CA2516863A1 - Poloxamer emulsion preparations - Google Patents
Poloxamer emulsion preparations Download PDFInfo
- Publication number
- CA2516863A1 CA2516863A1 CA002516863A CA2516863A CA2516863A1 CA 2516863 A1 CA2516863 A1 CA 2516863A1 CA 002516863 A CA002516863 A CA 002516863A CA 2516863 A CA2516863 A CA 2516863A CA 2516863 A1 CA2516863 A1 CA 2516863A1
- Authority
- CA
- Canada
- Prior art keywords
- composition
- copolymer
- oil
- emulsion
- weight
- 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
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Classifications
-
- 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
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/90—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
- A61K9/0012—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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0034—Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/58—Ethylene oxide or propylene oxide copolymers, e.g. pluronics
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
An emulsion composition comprising: an aqueous component, a non-ionic block copolymer, and an oil wherein the copolymer comprises at least 10% by weight of the composition.
Claims (61)
1. An emulsion composition comprising: an aqueous component, a non-ionic block copolymer, and an oil wherein the copolymer comprises at least 10% by weight of the composition, and wherein the composition is thermoreversible.
2. An emulsion composition comprising: an aqueous component, a non-ionic block copolymer, a hydrophilic, non-ionic short chain fatty acid emulsifier, and an oil wherein the copolymer comprises at least 10% by weight of the composition, and wherein the composition is thermoreversible.
3. A method for preparing an emulsion composition, comprising the steps of:
(a) Mixing a copolymer with an aqueous solution at a suitable temperature to substantially dissolve the copolymer in the aqueous solution; and (b) Mixing, at cold temperature, an oil that is the active agent or has a water-insoluble active agent dissolved therein, with the aqueous copolymer solution prepared in step (a) to form an emulsion;
wherein said composition comprises at least 10% by weight of copolymer.
(a) Mixing a copolymer with an aqueous solution at a suitable temperature to substantially dissolve the copolymer in the aqueous solution; and (b) Mixing, at cold temperature, an oil that is the active agent or has a water-insoluble active agent dissolved therein, with the aqueous copolymer solution prepared in step (a) to form an emulsion;
wherein said composition comprises at least 10% by weight of copolymer.
4. The method of claim 3 wherein the oil is mixed with the aqueous copolymer solution prepared in step (a) at a temperature less than about 15°C.
5. The method of claim 3 wherein the oil is mixed with the aqueous copolymer solution prepared in step (a) at a temperature between about 4°C to 12°C
6. The method of claim 3 wherein the oil is mixed with the aqueous copolymer solution prepared in step (a) at a temperature less than about 10°C.
7. A method for preparing an emulsion composition, comprising the steps of:
(a) Mixing a copolymer with an aqueous solution at a suitable temperature to substantially dissolve the copolymer in the aqueous solution;
(b) Mixing a hydrophilic, non-ionic short chain fatty acid emulsifier with an oil that is the active agent or has a water-insoluble active agent dissolved therein, at a low temperature to form an oil mixture; and (c) Mixing the solution prepared in step (a) with the solution prepared in step (b) at a low temperature to form an emulsion;
wherein said composition comprises at least 10% by weight of copolymer.
(a) Mixing a copolymer with an aqueous solution at a suitable temperature to substantially dissolve the copolymer in the aqueous solution;
(b) Mixing a hydrophilic, non-ionic short chain fatty acid emulsifier with an oil that is the active agent or has a water-insoluble active agent dissolved therein, at a low temperature to form an oil mixture; and (c) Mixing the solution prepared in step (a) with the solution prepared in step (b) at a low temperature to form an emulsion;
wherein said composition comprises at least 10% by weight of copolymer.
8. The method of claim 7 wherein the solution prepared in step (a) is mixed with the solution prepared in step (b) at a temperature less than about 60°C.
9. The method of claim 7 wherein the solution prepared in step (a) is mixed with the solution prepared in step (b) at a temperature between about 15°C to 40°C
10. The method of claim 7 wherein the solution prepared in step (a) is mixed with the solution prepared in step (b) at a temperature between about 20°C to 30°C
11. The method of claim 7 wherein the solution prepared in step (a) is mixed with the solution prepared in step (b) at room temperature.
12. The method of claim 3 or 7 wherein the copolymer is dissolved at a temperature of about 6°C.
13. The method of claim 3 or 7 wherein the copolymer is dissolved at room temperature with semi-continuous or continuous stirring.
14. An emulsion composition formed by the method of claim 3.
15. An emulsion composition formed by the method of claim 7.
16. The composition of any one of claims 1, 2, 14 or 15 wherein the emulsion is a microemulsion.
17. The composition of any one of claims 1, 2, 14 or 15 wherein the copolymer comprises about 10% to 50% by weight of the composition.
