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Details for Patent: 7,683,053

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Details for Patent: 7,683,053

Title:Phenyl-piperazine derivatives as serotonin reuptake inhibitors
Abstract: The invention provides compounds represented by the general formula I ##STR00001## wherein the substituents are defined in the application. The compounds are useful in the treatment of an affective disorder, including depression, anxiety disorders including general anxiety disorder and panic disorder and obsessive compulsive disorder.
Inventor(s): Ruhland; Thomas (Roskilde, DK), Smith; Garrick Paul (Valby, DK), Bang-Andersen; Benny (Copenhagen S, DK), Moltzen; Ejner Knud (Gentofte, DK), Andersen; Kim (Ridgewood, NJ)
Assignee: H. Lundbeck A/S (Valby-Copenhagen, DK)
Filing Date:Oct 19, 2006
Application Number:11/551,188
Claims:1. A compound represented by the formula I ##STR00015## wherein Y is N; X represents O or S; m is 2; p is 0, 1, 2, 3, 4, 5, 6, 7 or 8; q is 0, 1, 2, 3 or 4; s is 0, 1, 2, 3, 4 or 5; the dotted line represents an optional bond; each R.sup.1 is independently selected from the group represented by C.sub.1-6-alkyl, or two R.sup.1 attached to the same carbon atom may form a 3-6-membered spiro-attached cycloalkyl; each R.sup.2 is independently selected from the groups represented by halogen, cyano, nitro, C.sub.1-6-alkyl, C.sub.2-6-alkenyl, C.sub.2-6-alkynyl, C.sub.1-6-alkyloxy, C.sub.2-6-alkenyloxy, C.sub.2-6-alkynyloxy, C.sub.1-6-alkylsulfanyl, C.sub.2-6-alkenylsulfanyl, C.sub.2-6-alkynylsulfanyl, hydroxy, hydroxy-C.sub.1-6-alkyl, hydroxy-C.sub.2-6-alkenyl, hydroxy-C.sub.2-6-alkynyl, halo-C.sub.1-6-alkyl, halo-C.sub.2-6-alkenyl, halo-C.sub.2-6-alkynyl, halo-C.sub.1-6-alkyloxy, halo-C.sub.2-6-alkenyloxy, halo-C.sub.2-6-alkynyloxy, C.sub.3-8-cycloalkyl, C.sub.3-8-cycloalkenyl, C.sub.3-8-cycloalkyl-C.sub.1-6-alkyl, C.sub.3-8-cycloalkyl-C.sub.2-6-alkenyl, C.sub.3-8-cycloalkyl-C.sub.2-6-alkynyl, C.sub.3-8-cycloalkenyl-C.sub.1-6-alkyl, C.sub.3-8-cycloalkenyl-C.sub.2-6-alkenyl, C.sub.3-8-cycloalkenyl-C.sub.2-6-alkynyl, acyl, C.sub.1-6-alkyloxycarbonyl, C.sub.2-6-alkenyloxycarbonyl, C.sub.2-6-alkynyloxycarbonyl, C.sub.1-6-alkylsulfonyl, C.sub.2-6-alkenylsulfonyl, C.sub.2-6-alkynylsulfonyl, --NR.sup.xR.sup.y, --NR.sup.xCO--C.sub.1-6-alkyl, NR.sup.xCO--C.sub.2-6-alkenyl or NR.sup.xCO--C.sub.2-6-alkynyl; each R.sup.3 is independently selected from a group represented by halogen, cyano, nitro, C.sub.1-6-alkyl, C.sub.2-6-alkenyl, C.sub.2-6-alkynyl, C.sub.1-6-alkyloxy, C.sub.2-6-alkenyloxy, C.sub.2-6-alkynyloxy, C.sub.1-6-alkylsulfanyl, C.sub.2-6-alkenylsulfanyl, C.sub.2-6-alkynylsulfanyl, hydroxy, hydroxy-C.sub.1-6-alkyl, hydroxy-C.sub.2-6-alkenyl, hydroxy-C.sub.2-6-alkynyl, halo-C.sub.1-6-alkyl, halo-C.sub.2-6-alkenyl, halo-C.sub.2-6-alkynyl, halo-C.sub.1-6-alkyloxy, halo-C.sub.2-6-alkenyloxy, halo-C.sub.2-6-alkynyloxy, C.sub.3-8-cycloalkyl, C.sub.3-8-cycloalkenyl, C.sub.3-8-cycloalkyl-C.sub.1-6-alkyl, C.sub.3-8-cycloalkyl-C.sub.2-6-alkenyl, C.sub.3-8-cycloalkyl-C.sub.2-6-alkynyl, C.sub.3-8-cycloalkenyl-C.sub.1-6-alkyl, C.sub.3-8-cycloalkenyl-C.sub.2-6-alkenyl, C.sub.3-8-cycloalkenyl-C.sub.2-6-alkynyl, C.sub.1-6-alkylsulfonyl, C.sub.2-6-alkenylsulfonyl, C.sub.2-6-alkynylsulfonyl, aryl, C.sub.1-6-alkyloxycarbonyl, C.sub.2-6-alkenyloxycarbonyl, C.sub.2-6-alkynyloxycarbonyl, acyl, --NR.sup.xCO--C.sub.1-6-alkyl, NR.sup.xCO--C.sub.2-6-alkenyl, NR.sup.xCO--C.sub.2-6-alkynyl, --CONR.sup.xR.sup.y or NR.sup.xR.sup.y; or two adjacent R.sup.3 substituents together form a heterocycle fused to the phenyl ring selected from the group consisting of ##STR00016## wherein W is O or S, and R' and R'' are hydrogen or C.sub.1-6-alkyl: or two adjacent R.sup.3 substituents together form a fused heteroaromatic system containing one, two or three heteroatoms, wherein each R.sup.x and R.sup.y is independently selected from the group represented by hydrogen, C.sub.1-6-alkyl, C.sub.2-6-alkenyl, C.sub.2-6-alkynyl, C.sub.3-8-cycloalkyl, C.sub.3-8-cycloalkenyl, C.sub.3-8-cycloalkyl-C.sub.1-6-alkyl, C.sub.3-8-cycloalkyl-C.sub.2-6-alkenyl, C.sub.3-8-cycloalkyl-C.sub.2-6-alkynyl, C.sub.3-8-cycloalkenyl-C.sub.1-6-alkyl, C.sub.3-8-cycloalkenyl-C.sub.2-6-alkenyl, C.sub.3-8-cycloalkenyl-C.sub.2-6-alkynyl, or aryl; or R.sup.x and R.sup.y together with the nitrogen to which they are attached form a 3-7-membered ring which optionally contains one further heteroatom; or a pharmaceutically acceptable acid addition salt thereof provided that said compound is not 1-[2-(2,6-dimethoxyphenoxy)phenyl]-[1, 4]-diazepane.

