WO2014088279A1 - 식품 조성물 및 이를 포함하는 연질 캡슐 - Google Patents
식품 조성물 및 이를 포함하는 연질 캡슐 Download PDFInfo
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- WO2014088279A1 WO2014088279A1 PCT/KR2013/011082 KR2013011082W WO2014088279A1 WO 2014088279 A1 WO2014088279 A1 WO 2014088279A1 KR 2013011082 W KR2013011082 W KR 2013011082W WO 2014088279 A1 WO2014088279 A1 WO 2014088279A1
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- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
-
- 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
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- 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
- Food compositions and soft capsules comprising the same are disclosed. More specifically, a food composition excellent in water dispersibility or water solubility and a soft capsule containing the same are disclosed.
- the dietary supplement market has been growing at an average annual rate of 6% over the past five years.
- the health functional food market is considered to have high potential because the demand for health functional foods is increasing with the economic growth of emerging countries.
- the materials of these health functional foods contain many functional natural products in their natural state. However, most of these functional natural products are poorly water-soluble and have very low bioabsorption.
- One embodiment of the present invention provides a food composition excellent in water dispersibility or water solubility.
- Another embodiment of the present invention provides a soft capsule comprising the food composition.
- compositions having water dispersibility or water solubility.
- the poorly water-soluble natural product may include at least one poorly water-soluble natural polyphenol compound selected from the group consisting of curcumin, silymarin, and resveratrol.
- the edible surfactant may include polysorbates.
- the edible cosurfactant may include at least one compound selected from the group consisting of glycerol fatty acid esters, propylene glycol and propylene glycol fatty acid esters.
- the edible oil may include at least one selected from the group consisting of vegetable oils, refined fish oils and oils derived from seaweeds.
- the food composition may further comprise 500 parts by weight or less of the edible additive.
- the edible additive may include at least one compound selected from the group consisting of lecithin, viscosity modifiers, fragrances, preservatives, pigments, glycerol, sorbitol and gelatin.
- Food composition according to an embodiment of the present invention is excellent in water dispersibility or water solubility, has a high bioavailability when used in the field of soft capsules.
- 1A to 1C are graphs showing the dissolution rate in water of the food compositions prepared in Examples 1 to 22.
- Figure 2a to 2c is a graph showing the dissolution rate in the buffer of pH 1.2 of the food composition prepared in Examples 1 to 22.
- 3A to 3C are graphs showing the dissolution rate in a buffer of pH 6.8 of the food composition prepared in Examples 1 to 22.
- 4A to 4C are graphs showing PK experimental data for the food compositions prepared in Examples 2, 13, 20, and 21 together with PK experimental data for three commercial food compositions and blanks.
- Food composition according to an embodiment of the present invention is 100 parts by weight of poorly water-soluble natural product, 400 to 8,000 parts by weight of edible surfactant, 40 to 2,500 parts by weight of edible surfactant, and 40 to edible oil It contains 1,500 parts by weight and is water dispersible or water soluble.
- edible means food acceptable
- water dispersibility means the property that the food composition is present in the emulsion state in water
- water soluble water solubility
- the poorly water-soluble natural product may have a health promoting function and / or a physiological function.
- the poorly water-soluble natural product may include a poorly water-soluble natural polyphenol compound.
- the poorly water-soluble natural polyphenol compound may include curcumin, silymarin, resveratrol, or a combination thereof.
- the curcumin may be derived from turmeric root extract
- the silymarin may be derived from milk thistle (milk thistle) extract.
- the silymarin may include silybin (silybin), isosilily (isosilybin), silycristine (silychristin) and sillydianin.
- the edible surfactant plays a role of improving water dispersibility or water solubility of the poorly water-soluble natural product.
- the edible surfactant may include polysorbates.
- the polysorbates may be polysorbate 20, polysorbate 40, polysorbate 60, polysorbate 80, or a combination thereof.
- the content of the edible surfactant is less than 400 parts by weight based on 100 parts by weight of the poorly water-soluble natural product, the poorly water-soluble natural product is not sufficiently dissolved in the food composition, and when the content of the edible surfactant exceeds 8,000 parts by weight, It does not form an emulsion.
