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WO1998002184A1 - Preparation topique a base d'acyclovir et contenant un phospholipide - Google Patents

Preparation topique a base d'acyclovir et contenant un phospholipide Download PDF

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Publication number
WO1998002184A1
WO1998002184A1 PCT/DE1996/001271 DE9601271W WO9802184A1 WO 1998002184 A1 WO1998002184 A1 WO 1998002184A1 DE 9601271 W DE9601271 W DE 9601271W WO 9802184 A1 WO9802184 A1 WO 9802184A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
preparation
phospholipid
preparation according
pharmaceutical preparation
Prior art date
Application number
PCT/DE1996/001271
Other languages
German (de)
English (en)
Inventor
Joachim Röding
Original Assignee
Mika Pharma Gesellschaft Für Die Entwicklung Und Vermarktung Pharmazeutischer Produkte Mbh
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
Application filed by Mika Pharma Gesellschaft Für Die Entwicklung Und Vermarktung Pharmazeutischer Produkte Mbh filed Critical Mika Pharma Gesellschaft Für Die Entwicklung Und Vermarktung Pharmazeutischer Produkte Mbh
Priority to AU76827/96A priority Critical patent/AU7682796A/en
Priority to EP96923837A priority patent/EP0914159A1/fr
Priority to PCT/DE1996/001271 priority patent/WO1998002184A1/fr
Publication of WO1998002184A1 publication Critical patent/WO1998002184A1/fr

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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A61K31/52—Purines, e.g. adenine
    • A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
    • 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
    • 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
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
    • 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

