Pyridazinones, their preparation and use, and bronchospasmolytic

Details Pyridazinones, their preparation and use, and bronchospasmolytic Pyridazinones, their preparation and use, and bronchospasmolytic

1985-01-04

1987-11-17

Berch, Mark L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

544239, A61K 3150, C07D23714

Patent

active

047074817

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The invention relates to pyridazinones, their preparation and use, and medicaments containing pyridazinones.


PRIOR ART

6-Aryl-3[2H]pyridazinones as starting materials or intermediates for the synthesis of pharmaceuticals and plant protection agents and processes for their preparation are described, for example, by Baddar et al. [J.Chem. Soc. 1965, 3342], Steck [J.Heterocycl.Chem. 11(1974)755], Albright et al. [J.Heterocycl.Chem. 15(1978)881], Schreiber et al. [Bull.Soc.Chim.France 2(1973)625], Pitarch et al. [Eur.J.Med.Chem.-Chimica Therapeutica 9(1974)644] and Curran et al. [J.Med.Chem. 17(1974)273], or are known, inter alia, from the following descriptions: German Offenlegungsschrift 2,435,244, German Offenlegungsschrift 2,445,681 and German Offenlegungsschrift 2,757,923.
6-Aryl-3[2H]pyridazinones with a certain action are known, for example, from the following descriptions: German Offenlegungsschrift 2,427,943, German Offenlegungsschrift 2,810,267, German Offenlegungsschrift 2,845,220, European Offenlegungsschrift 8,391, European Offenlegungsschrift 10,156, Japanese Preliminary Published Application 58,008,015 and U.S.Patent Specification 4,397,854.
6-(3,4-Dimethoxyphenyl)-3[2H]pyridazinone is described by Pitarch et al. and in German Offenlegungsschrift 2,810,267.


SUMMARY OF THE INVENTION

Certain 6-aryl-3[2H]pyridazinones of the general formula I now have an advantageous pharmacological action.
The invention relates to 6-aryl-3[2H]pyridazinones of the general formula I ##STR2## wherein one of the substituents R1 or R2 denotes a methoxy group and the other denotes an alkoxy group with 2 to 5 carbon atoms or an alkenyloxy group with 3 to 5 carbon atoms and X denotes an oxygen atom or a sulfur atom, and their parmacologically acceptable salts with bases.
Alkoxy and alkenyloxy are straight-chain or branched. The double bond of alkenyloxy does not start from the carbon atom bonded to the oxygen atom. Examples of alkoxy and alkenyloxy which may be mentioned are n-butoxy, n-propoxy, ethoxy, amyloxy, 2,2-dimethylpropyloxy, isopentyloxy, isobutoxy, sec.-butoxy, isopropoxy, buten-2-yloxy, allyloxy and methallyloxy; preferred alkoxy radicals contain 3 or 4 carbon atoms.
Possible salts are salts with inorganic and organic bases. Cations which are used for the salt formation are, in particular, the cations of the alkali metals or alkaline earth metals, but the corresponding cations of organic nitrogen bases, such as amines or aminoalkanols, aminosugars and the like, are also used. Examples which may be mentioned are the salts of sodium, magnesium, calcium, dimethylamine, diethylamine, ethanolamine, diethanolamine, triethanolamine, glucamine, N-methylglucamine, glucosamine and N-methylglucosamine.
6-Aryl-3[2H]pyridazinones of the general formula Ia ##STR3## wherein R1a denotes a methoxy group, with 3 or 4 carbon atoms and with bases, form an embodiment of the invention.
6-Aryl-3[2H]pyridazinones of the general formula Ib ##STR4## wherein R1b denotes an alkoxy group with 2 to 4 carbon atoms or an alkenyloxy group with 3 or 4 carbon atoms, with bases, form another embodiment of the invention.
Preferred representatives of embodiment Ia are those in which R2a represents an n-propoxy, isopropoxy or isobutoxy group. Particularly preferred representatives are the compounds 6-(3-methoxy-4-n-propoxyphenyl)-3(2H)pyridazinone and 6-(4-isobutoxy-3-methoxyphenyl)-3(2H)pyridazinone.
Preferred representatives of the embodiment Ib are those in which R1b represents an n-propoxy, isopropoxy, allyl or isobutoxy group. Particularly preferred representatives are the compounds 6-(3-isobutoxy-4-methoxyphenyl)-3[2H]pyridazinone and 6-(4-methoxy-3-n-propoxyphenyl)-3[2H]pyridazinone.
The invention also relates to the use of the compounds according to claim 1 for the treatment or prophylaxis of diseases which are based on disorders of the bronchi and/or cardiac insufficiency, or for strengthening the heart, and to the appropriate medicaments.
The compounds 6-(3-methoxy-4-n-propoxyphenyl)-3[2H]pyridazinone, 6-(4-i

REFERENCES:
patent: 4397854 (1983-08-01), Sircar
Derwent, #B03, 18917 K/08 for JP58008-015 (Chem. Ab. 98, 137630) 1983.
Derwent, #B03, 18918 K/08 for JP58008016 (Mitsubishi) 1983.
Derwent, #B02, 16839 C/10 for EP8391 (Thomae) 3/80.
Derwent, #B03C02 11413X/07 for DT2435244 (Lentia) 1974.
Derwent, #B03, 33034C/19 for EP10156 (Merck) 1980.
Derwent, B03 49295B/27, Hoechst for DT2757923, 1979.
Derwent, B03 67389A/38 for DT2810267 (Sankyo) 9/78.
Derwent, B03C02 30268X/17 DT2445681, Lentia, 4/76.
"Attorney's Dictionary of Patent Claims", vol. 1, pp. A-21, A-22.
Baddar et al., J. Chem. Soc., 3342-3348, 1965.
Steck et al., J. Heterocycl. Chem., vol. 11, 755-761, 1974.
Albright et al., J. Heterocycl. Chem., vol. 15, 881-892, 1978.
Schreiber et al., Bull. Soc. Chim., France, 2, 625-629, 1973.
Pitarch et al., Eur. J. Med. Chem.-Chimica Therapeutica, vol. 9, No. 6, 644-650, 1974.
Curran et al., J. Med. Chem., vol. 17, No. 3, 273-281, 1974.

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