- the edible cosurfactant serves to further improve the water dispersibility or water solubility of the poorly water-soluble natural product.
- the edible cosurfactant may comprise at least one compound selected from the group consisting of glycerol fatty acid esters, propylene glycol and propylene glycol fatty acid esters.
- the glycerol fatty acid esters may include glycerol dibehenate, glycerol monooleate, polyglycerol oleate, glycerol palmitostearate or a combination thereof.
- the propylene glycol fatty acid esters may include propylene glycol monocaprylate, propylene glycol dicaprylocaprate, propylene glycol laurate, or a combination thereof.
- the edible cosurfactant may include Plurol Oleique ®, Capryol PGMC TM, propylene glycol, or a combination of both.
- the food composition does not form a microemulsion in water or an aqueous solution, or an emulsion having a large particle size Particles are formed, which reduces absorption in the body and decreases bioavailability.
- the content of the glycerol fatty acid esters may be 40 to 1,500 parts by weight, for example, 60 to 1,000 parts by weight based on 100 parts by weight of the poorly water-soluble natural product.
- the content of the propylene glycol fatty acid ester is 100 to 2,500 parts by weight, for example 120 to 2,000 parts by weight, based on 100 parts by weight of the poorly water-soluble natural product. It may be wealth.
- the edible oil further serves to further improve the water dispersibility or water solubility of the poorly water-soluble natural product.
- the edible oil may be one having a physiological control activity.
- the edible oil may include at least one selected from the group consisting of vegetable oils, refined fish oils and oils derived from seaweeds.
- the edible oil may include olive oil, medium chain triglyceride oil (MCT oil), fish oil, Ahi flower oil, Algae oil, or a combination thereof.
- MCT oil may be a refined oil and fat as a kind of edible oil and fat.
- the food composition does not form a microemulsion in water or an aqueous solution.
- the food composition may further include more than 0 parts by weight to 500 parts by weight or less of the edible additive based on 100 parts by weight of the poorly water-soluble natural product.
- the edible additive may include at least one compound selected from the group consisting of lecithin, viscosity modifiers, fragrances, preservatives, pigments, glycerol, sorbitol and gelatin.
- the viscosity modifier may include a water-soluble polymer such as polyvinylpyrrolidone to increase the dispersibility and absorption of the solids.
- the fragrance may include ethers, esters, ketones, fatty acids, phenols, aromatic alcohols or combinations thereof.
- the fragrance may include formic acid keranyl, formic acid citronelyl, formic acid isoamyl, cinnamic acid, or a combination thereof.
- the preservative may include dihydroacetic acid, sorbic acid, benzoic acid, propionic acid or a combination thereof.
- the preservative may be a synthetic additive such as dibutylhydroxytoluene or butylhydroxyanisole; Natural additives such as D-tocopherol or degreasing rice extract; Or combinations thereof.
- the pigment may be a natural pigment such as turmeric, saffron or green chlorophyll; Pigments as artificial pigments listed in food additives such as food coloring green No. 3, food coloring red No. 3 or food coloring yellow No. 5; Or combinations thereof.
- the food composition is emulsified quickly in gastric juice condition (pH 1.2) and small intestine condition (pH 6.8) so that the active ingredient in the poorly water-soluble natural product is absorbed into the body in minutes. Therefore, the food composition may maximize the bioavailability of the poorly water-soluble natural product.
- Another embodiment of the present invention provides a soft capsule comprising the food composition.
- Such soft capsules may be prepared by methods well known in the art.
- the soft capsule may further include a conventional food excipient in addition to the food composition.
- the edible surfactant, the edible cosurfactant and the edible oil were mixed uniformly in the ratio as shown in Tables 1 to 3 below. Thereafter, the poorly water-soluble natural product was added to the resultant in the same ratio as in the following Tables 1 to 3, and uniformly mixed, thereby sufficiently dissolving the poorly water-soluble natural product to prepare a food composition. As a result, 18 kinds of food compositions were obtained. However, each numerical value shown in Tables 1-3 is content, and the unit is a weight part.
