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WO1994017794A1 - Blends of glycine derivatives and sugars - Google Patents

Blends of glycine derivatives and sugars Download PDF

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Publication number
WO1994017794A1
WO1994017794A1 PCT/GB1994/000181 GB9400181W WO9417794A1 WO 1994017794 A1 WO1994017794 A1 WO 1994017794A1 GB 9400181 W GB9400181 W GB 9400181W WO 9417794 A1 WO9417794 A1 WO 9417794A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
derivative
sugar
weight
hydrogen
Prior art date
Application number
PCT/GB1994/000181
Other languages
French (fr)
Inventor
Steven Andrew Jennings
Original Assignee
Steven Andrew Jennings
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from GB939302070A external-priority patent/GB9302070D0/en
Priority claimed from GB939320187A external-priority patent/GB9320187D0/en
Priority claimed from GB939325374A external-priority patent/GB9325374D0/en
Application filed by Steven Andrew Jennings filed Critical Steven Andrew Jennings
Priority to AU58903/94A priority Critical patent/AU5890394A/en
Publication of WO1994017794A1 publication Critical patent/WO1994017794A1/en

Links

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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7004—Monosaccharides having only carbon, hydrogen and oxygen atoms
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof

Definitions

  • compositions which comprise glycine derivatives and sugars to pharmaceutical compositions which comprise those compositions and methods of making the compositions .
  • Creatine exists in muscular tissue of many vertebrates and can be isolated from meat extracts. It has the formula
  • HN C(NH 2 ) -N(CH 3 )-CH 2 -C0 2 H
  • creatine derivatives blended with one or more sugars can enhance tissue formation in animals.
  • the invention provides a composition which comprises (a) glycine derivative I
  • X 1 , X 2 , X 3 , X 4 and X s is hydrogen or lower alkyl
  • Y is hydrogen, lower alkyl, or H 2 P0 3 or a substituted variant thereof, or a salt of the derivative I
  • a sugar in an amount of from about 2% to about 98% by weight of the derivative I.
  • X 3 is methyl
  • one or more of X 1 , X 2 , X 4 and X s is hydrogen.
  • Y is hydrogen, or H 2 P0 3 as will result from a reaction of a glycine derivative with phosphoric acid.
  • Suitable lower alkyl groups which can be used as substituents in the glycine derivative I are C ⁇ to C Motivation, straight or branched, groups .
  • the glycine derivative I may be present in a hydrated form, for example as the monohydrate.
  • the glycine derivative may be present as a salt, for example as the sodium or potassium salt.
  • the sugar may be selected from a group consisting of dextrose fructose, glucose and maltose. It is preferred that the sugar is a maltodextrin.
  • Maltodextrins comprise polymers of glucose, and will generally have a dextrose equivalent which is less than about 20, as determined by the Lane-Eynon titration technique (see Pearson's Chemical Analysis of Foods) .
  • Maltodextrins can be derived from corn or maize. They often include small amounts of potassium, sodium, and sulphur dioxide.
  • the amount of sugar present in the composition is at least about 30%, more preferably at least about 40%, by weight of the glycine derivative.
  • the amount of sugar present in the composition is not more than about 70%, more preferably not more than about 60%, by weight of the glycine derivative.
  • the invention provides a pharmaceutical composition which comprises a composition of the type referred to above, in association with a solid or liquid a pharmaceutical carrier or diluent.
  • the invention provides a method of making a pharmaceutical composition which comprises mixing (a) glycine derivative I
  • X 1 , X 2 , X 3 , X 4 and X s is hydrogen or lower alkyl
