DE2932691A1 - Antimycotic tablets contg. micronised azole derivs. - together with acid and/or buffer - Google Patents

Antimycotic tablets contg. micronised azole derivs. - together with acid and/or buffer

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Publication number
DE2932691A1
DE2932691A1 DE19792932691 DE2932691A DE2932691A1 DE 2932691 A1 DE2932691 A1 DE 2932691A1 DE 19792932691 DE19792932691 DE 19792932691 DE 2932691 A DE2932691 A DE 2932691A DE 2932691 A1 DE2932691 A1 DE 2932691A1
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DE
Germany
Prior art keywords
acid
contain
active ingredient
antimycotic
buffer
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.)
Withdrawn
Application number
DE19792932691
Other languages
German (de)
Inventor
Karl-Heinz Prof. Dr. B+chel
Manfred 5063 Overath Bücheler
Wolfgang Dr. Gau
Manfred Dr. 5600 Wuppertal Plempel
Hansjürgen 5600 Wuppertal Ploschke
Erik Regel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
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Bayer AG
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 Bayer AG filed Critical Bayer AG
Priority to DE19792932691 priority Critical patent/DE2932691A1/en
Priority to EP80104555A priority patent/EP0024023B2/en
Priority to DE8080104555T priority patent/DE3070778D1/en
Priority to FI802488A priority patent/FI802488A/en
Priority to JP10838380A priority patent/JPS5629516A/en
Priority to NZ194602A priority patent/NZ194602A/en
Priority to ZA00804830A priority patent/ZA804830B/en
Priority to IL60803A priority patent/IL60803A/en
Priority to IE1677/80A priority patent/IE50091B1/en
Priority to GR62636A priority patent/GR69897B/el
Priority to CA000357971A priority patent/CA1141297A/en
Priority to AU61700/80A priority patent/AU534014B2/en
Publication of DE2932691A1 publication Critical patent/DE2932691A1/en
Priority to US06/581,527 priority patent/US4585782A/en
Priority to SG120/88A priority patent/SG12088G/en
Priority to HK179/89A priority patent/HK17989A/en
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • A61P31/10—Antimycotics

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  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Reproductive Health (AREA)
  • Urology & Nephrology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Antimycotic compsns. contain azole (pref. imidazole or triazole) derivs. (I) and conventional tabletting aids, with the improvement that (I) are present as particles smaller than 4 microns and the compsns. also contain an acid and/or a buffer system comprising an organic acid and its salt.. The tabletted compsns. are esp. useful for intravaginal treatment of vaginal mycosis (e.g. due to Candida or Torulopsis spp.). They provide more rapid release of (I) than conventional tablets.

Description

Antimykotische Mittel mit höherer Freisetzung derAntifungal agents with higher release of the

Wirkstoffe Die vorliegende Erfindung betrifft neuartige Formulierungen der bekannten antimykotischen Azolderivate, die eine höhere Freisetzung der Wirkstoffe aufweisen und dadurch eine Kurzzeittherapie ermöglichen.Active ingredients The present invention relates to novel formulations the well-known antifungal azole derivatives, which have a higher release of the active ingredients and thus enable short-term therapy.

Für die Behandlung von Vaginal-Infektionen mit Pilzen sind bereits Zubereitungen von antimykotischen Azolderivaten bekannt geworden, die Vaginaltabletten darstellen. Mit diesen Zubereitungen werden für eine vollständige Vaginal-Sanierung 14 bis 3 Tage Therapiezeit benötigt. Dies ist u.a. darauf zurückzuführen, daß in den üblichen Vaginaltablettenzubereitungen die enthaltenen Wirkstoffe nur zum Teil in wäßrigen Medien löslich sind.For the treatment of vaginal infections with fungi are already available Preparations of antifungal azole derivatives have become known, the vaginal tablets represent. These preparations are used for a complete vaginal cleanup 14 to 3 days of therapy time are required. This is due, among other things, to the fact that in the usual vaginal tablet preparations only partially contain the active ingredients are soluble in aqueous media.

Um zu einer Verkürzung der Therapiedauer zu kommen, benötigt man, besonders zur Eliminierung der Keime in Vaginalsekret, eine höhere Freisetzung der Wirkstoffe im wäßrigen Milieu. Dafür sind die bekannten Formulierungen nur begrenzt geeignet, weil sich von dem vorhandenen Wirkstoffangebot nur ein kleiner Anteil im Flüssigkeits-olumen der Vagina löst.In order to shorten the duration of therapy, you need especially to eliminate the germs in vaginal secretions, a higher release of the Active ingredients in an aqueous medium. The known formulations are only limited for this suitable because only a small one differs from the existing range of active ingredients proportion of dissolves in the fluid volume of the vagina.