- curcumin, silymarin and resveratrol are manufactured by NATUREX of France
- polysorbate 80 is EMASOL O-120V of KAO Chemical of Japan
- Plurol ® Oleique is a brand name of polyglyceryl-3 dioleate
- Capryol TM PGMC is a trade name of propylene glycol monocaprylate (type I), a product of Gattefosse Co. of France, olive oil is a product of Borges extra virgin of Spain, and fish oil is an ethyl ester form of Korean NeoMega product.
- Ahi flower oil is a vegetable oil and is a TCI product of the United States
- algae oil is an algae extract oil of NeoMega of Korea.
- the food compositions prepared in Examples 1 to 22 were prepared using nanometer or micrometer emulsions in water, gastric fluid buffer (pH 1.2) or small intestine buffer (pH 6.8). It was found to form. From this, when orally ingesting each of the food compositions, it can be easily expected that the bioavailability will be high absorption in the human body. For reference, the smaller the size of the formed emulsion is effective absorption in the gastrointestinal tract membrane and at the same time structurally stabilized state is higher bioavailability.
- the food composition prepared in Examples 1 to 22 was filled in a capsule of size 0, and then the dissolution test was performed using the paddle method according to the USP 35 dissolution rule.
- the dissolution test refers to a test for investigating the solubility of a physiologically regulating active substance (drug, etc.) injected into the dispersion medium after the formulation such as tablets or capsules is administered to the dispersion medium and then disintegrated in the dispersion medium.
- the dissolution rate of 50% means that 50% of the poorly water-soluble natural substances included in each food composition are solubilized to form an emulsion.
- the dissolution test was carried out for 2 hours with a paddle speed of 50 rpm, using a dispersion medium 900 ml as the dissolution medium, the temperature was set to 37 ⁇ 0.5 °C.
- a dispersion medium water (Figs. 1A to 1C), a buffer of pH 1.2 (Figs. 2A to 2C), or a buffer of pH 6.8 (Figs. 3A to 3C) were used.
- the dispersion medium containing the poorly water-soluble natural product solubilized in the dispersion medium was intermittently collected by an autosampler, and the concentration of the poorly water-soluble natural product was analyzed by liquid chromatography.
- the dissolution rate was calculated from the concentration of the poorly water-soluble natural product according to the USP 35 dissolution rule. As a result, the obtained dissolution rate was shown to FIGS. 1A-1C, FIGS. 2A-2C, and FIGS. 3A-3C, respectively.
