Phenyl propane derivatives as antibiotics and lipoxygenase inhib

Details Phenyl propane derivatives as antibiotics and lipoxygenase inhib Phenyl propane derivatives as antibiotics and lipoxygenase inhib

1996-07-30

1998-09-22

Reamer, James H.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

560144, 514475, 514546, 549549, A61K 31235

Patent

active

058114580

DESCRIPTION:

BRIEF SUMMARY
In recent times the use of natural materials in medicine has become increasingly important. Such analogue natural materials must however be simple and cost-effective to produce, and their therapeutic action must at least approximate to or even entirely equate to that of synthetically-produced preparations. Until now, these requirements have been satisfied by very few natural preparations.
Proceeding from this basis it is the object of the present invention to propose therapeutic active ingredients which are derived from natural materials, these analogue natural materials having to be capable of manufacture by simple and cost-effective methods. The therapeutic action is to correspond approximately to that of synthetic preparations.
This object is achieved by the phenyl propane derivatives defined in more detail in Patent claim 1. Patent claims 4 to 6 show preferred uses of the phenyl propane derivates, while Patent claims 6 and 7 feature the use of the phenyl propane derivates as medicine.
Surprisingly, it has become apparent that the phenyl propane derivates (phenyl proponoids) contained in coreopsis types (asteraceae), with their unusual structural features, are outstandingly suitable as a therapeutic active ingredient, particularly as an antibacterial agent. The phenyl propane derivates according to the invention are diesters of 1'-hydroxyeugenol or diesters of (epoxy)-E/Z-coniferyl alcohols. The occurrence of the diesters of 1'-hydroxyeugenol and of the epoxy-Z coniferyl alcohol (natural substances) appears to be largely restricted to the species coreopsis. Until now only the diacetate of 1'-hydroxyeugenol has been found outwith the species coreopsis in alpinia galanga (zingiberaceae).
It is particularly preferred if the alkyl residue R1 or R2 of the ester group is either methyl, isopropyl, 1-methylpropyl or isobutyl. Quite particularly preferred are the phenyl propane derivates with R1 isopropyl and R2 methyl, isopropyl, 1-methylpropyl or isobutyl.
The phenyl propane derivates described above have surprisingly proved to be extensively selectively-acting antibacterial materials. They are capable of selectively combating problem germs such for example as staph. epidermidis, staph. haemolyticus, or acinetobacter calcoaceticus. In this respect it has become apparent that the antibacterial effect is in part better than for example that of the known antibiotic Cefuroxim.RTM..
Apart from this use as antibiotics, the abovenamed, more extensively described phenyl propane derivates are also suitable for inhibiting the activity of 5-lipoxygenase in human leucocytes. That is, 5-lipoxygenase catalyses the first two reaction stages of the conversion of arachidonic acid to the biologically highly-active leucotrienes B.sub.4, C.sub.4, D.sub.4 and E.sub.4. Leucotrienes are important mediators in infective and allergenic reactions. There is therefore great interest in developing corresponding inhibitors which suppress the activity of 5-lipoxygenase. It is now surprisingly revealed that the phenyl propane derivates described above are also suitable for inhibition of the 5-lipoxygenase activity in basophile leukaemia cells of the rat, and in human leucocytes.
Accordingly, by means of the phenyl propane derivates proposed according to the invention, there is proposed a new therapeutic active ingredient with interesting properties in various fields of application.
The phenyl propane derivates may thus be used in medicines with carrier, additive and accessory agents known per se.
The phenyl propane derivates according to the invention may in this case preferably be applied percutaneously, per orem or rectally. A further field of application is the coating of catheters.
In the case of percutaneous application, the phenyl propane derivates are preferably used in the form of powders, ointments, solutions or occlusion dressings. This is advantageous as, after penetration of the skin (hair follicles, injuries) or of the mucous membrane, staphylococci show a tendency to remain at the locus of penetration, causing local infections

REFERENCES:
patent: 4533746 (1985-08-01), Wilson et al.
patent: 5283352 (1994-02-01), Backstrom et al.
Mitsui et al, Chem. Abst, vol. 86, #106, 806 h (1977).

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