Wenn man nun durch weitere Erhöhung der Wirkstoffkonzentration eine Verkürzung der Therapiedauer, z.B.If you now, by further increasing the concentration of the active ingredient, a Shortening the duration of therapy, e.g.

auf einen Tag bei einmaliger Applikation, erreichen will, muß man für eine optimale Freisetzung des Wirkstoffes Sorge tragen.on a day with a single application, you have to ensure an optimal release of the active ingredient.

Es wurde nun gefunden, daß solche Formulierungen antimykotischer Azolderivate, die den Wirkstoff in feinstgemahlener Form, d.h. im Partikelgrößen unter 4ß, die üblichen Tablettenhilfsstoffe und außerdem eine Säure und/oder ein Puffersystem, bestehend aus einer organischen Säure und deren Salzen, enthalten, eine optimale Freisetzung des Wirkstoffes und damit eine verkürzte Therapiedauer von einem Tag durch das Erreichen von fungiziden Konzentrationen des Wirkstoffs, z.B. Clotrimazol, ermöglichen.It has now been found that such formulations of antifungal azole derivatives, which the active ingredient in finely ground form, i.e. in particle sizes below 4ß, the usual tablet excipients and also an acid and / or a buffer system, consisting of an organic acid and its salts, contain an optimal Release of the active ingredient and thus a shortened therapy duration of one day by achieving fungicidal concentrations of the active ingredient, e.g. clotrimazole, enable.

Dieser Effekt wird dadurch erreicht, daß der in den bekannten Formulierungen enthaltene pH-Wert von über 5 bis 6 auf unter 3 bis 4 in wäßriger Lösung vermindert wird.This effect is achieved by the fact that in the known formulations contained pH value reduced from over 5 to 6 to below 3 to 4 in aqueous solution will.

Die dadurch erzielte Erhöhung der Wirkstofffreisetzung kann bis zu einer Zehnerpotenz betragen.The resulting increase in the release of active ingredients can be up to be a power of ten.

Wenn man darüber hinaus noch für eine bestimmte Ionenkonzentration sorgt, wird die Löslichkeit der Azolderivate vermöge der Ionenstärke durch Ionenbindung weiter gesteigert. Die Ionenstärke liegt hierbei zwischen 0,1 - 0,8.If you also look for a certain ion concentration ensures the solubility of the azole derivatives by virtue of the ionic strength through ionic bonding further increased. The ionic strength is between 0.1 and 0.8.

Wirkstoffe, die in dieser Weise formuliert werden können, sind alle antimykotisch wirksamen Azolderivate, insbesondere Imidazol- und Triazolderivate.Active ingredients that can be formulated in this way are all antifungal azole derivatives, especially imidazole and triazole derivatives.

Beispielsweise seien die Verbindungen der nachstehenden Formeln genannt: Zahlreiche weitere antimykotisch wirksame Azolderivate sind bekannt aus der DE-OS 24 30 039.The compounds of the following formulas may be mentioned as examples: Numerous other antifungal azole derivatives are known from DE-OS 24 30 039.

Insbesondere wurde gefunden, daß solche Vaginaltablettenzubereitungen der Verbindung der Formel II, die außerdem Milchsäure und Calciumlactat, oder der Formeln I und III, die außerdem Citronensäure und primäres Natriumcitrat enthalten, so viel besser formuliert sind, daß eine einmalige Applikation Vaginalmykosen, z.B. hervorgerufen durch Candida-Arten und Torulopsis-Arten, zur Abheilung gebracht werden können. Die Verträglichkeit solcher Formulierungen ist einwandfrei.In particular, it has been found that such vaginal tablet preparations the compound of the formula II, which also contains lactic acid and calcium lactate, or the Formulas I and III, which also contain citric acid and primary sodium citrate, are so much better formulated that a single application of vaginal mycoses, e.g. caused by Candida species and Torulopsis species can. Such formulations are perfectly compatible.

