WO2015137965A1 - Liquids and foodstuffs containing beta-hydroxy-beta-methylbutyrate (hmb) in free acid form - Google Patents
Liquids and foodstuffs containing beta-hydroxy-beta-methylbutyrate (hmb) in free acid form Download PDFInfo
- Publication number
- WO2015137965A1 WO2015137965A1 PCT/US2014/027596 US2014027596W WO2015137965A1 WO 2015137965 A1 WO2015137965 A1 WO 2015137965A1 US 2014027596 W US2014027596 W US 2014027596W WO 2015137965 A1 WO2015137965 A1 WO 2015137965A1
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- WIPO (PCT)
- Prior art keywords
- hmb
- acid
- composition
- liquid
- free acid
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Classifications
-
- 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
-
- 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
-
- 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
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
- A61K31/592—9,10-Secoergostane derivatives, e.g. ergocalciferol, i.e. vitamin D2
-
- 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
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
- A61K31/593—9,10-Secocholestane derivatives, e.g. cholecalciferol, i.e. vitamin D3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay
- A61K33/10—Carbonates; Bicarbonates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- the invention relates generally to nutritional supplements containing P-Hydroxy-P- methylbutyrate (HMB) and more specifically to nutritional supplements containing HMB in the free acid form.
- HMB P-Hydroxy-P- methylbutyrate
- HMB has been found to be useful within the context of a variety of applications. Specifically, in U.S. Patent No. 5,360,613 (Nissen), HMB is described as useful for reducing blood levels of total cholesterol and low-density lipoprotein cholesterol. In U.S. Patent No. 5,348,979 (Nissen et al.), HMB is described as useful for promoting nitrogen retention in humans. U.S. Patent No. 5,028,440 (Nissen) discusses the usefulness of HMB to increase lean tissue development in animals. Also, in U.S. Patent No. 4,992,470 (Nissen), HMB is described as effective in enhancing the immune response of mammals. U.S. Patent No.
- HMB is described as increasing the aerobic capacity of muscle of an animal without a substantial increase in the mass of the muscle.
- HMB has been described as useful for improving a human's perception of his emotional state in U.S. Patent No. 6,291,525.
- HMB has been shown to have positive effects on maintaining and increasing lean muscle mass in cancer cachexia and AIDS wasting.
- a positive effect on muscle damage and the resulting inflammatory response caused by exercising which leads to muscle soreness, strength loss, and an increase in pro-inflammatory cytokines is seen with use of HMB.
- HMB alone or in combination with other amino acids is an effective supplement for restoring muscle strength and function in young athletes.
- HMB in combination with two amino acids, arginine and lysine is effective in increasing muscle mass in elderly persons.
- Nutritional supplements come in many forms; for the present invention, the focus is on nutritional supplements in a non-emulsified substantially clear liquid form. These substantially clear liquid supplements often include vitamins, carbohydrates, soluble protein, amino acids, minerals and other nutrients. It is desirable to include HMB in these liquid supplements because of the known benefits of consuming HMB.
- HMB in other liquids, such as water, sports drinks, fruit juices, soft drinks, and other carbonated and noncarbonated beverages.
- HMB-acid is a liquid and much more difficult to deliver or incorporate into products.
- HMB free acid also called HMB-acid
- HMB-acid improves HMB availability to tissues and thus provides a more rapid and efficient method to get HMB to the tissues than administration of CaHMB. It was shown that in many instances HMB free acid is a better delivery form of HMB.
- HMB-acid to a non-emulsified liquid nutritional supplement would have similar results to the results observed when CaHMB is added to a liquid. Specifically, it was expected that addition of HMB-acid would result in a layer of HMB-acid appearing at the top of the liquid, that the HMB acid would be observed floating through the liquid and/or that the HMB-acid would interact with the other ingredients in the liquid causing clumping, sedimentation and changes to the physical appearance of the beverage. It was thus surprising and unexpected that the addition of HMB-acid to a liquid nutritional supplement resulted in the HMB-acid
- the present invention is a liquid nutritional supplement containing HMB in the free acid form.
- the present invention is a clear liquid beverage containing HMB in the free acid form.
- the nutritional supplement or beverage may contain calcium and soluble protein.
- the present invention is a method of adding free acid HMB to a liquid nutritional supplement or beverage.
