WO1992014472A1 - Compositions for topical administration containing fluticasone propionate and oxiconazole or its salts - Google Patents
Compositions for topical administration containing fluticasone propionate and oxiconazole or its salts Download PDFInfo
- Publication number
- WO1992014472A1 WO1992014472A1 PCT/EP1992/000364 EP9200364W WO9214472A1 WO 1992014472 A1 WO1992014472 A1 WO 1992014472A1 EP 9200364 W EP9200364 W EP 9200364W WO 9214472 A1 WO9214472 A1 WO 9214472A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oxiconazole
- fluticasone propionate
- compositions
- topical administration
- present
- 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
Links
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
Definitions
- the present invention relates to topical pharmaceutical compositions containing fluticasone propionate and oxiconazole as active ingredients.
- Fluticasone propionate is the approved name for (S-fl ⁇ oromethyl 6a,9a- difluoro- 11 b-hydroxy- 16a-methyl- 17 a-propionyloxy- 3-oxandrosta- 1 ,4-diene 17b- carbothioate), which is disclosed in United Kingdom Patent Specification No. 2088877.
- Fluticasone propionate is a corticosteroid having good topical anti- inflammatory activity with minimal liability to cause undesired systemic side effects.
- Oxiconazole is the approved name for l -(2-(4-chlorophenyl)-2-((2,4- dichlorophenyl)methoxyimino)ethyl)-lH-imidazole. Oxiconazole has antifungal and antibacterial actions.
- Topical corticosteroids arc widely used for the treatment of inflammatory skin conditions such as, for example, inflammatory dermatoses and eczemas.
- inflammatory skin conditions such as, for example, inflammatory dermatoses and eczemas.
- skin conditions such as, for example, infected dermatoses and eczema wherein infection by gram positive bacteria especially Staphylococci aureus and Streptococcus species and/or fungi, such as dermatophytes, yeasts and moulds, co ⁇ exist with inflammation.
- the invention thus provides a method of treating skin disorders which comprises the topical administration to an animal, including a human, of fluticasone propionate and oxiconazole or a physiologically acceptable salt thereof.
- Suitable physiologically acceptable salts of oxiconazole include the hydrochloride, sulphate and nitrate salts.
- oxiconazole will be in the form of its nitrate.
- the invention provides topical pharmaceutica compositions comprising fluticasone propionate and oxiconazole or physiologically acceptable salt thereof.
- compositions according to the invention can conveniently be formulated in conventional manner using one or more pharmaceutically acceptable carriers or excipients.
- Such compositions may take the form of, for example, ointments, lotions, creams, powders, drops (e.g. eye or ear drops) or sprays.
- the compositions of the invention will be in the form of creams or ointments.
- Ointments may normally be prepared by melting white soft paraffin, (white petrolatum) incorporating any additives e.g. surfactants and solvents, and blending in a slurry of the drug in a minimum quantity of liquid paraffin. The melt is then cooled under controlled conditions and stirred until solidification occurs.
- white soft paraffin white petrolatum
- additives e.g. surfactants and solvents
- Creams may normally be prepared by combining the oily phase of an ointment as a melt as described above, with suitable oil and water soluble surfactants and an aqueous phase containing the drug and suitable anti-microbial preservatives, homogenising to form the cream and stirring gently until cool.
- compositions according to the invention will generally contain additional excipients, for example preservatives (such as benzoic acid), emulsifying agents (such as polysorbates, e.g. polysorbate 60), and viscosity enhancing agents (such as cetostearyl alcohol).
- preservatives such as benzoic acid
- emulsifying agents such as polysorbates, e.g. polysorbate 60
- viscosity enhancing agents such as cetostearyl alcohol
- compositions of the present invention that, due to their improved effectiveness, they generally need be applied only once or twice daily. This is in contrast to known combined therapies comprising a corticosteroid and an antibacterial and/or antifungal agent, which all require multiple daily applications.
- the amount of fluticasone propionate contained in the compositions of the invention will depend on the particular type of formulation concerned but will generally be in the range of from 0.0005% to 1.0% by weight of the formulation, preferably about 0.05% w/w.
- the amount of oxiconazole in the compositions will also depend on the particular formulation but the content of free base will generally be in the range of from 0.01 to 10.00% by weight of the formulation, preferably about 1.00% w/w.
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Steroid Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
A method for the treatment of skin disorders comprising the topical administration of fluticasone propionate and oxiconazole or a physiologically acceptable salt thereof and pharmaceutical formulations adapted for topical use and comprising fluticasone propionate, oxiconazole or a physiologically acceptable salt thereof and a pharmaceutically acceptable carrier are disclosed.