Auch andere Puffersysteme und/oder die Säuren oder die sauren Salze allein beeinflussen die Zubereitungen in der angegebenen günstigen Weise. Solche können sein: Citronensäure / Na-citrat primär Milchsäure / Na-lactat Weinsäure DL / K-Na-tartrat Adipinsäure Ascorbinsäure / Ethylendiamintetraessigsäure - 1/2 Na-salz bzw. Na-salz Fumarsäure Glykokoll-Puffer Kaliumhydrogenphthalat-Puffer Tartrat-Puffer (KHC2H406) Phosphat-Puffer Unter üblichen Tabelettenhilfsstoffen werden hier die nachstehenden verstanden.Also other buffer systems and / or the acids or the acidic salts alone influence the preparations in the indicated favorable manner. Such can be: citric acid / sodium citrate primarily lactic acid / sodium lactate tartaric acid DL / K sodium tartrate adipic acid ascorbic acid / ethylenediaminetetraacetic acid - 1/2 Na salt or Na salt fumaric acid glycocolla buffer potassium hydrogen phthalate buffer tartrate buffer (KHC2H406) phosphate buffer Among the usual tablet auxiliaries the following are understood here.

Stärke, z.B. Maisstärke, Reisstärke, Kartoffelstärke, Weizenstärke; Milchzucker, Glukose, Saccharose, mikrokristalline Cellulose, Siliciumdioxid kolloidal, Magnesiumstearat, Stearinsäure, Talcum, Polyvinylpyrrolidon (linear und quervernetzt), Natriumchlorid, Polyethylenglykol, Hydroxypropylmethylcellulose, Gelatine, Ca-Phosphate, Cellulose, Mannit, Natriumcarboxymethylstärke, Natriumcarbonat, Natriumbicarbonat, Calciumcarbonat, Natriumcarboxymethylcellulose (linear und quervernetzt), Magnesiumcarbonat.Starch, e.g., corn starch, rice starch, potato starch, wheat starch; Lactose, glucose, sucrose, microcrystalline cellulose, colloidal silicon dioxide, Magnesium stearate, stearic acid, talc, polyvinylpyrrolidone (linear and cross-linked), Sodium chloride, polyethylene glycol, hydroxypropylmethyl cellulose, gelatin, calcium phosphate, Cellulose, mannitol, sodium carboxymethyl starch, sodium carbonate, sodium bicarbonate, Calcium carbonate, sodium carboxymethyl cellulose (linear and cross-linked), magnesium carbonate.

Weitere Tabelettenhilfsstoffe siehe "Die Tablette, Grundlagen und Praxis des Tablettierens, Granulierens und Dragierens" von W. A. Ritschel, S. 85 - 144, sowie "Katalog pharmazeutischer Hilfsstoffe" verfaßt von einer Arbeitsgruppe der Firmen Ciba-Geigy, Hoffmann-La Roche und Sandoz, Basel 1974.For more tablet additives see "The tablet, basics and The practice of tabletting, granulating and coating "by W. A. Ritschel, p. 85 - 144, as well as "Catalog of pharmaceutical auxiliaries" written by a working group of the companies Ciba-Geigy, Hoffmann-La Roche and Sandoz, Basel 1974.

Beispiel 1 500 g Wirkstoff der Formel I, werden in einem Wirbelschichtgranulator mit folgenden Mengen an Tablettenhilfsstoffen zunächst trocken gemischt: 190 g Citronensäure, 195 g Na-citrat prim., 314 g Milchzucker, 148 g Maisstärke, 230 g mikrokristalline Cellulose, 4 g Polyethylenglykol-Sorbitanoleat, dann wird durch Einsprühen von Wasser granuliert und getrocknet. Dann werden dem Granulat 34 g Mg-stearat und 85 g quervernetztes Polyvinylpyrrolidon zugemischt und zu Vaginaltabeletten mit einem Gesamtgewicht von 1700 mg tablettiert.Example 1 500 g of active ingredient of the formula I are in a fluidized bed granulator dry mixed with the following amounts of tablet excipients: 190 g citric acid, 195 g Na citrate prim., 314 g lactose, 148 g corn starch, 230 g microcrystalline Cellulose, 4 g of polyethylene glycol sorbitan oleate, then is sprayed with water granulated and dried. Then 34 g of Mg stearate and 85 g of cross-linked stearate are added to the granulate Polyvinylpyrrolidone mixed in and made into vaginal tablets with a total weight of 1700 mg tabletted.

Beispiel 2 100 g Wirkstoff der Formel II, werden im Planetenmischer mit 140 g Milchsäure, 60 g Ca-lactat, 1010 g Milchzucker, 238 g Maisstärke trocken gemischt, mit einem Kleister bestehend aus 50 g Maisstärke und 300 g Wasser granuliert, in einem Wirbelschicht-, Vakuum- oder Umlufttrockner getrocknet, dann die Granulate mit 17 g Mg-stearat und 85 g quervernetztem Polyvinylpyrrolidon versetzt und zu 1700 mg schweren Vaginaltabletten verpreßt.Example 2 100 g of active ingredient of the formula II are placed in a planetary mixer with 140 g lactic acid, 60 g calcium lactate, 1010 g lactose, 238 g dry corn starch mixed, granulated with a paste consisting of 50 g corn starch and 300 g water, dried in a fluidized bed, vacuum or circulating air dryer, then the granules mixed with 17 g of magnesium stearate and 85 g of crosslinked polyvinylpyrrolidone and added 1700 mg vaginal tablets compressed.

