Methods and compositions for treating viral infections and guanine acyclic nucleosides
AssigneeBurroughs Wellcome Co.
InventorHoward J. Schaeffer
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Abstract
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.
Claims81
A substituted purine of formula (I) ##STR12## wherein X is sulphur or oxygen;
- R.sup.1 is hydroxy, R.sup.2 is amino;
- R.sup.3 is hydrogen, straight or branched chain or cyclic alkyl, hydroxyalkyl, benzyloxyalkyl or phenyl;
- R.sup.4 is hydrogen, hydroxy, or lower alkyl;
- R.sup.5 is hydrogen, hydroxy, amino, alkyl, hydroxyalkyl, benzoyloxy, benzoyloxyalkyl, benzyloxy, sulphamoyloxy, phosphate, carboxypropionyloxy, or acetoxy;
- R.sup.6 is hydrogen, alkyl, hydroxyalkyl or a pharmaceutically acceptable salt thereof.
A pharmaceutical composition which comprises an effective non-toxic antiviral treatment amount of a substituted purine of the formula (I) ##STR13## wherein X is sulphur or oxygen;
- R.sup.1 is hydroxy, R.sup.2 is amino;
- R.sup.3 is hydrogen, straight or branched chain or cyclic alkyl, hydroxyalkyl, benzoylalkyl or phenyl;
- R.sup.4 is hydrogen, hydroxy, or alkyl;
- R.sup.5 is hydrogen, hydroxy, amino, alkyl, hydroxyalkyl, benzoyloxy, benzoyloxyalkyl, benzyloxy, sulphamoyloxy, phosphate, carboxypropionyloxy, or acetoxy;
- R.sup.6 is hydrogen, alkyl, or hydroxyalkyl;
- or a pharmaceutically acceptable salt thereof;
- together with a pharmaceutically acceptable carrier therefor.
A purine selected from the group consisting of:
- 9-(3-Benzoylpropoxymethyl)guanine
- 9-[1-(2-Hydroxyethoxy)ethyl]guanine
- 9-Ethoxymethylguanine and
- 9-(4-Hydroxy-n-butoxymethyl)guanine hemihydrate.
9-(2-Formyloxyethoxymethyl) guanine or a pharmaceutically acceptable salt thereof.
A pharmaceutical composition comprising an effective non-toxic antiviral infection treatment amount of 9-(2-formyloxyethoxymethyl)guanine or a pharmaceutically acceptable salt thereof and a pharmaceutical acceptable carrier therefor.
A method of treating a susceptible viral infection in a mammal which comprises administering an effective non-toxic anti-viral amount of 9-(2-formyloxyethoxymethyl)guanine or a pharmaceutically acceptable salt thereof to said mammal.
The compound of the formula I ##STR14## wherein X is sulphur or oxygen, R.sup.1 is hydroxy;
- R.sup.2 is amino;
- R.sup.3 is hydrogen, straight or branch chain or cyclic alkyl, hydroxyalkyl, benzyloxyalkyl or phenyl;
- R.sup.4 is hydrogen, hydroxy or alkyl;
- R.sup.5 is hydrogen, hydroxy, amino, alkyl, hydroxyalkyl, benzyloxy, benzoyloxy, benzoyloxymethyl, sulphamoyloxy, phosphate or straight chain or cyclic acyloxy having from 1 to 8 carbon atoms;
- R.sup.6 is hydrogen or alkyl, or a pharmaceutically acceptable salt thereof.
9-(2-hydroxyethoxymethyl)guanine.
A pharmaceutically acceptable salt of 9-(2-hydroxyethoxymethyl)guanine.
A pharmaceutical composition comprising an effective non-toxic antiviral treatment amount of 9-(2-hydroxyethoxymethyl) guanine or a pharmaceutically acceptable salt thereof together with a pharmaceutically acceptable carrier therefore.
The method of treating a susceptible viral infection in a mammal having said viral infection which comprises the administration of an effective antiviral non-toxic amount of 9-(2-hydroxyethoxymethyl)guanine or a pharmaceutically acceptable salt thereof.
9-[2-(3-carboxypropionyloxy)ethoxymethyl]guanine.
A pharmaceutically acceptable salt of:
- 9-[2-(3-carboxypropionyloxy)ethoxymethyl]guanine.
A pharmaceutical composition comprising an effective non-toxic antiviral infection treatment amount of 9-[2-(3-carboxypropionyloxy)ethoxymethyl]guanine or a pharmaceutically acceptable salt thereof.
A method of treating a susceptible viral infection in a mammal which comprises administering an effective non-toxic antiviral amount of 9-[2-(3-carboxypropionyloxy)ethoxymethyl]guanine or a pharmaceutically acceptable salt thereof to said mammal.
Dependencies are inferred from the claim text.