Farmos Group Ltd.

Orion-Yhtyma Oy

Marja-Liisa Soderwall

Arto J Karjalainen

Lauri V Kangas

Kauko O Kurkela

Reijo J Toivola

Guillermo L Blanco

Hannu K Sundquist

Arja Marketta Kalapudas

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

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Oulu, Finland

Marja-Liisa Soderwall