Optically pure stereogenically labile 4-substituted-2-hydroxytet

Details Optically pure stereogenically labile 4-substituted-2-hydroxytet Optically pure stereogenically labile 4-substituted-2-hydroxytet

1992-03-06

1994-03-29

Raymond, Richard L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514444, 514474, 549 60, 549315, 549316, A61K 31365, C07D30762

Patent

active

052985261

ABSTRACT:
The present invention relates to a method for synthesis of optically pure stereogenically labile 4-substituted-2-hydroxytetronic acids from an asymmetric .alpha.-hydroxy ester. The chiron approach of the present invention utilizes a non-nucleophilic lithium amide base under kinetically controlled Claisen conditions to produce a 4-substituted-2-pheylmethoxy precursor to the 4-substituted-2-hydroxy tetronic acid. The invention further relates to the use of such optically pure compounds as potent inhibitors of platelet aggregation by working at the level of cyclooxygenase. The invention further relates to the pharmaceutical use of such compounds in the treatment of coronary artery diseases, especially in the treatment and/or prevention of atherosclerosis.

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