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Thieno[2,3-d]pyrimidine diones and their use in the treatment of reversible obstructive airways diseases

  • US 6,342,502 B1
  • Filed: 10/23/2000
  • Issued: 01/29/2002
  • Est. Priority Date: 05/28/1997
  • Status: Expired due to Fees
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1. A method of treating, or reducing the risk of, asthma in a patient suffering from, or at risk of, said disease, which comprises administering to the patient a therapeutically effective amount of a compound of formula (I):

  • embedded imagewherein;

    R is —

    C(O)Ar1, —

    C(R4)(R5)Ar1, or Ar2;

    Ar1 is naphthyl, quinolyl, isoquinolyl, indolyl, benzofuranyl or benzothienyl, each of which can be optionally substituted by one or more substituents selected from C1-4 alkyl, C1-4 alkoxy, halogen or trifluoromethyl, or Ar1 is phenyl optionally substituted by one or more substituents selected from C1-4 alkyl, C1-4 alkoxy, halogen, trifluoromethyl, amino, nitro, cyano, trifluoromethoxy, phenoxy, —

    CH2N(R6)2, —

    NHSO2CF3, C1-4 alkylsulphonylamino, —

    NHC(O)R6a, CO2R7 or —

    C(O)NR8R8a;

    R4 represents H or C1-4 alkyl;

    R5 represents H or OH;

    each R6 independently represents H or C1-4 alkyl;

    R6a represents H, C1-6 alkyl, aryl or arC1-4 alkyl, wherein the aryl group or aryl moiety in the aralkyl group is phenyl or pyridyl, each of which may be optionally substituted by one or more substituents selected from C1-4 alkyl, C1-4 alkoxy, C1-4 alkylcarbonylamino, halogen or trifluoromethyl;

    R7 represents H or C1-4 alkyl;

    R8 and R8a each independently represent H, C1-4 alkyl, phenyl or pyridyl;

    Ar2 is acenaphthenyl, indanyl, iminodihydrobenzofuranyl or fluorenyl, each of which can be optionally substituted by one or more substituents selected from OH, C1-4 alkyl, C1-4 alkoxy, halogen, or trifluoromethyl;

    R1 and R2 are independently H, C1-6 alkyl, C3-6 alkenyl, CH2CH3-5 cycloalkyl or C3-6 cycloalkyl;

    R3 represents H, X—

    R9 or X—

    Ar3;

    X represents S(O)n, C(O)NR10, C(O)O, NH(CO)NR10, NH(CO)O or SO2NR10;

    n is 0, 1 or 2;

    R9 represents a methyl group optionally substituted by one or more substituents selected from CN, CO2H, C1-5 alkoxycarbonyl, 5-tetrazolyl, SO2NH2 or C(O)NR11R12, or represents C2-6 alkyl or C3-6 alkenyl, each of which may be optionally substituted by one or more substituents selected from OH, CN, CO2H, C1-5 alkoxy, C1-5 alkoxycarbonyl, 5-tetrazolyl, azide, phthalimido, SO2NH2, C(O)NR11R12, NR13R14, NHC(O)R15 or NHSO2R16 where R11, R12, R13 and R14 each independently represent H or C1-4 alkyl, R15 represents C1-4 alkyl, C1-4 alkoxy, di(C1-4alkyl)amino, or alkoxyalkylene containing up to 6 carbon atoms, and R16 represents C1-4 alkyl or trifluoromethyl;

    or, additionally, in the case where X represents C(O)NR10, NH(CO)NR10 or SO2NR10, R9 and R10 together with the nitrogen atom to which they are attached may form a 4- to 7-membered heterocyclic ring which may be optionally substituted by one or more OH groups;

    R10 represents H, C1-6 alkyl or is linked to as defined above; and

    Ar3 is phenyl, pyridyl or pyridine N-oxide, each of which may be optionally substituted by one or more substituents selected from OH, NO2, NH2, NHSO2CF3, C1-4 alkoxy, bis C1-4 alkanesulphonylamino, C1-4 alkylcarbonylamino or alkoxycarbonylamino;

    or a pharmaceutically-acceptable salt or solvate thereof.

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