Aminoalkyl-substituted 5-mercaptothiazoles, the preparation and

Details Aminoalkyl-substituted 5-mercaptothiazoles, the preparation and Aminoalkyl-substituted 5-mercaptothiazoles, the preparation and

1993-12-13

1995-05-23

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

514326, 514342, 544364, 544369, 544367, 546204, 546280, 548184, C07D41712, C07D27740, A61K 31425, A61K 31435

Patent

active

054182352

DESCRIPTION:

BRIEF SUMMARY
This application is a 371/of PCT/EP92/01004 filed May 8, 1992.
The present invention relates to novel amino-alkyl-substituted 5-mercaptothiazoles, the preparation thereof and the use thereof for controlling diseases.
U.S. Pat. No. 3,717,651 describes, inter alia, 5-mercapto-substituted thiazoles which have herbicidal properties.
We have now found that aminoalkyl-substituted 5-mercaptothiazoles of the formula I ##STR2## where R.sup.1 is H, C.sub.1 -C.sub.5 -alkyl, phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.5 -alkyl or C.sub.1 -C.sub.5 -alkoxy, or is thienyl, different, are each hydrogen, C.sub.1 -C.sub.5 -alkyl, which is unsubstituted or substituted by phenyl or thienyl, or is ##STR3## where Ar is phenyl which is unsubstituted or mono-substituted by C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -alkoxy, halogen, nitro, hydroxyl, trifluoromethyl or cyano, or is pyridyl, pyrimidinyl or thienyl, controlling diseases.
In the formula I, R.sup.1 is preferably H or C.sub.1 -C.sub.5 -alkyl, A is preferably ##STR4## or C.sub.1 -C.sub.5 -alkyl A.sub.r is unsubstituted phenyl or phenyl monosubstituted by and n is preferably 2 or 3.
The compounds of the formula I can be prepared by ##STR5## where R.sup.1 is as defined above, or a salt of this compound, with an .omega.-X-alkylamine of the formula III chlorine, bromine or R.sup.4 SO.sub.2 O--[R.sup.4 =C.sub.1 -C.sub.4 -alkyl or phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.3 -alkyl or halogen], or IV ##STR6## where R.sup.1, n and X have the stated meanings, or a salt of this compound, with an amine of the formula V formula VII ##STR7## where R.sup.1 is as defined above, and Y is chlorine or bromine, or with a hydrohalic acid salt of this compound, with physiologically tolerated acids.
The reactions in process a) preferably take place in a solvent at from room temperature to the boiling point of the solvent, where appropriate in the presence of an acid acceptor. Examples of solvents which can be used are dimethylformamide, or ketones such as acetone or butanone, and of acid acceptors are inorganic bases such as sodium or potassium carbonate or tertiary organic bases such as triethylamine or pyridine. In excess, the latter can also act as solvent.
The crude product is isolated in a conventional way, eg. by filtration, removal of the solvent by distillation, or extraction from the reaction mixture. The resulting compound is purified in a conventional way, for example by recrystallization from a solvent, chromatography or conversion into an acid addition compound.
The 5-mercaptothiazoles of the formula II used as starting materials are known from the literature or can be prepared by treating a thiazole of the formula VIII ##STR8## where R.sup.1 is as defined above, or a hydrohalic acid salt of this compound, with bases such as aqueous ammonia solution or sodium hydroxide solution, if required also in a two-phase mixture. Another possibility for the synthesis comprises reacting the thiazoles of the formula VII with inorganic sulfides such as potassium hydrogen sulfide. The mercaptothiazoles of the formula II need not be isolated for subsequent reactions. Thus, for example, it is also possible to obtain the compounds of the formula I according to the invention by treating a mixture of the thiazoles of the formula VIII and of the .omega.-X-alkylamines of the formula III with a base, in which case the mercaptothiazole of the formula II which is formed in situ immediately reacts with the alkylamines of the formula III.
The reactions in process b) take place in the melt, if required also in the presence of a solvent such as ethyl acetate, tetrahydrofuran, dimethylformamide, dimethoxyethane, toluene or xylene, at from room temperature to the boiling point of the solvent, preferably in the presence of a base such as sodium methylate, sodium ethylate, sodium hydride, sodium carbonate, potassium carbonate, or of an amine such as pyridine. It is also possible where appropriate for the amine component IV in excess to act as reagent, base and sol

REFERENCES:
patent: 3717651 (1973-02-01), Pilgram et al.
patent: 5071864 (1991-12-01), Rendenbach-Mueller et al.

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