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WO2008122613A2 - Complément alimentaire contenant des alpha-céto-acides - Google Patents

Complément alimentaire contenant des alpha-céto-acides Download PDF

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Publication number
WO2008122613A2
WO2008122613A2 PCT/EP2008/054103 EP2008054103W WO2008122613A2 WO 2008122613 A2 WO2008122613 A2 WO 2008122613A2 EP 2008054103 W EP2008054103 W EP 2008054103W WO 2008122613 A2 WO2008122613 A2 WO 2008122613A2
Authority
WO
WIPO (PCT)
Prior art keywords
alpha
dietary supplement
keto
dietary
keto acids
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2008/054103
Other languages
German (de)
English (en)
Other versions
WO2008122613A3 (fr
Inventor
Andreas Karau
Matthias Kottenhahn
Karlheinz Drauz
Norbert Windhab
Adolf GRÜNERT
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Evonik Degussa GmbH filed Critical Evonik Degussa GmbH
Priority to RU2009140373/13A priority Critical patent/RU2492705C2/ru
Priority to CN2008800106901A priority patent/CN101646358B/zh
Priority to BRPI0810099-3A priority patent/BRPI0810099A2/pt
Priority to EP08735843A priority patent/EP2129241A2/fr
Publication of WO2008122613A2 publication Critical patent/WO2008122613A2/fr
Publication of WO2008122613A3 publication Critical patent/WO2008122613A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • 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 dietary supplements containing alpha-keto analogs of branched-chain amino acids in support of the
  • Muscle building increased muscle performance and improvement of general well-being while relieving the metabolism to nitrogen detoxification by reduced nitrogen intake compared to the intake of the corresponding amino acids and an improved nitrogen metabolism in the body.
  • Physical inactivity is a risk factor that can lead to decreased physical performance and thus reduced quality of life.
  • a physical training is essential, with a
  • the average requirement for protein is about 660 mg / kg body weight, which can be significantly increased by physical training.
  • the need for protein can usually be met by a balanced diet, which is not easy to achieve.
  • Physical training leads, caused by increased protein degradation and humiliated Protein synthesis, to a changed need for nutrients, continues to result in a changed metabolic situation, which is due for example to the influence of physical training on the hormone system and ultimately also lack knowledge about a suitable diet with increasing physical stress, especially in relation to the age, so that fast one
  • BCAA branched chain amino acids
  • Branched-chain amino acids alpha-keto acids also play an important role in amino acid metabolism, especially in skeletal muscle and in the liver.
  • One-third of the muscle protein consists of the branched-chain amino acids, which can not be formed by the body, but must be taken with the food. In muscle, especially during physical exertion, proteins are constantly being built up and broken down
  • the corresponding alpha-keto acid is formed by transfer of the amino group to a carrier.
  • the obtained keto acid can then be further enzymatically oxidized for energy.
  • the carrier is transported to the liver where it releases toxic ammonia, which must be converted to urea and excreted via the kidney.
  • alpha-keto acids which are branched-chain
  • alpha-ketoisocaproate ketoleucine
  • ketoleucine can be used to reduce protein breakdown in muscle and to reduce urea formation resulting from protein degradation after muscle surgery (US Pat. No. 4,677,121).
  • ketoleucine in malnutrition
  • ketoleucine takes place intravenously.
  • the administration of the alpha-keto acids of leucine, isoleucine and VaNn has been proposed in patients who have a protein-reduced diet, e.g. due to kidney failure (US 4,100,161).
  • the role of the alpha-keto acids within protein metabolism with respect to various medical indications is also discussed in Walser, M. et al., Kidney International, Vol. 38 (1990), pp. 43-39. 595-604.
  • dietary supplements which contain at least one alpha-keto acid selected from the group alpha- ketoisocaproate (KIC), alpha-ketoisovalerate (KIV) and alpha-keto-beta-methylvalerate (KMV) and / or a salt thereof alpha-keto acids, wherein the supplement may optionally additionally contain one or more amino acids, in particular leucine, isoleucine and / or VaNn, but otherwise is nitrogen-free.
  • KIC alpha- ketoisocaproate
  • KIV alpha-ketoisovalerate
  • KMV alpha-keto-beta-methylvalerate
  • Nutritional supplements comprising nitrogenous additives which may be added to the dietary supplement in a very low amount of less than 5 mg (daily dose), e.g. nitrogenous vitamins.
  • nitrogenous additives which may be added to the dietary supplement in a very low amount of less than 5 mg (daily dose), e.g. nitrogenous vitamins.
  • dietary supplements which have no nitrogen-containing constituents, in particular no cationic ones, are preferred.
  • nitrogen-free refers to the supplement itself.
  • functional foods containing the claimed dietary supplement may also contain nitrogen-containing ingredients contain, in particular, no supplements that increased an additional Include supplementation with nitrogenous compounds.