- the addition of free acid HMB may occur during the process of manufacturing a liquid or beverage product or it may be done immediately prior to consuming the liquid or beverage.
- the present invention comprises such a nutritional supplement containing soluble protein and free acid HMB and is still shelf stable.
- the addition of free acid HMB to a liquid that does not contain soluble protein also surprisingly does not result in a liquid sedimentation and separation that would be expected upon the addition of free acid HMB.
- Fig. 1 shows photographs of the bottles showing the physical appearance of the liquid supplements studied in Example 1 at days 1, 4, 14 and 21.
- Fig. 2a shows photographs of the bottles of ISOPURE showing the physical appearance of the ISOPURE samples studied in Example 3 at days 0, 7, 14, 28 and 42.
- Fig. 2b shows photographs of the bottles of GNC-Protein Juice showing the physical appearance of the GNC-Protein Juice samples studied in Example 3 at days 0, 7, 14, 28 and 42.
- Fig. 2c shows photographs of the bottles of Gatorade Recovery showing the physical appearance of the Gatorade Recovery samples studied in Example 3 at days 0, 7, 14, 28 and 42.
- Fig. 2d shows photographs of the bottles of Spartos Protein water showing the physical appearance of the Spartos Protein water samples studied in Example 3 at days 0, 7, 14, 28 and 42.
- Fig. 3 is a graph depicting the stability results of 300mg of HMB-acid over 120 days.
- Fig. 4 is a graph depicting the stability results of lOOOmg of HMB-acid over 120 days.
- Fig. 5 is a graph depicting the stability results of 3000mg of HMB-acid over 120 days.
- the invention is a non-emulsified, substantially clear liquid nutritional supplement, most typically a beverage or drink, containing free acid HMB.
- the liquids of the present invention may contain water and free acid HMB. Additional ingredients may include soluble protein, amino acids, carbohydrates, vitamins and minerals such as calcium.
- the invention comprises, at its base, HMB-acid and a liquid.
- the liquid has a crude fat content of less than 1%.
- the invention may include free fatty acids, such as DHA or EPA, yet still be considered to have less than 1% crude fat content.
- Water, sports drinks, juices, soft drinks, pharmaceutical liquids and substantially clear nutritional supplements such as Ensure Clear, IsoPure protein drink, GNC protein juice, Gatorade Recover, and Spartos protein water may comprise the liquid of the present invention, although the invention is not limited to these liquids.
- HMB-acid in a liquid nutritional supplement
- HMB-acid may be added to food, such as honey, applesauce, fruit ribbons and other foodstuffs in the manufacturing process or after manufacturing prior to ingestion by the consumer.
- HMB-acid is present in an effective amount.
- An effective amount includes a range from about 0.01 grams to about 0.2 grams of HMB-acid per kilogram body weight in twenty-four (24) hours.
- HMB-acid may also be administered to a human in an effective amount from about 0.5 grams to about 30 grams of HMB-acid per day.
- premade products that include HMB-acid will have HMB-acid present substantially in these ranges.
- HMB-acid Individual servings of HMB-acid to be added to a liquid or foodstuff will also have HMB-acid present substantially within these ranges.
- Any soluble protein source is suitable for use in the present invention, including but not limited to whey protein concentrate, whey protein isolate, casein hydrolysate, hydrolyzed collagen and combinations thereof.
- the liquid nutritional supplement may also include calcium, most preferably in a soluble form to minimize interaction with other components of the supplement (such as the free acid HMB or soluble protein if present).
- suitable forms of calcium include calcium carbonate, calcium citrate, calcium gluconate, calcium lactate, calcium phosphate and calcium pantothenate.
- the liquid nutritional supplement of the present invention may also include vitamins, such as vitamin D.
- vitamins such as vitamin D.
- Vitamin D may be included in any form, and most preferably as Vitamin D 3 , also known as cholecalciferol.
- the amount of vitamin D to be included can be any amount of vitamin D, up to an amount causing toxicity. Typical amounts of vitamin D are up to 4000IU, though much higher amounts may be included as described in U.S. Patent Application Publication No. 2010/0179112.
- HMB-acid as used in this invention is generally in a liquid form.
- Other forms of HMB-acid within the scope of this invention include HMB-acid in a gel or gel-matrix form. Any and all forms of HMB-acid may be used in the present invention.
- free acid HMB may be added to a liquid at any point prior to consumption.
