EP1345502A1 - Compose acide citrique/creatine, procede de fabrication et utilisation - Google Patents
Compose acide citrique/creatine, procede de fabrication et utilisationInfo
- Publication number
- EP1345502A1 EP1345502A1 EP01272630A EP01272630A EP1345502A1 EP 1345502 A1 EP1345502 A1 EP 1345502A1 EP 01272630 A EP01272630 A EP 01272630A EP 01272630 A EP01272630 A EP 01272630A EP 1345502 A1 EP1345502 A1 EP 1345502A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- citric acid
- creatine
- water
- temperatures
- formulation
- 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.)
- Withdrawn
Links
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 title claims abstract description 111
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 title claims abstract description 93
- 229960003624 creatine Drugs 0.000 title claims abstract description 46
- 239000006046 creatine Substances 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 11
- -1 citric acid compound Chemical class 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 238000009472 formulation Methods 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 235000015872 dietary supplement Nutrition 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 239000003674 animal food additive Substances 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 3
- 239000002537 cosmetic Substances 0.000 claims abstract description 3
- 235000013376 functional food Nutrition 0.000 claims abstract description 3
- 238000002329 infrared spectrum Methods 0.000 claims abstract description 3
- 239000004090 neuroprotective agent Substances 0.000 claims abstract description 3
- 239000007787 solid Substances 0.000 claims abstract description 3
- 229960004106 citric acid Drugs 0.000 claims description 29
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 229960002303 citric acid monohydrate Drugs 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 9
- 230000008018 melting Effects 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 7
- 229960004543 anhydrous citric acid Drugs 0.000 claims description 5
- 238000000227 grinding Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 235000014633 carbohydrates Nutrition 0.000 claims description 3
- 150000001720 carbohydrates Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 208000021642 Muscular disease Diseases 0.000 claims description 2
- 201000009623 Myopathy Diseases 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 235000001014 amino acid Nutrition 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims description 2
- 239000002858 neurotransmitter agent Substances 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 235000000053 special nutrition Nutrition 0.000 claims description 2
- 239000000021 stimulant Substances 0.000 claims description 2
- 235000000346 sugar Nutrition 0.000 claims description 2
- 239000011573 trace mineral Substances 0.000 claims description 2
- 235000013619 trace mineral Nutrition 0.000 claims description 2
- 239000011782 vitamin Substances 0.000 claims description 2
- 229940088594 vitamin Drugs 0.000 claims description 2
- 229930003231 vitamin Natural products 0.000 claims description 2
- 235000013343 vitamin Nutrition 0.000 claims description 2
- 230000029663 wound healing Effects 0.000 claims description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 claims description 2
- 229910004298 SiO 2 Inorganic materials 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 150000008163 sugars Chemical class 0.000 claims 1
- 235000005911 diet Nutrition 0.000 abstract description 3
- 230000000378 dietary effect Effects 0.000 abstract description 3
- 210000003205 muscle Anatomy 0.000 description 6
- MEJYXFHCRXAUIL-UHFFFAOYSA-N 2-[carbamimidoyl(methyl)amino]acetic acid;hydrate Chemical compound O.NC(=N)N(C)CC(O)=O MEJYXFHCRXAUIL-UHFFFAOYSA-N 0.000 description 5
- 229960004826 creatine monohydrate Drugs 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- MBBREGJRSROLGD-UHFFFAOYSA-N 2-[carbamimidoyl(methyl)amino]acetic acid;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical class NC(=N)N(C)CC(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O MBBREGJRSROLGD-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-phosphocreatine Chemical compound OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 description 2
- 229940109239 creatinine Drugs 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000006069 physical mixture Substances 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 235000019647 acidic taste Nutrition 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 235000015122 lemonade Nutrition 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000000944 nerve tissue Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000009984 peri-natal effect Effects 0.000 description 1
- 229950007002 phosphocreatine Drugs 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/17—Amino acids, peptides or proteins
- A23L33/175—Amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
-
- 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
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
-
- 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
- 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
- Creatine / citric acid compound process for its preparation and use
- the present application relates to creatine / citric acid compounds, their preparation and suitable formulations and their corresponding use.
- Creatine is primarily found in muscle and nerve tissue and, in the form of its metabolic secondary product, phosphocreatine, is an important energy reserve for the muscle and brain.
- creatine appears to have a prophylactic and therapeutic effect in ischemia, such as that described in B. caused by inf rct events or by pre- and perinatal oxygen deficit conditions.
- Creatine has been known as a muscle substance for over 100 years, and it serves as a source of energy for the muscle.
- creatine is not only a valuable nutritional supplement, but also has valuable therapeutic properties.
- a number of scientific studies have shown that the controlled intake of creatine over a longer period of time can lead to a significant increase in muscle mass and muscle performance as well as strength and endurance.
