WO1995024193A1 - Topical preparations - Google Patents

Topical preparations Download PDF

Info

Publication number
WO1995024193A1
WO1995024193A1 PCT/EP1995/000902 EP9500902W WO9524193A1 WO 1995024193 A1 WO1995024193 A1 WO 1995024193A1 EP 9500902 W EP9500902 W EP 9500902W WO 9524193 A1 WO9524193 A1 WO 9524193A1
Authority
WO
WIPO (PCT)
Prior art keywords
pharmaceutical preparations
preparations according
topical pharmaceutical
organic solvents
topical
Prior art date
Application number
PCT/EP1995/000902
Other languages
German (de)
French (fr)
Inventor
Rudolf Linder
Original Assignee
Byk Gulden Lomberg Chemische Fabrik Gmbh
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 Byk Gulden Lomberg Chemische Fabrik Gmbh filed Critical Byk Gulden Lomberg Chemische Fabrik Gmbh
Publication of WO1995024193A1 publication Critical patent/WO1995024193A1/en

Links

Classifications

    • 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
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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
    • 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 invention relates to pharmaceutical preparations for the topical application of proliferation-inhibiting pyridine derivatives with basic substituted side chains.
  • WO 91/15484 proliferation-inhibiting pyridine derivatives with basic substituted side chains are known. According to the teaching of WO 93/11766, these compounds are suitable for the topical treatment of dermatoses.
  • Dermatoses include, for example, inflammatory and allergic skin diseases and, in particular, skin diseases that are based on pathologically increased cell formation.
  • Lipophilic active ingredients are usually incorporated into fatty ointments or creams or are dissolved in a suitable organic solvent with subsequent thickening by adding
  • the invention therefore relates to pharmaceutical preparations of pyridine derivatives with basic substituted side chains for topical use, characterized in that the active compounds are incorporated in a mixture comprising lecithins and organic solvents and water.
  • the active substances are contained in the pharmaceutical preparations according to the invention in a concentration of 2 to 5, preferably 3 to 4,% by weight.
  • lecithins are those which contain at least 70% by weight of hydrogenated and / or unsaturated phosphatidylcholines.
  • the proportion of lecithin in the pharmaceutical preparations according to the invention is 8 to 20, preferably 12 to 17,% by weight.
  • organic solvents are polyethylene glycols, in particular polyethylene glycol 400, propylene glycol and ethanol, the Use of ethanol is preferred.
  • the proportion of organic solvents in the pharmaceutical preparations according to the invention is 5 to 30% by weight, preferably 8 to 15% by weight.
  • the pharmaceutical preparations according to the invention contain 0.5 to 7, preferably 2 to 5% by weight of oily triglycerides.
  • the pharmaceutical preparations according to the invention can be customary physiologically tolerated auxiliaries, such as, for. B. fragrances, antioxidants and preservatives are added in the commonly used amounts.
  • auxiliaries such as, for. B. fragrances, antioxidants and preservatives are added in the commonly used amounts.
  • the pharmaceutical preparations according to the invention are produced by first dissolving the active ingredient (s) together with the lecithin (s) in the organic solvent heated to 30 to 40 ° C.
  • the water, likewise heated to 30 to 40 ° C., is then added with stirring.
  • transparent ointments are obtained.
  • the active ingredient and the two phospholipids are dissolved in the stated amount of ethanol at 30 to 40 ° C.
  • the amount of water heated to 30 to 40 ° C is added with stirring.
  • the transparent ointment obtained on cooling to room temperature is filled into tubes.

Landscapes

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

Abstract

Topical medicinal preparations of pyridine derivatives having side chains substituted with bases for topical application are described. The preparations are characterized in that the active substances are incorporated in a mixture containing lecithins, organic solvents and water. The medicaments according to the invention are stable on storage.

