Heteroaryl diazacycloalkanes, their preparation and use

The present invention discloses compounds of the formula ##STR1##

any of its enantiomers or any mixture thereof, isotopes thereof or a pharmaceutically acceptable salt thereof;

wherein

• n is 1, 2 or 3;
• m is 0, 1 or 2;
• R represents hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, or aralkyl; and

  R¹ represents aminophenyl; nitrophenyl; hydroxyphenyl, alkoxyphenyl;

  a monocyclic 5 to 6 membered heterocyclic group which may be substituted one or more times with substituents selected from the group consisting of alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, alkoxy, cycloalkoxy, alkenoxy, alkynoxy, alkynoxy, methylenedioxy, halogen, CF₃, OCF₃, CN, amino, nitro, COOR³, CONR²R³, NHCO₂R², NHCOR², OCONR²R³;

  wherein R² and R³ independently represents hydrogen or alkyl;

• aryl optionally substituted one or more times with alkyl, cycloalkyl, cycloalkylalkyl alkenyl, alkynyl, alkoxy, cycloalkoxy, alkenoxy, alkynoxy, methylenedioxy, halogen, CF₃, OCF₃, CN, amino and nitro;
• X-alkyl-Y-alkyl wherein X and Y independently represents O, S, NH, N-alkyl or Se; and alkyl is optionally substituted with alkoxy or thioalkoxy;
• X-(alkyl)_o-aryl wherein o is 0 or 1 and X represents O, S, NH, N-alkyl or Se; optionally substituted one or more times with alkyl, cycloalkyl, cycloalkylalkyl alkenyl, alkynyl, alkoxy, cycloalkoxy, alkenoxy, alkynoxy, methylenedioxy, halogen, CF₃, OCF₃, CN, amino and nitro;
• X-(alkyl)_o-Z wherein o is 0 or 1 and X represents O, S, NH, N-alkyl or Se and Z represents a 5- or 6-membered monocyclic heterocyclic group; optionally substituted one or more times with alkyl, cycloalkyl, cycloalkylalkyl alkenyl, alkynyl, alkoxy, cycloalkoxy, alkenoxy, alkynoxy, methylenedioxy, halogen, CF₃, OCF₃, CN, amino and nitro;
• a monocyclic 5 to 6 membered heterocyclic group optionally substituted one or more times with alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, alkoxy, cycloalkoxy, alkenoxy, alkynoxy, methylenedioxy, halogen, CF₃, OCF₃, CN, amino and nitro; or

  or R¹ represents a bicyclic heterocyclic group, composed of a 5 to 6 membered monocyclic heterocyclic group fused to a benzene ring, and which may be substituted one or more times with substituents selected from the group consisting of alkyl, cycloalkyl, cycloalkylalkyl alkenyl, alkynyl, alkoxy, alkoxy-alkoxy, cycloalkoxy, alkenoxy, alkynoxy, methylenedioxy, halogen, CF₃, OCF₃, CN, amino, nitro, aryl optionally substituted one or more times with alkyl, cycloalkyl, cycloalkylalkyl alkenyl, alkynyl, alkoxy, cycloalkoxy, alkenoxy, alkynoxy, methylenedioxy, halogen, CF₃, OCF₃, CN, amino and nitro; and a monocyclic 5 to 6 membered heterocyclic group optionally substituted one or more times with alkyl, cycloalkyl, cycloalkylalkyl alkenyl, alkynyl, alkoxy, cycloalkoxy, alkenoxy, alkynoxy, methylenedioxy, halogen, CF₃, OCF₃, CN, amino and nitro;

The compounds of the invention are useful as nicotinic ACh receptor ligands.