WO2003070023A1 - Poudre d'acides amines et procede de production de cette poudre - Google Patents
Poudre d'acides amines et procede de production de cette poudre Download PDFInfo
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- WO2003070023A1 WO2003070023A1 PCT/JP2003/001198 JP0301198W WO03070023A1 WO 2003070023 A1 WO2003070023 A1 WO 2003070023A1 JP 0301198 W JP0301198 W JP 0301198W WO 03070023 A1 WO03070023 A1 WO 03070023A1
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- Prior art keywords
- powder
- amino acid
- amino acids
- spray
- producing
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- 150000001413 amino acids Chemical class 0.000 title claims abstract description 101
- 239000000843 powder Substances 0.000 title claims abstract description 99
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- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims abstract description 35
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 206010019663 Hepatic failure Diseases 0.000 description 2
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Classifications
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid, pantothenic acid
- A61K31/198—Alpha-aminoacids, e.g. alanine, edetic acids [EDTA]
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/17—Amino acids, peptides or proteins
- A23L33/175—Amino acids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P10/00—Shaping or working of foodstuffs characterised by the products
- A23P10/40—Shaping or working of foodstuffs characterised by the products free-flowing powder or instant powder, i.e. powder which is reconstituted rapidly when liquid is added
-
- 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
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
- A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
-
- 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
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates to a fine or granulated powder of amino acids containing torayose, and a method for producing the same.
- amino acids are medical foods for nutritional enhancement, oral and tube-based amino acid preparations for patients with renal or hepatic failure, nutritional formulas for infants and infants It is widely used as a composition, diet food material, health food, and functional food.
- amino acids are also used in veterinary drugs for administration to animals when mixed with cosmetics and feeds.
- trehalose in amino acids is not only a carbohydrate nutrient, but it is also superior in that it can reduce the bitterness of amino acids and does not cause the Maillard reaction (browning reaction).
- Maillard reaction browning reaction
- powders of amino acids coated (coated) with trehalose are known.
- a binder is added to a mixed powder of amino acids, and granules are prepared by an extrusion granulation method.
- a method of atomizing and granulating is disclosed (JP-A-6-227975).
- an aqueous solution containing an amino acid-sugar composition containing at least 13 kinds of amino acids and trehalose is disclosed to improve exercise function. It is said to be effective in improving fatigue (JP-A-2000-72669).
- the spray drying method that can produce fine particles is a drying method in which a solution / fine particle slurry is atomized and dispersed in hot air to obtain spherical and spherical shell-shaped powder dry powder. Pressurized nozzles, rotating disks, two-fluid nozzles, etc. are used. In many cases, the average particle size of dry powder is 20 rr!
- interferon is an essential pharmacologically active ingredient, and selected from leucine, isoleucine, and valine with the aim of preventing deliquescence even when left in high humidity.
- a dry composition for inhalation (average particle size (volume-based distribution) 0.1 m or more and 10 m or less) containing 60% or more and less than 100% of a hydrophobic amino acid to be used is disclosed (Japanese Patent Application Laid-Open No. 235238).
- Example 2 of the publication as a control, a solution for spray drying containing 3.5 g of isoleucine, 0.7 g of serum albumin, 695.8 g of deionized water, and 300 g of ethanol was used. Prepared, The solution is sprayed with a spray drying apparatus to obtain a dry fine powder (aerodynamic average particle diameter 0.98997 m).
- solubility in the mouth, solubility, and taste masking there is no description of solubility in the mouth, solubility, and taste
- An object of the present invention is to develop a dry powder (referred to as a fine powder or a granulated powder) of an amino acid having excellent mouth-solubility and solubility and an excellent taste-masking effect, and a method for drying it by spray drying.
- a dry powder referred to as a fine powder or a granulated powder
- an amino acid having excellent mouth-solubility and solubility and an excellent taste-masking effect
- the inventors of the present invention have studied to solve the above-mentioned problems.As a result, the amino acid solution containing trehalose was dried with a spray drying apparatus capable of forming droplets (fine particles) of several tm, whereby the solubility in the mouth was improved. The present inventors have found that a dry powder of an amino acid having excellent solubility can be produced, and have completed the present invention.
- the present invention includes the following inventions.
