US20070231370A1 - Guanidino Acetic Acid Used as an Animal Food Additive - Google Patents

Guanidino Acetic Acid Used as an Animal Food Additive Download PDF

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Publication number
US20070231370A1
US20070231370A1 US11/596,771 US59677105A US2007231370A1 US 20070231370 A1 US20070231370 A1 US 20070231370A1 US 59677105 A US59677105 A US 59677105A US 2007231370 A1 US2007231370 A1 US 2007231370A1
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composition
acid
salt
creatine
animal
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Thomas Gastner
Hans-Peter Krimmer
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Alzchem Trostberg GmbH
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Alzchem Trostberg GmbH
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Publication of US20070231370A1 publication Critical patent/US20070231370A1/en
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    • 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
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01K—ANIMAL HUSBANDRY; AVICULTURE; APICULTURE; PISCICULTURE; FISHING; REARING OR BREEDING ANIMALS, NOT OTHERWISE PROVIDED FOR; NEW BREEDS OF ANIMALS
    • A01K61/00—Culture of aquatic animals
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/105—Aliphatic or alicyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/142—Amino acids; Derivatives thereof
    • A23K20/147—Polymeric derivatives, e.g. peptides or proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/153—Nucleic acids; Hydrolysis products or derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/158—Fatty acids; Fats; Products containing oils or fats
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/174—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/20—Inorganic substances, e.g. oligoelements
    • A23K20/30—Oligoelements
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/30—Feeding-stuffs specially adapted for particular animals for swines
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/80—Feeding-stuffs specially adapted for particular animals for aquatic animals, e.g. fish, crustaceans or molluscs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01K—ANIMAL HUSBANDRY; AVICULTURE; APICULTURE; PISCICULTURE; FISHING; REARING OR BREEDING ANIMALS, NOT OTHERWISE PROVIDED FOR; NEW BREEDS OF ANIMALS
    • A01K61/00—Culture of aquatic animals
    • A01K61/10—Culture of aquatic animals of fish
    • A01K61/13—Prevention or treatment of fish diseases
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/80—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in fisheries management
    • Y02A40/81—Aquaculture, e.g. of fish
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/80—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in fisheries management
    • Y02A40/81—Aquaculture, e.g. of fish
    • Y02A40/818—Alternative feeds for fish, e.g. in aquacultures