18. The composition of any one of claims 1, 2, 14 or 15 wherein the copolymer comprises about 10.1 % to 40% by weight of the composition.
19. The composition of any one of claims 1, 2, 14 or 15 wherein the copolymer comprises an amount by weight of the block copolymer between any of the following ranges: 10.5% to 35%, 11% to 30%, 12% to 25%, 13% to 20% or 14% to 18% by weight of the composition.
20. The composition of any one of claims 1, 2, 14 or 15 wherein the copolymer comprises 15% by weight of the composition.
21. The composition of any one of claims 1, 2, 14 or 15 wherein the copolymer comprises a thermo-reversible copolymer.
22. The composition of claim 20 wherein the copolymer comprises a block copolymer of ethylene oxide and propylene oxide (poloxamer).
23. The composition of claim 22 wherein the copolymer is represented by the formula:
HO(C2H4O)a(C3H6O)b(C2H4O)a H
Where 'b' is between 15 and 67 and 'a' is between 2 and 130, and the total proportion of 'a' units amounts to from 20% to 90% by weight of the copolymer.
HO(C2H4O)a(C3H6O)b(C2H4O)a H
Where 'b' is between 15 and 67 and 'a' is between 2 and 130, and the total proportion of 'a' units amounts to from 20% to 90% by weight of the copolymer.
24. The composition of claim 23 wherein the molecular weight of the copolymer ranges from about 1,000 to 20,000.
25. The composition of claim 22 wherein the copolymer is poloxamer 407.
26. The composition of claim 2 or 15 wherein the emulsifier is a fatty acid component with a polyethoxylated side chain.
27. The composition of claim 2 or 15 wherein the emulsifier is chosen from the list comprising: Laureth-4, Laureth-9, Laureth-23, PPG-26-Buteth-26/PEG-40 Hydrogenated castor oil, and PEG-40 Hydrogenated castor oil.
28. The composition of claim 2 or 15 wherein the emulsifier comprises about 0.5% to 50% by weight of the microemulsion.
29. The composition of any one of claims 1, 2, 14 or 15 wherein the oil is an active agent or has a water-insoluble active agent dissolved therein.
30. The composition of any one of claims 1, 2, 14 or 15 wherein the oil is chosen from the list comprising: long chain alcohols, glyceryl esters of fatty acids or fatty esters of monohydric alcohols.
31. The composition of claim 30 wherein the esters and alcohols are liquids at room temperature.
32. The composition of any one of claims 1, 2, 14 or 15 wherein the oil contains active agents that are soluble in or miscible with the oil phase.
33. The composition of any one of claims 1, 2, 14 or 15 wherein the oil constitutes the active agent of the emulsion.
34. The composition of claim 33 wherein the oil contains active agents that are soluble in or miscible with the oil phase.
35. The composition of any one of claims 32 to 34 wherein the active agents are drawn from the group comprising: antimicrobials (such as antibiotics, antifungals and antivirals), anti-inflammatories, antihistaminics, antidepressants, anaesthetics antineoplastics, enzymes, cardiovascular agents, polynucleotides, genetic material, viral vectors, immunoactive agents, imaging agents, immunosuppressive agents, peptides, proteins and combinations thereof.
36. The composition of any one of claims 32 to 34 wherein the active agent is present in a pharmaceutically effective amount.
37. The composition of any one of claims 1, 2, 14 or 15 wherein the oil comprises about 0.1% to 80% by weight of the emulsion.
38. The composition of any one of claims 1, 2, 14 or 15 wherein the oil comprises about 1% to 30% by weight of the emulsion.
39. The composition of any one of claims 1, 2, 14 or 15 wherein the oil comprises about 3% to 15% by weight of the emulsion.
40. The composition of any one of claims 1, 2, 14 or 15 wherein the oil comprises 6% by weight of the emulsion.
41. The composition of any one of claims 1, 2, 14 or 15 wherein the oil is tea tree oil (TTO).
42. The composition of claim 41 that has microbicide activity.
43. The composition of any one of claims 1, 2, 14 or 15 wherein the emulsion possesses bioadhesive or mucoadhesive properties.
44. The composition of any one of claims 1, 2, 14 or 15 wherein the emulsion is in the form of a liquid or a gel.
45. The composition of claim 44 wherein the emulsion composition is a gel.
46. The composition of any one of claims 1, 2, 14 or 15 wherein the emulsion composition is a liquid that is capable of gelatinising upon contact with dermal or mucosal tissue.
47. Use of the composition of any one of claims 1, 2, 14 or 15 for topically application to the epidermal surfaces of an animal.
