(12) United States Patent (10) Patent No.: US 7,777,074 B2 Kramer Et Al
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US007777074 B2 (12) United States Patent (10) Patent No.: US 7,777,074 B2 Kramer et al. (45) Date of Patent: Aug. 17, 2010 (54) AMINO ACID COMPOUNDS (52) U.S. Cl. .................................... 562/512:548/335.5 (58) Field of Classification Search ................. 514/400, (75) Inventors: Ronald Kramer, Phoenix, AZ (US); 514/561, 563: 548/335.5; 562/512 hander Nikolaidis, New Kallikratia See application file for complete search history. GR (56) References Cited (73) Assignee: Estol,Inisational LLC, OTHER PUBLICATIONS Mostad et al., 1986, CAS: 104:197543.* (*) Notice: Subject to any disclaimer, the term of this Pradhan et al. publication, Journal of Chemical and Engineering patent is extended or adjusted under 35 Data, 2000, 45(1): 140-143.* U.S.C. 154(b) by 58 days. * cited by examiner (21) Appl. No.: 11/950,273 Primary Examiner Rei-tsang Shiao (22) Filed: Dec. 4, 2007 (74) Attorney, Agent, or Firm Booth Udall, PLC (65) Prior Publication Data (57) ABSTRACT US 2009/007611.0 A1 Mar. 19, 2009 An Amino Acid Compound is described. The Amino Acid Related U.S. Application Data Compound may comprise an Amino Acid and one of a Nitrate (60) Provisional application No. 60/973.229, filed on Sep. and a Nitrite. The Amino Acid may be one of Agmatine, 18, 2007 Arginine, Beta Alanine, Citrulline, Creatine, Glutamine, s L-Histidine, Isoleucine, Leucine, Norvaline, Ornithine, and (51) Int. Cl. Valine. C07C 53/00 (2006.01) CO7D 233/6 (2006.01) 2 Claims, No Drawings US 7,777,074 B2 1. 2 AMINO ACID COMPOUNDS of an Amino Acid Compound comprising an Amino Acid and one of a Nitrate and a Nitrite to the human or animal. CROSS REFERENCE TO RELATED Embodiments may include the following. The Amino Acid APPLICATIONS may be Agmatine. The Amino Acid may be Beta Alanine. The Amino Acid may be Arginine. The Amino Acid may be Cit This document claims the benefit of the filing date of U.S. Provisional Patent Application 60/973,229 entitled “Amino rulline. The Amino Acid may be Creatine. The Amino Acid Acid Compounds' to Alexander Nikolaidis and Ronald may be Histidine. The Amino Acid may be Isoleucine. The Kramer which was filed on Sep. 18, 2007, the disclosure of Amino Acid may be Leucine. The Amino Acid may be Nor which is hereby incorporated entirely herein by reference. 10 valine. The Amino Acid may be Ornithine. The Amino Acid may be Valine. BACKGROUND In another aspect, the invention features a method for increasing the bioabsorption of Amino Acids. The method 1. Technical Field includes administering a pharmaceutically effective amount Aspects of this document relate generally to Amino Acid 15 of an Amino Acid Compound comprising an Amino Acid and Compounds. one of a Nitrate and a Nitrite to the human or animal. 2. Background Embodiments may include the following. The Amino Acid It is desirable to design new Amino Acid compounds that may be Agmatine. The Amino Acid may be Beta Alanine. The have properties lacking in conventional Amino Acid com Amino Acid may be Arginine. The Amino Acid may be Cit pounds, conventional Nitrate compounds, conventional rulline. The Amino Acid may be Creatine. The Amino Acid Nitrite compounds, and in single-administration Amino may be Histidine. The Amino Acid may be Isoleucine. The Acids. Amino Acid may be Leucine. The Amino Acid may be Nor SUMMARY valine. The Amino Acid may be Ornithine. The Amino Acid 25 may be Valine. In one aspect, the invention features an Amino Acid Com In another aspect, the invention features a method for pound. The Amino Acid Compound may comprise an Amino increasing the vasodilative characteristics of Amino Acids. Acid and one of a Nitrate and a Nitrite. The method includes administering a pharmaceutically effec Embodiments may comprise one or more of the following. tive amount of an Amino Acid Compound comprising an The Amino Acid may be Agmatine. The Amino Acid may be 30 Amino Acid and one of a Nitrate and a Nitrite to the human or Beta Alanine. The Amino Acid may be Arginine. The Amino animal. Acid may be Citrulline. The Amino Acid may be Creatine. Embodiments may include the following. The Amino Acid The Amino Acid may be Histidine. The Amino Acid may be may be Agmatine. The Amino Acid may be Beta Alanine. The Isoleucine. The Amino Acid may be Leucine. The Amino Amino Acid may be Arginine. The Amino Acid may be Cit Acid may be Norvaline. The Amino Acid may be Ornithine. 