Oxypricin, a new antibiotic

Details Oxypricin, a new antibiotic Oxypricin, a new antibiotic

1986-03-10

1989-10-10

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D31304

Patent

active

048733482

DESCRIPTION:

BRIEF SUMMARY
CROSS REFERENCE TO RELATED APPLICATIONS

This application is a national phase application corresponding to PCT/HU85/00034 filed 31 May 1985 based upon Hungarian national applications 2125/84 of 31 May 1984 and 2869/84 filed 26 July 1984 under the International Convention.


FIELD OF THE INVENTION

The present invention relates to different components of primycin obtained by the separation of primycin-mixture and to a process for the separation of these components from the antibiotic complex. The invention also relates to a synergistic pharmaceutical composition comprising the said components and to a process for the preparation thereof.


BACKGROUND OF THE INVENTION

The primycin antibiotic complex can be obtained from the culture of strain Thermopolyspora galeriensis belonging to the species of Streptomycetae, its preparation by fermentation is described by Hungarian patent specification No. 153,593.
Primycin is an antibiotic of macrolide type which is characterized in the prior art (J. Chem. Soc., Perkin I. page 816, 1974) by one single formula: [5-{18-(.alpha.-D-arabinofuranosyloxy)-2-butyl-3,7,11,15,19,21,23,25,27-no nahydroxy-4,16,32,34-tetramethyl-1-oxo-oxacyclohexatriaconta-16,32-diene-35 -yl}-4-hydroxyhexyl]-quanidinum sulphate.
Primycin is a very effective antibiotic which can be widely used; it is effective primarily against gram-positive bacterias but also against the polyresistant human pathogenic strains. Resistance has not developed against it as yet.
Our former experiments have already referred to the fact that the primycin composition obtained by fermentation is not a homogeneous substance. Recent developments of chromatography have enabled us to subject the primycin substance mixture to a more detailed searching examination.


DETAILED DESCRIPTION OF THE INVENTION

We have now discovered that the primycin composition obtained by fermentation comprises three major and six minor components and the process of our invention is suitable for the qualitative and micropreparative separation of these components. Surprisingly we have also found that components enhance each other in effect, i.e. they show synergistic activity in various combinations.
We targeted our efforts at separating and isolating the different components of the antibiotic complex produced by strain Thermopolyspora galeriensis. Several chromatographic methods were tested and it was found that thin-layer and coloumn chromatography are the most effective for this purpose.
In the field of thin-layer chromatography (TLC) the use of commercial chromatographic plates, with silica gel adsorbent layer thereafter the high performance thin-layer chromatographic plates with suitable solvent system resulted in the separation of the components with surprisingly high resolution.
According to a preferred embodiment of the separation process of our invention the stock solution of the fat-free, crude, semi-half or pure product derived from the mycelium of strain Thermopolyspora galeriensis is applied onto a TLC chromatoplate, developed, the spots thus obtained are detected and the major and/or minor components of the antibiotic complex are separated.
For the preparation of the stock solution of the crude, semi-half or pure product recovered from the culture medium aqueous solutions of alcohols of 1 to 4 carbon atoms or a mixture thereof, preferably a 25:25:50 by volume mixture of ethanol:n-butanol:water is used. 0.5 to 1 w/v % solution is prepared by the aid of the above mixture and 50 to 200 .mu.g of the substance to be examined is applied to the plate.
In our experiments we used a commercial silica gel chromatographic plate typ Kieselgel 60 F.sub.254 (size: 20.times.20 cm, thickness of the silica gel layer: 0.2 mm). Several solvent mixtures were tested on this plate in order to achieve the best separation of the primycin mixture.
The best separation can be attained when the eluent used comprises halogenated hydrocarbons, organic acids, alcohols, water, and preferably aldehydes.
The following solvents can be used as eluent: halogenated aliphatic

REFERENCES:
patent: 4070376 (1978-01-01), LeMahieu et al.
Aberhart, J., et al., J. Am. Chem. Soc. (1970) 92, pp. 5816-5817.
Aberhart, J., et al., J.C.S. Perkin I (1974), pp. 816-826.

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