- a method for producing an amino acid powder which is a powder of 1 m to 15 / im.
- a method for producing a powder by spray-drying from an aqueous solution containing amino acids wherein the aqueous solution containing amino acids is spray-dried into fine droplets in the presence of treoctose, and spray-dried or sprayed.
- a method for producing an amino acid powder comprising granulating and drying after drying to obtain a granulated powder having an average particle diameter of 20 ⁇ m to 100 m.
- the trehalose is added to the amino acid-containing aqueous solution or supplied as a fine droplet state trehalose solution to a spray dryer and a Z or granulation dryer. ) Or (2).
- the upper line is the spray-dried granulated powder of Example II
- the lower line is the X-ray diffraction chart of the mixed powder before drying of Comparative Example 2.
- the upper line in FIG. 2 is trehalose, the middle line is “amino acid mixed powder” as a raw material of Comparative Example 2, and the lower line is an X-ray diffraction chart of hydroxypropylcellulose powder.
- amino acids used in the present invention are amino acids, amino acid salts, and amino acid derivatives, for example, branched-chain amino acids such as leucine, isoleucine and palin, sulfur-containing amino acids such as cystine and methinenin, and phenylalanine-tyrosine.
- the aqueous solution containing amino acid is
- the target is a solution state or a fine particle slurry solution state (for example, a slurry containing 0.15 m fine particles), and the solvent may include ethyl alcohol or the like.
- Amino acids that are effective when the present invention is applied are preferably amino acids that are relatively insoluble in water, and amino acids having a solubility of 20 g or less per 100 g of water at 20 are particularly suitable for the present invention.
- Preferred amino acids are sparingly soluble amino acids, and are preferred in the present invention when applied to amino acids having a solubility of 5 g or less per 100 g of water at 20 ° C.
- the present invention can be applied to leucine, isoleucine, cystine, phenylalanine, tyrosine, tributan, aspartic acid, and salts and derivatives thereof.
- the amount of amino acids used is not particularly limited, but generally 20 to 95% by weight may be contained in the dry powder, and 50 to 95% by weight if necessary. % By weight, 60% by weight to 95% by weight, and 70% by weight to 95% by weight. The amount used may be determined based on the product design conditions, that is, the balance between the amount of amino acids required as an active ingredient and the specific volume of the dried powder of amino acids.
- the trehalose raw material used in the present invention is a, ⁇ -trehalose, ⁇ , ⁇ -trehalose, ⁇ .) 3-trehalose.
- ⁇ , ⁇ -trehalose which is naturally occurring and inexpensive in cost, is good, and if necessary, a dihydrate having little moisture absorption over time may be used.
- Tehachi (( ⁇ ) Hayashibara Shoji) as a commercial product.
- the content of trehalose (in terms of anhydrous) may be 5% to 80% by weight in the dry powder, and may be 5% to 50%, 5% to 40% by weight, if necessary. It can be from 5% by weight to 30% by weight.
- the amount of trehalose used may be adjusted to the product design conditions as described above.
- the mixture of trehalose and amino acids may be mixed before spray drying, or an aqueous solution containing amino acids as a main component and an aqueous solution containing trehalose as a main component may be simultaneously sprayed during spray drying. You may. After spray-drying an aqueous solution containing amino acids as a main component, the aqueous solution containing trehalose as a main component is coated. It may be sprayed and / or granulated as a binder or binder. If necessary, additives other than trehalose may of course be added.
- a commercially available apparatus for spray drying used in the present invention can be used.
- an apparatus for spray drying having a function of a vertical co-current type is preferable.
- a system having a dehumidifying and drying function because productivity can be maintained even under low-temperature dehumidifying drying conditions, and the quality of dry powder can be maintained at a high level.
- the dehumidifying device a device capable of blowing a large amount of dehumidified dry gas of 1% RH or less is particularly preferable. Examples include the Muntars dry dehumidifier BX series, Nichias HCS series, and the HCP series.
- Spray drying-related equipment includes Micromist Dryer MD series manufactured by Fujisaki Electric Co., Ltd. 1. L-8 type spray dryer. 1. DL-21 type manufactured by Yamato Kagaku Co., Ltd., GB-21 type.
- a spray nozzle capable of generating droplets (fine particles, single particles) having an average particle diameter of 0.1 / im or more and less than 20 tm.
