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BE806838A - Oral hypoglycaemic compsns - contg. N-4-(2-(5-chloro-2-methoxy-benzamido)ethyl-phenylsulphonyl-N'-cyc- lohexylurea in a form for improved absorption - Google Patents

Oral hypoglycaemic compsns - contg. N-4-(2-(5-chloro-2-methoxy-benzamido)ethyl-phenylsulphonyl-N'-cyc- lohexylurea in a form for improved absorption

Info

Publication number
BE806838A
BE806838A BE137345A BE137345A BE806838A BE 806838 A BE806838 A BE 806838A BE 137345 A BE137345 A BE 137345A BE 137345 A BE137345 A BE 137345A BE 806838 A BE806838 A BE 806838A
Authority
BE
Belgium
Prior art keywords
emi
contg
compsns
chloro
ethyl
Prior art date
Application number
BE137345A
Other languages
French (fr)
Original Assignee
Hoechst 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 Hoechst Ag filed Critical Hoechst Ag
Publication of BE806838A publication Critical patent/BE806838A/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841Filling excipients; Inactive ingredients
    • A61K9/4866Organic macromolecular compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/14Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/146Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/14Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605Excipients; Inactive ingredients
    • A61K9/1611Inorganic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/14Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605Excipients; Inactive ingredients
    • A61K9/1629Organic macromolecular compounds
    • A61K9/1641Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841Filling excipients; Inactive ingredients
    • A61K9/485Inorganic compounds

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)

Abstract

Title compsns are prepd by dissolving the active cpd (I) in a molten water sol carrier esp. a polyglycol of m.wt 2,000-20,000, opt. contg a surfactant and/or a solubilising agent and an alkaline material, and granulating the molten mass.

Description

       

   <EMI ID=1.1> 

  
 <EMI ID=2.1> 

  
urée et de ses sels et leur procédé de préparation"  <EMI ID=3.1> 

  
 <EMI ID=4.1> 

  
 <EMI ID=5.1> 

  
Pour assurer un début optimum de l'action et obtenir une durée

  
 <EMI ID=6.1> 

  
 <EMI ID=7.1> 

  
solution du médicament par broyage fin ou par micro-précipitation  et on transformes le médicament finement divisé en des préparations

  
 <EMI ID=8.1> 

  
 <EMI ID=9.1> 

  
représente des. opérations additionnelles coûteuses pour que la substance active soit obtenue dans une grandeur des particules optimale. En particulier.-,.Le broyage fin nécessite des dépenses techniques considérables pour éviter la formation de poussière de la substance très active. 

  
Or la demanderesse a trouvé que l'on peut éviter les opérations

  
 <EMI ID=10.1> 

  
obtenir des compositions pharmaceutiques si l'on dissout ou disperse

  
 <EMI ID=11.1> 

  
 <EMI ID=12.1> 

  
 <EMI ID=13.1> 

  
sous. une formel pharmaceutique, éventuellement en ajoutant d'autres auxiliaires. 

  
 <EMI ID=14.1> 

  
 <EMI ID=15.1> 

  
vitesse de dissolution de diverses autres substances actives. Mais cette publication ne dit rien de la forme finale du médicament et on

  
 <EMI ID=16.1> 

  
substances tensio-actives. 

  
 <EMI ID=17.1> 

  
plupart des cas, substance-active sous forme de solution dans un  <EMI ID=18.1> 

  
comme véhicules on peut utiliser toutes les substances qui dis- 

  
 <EMI ID=19.1> 

  
 <EMI ID=20.1> 

  
qui sont pharmacologiquement acceptables.

  
On utilise, de préférence, des polyglycols ayont un poids molé-  culaire compris entre 2 000 et 20 000, le cas échéant sous forme de mélanges. De plus, on peut utiliser des produits d'addition de polyglycol et d'oxyde de propylène ayant des poids moléculaires compris  entre 5 000 et 15 000, ainsi que leurs mélanges avec des polyglycols.

