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Antidiabetic alpha-substituted phosphonates

  • US 4,943,629 A
  • Filed: 08/12/1988
  • Issued: 07/24/1990
  • Est. Priority Date: 08/12/1988
  • Status: Expired due to Fees
First Claim
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1. A compound selected from those of the formula:

  • ##STR107## wherein A is selected from the group consisting of C1 -C4 alkylene and C2 to C4 hydroxyalkylene;

    B is selected from the group consisting of C1 to C4 alkylene and C2 to C4 hydroxyalkylene in which the carbon atom of the alkylene moiety or the hydroxyalkylene moiety which is adjacent to the phosphorous atom is mono- or disubstituted with a substituent selected from the group consisting of halogen, hydroxy, and C1 to C4 alkoxy;

    R1 is selected from the group consisting of hydrogen, C1 to C4 alkyl, C1 to C4 hydroxyalkyl, C2 to C4 dihydroxyalkyl, C3 or C4 trihydroxyalkyl and C4 tetrahydroxyalkyl;

    R'"'"', R", R"'"'"' and R"" are selected independently from the group consisting of hydrogen, C1 to C18 alkyl, C3 to C6 cycloalkyl, phenyl, C3 to C8 isoalkyl, Cl3 CCH2 --, CH2 CH═

    CH2 --, ZCH2 CHh2 -- [where Z is SO2 R2, SR2, OR2, or Si(R2)3, and R2 is C1 to C3 alkyl], ##STR108## [where R3 is C1 to C3 alkyl and R3 -R3 is alkylene or acetal], ##STR109## (where R4 is hydrogen or methyl), ##STR110## [where, when R5

    R6, they are both hydrogen, fluoro or C1 -C4 alkyl, R5 is hydrogen, R6 is fluoro, oxy or OR7 [where R7 is C1 to C6 alkyl, C3 to C6 cycloalkyl or aryl]], ##STR111## [where R8 is hydrogen or C1 to C18 alkyl], ##STR112## phenylmethyl, substituted phenylmethyl wherein the substituents are selected from C1 to C18 alkyl, C1 to C6 alkoxy, NO2 and halogen, and mono- and disubstituted phenyl wherein the substituents are selected from C1 to C18 alkyl, C1 to C6 alkoxy, NO2 and halogen; and

    , when any one or more of R'"'"', R", R"'"'"' or R"" are hydrogen, the pharmacologically acceptable salts thereof.

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