- droplets having an average particle size of 0.1 ⁇ or more and less than 20 Atm, preferably 0.1 / tm to 10 Atm, more preferably 1 rr!
- a dry powder having an average particle size of 0.1 ⁇ to 15 m, preferably 0.1 tm to 7 Atm, and more preferably 0.7 Atm to 6 im is obtained. Since this can be dried in a short time and under low temperature conditions, it is preferable from the viewpoint of maintaining product quality and productivity.
- Fujisaki Electric Co., Ltd.'s four-fluid nozzle Patent No. 2797080. “Chemical Equipment” June 2000, p60-p65) capable of spraying a large number of droplets (eg, I kg / min) 1 Fukusen Manufacturing Co., Ltd. that can spray droplets of / zm to 10 im (example: 150 g / min)
- the four-fluid nozzle is particularly preferable because it can spray a large amount.
- the spray-drying device is a device having a granulating function, or it is preferable that a spray-drying device is additionally provided (referred to as “spray-drying granulating device”).
- the granulated powder is designed to be capable of finishing and drying to a desired moisture content.
- fine particles having a low specific gravity such as amino acids used in the present invention
- fine particles of 0.1 / im to 15 / zm have a drawback that they are difficult to handle. It is preferable to attach a granulation drying device in the state of being linked.
- the granulation size may be appropriately selected as required, and is, for example, 20 / xm to 1,000 m, and preferably 20 Atm to 500 tm.
- the granulation may be performed at the same time as granulation at the same time as granulation, at the same time as fluid granulation after granulation, or at both.
- the material can be finish-dried during and immediately after granulation.
- the conditions of the outlet temperature also referred to as “drying temperature” and “exhaust air temperature”
- inlet temperature outlet relative humidity
- outlet relative humidity inlet relative humidity of the spray-drying granulator
- the outlet temperature of the spray-drying granulation apparatus is from 20 ° C to less than 97, preferably from 20 ° C to 80 ° C, more preferably from 20 ° C to 60 ° C.
- the relative humidity at the outlet of the spray-drying granulator is 1% RH to 50% RH, preferably 3% RH to 35% RH, more preferably 6% RH to 30% RH.
- the inlet temperature of the mist drying granulation apparatus is preferably 60 ° C to 300 ° C, more preferably 70 ° C to 180 ° C. It is not preferable that the condition is lower than 6 mm because the productivity will decrease. If the temperature is higher than 300 ° C., the quality of the dried powder deteriorates, which is not preferable.
- the relative humidity at the inlet of the spray-drying granulation apparatus of the present invention is preferably 35% RH or less, preferably 15% RH or less, more preferably 7% RH or less, and most preferably 1% RH or less. good.
- These more preferable conditions are selected from the viewpoint of maintaining the quality of the product such as suppressing the Maillard reaction and increasing the productivity.
- An example of a spray-granulation apparatus equipped with a granulation function is a filter-on-filter-granulation apparatus with a spray-drying function, "Hybrid Granule Yule-Series J" manufactured by Fujisaki Electric Co., Ltd.
- the outlet temperature of the spray drying device (also referred to as “drying temperature” or “exhaust air temperature”) is 20 ° C to less than 97 ° C, preferably 20 ° C to 80 ° C. And more preferably 20 to 60 ° C. Temperatures lower than 20 ° C are not preferred because productivity is reduced. Further, since the melting point of trehalose is 97 ° C. in the case of dihydrate, and from the viewpoint of maintaining quality, it is preferable to set the temperature range not to exceed this.
- the relative humidity at the outlet of the spray drying apparatus set in the present invention is 1% RH to 50% RH, preferably 1% RH to 35% RH, and more preferably 1% RH to 30% RH.
- the relative humidity at the outlet of the spray drying device referred to in the present invention indicates the relative humidity near the powder collecting portion of the spray drying device.
- the relative humidity at the air discharge portion (exhaust air humidity)
- the inlet temperature of the spray drying apparatus is preferably 60 ° C to 300 ° C, and more preferably 70 ° C to 180 ° C. A lower value of 60 is not preferable because productivity is reduced. On the other hand, if the condition is higher than 300, the quality of the dry powder is undesirably reduced.
