WO2008024006A2 - Pharmaceutical preparation in a gel form - Google Patents

Pharmaceutical preparation in a gel form Download PDF

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Publication number
WO2008024006A2
WO2008024006A2 PCT/PL2007/000024 PL2007000024W WO2008024006A2 WO 2008024006 A2 WO2008024006 A2 WO 2008024006A2 PL 2007000024 W PL2007000024 W PL 2007000024W WO 2008024006 A2 WO2008024006 A2 WO 2008024006A2
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Prior art keywords
preparation
agent
amounts
weight
parts
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Application number
PCT/PL2007/000024
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French (fr)
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WO2008024006A3 (en
Inventor
Grzegorz Nowakowski
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Przedsiebiorstwo Produkcji Farmaceutycznej Gemi
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Publication of WO2008024006A3 publication Critical patent/WO2008024006A3/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/40—Peroxides
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/18—Iodine; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/51—Gentianaceae (Gentian family)
    • A61K36/515—Gentiana
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • 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
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • A61P23/02—Local anaesthetics

Definitions

  • the invention provides a pharmaceutical preparation in a gel form exhibiting a disinfecting and therapeutic activity.
  • GB 2068225 discloses dermatological compositions comprising hydrogen peroxide in a form of an aqueous solution and a gelling agent.
  • gelling agents the following substances are taught in the specification: carboxyvinyl polymers, colloidal silicates, natural gums, starch, cellulose derivatives.
  • US 4401651 discloses a pharmaceutical preparation for application on wounds comprising gentian violet as an active agent and polyethylene glycol as a gelling agent.
  • the document discloses also a preparation comprising iodine-polyvinylpyrrolidone complex as an active agent and polyethylene glycol.
  • the Polish patent application No P-332783 discloses a gelatinous pharmaceutical preparation comprising perhydrol or gentian violet, or iodine as active agents, combined with polyvinylpyrrolidone (iodopoly vinylpyrrolidone), with a viscosity of from 2000 to 10000 cnp. Hydroxycellulose was used as a gelling agent.
  • Preparations known from the prior art have a form of gel, which facilitates their precise application onto spots requiring treatment with the preparation, such as injuries, abrasions etc.
  • a condensed preparation may be applied precisely onto a wound, excluding healthy skin around the affected spot.
  • Critical for the process for the manufacture of such products and for their usability is the kind of gelling agent. It is important for the gelling agent to allow for thorough mixing of the components in a liquid form and provide a sufficient stability of the final preparations. In the case of active agents of high chemical and biological activity, such as e.g. hydrogen peroxide, numerous gelling agents are excluded.
  • a pharmaceutical preparation in a gel form comprising hydrogen peroxide or gentian violet, or iodine as an active agent, a gelling agent, a solvent and optional auxiliary agents is provided, which comprises as a gelling agent a block copolymer of ethylen oxide and propylen oxide of formula HO(C 2 H 4 O) a (C 3 H 6 O) b (C 2 H 4 O) a H, wherein a is an integer from 6 to 160, and b is an integer from 8 to 100, and the preparation comprises the gelling agent in amounts of from 10 to 40 parts by weight, and the active agent in amounts of from 0,5 to 15 parts by weight.
  • the preparation comprises gelling agent of formula HO(C 2 H 4 O) a (C3H 6 O)b(C 2 H4 ⁇ ) a H, wherein a is an integer from 80 to 120, and b is an integer from 37 to 80.
  • the preparation preferably comprises water and/or an aliphatic alcohol, most preferably ethanol, in amounts of from 10 to 80 parts by weight.
