Pharmaceutically active 9-chloroprostaglandins

A 9-chloroprostane of the formula ##STR7## wherein the 9-chlorine atom can be in the .alpha.- or .beta.-position

• R.sub.1 is OR.sub.2 wherein,
• R.sub.2 is H;
• C.sub.1-10 -alkyl;
• C.sub.1-10 -alkyl substituted by halogen, C.sub.1-4 -alkoxy, C.sub.6-10 -aryl or -aroyl, C.sub.6-10 -aryl or -aroyl substituted by the substituents defined below for the R.sub.2 aryl groups, di-C.sub.1-4 -alkylamino, or tri-C.sub.1-4 -alkylammonium;
• C.sub.4-10 -cycloalkyl;
• C.sub.4-10 -cycloalkyl-substituted by C.sub.1-4 -alkyl;
• C.sub.6-10 -aryl;
• C.sub.6-10 -aryl substituted by 1-3 halogen atoms, phenyl, 1-3 C.sub.1-4 -alkyl groups, or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 -alkoxy group;
• or an aromatic heterocycle of 5- or 6-total ring atoms and 1-2 hetero N, O or S atoms, the remainder being carbon atoms;
• A is cis--CH.dbd.CH--,
• B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--,
• W is hydroxymethylene or ##STR8## wherein the OH-group in each case can be in the .alpha.- or .beta.-position, and can be etherified or esterified by tetrahydropyranyl, tetrahydrofuranyl, .alpha.-ethoxyethyl, trimethylsilyl, dimethyl-tert-butylsilyl, tribenzylsilyl, acetyl, propionyl, butyryl or benzoyl;
• D and E together represent a direct bond or
• D is a straight-chain or branched alkylene group of 1-10 carbon atoms, optionally substituted by fluorine, and
• E is a direct bond, and
• R.sub.4 is hydroxy or hydroxy etherified or esterified as defined for W above;
• R.sub.5 is unsaturated and is a C.sub.1-10 hydrocarbon aliphatic group;
• or a C.sub.1-10 -hydrocarbon aliphatic group substituted by halogen;
• or a physiologically acceptable salt thereof with a base when R.sub.1 is OH.

A 9-chloroprostane of the formula ##STR9## wherein the 9-chlorine atom can be in the .alpha.- or .beta.-position

• R.sub.1 is OR.sub.2 wherein,
• R.sub.2 is H;
• C.sub.1-10 -alkyl;
• C.sub.1-10 -alkyl substituted by halogen, C.sub.1-4 -alkoxy, C.sub.6-10 -aryl or -aroyl, C.sub.6-10 -aryl or -aroyl substituted by the substituents defined below for the R.sub.2 aryl groups, di-C.sub.1-4 -alkylamino, or tri-C.sub.1-4 -alkylammonium;
• C.sub.4-10 -cycloalkyl;
• C.sub.4-10 -cycloalkyl substituted by C.sub.1-4 -alkyl;
• C.sub.6-10 -aryl;
• C.sub.6-10 -aryl substituted by 1-3 halogen atoms, phenyl, 1-3 C.sub.1-4 -alkyl groups, or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 -alkoxy group;
• or an aromatic heterocycle of 5- or 6-total ring atoms and 1-2 hetero N, O or S atoms, the remainder being carbon atoms;
• A is cis--CH.dbd.CH--,
• B is --CH.sub.2 --CH.sub.2 -- or --C.tbd.C--,
• W is hydroxymethylene or ##STR10## wherein the OH-group in each case can be in the .alpha.-or .beta.-position, and can be etherified or esterified by tetrahydropyranyl, tetrahydrofuranyl, .alpha.-ethoxyethyl, trimethylsilyl, dimethyl-tert-butylsilyl, tribenzylsilyl, acetyl, propionyl, butyryl or benzoyl;
• D and E together represent a direct bond or
• D is a straight-chain or branched alkylene group of 1-10 carbon atoms, optionally substituted by fluorine, and
• E is a direct bond, and
• R.sub.4 is hydroxy or hydroxy etherified or esterified as defined for W above;
• R.sub.5 is a C.sub.1-10 hydrocarbon aliphatic group;
• or a C.sub.1-10 -hydrocarbon aliphatic group substituted by halogen;
• or a physiologically acceptable salt thereof with a base when R.sub.1 is OH.