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Amino acid complexes of C-aryl glucosides for treatment of diabetes and method

  • US 6,774,112 B2
  • Filed: 04/08/2002
  • Issued: 08/10/2004
  • Est. Priority Date: 04/11/2001
  • Status: Expired due to Term
First Claim
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1. Crystalline complexes between either (D) or (L) enantiomers of natural amino acids and compounds of formula I embedded imagewhereinR1, R2 and R2a are independently hydrogen, OH, OR5, alkyl, —

  • OCHF2, —

    OCF3, —

    SR5a or halogen;

    R3 and R4 are independently hydrogen, OH, OR5b, alkyl, cycloalkyl, CF3, —

    OCHF2, —

    OCF3, halogen, —

    CONR6R6a, —

    CO2R5c, —

    CO2H, —

    COR6b, —

    CH(OH)R6c, —

    CH(OR5d)R6d, —

    CN, —

    NHCOR5e, —

    NHSO2R5f, —

    NHSO2Aryl, —

    SR5g, —

    SOR5h, —

    SO2R5i, or a five, six or seven membered heterocycle which may contain 1 to 4 heteroatoms in the ring which are N, O, S, SO, and/or SO2, or R3 and R4 together with the carbons to which they are attached form an annelated five, six or seven membered carbocycle or heterocycle which may contain 1 to 4 heteroatoms in the ring which are N, O, S, SO, SO2;

    R5, R5a, R5b, R5c, R5d, R5e, R5f, R5g, R5h and R5i are independently alkyl;

    R6, R6a, R6b, R6c and Rd are independently hydrogen, alkyl, aryl, alkylaryl or cycloalkyl, or R6 and R6a together with the nitrogen to which they are attached form an annelated five, six or seven membered heterocycle which may contain 1 to 4 heteroatoms in the ring which are N, O, S, SO, and/or SO2.

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