  • the preparation preferably comprises a pH regulator, most preferably orthophosphoric acid, in such amounts that pH of the preparation is from 3,5 to 4,5.
  • the preparation preferably comprises a chelating agent, most preferably disodium edetate, in amounts of 0,1-0,5 parts by weight.
  • the preparation preferably comprises aliphatic alcohol, most preferably ethanol, in amounts of from 3 to 10 parts by weight.
  • the preparation of the invention preferably comprises the second active agent with the topical anesthetic activity, in amounts of from 0,1 to 10%.
  • the preparation comprises a substance selected from the group comprising benzocaine, lidocaine, mesocaine, mepivacaine, bupivacaine, articaine, diclonine, carbocaine.
  • the preparation of the invention by the use of the block copolymer of ethylen oxide and propylen oxide as a gelling agent, acquires thermoreversible properties. It means the entirely reversible change of form depending on the temperature: from a liquid into a gel and again into a liquid.
  • This property of the preparation of the invention is beneficial in many ways. Firstly, during the manufacture of the preparation the components are combined at below 15°C and the mixture is deaerated, a process being more efficient for liquid mixtures. The temperature is then increased to the room temperature, resulting in a conversion of the mixture into a gel form. Filling of unit dosage forms with the preparation can be carried out, when the preparation is a setting liquid or an already set gel.
  • the ready preparation is stable during at least 24 months and at a wide temperature range.
  • the preparations examined at temperatures from 5 0 C to 4O 0 C during 24 months retained the required contents of the active substance and the gel form at the proper temperature range during the entire examined period.
  • the density of gel can be controlled freely by proper choice of ethylen oxide and propylen oxide segments and their ratio.
  • Thermoreversibility of the preparation has no impact on the contents of the active substance - after a change of the preparation form into the liquid form resulting from the temperature increase or decrease and returning to the gel form the contents of the active substance remains unchanged.
  • Stability of the preparation at a wide temperature range allows to use the preparation in different climatic zones.
  • the addition of the analgesic allows for a simultaneous disinfection of injuries and lessening or elimination of the accompanying pain.
  • Example 1 The invention is further illustrated by the working examples.
  • Example 1 The invention is further illustrated by the working examples.
  • gentian violet and 5 kg of benzocaine are dissolved in 64 kg of ethanol of 96 proof and cooled down to below 15°C.
  • the composition is then left for complete gelling or formulated directly into unit dosage forms.
  • the preparation of gentian violet in gel with the active agent concentration of 1% (gentian) and 5% (benzocaine) is obtained.
  • Example 1 The preparations obtained according to Example 1 were tested for stability in a climatic chamber, at 40 0 C, and humidity of 75°, for 24 months.
  • the preparations were stable upon storage within the test period.
  • Example 1 The preparations obtained according to Example 1 were tested for stability in a climatic chamber, at 5 0 C, for 24 months.
  • the preparations were stable upon storage within the test period.
  • the preparations were prepared as in Example 1 except that as the gelling agent, carboxymethylcellulose (trade name Tylopur CB 3000 Gl) was used.
  • the preparations were tested for stability in a climatic chamber, at 25°C and a humidity of 60° for 18 months. After 12 months the preparations were irreversibly turned from a gel to a liquid form, and the contents of the active substance was decreased to below the normal required level. The results are presented in the table below.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Inorganic Chemistry (AREA)
  • Anesthesiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Engineering & Computer Science (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Botany (AREA)
  • Medical Informatics (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

