WO2001072138A1 - Chewing gum containing sulfurated amino acid compounds - Google Patents

Chewing gum containing sulfurated amino acid compounds Download PDF

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Publication number
WO2001072138A1
WO2001072138A1 PCT/EP2001/003460 EP0103460W WO0172138A1 WO 2001072138 A1 WO2001072138 A1 WO 2001072138A1 EP 0103460 W EP0103460 W EP 0103460W WO 0172138 A1 WO0172138 A1 WO 0172138A1
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WO
WIPO (PCT)
Prior art keywords
chewing gum
gum according
agent
chosen
group
Prior art date
Application number
PCT/EP2001/003460
Other languages
French (fr)
Inventor
Mauro Castiglioni
Fabrizio Tencone
Original Assignee
F.T. Holding S.A.
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
Application filed by F.T. Holding S.A. filed Critical F.T. Holding S.A.
Priority to AU62137/01A priority Critical patent/AU6213701A/en
Publication of WO2001072138A1 publication Critical patent/WO2001072138A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/14—Chewing gum characterised by the composition containing organic or inorganic compounds containing peptides or proteins
    • 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
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/06—Tripeptides
    • A61K38/063—Glutathione
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • A61K9/0058—Chewing gums
    • 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

  • a chewing gum containing glutathione with methionine and/or taurine, or methionine and/or taurine, enables transmucosal absorption of said active agents pre- venting their degradation in the stomach.
  • Glutathione ( ⁇ -L-glutamyl-L-cysteinylglycin), methionine (2-amino-4- methylthiobutanoic acid) and taurine (2-aminoethansolfonic acid) are sulfurated amino acid compounds with a high pharmacological relevance.
  • Glutathione is an antioxidant and is useful as such for all those situations in which there is an increase of free radicals, highly reactive molecules which can damage the organism. The increase of free radicals can occur in pathologic situations such as HIV infections, hepatic cirrhosis, or in more common conditions such as the abuse of spirits, fasting or physical weariness.
  • Taurine is an antioxidant too, and it also favors the absorption and elimination of fats and can act as neurotransmitter in some brain areas and in the retina.
  • Methionine is a cystine and creatine precursor, both cystine and creatine being antioxidant amino acids, it favors the reduction of cholesterol levels in blood, the elimination of toxic substances from the liver and the regeneration of hepatic and kidney tissue.
  • glutathione As far as glutathione is concerned, despite its above-mentioned importance, it is commercially available in oral form only as a component of integrating food. As far as drugs containing it are concerned, these are present on the market in an extremely limited number and only as injectable substances, because said molecule is mostly de-activated by peptidase acting in the stomach.
  • EP 0 339 508 describes a tablet to dissolve in the mouth, containing acetyl- cysteine mixed with sodium or potassium bicarbonate, a sweetener and a flavoring agent.
  • acetyl- cysteine mixed with sodium or potassium bicarbonate, a sweetener and a flavoring agent.
  • bicarbonate salts consists in neutralizing the pH of N-acetyl-cysteine, which is quite acid and can therefore cause irritation in the oral cavity.
  • EP 0 349 797 describes among other things a chewing gum containing N-acetyl- cysteine stabilized by adding ascorbic acid or one of its salts.
  • This patent is criticized in the following patent application WO 98/47534, since the use of ascorbic acid alone makes pH more acid, which increases the oxidative phenomenon of the active agent and makes its quite unpleasant taste even more disagreeable.
  • This patent application describes among other things chewing gums containing cysteine or dicysteine compounds, in particular N-acetyl-cysteine, and/or glutathione in combination with a non steroidal anti-inflammatory, characterized by a mixture of stabilizers consisting of at least three components such as ascorbic acid, a salt or an ester thereof, one or more tocopherols, one or more carotenoids, one or more flavonoids or derivatives thereof.
  • the amount of ascorbic acid in this mixture is quite lower than formulations of the state of the art.
  • IT-1248998 discloses a chewing gum containing N-acetyl-cysteine which can be used in the prevention and treatment of dental plaque. To this purpose it is pointed out that the higher is the amount of gum, the slower is the release of the active agent.
  • WO 91/15204 discloses among other things chewing gums containing active agents which can lower plasma levels of lipoprotein (a), such as for instance N- acetyl-cysteine, glutathione and other sulfurated compounds. No indication is provided concerning the excipients of the formulation.
  • WO 99/00106 claims oral compositions to reduce damages caused by free radicals originated from smoking habits and environmental pollution, comprising a combination of reduced glutathione, a selenium source chosen among selenium methionine and selenium cysteine, ascorbic acid, ⁇ -tocopherol and an amino acid containing sulfur, in order to reduce said damage in the oral cavity, in the pharynx and in the first respiratory tract.
