Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-04-04
2000-09-19
Rotman, Alan L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546 15, 5462827, 5462841, 549331, 549343, 549345, 549469, 549471, 514337, 514450, 514451, 514456, 514461, 514462, A61K 31438, A61K 31343, C07D40504, C07D40506
Patent
active
061212741
DESCRIPTION:
BRIEF SUMMARY
FIELD OF APPLICATION OF THE INVENTION
The invention relates to novel compounds 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 been found that the benzamides described in greater detail below, which differ from the previously published compounds by completely different substitution in positions 2 and 3 on the benzamide, have surprising and particularly advantageous properties.
The invention thus relates to compounds of the formula I (see attached formula sheet I) in which completely or partially fluorine-substituted 1-4C-alkoxy, bonded, are a 5-, 6- or 7-membered hydrocarbon ring, if desired interrupted by an oxygen atom, R46- and R47-substituted pyridyl, 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, beside 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 here 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.
Completely or partially fluorine-substituted 1-4C-alkoxy radicals which may be mentioned are, 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 radicals.
5-, 6- or 7-membered hydrocarbon rings, if desired interrupted by an oxygen atom, which may be mentioned are the cyclopentane, the cyclohexane, the cycloheptane, the tetrahydrofuran and the tetrahydropyran rings. If R2 and R3, together and including the two carbon atoms to which they are bonded, form a 5-, 6- or 7-membered ring, a spiro compound is present.
1-4C-alkyl is straight-chain or branched alkyl radicals having 1 to 4 carbon atoms. Examples which may be mentioned are the butyl, isobutyl, sec-butyl, tert-butyl, propyl, isopropyl, ethyl and methyl radicals.
Halogen within the meaning of the present invention is bromine, chlorine or fluorine.
1-4C-alkoxy is a radical which, beside the oxygen atom, contains one of the abovementioned 1-4C-alkyl radicals. Examples which may be mentioned are the methoxy and the ethoxy radicals.
1-4C-alkoxycarbonyl is a carbonyl group to which one of the abovementioned 1-4C-alkoxy radicals is bonded.
Examples which may be mentioned are the methoxycarbonyl (CH.sub.3 O--CO--) and the ethoxycarbonyl radicals (CH.sub.3 CH.sub.2 O--CO).
1-4C-alkylcarbonyl is a carbonyl group to which one of the abovementioned 1-4C-alkyl radicals is bonded. An example which may be mentioned is the acetyl radical (CH.sub.3 CO--).
1-4C-alkylcarbonyloxy radicals contain, beside the oxygen atom, one of the abovementioned 1-4C-alkylcarbonyl radicals. An example which may be mentioned is the acetoxy radical (CH.sub.3 CO--O--).
Mono- or di-1-4C-alkylamino radicals which may be mentioned are, for example, the methylamino, the dimethylamino and the diethylamino radicals.
A 1-4C-alkylcar
REFERENCES:
patent: 5340827 (1994-08-01), Beeley et al.
Thibaut Ulrich
Ulrich Wolf-Rudiger
ByK Gulden Lomberg Chemische Fabrik GmbH
Rotman Alan L.
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