US20020111383A1 - Ultrafine L-carnitine, methods of preparing the same, compositions containing the same, and methods of using the same - Google Patents

Ultrafine L-carnitine, methods of preparing the same, compositions containing the same, and methods of using the same Download PDF

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Publication number
US20020111383A1
US20020111383A1 US10/073,978 US7397802A US2002111383A1 US 20020111383 A1 US20020111383 A1 US 20020111383A1 US 7397802 A US7397802 A US 7397802A US 2002111383 A1 US2002111383 A1 US 2002111383A1
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United States
Prior art keywords
carnitine
alkanoyl
acid
tartrate
pamoate
Prior art date
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Abandoned
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US10/073,978
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English (en)
Inventor
Ken Hassen
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Sigma Tau HealthScience SpA
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Sigma Tau HealthScience SpA
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Application filed by Sigma Tau HealthScience SpA filed Critical Sigma Tau HealthScience SpA
Priority to US10/073,978 priority Critical patent/US20020111383A1/en
Publication of US20020111383A1 publication Critical patent/US20020111383A1/en
Priority to US11/041,272 priority patent/US7303765B2/en
Abandoned legal-status Critical Current

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Classifications

    • 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
    • A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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 an ultra-fine L-carnitine and salts thereof.
  • the present invention relates to L-carnitine and salts thereof which exist in the form of ultra-fine particles.
  • the present ultra-fine L-carnitine is capable of being uniformly blended with fine particles of other raw materials, while maintaining its own discrete shape.
  • the overall fineness of the present ultra-fine L-carnitine makes it ideal for blending with oil-based raw materials with which conventional bulk carnitine is not entirely miscible.
  • the overall fineness of the present ultra-fine L-carnitine also facilitates the ready absorption in the gut due to the increased overall surface area of the fine material.
  • the present invention also relates to methods for preparing such ultra-fine L-carnitine and salts thereof.
  • the present invention further relates to compositions which comprise such ultra-fine L-carnitine and salts thereof.
  • the present invention additionally relates to methods of using such ultra-fine L-carnitine and salts thereof.
  • L-carnitine is known to have many uses.
  • the oral administration of L-carnitine has been shown to be an effective therapy for cardiovascular diseases.
  • L-carnitine and its salts are also known to be useful as dietary supplements, in particular for the facilitation of the metabolism of lipids.
  • L-carnitine and salts thereof which exist in the form of ultra-fine particles exhibit a high bioavailability upon oral administration.
  • the inventors have also discovered that such L-carnitine may be conveniently formulated with oil-based raw materials.
  • the inventors have also discovered that such L-carnitine exhibits a reduced hygroscopicity.
  • the present invention provides ultra-fine L-carnitine and salts thereof.
  • L-carnitine and salts thereof includes not only L-carnitine itself, but also salts of L-carnitine , alkanoyl L-carnitines, and salts of alkanoyl L-carnitine.
  • Suitable salts of L-carnitine include L-carnitine chloride, L-carnitine bromide, L-carnitine orotate, L-carnitine acid aspartate, L-carnitine acid phosphate, L-carnitine fumarate, L-carnitine lactate, L-carnitine maleate, L-carnitine acid maleate, L-carnitine acid oxalate, L-carnitine acid sulfate, L-carnitine glucose phosphate, L-carnitine tartrate, L-carnitine acid tartrate, L-carnitine iodate, L-carnitine aspartate, L-carnitine citrate, L-carnitine acid citrate, L-carnitine acid fumarate, L-carnitine glycerophosphate, L-carnitine mucate, L-carnitine orotate, L-carnitine oxalate, L-carnitine sulfate, L-carnitine trichloroacetate, L
  • Suitable alkanoyl L-carnitines include C 2-8 alkanoyl L-carnitines, particularly acetyl, butyryl, isobutyryl, valeryl, isovaleryl and more particularly propionyl L-carnitine.
  • Suitable salts of alkanoyl L-carnitines include C 2-8 alkanoyl L-carnitine chloride, C 2-8 alkanoyl L-carnitine bromide, C 2-8 alkanoyl L-carnitine orotate, C 2-8 alkanoyl L-carnitine acid aspartate, C 2-8 alkanoyl L-carnitine acid phosphate, C 2-8 alkanoyl L-carnitine fumarate, C 2-8 alkanoyl L-carnitine lactate, C 2-8 alkanoyl L-carnitine maleate, C 2-8 alkanoyl L-carnitine acid maleate, C 2-8 alkanoyl L-carnitine acid oxalate, C 2-8 alkanoyl L-carnitine acid sulfate, C 2-8 alkanoyl L-carnitine glucose phosphate, C 2-8 alkanoyl L-carnitine tartrate, C 2-8 alkanoyl
  • the present invention provides ultra-fine particles of L-carnitine, as well as ultra-fine particles of a salt of L-carnitine.
  • the present invention also provides mixtures of ultra-fine particles of L-carnitine and ultra-fine particles of one or more salts of L-carnitine, as well as mixtures of ultra-fine particles of two or more salts of L-carnitine.
  • the ultra-fine L-carnitine and salts thereof of the present invention has a particle sufficiently small that substantially all of it passes through a 100 United State Bureau of Standards (USBS) mesh screen.
  • the ultra-fine L-carnitine and salts thereof of the present invention has a particle sufficiently small that substantially all of it passes through a 150 USBS mesh screen.