  • EP-A- 0 890 538 describes chewing tablets containing an antiemetic or therapeutic active agent for the oral cavity and the throat.
  • an antiemetic or therapeutic active agent for the oral cavity and the throat.
  • one of the examples of this application deals with a tablet based on chewing soluble gum containing N-acetyl-cysteine.
  • These tablets contain chewing components such as natural gums and dry syrups, syrup components, fat compo- nents such as esters of glycerol with long-chain acids, wax components such as bee wax, paraffin and ozokerite.
  • the present invention therefore, relates to a chewing gum containing glutathione with methionine and/or taurine, or methionine and/or taurine, and as excipients gums, antioxidants, wetting agents, flavoring agents and sweetening agents. DESCRIPTION OF THE INVENTION
  • the present invention therefore, relates to a chewing gum containing glutathione in association with methionine and/or taurine, or methionine and/or taurine, and as excipients at least one gum, at least one antioxidant, at least one wetting agent, flavoring and sweetening agents.
  • the chewing gum according to the present invention can optionally contain at least one complexing agent, at least one neutralizing agent and/or at least one preserving agent.
  • glutathione means both the reduced form (GSH) and the reduced form of ethyl ester.
  • the chewing gum according to the present invention contains 1 to 300 mg, preferably 48 mg of single active principle per product unit.
  • Gums which can be used in the present invention are all those which are commonly used to this purpose in the pharmaceutical field and in food industries.
  • Examples of gums which can be used in the present invention are those which are marketed with the trademarks H Maryl T ® (Gum Base Co.) and Balear-T ® (Cafosa Gum SA).
  • Antioxidants contained in the chewing gum according to the invention are chosen from the group consisting of ascorbic acid salts and esters thereof, butylated hy- droxyanisol (BHA), butylated hydroxytoluene (BHT), monothioglycerol, sodium metabisulfite, sodium thiosulfate, ⁇ -tocopherol. They are used in percentages of 0.001 to 0.1% with respect to the base gum, preferably 0.01%. Butylated hy- droxyanisol is preferably used.
  • Complexing agents which can be used in the present invention are those which are commonly used in the pharmaceutical field and/or in food industries, such as for instance ethylenediaminotetraacetic acid (EDTA) and pharmaceutically acceptable salts thereof.
  • Neutralizing agents which can be used in the present invention are sodium or potassium hydroxide in aqueous solution in such a concentration to be able to bring pH to physiologic values.
  • Preservatives which can be used in the present invention can be chosen from the group consisting of methyl-p-hydroxybenzoate, propyl-p-hydroxybenzoate, ascor- bic acid, potassium sorbate and mixtures thereof.
  • Flavors which can be used in the present invention are all those which are commonly used in the pharmaceutical field to improve/mask the unpleasant taste of sulfurated compounds. These are for instance citrus flavors, mint, chocolate, berries, which can be used both singularly and in suitable combinations. Flavors which are preferably used are citrus flavors or mint, still more preferably the chewing gum contains citric acid, malic acid, and citrus flavor.
  • the chewing gum according to the present invention also contains sweetening agents, such as for instance acesulfame, aspartame, sucrose, fructose, maltose, glucose, mannitol, sorbitol, xylitol, maltitol, saccharine, maltodextrin.
  • wetting agents which can be used in the present invention are one or more among those which are commonly used in the pharmaceutical field or in food industries, such as for instance glycerol, Twin, Span, PEG, triethyl citrate, tributyl citrate and mixtures thereof.
  • the preferred wetting agent in the present invention is glycerol. These agents are present in amounts of 10 to 40 mg, preferably 27 mg per prod- uct unit.
  • the units of chewing gum can optionally be prepared in the form of dragees with substances and methods commonly used in the pharmaceutical field. They can also contain suitable coloring agents.
  • the chewing gum according to the present invention is prepared with methods known in the field.
  • a chewing gum according to the invention is prepared, containing the following components whose amount is defined as g/100 g of final product: Reduced glutathione 2.5 g
  • Flavoring agents 3.8 g
  • the chewing gum according to the present invention has a pleasant taste and its use causes no irritation in the mucosa of the oral cavity. It releases the active agent/s which is/are absorbed by the mucosa, thus resulting in a significant hematic increase of said agent s.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Food Science & Technology (AREA)
  • Public Health (AREA)
  • Nutrition Science (AREA)
  • Polymers & Plastics (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Physiology (AREA)
  • Inorganic Chemistry (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Mycology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

