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4-(2-phenylsulfanyl-phenyl)-1,2,3,6-tetrahydropyridine derivatives as serotonin reuptake inhibitors

A thio- and hydroxyl-based technology is applied in the field of 4-(2-phenylthio-phenyl)-1,2,3,6-tetrahydropyridine derivatives as a serotonin reuptake inhibitor, and can solve the problem of Drug therapy can not wait for the problem

Inactive Publication Date: 2006-05-24
H LUNDBECK AS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Second, the side effect of sexual dysfunction is common to all SSRIs
Without addressing these issues, no real progress can be made in drug therapy for depression and anxiety

Method used

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  • 4-(2-phenylsulfanyl-phenyl)-1,2,3,6-tetrahydropyridine derivatives as serotonin reuptake inhibitors
  • 4-(2-phenylsulfanyl-phenyl)-1,2,3,6-tetrahydropyridine derivatives as serotonin reuptake inhibitors
  • 4-(2-phenylsulfanyl-phenyl)-1,2,3,6-tetrahydropyridine derivatives as serotonin reuptake inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0316] Synthetic method A:

[0317] Compound 2: 4-[2-(4-Chlorophenylthio)-phenyl]-1,2,3,6-tetrahydropyridine

[0318] Concentrated aqueous hydrochloric acid (10 mL) was added to a stirred solution of 1-tert-butoxycarbonyl-4-[2-(4-chlorophenylthio)phenyl]piperidin-4-ol (0.84 g, 2 mmol) in acetic acid ( 30mL). The solution was boiled at reflux overnight, cooled to room temperature, then stirred in an ice bath. Aqueous NaOH (9.1 M, 40 mL) was slowly added and the cloudy solution was extracted with ethyl acetate (2 x 40 mL). The combined organic phases were dried (MgSO4) and the solvent was evaporated in vacuo. The crude product (0.48 g) was dissolved in ethyl acetate (3.2 mL) at 50 °C, and a solution of oxalic acid (0.11 g) in EtOH (3.2 mL) was added slowly. Collect the white oxalate salt of the target compound. 1 H(DMSO-d 6 )δ7.3-7.2(m, 7H); 7.15(m, 1H); 7.00(m, 1H); 5.6(d, 1H); 3.7(d, 2H); 3.25(t, 2H); , 2H); LC / MS (m / z) 302.1 (MH + ); RT = 2.29; Purity (UV, ELSD): 100%...

Embodiment 2

[0320] Synthetic method B:

[0321] Compound 24: 4-[2-(2-Chlorophenylthio)-phenyl]-1,2,3,6-tetrahydropyridine

[0322] Bis[(2-diphenylphosphino)phenyl]ether (22mg; 0.04mmol) and bis(dibenzylidene)palladium (23mg; 0.04mmol) were dissolved in 2.5mL of toluene and added to 4-hydroxy -4-(2-Mercapto-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (200 mg; 0.64 mmol) and 1-chloro-2-iodobenzene (200 mg; 0.84 mmol) in 4 mL of toluene. Potassium tert-butoxide (80 mg; 0.68 mmol) was added and the reaction mixture was stirred at 100° C. under argon for 16 hours. The reaction mixture was filtered through silica gel, eluting with ethyl acetate. Solvent was removed in vacuo. The residue was dissolved in 4 mL of glacial acetic acid and 1 mL of concentrated HCl. The mixture was stirred at 100°C for 16 hours. The solution was poured onto ice and 8 mL of 28% aqueous NaOH was added. The base suspension was extracted with ethyl acetate (2 x 50 mL). The combined organic phases were wa...

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PUM

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Abstract

The present invention provides compounds represented by general formula (I), wherein the substituents are as defined in the application. The compounds are useful in the treatment of affective disorders including depression, anxiety disorders including generalized anxiety disorder, panic disorder and obsessive-compulsive disorder.

Description

[0001] The present invention relates to novel compounds which are serotonin reuptake inhibitors and are therefore useful in the treatment of, for example, depression and anxiety. Background of the invention [0002] Selective serotonin reuptake inhibitors (hereafter referred to as SSRIs) have become the treatment of choice in the treatment of depression, some forms of anxiety, and social phobia because of their efficacy, favorable well tolerated and with a good safety profile. However, clinical studies on depression have shown considerable non-response to SSRIs, up to 30%. [0003] Additionally, an often overlooked factor in antidepressant treatment is adherence, which has a rather profound impact on driving patients to continue drug therapy. [0004] First, SSRIs are slow to respond. Sometimes, symptoms even worsen during the first week of treatment. Second, the side effect of sexual dysfunction is common to all SSRIs. Without addressing these issues, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/70A61K31/4409A61P25/00C07D405/12
CPCC07D211/70C07D405/12A61P25/00A61P25/18A61P25/20A61P25/22A61P25/24A61P43/00
Inventor A·皮施尔B·邦-安德森M·约尔根森K·于尔T·鲁兰德K·安德森J·克勒
Owner H LUNDBECK AS
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