  • nitrogen-containing ingredients contain, in particular, no supplements that increased an additional Include supplementation with nitrogenous compounds.
  • Suitable salts are in particular the alkali or alkaline earth metal salts, in particular the Na + , K + , Ca 2+ and Mg 2+ salts, of the stated alpha-keto acids.
  • a preferred embodiment is nutritional supplements comprising a combination of alpha-ketoisocaproate and alpha-ketoisovalerate or alpha-keto-beta-methylvalerate or a combination of alpha-ketoisovalerate and alpha-keto-beta-methylvalerate or a combination of all three alpha-keto acids or their salts.
  • Preferred weight ratios for KIC / KIV are between 3: 1 and 1: 1, for KIC / KMV between 3: 1 and 1: 1 and for KIV / KMV between 2: 1 and 1: 2.
  • Corresponding ratios are also for a KIC / KIV / KMV mixture advantageous.
  • a particularly suitable combination of KIC / KIV / KMV represents a weight ratio of 2: 1: 1, wherein said proportions can be varied +/- 10%.
  • the weight ratios mentioned are particularly suitable for rapid regenerative muscle growth.
  • the daily dose of alpha-ketoacids taken up by the dietary supplement should not exceed the levels of 2000 mg / kg body weight for KIC, 1000 mg / kg body weight for KIV and 1500 mg / kg body weight for BMV, preferably doses of between 2.5 mg / kg and 500 mg / kg body weight for each of the three alpha keto acids.
  • Particularly preferred dosages are in the range of 25 mg / kg to 250 mg / kg body weight for KIC, KIV and KMV, so that at
  • An adult (eg at a body weight between 50 and 100 kg) has an approximate preferred total amount per ingested alpha-keto acid of 1, 25 g to 25 g.
  • the following preferred dosages are given for the alpha-keto acids: for KIC between 50 mg / kg to 200 mg / kg, for KIV between 25 mg / kg to 150 mg / kg and for KMV between 25 mg / kg to 100 mg / kg.
  • Usual daily dosages range from 0.5 g to 50 g per alpha-keto acid per day. In terms of the amount of cations contained should be in
  • Nutritional supplement preferably not more than 10g, more preferably between 0.5g and 2g, of Na + , K + ions, preferably not more than 5g, more preferably between 0.2 and 2.5g Ca 2+ ions and not more than 2g better between 0.2 and 1 g, containing the corresponding Mg 2+ ions.
  • the branched-chain amino acids leucine, isoleucine and VaNn can also be added to the dietary supplement described here.
  • the amino acids mentioned are preferably used in small amounts.
  • the amount added to the dietary supplement should not exceed a ratio of 1: 0.5, more preferably 1: 0.1 (alpha-keto acid: corresponding amino acid).
  • particularly preferred dietary supplements do not contain leucine, isoleucine or VaNn.
  • Particularly preferred dietary supplements contain further keto acids derived from naturally occurring amino acids or salts thereof, particularly preferably alpha-ketoglutaric acid or its salts, in particular alpha-ketoglutarate (AKG).
  • alpha-ketoglutaric acid or its salts in particular alpha-ketoglutarate (AKG).
  • AKG alpha-ketoglutarate
  • the abovementioned dosage information also applies to the additionally contained alpha-keto acids or their salts.
  • Dietary supplements containing a combination of KIC, KIV and / or KMV and AKG include a particularly preferred embodiment of the present invention.
  • preferred dietary supplements also contain creatine as an ingredient.
  • the dietary supplement can be added to other nitrogen-free additives.
  • energy-giving compounds preferably from the group of carbohydrates, such. Glucose, but also additives that promote the regeneration process, such. Vitamins, especially Vitamin A, Vitamin Bi, B2, B & and B12, Vitamin C, Vitamin D, Vitamin E, Vitamin K, Pantothenic acid, Niacin, Folic Acid, Biotin, Choline and Inositol.
  • antioxidants e.g. beta-carotene, potassium citrate, citric acid, lactic acid, tocopherol, sodium or potassium ascorbates or ascorbic acid may be included in the dietary supplement.
  • Preferred dietary supplements may be e.g. contained (the quantities represent the preferred daily dose):
  • 5-100 ⁇ g of chromium up to 100 mg Vitamin Bi, up to 100 mg Vitamin B2, up to 100 mg Vitamin B ⁇ , up to 200 ⁇ g Vitamin B12, up to 5 g Vitamin C, up to 500 mg Vitamin E, up to 300 mg pantothenic acid, up to 1 g niacin, up to 10 mg folic acid, up to 1 mg biotin.
  • additives include saturated or unsaturated fatty acids, in particular C 6 -C 22 -fatty acids, as an additive.
  • coconut, safflower, soybean oil, lard and beef tallow coconut, safflower, soybean oil, lard and beef tallow.
  • preservatives, food colors, sweeteners, flavor enhancers and / or flavorings in the dietary supplement may also be included in the usual amounts known to those skilled in the art.
  • flavoring substances are considered as additives, since e.g. free alpha-keto acids acidic or their salts can taste unpleasant. If the additives used are used in larger quantities, nitrogen-free additives are used. However, particularly preferred dietary supplements do not contain nitrogenous additives.
  • the claimed dietary supplements may be used, for example, in the form of a powder, a tablet or in the form of a solution or suspension.