Description
COMPOSITIONS FOR TOPICAL ADMINISTRATION CONTAINING FLUTICASONE PROPIONATE AND OXICONAZOLE OR ITS SALTS
The present invention relates to topical pharmaceutical compositions containing fluticasone propionate and oxiconazole as active ingredients.
Fluticasone propionate is the approved name for (S-flβoromethyl 6a,9a- difluoro- 11 b-hydroxy- 16a-methyl- 17 a-propionyloxy- 3-oxandrosta- 1 ,4-diene 17b- carbothioate), which is disclosed in United Kingdom Patent Specification No. 2088877. Fluticasone propionate is a corticosteroid having good topical anti- inflammatory activity with minimal liability to cause undesired systemic side effects.
Oxiconazole is the approved name for l -(2-(4-chlorophenyl)-2-((2,4- dichlorophenyl)methoxyimino)ethyl)-lH-imidazole. Oxiconazole has antifungal and antibacterial actions.
Topical corticosteroids arc widely used for the treatment of inflammatory skin conditions such as, for example, inflammatory dermatoses and eczemas. There arc many skin conditions such as, for example, infected dermatoses and eczema wherein infection by gram positive bacteria especially Staphylococci aureus and Streptococcus species and/or fungi, such as dermatophytes, yeasts and moulds, co¬ exist with inflammation.
We have now found that a combination of fluticasone propionate and oxiconazole is particularly effective in the treatment of skin disorders wherein inflammation and infection by bacteria and/or fungi coexist.
The invention thus provides a method of treating skin disorders which comprises the topical administration to an animal, including a human, of fluticasone propionate and oxiconazole or a physiologically acceptable salt thereof.
It will be appreciated that reference to treatment is intended to include prophylaxis as well as the alleviation of established symptoms.
Suitable physiologically acceptable salts of oxiconazole include the hydrochloride, sulphate and nitrate salts. Preferably oxiconazole will be in the form of its nitrate.
According to a further aspect the invention provides topical pharmaceutica compositions comprising fluticasone propionate and oxiconazole or physiologically acceptable salt thereof.
Compositions according to the invention can conveniently be formulated in conventional manner using one or more pharmaceutically acceptable carriers or excipients. Such compositions may take the form of, for example, ointments, lotions, creams, powders, drops (e.g. eye or ear drops) or sprays. Preferably the compositions of the invention will be in the form of creams or ointments.
Ointments may normally be prepared by melting white soft paraffin, (white petrolatum) incorporating any additives e.g. surfactants and solvents, and blending in a slurry of the drug in a minimum quantity of liquid paraffin. The melt is then cooled under controlled conditions and stirred until solidification occurs.
Creams may normally be prepared by combining the oily phase of an ointment as a melt as described above, with suitable oil and water soluble surfactants and an aqueous phase containing the drug and suitable anti-microbial preservatives, homogenising to form the cream and stirring gently until cool.
Compositions according to the invention will generally contain additional excipients, for example preservatives (such as benzoic acid), emulsifying agents (such as polysorbates, e.g. polysorbate 60), and viscosity enhancing agents (such as cetostearyl alcohol).
It is an advantage of the compositions of the present invention that, due to their improved effectiveness, they generally need be applied only once or twice daily. This is in contrast to known combined therapies comprising a corticosteroid and an antibacterial and/or antifungal agent, which all require multiple daily applications.
The amount of fluticasone propionate contained in the compositions of the invention will depend on the particular type of formulation concerned but will generally be in the range of from 0.0005% to 1.0% by weight of the formulation, preferably about 0.05% w/w.
The amount of oxiconazole in the compositions will also depend on the particular formulation but the content of free base will generally be in the range of from 0.01 to 10.00% by weight of the formulation, preferably about 1.00% w/w.
The invention is further illustrated by the following non-limiting example :
Example 1
% w/w
Oxiconazole Nitrate 1.147 *
Fluticasone Propionate (micronised) 0.05
Cetostearyl Alcohol 10.00
White Soft Paraffin 10.00
Polysorbate 60 2.50
Propylene Glycol 10.00
Benzoic Acid 0.20
Purified Water to 100.00
equivalent to 1.00% oxiconazole base.
Claims
1. A method of treating skin disorders in an animal including man comprising the topical administration fluticasone propionate and oxiconazole or a pharmaceutically acceptable salt thereof.
2. A method according to Claim 1 wherein the fluticasone propionate and oxiconazole or pharmaceutically acceptable salt thereof are administered sequentially.
3. A method according to Claim 1 wherein the fluticasone propionate and oxiconazole or pharmaceutically acceptable salt thereof are administered simultaneously.
