Antiretroviral enantiomeric nucleotide analogs
AssigneesInstitute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.
InventorsAntonin Holy, Hana Dvorakova, Erik Desire Alice De Clercq, Jan Marie Rene Balzarini
Life of this patent
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Abstract
Resolved enantiomers of the formula (IA) and (IB) 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.
Claims40
A compound of the formula:
- including salts of such compounds, wherein said compound of Formula IA is substantially free of its enantiomer and wherein B is (a) an unsubstituted purine moiety, (b) a substituted purine moiety substituted independently at the 2 and/or 6 and/or 8 position by amino, halogen, hydroxy, alkoxy, alkylamino, dialkylamino, aralkylamino, pyrrolidino, morpholino, piperidino, benzoylamino, azido, mercapto or alkylthio, or (c) the 8-aza analog thereof, and wherein
- B is other than guanine or 2-amino-6-halopurine;
- R is H;
- and aryl in aralkylamino is a 6-10C aromatic group.
9-(R)-(2-Phosphonomethoxypropyl)-2-amino-6-dimethylaminopurine.
9-(R)-(2-Phosphonomethoxypropyl)-2-amino-6-diethylaminopurine.
9-(R)-(2-Phosphonomethoxypropyl)-2-amino-6-butylaminopurine.
9-(R)-(2-Phosphonomethoxypropyl)-2-amino-6-(2-butyl)aminopurine.
9-(R)-(2-Phosphonomethoxypropyl)-2-amino-6-cyclopropylaminopurine.
9-(R)-(2-Phosphonomethoxypropyl)-2-amino-6-cyclopentylaminopurine.
9-(R)-(2-Phosphonomethoxypropyl)-2-amino-6-cyclohexylaminopurine.
9-(R)-(2-Phosphonomethoxypropyl)-2-amino-6-pyrrolidinopurine.
9-(R)-(2-Phosphonomethoxypropyl)-2-amino-6-piperidinopurine.
9-(R)-(2-Phosphonomethoxypropyl)-2-amino-6-morpholinopurine.
9-(R)-(2-Phosphonomethoxypropyl)-2-amino-6-benzylaminopurine.
9-(R)-(2-Phosphonomethoxypropyl)-8-azaguanine.
8-(R)-(2-Phosphonomethoxypropyl)-8-azaguanine.
7-(R)-(2-Phosphonomethoxypropyl)-8-azaguanine.
9-(R)-(2-Phosphonomethoxypropyl)-8-aza-2,6-diaminopurine.
8-(R)-(2-Phosphonomethoxypropyl)-8-aza-2,6-diaminopurine.
9-(R)-(2-Phosphonomethoxypropyl)-6-mercaptopurine.
9-(R)-(2-Phosphonomethoxypropyl)-N1,N6-ethenoadenine.
A compound selected from the group consisting of 9-(R)-(2-phosphonomethoxypropyl)-2,6-diaminopurine and the 8-aza analog thereof.
Dependencies are inferred from the claim text.