Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-04-16
2000-04-25
Richter, Johann
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514462, 540543, 540597, 5462681, 548409, 549 28, 549331, 549345, 549414, 549469, A61K 31343, A61K 31382, C07D30779, C07D30904, C07D33502
Patent
active
060544759
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The invention relates to novel compounds which are used in the pharmaceutical industry for the production of medicaments.
1. Known Technical Background
International Patent Application WO92/12961 describes benzamides having PDE-inhibiting properties. International Patent Applications WO93/25517 and WO93/19749 disclose trisubstituted phenyl derivatives as selective PDE4 inhibitors. International Patent Application WO94/02465 describes inhibitors of c-AMP phosphodiesterase (PDE) and of tumor necrosis factor (TNF).
2. Description of the Invention
It has been found that the dihydrobenzofurans described below in greater detail, which differ from the previously published compounds by a 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 predominantly substituted by fluorine, bonded, are a spiro-linked 5-, 6- or 7-membered hydrocarbon ring, if desired interrupted by an oxygen atom or an imino (--NH--) group, 1-4C-alkoxycarbonyl, (O).sub.2 --) or carbonylimino (--C(O)NH--) and di-1-4C-alkylaminocarbonyl, hydroxylaminocarbonyl (--C(O)NHOH), 1-4C-alkoxyaminocarbonyl or a radical of the formula (a) ##STR2## where R51 is hydrogen, 1-4C-alkyl or aryl and unsubstituted or mono- or disubstituted by hydroxyl, 1-4C-alkoxy, halogen, amino, cyano or nitro,
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.
1-6C-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. Alkoxy radicals having 1 to 6 carbon atoms which may be mentioned, for example, are the hexyloxy, isohexyloxy (4-methylpentyloxy), neohexyloxy (3,3-dimethylbutoxy), pentyloxy, isopentyloxy (3-methylbutoxy), neopentyloxy (2,2-dimethylpropoxy), butoxy, isobutoxy, sec-butoxy, tert-butoxy, propoxy, isopropoxy, ethoxy and methoxy radicals.
3-7C-Cycloalkoxy represents cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy and cycloheptyloxy, of which cyclopropyloxy, cyclobutyloxy and cyclopentyloxy are preferred.
3-7C-Cycloalkylmethoxy represents cyclopropyl-methoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclo-hexylmethoxy and cycloheptylmethoxy, of which cyclopropylmethoxy, cyclobutylmethoxy and cyclopentyl-methoxy are preferred.
1-4C-Alkoxy which is completely or predominantly substituted by fluorine and which may be mentioned, for example, is the 2,2,3,3,3-pentafluoropropoxy, the perfluoroethoxy, the 1,1,2,2-tetrafluoroethoxy, the 1,2,2-trifluoroethoxy, the trifluoromethoxy, in particular the 2,2,2-trifluoroethoxy, and preferably the difluoromethoxy radical.
A spiro-linked, 5-, 6- or 7-membered hydrocarbon ring, if desired interrupted by an oxygen atom or an imino (--NH--) group, which may be mentioned is the cyclopentane, the cyclohexane, the cycloheptane, the tetrahydrofuran, the tetrahydropyran or the piperidine ring.
1-4C-Alkoxy represents a radical which, in addition to the oxygen atom, contains one of the above-mentioned 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 radical (CH.sub.3 O--C(O)--) and the ethoxycarbonyl radical (CH.sub.3 CH.sub.2 O--C(O)--).
In addition to the carbonyl group, mono- or di-1-4C-alkylaminocarbonyl radicals contain a mono- or di- 1-4C-alkylamino radical. Examples which may be mentioned are the N-methyl-, the N,N-dimethyl-, the N-ethyl-, the N-propyl-, the N,N-diethyl- and the N-isopropylaminocarbonyl radicals.
A 1-4C-alkoxyaminocarbonyl radical which may be mentioned is, for example, the methoxyaminocarbonyl radical (--C(O)NHOCH.sub.3).
1-4C-Alkylcarbonyloxy represents a car
REFERENCES:
patent: 5552438 (1996-09-01), Christensen, IV
patent: 5602157 (1997-02-01), Christensen, IV
patent: 5614540 (1997-03-01), Christensen, IV
patent: 5643946 (1997-07-01), Christensen, IV
Martin Thomas
Ulrich Wolf-Rudiger
ByK Gulden Lomberg Chemische Fabrik GmbH
Richter Johann
Solola Taofiq A.
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