  • the ultra-fine L-carnitine and salts thereof of the present invention has a particle sufficiently small that substantially all of it passes through a 200 USBS mesh screen.
  • the ultra-fine L-carnitine and salts thereof of the present invention may be prepared by reducing the size of conventional L-carnitine and salts thereof and selecting the appropriately sized particles by sieving.
  • L-carnitine and salts thereof are conveniently prepared by the methods described in U.S. Pat. Nos. 4,254,053; 4,602,039; and 5,412,113 and European Patent Application EP-A-0150688, which are incorporated herein by reference.
  • Such procedures typically yield L-carnitine having a size of such that greater than 10% by weight of the L-carnitine is retained by a 50 mesh sieve and more than 40% by weight is retained by a 100 mesh sieve.
  • the present ultra-fine L-carnitine may be produced by subjecting such L-carnitine to size reduction.
  • the size reduction may be carried out by any suitable technique, such as grinding, milling, etc. Methods of size reduction are well known and are described in Kirk-Othmer, Encyclopedia of Chemical Technology, 4 th Ed., Wiley, New York, vol. 22, pp. 279-296, 1999, which is incorporated herein by reference.
  • the ultra-fine 1-carnitine of the present invention may be selected by subjecting the size-reduced L-carnitine to sieving.
  • Sieving is a well known technique for selecting materials of a particular size and is described in Kirk-Othmer, Encyclopedia of Chemical Technology, 4 th Ed., Wiley, New York, vol. 22, pp. 256-278, 1999, which is incorporated herein by reference.
  • the ultra-fine L-carnitine of the present invention is obtained by selecting that material which passes through a 100 USBS mesh sieve, preferably a 150 USBS mesh sieve, more preferably a 200 mesh USBS mesh sieve.
  • the present invention provides compositions which contain the ultra-fine L-carnitine and a pharmaceutically acceptable excipient or carrier.
  • Suitable pharmaceutically acceptable excipients or carriers are described in Remington's Pharmaceutical Sciences Handbook, Mack Publishing, which is incorporated herein by reference.
  • the pharmaceutically acceptable excipient or carrier is an oil-based material, such as synthetic or natural oil based vitamins including, but not limited to vitamin E, oils extracted from any seed or vegetable such as, but not limited to soy, olive, palm, or corn oil, and any nutritive substance that maybe previously dissolved suspended or mixed in one or more of such oils.
  • oil-based material such as synthetic or natural oil based vitamins including, but not limited to vitamin E, oils extracted from any seed or vegetable such as, but not limited to soy, olive, palm, or corn oil, and any nutritive substance that maybe previously dissolved suspended or mixed in one or more of such oils.
  • the present composition may further comprise any of the additional active ingredients which L-carnitine or salts thereof are known to be combined with, e.g., hydroxycitric acid, Co-enzyme Q10, chromium picolinate, gamma linolenic acid, resveratrol, omega 3 acids, antioxidants, vitamins, etc.
  • additional active ingredients which L-carnitine or salts thereof are known to be combined with, e.g., hydroxycitric acid, Co-enzyme Q10, chromium picolinate, gamma linolenic acid, resveratrol, omega 3 acids, antioxidants, vitamins, etc.
  • the compound of the invention may be certified “BSE Safe,” since it contains no animal products and is based upon chemical synthesis. Avoidance of potential health risks and unnecessary consumption of unknown organisms, since tartrate is a bioferm. “International Food Marketing,” GreenPeace and others have published articles on the future risk of BSE. The buying public has a heightened awareness to this risk.
  • the compound of the present invention requires no reworking (regranulation, conditioning) as tartrate does. Lowered production costs, labor, environmental exposure. If transformer is not reworking tartrate, they should, since tablets made with tartrate as is will not hold up well in gelatine capsules or on shelves.
  • the fine particle size (200 Mesh) and coating of hydrophilic and or hydrophobic silicas provides excellent mixing and content uniformity properties especially for formulations that use other finely particled ingredients such as chromium picolinate and Co-enzyme Q10, as well as extended shelf life due to its inherently low hygroscopicity. Tooling (punches) and presses theoretically run cooler, than with tartrate, due to increased lubricity offered by the silica, which will save expensive downtime thereby reducing costs.
  • L-carnitine fumarate is milled to an over all particle size so as to minimally pass a number 100 USBS Mesh screen. Particles utilized to evaluate the efficacy of the invention to date have actually been milled to pass 150-200 Mesh with outstanding results. Particles are then blended with a food grade hydrophilic and/or hydrophobic fumed or precipitated silica(s) of the type available from Degussa, Inc. that poses an overall surface area of 190-475 square meters per gram and a tapped density of 80-275 grams per liter.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Cosmetics (AREA)
US10/073,978 1999-09-03 2002-02-14 Ultrafine L-carnitine, methods of preparing the same, compositions containing the same, and methods of using the same Abandoned US20020111383A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US10/073,978 US20020111383A1 (en) 1999-09-03 2002-02-14 Ultrafine L-carnitine, methods of preparing the same, compositions containing the same, and methods of using the same
US11/041,272 US7303765B2 (en) 1999-09-03 2005-01-25 Ultrafine-L-carnitine, methods of preparing the same, compositions containing the same, and methods of using the same

