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WO2019112383A1 - Diaminate minéral métallique et procédé de préparation associé - Google Patents

Diaminate minéral métallique et procédé de préparation associé Download PDF

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Publication number
WO2019112383A1
WO2019112383A1 PCT/KR2018/015552 KR2018015552W WO2019112383A1 WO 2019112383 A1 WO2019112383 A1 WO 2019112383A1 KR 2018015552 W KR2018015552 W KR 2018015552W WO 2019112383 A1 WO2019112383 A1 WO 2019112383A1
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Prior art keywords
aspartate
glutamate
amino acid
bisaspartate
bisglutamate
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Ceased
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PCT/KR2018/015552
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English (en)
Korean (ko)
Inventor
윤주석
김누리
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Huen Co ltd
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Huen Co ltd
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Priority claimed from KR1020180156669A external-priority patent/KR102010558B1/ko
Publication of WO2019112383A1 publication Critical patent/WO2019112383A1/fr
Anticipated expiration legal-status Critical
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
    • A61K36/537—Salvia (sage)
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/08—Copper compounds

Definitions

  • the present invention relates to a metal mineral dianimate and a novel process for producing the same, wherein a metal mineral source and a mono-molecular amino acid are reacted in an aqueous solution, selectively filtered, concentrated and dried under reduced pressure or spray-
  • the present invention relates to a method for producing a metallic mineral diamine which does not occur. More specifically, the present invention relates to a method for producing a metal mineral dianimide which is electrically neutral and has no byproducts by preparing a metal mineral source and an acidic amino acid by reacting them in an aqueous solution or by reacting a metal mineral source with an amino acid in an acidic aqueous solution .
  • Minerals are the main constituent of the body, and they are essential nutrients that play important physiological control functions such as permeability regulation and metabolism of cell membrane.
  • modern people eat a lot of supplements because it is difficult to consume all the necessary minerals in the body by the diet added to the food.
  • mineral supplements the most important thing when ingesting is absorption rate and utilization rate in vivo, and in order for the minerals to be absorbed to the metal ion in the small intestine, ionized minerals are more absorbed than a single substance.
  • Recent studies have also shown that when minerals are bound to proteins or amino acids, they are absorbed into the small intestine by the absorption pathway of amino acids. Accordingly, many studies on the binding of minerals and amino acids have been conducted, and metallic mineral chelates or mineral diaminates having enhanced bioabsorption rates have been developed.
  • the metal mineral diamine is a compound in which two molecules of amino acid monomers and divalent mineral ions are ionically and coordinately bound to each other.
  • the mineral chelate is a compound in which oligopeptides and mineral ions having about 6 to 10 amino acids are ion- And it means a structure that completely encloses minerals.
  • the minerals diaminate has a stronger binding force than a simple salt in which a mineral is combined with a single amino acid but has weaker binding force than a chelate in which the mineral is completely surrounded, such as a mineral chelate.
  • This difference in binding force shows a bioabsorption rate similar to that of the mineral chelate compound, but the bioavailability is higher than that of the mineral chelate compound.
  • mineral diamine binds mono-molecular amino acid to a single element of mineral, its molecular size is easy to permeate through the cell membrane and is directly absorbed through the barrier, so that the bioabsorption and bioavailability are high.
  • the metal mineral diaminate is a double bond structure of ionic bonding and coordination bonding. It is not decomposed while digestive organs go through, and active absorption occurs in the small intestine. It passes through the stomach and does not go through the same ionization process.
  • Prior Art Korean Patent Registration No. 10-0481326 discloses a method for producing an organic chelate according to claim 1, wherein 1) a salt containing a metal mineral to be coordinated with an amino acid is dissolved in water and then NaOH or KOH is used Thereby precipitating a metal hydroxide; 2) removing the water-soluble K 2 SO 4 , Na 2 SO 4 or KCl, NaCl salt in the aqueous solution with a filter press; 3) dissolving the metal hydroxide of filtered M (OH) 2 (wherein M is a metal ion) with hydrochloric acid; 4) completely dissolving and mixing the amino acid in the solution; 5) After the above mixing, slowly titrating to the pI value of the amino acid with NaOH; And 6) filtering and drying the resulting particles.
  • X is a divalent metal ion and AA is an amino acid.
  • X is a divalent metal ion
  • M is a divalent metal ion other than X
  • AA is an amino acid
  • X is a divalent metal ion and AA is an amino acid.
