Patent ID: 6225347
Filing Date: 2001-05-01
Classification: A61P,C07C

Abstract:
A 9-halogen-(Z) prostane derivative of the formula ##STR29##in whichZ is ##STR30##Hal is a chlorine or fluorine atom in alpha or beta position,R.sub.1 is ##STR31##wherein R.sub.2 is (a) hydrogen;(b) C.sub.1-10 -alkyl;(c) C.sub.1-10 -alkyl substituted by halogen, C.sub.1-4 -alkoxy, C.sub.6-10 -aryl, C.sub.6-10 -aroyl, C.sub.6-10 -aryl or C.sub.6-10 -aroyl each substituted as defined below for aryl, dialkylamino or trialkylammonium;(d) C.sub.3-10 -cycloalkyl or C.sub.3-10 -cycloalkyl substituted by C.sub.1-4 -alkyl;(e) C.sub.6-10 -aryl or C.sub.6-10 -aryl substituted by 1-3 halogen atoms, phenyl, 1-3 C.sub.1-4 -alkyl groups, chloromethyl, fluoromethyl, trifluoromethyl, carboxyl, hydroxy or C.sub.1-4 -alkoxy;(f) a 5- or 6-membered aromatic heterocyclic ring containing an N, O or S atom;R.sub.3 is an acyl group of a C.sub.1-15 -hydrocarbon carboxylic or sulfonic acid, or a group defined for R.sub.2 ;A is a --CH.sub.2 --CH.sub.2 -, a trans-CH.dbd.CH-- or --C.tbd.C-- group,W is hydroxymethylene or ##STR32##wherein the hydroxy and OR group can be in the alpha or beta position,D and E together are a single bond orD is C.sub.1-10 -alkylene; C.sub.1-10 -alkylene substituted by fluorine; annular C.sub.3-10 -alkylene; annular C.sub.3-10 -alkylene substituted by fluorine; C.sub.2-10 -alkenylene; C.sub.2-10 -alkenylene substituted by fluorine; annular C.sub.3-10 -alkenylene; or annular C.sub.3-10 -alkenylene substituted by fluorine;E is oxygen, sulfur, a single bond, a --C.tbd.C-- bond or --CR.sub.6.dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 are different from each other and are hydrogen, chlorine, or C.sub.1-4 -alkyl;R.sub.4 is OR;R is H; an acyl group of a C.sub.1-15 -hydrocarbon carboxylic or sulfonic acid; tetrahydropyranyl; tetrahydrofuranyl; alpha-ethoxyethyl; trimethylsilyl; dimethyl tert-butylsilyl; dimethyl hexylsilyl; diphenyl tert-butylsilyl or tribenzylsilyl;R.sub.5 is hydrogen; C.sub.1-10 -alkyl; C.sub.1-10 -alkyl substituted by hydrogen, phenyl or C.sub.1-4 -alkyl; C.sub.2-10 -alkenyl; C.sub.2-10 -alkenyl substituted by halogen, phenyl or C.sub.1-4 -alkyl; in the case where D and E together are a single bond C.sub.2-6 -alkinyl or C.sub.2-6 -alkinyl 1-substituted by fluorine or by C.sub.1-4 -alkyl; C.sub.3-10 -cycloalkyl or C.sub.3-10 -cycloalkyl substituted by C.sub.1-4 -alkyl; C.sub.6-10 -aryl or C.sub.6-10 -aryl substituted by 1-3 halogen atoms, phenyl, 1-3 C.sub.1-4 -alkyl, chloromethyl, fluoromethyl, trifluoromethyl, carboxyl, hydroxy or C.sub.14 -alkoxy; or a 5- or 6-membered aromatic heterocyclic ring containing a N, O or S atom;or there R.sub.2 is H, a physiologically compatible salt thereof or a cyclodextrin chlathrate thereof.