- free acid HMB may be added to a liquid or foodstuff during the manufacturing process and at any time during the manufacturing process.
- Suitable methods of manufacturing include but are not limited to a hot fill process, retort or aseptic filling of liquid products and the HMB-acid may be added at any time during any of these manufacturing processes.
- the HMB-acid can be added at any time during any manufacturing process and the product will be shelf-stable with minimal separation or sedimentation of the HMB-acid interacting with other components of the liquid or foodstuff.
- HMB-acid may be added to a liquid or foodstuff after manufacture and prior to consumption.
- HMB-acid may be provided separate from the liquid or foodstuff for a consumer to add to a liquid or foodstuff of their choice.
- Discretely measured packages of HMB-acid most typically in a concentrate form, and most typically a gel form, may be provided to add to a defined amount of water, sports beverage, juice, substantially clear nutritional liquid, etc.
- the HMB-acid may be provided in single or multiple dose packages. The HMB-acid will mix in any potable liquid or foodstuff and is soluble in the aforementioned liquids and foodstuffs.
- the present invention is not dependent on the pH of the liquid base to which HMB- acid is added.
- the pH of the liquid base may be as low as about 2.0.
- HMB-acid is by definition HMB in a dissociated form and it was expected that the free acid form would interact with soluble proteins and other components of the liquid which would result in sedimentation, etc. Surprisingly, the free acid form of HMB does not interact with any of the other components, thus providing a stable product with little to no separation or sedimentation. The observation that HMB-acid goes into solution almost instantly when added to a liquid was also unexpected.
- HMB-acid it was expected that the addition of HMB-acid to a liquid would result in the HMB-acid forming a layer at the top of the liquid, or floating throughout the liquid or that the HMB-acid would interact with the other ingredients in the liquid causing clumping, sedimentation and changes to the physical appearance of the beverage. Instead, addition of HMB-acid followed by slight shaking results in the immediate disappearance of the HMB-acid and a crystal clear liquid.
- HMB-acid had little to no impact on the flavor, texture, mouthfeel and stability of the liquid drink matrix.
- Example 1 Stability of Product Composition with the addition of HMB (free acid and Calcium salt forms)
- N 2 (Two flavors of a commercially available ready-to-drink soluble-protein product; Ensure Clear, pH approximately 2.74)
- Bottles were sealed with rubber caps and crimped shut. Then, they were mixed well and placed on shelf.
- N 2 (Two flavors of a commercially available ready-to-drink soluble-protein product; Ensure Clear, pH approximately 2.74)
- the soluble-protein ready-to-drink products containing HMB free acid were surprisingly stable compared to those containing CaHMB. Additionally, the addition of HMB free acid had no impact on the physical appearance, mouthfeel or texture of the product when compared to the control with only a slight change in after-taste (more sour which is likely due to the low pH of the HMB free acid).
- Gatorade Recover to C1-C3, and 40ml Spartos protein water to D1-D3.
- the following tables 6-9 provide the nutritional information for each of the liquids tested (ISOPURE, GNC Protein Juice, Gatorade G3-Recover, and Spartos protein water.)
- Gatorade G3 Recover- Mixed Berry- Serving size 8 fl. oz/240ml
- the liquids to which calcium HMB was added are cloudy and contain precipitate by 42 days.
- the calcium HMB bottles are bottles A2, B2, C2 and D2.
- the bottles containing liquid and HMB-acid (A3, B3, C3 and D3) are clear and precipitate-free at 42 days and look the same as the control bottles (no HMB) (Al, Bl, CI and Dl).
- This experiment was designed to observe the stability of HMB-acid at various concentrations in soluble protein over 120 days.
- HMB free acid was measured for each solution using HPLC at 5 different time points: 0, 30, 60, 90, and 120 d.
- HMB free acid used was MTI 1301-100-03 (Lot 120111036).
- ISOPURE protein drink used was Lot 1212111132310.
- ISOPURE protein drink has a pH of approximately 2.54.
- Table 10 shows bottle labeling: Table 10
- HMBFA For bottles in group A, 60mg of HMBFA into each of the five bottles was added, and then 48ml of ISOPURE protein drink was added.
- the HMBFA concentration was 1.25mg/ml.
- HMBFA For bottles in group C, 600mg of HMBFA into each of the five bottles was, and then 48ml of ISOPURE protein drink was added.
- the HMBFA concentration was 12.5mg/ml.