4. A method according to any one of Claims 1 to 3 wherein the oxiconazole is present as oxiconazole nitrate.
5. A method as claimed in any one of Claims 1 to 4 wherein the ratio of fluticasone propionate to oxiconazole is about 0.05:1.00% w/w.
6. A pharmaceutical formulation adapted for topical administration and comprising fluticasone propionate, oxiconazole or a pharmaceutically acceptable salt thereof and pharmaceutically acceptable carrier therefor.
7. A pharmaceutical formulation according to Claim 6 wherein oxiconazole is present as oxiconazole nitrate.
8. A pharmaceutical formulation according to Claim 6 or Claim 7 in the form of an ointment, lotion, cream, powder, drops or sprays.
9. A pharmaceutical formulation as claimed in any one of Claims 6 to 8 wherein the fluticasone propionate is present in an amount of from 0.0005% to 1% by weight and the oxiconazole is present in an amount of 0.01 to 10.00% by weight.
10. A pharmaceutical formulation as claimed in any one of Claims 6 to 9 wherein the fluticasone propionate is present in an amount of about 0.05% w/w and the oxiconazole is present in an amount of about 1.00% w/w based upon the free base.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69200711T DE69200711T2 (en) | 1991-02-22 | 1992-02-21 | Pharmaceutical compositions containing fluticasone propionate and oxikonazole or its salt for topical use. |
| EP92905462A EP0573492B1 (en) | 1991-02-22 | 1992-02-21 | Compositions for topical administration containing fluticasone propionate and oxiconazole or its salts |
| GR950400256T GR3015014T3 (en) | 1991-02-22 | 1995-02-08 | Compositions for topical administration containing fluticasone propionate and oxiconazole or its salts. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9103764.8 | 1991-02-22 | ||
| GB919103764A GB9103764D0 (en) | 1991-02-22 | 1991-02-22 | Compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1992014472A1 true WO1992014472A1 (en) | 1992-09-03 |
Family
ID=10690429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1992/000364 Ceased WO1992014472A1 (en) | 1991-02-22 | 1992-02-21 | Compositions for topical administration containing fluticasone propionate and oxiconazole or its salts |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0573492B1 (en) |
| AT (1) | ATE114244T1 (en) |
| AU (1) | AU1277792A (en) |
| CA (1) | CA2104677A1 (en) |
| DE (1) | DE69200711T2 (en) |
| DK (1) | DK0573492T3 (en) |
| ES (1) | ES2064166T3 (en) |
| GB (1) | GB9103764D0 (en) |
| GR (1) | GR3015014T3 (en) |
| MX (1) | MX9200728A (en) |
| WO (1) | WO1992014472A1 (en) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0577760A4 (en) * | 1991-03-26 | 1994-10-19 | Glaxo Inc | Sequential dosing of antifungal and antiinflammatory compositions. |
| WO2000024401A1 (en) * | 1998-10-22 | 2000-05-04 | Glaxo Group Limited | Fluticasone lotion having improved vasoconstrictor activity |
| WO2002013868A1 (en) * | 2000-08-14 | 2002-02-21 | Glaxo Group Limited | Dermatological formulation |
| US6479058B1 (en) | 1999-09-02 | 2002-11-12 | Mccadden Michael E. | Composition for the topical treatment of poison ivy and other forms of contact dermatitis |
| US6656928B1 (en) * | 1999-09-02 | 2003-12-02 | Mccadden Michael E. | Composition for the topical treatment of rashes, dermatoses and lesions |
| US6750210B2 (en) | 2000-08-05 | 2004-06-15 | Smithkline Beecham Corporation | Formulation containing novel anti-inflammatory androstane derivative |
| US6759398B2 (en) | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
| US6777400B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6777399B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6787532B2 (en) | 2000-08-05 | 2004-09-07 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivatives |
| US6858593B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6858596B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
| US6878698B2 (en) | 2001-04-07 | 2005-04-12 | Glaxo Group Limited | Anti-inflammatory androstane derivatives |
| US7125985B2 (en) | 2000-08-05 | 2006-10-24 | Glaxo Group Limited | Compounds useful in the manufacture of an anti-inflammatory androstane derivative |
| US7291608B2 (en) | 2001-04-30 | 2007-11-06 | Glaxo Group Limited | Anti-inflammatory 17.β.-carbothioate ester derivatives of androstane with a cyclic ester group in position 17.α |
