Novel 6-amino-9-(substituted benzyl) purines are prepared by allowing an appropriate substituted benzyl halide, e.g., a substituted benzyl chloride, to react with adenine under the appropriate conditions. Oxidation of the resulting purine derivatives yields the corresponding N.sup.1 -oxides. These compounds, i.e., both the purine derivatives and the N.sup.1 -oxides thereof, have anti-coccidial activity and are useful for controlling cecal and/or intestinal coccidiosis when administered in minor quantities to animals, in particular to poultry, usually in admixture with animal sustenance.
This invention is concerned with 6-(substituted amidino-9-substituted benzyl purine derivatives and in particular 6-(aminomethylideneamino)-9-substituted benzyl purines. The compounds are active anticoccidial agents and suitable compositions and methods are described for the administration of such compounds to poultry for the prevention and treatment of coccidiosis.
An efficient method has been found for the removal of the 3-isomer present in crude 9-(2-chloro-6-fluorobenzyl)adenine. Crude 9-(2-chloro-6-fluorobenzyl)adenine is transalkylated in sulfuric acid-toluene to reduce the 3-isomer to undetectable levels (<100 ppm). Alternately, crude 9-(3-chloro-6-fluorobenzyl)adenine is first treated with dilute nitric acid to remove the bulk of the 3-isomer followed by transalkylation to sulfuric acid-toluene to reduce the 3-isomer to undetectable levels (<100 ppm). The overall yield for this purification is about 95% based on the 9-(2-chloro-6-fluorobenzyl)adenine content of the crude material. The resulting pure 9-(2-chloro-6-fluorobenzyl)adenine has anticoccidial activity and is useful in controlling cecal and/or intestinal coccidiosis when administered in minor quantities to animals, in particular to poultry usually in admixture with animal sustenance.
Novel purine derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen or alkyl of 1 to 3 carbon atoms, R.sup.2 is alkyl of 1 to 3 carbon atoms or allyl, and R.sup.3 and R.sup.4, respectively, mean halogen, and their acid addition salts are provided. These compounds have anticoccidial activity and are useful for treating caecal and/or intestinal coccidiosis in poultry and domestic animals.
This invention is concerned with a novel process for the preparation of N.sup.6 -alkyl-arprinocid (6-alkyl-amino-9-substituted benzyl purines). Such compounds are active anticoccidial agents. The process involves the preparation of a Schiff base from an acetal of dialkylformamide and reduction with a metal hydride.
9-(2,6-Dihalobenzyl)adenines are prepared by allowing 2,6-dihalobenzyl halides to react with a salt of adenine in a solid-liquid or liquid-liquid two phase system in the presence of an onium salt phase transfer catalyst. The resulting compounds have anticoccidial activity and are useful in controlling cecal and/or intestinal coccidiosis when administered in minor quantities to animals, in particular to poultry usually in admixture with animal sustenance.