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US15224099P 1999-09-03 1999-09-03
US15824599P 1999-10-08 1999-10-08
US65386100A 2000-09-01 2000-09-01
US10/073,978 US20020111383A1 (en) 1999-09-03 2002-02-14 Ultrafine L-carnitine, methods of preparing the same, compositions containing the same, and methods of using the same

Related Parent Applications (2)

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US65386100A Continuation 1999-09-03 2000-09-01
US09653861 Continuation 2002-09-01

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US11/041,272 Continuation US7303765B2 (en) 1999-09-03 2005-01-25 Ultrafine-L-carnitine, methods of preparing the same, compositions containing the same, and methods of using the same

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US11/041,272 Expired - Lifetime US7303765B2 (en) 1999-09-03 2005-01-25 Ultrafine-L-carnitine, methods of preparing the same, compositions containing the same, and methods of using the same

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US (2) US20020111383A1 (de)
EP (1) EP1218001B1 (de)
JP (3) JP2003508488A (de)
KR (1) KR100827900B1 (de)
CN (1) CN1399549A (de)
AT (1) ATE418978T1 (de)
AU (1) AU770563B2 (de)
CA (1) CA2383814C (de)
CY (1) CY1110223T1 (de)
DE (1) DE60041269D1 (de)
DK (1) DK1218001T3 (de)
ES (1) ES2322328T3 (de)
HK (1) HK1047889B (de)
MX (1) MXPA02002327A (de)
NZ (1) NZ517597A (de)
PT (1) PT1218001E (de)
WO (1) WO2001017525A1 (de)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040176448A1 (en) * 2001-06-19 2004-09-09 Thomas Blatt Use of carnitine and/or one or more acyl-carnitines for producing cosmetic or dermatological preparations, which increase ceramide biosynthesis
US20050136537A1 (en) * 2003-07-01 2005-06-23 President And Fellows Of Harvard College Compositions for manipulating the lifespan and stress response of cells and organisms
US20050267023A1 (en) * 2002-08-09 2005-12-01 Sinclair David A Methods and compositions for extending the life span and increasing the stress resistance of cells and organisms
US20060014705A1 (en) * 2004-06-30 2006-01-19 Howitz Konrad T Compositions and methods for selectively activating human sirtuins
US20060084085A1 (en) * 2004-06-16 2006-04-20 Sinclair David A Methods and compositions for modulating Bax-mediated apoptosis
US20060111435A1 (en) * 2003-12-29 2006-05-25 President And Fellows Of Harvard College Compositions for treating or preventing obesity and insulin resistance disorders
US8242171B2 (en) 2003-12-29 2012-08-14 President And Fellows Of Harvard College Method for reducing the weight of a subject or inhibiting weight gain in a subject
US9241916B2 (en) 2005-06-14 2016-01-26 President And Fellows Of Harvard College Cognitive performance with sirtuin activators
WO2020092243A1 (en) * 2018-10-29 2020-05-07 Lonza Inc. Method and composition for increasing the bioavailability of carnitine

