Phenyl-piperazine derivatives as serotonin reuptake inhibitors

Patent metadata

Field	Value
Publication number	US-10844029-B2
Application number	US-201715624417-A
Country	US
Kind code	B2
Filing date	Jun 15, 2017
Priority date	Oct 4, 2001
Publication date	Nov 24, 2020
Grant date	Nov 24, 2020

Abstract

The invention provides compounds represented by the general formula I

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.

First claim

The invention claimed is:

1. A compound represented by the formula I

wherein
Y is N;
X is S;
m is 1;
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 1 is independently C 1-6 -alkyl, or two R 1 attached to the same carbon atom form a 3-6-membered spiro-attached cycloalkyl;
each R 2 is independently halogen, cyano, nitro, C 1-6 -alkyl, C 1-6 -alkyloxy, C 1-6 -alkylsulfanyl, hydroxy, hydroxy-C 1-6 -alkyl, halo-C 1-6 -alkyl, halo-C 1-6 -alkyloxy, C 3-8 -cycloalkyl, C 3-8 -cycloalkyl-C 1-6 -alkyl, acyl, C 1-6 -alkyloxycarbonyl, or C 1-6 -alkylsulfonyl;
each R 3 is independently halogen;
or a pharmaceutically acceptable acid addition salt thereof.

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

3. The compound according to claim 1 , wherein R 1 is C 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 2 is trifluoromethyl, or C1-6-alkyl.

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

7. The compound according to claim 1 , wherein R 3 is fluoro.

8. 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.

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

10. The method of claim 9 , wherein the affective disorder is depression or an anxiety disorder.

11. The method of claim 10 , wherein the anxiety disorder is general anxiety disorder, panic disorder, or obsessive compulsive disorder.

12. The method of claim 9 , wherein the living animal is a human.

Assignees

• H Lundbeck As

Inventors

• Ruhland Thomas
• Smith Garrick Paul
• Bang-Andersen Benny
• Puschl Ask
• Moltzen Ejner Knud
• Andersen Kim

Classifications

• C07D211/20

  with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms · CPC title

• C07D211/70

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07D295/096 Primary

  with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings · CPC title

• A61P25/24

  Antidepressants · CPC title

• C07D295/033

  with the ring nitrogen atoms directly attached to carbocyclic rings · CPC title