| US7498321B2 (en) | 2000-08-05 | 2009-03-03 | Glaxo Group Limited | 17β-carbothioate 17α-arylcarbonyloxyloxy androstane derivative as anti-inflammatory agents |
| WO2012023077A1 (en) * | 2010-08-17 | 2012-02-23 | Sulur Subramaniam Vanangamudi | A medicinal fusidic acid cream made using sodium fusidate and incorporating a biopolymer, a corticosteroid - clobetasol propionate, and an antifungal agent - oxiconazole nitrate, and a process to make it |
| US8933060B2 (en) | 2002-06-14 | 2015-01-13 | Cipla Limited | Combination of azelastine and ciclesonide for nasal administration |
-
1991
- 1991-02-22 GB GB919103764A patent/GB9103764D0/en active Pending
-
1992
- 1992-02-21 ES ES92905462T patent/ES2064166T3/en not_active Expired - Lifetime
- 1992-02-21 WO PCT/EP1992/000364 patent/WO1992014472A1/en not_active Ceased
- 1992-02-21 AT AT92905462T patent/ATE114244T1/en not_active IP Right Cessation
- 1992-02-21 CA CA002104677A patent/CA2104677A1/en not_active Abandoned
- 1992-02-21 DE DE69200711T patent/DE69200711T2/en not_active Expired - Fee Related
- 1992-02-21 AU AU12777/92A patent/AU1277792A/en not_active Abandoned
- 1992-02-21 MX MX9200728A patent/MX9200728A/en not_active IP Right Cessation
- 1992-02-21 DK DK92905462.5T patent/DK0573492T3/en active
- 1992-02-21 EP EP92905462A patent/EP0573492B1/en not_active Expired - Lifetime
-
1995
- 1995-02-08 GR GR950400256T patent/GR3015014T3/en unknown
Non-Patent Citations (2)
| Title |
|---|
| See also references of EP0573492A1 * |
| Weekly Pharmacy Reports: "The Green Sheet", vol. 40, no. 1, 7 January 1991, "Glaxo's cultivate (fluticasone propionate) ointment and cream approved as twice daily", pages 2,3, see publication * |
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0577760A4 (en) * | 1991-03-26 | 1994-10-19 | Glaxo Inc | Sequential dosing of antifungal and antiinflammatory compositions. |
| WO2000024401A1 (en) * | 1998-10-22 | 2000-05-04 | Glaxo Group Limited | Fluticasone lotion having improved vasoconstrictor activity |
| US7300669B2 (en) | 1998-10-22 | 2007-11-27 | Altana Inc. | Fluticasone lotion having improved vasoconstrictor activity |
| US6890544B2 (en) | 1999-09-02 | 2005-05-10 | Mccadden Michael E. | Gel composition for the topical treatment of poison ivy and other forms of contact dermatitis |
| US6479058B1 (en) | 1999-09-02 | 2002-11-12 | Mccadden Michael E. | Composition for the topical treatment of poison ivy and other forms of contact dermatitis |
| US6656928B1 (en) * | 1999-09-02 | 2003-12-02 | Mccadden Michael E. | Composition for the topical treatment of rashes, dermatoses and lesions |
| US7125985B2 (en) | 2000-08-05 | 2006-10-24 | Glaxo Group Limited | Compounds useful in the manufacture of an anti-inflammatory androstane derivative |
| US6759398B2 (en) | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
| US6777399B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6787532B2 (en) | 2000-08-05 | 2004-09-07 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivatives |
| US6858593B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6858596B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
| US6777400B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US7531528B2 (en) | 2000-08-05 | 2009-05-12 | Glaxo Group Limited | Formulation containing anti-inflammatory androstane derivatives |
| US6750210B2 (en) | 2000-08-05 | 2004-06-15 | Smithkline Beecham Corporation | Formulation containing novel anti-inflammatory androstane derivative |
| US7132532B2 (en) | 2000-08-05 | 2006-11-07 | Glaxo Group Limited | Compounds useful in the manufacture of an anti-inflammatory androstane derivative |
| US7144845B2 (en) | 2000-08-05 | 2006-12-05 | Glaxo Group Limited | Compounds useful in the manufacture of an anti-inflammatory androstane derivative |
| US7629335B2 (en) | 2000-08-05 | 2009-12-08 | Glaxo Group Limited | Anti-inflammatory androstane derivative |
| US7498321B2 (en) | 2000-08-05 | 2009-03-03 | Glaxo Group Limited | 17β-carbothioate 17α-arylcarbonyloxyloxy androstane derivative as anti-inflammatory agents |
| WO2002013868A1 (en) * | 2000-08-14 | 2002-02-21 | Glaxo Group Limited | Dermatological formulation |
| US6878698B2 (en) | 2001-04-07 | 2005-04-12 | Glaxo Group Limited | Anti-inflammatory androstane derivatives |