Description

Topische ZubereitungenTopical preparations
Technisches GebietTechnical field
Die Erfindung betrifft Arzneimittelzubereitungen zur topischen Anwendung von proliferationshemmenden Pyridinderivaten mit basisch substituierten Seitenketten.The invention relates to pharmaceutical preparations for the topical application of proliferation-inhibiting pyridine derivatives with basic substituted side chains.
Stand der TechnikState of the art
Aus WO 91/15484 sind proliferationshem ende Pyridinderivate mit basisch substituierten Seitenketten bekannt. Gemäß der Lehre der WO 93/11766 eignen sich diese Verbindungen zur topischen Behandlung von Dermatosen. Als Derma- tosen seien beispielsweise entzündliche und allergische Hauterkrankungen erwähnt sowie insbesondere solche Hauterkrankungen, die auf einer krankhaft vermehrten Zellneubildung beruhen. Besonders interessant sind die Verbin¬ dungen (-)l,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridin-3,5-dicarbon- säure-3-methyl-5-[3-(4,4-diphenyl-l-piperidinyl)propyl]ester (B8509-035, International Nonproprietary Name: Dexniguldipin, beschrieben in EP-A 0296316), 5-Acetyl-2,6-dimethyl-3-[8-(4,4-diphenyl-l-piperidinyl)octanoyl]- 4-(3-nitrophenyl)pyridin (B9203-009), 3-[8-(4,4-Diphenyl-l-piperidinyl)oc- tanoyl]-2-methyl-4-(3-nitrophenyl)-5-oxo-5,6,7,8-tetrahydrochinolin (B9203-016), (-)l,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridin-3,5-di- carbonsäure-3-methyl-5-[3-(4-diphenyl-l-piperazinyl)propyl]ester (B8709-025), (-)l,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridin-3,5- dicarbonsäure-3-[3-(4-diphenylmethylen-l-piperidinyl)propyl]-5-methylester (B8909-034), 5-Acetyl-2,6-dimethyl-3-[5-(4,4-diphenyl-l-piρeridinyl)penta- noyl]-4-(3-nitrophenyl)pyridin (B9003-001) und deren Salze.From WO 91/15484 proliferation-inhibiting pyridine derivatives with basic substituted side chains are known. According to the teaching of WO 93/11766, these compounds are suitable for the topical treatment of dermatoses. Dermatoses include, for example, inflammatory and allergic skin diseases and, in particular, skin diseases that are based on pathologically increased cell formation. The compounds (-) 1,4-dihydro-2,6-dimethyl-4- (3-nitrophenyl) pyridine-3,5-dicarboxylic acid-3-methyl-5- [3- (4th , 4-diphenyl-l-piperidinyl) propyl] ester (B8509-035, International Nonproprietary Name: Dexniguldipin, described in EP-A 0296316), 5-acetyl-2,6-dimethyl-3- [8- (4,4 -diphenyl-l-piperidinyl) octanoyl] - 4- (3-nitrophenyl) pyridine (B9203-009), 3- [8- (4,4-diphenyl-l-piperidinyl) octanoyl] -2-methyl-4 - (3-nitrophenyl) -5-oxo-5,6,7,8-tetrahydroquinoline (B9203-016), (-) 1,4-dihydro-2,6-dimethyl-4- (3-nitrophenyl) pyridine- 3,5-dicarboxylic acid-3-methyl-5- [3- (4-diphenyl-l-piperazinyl) propyl] ester (B8709-025), (-) l, 4-dihydro-2,6-dimethyl- 4- (3-nitrophenyl) pyridine-3,5-dicarboxylic acid 3- [3- (4-diphenylmethylene-1-piperidinyl) propyl] -5-methyl ester (B8909-034), 5-acetyl-2,6-dimethyl -3- [5- (4,4-diphenyl-l-piperidinyl) penta- noyl] -4- (3-nitrophenyl) pyridine (B9003-001) and its salts.
Es bestand daher das Bedürfnis, für die genannten Verbindungen Zubereitun¬ gen zur topischen Anwendung zur Verfügung zu stellen. Diese Wirkstoffe zei¬ gen lipophiles Verhalten. Lipophile Wirkstoffe werden üblicherweise in Fettsalben oder Cremes eingearbeitet oder werden in einem geeigneten orga¬ nischen Lösungsmittel gelöst mit anschließender Eindickung durch Zusatz ge-There was therefore a need to provide preparations for the compounds mentioned for topical use. These active substances show lipophilic behavior. Lipophilic active ingredients are usually incorporated into fatty ointments or creams or are dissolved in a suitable organic solvent with subsequent thickening by adding
