Organic compounds -- part of the class 532-570 series – Organic compounds – Cyclopentanohydrophenanthrene ring system containing
Patent
1993-09-28
1995-12-26
Wu, Shean
Organic compounds -- part of the class 532-570 series
Organic compounds
Cyclopentanohydrophenanthrene ring system containing
552508, 552544, 552548, 552553, 514169, 514172, 514173, 514175, 514177, 514178, 514179, C07J 5300, A61K 3156
Patent
active
054789567
DESCRIPTION:
BRIEF SUMMARY
This invention relates to the new 8-En-19,11.beta.-bridged steroids, process for their production, pharmaceutical preparations containing these compounds, their use for the production of pharmaceutical agents as well as the new intermediate products necessary for this purpose.
The 8-En-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,
X stands for an oxygen atom, a hydroxyimino group or two hydrogen atoms,
Z stands for the radical of a ring of formula ##STR3## in which
R.sup.1 has the meaning mentioned in formula I, the broken 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, ##STR4## with R.sup.7 meaning a hydrogen atom, an alkyl or acyl radical with 1 to 4 carbon atoms, U meaning a hydrogen atom, an alkyl, hydroxyalkyl, alkoxyalkyl, acyloxyalkyl group with 1 to 4 carbon atoms each in the alkyl or acyl radical or a halogen atom,
R.sup.8 means a hydrogen atom, a hydroxy group, an alkyl, O-alkyl or O-acyl group with 1 to 4 carbon atoms each,
R.sup.9 means a hydrogen atom, a hydroxy or cyanide radical, an O-alkyl or O-acyl group with 1 to 4 carbon atoms each,
R.sup.10 means a hydrogen atom, an alkyl or acyl group with 1 to 10 carbon atoms each,
m means 0, 1, 2 or 3,
k means 0, 1 or 2,
R.sup.4 and R.sup.4' are the same or different, respectively standing for a hydrogen atom, a cyanide radical an --OR.sup.11 --S(O).sub.k R.sup.11, --N(O).sub.n R.sup.12, --O--SO.sub.2 --R.sup.13, --P(O)(OR.sup.14).sub.2, --SiR.sub.3.sup.14 or --SnR.sub.3.sup.14 group with k meaning the numbers 0, 1 or 2, n meaning the 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 within a --N(O).sub.n R.sup.11 R.sup.12 group together, with the inclusion of N, form a 5 or 6 membered heterocyclic ring, and another heteroatom N, O or S can also be contained in the ring,
Y and Y' are the same or different, respectively mean an alkylene group with up to 20 carbon atoms having a direct bond, a straight-chain or branched, optionally double or triple bond(s), that 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(s) an optionally substituted carbocyclic or heterocyclic aryl radical or R.sup.4 --Y and R.sup.4' --Y' together mean the radical of an optionally substituted saturated, unsaturated or aromatic 5 or 6 membered ring with 0 to 2 oxygen atoms, sulfur atoms and/or NR.sup.11 -groups, provided that k and n are greater than 0, only when R.sup.11 stands for a C.sub.1 -C.sub.8 -alkyl radical,
and optionally their pharmaceutically compatible addition salts with acids.
Monosubstitution in 3, 4 or 5 position as well as disubstitution in 4 and 5 or 3 and 4 position with the formation of a fused second ring, for example a cyclohexene, pyrrole, furyl, pyrroline, 1,3-dioxacyclopentene, pyrazoline, didehydromorpholine, didehydropiperidine, didehydropiperazine, dihydropyrane, pyrimidine, pyridine, pyrazine, 1,4-dioxacyclohexene ring is preferred in the substitution of the phenyl ring.
The alkyl radicals standing for R.sup.1 and R.sup.11 should have, in the case of R.sup.1, 1 or 2 carbon atoms, in the case of R.sup.11, 1 to 8 carbon atoms and otherwise 1 to 4 carbon atoms, and the methyl, ethyl, propyl, isopropyl, butyl or methyl, ethyl, propyl groups are preferred.
If R.sup.12 stands for an acyl radical, then a formyl, acetyl, propionyl, butyryl and benzoyl group is preferred.
R.sup.11 and R.sup.12 together with the inclusion of the nitrogen atom also stand for heterocyclic five or six ring, that in addition to N and C atoms can also additionally contain an O or S atom; for example the pyrrole, pyrrolidine, piperid
REFERENCES:
patent: 3127423 (1964-03-01), Fried et al.
patent: 5041434 (1991-08-01), Liebkin
patent: 5095129 (1992-03-01), Ottow et al.
patent: 5232915 (1993-08-01), Ottow et al.
Elger Walter
Fritzemeier Karl
Neef Gunter
Ottow Eckhardt
Schneider Martin
Schering Aktiengesellschaft
Wu Shean
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