Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-01-06
1998-05-26
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546114, A61K 3144, C07D49504
Patent
active
057565155
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to dioxo-thiopyrano-pyridine-carboxylic acid derivatives, a process for their preparation and their use as medicaments, in particular as cerebrally active agents. Chem. 27 (5), 1453-6, 1990!.
The present invention relates to new esters of the general formula (I) ##STR1## in which A represents aryl having 6 to 10 carbon atoms, or pyridyl, each of which is optionally substituted up to 3 times by identical or different substituents from the group consisting of nitro, cyano, cycloalkyl having 3 to 7 carbon atoms, halogen and trifluoromethyl or by straight-chain or branched alkylthio, alkyl or alkoxy in each case having up to 6 carbon atoms, to 8 carbon atoms,
In the context of the invention, physiologically acceptable salts are preferred. In general, physiologically acceptable salts are salts of the compounds according to the invention with inorganic or organic acids. Salts with inorganic acids such as, for example, hydrochloric acid, hydrobromic acid, phosphoric acid or sulphuric acid, or salts with organic carboxylic or sulphonic acids such as, for example, acetic acid, maleic acid, fumaric acid, malic acid, citric acid, tartaric acid, lactic acid, benzoic acid, or methanesulphonic acid, ethanesulphonic acid, phenylsulphonic acid, toluenesulphonic acid or naphthalenedisulphonic acid are preferred.
The compounds according to the invention can exist in stereoisomeric forms which behave either as image and mirror image (enantiomers) or which do not behave as image and mirror image (diastereomers). The invention relates both to the antipodes and to the racemic forms as well as the diastereomer mixtures. Like the diastereomers, the racemic forms can be separated into the stereoisomerically homogeneous constituents in a known manner.
Preferred compounds of the general formula (I) are those substituted up to 3 times by identical or different substituents from the group consisting of nitro, cyano, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclopentyl, cyclohexyl and trifluoromethyl or by straight-chain or branched alkylthio, alkyl or alkoxy in each case having up to 4 carbon atoms, to 6 carbon atoms,
Particularly preferred compounds of the general formula (I) are those to 3 times by identical or different substituents from the group consisting of nitro, cyano, fluorine, chlorine, bromine, iodine, trifluoromethyl, cyclohexyl, methyl and methoxy or by methylthio, to 4 carbon atoms,
A process for the preparation of the compounds of the general formula (I) according to the invention has additionally been found, characterized in that aldehydes of the general formula (II) ##STR2## in which R.sup.3 has the abovementioned meaning of R.sup.1 , but does not represent hydrogen, ##STR3## in which A and R.sup.3 have the abovementioned meaning,
The process according to the invention can be illustrated by way of example by the following reaction scheme: ##STR4##
Suitable solvents in this connection are all inert organic solvents which do not change under the reaction conditions. These preferably include alcohols such as methanol, ethanol, propanol or isopropanol, or ethers such as diethyl ether, dioxane, tetrahydrofuran, glycol dimethyl ether or diethylene glycol dimethyl ether, acetonitrile, or amides such as hexamethylphosphoramide or dimethylformamide, or acetic acid or halogenated hydrocarbons such as methylene chloride or carbon tetrachloride or hydrocarbons such as benzene or toluene. It is also possible to use mixtures of the solvents mentioned. Ethanol is preferred.
The reaction temperatures can be varied within a relatively wide range. In general, the reaction is carried out between +10.degree. C. and +150.degree. C., preferably between +20.degree. C. and +100 C., in particular at the boiling point of the particular solvent.
The reactions can be carried out at normal pressure, but also at elevated or reduced pressure (e.g. 0.5 to 3 bar). In general the reactions are carried out at normal pressure.
Suitable solvents for the oxidation are all inert organic solvents which do not change u
REFERENCES:
patent: 4705785 (1987-11-01), Schwender et al.
P.W.L. Tas, et al., Neuroscience Letters, vol. 94, pp. 279-284 (1985).
J. Dodd, J. Het. Chem., vol. 27, No. 5, pp. 1453-1456 (1990).
de Vry Jean-Marie-Viktor
Glaser Thomas
Heine Hans-Georg
Junge Bodo
Schohe-Loop Rudolf
Bayer Aktiengesellschaft
Morris Patricia L.
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