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Pyrimidine nucleosides

  • US 6,369,040 B1
  • Filed: 08/27/1999
  • Issued: 04/09/2002
  • Est. Priority Date: 01/11/1990
  • Status: Expired due to Fees
First Claim
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1. A pharmaceutical composition comprising a compound having the following formula:

  • embedded imagewherein;

    R5 is H or CH3;

    one of R2 and R4 is ═

    O, ═

    NH, or ═

    NH2+; and

    the other of R2 and R4 is Q, ═

    C(RA)—

    Q, C(RA)(RB)—

    C(RC)(RD)—

    Q, C(RA)═

    C(RC)—

    Q or C≡

    C—

    Q;

    each RA, RB, RC and RD is, independently [are] H, SH, OH, NH2, or C1-C20 alkyl, or one of (RA) and (RB) or (RC) and (RD) is combined to give ═

    O and each of the other of (RA) and (RB) or (RC) and (RD) is, independently H, SH, OH, NH2, or C1-C20 alkyl;

    Q is halogen, hydrogen, C1-C20 alkyl, C1-C20 alkylamine, C1-C20 alkyl-N-phthalimide, C1-C20 alkylimidazole, C1-C20 alkylbis-imidazole, NH2, C2-C20 alkenyl, C2-C20 alkynyl, hydroxyl, thiol, keto, carboxyl, nitrates, nitro, nitroso, nitrile, trifluoromethyl, trifluoromethoxy, O-alkyl, S-alkyl, NH-alkyl, N-dialkyl, O-aralkyl, S-aralkyl, NH-aralkyl, azido, hydrazino, hydroxylamino, isocyanato, sulfoxide, sulfone, sulfide, disulfide, silyl, O-(hydroxyl protecting group), a leaving group, a heterocycle, a polyamine, a polyamide, a polyether, or a depurination enhancing group;

    T3 and T5 independently are H, phosphate, an activated phosphate, a hydroxyl protecting group, a nucleoside, a nucleotide, an oligonucleotide comprising up to 50 nucleosides joined together by 3′

    -5′

    internucleoside linkages, or an oligonucleoside comprising up to 50 nucleosides joined together by 3′

    -5′

    internucleoside linkages;

    X1 and X2 independently are hydrogen, halogen, hydroxyl, O-(hydroxyl protecting group), thiol, carboxyl, nitrate, nitro, nitroso, nitrile, trifluoromethyl, trifluoromethoxy, O-alkyl, S-alkyl, NH-alkyl, N-dialkyl, O-aralkyl, S-aralkyl, NH-aralkyl, amino, azido, hydrazino, hydroxylamino, isocyanato, sulfoxide, sulfone, sulfide, disulfide, silyl, heterocyclic, alicyclic, carbocyclic, polyamines, polyamides, or polyethers;

    or T3 and one of X1 or X2, together, form a hydroxyl protecting group; and

    provided that when T5 is a hydroxyl protecting group or together T3 and one of X1 or X2 is a hydroxyl protecting group, then R2 is not CH3; and

    that when T3 and T5 are OH or O-benzoyl, then R2 is not CH2OC6H5; and

    that when R4 is Q, then Q is not hydrogen, hydroxyl, thiol, amino or hydrogen.

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