ORIGINAL UNTERLAGEN eigneter Hilfsstoffe. Es zeigte sich nun, daß es nicht möglich ist, lager¬ stabile Zubereitungen der genannten Wirkstoffe durch Einarbeiten in Fett¬ salben oder Cremes zu erhalten, weil sich hierin ein unerwünschtes Teil- chenwachstu zeigt. Da die Wirkstoffe auf bereits vorgeschädigte Hautareale aufgetragen werden müssen, kommt auch eine Einarbeitung in verdickte orga¬ nische Lösungsmittel nicht in Frage, weil starke Hautirritationen zu erwar¬ ten sind.ORIGINAL DOCUMENTS suitable auxiliaries. It has now been shown that it is not possible to obtain preparations of the active compounds mentioned which are stable in storage by incorporating them into fatty ointments or creams, because this shows an undesirable particle growth. Since the active ingredients have to be applied to previously damaged skin areas, incorporation into thickened organic solvents is also out of the question, because severe skin irritation can be expected.
Beschreibung der ErfindungDescription of the invention
Es wurde nun überraschenderweise festgestellt, daß Zubereitungen enthaltend Pyridinderivate mit basisch substituierten Seitenketten, Lecithin, organi¬ sche Lösungsmittel und Wasser streichfähige, transparente Formen bilden, die lagerstabil sind und auch auf vorgeschädigter Haut überraschend ver¬ träglich sind. Daß diese Zubereitungen streichfähig und transparent sind überrascht, da die entsprechenden wirkstofffreien Mischungen der Hilfsstof¬ fe dünnflüssig und milchig trüb sind.It has now surprisingly been found that preparations containing pyridine derivatives with base-substituted side chains, lecithin, organic solvents and water form spreadable, transparent forms which are stable on storage and are surprisingly tolerable even on previously damaged skin. The fact that these preparations are spreadable and transparent are surprising, since the corresponding active ingredient-free mixtures of the auxiliaries are thin and milky.
Gegenstand der Erfindung sind daher Arzneimittelzubereitungen von Pyridin- derivaten mit basisch substituierten Seitenketten zur topischen Anwendung dadurch gekennzeichnet, daß die Wirkstoffe in einer Mischung enthaltend Le¬ cithine und organische Lösungsmittel und Wasser eingearbeitet sind.The invention therefore relates to pharmaceutical preparations of pyridine derivatives with basic substituted side chains for topical use, characterized in that the active compounds are incorporated in a mixture comprising lecithins and organic solvents and water.
Weitere Gegenstände ergeben sich aus den Unteransprüchen.Further objects result from the subclaims.
Die Wirkstoffe sind in den erfindungsgemäßen Arzneimittelzubereitungen ei¬ ner Konzentration von 2 bis 5, vorzugsweise 3 bis 4 Gew.-% enthalten.The active substances are contained in the pharmaceutical preparations according to the invention in a concentration of 2 to 5, preferably 3 to 4,% by weight.
Als Lecithine kommen insbesondere solche in Frage, die mindestens 70 Gew.-?- an hydrierten und/oder ungesättigten Phosphatidylcholinen enthalten. Der Lecithinanteil an den erfindungsgemäßen Arzneimittelzubereitungen beträgt 8 bis 20, vorzugsweise 12 bis 17 Gew.-%.Particularly suitable lecithins are those which contain at least 70% by weight of hydrogenated and / or unsaturated phosphatidylcholines. The proportion of lecithin in the pharmaceutical preparations according to the invention is 8 to 20, preferably 12 to 17,% by weight.