A pharmaceutical preparation in a gel form, comprising hydrogen peroxide or gentian violet, or iodine as an active agent, and a gelling agent, a solvent and optional auxiliary agents, characterized in that the preparation comprises as a gelling agent a block copolymer of ethylen oxide and propylen oxide of formula HO(C2H4O)a(C3H6O)a(C2H4O)3H, wherein a is an integer from 6 to 160, and b is an integer from 8 to 100, and wherein the preparation comprises the gelling agent in amounts of from 10 to 40 parts by weight, and the active agent in amounts of from 0,5 to 15 parts by weight.

Description

Pharmaceutical preparation
The invention provides a pharmaceutical preparation in a gel form exhibiting a disinfecting and therapeutic activity.
GB 2068225 discloses dermatological compositions comprising hydrogen peroxide in a form of an aqueous solution and a gelling agent. As gelling agents, the following substances are taught in the specification: carboxyvinyl polymers, colloidal silicates, natural gums, starch, cellulose derivatives.
US 4401651 discloses a pharmaceutical preparation for application on wounds comprising gentian violet as an active agent and polyethylene glycol as a gelling agent. The document discloses also a preparation comprising iodine-polyvinylpyrrolidone complex as an active agent and polyethylene glycol.
The Polish patent application No P-332783 discloses a gelatinous pharmaceutical preparation comprising perhydrol or gentian violet, or iodine as active agents, combined with polyvinylpyrrolidone (iodopoly vinylpyrrolidone), with a viscosity of from 2000 to 10000 cnp. Hydroxycellulose was used as a gelling agent.
Preparations known from the prior art have a form of gel, which facilitates their precise application onto spots requiring treatment with the preparation, such as injuries, abrasions etc. A condensed preparation may be applied precisely onto a wound, excluding healthy skin around the affected spot. Critical for the process for the manufacture of such products and for their usability is the kind of gelling agent. It is important for the gelling agent to allow for thorough mixing of the components in a liquid form and provide a sufficient stability of the final preparations. In the case of active agents of high chemical and biological activity, such as e.g. hydrogen peroxide, numerous gelling agents are excluded.
The problem was solved by a preparation of the present invention. A pharmaceutical preparation in a gel form, comprising hydrogen peroxide or gentian violet, or iodine as an active agent, a gelling agent, a solvent and optional auxiliary agents is provided, which comprises as a gelling agent a block copolymer of ethylen oxide and propylen oxide of formula HO(C2H4O)a(C3H6O)b(C2H4O)aH, wherein a is an integer from 6 to 160, and b is an integer from 8 to 100, and the preparation comprises the gelling agent in amounts of from 10 to 40 parts by weight, and the active agent in amounts of from 0,5 to 15 parts by weight.
Preferably the preparation comprises gelling agent of formula HO(C2H4O)a(C3H6O)b(C2H4θ)aH, wherein a is an integer from 80 to 120, and b is an integer from 37 to 80.
As the solvent, the preparation preferably comprises water and/or an aliphatic alcohol, most preferably ethanol, in amounts of from 10 to 80 parts by weight.
As the auxiliary agent, the preparation preferably comprises a pH regulator, most preferably orthophosphoric acid, in such amounts that pH of the preparation is from 3,5 to 4,5.
As the auxiliary agent, the preparation preferably comprises a chelating agent, most preferably disodium edetate, in amounts of 0,1-0,5 parts by weight.
As the auxiliary agent, the preparation preferably comprises aliphatic alcohol, most preferably ethanol, in amounts of from 3 to 10 parts by weight.
The preparation of the invention preferably comprises the second active agent with the topical anesthetic activity, in amounts of from 0,1 to 10%. Most preferably as the anesthetic agent, the preparation comprises a substance selected from the group comprising benzocaine, lidocaine, mesocaine, mepivacaine, bupivacaine, articaine, diclonine, carbocaine.
The preparation of the invention, by the use of the block copolymer of ethylen oxide and propylen oxide as a gelling agent, acquires thermoreversible properties. It means the entirely reversible change of form depending on the temperature: from a liquid into a gel and again into a liquid. This property of the preparation of the invention is beneficial in many ways. Firstly, during the manufacture of the preparation the components are combined at below 15°C and the mixture is deaerated, a process being more efficient for liquid mixtures. The temperature is then increased to the room temperature, resulting in a conversion of the mixture into a gel form. Filling of unit dosage forms with the preparation can be carried out, when the preparation is a setting liquid or an already set gel. Secondly, the ready preparation is stable during at least 24 months and at a wide temperature range. The preparations examined at temperatures from 50C to 4O0C during 24 months retained the required contents of the active substance and the gel form at the proper temperature range during the entire examined period. Thirdly, the density of gel can be controlled freely by proper choice of ethylen oxide and propylen oxide segments and their ratio. Thermoreversibility of the preparation has no impact on the contents of the active substance - after a change of the preparation form into the liquid form resulting from the temperature increase or decrease and returning to the gel form the contents of the active substance remains unchanged. Stability of the preparation at a wide temperature range allows to use the preparation in different climatic zones. The addition of the analgesic allows for a simultaneous disinfection of injuries and lessening or elimination of the accompanying pain.