  
 <EMI ID=21.1> 

  
 <EMI ID=22.1> 

  
On peut utiliser comme véhicules également des amides d'aides,  par exemple l'éthyl-urée, l'anhydride de sarcosine, des amides d'

  
 <EMI ID=23.1> 

  
acide ou l'anhydride glutarique ou d&#65533;autres mélanges eutectiques.

  
Comme additifs tensio -actifs utilisables on peut citer des substances ioniques et non ioniques, physiologiquement acceptables, de préférence des esters de polyéthylène-glycol et d'acides gras.

  
Conviennent comme auxiliaires hydrosolubles additionnels des sels minéraux et organiques, des polymères tels que la polyvinylpyrrolidonc, et du sucre. 

  
Etant donné que la substance active est soumise à des températures élevées lors de la fabrication des préparations conformes à l'invention et qu'une stabilité optimale n'est pas assurée dans tous les cas, selon la constitution des véhicules mis en jeu, il est recommandé d'utiliser le Glibenclamid sous_forme de sel ou d'ajouter au'mélange constitué de la substance active, de l'auxiliaire et du véhicule, des substances alcalines avec lesquelles le Glibenclamid peut former des sels.. 

  
Dans ces systèmes spéciaux, en particulier en présence de polyglycols, des sels organiques bien hydrosolubles, par exemple des sels de pyrrolidine ou de pipéridine, peuvent avoir une stabilité plus mauvaise que le Glibenclamid sous forme d'acide libre. Par consé-  quent, il est particulièrement recommandé d'utiliser des.sels miné- <EMI ID=24.1> 

  
mélanges de Glibenclamid avec des substances alcalines ou faiblement alcalines, par exemple des carbonates ou des.bicarbonates.

  
L'emploi des carbonates ou bicarbonates provoque, par exemple dans du liquide gastrique artificiel, un effet tampon additionnel et en milieu acide il produit une désagrégation des noyaux du granulé, ce qui a pour conséquence une meilleure libération du médicament avec ameublissement de la préparation sous l'action de gaz carbonique. De plus, le gaz carbonique libéré du carbonate ou bicarbonate assure une dispersion fine de la substance active dans l'estomac.

  
Un mode d'exécution préféré du procédé conforme à l'invention consiste donc à disperser ou dissoudre le Glibenclamid dans la masse fondue des véhicules spécifiés ci-dessus, à ajouter à la dispersion ou solution un carbonate ou bicarbonate alcalin ou alcalino-terreux, à transformer la masse fondue en granulé, que l'on utilise, par exemple, pour remplir des capsules.

  
Dans le tableau suivant on a indiqué la stabilité de différentes préparations contenant du Glibenclamid et comme véhicule ou bien une masse fondue de polyglycol 4000 ou un produit d'addition de polypropylène-glycol et d'oxyde d'éthylène. Pour déterminer la stabilité on mesure la quantité de substance active décomposée après chauffage

  
 <EMI ID=25.1> 

  
 <EMI ID=26.1> 

TABLEAU 

  

 <EMI ID=27.1> 
 

  

 <EMI ID=28.1> 


  
+ stéarate de polyoxéthylène 40 

  
+ bicarbonate de potassium 

  
 <EMI ID=29.1> 

  
nettement supérieure à la stabilité de sels organiques de Gliben-. clamid et de l'acide libre dans les mêmes véhicules. 

  
 <EMI ID=30.1> 

  
adjuvants selon des procédés connus par granulation de la matière sèche, de la masse fondue ou avec un solvant. Il est recommandé de préparer le granulé en forme de perles à partir de la masse fondue

  
 <EMI ID=31.1> 

  
 <EMI ID=32.1> 

  
Les granulés eu granulés en forme de perles sont utilisés, de préférence, pour remplir des capsules de gélatine dure. On-peut les transformer également en comprimé.*?, le plus souvent avec addition d'autres adjuvants à action de désagrégation.

  
Les préparations conformes à l'invention se signalent non seule cent par des avantages pharmaceutiques et techniquea mais encore un bon effet thérapeutique de la substance active très peu hydrosoluble dans le but d'assurer une bio-disposition et une résorption sûres.

