Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-09-03
2000-10-03
Seaman, D. Margaret
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514284, 514287, 514290, 546 65, 546 74, 546108, 546109, A61K 3144, C07D22112, C07D22122, C07D22128
Patent
active
061273783
DESCRIPTION:
BRIEF SUMMARY
FIELD OF APPLICATION OF THE INVENTION
The invention relates to novel phenanthridines substituted in the 6-position, 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 describe the synthesis of 6-phenylphenanthridines.
DESCRIPTION OF THE INVENTION
It has now been found that the novel phenanthridines substituted in the 6-position described in greater detail below 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 1-4C-alkoxy which is completely or partially substituted by fluorine, 1-4C-alkoxy which is completely or partially substituted by fluorine, which is substituted by R7 and R8, where trifluoromethyl, 1-4C-alkoxycarbonyl or 1-4C-alkoxy which is completely or partially substituted by fluorine, 1-4C-alkylcarbonyloxy, trifluoromethyl, phenyl, phenyl-1-4C-alkyl, nitro, amino, 1-4C-alkoxy which is completely or partially substituted by fluorine, or is SO.sub.2 -R70 or N(R71)R72, where phenyl-1-4C-alkyl or phenyl which is substituted by one or more identical or different substituents, where the substituents are selected from the group consisting of nitro, 1-4C-alkyl, halogen, 1-4C-alkylcarbonylamino, 1-4C-alkoxy, 1-4C-alkoxy which is completely or partially substituted by fluorine, cyano, phenyl, naphthyl, trifluoromethyl and 1-4C-alkoxycarbonyl,
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 radical, isobutoxy radical, sec-butoxy radical, tert-butoxy radical, propoxy radical, isopropoxy radical and preferably the ethoxy radical and methoxy radical.
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.
Examples which may be mentioned of 1-4C-alkoxy which is completely or partially substituted by fluorine are the 1,2,2-trifluoroethoxy radical, the 2,2,3,3,3-pentafluoropropoxy radical, the perfluoroethoxy radical, the 1,1,2,2-tetrafluoroethoxy radical, the trifluoromethoxy radical, in particular the 2,2,2-trifluoroethoxy radical and preferably the difluoromethoxy radical.
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 radical, isobutyl radical, sec-butyl radical, tert-butyl radical, propyl radical, isopropyl radical and preferably the ethyl radical and methyl radical.
1-2C-Alkylenedioxy represents, for example, the methylenedioxy radical (--O--CH.sub.2 --O--) and the ethylenedioxy radical (--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 --].
Halogen within the meaning of the present invention is bromine, chlorine and fluorine.
In addition to the carbonyl group, 1-4C-alkoxycarbonyl contains one of the abovementioned 1-4C-alkoxy radicals. Examples which may be mentioned are the methoxycarbonyl radical and the ethoxycarbonyl radical.
If R5 and R51 together are an additional bond, then the carbon atoms in the po
REFERENCES:
ChemischeBerichte, vol. 103(6), 1970, Weinheim, pp. 1674-1691.
Journal of Liquid Chromatography, vol. 13(3), pp. 543-555, Moriyasu, 1990.
Berichte Der Deutschen Chemischen Gesellschaft, vol. 4, pp. 675-678, Sugasawa, 1939.
ByK Gulden Lomberg Chemische Fabrik GmbH
Seaman D. Margaret
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