Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1991-07-26
1994-01-25
Ford, John M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514245, 514503, 514504, 544181, 556 72, A61K 31555, A61K 31285, A61K 3129, C07F 976
Patent
active
052815889
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to organometallic compounds, methods for their preparation as well as pharmaceutical compositions containing the said compounds. The subject of the invention is more particularly the use of such pharmaceutical compositions in the treatment of parasitic diseases such as the trypanosomiases and the filariases.
The chemotherapeutic treatment of these parasitic diseases in man and animals poses serious problems at the present time.
The compound Mel B, discovered by E. FRIEDHEIM (patent filed in the UNITED STATES and published in 1953 under the U.S. Pat. No. 2,659,723) is the most commonly used medicine for the treatment of second stage human trypanosomiases. However, this compound possesses many disadvantages, one of the most serious of which is the triggering of unpredictable lethal encephalopathies which are produced in 5% of the individuals treated with Mel B (WHO/FAO EXPERT COMMITTEE (1979); The African Trypanosomiases. WHO TECHNICAL REPORT SERIES, N 635).
This patent also describes other compounds related to Mel B possessing an atom of arsenic (As) or antimony (Sb) forming part of a 5-membered ring structure. A process likely to lead to the production of a derivative related to Mel B in which an atom of antimony forms parts of a 6-membered ring structure is described as an example in this patent.
However, no physicochemical or biological property of the product likely to be obtained in the above-mentioned example (which corresponds to 2-p-(4,6-diamino-s-triazin-2-yl-amino) phenyl-1,3,2-dithia stibane-4,5,6-triol) was mentioned in this patent.
The compound Mel W (FRIEDHEIM E. A. H. (1966) German patent No. 1,229,543) is a water-soluble derivative of Mel B, and has been used in veterinary and human therapy. However, this latter application has been abandoned on account of many problems of toxicity.
In addition to the problem of the toxic effect of the medicines mentioned above, a considerable number of strains of trypanosomes resistant to these products has also been discovered.
These two medicines, Mel B and Mel W, are compounds similar to the dithiarsolane type with 5 members (5-membered ring); the only structural difference between these two compounds consists of a different substituent on the 5-membered ring. The synthesis of this 5-membered ring is carried out starting from vicinal dithiols (i.e. thiols borne by two neighbouring carbon atoms).
The present invention relates to the organometallic compounds represented by the following general formula: ##STR4## in which: M represents arsenic (As) or antimony (Sb), represent: substituted by one or two alkyl groups of 1 to 18 carbon atoms, a group of formula ##STR5## in which R.sub.6 represents a methyl --CH.sub.3 or an amine --NH.sub.2, a group ##STR6## a --NO.sub.2 group a --COOH group ##STR7## in which X represents a nitrogen atom or a CH group, particular from 4 to 6 carbon atoms, this alkylene group being substituted, where appropriate: represents a hydrogen atom, or a hydroxyl --OH, or an acid --COOH, or an amine --NH.sub.2, or a sulfonic --SO.sub.3 H function, and n represents an integer varying from 0 to 10, or by several identical or different groups of formula --(CH.sub.2).sub.n --R.sub.7 mentioned above, --R.sub.7 defined above, in particular one or more salts of Na or K when R.sub.7 represents an acidic function or one or more hydrochlorides when R.sub.7 represents an amine function, ##STR8## designated hereafter by: 2-p-(4,6-diamino-s-triazin-2-yl-amino)phenyl-1,3,2-dithia-stibane-4,5,6-tr iol.
The present invention relates more particularly to the compounds represented by the following general formula: ##STR9## in which: M represents arsenic (As) or antimony (Sb), ##STR10## A represent an alkylene group of 1 to 18 carbon atoms, in particular from 2 to 4 carbon atoms, possibly substituted by one or more hydroxyl --OH functions.
The subject of the invention is more particularly the following compounds: ##STR11##
The present invention also relates to the process for obtaining the compounds defined above, comprising t
REFERENCES:
patent: 2659723 (1947-01-01), Friedheim
patent: 2664432 (1953-12-01), Friedheim
Bajyana-Songa Emmanuel
Hamers Raymond
Maes Ludo
Ford John M.
Gupta Y. N.
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