6-.alpha.-hydroxy derivatives of mevinic acids
AssigneeE. R. Squibb & Sons, Inc.
InventorsRavi K. Varma, Sam T. Chao, Eric M. Gordon
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Abstract
Compounds of the formula ##STR1## and pharmaceutically acceptable salts thereof have been found to possess activity as cell-selective HMG-CoA reductase inhibitors, thus making them useful as antihypercholesterolemic agents. In the above formula, ##STR2## R.sup.1 is hydrogen, alkyl, cycloalkyl, aryl or arylalkyl; and R.sup.2 is hydrogen, alkyl, ammonium, or alkali metal.
Claims16
A compound of the formula
- and pharmaceutically acceptable salts thereof, wherein ##STR18## R.sub.1 is hydrogen, alkyl, cycloalkyl, aryl or arylalkyl;
- R.sup.2 is hydrogen, alkyl, ammonium, or alkali metal;
- "alkyl" refers to straight and branched chain groups of up to twelve carbons;
- "cycloalkyl" refers to cyclic hydrocarbon groups of three to twelve carbons;
- and
- "aryl" refers to monocyclic or bicyclic aromatic hydrocarbon groups of six to ten carbons.
A process for preparing a compound of the formula ##STR21## which comprises treating a compound of the formula ##STR22## with a base selected from 2,6-lutidine, collidine, pyridine, quinoline, 2-methylquinoline, sodium bicarbonate and potassium bicarbonate and sulfonic anhydride, wherein:
- R.sup.1 is hydrogen, alkyl cycloalkyl, aryl, or arylalkyl;
- and
- Pro.sup.2 is a protecting group.
A process for preparing a product of the formula ##STR23## which comprises:
- (a) treating a compound of the formula ##STR24## wherein Pro.sup.2 is a protecting group with a base selected from 2,6-lutidine, collidine, pyridine, quinoline, 2-methylquinoline, sodium bicarbonate and potassium bicarbonate and a sulfonic anhydride to form an alpha-hydroxy intermediate of the formula ##STR25## (b) deprotecting the alpha-hydroxy intermediate in the presence of a catalyst to form the product;
- wherein R.sup.1 is hydrogen, alkyl, cycloalkyl, aryl or arylalkyl.
A process for preparing a product of the formula ##STR26## which comprises:
- (a) treating a compound of the formula ##STR27## wherein Pro.sup.2 is a protecting group with an organic base selected from 2,6-lutidine, collidine, pyridine, quinoline, 2-methylquinoline, sodium bicarbonate and potassium bicarbonate, and a sulfonic anhydride to form an alpha-hydroxy intermediate of the formula ##STR28## (b) deprotecting the alpha-hydroxy intermediate in the presence of a catalyst to form a lactone of the formula ##STR29## (c) hydrolyzing the lactone with an aqueous ammonium or alkali metal base to form the product;
- wherein:
- R.sup.1 is hydrogen, alkyl, cycloalkyl, aryl or arylalkyl;
- and
- R.sup.2 is hydrogen, alkyl, ammonium, or alkali metal.
Dependencies are inferred from the claim text.