The invention is further illustrated by the working examples. Example 1.
15 kg of water and 15 kg of hydrogen peroxide as a 30% aqueous solution and 7,5 kg of ethanol of 96 proof are mixed together. A solution of 0,15 kg disodium edetate in 80 kg of water is simultaneously prepared, the solution is cooled down to below 15°C and a gelling agent of formula HO(C2H4O)3(C3H6OX(C2H4O)3H, wherein a = 101 , b = 56, in an amount of 33 kg is introduced. After mixing the components, both solutions are combined, stirred for Ih, orthophosphoric acid (about 20Og) is added to reach pH level of 3,5-4,5 and stirred for additional 2 h in vacuo, at about 15°C. The composition is then left for complete gelling or formulated directly into unit dosage forms. The perhydride preparation in gel with 3% concentration of the active agent is obtained. Example 2.
15 kg of water and 15 kg of hydrogen peroxide as a 30% aqueous solution and 7,5 kg of ethanol of 96 proof containing 4,5 kg of lidocaine are mixed together. A solution of 0,15 kg disodium edetate in 75,5 kg of water is simultaneously prepared, the solution is cooled down to below 150C and a gelling agent of formula HO(C2H4O)3(C3H6O)15(C2H4O)3H, wherein a - 101, b = 56, in an amount of 33 kg is introduced. After mixing the components, both solutions are combined, stirred for Ih, orthophosphoric acid (about 20Og) is added to reach pH level of 3,5-4,5 and stirred for additional 2 h in vacuo, at about 15°C. The composition is then left for complete gelling or formulated directly into unit dosage forms. The perhydride preparation in gel with concentration of the active agents of 3% (hydrogen peroxide) and 3% (lidocaine) is obtained. Example 3.
1 kg of gentian violet and 5 kg of benzocaine are dissolved in 64 kg of ethanol of 96 proof and cooled down to below 15°C. A gelling agent (dissolved in 10 kg of water) of formula HO(C2H4O)3(C3H6O)5(C2H4O)3H, wherein a = 141 , b = 44, in an amount of 20 kg is then introduced and the mixture is stirred for 2 h in vacuo at about 150C. The composition is then left for complete gelling or formulated directly into unit dosage forms. The preparation of gentian violet in gel with the active agent concentration of 1% (gentian) and 5% (benzocaine) is obtained.
Example 4.
1 kg of potassium iodide and 3 kg of iodine are dissolved in 56 kg of ethanol of 96 proof.
Simultaneously, 10 kg of water is cooled down to below 15°C and a gelling agent of formula
HO(C2H4O)3(C3H6O)5(C2H4O)3H, wherein a=64, b=37, in amounts of 30 kg is introduced.
After mixing the components, both solutions are combined and stirred for additional 2 hrs in vacuo at about 15°C. The composition is then left for complete gelling or formulated directly into dosage forms. The iodine in gel with the active agent concentration of 3% of iodine and
1% of potassium iodide is obtained.
Example 5.
10 kg of PVP-Iodine is slowly added to 10 kg of propylene glycol with constant stirring by means of an anchor stirrer. The mixture is heated to 60°C and stirred for about 30 minutes until homogeneous. The mixture is then cooled to below 15°C and a gelling agent of formula
HO(C2H4O)3(C3H6O)5(C2H4O)3H, wherein a=101, b=56, in an amount of 20 kg, dissolved in
DI water in an amount of 60 kg is added, followed by stirring for 3 hrs in vacuo at 15°C until the gel is homogeneous. The gel with the active agent concentration of 10% is obtained.
Example 6.
The preparations obtained according to Example 1 were tested for stability in a climatic chamber, at 400C, and humidity of 75°, for 24 months.
The preparations were stable upon storage within the test period.
The results are presented in the table below.
Figure imgf000005_0001
Figure imgf000006_0001
Figure imgf000007_0001
Example 7.
The preparations obtained according to Example 1 were tested for stability in a climatic chamber, at 50C, for 24 months.
The preparations were stable upon storage within the test period.
The results are presented in the table below.
Figure imgf000007_0002
Figure imgf000008_0001
Figure imgf000009_0001
Example 8, comparative
The preparations were prepared as in Example 1 except that as the gelling agent, carboxymethylcellulose (trade name Tylopur CB 3000 Gl) was used. The preparations were tested for stability in a climatic chamber, at 25°C and a humidity of 60° for 18 months. After 12 months the preparations were irreversibly turned from a gel to a liquid form, and the contents of the active substance was decreased to below the normal required level. The results are presented in the table below.
Figure imgf000009_0002
Figure imgf000010_0001

