Initial compounds for the production of 10.beta.-H-steroids and

Details Initial compounds for the production of 10.beta.-H-steroids and Initial compounds for the production of 10.beta.-H-steroids and

1992-11-30

1994-10-25

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540107, 540108, 540114, 540116, 540120, 540 36, 540 37, 552505, 552612, 552642, C07J 100, C07J 1700, C07J 2100

Patent

active

053590546

DESCRIPTION:

BRIEF SUMMARY
This invention relates to compounds of general formula III ##STR3## in which A and B together mean an additional bond and
R.sup.4 stands for a hydrogen atom, a cyano group, a chlorine, fluorine, bromine, iodine atom, for a trialkylsilyl, trialkylstannyl group, for a straight-chain or branched, saturated or unsaturated C.sub.1 -C.sub.8 -alkyl, acyl or alkoxyalkyl radical, for an amino group ##STR4## in which R.sup.7 and R.sup.8 independently of one another mean a hydrogen atom or a C.sub.1 -C.sub.4 -alkyl group or for a corresponding amine oxide ##STR5## or for the groupings --OR.sup.9 or --S(O).sub.i R.sup.9 with i=0, 1 or 2, in which R.sup.9 means a hydrogen atom, a methyl, ethyl, propyl, isopropyl, methoxyphenyl, allyl or a 2-dimethylaminoethyl group, or for a heteroaryl radical of formula I.alpha. ##STR6## in which A symbolizes a nitrogen, oxygen, or sulfur atom, --B--D--E the element sequence --C--C--C, --N--C--C-- or --C--N--C-- and R.sup.10 a hydrogen atom, a cyano group, a chlorine, fluorine, bromine, iodine atom, a trialkylsilyl, trialkylstannyl group, a straight-chain or branched, saturated or unsaturated C.sub.1 -C.sub.8 -alkyl, acyl or alkoxyalkyl radical, an amino group ##STR7## in which R.sup.7 and R.sup.8 independently of one another mean a hydrogen atom or a C.sub.1 -C.sub.4 -alkyl group, or a corresponding amine oxide ##STR8## or the grouping --OR.sup.9 or --S(O).sub.i R.sup.9 with i=0, 1 or 2 in which R.sup.9 means a hydrogen atom, a methyl, ethyl, propyl, isopropyl, methoxyphenyl, allyl or a 2-dimethylaminoethyl group, ##STR9## in which A means a nitrogen atom and --B--D--E-- the element sequence --C--C--C--, --N--C--C--, --C--N--C-- or --C--C--N-- and R.sup.10 has the already indicated meaning, ##STR10## in which R.sup.10 has the already indicated meaning,
Y and Y' mean a protected keto group or a protected hydroxy group and a hydrogen atom, and Y and Y' can be identical or different, and production process.
Preferred are the following compounds:
In addition to the ethylenedioxy group, for example, the 2,2-dimethylpropylene-1,3-dioxy group can also, stand for Y/Y'. Other common protective groups are also possible. If Y and/or Y' stand for a protected hydroxy group and a hydrogen atom, the hydroxy group can be protected, for example as methoxymethyl, methoxyethyl, tetrahydropyranyl or silyl ether.
The compounds of general formula III themselves are used as initial products for the new process for the production of end compounds of general formula I described in the simultaneously filed German patent application . . . ##STR11## in which
X stands for an oxygen atom, the hydroxyimino grouping >N.about.OH or two hydrogen atoms,
R.sup.1 stands for a hydrogen atom or a methyl group,
R.sup.2 stands for a hydroxy group, a C.sub.1 -C.sub.10 -alkoxy or C.sub.1 -C.sub.10 -acyloxy group,
R.sup.3 stands for a hydrogen atom, the grouping --(CH.sub.2).sub.n CH.sub.2 Z, and n is 0, 1, 2, 3, 4 or 5, Z means a hydrogen atom, the cyano group or the radical --OR.sup.5 with R.sup.5 =H, C.sub.1 -C.sub.10 -alkyl or C.sub.1 -C.sub.10 -acyl, the grouping --(CH.sub.2).sub.m --C.ident.C--Y, and m is 0, 1 or 2 and Y means a hydrogen, fluorine, chlorine, bromine or iodine atom, a C.sub.1 -C.sub.10 -hydroxyalkyl-, C.sub.1 -C.sub.10 -alkoxyalkyl-, C.sub.1 -C.sub.10 -acyloxyalkyl radical, the grouping --CH=--CH--(CH.sub.2).sub.k CH.sub.2 R.sup.6, and k means 0, 1 or 2 and R.sup.6 means a hydrogen, a hydroxy group, a C.sub.1 -C.sub.4 -alkoxy- or C.sub.1 -C.sub.4 -acyloxy radical, or else R.sup.2 and R.sup.3 together stand for a radical of formula ##STR12## and R.sup.4 has the meaning indicated already in formula III for this substituent.
Also their pharmacologically compatible addition salts with acids belong to the end compounds of general formula I.
The compounds of general formula I themselves have already been described for the most part in German patent application P 39 21 059.6. They are of great interest first of all because of their strong antigestagen properties.
According to this invention the compounds of g

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