1.2) were used. From 180 minutes after the start of the test, the dissolution and narrow results of the Japanese second solution (PH6.8) were obtained. Shown. The horizontal axis represents time (minutes), and the vertical axis represents the dissolution rate (%) of compound A, respectively. In the figure, Hata indicates the elution curve of the solid component obtained in Example 1, and ⁇ indicates the elution curve of the solid component obtained in Comparative Example 1.
- FIG. 2 shows the results of powder X-ray diffraction of a compound A-containing face dispersion.
- the top X-ray diffraction pattern shows the X-ray diffraction result of the solid dispersion obtained in Example 1, and the X-ray diffraction pattern at the second * from the top shows the solid dispersion obtained in Comparative Example 1.
- X »From the diffraction results the third X-ray diffraction from the top 0 shows that the ratio of compound A to hydroxymethyl virmethylcell ⁇ -succinate succinate (A coat, AS-MP grade) is 1: 5 (compound A: The A-coat, the same ratio as in Example 1 and Comparative Example 1).
- the X-ray diffraction result of the physical mixture is as follows. Shown respectively. The horizontal axis represents the diffraction angle (2 ⁇ ), and the vertical axis represents the diffraction intensity (CPS).
- FIG. 3 shows the results of a dissolution test of the solid dispersion obtained from Example 2 obtained in Example 2.
- the horizontal axis is the time (minutes), and the vertical axis is the The dissolution rate (%) is shown.
- FIG. 4 shows the results of powder X-ray diffraction of a solid dispersion containing indomethacin and the like.
- the top X-ray diffraction pattern shows the results of X-ray diffraction of the solid dispersion obtained in Example 2, and the second X-ray diffraction pattern from the top shows indomethacin and hydroxymethyl bil methylcell monophthalate.
- the third X-ray diffraction E shows the X-ray diffraction result of a physical mixture in which the ratio of indomethacin to HPMCP is 1: 5 (indomethacin: HPMCP, the same ratio as in Example 2).
- Diffraction H shows the results of X-ray diffraction of bulk indomethacin powder.
- the «axis indicates the diffraction angle (2), and the slow axis indicates the diffraction intensity (CPS).
- FIG. 5 shows the results of a dissolution test of the indomethacin-shape-planed solid dispersion obtained in Example 5 in the Japanese Pharmacopoeia First Solution (PH1.2).
- the horizontal pot represents the hour K (minutes), and the vertical port represents the elution rate (%) of indomethacin.
- the graph shows the elution curve of the solid dispersion obtained by adding 300 g of wheat flour in Example 5, and the graph shows the elution of the planar dispersion obtained by adding 500 g of wheat flour in Example 5.
- ⁇ represents the elution curve of the solid dispersion obtained by adding 1000 g of wheat »flour in Example 5, respectively.
- FIG. 6 shows the dissolution test results of Nif X divin-containing face dispersion ft obtained in Example 6 and Comparative Example 2.
- the horizontal axis represents time (minutes), and the vertical tt represents the dissolution rate (%) of diphediobin.
- FIG. 1 Shows the results of powder X-ray diffraction of Nifuedibin-Shain-I dispersion.
- the top X-ray diffraction pattern is the X-ray of the solid dispersion obtained in Example 6.
- the X-ray diffraction pattern at the second * from the top is the X-ray diffraction pattern of the solid dispersion obtained in Comparative Example 2.
- the X-ray diffraction pattern at the third from the top is Nifdibin and hydroxypropyl methylcellulose.
- the ratio of acetate succinates (A-coat, AS-P grade) is 1: 5 (diphenyl: A-coat, the same ratio as in Example 6 and Comparative Example 2).
- the X-ray diffraction results are shown, and the X-ray diffraction diagram at the bottom shows the X-ray diffraction results of the raw powder of ufuzivin.
- the horizontal axis represents the diffraction angle (2 ⁇ ), and the gentle axis represents the diffraction intensity (CPS).
- FIG. 8 shows the dissolution test results of the solid oxypeptinin halite obtained in Example 7 and Comparative Example 3.
- the horizontal axis represents time (minutes), and the vertical axis represents the dissolution rate (%) of oxybutun chanate.
- FIG. 9 shows the results of X-ray powder diffraction of a solid dispersion containing oxyptinin-supported acid and the like.
- the top-level X-ray diffraction H is the X-ray diffraction result of the planar solid obtained in Example 7, and the X-ray diffraction at the second * from the top is the X-ray diffraction of the solid sample obtained in Comparative Example 3.