  • the present inventors have completed the present invention by developing a process for producing metallic mineral diamines that overcomes the above-mentioned problem of by-products.
  • the present invention provides metal mineral diamines and processes for their preparation.
  • the present invention also provides a composition comprising the metal mineral diaminate prepared by the above method in a pharmacologically effective amount, a nutritionally effective amount or a cosmetically effective amount.
  • the present invention also provides a cosmetic composition comprising a uridine or uridine derivative and a metallic mineral diaminate.
  • the present invention relates to a method for producing a metal mineral / mono-molecular amino acid aqueous solution, comprising the steps of: adding a metal mineral source and an amino acid to water at a concentration of 0.1 to 70% by weight; Reacting the prepared metal mineral amino acid aqueous solution under an acidic condition for a predetermined time; Optionally filtering or concentrating the reaction aqueous solution; And drying and pulverizing; And a method for producing the metal mineral diamine.
  • the present invention relates to a method for producing a metal mineral / mono-molecular amino acid aqueous solution, comprising the steps of: adding a metal mineral source and an amino acid to water at a concentration of 0.1 to 70% by weight; Reacting the aqueous solution of the metal mineral and amino acid by heating at 40 to 100 ⁇ with stirring for a certain period of time; Optionally filtering or concentrating the reaction aqueous solution; And drying and pulverizing; As a further means for solving the problems.
  • the metal mineral source solution and the amino acid solution may be mixed at a ratio of 1: 1 to 4 based on the molar ratio of the mineral and amino acid of the metal mineral source.
  • the pH of the metal mineral / amino acid aqueous solution is adjusted to a pH of 4 to 8 by using a buffer solution. I want to.
  • the present invention further provides a process for producing metallic mineral diamines characterized by further comprising the step of pulverizing the metallic mineral-amino acid aqueous solution by vacuum drying, freeze-drying or spray-drying, .
  • the present invention provides a method for producing metal mineral diamines, wherein the metal amino acid is an acidic amino acid.
  • the present invention provides a method for producing metallic mineral diamines, which comprises at least one metal mineral source and at least one amino acid, respectively, to solve the technical problems.
  • the present invention is based on the finding that the metal mineral diaminates are selected from the group consisting of copper glutamate / aspartate, cooper bisglutamate, cooper bisaspartate, zinc glutamate / aspartate, Zinc bisglutamate, zinc bisaspartate, iron glutamate / aspartate, iron bisglutamate, iron bisaspartate, iron bisglutamate, / Iron aspartate, iron glutamate / bisaspartate, chromium glutamate / aspartate, chromium bisglutamate, chromium bisaspartate, ), Chromium bisglutamate / aspartate, aspartate, chromium glutamate / bisaspartate, covalt glutamate / aspartate, covalt bisglutamate, covalt bisaspartate, magnesium glutamate / for example, magnesium glutamate / aspartate, magnesium bisglutamate, magnesium bisaspartate, manganese glutamate
  • the present invention aims to solve the technical problem by providing an electrically neutral metal mineral dianimate produced by the above method.
  • the present invention relates to the above-mentioned metal mineral dianimide, which comprises copper glutamate / aspartate, cooper bisglutamate, cooper bisaspartate, zinc glutamate / aspartate, zinc glutamate / aspartate, ), Zinc bisglutamate, zinc bisaspartate, iron glutamate / aspartate, iron bisglutamate, iron bisaspartate, iron bis
  • the present invention relates to a method for the treatment and / or prophylaxis of an inflammatory disease or condition selected from the group consisting of iron bisglutamate / aspartate, iron glutamate / bisaspartate, chromium glutamate / aspartate, chromium bisglutamate, chromium bisaspartate, bisaspartate, chromium bisglue / aspartate, cobalt bisaspartate, cobalt glutamate / aspartate, cobalt bisglutamate, cobalt bisaspartate,
  • the present invention aims at solving the technical problems by providing an antiinflammatory pharmaceutical composition comprising a uridine or uridine derivative and a metal mineral diamine.
  • the present invention aims at solving technical problems by providing a cosmetic composition comprising a uridine or uridine derivative and a metallic mineral diaminate.
  • the present invention relates to a process for producing a novel metal mineral dianimate by reacting a metal mineral source with an acidic amino acid in an aqueous solution or by reacting a metal mineral source with an amino acid in an acidic aqueous solution, Dried, freeze-dried or spray-dried to produce a metal-mineral dianimide which is electrically neutral and free of byproducts.
  • the present invention relates to a metal mineral dianimate produced by the above method, which maintains stability at a temperature and a pH, does not affect the physical properties and taste of the product, exhibits a high absorption rate in the body, , Feed, and plant growth promoters.
  • FIG. 1 is a view showing the bonding and structural formula of a metallic mineral diaminate.