| US7291608B2 (en) | 2001-04-30 | 2007-11-06 | Glaxo Group Limited | Anti-inflammatory 17.β.-carbothioate ester derivatives of androstane with a cyclic ester group in position 17.α |
| US7592329B2 (en) | 2002-02-04 | 2009-09-22 | Glaxo Group Limited | Crystalline complexes of fluticasone-2-furoate |
| US8933060B2 (en) | 2002-06-14 | 2015-01-13 | Cipla Limited | Combination of azelastine and ciclesonide for nasal administration |
| US8937057B2 (en) | 2002-06-14 | 2015-01-20 | Cipla Limited | Combination of azelastine and mometasone for nasal administration |
| US9259428B2 (en) | 2002-06-14 | 2016-02-16 | Cipla Limited | Combination of azelastine and fluticasone for nasal administration |
| US9901585B2 (en) | 2002-06-14 | 2018-02-27 | Cipla Limited | Combination of azelastine and fluticasone for nasal administration |
| WO2012023077A1 (en) * | 2010-08-17 | 2012-02-23 | Sulur Subramaniam Vanangamudi | A medicinal fusidic acid cream made using sodium fusidate and incorporating a biopolymer, a corticosteroid - clobetasol propionate, and an antifungal agent - oxiconazole nitrate, and a process to make it |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2104677A1 (en) | 1992-08-23 |
| ES2064166T3 (en) | 1995-01-16 |
| EP0573492B1 (en) | 1994-11-23 |
| EP0573492A1 (en) | 1993-12-15 |
| DE69200711T2 (en) | 1995-03-30 |
| DK0573492T3 (en) | 1995-01-09 |
| MX9200728A (en) | 1992-10-01 |
| ATE114244T1 (en) | 1994-12-15 |
| DE69200711D1 (en) | 1995-01-05 |
| GR3015014T3 (en) | 1995-05-31 |
| GB9103764D0 (en) | 1991-04-10 |
| AU1277792A (en) | 1992-09-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0573492B1 (en) | Compositions for topical administration containing fluticasone propionate and oxiconazole or its salts | |
| US8232304B2 (en) | Antifungal formulations | |
| US5854246A (en) | Topical ketoconazole emulsions | |
| US6905675B2 (en) | Sulfur containing dermatological compositions and methods for reducing malodors in dermatological compositions | |
| EP2450043B1 (en) | Pharmaceutical composition for dermal use to treat psoriasis comprising calcipotriol and betamethasone | |
| US4661524A (en) | Topical treatment and composition | |
| JP3918119B2 (en) | Topical ketoconazole composition | |
| US4808610A (en) | Mometasone furoate anti-inflammatory cream composition using hexylene glycol | |
| US4298604A (en) | Clotrimazole-betamethasone dipropionate combination | |
| US5036095A (en) | Therapeutic use of DMDM Hydantoin | |
| CA1238276A (en) | Betamethasone dipropionate cream | |
| US5208015A (en) | Topical anti-fungal agents having anti-inflammatory activity | |
| ZA200102971B (en) | Fluticasone lotion having improved vasoconstrictor activity | |
| CA2220687A1 (en) | Use of a pharmaceutically acceptable oxalate derivative in the manufacture of a medicament for the treatment of skin conditions | |
| US6077865A (en) | Topical antifungal formulation containing tolnaftate | |
| KR950000032B1 (en) | Mixed Solution of Nitrate Econazole and Triamcinolone Acetonide | |
| HK1005999B (en) | Topical ketoconazole compositions | |
| JPWO1999061059A1 (en) | Minoxidil-containing topical composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AK | Designated states |
Kind code of ref document: A1 Designated state(s): AT AU BB BG BR CA CH CS DE DK ES FI GB HU JP KP KR LK LU MG MN MW NL NO PL RO RU SD SE US |
|
| AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE BF BJ CF CG CH CI CM DE DK ES FR GA GB GN GR IT LU MC ML MR NL SE SN TD TG |
|
| DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
| WWE | Wipo information: entry into national phase |
Ref document number: 1992905462 Country of ref document: EP |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 2104677 Country of ref document: CA |
|
| ENP | Entry into the national phase |
Ref document number: 1993 104155 Country of ref document: US Date of ref document: 19931122 Kind code of ref document: A |
|
| WWP | Wipo information: published in national office |
Ref document number: 1992905462 Country of ref document: EP |
|
| REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
| WWG | Wipo information: grant in national office |
Ref document number: 1992905462 Country of ref document: EP |