Alkane and alkene derivatives and their use

Abstract

The invention provides novel compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, hydroxy, alkoxy of 1 to 4 carbon atoms, benzyloxy, allyloxy, 2,3-epoxypropoxy, methoxymethoxy, ethoxymethoxy, or 2,3-dihydroxypropoxy or ##STR2## wherein one of R.sub.5 and R.sub.6 is hydrogen or R.sub.5 and R.sub.6 are alkyl groups of 1-4 carbon atoms which may be the same or different, or the --NR.sub.5 R.sub.6 group stands for a nitrogen containing 5 to 7 membered heterocyclic radical and m is 1 or 2; R.sub.2 is an alkyl of 1 to 4 carbon atoms or ##STR3## wherein R.sub.7 has the same meanings as R.sub.1 except that R.sub.7 and R.sub.1 cannot simultaneously be the same; R.sub.3 is an alkyl of 2 to 4 carbon atoms, cyclopentyl or hydroxy-cyclopentyl; R.sub.4 is hydrogen or hydroxy; and n is 0 to 3, provided that when R.sub.4 is hydrogen, then R.sub.2 and R.sub.3 are not simultaneously lower alkyl containing up to 4 carbon atoms, and their non-toxic pharmaceutically acceptable acid addition salts and esters and mixtures thereof. Processes for the preparation of these compounds are described, as are novel pharmaceutical compositions of the compounds or their salts. The compounds and their non-toxic salts exhibit valuable pharmacological properties as estrogenic, anti-estrogenic, progestanic and anti-tumor activity. Certain compounds of the group are useful as chemical intermediates for the preparation of pharmaceutically active compounds of the invention.