- ISOPURE protein drink has a protein concentration of 0.0677g/ml; the amount of protein in each sample was 3.25 g.
- Table 11 shows actual weight(mg) and concentrations(mg/48ml) of samples.
- Table 12 shows the HMB standard curve to use.
- the concentrations of each HMBFA sample were now: 0.625mg/ml, 2.08mg/ml, and 6.25mg/ml respectively.
- the three prepared concentrations of HMB Free acid with ISOPURE sports drink were analyzed for HMB concentrations using HPLC at 0, 30, 60, 90 and 120 d.
- the ingredients in the ISOPURE sports drink interfered with our KIV internal standard peak so external standard based calculations were used to quantify HMB in each sample.
- the quantified amount of HMB was compared to the expected amount of HMB for each sample at each test time and expressed in percent of expected.
- the results are presented in Figs.3-5.
- the three different concentrations of HMB-FA in the sports drink tended to numerically decrease over time but no significant linear decrease was detected, p > 0.05.
- the changes were less than 8.0 %.
- the 300, 1000, and 3000 mg /serving of HMB-FA sample varied from 98.6% to 91.84, 98.1% to 94.96, and 97.28% to 93.57%% of expected, respectively.
- Fig 3 shows samples containing 300mg of HMB free acid/serving of soluble protein that were evaluated for stability for 120 days.
- the decrease in HMB free acid was less than 8% of the expected amount of HMB free acid and there was no significant linear decrease, p ⁇ 0.05.
- Fig. 4 shows samples containing lOOOmg of HMB free acid/serving of soluble protein that were evaluated for stability for 120 days.
- the decrease in HMB free acid was less than 8% of the expected amount of HMB free acid and there was no significant linear decrease, p ⁇ 0.05.
- Fig. 5 shows samples containing 3000mg of HMB free acid/serving of soluble protein that were evaluated for stability for 120 days.
- the decrease in HMB free acid was less than 8% of the expected amount of HMB free acid and there was no significant linear decrease, p ⁇ 0.05.
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Abstract
Description
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Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP14885107.4A EP2993994A4 (en) | 2013-03-14 | 2014-03-14 | Liquids and foodstuffs containing beta-hydroxy-beta-methylbutyrate (hmb) in free acid form |
AU2014386220A AU2014386220B2 (en) | 2013-03-14 | 2014-03-14 | Liquids and foodstuffs containing beta-hydroxy-beta-methylbutyrate (HMB) in free acid form |
CA2942646A CA2942646C (en) | 2014-03-14 | 2014-03-14 | Liquids and foodstuffs containing beta-hydroxy-beta-methylbutyrate (hmb) in free acid form |
JP2016575295A JP6480964B2 (en) | 2014-03-14 | 2014-03-14 | Liquid and food containing β-hydroxy-β-methylbutyric acid (HMB) in free acid form and process for producing the same |
CN201480025055.6A CN105578901A (en) | 2014-03-14 | 2014-03-14 | Liquids and foodstuffs containing beta-hydroxy-beta-methylbutyrate (hmb) in free acid form |
PCT/US2014/027596 WO2015137965A1 (en) | 2014-03-14 | 2014-03-14 | Liquids and foodstuffs containing beta-hydroxy-beta-methylbutyrate (hmb) in free acid form |
HK16111886.6A HK1223509A1 (en) | 2014-03-14 | 2016-10-14 | Liquids and foodstuffs containing beta-hydroxy-beta-methylbutyrate (hmb) in free acid form ---(hmb) |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US2014/027596 WO2015137965A1 (en) | 2014-03-14 | 2014-03-14 | Liquids and foodstuffs containing beta-hydroxy-beta-methylbutyrate (hmb) in free acid form |
Publications (1)
Publication Number | Publication Date |
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WO2015137965A1 true WO2015137965A1 (en) | 2015-09-17 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/US2014/027596 WO2015137965A1 (en) | 2013-03-14 | 2014-03-14 | Liquids and foodstuffs containing beta-hydroxy-beta-methylbutyrate (hmb) in free acid form |
