Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-12-19
1998-01-27
Davis, Zinna Northington
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514617, 546309, 564170, C07D21375, C07C23556, A61K 3144, A61K 31165
Patent
active
057122989
DESCRIPTION:
BRIEF SUMMARY
CONTINUING DATA
This Application is a .sctn.371 of PCT/EP94/02169, filed Jul. 2, 1994.
FIELD OF APPLICATION OF THE INVENTION
The invention relates to novel fluoroalkoxy-substituted benzamides, which are used in the pharmaceutical industry for the production of medicaments.
KNOWN TECHNICAL BACKGROUND
International Patent Application WO92/12961 describes benzamides having PDE-inhibiting properties. International Patent Application WO93/25517 discloses trisubstituted phenyl derivatives as selective PDE-IV inhibitors. International Patent Application WO94/02465 describes inhibitors of c-AMP phosphodiesterase and of TNF.
DESCRIPTION OF THE INVENTION
It has now been found that the benzamides which are described in greater detail below, which differ from the previously published compounds in particular by the fluoroalkoxy substitution in the 3- or 4-position on the benzamide, have surprising and particularly advantageous properties.
BRIEF DESCRIPTION OF THE DRAWINGS
FIGS. 1 and 2 are respective formulae of compounds represented thereby.
The invention thus relates to compounds of the formula I, in which 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy, benzyloxy or 1-4C-alkoxy which is completely or partially substituted by fluorine, and the other is 1-4C-alkoxy which is completely or partially substituted by fluorine, and pyridyl which is substituted by R34, R35, R36 and R37, where 1-4C-alkoxy, 1-4C-alkoxycarbonyl, 1-4C-alkylcarbonyl, 1-4C-alkylcarbonyloxy, amino, mono- or di-1-4C-alkylamino or 1-4C-alkylcarbonylamino, 1-4C-alkoxy, 1-4C-alkoxycarbonyl or amino, salts.
One embodiment (embodiment a) of the invention consists of compounds of the formula I, in which 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy, benzyloxy or 1-4C-alkoxy which is completely or partially substituted by fluorine, and the other is 1-4C-alkoxy which is completely or partially substituted by fluorine, and pyridyl which is substituted by R34, R35, R36 and R37, where 1-4C-alkoxy, 1-4C-alkoxycarbonyl, 1-4C-alkylcarbonyl, 1-4C -alkylcarbonyloxy, amino, mono- or di-1-4C-alkylamino or 1-4C-alkylcarbonylamino, 1-4C-alkoxy, 1-4C-alkoxycarbonyl or amino, salts, where those compounds are excluded in which R1 is 1-4C-alkoxy which is completely or partially substituted by fluorine and R2 is 3-7C-cycloalkoxy.
A further embodiment (embodiment b) of the invention are compounds of the formula I, in which either and benzyloxy or 1-4C-alkoxy which is completely or partially substituted by fluorine and and pyridyl which is substituted by R34, R35, R36 and R37, where 1-4C-alkoxy, 1-4C-alkoxycarbonyl, 1-4C-alkylcarbonyl, 1-4C-alkylcarbonyloxy, amino, mono- or di-1-4C-alkylamino or 1-4C-alkylcarbonylamino, 1-4C-alkoxy, 1-4C-alkoxycarbonyl or amino, salts.
1-6C-Alkoxy is a radical which, in addition to the oxygen atom, contains a straight-chain or branched alkyl radical having 1 to 6 carbon atoms. Alkyl radicals having 1 to 6 carbon atoms which may be mentioned in this context are, for example, the hexyl, isohexyl (2-methylpentyl), neohexyl (2,2-dimethylbutyl), pentyl, isopentyl (3-methylbutyl), neopentyl (2,2-dimethylpropyl), butyl, isobutyl, sec-butyl, tert-butyl, propyl, isopropyl, ethyl and methyl radicals.
3-7C-Cycloalkoxy is, for example, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy and cycloheptyloxy, of which cyclopropyloxy, cyclobutyloxy and cyclopentyloxy are preferred.
3-7C-Cycloalkylmethoxy is, for example, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy and cycloheptylmethoxy, of which cyclopropylmethoxy, cyclobutylmethoxy and cyclopentylmethoxy are preferred.
1-4C-Alkoxy which is completely or partially substituted by fluorine is, for example, the 1,2,2-trifluoroethoxy, the 2,2,3,3,3-pentafluoropropoxy, the perfluoroethoxy and in particular the 1,1,2,2-tetrafluoroethoxy, the trifluoromethoxy, the 2,2,2-trifluoroethoxy and the difluoromethoxy radical.
Halogen within the meaning of the present invention is bromine, chlorine and fluorine.
1-4C-Alkyl is a straight-chain or branched alkyl radical having 1 to
REFERENCES:
patent: 5340827 (1994-08-01), Beeley et al.
Fialkov et al., Chemical Abstracts, vol. 98, No. 23, Abstract 197,713n, Jun. 6, 1983, p. 603.
Yagupolskuet al., Chemical Abstracts, vol. 55, No. 18 Abstract 17.563i Sep. 4, 1961.
Hahn, Chemical Abstracts, vol. 58, No. 9, Abstract 8944b/c, Apr. 29, 1963.
ByK Gulden Lomberg Chemische Fabrik GmbH
Davis Zinna Northington
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