Definitions

  • the present invention relates to the use of guanidinoacetic acid or of salts of guanidinoacetic acid as feed additive.
  • Guanidinoacetic acid is an endogenous substance in animals and humans which takes a central role in the biosynthesis of creatine. Creatine can be both taken by the diet, and also formed endogenously. Its biosynthesis proceeds from glycine and L-arginine. In mammals, primarily in the kidneys, but also in the liver and pancreas, the guanidino group of the L-arginine is cleaved by the enzyme aminotransferase and an N—C—N group is transferred to the glycine. The L-arginine is converted in this case to L-ornithine.
  • the guanidinoacetic acid thus formed is converted in the next step to creatine using the enzyme transmethylase, in vertebrates this takes place exclusively in the liver.
  • the S-adenosylmethionine acts as methyl group donor. Creatine then diffuses into the blood circulation and is thus transported to the target organs. Transport through the cell membrane into the cells takes place in this case via a specific creatine transporter.
  • the abovementioned creatine takes an important role in the energy metabolism of the cell, it being, as high-energy phosphocreatine, in addition to adenosin triphosphate (ATP), an important energy reserve of muscle.
  • ATP adenosin triphosphate
  • ATP can transfer a phosphate group to creatine, phosphate creatine being formed which is then in direct equilibrium with ATP.
  • the phosphocreatine is available therefor in the first seconds of maximum muscle load. This phosphocreatine can transfer a phosphate group to adenosin diphosphate by the enzyme creatine kinase in a very rapid reaction and thus reform ATP. This is also termed the Lohmann reaction.
  • Creatine has long been known as a suitable food and feed supplement.
  • the creatine reserves which natural are present in the body are rapidly exhausted.
  • targeted creatine administration has had beneficial effects on stamina and performance, with unwanted enrichment processes in the body or disadvantageous degradation products being unknown.
  • the reason for this is that creatine is excreted by the body as creatinine in the case of excess supply.
  • creatine supplementation leads to increase in body mass. This is at the beginning ascribed to increased uptake of water into the muscle. In the long term, creatine indirectly leads to an increase in muscle mass (Int J Sports Med 21 (2000), 139-145) via increased protein synthesis or a decreased protein catabolism in the myofibrils. As a result increased fat-free body mass is thus obtained.
  • Creatine also exhibits the effects demonstrated as beneficial to humans in animals, for which reason its use has likewise been sufficiently previously described in diverse feeds.
  • the international patent application WO 00/67 590 has previously described the use of creatine or creatine salts as feed additive for breeding and growing livestock, as replacement for meat meal, fish meal and/or antimicrobial performance enhancers, growth hormones as well as anabolic agents.
  • GB 2 300 103 teaches the use of creatine in the form of a dog biscuit, for which creatine monohydrate is offered together with meat in an extruded mix. Since creatine monohydrate, owing to its poor solubility, is only insufficiently bioavailable, its joint use together with other physiologically active compounds, preferably in salt form, is recommended.
  • German Laid-Open application DE 198 36 450 A1 has, as subject matter, the use of stable pyruvic acid salts, and in particular creatine pyruvate, in formulations which are suitable for animal nutrition.
  • DE 100 03 835 A1 has, as subject matter, formulations for dehydration conditions as generally occur in older persons, in particular those having restricted mobility.
  • creatine acts as a transport medium for water in order in this manner to supply moisture to the tissues most severely affected by dehydration symptoms.
  • creatine In addition to its undisputed beneficial physiological properties, creatine, however, has the disadvantage that, as creatine monohydrate, it does not have pronounced stability in the corresponding aqueous solutions in that it converts itself over a relatively long period into creatinine. This is a problem especially in acidic solutions and is thus also of importance for oral intake and bioavailability of creatine.
  • the pH of the stomach of 1 to 2 can, depending on the residence time, lead to significant breakdown of the creatine to form creatinine. For instance, in humans it has been found that after oral application of creatine, only about 15 to 30% can be resorbed by the musculature (Greenhaff, P. L.: Factors Modifying Creatine Accumulation in Human Skeletal Muscle. In: Creatine, From Basic Science to Clinical Application. Medical Science Symposia Series Volume 14, 2000, 75-82).
  • the disadvantages of the prior art with respect to creatine have produced the object of the present invention to find compounds which can be used as feeds or feed additive for breeding and growing livestock and have a beneficial effect on improving feed uptake, increasing the growth performance, raising the muscle flesh gain, meat quality and/or the reproduction performance.
  • the compounds should have as low an instability as possible, in particular in aqueous solution, and preferably not be converted into creatine until after application or physiological uptake.
  • the feeds or feed additives used should not themselves develop any physiologically disadvantageous effects and be readily detectable. From commercial aspects, of primary importance for the substances to be used according to the invention was also the fact that they should be able to be produced in an economically expedient manner.
  • This object has been achieved by the use of guanidinoacetic acid and/or salts of guanidinoacetic acid as feed additive for breeding and growing livestock in predominantly vegetarian diets to improve feed uptake, to increase growth performance, muscle meat gain, meat quality and/or reproduction performance.
  • predominantly vegetarian diet describes a diet which preferably contains no animal components in agreement with the legal directives in the European Union. The only exception in this case is a possible addition of fish meal.
  • the “predominantly vegetarian diet” according to this invention is also to be taken to mean a partial replacement of fish meal or meat meal by guanidinoacetic acid.
  • the claimed compounds in fact have the properties desired according to the object, since they can be produced in a simple and economic manner, for example by methods such as the reaction of glycine and cyanamide in aqueous solutions (Production of guanidino fatty acids (Vassel, Bruno; Janssens, Walter D.) (1952), U.S. Pat. No. 2,620,354; Method of preparation of guanidino fatty acids (Vassel, Bruno; Garst, Roger) (1953), 5 pp U.S. Pat. No. 2,654,779).
