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WO1994015595A1 - Preparation comprenant une substance active pharmacologique/biologique - Google Patents

Preparation comprenant une substance active pharmacologique/biologique Download PDF

Info

Publication number
WO1994015595A1
WO1994015595A1 PCT/DK1994/000007 DK9400007W WO9415595A1 WO 1994015595 A1 WO1994015595 A1 WO 1994015595A1 DK 9400007 W DK9400007 W DK 9400007W WO 9415595 A1 WO9415595 A1 WO 9415595A1
Authority
WO
WIPO (PCT)
Prior art keywords
ubiquinone
medium
fact
medium according
plaster
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.)
Ceased
Application number
PCT/DK1994/000007
Other languages
English (en)
Inventor
Lasse Hessel
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.)
JEMO-PHARM AS
Original Assignee
JEMO-PHARM AS
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 DK9300009U external-priority patent/DK9300009U4/da
Priority claimed from DK9300080U external-priority patent/DK9300080U4/da
Priority claimed from DK9300137U external-priority patent/DK9300137U3/da
Application filed by JEMO-PHARM AS filed Critical JEMO-PHARM AS
Priority to AU58327/94A priority Critical patent/AU5832794A/en
Publication of WO1994015595A1 publication Critical patent/WO1994015595A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7084—Transdermal patches having a drug layer or reservoir, and one or more separate drug-free skin-adhesive layers, e.g. between drug reservoir and skin, or surrounding the drug reservoir; Liquid-filled reservoir patches
    • 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
    • A61K31/12—Ketones
    • 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
    • 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