  • Y is hydrogen, lower alkyl, or H,PO, or a substituted variant thereof, or a salt of the derivative I
  • a sugar in an amount of from about 2% to about 98% by weight of the derivative I.
  • the composition of the present invention can be used as a metabolic supplement. It can be used to enhance tissue formation, for example in the treatment of diseases, especially wasting diseases such as multiple sclerosis. It has been found that the composition is particularly well suited to enhancing cardiac tissue formation. It can also be used to prevent disease. It has the advantage that its principal constituents are occur naturally. Furthermore, the composition has a pleasant taste, and is stable under normal conditions.
  • composition has been found to be suitable for use in the treatment of :
  • mood disorders such as bipolar, depressive disorders; recurrent depression disorders; schizo-affective dis ⁇ orders; dysthymia;
  • dementias such as Alzheimer's disease; neurotic illness includning phobic anxiety disorders; obsessive compulsive disorders; reaction to severe stress; neur ⁇ asthenia, general anxiety states;
  • the invention provides the use of a composition of the type discussed above in the manufacture of a medicament, especially for the treatment of one or more of the conditions referred to above.
  • the composition of the invention can be administered in tablet form. It can be administered in powder form. It can be preferred for the composition to be administered in solution, in particular in aqueous solution; it can be particularly preferred to administer the composition in solution, possibly at elevated temperature, which might be the highest temperature at which the solution can comfortably be consumed. For example, the solution might be heated to a temperature which is greater than about 40°C, preferably greater than about 50°C, for example greater than about 60°C, or even higher. Administering the composition in this way has been found to facilitate absorption.
  • the temperature of solution can be less than about 55°C when administered, more preferably less than about 45°C, even less than 40°C. This feature allows breakdown of the glycine derivative to be minimised.
  • the temperature is preferably then lowered by addition of a liquid at lower temperature (which might be flavoured) to reduce the overall temperature of the solution.
  • the effective concentration of the glycine derivative When administered in solution, it can be preferred for the effective concentration of the glycine derivative to be greater than about 0.5% by weight, more preferably greater than about 0.7%, especially greater than about 1.0%.
  • the concentration can be less than about 15% by weight, preferably less than about 10%, more preferably less than about 5%. Suitable concentrations are from about 1.5% to about 5%.
  • EXAMPLE 1 Tablets were formed from a mixture of creatine monohydrate supplied by Chemielinz A G, and a maltodextrin supplied by Roquette Freres S A under the trade name Glucidex 19, in a ratio by weight 2:1, the two constituents being provided in powder form. Tablets were formed using conventional tablet presses from the resulting mixture.
  • Tablets were formed from a mixture of the creatine monohydrate used in Example 1 and a glucose polymer supplied by Edward Mendell & Co under the trade name Emdex, in a ratio by weight 2:1, the two constituents being provided in powder form. Tablets were formed using conventional tablet presses from the resulting mixture.
  • Tablets were formed from a mixture of the creatine monohydrate used in Example 1 and a dextrose polymer supplied by Cerestar Limited under the trade name Celellose, in a ratio by weight 2:1, the two constituents being provided in powder form.
  • the mixture of the powders was supplied for ingestion in powder form.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)