- creatine in a wide variety of application forms (e.g. oral, intravenous, etc.) requires high bioavailability and therefore good water solubility. However, this is usually not sufficient for creatine, which is present as an amino acid derivative in the form of an inner salt, which is why the creatine benefits from its undisputed advantages Supplements and therapies mostly achieved through one of its physiologically tolerable creatine salts.
- Citric acid is a tricarboxylic acid that is known to be common in the plant kingdom as well as in many animal tissues and body fluids. Citric acid counts u. a. to the series of prominent compounds that are involved in the physiological oxidation of fats, proteins and carbohydrates to carbon dioxide and water (see, inter alia, tricarboxylic acid cycle).
- Citric acid which was first isolated from lime juice by the Swedish chemist Karl Wilhelm Scheele in 1784, is currently produced biotechnologically by fermentation of cane sugar or molasses by the Aspergillus niger mold. Citric acid is used in its natural form or as a food additive E 330 in the packaging of food, but also in baking powders, effervescent lemonades and generally for acidification and as a flavoring agent. It also serves
- Citric acid to increase the stability of food or other organic substances.
- the pure, anhydrous citric acid mostly forms colorless, rhombic crystals with a slightly acidic taste.
- Effervescent formulations which contain creatine citrate as a 1: 1 salt or physical mixtures of creatine and citric acid are known from US Pat. No. 5,925,378.
- the object of the present invention was to develop compounds consisting of creatine and citric acid which are particularly valuable physiologically, at the same time have good water solubility and adequate storage stability and can be prepared in a simple manner.
- the creatine / citric acid compounds according to the invention have good storage stability, although the previously known salts of creatine easily decompose to form creatinine.
- pure salts would be obtained. a. can be excluded by the IR bands as well as the presence of simple physical mixtures.
- the addition and / or complex compounds according to the invention are particularly characterized in that they have a melting point which is between 110 and 160 ° C. and that they are generally free of organic Solvent proportions are contained, but a maximum of 0.1% by weight, which further increases the quality of the product properties.
- the present invention takes into account that the addition and / or complex compounds consisting of creatine and citric acid are in a solid state, with powdery variants having proven to be particularly suitable.
- Creatine and citric acid with a total water content of 5 to 15% by weight at temperatures between 0 and 70 ° C, in particular between 10 and 25 ° C, are mixed without solvents or dispersants and then by grinding in a mill, preferably in one Impact mill or other suitable grinding device;
- citric acid component can also be used alternatively or additionally in the form of suitable citric acid salts.
- the present invention also claims stable, physiologically tolerable formulations which contain the additive and / or complex compound consisting of creatine and citric acid, formulations being particularly preferred which contain further physiologically tolerable and / or physiologically active additives and / or contain formulation aids.
- the present invention also includes the use of the additive and / or complex compound as a dietary supplement, feed additive, dietetic, in Functional Foods, for special nutrition, as well as for increasing endurance and strength in the sports area; but the compounds according to the invention can also be used for rehabilitation, as a neuroprotective agent, for improving wound healing, for myopathies and dystrophies and in the cosmetics sector, which also takes into account the invention.
- Example 4 Production process for a creatine / citric acid compound of the composition creatine / citric acid in a molar ratio of 3: 1
- the creatinine content was below the detection limit, ie below 100 pprn.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nutrition Science (AREA)
- Mycology (AREA)
- Hematology (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Cosmetics (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Fodder In General (AREA)
Abstract