A chewing gum containing glutathione with methionine and/or taurine, or methionine and/or taurine, can provide suitable hematic levels of said active agents through a transmucosal absorption.

Description

Chewing gum containing sulfurated amino acid compounds
FIELD OF THE INVENTION
A chewing gum containing glutathione with methionine and/or taurine, or methionine and/or taurine, enables transmucosal absorption of said active agents pre- venting their degradation in the stomach. STATE OF THE ART
Glutathione (γ-L-glutamyl-L-cysteinylglycin), methionine (2-amino-4- methylthiobutanoic acid) and taurine (2-aminoethansolfonic acid) are sulfurated amino acid compounds with a high pharmacological relevance. Glutathione is an antioxidant and is useful as such for all those situations in which there is an increase of free radicals, highly reactive molecules which can damage the organism. The increase of free radicals can occur in pathologic situations such as HIV infections, hepatic cirrhosis, or in more common conditions such as the abuse of spirits, fasting or physical weariness. Taurine is an antioxidant too, and it also favors the absorption and elimination of fats and can act as neurotransmitter in some brain areas and in the retina. Methionine is a cystine and creatine precursor, both cystine and creatine being antioxidant amino acids, it favors the reduction of cholesterol levels in blood, the elimination of toxic substances from the liver and the regeneration of hepatic and kidney tissue.
As far as glutathione is concerned, despite its above-mentioned importance, it is commercially available in oral form only as a component of integrating food. As far as drugs containing it are concerned, these are present on the market in an extremely limited number and only as injectable substances, because said molecule is mostly de-activated by peptidase acting in the stomach.
Taurine is marketed both as injectable substance and in oral form, in particular as a capsule of hard gelatin. This oral administration form is unacceptable for some patients for whom digesting said capsule can be difficult. EP 0 339 508 describes a tablet to dissolve in the mouth, containing acetyl- cysteine mixed with sodium or potassium bicarbonate, a sweetener and a flavoring agent. In particular, the role of bicarbonate salts consists in neutralizing the pH of N-acetyl-cysteine, which is quite acid and can therefore cause irritation in the oral cavity.
EP 0 349 797 describes among other things a chewing gum containing N-acetyl- cysteine stabilized by adding ascorbic acid or one of its salts. This patent is criticized in the following patent application WO 98/47534, since the use of ascorbic acid alone makes pH more acid, which increases the oxidative phenomenon of the active agent and makes its quite unpleasant taste even more disagreeable. This patent application describes among other things chewing gums containing cysteine or dicysteine compounds, in particular N-acetyl-cysteine, and/or glutathione in combination with a non steroidal anti-inflammatory, characterized by a mixture of stabilizers consisting of at least three components such as ascorbic acid, a salt or an ester thereof, one or more tocopherols, one or more carotenoids, one or more flavonoids or derivatives thereof. The amount of ascorbic acid in this mixture is quite lower than formulations of the state of the art. IT-1248998 discloses a chewing gum containing N-acetyl-cysteine which can be used in the prevention and treatment of dental plaque. To this purpose it is pointed out that the higher is the amount of gum, the slower is the release of the active agent.
WO 91/15204 discloses among other things chewing gums containing active agents which can lower plasma levels of lipoprotein (a), such as for instance N- acetyl-cysteine, glutathione and other sulfurated compounds. No indication is provided concerning the excipients of the formulation.
WO 99/00106 claims oral compositions to reduce damages caused by free radicals originated from smoking habits and environmental pollution, comprising a combination of reduced glutathione, a selenium source chosen among selenium methionine and selenium cysteine, ascorbic acid, α-tocopherol and an amino acid containing sulfur, in order to reduce said damage in the oral cavity, in the pharynx and in the first respiratory tract.
EP-A- 0 890 538 describes chewing tablets containing an antiemetic or therapeutic active agent for the oral cavity and the throat. Although not specified in the de- scription, one of the examples of this application deals with a tablet based on chewing soluble gum containing N-acetyl-cysteine. These tablets contain chewing components such as natural gums and dry syrups, syrup components, fat compo- nents such as esters of glycerol with long-chain acids, wax components such as bee wax, paraffin and ozokerite. SUMMARY OF THE INVENTION