Abstract

A composition which comprises (a) glycine derivative: X1N = C(NX?2Y) -NX3 -C(X4.X5) -CO¿2H where any one or more of X?1, X2, X3, X4 and X5¿ is hydrogen or lower alkyl, and Y is hydrogen, lower alkyl, or H¿2?PO3 or a substituted variant thereof, or a salt of the derivative, and (b) a sugar in an amount of from about 2 % to about 98 % by weight of the derivative. Preferably, X?3¿ is methyl, Y is H¿2?PO3, and the sugar is a maltodextrin. The sugar is preferably present in an amount of from 40 to 60 % by weight of the glycine derivative.

Description

BLENDS OF GLYCINE DERIVATIVES AND SUGARS
This invention relates to compositions which comprise glycine derivatives and sugars, to pharmaceutical compositions which comprise those compositions and methods of making the compositions .
Creatine exists in muscular tissue of many vertebrates and can be isolated from meat extracts. It has the formula
HN=C(NH2) -N(CH3)-CH2-C02H
According to the present invention, it has been found that creatine derivatives blended with one or more sugars can enhance tissue formation in animals.
In one aspect, the invention provides a composition which comprises (a) glycine derivative I
X1N=C(NX2Y) -NX3-C(X4.X5) -C02H I
where any one or more of X1, X2, X3, X4 and Xs is hydrogen or lower alkyl, and Y is hydrogen, lower alkyl, or H2P03 or a substituted variant thereof, or a salt of the derivative I, and (b) a sugar in an amount of from about 2% to about 98% by weight of the derivative I.
Preferably, X3 is methyl.
Preferably, one or more of X1, X2, X4 and Xs is hydrogen.
Preferably, Y is hydrogen, or H2P03 as will result from a reaction of a glycine derivative with phosphoric acid.
Suitable lower alkyl groups which can be used as substituents in the glycine derivative I are Cα to C„, straight or branched, groups . The glycine derivative I may be present in a hydrated form, for example as the monohydrate.
The glycine derivative may be present as a salt, for example as the sodium or potassium salt.
The sugar may be selected from a group consisting of dextrose fructose, glucose and maltose. It is preferred that the sugar is a maltodextrin. Maltodextrins comprise polymers of glucose, and will generally have a dextrose equivalent which is less than about 20, as determined by the Lane-Eynon titration technique (see Pearson's Chemical Analysis of Foods) . Maltodextrins can be derived from corn or maize. They often include small amounts of potassium, sodium, and sulphur dioxide.
Preferably, the amount of sugar present in the composition is at least about 30%, more preferably at least about 40%, by weight of the glycine derivative.
Preferably, the amount of sugar present in the composition is not more than about 70%, more preferably not more than about 60%, by weight of the glycine derivative.
In another aspect, the invention provides a pharmaceutical composition which comprises a composition of the type referred to above, in association with a solid or liquid a pharmaceutical carrier or diluent.
In a further aspect, the invention provides a method of making a pharmaceutical composition which comprises mixing (a) glycine derivative I
X1N=C(NX2Y) -NX3-C(X4.X5) -C02H I
where any one or more of X1, X2, X3, X4 and Xs is hydrogen or lower alkyl, and Y is hydrogen, lower alkyl, or H,PO, or a substituted variant thereof, or a salt of the derivative I, and (b) a sugar, in an amount of from about 2% to about 98% by weight of the derivative I.
The composition of the present invention can be used as a metabolic supplement. It can be used to enhance tissue formation, for example in the treatment of diseases, especially wasting diseases such as multiple sclerosis. It has been found that the composition is particularly well suited to enhancing cardiac tissue formation. It can also be used to prevent disease. It has the advantage that its principal constituents are occur naturally. Furthermore, the composition has a pleasant taste, and is stable under normal conditions.
The composition has been found to be suitable for use in the treatment of :
• mood disorders, such as bipolar, depressive disorders; recurrent depression disorders; schizo-affective dis¬ orders; dysthymia;
• schizophrenia
dementias, such as Alzheimer's disease; neurotic illness includning phobic anxiety disorders; obsessive compulsive disorders; reaction to severe stress; neur¬ asthenia, general anxiety states;
• chronic fatigue syndrome, including myalgia encephalo- yeletis (ME) .
In another aspect, the invention provides the use of a composition of the type discussed above in the manufacture of a medicament, especially for the treatment of one or more of the conditions referred to above. The composition of the invention can be administered in tablet form. It can be administered in powder form. It can be preferred for the composition to be administered in solution, in particular in aqueous solution; it can be particularly preferred to administer the composition in solution, possibly at elevated temperature, which might be the highest temperature at which the solution can comfortably be consumed. For example, the solution might be heated to a temperature which is greater than about 40°C, preferably greater than about 50°C, for example greater than about 60°C, or even higher. Administering the composition in this way has been found to facilitate absorption.
It can be preferred for the temperature of solution to be less than about 55°C when administered, more preferably less than about 45°C, even less than 40°C. This feature allows breakdown of the glycine derivative to be minimised. When the composition is dissolved in solution at a temperature which is elevated to facilitate dissolution, the temperature is preferably then lowered by addition of a liquid at lower temperature (which might be flavoured) to reduce the overall temperature of the solution.
When administered in solution, it can be preferred for the effective concentration of the glycine derivative to be greater than about 0.5% by weight, more preferably greater than about 0.7%, especially greater than about 1.0%. The concentration can be less than about 15% by weight, preferably less than about 10%, more preferably less than about 5%. Suitable concentrations are from about 1.5% to about 5%.
The invention will now be described with reference to certain examples.
EXAMPLE 1 Tablets were formed from a mixture of creatine monohydrate supplied by Chemielinz A G, and a maltodextrin supplied by Roquette Freres S A under the trade name Glucidex 19, in a ratio by weight 2:1, the two constituents being provided in powder form. Tablets were formed using conventional tablet presses from the resulting mixture.
EXAMPLE 2
Tablets were formed from a mixture of the creatine monohydrate used in Example 1 and a glucose polymer supplied by Edward Mendell & Co under the trade name Emdex, in a ratio by weight 2:1, the two constituents being provided in powder form. Tablets were formed using conventional tablet presses from the resulting mixture.
EXAMPLE 3
Tablets were formed from a mixture of the creatine monohydrate used in Example 1 and a dextrose polymer supplied by Cerestar Limited under the trade name Celellose, in a ratio by weight 2:1, the two constituents being provided in powder form. The mixture of the powders was supplied for ingestion in powder form.