Definitions

  • This invention concerns a medium containing a pharmacolcgically/biologically active substance which can be released from the medium in controlled fashion.
  • this invention concerns a type of chewing gum and a lozenge for sucking/chewing for use in controlled release or the medium to the mucous membr ana in the mouth and elsewhere, and a plaster for use in controlled release of the medium through t he skin.
  • Ubiquinone is the name given to the co-enzyme Q10 ⁇ CoQ10), which is also Known as vitamin Q, and whose chemical name is 2,3-dimethoxy-5-methyl-6-decaprenyl-1.4-benzoquinone.
  • Ubi quinone forms an important part of the so-called electron transport chain in the membrane of the mitochondrions, which binde the energy in nutrients to adenosine triphosphate (ATP), the energy store of the body cells.
  • ATP adenosine triphosphate
  • ubiquinone is part of the enzyme known as succinate dehydrogenase-co-Q10 (see Flytlie, K.T.
  • ubiquinone to chewing gum leads to the slow release or the substance during the period in which the chewing gum is chewed.
  • ubiquinone to lozenges for sucking or chewing leads to the slow release of the substance during tha period in which the lozenges are sucked or chewed.
  • plaster containing ubiquinone leads to the controlled release of the substance through the skin.
  • European patent application no. EP-472428-A describes a type of chewing gum containing stimulants such as nicotins and caffeine, antibiotics, water-soluble vitamins and minerals.
  • European patent application no. EP-205133-A also describes a type of chewing gum that contains a tincture of herbal derivatives which have, among other things, an anti-paradentosis effect or refreshing effect, or which provide compensation for nicotins.
  • these well-known chewing gum compounds do not contain ubiquinone, and the aim of this invention is to provide a chewing gum with an improved effect on complaints in the oral cavity, including paradentosis.
  • a number of other beneficial effects are obtained which are not limited to the oral cavity, since once released the ubiquinone will pass with the saliva through the oesophagus and stomach, and will then be absorbed in the alimentary canal.
  • the beneficial effects of ubiquinone comprise both a prophylactic effect and treatment of a range of complaints such as angina pectoris, hypertension, muscular dystrophy and periodontal complaints (see Greenberg: J. Clin. Pharmacol. 1990, 30:596-608).
  • lozenges are often used to treat complaints in the oral cavity and pharynx, e.g. Hexokain ® lozenges from DAK-Laboratoriet A/S in Copenhagen, which contain the act ive subatances benzocaine and chlorhexadine hydrochloride.
  • Hexokain ® lozenges from DAK-Laboratoriet A/S in Copenhagen, which contain the act ive subatances benzocaine and chlorhexadine hydrochloride.
  • sweets contai- ning anti-cough medicine is also well-known.
  • lozenges or sweets do not contain ubiquinone, and the aim of this invention is to provide a lozenge with an improved effect on complaints in the oral cavity, including paradentosis .
  • a number of other beneficial effects are obtained which are not limited to the oral cavity, since once released the ubiquinone will pass with the saliva through the ossophagus and stomach, and will then be absorbed in the alimentary canal
  • plasters containing nicotine have been produced to counteract the unpleasant effects experienced by people trying to stop smoking. Car sickness can also be counteracted by the application of a plaster containing ginger or scopolamine.
  • the purpose of this invention is to provide a plaster which has an effect on complaints associated with ubiquinone deficiency, or complaints for which ubiquinone has a soothing, prophylactic or healing effect.
  • the oral application ot ubiquinone does not ensure the optimum absorption and/or effect of ubiquinone. in such cases, the maintenance of a constant. high level of ubiquinone in the blood is desirable, and this can be achieved by using plasters for the controlled release of ubiquinone through the skin into the bloodstream.
  • the active substance used is ubiquinone
  • the medium used is chosen from among media used for the release or the active substance through the mouth or skin (primarily a chewing gum, a plaster, or a lozenge for sucking/chewing).
  • the medium used is infused with ubiquinone in a prophylactic and/or therapeutic dosage.
  • Chewing this new type of chewing gum leads to the extended or controlled release of ubiquinone to the mucous membrane in the mouth and, secondarily, to the gastrointestinal canal. This ensures the direct effect of ubiquinone for the prevention or treatment of complaints in the oral cavity (primarily paraden tosis).
  • an amount of ubiquinone ranging from 1 mg to 200 mg iprimarily trom 10 to 30 mg , from 50 to 75 mg, or from 100 to 150 mg , and primarily in the form of micro-capsules) is added to each piece of chewing gum weighing 1 g.
  • Micro-encapsulation protects the ubiqinone from the surrounding chewing gum matrix, and ensures protection from oxidation and slow release during chewing.
  • the micro-capsules have a diameter of less than 100 ⁇ m.
  • Ubiguinone is lipid soluble, so an oil solution is preferred, e.g. a soya oil solution, to which a natural emulsifier such as lecithin (primarily soya lecithin or a suspension or emulsion in soya lecithin) is added to ensure absorption in the aqueous environment in the oral cavity and gastrointestinal canal.
  • a natural emulsifier such as lecithin (primarily soya lecithin or a suspension or emulsion in soya lecithin) is added to ensure absorption in the aqueous environment in the oral cavity and gastrointestinal canal.
  • lecithin primarily soya lecithin or a suspension or emulsion in soya lecithin
  • Hiro et al. Biomedical and clinical aspects of coenzyme Q. Volume 4, Elsevier, (1984) have shown that ubiquinone is absorbed best in the form of a lipid solution.
  • other additives may
  • the ubiquinone solution, suspension or emulsion can be micro- encapsulated in a colloid matrix such as gelatins, gum acacia (gum arabic), starch, etc., or in sugar.
  • a colloid matrix such as gelatins, gum acacia (gum arabic), starch, etc., or in sugar.
  • Ubiquinone can also be added to the chewing gum direct in solid form (e.g. as a granulate), or in powder form in a blend with soya lecithin primarily in the ratio 1;1, but in such cases dosages should be increased by the amount of the active substance fixed in the gum base.
  • the minimum daily dosage should be approx. 30 mg to approx. 100 mg of ubiquinone, which has been declared to be almost free from side effects, see Langsjoen, P.H. and Folkers , K.: Am. J. Cardiol.: 65:7:521-3 (1990). Consequently, the recommended dosage is to Chew at least one piece of chewing gum containing 30 mg of micro-encapsulated ubiquinone for at least 10 minutes per day.
  • the chewing gum also contains a gum base and primarily flavourings such as oil of peppermint and fruit flavours, and sweeteners such as sugar, including saccharose, fructose and glucose, or sugar alcohols, primarily sorbitol or xylitol.
  • flavourings such as oil of peppermint and fruit flavours
  • sweeteners such as sugar, including saccharose, fructose and glucose, or sugar alcohols, primarily sorbitol or xylitol.
  • the gum base contains gums, natural and synthetic resins, synthetic polymers, paraffins and waxes.
  • Ubiquinone has no distinctive taste, so it can be mixed into most standard chewing gum recipes without adding any other flavourings or sweeteners.