L'invention concerne des composés d'addition et/ou complexes constitués de créatine et d'acide citrique dans le rapport >1,0 à 3,0 : 1,0. Les composés selon l'invention sont caractérisés en ce qu'ils présentent dans le spectre infrarouge des bandes dont ξ= 3425 (± 5) cm-1 (s), 1624 (± 5) cm-1 (m-s) et 1247 (± 5) cm-1 (m). Lesdits composés ne contenant de préférence pas de solvant organique et se présentant à l'état solide pulvérulent sont notamment fabriqués au moyen d'un procédé consistant a¿1?) à transformer de la créatine contenant au plus 20 % en poids d'eau avec de l'acide citrique ou des sels de celui-ci à des températures de 0 à 70 °C ; ou, a2) à moudre de la créatine et de l'acide citrique ou des sels de celui-ci ayant une teneur totale en eau de 5 à 15 % en poids à des températures de 0 à 70 °C ; ou, a3) à transformer de la créatine en présence d'un solvant avec de l'acide citrique ou des sels de celui-ci à des températures de 0 à 70 °C. Ledit procédé consiste à extraire ensuite le solvant correspondant jusqu'à une teneur restante de 1 % en poids au plus. L'invention concerne également des formulations adaptées pouvant notamment servir d'additif alimentaire, de complément de nutrition animale, d'agent diététique, d'agent neuroprotecteur, ou dans le domaine cosmétique et similaires.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10065478 | 2000-12-28 | ||
| DE10065478A DE10065478C1 (de) | 2000-12-28 | 2000-12-28 | Kreatin/Citronensäure-Verbindung, Verfahren zu ihrer Herstellung und Verwendung |
| PCT/EP2001/013332 WO2002052957A1 (fr) | 2000-12-28 | 2001-11-16 | Compose acide citrique/creatine, procede de fabrication et utilisation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1345502A1 true EP1345502A1 (fr) | 2003-09-24 |
Family
ID=7669285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP01272630A Withdrawn EP1345502A1 (fr) | 2000-12-28 | 2001-11-16 | Compose acide citrique/creatine, procede de fabrication et utilisation |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20040077719A1 (fr) |
| EP (1) | EP1345502A1 (fr) |
| JP (1) | JP2005500978A (fr) |
| DE (1) | DE10065478C1 (fr) |
| WO (1) | WO2002052957A1 (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2235350C (fr) * | 1994-11-08 | 2009-01-06 | Avicena Group, Inc. | Utilisation de la creatine ou d'analogues de la creatine pour le traitement de maladies du systeme nerveux |
| US20030212130A1 (en) * | 2000-09-14 | 2003-11-13 | Miller Donald W. | Creatine ester anti-inflammatory compounds and formulations |
| US20030212136A1 (en) | 2001-09-14 | 2003-11-13 | Vennerstrom Jonathan L. | Creatine ester pronutrient compounds and formulations |
| US9833427B2 (en) | 2000-09-14 | 2017-12-05 | Board Of Regents Of The University Of Nebraska | Creatine ester anti-inflammatory compounds and formulations |
| DE10159244A1 (de) * | 2001-12-03 | 2003-06-18 | Degussa Bioactives Deutschland | Feste und stabile Kreatin/Citronensäure-Zusammensetzung(en) und Kohlenhydrat(e) bzw. deren Hydrate enthaltende Formulierung, Verfahren zu ihrer Herstellung und deren Verwendung |
| US20040126366A1 (en) * | 2002-06-04 | 2004-07-01 | Rima Kaddurah-Daouk | Methods of treating cognitive dysfunction by modulating brain energy metabolism |
| EP2468272A1 (fr) * | 2006-05-11 | 2012-06-27 | Avicena Group, Inc. | Procédés de traitement d'un trouble neurologique avec monohydrate de créatine |
| US20080003208A1 (en) * | 2006-05-11 | 2008-01-03 | Avicena Froup, Inc. | Creatine-ligand compounds and methods of use thereof |
| WO2009002913A1 (fr) * | 2007-06-22 | 2008-12-31 | Avicena Group, Inc. | Utilisation de composés de créatine pour traiter une dermatite |
| EP2269980A4 (fr) | 2008-12-24 | 2011-05-18 | Vertex Closed Joint Stock Company | Amides de créatine, procédé de production, et produit possédant une action neuroprotectrice |
| RU2428414C2 (ru) | 2009-11-03 | 2011-09-10 | Закрытое Акционерное Общество "Вертекс" | Способ получения амидов креатина |
| US9233099B2 (en) | 2012-01-11 | 2016-01-12 | University Of Cincinnati | Methods of treating cognitive dysfunction by modulating brain energy metabolism |
| US20220087966A1 (en) * | 2020-09-24 | 2022-03-24 | Southern Methodist University | Mechanosynthesis of a Co-Amorphous Formulation of Creatine with Citric Acid and Humidity-Mediated Transformation into a Co-Crystal |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1271687B (it) * | 1994-08-04 | 1997-06-04 | Flamma Spa | Sali organici idrosolubili della creatina |
| JP3690861B2 (ja) * | 1996-03-15 | 2005-08-31 | 富士写真フイルム株式会社 | 磁気記録媒体およびその製造方法 |
| US5925378A (en) * | 1997-03-31 | 1999-07-20 | Fortress Systems, L.L.C. | Method for enhancing delivery and uniformity of concentration of cellular creatine |
| US6211407B1 (en) * | 2000-05-03 | 2001-04-03 | Pfanstiehl Laboratories, Inc. | Dicreatine citrate and tricreatine citrate and method of making same |
-
2000
- 2000-12-28 DE DE10065478A patent/DE10065478C1/de not_active Expired - Fee Related
-
2001
- 2001-11-16 JP JP2002553921A patent/JP2005500978A/ja active Pending
- 2001-11-16 WO PCT/EP2001/013332 patent/WO2002052957A1/fr not_active Application Discontinuation
- 2001-11-16 EP EP01272630A patent/EP1345502A1/fr not_active Withdrawn
- 2001-11-16 US US10/465,917 patent/US20040077719A1/en not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| See references of WO02052957A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE10065478C1 (de) | 2002-08-29 |
| US20040077719A1 (en) | 2004-04-22 |
| JP2005500978A (ja) | 2005-01-13 |
| WO2002052957A1 (fr) | 2002-07-11 |
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