  • the alpha-keto acids or their salts are preferably formulated with about 30 to 80 percent by volume in the dietary supplement, preferably using nitrogen-free additives, in particular carbohydrates, fats and oils, and optionally also of amino acids, such as leucine, isoleucine and VaNn, which may be present at about 70 to 20 volume percent in the dietary supplement
  • Suitable carriers are e.g. linear or (hyper) branched polyesters, polyethers, polyglycerols, polyglycolides, polylactides, polylactide-co-glycolides, polytartrates and polysaccharides, or polyethylene oxide-based dendrimers, polyether-dendrimers, coated PAMAM dendrimers, e.g. Polylactide-co-glycolide coating, or polyarylether.
  • the powder or tablet may further be provided with a coating, e.g. allow the release of the dietary supplement only in the intestinal tract.
  • a coating e.g. allow the release of the dietary supplement only in the intestinal tract.
  • the following capsule shell materials are preferably used: carboxymethylcellulose, nitrocellulose, polyvinyl alcohol, shellac, carrageenan,
  • emulsifiers or colloids may be useful in order to be able to absorb all desired components as well as possible in an aqueous system.
  • Suitable additives are e.g. Polyvinyl alcohols, glycerides of fatty acids, their acetic, citric, lactic or tartaric acid esters, polyoxyethylene stearates, carbohydrate esters, propylene glycol esters, glycerol esters or sorbitan esters of fatty acids or sodium lauryl sulfate.
  • Another object of the present invention are food (Functional Food) containing the claimed dietary supplement.
  • These may be, for example, drinks or bars, which are particularly suitable for receiving the dietary supplement.
  • the foods may be added during their production with the claimed dietary supplement or it may later be added a formulation of the dietary supplement to the food, for example in the form of a powder or a tablet.
  • a formulation of the dietary supplement to the food, for example in the form of a powder or a tablet.
  • the dissolution of effervescent tablets or a powder in mineral water can be cited here.
  • Training causes muscular adjustment including muscle damage, muscle hypertrophy and muscle transformation.
  • a training session is a combination of a training phase and a regeneration phase.
  • a suboptimal embodiment of the training unit may e.g. lead to overtraining syndrome resulting in prolonged fatigue with reduced physical capacity. Such overtraining syndrome is often caused or exacerbated by malnutrition.
  • ammonia detoxification is accelerated, which leads to a faster muscle recovery or reduced fatigue of the muscles.
  • a faster regeneration can also be increased training or increased
  • Dietary supplements especially for athletes, as well as recreational and top athletes, including strength athletes, as well as to wellness and fitness enthusiasts.
  • the use of nutritional supplements by the elderly, who are known to often have limited nitrogen economy or limited nitrogen excretion capacity, is also particularly advantageous. Therefore, another object of the present invention is the use of the claimed dietary supplements for the production of orally absorbable products, such as functional food, in particular drinks, gels, creams, mash, power bars, etc., as well as tablets, powders, for example, in letters, Bags, tubes can be offered, and to
  • another object of the present invention is the use of the dietary supplements or foods described in combination with a targeted diet, in particular a calorie-reduced diet, slimming or fitness diets.
  • claimed dietary supplements can also be used for the production of animal feed.
  • the higher performance of the muscles which is achieved by taking the dietary supplements or the thus modified foods, can show on the one hand in an improved endurance ability, on the other hand also in an increased bounce and other performance.
  • subjects can be put into a state of overtraining (intensive training with insufficient regeneration).
  • the keto acid substitution can be e.g. by effervescent tablets, which are dissolved in water, the amount of alpha-keto acids should be adjusted to the body weight of the subject.
  • the freshly mixed drinks are preferred during or shortly after each
  • the preferred formulation for such a test is the use of 0.2 g / kg / d calcium or sodium alpha-ketoglutarate or the corresponding free acid, or 0.2 g / kg / d calcium or sodium alpha-ketoisocaproate or the corresponding free acid or of 0.2 g / kg / d calcium or sodium alpha-ketoisovalerate or the corresponding free acid or 0.2 g / kg / d Calcium
  • Sodium alpha-Ketomethylvalerat or the corresponding free acid or 0.2 g / kg / d of a mixture of these components in particular from the calcium or sodium salts of KIC (eg 95 mg / kg / d), MIV (eg 60 mg / kg / d) and KMV (eg 45 mg / kg / d).
  • KIC eg 95 mg / kg / d
  • MIV eg 60 mg / kg / d
  • KMV eg 45 mg / kg / d
  • calcium and / or sodium glucose or free glucose can be used as placebo.
  • the appearance and taste should be as identical as possible for all formulations.
