Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-04-25
1996-07-09
Bernhardt, Emily
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
544236, 548533, A61K 3150, C07D48704
Patent
active
055345158
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP92/02418, filed Oct. 21, 1992.
FIELD OF APPLICATION OF THE INVENTION
The invention relates to novel compounds, processes for their preparation and their use as active ingredients in medicaments.
KNOWN TECHNICAL BACKGROUND
In J. Heterocyclic Chem. 10, 551 (1973), pyrrolopyridazines substituted in a certain manner are described. In U.S. Pat. No. 4,988,695, pyrrolo- and dihydropyrroloquinolines and their use as gastric acid secretion inhibitors are described.
BRIEF DESCRIPTION OF THE DRAWINGS
FIGS. 1 to 4 are structural formulae of compounds referred to in the specification by designations I to IV, respectively.
FIG. 5 is a synthesis scheme for preparing compounds of formula II.
DESCRIPTION OF THE INVENTION
The invention relates to novel compounds of the formula I (see FIG. 1), substituent --CH.sub.2 O--COR7, or two identical or different substituents from the group consisting of halogen, 1-4C-alkyl and 1-4C-alkoxy, identical or different substituents from the group consisting of halogen, 1-4C-alkyl, 1-4C-alkoxy, nitro, --NH--CO--NH.sub.2 (ureido), amino, 1-4C-alkylcarbonylamino and 1-4C-alkoxycarbonylamino, carboxy-1-4C-alkyl, (1,2-ethylene) and
1-4C-alkyl stands for straight-chain or branched alkyl radicals having 1 to 4 carbon atoms. Examples which may be mentioned are the butyl, isobutyl, sec-butyl, tertbutyl, propyl, isopropyl, ethyl and methyl radicals.
1-3C-alkylene stands for trimethylene, ethylene and in particular methylene.
Halogen within the meaning of the present invention is bromine, chlorine or fluorine.
In addition to the oxygen atom, 1-4C-alkoxy radicals contain one of the abovementioned 1-4C-alkyl radicals. The methoxy radical is preferred.
In addition to the carbonyl group, 1-4C-alkylcarbonyl radicals in the 1-4C-alkylcarbonylamino group contain one of the abovementioned 1-4C-alkyl radicals. The acetyl radical is preferred.
In addition to the carbonyl group, 1-4C-alkoxycarbonyl radicals in the 1-4C-alkoxycarbonylamino group contain one of the abovementioned 1-4C-alkoxy radicals. The methoxycarbonyl and the ethoxycarbonyl radicals are preferred.
1-4C-alkoxy-1-4C-alkyl stands for the abovementioned 1-4C-alkyl radicals, to which one of the abovementioned 1-4C-alkoxy radicals is bonded. The methoxymethyl radical is preferred.
1-4C-alkoxycarbonyl-1-4C-alkyl stands for the abovementioned 1-4C-alkyl radicals, to which a 1-4C-alkoxycarbonyl radical (carbonyl with one of the abovementioned 1-4C-alkoxy radicals) is bonded. The methoxycarbonylmethyl and the methoxycarbonylethyl radicals are preferred.
Carboxy-1-4C-alkyl stands for the abovementioned 1-4C-alkyl radicals, to which a carboxyl radical (--COOH) is bonded. The carboxymethyl and the carboxyethyl radicals are preferred.
Suitable salts of compounds of the formula I are preferably all acid addition salts. Particular mention may be made of the pharmacologically tolerable salts of the inorganic and organic acids customarily used in pharmacy. Pharmacologically intolerable salts which, for example, can be obtained initially as process products in the preparation of the compounds according to the invention on the industrial scale, are converted into pharmacologically tolerable salts by processes known to the person skilled in the art. Suitable salts of this type are, for example, water-soluble and water-insoluble acid addition salts, such as the hydrochloride, hydrobromide, hydriodide, phosphate, nitrate, sulfate, acetate, citrate, gluconate, benzoate, hibenzate, fendizoate, butyrate, sulfosalicylate, maleate, laurate, malate, fumarate, succinate, oxalate, tartrate, amsonate, embonate, metembonate, stearate, rosylate, 2-hydroxy-3naphthoate or mesylate.
One embodiment (embodiment a) of the invention is compounds of the formula I in which R3 is hydrogen, R6 is hydrogen, B is a valence bond and n is the number 0, and R1, R2, R4, R5 and A have the meanings indicated at the beginning, and their salts. These compounds are novel intermediates for the preparation of the pharmacologically active final products.
REFERENCES:
patent: 4988695 (1991-01-01), Brown et al.
Marquet et al, Chimie Therapeutique, 3(5) pp. 348-355 (1968).
Marquet et al, Chemical Abstracts vol. 71, No. 38885 (1969).
Modern Synthetic Reactions by Herbert O. House, pp. 8-13 (1965).
Bernhardt Emily
ByK Gulden Lomberg Chemische Fabrik GmbH
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