CA2578594A1 - Microemulsion & sub-micron emulsion process & compositions - Google Patents

Microemulsion & sub-micron emulsion process & compositions Download PDF

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Publication number
CA2578594A1
CA2578594A1 CA002578594A CA2578594A CA2578594A1 CA 2578594 A1 CA2578594 A1 CA 2578594A1 CA 002578594 A CA002578594 A CA 002578594A CA 2578594 A CA2578594 A CA 2578594A CA 2578594 A1 CA2578594 A1 CA 2578594A1
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CA
Canada
Prior art keywords
surfactant
water
microemulsion
sub
micron emulsion
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.)
Granted
Application number
CA002578594A
Other languages
French (fr)
Other versions
CA2578594C (en
Inventor
Maria Graziella Larm
Ronald Harding
Michael Johnston
Prema Vijayakumar
Phoebe Sun
Albert Zorko Abram
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.)
Mayne Pharma LLC
Original Assignee
Individual
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Filing date
Publication date
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Application filed by Individual filed Critical Individual
Priority to CA2756674A priority Critical patent/CA2756674C/en
Publication of CA2578594A1 publication Critical patent/CA2578594A1/en
Application granted granted Critical
Publication of CA2578594C publication Critical patent/CA2578594C/en
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • 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
    • A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/068—Microemulsions
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/12—Aerosols; Foams
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Abstract

There is provided a process for the preparation of an oil in water (O/W) microemulsion or sub-micron emulsion composition for dermal delivery of at least one pharmaceutically active ingredient, the method including the steps of a) Admixing a first part including at least one of the group consisting of animal, mineral or vegetable oils, silanes, siloxanes, esters, fatty acids, fats, halogen compounds or alkoxylated alcohols; and one or more lipophilic surfactants, and a second part including water and at least one hydrophilic surfactant to achieve homogeneity, b) heating the mix of step a) to a phase assembly temperature in the range of 40 - 99~C, preferably 45 - 950C, more preferably 65 - 850C with continuous mixing to obtain a microemulsion or sub-micron emulsion, c) allowing said microemulsion or sub-micron emulsion to cool, and d) adding a third part to said microemulsion or sub-micron emulsion at a temperature between 2~C and said phase assembly temperature, said third part if necessary being premixed and heated until the components are dissolved and including at least one component selected from the group consisting of non-surfactant amphiphilic type compound, surfactant and water with the proviso that when the third part includes water it also includes a non-surfactant amphiphilic type compound and/or surfactant. The phase assembly temperature can be determined visually by the achievement of translucence in the composition or by measures such as conductivity which peaks and then is maintained at a plateau whilst phase assembly occurs. It has been found that whilst if a non-surfactant amphiphilic type compound such as the polyol is added together with the second part as would conventionally be the case, a microemulsion or sub-micron emulsion is not formed, by adding the so called third part, phase assembly occurs at a lower temperature than would be expected and moreover, this phase appears to assist in maintaining the microemulsion or sub-micron emulsion characteristics of the formulation during storage at normal temperatures.

Claims (22)