  • This invention concerns primarily a chewing gum containing 60- 80% sugar, 17-37% gum base, 0.1-0.3% flavourings, and 1.9-3.7% of a mixture of ubiquinone and lecithin in a ratio of from 1:0.5 to 0.5: 1, or a sugar free chewing gum containing 10-30% sorbitol, 67-67% gum base, 0.1 0.3% flavourings, and 1.9-3.7% of a mixture of ubiquinone and lecithin in a ratio of from 1 : 0 . 5 to 0 . 5 : 1 .
  • lozenges for sucking containing ubiquinone, a hard tablet is preferred which dissolves or disintegrates slowly in the oral cavity while ubiquinone is released.
  • Lozenges are made by moulding and cutting, or by compression. During moulding the components are mixed in the form of a powder or in liquid form with the tablet base (usually sucrose, gum acacia or tragacanth) to produce a paste which is than cut into uniform pieces which are dried in a heat chamber. Flavourings and colourings may be added.
  • Lozenges produced by compression are made like standard tablets, using standard tablet additives such as lactose, dextrose, starch, sodium chloride and gum acacia, by dry or moist granulation, but by compression when a higher pressure is applied.
  • a softer tablet is preferred, primarily a gelatine, starch or pectin tablet in which ubiquinone is distributed, primarily in the form of a dispersed powder.
  • an amount of ubiquinone ranging from 1 mg to 200 mg (primarily from 10 to 30 mg, from 50 to 75 mg, or from 100 to 150 mg, and primarily in the form of micro-capsules) is added to each lozenge weighing 1 g, Micro-encapsulation ensures protection from oxidation and slow release during sucking/chewing.
  • the micro- capsuies have a diameter of less than 100 ⁇ m .
  • Ubiquinone is lipid soluble, so an oil solution is preferred, e.g. a soya oil solution, to which a natural emulsifier such as lecithin (primarily soya lecithin or a suspension or emulsion in soya lecithin) is added to ensure absorption in the aqueous environment in the oral cavity and gastrointestinal canal.
  • a natural emulsifier such as lecithin (primarily soya lecithin or a suspension or emulsion in soya lecithin)
  • Hiro et al. Biomedical and clinical aspects of coenzyme Q. Volume 4, Elsevier, (1984) have shown that ubiquinone is absorbed best in the form of a lipid solution.
  • other additives may be used to promote the absorption of ubiquinone either on their own or in connection with lecithin.
  • the ubiquinone solution, suspension or emulsion can be micro- encapsulated in a colloid matrix such as gelatine, gum acacia, starch, etc., or in sugar.
  • Ubiquinone can also be added to the lozenge direct in solid form (e.g. as a granulate or in powder form), in a blend with soya lecithin primarily in the ratio 1:1.
  • the minimum daily dosage should be approx. 30 mg to approx. 100 mg of Ubiquinone, which has been declared to be almost free from side effects, see Langsjoen, P.H, and Folkers, K.: Am. J. Cardiol.: 65:7:521-3 (1990). Consequently, the recommended dosage is to suck or chew at least one tablet containing 30 mg of micro-encapsulated ubiquinone for at least 10 minutes per day,
  • the tablet also contains primarily flavourings such as oil of peppermint and fruit flavours, and sweeteners such as sugar, including saccharose, fructose and glucose, or sugar alcohols, primarily sorbitol or xylitol.
  • flavourings such as oil of peppermint and fruit flavours
  • sweeteners such as sugar, including saccharose, fructose and glucose, or sugar alcohols, primarily sorbitol or xylitol.
  • Ubiquinone has no distinctive taste, so it can be mixed into most standard lozenge recipes without adding any other flavourings or sweeteners,
  • This invention concerns primarily a lozenge containing 10-100 mg, primarily 30-70 mg, of a mixture of ubiquinone and lecithin in a ratio of from 1:0.5 to 0.5:1.
  • Using the new plaster leads to the extended and/or controlled absorption of ubiquinons through the skin. This ensures the direct effect of ubiquinone for the prevention or treatment of iliness or obesity. Shortly after application of the plaster the skin starts to sweat. The skin dissolves slightly; thereby allowing the ubiquinone to be absorbed.
  • an amount of ubiquinone ranging from 1 mg to 200 mg (primarily from 10 to 30 mg, from 50 to 75 mg. or from 100 to 150 mg) is suspended in a gel or gel-like substance, which seeps through a permeable membrane under almost complete control and through the skin for absorption by the body, using a plaster.
  • Ubiquinone in the form of a powder, solution, suspension or emulsion can be distributed in a gel such as ethanol gel or propanol gel consisting of alcohol, in which hydroxy propyl cellulose or similar cellulose derivatives have been dissolved or absorbed.
  • the gel may also consist of paraffinum liquidum, polyisobutylenum, or other lipophilic gelling agents to promote absorption through the skin.
  • the gel may contain the granulation agent known as Eudragit E100.
  • the minimum daily dosage should be approx. 30 mg to approx. 100 mg of ubiquinone, which has been declared to be almost free from side effects, see Liangajoen, P.K, and Folkers, K. : Am. J. Cardiol.: 65:7:521-3 (1950). Consequently, the recommended dosage is to apply at leaat one plaster containing 30 mg of ubiquinone daily. Direct absorption through the skin makes it possible to avoid passing with the blood through the liver first, which would result in the partial break-down of ubiquinone. Consequently , It may be assumed that the effective daily dosage is less when ubiquinone plaster ie used.
  • Figure 1 shows the preferred design of the plaster containing ubiquinone.
  • Chewing gum is produced in standard fashion weighing 1.2 g per piece, with the following contents (percentages in terms of weight);
  • the chewing gum should be packed in light-proof packaging, since ubiquinone breaks down when exposed to sunlight.
  • Lozenges are produced in standard fashion weighing 1 g each, with the following contents (expressed in mg);
  • the tablets should be packed in light-proof packaging, since ubiquinone breaks down when exposed to sunlight.
  • Lozenges are produced in standard fashion weighing 1 g each, with the following concents (expressed in mg):
  • Lozenges are produced in standard fashion weighing 1 g each, with the following contents (expressed in mg):
  • mixture 1:1 100 mg (1) is a leak-proof plastic membrane on tha outside of the plaster.
  • the material used is primarily polypropylene or polyethylene.
  • (2) is the carrier, primarily a hydroxy propyl cellulose/ethanol gel, in which ubiquinone is incorporated.
  • (3) is a semi-permeable or perforated plastic membrane, the pore size of which regulates the race of release of the active substance (in this case ubiquinone) .
  • the preferred diameter of the pores ensure the regular release of ubiquinone over a period ot 6-12 hours.
  • the middle field contains ubiquinone, and the edges are coated with a skin-friendly adhesive.
  • the plaster is packed primarily in a light-proof foil pack (e.g. aluminium foil), which exposes the adhesive field when removed.
  • a light-proof foil pack e.g. aluminium foil
  • the plaster should not be applied to the same area of skin two or more times in a row.
  • a new area of skin should be chosen each time a new plaster is applied, and ubiquinone is absorbed most easily by areas of skin in which there is no hair.
  • the speed of absorption is determined by the area of the plaster, the permeability, and the concentration of ubiquinone in the carrier.