  • FIG. 2 is a photograph of a zinc aspartate diaminate prepared by spray drying.
  • Figure 3 is a photograph of manganese aspartic acid diaminate prepared by spray drying.
  • 4 is a photograph of calcium glutamic acid diaminate prepared by spray drying.
  • Figure 5 shows the effect of zinc aspartate diaminate on the production of nitric oxide of RAW 264.7 cells treated with lipopolysaccharide.
  • the molar ratio of the minerals to the amino acids in the metal mineral source is 1: 1 to 4, and as the solvent, water can be preferably used. However, if it can be easily removed after the reaction without affecting other reactants, It is not.
  • the solvent may be water, an alkaline solvent, an acidic solvent or an organic solvent. Further, in the case of using a neutral or alkaline amino acid in order to increase the efficiency of the process in an aqueous solution, a buffer solution may be added to satisfy an acidic aqueous solution condition.
  • the pH is preferably adjusted to a pH of from 4 to 8, more preferably from 5 to 7.5, in order to maintain smooth reactivity and neutrality of the product.
  • the reaction temperature is preferably from 0 to 100 ° C, and if the temperature is too low, the reactivity is deteriorated. On the other hand, if the temperature is too high, there is a problem of excessive energy use and a possibility that some amino acids are altered.
  • the metal mineral source that can be used in the present invention is not particularly limited and includes salts of metals having a valence of 2 or more such as calcium, copper, zinc, iron, chromium, cobalt, manganese, magnesium, selenium, , And in some cases, a mixture of two or more thereof may be used.
  • the metallic mineral source include copper sulfate, magnesium carbonate, magnesium lactate, magnesium carbonate, magnesium sulfate, magnesium gluconate, magnesium chloride, manganese sulfate, manganese chloride, zinc oxide, zinc sulfate, zinc gluconate, Calcium ferric oxide, calcium ferric oxide, calcium lactate, calcium carbonate, calcium citrate, calcium phosphate dibasic, calcium hydroxide, tribasic calcium phosphate, calcium gluconate, and chromium chloride.
  • the metal mineral source of the present invention may be a natural or artificially synthesized non-natural metal mineral resource present in nature, or it may be a pharmaceutical raw material, a food raw material, a cosmetic raw material, or an industrial raw material, Or a mixture of two or more thereof.
  • the amino acid which can be used in the present invention is not particularly limited, but in order to satisfy the acidic reaction condition, the amino acid is preferably, for example, glutamic acid or aspartic acid, and may be used in a mixture form of two or more thereof have.
  • the amino acid is not an acidic amino acid such as glutamic acid and aspartic acid, it is preferable to use an acidic aqueous solution. In some cases, a heating process may be required for the production of smooth diaminates.
  • the diamination reaction using the metal mineral source and the amino acid of the present invention can be expressed as shown in the following reaction formula (1).
  • X is a divalent metal ion
  • AA is an amino acid
  • X is a divalent metal ion
  • AA is an amino acid
  • X is a divalent metal ion
  • AA is an amino acid
  • X is a divalent metal ion
  • AA is an amino acid
  • X is a divalent metal ion
  • AA is an amino acid
  • X is a divalent metal ion
  • AA is an amino acid
  • the present invention relates to a metal mineral diamine represented by the following formula (1) or (2) prepared by the above method.
  • M is a divalent metal ion and AA is an amino acid.
  • M ' is a trivalent metal ion and AA is an amino acid.
  • Spray drying technology is a process in which a liquid sample such as a liquid, an organic solution, an emulsion, a dispersion or a suspension is sprayed, atomized, and brought into contact with a hot air stream.
  • the spray dryer is a device for spraying a liquid sample into a fine droplet form, and then evaporating water (water) or an organic solvent using a hot dry gas to produce a powder.
  • Spray drying takes place in a single step of liquid phase drying and has advantages such as cost reduction, easy scale-up, and simplification of processing process.
  • temperature-sensitive materials such as enzymes, proteins, or antibiotics can be pulverized without thermal deformation by using a spray drying technique, in the present invention,
  • the amino acid solution was prepared by powder drying and mineral chelate formation.
  • the sample solution must be pumpable, uniform, and free from impurities such as aqueous solutions, emulsions, suspensions or organic solutions.
  • pretreatment of the sample solution will greatly affect the particle size, shape and particle coating of the final spray product.
  • Additives such as lubricants, defloccants or other special substances must be incorporated into the sample solution in very small amounts.
  • a metal mineral / amino acid aqueous solution prepared by stirring each metal mineral aqueous solution and an amino acid aqueous solution was used as a sample.
  • a variety of nozzles are used to dispense the sample solution to obtain finer droplets.
  • a commonly used type of nozzle is a two fluid nozzle, a pressure nozzle, a rotary disk atomizer, or an ultrasonic nozzle.