- the X-ray diffractogram of the third test from the top shows that the ratio of oxyptinin hydrochloride to hydroxymethyl mouth virmethylcellulose acetate succinate (A coat, AS-MP grade) is 1: 5 (oxyptinin hydrochloride: X-ray diffraction results of the physical mixture (A coat, Example 7 and Comparative Example 3) are shown, and the X-ray diffraction diagram at the bottom shows the X-ray diffraction results of the raw powder of oxypeptinine hydrochloride.
- the horizontal axis represents the diffraction angle (2 ⁇ ), and the vertical axis represents the diffraction intensity (CPS).
- FIG. 10 shows the dissolution test results of the solid dispersions of dicardipine hydrochloride obtained in Example 8 and Comparative Example 4.
- the horizontal axis represents time M (minutes), and the vertical axis represents the dissolution rate (%) of dicardivine hydrochloride.
- FIG. 11 shows the results of powder X-ray diffraction of a solid dispersion of dicardipine hydrochloride. 3 ⁇ 4The top X-ray diffraction pattern shows the X-ray diffraction result of the solid dispersion obtained in Example 8, and the second X-ray diffraction pattern from the top shows the X-ray diffraction result of the solid dispersion obtained in Comparative Example 4.
- the third X-ray diffractogram from the top shows that the ratio of dicardibin hydrochloride to hydroxymethyl mouth vir methylcellulose phthalate (HPMCP, HP-55P grade) is 1: 5 (dicardibin dibasic acid: HPMCP, Example 8). And the same ratio as in Comparative Example 4), the X-ray diffraction result of the physical mixture, and the X-ray diffraction diagram at the bottom represent the X »diffraction result of the raw powder of dicardivin hydrochloride.
- the horizontal tt indicates the diffraction angle (2), and the potter indicates the diffraction intensity (CPS).
- FIG. 12 shows the results of a dissolution test of the solid dispersions of dichroknack nutshell obtained in Example 9 and Comparative Example 5. Indignation tt indicates time (minutes), and ⁇ ⁇ indicates the elution rate (%) of dichroknack nutrium.
- FIG. 13 shows the results of powder X-ray diffraction of a dispersion of a dihedral napkin-containing cuboid.
- the top X-ray diffraction pattern is the X-ray diffraction result of the solid dispersion obtained in Example 9, and the second X-ray diffraction pattern from the top is the X-ray diffraction result of the planar dispersion obtained in Comparative Example 5.
- the third X-ray diffraction diagram from the top shows that the ratio of Zinc ⁇ -F x NacNa and Hydroxyb mouth bil methylcellulose phthalate (HPMCP, HP-55P grade) is 1: 5 (Diclonapnax (The same ratio as that of HPMCP in Example 9 and Comparative Example 5).
- the X-ray diffraction result of the physical mixture is as follows. Shown respectively. The horizontal bow indicates the diffraction angle (2), and the Sui axis indicates the diffraction intensity (CPS).
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Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK92907654T DK0580860T4 (da) | 1991-04-16 | 1992-04-14 | Fremgangsmåde til fremstilling af en fast dispersion |
DE69222847T DE69222847T3 (de) | 1991-04-16 | 1992-04-14 | Verfahren zur herstellung einer festen dispersion |
EP92907654A EP0580860B2 (en) | 1991-04-16 | 1992-04-14 | Method of manufacturing solid dispersion |
CA002108575A CA2108575C (en) | 1991-04-16 | 1992-04-14 | Method of manufacturing solid dispersion |
KR1019930703143A KR0182801B1 (ko) | 1991-04-16 | 1992-04-14 | 고체 분산체의 제조방법 |
US08/129,133 US5456923A (en) | 1991-04-16 | 1993-12-23 | Method of manufacturing solid dispersion |
