Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-02-14
1999-02-23
Stockton, Laura L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
549424, 5462821, 514336, A61K 3135, A61K 3144, C07D30932, C07D40504
Patent
active
058744622
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/03168 filed Aug. 10, 1995.
The present invention related to the use of substituted 6-amino-4H-pyrans, some of which are known, as medicaments, new active compounds and a process for their preparation, in particular their use as cerebrally active agents. this Magn. Reson. Chem. 23 (9), 793-4, 1985; Nor. Khim. Sredstva Zashch. Rast. 7-11, 1979!.
It has now been found that the substituted 6-amino-4H-pyrans 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, phenyl, halogen and trifluoromethyl or straight-chain or branched alkylthio or alkoxy in each case having up to 6 carbon atoms,
R.sup.1 represents hydrogen or straight-chain or branched alkyl having up to 8 carbon atoms,
R.sup.2 and R.sup.3 are identical or different and represent hydrogen or straight-chain or branched alkyl or acyl in each case having up to 6 carbon atoms,
D represents cyano, nitro or straight-chain or branched alkoxycarbonyl having up to 8 carbon atoms,
surprisingly have a modulating action on potassium channels and are thus suitable for use in the control of cerebral disorders and sickle cell anemia.
In the context of the invention, physiologically acceptable salts are preferred. Physiologically acceptable salts are in general salts of the compounds according to the invention with inorganic or organic acids. Preferred salts are those 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.
The compounds according to the invention can exist in stereoisomeric forms which either behave 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 also be separated into the stereoisomerically uniform constituents in a known manner.
Preferred are those compounds of the general formula (I) in which
A represents phenyl, naphthyl or pyridyl, each of which is optionally substituted up to 3 times by identical or different substituents from the group consisting of nitro, cyano, fluorine, chlorine, bromine, iodine, phenyl and trifluoromethyl or straight-chain or branched alkylthio or alkoxy in each case having up to 4 carbon atoms.
R.sup.1 represents hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms,
R.sup.2 and R.sup.3 are identical or different and represent hydrogen or straight-chain or branched alkyl or acyl in each case having up to 4 carbon atoms,
D represents cyano or straight-chain or branched alkoxycarbonyl having up to 6 carbon atoms,
Particularly preferred are those compounds of the general formula (I) in which
A represents phenyl or pyridyl, each of which is optionally substituted up to 2 times by identical or different substituents from the group consisting of nitro, cyano, fluorine, chlorine, bromine, iodine, trifluoromethyl, methoxy and phenyl or methylthio,
D represents cyano,
R.sup.1 represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms,
R.sup.2 and R.sup.3 are identical or different and represent hydrogen or straight-chain or branched alkyl or acyl in each case having up to 3 carbon atoms,
The compound of the formula (I) according to the invention show an unforeseeable, useful spectrum of pharmacological action.
They are channel modulators having selectivity for calcium-dependent potassium channel of high conductivity (BK(Ca) channels), in particular of the central nervous system.
On account of their pharmaco
REFERENCES:
patent: 3981893 (1976-09-01), Meyer et al.
patent: 4622332 (1986-11-01), Wehinger et al.
Tetrahedron Letters No. 21, pp. 1835-1836, 1977 "Synthesis of Heterocyclic Compounds".
Pascual et al., Magn.Res.Chem. 23(9), 1985, 793-194.
Tas et al., Neuro.Letters 94, 1988, 279-284.
Abramenko et al., Simple Methods of Preparing Derivatives of 2-amino-3-cyano-4N-Pyranes, Nov.Khim.Sredstva Zanshch.Rast., 7-11 (1979) (English Translation of Russian Publication, both of which are submitted herewith).
Soto et al., Heterocycles, vol. 22, No. 1, 1984, pp. 1-6, 1984.
Pascual et al., CA 104:148178, 1986.
de Vry Jean-Marie-Viktor
Glaser Thomas
Heine Hans-Georg
Junge Bodo
Schohe-Loop Rudolf
Bayer Aktiengesellschaft
Stockton Laura L.
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