Antidiabetic phosphonates
First Claim
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1. A compound selected from those of the formula:
- ##STR39## wherein A and B are selected independently of each other from the group consisting of C1 to C4 alkylene and C2 to C4 hydroxyalkylene R1 is selected from the group consisting of hydrogen, hydroxy, 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, mono- and disubstituted phenyl (wherein the substituents are selected from alkyl C1 to C6, alkoxy C1 -C6, NO2 or halo), C3 to C8 isoalkyl, Cl3 CCH2 --, CH2 ═
CHCH2 --, ZCH2 CH2 -- (where Z is SO2 R2, SR2, OR2 or Si(R2)3 and R2 is C1 to C3 alkyl), ##STR40## where R3 is C1 to C3 alkyl and R3 -R3 is alkylene or acetal), ##STR41## where R4 is hydrogen or methyl), ##STR42## ##STR43## (where R8 is hydrogen or C1 to C18 alkyl, ##STR44## phenylmethyl, substituted phenylmethyl wherein the substituents are selected from C1 to C18 alkyl, C1 to C6 alkoxy, nitro and halogen; and
with the provisos that (a) when A and B are both --CH2 -- and R'"'"', R", R'"'"'" and R"" are the same and are phenyl or ethyl, then R1 may not be hydrogen, and (b) when A and B are both --CH2 -- and R'"'"', R", R'"'"'" and R"" are hydrogen, then R1 may not be hydrogen or --CH2 OH; and
, when any one or more of R'"'"', R", R'"'"'", or R"" are hydrogen, the pharmaceutically acceptable salts thereof.
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Abstract
Phosphonates are disclosed which stimulate the enzyme fructose-1,6-bisphosphatase and inhibit the enzyme 6-phosphofructo-1-kinase, thereby lowering glucose levels in mammals. These phosphonates may thus be used to treat hyperglycemia and/or diabetes. Processes for the synthesis of the phosphonates are also disclosed.
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Citations
17 Claims
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1. A compound selected from those of the formula:
- ##STR39## wherein A and B are selected independently of each other from the group consisting of C1 to C4 alkylene and C2 to C4 hydroxyalkylene R1 is selected from the group consisting of hydrogen, hydroxy, 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, mono- and disubstituted phenyl (wherein the substituents are selected from alkyl C1 to C6, alkoxy C1 -C6, NO2 or halo), C3 to C8 isoalkyl, Cl3 CCH2 --, CH2 ═
CHCH2 --, ZCH2 CH2 -- (where Z is SO2 R2, SR2, OR2 or Si(R2)3 and R2 is C1 to C3 alkyl), ##STR40## where R3 is C1 to C3 alkyl and R3 -R3 is alkylene or acetal), ##STR41## where R4 is hydrogen or methyl), ##STR42## ##STR43## (where R8 is hydrogen or C1 to C18 alkyl, ##STR44## phenylmethyl, substituted phenylmethyl wherein the substituents are selected from C1 to C18 alkyl, C1 to C6 alkoxy, nitro and halogen; and
with the provisos that (a) when A and B are both --CH2 -- and R'"'"', R", R'"'"'" and R"" are the same and are phenyl or ethyl, then R1 may not be hydrogen, and (b) when A and B are both --CH2 -- and R'"'"', R", R'"'"'" and R"" are hydrogen, then R1 may not be hydrogen or --CH2 OH; and
, when any one or more of R'"'"', R", R'"'"'", or R"" are hydrogen, the pharmaceutically acceptable salts thereof. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17)
- ##STR39## wherein A and B are selected independently of each other from the group consisting of C1 to C4 alkylene and C2 to C4 hydroxyalkylene R1 is selected from the group consisting of hydrogen, hydroxy, C1 to C4 alkyl, C1 to C4 hydroxyalkyl, C2 to C4 dihydroxyalkyl, C3 or C4 trihydroxyalkyl and C4 tetrahydroxyalkyl;
Specification
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Current AssigneeAmerican Cyanamid Co (Pfizer Inc.)
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Original AssigneeAmerican Cyanamid Co (Pfizer Inc.)
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InventorsAyral-Kaloustian, Semiramis, Floyd, Middleton B. Jr., Claus, Thomas H., DeVries, Vern G.
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Primary Examiner(s)WHITE, EVERETT
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Application NumberUS07/232,333Time in Patent Office718 DaysField of Search536/117, 514/24, 514/25US Class Current536/117CPC Class CodesA61P 3/08 for glucose homeostasis pan...A61P 3/10 for hyperglycaemia, e.g. an...A61P 43/00 Drugs for specific purposes...C07F 9/65515 the oxygen atom being part ...C07H 11/04 Phosphates; Phosphites; Pol...