GR980400035T GR3025864T3 (en) | 1991-04-16 | 1998-01-08 | Method of manufacturing solid dispersion |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11255491 | 1991-04-16 | ||
JP3/112554 | 1991-04-16 |
Publications (1)
Publication Number | Publication Date |
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WO1992018106A1 true WO1992018106A1 (en) | 1992-10-29 |
Family
ID=14589572
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1992/000470 WO1992018106A1 (en) | 1991-04-16 | 1992-04-14 | Method of manufacturing solid dispersion |
Country Status (12)
Country | Link |
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US (1) | US5456923A (ja) |
EP (1) | EP0580860B2 (ja) |
JP (1) | JP2527107B2 (ja) |
KR (1) | KR0182801B1 (ja) |
AT (1) | ATE159426T1 (ja) |
AU (1) | AU1537292A (ja) |
CA (1) | CA2108575C (ja) |
DE (1) | DE69222847T3 (ja) |
DK (1) | DK0580860T4 (ja) |
ES (1) | ES2111065T5 (ja) |
GR (1) | GR3025864T3 (ja) |
WO (1) | WO1992018106A1 (ja) |
Cited By (18)
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WO1995005809A1 (fr) * | 1993-08-20 | 1995-03-02 | Nippon Shinyaku Co., Ltd. | Preparation restant dans l'estomac, forme moulee gonflee, et procede de preparation |
EP0642786A1 (en) * | 1993-09-14 | 1995-03-15 | Euro-Celtique S.A. | Method for the manufacture of a laxative composition |
EP0665010A4 (en) * | 1992-10-16 | 1996-02-28 | Nippon Shinyaku Co Ltd | METHOD FOR PRODUCING WAX MATRICES. |
EP0665009A4 (en) * | 1992-10-14 | 1996-02-28 | Nippon Shinyaku Co Ltd | PROCESS FOR DISLOCATION OF A CRYSTALLINE STATE. |
EP0729748A4 (en) * | 1993-11-18 | 1997-09-10 | Nippon Shinyaku Co Ltd | METHOD FOR PRODUCING STABLE MEDICINAL PRODUCTS AND PHARMACEUTICAL PREPARATION |
JP2000281561A (ja) * | 1999-03-26 | 2000-10-10 | Ajinomoto Co Inc | 新規溶媒法固体分散体製剤 |
US6139872A (en) * | 1996-08-14 | 2000-10-31 | Henkel Corporation | Method of producing a vitamin product |
US6462093B1 (en) | 1995-08-11 | 2002-10-08 | Nissan Chemical Industries, Ltd. | Method for converting sparingly water-soluble medical substance to amorphous state |
JP2003522097A (ja) * | 1998-02-16 | 2003-07-22 | フイズ インターナショナル リミテッド | 可溶化デリバリーシステムおよび製造方法 |
JP2004505911A (ja) * | 2000-08-03 | 2004-02-26 | ファイザー・プロダクツ・インク | コレステリルエステル転移蛋白質阻害薬の医薬用組成物 |
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- 1992-04-14 DK DK92907654T patent/DK0580860T4/da active
- 1992-04-14 AT AT92907654T patent/ATE159426T1/de active
- 1992-04-14 WO PCT/JP1992/000470 patent/WO1992018106A1/ja active IP Right Grant
- 1992-04-14 EP EP92907654A patent/EP0580860B2/en not_active Expired - Lifetime
- 1992-04-14 ES ES92907654T patent/ES2111065T5/es not_active Expired - Lifetime
- 1992-04-14 JP JP4507772A patent/JP2527107B2/ja not_active Expired - Lifetime
- 1992-04-14 DE DE69222847T patent/DE69222847T3/de not_active Expired - Lifetime
- 1992-04-14 KR KR1019930703143A patent/KR0182801B1/ko not_active IP Right Cessation
- 1992-04-14 CA CA002108575A patent/CA2108575C/en not_active Expired - Lifetime
-
1993
- 1993-12-23 US US08/129,133 patent/US5456923A/en not_active Expired - Lifetime
-
1998
- 1998-01-08 GR GR980400035T patent/GR3025864T3/el unknown
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Cited By (29)
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EP0665009A4 (en) * | 1992-10-14 | 1996-02-28 | Nippon Shinyaku Co Ltd | PROCESS FOR DISLOCATION OF A CRYSTALLINE STATE. |
EP0665010A4 (en) * | 1992-10-16 | 1996-02-28 | Nippon Shinyaku Co Ltd | METHOD FOR PRODUCING WAX MATRICES. |
WO1995005809A1 (fr) * | 1993-08-20 | 1995-03-02 | Nippon Shinyaku Co., Ltd. | Preparation restant dans l'estomac, forme moulee gonflee, et procede de preparation |
EP0642786A1 (en) * | 1993-09-14 | 1995-03-15 | Euro-Celtique S.A. | Method for the manufacture of a laxative composition |
