6-aryl-3-cyanaminopyridazines, their preparation and use and med

Details 6-aryl-3-cyanaminopyridazines, their preparation and use and med 6-aryl-3-cyanaminopyridazines, their preparation and use and med

1991-12-13

1993-08-17

Bernhardt, Emily

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

544224, 544239, A61K 3150, C07D23720

Patent

active

052369188

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The invention relates to 6-aryl-3-cyanaminopyridazines, their preparation and use and medicaments containing them.


PRIOR ART

6-Aryl-3-cyanoaminopyridazines are not known.


DESCRIPTION OF THE INVENTION

It has been found that certain 6-aryl-3-cyanaminopyridazines have advantageous pharmacological actions.
The invention relates to 6-aryl-3-cyanaminopyridazines of the general formula I ##STR1## wherein one of the substituents R1 and R2 denotes methoxy, difluoromethoxy or ethoxy and the other denotes C1-C5-alkoxy, C4-C7-cycloalkoxy, C3-C7-cycloalkylmethoxy, C3-C5-alkenyloxy or C1-C4-polyfluoroalkoxy, and X denotes cyanamino, and their salts with bases.
C1-C5-Alkoxy is straight-chained or branched. Examples of C1-C5-alkoxy radicals which may be mentioned are the methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec.-butoxy, tert-butoxy, n-pentyloxy, isopentyloxy and the 2,2-dimethylpropoxy radical. C3-C4-Alkoxy is preferred.
C4-C7-Cycloalkoxy represents, for example, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy or cycloheptyloxy, cyclopentyloxy being preferred.
C3-C7-Cycloalkylmethoxy represents, for example, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy or cycloheptylmethoxy, cyclopropylmethoxy and cyclobutylmethoxy being preferred.
C3-C5-Alkenyloxy is straight-chain or branched. The double bond of alkenyloxy does not originate from the carbon atom to which the oxygen atom is bonded. Examples of C3-C5-alkenyloxy radicals which may be mentioned are the buten-2-yloxy, the allyloxy and the methallyloxy radical.
C1-C5-Alkoxy is preferable to C3-C5-alkenyloxy.
C1-C4-Polyfluoroalkoxy is understood as meaning straight-chain or branched C1-C4-alkoxy in which at least 2 hydrogen atoms are replaced by fluorine. Straight-chain C1-C3-alkoxy in which at least 2 hydrogen atoms are replaced by fluorine is preferred. Preferred C1-C4-polyfluoroalkoxy groups are trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy and, in particular, difluoromethoxy and 2,2,2-trifluoroethoxy.
By cyanamino there is understood the --NHCN group.
Possible salts are salts with inorganic and organic bases. The pharmacologically tolerated salts of the inorganic and organic bases usually used in galenics may be mentioned in particular. Salts which are not pharmacologically tolerated and may initially be obtained as process products, for example, in the preparation of the compounds according to the invention on an industrial scale are converted into pharmacologically tolerated salts by processes known to the expert. Examples of such suitable salts are water-soluble and water-insoluble salts with bases, the cations of the alkali metals or alkaline earth metals being used above all as the cations for the salt formation; however, it is also possible to use the corresponding cations of organic nitrogen bases, such as amines or amino-alkanols, amino-sugars etc. Salts which may be mentioned as examples are those of sodium, magnesium, calcium, dimethylamine, diethylamine, ethanolamine, diethanolamine, triethanolamine, glucamine, N-methylglucamine (meglumine), glucosamine and N-methylglucosamine.
One embodiment (embodiment a) of the invention comprises 6-aryl-3-cyanaminopyridazines of the abovementioned general formula I, wherein C3-C4-alkenyloxy or C1-C2-polyfluoroalkoxy and
A further embodiment (embodiment b) of the invention comprises 6-aryl-3-cyanaminopyridazines of the abovementioned general formula I, wherein C3-C4-alkenyloxy or C1-C2-polyfluoroalkoxy,
Preferred compounds according to the invention are those of the formula I wherein one of the substituents R1 and R2 denotes methoxy, difluoromethoxy or ethoxy and the other denotes C1-C4-alkoxy, C4-C6-cycloalkoxy, C3-C6-cycloalkylmethoxy or C1-C2-polyfluoroalkoxy, and X denotes cyanamino, and their salts with bases.
Preferred representatives of embodiment a are those in which R2 denotes C1-C4-alkoxy, C3-C6-cycloalkylmethoxy or C1-C2-polyfluoroalkoxy.
Preferred representatives of embodiment b are those in which R1 denotes C2-C4-alkoxy, C4-C6-cycloalkoxy,

REFERENCES:
patent: 4235928 (1980-11-01), Eicken et al.
patent: 4665074 (1987-05-01), Amschler
patent: 4707481 (1987-11-01), Amschler et al.
patent: 4711959 (1987-12-01), Kluth et al.
Chapleo et al., J. Med. Chem. 25, p. 821 (1982).
Stanovnik et al., J. Heterocyclic. Chem. 19, p. 577 (1982).

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