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Imine compound

A technology of imine compounds and alkyl groups, applied in the field of imine compounds, can solve problems such as the agonism of cannabinoid receptors that have not been reported

Inactive Publication Date: 2007-10-31
TAISHO PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no reports of cannabinoid receptor agonism using imine compounds as active ingredients

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0636] Preparation of 1-cyclopropylmethyl-2-(trifluoroacetylimino)-1,2-dihydropyridine (Compound No. 1)

[0637] 【化31】

[0638]

[0639] To a solution of 2-aminopyridine (2.0 g) and pyridine (1.9 ml) in chloroform (20 ml), trifluoroacetic anhydride (3.3 ml) was added under ice-cold conditions, and the mixture was stirred at room temperature for 3 days. The reaction solution was washed (in the order of water and saturated brine), dried (anhydrous sodium sulfate), filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane-ethyl acetate = 3:1) to obtain 2-(trifluoroacetylamino)pyridine (2.3 g) as a colorless liquid.

[0640] The obtained 2-(trifluoroacetylamino)pyridine (1.3g) was dissolved in N,N-dimethylformamide (13ml), and sodium iodide (0.01g) and 60% sodium hydride ( 0.27g) and cyclopropylmethyl bromide (1.1g) were heated and stirred at 50°C for 5 hours. The reaction s...

Embodiment 2

[0643] Preparation of 1-cyclopropylmethyl-2-{3-(trifluoromethyl)benzoylimino}-1,2-dihydropyridine (Compound No. 2)

[0644] (1) 1-Cyclopropylmethyl-2-imino-1,2-dihydropyridine

[0645] 【化32】

[0646]

[0647] Dissolve 1-cyclopropylmethyl-2-(trifluoroacetylimino)-1,2-dihydropyridine (1.1g) prepared according to the preparation method shown in Example 1 in methanol (25ml), An aqueous solution obtained by dissolving anhydrous potassium carbonate (1.2 g) in water (12.5 ml) was added at room temperature, and the mixture was stirred for 2 hours. The reaction solution was extracted (ethyl acetate), dried (anhydrous sodium sulfate), and after filtration, the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (developing solvent: chloroform-methanol = 18:1) to obtain 1-cyclopropylmethyl-2-imino-1,2-dihydropyridine (0.5g) as a yellow liquid ).

[0648] 1 H-NMR (200MHz, CHLOROFORM-d) d ppm; 0.31-0.37 (m, 2H), 0.58-0.67 (m...

Embodiment 3

[0656] Preparation of 1-cyclopropylmethyl-2-{3-(trifluoromethyl)phenylsulfonylimino}-1,2-dihydropyridine (Compound No. 50)

[0657] 【化34】

[0658]

[0659] According to the preparation method shown in Example 2, 3-(trifluoromethyl)phenylsulfonyl chloride was used instead of 3-(trifluoromethyl)benzoyl chloride to obtain 1-cyclopropylmethyl- as a colorless solid. 2-{3-(Trifluoromethyl)phenylsulfonylimino}-1,2-dihydropyridine.

[0660] 1 H-NMR, Mass and melting point are shown in Table 8.

[0661] Compound Nos. 3-49 and 51-59 shown in Table 1, Compound Nos. 60, 71-107, 116-174, 178-213, 215-342, 343-351, and 369-372 shown in Table 2 Compound Nos. 504-515 shown in Table 3 were prepared according to the preparation methods shown in Examples 1 and 2.

[0662] Of these compounds 1 H-NMR, Mass and melting point are shown in Table 8, Table 9 and Table 11.

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Abstract

An imine compound represented by the formula (I) (wherein A represents a heterocyclic group; R<1>, R<2>, and R<3> each represents hydrogen, halogeno, C1-10 alkyl optionally substituted by haloaryl, C3-10 cycloalkyl, C1-6 haloalkyl, C1-10 alkoxy, etc.; R<4> represents optionally substituted C1-10 alkyl, C2-6 alkenyl, or aryl; R<5> represents hydrogen, C1-10 alkoxy, C1-6 haloalkyl, optionally substituted C1-10 alkyl or C2-6 alkenyl, optionally substituted aryl or heterocyclic group, etc.; and W represents -CO-, -CO-CO-, -CO-NH-, -CS-NH-, or -SO2-) or a cannabinoid receptor agonist containing the compound as an active ingredient. The imine compound has agonistic activity against a cannabinoid receptor and is useful as a therapeutic or preventive agent for pains and autoimmune diseases.

Description

Technical field [0001] The present invention relates to imine compounds having cannabinoid receptor agonism (excitatory action). Background technique [0002] Cannabinoids are substances isolated as the physiologically active components of cannabis in 1960. They have analgesic, anti-anxiety, sedative, and euphoric effects. Later, by identifying its receptors, endogenous ligands with cannabinoid-like physiological activities such as anandamide were discovered. [0003] As a cannabinoid receptor, the cannabinoid type 1 (CB1) receptor was discovered in 1990. It is known to be distributed in the central nervous system such as the brain, and its agonist shows analgesic effects. The cannabinoid type 2 (CB2) receptor was discovered in 1993. It is known to be distributed in the tissues or cells of the immune system including the spleen, lymph nodes, white blood cells, B cells, T cells, macrophages, mast cells and other blood cell line cells. Among them, its agonists show immunosuppressiv...

Claims

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Application Information

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IPC IPC(8): A61K31/426A61K31/415A61K31/4155A61K31/42A61K31/421A61K31/422A61K31/4245A61K31/425A61K31/427A61K31/428A61K31/429A61K31/433A61K31/4365A61K31/437A61K31/4375A61K31/44A61K31/4409A61K31/4418A61K31/4427A61K31/443A61K31/4433A61K31/4436A61K31/4439A61K31/444A61K31/454A61K31/47A61K31/4709A61K31/472A61K31/4725A61K31/496A61K31/497A61K31/498A61K31/501A61K31/502A61K31/5025A61K31/505A61K31/506A61K31/5377A61K31/538A61K31/541A61K31/55A61P25/04A61P29/00A61P37/06A61P43/00C07D213/75C07D213/76C07D213/84C07D215/38C07D217/22C07D231/38C07D231/40C07D239/42C07D261/14C07D263/48C07D271/10C07D275/02C07D277/20C07D277/46C07D277/56C07D277/82C07D285/12C07D401/12C07D405/12C07D409/12C07D409/14C07D413/12C07D417/06C07D417/12C07D417/14C07D471/04C07D487/04C07D495/04C07D513/04
Inventor 斋藤秀次太田裕之石坂知子吉永光周田续诚横堀祐治富岛保光森田亚纪户田喜久德川纪美子加来绫香村上智美吉村广光关根伸吾吉水孝绪
Owner TAISHO PHARMACEUTICAL CO LTD
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