  
Les exemples suivants illustrent la présente invention. 

  
 <EMI ID=33.1> 

  
 <EMI ID=34.1> 

  
2) 79,10 g de polyglycol 4000 

  
3) 5,00 g de stéarate de polyoxéthylène 40

  
 <EMI ID=35.1> 

  
100,00 g

  
Préparation

  
On mélange les substances 1) à 3), on les fait fondre à une

  
 <EMI ID=36.1>   <EMI ID=37.1> 

  
 <EMI ID=38.1> 

  
l'appareil décrit dans le brevet français sus-mentionné, ou on prépare le granulé de manière connue après solidification de la masse

  
 <EMI ID=39.1> 

  
 <EMI ID=40.1> 

  
chacune correspondant à une teneur de 2,5 mg de Glibenclamid par capsule. 

  
 <EMI ID=41.1> 

  
 <EMI ID=42.1> 

  
 <EMI ID=43.1> 

  
 <EMI ID=44.1> 

  
 <EMI ID=45.1> 

  
 <EMI ID=46.1> 

  
 <EMI ID=47.1> 

  
 <EMI ID=48.1> 

  
 <EMI ID=49.1> 

  
On mélange les substances 1 à 3 et on les fait fondre à 70 -

  
&#65533; a¯ &#65533;?&#65533; -

  
 <EMI ID=50.1> 

  
lution on diverse le bicarbonate de potassium 4).

  
On transforme la masse fondue en perles, avantageusement dans

  
 <EMI ID=51.1> 

  
pare le granulé de manière connue après solidification de la masse fondue.

  
Du granulé on remplit, par exemple des capsules de gélatine

  
 <EMI ID=52.1> 

  
à une teneur de 2,5 mg de Glibenclamid par capsule. 

  
 <EMI ID=53.1>  <EMI ID=54.1> 

  
craie ayant une vitesse de dissolution optimale, caractérisée en ce. qu'elle contient comme substance active la N-4 /-2-(5-chloro-2-mé-

  
 <EMI ID=55.1> 

  
physiologiquement acceptable de ce composé, en association avec des véhicules et éventuellement des auxiliaires solubles dans le liquide gastrique.

  
2 - Procédé de préparation d'une composition selon la revendication 1, caractérisé en ce que l'on prépare une solution ou une dispersion de la N-4-/ 2-(5-chloro-2-méthoxybenzamido)-éthyl_7-phénylsulfonyl-N'-cyclohexyl-urée et/ou de ses sels dans des masses fondues de véhicules hydrosolubles, le cas échéant avec addition de substances tensio-actives et/ou d'auxiliaires hydrosolubles et de substances alcalines, on transforme la masse fondue en granulé et l'on met ce granulé sous une forme pharmaceutique.



   <EMI ID = 1.1>

  
 <EMI ID = 2.1>

  
urea and its salts and process for their preparation "<EMI ID = 3.1>

  
 <EMI ID = 4.1>

  
 <EMI ID = 5.1>

  
To ensure an optimum start of the action and obtain a duration

  
 <EMI ID = 6.1>

  
 <EMI ID = 7.1>

  
solution of the drug by fine grinding or micro-precipitation and the finely divided drug is processed into preparations

  
 <EMI ID = 8.1>

  
 <EMI ID = 9.1>

  
represents. costly additional operations so that the active substance is obtained in an optimum particle size. In particular, fine grinding requires considerable technical expenditure to avoid the formation of dust of the highly active substance.

  
However, the applicant has found that it is possible to avoid operations

  
 <EMI ID = 10.1>

  
obtain pharmaceutical compositions if one dissolves or disperses

  
 <EMI ID = 11.1>

  
 <EMI ID = 12.1>

  
 <EMI ID = 13.1>

  
under. a formal pharmaceutical, possibly by adding other auxiliaries.

  
 <EMI ID = 14.1>

  
 <EMI ID = 15.1>

  
rate of dissolution of various other active substances. But this publication does not say anything about the final form of the drug and we

  
 <EMI ID = 16.1>

  
surfactants.