48. Use of the composition of any one of claims 1, 2, 14 or 15 for mucosal application to the oesophageal, otic, vaginal, rectal or ophthalmic surfaces of an animal.
49. Use according to claim 47 wherein the composition further comprises agents to promote bodily attractiveness or to mask the physical manifestations of a disorder or disease.
50. Use according to claim 49 wherein the composition also treats a physical disorder.
51. Use of the composition of any one of claims 1, 2, 14 or 15 to impart thickening properties to other compositions.
52. Use according to claim 51 wherein the composition imparts enhanced overall viscosity.
53. Use according to claim 51 wherein the composition imparts a viscosity response with temperature.
54. Use of the composition of any one of claims 1, 2, 14 or 15 to impart emolliency properties to other compositions.
55. Use of the composition of any one of claims 1, 2, 14 or 15 as a film-forming bioactive agent on the skin or other mucosal membrane.
56. A use according to claim 55 wherein the film-forming bioactive agent further acts as a barrier to prevent water loss from the skin.
57. Use of the composition of claim 42 to treat a disease selected from the group comprising: sexually transmitted diseases, HIV, impetigo, cold sores, otitis media, otitis externs, acne, periodontitis, gingivitis, paronychia, onychomycosis and secondary infections in connection with operations, dermatitis, burns, etc.
58. The composition of any one of claims 1, 2, 14 or 15 further comprising one or more pharmaceutically acceptable additives, excipients, carriers or diluents.
59. The composition of any one of claims 1, 2, 14 or 15 wherein the composition further comprises one or more pharmaceutically acceptable acids or a bases.
60. The composition of any one of claims 1, 2, 14 or 15 wherein the composition further comprises one or more pharmaceutically acceptable salts of an acid or a base.
61. The composition of any one of claims 1, 2, 14 or 15 wherein the composition further comprises one or more pharmaceutically acceptable enzyme inhibiting agents.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2003900887A AU2003900887A0 (en) | 2003-02-27 | 2003-02-27 | Poloxamer emulsion preparations |
AU2003900887 | 2003-02-27 | ||
PCT/AU2004/000218 WO2004076561A1 (en) | 2003-02-27 | 2004-02-20 | Poloxamer emulsion preparations |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2516863A1 true CA2516863A1 (en) | 2004-09-10 |
CA2516863C CA2516863C (en) | 2011-12-06 |
Family
ID=31499933
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2516863A Expired - Fee Related CA2516863C (en) | 2003-02-27 | 2004-02-20 | Poloxamer emulsion preparations |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP1597318A4 (en) |
JP (1) | JP2006519272A (en) |
CN (1) | CN100591721C (en) |
AU (3) | AU2003900887A0 (en) |
BR (1) | BRPI0408056A (en) |
CA (1) | CA2516863C (en) |
EA (1) | EA017434B1 (en) |
NO (1) | NO20054395L (en) |
WO (1) | WO2004076561A1 (en) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20190026056A (en) * | 2008-04-21 | 2019-03-12 | 오토노미, 인코포레이티드 | Auris formulations for treating otic diseases and conditions |
WO2010076730A1 (en) * | 2009-01-02 | 2010-07-08 | Donald, Jenny | Method for the treatment of an hiv infection |
PL2552487T3 (en) * | 2010-04-01 | 2017-04-28 | Pharmanest Ab | Thermogelling anaesthetic compositions |
HUE042252T2 (en) * | 2011-03-21 | 2019-06-28 | Broda Tech Co Ltd | Reversely thermo-reversible hydrogel compositions |
ITMI20131927A1 (en) | 2013-11-20 | 2015-05-21 | Cosmo Technologies Ltd | EMULSIONS OR MICROEMULSIONS FOR USE IN ENDOSCOPIC MUCOSAL RESECTIONING AND / OR ENDOSCOPIC SUBMUCOSAL DISSECTION. EMULSIONS OR MICROEMULSIONS FOR USE IN ENDOSCOPIC MUCOSAL RESECTION AND / OR ENDOSCOPIC SUBMUCOSAL DISSECTION |
KR102352250B1 (en) * | 2014-03-25 | 2022-01-17 | 제넨테크, 인크. | Methods of preparing a poloxamer for use in cell culture medium |