US5525355A (en) * | 1993-09-14 | 1996-06-11 | Euro-Celtique, S.A. | Laxative compositions |
EP0729748A4 (en) * | 1993-11-18 | 1997-09-10 | Nippon Shinyaku Co Ltd | METHOD FOR PRODUCING STABLE MEDICINAL PRODUCTS AND PHARMACEUTICAL PREPARATION |
US6462093B1 (en) | 1995-08-11 | 2002-10-08 | Nissan Chemical Industries, Ltd. | Method for converting sparingly water-soluble medical substance to amorphous state |
US6139872A (en) * | 1996-08-14 | 2000-10-31 | Henkel Corporation | Method of producing a vitamin product |
JP2003522097A (ja) * | 1998-02-16 | 2003-07-22 | フイズ インターナショナル リミテッド | 可溶化デリバリーシステムおよび製造方法 |
JP2000281561A (ja) * | 1999-03-26 | 2000-10-10 | Ajinomoto Co Inc | 新規溶媒法固体分散体製剤 |
JP2004505911A (ja) * | 2000-08-03 | 2004-02-26 | ファイザー・プロダクツ・インク | コレステリルエステル転移蛋白質阻害薬の医薬用組成物 |
JP2007314573A (ja) * | 2000-08-03 | 2007-12-06 | Pfizer Prod Inc | コレステリルエステル転移蛋白質阻害薬の医薬用組成物 |
JP4997683B2 (ja) * | 2000-09-25 | 2012-08-08 | 日本新薬株式会社 | 医薬固体分散体の製法 |
JP2005523895A (ja) * | 2002-02-01 | 2005-08-11 | ファイザー・プロダクツ・インク | コレステリルエステル輸送タンパク質阻害剤の固体非晶質分散物を含む医薬組成物 |
JP2009529516A (ja) * | 2006-03-10 | 2009-08-20 | アボット ゲーエムベーハー ウント コンパニー カーゲー | 活性成分の固体分散体を生産するためのプロセス |
US9414992B2 (en) | 2006-03-10 | 2016-08-16 | Abbvie Deutschland Gmbh & Co Kg | Process for producing a solid dispersion of an active ingredient |
JP2009533320A (ja) * | 2006-03-10 | 2009-09-17 | アボット ゲーエムベーハー ウント コンパニー カーゲー | 活性成分の固体分散体を生産するための改良プロセス |
JP2015038115A (ja) * | 2006-03-10 | 2015-02-26 | アボット ゲーエムベーハー ウント コンパニー カーゲー | 活性成分の固体分散体を生産するための改良プロセス |
US9205027B2 (en) | 2006-03-10 | 2015-12-08 | Abbvie Deutschland Gmbh & Co Kg | Process for producing a solid dispersion of an active ingredient |
JPWO2009038112A1 (ja) * | 2007-09-21 | 2011-01-06 | 塩野義製薬株式会社 | Npyy5受容体拮抗剤を含有する固形製剤 |
WO2009038112A1 (ja) * | 2007-09-21 | 2009-03-26 | Shionogi & Co., Ltd. | Npyy5受容体拮抗剤を含有する固形製剤 |
WO2014073889A1 (en) * | 2012-11-07 | 2014-05-15 | Sk Biopharmaceuticals Co., Ltd. | Solid dispersions of insoluble drug and preparation method thereof |
US9439970B2 (en) | 2012-11-07 | 2016-09-13 | Sk Biopharmaceuticals Co., Ltd. | Solid dispersions of insoluble drug and preparation method thereof |
US9566268B2 (en) | 2012-11-07 | 2017-02-14 | Sk Biopharmaceuticals Co., Ltd. | Solid dispersions of insoluble drug and preparation method thereof |
US9724335B2 (en) | 2012-11-07 | 2017-08-08 | Sk Biopharmaceuticals Co., Ltd. | Solid dispersions of insoluble drug and preparation method thereof |
RU2646491C2 (ru) * | 2012-11-07 | 2018-03-05 | ЭсКей БАЙОФАРМАСЬЮТИКАЛЗ КО., ЛТД. | Твердые дисперсии нерастворимого лекарственного средства и способы их приготовления |
US9669047B2 (en) | 2012-12-27 | 2017-06-06 | Kao Corporation | Method for producing polyphenol composition |
US10894058B2 (en) | 2014-08-29 | 2021-01-19 | Kao Corporation | Method for producing solid dispersion containing hardly soluble polyphenol |
JP7082067B2 (ja) | 2016-05-13 | 2022-06-07 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 溶融押出用途のためのポリマーの粒子サイズおよび分布 |
Also Published As
Publication number | Publication date |
---|---|
CA2108575A1 (en) | 1992-10-17 |
DK0580860T4 (da) | 2005-03-21 |
KR0182801B1 (ko) | 1999-05-01 |
DE69222847D1 (de) | 1997-11-27 |
ES2111065T5 (es) | 2005-06-16 |
EP0580860B2 (en) | 2004-12-15 |
DK0580860T3 (da) | 1998-05-25 |
CA2108575C (en) | 2002-10-22 |
AU1537292A (en) | 1992-11-17 |
EP0580860B1 (en) | 1997-10-22 |
DE69222847T2 (de) | 1998-05-20 |
GR3025864T3 (en) | 1998-04-30 |
JP2527107B2 (ja) | 1996-08-21 |
ATE159426T1 (de) | 1997-11-15 |
EP0580860A1 (en) | 1994-02-02 |
DE69222847T3 (de) | 2005-09-15 |
EP0580860A4 (en) | 1994-06-15 |
US5456923A (en) | 1995-10-10 |
ES2111065T3 (es) | 1998-03-01 |
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