  • guanidinoacetic acid and salts thereof in addition exhibit a significantly higher stability in acidic aqueous solution and they are not converted to creatine until under physiological conditions.
  • the guanidinoacetic acid and salts thereof used according to the invention in contrast to creatine, are in fact not converted to creatine until after resorption, principally in the liver.
  • the majority of the compounds administered or fed, guanidinoacetic acid and/or salts of guanidinoacetic acid are not degraded by instability reactions, for example in the stomach, and excreted before resorption, but are in fact available in the corresponding physiological metabolic reactions.
  • Guanidinoacetic acid and salts thereof can be used according to the invention, but again in contrast to creatine and derivatives thereof, with identical activity at significantly lower dosage.
  • the advantages of the use claimed by the invention could not be predicted in their totality, in particular because guanidinoacetic acids, for example in chicks, had been ascribed adverse activity on feed utilization and weight gain.
  • guanidinoacetic acid and salts thereof as feed additive has proved very effective, for example, for poultry such as, for example, chicks, turkeys, ducks and geese, but also for pigs.
  • the present invention in another embodiment, provides using guanidinoacetic acid and/or suitable salts thereof as supplementation or alternatively as feed additive in aquacultures, preferably as partial or total replacement of fish meal and/or antimicrobial performance enhancers, whereas the proposed use being preferred for salmon types (Salmonides) and shrimp types (Natania).
  • Antimicrobial performance enhancers are substances such as, for example, carbadox, olaquindox, salinomycin, monensin, avilamycin or flavomycin. These are used in particular to prevent the spread of diseases in animals. Further, increased efficiency in animal production shall be achieved. Antimicrobial performance enhancers are also used to avoid transmission of the zoonoses to humans and thus enable the production of high quality and safe animal foods.
  • the present invention also relates to the use of guanidinoacetic acid and/or salts thereof for the production of a therapeutic composition for breeding and growing livestock which can be used to strengthen the immune system and to improve reproduction performance.
  • the described therapeutic composition in a preferred embodiment, is preferably used in poultry and/or pigs.
  • guanidinoacetic acid salts are suitable which are acceptable in terms of nutritional physiology.
  • salts of guanidinoacetic acid have proved expedient which are obtained with hydrochloric acid, hydrobromic acid and phosphoric acid. Mixtures of guanidinoacetic acid with one or more of these salts or else mixtures of the salts with one another can also be used.
  • guanidinoacetic acid and salts thereof can be used in a wide dose range.
  • Daily doses in chicks, per kg of live mass are, for example, in the range between about 10 mg and about 1200 mg, in particular in the range from about 50 mg to about 250 mg.
  • Individual doses are generally in the range from about 10 mg and about 600 mg, preferably in the range from about 25 to about 125 mg.
  • daily doses, per kg of live mass are, for example, in the range from about 10 mg and about 1000 mg, in particular in the range from about 25 mg to about 150 mg.
  • Individual doses are generally in the range from about 10 mg and about 500 mg, preferably in the range from about 10 mg to about 500 mg, preferably in the range from about 10 to 100 mg.
  • feed additive depending on animal species, preferably doses of about 0.01 to about 100 g/kg of feed or therapeutic composition come into consideration, amounts from about 1.0 to about 5.0 g being considered as particularly preferred.
  • feed additives Since the claimed use is preferably performed in the non-veterinary field of use, application forms of feed additives have proved particularly suitable which represent powders, granules, pastilles, capsules, pellets or gel (hydrocolloid) products. It is preferred here, depending on the respective specific application, to use guanidinoacetic acid and salts thereof as feed additive in combination with other physiologically active compounds, in particular carbohydrates, fats, amino acids (e.g. creatine), proteins, vitamins, minerals, trace elements and derivatives thereof and any desired mixtures thereof being particularly suitable. Preference is given to methionine, betaine and choline and also other physiologically active methyl group donors.
  • Betaine and choline in the presence of homocysteine, can be converted to methionine in the body, which especially plays a role in the synthesis of creatine from guanidinoacetic acid.
  • methyl groups are required which are transferred from S-adenosylmethionine with formation of homocysteine. If betaine or choline are insufficiently available, methionine is consumed and a methionine deficit can occur in metabolism.
  • a further aspect of the present invention is thus the use of guanidinoacetic acid and/or salts thereof for production of a composition for breeding and growing livestock for prevention and mitigation of the consequences of heat stress, in particular for reducing mortality as a result of elevated ambient temperatures.
  • the invention provides, in particular, that the therapeutic composition serves in predominantly vegetarian diets as partial and/or total replacement of fish meal, meat meal, anabolic agents (e.g. stilbenes, steroids, thyreostatics and ⁇ -agonists), antimicrobial performance enhancers and/or growth hormones.
  • guanidinoacetic acid and salts thereof can be used as feed additive for wet and dry feeds for dogs and cats, whereas positive effects result on the immune system and the general status of the animals.
  • guanidinoacetic acid and salts thereof are supplied to new applications as feeds and feed additive, respectively, in the nutrition of breeding and growing livestock or as therapeutic composition for breeding and growing livestock, which, in contrast to the creatine compounds previously used, have significant and surprising advantages.
  • the examples hereinafter further illustrate the present invention.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • Inorganic Chemistry (AREA)
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US11/596,771 2004-06-09 2005-06-07 Guanidino Acetic Acid Used as an Animal Food Additive Abandoned US20070231370A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE102004028193.9 2004-06-09
DE102004028193 2004-06-09
DE102004059761 2004-12-11
DE102004059761.8 2004-12-11
PCT/EP2005/006110 WO2005120246A1 (de) 2004-06-09 2005-06-07 Guanidinoessigsäure als futtermittelzusatz

