WO2006028074A1 - 微粒子化された物質の製造方法および微粒子化された物質 - Google Patents
微粒子化された物質の製造方法および微粒子化された物質 Download PDFInfo
- Publication number
- WO2006028074A1 WO2006028074A1 PCT/JP2005/016301 JP2005016301W WO2006028074A1 WO 2006028074 A1 WO2006028074 A1 WO 2006028074A1 JP 2005016301 W JP2005016301 W JP 2005016301W WO 2006028074 A1 WO2006028074 A1 WO 2006028074A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fine particles
- particle size
- substrate
- substance
- fine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 42
- 239000000126 substance Substances 0.000 title abstract description 18
- 239000002245 particle Substances 0.000 claims abstract description 47
- 239000010419 fine particle Substances 0.000 claims abstract description 44
- 239000000758 substrate Substances 0.000 claims abstract description 29
- 238000002425 crystallisation Methods 0.000 claims abstract description 10
- 239000002270 dispersing agent Substances 0.000 claims abstract description 10
- 239000013543 active substance Substances 0.000 claims abstract description 6
- 239000002244 precipitate Substances 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 9
- 239000013076 target substance Substances 0.000 claims description 4
- 230000001376 precipitating effect Effects 0.000 claims 1
- 239000013077 target material Substances 0.000 claims 1
- 238000009826 distribution Methods 0.000 abstract description 19
- 230000008025 crystallization Effects 0.000 abstract description 3
- 230000004931 aggregating effect Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 27
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002994 raw material Substances 0.000 description 11
- 239000003814 drug Substances 0.000 description 10
- 239000002105 nanoparticle Substances 0.000 description 10
- 229960002989 glutamic acid Drugs 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 238000004220 aggregation Methods 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
- 239000002002 slurry Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000002296 dynamic light scattering Methods 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000012454 non-polar solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000696 magnetic material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
-
- 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
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0021—Intradermal administration, e.g. through microneedle arrays, needleless injectors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0004—Crystallisation cooling by heat exchange
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0063—Control or regulation
Definitions
- the present invention relates to a method for producing a finely divided substance and a finely divided substance.
- the methods include a breakdown method in which a bulk is reduced to a nano size by enclosing a bulk and a cluster-sized fine particle is grown to increase to a nano size.
- the build-up method is roughly divided into two methods.
- a force that can be classified as a breakdown method is the ball mill method (see, for example, Patent Document 1).
- this method can obtain pharmaceutical fine particles smaller than 400 nm, it avoids the inclusion of foreign substances such as grinder materials. There is a disadvantage that it is not possible.
- both breakdown and build-up methods have the disadvantage that control of the particle size of the resulting fine particles is difficult, and that the particle size distribution becomes large. Because of its easy-to-collect nature, it is usually necessary for both breakdown and build-up methods to use a dispersing agent such as a surfactant to prevent the aggregation of the fine particles, which is desirable for pharmaceuticals. I can't avoid mixing the compounds.
- Patent Document 1 US Pat. No. 5,145,684 Specification
- Patent Document 2 US Patent Application Publication No. 2003Z0049323
- an object of the present invention is a method for producing a material finely divided by a crystallization method, and obtains fine particles having a narrow particle size distribution.
- an object of the present invention is to provide a method for producing a granulated substance and a finely divided substance that can suppress aggregation between fine particles without using a dispersant.
- the inventors of the present invention have a narrow particle size distribution by bringing a supersaturated solution into contact with a substrate having a large number of fine protrusions when performing a crystallization method.
- the inventors have found that fine particles not containing a dispersant can be produced without agglomerates, and reached the present invention.
- the first gist of the present invention is a method for producing a substance micronized by a crystallization method, wherein a solution containing a target substance to be micronized is prepared, and fine protrusions are formed on the surface.
- the present invention lies in a method for producing a material finely divided by a crystallization method, wherein fine particles are precipitated by contacting with a substrate having a density of cm 2 or more.
- the second gist of the present invention resides in the fine particles of the physiologically active substance obtained by the production method described above, which do not contain a dispersant.
- fine particles having a narrow particle size distribution can be obtained, and aggregation can also be suppressed without using a dispersant. Therefore, for example, in pharmaceuticals that are hardly soluble in water, the bioavailability can be increased by increasing the specific surface area by increasing the particle size and improving the dissolution rate.
