Farmos Group Ltd.

Orion-Yhtyma Oy

Guillermo L Blanco

Arto J Karjalainen

Lauri V Kangas

Kauko O Kurkela

Reijo J Toivola

Marja-Liisa Soderwall

Hannu K Sundquist

Arja Marketta Kalapudas

Marja-Liisa Sodervall

Hannu K Sunduiqst

The invention provides novel compounds of the formula: ##STR1## wherein R.sub.1 and R.sub.2, which can be the same or different are H or OH, R.sub.3 is ##STR2## wherein R.sub.4 and R.sub.5, which can be the same or different are H or an alkyl group of 1 to 4 carbon atoms, and their non-toxic pharmaceutically acceptable salts and esters and mixtures thereof, which compounds include metabolites of toremifene and exhibit valuable pharmacological properties as oestrogenic, anti-oestrogenic, and progestanic agents.

Tri-phenyl alkene derivatives and their preparation and use

##STR1## wherein n is 0 to 4, R.sub.1 and R.sub.2, which can be the same or different, are H or OH; R.sub.3 is --O--(CH.sub.2).sub.m --CH.sub.2 --NR.sub.6 R.sub.7 wherein m is 1 or 2, R.sub.6 and R.sub.7, which can be the same or different, are H or an alkyl group of 1 to 4 carbon atoms, or --NR.sub.6 R.sub.7 can form a pyrrolidinyl group; and R.sub.4 is halogen, and their non-toxic pharmaceutically acceptable salts and phenolic esters of aliphatic or aromatic carboxylic acids, acid anhydrides or acid chlorides thereof are disclosed. These compounds exhibit valuable pharmacological properties as estrogenic, anti-estrogenic, and progestanic agents. They show activity against oestrogen-dependent tumors.

Tri-phenyl alkane derivatives and their oestrogenic, anti-oestrogenic

The invention provides novel compounds of the formula: ##STR1## wherein n is 0 to 4, R.sub.1 and R.sub.2, which can be the same or different are H, OH, alkoxy of 1 to 4 carbon atoms, benzyloxy or methoxymethoxy; R.sub.3 is H, OH, halogen, alkoxy of 1 to 4 carbon atoms, benzyloxy, methoxymethoxy, 2,3-dihydroxypropoxy or ##STR2## wherein m is 1 or 2, R.sub.6 and R.sub.7, which can be the same or different are H or an alkyl group of 1 to 4 carbon atoms, or ##STR3## can form an N-containing three-, four-, five- or six-membered heterocyclic ring; R.sub.4 is OH, F, Cl, Br, I, mesyloxy, tosyloxy, alkylcarbonyloxy of 1 to 4 C-atoms, formyloxy or CH.sub.2 R.sub.4 is replaced by CHO; R.sub.5 is H or OH; or R.sub.4 and R.sub.5 together form an --O-- bridge between the carbon atoms to which they are attached, and their non-toxic pharmaceutically acceptable salts and esters and mixtures thereof. Processes for the preparation of these compounds are described, and also novel pharmaceutical compositions containing them. These compounds exhibit valuable pharmacological properties as estrogenic, anti-estrogenic, and progestanic agents. They are also effective against oestrogen-dependent tumors. Certain compounds are useful as chemical intermediates for the preparation of pharmacologically active compounds of the invention.

Novel tri-phenyl alkane and alkene derivatives and their preparation and

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.

Alkane and alkene derivatives and their use

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Oulu, Finland

Guillermo L Blanco