Beispiel 3 500 g Wirkstoff der Formel III, werden mit 831 g Milchzucker, 200 g Ethylendiamintetraessigsäure - 1/2 Na-Salz, 126 g Maisstärke, 4 g Siliciumdioxid kolloidal und 4 g Polyethylenglykol-Sorbitanoleat in einem Planetenmischer trocken vermischt, mit Wasser im selben Gerät granuliert, in der Wirbelschicht im Vakuum oder Umlufttrockenschrank getrocknet, dem erhaltenen Granulat noch 39 g Mg-stearat zugemischt und dann zu 1700 g schweren Vaginaltabletten verpreßt.Example 3 500 g of active ingredient of the formula III are mixed with 831 g of lactose, 200 g of ethylenediaminetetraacetic acid - 1/2 Na salt, 126 g of corn starch, 4 g of silicon dioxide colloidal and 4 g of polyethylene glycol sorbitan oleate dry in a planetary mixer mixed, granulated with water in the same device, in the fluidized bed in a vacuum or a circulating air dryer, 39 g of Mg stearate are added to the granules obtained mixed in and then compressed into 1700 g vaginal tablets.

Claims (1)

Patentansprüche: 1. Antimykotische Mittel mit höherer Freisetzung der Wirkstoffe, enthaltend Azolderivate und übliche Tablettenhilfsstoffe, dadurch gekennzeichnet, daß sie den Wirkstoff in Partikeln unter 4 und außerdem eine Säure und/oder ein Puffersystem, bestehend aus einer organischen Säure und deren Salzen enthalten. Claims: 1. Higher release antifungal agents the active ingredients, containing azole derivatives and customary tablet auxiliaries, thereby characterized in that they contain the active ingredient in particles below 4 and also an acid and / or a buffer system consisting of an organic acid and its salts contain. /2, Antimykotische Mittel nach Anspruch 1, dadurch gekennzeichnet, daß sie als Wirkstoff die Verbindung der Formel und außerdem Citronensäure und primäres Natriumcitrat enthalten./ 2, Antimycotic agents according to claim 1, characterized in that they use the compound of the formula as active ingredient and also contain citric acid and primary sodium citrate. 3. Antimykotische Mittel nach Anspruch 1, dadurch gekennzeichnet, daß sie als Wirkstoff die Verbindung der Formel und außerdem Milchsäure und Calciumlactat enthalten.3. Antifungal agents according to claim 1, characterized in that they are the compound of the formula as active ingredient and also contain lactic acid and calcium lactate. 4. Antimykotische Mittel nach Anspruch 1, dadurch gekennzeichnet, daß sie als Wirkstoff die Verbindung der Formel und außerdem Citronensäure und primäres Natriumcitrat enthalten.4. Antifungal agents according to claim 1, characterized in that they are the compound of the formula as active ingredient and also contain citric acid and primary sodium citrate. 5. Antimykotische Mittel nach Anspruch 1, dadurch gekennzeichnet, daß sie in wäßriger Lösung einen pH-Wert von 3 - 4 aufweisen.5. Antifungal agents according to claim 1, characterized in that that they have a pH of 3-4 in aqueous solution. 6. Antimykotische Mittel nach Anspruch 1, dadurch gekennzeichnet, daß sie eine Ionenstärke von 0,1 - 0,8 aufweisen.6. Antifungal agents according to claim 1, characterized in that that they have an ionic strength of 0.1-0.8.
DE19792932691 1979-08-11 1979-08-11 Antimycotic tablets contg. micronised azole derivs. - together with acid and/or buffer Withdrawn DE2932691A1 (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
DE19792932691 DE2932691A1 (en) 1979-08-11 1979-08-11 Antimycotic tablets contg. micronised azole derivs. - together with acid and/or buffer
EP80104555A EP0024023B2 (en) 1979-08-11 1980-08-01 Antimycotic agents with enhanced release of the active ingredients
DE8080104555T DE3070778D1 (en) 1979-08-11 1980-08-01 Antimycotic agents with enhanced release of the active ingredients
FI802488A FI802488A (en) 1979-08-11 1980-08-07 ANTIMYKOTISKA MEDEL MED HOEGRE FRIGOERING AV VERKSAMMA MEDEL
IL60803A IL60803A (en) 1979-08-11 1980-08-08 Vaginal tablets comprising antimycotic azole derivatives with a relatively high release rate
NZ194602A NZ194602A (en) 1979-08-11 1980-08-08 Fast-release antimycotic agents containing an azole derivatives
ZA00804830A ZA804830B (en) 1979-08-11 1980-08-08 Antimycotic agents which release the active compounds at a relatively high rate
JP10838380A JPS5629516A (en) 1979-08-11 1980-08-08 Antiieumycetes agent
IE1677/80A IE50091B1 (en) 1979-08-11 1980-08-08 Antimycotic vaginal tablets with increased bioavailability of the active compounds
GR62636A GR69897B (en) 1979-08-11 1980-08-09
CA000357971A CA1141297A (en) 1979-08-11 1980-08-11 Antimycotic agents which release the active compounds at a relatively high rate
AU61700/80A AU534014B2 (en) 1979-08-11 1980-08-25 Antimycotic agents
US06/581,527 US4585782A (en) 1979-08-11 1984-02-21 Azole derivatives antimycotic agents which release the active compounds at a relatively high rate
SG120/88A SG12088G (en) 1979-08-11 1988-02-19 Antimycotic agents with enhanced release of the active ingredients
HK179/89A HK17989A (en) 1979-08-11 1989-03-02 Antimycotic agents with enhanced release of the active ingredients