2. The compound according to claim 1, wherein p is 0, 1 or 2.

3. The compound according to claim 1, wherein R.sup.1 is C.sub.1-6-alkyl.

4. The compound according to claim 1, wherein q is 0, 1 or 2.

5. The compound according to claim 1, wherein R.sup.2 is trifluoromethyl, or C.sub.1-6-alkyl.

6. The compound according to claim 1, wherein s is 1 or 2.

7. The compound according to claim 1, wherein R.sup.3 is selected from the group consisting of halogen, C.sub.1-6-alkoxy, C.sub.1-6-sulfanyl, C.sub.1-6-alkyl, hydroxy or trifluoromethyl.

8. The compound according to claim 1, said compound being 1-[2-(2-Trifluoromethylphenylsulfanyl)phenyl][1, 4]diazepane, 1-[2-(3-Methylphenylsulfanyl)phenyl]-[1, 4]-diazepane, or a pharmaceutically acceptable acid addition salt thereof.

9. A pharmaceutical composition comprising a compound according to claim 1 or a pharmaceutically acceptable acid addition salt thereof and at least one pharmaceutically acceptable carrier or diluent.

10. A method for the treatment of an affective disorder in a living animal body, comprising administering a therapeutically effective amount of a compound according to claim 1 or a pharmaceutically acceptable acid addition salt thereof.

11. The method of claim 10, wherein the living animal body is a human.

12. The method of claim 10, wherein the affective disorder is selected from the group consisting of depression, anxiety disorder, and obsessive compulsive disorder.

13. The method of claim 12, wherein the anxiety disorder is selected from the group consisting of general anxiety disorder and panic disorder.
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