Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-12-13
1995-03-28
Gerstl, Robert
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514326, 514333, 514363, 544367, 546209, 546277, 548141, C07D285135, C07D41712, A01K 3141, A01K 31435
Patent
active
054017432
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to aminoalkyl-substituted 2-amino-5-mercaptothiadiazoles, the preparation thereof and the use thereof for controlling diseases.
U.S. Pat. No. 4,074,049 describes aminoalkylthiothiadiazoles which act as fungicides and inhibitors of platelet aggregation. JP 2 153 276 describes similar compounds which are used for treating liver disorders.
We have now found that aminoalkyl-substituted 2-amino-5-mercapto-1,3,4-thiadiazole derivatives of the formula I ##STR2## where n is an integer from 2 to 6, and ##STR3## where Ar is phenyl which is unsubstituted or monosubstituted 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, R.sup.1 is hydrogen or C.sub.1 -C.sub.5 -alkyl, and R.sup.2 is phenyl which is unsubstituted or monosubstituted by C.sub.1 -C.sub.5 -alkyl, C.sub.2539Y1 -C.sub.5 -alkoxy, halogen, hydroxyl or trifluoromethyl, or is thienyl, and m is 0, 1 or 2, pharmacological properties.
In the formula I, A is preferably ##STR4## (m=0), Ar=phenyl, pyridyl, pyrimidinyl), ##STR5## (R.sup.1 -C.sub.1 -C.sub.4 -Alkyl, R.sup.2 -phenyl, thienyl) and n is preferably 2 or 3.
The compounds of the formula I can be prepared by chlorine, bromine or R.sup.3 SO.sub.2 O--(where R.sup.3 is lower alkyl or phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.3 -alkyl or halogen), or a hydrohalic acid salt of these compounds, with 2-amino-5-mercaptothiadiazole or an alkali metal salt of this compound, or ##STR6## where n has the abovementioned meanings, and X is as defined in a), with an amine of the formula IV where appropriate into their salts 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 aliphatic alcohols, dimethylformamide, dimethoxyethane, tetrahydrofuran, toluene, xylene or a ketone such as acetone or butanone, and suitable acid acceptors are inorganic bases such as sodium or potassium carbonate or organic bases such as triethylamine or pyridine. 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 recrystallisation from a solvent, chromatography or conversion into an acid addition compound.
The alkylamines of the formula II used as starting materials are known from the literature or can be obtained in a conventional way by alkylation of the amines of the formula IV with .omega.-X-substituted C.sub.2 -C.sub.6 -alkyl halides.
The reactions in process b) take place in the melt, if required also in the presence of a solvent, eg. 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, eg. pyridine. It is also possible where appropriate for the amine component IV in excess to act as reagent, base and solvent.
The resulting compounds according to the invention are, where appropriate, converted into their addition salts with physiologically tolerated acids. Examples of suitable physiologically tolerated organic and inorganic acids are hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, oxalic acid, maleic acid, fumaric acid, lactic acid, tartaric acid, adipic acid and benzoic acid. Others are to be found in Fortschritte der Arzneimittelforschung, Vol. 10, pp. 224 et seq., Birkh,uml/a/ user Verlag, Basel and Stuttgart, 1966.
The acid addition salts are usually obtained in a conventional way by mixing the free base or solutions thereof with the appropriate acid or solutions thereof in an organic solvent, for example a lower alcohol s
REFERENCES:
patent: 4074049 (1978-02-01), Begin et al.
Chem. Abstr. JP 2 153 276 vol. 107, 1987--p. 791.
Rendenbach-Mueller Beatrice
Teschendorf Hans-Juergen
Unger Liliane
BASF - Aktiengesellschaft
Gerstl Robert
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