9-Fluoroprostaglandin derivatives, and use as medicinal agents

Claim 1

A 9-Fluoroprostane derivative of the formula ##STR18## wherein R 1 is CH 2 OH or ##STR19## wherein R 2 is (a) hydrogen, (b) C 1-10 alkyl, (c) C 1-10 alkyl substituted by halogen; C 1-4 alkoxy; C 6-10 -aryl or aroyl; C 6-10 -aryl or aroyl each substituted by 1-3 halogen atoms, a phenyl group, 1-3 C 1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C 1-4 alkoxy group; di-C 1-4 -alkylamino; or tri-C 1-4 -alkylammonium; (d) C 3-10 cycloalkyl, (e) C 3-10 cycloalkyl substituted by C 1-4 alkyl, (f) C 6-10 aryl, (g) C 6-10 aryl substituted by 1-3 halogen atoms, a phenyl group, 1-3 C 1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C 1-4 alkoxy group, or (h) an aromatic heterocycle of 5 or 6 ring atoms, one or two of which are O, N or S, the remainder being carbon atoms; or R 1 is ##STR20## wherein R 3 is an acyl group of a hydrocarbon C 1-5 carboxylic or sulfonic acid or is one of the R 2 groups; A is --CH 2 --CH 2 -- or cis--CH═CH--; B is --CH 2 --CH 2 --, trans--CH═CH-- or C.tbd.C--; W is hydroxymethylene or RO-methylene, wherein the OR or OH group is in a α- or β-position; R is tetrahydropyranyl, tetrahydrofuranyl, α-ethoxyethyl, trimethylsilyl, dimethyl-tert-butylsilyl, tribenzylsilyl or an acyl group of a C 1-5 -hydrocarbon carboxylic or sulfonic acid. D and E jointly are a direct bond or D is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms, optionally substituted by 1-2 fluorine atoms and E is oxygen, sulfur, a direct bond, C.tbd.C-- or --CR 6 ═CR 7 -- wherein R 6 and R 7 differ from each other and each is hydrogen, chlorine or C 1-6 -alkyl; R 4 is OH or OR; R 5 is (a) a C 6-10 hydrocarbon aliphatic radical substituted by C 6-10 -aryl or by C 6-10 -aryl substituted by 1-3 halogen atoms, a phenyl group, 1-3 C 1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, caboxy, hydroxy or C 1-4 alkoxy group; (b) C 3-10 cycloalkyl, (c) C 3-10 cycloalkyl substituted by C 1-4 alkyl; (d) C 6-10 aryl, (e) C 6-10 aryl substituted by 1-3 halogen atoms, a phenyl group, 1-3 C 1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C 1-4 alkoxy group; or (f) an aromatic heterocycle of 5 or 6 ring atoms, one or two of which are O, N or S, the remainder being carbon atoms; or when R 2 is hydrogen, a physiologically compatible salt thereof with a base.