Claims

CLAIMS :
1. A composition which comprises (a) glycine derivative I
XλN=C(NX2Y) -NX3-C(X4.X5) -C02H I
where any one or more of X1, X2, X3, X4 and Xs is hydrogen or lower alkyl, and Y is hydrogen, lower alkyl, or H2P03 or a substituted variant thereof, or a salt of the derivative I, and (b) a sugar in an amount of from about 2% to about 98% by weight of the derivative I.
2. A composition as claimed in claim 1, in which X3 is methyl.
3. A composition as claimed in claim 1 or claim 2, in which Y is H2P03.
4. A composition as claimed in any one of claims 1 to 3, in which the sugar is selected from a group consisting of dextrose fructose, glucose and maltose.
5. A composition as claimed in claim 4, in which the sugar is a maltodextrin.
6. A composition as claimed in any one of claims 1 to 5, in which the sugar is present in an amount of from about 30% to about 70% by weight of the glycine derivative.
7. A composition as claimed in claim 6, in which the sugar is present in an amount of from about 40% to about 60% by weight of the glycine derivative.
8. A pharmaceutical composition which comprises a composition as claimed in any one of claims 1 to '7 in association with a solid or liquid carrier or diluent.
9 . A method of making a pharmaceutical composition which comprises mixing (a) glycine derivative I
X1N=C (NX2Y) -NX3-C (X4 . X5) -C02H I
where any one or more of X1, X2, X3, X4 and X5 is hydrogen or lower alkyl, and Y is hydrogen, lower alkyl, or H2P03 or a substituted variant thereof, or a salt of the derivative I, and (b) a sugar in an amount of from about 2% to about 98% by weight of the derivative I.
10. A method as claimed in claim 9, in which the glycine derivative I and the sugar are mixed in powder form.
11. Use of a composition as claimed in any one of claims 1 to 7 in the manufacture of a medicament.
PCT/GB1994/000181 1993-02-03 1994-01-31 Blends of glycine derivatives and sugars WO1994017794A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU58903/94A AU5890394A (en) 1993-02-03 1994-01-31 Blends of glycine derivatives and sugars

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB939302070A GB9302070D0 (en) 1993-02-03 1993-02-03 Blends of glycine derivatives and sugars
GB9302070.9 1993-02-03
GB939320187A GB9320187D0 (en) 1993-09-30 1993-09-30 Blends of glycine derivatives and sugars
GB9320187.9 1993-09-30
GB9325374.8 1993-12-10
GB939325374A GB9325374D0 (en) 1993-12-10 1993-12-10 Blends of glycine derivatives and sugars

Publications (1)

Publication Number Publication Date
WO1994017794A1 true WO1994017794A1 (en) 1994-08-18

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WO (1) WO1994017794A1 (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996014063A1 (en) * 1994-11-08 1996-05-17 Avicena Group, Inc. Use of creatine or creatine analogs for the treatment of diseases of the nervous system
GB2313544A (en) * 1996-05-31 1997-12-03 Howard Foundation Improvements in or relating to compositions containing creatine
US6168802B1 (en) 1996-05-31 2001-01-02 The Howard Foundation Compositions containing creatine and aloe vera extract
WO2001003325A3 (en) * 1999-06-30 2001-08-02 Sueddeutsche Kalkstickstoff Use of creatine and/or creatine derivatives for treating feelings of ill-health in women
US6274161B1 (en) 1996-05-31 2001-08-14 The Howard Foundation Compositions containing creatine in suspension
US6503951B2 (en) 1999-06-30 2003-01-07 Skw Trostberg Aktiengesellschaft Use of creatine and/or creatine derivatives for treating typical disorders in women
US6524611B2 (en) 1996-05-31 2003-02-25 The Howard Foundation Compositions containing creatine and creatinine
EP1695703A2 (en) 2000-08-25 2006-08-30 Research Corporation Technologies, Inc. Anticonvulsant amino acids for the treatment of pain
EP1065931A4 (en) * 1998-04-02 2006-10-11 Avicena Group Inc COMPOSITIONS CONTAINING CREATINE COMBINED WITH A SECOND AGENT
US7150880B2 (en) 1996-05-31 2006-12-19 The Original Creatine Patent Co. Ltd. Compositions containing creatine and creatinine and a methyl xanthine
US8128955B2 (en) 1996-05-31 2012-03-06 The Original Creatine Patent Company Food compositions containing creatine
EP2468272A1 (en) * 2006-05-11 2012-06-27 Avicena Group, Inc. Methods of treating a neurological disorder with creatine monohydrate
US9233099B2 (en) 2012-01-11 2016-01-12 University Of Cincinnati Methods of treating cognitive dysfunction by modulating brain energy metabolism
DE102022114966A1 (en) 2022-06-14 2023-12-14 Alzchem Trostberg Gmbh Water-soluble creatine agglomerate