- a physiologically active substance such as nano-particle pharmaceuticals that do not contain undesirable compounds such as dispersants.
- the target substance (raw material) to be microparticulated by the crystallization method is not particularly limited as long as it is soluble in a solvent.
- the solubility of the raw material in the solvent is usually 1 mgZml or more, preferably 5 mgZml or more.
- constituent materials such as pharmaceuticals, inks, pigments, cosmetics and the like that require particles having an average particle size of less than 1 ⁇ m are preferable.
- pharmaceuticals that are sparingly soluble in water is usually 10 mgZml or less, preferably 10 mgZml or less) can be biodiversified by increasing the specific surface area by increasing the specific surface area and improving dissolution rate.
- it is preferable because it can be administered in the right place because the timing of incorporation into the body is aligned by aligning the particle size distribution.
- the solvent can be appropriately selected from those having a solubility of the starting material of usually 1 mgZml or more, preferably 5 mgZml or more, depending on the kind of the starting material.
- the solvent is preferably in a liquid state at a temperature of at least 0 to 30 ° C., and particularly preferably in a liquid state at 20 to 30 ° C.
- Specific examples of the solvent include water; polar solvents such as alcohol, acetone, tetrahydrofuran (THF), methyl ethyl ketone (MEK), and dimethyl sulfoxide (DMSO); nonpolar solvents such as ether, toluene, and chloroform. Can be mentioned.
- a non-polar solvent is preferred as the solvent when water is the preferred oil-soluble compound.
- the solubility is changed by a temperature raising / lowering operation of the solution.
- a nonpolar solvent can be used as a solvent, and vice versa.
- the substrate that is brought into contact with the solution containing the raw material in a supersaturated state has fine protrusions on the surface.
- the density of the fine protrusions is a force that is essential to be 100 Zcm 2 or more, preferably 10,000 Zcm 2 or more, and more preferably 100 million Zcm 2 or more.
- the upper limit of the density of fine protrusions is usually 10 billion Zcm 2 . If the density of the fine protrusions is less than the above range, it is difficult to produce the desired fine particles.
- the shape of the fine protrusions is a cone, a truncated cone, a polygonal pyramid, a polygonal truncated cone, a cylinder
- the shape is not limited, but it is thought that the shape of the fine protrusions may affect the shape of the precipitated fine particles.
- each of the fine protrusions formed at the above-mentioned density has substantially the same shape.
- the lower limit of the height of the fine protrusion is usually 10 nm, preferably 50 nm, and the upper limit is usually 5,000, preferably 1, OOOnm.
- the arrangement of the fine protrusions on the substrate surface preferably has regularity in surface area of the particle size distribution, for example, a staggered arrangement, a hexagonal arrangement, a cubic arrangement, and the like.
- the material of the substrate having fine protrusions on the surface is capable of forming the fine protrusions described above, and has a solvent resistance to the solvent of the solution to be contacted, and also has a solute and chemical structure. Although it will not specifically limit if it does not raise
- a method for forming fine protrusions for example, a method in which nickel is applied to an original plate patterned by a semiconductor lithography method or an interference exposure method, or a semiconductor is vapor-grown on a substrate.
- a method of self-organizing island-like protrusions can be used.
- the protrusion surface may be hydrophobized or conversely hydrophilized.
- a solution having a saturation solubility lower than that of the raw material is used.
- the substrate may be brought into contact with the substrate after being in a supersaturated state.
- the surface of the substrate surface may regularly deposit the fine particles of the source material on the tops of the fine protrusions on the substrate surface, Z, or side surfaces or valleys of the protrusions.
- the solution is brought into a supersaturated state.
- a method of lowering the temperature of the solution there are a method of lowering the temperature of the solution and a method of lowering the concentration of the solute by evaporating the solvent in order to bring the solution of less than the saturation solubility into the supersaturated state.
- a method of lowering the temperature of the solution is preferable.
- the temperature range to be lowered is usually in the range of 1 to 100 ° C.
- the fine particles of the raw material become the top of fine protrusions on the surface of the substrate, Z, or the side surfaces or valleys of the protrusions. It is deposited around the protrusion.
