Processes for the preparation of D-chiro-inositol

Details Processes for the preparation of D-chiro-inositol Processes for the preparation of D-chiro-inositol

1996-02-09

1998-02-03

Kight, John

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

Organic compounds

Oxygen containing

C07C 3514, C07C 3516

Patent

active

057146438

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to improved processes for the preparation of D-chiro-inositol (hereinafter sometime abbreviated simply as "DCI").
In recent years, DCI is receiving attention as a therapeutic drug or preventive drug for non-insulin-dependent diabetes mellitus.


BACKGROUND ART

As processes for the preparation of DCI, the following processes (1) to (4) are known to date: a monomethyl ether derivative of DCI) as contained in a plant such as Bougainviiles spectabilis, sugar pine or redwood, by extracting said plant with a suitable solvent and then demethylating pinitol with hydroiodic acid or the like to produce DCI. material 1-chloro-2,3-dihydroxycyclohexa-4,6-diene, and producing DCI (1993)!. a starting material, and producing DCI therefrom via several reaction kasugamycin of high purity, heating it in 2N aqueous trifluoroacetic acid or 5N aqueous hydrochloric acid to hydrolyze kasugamycin and produce DCI, passing the resulting reaction solution, for the purpose of neutralization and elimination of impurities, through a column containing a strongly basic ion-exchange resin and a column containing a strongly acidic ion-exchange resin, and then crystallizing DCI from the liquid effluent as finally flown out of said resin column, by addition of ethanol to said
Although a variety of the above-mentioned processes have been proposed as processes for the preparation of DCI as described above, they are accompanied by various drawbacks which do not allow advantageous preparation of DCI to be achieved on a commercial scale.
Thus, the process for the preparation of DCI according to said process (1), which includes the step of extracting pinitol from the plant, is cumbersome in making the extraction of pinitol and the purification of DCI formed, and can give only a low yield of DCI.
On the other hand, the process for the preparation of DCI according to said process (2) or (3), which includes the chemical synthesis steps, requires a stereospecific synthesis so that the reaction efficiency is low and the production cost of DCI is high.
The process (4) must use a very strong acid (aqueous solution of 5N hydrochloric acid or 2N trifluoroacetic acid, etc.) for the hydrolytic reaction of kasugamycin. Due to this very strong acid, side reactions can take place upon cleavage of kasugamycin molecules, and hence useless by-products are formed, resulting in a reduced yield of DCI. Further, this process requires such steps for the recovery and purification of DCI, where the strongly basic ion-exchange is used in a large quantity to neutralize the strong acid employed for the hydrolysis and also, the strongly acidic ion-exchange resin is also employed in a significant quantity to get rid of the basic compounds which have been formed as by-products, so that a further reduction can be involved in the yield of DCI. Besides, said process takes long time for operating the respective steps. In addition, a great deal of water is needed for the recovery of DCI and also for the regeneration etc., of the ion-exchange resins which were used in the purification of DCI. As a consequence, post-treatment of a large amount of waste water so formed is also needed. The process (4) therefore involves many problems.
There is hence an outstanding desire for the development of an industrially advantageous process for the preparation of DCI which can substitute for the above known preparation processes. In the above-mentioned circumstances, an object of this invention is to provide such a process which permits DCI to be produced at a high purity and high yield by simple and facile procedures.


DISCLOSURE OF THE INVENTION

We, the present inventors, have proceeded with an extensive investigation to solve the above problems. As a result, we have now devised such processes which can prepare DCI with commercial and many advantages by using kasugamycin as a raw material. Specifically, the present inventors have found that DCI can be produced with good reaction efficiency when hydrolysis of kasugamycin or its salt (unless otherwise spe

REFERENCES:
patent: 5091596 (1992-02-01), Kennington et al.

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