  • a nutritional protocol should also be used, using as standardized a diet as possible (for example Nutritional Protocol Program Prodi).
  • the determination of the general state of health and the stress recovery can be made by questioning the subjects. Further information about changes in overall performance can be found in the change in body weight and body fat percentage.
  • V ⁇ 2max the maximum oxygen uptake
  • the load on a cycle ergometer is increased by means of a ramp protocol (for example beginning 0 watt, continuous increase of the power with 50)
  • the heart rate can be determined synchronously by means of electrocardiography.
  • Oxygen uptake is calculated from online minute ventilation and the difference in oxygen concentration between inspiratory and expiratory gases.
  • IAAS Individual Anaerobic Aerobic Threshold
  • the measurement of the bounce improvement can by means of a
  • Bounce plate of the company Kistler, Winterthur, Switzerland be determined.
  • the device's own protocols "Squat-Jump” and “Count-Movement Jump” are used. The bounce is measured based on the contact time on the measuring plate and the jump height and calculated in comparison with the body weight.
  • the maximum force e.g. the leg muscles are stressed at a defined angle and the maximum force is measured.
  • Metabolic parameters e.g. the concentrations of BCKA and AKG or urea or uric acid concentration in the blood can be determined by HPLC
  • Measurements are measured. To determine the damage of muscle cells, e.g. During physical exercise, uric acid levels in the blood or urine or creatine kinase activity in the blood are determined. The increase in creatine kinase activity correlates with the extent of muscle damage and may be due to an enzymatic reaction
  • kit no. 1087533 from Roche Diagnostics, Mannheim, Germany.
  • the uric acid concentrations can be determined photometrically using the "Fluitest IIA®” kit from Biocon Diagnostics, Vöhl / Marienhagen, Germany.
  • the effects of the claimed dietary supplement on protein metabolism can be demonstrated by measurements of urea concentrations in the blood or urine.
  • the urea concentrations can be determined by photometric end point determination at a wavelength of 334 nm using the urea S test combination (reagent kit No. 777510 from Boehringer Mannheim, Germany).
  • a supportive effect of the claimed dietary supplement with regard to muscle growth can be made by determining the expression of the myogenic factors Myo D and myogenin by RT-PCR.
  • the subjects are given tissue samples before and after the training phase from the muscle by biopsy, using a biopsy needle (e.g., a 13-gauge biopsy needle of the
  • the muscular adaptation can also be checked by the analysis of the myosin heavy chain (MHC) isoforms or by the determination of the stress protein Hsp70 (inducible form) (analytical method, for example according to Liu et al., Eur. J. Appl. Physiol. 91: 330-335, 2004, Liu et al., Int J. Sports Med. 21: 351-355, 200, Liu et al., J. Appl.
  • MHC myosin heavy chain
  • BCKAs branched-chain alpha-keto acids
  • Training 30 minutes of endurance training (running) per day 3x3 minutes of high-speed running per day
  • Keto acids in the composition described below or Mix 2 (placebo) in which a subject always took the same mix over the entire duration.
  • keto acid mixtures can be stirred into commercially available sweet or salty products such as yoghurts, whey drinks, fruit compote and dessert soups.
  • the training was performed according to the above form and controlled by the subjects themselves.
  • the training was carefully documented by the test persons in the training protocol and regularly checked in random samples. Therefore, we assume that the completed training questionnaire is essentially plausible.
  • Performance in particular the parameter "sustained exercise time” as an expression of exercise tolerance, on general physical performance as well as on muscle function. According to our study design, the training was to be done with 5 units per week, with each training session providing 30 minutes of endurance training
  • Figure 1 shows the total exercise time per week. The total training time in the 1st week did not differ between the groups.
  • the urea concentration in the plasma had a similar level before training in both groups. At the end of training, the urea concentration in both groups was higher than before, but to varying degrees depending on the dietary supplement. The increased urea concentrations after the training indicated an increased urea synthesis, which resulting from a reduced due to physical training protein degradation.
  • Plasma urea concentration at the end of exercise in the BCKA group was significantly higher than that in the placebo group. After one week of regeneration, no further increase was found in the BCKA group, while there was a marked increase in the placebo group.
  • urea synthesis is based on the protein-derived ammonia
  • increased urea synthesis may be explained by the fact that the ammonia produced in the working musculature, resulting from protein degradation by catabolism, is more rapidly transported to the liver; or possibly KAS has favored urea synthesis in the liver.

