Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Cyclopentanohydrophenanthrene ring system doai
Patent
1991-03-20
1993-09-14
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Cyclopentanohydrophenanthrene ring system doai
514176, 514179, 514180, 540 23, 540 41, 540 44, 540 47, 540106, 540107, 540108, 540114, 552510, 552511, 552520, 552540, 552541, 552544, 552548, 552553, 552592, 552593, C07J 430, C07J 5100, C07J 4100, C07J 1900
Patent
active
052448860
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
This invention relates to 11beta-phenyl-14betaH steroids of general formula I ##STR1## in which
Z stands for an oxygen atom or the hydroxyimino grouping N OH as well as L and M either together stand for a second bond or L for a hydrogen atom and M for an alpha-position hydroxy group and either A and B together mean a second bond and D means a hydrogen atom, and
R.sup.1 stands either
a) for a heteroaryl radical of formula Ia ##STR2## and A=N, O or S and B-D-E mean the element sequence C--C--C--, N--C--C or C--N--C, or
b) stands for a heteroaryl radical of formula Ib ##STR3## and A=N and B-D-E mean the element sequence C--C--C--, N--C--C, C--N--C or C--C--N or
c) stands for cycloalkyl, cycloalkenyl or aryl radical Ic
or else A means a hydrogen atom and B and D together mean a methylene group bridging the C 10 atom of the steroid skeleton and the ortho-carbon atom of the 11beta phenyl ring, and then
Z additionally stands for 2 hydrogen atoms and
R.sup.1 has the meaning indicated above in this claim under a), b) or c) or
d) stands for a straight-chain, branched, saturated or unsaturated hydrocarbon radical with up to 10 carbon atoms or
e) stands for ##STR4## with R' and R" meaning hydrogen or alkyl with 1 to 4 carbon atoms or R' and R" with the inclusion of N meaning a saturated 5- or 6-membered ring, and in the ring can contain another heteroatom such as O, N, S besides N, as well as the corresponding tertiary N oxides and the acid addition salts or
f) stands for OR"' with R"'=H, C.sub.1 -C.sub.8 alkyl or
g) stands for SR.sup.IV with R.sup.IV meaning R"' or
h) stands for a straight-chain, branched, saturated or unsaturated hydrocarbon radical with up to 10 carbon atoms, which is substituted with one or more oxo, hydroxyimino, C.sub.1 -C.sub.10 acyloxy or OR.sup.V group(s) with R.sup.V meaning a hydrogen atom or a C.sub.1 -C.sub.8 alkyl radical,
and optionally the heteroaryl radical of formula Ia is substituted by one or more halogen radicals and/or one or more alkyl radicals with 1 to 3 carbon atoms
and cycloalkyl, cycloalkenyl or aryl radical Id is substituted by one or more halogen, optionally protected hydroxy, alkoxy, optionally in the form of the sulfoxide or sulfone and/or of the N oxide, oxidized alkylthio and/or dialkylamino radicals,
R.sup.2 stands for a methyl or ethyl radical,
R.sup.3 /R.sup.4 stand for ##STR5## with R.sub.5 meaning a hydrogen atom or acyl radical with 1 to 4 carbon atoms
and Y means a hydrogen, chlorine, iodine or bromine atom, an alkyl, hydroxyalkyl, alkoxyalkyl or acyloxyalkyl group with 1 to 4 carbon atoms each in the alkyl or acyl radical
R.sub.6 stands for a hydrogen atom, a hydroxy group, an alkyl, O alkyl or O acyl group with 1 to 4 carbon atoms each,
O stands for the numbers 0, 1, 2 or 3,
R.sub.7 stands for a hydroxy or cyanide radical, an O alkyl or an O acyl group with 1 to 4 carbon atoms each,
k stands for the numbers 0, 1 or 2 and
Q stands for an oxygen atom or two hydrogen atoms.
As a special feature the compounds of this invention, deviating from naturally occurring steroids, exhibit a beta-position hydrogen atom on the 14 carbon atom. Such 14beta H steroids have already recently become known to a limited extent from European patent application 0 277 676. These known compounds with .DELTA..sup.4,9 -3-keto steroid skeleton exhibit in the 11 position a p-substituted (hetero)aryl ring. There are described as p-substituents: optionally saturated or unsaturated, straight-chain or branched hydrocarbon radicals with 1-10 carbon atoms, and the hydrocarbon radical additionally can also carry a hydroximino, oxo and/or hydroxy group of an amino group --NXY, with X and Y=H or C.sub.1 -C.sub.4 alkyl, and if X and Y=alkyl, these, together with N, can also form a heterocyclic 3- to 7-ring.
The substitution pattern obtainable according to EP-A 0 277 676 on the 11beta phenyl ring is relatively limited. The search for other 14beta H steroids, which exhibit substituents on the 11beta phenyl ring exceeding EP-A 0 277 676, therefore seems urgently necessary to achieve compou
REFERENCES:
patent: 4386085 (1983-05-01), Teutsch et al.
patent: 4954490 (1990-09-01), Cook et al.
Grant and Hackh's Chemical Dictionary (New York, McGraw-Hill Books, 1987) p. 14.
Beier Sybille
Chwalisz Krzysztof
Elger Walter
Neef Gunter
Ottow Eckhard
Schering Aktiengesellschaft
Shah Mukund J.
Ward E. C.
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