Definitions

  • the present invention relates to a pharmaceutical preparation for the therapy and / or prophylaxis of diseases of the skin and / or mucous membrane caused by viruses with the features of the preamble of the patent claim
  • viruses such as in particular herpes simplex, herpes labialis, genital herpes, herpes analis, herpes gestationis, herpes facial, herpes febrilis, herpes menstrualis or herpes zo - ster, are usually such pharmaceutical today
  • Preparations applied externally to the affected areas which contain aciclovir as the active ingredient.
  • These known pharmaceutical preparations represent dispersions of the virtually insoluble aciclovir in water, with a gel former and / or a pharmaceutically customary thickener based on a synthetic or natural polymer then being added to facilitate the application and use of such known pharmaceutical preparations so that these known preparations have a cream-like viscosity.
  • EP 0 394 928 gives an example of this mchtionogenes surfactant, which in the known preparation m of the order of 5 wt. % and about 10 Ge. % is included.
  • the preamble of claim 1 is known from WO 94/15614, the known preparation, in addition to the aforementioned active ingredient based on acyclovir, a salt and / or a derivative thereof, also containing at least one alcohol.
  • the known preparation contains, in addition to the aforementioned gel former, a water-soluble C j g - C - ⁇ -carboxylic acid salt.
  • the known pharmaceutical preparations described above have the disadvantage that they have a relatively low pharmaceutical activity, which is expressed in that, for example, the commercially available preparations have to be used every four hours over a treatment period of about five to ten days.
  • Such frequent and regular use of the known preparations can, however, result in the patient not carrying out the regular application of the known preparations with the necessary care, so that the treatment result when using the known preparations is ultimately not ensured.
  • the present invention is based on the object of making available a pharmaceutical preparation for the therapy and / or prophylaxis of diseases caused by viruses of the type mentioned at the outset, which has a particularly high pharmaceutical activity and is therefore used much less frequently by the patient over a predetermined period of time got to.
  • this object is achieved by a pharmaceutical see preparation with the characterizing features of claim 1 solved.
  • the pharmaceutical preparation according to the invention for the therapy and / or prophylaxis of diseases of the skin and / or mucous membrane caused by viruses, in particular for the therapy and / or prophylaxis of herpes has at least one active ingredient based on acyclovir, a salt and / or a derivative thereof, the at least one active ingredient m having a concentration between 1% by weight and 20
  • the preparation according to the invention contains at least one active ingredient
  • the preparation according to the invention thus has, as the alcoholic constituent, either at least one dihydric and / or trihydric C2-C5 alcohol or a mixture of at least one dihydric and / or trihydric C2-C5 alcohol with ethanol, propanol-1 and / or propanol -2, whereby this alcoholic constituent can then be supplemented by water in the preparation according to the invention
  • aqueous systems which can usually be contained in pharmaceutical preparations, in particular distilled or deionized water, Some physiological salt solutions, preferably saline solutions, aqueous buffers and / or buffer mixtures, preferably conventional physiological phosphate buffers.
  • the preparation according to the invention reproduced above has a particularly high pharmaceutical activity, so that the times between the use of the preparation according to the invention can be extended considerably.
  • the preparation according to the invention can generally be used only a maximum of twice a day for a few days, preferably three to five days, in order to effectively cure the aforementioned diseases.
  • subjects who suffered from herpes simplex or the aforementioned other herpes diseases reported that the prophylactic use of the preparation according to the invention, for example once or twice a week, did not occur at all at the outset.
  • the supply of moisture causes the walls of the herpes blisters to remain elastic and not tear, so that predominantly no fluids contaminated with viruses emerge from the herpes blisters and even if a herpes blister tears open as a result of mechanical destruction and thus liquid contaminated with viruses escapes, and the skin areas adjacent to it do not absorb the skin areas of this liquid contaminated with viruses due to the lack of cracking described above, so that here too no new herpes vesicles can be formed.
  • This effect is further increased by the phospholipid or phospholipid mixture contained in the preparation according to the invention, since this results in a high elasticity of the walls of the herpes vesicles in that the phospholipid or the phospholipid mixture m the wall the herpes vesicle penetrates and makes them more elastic.
  • This also applies to neighboring, non-diseased areas of the skin, so that these areas of the skin are changed in such a way that they become both more elastic and therefore not cracked and / or that they become so hydrophobic and through a layer of the phospholipid or phospholipid mixture are protected so that penetration of virus-contaminated liquid cannot occur with mechanical damage to the herpes blisters.
  • the phospholipid or phospholipid mixture contained in the preparation according to the invention obviously causes one
  • the principle of water-insoluble active ingredient aciclovir is better, more uniform and / or much finer, so that this active ingredient can also be transported more easily, in larger amounts and faster through the wall of the herpes vesicles, with the membrane structure of the walls additionally Herpes vesicles are changed by the phospholipid or the phospholipid mixture in such a way that the throughput of the active ingredient is increased.
  • the preparation according to the invention has relatively few constituents compared to the known preparations, so that an undesirable side effect as a result of additive effects Individual components are to be feared, especially since a main component of the preparation according to the invention, namely the phospholipid or the phospholipid mixture, is an essential component of the human body.
  • a main component of the preparation according to the invention namely the phospholipid or the phospholipid mixture
  • the preparation according to the invention has a semi-solid consistency, particularly the consistency of a hydrogel, which is ideal for topical use, simply because of the presence of the phospholipid, the presence of the usual gelling agents and / or thickeners are completely dispensed with in the preparation according to the invention.
  • the preparation according to the invention forms a gel and in particular a hydrogel with a finely divided active ingredient, the pharmaceutical effectiveness of the preparation according to the invention being far superior to that of the known preparations.
  • the at least one acyclovir contained as active ingredient in the preparation according to the invention has a chemical formula as shown below.
  • a first embodiment variant of the preparation according to the invention has a total concentration of water, alcohol and / or alcohol mixture which is between 90% by weight. and 40 wt.%, preferably between 85 wt.% and 65 wt.%,] varies depending on the ready-to-use preparation. It was found here that such an embodiment variant of the preparation according to the invention can be applied without pain by the patient without difficulty even if the diseased areas of the skin or mucous membrane are particularly sensitive to pressure.
  • the mass ratio of water to the alcohol or the mass ratio of water to the alcohol mixture is preferably between 1: 0.2 to 1: 1.2, in particular between 1: 0, 4 to 1: 0.7, varies.
  • the phospholipid or the phospholipid mixture contained in the preparation according to the invention there are several possibilities, it being particularly preferred that the preparation according to the invention has a phospholipid mixture isolated from plants, in particular from soybeans or sunflowers.
  • the preparation according to the invention contains a phospholipid or a phospholipid mixture which contains at least 60% by weight phosphatidylcholm, preferably at least 76% by weight phosphatidylcholm and in particular at least 90% by weight phosphatidylcholm.