1. A process for the preparation of an oil in water (O/W) microemulsion or sub-micron emulsion composition for dermal delivery of at least one pharmaceutically active ingredient, the method including the steps of a) admixing a first part including at least one of the group consisting of animal, mineral or vegetable oils, silanes, siloxanes, esters, fatty acids, fats, halogen compounds or alkoxylated alcohols; and one or more lipophilic surfactants, and a second part including water and at least one hydrophilic surfactant to achieve homogeneity, b) heating the mix of step a) to a phase assembly temperature in the range of 40 - 99°C, preferably 45 - 95°C, more preferably 65 -85°C with continuous mixing to obtain an oil in water microemulsion or sub-micron emulsion, c) allowing said microemulsion or sub-micron emulsion to cool, and d) adding a third part to said microemulsion or sub-micron emulsion at a temperature between 2°C and said phase assembly temperature, said third part if necessary being premixed and heated until the components are dissolved and including at least one component selected from the group consisting of non-surfactant amphiphilic type compound, surfactant and water with the proviso that when the third part includes water it also includes a non-surfactant amphiphilic type compound and/or surfactant.
2. A process according to claim 1 wherein said second part is added in two aliquots, said aliquots preferably being of about 70% and 30% by weight of the second part.
3. A process according to claim 2 wherein the second aliquot is added after said microemulsion or sub-micron emulsion has formed, at a temperature substantially below the temperature of the first aliquot, and at a rapid rate so as to reduce the overall temperature of the composition preferably to below about 60°C
whereby the microemulsion or sub-micron emulsion structure is fixed.
4. A process according to any one of claims 1-3 wherein a pharmaceutically active agent is included in said first part.
5. A process according to any one of claims 1-3 wherein a pharmaceutically active agent is included in said second part.
6. A process according to any one of claims 1-3 wherein a pharmaceutically active agent is included in said third part.
7. A process according to any one of claims 4-6 wherein said pharmaceutically active ingredient is insoluble or only sparingly soluble in water.
8. A process according to any one of claims 4-6 wherein said pharmaceutically active ingredient is one or more water insoluble compounds selected from the group consisting of corticosteroids, desonide, clobetasol, betamethasone, vitamin D analogues and vitamin A analogues.
9. A process according to any one of claims 1-7 wherein an occlusive agent is present in said first part.
10. A process according to claim 9 wherein said occlusive agent is petrolatum.
11. A process according to claim 1 including the steps of a) heating a first part including at least one of the group consisting of animal, mineral or vegetable oils, silanes, siloxanes, esters, fatty acids, fats, halogen compounds or alkoxylated alcohols, and one or more lipophilic surfactants to a temperature of 40 - 99°C, preferably 45 - 95°C and more preferably 65 - 85°C and mixing to homogeneity, b) heating a second part including water and at least one hydrophilic surfactant to a temperature of 40 - 99°C, preferably 45 - 95°C, and more preferably 65 - 85°C and mixing to achieve homogeneity, c) adding said second part to said first part at a temperature of 40 -99°C, preferably 45 - 95°C, and more preferably 65 - 85°C with continuous mixing whereby a microemulsion or sub-micron emulsion is formed at a phase assembly temperature, d) allowing said microemulsion or sub-micron emulsion to cool, and e) adding a third part to said microemulsion or sub-micron emulsion at a temperature between room temperature and said phase assembly temperature said third part having been premixed, and if necessary heated until the components are dissolved and including at least one component selected from the group consisting of non-surfactant amphiphilic type compound, surfactant and water with the proviso that when the third part includes water it also includes a non-surfactant amphiphilic type compound and/or surfactant.
12. An oil in water microemulsion or sub-micron emulsion composition for dermal delivery of at least one pharmaceutically active ingredient including an oil phase dispersed throughout a water phase, said oil phase including at least one of the group consisting of animal, mineral or vegetable oils, silanes, siloxanes, esters, fatty acids, fats, halogen compounds or alkoxylated alcohols; and at least one lipophilic surfactant; and said water phase including at least one hydrophilic surfactant, water and optionally non-surfactant amphiphilic compound, the weight ratio of the at least one hydrophilic surfactant to the at least one lipophilic surfactant being approximately 9.0:1.0 to 2.0:3Ø
13. A composition according to claim 12 wherein said surfactants have an aggregated HLB number between 8.0 and 15.0, more preferably between 10 and 12, and still more preferably between 9.7 and 11.8.
14. A composition according to claim 11 or 12 wherein the lipophilic surfactant has an HLB number of less than 10, and the hydrophilic surfactant has an HLB
number of greater than 10.
15. A composition according to any one of claims 11-13 including a pharmaceutically active agent which is insoluble or only sparingly soluble in water.
16. A composition according to claim 15 wherein the pharmaceutically active agent is one or more water insoluble compounds selected from the group consisting of corticosteroids, desonide, clobetasol, betamethasone, vitamin D
analogues and vitamin A analogues.
17. A composition according to any one of claims 14-16 wherein said pharmaceutically active agent is in said water phase.
18. A composition according to any one of claims 14-16 wherein said pharmaceutically active agent is in said oil phase.
19. A composition according to any one of claims 14-16 wherein said pharmaceutically active agent is in both said oil phase and said water phase.
20. A composition according to any one of claims 11-19 wherein an occlusive agent is included in said oil phase.
21. A composition according to claim 20 wherein said occlusive agent is petrolatum.
22. A method of medical or cosmetic treatment of a dermal condition including applying to the skin of a patient requiring such treatment an effective amount of oil in water microemulsion or sub-micron emulsion corriposition including at least one pharmaceutically active ingredient, said oil phase including an oil phase dispersed throughout a water phase said oil phase including at least one of the group consisting of animal, mineral or vegetable oils, silanes, siloxanes, esters, fatty acids,, fats, halogen compounds or alkoxylated alcohols; and at least one lipophilic surfactant, and said water phase includes at least one hydrophilic surfactant, water and optionally a non-surfactant amphiphilic type compound, the weight ratio of the at least one hydrophilic surfactant to the at least one lipophilic surfactant being approximately 9.0:1.0 to 2.0:3Ø
CA2578594A 2004-08-31 2005-08-31 Microemulsion & sub-micron emulsion process & compositions Active CA2578594C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2756674A CA2756674C (en) 2004-08-31 2005-08-31 Microemulsion & sub-micron emulsion process & compositions

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US60627804P 2004-08-31 2004-08-31
US60/606,278 2004-08-31
US67072205P 2005-04-12 2005-04-12
US60/670,722 2005-04-12
PCT/AU2005/001321 WO2006024095A1 (en) 2004-08-31 2005-08-31 Microemulsion & sub-micron emulsion process & compositions

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA2756674A Division CA2756674C (en) 2004-08-31 2005-08-31 Microemulsion & sub-micron emulsion process & compositions

Publications (2)

Publication Number Publication Date
CA2578594A1 true CA2578594A1 (en) 2006-03-09
CA2578594C CA2578594C (en) 2012-04-17

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Family Applications (1)

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Country Status (15)

Country Link
US (1) US8460641B2 (en)
EP (2) EP1796636B2 (en)
JP (1) JP4972553B2 (en)
KR (1) KR101243526B1 (en)
AR (1) AR051197A1 (en)
AU (1) AU2005279704B2 (en)
BR (1) BRPI0514806A (en)
CA (1) CA2578594C (en)
ES (1) ES2429040T5 (en)
HK (1) HK1110198A1 (en)
IL (1) IL181632A (en)
PL (1) PL1796636T5 (en)
RU (1) RU2381023C2 (en)
TW (1) TWI397427B (en)
WO (1) WO2006024095A1 (en)

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