- the deposited fine particles of the raw material may be crystalline or amorphous.
- the crystal system of the deposited fine particles can be controlled by the crystal structure of the surface of the fine protrusions on the substrate surface.
- the fine particles precipitated as described above are recovered after removing the residual solution.
- a force that requires a complicated operation such as filtration and centrifugation in order to separate the fine particles from the residual solution.
- the fine particles and the residual solution can be easily separated by a method of washing the whole, a method of blowing off the residual solution with an inert gas such as air or nitrogen, or a method combining these methods.
- the fine particles can be recovered in a slurry state by a method of ultrasonication in a poor solvent, a method of flowing a solvent having a medium solubility, a method of heating the substrate by dipping in the poor solvent, or the like. I can do it.
- the obtained fine particle slurry adheres to the periphery of the fine protrusions on the surface of the substrate until it is separated from the substrate after being deposited on the surface of the substrate, so that mutual contact is avoided. Aggregation is suppressed, and it can be used in a state where nanoparticle aggregation does not proceed by promptly performing the desired operation thereafter. Even if the aggregation proceeds to some extent, ultrasonic treatment or the like can be performed. It is easy to redisperse by a simple method.
- the production method of the present invention is excellent in controllability of the size and particle size distribution of the fine particles, and the average particle size of the obtained fine particles is usually in the range of 1 nm to less than 1 mm, preferably 1 nm to less than 500 ⁇ m. In the range of 1 nm or more and less than 50 ⁇ m, particularly preferably in the range of 1 nm or more and less than 1 ⁇ m.
- the average particle diameter means a weight average particle diameter.
- the weight average particle diameter can be measured by a dynamic light scattering method.
- the fine particles obtained have the following narrow particle size distribution. That is, in the weight conversion distribution, 90% of the total weight is similarly applied to the 50% by weight particle size (D) under the sieve, which is the diameter that gives a particle group up to 50% by weight of the total weight.
- the particle size distribution is 2 or less, preferably 1. 8 or less, particularly preferably 1.5 or less, with few coarse particles.
- particles with a diameter of 10% by weight under the sieve (D), which is the diameter that gives a group of particles up to 10% by weight of the total weight, are also particles with up to 50% by weight of the total weight.
- the ratio (D / ⁇ ) of the 50% by weight particle size (D) under the sieve, which is the diameter giving the subpopulation, is usually 2 or less, preferably
- the particle size distribution can be measured by a dynamic light scattering method.
- L-glutamic acid was weighed out and poured into 10 ml of water in a 30 ml screw cap bottle to prepare a solution.
- the solubility of L-glutamic acid in water at 20 ° C is 7.2 mgZml, whereas the concentration of the prepared L-glutamic acid solution is 6.2 mgZml, which is below the saturation solubility.
- a SUS bulb having a flat surface of 19 x 23 mm on the bottom surface is fixed upside down, and a pyramidal nickel with a height of 450 nm is formed on the surface by a semiconductor lithography method at intervals of 450 nm in length and breadth.
- microprojections are patterned Jung at a density of 500 million ZCM 2, the rear surface is a flat surface, size 9 X 10 mm, place the substrate having a thickness of 0. 3 mm, on the substrate, at room temperature, resulting in the After 0.05 g of the resulting solution was dropped with a micropipette to form droplets, a refrigerant cooled to 0 ° C. was continuously passed through the valve and maintained for 16 minutes. Since the solubility of L-glutamic acid in water at 0 ° C was 3.3 mgZml, the solution was assumed to be supersaturated and L-glutamic acid fine particles were precipitated.
- the obtained L-glutamic acid nanoparticles are nanoparticles including a dispersant such as a surfactant.
