Heteroaryl diazacycloalkanes, their preparation and use

The dimeric diazacycloalkane represented by Formula II, III, or IV

• any of its enantiomers or any mixture thereof, an N oxide thereof, a pharmaceutically acceptable salt thereof, in a labelled or un-labelled form,
• wherein,
• n is 1;
• and
• m is 2;
• and
• R represents hydrogen, an alkyl group, a cycloalkyl group, a cycloalkylalkyl group, or an alkenyl group, or, when R is shown with two valences, R represents an alkylene group, a cycloalkylene group, a cycloalkylalkylene group, or an alkenylene group;
• and
• R1 represents pyridyl, pyridazinyl, quinolinyl or isoquinolinyl, which monocyclic or bicyclic heterocyclic group is optionally substituted one or more times with substitutents selected from the group consisting of alkyl, alkoxy, cycloalkoxy, alkoxyalkoxy, alkoxyalkenyl, alkoxyalkynyl, alkynyl, alkenyl, alkenylthio, alkylseleno, alkoxycycloalkyl, hydroxyalkoxy, alkylthio, arylalkylthio, alkenoxy, alkynoxy, carboxylamido, arylthio, hydroxy, trifluoromethanesulfonyloxy, halogen;
• phenyl;
• phenyl substituted with alkyl, alkoxy, hydroxy, amino, or nitro;
• a pyrrolinyl, a piperidinyl, a tetrahydropyridyl, or a morpholinyl group, or, when R1 is shown with two valences, R1 is a divalent bridging radical derived by removal of a hydrogen atom from one of the groups listed in this definition of R1;
• and
• “—R—B—R—” in Formula II represents a single bond bridge or a bridging group of the formula “—R—R—” or a bridging group of the formula “—R—”;
• or
• “—R—B—R1—” or “—R—B—” in Formula IV represents a single bond bridge;
• or
• “—R—B—R1—” in Formula III represents a single bond bridge or a bridging group of the formula “—R1—R1—” or a bridging group of the formula “—R1—”;
• or
• “—R—B—R—” in Formula IV represents a single bond bridge or a bridging group of the formula “—R1—R—”;
• or “—R1—B—” in Formula IV represents a single bond bridge;
• and
• B represents a single bond bridge or a bridging element of the formula “—ALK—”, “—ALK—X—ALK—”, “—X—ALK—X—”, “—PHE—”, “—X—PHE—X—”, or “—ALK—PHE—ALK—”;
• wherein “ALK” represents a single bond bridge or alkylene, alkenylene, or alkynylene;
• and “PHE” represents a phenylene group;
• and X represents O, S, NH, N-alkyl, or Se.