- the relative humidity at the inlet of the spray drying apparatus of the present invention is preferably 35% RH or less, preferably 15% RH or less, more preferably 7% RH or less, and most preferably 1% RH or less. .
- the preferable conditions of the inlet temperature, the outlet temperature, the inlet relative humidity, and the outlet relative humidity are selected from the viewpoint of maintaining the quality of the product such as suppressing the mailing reaction and increasing the productivity. is there.
- the amount of dry gas used in the present invention is preferably 0.5 m / min or more, and more preferably 1 m / mii !, particularly from the viewpoint of improving the productivity of dry powder. ⁇ 5 m / min, more preferably 1 m / mii! ⁇ 3.5m / min is good.
- the amount of dry air means the wind speed (m / min) in the cylindrical portion (straight body portion) of the main body of the spray drying device or spray drying granulation device. Fujizaki Electric Co., Ltd.
- Hybrid Dara Niure Igura HGL-130J it can be expressed as the filtration rate.
- aqueous solutions containing amino acids and trehalose The feed rate of the raw material solution is the inlet temperature, Outlet temperature, exhaust air humidity, the other can be set properly in relation to the source solution types and desired particle diameter and the like, the spray pressure is preferably 0. 5 kg / cm 2 or more, more preferably 1 kg / cm 2 to 5 kg / cm 2 , more preferably 1 kg / cm 2 to 3 kg / cm 2 .
- the gas used in the present invention may be air, but may be other than air.
- an inert gas such as nitrogen gas or carbon dioxide gas may be used. Oxidizing substances ⁇ Inert gases are effective when adding substances that are easily denatured.
- the water content (loss on drying) of the dry powder thus produced is preferably 5% or less when dried at 60 ° C. for 5 hours.
- An aqueous solution containing trehalose and an amino acid, or an aqueous solution containing an amino acid and an aqueous solution of trehalose are mixed with a droplet having an average particle diameter of 0.1 Atm or more and less than 20 zm, preferably a liquid of 0.1 m to 10 m.
- the droplets dry instantaneously.
- instantaneously drying at less than 97 ° C., preferably at 20 ° C. to 60 ° C. the trehalose in the dried powder is present in a substantially amorphous state structure. It is considered that the presence of the amorphous state has produced excellent effects such as the solubility of the dry powder in the mouth, the solubility, and the taste masking effect.
- the amino acids according to the method of the present invention, a decrease in the crystallinity was observed, and it is considered that the amount of the amorphous was increased.
- the dry powder thus produced can be used as it is or as an intermediate material in the fields of medicine, cosmetics, etc., such as pathological amino acid preparations for oral and tube administration for patients with renal or hepatic failure.
- foods such as sports drinks, diet food materials, health foods, and functional foods, and amino acid cosmetics can be used in the form of powders, tablets, capsules, and the like.
- the average particle size of the fine powder was measured by visual observation with a microscope, and the average particle size of the granulated powder was determined by “laser light diffraction / scattering microtrack 9320”. The measurement was performed using HRAJ dry particle size distribution measurement system (Honeywe II). (Example 1)
- the flow rate of hot air dehumidified at 25 ° C to a relative humidity of 1% RH is 5.5 m 3 / min (filtration speed about 3 m / min)
- the inlet temperature of the spray-drying granulation apparatus described below is 13 ° C to 139 ° C, and the supply rate of the amino acid aqueous solution is 6.7 to 7.3 kgZhr.
- the flow rate of hot air dehumidified by Munters BX-600 type dehumidified at 25 ° C and a relative humidity of 1% RH
- the inlet temperature of the spray-drying granulator described below was set at 130 ° C to 137 ° C, and the feed rate of the aqueous amino acid solution was set at 6.1 to 7.7 kgZhr.
- Leucine, isoleucine, and valine manufactured by Ajinomoto Co., Ltd.
- Leucine, isoleucine, and valine manufactured by Ajinomoto Co., Ltd.
- Leucine, isoleucine, and valine manufactured by Ajinomoto Co., Ltd.
- a ratio of 47.8% by weight of the amino acid mixed powder 47.8% by weight of trehalose dihydrate ("Treha J" (Hayashibara Corporation)
- Reha J trehalose dihydrate
- hydroxypropylcellulose powder The powder was uniformly mixed.
