EP1385856A2 — Amino acid complexes of c-aryl glucosides for treatment of diabetes and method

USPTO Abstract

Crystalline complexes are obtained from a 1:1 or 2:1 mixtures of either the (D) or (L) enantiomer of natural amino acids and compounds of formula (I) wherein R1, R2 and R2a are independently hydrogen, OH, OR5, alkyl, -OCHF?2, -OCF3¿, -SR¿5a? or halogen; R3 and R4 are independently hydrogen, OH, OR5b, alkyl, cycloalkyl, CF?3, -OCHF2, -OCF3¿, halogen, -CONR¿6?R6a, -CO?2R¿5c, -CO2H, -COR¿6b?, -CH(OH)R6c, -CH(OR5d)R6d, -CN, -NHCOR5e, -NHSO?2R¿5f, -NHSO2Aryl, -SR¿5g?, -SOR5h, -SO?2R¿5i, 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 R¿3? 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, and/or SO?2; R¿5, R5a, R5b, R5c, R5d, R5e, R5f, R5g, R5h and R5i are independently alkyl; R6, R6a, R6b, R6c and R6d 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. A method is also provided for treating diabetes and related diseases employing an SGLT2 inhibiting amount of the above complex alone or in combination with another antidiabetic agent or other therapeutic agent.