- Example 2 When 5 ml of the same solution used in Example 1 was put in a ⁇ vial, immersed in a refrigerant at 0 ° C. and kept for 16 minutes, a cloudy fine particle slurry was obtained. The particle size distribution of this slurry was measured in the same manner as in Example 1. As a result, the average particle size was 8 m, and D
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Peptides Or Proteins (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05781937A EP1797934A4 (en) | 2004-09-07 | 2005-09-06 | METHOD FOR MANUFACTURING FINULY PARTICULATE SUBSTANCE AND FINALLY PARTICULATE SUBSTANCE |
US11/713,811 US20070193502A1 (en) | 2004-09-07 | 2007-03-05 | Method of producing fine particle-like materials, and fine particle-link materials |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004259487 | 2004-09-07 | ||
JP2004-259487 | 2004-09-07 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/713,811 Continuation-In-Part US20070193502A1 (en) | 2004-09-07 | 2007-03-05 | Method of producing fine particle-like materials, and fine particle-link materials |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006028074A1 true WO2006028074A1 (ja) | 2006-03-16 |
Family
ID=36036355
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2005/016301 WO2006028074A1 (ja) | 2004-09-07 | 2005-09-06 | 微粒子化された物質の製造方法および微粒子化された物質 |
Country Status (3)
Country | Link |
---|---|
US (1) | US20070193502A1 (ja) |
EP (1) | EP1797934A4 (ja) |
WO (1) | WO2006028074A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102858682A (zh) * | 2010-03-22 | 2013-01-02 | 株式会社Bio-Synectics | 纳米颗粒制备方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1878602A (zh) * | 2003-11-28 | 2006-12-13 | 三菱化学株式会社 | 有机化合物微粒的制造方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01274803A (ja) * | 1988-04-28 | 1989-11-02 | Toshiba Corp | 過冷却液体用結晶化開始装置 |
JPH107500A (ja) * | 1996-06-26 | 1998-01-13 | Sumitomo Metal Ind Ltd | 結晶成長方法および結晶成長用固体素子 |
JP2001187301A (ja) * | 2000-01-04 | 2001-07-10 | Sumitomo Metal Ind Ltd | 有機分子の結晶調製装置および結晶調製方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4024057A (en) * | 1976-06-04 | 1977-05-17 | Mccoy Dorothy Joan | Portable, cold grease remover |
US5399363A (en) * | 1991-01-25 | 1995-03-21 | Eastman Kodak Company | Surface modified anticancer nanoparticles |
US5145684A (en) * | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
AU642066B2 (en) * | 1991-01-25 | 1993-10-07 | Nanosystems L.L.C. | X-ray contrast compositions useful in medical imaging |
US5552160A (en) * | 1991-01-25 | 1996-09-03 | Nanosystems L.L.C. | Surface modified NSAID nanoparticles |
EP0909841A4 (en) * | 1996-06-26 | 2001-12-19 | Sumitomo Metal Ind | CRYSTALLOGENESIS PROCESS, SOLID MEMBER AND CRYSTALLOGENESIS DEVICE USED IN THE SAME |
DE10047162A1 (de) * | 2000-09-22 | 2002-04-11 | Basf Ag | Kristallisator mit mikrostrukturierter, selbstreinigender Oberfläche |
CA2458889C (en) * | 2001-08-29 | 2011-06-21 | Dow Global Technologies Inc. | A process for preparing crystalline drug particles by means of precipitation |
-
2005
- 2005-09-06 EP EP05781937A patent/EP1797934A4/en not_active Withdrawn
- 2005-09-06 WO PCT/JP2005/016301 patent/WO2006028074A1/ja active Application Filing
-
2007
- 2007-03-05 US US11/713,811 patent/US20070193502A1/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01274803A (ja) * | 1988-04-28 | 1989-11-02 | Toshiba Corp | 過冷却液体用結晶化開始装置 |
JPH107500A (ja) * | 1996-06-26 | 1998-01-13 | Sumitomo Metal Ind Ltd | 結晶成長方法および結晶成長用固体素子 |
JP2001187301A (ja) * | 2000-01-04 | 2001-07-10 | Sumitomo Metal Ind Ltd | 有機分子の結晶調製装置および結晶調製方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP1797934A4 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102858682A (zh) * | 2010-03-22 | 2013-01-02 | 株式会社Bio-Synectics | 纳米颗粒制备方法 |
CN102858682B (zh) * | 2010-03-22 | 2014-07-16 | 株式会社Bio-Synectics | 纳米颗粒制备方法 |
Also Published As
Publication number | Publication date |
---|---|
EP1797934A8 (en) | 2007-09-26 |
EP1797934A1 (en) | 2007-06-20 |
EP1797934A4 (en) | 2009-09-02 |
US20070193502A1 (en) | 2007-08-23 |
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