Claims
- 1. A compound of formula I whereinR1, R3, R4, R5 and R7 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 is hydrogen, hydroxy, halo, cyano, carboxamido, carboalkoxy of two to six carbon atoms, alkyl 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; R6 is hydrogen or alkyl of 1 to 6 carbon atoms; A dotted line represents an optional double bond; (O) represents optional oxidation; X is CR7 or N; and n is an integer 0, 1 or 2; or a pharmaceutically acceptable salt thereof.
- 2. A compound of claim 1 wherein R1 is hydrogen, hydroxy, halo, cyano, trifluoromethyl, alkyl of one to six carbon atoms or alkoxy of one to six carbon atoms.
- 3. A compound of claim 2 wherein R1 is hydrogen.
- 4. A compound of claim 1 wherein R2 is hydrogen, hydroxy, halo, alkyl of one to six carbon atoms, amino, mono- or di-alkylamino in which each alkyl group has one to six carbon atoms.
- 5. A compound of claim 4 wherein R2 is hydrogen or lower alkyl.
- 6. A compound of claim 1 wherein R3, R4, R5 are independently selected from hydrogen, hydroxy, halo, cyano, carboxamido, alkyl of one to six carbon atoms, and alkoxy of one to six carbon atoms.
- 7. A compound of claim 6 wherein R3, R4 and R5 are independently selected from halogen and hydrogen.
- 8. A compound of claim 1 in which R1 is hydrogen, hydroxy, halo, cyano, trifluoromethyl, alkyl of one to six carbon atoms or alkoxy of one to six carbon atoms; R2 is hydrogen, hydroxy, halo, alkyl of one to six carbon atoms, amino, mono- or di-alkylamino in which each alkyl group has one to six carbon atoms; R3, R4 and R5 are independently selected from hydrogen, hydroxy, halo, cyano, carboxamido, alkyl of one to six carbon atoms, and alkoxy of one to six carbon atoms; n is an integer 0 or 1; or a pharmaceutically acceptable salt thereof.
- 9. A compound of claim 1 in which R1 is hydrogen, hydroxy, halo, cyano, trifluoromethyl, alkyl of one to six carbon atoms or alkoxy of one to six carbon atoms, R2 is hydrogen or alkyl of one to six carbon atoms, R3, R4 and R5 are independently selected from hydrogen, halo and cyano, R6 is hydrogen, X is CR7, R7 is hydrogen, halo or cyano, n is 0 and the dotted line represents a double bond; or a pharmaceutically acceptable salt thereof.
- 10. A compound of claim 1 in which R1 is hydrogen, R2 is hydrogen or lower alkyl, and R3, R4 and R5 are independently selected from hydrogen and halogen, X is CR7, R7 is hydrogen or halogen, R6 is hydrogen and n is an integer 0.
- 11. The compound of claim 1 which is 2-[(4-(5-fluoro-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl)methyl]-2,3-dihydro[1,4]dioxino[2,3-f]quinazoline or a pharmaceutically acceptable salt thereof.
- 12. The compound of claim 1 which is 2-[(4-(1H-indol-3-yl)-3,6-dihydro-pyridin-1(2H)-yl)methyl]-2,3-dihydro[1,4]dioxino[2,3-f]quinazoline or a pharma-ceutically acceptable salt thereof.
- 13. The compound of claim 1 which is 2-[(4-(1H-indol-3-yl)-3,6-dihydro-pyridin-1(2H)-yl)methyl]-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]-quinazoline 9-oxide or a pharmaceutically acceptable salt thereof.
- 14. The compound of claim 1 which is 2-[(4-(1H-indol-3-yl)-3,6-dihydro-pyridin-1(2H)-yl)methyl]-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]-quinazoline or a pharmaceutically acceptable salt thereof.
- 15. The compound of claim 1 which is 2-[(4-(1H-indol-3-yl)-3,6-dihydro-pyridin-1(2H)-yl)methyl]-8-ethyl-2,3-dihydro[1,4]dioxino[2,3-f]quinazoline or a pharma-ceutically acceptable salt thereof.
- 16. A compound of the formula whereinR1 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 is hydrogen, hydroxy, halo, cyano, carboxamido, carboalkoxy of two to six carbon atoms, alkyl 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; X is halogen, hydroxy, 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; (O) represents optional oxidation.
- 17. A compound of claim 16 which is selected from:2,3-Dihydro[1,4]dioxino[2,3-f]quinazolin-2-ylmethyl 4-methylbenzene-sulfonate; (8-Methyl-2,3-dihydro[1,4]dioxino-[2,3-f]-quinazolin-2-yl)methyl 4-methyl-benzene sulfonate; (8-Methyl-9-oxo-2,3-dihydro[1,4]dioxino-[2,3-f]-quinazolin-2-yl)methyl 4-methylbenzene sulfonate; and (8-Ethyl-2,3-dihydro[1,4]dioxino-[2,3-f]-quinazolin-2-yl)-methyl 4-methyl-benzene sulfonate.
- 18. 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, anorexia nervosa, bulimia nervosa, vasomotor flushing, 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 whereinR1, R3, R4, R5 and R7 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 is hydrogen, hydroxy, halo, cyano, carboxamido, carboalkoxy of two to six carbon atoms, alkyl 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; R6 is hydrogen or alkyl of 1 to 6 carbon atoms; A dotted line represents an optional double bond; (O) represents optional oxidation; X is CR7 or N; and n is an integer 0, 1 or 2; or a pharmaceutically acceptable salt thereof.
- 19. The method of claim 18 wherein the condition is depression.
- 20. The method of claim 18 wherein the condition is obsessive compulsive disorder, panic attacks, generalized anxiety disorder or social anxiety disorder.
- 21. The method of claim 18 wherein the subject is a human.
- 22. A pharmaceutical composition comprising a compound of formula I whereinR1, R3, R4, R5 and R7 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 is hydrogen, hydroxy, halo, cyano, carboxamido, carboalkoxy of two to six carbon atoms, alkyl 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; R6 is hydrogen or alkyl of 1 to 6 carbon atoms; A dotted line represents an optional double bond; (O) represents optional oxidation; X is CR7 or N; and n is an integer 0, 1 or 2; or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or excipient.
Parent Case Info
This application claims priority from provisional application Ser. No. 60/286,573, filed on Apr. 26, 2001, the entire disclosure of which is hereby incorporated by reference.
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Provisional Applications (1)
|
Number |
Date |
Country |
|
60/286573 |
Apr 2001 |
US |