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1208398A (en) * 1966-06-30 1970-10-14 Calbiochem Reagent for assaying creatine phosphokinase
EP0339814A1 (en) * 1988-04-06 1989-11-02 Unitika Ltd. Reagent for measuring creatine kinase activity and measuring method thereof
EP0370994A2 (en) * 1988-11-25 1990-05-30 Gert Prof. Dr. Lubec Treatment of glucose-intermediated cross-linking of collagen in patients with diabetes mellitus by arginin, spermidin, creatin or agmatin

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1208398A (en) * 1966-06-30 1970-10-14 Calbiochem Reagent for assaying creatine phosphokinase
EP0339814A1 (en) * 1988-04-06 1989-11-02 Unitika Ltd. Reagent for measuring creatine kinase activity and measuring method thereof
EP0370994A2 (en) * 1988-11-25 1990-05-30 Gert Prof. Dr. Lubec Treatment of glucose-intermediated cross-linking of collagen in patients with diabetes mellitus by arginin, spermidin, creatin or agmatin

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6706764B2 (en) 1994-11-08 2004-03-16 Avicena Group, Inc. Use of creatine or creatine analogs for the treatment of diseases of the nervous system
US7285573B2 (en) 1994-11-08 2007-10-23 Avicena Group, Inc. Use of creatine or creatine analogs for the treatment of diseases of the nervous system
EP1719510A1 (en) * 1994-11-08 2006-11-08 Avicenda Group, Inc. Use of creatine or creatine analogs for the tratment of diseases of the nervous system
US20100303840A1 (en) * 1994-11-08 2010-12-02 Avicena Group, Inc. Use of creatine or creatine analogs for the treatment of diseases of the nervous system
EP2327404A1 (en) * 1994-11-08 2011-06-01 Avicena Group, Inc. Use of creatine or creatine analogs for the treatment of diseases of the nervous system
WO1996014063A1 (en) * 1994-11-08 1996-05-17 Avicena Group, Inc. Use of creatine or creatine analogs for the treatment of diseases of the nervous system
GB2313544B (en) * 1996-05-31 2000-01-12 Howard Foundation Improvements in or relating to compositions containing creatine
US8128955B2 (en) 1996-05-31 2012-03-06 The Original Creatine Patent Company Food compositions containing creatine
US6524611B2 (en) 1996-05-31 2003-02-25 The Howard Foundation Compositions containing creatine and creatinine
US6274161B1 (en) 1996-05-31 2001-08-14 The Howard Foundation Compositions containing creatine in suspension
US6168802B1 (en) 1996-05-31 2001-01-02 The Howard Foundation Compositions containing creatine and aloe vera extract
US5968544A (en) * 1996-05-31 1999-10-19 The Howard Foundation Compositions containing creatine
US7150880B2 (en) 1996-05-31 2006-12-19 The Original Creatine Patent Co. Ltd. Compositions containing creatine and creatinine and a methyl xanthine
GB2313544A (en) * 1996-05-31 1997-12-03 Howard Foundation Improvements in or relating to compositions containing creatine
EP1065931A4 (en) * 1998-04-02 2006-10-11 Avicena Group Inc COMPOSITIONS CONTAINING CREATINE COMBINED WITH A SECOND AGENT
WO2001003325A3 (en) * 1999-06-30 2001-08-02 Sueddeutsche Kalkstickstoff Use of creatine and/or creatine derivatives for treating feelings of ill-health in women
US6503951B2 (en) 1999-06-30 2003-01-07 Skw Trostberg Aktiengesellschaft Use of creatine and/or creatine derivatives for treating typical disorders in women
EP1695703A2 (en) 2000-08-25 2006-08-30 Research Corporation Technologies, Inc. Anticonvulsant amino acids for the treatment of pain
EP2468272A1 (en) * 2006-05-11 2012-06-27 Avicena Group, Inc. Methods of treating a neurological disorder with creatine monohydrate
US9233099B2 (en) 2012-01-11 2016-01-12 University Of Cincinnati Methods of treating cognitive dysfunction by modulating brain energy metabolism
DE102022114966A1 (en) 2022-06-14 2023-12-14 Alzchem Trostberg Gmbh Water-soluble creatine agglomerate
WO2023242126A1 (en) 2022-06-14 2023-12-21 Alzchem Trostberg Gmbh Water-soluble creatine agglomerate

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