It has now been surprisingly found a kind of transmucosal formulation to adminis- ter glutathione, methionine and/or taurine, which ensures the absorption of said active agents.
The present invention, therefore, relates to a chewing gum containing glutathione with methionine and/or taurine, or methionine and/or taurine, and as excipients gums, antioxidants, wetting agents, flavoring agents and sweetening agents. DESCRIPTION OF THE INVENTION
The present invention, therefore, relates to a chewing gum containing glutathione in association with methionine and/or taurine, or methionine and/or taurine, and as excipients at least one gum, at least one antioxidant, at least one wetting agent, flavoring and sweetening agents. Moreover, the chewing gum according to the present invention can optionally contain at least one complexing agent, at least one neutralizing agent and/or at least one preserving agent.
For the purpose of the present invention glutathione means both the reduced form (GSH) and the reduced form of ethyl ester. The chewing gum according to the present invention contains 1 to 300 mg, preferably 48 mg of single active principle per product unit.
Gums which can be used in the present invention are all those which are commonly used to this purpose in the pharmaceutical field and in food industries. Examples of gums which can be used in the present invention are those which are marketed with the trademarks H Maryl T® (Gum Base Co.) and Balear-T® (Cafosa Gum SA).
Antioxidants contained in the chewing gum according to the invention are chosen from the group consisting of ascorbic acid salts and esters thereof, butylated hy- droxyanisol (BHA), butylated hydroxytoluene (BHT), monothioglycerol, sodium metabisulfite, sodium thiosulfate, α-tocopherol. They are used in percentages of 0.001 to 0.1% with respect to the base gum, preferably 0.01%. Butylated hy- droxyanisol is preferably used. Complexing agents which can be used in the present invention are those which are commonly used in the pharmaceutical field and/or in food industries, such as for instance ethylenediaminotetraacetic acid (EDTA) and pharmaceutically acceptable salts thereof. Neutralizing agents which can be used in the present invention are sodium or potassium hydroxide in aqueous solution in such a concentration to be able to bring pH to physiologic values.
Preservatives which can be used in the present invention can be chosen from the group consisting of methyl-p-hydroxybenzoate, propyl-p-hydroxybenzoate, ascor- bic acid, potassium sorbate and mixtures thereof.
Flavors which can be used in the present invention are all those which are commonly used in the pharmaceutical field to improve/mask the unpleasant taste of sulfurated compounds. These are for instance citrus flavors, mint, chocolate, berries, which can be used both singularly and in suitable combinations. Flavors which are preferably used are citrus flavors or mint, still more preferably the chewing gum contains citric acid, malic acid, and citrus flavor. The chewing gum according to the present invention also contains sweetening agents, such as for instance acesulfame, aspartame, sucrose, fructose, maltose, glucose, mannitol, sorbitol, xylitol, maltitol, saccharine, maltodextrin. Wetting agents which can be used in the present invention are one or more among those which are commonly used in the pharmaceutical field or in food industries, such as for instance glycerol, Twin, Span, PEG, triethyl citrate, tributyl citrate and mixtures thereof. The preferred wetting agent in the present invention is glycerol. These agents are present in amounts of 10 to 40 mg, preferably 27 mg per prod- uct unit.
The units of chewing gum can optionally be prepared in the form of dragees with substances and methods commonly used in the pharmaceutical field. They can also contain suitable coloring agents. The chewing gum according to the present invention is prepared with methods known in the field.
The following provides an example of chewing gum compositions according to the present invention. EXAMPLE 1
A chewing gum according to the invention is prepared, containing the following components whose amount is defined as g/100 g of final product: Reduced glutathione 2.5 g
Sorbitol 32.7 g
Xylitol 14.3 g
Maltitol 4.7 g
Mannitol 2.4 g
Base gum H Maryl T® 35.7 g
Butyl hydroxyanisol 0.02 g
Glycerol 1.4 g
Flavoring agents 3.8 g
Malic acid + citric acid 2 g
Potassium acesulfame + aspartame 0.5 g
The chewing gum according to the present invention has a pleasant taste and its use causes no irritation in the mucosa of the oral cavity. It releases the active agent/s which is/are absorbed by the mucosa, thus resulting in a significant hematic increase of said agent s.