Country Status (6)
Country | Link |
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JP (1) | JP6480964B2 (en) |
CN (1) | CN105578901A (en) |
AU (1) | AU2014386220B2 (en) |
CA (1) | CA2942646C (en) |
HK (1) | HK1223509A1 (en) |
WO (1) | WO2015137965A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3836803A4 (en) * | 2018-06-25 | 2022-07-20 | Metabolic Technologies, Inc. | Stability of vitamin d in beta-hydroxy- beta-methylbutyrate (hmb) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP7286964B2 (en) * | 2018-12-28 | 2023-06-06 | 日油株式会社 | Liquid nutritional composition containing β-hydroxy-β-methylbutyric acid, protein, and liquid oil |
SG11202012984YA (en) * | 2019-06-25 | 2021-01-28 | Metabolic Technologies Inc | STABILITY OF VITAMIN D IN ß-HYDROXY- ß-METHYLBUTYRATE (HMB) |
JP2021069308A (en) * | 2019-10-30 | 2021-05-06 | 小林製薬株式会社 | Orally-taken composition |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US20100179112A1 (en) | 2008-12-09 | 2010-07-15 | Metabolic Technologies, Inc. | Nutritional Intervention for Improving Muscular Function and Strength |
US20110256272A1 (en) * | 2010-01-29 | 2011-10-20 | Johns Paul W | Aseptically Packaged Nutritional Liquids Comprising HMB |
WO2012109105A1 (en) * | 2011-02-07 | 2012-08-16 | Abbott Laboratories | Nutritional products comprising beta-hydroxy-beta-methylbutyrate |
WO2014043685A1 (en) * | 2012-09-17 | 2014-03-20 | Abbott Laboratories | Beta-hydroxy-beta-methylbutryic acid- containing compositions and uses thereof |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050215640A1 (en) * | 2004-03-26 | 2005-09-29 | Baxter Jeffrey H | HMB compositions and uses thereof |
CN101524155B (en) * | 2009-04-20 | 2012-10-10 | 北京康比特体育科技股份有限公司 | Amino acid composition |
JP6077857B2 (en) * | 2009-12-18 | 2017-02-08 | メタボリック・テクノロジーズ,インコーポレーテッド | Improved method of administration of β-hydroxy-β-methylbutyrate (HMB) |
CN101785566A (en) * | 2010-01-22 | 2010-07-28 | 北京康比特体育科技股份有限公司 | Sports beverage containing HMB |
TWI526161B (en) * | 2010-06-10 | 2016-03-21 | 亞培公司 | Substantially clear nutritional liquids comprising calcium hmb and soluble protein |
-
2014
- 2014-03-14 CN CN201480025055.6A patent/CN105578901A/en active Pending
- 2014-03-14 CA CA2942646A patent/CA2942646C/en active Active
- 2014-03-14 WO PCT/US2014/027596 patent/WO2015137965A1/en active Application Filing
- 2014-03-14 AU AU2014386220A patent/AU2014386220B2/en active Active
- 2014-03-14 JP JP2016575295A patent/JP6480964B2/en active Active
-
2016
- 2016-10-14 HK HK16111886.6A patent/HK1223509A1/en unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100179112A1 (en) | 2008-12-09 | 2010-07-15 | Metabolic Technologies, Inc. | Nutritional Intervention for Improving Muscular Function and Strength |
US20110256272A1 (en) * | 2010-01-29 | 2011-10-20 | Johns Paul W | Aseptically Packaged Nutritional Liquids Comprising HMB |
WO2012109105A1 (en) * | 2011-02-07 | 2012-08-16 | Abbott Laboratories | Nutritional products comprising beta-hydroxy-beta-methylbutyrate |
WO2014043685A1 (en) * | 2012-09-17 | 2014-03-20 | Abbott Laboratories | Beta-hydroxy-beta-methylbutryic acid- containing compositions and uses thereof |
Non-Patent Citations (1)
Title |
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See also references of EP2993994A4 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3836803A4 (en) * | 2018-06-25 | 2022-07-20 | Metabolic Technologies, Inc. | Stability of vitamin d in beta-hydroxy- beta-methylbutyrate (hmb) |
Also Published As
Publication number | Publication date |
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AU2014386220A1 (en) | 2015-11-05 |
CA2942646C (en) | 2021-12-28 |
AU2014386220B2 (en) | 2018-04-26 |
HK1223509A1 (en) | 2017-08-04 |
CN105578901A (en) | 2016-05-11 |
JP6480964B2 (en) | 2019-03-13 |
CA2942646A1 (en) | 2015-09-17 |
JP2017510629A (en) | 2017-04-13 |
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