Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-04-16
1994-12-27
Bernhardt, Emily
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
544239, C07D23714, A61K 3150
Patent
active
053766563
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The invention relates to 6-aryl-3[2H]pyridazinones, their preparation and use and medicaments containing them.
PRIOR ART
From European patent 163 965 certain pyridazinones are known which have bronchospasmolytic and/or cardiotonic activity.
DESCRIPTION OF THE INVENTION
It has been found that the 6-aryl-3[2H]pyridazinones described below have advantageous pharmcological properties by which they differ surprisingly from the compounds of European patent 163 965.
The invention relates to 6-aryl-3[2H]pyridazinones of the general formula I ##STR2## wherein one of the substituents R1 and R2 denotes methoxy, difluoromethoxy or ethoxy and the other denotes C4-C7-cycloalkoxy or C3-C7-cycloalkylmethoxy, and their salts with bases.
C4-C7-Cycloalkoxy represents, for example, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy and cycloheptyloxy, cyclopentyloxy being preferred.
C3-C7-Cycloalkylmethoxy represents, for example, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy and cycloheptylmethoxy, cyclopropylmethoxy and cyclobutylmethoxy being preferred.
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, aminosugars, 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[2H]pyridazinones of the abovementioned general formula I, wherein R1 denotes methoxy, difluoromethoxy or ethoxy, R2 denotes C4-C6-cycloalkoxy or C3-C6-cycloalkylmethoxy, and their salts with bases.
A further embodiment (embodiment b) of the invention comprises 6-aryl3.mu.H]pyridazinones of the abovementioned general formula I, wherein R1 denotes C4-C6-cycloalkoxy or C3-C6-cycloalkylmethoxy and R2 denotes methoxy, difluoromethoxy or ethoxy, and their salts with bases.
Embodiment b is preferable to embodiment a.
Preferred compounds according to the invention are those of the formula I, wherein one of the substituents R1 and R2 denotes cyclopentyloxy, cycloheptyloxy, cyclopropylmethoxy or cyclobutylmethoxy, and the other denotes methoxy or difluoromethoxy, and their pharmacologically tolerated salts with bases.
The invention furthermore relates to the use of the compounds according to the invention in the treatment or prophylaxis of illnesses based on a disease of the bronchi.
The invention furthermore relates to the use of the compounds according to the invention and their pharmacologically tolerated salts for the preparation of medicaments for the treatment and/or prophylaxis of diseases of the bronchi.
The invention furthermore relates to a process for the preparation of the 6-aryl-3[2H]pyridazinones of the general formula I and of their salts with bases, which comprises ##STR3## in which R1 and R2 have the abovementioned meaning, and, if desired, then converting the resulting pyridazinone into a salt, or ##STR4## in which R1 and R2 have the abovementioned meaning, with hydrazine and, if desired, then converting the resulting pyridazinone into a salt, or ##STR5## in which R1 and R2 have the abovementioned meaning, with hydrazine and, if desired, then converting the resulting pyridazinone into a salt.
The process according to
REFERENCES:
patent: 4088762 (1978-05-01), Hakim et al.
patent: 4665074 (1987-05-01), Amschler
patent: 4707481 (1987-11-01), Amschler et al.
patent: 5236918 (1993-08-01), Amschler et al.
Bernhardt Emily
ByK Gulden Lomberg Chemische Fabrik GmbH
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