- the granulated powder containing trehalose had good mouth-solubility, solubility and bitterness masking effects.
- the granulated powder containing sugar (Comparative Example 1) had good solubility, but poor solubility in the mouth, unmasked bitterness, powdery taste, and poor aftertaste.
- FIGS. 1 and 2 show the results of powder X-ray diffraction analysis of each raw material powder such as spray-dried granulated powder containing trehalose (Example 1), powder mixed powder (Comparative Example 2), and trehalose.
- Trehalose in the spray-dried granulated powder of Example 1 was clearly confirmed to be amorphous, which is considered to contribute to the solubility in the mouth and the effect of masking bitterness.
- the dried mist granulated powder (Example 1) also lost the original crystallinity of amino acids.
- the spray-dried granulated powder (Example 1) was found to have a very large amount of amorphous portion as compared with Comparative Example 2 although it was partially crystalline.
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Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2003207244A AU2003207244A1 (en) | 2002-02-22 | 2003-02-05 | Amino acid powder and process for producing the same |
EP03703198A EP1479300B1 (en) | 2002-02-22 | 2003-02-05 | Amino acid powder and process for producing the same |
DE60329744T DE60329744D1 (de) | 2002-02-22 | 2003-02-05 | Aminosäurepulver und verfahren zu seiner herstellung |
JP2003568996A JP4482925B2 (ja) | 2002-02-22 | 2003-02-05 | アミノ酸類粉末及びその製造方法 |
BR0306741-6A BR0306741A (pt) | 2002-02-22 | 2003-02-05 | Método para produzir um pó de aminoácidos, e, pó de aminoácidos |
US10/921,895 US20050080136A1 (en) | 2002-02-22 | 2004-08-20 | Powder of amino acids and method for producing the same |
US12/168,566 US7662799B2 (en) | 2002-02-22 | 2008-07-07 | Powder of amino acids and method for producing the same |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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JP2002046580 | 2002-02-22 | ||
JP2002-46580 | 2002-02-22 | ||
JP2002-201848 | 2002-07-10 | ||
JP2002201848 | 2002-07-10 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US10/921,895 Continuation US20050080136A1 (en) | 2002-02-22 | 2004-08-20 | Powder of amino acids and method for producing the same |
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WO2003070023A1 true WO2003070023A1 (fr) | 2003-08-28 |
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ID=27759684
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2003/001198 WO2003070023A1 (fr) | 2002-02-22 | 2003-02-05 | Poudre d'acides amines et procede de production de cette poudre |
Country Status (9)
Country | Link |
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US (2) | US20050080136A1 (ja) |
EP (1) | EP1479300B1 (ja) |
JP (1) | JP4482925B2 (ja) |
CN (1) | CN100356871C (ja) |
AU (1) | AU2003207244A1 (ja) |
BR (1) | BR0306741A (ja) |
DE (1) | DE60329744D1 (ja) |
MY (1) | MY140392A (ja) |
WO (1) | WO2003070023A1 (ja) |
Cited By (4)
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JP2004305201A (ja) * | 2002-11-27 | 2004-11-04 | Hayashibara Biochem Lab Inc | アクリルアミドの生成抑制方法とその用途 |
WO2006062238A1 (ja) * | 2004-12-07 | 2006-06-15 | Ajinomoto Co., Inc. | アミノ酸の微粉末及びその懸濁液 |
JP2009286755A (ja) * | 2008-05-30 | 2009-12-10 | Nippon Rikagaku Yakuhin Kk | 難溶性アミノ酸類微細粒子、難溶性アミノ酸類含有混合組成物及びこれらの製造方法並びに皮膚外用剤及び食品添加物 |
KR20110053268A (ko) | 2008-09-09 | 2011-05-19 | 아지노모토 가부시키가이샤 | 분지쇄 아미노산 함유 경구제제 |
