Antidepressant azaheterocyclylmethyl derivatives of 2,3-dihydro-1,4-dioxino[2,3-f]quinoxaline

A compound of the formula

• wherein
• R1 is hydrogen, hydroxy, halo, cyano, carboxamido, carboalkoxy of two to six carbon atoms, trifluoromethyl, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkanoyloxy of 2 to 6 carbon atoms, amino, mono- or di-alkylamino in which each alkyl group has 1 to 6 carbon atoms, alkanamido of 2 to 6 carbon atoms, or alkanesulfonamido of 1 to 6 carbon atoms;
• R2 and R3 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, halogen, hydroxy, cyano or amino;
• X is hydroxy, halogen, alkylsulfonate of 1 to 6 carbon atoms, trifluoromethanesulfonate or benzenesulfonate, in which the benzene ring is optionally substituted with halogen, nitro, trifluoromethyl, cyano, alkyl of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms.

A method of treating a subject suffering from a condition selected from the group consisting of depression, anxiety, panic disorder, post-traumatic stress disorder, premenstrual dysphoric disorder, attention deficit disorder, obsessive compulsive disorder, social anxiety disorder, generalized anxiety disorder, obesity, eating disorders, vasomotor flushing, cocaine and alcohol addiction, and sexual dysfunction, which comprises providing to the subject suffering from said condition, a therapeutically effective amount of a compound of formula I

• wherein
• R1, R4, R5, R6 and R8 are, independently, hydrogen, hydroxy, halo, cyano, carboxamido, carboalkoxy of two to six carbon atoms, trifluoromethyl, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkanoyloxy of 2 to 6 carbon atoms, amino, mono- or di-alkylamino in which each alkyl group has 1 to 6 carbon atoms, alkanamido of 2 to 6 carbon atoms, or alkanesulfonamido of 1 to 6 carbon atoms;
• R2 and R3 are, independently, hydrogen, alkyl of 1 to 6 carbon atoms, halogen, hydroxy, cyano or amino;
• R7 is hydrogen or alkyl of 1 to 6 carbon atoms;
• the dotted line represents an optional double bond;
• Z is CR8 or N;
• and
• n is an integer 0, 1 or 2;
• or a pharmaceutically acceptable salt thereof.

A pharmaceutical composition comprising a compound of formula I

• wherein
• R1, R4, R5, R6 and R8 are, independently, hydrogen, hydroxy, halo, cyano, carboxamido, carboalkoxy of two to six carbon atoms, trifluoromethyl, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkanoyloxy of 2 to 6 carbon atoms, amino, mono- or di-alkylamino in which each alkyl group has 1 to 6 carbon atoms, alkanamido of 2 to 6 carbon atoms, or alkanesulfonamido of 1 to 6 carbon atoms;
• R2 and R3 are, independently, hydrogen, alkyl of 1 to 6 carbon atoms, halogen, hydroxy, cyano or amino;
• R7 is hydrogen or alkyl of 1 to 6 carbon atoms;
• the dotted line represents an optional double bond;
• Z is CR8 or N;
• and
• n is an integer 0, 1 or 2;
• or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier or excipient.