  
 <EMI ID = 17.1>

  
most cases, active substance as a solution in an <EMI ID = 18.1>

  
as vehicles it is possible to use all the substances which disperse

  
 <EMI ID = 19.1>

  
 <EMI ID = 20.1>

  
which are pharmacologically acceptable.

  
Preferably, polyglycols having a molecular weight of between 2000 and 20,000 are used, optionally in the form of mixtures. Additionally, polyglycol and propylene oxide adducts having molecular weights between 5,000 and 15,000 can be used, as well as mixtures thereof with polyglycols.

  
 <EMI ID = 21.1>

  
 <EMI ID = 22.1>

  
Aid amides, for example ethyl urea, sarcosine anhydride, acid amides, can also be used as vehicles.

  
 <EMI ID = 23.1>

  
glutaric acid or anhydride or other eutectic mixtures.

  
As surfactant additives which can be used, mention may be made of physiologically acceptable ionic and nonionic substances, preferably esters of polyethylene glycol and of fatty acids.

  
Inorganic and organic salts, polymers such as polyvinylpyrrolidonc, and sugar are suitable as additional water-soluble auxiliaries.

  
Given that the active substance is subjected to high temperatures during the manufacture of the preparations in accordance with the invention and that optimum stability is not ensured in all cases, depending on the constitution of the vehicles involved, it is necessary Recommended to use Glibenclamid as a salt or to add to the mixture consisting of the active substance, the helper and the vehicle, alkaline substances with which Glibenclamid can form salts.

  
In these special systems, especially in the presence of polyglycols, well water soluble organic salts, for example pyrrolidine or piperidine salts, may have poorer stability than Glibenclamid as free acid. Therefore, it is particularly recommended to use. Mineral salts- <EMI ID = 24.1>

  
mixtures of Glibenclamid with alkaline or weakly alkaline substances, for example carbonates or bicarbonates.

  
The use of carbonates or bicarbonates causes, for example in artificial gastric fluid, an additional buffering effect and in an acidic medium it produces a disintegration of the nuclei of the granule, which results in better release of the drug with loosening of the preparation under the action of carbon dioxide. In addition, the carbon dioxide released from the carbonate or bicarbonate ensures a fine dispersion of the active substance in the stomach.

  
A preferred embodiment of the process in accordance with the invention therefore consists in dispersing or dissolving the Glibenclamid in the melt of the vehicles specified above, in adding to the dispersion or solution an alkali or alkaline earth carbonate or bicarbonate, to transforming the melt into a granule, which is used, for example, to fill capsules.

  
The following table shows the stability of various preparations containing Glibenclamid and as vehicle or a melt of polyglycol 4000 or an adduct of polypropylene glycol and ethylene oxide. To determine the stability, the amount of active substance decomposed after heating is measured.

  
 <EMI ID = 25.1>

  
 <EMI ID = 26.1>

BOARD

  

 <EMI ID = 27.1>
 

  

 <EMI ID = 28.1>


  
+ polyoxethylene 40 stearate

  
+ potassium bicarbonate

  
 <EMI ID = 29.1>

  
significantly higher than the stability of organic salts of Gliben-. clamid and free acid in the same vehicles.

  
 <EMI ID = 30.1>

  
adjuvants according to known methods by granulation of the dry matter, of the melt or with a solvent. It is recommended to prepare the pearl-shaped granule from the melt

  
 <EMI ID = 31.1>

  
 <EMI ID = 32.1>

  
The granules or pearl shaped granules are preferably used to fill hard gelatin capsules. They can also be converted into a tablet. * ?, most often with the addition of other adjuvants with disintegrating action.

  
The preparations in accordance with the invention are not only distinguished by pharmaceutical and technical advantages but also by a good therapeutic effect of the active substance which is very poorly soluble in water with the aim of ensuring safe bio-disposition and absorption.

  
The following examples illustrate the present invention.

