Interaction of 5-diazoimidazole-4-carboxamide and alkyl and aryl isocyanates in the dark affords 8-carbamoyl-3-substituted-imidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-on es. In cold methanol or ethanol, the 3-(2-chloroethyl) derivative 7a decomposes to afford 2-azahypoxanthine (14) and methyl and ethyl N-(2-chloroethyl)carbamates, respectively. Compound 7a has curative activity against L-1210 and P388 leukemia and may act as a prodrug modification of the acyclic triazene 5-[3-(2-chloroethyl)triazen-1-yl]imidazole-4-carboxamide (MCTIC), since it ring opens to form the triazene in aqueous sodium carbonate.

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Immunosuppressive Compoundswas added, and the flask was tightly closed and left at room temp.At the end of the required reaction time the solvent was removed under reduced pressure, and the product was purified as described in Table I.Method C.-In a flask as above and using a condenser, d-pilocarpine (0.02 mole) was dissolved in Me»CO (10 ml) with constant stirring while heating to about 50°. A freshly prepd soln of 0.025 mole of the halo organic reagent in 10 ml of Me2CO was then slowly added and the mixt was heated to reflux for 30 min (reflux was not necessary for 9). After cooling, the soln was transferred to a dry flask with 20 ml of dry Me2CO and kept tightly closed at room temp for the required period. The Me2CO was then removed under reduced pressure above a H20 bath, and the residue was dried. For purification of the products see Table I. In the case of 23, d-pilocarpine was added to a suspension of the halo org reagent in dry Me2CO at reflux temp, and the product was collected by filtration.Method D.-In a flask equipped as above, a soln of halo org reagent (0.02 mole) in 2-methoxyethanol (20 ml) was heated to 50°with stirring; then a soln of d-pilocarpine (0.02 mole in 25 ml of the same solvent) was added dropwise. The mixt was heated with stirring to 80°for 30 min and left tightly closed at room temp for the required period. The solvent was removed at 80°under reduced pressure, and the residue was dried over PA. For 4 no heating was required and the molar ratio was 1.5:1. Whenever min amounts of the HBr of the pilocarpine were obtd as a side product, the sepn from the quaternary compds was accomplished from an aq soln at pH 7.5. The free pilocarpine was extd with CHClg leaving the quaternary compd in the aq layer which was then lyophilized.Compd 25 (R = p-BrC6H5C6HOHCH2).-3-(iV-p-Bromophenacy 1 )-d-pilocarpinium bromide (20) (0.24 g, 5 X 10-4 mole) was dissolved in MeOH (30 ml), and NaBH4 (0.12 g, 3 X 10~3 mole) was added and stirred for 1 hr. The soln was then filtered and adjusted to pH ~7 (with HC11:4). The solvent was removed under reduced pressure, and the residue was dried overnight in a desiccator over PA. This residue was then dissolved in a min quantity of abs EtOH and filtered. After evapn of the solvent, the yellowish product (0.29 g, 93%) was redissolved in abs EtOH, decolorized with activated C (Darco G 60; 15 min at

Method R. a-(m-Trifluoromethylanilino)phenylacetic Acid.-A solution of m-trifluoromethylaniliue (12.0 g) and o-bromophenylacetic acid (6.5 g) in EtOH (100 ml) was healed at 100°for 5 hr, and the solvent was evaporated at 40°. The residue was

A previous report from these laboratories (Stone et al., 1953) described a bacteriophage active against one of the chromogenic nasopharyngeal neisseriae. The purpose of this paper is to describe further studies of the bacteriophage and the host organism. MATERIALS AND METHODS Cultures and media. Of the 36 strains of Neisseria employed in this study, two strains (155B and 157