35 rulline. The Amino Acid may be Creatine. The Amino Acid The Amino Acid may be Valine. may be Histidine. The Amino Acid may be Isoleucine. The The Amino Acid Compound may include a pharmaceuti Amino Acid may be Leucine. The Amino Acid may be Nor cally acceptable additive. The additive may be a carrier, an excipient, a binder, a colorant, a flavoring agent, a preserva valine. The Amino Acid may be Ornithine. The Amino Acid 40 may be Valine. tive, a buffer, a dilutant, and/or combinations thereof. The Amino Acid Compound may be in the form of a cap In another aspect, the invention features a method for Sule, tablet, pill, liquid, liquid Suspension, vapor, gas, powder, increasing distribution of Amino Acids to muscles. The granulate or pulverulence. A pharmaceutically acceptable method includes administering a pharmaceutically effective additive may be used such as a carrier, excipient, binder, amount of an Amino Acid Compound comprising an Amino colorant, flavoring agent, preservative, buffer, dilutant, and 45 Acid and one of a Nitrate and a Nitrite to the human or animal. combinations thereof. Embodiments may include the following. The Amino Acid In another aspect, the invention features a process for mak may be Agmatine. The Amino Acid may be Beta Alanine. The ing an Amino Acid Compound. The method includes prepar Amino Acid may be Arginine. The Amino Acid may be Cit ing a first solution of Nitric Acid and an Amino Acid. A rulline. The Amino Acid may be Creatine. The Amino Acid mixture is then formed by adding to the first Solution a quan 50 may be Histidine. The Amino Acid may be Isoleucine. The tity of water sufficient to ionize the Nitric Acid into a Nitrate Amino Acid may be Leucine. The Amino Acid may be Nor ion. The mixture is then allowed to crystallize. valine. The Amino Acid may be Ornithine. The Amino Acid Embodiments may comprise the following. The mixture may be Valine. may be placed under vacuum prior to being allowed to crys 55 In another aspect, the invention features a method for pre tallize. venting the development of Nitrate tolerances. The method In another aspect, the invention features a process for mak includes administering a pharmaceutically effective amount ing an Amino Acid Compound. The method comprises pre of an Amino Acid Compound comprising an Amino Acid and paring a first Solution of Nitrous Acid and an Amino Acid. A one of a Nitrate and a Nitrite to the human or animal. mixture is then formed by adding to the first Solution a quan 60 Embodiments may include the following. The Amino Acid tity of water sufficient to decompose the Nitrous Acid into may be Agmatine. The Amino Acid may be Beta Alanine. The Nitric Acid. The mixture is then allowed to crystallize. Amino Acid may be Arginine. The Amino Acid may be Cit Embodiments may include the following. The mixture may rulline. The Amino Acid may be Creatine. The Amino Acid be placed under vacuum prior to being allowed to crystallize. may be Histidine. The Amino Acid may be Isoleucine. The In another aspect, the invention features a method for 65 Amino Acid may be Leucine. The Amino Acid may be Nor increasing the water solubility of Amino Acids. The method valine. The Amino Acid may be Ornithine. The Amino Acid includes administering a pharmaceutically effective amount may be Valine. US 7,777,074 B2 3 4 DESCRIPTION The R group for the Amino Acid Creatine is: Overview HN H A Compounds containing both a carboxyl group and an 5 N amino group are typically known as Amino Acids. Amino Acids typically have the basic formula X-R, wherein X is: -N CH-COOH 10 Creatine is a nonessential Amino Acid and is also a nitrog enous organic acid. Creatine is independently manufactured by the human body, and does not need to be obtained directly Amino Acids typically differ from one another with respect through dietary intake. Creatine plays a significant role in to the structure of the R group. It is the structure of the R group 15 providing muscles with energy. Creatine is presently used in that typically determines the individuality and character of the dietary Supplement industry to Supplement Creatine pro each Amino Acid. duction in the body. Creatine is also presently used in the For example, the R group for the Amino Acid Arginine is: dietary Supplement industry to increase muscle-mass gains, improve athletic performance and strength. Creatine, by 2O itself, has no vasodilating properties. Citrulline is also water insoluble, which reduces its bioavailability and limits the in-chi-ch-ch, forms in which Citrulline may be effectively used. = NH The R group for the Amino Acid Glutamine is: NH2 25 HN-C-CH-CH Arginine is characterized as a nonessential Amino Acid. Spe O cifically, Arginine can be independently manufactured by the human body, and does not need to be obtained directly 30 through dietary intake. Arginine plays a significant role in Glutamine is a nonessential Amino Acid. Glutamine is the healing, cell division, immune function, the elimination of most abundant naturally occurring, non-essential amino acid ammonia from the body and the release of hormones.