  • the inlet temperature (the temperature of the drying gas) can be spray dried at a temperature of 50 to 550 ° C.
  • a metal mineral / amino acid aqueous solution is spray dried at a temperature of preferably 50 to 150 ° C.
  • the selection of the dispensing device takes into account the amount and nature of the sample solution to be treated and the nature of the spray dryer desired to be made.
  • the nozzle is selected according to the particle size of the mineral diamine, which is the final product.
  • a metallic mineral / amino acid aqueous solution prepared by stirring a metallic mineral aqueous solution and an amino acid aqueous solution is pulverized using the above-described spray drying apparatus to prepare a metallic mineral diaminate.
  • Representative amino acid metal mineral diamines that can be prepared through the reaction of the present invention include, but are not limited to, the following.
  • the metal mineral chelate produced by the method described above may be selected from the group consisting of calcium glutamate / aspartate, calcium glutamate / methionine, calcium glutamate / glycine, calcium aspartate / methionine calcium aspartate / methionine, calcium aspartate / glycine, calcium methionine / glycine, calcium bisglutamate, calcium bisaspartate, calcium bis-methionine calcium bismethionine or calcium bisglycine, and furthermore, one or more of these may be combined to produce a new metal mineral diaminate mixture.
  • the metal mineral diaminate is analyzed by the method of 1 FT-IR infrared spectroscopy (metal mineral diamine structure), 3 ICP emission spectrometry (element content measurement), and 3 amino acid analysis (amino acid content measurement) Respectively.
  • the metal mineral diaminate compound obtained in Example 1 was subjected to a safety test according to long-term preservation in an aqueous solution.
  • Experimental conditions were as follows: 1) the pH of the distilled water was adjusted to 3, 5, 7, and 9, the sample was added with the compound, and 2) the pH was adjusted to 3, 5, 7, A sample to which the above compound is added in a commercially available beverage (Vita 500, Bacchus, or Orange juice), 4) a sample in which the compound is added to skin lotion in commercially available cosmetics, 5) A sample in which the compound is added to a plant growth promoter.
  • a commercially available beverage Vita 500, Bacchus, or Orange juice
  • the present invention relates to a composition containing the amino acid diaminate of the above formula (1) or (2) in a pharmaceutical or nutritional or cosmetically effective amount.
  • the metal mineral diaminates of formula (I) or (II) may be formulated into various pharmaceutical dosage forms as desired.
  • the diaminates of formula (I) or (II) may be mixed with various pharmaceutically acceptable carriers which may be selected according to the formulations to be prepared.
  • the pharmaceutical composition according to the present invention can be formulated into injectable or oral formulations as desired.
  • the metal mineral diaminates of formula (I) or (II) as active ingredients can be formulated in a known manner using known pharmaceutical carriers and excipients and incorporated into unit dose forms or multi-dose containers.
  • the formulation form may be in the form of a solution, suspension or emulsion in an oil or aqueous medium, and may contain conventional dispersing agents, suspending agents or stabilizing agents. It may also be in the form of a dry powder, for example, dissolved in sterile, pyrogen-free water before use.
  • the metal mineral diaminates of formula (I) or (II) may also be formulated as suppositories using conventional suppository bases such as corn butter or other glycerides.
  • Solid dosage forms for oral administration may be capsules, tablets, pills, powders, and granules, with capsule and tablet being particularly useful. Tablets and pills are preferably prepared as preservative.
  • the active ingredient metal mineral diaminate of formula (I) or (II) is mixed with one or more inert diluents such as sucrose, lactose, starch and the like, and a lubricant such as magnesium stearate, disintegrants, .
  • the metal mineral diamine of formula (I) or (II) according to the present invention or the composition containing it may be administered in combination with other medicaments.
  • the therapeutically effective amount means the amount of active ingredient effective to reduce or delay the onset of a clinical marker or symptom of a disease that alleviates, reduces or prevents symptoms of the disease requiring treatment.
  • a pharmacologically effective amount can be determined empirically by testing compounds in known in vivo and in vitro model systems for diseases in need of treatment.
  • the metal mineral diamine of formula (I) or (II) as the active ingredient is preferably contained in a unit dose of about 0.1 to 1000 mg.
  • the dosage depends on the physician's prescription depending on factors such as the patient's weight, age and the particular nature and severity of the disease. However, the dosage required for adult therapy is usually in the range of about 1 to 1000 mg per day, depending on the frequency and intensity of administration.
  • a total dosage of about 1 to 500 mg per day, separated by a single dose at the time of intramuscular or intravenous administration to an adult would suffice, but in some patients a higher daily dose may be desirable.