Claims

Claims
1. A pharmaceutical preparation in a gel form, comprising hydrogen peroxide or gentian violet, or iodine as an active agent, and a gelling agent, a solvent and optional auxiliary agents, characterized in that the preparation comprises as a gelling agent a block copolymer of ethylen oxide and propylen oxide of formula HO(C2H4θ)a(C3H6O)b(C2H4θ)aH, wherein a is an integer from 6 to 160, and b is an integer from 8 to 100, and wherein the preparation comprises the gelling agent in amounts of from 10 to 40 parts by weight, and the active agent in amounts of from 0,5 to 15 parts by weight.
2. The preparation of claim 1 , characterized in that the preparation comprises a gelling agent of formula HO(C2H4O)3(C3H6OMC2H4O)3H, wherein a is an integer from 80 to 120, and b is an integer from 37 to 80.
3. The preparation of claim 1, characterized in that it comprises water and/or aliphatic alcohol as a solvent.
4. The preparation of claim 3, characterized in that it comprises ethanol as aliphatic alcohol.
5. The preparation of claim 1, characterized in that it comprises the solvent in amounts of from 10 to 80 parts by weight.
6. The preparation of claim 1, characterized in that it comprises a pH regulator as the auxiliary agent.
7. The preparation of claim 6, characterized in that it comprises orthophosphoric acid as the pH regulator.
8. The preparation of claim 6 and 7, characterized in that it comprises the pH regulator in such amounts that pH level of the preparation is from 3,5 to 4,5.
9. The preparation of claim 1 , characterized in that it comprises a chelating agent as the auxiliary agent.
10. The preparation of claim 9, characterized in that it comprises disodium edetate as a chelating agent.
11. The preparation of claim 9 and 10, characterized in that it comprises the chelating agent in amounts of 0,1-0,5 parts by weight.
12. The preparation of claim 1, characterized in that it comprises an aliphatic alcohol as the auxiliary agent.
13. The preparation of claim 12, characterized in that it comprises ethanol as the aliphatic alcohol.
14. The preparation of claim 12 and 13, characterized in that it comprises the aliphatic alcohol in amounts of from 3 to 10 parts by weight.
15. The preparation of claim 1, characterized in that it additionally comprises an active agent with the topical anesthetic activity.
16. The preparation of claim 15, characterized in that it comprises the active agent with the topical anesthetic activity in amounts of from 0,1% to 10%.
17. The preparation of claim 15 and 16, characterized in that as the topical anesthetic it comprises a substance selected from the group comprising benzocaine, lidocaine, mezocaine, mepivacaine, bupivacaine, articaine, diclonine, carbocaine.
PCT/PL2007/000024 2006-08-21 2007-05-08 Pharmaceutical preparation in a gel form WO2008024006A2 (en)

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PL380476A PL380476A1 (en) 2006-08-21 2006-08-21 Pharmeceutical preparation

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4381920A (en) * 1979-08-03 1983-05-03 Michael-David Laboratories Method and composition for dyeing human hair
US4401651A (en) * 1979-04-18 1983-08-30 Knutson Richard A Wound-healing compositions containing povidone-iodine
WO1998010738A1 (en) * 1996-09-16 1998-03-19 The Procter & Gamble Company Antimicrobial oral care compositions
WO1999020226A1 (en) * 1997-10-23 1999-04-29 Pellico Michael A Two-component dental bleaching system and method
WO2000064255A1 (en) * 1999-04-27 2000-11-02 Grzegorz Nowakowski Pharmaceutical gel formulation
WO2001070242A2 (en) * 2000-03-22 2001-09-27 Ben Gurion University Of The Negev Research And Development Authority Compositions containing molecular iodine
US20050271595A1 (en) * 2004-06-03 2005-12-08 Brown James S Sanitizing composition and method of preparation

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4401651A (en) * 1979-04-18 1983-08-30 Knutson Richard A Wound-healing compositions containing povidone-iodine
US4381920A (en) * 1979-08-03 1983-05-03 Michael-David Laboratories Method and composition for dyeing human hair
WO1998010738A1 (en) * 1996-09-16 1998-03-19 The Procter & Gamble Company Antimicrobial oral care compositions
WO1999020226A1 (en) * 1997-10-23 1999-04-29 Pellico Michael A Two-component dental bleaching system and method
WO2000064255A1 (en) * 1999-04-27 2000-11-02 Grzegorz Nowakowski Pharmaceutical gel formulation
WO2001070242A2 (en) * 2000-03-22 2001-09-27 Ben Gurion University Of The Negev Research And Development Authority Compositions containing molecular iodine
US20050271595A1 (en) * 2004-06-03 2005-12-08 Brown James S Sanitizing composition and method of preparation

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