  • a further development of the preparation according to the invention provides that the concentration of lysophosphatidylcholm to a maximum value of 6% by weight, in particular to a maximum value of 4% by weight %, based on the amount of the phospholipid mixture, is limited.
  • Phosphatidylcholm in the sense of the present description represents, chemically, 1, 2-d ⁇ acylglycero-3-phosphochol (3 -sn-phosphatidylcholine), this 1,2 -diacylglycero-3-phosphocholm corresponding acyl residues both in 1- and m 2 Position can have.
  • a preferred development of the pharmaceutical preparation according to the invention has a phosphatidylcholm, the acyl residues in the 1- and 2-position to 10-15% by weight consist of the palmitic acid, 1.5 - 4% by weight of the stearic acid residue, 3 - 10% by weight of the oleic acid residue, 61 - 71% by weight of the lmoleic acid residue and 3 - 7% by weight of the lmoleic acid residue.
  • the fluctuations in the percentages given above for "each acyl residue are related to the fact that the phosphatidylchol preferably used in the preparation according to the invention is such a phosphatidylcholm which is isolated from natural sources, in particular from sun and / or from sunflowers, and is purified accordingly has been
  • the preparation according to the invention has a different consistency within a certain limit concentration of phospholipid mixture
  • a hydrogenated phospholipid or hydrogenated phospholipid mixture is preferably used, in which the concentration of the hydrogenated phosphatidylcholm varies within the above-mentioned limits.
  • a hydrogenated phosphatidylcholm preferably has 85% by weight + _ 3% by weight of the stearic acid residue and 15% by weight _ + 2% by weight of the palmitic acid residue in the 1- and m-2 positions as acyl residues, where the percentages by weight given above do not relate to the ready-to-use preparation but to the concentration of the phospholipid mixture in the preparation.
  • the pharmaceutical preparation according to the invention has a phospholipid mixture which, as the main constituent, contains phosphatidylcholm with the concentration data mentioned above.
  • a maximum of 6% by weight of lysophosphatidylcholm, 0-12% by weight of phosphatidylethanolamm, 0-8% by weight of phosphatidylmositol and / or 0-8% by weight of phosphatidic acid are then preferably present in the phospholipid mixture, the fluctuations in the concentration data given above being included
  • the other constituents can be explained by the fact that the phospholipid mixture used in the pharmaceutical preparation is preferably isolated from a natural source. Furthermore, small proportions of oils and / or sterms can also be contained in this phospholipid mixture, the concentration information given above referring to the phospholipid mixture itself and not to the ready-to-use pharmaceutical preparation according to the invention.
  • the preparation according to the invention contains between 23% by weight and 35% by weight of the phospholipid or of the phospholipid mixture, based on the ready-to-use preparation, such embodiments have a form of administration which is particularly convenient to use.
  • concentration of active substance contained in the preparation according to the invention it should be noted that this concentration preferably depends on the body location and how often the body according to the invention
  • the concentration of the at least one active ingredient m of the preparation according to the invention varies between 1% by weight and 20% by weight, preferably between 1% by weight and 7% by weight, the concentration information of the at least one active ingredient given above being based on the obtain ready-to-use preparations
  • an alkali metal salt preferably a sodium or potassium salt, of the aciclovir and / or e Ester, preferably the ester of a C ⁇ - ⁇ -Carßon ⁇ aure, may contain.
  • compositions according to the invention have a semi-solid consistency desired for the application, so that the preparation according to the invention is preferably free of thickeners and / or gelling agents
  • the preparation according to the invention preferably has propanediol, in particular propanediol-1.2, as the dihydric alcohol.
  • the concentration of the aforementioned propanediol in the preparation varies depending on the concentration tion of the at least one active substance, the concentration of the phospholipid or phospholipid mixture and the chemical structure of the phospholipid or phospholipid mixture between 15% by weight and 50% by weight, so that in this embodiment of the preparation according to the invention it does not contain an alcohol mixture, but instead the alcoholic component is formed solely by propanediol, preferably propanediol-1.2.
  • the preparation according to the invention contains glycerol as the trihydric alcohol, this glycerol then either being contained exclusively in the preparation as an alcoholic component or optionally with ethanol, propanol-1 and / or propanol-2 and / or with and / / or several divalent C2-C5-alcohols can be added.
  • a particularly suitable embodiment of the preparation according to the invention has 5% by weight of the at least one active ingredient reproduced above, 24% by weight of the previously described phospholipids or phospholipid mixtures, 16% by weight of propanediol -1.2 and 55% by weight of water, where refer all of this concentration information to the ready-to-use preparation.
  • a further embodiment of the preparation according to the invention comprises 5% by weight of the at least one active ingredient, 15% by weight of the previously described phospholipids, 55% by weight of water, 16% by weight of propanediol and 9
  • % By weight contains glycerin, these percentages referring to the ready-to-use preparation.
  • a further embodiment of the preparation according to the invention likewise has 5% by weight of the at least one active ingredient, 5% by weight of a hydrogenated phospholipid mixture, 15% by weight of 1,2-propanediol and 75% by weight of water, the preparation also specifically as that previously described preparations have a semi-solid consistency.
  • the hydrogenated phospholipid mixture has at least 60% by weight of phosphatidylcholm, the acyl radicals in the 1- and 2-positions being 85% by weight + . 3% by weight of the stearic acid residue and 15% by weight ⁇ 2% by weight of the palmitic acid residue, and this hydrogenated phospholipid mixture further contains the above-mentioned further phospholipids.
  • the pharmaceutical preparation according to the invention preferably has a semi-solid consistency, so that this simplifies the use of the preparation according to the invention.
  • a semi-solid consistency is always given when the preparation according to the invention has a viscosity between 50 x 10 3 Pas and 3 x 103 mPas, preferably between 40 x 10 3 mPas and 10 x 103 mPas, this viscosimetric data with a Rotation viscometers can be measured at a rotational speed of 20 revolutions / min and a temperature of 20 + 1 ° C, as described in detail in the exemplary embodiments.
  • the active ingredient, the phospholipid and the alcohol component were combined and stirred vigorously at 40 ° C. for five minutes using a suitable stirrer at a speed of approximately 1,300 revolutions / min. After the stirring time of five minutes had elapsed, water was added to the mixture and stirring was continued for a further five minutes. Even after adding water, the temperature was still 40 ° C. After the water was mixed in, the mixture was further stirred for 15 minutes, the speed during which further stirring was 2,300 revolutions / mm. During this further stirring, the mixture cooled from 40 ° C to room temperature, ie about 20 to 22 ° C. This was followed by the addition of sodium hydroxide solution in order to adjust the pH of the finished mixture to 6.5 to 6.8.
  • Preparations 1 to 7 had the ingredients shown in Table 1, these details relating to% by weight, based on the ready-to-use preparation.
  • the phospholipid mixture used in preparations 1 to 7 consisted of
  • the phosphatidylcholine had the following acyl residues in the 1- and 2-positions:
  • Preparations 8 to 10 were produced by the same method as that described above for preparations 1 to 7. Deviating from this, however, the mixing was not carried out at a temperature of 40 ° C. but at 60 ° C.
  • Preparations 8 to 10 had the ingredients shown in Table 2 below.
  • the phospholipid used for the preparation of preparations 8 to 10 was a hydrogenated phospholipid and consisted of the following ingredients:
  • the preparation 6 had a viscosity of 40.20 x 10 mPas, the preparation 7 a viscosity of 16.20 x 10 ⁇ mPas and the preparation 8 a viscosity of 10.6 x 10 mPas