Als organische Lösungsmittel kommen vor allem Polyethylenglycole, insbeson¬ dere Polyethylenglycol 400, Propylenglycol und Ethanol in Frage, wobei die Verwendung von Ethanol bevorzugt ist. Der Anteil organischer Lösungsmittel an den erfindungsgemäßen Arzneimittelzubereitungen beträgt 5 bis 30, vor¬ zugsweise 8 bis 15 Gew.-%.Particularly suitable organic solvents are polyethylene glycols, in particular polyethylene glycol 400, propylene glycol and ethanol, the Use of ethanol is preferred. The proportion of organic solvents in the pharmaceutical preparations according to the invention is 5 to 30% by weight, preferably 8 to 15% by weight.
Wasser ist zu 40 bis 85, vorzugsweise 65 bis 75 Gew.-% in den erfindungsge¬ mäßen Zubereitungen enthalten.40 to 85, preferably 65 to 75% by weight of water is present in the preparations according to the invention.
Gewünschtenfalls enthalten die erfindungsgemäßen Arzneimittelzubereitungen 0,5 bis 7, vorzugsweise 2 bis 5 Gew.-% ölige Triglyceride.If desired, the pharmaceutical preparations according to the invention contain 0.5 to 7, preferably 2 to 5% by weight of oily triglycerides.
Weiterhin können den erfindungsgemäßen Arzneimittelzubereitungen übliche physiologisch verträgliche Hilfsstoffe, wie z. B. Duftstoffe, Antioxidan- tien und Konservierungsstoffe, in den üblicherweise verwendeten Mengen zu¬ gefügt werden.Furthermore, the pharmaceutical preparations according to the invention can be customary physiologically tolerated auxiliaries, such as, for. B. fragrances, antioxidants and preservatives are added in the commonly used amounts.
Die Herstellung der erfindungsgemäßen Arzneimittelzubereitungen erfolgt, indem zuerst der bzw. die Wirkstoffe zusammen mit dem bzw. den Lecithinen in dem auf 30 bis 40°C erwärmten organischen Lösungsmittel gelöst werden. Das ebenfalls auf 30 bis 40°C erwärmte Wasser wird sodann unter Rühren hin¬ zugefügt. Beim Abkühlen auf Raumtemperatur erhält man transparente Salben. The pharmaceutical preparations according to the invention are produced by first dissolving the active ingredient (s) together with the lecithin (s) in the organic solvent heated to 30 to 40 ° C. The water, likewise heated to 30 to 40 ° C., is then added with stirring. When cooling to room temperature, transparent ointments are obtained.
HerstellunqsbeispieleManufacturing examples
Beispiel 1example 1
Zusammensetzung für 1 kg SalbeComposition for 1 kg of ointment
B9203-009 20,0 gB9203-009 20.0 g
Epikuron® 200Epikuron ® 200
(Phosphatidylcholin, MG -790) 80,0 g(Phosphatidylcholine, MW -790) 80.0 g
Epikuron® 200 SHEpikuron ® 200 SH
(hydriertes Epikuron® 200) 80,0 g(hydrogenated Epikuron ® 200) 80.0 g
Ethanol 100,0 gEthanol 100.0 g
Gereinigtes Wasser 720,0 gPurified water 720.0 g
In der angegebenen Menge Ethanol werden bei 30 bis 40°C der Wirkstoff und die beiden Phosphol ipide gelöst. Die auf 30 bis 40°C erwärmte Wassermenge wird unter Rühren hinzugegeben. Die beim Abkühlen auf Raumtemperatur erhal¬ tene transparente Salbe wird in Tuben abgefüllt.The active ingredient and the two phospholipids are dissolved in the stated amount of ethanol at 30 to 40 ° C. The amount of water heated to 30 to 40 ° C is added with stirring. The transparent ointment obtained on cooling to room temperature is filled into tubes.
Beispiel 2Example 2
Zusammensetzung für 1 kg SalbeComposition for 1 kg of ointment
B9203-016 20,0 g Epikuron® 200B9203-016 20.0 g Epikuron ® 200
(Phosphatidylcholin, MG -790) 160,0 g(Phosphatidylcholine, MW -790) 160.0 g
Ethanol 100,0 gEthanol 100.0 g
Gereinigtes Wasser 720,0 gPurified water 720.0 g
Die Herstellung erfolgt analog Beispiel 1. The production takes place analogously to example 1.