- "blank” means a test result of the poorly water-soluble natural product itself (that is, nothing added) used in the embodiments shown in each of the drawings.
- the unit of the dissolution rate in FIGS. 1A-1C, 2A-2C, and 3A-3C is weight%.
- the food composition prepared in Examples 1 to 22 was found to have a very high dissolution rate and dissolution rate compared to the poorly water-soluble food composition itself (ie, blank).
- the food compositions prepared in Examples 2, 13, 20, and 21 have a higher bioabsorption rate in rats (about 5 to 20 times) compared to commercial food compositions or poorly water-soluble food compositions themselves. Appeared.
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Abstract
Description
구분 | 구성 성분 | 실시예 | ||||||
1 | 2 | 3 | 4 | 13 | 14 | 19 | ||
수난용성 천연물 | 커큐민 | 4.8 | 4.8 | 4.8 | 4.8 | 4.8 | 4.8 | 7.3 |
식용 계면활성제 | 폴리소르베이트 80 | 76.2 | 76.2 | 66.7 | 66.7 | 76.2 | 76.2 | 45.8 |
식용 공계면활성제 | Plurol®Oleique | 9.5 | 9.5 | 0 | 0 | 9.5 | 9.5 | 9.2 |
Capryol™ PGMC | 0 | 0 | 19.0 | 19.0 | 0 | 0 | 9.2 | |
프로필렌글리콜 | 0 | 0 | 0 | 0 | 0 | 0 | 0.9 | |
식용 오일 | 올리브오일 | 9.5 | 0 | 9.5 | 0 | 0 | 0 | 0 |
Fish oil | 0 | 9.5 | 0 | 9.5 | 0 | 0 | 0 | |
MCT oil | 0 | 0 | 0 | 0 | 0 | 0 | 27.5 | |
Ahi flower oil | 0 | 0 | 0 | 0 | 9.5 | 0 | 0 | |
Algae oil | 0 | 0 | 0 | 0 | 0 | 9.5 | 0 |
구분 | 구성 성분 | 실시예 | |||||||
5 | 6 | 7 | 8 | 15 | 16 | 20 | 21 | ||
수난용성 천연물 | 실리마린 | 11.6 | 11.6 | 9.1 | 9.1 | 11.6 | 11.6 | 10.7 | 10.6 |
식용 계면활성제 | 폴리소르베이트 80 | 70.8 | 70.8 | 63.6 | 63.6 | 70.8 | 70.8 | 40.2 | 44.2 |
식용 공계면활성제 | Plurol®Oleique, | 8.8 | 8.8 | 0 | 0 | 8.8 | 8.8 | 46.9 | 8.8 |
Capryol™ PGMC | 0 | 0 | 18.2 | 18.2 | 0 | 0 | 0 | 8.8 | |
프로필렌글리콜 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0.9 | |
식용 오일 | 올리브오일 | 8.8 | 0 | 9.1 | 0 | 0 | 0 | 2.2 | 0 |
Fish oil | 0 | 8.8 | 0 | 9.1 | 0 | 0 | 0 | 0 | |
MCT oil | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 26.5 | |
Ahi flower oil | 0 | 0 | 0 | 0 | 8.8 | 0 | 0 | 0 | |
Algae oil | 0 | 0 | 0 | 0 | 0 | 8.8 | 0 | 0 |
구분 | 구성 성분 | 실시예 | ||||||
9 | 10 | 11 | 12 | 17 | 18 | 22 | ||
수난용성 천연물 | 레스베라트롤 | 7.4 | 7.4 | 7.4 | 7.4 | 7.4 | 7.4 | 5.6 |
식용 계면활성제 | 폴리소르베이트 80 | 64.8 | 64.8 | 74.0 | 74.0 | 74.0 | 74.0 | 46.6 |
식용 공계면활성제 | Plurol®Oleique, | 0 | 0 | 9.3 | 9.3 | 9.3 | 9.3 | 9.3 |
Capryol™ PGMC | 18.5 | 18.5 | 0 | 0 | 0 | 0 | 9.3 | |
프로필렌글리콜 | 0 | 0 | 0 | 0 | 0 | 0 | 0.9 | |
식용 오일 | 올리브오일 | 9.3 | 0 | 9.3 | 0 | 0 | 0 | 0 |
Fish oil | 0 | 9.3 | 0 | 9.3 | 0 | 0 | 0 | |
MCT oil | 0 | 0 | 0 | 0 | 0 | 0 | 28 | |