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne une préparation pharmaceutique pour la thérapie et/ou prophylaxie d'affections virales de la peau et/ou des muqueuses, de préférence pour la thérapie et/ou prophylaxie de l'herpès. Cette préparation contient au moins une matière active à base d'acyclovir, d'un sel et/ou d'un de ses dérivés. La/les matières(s) active(s) est/sont présente(s) avec une concentration de 1 à 20 % en poids par rapport à la préparation prête à l'emploi. La préparation de l'invention contient également un phospholipide ou un mélange phospholipidique à hauteur de 5 à 35 % en poids, un alcool ou un mélange d'alcools à hauteur de 15 à 50 % en poids et de l'eau à hauteur de 79 à 0 % en poids d'eau, toujours par rapport à la préparation prête à l'emploi. Les 15 à 50 % en poids d'alcool ou de mélange d'alcools se composent de 0 à 41 % en poids d'éthanol, de propanol-1 et/ou propanol-2 et de 100 à 59 % en poids d'au moins un alcool C2-C5 bivalent et/ou trivalent.
PCT/DE1996/001271 1996-07-13 1996-07-13 Preparation topique a base d'acyclovir et contenant un phospholipide WO1998002184A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU76827/96A AU7682796A (en) 1996-07-13 1996-07-13 Topical phospholipid-containing acyclovir preparation
EP96923837A EP0914159A1 (fr) 1996-07-13 1996-07-13 Preparation topique a base d'acyclovir et contenant un phospholipide
PCT/DE1996/001271 WO1998002184A1 (fr) 1996-07-13 1996-07-13 Preparation topique a base d'acyclovir et contenant un phospholipide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/DE1996/001271 WO1998002184A1 (fr) 1996-07-13 1996-07-13 Preparation topique a base d'acyclovir et contenant un phospholipide

