Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
2000-01-24
2000-09-19
Badio, Barbara
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546109, A61K 3144, C07D22112
Patent
active
061212792
DESCRIPTION:
BRIEF SUMMARY
FIELD OF APPLICATION OF THE INVENTION
The invention relates to novel 6-phenylphenanthridines which are used in the pharmaceutical industry for the production of medicaments.
KNOWN TECHNICAL BACKGROUND
Chem. Ber. 1939, 72, 675-677, J. Chem. Soc., 1956, 4280-4283 and J. Chem. Soc. (C), 1971, 1805 describes the synthesis of 6-phenylphenanthridines.
DESCRIPTION OF THE INVENTION
It has now been found that the novel 6-phenylphenanthridines which are described below in greater detail have surprising and particularly advantageous properties.
The invention thus relates to compounds of the formula I ##STR1## in which R1 is hydroxyl, 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy or completely or predominantly fluorine-substituted 1-4C-alkoxy, completely or predominantly fluorine-substituted 1-4C-alkoxy, 3-7C-cycloalkyl, 3-7C-cycloalkylmethyl or an unsubstituted or R12- and/or R13-substituted phenyl radical, or where R7 and R8, together and including the nitrogen atom to which both are bonded, are a 1-pyrrolidinyl, 1-piperidyl, 1-hexahydroazepinyl or 4-morpholinyl radical, unsubstituted or R12- and/or R13-substituted phenyl radical, where 1-4C-alkyl, trifluoromethyl or completely or predominantly fluorine-substituted 1-4C-alkoxy, trifluoromethyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl, 1-4C-alkylcarbonyloxy, amino, mono- or di-1-4C-alkylamino, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl or completely or predominantly fluorine-substituted 1-4C-alkoxy,
1-4C-Alkyl represents a straight-chain or branched alkyl radical having 1 to 4 carbon atoms. Examples which may be mentioned are the butyl, isobutyl, sec-butyl, tert-butyl, propyl, isopropyl and, preferably, the ethyl and methyl radicals.
1-4C-Alkoxy represents radicals which, in addition to the oxygen atom, contain a straight-chain or branched alkyl radical having 1 to 4 carbon atoms. Examples which may be mentioned are the butoxy, isobutoxy, sec-butoxy, tert-butoxy, propoxy, isopropoxy and, preferably, the 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 cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy and cycloheptylmethoxy, of which cyclopropylmethoxy, cyclobutylmethoxy and cyclopentylmethoxy are preferred.
Completely or predominantly fluorine-substituted 1-4C-alkoxy which may be mentioned are, for example, the 2,2,3,3,3-pentafluoropropoxy, the perfluoroethoxy, the 1,2,2-trifluoroethoxy, in particular the 1,1,2,2-tetrafluoroethoxy, the 2,2,2-trifluoroethoxy, the trifluoromethoxy and, preferably, the difluoromethoxy radicals. "Predominantly" in this connection means that more than half of the hydrogen atoms are substituted by fluorine atoms.
1-2C-Alkylenedioxy represents, for example, the methylenedioxy (--O--CH.sub.2 --O--) and the ethylenedioxy radicals (--O--CH.sub.2 --CH.sub.2 --O--).
If R3 and R31 together have the meaning 1-4C-alkylene, the positions 1 and 4 in compounds of the formula I are linked to one another by a 1-4C-alkylene bridge, 1-4C-alkylene representing straight-chain or branched alkylene radicals having 1 to 4 carbon atoms. Examples which may be mentioned are the radicals methylene (--CH.sub.2 --), ethylene (--CH.sub.2 CH.sub.2 --), trimethylene (--CH.sub.2 --CH.sub.2 --CH.sub.2 --), 1,2-dimethylethylene [--CH(CH.sub.3)--CH(CH.sub.3)--] and isopropylidene [--C(CH.sub.3).sub.2 --].
If R5 and R51 together are an additional bond, then the carbon atoms in the positions 2 and 3 in compounds of the formula I are linked to one another via a double bond.
1-7C-Alkyl represents straight-chain or branched alkyl radicals having 1 to 7 carbon atoms. Examples which may be mentioned are the heptyl, isoheptyl (5-methylhexyl), hexyl, isohexyl (4-methylpentyl), neohexyl (3,3-dimethylbutyl), pentyl, isopentyl (3-methylbutyl), neopentyl (2,2-dimethylpropyl), butyl, isobutyl, sec-butyl, tert-butyl, propyl, isopropyl, ethyl and methyl
REFERENCES:
Kametani et al., "Cyclised Products in the Synthesis of 6-Substituted Phenanthridines by Phenolic Cyclisation." J. Chem. Soc., Section C: Organic Chemistry, pp. 1805-1808, 1971.
Badio Barbara
ByK Gulden Lomberg Chemische Fabrik GmbH
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