Claims

Patentansprüche claims
1. Topische Arzneimittelzubereitungen von Pyridinderivaten mit basisch substituierten Seitenketten zur topischen Anwendung, dadurch gekennzeich¬ net, daß die Wirkstoffe in einer Mischung enthaltend Lecithine und organi¬ sche Lösungsmittel und Wasser eingearbeitet sind.1. Topical pharmaceutical preparations of pyridine derivatives with basic substituted side chains for topical use, characterized in that the active ingredients are incorporated in a mixture comprising lecithins and organic solvents and water.
2. Topische Arzneimittelzubereitungen nach Anspruch 1, dadurch gekenn¬ zeichnet, daß die Wirkstoffe in einer Menge von 2 bis 5, Lecithine in einer Menge von 8 bis 20, organische Lösungsmittel in einer Menge von 5 bis 30 und Wasser in einer Menge von 40 bis 85 Gew.-% enthalten sind.2. Topical pharmaceutical preparations according to claim 1, characterized gekenn¬ characterized in that the active ingredients in an amount of 2 to 5, lecithins in an amount of 8 to 20, organic solvents in an amount of 5 to 30 and water in an amount of 40 to 85 wt .-% are included.
3. Topische Arzneimittelzubereitungen nach Anspruch 2, dadurch gekenn¬ zeichnet, daß zusätzlich 2 bis 5 Gewichtsprozent ölige Triglyceride enthal¬ ten sind.3. Topical pharmaceutical preparations according to claim 2, characterized gekenn¬ characterized in that 2 to 5 percent by weight of oily triglycerides are included.
4. Topische Arzneimittelzubereitungen nach Anspruch 1, dadurch gekenn¬ zeichnet, daß die Lecithine mindestens 70 Gew.-% hydrierte und/oder unge¬ sättigte Phosphatidylcholine enthalten.4. Topical pharmaceutical preparations according to claim 1, characterized gekenn¬ characterized in that the lecithins contain at least 70 wt .-% hydrogenated and / or unsaturated phosphatidylcholines.
5. Topische Arzneimittelzubereitungen nach Anspruch 1, dadurch gekenn¬ zeichnet, daß als organische Lösungsmittel Polyethylenglycole, Propylengly- col und/oder Ethanol enthalten sind.5. Topical pharmaceutical preparations according to claim 1, characterized gekenn¬ characterized in that polyethylene glycols, propylene glycol and / or ethanol are included as organic solvents.
6. Topische Arzneimittelzubereitungen nach Anspruch 5, dadurch gekenn¬ zeichnet, daß als organisches Lösungsmittel Ethanol enthalten ist.6. Topical pharmaceutical preparations according to claim 5, characterized gekenn¬ characterized in that ethanol is contained as the organic solvent.
7. Topische Arzneimittelzubereitungen nach Anspruch 1, dadurch gekenn¬ zeichnet, daß als Wirkstoffe Dexniguldipin, B9203-009, B9203-016, B8709-025, B8909-034 und/oder B9003-001 enthalten sind. 7. Topical pharmaceutical preparations according to claim 1, characterized gekenn¬ characterized in that dexniguldipine, B9203-009, B9203-016, B8709-025, B8909-034 and / or B9003-001 are contained as active ingredients.
PCT/EP1995/000902 1994-03-10 1995-03-10 Topical preparations WO1995024193A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944407995 DE4407995C2 (en) 1994-03-10 1994-03-10 Topical preparations
DEP4407995.8 1994-03-10

Publications (1)

Publication Number Publication Date
WO1995024193A1 true WO1995024193A1 (en) 1995-09-14

Family

ID=6512355

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/000902 WO1995024193A1 (en) 1994-03-10 1995-03-10 Topical preparations

Country Status (2)