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Dermatology (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)

Abstract

Préparation, principalement sous forme de chewing-gum, de pastilles à sucer ou à mâcher, ou de sparadrap (4). Cette préparation contient de l'ubiquinone, principalement en une dose prophylactique et/ou thérapeutique.
PCT/DK1994/000007 1993-01-06 1994-01-05 Preparation comprenant une substance active pharmacologique/biologique Ceased WO1994015595A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU58327/94A AU5832794A (en) 1993-01-06 1994-01-05 Medium comprising a pharmacological/biological active substance

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
DK9300009U DK9300009U4 (da) 1993-01-06 1993-01-06 Tyggegummi indeholdende ubiqinon
DK0009/93 1993-01-06
DK9300080U DK9300080U4 (da) 1993-02-09 1993-02-09 Suge- eller tyggetablet indeholdende ubiqinon
DK0080/93 1993-02-09
DK9300137U DK9300137U3 (da) 1993-03-04 1993-03-04 Plaster indeholdende ubiqinon
DK0137/93 1993-03-04

Publications (1)

Publication Number Publication Date
WO1994015595A1 true WO1994015595A1 (fr) 1994-07-21

Family

ID=27222228

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DK1994/000007 Ceased WO1994015595A1 (fr) 1993-01-06 1994-01-05 Preparation comprenant une substance active pharmacologique/biologique

Country Status (2)

Country Link
AU (1) AU5832794A (fr)
WO (1) WO1994015595A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996021432A1 (fr) * 1995-01-11 1996-07-18 Cygnus, Inc. Administration de substances actives par les muqueuses pharyngiennes et ×sophagiennes
US6372198B1 (en) * 2000-09-14 2002-04-16 Joseph M. Abbate Dentifrice for the mineralization and remineralization of teeth
EP1135100A4 (fr) * 1998-12-11 2002-07-17 Pharma Inc Q Compositions pour soins buccaux comprenant une coenzyme q 10?
US6503483B2 (en) * 1997-06-12 2003-01-07 C.S. Bioscience, Inc. Dental formulation
WO2003037284A1 (fr) * 2001-10-31 2003-05-08 Smithkline Beecham P.L.C. Composition pour hygiene buccale
WO2003077951A1 (fr) * 2002-03-20 2003-09-25 Kaneka Corporation Promoteurs d'absorption percutanee et compositions servant a traiter le pied apres un effort sportif
EP1729767A1 (fr) * 2004-03-31 2006-12-13 Les Laboratoires Servier Association entre un compose heterocyclique et un agent antioxydant et son utilisation pour le traitement de l'obesite

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2157171A (en) * 1984-04-09 1985-10-23 Seuref Ag Pharmaceutical compositions having cerebral antianoxic and metabolic activities
WO1986004503A1 (fr) * 1985-02-01 1986-08-14 Zambon S.P.A. Composition pharmaceutique contenant de l'ubidecarenone
EP0205133A1 (fr) * 1985-06-14 1986-12-17 Marie Luise Dr. Schicht Masse à mâcher plastique à base de gomme à mâcher
US4751241A (en) * 1981-07-14 1988-06-14 Freund Industrial Company, Ltd. Pharmaceutical composition of cyclandelate having a high degree of bioavailability
EP0472428A2 (fr) * 1990-08-23 1992-02-26 Wm. Wrigley Jr. Company Chewing gum à humidité réduite
WO1994006418A1 (fr) * 1992-09-16 1994-03-31 Institut Für Sozial-Medizinische Forschung Composition a macher contenant le coenzyme q 10

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4751241A (en) * 1981-07-14 1988-06-14 Freund Industrial Company, Ltd. Pharmaceutical composition of cyclandelate having a high degree of bioavailability
GB2157171A (en) * 1984-04-09 1985-10-23 Seuref Ag Pharmaceutical compositions having cerebral antianoxic and metabolic activities
WO1986004503A1 (fr) * 1985-02-01 1986-08-14 Zambon S.P.A. Composition pharmaceutique contenant de l'ubidecarenone
EP0205133A1 (fr) * 1985-06-14 1986-12-17 Marie Luise Dr. Schicht Masse à mâcher plastique à base de gomme à mâcher
EP0472428A2 (fr) * 1990-08-23 1992-02-26 Wm. Wrigley Jr. Company Chewing gum à humidité réduite
WO1994006418A1 (fr) * 1992-09-16 1994-03-31 Institut Für Sozial-Medizinische Forschung Composition a macher contenant le coenzyme q 10

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BIOMEDICAL AND CLINICAL ASPECTS OF COENZYME Q, Volume 4, 1984, LUC VAN GAAL et al., "Exploratory Study of Coenzyme Q10 in Obesity", page 369 - page 373. *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996021432A1 (fr) * 1995-01-11 1996-07-18 Cygnus, Inc. Administration de substances actives par les muqueuses pharyngiennes et ×sophagiennes
US6503483B2 (en) * 1997-06-12 2003-01-07 C.S. Bioscience, Inc. Dental formulation
EP1135100A4 (fr) * 1998-12-11 2002-07-17 Pharma Inc Q Compositions pour soins buccaux comprenant une coenzyme q 10?
US6372198B1 (en) * 2000-09-14 2002-04-16 Joseph M. Abbate Dentifrice for the mineralization and remineralization of teeth
WO2003037284A1 (fr) * 2001-10-31 2003-05-08 Smithkline Beecham P.L.C. Composition pour hygiene buccale
WO2003077951A1 (fr) * 2002-03-20 2003-09-25 Kaneka Corporation Promoteurs d'absorption percutanee et compositions servant a traiter le pied apres un effort sportif
EP1729767A1 (fr) * 2004-03-31 2006-12-13 Les Laboratoires Servier Association entre un compose heterocyclique et un agent antioxydant et son utilisation pour le traitement de l'obesite

Also Published As

Publication number Publication date
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