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  • Life Sciences & Earth Sciences (AREA)
  • Mycology (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

Complément alimentaire qui peut contenir au moins un acide aminé, ledit complément alimentaire étant par ailleurs essentiellement exempt d'azote et renfermant au moins un alpha-céto-acide choisi dans le groupe constitué par l'alpha-céto-isocaproate, l'alpha-céto-isovalérate et l'alpha-céto-bêta-méthylvalérate et / ou un sel de ces alpha-céto-acides. Les compléments alimentaires décrits favorisent le développement musculaire et soulagent simultanément le métabolisme lors de l'élimination de l'azote par un apport réduit d'azote et une meilleure rétention de l'azote.
PCT/EP2008/054103 2007-04-04 2008-04-04 Complément alimentaire contenant des alpha-céto-acides Ceased WO2008122613A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
RU2009140373/13A RU2492705C2 (ru) 2007-04-04 2008-04-04 ПИЩЕВАЯ ДОБАВКА, СОДЕРЖАЩАЯ α-КЕТОКИСЛОТЫ
CN2008800106901A CN101646358B (zh) 2007-04-04 2008-04-04 含有a-酮酸的食品补充剂
BRPI0810099-3A BRPI0810099A2 (pt) 2007-04-04 2008-04-04 Suplemento alimentar contendo alfa-ceto ácidos
EP08735843A EP2129241A2 (fr) 2007-04-04 2008-04-04 Complément alimentaire contenant des alpha-céto-acides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007016715.8 2007-04-04
DE102007016715A DE102007016715A1 (de) 2007-04-04 2007-04-04 Nahrungsergänzungsmittel enthaltend alpha-Ketosäuren

Publications (2)

Publication Number Publication Date
WO2008122613A2 true WO2008122613A2 (fr) 2008-10-16
WO2008122613A3 WO2008122613A3 (fr) 2009-06-04

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PCT/EP2008/052724 Ceased WO2008122473A2 (fr) 2007-04-04 2008-03-06 Complément alimentaire contenant des acides alpha-céto
PCT/EP2008/054103 Ceased WO2008122613A2 (fr) 2007-04-04 2008-04-04 Complément alimentaire contenant des alpha-céto-acides

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PCT/EP2008/052724 Ceased WO2008122473A2 (fr) 2007-04-04 2008-03-06 Complément alimentaire contenant des acides alpha-céto

