Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-11-18
1999-05-11
Dentz, Bernard
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514469, 549345, 549462, A61K31/34
Patent
active
059028246
DESCRIPTION:
BRIEF SUMMARY
RELATED APPLICATION
The subject application is related to a concurrently-filed application Ser. No. 08/952,275.
1. Technical field
The invention relates to novel compounds which are used in the pharmaceutical industry for the production of medicaments.
2. Prior art
International Patent Application WO092/12961 describes benzamides having PDE inhibiting properties. International Patent Application WO093/25517 discloses trisubstituted phenyl derivatives as selective PDE IV inhibitors. International Patent Application WO094/02465 describes inhibitors of c-AMP phosphodiesterase and of TNF.
DESCRIPTION OF THE INVENTION
It has now been found that the phenyldihydrobenzofurans described in greater detail below, which differ from the previously published compounds by a completely different type of substitution, have surprising and particularly advantageous properties.
The invention thus relates to compounds of the formula I (see attached formula sheet I), in which 1-4C-alkoxy which is completely or partially substituted by fluorine, bonded, are a 5-, 6- or 7-membered hydrocarbon ring, if desired interrupted by an oxygen atom, di-1-4C-alkylamino, 1-4C-alkylcarbonylamino, 1-4C-alkylsulphonylamino, trifluoromethylsulphonylamino, cyanoamino, nitro, cyano, mono- or di-1-4C-alkylaminocarbonyl, 5-tetrazolyl or carbamoyl and the radicals R3, R4 and R5 has a meaning other than hydrogen,
1-6C-Alkoxy represents 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 here are, for example, the hexyl, isohexyl (2-methylpentyl), neohexyl (2,2-dimethylbutyl), pentyl, isopentyl (3-methylbutyl), neopentyl (2,2-dimethyl-propyl), butyl, isobutyl, sec-butyl, tert-butyl, propyl, isopropyl, ethyl and methyl radicals.
3-7C-Cycloalkoxy represents, for example, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy and cycloheptyloxy, of which cyclopropyloxy, cyclobutyloxy and cyclopentyloxy are preferred.
3-7C-Cycloalkylmethoxy represents, 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 which may be mentioned, for example, are 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.
A 5-, 6- or 7-membered hydrocarbon ring, if desired interrupted by an oxygen atom, which may be mentioned is the cyclopentane, the cyclohexane, the cycloheptane, the tetrahydrofuran and the tetrahydropyran ring. If R2 and R3, together and including the two carbon atoms to which they are bonded, form a 5-, 6- or 7-membered ring, then a spiro compound is present.
1-4C-Alkyl represents 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.
1-4C-Alkoxy represents a radical which, in addition to 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 represents 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 (CH.sub.3 CH.sub.2 O--CO--) radicals.
Mono- or di-1-4C-alkylamino radicals which may be mentioned, for example, are the methylamino, the dimethylamino, the ethylamino, the diethylamino, the propylamino and the isopropylamino radicals.
A 1-4C-alkylcarbonylamino radical which may be mentioned, for example, is the acetylamino radical (--NH--CO--CH.sub.3).
1-4C-Alkylsulphonylamino represents a sulphonylamino radical which is substituted by one of the abovementioned 1-4C-alkyl
ByK Gulden Lomberg Chemische Fabrik GmbH
Dentz Bernard
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