Ceskoslovenska Akademie Ved

Institute of Organic Chemistry and Biochemistry of the Academy of

Rega Stichting, V.z.w.

Stichting Rega Vzw

Rega Institut

Antonin Holy

Erik D De Clercq

Ivan Rosenberg

Jan Marie Balzarini

Jindrich Jindrich

Hana Dvorakova

Karel Slama

Petr Alexander

Erik Desire DeClercq

Resolved enantiomers of the formula ##STR1## wherein B is a purine or pyrimidine base or aza and/or deaza analogs thereof are useful in antiviral pharmaceutical compositions to treat retroviral infections.

Antiretroviral enantiomeric nucleotide analogs

This invention relates to new nucleotide analogues and solves the technical problem of their use as biologically active compounds. The subject of this invention are N-(2-phosphonylmethoxyethyl) and N-(3-hydroxy-2-phosphonylmethoxypropyl) derivatives of pyrimidine and purine bases, easily accessible from heterocyolic bases and their N-(2-hydroxyethyl) or N-(2,3-dihydroxypropyl) derivatives. Some of the compounds, according to this invention, exhibit a marked antiviral activity or can be converted into such active compounds by chemical transformations.

9-(2-phosphonylmethoxyethyl) guanine

N-(3-Fluoro-2-phosphonylmethoxypropyl) derivatives of purine and pyrimidine heterocyclic bases, method of producing them and their use as active principles of drugs. The invention relates to suppression of multiplication of viruses, particularly retroviruses, by application of the new compounds, N-(3-fluoro-2-phosphonylmethoxypropyl) derivatives of purine and pyrimidine heterocyclic bases. These compounds are obtained by the reaction of the N-(3-fluoro-2-hydroxypropyl) derivatives of purine and pyrimidine heterocyclic bases with diesters of p-toluenesulfonyloxymethylphosphonic acid in the presence of sodium hydride.

N-(3-fluoro-2-phosphonylmethoxypropyl) derivatives of purine and

This invention relates to new nucleotide analogues and solves the technical problem of their use as biologically active compounds. The subject of this invention are N-(2-phosphonylmethoxyethyl) and N-(3-hydroxy-2-phosphonylmethoxypropyl) derivatives of pyrimidine and purine bases, easily accessible from heterocyclic bases and their N-(2-hydroxyethyl) or N-(2,3-dihydroxypropyl) derivatives. Some of the compounds, according to this invention, exhibit a marked antiviral activity or can be converted into such active compounds by chemical transformations.

N-phosphonylmethoxyalkyl derivatives of pyrimdine and purine bases and a

Di(2-propyl)esters of

This invention relates to new nucleotide analogues and solves the technical problem of their use as biologically active compounds. The subject of this invention are N-(2-phosphonylmethoxyethyl) and N-(3-hydroxy-2-phosphonylmethoxypropyl) derivatives of pyrimidine and purine bases, easily accessible from heterocyclic bases andd their N-(2-hydroxyethyl) or N-(2,3-dihydroxypropyl) derivatives. Some of the compounds, according to this invention, exhibit a marked antiviral activity or can be converted into such active compounds by chemical transformations.

N-phosphonylmethoxyalkyl derivatives of pyrimidine and purine bases and

The invention relates to the new compound (2R)-2-[di(2-propyl)phosphonylmethoxy]-3-p-toluenesulfonyloxy-1-trimethyla cetoxypropane and the method of producing it. The compound may be used for producing (S)-N-(3-hydroxy-2-phosphonylmethoxypropyl) derivatives of the heterocyclic purine and pyrimidine bases of antiviral activity.

(2R)-2-[di(2-propyl)phosphonylmethoxy]-3-p-to

The invention relates to 9-(phosphonylmethoxyalkyl)adenines of the general formula I ##STR1## wherein R.sup.1 is a hydrogen atom, and alkyl group containing one to three carbon atoms, or a hydroxymethyl group, R.sup.2 is a methylene, ethylene, propylene, ethylidene, methoxyethylene, benzyloxyethylene, tetrahydropyran-2-yloxyethylene, (1-ethoxyethoxy)ethylene or 1,2-O-isopropylidene-1,2-dihydroxypropylene group the method of their preparation and utilization. Compounds of the general formula I exhibit biological effects (e.g. antiviral) or can be converted into compounds with such effects.

9-(phosponylmethoxyalkyl) adenines, the method of preparation and

The (S) and (RS) forms of certain phosphonylmethoxyalkyl adenines and their salts have an antiviral effect against several DNA viruses and can be used for the treatment of virus diseases in human and veterinary medicine.

Therapeutical application of phosphonylmethoxyalkyl adenines

This invention relates to isomeric O-phosphonylmethyl derivatives of the formula I ##STR1## wherein R.sup.5 designates an adenin-9-yl moiety, R.sup.4 are alternately a hydrogen atom and a --CH.sub.2 P(O)(OH).sub.2 group, and the configuration at the carbon atom in the position 2 is S, R or RS. The compounds according to the invention are biologically active as inhibitors of metabolic processes and in organism they are stable towards enzymes, cleaving phosphomonoester bonds. The said compounds exhibit also chemosterilizing action on insects.

Isomeric O-phosphonylmethyl derivatives of enantiomeric and racemic

Certain esters of 3-(adenin-9-yl)-2-hydroxypropanoic acid are disclosed which exhibit an improved broad spectrum antiviral activity while having a low toxicity for living cells. They can be used for treatment of virus diseases in human and veterinary practice.

Antivirally active adenine derivatives

The specification describes the use of S or RS 9-(2, 3-dihydroxypropyl) adenine either alone or in combination with ara-A for the treatment of virus diseases.

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Horni Pocernice, Czechia

Antonin Holy