Country Status (6)

Country Link
EP (2) EP2175747A2 (fr)
CN (1) CN101646358B (fr)
BR (1) BRPI0810099A2 (fr)
DE (1) DE102007016715A1 (fr)
RU (1) RU2492705C2 (fr)
WO (2) WO2008122473A2 (fr)

Cited By (3)

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Publication number Priority date Publication date Assignee Title
WO2010112362A1 (fr) * 2009-04-03 2010-10-07 Evonik Degussa Gmbh Compléments alimentaires contenant des alpha-céto-acides, pour étayer le traitement du diabète
US9879289B2 (en) 2009-06-05 2018-01-30 Evonik Degussa Gmbh Method for the preparation of 2-keto carboxylic acid
EP3603419A1 (fr) 2018-07-31 2020-02-05 Evonik Operations GmbH Mélanges d'acides cétoniques à chaîne ramifiée (bcka) et procédé de production de tels mélanges

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CN101975827A (zh) * 2010-09-06 2011-02-16 江南大学 一种α-酮异己酸含量的检测方法
CN106963749A (zh) * 2017-03-23 2017-07-21 华南农业大学 α‑酮戊二酸（盐）在抗疲劳和提高肌肉运动力量方面的应用
US11484579B2 (en) 2017-11-29 2022-11-01 Edgar L Hull Vitamins and alpha keto acid compositions for use in a treatment program for chronic kidney disease patients
US11253496B2 (en) 2017-11-29 2022-02-22 Edgar L. Hull Alpha keto acid compositions for treating hypo-albuminemia
US12109254B2 (en) 2017-11-29 2024-10-08 Edgar Hull Vitamins and alpha keto acid compositions for use in a treatment program for chronic kidney disease patients
CN109011464B (zh) * 2018-08-08 2020-06-05 南通市多乾新材料科技有限公司 一种用于篮球进攻对抗上篮的训练装置
EP3797766A1 (fr) 2019-09-24 2021-03-31 Evonik Operations GmbH Compositions à utiliser pour réduire l'inflammation

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EP1754415A1 (fr) * 2005-08-18 2007-02-21 Gakic Formulations Ltd. Compositions diététiques supplémentaires pour améliorer les performances musculaires et/ou faciliter la récupération après l'effort
AU2006320670B8 (en) * 2005-11-30 2011-04-07 Nestec S.A. Methods for the treatment of muscle loss
FR2907011B1 (fr) * 2006-10-17 2010-05-14 Univ Paris Descartes Utilisation de la citrulline pour le traitement des etats de denutrition

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WO2010112362A1 (fr) * 2009-04-03 2010-10-07 Evonik Degussa Gmbh Compléments alimentaires contenant des alpha-céto-acides, pour étayer le traitement du diabète
CN102448452A (zh) * 2009-04-03 2012-05-09 赢创德固赛有限公司 用于支持糖尿病治疗的包含α-酮酸的膳食补充剂
JP2012522739A (ja) * 2009-04-03 2012-09-27 エボニック デグサ ゲーエムベーハー 糖尿病療法の支援のためのα−ケト酸を含有する栄養補助剤
US9879289B2 (en) 2009-06-05 2018-01-30 Evonik Degussa Gmbh Method for the preparation of 2-keto carboxylic acid
EP3603419A1 (fr) 2018-07-31 2020-02-05 Evonik Operations GmbH Mélanges d'acides cétoniques à chaîne ramifiée (bcka) et procédé de production de tels mélanges
WO2020025489A1 (fr) 2018-07-31 2020-02-06 Evonik Operations Gmbh Mélanges de cétoacides à chaîne ramifiée (bcka) et procédé pour la production de tels mélanges

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EP2129241A2 (fr) 2009-12-09
DE102007016715A1 (de) 2008-10-09
RU2492705C2 (ru) 2013-09-20
WO2008122473A3 (fr) 2009-04-23
BRPI0810099A2 (pt) 2014-09-23
CN101646358B (zh) 2013-05-29
WO2008122473A2 (fr) 2008-10-16
RU2009140373A (ru) 2011-06-20
CN101646358A (zh) 2010-02-10
EP2175747A2 (fr) 2010-04-21
WO2008122613A3 (fr) 2009-06-04

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