Claims

I . Chewing gum containing glutathione in association with methionine and/or taurine, or methionine and/or taurine, and as excipients at least one gum, at least one antioxidant, at least one wetting agent, flavoring agents and sweeteners.
2. Chewing gum according to claim 1 , containing at least one complexing agent, at least one neutralizing agent and/or at least one preserving agent.
3. Chewing gum according to claim 1 , in which glutathione is in reduced form (GSH) or in ethyl ester reduced form.
4. Chewing gum according to claim 1 , containing 1 to 300 mg of single active agent per product unit.
5. Chewing gum according to claim 4, containing 48 mg of single active agent per product unit.
6. Chewing gum according to claim 1 , in which the antioxidant is chosen from the group consisting of ascorbic acid and salts and esters thereof, butylated hy- droxyanisol, butylated hydroxytoluene, monothioglycerol, sodium metabisulfite, sodium thiosulfate, α-tocopherol.
7. Chewing gum according to claim 6, in which the amount of antioxidant is of 0.001 to 0.1% with respect to the base gum.
8. Chewing gum according to claim 7, in which the amount of antioxidant is of 0.01 % with respect to the base gum.
9. Chewing gum according to claim 6, in which said antioxidant is butylated hydroxyanisol.
10. Chewing gum according to claim 2, in which the complexing agent is ethyl- enediaminotetraacetic acid (EDTA) and pharmaceutically acceptable salts thereof.
I I . Chewing gum according to claim 2, in which the neutralizing agent is sodium or potassium hydroxide in aqueous solution.
12. Chewing gum according to claim 2, in which the preserving agent is chosen from the group consisting of methyl-p-hydroxybenzoate, propyl-p- hydroxybenzoate, ascorbic acid, potassium sorbate.
13. Chewing gum according to claim 1 , in which the flavoring agent is chosen from the group consisting of citrus flavors, mint, chocolate, berries, which can be used both singularly and in suitable combinations.
14. Chewing gum according to claim 13, in which said flavoring agent is chosen form the group consisting of citrus flavors or mint.
15. Chewing gum according to claim 14, containing citric acid, malic acid, and cit- rus flavor.
16. Chewing gum according to claim 1 , in which the sweetening agent is chosen from the group consisting of acesulfame, aspartame, sucrose, fructose, maltose, glucose, mannitol, sorbitol, xylitol, maltitol, saccharine, maltodextrin and mixture thereof.
17. Chewing gum according to claim 1 , in which the wetting agent is chosen from the group consisting of glycerol, Twin, Span, PEG, triethyl citrate, tributyl citrate and mixture thereof.
18. Chewing gum according to claim 17, in which said wetting agent is glycerol.
19. Chewing gum according to claim 1 , in which said wetting agent is contained in amounts of 10 to 40 mg per product unit.
20. Chewing gum according to claim 19, in which said wetting agent is contained in an amount of 27 mg per product unit.
21. Chewing gum according to claim 1 , containing coloring agents.
22. Chewing gum according to claim 1, in which said chewing gum is in the form of a dragee.
PCT/EP2001/003460 2000-03-27 2001-03-27 Chewing gum containing sulfurated amino acid compounds WO2001072138A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU62137/01A AU6213701A (en) 2000-03-27 2001-03-27 Chewing gum containing sulfurated amino acid compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT2000MI000639A IT1318427B1 (en) 2000-03-27 2000-03-27 CHEWING RUBBER CONTAINING SULFURATED AMINO ACIDS COMPOUNDS.
ITMI2000A000639 2000-03-27

