Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Patent
1991-08-05
1992-11-24
Berch, Mark L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
544 9, 544343, C07D51304, C07D51314, C07D491048
Patent
active
051663481
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE ART
This invention relates to organic chemistry, and more particularly it relates to new compounds, bornyl and isobornyl esters of carboxylic acids of condensed tetrahydroquinoxalines having antiviral properties.
PRIOR ART
Known in the prior art are derivatives of 3a, 4, 9,9a-tetrahydrofuro (2,3a-b) quinoxaline (O. N. Chupakhin, V. N. Charushin, A. I. Chernyshev, "Application of .sup.1 H, .sup.13 C and .sup.15 N NMR in the Chemistry of 1,4-Diazines", Progress in Nuclear Magnetic Resonance Spectroscopy, Oxford; Pergamon Press, 1988, vol. 20 (2), pp. 177-184. However, the compound are not effective against viruses.
DISCLOSURE OF THE INVENTION
The proposed compounds are novel and have not been described in the literature.
The object of the invention is to provide new compounds having high antiviral activity and low toxicity.
The object is accomplished by provision of new compounds, which, according to the invention, are bornyl and isobornyl esters of carboxylic acids of condensed tetrahydroquinoxalines of the general formula: ##STR4## where: R.sup.1 =CH.sub.3 ; C.sub.2 H.sub.5 ; ##STR5##
The proposed compounds have low toxicity and are active against influenza virus A and B. The most active compound, according to the invention, is isobornyl ester of 2,9-dimethyl-3a,4,9,9a-tetrahydrofuro 2,3-b quinoxaline-3-carboxylic acid of the formula ##STR6##
Said compound has a broad spectrum of antiviral activity, i.e., it is highly active against tick-borne encephalitis virus, epidemic strains of influenza virus A, B and C resistant to remantadine, and also against the agent causing respiratory syncytial infection.
Best Mode of Carrying Out the Invention
The proposed new compounds-bornyl and isobornyl esters of carboxylic acid of condensed tetrahydroquinoxalines are colorless crystals readily soluble in chloroform and dimethylsulphoxide, moderately soluble in ethyl ether and ethyl alcohol, and sparingly soluble in water.
The structure of the proposed compounds was confirmed by the findings of elemental analysis and .sup.1 H NMR spectroscopy. The proposed compounds are active against viruses. The antiviral activity of the proposed compounds was studied on experimental animals.
The activity of the proposed compounds against influenza virus A and B was tested. The following compounds were tested: quinoxaline-3-carboxylic acid (compound 1a); quinoxaline-3-carboxylic acid (compound 1b); quinozaline-3-carboxylic acid (compound 1c); 4a,5,10,10a-hexahydro-1,3,4-thiadiazole [2,3-a] quinoxaline (2,3-d) pyrrole-4carboxylic acid (compound 1d); 4a,5,10,10a-hexahydro-1,3,4-thiadiazole [2,3-a] quinoxaline [2,3-d]-pyrrole-4-carboxylic acid (compound 1e).
The proposed compounds were compared with the known antivirus drugs remantadine and adapromine.
The antiviral activity of the compounds was studied on chick embryos and albino mice infected with the virus.
The studies and estimation of efficacy of the compounds were performed according to the known procedure.
Experiments were carried out on 3 groups of animals (or embryos): test group (the virus and the proposed compounds were given), control group (the virus and distilled water or a 0.9% sodium chloride solution were given) and the group for comparison (the virus and the known antiviral compounds remantadine or adapromine were given).
The virus was given intransally to mice under a mild ether anaesthesia. The antiviral compounds were given per os a in dose of 1 mg per animal.
The results of the test are given in Tables 1 through 5.
TABLE 1 __________________________________________________________________________
Studies on the Antiviral Activity of the Proposed Compound 1a in
Experiments
on Mice Infected with Influenza Virus A and B Compared with the Known
Drugs Remantadine, Adapromine and Control.
Mice infected with influenza virus
influenza virus A
influenza virus B
compound compound
Indices 1a remantadine
control
1a adapromine
control
1 2 3 4 5 6 7
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% of d
Baklykov Vasily G.
Biseniex Egils A.
Charushin Valery N.
Chupakhin Oleg N.
Dubur Gunar Y.
Berch Mark L.
Institut organicheskogo sinteza AN Latvii
Uralsky politekhnichesky institut
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