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WO2004096113A2 (en) | 2003-04-28 | 2004-11-11 | Medical Instill Technologies, Inc. | Container with valve assembly for filling and dispensing substances, and apparatus and method for filling |
WO2007023172A2 (de) * | 2005-08-23 | 2007-03-01 | Armand Herberger | Proteinzusammensetzung zur behandlung eines physiologisch bedingten, klinisch unauffälligen proteinmehrbedarfs |
WO2007022968A1 (de) * | 2005-08-23 | 2007-03-01 | Hans Leweling | Proteinzusammensetzung zur behandlung von proteinmangelzuständen |
WO2007127286A2 (en) | 2006-04-24 | 2007-11-08 | Medical Instill Technologies, Inc. | Needle penetrable and laser resealable lyophilization device and related method |
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US20080132604A1 (en) * | 2006-11-30 | 2008-06-05 | Terumo Kabushiki Kaisha | Poly-(alpha-hydroxy acid) composition and method of producing molded article using the same |
US20110305798A1 (en) * | 2008-12-17 | 2011-12-15 | Igelosa Nutrition Science AB | Nutritional supplement with specific amino acid profile |
WO2011043647A1 (en) * | 2009-10-09 | 2011-04-14 | N.V. Nutricia | Amino acid composition with improved dispersibility |
CA2861956A1 (en) * | 2012-01-20 | 2013-07-25 | Milk Specialties Company D/B/A Milk Specialties Global | Method of instantizing amino acids |
JP5917964B2 (ja) | 2012-03-19 | 2016-05-18 | 富士ゼロックス株式会社 | 錠剤、錠剤の製造方法、錠剤管理装置、錠剤照合装置及びプログラム |
CN102908337B (zh) * | 2012-10-12 | 2014-03-05 | 大连医诺生物有限公司 | 微囊化氨基酸组合物及其制备方法 |
CN103734716A (zh) * | 2013-12-16 | 2014-04-23 | 无锡金维氨生物科技有限公司 | 一种支链氨基酸 |
MX2017005692A (es) | 2014-10-31 | 2017-08-07 | Glaxosmithkline Ip Dev Ltd | Formulacion en polvo. |
CN105288638B (zh) * | 2015-10-27 | 2018-07-06 | 江苏金维氨生物工程有限公司 | 一种提高支链氨基酸粉剂堆积密度的方法 |
WO2023222797A1 (en) * | 2022-05-18 | 2023-11-23 | Société des Produits Nestlé S.A. | Method for the preparation of a nutritional powder |
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- 2003-02-05 BR BR0306741-6A patent/BR0306741A/pt not_active IP Right Cessation
- 2003-02-05 DE DE60329744T patent/DE60329744D1/de not_active Expired - Lifetime
- 2003-02-05 CN CNB038028492A patent/CN100356871C/zh not_active Expired - Fee Related
- 2003-02-05 AU AU2003207244A patent/AU2003207244A1/en not_active Abandoned
- 2003-02-05 EP EP03703198A patent/EP1479300B1/en not_active Expired - Lifetime
- 2003-02-20 MY MYPI20030590A patent/MY140392A/en unknown
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2004
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JP2004305201A (ja) * | 2002-11-27 | 2004-11-04 | Hayashibara Biochem Lab Inc | アクリルアミドの生成抑制方法とその用途 |
WO2006062238A1 (ja) * | 2004-12-07 | 2006-06-15 | Ajinomoto Co., Inc. | アミノ酸の微粉末及びその懸濁液 |
JP2009286755A (ja) * | 2008-05-30 | 2009-12-10 | Nippon Rikagaku Yakuhin Kk | 難溶性アミノ酸類微細粒子、難溶性アミノ酸類含有混合組成物及びこれらの製造方法並びに皮膚外用剤及び食品添加物 |
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Also Published As
Publication number | Publication date |
---|---|
US20050080136A1 (en) | 2005-04-14 |
EP1479300A1 (en) | 2004-11-24 |
EP1479300B1 (en) | 2009-10-21 |
BR0306741A (pt) | 2004-12-28 |
EP1479300A4 (en) | 2005-09-14 |
JPWO2003070023A1 (ja) | 2005-06-09 |
CN100356871C (zh) | 2007-12-26 |
JP4482925B2 (ja) | 2010-06-16 |
CN1625346A (zh) | 2005-06-08 |
US20080275124A1 (en) | 2008-11-06 |
MY140392A (en) | 2009-12-31 |
DE60329744D1 (de) | 2009-12-03 |
AU2003207244A1 (en) | 2003-09-09 |
US7662799B2 (en) | 2010-02-16 |
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