Burroughs Wellcome Co.

Howard J Schaeffer

Gertrude B Elion

George H Hitchings

Paulo M DeMiranda

The novel compound 6-deoxyacyclovir, which itself has antiviral activity against herpes viruses, is converted enzymatically to acyclovir by xanthine oxidase/dehydrogenase or aldehyde oxygenase.

Purine derivatives

9-Hydroxyethoxymethyl (and related) derivatives of certain 6-, and 2,6-substituted purines have been discovered to have potent anti-viral activities. Novel compounds and their pharmaceutically acceptable salts, pharmaceutical formulations containing the compounds of this invention, and the treatment of viral infections with these formulations are all disclosed. 9-(2-hydroxyethoxymethyl) guanine and 2-amino-9-(2-hydroxyethoxymethyl)adenine are examples of especially active compounds of this invention.

Novel 2-amino substituted adenine compounds and their use as antiviral compounds are disclosed. In particular the compound 2-amino-9-(2-hydroxyethoxymethyl) adenine is particularly advantageous as an antiviral in that it has high oral absorption and that upon metabolism in mammals, it has the property of being converted to 9-(2-hydroxyethoxymethyl) guanine which is also a highly active antiviral.

Adenine derivatives

Pharmaceutical preparations containing compounds of the formula ##STR1## where R is alkyl of 1 to 11 carbons. The preparations are useful in inhibiting adenosine deaminase in mammals thereby providing a method for prolonging the effectiveness of pharamaceutical agents which are biologically degraded by adenosine deaminase and thus converted into other compounds.

Adenosine deaminase inhibitors

9-(2-Hydroxyethoxymethyl) (and related) derivatives of certain 6-, and 2,6-substituted purines have been discovered to have potent anti-viral activities. Novel compounds and their pharamceutically acceptable salts, pharmaceutical formulations containing the compounds of this invention, and the treatment of viral infections with these formulations are all disclosed. 9-(2-Hydroxyethoxymethyl)guanine and 2-amino-9-(2-hydroxyethoxymethyl) adenine are examples of especially active compounds of this invention. Also preferred because of its high oral absorption is the phosphate and especially the monophosphate of 9-(2-hydroxyethoxymethyl)guanine as well as pharmaceutically acceptable salts thereof.

9-Hydroxyethoxymethyl (and related) derivatives of certain 6-, and 2,6-substituted purines have been discovered to have potent anti-viral activities. Novel compounds and their pharmaceutically acceptable salts, pharmaceutical formulation containing the compounds of this invention, and the treatment of viral infections with these formulations are all disclosed. 9-(2-hydroxyethoxymethyl) guanine and 2-amino-9-(2-hydroxyethoxymethyl)adenine are examples of especially active compounds of this invention.

Methods and compositions for treating viral infections and guanine

Method of preparing 9-(2-hydroxyethoxymethyl)guanine which comprises preparing the compound ##STR1## wherein R and R.sup.1 are hydrogen, lower alkyl and phenyl and then hydrolyzing same. 9-(2-hydroxyethoxymethyl)guanine is useful as an antiviral.

2-Amido-9-(2-acyloxyethoxymethyl)hypoxanthines

9-[2-(2-Hydroxyethoxy)ethoxymethyl] and related derivatives of certain 2-amino-6-substituted purines have been discovered to have potent anti-viral activities. Novel compounds and their pharmaceutically acceptable salts, pharmaceutical formulations containing the compounds of this invention, and the treatment of viral infection with these formulations are all disclosed. 9-[2-(2-hydroxyethoxy)ethoxymethyl] guanine and 2-amino-9-[2-(2-hydroxyethoxy)ethoxymethyl] adenine, i.e. 2,6-diamino-9-[2-(2-hydroxyethoxy)ethoxymethyl] purine, are examples of especially active compounds of this invention.

Purine derivatives with repeating unit

9-Hydroxyethoxymethyl (and related) derivatives of 2-amino-6-substituted-8-azapurines have been found to have potent anti-viral activities. Novel compounds and their pharmaceutically acceptable salts, pharmaceutical formulations containing the compounds of this invention, and the treatment of viral infections with these formulations are all disclosed. 9-(2-Hydroxyethoxymethyl)-8-azaguanine and 9-(2-benzoyloxyethoxymethyl)-8-azaguanine are examples of active compounds of this invention.

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Raleigh, NC, United States of America

Howard J Schaeffer