Process for preparing optically active mevalonolactone compounds

Details Process for preparing optically active mevalonolactone compounds Process for preparing optically active mevalonolactone compounds

1996-08-22

1999-08-17

Owens, Amelia

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546174, C07D21500

Patent

active

059395524

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD THE INVENTION

This invention relates to a process for preparing optically active mevalonolactone compounds. More particularly, this invention relates to a commercial process for preparing optically active mevalonolactone compounds which are useful for prevention and treatment of hyperlipemia, arteriosclerosis, etc.


BACKGROUND OF THE INVENTION

With respect to pharmaceutical compounds which have an asymmetric center, it is known that optical isomers of some of such compounds respectively have different physiological activities. That is, often only one of the isomers has physiological effect in vivo or only one of them has terato-geneticity as seen in thalidomide. However, it is difficult to optically separate a racemic compound by a conventional method such as distillation, crystallization, etc. Thus most of the pharmaceutical compounds having an asymmetric center are marketed in the form of a racemic compound.
Under the circumstances, a commercial process, by which only an optical isomer of various such pharmaceutical compounds and intermediate compounds therefor can be isolated, is strongly desired. Because, if only physiologically active and useful isomers can be used as therapeutics, a small dose suffices and abatement of undesirable side effect is expected.
Although physiologically active isomers of mevalonolactone compounds are very useful for prevention and treatment of hyperlipemia, arteriosclerosis, etc., there has been no commercial process for optical resolution.
The object of this invention is to solve the above-described problem. In other words, the object of this invention is to isolate optically active isomers of mevalonolactone compounds with high purity in a commercial scale.


DISCLOSURE OF THE INVENTION

In the present invention, batch system chromatography and simulated moving bed chromatographic process using columns filled with a filler for optical resolution are employed in order to solve the above-described problem.
More particularly, the invention described in claim 1 is a process for preparing an optically active mevalonolactone compound comprising conducting optical resolution of the racemic mixture of an optically active mevalonolactone compound by means of batch system chromatography which uses a column filled with a filler selected from a group consisting of particles of a polysaccharide ester derivative, particles of a polysaccharide carbamate derivative and particles of a support which carries a polysaccharide ester derivative and/or a polysaccharide carbamate derivative.
The invention described in claim 2 is a process for preparing an optically active mevalonolactone compound as described in claim 1, wherein the polysaccharide ester derivative and the polysaccharide carbamate derivative are those in which part of or all of the hydrogen atoms on the hydroxy groups or amino groups of the polysaccharide are substituted with an atom groups represented by any of the following chemical formulas (1) to (4): ##STR1## wherein R stands for an aromatic group which may contain a hetero atom and may be unsubstituted or substituted with at least one selected from a group consisting of an alkyl group having 1-12 carbon atoms, an alkoxy group having 1-12 carbon atoms, an alkylthio group having 1-12 carbon atoms, a cyano group, a halogen atom, an acyl group having 1-8 carbon atoms, an acyloxy group having 1-8 carbon atoms, a hydroxy group, an alkoxycarbonyl group having 1-12 carbon atoms, a nitro group, an amino group and an alkylamino group having 1-8 carbon atoms; and X stands for a hydrocarbon group having 1-4 carbon atoms, which may contain a double bond or triple bond.
The invention described in claim 3 is a process for preparing an optically active mevalonolactone compound comprising forming a circulation flow circuit comprising a plurality of columns filled with an optical resolution filler and endlessly connected in series; enforcing a fluid to flow through the circuit in one direction; providing each with an inlet port through which the fluid is introduced into th

REFERENCES:
patent: 5284953 (1994-02-01), Ohara et al.

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