Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-12-06
1996-12-31
Bond, Robert T.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
540488, A61K 3155, C07D26720
Patent
active
055894747
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel dibenzothiazepinthione derivatives and to the use of these and certain related compounds as antiviral agents.
A group of dibenzothiazepinthione derivatives has now been found which show activity as antiviral agents. Thus, according to one aspect, the present invention provides compounds of formula (I) ##STR2## wherein: n is 0, 1 or 2; and or more ring substituent(s) selected from: cycloalkyl or C.sub.1-6 alkoxy (where the alkyl or cycloalkyl moiety may be optionally substituted by one or more substituents selected from halogen atoms and hydroxyl groups); different, each represent hydrogen or C.sub.1-6 alkyl; C.sub.1-6 alkyl or C.sub.3-6 cycloalkyl; above; group may be optionally substituted by one or more substituents independently selected from C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy, nitro, halogen and amino; and cycloalkyl; for use in therapy, more particularly for use as an antiviral agent.
According to one embodiment R.sup.3 represents hydrogen.
As used herein the term "alkyl" as a group or part of a group means a straight or branched chain alkyl group. Such alkyl groups preferably have 1 to 3 carbon atoms and are more preferably methyl or ethyl, most preferably methyl.
The present invention also provides the use of a compound of formula (I) or an ester, salt or other physiologically functional derivative thereof for the manufacture of a medicament for the treatment of a viral infection.
The majority of the compounds of formula (I) are novel. According to a further aspect the invention provides compounds of formula (I) as defined above with the provisos applying to those compounds in which R.sup.3 is hydrogen and n is zero that at least one ring substituent R.sup.1 or R.sup.2 is other than hydrogen and that when there is only a single ring substituent R.sup.1 or R.sup.2 other than hydrogen then this substituent is not a chlorine atom in the 2-, 7-, or 8- position.
According to a yet further aspect the invention provides compounds of formula (I) as defined above with the following provisos applying to those compounds in which R.sup.3 is hydrogen and n is zero: hydrogen; then hydrogen this is not a chlorine atom in the 2-, 7-, or 8-position. not:
According to another aspect the invention provides compounds of formula (I) wherein: or more ring substituent(s) selected from: the alkyl or cycloalkyl moiety may be substituted by one or more substituents selected from halogen atoms and hydroxyl groups); represents hydrogen, C.sub.1-6 alkyl or C.sub.3-6 cycloalkyl; group may be optionally substituted by one or more substituents independently selected from C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy, nitro, halogen and amino; and cycloalkyl; other than hydrogen;
Depending on the nature of the substituents R.sup.1 and R.sup.2, centres of optical and geometric isomerism may be introduced into the molecule. All optical and geometric isomers of compounds of formula (I) and mixtures thereof are embraced by the invention.
According to one preferred embodiment of the present invention, both R.sup.1 and R.sup.2 in formula (I) represent hydrogen atoms.
According to another preferred embodiment of the present invention, the compounds of formula (I) contain ring substituents for example a single ring substituent, R.sup.1 and R.sup.2 selected from halogen, more preferably fluorine or chlorine; nitro; C.sub.1-6 alkyl, more preferably C.sub.1-3 alkyl, for example methyl; C.sub.1-6 alkoxy, more preferably C.sub.1-3 alkoxy, for example methoxy; haloC.sub.1-6 alkyl, more preferably haloC.sub.1-3 alkyl, for example triflouromethyl; --NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5, which may be the same or different, each represent hydrogen or C.sub.1-6 alkyl, preferably hydrogen or C.sub.1-3 alkyl, more preferably both of R.sup.4 and R.sup.5 represent hydrogen or one represents hydrogen and the other represents methyl; --SO.sub.3 H; phenyl; phenylC.sub.1-3 alkoxy, preferably phenylmethoxy; or --CO.sub.2 H.
Ring substituent R.sup.1 or R.sup.2 may be in any one of the 1-, 2-, 3-, 4-, 6-, 7-, 8-
REFERENCES:
Z. Polivka, J. Holubek, E. Svatek, A. Dlabac, D. Pucek, ZZ. Sedivy and M. Protiva, Collection Czechoslovak Chem Commun., vol. 48, pp. 1465-1476, "3-(4-Methylpiperazino)Dibenzo[b,f]-1,2,4-Triazolo[4,3-d]-1,4-Thiazepine and its 6-Chloro and 12-Chloro Derivatives; Synthesis and Pharmacology", (1983).
Hodgson Simon T.
Nicol Robin H.
Slater Martin J.
Bond Robert T.
Glaxo Wellcome Inc.
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