Publications (1)

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WO2001072138A1 true WO2001072138A1 (en) 2001-10-04

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IT (1) IT1318427B1 (en)
WO (1) WO2001072138A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017004396A1 (en) * 2015-06-30 2017-01-05 Nucorplabs, Inc. Chewable composition to deliver gsh
US10787476B2 (en) 2013-09-24 2020-09-29 Ajinomoto Co., Inc. Glycoamino acid and use thereof

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5272166A (en) * 1990-04-09 1993-12-21 The Rockefeller University Method for selective reduction of Lp(a)
WO1996005803A1 (en) * 1994-08-22 1996-02-29 Quest International B.V. Breath malodour reduction
WO1998047534A1 (en) * 1997-04-18 1998-10-29 Klinge Pharma Gmbh Stabilized medicaments containing cysteinyl derivatives
WO1999000106A1 (en) * 1997-06-27 1999-01-07 Thione International, Inc. Intra-oral antioxidant preparations
US5922346A (en) * 1997-12-01 1999-07-13 Thione International, Inc. Antioxidant preparation
CN1272324A (en) * 1999-04-29 2000-11-08 长春市芦荟应用研究所 Aloe chewing sweets
WO2000069470A2 (en) * 1999-05-17 2000-11-23 Aesgen, Inc. Improved cellular uptake of bioactive agents

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5272166A (en) * 1990-04-09 1993-12-21 The Rockefeller University Method for selective reduction of Lp(a)
WO1996005803A1 (en) * 1994-08-22 1996-02-29 Quest International B.V. Breath malodour reduction
WO1998047534A1 (en) * 1997-04-18 1998-10-29 Klinge Pharma Gmbh Stabilized medicaments containing cysteinyl derivatives
WO1999000106A1 (en) * 1997-06-27 1999-01-07 Thione International, Inc. Intra-oral antioxidant preparations
US5922346A (en) * 1997-12-01 1999-07-13 Thione International, Inc. Antioxidant preparation
CN1272324A (en) * 1999-04-29 2000-11-08 长春市芦荟应用研究所 Aloe chewing sweets
WO2000069470A2 (en) * 1999-05-17 2000-11-23 Aesgen, Inc. Improved cellular uptake of bioactive agents

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 200121, Derwent World Patents Index; Class A96, AN 2001-203307, XP002173701 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10787476B2 (en) 2013-09-24 2020-09-29 Ajinomoto Co., Inc. Glycoamino acid and use thereof
WO2017004396A1 (en) * 2015-06-30 2017-01-05 Nucorplabs, Inc. Chewable composition to deliver gsh

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IT1318427B1 (en) 2003-08-25
AU6213701A (en) 2001-10-08
ITMI20000639A1 (en) 2001-09-27
ITMI20000639A0 (en) 2000-03-27

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