Compounds as cannabinoid receptor ligands

A technology of compounds and solvates, applied in the field of compounds as ligands of cannabinoid receptors, can solve problems such as no effective therapeutics or drugs yet

Inactive Publication Date: 2012-05-09
ABBOTT LAB INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are currently no effective therapies or medications for all types of nociceptive and neuropathic pain states

Method used

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  • Compounds as cannabinoid receptor ligands
  • Compounds as cannabinoid receptor ligands
  • Compounds as cannabinoid receptor ligands

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0442] 5-Chloro-2-methoxy-N-[(2Z)-3-[(2R)-tetrahydrofuran-2-ylmethyl]-5-[1-(trifluoromethyl)cyclopropyl]-1 ,3,4-Thiadiazole-2(3H)-ylidene]benzamide

Embodiment 1A

[0444] 5-[1-(trifluoromethyl)cyclopropyl]-1,3,4-thiadiazol-2-amine

[0445] A mixture of 1-(trifluoromethyl)cyclopropanecarboxylic acid (1 g, 6.5 mmol) and thiosemicarbazide (0.6 g, 6.5 mmol) / dioxane (8 ml) was heated to 90°C. Phosphorus oxychloride (0.6ml, 6.5mmol) was added to the hot reaction mixture. The reaction mixture was stirred at 90°C for 16 hours. The reaction mixture was then cooled, diluted with ethyl acetate (10ml) and washed with saturated NaHCO 3(10ml) quenched. The aqueous layer was extracted with ethyl acetate (2 x 10 mL). The combined organic extracts were washed with water (15 mL), dried (Na 2 SO 4 ), filtered and concentrated. The residue was triturated in hot hexanes to afford 0.5 g (37%) of the title compound. LC / MS (ESI + ) m / z 210 (M+H) + .

Embodiment 1B

[0447] (2R)-4-Tetrahydrofuran-2-ylmethylbenzenesulfonate

[0448] The title compound was prepared from commercially available (R)-(tetrahydrofuran-2-yl)methanol (Fluka) according to procedures as described in: Ebata, T.; Kawakami, H.; Koseki, K.; Matsushita, H. Agricultural and Biological Chemistry, 1991, 55(6), 1685-6. MS (ESI + ) m / z 257 (M+H) + .

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Abstract

Disclosed herein are compounds of formula (I) wherein Ring A and R1 are as defined in the specification. Pharmaceutical compositions comprising such compounds, and methods for treating conditions and disorders using such compounds and pharmaceutical compositions are also disclosed.

Description

technical field [0001] CB is disclosed 2 Receptor ligands, compositions including such compounds, and methods of using such compounds and compositions to treat conditions and disorders. Background technique [0002] (-)-Δ 9 - THC (Δ 9 -THC) is the main psychoactive component of cannabis, which interacts with two cannabinoid (CB) receptor subtypes CB 1 and CB 2 Interactions exert various biological effects. CB 1 Receptors are highly expressed in the central nervous system and to a lesser extent in various peripherally located cardiovascular tissues and the gastrointestinal system. In contrast, CB 2 Receptors are highest expressed in various lymphoid organs and cells of the immune system, including spleen, thymus, tonsils, bone marrow, pancreas, and mast cells. [0003] by Δ 9 - Psychotropic effects caused by THC and other non-selective CB agonists by CB 1 Receptor mediated. These CBs 1 Receptor-mediated effects such as euphoria, sedation, hypothermia, stubbornness...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06C07D413/06C07D417/06A61K31/433A61P25/04
CPCC07D405/06C07D417/06C07D413/06A61P9/00A61P11/00A61P25/00A61P25/04A61P29/00A61P35/00A61P37/02A61P43/00
Inventor W. A. 卡罗尔M. J. 达特J. M. 弗罗斯特S. P. 拉特肖李彤梅刘波S. 佩迪王学庆T. 科拉萨D. W. 纳尔逊A. 佩雷斯-梅德拉诺
Owner ABBOTT LAB INC
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