Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1992-11-04
1994-09-13
Cintins, Marianne M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546 81, 546 92, A61K 31445, C07D47104
Patent
active
053469046
DESCRIPTION:
BRIEF SUMMARY
SCOPE OF APPLICATION OF THE INVENTION
The invention relates to new sulphonyl compounds, processes for their preparation, their use and medicaments containing them. The compounds according to the invention are used in the pharmaceutical industry for the preparation of medicaments.
KNOWN TECHNICAL BACKGROUND
Substituted benzo-naphthyridines which are distinguished by a pronounced inhibition of blood platelet aggregation are described in DE-OS 21 23 328 and in U.S. Pat. No. 3,899,494. The use of the compound with the proposed INN benafentrin, which falls under these protective rights, as a bronchodilator and for the treatment of inflammatory diseases of the respiratory tract is disclosed in European Patent Application 247 971.
DESCRIPTION OF THE INVENTION
It has now been found that the compounds described in more detail below, which differ from the compound benafentrin in particular by the sulphonyl substitution instead of the acetyl substitution on the amino group, have surprising and particularly advantageous properties.
The invention thus relates in a first aspect to compounds of the formula I ##STR2## wherein R1 denotes 1-4C,-alkyl, identical or different substituents from the group comprising 1-4C-alkyl, 1-4C-alkoxy, hydroxyl and halogen,
1-4C-Alkyl represents straight-chain or branched alkyl radicals having 1 to 4 carbon atoms. Examples which may be mentioned are the butyl, iso-butyl, sec.-butyl, tert.-butyl, propyl, isopropyl, ethyl and in particular the methyl radical.
1-4C-Alkoxy radicals contain one of the abovementioned 1-4C-alkyl radicals in addition to the oxygen atom. The methoxy radical is preferred.
Halogen in the context of the present invention is bromine, chlorine or fluorine.
Examples which may be mentioned of substituted phenyl radicals R6 are the radicals: 4-methylphenyl, 4-tert.-butylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 2,5-dichlorophenyl and 4-hydroxyphenyl.
Preferred possible salts for compounds of the formula I are all the acid addition salts. Salts which may be mentioned in particular are the pharmacologically tolerated salts of the inorganic and organic acids usually used in galenics. Salts which are not pharmacologically tolerated and may initially be obtained, for example, as process products during preparation of the compounds according to the invention on an industrial scale are converted into pharmacologically tolerated salts by processes which are known to the expert. Examples of such suitable salts are water-soluble and water-insoluble acid addition salts, such as the hydrochloride, hydrobromide, hydriodide, phosphate, nitrate, sulphate, acetate, citrate, gluconate, benzoate, hibenzate, fendizoate, butyrate, sulphosalicylate, maleate, laurate, realate, fumarate, succinate, oxalate, tartrate, aresonata, embonate, metembonate, stearate, rosylate, 3-hydroxy-2-naphthoate or mesylate.
Compounds of the formula I which are to be singled out are those in which from the group comprising 1-4C-alkyl, 1-4C-alkoxy and halogen,
Compounds of the formula I which are to be singled out in particular are those in which 4-position of the phenyl radical bonded in the 6-position on the benzo-naphthyridine ring,
The benzo-naphthyridine ring has (at positions 4a and 10b) two chirality centers. The invention therefore relates to all the conceivable enantiomers and diastereomers, as well as the racemates and mixtures thereof. Those compounds of the formula I in which the hydrogen atoms positions 4a and 10b are in the cis-position are preferred.
The enantiomerically pure cis-compounds which are mirror images of one another and rotate linearly polarized light in the (+) or (-) direction [(+)-enantiomer and (-)-enantiomer] are particularly preferred. The trans-compounds are separated from the (diastereomeric) cis-compounds--in the same way as the (+)- and (-)-enantiomers are separated--in a manner with which the expert is familiar, e.g. as described in European Patent Application 247 971.
Those compounds of the formula I which are derived from compounds of the formula II which
REFERENCES:
patent: 3899494 (1975-08-01), Ott et al.
patent: 4087530 (1978-05-01), Ott et al.
Morrison & Boyd, Allyn and Bacon, Inc. Boston, second edition, 1971, pp. 751-753.
Flockerzi Dieter
Klemm Kurt
ByK Gulden Lomberg Chemische Fabrik GmbH
Cintins Marianne M.
Spivack Phyllis G.
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