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Antiviral phosphonate nucleotides

  • US 6,444,656 B1
  • Filed: 03/24/2000
  • Issued: 09/03/2002
  • Est. Priority Date: 12/23/1992
  • Status: Expired due to Fees
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First Claim
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1. A nucleotide analogue according to formula (I):

  • embedded imageor a pharmaceutically acceptable salt, a pharmaceutically acceptable ester, or a pharmaceutically acceptable salt of an ester wherein;

    n is 0;

    X is O;

    Q is CH2;

    U is C═

    CH2 or CH(Ra);

    Ra is OH, CN, halogen, N3, or NH2;

    Z is (CH2)m wherein m is 1;

    R1 and R1′

    are each independently selected from H, C1-6 alkyl, phosphate or diphosphate; and

    R2 is embedded image 

    wherein x is oxygen or sulfur;

    y is oxygen or sulfur;

    R3 and R4 are each independently selected from hydrogen, hydroxyl, amino, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-10 acyl, or C6-12 aryl;

    R5 and R6 are each independently selected from hydrogen, F, Cl, Br, I, hydroxyl, methyl or amino;

    R7 is H, F, Cl, I, Br, hydroxyl, amino or the formulas embedded image 

    wherein;

    q is an integer selected from 1 to 4;

    R18 is selected from H, COOH, C(O)NH2, OH, SH, NH2, NO2,or C1-6 alkyl;

    R17 is H or a C1-6 alkyl; and

    R8 and R9 are each independently chosen from hydrogen, hydroxyl, amino, substituted amino, halogen, azido or methyl;

    provided that when R2 is adenine Ra, if present, is CN, halogen, N3, or NH2.

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