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Phosphoramidate and phosphorothioamidate oligomeric compounds

  • US 5,637,684 A
  • Filed: 02/23/1994
  • Issued: 06/10/1997
  • Est. Priority Date: 02/23/1994
  • Status: Expired due to Term
First Claim
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1. A compound of the structure:

  • ##STR3## wherein;

    X0 and each Xm, independently, are O or S;

    Y0 and each Ym, independently, are H, or [Q2 ]j --Z2 ;

    T0 and each Tm, independently, are [Q1 ]k --Z1, or together Y and T are joined in a nitrogen heterocycle;

    Q1, Q2, L0, Lm+1 and each Lm, independently, are C2 -C10 alkyl, C2 -C10 alkenyl, C2 -C10 alkynyl, C4 -C7 carbocylo alkyl or alkenyl, a heterocycle, a polyalkyl glycol, or C7 -C14 aralkyl;

    E1 and E2, independently, are H, a hydroxyl protecting group, an activated solid support, a conjugate group, a reporter group, a polyethylene glycol, alkyl, oligonucleotide, peptide nucleic acid, a phosphate, a phosphite, an activated phosphate, or an activated phosphite;

    j and k independently are 0 or 1;

    m is 1 to about 50;

    Z1 and Z2, independently, are H, C1 -C2 alkyl, C2 -C20 alkenyl, C2 -C20 alkynyl, C6 -C14 aryl, C7 -C15 aralkyl, CH═

    O, OR1, SR2, NR3 R4, C(═

    NH)NR3 R4, CH(NR3 R4), NHC(═

    NH)NR3 R4, CH(NH2)C(═

    O)OH, C(═

    O)NR3 R4, C(═

    O)OR5, a metal coordination group, a reporter group, a nitrogen-containing heterocycle, a purine, a pyrimidine, a phosphate group, a polyether group, or a polyethylene glycol group;

    R1 is H, alkyl having 1 to about 6 carbon atoms, or a hydroxyl protecting group;

    R2 is H, alkyl having 1 to about 6 carbon atoms, or a thiol protecting group;

    R3 and R4 are, independently, H, alkyl having 1 to about 6 carbon atoms, or an amine protecting group; and

    R5 is H, alkyl having 1 to about 6 carbon atoms, or an acid protecting group.

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