Azetidin compounds suitable for treating disorders that respond to modulation of the serotonin 5-HT6 receptor

Compounds of formula (I)

• wherein
• A is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C3-C6-cycloalkyl, aryl-C1-C4-alkyl, aryl-C2-C4-alkenyl, aryl or hetaryl wherein cycloalkyl and the aryl or hetaryl moieties in the 5 last mentioned radicals may be unsubstituted or may carry 1, 2 or 3 substituents Ra, wherein
• Ra is selected from the group consisting of halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-hydroxyalkoxy, C1-C6-alkoxy-C1-C4-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylcarbonyl, C1-C6-haloalkyl-carbonyl, C1-C6-alkylcarbonylamino, C1-C6-haloalkylcarbonylamino, carboxy, NH—C(O)—NR3R4, NR3R4, NR3R4—C1-C6-alkylene, O—NR3R4, wherein R3 and R4 in the last 4 mentioned radicals are independently of each other hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or together with the nitrogen atom form an N-bound 5- to 7-membered saturated heterocycle, which may contain a further heteroatom selected from O, S and N as ring member, a saturated or unsaturated 3- to 7-membered heterocyclic ring, phenyl, benzyl, phenylsulfonyl, phenoxy and benzyloxy, wherein the 3- to 7-membered heterocyclic ring comprises as ring members 1, 2, 3 or 4 heteroatoms selected from N, O and S and may carry 1, 2 or 3 substituents selected from the group consisting of hydroxy, halogen, C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy and wherein the phenyl radical in phenyl, benzyl, phenylsulfonyl, phenoxy or benzyloxy is unsubstituted or may carry 1, 2 or 3 substituents selected from the group consisting of halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkylcarbonylamino, C1-C6-haloalkylcarbonylamino, carboxy, NH—C(O)—NR5R6, NR5R6, NR5R6—C1-C6-alkylene, O—NR5R6, wherein R5 and R6 are independently of each other hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and together with the nitrogen atom form an N-bound 5- to 7-membered saturated heterocycle, which may contain a further heteroatom selected from O, S and N as ring member;
• is a single bond or a double bond;
• X1 and X2 are independently from each other N or CRx1, if is a double bond, or NRx2 or CRx3Rx4, if is a single bond, wherein
• Rx1, Rx3 and Rx4 are selected from the group consisting of hydrogen, halogen, CN, NO2, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylcarbonyl, C1-C6-haloalkyl, C1-C6-haloalkoxy, C1-C6-haloalkylcarbonyl, C1-C6-hydroxyalkyl, C3-C6-cycloalkyl, phenyl, phenoxy and benzyloxy, wherein the last four mentioned radicals may be unsubstituted or may carry 1, 2 or 3 substituents selected from halogen, CN, NO2, C1-C4-alkyl, C1-C4-fluoroalkyl, C1-C4-alkoxy or C1-C4-fluoroalkoxy,
• or two geminal radicals Rx3 and Rx4 together with the carbon atom to which they are bound may form a carbonyl group or a 3- to 6-membered carbocyclic or heterocyclic spiro-annulated ring, which may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents selected from halogen, CN, NO2, C1-C4-alkyl, C1-C4-fluoroalkyl, C1-C4-alkoxy or C1-C4-fluoroalkoxy, and
• Rx2 is hydrogen, C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkyl, C1-C6-haloalkylcarbonyl, C1-C6-hydroxyalkyl, C3-C6-cycloalkyl or phenyl, wherein the last two mentioned radicals may be unsubstituted or may carry 1, 2 or 3 substituents selected from halogen, CN, NO2, C1-C4-fluoroalkyl, C1-C4-alkoxy or C1-C4-fluoroalkoxy;
• or two vicinal radicals selected from Rx1, Rx2, Rx3 or Rx4 together with X1 and X2 form a five- or six-membered carbocyclic or heterocyclic fused ring, which may be unsubstituted or may carry 1, 2, 3 or 4 substituents selected from halogen, CN, NO2, C1-C4-fluoroalkyl, C1-C4-alkoxy or C1-C4-fluoroalkoxy;
• Y1, Y2 and Y3 are independently from each other N or CRy, wherein
• Ry is hydrogen, halogen, CN, NO2, C1-C6-alkoxy, C1-C6-alkylcarbonyl, C1-C6-haloalkyl, C1-C6-haloalkoxy, C1-C6-halo-alkylcarbonyl, C1-C6-hydroxyalkyl, C3-C6-cycloalkyl, phenyl, phenoxy or benzyloxy wherein the last four mentioned radicals may be unsubstituted or may carry 1, 2 or 3 substituents selected from halogen, CN, NO2, C1-C4-fluoroalkyl, C1-C4-alkoxy or C1-C4-fluoroalkoxy;
• wherein a maximum of 3 of the moieties X1, X2, Y1, Y2 and Y3 are NRx1 or N;
• and wherein
• R1 is hydrogen, C1-C6-alkyl, C1-C6-hydroxyalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-haloalkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, aryl C1-C4-alkyl, hetaryl-C1-C4-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, formyl, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl;
• R2 is C1-C4-alkyl or C1-C4-haloalkyl;
• n is 0, 1 or 2;
• and physiologically tolerated acid addition salts and the N-oxides thereof.