Carlo Erba S.p.a.

Farmitalia Carlo Erba

Farmitalia Carlo Erba S.p.a.

Isf S.p.a.

Renato Pellegata

Carmelo Gandolfi

Maria M Usardi

Roberto Ceserani

Franco Faustini

Angelo Fumagalli

Gianfederico Doria

Mario Pinza

Giorgio Pifferi

Silvano Banfi

Fluoro-prostaglandin compounds are disclosed, such as, for instance, 18,19,20-trinor-17-cyclohexyl-16(S,R)-fluoro-PGF.sub.2.alpha.. The fluoro-prostaglandins of the present invention have the same therapeutical uses as natural prostaglandins, but have the advantage of being resistant to the enzyme 15-prostaglandin dehydrogenase, and also exhibit a more selective therapeutical action. Certain of the compounds of the present invention exhibit very favorable luteolytic and antiulcer activity.

Fluoro-prostaglandins and process for their preparation

16-Fluoro-13,14-dehydro-PG.sub.2 series have been prepared, and their pharmaceutical use.

.omega.-Nor-cycloalkyl-13,14-dehydro-prostaglandin compounds, specifically 5c-9-oxo-11.alpha.,15S-dihydroxy-20,19,18-tirnor-17-cyclohexyl-prost-5-en- 13-ynoic acid, the esters and salts thereof, having antiulcer and luteolytic activity, are disclosed.

.omega.-Nor-cycloalkyl-13,14-dehydro-prostaglandins and process for

16-Fluoro-prostaglandins and pharmaceutical compositions containing the same are prepared. They are useful, for example, as anti-ulcer agents.

Cyclopenta[b]furan-2-one and -2-ol intermediates for

16-Fluro-13, 14-dehydro-PG.sub.2 series compounds have been prepared.

Fluoro-prostaglandins

Fluoro-prostaglandin compounds are disclosed, such as, for instance, 18,19,20-trinor-17-cyclohexyl-13-14-dehydro-16(S,R)-fluoro-PGF.sub.2.alpha .. The fluoro-prostaglandins of the present invention have the same therapeutical uses as natural prostaglandins, but have the advantage of being resistant to the enzyme 15-prostaglandin dehydrogenase, and also exhibit a more selective therapeutical action. Certain of the compounds of the present invention exhibit very favorable luteolytic and antiulcer activity.

Novel optically active 13,14-dehydro-11-deoxy-prostaglandins having a phenyl or substituted-phenyl group on the lower side chain are disclosed.

13,14-Dehydro-11-deoxy-prostaglandins and process for their preparation

16-fluoro-substituted prostaglandin analogs of the formula: ##STR1## in which R is hydrogen, a C.sub.1 -C.sub.12 alkyl group or a cation of a pharmaceutically acceptable base; one of R.sub.1 and R.sub.2 is hydrogen and the other is hydroxy or acyloxy or R.sub.1 and R.sub.2 take together, form a oxo group; one of R.sub.4 and R.sub.5 is hydroxy and the other is hydrogen; R.sub.6 is hydrogen, methyl or fluorine; n is zero or an integer of 1 to 6; and R.sub.7 is phenyl or phenyl substituted by at least one of halogen C.sub.1 -C.sub.6 alkoxy or trihalomethyl.

14-Halo lactone and lactol prostaglandin intermediates have been prepared.

Preparation of compounds of the formula: ##STR1## wherein n is 1, 2 or 3, R.sub.1 and R.sub.2, which may be the same or different, are hydrogen or alkyl containing 1 to 3 carbon atoms and the asterisk indicates the center of asymmetry of the molecule, and compounds of the formula ##STR2## wherein R' is a saturated or unsaturated aliphatic hydrocarbon containing 1 to 6 carbon atoms, R.sub.3 is hydrogen or acyl containing 1 to 7 carbon atoms and the asterisk indicates the center of asymmetry of the molecule. The compounds produced by the present invention improve learning memory and display a protecting effect against the E.E.G. consequence of an overdose of barbiturates and against the reduced performance following brain damage (e.g. cerebral edema).

Preparation of pyrrolidine and pyrrolidin-2-one derivatives

.omega.-NOR-CYCLOALKYL-13,14-DEHYDRO-PROSTAGLANDIN COMPOUNDS, SPECIFICALLY 13,14-DEHYDRO-17-CYCLOHEXYL-20,19,18-TRINOR-PGF.sub.2.alpha. having antiulcer and luteolytic activity, are disclosed.

.omega.-Nor-cycloalkyl-13,14-dehydro-prostaglandins

16S and 16R methyl 13, 14 dehydro PGE.sub.2 compounds have been prepared.

16-Methyl prost-5-en-13-ynoic acid derivatives

Omega-nor-cycloalkyl-13,14-dehydro-prostaglandin compounds, specifically 13,14-dehydro-17-cyclohexyl-20,19,18-trinor-PGF.sub.2.sub..alpha., having selective luteolytic, abortifacient and labor-inducing activity and extremely low untoward gastrointestinal effects are disclosed.

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Milan, Italy

Renato Pellegata