2-aminoethanesulfonic acid zinc complex compound

Details 2-aminoethanesulfonic acid zinc complex compound 2-aminoethanesulfonic acid zinc complex compound

1994-12-15

1996-02-06

Nazario-Gonzales, Porfirio

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heavy metal containing doai

514894, 514925, 556118, 556119, 556130, A61K 31315, C07F 306

Patent

active

054896096

DESCRIPTION:

BRIEF SUMMARY
CROSS REFERENCE TO RELATED APPLICATION

This aplication is a request for U.S. Examination under 35 U.S.C. .sctn.371 of International application No. PCT/JP93/00813 filed on Jun. 14, 1993.
1. Technical Field
The present invention relates to a novel 2-aminoethanesulfonic acid zinc complex compound, to a process for producing the same and to an anti-hepatitis agent, liver function improving agent and anti-ulcer agent which individually contain the same as an active ingredient.
2. Background Art
2-Aminoethanesulfonic acid (taurine) is already known to possess liver function protecting activity, but with its weak activity, cannot be expected to find application as an excellent anti-hepatitis agent and liver function improving agent.
The present inventors, with a specific view to preparing improved pharmaceuticals based on 2-aminoethanesulfonic acid derivatives, have conducted intensive testing for their pharmacological activities. In the course of this, it was discovered that the reaction of 2-aminoethanesulfonic acid with an alkali agent and zinc compound can yield [bis(2-aminoethanesulfonic acid).bis(alkali 2-aminoethanesulfonate)]zinc as represented by the following formula (Japanese Patent Application No. Hei 4-24642 (1992): ##STR2## (wherein M is an alkali metal).
The compounds of the formula (A), which possess greater antihepatitis activity, liver function improving activity and antiulcer activity than 2-aminoethanesulfonic acid, still show relatively reduced zinc contents as low as 10.76 and 10.21% in the cases of M being sodium and potassium, respectively. In the light of the above, the inventors carried out further research and synthesized bis(2-aminoethanesulfonic acid)zinc with a zinc content of 20.85%. Pharmacological tests indicate that the zinc complex compound, when compared with the compounds of the formula (A), exhibits more markedly potent anti-ulcer activity as well as comparable anti-hepatitis and liver function improving activities, and the finding was followed by additional research, leading to the completion of the present invention.


DISCLOSURE OF THE INVENTION

The present invention relates to a 2-aminoethanesulfonic acid zinc complex compound represented by formula [I]: ##STR3## and to a process for producing the same as well as to an antihepatitis agent, liver function improving agent and anti-ulcer agent.
The compound of formula (I) can be produced by reacting a zinc compound (0.5 mole) with an alkali metal 2-aminoethanesulfonate (1 mole).
The alkali metal 2-aminoethanesulfonate can be prepared by reacting 2-aminoethanesulfonic acid (1 mole) with an alkali agent (1 mole). The resultant alkali metal salt may be reacted with the zinc compound after being isolated, but can also be reacted with the zinc compound as such without being isolated.
As the alkali agent, there can desirably be used alkali metal alcoholates, such as sodium methylate, sodium ethylate, potassium methylate, potassium ethylate or potassium t-butoxide.
Referring to the zinc compound, zinc bromide and zinc iodide are preferred, but other zinc compounds may be utilized.
The reaction of the zinc compound with the alkali metal 2-aminoethanesulfonate is normally conducted in a suitable solvent, such as methanol and ethanol, at room temperature or under warming for several hours, and after conclusion of the reaction, the reaction product can be purified by conventional means.
The compound of formula (I) possesses improved anti-hepatitis, liver function improving and anti-ulcer activities, and shows reduced toxicity, thus being useful as an anti-hepatitis, liver function improving and anti-ulcer agent. The compound, either per se or after being mixed with pharmacologically acceptable, appropriate excipients, carriers, diluents, etc., can be administered orally or parenterally in various dosage forms, such as tablets, capsules, powders, syrups and ointments. The compound is administered to patients at varied doses depending upon their symptoms, age, body weight, route of administration and the like, and is normally given to

REFERENCES:
patent: 4355043 (1982-10-01), Durlach
Chemical Abstracts, vol. 88, No. 4, Jan. 23 1978, Abstract No. 30369m, p. 477.

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