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US 6,686,481 B2Granted
Highly purified simvastatin compositions
AssigneePlus Chemicals SA
InventorsSzabo Csaba, Ferenc Korodi, Melczer Istvan, Szabolcs Salyi, David Leonov
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Abstract
The present invention relates to a process to prepare semi synthetic statins, to intermediates formed during said process and to highly purified simvastatin produced by the process.
Claims17
A process for the formation of highly purified simvastatin from lovastatin, comprising the steps of:
- a) lactone ring opening by reacting lovastatin with an amine to form an amid;
- b) protecting a 1,3-diol moiety with a protecting group;
- c) removing a 2-methylbutyryl group attached by an ester linkage through an oxygen at position 8 of a hexahydronaphthalene ring;
- d) attaching a 2,2-dimethylbutyrate group by forming an ester linkage to a hydroxyl at position 8;
- e) removal of the protecting group;
- f) conversion of the amid to an acid salt;
- and,
- g) lactone ring closing to form simvastatin.
5 more elements
A process for the formation of a semisynthetic statin of Formula I,
- from a statin of Formula II,
- which comprises the steps of:
- a) lactone ring opening by reacting the statin of Formula II with an amine to form an amid;
- b) protecting a 1,3-diol moiety with a protecting group;
- c) removing a R1 group attached by an ester linkage through an oxygen at position 8 of a hexahydronaphthalene ring;
- d) attaching a R2 group by forming an ester linkage to a hydroxyl at position 8;
- b) removal of the protecting group;
- c) conversion of the amid to an acid salt;
- and,
- g) lactone ring closing to form the semi synthetic statin of Formula I
- wherein R1 and R2 are both acyl groups linked to the oxygen through an ester bond and R3 and R4 are independently selected from the group consisting of —H, —OH, —C1-10 alkyl, —C6-14 aryl, and —C6-14 aryl-C1-3.
8 more elements
Dependencies are inferred from the claim text.