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1,2,3-triazole derivatives as sigma receptor inhibitors

A solvate, C1-C6 technology, which can be used in medical preparations containing active ingredients, anti-inflammatory agents, drug combinations, etc., and can solve problems such as unreported effects

Inactive Publication Date: 2009-11-25
LAB DEL DR ESTEVE SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, none of these documents suggest an effect of these compounds on sigma receptors

Method used

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  • 1,2,3-triazole derivatives as sigma receptor inhibitors
  • 1,2,3-triazole derivatives as sigma receptor inhibitors
  • 1,2,3-triazole derivatives as sigma receptor inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0118] Example 1: 1-[3-[4-(p-chlorophenyl)-5-phenyl-([1,2,3]triazol-2-yl)propyl]-piperidine (compound 1) synthesis

[0119] Step A: A mixture of tri-n-butyltin azide (0.86 mL, 3.15 mmol) and 4-chlorophenylethynylbenzene (3 mmol) was heated in a sealed glass vial at 150 °C for 70 hours. The resulting solution was purified by column chromatography (cyclohexane / AcOEt, 5:1) and recrystallized from (cyclohexane / AcOEt) to give 4-(p-chlorophenyl)-5-phenyl-1H( 2H)-[1,2,3]triazole as a white solid (413 mg, 54% yield); melting point 124-126°C. 1 H NMR (200MHz, CDCl 3 , 25°C) δ=7.51-7.46 (m, 4H), 7.38-7.35 (m, 3H), 7.31 (dt, 3 J=8.6Hz, 4 J= 5 J = 2.2 Hz, 2H) ppm. ES-MS: m / z=278 [M + +Na], 256[M + ]. C 14h 10 ClN 3 (255.70): Calculated for C 65.76, H 3.94, N 16.43; found for C 65.93, H 3.84, N 16.37.

[0120] Step B: To a solution of 4-(p-chlorophenyl)-5-phenyl-1H(2H)-[1,2,3]triazole (0.16 mmol) in acetonitrile (3 mL) was added K 2 CO 3 (26mg, 0.19mmol) and Bu 4 NBr (5 mg,...

Embodiment 2

[0123] Example 2: 1-[3-[4-(p-chlorophenyl)-5-phenyl-([1,2,3]triazol-2-yl)propyl]-imidazole (Compound 2)

[0124] The melting point is 122-124°C. 1 HNMR (500MHz, CDCl 3 , 25°C) δ=7.60(1H, s), 7.54-7.52(2H, m), 7.49(2H, d, 3 J=8.5Hz), 7.40-7.38 (3H, m), 7.34 (2H, d, 3 J=8.5Hz), 7.10(1H, s), 7.02(1H, s), 4.48(2H, t, 3 J=6.5Hz), 4.09(2H,t, 3 J=6.5Hz), 2.49 (2H, qt, 3 J = 6.5 Hz) ppm. ES-MS: m / z=365(13), 364(8), 363(36) [M +· ]; 364(12), 362(38)[M-1]; 95(82)[M-269]; 82(100)[M-282]; 212(27)[M-165]; 165(21 )[M-212].

Embodiment 3

[0125] Embodiment 3: 1-[3-[4-(3,4-dichlorophenyl)-5-phenyl-([1,2,3]triazol-2-yl)propyl]-pyrrolidine ( Compound 3)

[0126] 1 HNMR (500MHz, CDCl 3 , 25°C) δ=7.70(1H, d, 4 J=2.0Hz), 7.51-7.49 (2H, m), 7.42-7.38 (4H, m), 7.33 (1H, dd, 3 J=8.3Hz, 4 J=2.0Hz), 4.56(2H,t, 3 J=7.0Hz), 2.75-2.72 (6H, m), 2.37 (2H, qt, 3 J=7.0Hz), 1.87 (4H, qt, 3 J = 3.4 Hz) ppm. ES-MS: m / z=402(1), 400(1)[M +· ]; 111(20)[M-290]; 84(100)[M-317]; 70(19)[M-331].

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PUM

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Abstract

The invention relates to compounds having pharmacological activity towards the sigma receptor, and more particularly to 1,2,3-triazole derivatives of formula (I) and to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use in therapy and prophylaxis, in particular for the treatment of psychosis or pain.

Description

field of invention [0001] The present invention relates to compounds having pharmacological activity on sigma receptors, more particularly to certain 1,2,3-triazole derivatives, processes for the preparation of these compounds, pharmaceutical compositions containing these compounds and their therapeutic and prophylactic Use in diseases mediated by sigma receptors. Background of the invention [0002] In recent years, the search for new therapeutic agents has been greatly assisted by a better understanding of the structures of proteins and other biomolecules associated with target diseases. An important class of these proteins are the sigma (σ) receptors, cell surface receptors of the central nervous system (CNS) that may be involved in the dysphoric, hallucinogenic and cardiostimulatory effects of opioids. From the biological and functional studies of σ receptors, there is evidence that σ receptor ligands may be used in the treatment of psychosis and movement disorders such...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06A61K31/4192A61P25/00A61P35/00
CPCC07D249/06A61P1/04A61P1/12A61P19/02A61P25/00A61P25/04A61P25/06A61P25/08A61P25/18A61P25/22A61P25/24A61P25/28A61P25/32A61P25/34A61P25/36A61P27/06A61P29/00A61P35/00A61P3/04A61P3/06A61P37/06A61P43/00A61P9/06A61P9/10A61P9/12A61K31/4192
Inventor 纳丁·贾戈洛维克克里斯蒂娜·安娜·戈梅兹-德拉奥利瓦玛利亚·皮拉尔·戈雅-拉扎埃尔伯特·多达尔卓尔拉斯玛莉亚·罗萨·库韦莱斯-阿尔蒂森特
Owner LAB DEL DR ESTEVE SA
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