Country Link
DE (1) DE4407995C2 (en)
WO (1) WO1995024193A1 (en)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61172831A (en) * 1985-01-26 1986-08-04 Nakanishi Michio Anti-inflammatory, analgesic drug composition
WO1989000077A1 (en) * 1987-07-01 1989-01-12 Pier Luigi Luisi Lecithin gel
WO1991011993A1 (en) * 1990-02-08 1991-08-22 Nattermann. A & Cie. Gmbh Alcoholic aqueous gel-type phospholipid composition, its use and topical preparations containing it
WO1993011766A1 (en) * 1991-12-13 1993-06-24 Byk Gulden Lomberg Chemische Fabrik Gmbh 1,4-dihydropyridines for use in the treatment of dermatosis
WO1994000123A1 (en) * 1992-06-24 1994-01-06 Byk Gulden Lomberg Chemische Fabrik Gmbh Micro-emulsion of dexniguldipin

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61172831A (en) * 1985-01-26 1986-08-04 Nakanishi Michio Anti-inflammatory, analgesic drug composition
WO1989000077A1 (en) * 1987-07-01 1989-01-12 Pier Luigi Luisi Lecithin gel
WO1991011993A1 (en) * 1990-02-08 1991-08-22 Nattermann. A & Cie. Gmbh Alcoholic aqueous gel-type phospholipid composition, its use and topical preparations containing it
WO1993011766A1 (en) * 1991-12-13 1993-06-24 Byk Gulden Lomberg Chemische Fabrik Gmbh 1,4-dihydropyridines for use in the treatment of dermatosis
WO1994000123A1 (en) * 1992-06-24 1994-01-06 Byk Gulden Lomberg Chemische Fabrik Gmbh Micro-emulsion of dexniguldipin

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 8637, Derwent World Patents Index; AN 86-242892 *

Also Published As

Publication number Publication date
DE4407995C2 (en) 1996-07-11
DE4407995A1 (en) 1995-09-14

Similar Documents

Publication Publication Date Title
DE1934334B2 (en) Anhydrous preparation based on saturated fatty alcohols and glycol solvents
DE2712030A1 (en) PHARMACEUTICAL COMPOSITION WITH LIPOSOME CONTENT
DE3402880C2 (en)
DE2707878C2 (en) Use of mono- and / or diglycerides of medium-chain fatty acids
DE3836971C1 (en)
DE3738236A1 (en) BIT CAPSULE
EP0456106B1 (en) Stable emulsion for pharmaceutical administration, process for its preparation and use thereof as pharmaceutical
DE4431251C2 (en) Skin cream
DE4018995C2 (en) Corticoid steroid-containing agent and method for improving the therapeutic efficacy of lipid-soluble corticosteroids
DE2447699A1 (en) STEROID TOPICAL OINTMENT BASE
DE2437847C3 (en) 16?, 17? -Cyclopentylidenedioxy-9α-fluorine-11β, 21-dihydroxy-1,4-pregnadiene-3,20-dione-21-acetate, process for its preparation and pharmaceutical agent containing it
DE3540175C2 (en) Dithranol-containing pharmaceutical preparation
EP0804150B1 (en) Lotions containing fatty acid derivatives
WO1995024193A1 (en) Topical preparations
DE69736678T2 (en) DERMATOLOGICAL COMPOSITIONS
DE19517147C2 (en) Acyclovir preparation
EP1325734B1 (en) Process for the preparation of ozone and peroxide derivatives of fatty acids or their esters in the form of a spreadable ointment
EP1344517A1 (en) Stable dispersion concentrates
DE2646435A1 (en) Stable oil in water emulsion - obtd. by adding water to oil in solvent emulsion
EP0230226B1 (en) Antimycotic emulsions
DE2526986C2 (en)
EP0003794A1 (en) Testosterone esters, process for their preparation and pharmaceutical compositions containing them
DE2256129C3 (en) 17-esters of 6α, 9α; -Difluoro-21-deoxyprednisolone, process for the production thereof and medicaments containing them
DE2809618A1 (en) NEW THERAPEUTIC PREPARATION AND METHOD FOR THE PRODUCTION THEREOF
DE2622856A1 (en) PROCESS FOR MANUFACTURING COCOA BUTTER SUBSTITUTE

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase