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Steroid compound

A technology of steroidal compounds and compounds, applied in the direction of steroidal compounds, drug combinations, organic chemistry, etc., can solve the problems of insufficiency, achieve the effects of less production, low activity, and reduced local side effects

Inactive Publication Date: 2015-01-07
MIKASA SEIYAKU
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although the compounds described in Non-Patent Document 1 and Patent Document 1 reduce the side effects of steroids, they are not enough

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Synthesis of Compound 1 ( figure 1 )

[0043]Synthesis of compound A: 1.2 g of D-(+)-glucose was dissolved in 40 mL of chloroform, and 14.5 mL of p-toluoyl chloride and 8.9 mL of pyridine were added dropwise at 0-5°C. The mixture was stirred for 6 hours while slowly returning the temperature to room temperature. The reaction solution was poured into ice water, extracted with chloroform, and the organic layer was washed with saturated aqueous copper sulfate, saturated aqueous sodium bicarbonate and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. Of the obtained residues, 5.33 g of the residue was isolated and purified by silica gel column chromatography (toluene:ethyl acetate=50:1), to obtain 4.5 g of Compound A as a white powder.

[0044] 1 H-NMR (CDCl 3 )δ: 2.309(3H, s), 2.315(3H, s), 2.362(3H, s), 2.408(3H, s), 2.474(3H, s), 7.101(2H, d, J=8.06), 7.106 (2H, d, J = 8.06), 7.156 (2H, d, J = 8.06...

Embodiment 2

[0054] Synthesis of Compound 2 ( figure 2 )

[0055] Compound 1 (887 mg) was dissolved in anhydrous methanol (10 mL) and anhydrous chloroform (5 mL), and 28% sodium methoxide (1 mL) was added dropwise at room temperature under an argon atmosphere, and the reaction was further stirred for 1 hour. Add strong acidic cation exchange resin Dowex50W (H + ) for neutralization, suction filtration, and after washing with methanol, the filtrate was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain 433mg (85.3%) of Compound 2.

[0056] Rf=0.36 (chloroform:methanol=5:1)

[0057] 1 HNMR (CD 3 OD)δ: 0.94(3H, s), 0.96-1.32(8H, m), 1.49(3H, s), 1.50-1.80(9H, m), 1.80-2.00(2H, m), 2.07-2.30(2H , m), 2.32-2.43(1H, m), 2.57-2.72(1H, m), 3.21-3.40(4H, m), 3.62-3.71(1H, m), 3.84-3.92(1H, m), 4.32 (1H, d, J = 7.8Hz), 4.36 (1H, d, J = 4, 2Hz), 4.54 (1H, d, J = 18.9Hz), 4.76 (1H, d, J = 18.9Hz), 4.84 ( ...

Embodiment 3

[0059] Synthesis of Compound 3 ( image 3 )

[0060] Synthesis of compound D: D-(+)-glucose (2.02g), acetic anhydride (10mL), 33wt% hydrogen bromide / acetic acid (2mL) were stirred overnight at room temperature and protected from light, and then 33wt% of Hydrogen bromide / acetic acid (10 mL) was stirred for 7 hours. Dichloromethane (50 mL) was added to the reaction liquid, and the mixture was poured into ice water (50 mL) for liquid separation. Extract the aqueous layer with dichloromethane (50mL×2), combine the dichloromethane layers, neutralize with aqueous sodium bicarbonate, wash with water, wash with brine, and dry (MgSO 4 ), and then concentrated under reduced pressure. Diisopropyl ether (6.5 g) was added to the concentrated residue (4.74 g), and compound D synthesized separately was inoculated. The solidified mass was crushed, collected by filtration, washed with diisopropyl ether, and dried under reduced pressure (room temperature) to obtain compound D (3.83 g, 83.1%...

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Abstract

A steroid compound of the Formula (1): [wherein R 1 represents a group selected from the group consisting of H, CH 3 , C 2 H 5 , C 3 H 7 and CH (CH 3 ) 2 , R 2 represents a group selected from NH 2 , NHAc and OCOR 1 , R 3 represents a group selected from the group consisting of CH 3 , COOCH 3 and CH 2 OCOR 1. ]

Description

technical field [0001] The present invention relates to a steroid compound. More specifically, the present invention relates to novel steroidal compounds having excellent pharmacological effects in which the 21-position of desmethylpropionyl-ciclesonide is substituted with an acylated monosaccharide. Background technique [0002] There are reports of prodrug steroids which themselves have no steroid-like activity but are converted into active forms at inflammatory sites (Non-Patent Document 1, Patent Document 1). However, although the compounds described in Non-Patent Document 1 and Patent Document 1 reduce the side effects of steroids, they are still insufficient. Therefore, a compound in which the hydroxyl group of a monosaccharide in a sugar-steroid compound is modified with a bulky protecting group was synthesized to suppress the release of the steroid compound to the outside of the inflammatory site and reduce side effects (Technical Document 2). Then, by replacing th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00A61K31/7048A61P1/04A61P11/06A61P17/00A61P19/02A61P27/14A61P27/16A61P29/00
CPCC07H15/24C07J71/0031A61P1/04A61P11/02A61P11/06A61P17/00A61P19/02A61P27/02A61P27/14A61P27/16A61P29/00
Inventor 石井隆幸
Owner MIKASA SEIYAKU
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