Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-05-14
2000-11-14
Fan, Jane
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514397, 514339, 514418, 548420, 5483114, 548484, 5462767, A61K 31403, C07D20982
Patent
active
061471054
DESCRIPTION:
BRIEF SUMMARY
This invention relates to 2-phenylindoles, a process for their production, pharmaceutical preparations that contain the latter as well as their use for the production of pharmaceutical agents.
The new 2-phenylindoles are reproduced by general formula I ##STR2## in which R.sup.1 means one of the radicals --(CH.sub.2).sub.n --S(O).sub.m --R.sup.4, --(CH.sub.2).sub.n --NR.sup.6 --SO.sub.2 --R.sup.4, --(CH.sub.2).sub.m, ##STR3## whereby n and n' are integers from 4 to 12 and m and m' are 0, 1 or 2, and X stands for a methylene group, an imino group .dbd.NR.sup.6, an oxygen or sulfur atom, C.sub.1 to C.sub.10 alkyl group, a benzyl, alkanoyl or alkanoyloxy or carbamoyl radical of formula --C(O)R.sup.5 or --C(O)NR.sup.6 R.sup.7 or a tetrahydropyranyl group, completely or partially fluorinated alkyl group --(CH.sub.2).sub.o --(CF.sub.2).sub.p CF.sub.3, whereby o and p, independently of one another, are in each case an integer from 0 to 6, an (alkyl)amino or (alkyl)carbamoyl group of formula --(CH.sub.2).sub.q --Y--NR.sup.8 R.sup.9, whereby q is an integer from 0 to 6 and Y stands for a direct bond, a methylene or carbonyl group, but if Y means a carbonyl group and m is 2, q cannot be 0, an aryl, aralkyl or heteroaryl radical, group, a phenyl or benzyl radical, hydrogen atom, a C.sub.1 to C.sub.10 alkyl or benzyl group, and R.sup.10 and R.sup.11 together mean a di-, tri- or tetramethylene bridge, which also can have a C--C double bond anywhere in the bridge.
As alkyl groups with 1 to 10 carbon atoms for radicals R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9, the radicals methyl, ethyl, propyl, butyl, pentyl, hexyl, hepty, octyl, nonyl and decanyl and also their branched-chain variants, for example the isopropyl, isobutyl or tert-butyl radicals, are suitable. Cycloalkyl groups with 3 to 10 carbon atoms, and among them especially the cyclopentyl or cyclohexyl radical, can also be mentioned.
A phenyl, 1- or 2-naphthyl radical can stand for an aryl radical R.sup.4 ; primarily a benzyl radical, but also a phenethyl, 1- or 2-naphthylmethyl radical can stand for an aralkyl radical R.sup.4 ; and mainly a 2-, 3- or 4-pyridinyl radical or an imidazolyl radical, which can carry a low alkyl group (C.sub.1 -C.sub.4), for example a methyl group, but also a 2-pyrazine, 2-, 4- or 5-pyrimidine, 3-pyrazine as well as a 2- or 3-thiophene radical on the nitrogen atom can stand for a heteraryl radical R.sup.4.
If R.sup.5 is to be a C.sub.1 -C.sub.10 alkoxy radical, this is primarily a methoxy, ethoxy, n- or isopropoxy, n-, iso- or tert-butoxy radical.
n or n' preferably stands for an integer from 6 to 12, m can be 0, 1 or 2, all indicated meanings are equally possible for o and p; the combinations o=3 and p=1 as well as o=0 and p=0 are to be emphasized for the partially fluorinated alkyl radical R.sup.4 ; finally, q is preferably selected from the range of 2 to 5.
Radicals R.sup.2 and R.sup.3 preferably each represent a hydrogen atom.
The meanings of n, n', m, m', R.sup.4 with o, p, q, Y, R.sup.8 and R.sup.9 and R.sup.6 are selected together such that R.sup.1 preferably forms one of the following side chains: H.sub.11 --CO--N(--CH.sub.3)--(CH.sub.2).sub.3 CH.sub.3
Radical --OR.sup.2 can be present in the 4-, 5-, 6- or 7-position of the bicyclic compound of the phenylindole (benzo[a]carbazole).
Especially preferred are those compounds of general formula I in which radical --OR.sup.2 is bound to carbon atom 5.
The compounds that are mentioned below are preferred within the scope of this invention: le fonyl)-nonyl]-indole indole ndecyl]-indole mido)-undecyl]-indole yphenyl)-3-methylindole finyl)-nonyl]-indole e le finyl)-nonyl]-indole ylindole ndecyl]-indole mido)-undecyl]-indole y-phenyl)-3-methylindole le e decyl]-indole methylthio]-decyl]-indole e nyl]benzo[a]carbazole nyl]benzo[a]carbazole arbazole zo[a]carbazole yl]-indole yl]-indole amino]-phenyl]-indole
Especially to be emphasized within the scope of this invention are those compounds of general formula I, in which R.sup.10 together with R.sup.11 stand f
REFERENCES:
Annals of the New York Academy of Sciences vol. 761 p. 178-180, 1995.
CA 107:39609, Kenlo et al., 1987.
CA 76: 14338, Kametani, 1972.
Biberger Christian
Schneider Martin
von Angerer Erwin
Fan Jane
Schering Aktiengesellschaft
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