2',5'-dideoxy-5'-fluoro nucleosides and process for preparing same

Abstract

Abstract A CYTOSTATIC COMPOSITION CAPABLE OF SUBSTANTIALLY INHIBITING THE DNA SYNTHESIS OF ASCITES TUMOR CELLS IN VITRO, HAVING THE FORMULA: 2-R2,4-(R1-O-),5-(H2CF-)TETRAHYDROFURAN WHEREIN R1 IS A HYDROGEN ATOM OR AN ACETYL RADICAL AND R2 IS SELECTED FROM THE GROUP CONSISTING OF 5-ALKYL AND 5HALOGEN SUBSTITUTED 2,4-DIHYDROXY-PYRIMIDINE, 5-ALKYL AND 5-HALOGEN SUBSTITUTED 2-HYDROXY-4-AMINO-PYRIMIDINE, AND PURINE SUBSTITUTED IN 2-POSITION, 6-POSITION OR 2 AND 6 POSITION WITH AN AMINE OR HYDROXYL GROUP. THESE COMPOUNDS MAY BE OBTAINED BY REACTING 5''-ARYLSULPHONYL- OR 5''-MESYL-SUBSTITUTED 2''-DEOXYRIBONUCLEOSIDE IN A SOLVENT MEDIUM WITH AN ALKALI METAL FLUORIDE, SEPARATING THE THEREBY-FORMED ALKALI METAL ARYLSULPHONATE FROM THE RESIDUAL REACTION MIXTURE, EVAPORATING THE RESIDUAL RECTION MIXTURE AT REDUCED PRESSURE, AND RECOVERING THE COMPOUND FROM THE DRY RESIDUE BY TAKING UP THE DRY RESIDUE WITH A MIXTURE OF POLAR AND NON-POLAR SOLVENTS, FOLLOWED BY CHROMATOGRAPHIC SEPARATION OF THE COMPOUNDS FROM THE THUS-FORMED SOLUTION.

Inventors

• 👤 Peter Langen
• 👤 Gotthard Kowollik

Bibliographic Details