  
 <EMI ID = 33.1>

  
 <EMI ID = 34.1>

  
2) 79.10 g of polyglycol 4000

  
3) 5.00 g of polyoxethylene 40 stearate

  
 <EMI ID = 35.1>

  
100.00 g

  
Preparation

  
We mix the substances 1) to 3), we melt them at a

  
 <EMI ID = 36.1> <EMI ID = 37.1>

  
 <EMI ID = 38.1>

  
the apparatus described in the aforementioned French patent, where the granule is prepared in a known manner after solidification of the mass

  
 <EMI ID = 39.1>

  
 <EMI ID = 40.1>

  
each corresponding to a content of 2.5 mg of Glibenclamid per capsule.

  
 <EMI ID = 41.1>

  
 <EMI ID = 42.1>

  
 <EMI ID = 43.1>

  
 <EMI ID = 44.1>

  
 <EMI ID = 45.1>

  
 <EMI ID = 46.1>

  
 <EMI ID = 47.1>

  
 <EMI ID = 48.1>

  
 <EMI ID = 49.1>

  
Mix substances 1 to 3 and melt them to 70 -

  
&#65533; at &#65533;? &#65533; -

  
 <EMI ID = 50.1>

  
lution on various potassium bicarbonate 4).

  
The melt is transformed into pearls, advantageously in

  
 <EMI ID = 51.1>

  
trim the granule in known manner after solidification of the melt.

  
Granules are filled, for example gelatin capsules

  
 <EMI ID = 52.1>

  
at a level of 2.5 mg of Glibenclamid per capsule.

  
 <EMI ID = 53.1> <EMI ID = 54.1>

  
chalk having an optimum dissolution rate, characterized in that. that it contains as active substance N-4 / -2- (5-chloro-2-me-

  
 <EMI ID = 55.1>

  
physiologically acceptable compound, in combination with vehicles and optionally auxiliaries soluble in gastric fluid.

  
2 - Process for preparing a composition according to claim 1, characterized in that a solution or a dispersion of N-4- / 2- (5-chloro-2-methoxybenzamido) -ethyl_7-phenylsulfonyl- is prepared N'-cyclohexyl-urea and / or its salts in melts of water-soluble vehicles, optionally with the addition of surface-active substances and / or water-soluble auxiliaries and alkaline substances, the melt is converted into a granule and this granule is put in a pharmaceutical form.


    

Claims (1)

3 - Procédé selon la revendication 2, caractérisé en ce que l'on utilise comme véhicule des polyglycols ayant un poids moléculaire compris entre 2 000 et 20 000 ou leurs produits d'addition avec de l'oxyde de propylène. 3 - Method according to claim 2, characterized in that one uses as vehicle polyglycols having a molecular weight between 2000 and 20,000 or their adducts with propylene oxide. 4 - Procédé selon la revendication 2 ou la revendication 3, caractérisé en ce que l'on ajoute des substances -tensio-actives qui sont physiologiquement acceptables. 4 - Method according to claim 2 or claim 3, characterized in that one adds -tensio-active substances which are physiologically acceptable. 5 - Procédé selon l'une quelconque des revendications 2 à 4, caractérisé en ce que l'on ajoute comme substance alcaline un carbonate ou un bicarbonate alcalin. 5 - Process according to any one of claims 2 to 4, characterized in that one adds as alkaline substance an alkaline carbonate or bicarbonate.
BE137345A 1972-10-31 1973-10-31 Oral hypoglycaemic compsns - contg. N-4-(2-(5-chloro-2-methoxy-benzamido)ethyl-phenylsulphonyl-N'-cyc- lohexylurea in a form for improved absorption BE806838A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2253318 1972-10-31

Publications (1)

Publication Number Publication Date
BE806838A true BE806838A (en) 1974-04-30

Family

ID=5860488

Family Applications (1)

Application Number Title Priority Date Filing Date
BE137345A BE806838A (en) 1972-10-31 1973-10-31 Oral hypoglycaemic compsns - contg. N-4-(2-(5-chloro-2-methoxy-benzamido)ethyl-phenylsulphonyl-N'-cyc- lohexylurea in a form for improved absorption

Country Status (1)

Country Link
BE (1) BE806838A (en)

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