CA2610821A1 - Organic salts of .beta.-alanine - Google Patents

Organic salts of .beta.-alanine Download PDF

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Publication number
CA2610821A1
CA2610821A1 CA002610821A CA2610821A CA2610821A1 CA 2610821 A1 CA2610821 A1 CA 2610821A1 CA 002610821 A CA002610821 A CA 002610821A CA 2610821 A CA2610821 A CA 2610821A CA 2610821 A1 CA2610821 A1 CA 2610821A1
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CA
Canada
Prior art keywords
organic acid
beta
alanine
salt
group
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.)
Granted
Application number
CA002610821A
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French (fr)
Other versions
CA2610821C (en
Inventor
Michele Molino
Joseph Macdougall
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.)
Northern Innovations and Formulations Corp
Original Assignee
Iovate T&P Inc
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Publication date
Application filed by Iovate T&P Inc filed Critical Iovate T&P Inc
Priority to CA2610821A priority Critical patent/CA2610821C/en
Publication of CA2610821A1 publication Critical patent/CA2610821A1/en
Application granted granted Critical
Publication of CA2610821C publication Critical patent/CA2610821C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • 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
    • A61P21/06—Anabolic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids
    • C07C57/15—Fumaric acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/265—Citric acid

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Endocrinology (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to stable salts of .beta.-alanine and an organic acid endowed with enhanced nutritional and/or therapeutical efficacy in respect to their individual effects and to solid compositions containing such salts, particularly suited to oral administration. A method of preparation is also provided.

Claims (16)

1. A salt of .beta.-alanine and an organic acid, having the general formula:

wherein:

A- represents a deprotonated organic acid selected from the group consisting of: malate, citrate and fumarate; and where A- is malate or fumarate, n = 2, and where A- is citrate; n = 3.
2. A composition comprising the salt of .beta.-alanine and an organic acid of claim 1, wherein the composition further comprises pharmaceutically acceptable excipients.
3. The composition of claim 2 wherein the pharmaceutically acceptable excipients are selected from the group consisting of monoglycerides, magnesium stearate, modified food starch, gelatin, microcrystalline cellulose, glycerin, stearic acid, silica, yellow beeswax, lecithin, hydroxypropylcellulose, croscarmellose sodium, and crosprovidone.
4. The salt of .beta.-alanine and an organic acid of claim 1 wherein said salt is provided in a dosage form selected from the group consisting of tablets, chewable tablets, capsules, granulates or powders.
5. The composition of claim 2 wherein the composition is provided in a dosage form selected from the group consisting of tablets, chewable tablets, capsules, granulates or powders.
6. The salt of .beta.-alanine and an organic acid of claim 4 wherein said salt is administered to a mammal.
7. The composition of claim 5 wherein the composition is administered to a mammal.
8. A method for producing a .beta.-alanine organic acid salt comprising at least the steps of:

a) dissolving .beta.-alanine in hot lower alcohol;

b) dissolving an organic acid in hot lower alcohol;
c) mixing the resultant solutions of a) and b);

d) cooling the resultant mixture; and e) isolating the resulting .beta.-alanine organic acid salt.
9. The method of claim 8 wherein the lower alcohol is selected from the group consisting of methanol, ethanol, propanol, butanol, and isopropanol.
10.The method of claim 8 wherein the .beta.-alanine and the organic acid are present in a 2:1 ratio.
11. The method of claim 10 wherein the organic acid is selected from the group consisting of malic acid and fumaric acid.
12. The method of claim 11 wherein the .beta.-alanine and the organic acid are present in a 3:1 ratio.
13. The method of claim 12 wherein the organic acid is citric acid.
14.The method of claim 8 wherein the resultant mixture is cooled until crystallization occurs.
15. The method of claim 8 wherein the .beta.-alanine organic acid salt is isolated by vacuum filtration followed by washing of the filtrate with cold lower alcohol.
16.The .beta.-alanine organic acid salt of claim 8 having the molecular structure of:

wherein:

A- represents a deprotonated organic acid selected from the group consisting of: malate, citrate and fumarate; and where A- is malate or fumarate, n = 2, and where A- is citrate; n = 3.
CA2610821A 2007-12-12 2007-12-12 Organic salts of .beta.-alanine Active CA2610821C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2610821A CA2610821C (en) 2007-12-12 2007-12-12 Organic salts of .beta.-alanine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA2610821A CA2610821C (en) 2007-12-12 2007-12-12 Organic salts of .beta.-alanine

Publications (2)

Publication Number Publication Date
CA2610821A1 true CA2610821A1 (en) 2008-11-14
CA2610821C CA2610821C (en) 2010-03-23

Family

ID=39971176

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2610821A Active CA2610821C (en) 2007-12-12 2007-12-12 Organic salts of .beta.-alanine

Country Status (1)

Country Link
CA (1) CA2610821C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113603603A (en) * 2021-08-05 2021-11-05 西北大学 Method for preparing beta-glycine by solution freezing and anti-solvent washing

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113603603A (en) * 2021-08-05 2021-11-05 西北大学 Method for preparing beta-glycine by solution freezing and anti-solvent washing
CN113603603B (en) * 2021-08-05 2023-09-15 西北大学 Method for preparing beta glycine by solution freezing and antisolvent washing

Also Published As

Publication number Publication date
CA2610821C (en) 2010-03-23

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