Publications (1)

Publication Number Publication Date
WO1998002184A1 true WO1998002184A1 (fr) 1998-01-22

Family

ID=6918362

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DE1996/001271 WO1998002184A1 (fr) 1996-07-13 1996-07-13 Preparation topique a base d'acyclovir et contenant un phospholipide

Country Status (3)

Country Link
EP (1) EP0914159A1 (fr)
AU (1) AU7682796A (fr)
WO (1) WO1998002184A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999044642A1 (fr) * 1998-03-05 1999-09-10 Phares Pharmaceutical Research Nv Compositions pharmaceutiques et leur utilisation
WO2004047790A3 (fr) * 2002-11-26 2004-09-30 Mcs Micro Carrier Systems Gmbh Gels phospholipidiques se formant d'eux-mêmes
WO2012083906A3 (fr) * 2010-12-20 2013-02-28 Mika Pharma Gesellschaft Für Die Entwicklung Und Vermarktung Pharmazeutischer Produkte Mbh Procédé pour développer une composition liquide à appliquer sur la peau sous forme de mousse ainsi que composition applicable topiquement
US9005626B2 (en) 2009-07-24 2015-04-14 Mika Pharma Gmbh Liquid compositions capable of foaming and including active agents, and methods for making or developing same

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991011993A1 (fr) * 1990-02-08 1991-08-22 Nattermann. A & Cie. Gmbh Composition phospholipidique aqueuse sous forme de gel a teneur en alcool, son utilisation et preparations topiques la renfermant
WO1995035095A1 (fr) * 1994-06-22 1995-12-28 Yissum Research Development Company Of The Hebrew University Of Jerusalem Compositions destinees a l'application de substances actives sur la peau
DE19517147A1 (de) * 1995-05-10 1996-11-14 Hexal Pharmaforschung Gmbh Aciclovir-Zubereitung

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991011993A1 (fr) * 1990-02-08 1991-08-22 Nattermann. A & Cie. Gmbh Composition phospholipidique aqueuse sous forme de gel a teneur en alcool, son utilisation et preparations topiques la renfermant
WO1995035095A1 (fr) * 1994-06-22 1995-12-28 Yissum Research Development Company Of The Hebrew University Of Jerusalem Compositions destinees a l'application de substances actives sur la peau
DE19517147A1 (de) * 1995-05-10 1996-11-14 Hexal Pharmaforschung Gmbh Aciclovir-Zubereitung

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999044642A1 (fr) * 1998-03-05 1999-09-10 Phares Pharmaceutical Research Nv Compositions pharmaceutiques et leur utilisation
US6605298B1 (en) 1998-03-05 2003-08-12 Phares Pharmaceutical Research N.V. Pharmaceutical compositions and their use
WO2004047790A3 (fr) * 2002-11-26 2004-09-30 Mcs Micro Carrier Systems Gmbh Gels phospholipidiques se formant d'eux-mêmes
US9005626B2 (en) 2009-07-24 2015-04-14 Mika Pharma Gmbh Liquid compositions capable of foaming and including active agents, and methods for making or developing same
US9693956B2 (en) 2009-07-24 2017-07-04 Mika Pharma Gmbh Liquid compositions capable of foaming and including active agents, and methods for making or developing same
WO2012083906A3 (fr) * 2010-12-20 2013-02-28 Mika Pharma Gesellschaft Für Die Entwicklung Und Vermarktung Pharmazeutischer Produkte Mbh Procédé pour développer une composition liquide à appliquer sur la peau sous forme de mousse ainsi que composition applicable topiquement

Also Published As

Publication number Publication date
AU7682796A (en) 1998-02-09
EP0914159A1 (fr) 1999-05-12

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