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19792932691 DE2932691A1 (en) 1979-08-11 1979-08-11 Antimycotic tablets contg. micronised azole derivs. - together with acid and/or buffer

Publications (1)

Publication Number Publication Date
DE2932691A1 true DE2932691A1 (en) 1981-04-09

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DE19792932691 Withdrawn DE2932691A1 (en) 1979-08-11 1979-08-11 Antimycotic tablets contg. micronised azole derivs. - together with acid and/or buffer

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Country Link
JP (1) JPS5629516A (en)
DE (1) DE2932691A1 (en)
ZA (1) ZA804830B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8322364D0 (en) * 1983-08-19 1983-09-21 May & Baker Ltd Compositions of matter
JPH01127796U (en) * 1988-02-22 1989-08-31
JP2020075921A (en) * 2018-11-02 2020-05-21 ロート製薬株式会社 Vaginal solid pharmaceutical composition

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2430039A1 (en) * 1974-06-22 1976-01-08 Bayer Ag AZOLANTIMYCOTICS AS COSMETIC AGENTS
DE1911646B2 (en) * 1969-03-07 1977-05-18 Bayer Ag, 5090 Leverkusen HETEROCYCLICALLY SUBSTITUTED N-DIPHENYLMETHYLIMIDAZOLE
DE2016839B2 (en) * 1970-04-09 1978-07-20 Bayer Ag, 5090 Leverkusen Phenyl- (4-phenoxyphenyl) -imidazol-1-yl-methanes, processes for their preparation and medicaments containing these compounds
DE2044621B2 (en) * 1970-09-09 1978-11-09 Bayer Ag, 5090 Leverkusen 33-D ^ phenyl-3-imidazol-l-yl-propine, process for their preparation and their use as medicaments
DE2053080B2 (en) * 1970-10-29 1978-12-14 Bayer Ag N-substituted imidazoles and their use as drugs

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1911646B2 (en) * 1969-03-07 1977-05-18 Bayer Ag, 5090 Leverkusen HETEROCYCLICALLY SUBSTITUTED N-DIPHENYLMETHYLIMIDAZOLE
DE2016839B2 (en) * 1970-04-09 1978-07-20 Bayer Ag, 5090 Leverkusen Phenyl- (4-phenoxyphenyl) -imidazol-1-yl-methanes, processes for their preparation and medicaments containing these compounds
DE2044621B2 (en) * 1970-09-09 1978-11-09 Bayer Ag, 5090 Leverkusen 33-D ^ phenyl-3-imidazol-l-yl-propine, process for their preparation and their use as medicaments
DE2053080B2 (en) * 1970-10-29 1978-12-14 Bayer Ag N-substituted imidazoles and their use as drugs
DE2430039A1 (en) * 1974-06-22 1976-01-08 Bayer Ag AZOLANTIMYCOTICS AS COSMETIC AGENTS

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HELWIG, B.: Moderne Arzneimittel, S. 643-648 (1972) *
RITSCHEL, W.A.: Angewandte Biopharmazie, S. 293- 301 (1973) *

Also Published As

Publication number Publication date
JPS5629516A (en) 1981-03-24
JPS6241566B2 (en) 1987-09-03
ZA804830B (en) 1981-08-26

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