Ahi flower oil | 0 | 0 | 0 | 0 | 9.3 | 0 | 0 | |
Algae oil | 0 | 0 | 0 | 0 | 0 | 9.3 | 0 |
실시예 | ||||||||
수난용성천연물 | 분산매 | 1 | 2 | 3 | 4 | 13 | 14 | 19 |
커큐민 | 물 | 7.0±0.2 | 20.2±1.0 | 26.5±8.4 | 8.3±0.1 | 8.4±0.9 | 7.7±0.1 | 34.3±0.9 |
pH 1.2 완충액 | 8.0±0.3 | 22.8±1.1 | 27.1±0.3 | 8.4±0.4 | 8.9±0.3 | 7.9±0.3 | 41.2±0.2 | |
pH 6.8 완충액 | 8.2±0.1 | 19.8±1.0 | 25.0±0.9 | 8.6±0.3 | 9.1±0.2 | 8.3±0.3 | 31.0±0.8 |
실시예 | |||||||||
수난용성천연물 | 분산매 | 5 | 6 | 7 | 8 | 15 | 16 | 20 | 21 |
실리마린 | 물 | 69.2±1.0 | 98.9±25.9 | 21.2±8.1 | 8.1±0.5 | 8.3±0.1 | 9.1±1.7 | 188.1±12.3 | 97.3±2.0 |
pH 1.2 완충액 | 100.3±3.3 | 140.8±1.0 | 34.7±0.9 | 8.4±0.3 | 9.1±0.2 | 8.4±0.3 | 218.3±53.4 | 102.4±4.9 | |
pH 6.8 완충액 | 98.7±0.7 | 129.2±0.7 | 29.3±0.8 | 8.2±0.1 | 8.6±0.2 | 8.6±0.2 | 303.7±73.3 | 109.9±20.4 |
실시예 | ||||||||
수난용성천연물 | 분산매 | 9 | 10 | 11 | 12 | 17 | 18 | 22 |
레스베라트롤 | 물 | 8.0±0.0 | 69.7±2.5 | 87.6±4.0 | 7.3±0.1 | 9.2±0.6 | 10.0±0.7 | 20.9±0.9 |
pH 1.2 완충액 | 8.9±0.0 | 83.0±2.5 | 107.6±2.9 | 7.8±0.3 | 10.1±0.2 | 9.0±0.3 | 24.3±0.8 | |
pH 6.8 완충액 | 9.1±0.1 | 78.9±3.0 | 101.6±3.7 | 8.6±0.4 | 10.0±0.5 | 10.5±0.8 | 37.8±0.1 |
혈액 중 커큐민의 함량 (ng/ml) | |||||||||
0시간 | 0.5시간 | 0.75시간 | 1시간 | 1.5시간 | 2시간 | 2.5시간 | 3시간 | 4시간 | |
실시예 2 | 106.5 | 136.8 | 69.5 | 81.1 | 70.5 | 73.4 | 74.4 | 75.9 | 68.6 |
실시예 13 | 52.5 | 57.7 | 51.9 | 55.0 | 74.7 | 54.4 | 53.5 | 54.6 | 49.0 |
Meriva* | 28.2 | 28.6 | 22.8 | 21.9 | 18.2 | 16.4 | 15.4 | 15.7 | 16.0 |
Blank | 1.7 | 6.0 | 2.0 | 2.9 | 3.0 | 3.3 | 3.3 | 3.7 | 3.1 |
혈액 중 실리빈의 함량 (ng/ml) | ||||||||||
0시간 | 0.25시간 | 0.5시간 | 1시간 | 2시간 | 3시간 | 4시간 | 6시간 | 8시간 | 12시간 | |
실시예 20 | 0.0 | 1969.3 | 918.7 | 753.2 | 659.5 | 185.1 | 242.0 | 22.9 | 19.9 | 12.4 |
레가론 캡슐** | 0.0 | 37.2 | 103.2 | 114.6 | 56.5 | 27.7 | 21.0 | 8.0 | 8.0 | 4.5 |
Blank | 0.0 | 56.0 | 59.1 | 33.5 | 31.6 | 21.4 | 13.5 | 5.7 | 4.3 | 0.8 |
혈액 중 실리빈의 함량 (ng/ml) | ||||||||||
0시간 | 0.25시간 | 0.5시간 | 1시간 | 2시간 | 3시간 | 4시간 | 6시간 | 8시간 | 12시간 | |
실시예 21 | 0.0 | 673.1 | 633.2 | 412.0 | 579.6 | 294.4 | 126.9 | 10.7 | 9.6 | 5.1 |
닥터슈퍼칸*** | 0.0 | 72.8 | 63.9 | 34.9 | 16.1 | 12.4 | 11.8 | 0.0 | 1.0 | 0.0 |
Blank | 0.0 | 28.9 | 43.5 | 40.8 | 32.8 | 19.4 | 8.6 | 1.6 | 0.9 | 0.0 |
Claims (8)
- 수난용성 천연물 100중량부;식용 계면활성제 400~8,000중량부;식용 공계면활성제 40~2,500중량부; 및식용 오일 40~1,500중량부를 포함하고,수분산성 또는 수용성을 갖는 식품 조성물.
- 제1항에 있어서,상기 수난용성 천연물은 커큐민(curcumin), 실리마린(silymarin) 및 레스베라트롤(resveratrol)로 이루어진 군으로부터 선택된 적어도 1종의 수난용성 천연 폴리페놀 화합물을 포함하는 식품 조성물.
- 제1항에 있어서,상기 식용 계면활성제는 폴리소르베이트류를 포함하는 식품 조성물.
- 제1항에 있어서,상기 식용 공계면활성제는 글리세롤 지방산 에스테르류, 프로필렌글리콜 및 프로필렌글리콜 지방산 에스테르류로 이루어진 군으로부터 선택되는 적어도 1종의 화합물을 포함하는 식품 조성물.
- 제1항에 있어서,상기 식용 오일은 식물성 오일, 정제 어유 및 해조류에서 유래된 오일로 이루어진 군으로부터 선택된 적어도 1종을 포함하는 식품 조성물.
- 제1항에 있어서,상기 식품 조성물은 식용 첨가제 500중량부 이하를 더 포함하는 식품 조성물.
- 제6항에 있어서,상기 식용 첨가제는 레시틴, 점도 조절제, 방향제, 보존제, 색소, 글리세롤, 소르비톨 및 젤라틴으로 이루어진 군으로부터 선택된 적어도 1종의 화합물을 포함하는 식품 조성물.
- 제1항 내지 제7항 중 어느 한 항에 따른 식품 조성물을 포함하는 연질 캡슐.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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US14/442,875 US20150282509A1 (en) | 2012-12-04 | 2013-12-03 | Food composition and soft capsule comprising same |
JP2015545375A JP2016502408A (ja) | 2012-12-04 | 2013-12-03 | 食品組成物、及びそれを含む軟質カプセル |
EP13860889.8A EP2929787A4 (en) | 2012-12-04 | 2013-12-03 | FOOD COMPOSITION AND MOLLE CAPSULE CONTAINING THE SAME |
CN201380063903.8A CN104837367A (zh) | 2012-12-04 | 2013-12-03 | 食品组合物及包括该食品组合物的软胶囊 |
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KR10-2012-0139846 | 2012-12-04 | ||
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KR10-2013-0147996 | 2013-11-29 | ||
KR1020130147996A KR20140071913A (ko) | 2012-12-04 | 2013-11-29 | 식품 조성물 및 이를 포함하는 연질 캡슐 |
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JP (1) | JP2016502408A (ko) |
KR (1) | KR20140071913A (ko) |
CN (1) | CN104837367A (ko) |
TW (1) | TW201438598A (ko) |
WO (1) | WO2014088279A1 (ko) |
Cited By (1)
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CN105267187A (zh) * | 2014-06-17 | 2016-01-27 | 优普生物科技股份有限公司 | 治疗脂肪肝的医药组合物及其制备方法与用途 |
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DK3468607T3 (da) * | 2016-06-14 | 2021-01-11 | Aquanova Ag | Resveratrolsolubilisat |
US20210195908A9 (en) * | 2018-11-30 | 2021-07-01 | Virun, Inc. | Creamy edible emulsions |
KR102394648B1 (ko) * | 2019-03-25 | 2022-05-09 | (주)아모레퍼시픽 | 실리마린의 생체이용률 향상용 첨가제 조성물 |
CN111329063A (zh) * | 2020-03-26 | 2020-06-26 | 江南大学 | 一种制备鱼油和白藜芦醇共包埋微胶囊粉末的方法 |
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- 2013-11-29 KR KR1020130147996A patent/KR20140071913A/ko not_active Application Discontinuation
- 2013-12-03 EP EP13860889.8A patent/EP2929787A4/en not_active Withdrawn
- 2013-12-03 US US14/442,875 patent/US20150282509A1/en not_active Abandoned
- 2013-12-03 WO PCT/KR2013/011082 patent/WO2014088279A1/ko active Application Filing
- 2013-12-03 JP JP2015545375A patent/JP2016502408A/ja active Pending
- 2013-12-03 CN CN201380063903.8A patent/CN104837367A/zh active Pending
- 2013-12-04 TW TW102144314A patent/TW201438598A/zh unknown
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CN105267187A (zh) * | 2014-06-17 | 2016-01-27 | 优普生物科技股份有限公司 | 治疗脂肪肝的医药组合物及其制备方法与用途 |
Also Published As
Publication number | Publication date |
---|---|
EP2929787A1 (en) | 2015-10-14 |
KR20140071913A (ko) | 2014-06-12 |
EP2929787A4 (en) | 2016-06-15 |
JP2016502408A (ja) | 2016-01-28 |
CN104837367A (zh) | 2015-08-12 |
TW201438598A (zh) | 2014-10-16 |
US20150282509A1 (en) | 2015-10-08 |
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