  • &quot cytologically effective amount " means an amount of the active ingredient that is effective for supplementing the nutritional metabolism of an object, which does not lead to disease, but which does not cause side effects due to overdosage.
  • the cosmetically effective amount refers to the amount of the active ingredient that is effective in improving the nutritional status related to the beauty of the object such as the health condition of the skin and the health condition of the hair and at the same time, do.
  • the nutritional effective amount and the cosmetically effective amount may be variably determined by various factors such as the use and properties of the composition to be used, so that the effective amount need not be particularly limited.
  • the composition according to the present invention may contain, depending on its use, for example, a pharmaceutical composition comprising a pharmaceutically acceptable carrier, a food comprising a nutraceutically acceptable carrier, a feed additive or beverage composition, And a cosmetic composition containing a carrier that is acceptable as a cosmetic composition.
  • the mineral diiminate compounds obtained in Experimental Examples 1 to 16 were added to commercially available Mierofhaiba (Hyundai Pharm) to confirm the effect on physical properties and taste.
  • 10 taste sensory evaluations were conducted on the taste, appearance and comprehensive evaluation of the sample aqueous solutions obtained in Experimental Examples 1 to 16 against 10 special sensory test agents.
  • the taste was evaluated by scoring five points of very weak (1), weak (2), normal (3), strong (4), and very strong (5) for bitter taste, pungent taste and strong taste. Color and clarification and comprehensive evaluation were performed in such a way as to score 5 points of very poor (1), poor (2), normal (3), good (4) and excellent (5).
  • the evaluation of taste is shown in Table 1 below, and the evaluation of appearance is shown in Table 2 below.
  • the mineral diiminate compound according to the present invention hardly affected the physical properties (taste, appearance, etc.) of the object to be added.
  • a powder mixture was prepared by mixing 0.5% by weight of 5-ribonucleotide with 99.5% by weight of the diaminate compound of Experimental Example 13, and the taste thereof was confirmed. As a result, it was confirmed that the same taste as that of sodium glutamate Respectively. Therefore, it was confirmed that the diaminate compound of the present invention had no problem in utilization as a seasoning.
  • the mineral diaminate compound obtained in Experimental Example 13 was mixed with 100 g of milk and kept for a long time. As a result, no precipitation was formed and no influence on the taste was observed.
  • the cosmetic lotion type containing the mineral diaminate compound obtained in Experimental Example 1 was prepared and maintained for a long time, and as a result, there was no discoloration and there was no problem even if it was used for skin.
  • Lipopolysaccharide is an outer membrane component of Gram-negative bacteria. When treated with cells, it induces inflammation and induces nitric oxide (NO) production. Since the produced nitric oxide induces inflammatory response to peripheral cells and induces proinflammatory stimulation, inhibition of nitric oxide production is important in the treatment of inflammatory diseases. Therefore, in order to examine the anti-inflammatory effect of the metal mineral diaiminate composite composition containing uridine, the degree of nitric oxide produced after lipopolysaccharide treatment of RAW 264.7 cells treated with the composite composition was observed.
  • RAW 264.7 macrophages used for the anti-inflammatory effect test were distributed from the Korean Cell Line Bank.
  • RAW264.7 macrophages were cultured in Dulbecco's modified Eagle minimal essential medium supplemented with 10% fetal bovine serum (FBS), 1% penicillin and 1% streptomycin , DMEM), and then cultured at 37 ° C under 5% carbon dioxide for 24 hours.
  • the badge was changed every 2 days.
  • the prepared zinc aspartate diaminate was used as a stock solution at a concentration of 1 mg / ml by adding tertiary distilled water and stored at 4 ° C.
  • RAW 264.7 cells were plated at 2.5 ⁇ 10 5 cells / ml in a 24-well plate and cultured at 37 ° C. under 5% carbon dioxide for 24 hours.
  • zinc aspartate diaminate was treated to 25, 50, 100 and 200 ug / ml, respectively, and added to 100 ug / ml of uridine.
  • lipopolysaccharide (LPS) was cultured at 200 ng / ml for 24 hours.
  • RAW 264.7 cells treated with nothing were treated with negative control
  • RAW 264.7 cells treated with only 200 ng / ml of lipopolysaccharide were treated with positive control
  • zinc ascapartate diaminate 25 50, 100 and 200 ug / ml each of uridine
  • RAW 264.7 cells treated with 200 ng / ml of lipopolysaccharide after one hour of treatment with ug / ml were designated Experimental Groups 1, 2, 3 and 4, respectively.
  • Figure 5 shows the effect of zinc aspartate diaminate on the production of nitric oxide of RAW 264.7 cells treated with lipopolysaccharide.
  • uridine derivatives uridine phosphate, uracil, uridine monophosphate, uridine diphosphate, triacetyl uridine, tribenzonyl uridine, uridine, 5-ethyl uridine, 2-deoxyuridine, or isopropylidene uridine may be used.