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WO2002085134A1 (en) * 2001-04-24 2002-10-31 Lonza Ltd. Method of enhancing reproductive performance in sows
US7169770B2 (en) 2001-04-24 2007-01-30 Lonza Ltd. Method of enhancing reproductive performance in sows
DE20321010U1 (de) * 2003-03-28 2005-12-29 Schymura, Martin Fruchtgummizusammensetzung
JP4539096B2 (ja) * 2004-01-16 2010-09-08 日油株式会社 油性成分被覆ｌ−カルニチン塩粉末およびその用途
ATE555774T1 (de) * 2005-07-05 2012-05-15 Lonza Ag Sprühtrockenverfahren zur herstellung eines trockenen carnitin-pulvers oder -granulats
DE102007009649A1 (de) 2007-02-26 2008-08-28 Beiersdorf Ag Nahrungsergänzungsmittel zur Pflege und/oder Verschönerung der Haut
DE102007009650A1 (de) 2007-02-26 2008-08-28 Beiersdorf Ag Kosmetisches Kombinationsprodukt zur Verbesserung des äußeren Erscheinungsbildes
CN101224202A (zh) * 2007-12-26 2008-07-23 广州康采恩医药有限公司 减肥组合物
PT3164125T (pt) 2014-07-03 2023-12-12 Silti Ag Métodos e composições para tratar obesidade, prevenir ganho de peso, promover perda de peso, promover emagrecimento ou tratar ou prevenir o desenvolvimento de diabetes
WO2017105090A1 (ko) * 2015-12-14 2017-06-22 제이투에이치바이오텍 (주) 오로트산 l-카르니틴의 결정질 다형체, 이의 제조방법 또는 용도
CN112250588B (zh) * 2020-11-06 2023-03-31 哈尔滨工业大学（深圳） 一种左旋肉碱离子液体及其制备方法、应用

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040176448A1 (en) * 2001-06-19 2004-09-09 Thomas Blatt Use of carnitine and/or one or more acyl-carnitines for producing cosmetic or dermatological preparations, which increase ceramide biosynthesis
US20050267023A1 (en) * 2002-08-09 2005-12-01 Sinclair David A Methods and compositions for extending the life span and increasing the stress resistance of cells and organisms
US7977049B2 (en) 2002-08-09 2011-07-12 President And Fellows Of Harvard College Methods and compositions for extending the life span and increasing the stress resistance of cells and organisms
US7544497B2 (en) 2003-07-01 2009-06-09 President And Fellows Of Harvard College Compositions for manipulating the lifespan and stress response of cells and organisms
US20050136537A1 (en) * 2003-07-01 2005-06-23 President And Fellows Of Harvard College Compositions for manipulating the lifespan and stress response of cells and organisms
US20100035885A1 (en) * 2003-07-01 2010-02-11 President And Fellows Of Harvard College Compositions for manipulating the lifespan and stress response of cells and organisms
US8017634B2 (en) 2003-12-29 2011-09-13 President And Fellows Of Harvard College Compositions for treating obesity and insulin resistance disorders
US20060111435A1 (en) * 2003-12-29 2006-05-25 President And Fellows Of Harvard College Compositions for treating or preventing obesity and insulin resistance disorders
US8242171B2 (en) 2003-12-29 2012-08-14 President And Fellows Of Harvard College Method for reducing the weight of a subject or inhibiting weight gain in a subject
US8846724B2 (en) 2003-12-29 2014-09-30 President And Fellows Of Harvard College Compositions for treating obesity and insulin resistance disorders
US9597347B2 (en) 2003-12-29 2017-03-21 President And Fellows Of Harvard College Compositions for treating obesity and insulin resistance disorders
US20060084085A1 (en) * 2004-06-16 2006-04-20 Sinclair David A Methods and compositions for modulating Bax-mediated apoptosis
US20060014705A1 (en) * 2004-06-30 2006-01-19 Howitz Konrad T Compositions and methods for selectively activating human sirtuins
US9241916B2 (en) 2005-06-14 2016-01-26 President And Fellows Of Harvard College Cognitive performance with sirtuin activators
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HK1047889A1 (en) 2003-03-14
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AU7347000A (en) 2001-04-10
PT1218001E (pt) 2009-03-31
DE60041269D1 (de) 2009-02-12
ES2322328T3 (es) 2009-06-19
US20050124558A1 (en) 2005-06-09
JP2013136635A (ja) 2013-07-11
EP1218001B1 (de) 2008-12-31
HK1047889B (zh) 2009-04-09
JP2003508488A (ja) 2003-03-04
KR20020066322A (ko) 2002-08-14
CY1110223T1 (el) 2015-01-14
CN1399549A (zh) 2003-02-26
MXPA02002327A (es) 2004-07-16
CA2383814A1 (en) 2001-03-15
EP1218001A1 (de) 2002-07-03
WO2001017525A1 (en) 2001-03-15
AU770563B2 (en) 2004-02-26
CA2383814C (en) 2010-08-17
NZ517597A (en) 2003-11-28
ATE418978T1 (de) 2009-01-15
KR100827900B1 (ko) 2008-05-07
DK1218001T3 (da) 2009-04-14
US7303765B2 (en) 2007-12-04

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