The invention comprises 1-substituted isatin b -thiosemicarbazones of the formula FORM:0975357/C1/1 with the exception of 1-methylisatin, b -thiosemicarbazone, wherein R1 is an acetyl group or an alkyl, alkenyl or alkynyl group of not more than 5 carbon atoms which may carry one or more substituents each of which is a halogen atom or a hydroxy group which may be esterified with an aliphatic carboxylic acid radical containing a total of not more than 5 carbon atoms, R2 is a hydrogen or a halogen atom or a methyl or ethyl group, or R1 and R2 form a trimethylene chain, and R3 and R4 are hydrogen or fluorine atoms, at least 2 of R2, R3 and R4 being hydrogen atoms, and the preparation thereof and of the extruded compound by converting an appropriately substituted isatin into its thiosemicarbazone by known methods of thiosemicarbazone formation. 1-Ethyl-, 1-butyl-, 1-pentyl-, 1-isopropyl-, 1-prop -21- ynyl-, and 1-allyl-isatin are prepared from sodioisatin and the appropriate alkyl, alkenyl or alkynyl halide. 1-(21-Hydroxyethyl)-isatin is prepared from sodioisatin and 2-chloroethanol. 1-Acetoxymethyl- and 1-(21-acetoxyethyl)-isatin are prepared from acetyl chloride and the corresponding 1-hydroxyalkylisatin. 1-(21-Bromoethyl)-isatin is prepared from 1,2-dibromoethane and sodioisatin. 5-Fluro -1- methyl- and 5-fluoro -1- ethyl)-isatin are prepared from 5-fluoro -1- sodioisatin and methyl and ethyl iodide.ALSO:Pharmaceutical preparations comprise a compound of the general formula FORM:0975357/A5-A6/1 wherein R1 is an acetyl group or is an alkyl, alkenyl or alkynyl group having not more than 5 carbon atoms which may carry one or more substituents, each of which is a halogen atom or a hydroxy group which may be esterified with an aliphatic carboxylic acid radical having a total of not more than 5 carbon atoms, R2 is a hydrogen or a halogen atom or a methyl or an ethyl group or R1 and R2 form a trimethylene chain, and R3 and R4 are hydrogen or fluorine atoms, at least two of R2, R3 and R4 being hydrogen atoms, and an acceptable carrier therefor, other than simple solutions of 1-methylizatin b -thiosemicarbazone in water, acetone, methanol, ethanol, acetic acid, aqueous ethanol or aqueous ethanolic caustic soda solutions and suspensions of the compound in those liquids of the above list which might be suitable pharmaceutical vehicles, unless other pharmaceutical ingredients or carriers are also included. The compositions may be formulated as tablets, capsules, cachets, ampoules, suppositories, powders, granules, solutions, suspensions, emulsions or ointments. The compositions are active against vaccinia virus and human smallpox.
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