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2-iminoisothiazole derivatives as cannabinoid receptor ligands

A technology of alkyl and alkynyl groups, applied in the field of compounds containing isothiazolylide groups, can solve the problems of ineffective treatment and the like

Inactive Publication Date: 2010-06-30
ABBOTT LAB INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are currently no viable treatments or medications that effectively treat all types of nociceptive and neuropathic pain states

Method used

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  • 2-iminoisothiazole derivatives as cannabinoid receptor ligands
  • 2-iminoisothiazole derivatives as cannabinoid receptor ligands
  • 2-iminoisothiazole derivatives as cannabinoid receptor ligands

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0365] N-[(5Z)-4-butyl-2-tert-butylisothiazole-5(2H)-ylidene]-5-chloro-2-methoxybenzamide

Embodiment 1A

[0367] N-(tert-butyl)-N-hexylideneamine

[0368] CH 2 Cl 2 (10 mL) in tert-butylamine (5.25 mL, 50.0 mmol) and MgSO 4 (2 g) was slowly added hexanal (6.0 mL, 50 mmol). The reaction became exothermic halfway through the addition, so an ice bath was used briefly to control reaction rate and avoid solvent and amine boil-off. After the addition was complete, the reaction was stirred at room temperature for 2 h, filtered through celite under a stream of nitrogen, and washed with 20 mL of anhydrous CH 2 Cl 2 washing. The solvent was evaporated to obtain a pale yellow liquid. 1 H NMR (300MHz, CDCl 3 )δ0.87-0.91(m, 3H), 1.17(s, 9H), 1.25-1.35(m, 4H), 1.45-1.55(m, 2H), 2.23(m, 2H), 7.59(t, 1H) .

Embodiment 1B

[0370] 5-Chloro-2-methoxybenzoyl chloride

[0371] 5-Chloro-2-methoxybenzoic acid (11.3g, 60.56mmol) and SOCl 2 (9 mL, 123.7 mmol) was heated slightly in toluene (20 mL), during which a vigorous gas evolution occurred. After the gas evolution had subsided, the reaction was heated to reflux for 1.5 hours, cooled and stirred at room temperature overnight. The volatiles were evaporated in vacuo and the remaining material was treated with toluene and evaporated (2x) to remove excess SOCl 2 , a white solid was obtained which was directly used in the next step without purification. 1 H NMR (300MHz, CDCl 3 )δ3.92(s, 3H), 6.95(d, 1H), 7.53(dd, 1H), 8.03(d, 1H).

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PUM

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Abstract

The present application relates to isothiazolylidene containing compounds of Formula (I) wherein R<1>, R<2>, R<3>, R<4>, and L are as defined in the specification, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

Description

field of invention [0001] The present invention relates to compounds containing an isothiazole group, compositions containing the compounds and methods of using the compounds and compositions to treat conditions and diseases. Background of the invention [0002] (-)-Δ 9 -tetrahydrocannabinol (Δ 9 -THC), the main psychoactive component of cannabis, through its interaction with two cannabinoid (CB) receptor subtypes, CB 1 and CB 2 The interaction showed a wide range of therapeutic effects. CB 1 Receptors are highly expressed in the central nervous system, but to a lesser extent in peripheral tissues of the cardiovascular and gastrointestinal systems. In contrast, CB 2 The receptor is extremely abundantly expressed in a variety of lymphoid organs and cells of the immune system, including spleen, thymus, tonsil, bone marrow, pancreas, and mast cells. [0003] by Δ 9 - Psychotropic side effects caused by THC and other non-selective CB agonists by CB 1 Receptor mediated. ...

Claims

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Application Information

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IPC IPC(8): C07D275/02C07D275/04C07D417/04C07D417/06C07D417/12C07D513/04C07D513/10A61K31/425A61P9/00A61P11/00A61P25/00A61P29/00A61P35/00A61P37/00
CPCC07D513/04A61K31/427C07D513/10A61K31/429A61K31/5377A61K31/4725A61K31/425C07D275/02C07D275/04A61K31/4436C07D417/06C07D417/04C07D417/12Y02P20/582A61P11/00A61P25/00A61P25/04A61P29/00A61P35/00A61P37/00A61P43/00A61P9/00
Inventor W·A·卡罗尔M·J·达特T·科拉萨李彤梅D·W·奈尔逊M·V·帕特尔S·佩迪A·佩雷斯-梅德拉诺X·王
Owner ABBOTT LAB INC
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