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Abstract

La présente invention concerne un diaminate minéral métallique et un nouveau procédé de préparation de celui-ci et, plus particulièrement, un procédé de préparation d'un diaminate minéral ne produisant pas de sous-produit qui consiste à permettre à une source minérale métallique de réagir avec un acide aminé monomoléculaire dans une solution aqueuse, ledit procédé consiste ensuite à procéder à une filtration sélective, une concentration et un séchage, par exemple, un séchage sous pression réduite ou un séchage par pulvérisation. Plus particulièrement, la présente invention concerne un procédé de préparation d'un diaminate minéral métallique, qui est électriquement neutre et n'ayant pas de sous-produit, ledit procédé consiste à préparer un diaminate minéral métallique au moyen par la mise en réaction d'une source minérale métallique et d'un acide aminé acide dans une solution aqueuse ou par la mise en réaction d'une source minérale métallique et d'un acide aminé dans une solution aqueuse acide.
PCT/KR2018/015552 2017-12-08 2018-12-07 Diaminate minéral métallique et procédé de préparation associé Ceased WO2019112383A1 (fr)

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KR20170168738 2017-12-08
KR10-2017-0168738 2017-12-08
KR20170168368 2017-12-08
KR10-2017-0168368 2017-12-08
KR10-2018-0156669 2018-12-07
KR1020180156669A KR102010558B1 (ko) 2017-12-08 2018-12-07 금속 미네랄 디아미네이트 및 이의 제조방법

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Cited By (2)

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CN113735729A (zh) * 2021-08-03 2021-12-03 四川吉隆达生物科技集团有限公司 饲料级谷氨酸亚铁的生产工艺
CN116120197A (zh) * 2023-02-09 2023-05-16 郑州瑞普生物工程有限公司 一种l-天门冬氨酸锌及其制备方法

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EP1790348A2 (fr) * 1999-05-05 2007-05-30 Srinivas Uppugunduri Utilisation de l'uridine pour le traitement d'inflammations et/ou de l'hémostase
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KR20100082835A (ko) * 2007-10-11 2010-07-20 다이호야쿠힌고교 가부시키가이샤 우라실 유도체를 유효 성분으로 하는 염증성 장질환 치료약
US20150265647A1 (en) * 2012-09-28 2015-09-24 Tufts University Uridine diphosphate derivatives, prodrugs, compositions and uses thereof

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CN113735729A (zh) * 2021-08-03 2021-12-03 四川吉隆达生物科技集团有限公司 饲料级谷氨酸亚铁的生产工艺
CN116120197A (zh) * 2023-02-09 2023-05-16 郑州瑞普生物工程有限公司 一种l-天门冬氨酸锌及其制备方法

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