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PCT/EP2005/006110 A-371-Of-International WO2005120246A1 (de) 2004-06-09 2005-06-07 Guanidinoessigsäure als futtermittelzusatz

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US13/164,973 Continuation US8501810B2 (en) 2004-06-09 2011-06-21 Guanidino acetic acid used as an animal food additive

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US13/164,973 Expired - Fee Related US8501810B2 (en) 2004-06-09 2011-06-21 Guanidino acetic acid used as an animal food additive
US13/738,452 Abandoned US20130296431A1 (en) 2004-06-09 2013-01-10 Guanidino acetic acid used as an animal food additive

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US13/738,452 Abandoned US20130296431A1 (en) 2004-06-09 2013-01-10 Guanidino acetic acid used as an animal food additive

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EP (1) EP1758463B1 (https=)
JP (1) JP5227021B2 (https=)
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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090098239A1 (en) * 2006-03-01 2009-04-16 Alzchem Trostberg Gmbh Ready-to-Eat Feed for Domestic Pets
US20090297656A1 (en) * 2005-08-02 2009-12-03 Thomas Gastner Liquid Formulation Based On a Guanidinoacetic Acid Component
US20100143703A1 (en) * 2007-07-21 2010-06-10 Stephan Winkler Abrasion-resistant free-flowing glycocyamine-containing mouldings and methods for their production
US8536222B2 (en) 2005-03-04 2013-09-17 Alzchem Ag Addition compounds of guanidinoacetic acid
CN114938830A (zh) * 2022-05-05 2022-08-26 北京中科万联科技有限公司 一种基于氨基酸提升畜禽瘦肉率的饲料添加剂及其制备方法和应用
CN115553403A (zh) * 2022-11-03 2023-01-03 上海海洋大学 凡纳滨对虾肉质改善剂及其制备方法和应用
US11633373B2 (en) 2020-03-04 2023-04-25 Alzchem Trostberg Gmbh Method for reduction of behavioral disorders in pigs
CN116268200A (zh) * 2023-03-15 2023-06-23 广东瑞科营养科技有限公司 提高动物肌细胞atp利用率的饲料添加剂、制法及应用
CN118401120A (zh) * 2021-10-13 2024-07-26 澳泽化学特罗斯特贝格有限公司 育肥期间胍基乙酸在猪用低能量饲料中的用途
US12252460B2 (en) 2019-07-12 2025-03-18 Alzchem Trostberg Gmbh Process for the preparation of a metastable crystal modification of n-(aminoiminomethyl)-2-aminoacetic acid (III)

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