US10266745B2 (en) | 2017-02-03 | 2019-04-23 | Saudi Arabian Oil Company | Anti-bit balling drilling fluids, and methods of making and use thereof |
KR101852718B1 (en) * | 2017-04-04 | 2018-05-18 | 주식회사 제네웰 | Kit for pain reduction of incision site after surgical operation |
WO2019125783A1 (en) * | 2017-12-21 | 2019-06-27 | Sigma-Aldrich Co. Llc | Poloxamer compositions and methods of making and using same |
IT201900018752A1 (en) * | 2019-10-14 | 2021-04-14 | Alessandro Tosetti | COMPOSITION BASED ON ESSENTIAL OILS FOR DENTAL USE FOR THE TREATMENT OF PERIODONTITIS AND PERIMPLANT MUCOSITE |
RU2762506C1 (en) * | 2021-01-20 | 2021-12-21 | Общество С Ограниченной Ответственностью «Диамед-Фарма» | Agent for applying oral and nasal cavities and method for its use as part of complex therapy of infectious and inflammatory diseases of nasal and oral cavities |
CN114455621B (en) * | 2022-01-11 | 2023-10-27 | 兰州交通大学 | Preparation method of needle-shaped calcium carbonate |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1990003429A1 (en) * | 1988-09-23 | 1990-04-05 | Cetus Corporation | Lipid microemulsions for culture media |
JPH0791555B2 (en) * | 1989-12-22 | 1995-10-04 | 株式会社資生堂 | Cleaning composition |
EP0788346B9 (en) * | 1994-03-18 | 2007-02-14 | Supernus Pharmaceuticals, Inc. | Emulsified drug delivery systems |
ES2094688B1 (en) * | 1994-08-08 | 1997-08-01 | Cusi Lab | MANOEMULSION OF THE TYPE OF OIL IN WATER, USEFUL AS AN OPHTHALMIC VEHICLE AND PROCEDURE FOR ITS PREPARATION. |
SE9601421D0 (en) * | 1996-04-12 | 1996-04-12 | Astra Ab | New composition |
DE19723308A1 (en) * | 1997-06-04 | 1998-12-10 | Wolfgang A Prof Dr Wohlrab | Microemulsions useful for topical administration of e.g. local anaesthetics |
FR2788007B1 (en) * | 1999-01-05 | 2001-02-09 | Oreal | NANOEMULSION BASED ON BLOCK COPOLYMERS OF ETHYLENE OXIDE AND PROPYLENE OXIDE, AND ITS USES IN THE COSMETIC, DERMATOLOGICAL AND / OR OPHTHALMOLOGICAL FIELDS |
AU2799099A (en) * | 1999-03-01 | 2000-09-21 | Basf Corporation | Cold processed water-in-oil emulsions |
CN1149984C (en) * | 1999-06-21 | 2004-05-19 | 健一制药株式会社 | Anesthetic compsn. for intravenous injection comprising propofol |
SE0000774D0 (en) * | 2000-03-08 | 2000-03-08 | Astrazeneca Ab | New formulation |
US6623765B1 (en) * | 2000-08-01 | 2003-09-23 | University Of Florida, Research Foundation, Incorporated | Microemulsion and micelle systems for solubilizing drugs |
-
2003
- 2003-02-27 AU AU2003900887A patent/AU2003900887A0/en not_active Abandoned
-
2004
- 2004-02-20 EA EA200501368A patent/EA017434B1/en not_active IP Right Cessation
- 2004-02-20 BR BRPI0408056-4A patent/BRPI0408056A/en not_active IP Right Cessation
- 2004-02-20 CA CA2516863A patent/CA2516863C/en not_active Expired - Fee Related
- 2004-02-20 JP JP2006501371A patent/JP2006519272A/en active Pending
- 2004-02-20 WO PCT/AU2004/000218 patent/WO2004076561A1/en active Search and Examination
- 2004-02-20 AU AU2004215921A patent/AU2004215921A1/en not_active Abandoned
- 2004-02-20 EP EP04712958A patent/EP1597318A4/en not_active Withdrawn
- 2004-02-20 CN CN200480005486A patent/CN100591721C/en not_active Expired - Fee Related
-
2005
- 2005-09-22 NO NO20054395A patent/NO20054395L/en not_active Application Discontinuation
-
2009
- 2009-06-09 AU AU2009202265A patent/AU2009202265B2/en not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
BRPI0408056A (en) | 2006-02-14 |
WO2004076561A1 (en) | 2004-09-10 |
CA2516863C (en) | 2011-12-06 |
EP1597318A1 (en) | 2005-11-23 |
CN100591721C (en) | 2010-02-24 |
AU2009202265B2 (en) | 2012-02-16 |
EA017434B1 (en) | 2012-12-28 |
AU2003900887A0 (en) | 2003-03-13 |
AU2009202265A1 (en) | 2009-07-02 |
JP2006519272A (en) | 2006-08-24 |
NO20054395L (en) | 2005-09-22 |
AU2004215921A1 (en) | 2004-09-10 |
EP1597318A4 (en) | 2006-06-14 |
EA200501368A1 (en) | 2006-02-24 |
CN1753949A (en) | 2006-03-29 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed |
Effective date: 20190220 |