Steroids with pregnane skeleton, pharmaceutical compositions con

Details Steroids with pregnane skeleton, pharmaceutical compositions con Steroids with pregnane skeleton, pharmaceutical compositions con

1994-12-08

1996-08-20

Rizzo, Nicholas

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Cyclopentanohydrophenanthrene ring system doai

540106, 540107, C07J 4300, A61K 3156

Patent

active

055479499

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/HU93100035 filed Jun. 8, 1993.


FIELD OF THE INVENTION

The invention relates to novel therapeutically active 21-aminosteroids of the formula ##STR2## with pregnane skeleton, wherein two of X, Y and Z are each a nitrogen atom each and the third one is a methine group; amino group bearing as substituent a branched-chain C.sub.4-8 alkyl, -alkenyl or -alkynyl group, or a C.sub.4-10 cycloalkyl group comprising 1 to 3 ring(s) and being optionally substituted by C.sub.1-3 alkyl group(s); or containing at most 10 carbon atoms and optionally at least one oxygen atom as additional heteroatom; or group containing 4 to 7 carbon atoms and the other one is an above-identified primary amino group, an above-identified spiro-heterocyclic secondary amino group, or a heterocyclic secondary amino group containing 4 to 7 carbon atoms and substituted by C.sub.1-4 -alkyl group(s); and containing these compounds.
Furthermore, the invention relates to a process for the preparation of the above compounds.
The compounds of the formula (I) according to the invention are new and possess a valuable biological activity, an antioxidant (lipid peroxidation-inhibiting) effect, when investigated under in vitro conditions. Some representatives of them show a remarkable effectivity in vivo on the cerebral trauma model.
Accordingly, the invention relates also to a method of treatment which comprises administering a therapeutically effective amount of a compound of the formula (I) or a pharmaceutically acceptable acid addition salt thereof into the organism of a patient for inhibiting the peroxidation of lipids.
Hereinafter and in the claims primary amino groups are meant to contain a hydrogen atom as one substituent whereas the other substituent is a branched-chain C.sub.4-8 alkyl, -alkenyl or -alkynyl group, or a C.sub.4-10 cycloalkyl group, comprising 1 to 3 rings, and being optionally substituted by C.sub.1-3 -alkyl group(s). The branched-chain C.sub.4-8 alkyl, -alkenyl and -alkynyl groups may be various iso-, sec- and tert-butyl, butenyl, pentyl, pentenyl, pentynyl, hexyl, hexenyl, hexynyl, pentyl, heptenyl, heptynyl, octyl, octenyl and octynyl groups. Preferred representatives of these are the 1,1-dimethylethyl, 2,2-dimethylpropyl and 2,2-dimethyl-4-penten-1-yl groups.
The C.sub.4-10 cycloalkyl group comprising 1 to 3 rings and being optionally substituted by C.sub.1-3 alkyl group(s) can be e.g. a cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or adamantyl group. These groups may be unsubstituted or bear one or more methyl, ethyl or propyl group(s) as substituents.
As R.sup.1 and R.sup.2, the spiro-heterocyclic secondary amino group containing at most 10 carbon atoms and optionally at least one additional oxygen heteroatom is exemplified by the 4,4-ethylenedioxy-1-piperidinyl group, without any limitation thereto.
When representing an unsubstituted heterocyclic secondary amino group containing 4 to 7 carbon atoms, one of R.sup.1 and R.sup.2 may preferably be a pyrrolidino, piperidino or azepino group. In this case, the other one of R.sup.1 and R.sup.2 means either a primary amino group mentioned above, or an above-defined secondary heterocyclic group having spiro structure, or an above-defined heterocyclic secondary amino group containing 4 to 7 carbon atoms and substituted by C.sub.1 -.sub.4 alkyl group(s). These C.sub.1 -.sub.4 alkyl groups may be the same or different, e.g. methyl, ethyl, n- or isopropyl, or n-, iso-, sec- or tert-butyl groups. A preferred representative of these substituted heterocyclic secondary amino groups is e.g. the 2,2,6,6-tetramethyl-1-piperidinyl group.


BACKGROUND OF THE INVENTION

There are a large number of pat hological processes known, in the case of which extremely reactive free radicals are accumulated. The formation of these free radicals leads to the oxidation of unsaturated fatty acids (lipid peroxidation), which are important components of the cell membranes. This is a less specific, cell-destroying process altering or damaging the biomolecules. In this process

REFERENCES:
patent: 5099019 (1992-03-01), Mc Call et al.
J. Med. Chem. 33(4), pp. 1145 to 1151 (1990).

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