Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Silicon containing doai
Patent
1992-01-14
1993-08-03
Bond, Robert T.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Silicon containing doai
514114, 514169, 514172, 514173, 514176, 514179, 514185, 5142295, 514248, 514250, 514257, 514279, 514379, 514406, 514410, 514493, 514506, 514647, 514681, 540 3, 540 4, 540 47, 540 52, 540 57, 552505, 552506, 552504, 552510, 544 99, 544140, 544154, 544333, 544335, 544369, 544370, 546 36, 546 38, 546295, 546198, 548148, 548242, 5483017, 548528, 556 95, 556436, 558 83, 558 29, 558 32, 558167, 558170, 558423, 558431, 564308, 568 27, 568326, 568309, 568423, 568431, C07J 6300, C07J 7100, C07J 7500, C07J 5300, A6
Patent
active
052329151
DESCRIPTION:
BRIEF SUMMARY
This invention relates to the object characterized in the claims, i.e., new 9.alpha.-hydroxy-19,11.beta.-bridged steroids, process for their production, pharmaceutical preparations containing these compounds, their use for production of pharmaceutical agents as well as the new intermediate products required for this purpose.
The 9.alpha.-hydroxy-19,11.beta.-bridged steroids according to the invention are described by general formula I ##STR2## in which
R.sup.1 stands for a methyl or ethyl radical,
R.sup.2 stands for a hydrogen atom, chlorine atom, a C.sub.1 -C.sub.4 alkyl radical,
B and G, which are the same or different, each stands for a hydrogen atom, a C.sub.1 -C.sub.4 alkyl radical or together for a second bond between carbon atoms 6 and 7,
B and R.sup.2 together stand for a methylene or ethylene group,
Z stand for the radical of a ring of formula ##STR3##
in which
R.sup.1 has the meaning mentioned in formula I,
the dotted line starting from W means the possible presence of a double bond,
W means a CH.sub.2, CH, CH.sub.2 CH.sub.2 or CHCH.sub.2 radical,
R.sup.5 /R.sup.6 means --OR.sup.7 /--C.tbd.C--U ##STR4## with
R.sup.7 meaning a hydrogen atom or acyl radical with 1 to 4 carbon atoms, U meaning a hydrogen atom, an alkyl, hydroxyalkyl, alkoxyalkyl, acyloxyalkyl group each with 1 to 4 carbon atoms in the alkyl or acyl radical or a halogen atom,
R.sup.8 meaning a hydrogen atom, a hydroxy group, an alkyl, o-alkyl or o-acyl group each with 1 to 4 carbon atoms,
R.sup.9 meaning a hydrogen atom, a hydroxy or cyanide radical, an o-alkyl or o-acyl group each with 1 to 4 carbon atoms,
R.sup.10 meaning a hydrogen atom, an alkyl or acyl group each with 1 to 10 carbon atoms,
m meaning 0, 1, 2 or 3,
k meaning 0, 1 or 2, in which
R.sup.4 and R.sup.4', which are the same or different, each stands for a hydrogen atom, a cyanide radical, an --OR.sup.11, --S(O).sub.k R.sup.11, --N(O).sub.n R.sup.11 R.sup.12,--O--SO.sub.2 R.sup.13, --P(O)(OR.sup.14).sub.2,--SiR.sup.14.sub.3 or --SnR.sup.14.sub.3 group with k meaning numbers 0, 1 or 2, n meaning numbers 0 or 1,
R.sup.11 meaning a hydrogen atom or a C.sub.1 -C.sub.8 alkyl radical,
R.sup.12 meaning R.sup.11, a cyanide or a C.sub.1 -C.sub.10 acyl radical,
R.sup.13 meaning a perfluorinated C.sub.1 -C.sub.4 alkyl radical,
R.sup.14 meaning a C.sub.1 --C.sub.4 alkyl radical or
R.sup.11 and R.sup.12 form a 5- or 6-membered heterocyclic ring inside an --N(O).sub.n R.sup.11 R.sup.12 group together with the inclusion of N, and still another heteroatom N, O or S can be contained in the ring,
Y and Y', which are the same or different, each means a direct bond, a straight-chain or branched alkylene group with up to 20 carbon atoms optionally exhibiting a double or triple bond or bonds, the alkylene group is optionally substituted by one or more oxo, C.sub.1 -C.sub.10 acyloxy, --OR.sup.11, --S(O).sub.k R.sup.11 and/or --N(O).sub.n R.sup.11 R.sup.12 group or groups, an optionally substituted arylene radical or
R.sup.4 --Y and R.sup.4' --Y' together mean the radical of a saturated, unsaturated or aromatic 5- or 6-membered ring optionally substituted with 0 to 2 oxygen atoms, sulfur atoms and/or NR.sup.11 groups, provided that only then are k and n greater than 0, if R.sup.11 stands for a C.sub.1 -C.sub.8 alkyl radical and ring A stands for ##STR5##
and M and N together mean a second bond
or M means a hydrogen atom and N means a hydroxy group, and then B, R.sup.2, G, R.sup.3, D and E are hydrogen atoms,
and X means an oxygen atom, two hydrogen atoms or a hydroxyimino grouping N.about.OH,
R.sup.3 and D, which are the same or different, each means a hydrogen atom, a nitrile radical or a C.sub.1 -C.sub.4 alkyl radical or together a methylene or ethylene group,
E means a hydrogen atom, a C.sub.1 -C.sub.4 alkyl radical,
D and E together mean a second bond between carbon atoms 1 and 2 or together mean a methylene group ##STR6## with R.sup.11 meaning a hydrogen atom or a C.sub.1 -C.sub.8 alky) radical, as well as optionally their pharmaceutically compatible addition salts with acids.
If Y--R.sup.
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Stork, et al., JACS, 1982, 104, 2321-2323.
Grant and Hackh's Chemical Dictionary, (McGraw-Hill Books, New York, 1987), p. 14.
Hutchinson, et al., Tetrahedron Letters, 28113, pp. 1313-1316, 1987.
Morrison and Boyd, Organic Chemistry, (Bostom, Allyn and Bacon, 1979), pp. 622 and 631.
Beier Sybille
Elger Walter
Fritzemeier Karl-Heinrich
Neef Gunter
Ottow Eckhard
Bond Robert T.
Schering Aktiengesellschaft
Ward E. C.
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