| abstract |
Aryl substituted phosphoryl derivatives of the formula n n n In which Ar is phenyl, naphthyl, or pyridyl, Y is O or S, X 1 is O, NR 3 , S, CR 3 R 4 , CR 3 W 1 or CW 1 W 2 , X 2 and X 6 are a bond or X 6 is CH 2 and X 2 is O, NR 3 , S, CR 3 R 4 , CR 3 W 1 or CW 1 W 2 , R 3 and R 4 are H, alkyl or phenyl, groups, W 1 and W 2 are heteroatoms, X 3 is alkylene, X 4 is oxygen or CH 2 , X 5 is a bond or CH 2 , Z is O, NR 5 , S, alkyl or phenyl, R 5 is H, alkyl or phenyl, J is H, alkyl, phenyl, or a heterocyclic or polycyclic group, Q is O, NR 6 , S, CR 6 R 7 , CR 6 W 3 or CW 3 W 4 , R 6 and R 7 are H, alkyl or phenyl, and W 3 and W 4 are hetero atoms, T 1 and T 2 are H or CH 2 R 8 , R 8 is H, OH or F, or T 1 and T 2 together are —CH═CH— or —C(R 9 )(R 10 )C(R 11 )(R 12 )—, R 9 is H, halogeno, CN, NH 2 , CO-alkyl, or alkyl, R 10 , R 11 , and R 12 are H, N 3 , halogen, CN, NH 2 , CO-alkyl, or alkyl, and B is a purine or pyrimidine base, have antiviral activity, as for example against HIV. Particularly preferred are thymine and adenine derivatives of amino acid phenoxyphosphoroamidates. A typical embodiment is 2′,3′-dideoxy-2′,3′-didehydrothymidine 5′-(phenyl methoxy alaninyl) phosphoroamidate which can be prepared from phenyl methoxy alaninyl phosphorochloridate and 2′,3′-dideoxy-2′,3′-didehydrothymidine. |