Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-03-28
1995-09-12
Bernhardt, Emily
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
544224, A61K 3150, C07D23720
Patent
active
054496764
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP92/00872 filed Apr. 21, 1992.
TECHNICAL FIELD
The invention relates to 3-amino-6-arylpyridazines, processes for their preparation, their use and pharmaceuticals containing them. The compounds according to the invention are used in the pharmaceutical industry for the production of medicaments.
PRIOR ART
The described 3-amino-6-arylpyridazines are novel.
DESCRIPTION OF THE INVENTION
It has been found that the novel compounds described in detail below have advantageous pharmacological properties by which they differ from known compounds in a surprising and particularly advantageous manner.
The invention relates to 3-amino-6-arylpyridazines of the general formula I (see attached sheet of formulae), in which one of the substituents R1 and R2 denotes methoxy, difluoromethoxy or ethoxy and the other denotes 1-5C-alkoxy, 4-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy, 3-5C-alkenyloxy or 1-4C-polyfluoroalkoxy, X denotes amino, and their salts with acids and their N-oxides.
1-5C-Alkoxy is straight-chain or branched. Examples of 1-5C-alkoxy radicals which may be mentioned are the methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec.-butoxy, tert.-butoxy, n-pentyloxy, isopentyloxy and 2,2-dimethylpropoxy radical. 3-4C-alkoxy is preferred.
4-7C-Cycloalkoxy represents, for example, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy and cycloheptyloxy, of which cyclopentyloxy is preferred.
3-7C-Cycloalkylmethoxy represents, for example, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy and cycloheptylmethoxy, of which cyclopropylmethoxy and cyclobutylmethoxy are preferred.
3-5C-Alkenyloxy is straight-chain or branched. The double bond of alkenyloxy does not start from the carbon atom which is bonded the oxygen atom. Examples of 3-5C-alkenyloxy radicals which may be mentioned are the buten-2-yloxy, the allyloxy and the methallyloxy radical.
1-5C-Alkoxy is preferred to 3-5C-alkenyloxy.
1-4C-Polyfluoroalkoxy means straight-chain or branched 1-4C-alkoxy in which at least two hydrogen atoms are replaced by fluorine. Straight-chain 1-3C-alkoxy in which at least two hydrogen atoms are replaced by fluorine is preferred. Preferred 1-4C-polyfluoroalkoxy groups are trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy and, in particular, difluoromethoxy and 2,2,2-trifluoroethoxy.
Amino means the group NH.sub.2.
Suitable and preferred salts for compounds of the formula I are all acid addition salts. Particular mention may be made of the pharmacologically acceptable salts of the inorganic and organic acids normally used in pharmaceutical technology. Pharmacologically unacceptable salts which may, for example, be the initial products of the process for the preparation of the compounds according to the invention on the industrial scale are converted into pharmacologically acceptable salts by processes known to the person skilled in the art. Suitable examples of these are acid addition salts which are soluble in water and insoluble in water, such as the hydrochloride, hydrobromide, hydroiodide, phosphate, nitrate, sulfate, acetate, citrate, gluconate, benzoate, hibenzate, fendizoate, butyrate, sulfosalicylate, maleate, laurate, malate, fumarate, succinate, oxalate, tartrate, amsonate, embonate, metembonate, stearate, tosylate, 3-hydroxy-2-naphthoate or mesylate.
The N-oxides of the compounds of the formula I can be described by the general formula I* (see sheet of formulae) in which R1, R2 and X have the abovementioned meanings.
The N-oxides of the 3-amino-6-arylpyridazines according to the invention can exist as tautomeric forms. One proton of the 3-amino group is able to migrate between this group and the oxygen in position 2 of the pyridazine ring. When only one tautomer is mentioned or depicted according to the invention, in each case the other tautomer is also to be understood.
One embodiment (embodiment a) of the invention comprises 3-amino-6-arylpyridazines of the general formula I in which 3-4C-alkenyloxy or 1-2C-polyfluoroalkoxy and
Another embodiment (embodiment b) o
REFERENCES:
patent: 4665074 (1987-05-01), Amschler
patent: 4707481 (1987-11-01), Amschler et al.
patent: 4791110 (1988-12-01), Arnold et al.
Amschler Hermann
Schudt Christian
Bernhardt Emily
ByK Gulden Lomberg Chemische Fabrik GmbH
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