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Benzodioxane and benzodioxolane derivatives and uses thereof

A phenyl, monocyclic technology, applied in the field of 5-HT2C receptor agonists or partial agonists, can solve the problem of not reducing the inflammation of the substantia nigra

Inactive Publication Date: 2008-07-09
WYETH LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, recent studies have demonstrated that 5-HT 2C Agonists reduce inflammation in the ventral tegmental area (VTA), but not in the substantia nigra

Method used

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  • Benzodioxane and benzodioxolane derivatives and uses thereof
  • Benzodioxane and benzodioxolane derivatives and uses thereof
  • Benzodioxane and benzodioxolane derivatives and uses thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0799] {[8-(2-chlorophenyl)-2,3-dihydro-1,4-benzodi-en-2-yl]methyl}amine: 2-azidomethyl-8-( 2-Chloro-phenyl)-2,3-dihydro-benzo[1,4]di-ene (100mg, 0.33mmol) and 5% Pt-S 2 Carbon (0.25 g) in methanol (50 mL) was hydrogenated overnight in a Parr apparatus at 55-60 Psi. The mixture was filtered through a pad of celite. The solvent was removed in vacuo to form a colorless oil. Dissolving the oil in ethanol converted to white solid fumarate (37mg); mp 210-211°C;

[0800] MS(ES)m / z 276[M+H] +

[0801] to C 15 h 14 ClNO 2 ·C 4 h 4 o 4 Elemental analysis of:

[0802] Theoretical values: C, 58.25; H 4.63; N, 3.57

[0803] Found values: C, 57.81; H, 4.58; N, 5.67

[0804] General procedure for the production of I from azide derivatives:

[0805] To a solution of the intermediate azide (1.0 mmol) in tetrahydrofuran was added polymer-supported triphenylphosphine (-3 mmol / g, 2.0 mmol) and water. The mixture was stirred at room temperature for 24 hours and filtered through a p...

Embodiment 2

[0808]{[8-(2-fluorophenyl)-2,3-dihydro-1,4-benzodi-en-2-yl]methyl}amine: with 2-azidomethyl-8-( Starting from 2-fluoro-phenyl)-2,3-dihydro-benzo[1,4]di-ene (140 mg, 0.5 mmol), 87 mg (47%) of the title compound were obtained as fumarate; mp188 -190°C;

[0809] MS(ESI)m / z 260[M+H] +

[0810] to C 15 h 14 FNO 2 ·C 4 h 4 o 4 Elemental analysis of:

[0811] Theoretical value: C, 60.80; H, 4.83; N, 3.73

[0812] Found values: C, 61.14; H, 4.42; N, 3.74

Embodiment 3

[0814] {[8-(2-methylphenyl)-2,3-dihydro-1,4-benzodi-en-2-yl]methyl}amine: with 2-azidomethyl-8- Starting from (2-methyl-phenyl)-2,3-dihydro-benzo[1,4]di-ene (110 mg, 0.39 mmol), 42 mg (29%) of the title compound were obtained as fumaric acid Salt, mp 201-202°C; MS (ESI) m / z 256 [M+H] + .

[0815] to C 16 h 17 NO 2 ·C 4 h 4 o 4 Elemental analysis of:

[0816] Theoretical values: C 64.68; H 5.70; N 3.77

[0817] Found: C, 64.70; H 5.46; N 3.71

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Abstract

Compounds of formula (I) or pharmaceutically acceptable salts thereof are provided, wherein each of R<1>, R<2>, R<3>, R<4>, y, n, m, and Ar are as defined, and described in classes and subclasses herein, which are agonists or partial agonists of the 2C subtype of brain serotonin receptors. The compounds, and compositions containing the compounds, can be used to treat a variety of central nervous system disorders such as schizophrenia.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Patent Application No. US 60 / 673,884, filed April 22, 2005, which is incorporated herein by reference in its entirety. field of invention [0003] The present invention relates to 5-HT 2C Receptor agonist or partial agonist, its preparation method and its use. Background of the invention [0004] Schizophrenia affects about 5 million people. Currently the most common treatment for schizophrenia is the combination of dopamine (D 2 ) and 5-hydroxytryptamine (5-HT 2A ) receptor antagonism of 'atypical' antipsychotics. Although atypical antipsychotics have been reported to have improved efficacy or side effect propensity over typical antipsychotics, these compounds have not been shown to adequately treat all symptoms of schizophrenia and are accompanied by questionable side effects such as weight gain (Allison, D....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/20C07D409/04C07D317/46A61K31/357A61K31/36A61K31/381A61P25/18
CPCC07D409/04C07D317/46C07D319/20A61P1/14A61P13/10A61P15/10A61P15/12A61P25/00A61P25/04A61P25/06A61P25/08A61P25/14A61P25/16A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P25/32A61P25/36A61P3/04A61P43/00C07D317/58
Inventor D·周G·P·斯塔克J·L·格罗斯H·高
Owner WYETH LLC
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