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Sinomenine derivatives and preparation and uses thereof

A technology of sinomenine and compound, which is applied in the field of preparation and application of sinomenine derivatives, and can solve problems such as low yield and the like

Inactive Publication Date: 2009-11-11
NATUREMED GROUP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, they have had little effect in increasing the activity of sinomenine

Method used

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  • Sinomenine derivatives and preparation and uses thereof
  • Sinomenine derivatives and preparation and uses thereof
  • Sinomenine derivatives and preparation and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0050] The preparation of example 1 17-demethylbenzyloxybenzyloxy sinomenine

[0051] The first step: preparation of benzyloxybenzyloxysinomenine (Hitotsuyanagi, Y.; Nishimura, K.; Ikuta, H.; Takeya, K.; Itokawa, H.J.Org.Chem., 1995, 60 (14), 4549-58.)

[0052]

[0053] Sinomenine (1.65g, 5mmol), PPh 3 (3.93g, 15mmol), BnOBnOH (3.17g, mmol) and anhydrous THF (50ml) were mixed in a 25ml 4-neck round bottom flask equipped with a magnetic stirring ladle and stirred. The reaction mixture was cooled with ice, and DEAD (2.61 g, 15 mmol) was slowly added dropwise over 30 minutes. After the addition, it was stirred at room temperature for 12 hours. The THF was spun off to leave a residue, which was purified through a silica gel column (ethyl acetate, then methanol) to obtain a flesh-colored solid. A white powder (2.6 g) was obtained by recrystallization of isopropyl ether. mp 72°C; [α] 25 D -69.0° (c=0.28CHCl 3 ); 1 HNMR (300MHz, CDCl 3 )δ: 7.56 (d, 2H, J = 8.6Hz.), 7.48-7....

example 2

[0058] Example 2 Preparation of 17-propanesulfonylsinomenine

[0059]

[0060] first step:

[0061] In a solution of 17-desmethylbenzyloxybenzyloxysinomenine (100mg) and dichloromethane (10ml) containing triethylamine, slowly add propanesulfone containing dichloromethane (5ml) under stirring acid chloride (50 mg) solution. Stirred for 5 minutes, the reaction mixture was evaporated under reduced pressure to obtain a residue, and the residue was refined with a silica gel column (ethyl acetate / petroleum ether at a volume ratio of 1:2) to obtain 17-propanesulfonylbenzyloxybenzyloxy ivy alkali. [α] 25 D +210.5°(c=0.06CHCl 3 ); 1 HNMR (300MHz, DCCl 3 )δ: 7.56(d, 1H, J=8.7Hz), 7.48-7.34(m, 4H), 7.03(d, 1H, J=8.7Hz), 6.81(d, 1H, J=8.7Hz), 6.78( d, 1H, J=8.7Hz), 5.47(s, 1H), 5.27(d, 1H, J=10.5Hz), 5.11(s, 1H), 5.01(d, 1H, J=10.5Hz), 4.37( s, 1H), 4.21(d, 1H, J=15.9Hz), 3.85(s, 3H), 3.53(s, 3H), 3.52-3.44(m, 1H), 3.28-3.20(m, 1H), 2.97 -2.85(m, 4H), 2.74-2.55(m, 1H), 2.47(d...

example 3

[0065] Example 3 Preparation of 17-p-toluenesulfonyl sinomenine

[0066]

[0067] first step:

[0068] In a mixture of 17-desmethylbenzyloxybenzyloxysinomenine (100mg) and triethylamine (0.1ml) in dichloromethane (10ml), add 5ml of dichloromethane containing 30mg of p-toluenesulfonyl chloride dropwise methane solution. Mix and stir at room temperature for 10 minutes, and then evaporate under reduced pressure to obtain a crude product of 17-p-toluenesulfonylbenzyloxybenzyloxysinomenine, which can be directly used in the next reaction without purification.

[0069]

[0070] Step two:

[0071] 100mg of 17-p-toluenesulfonylbenzyloxybenzyloxysinomenine obtained in the first step of this example, as shown in the second step in Example 2, after adding 10ml of 5% TFA / DCM solution, can produce 50 mg of 17-p-toluenesulfonyl sinomenine. mp 141.0-143.0°C; [α] 10 D +92.4°(c=0.49CHCl 3 ); 1 HNMR (300MHz, DCCl 3 )δ: 7.74(d, 2H, J=7.6Hz.), 7.33(d, 2H, J=7.6Hz.), 6.62(d, 1H, J=8...

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Abstract

The present invention relates to the preparation and pharmacological use of sinomenine derivatives of formula I . The approach disclosed herein is the modification of D ring by- substituting for R. Additional substitutions in the other rings are also provided herein. Several of the sinomenine derivatives have significantly greater anti-inflammation activity when compared with the parent compound.

Description

[0001] This patent application is based on Chinese Patent Application No. 200610038862.9 (filed on March 15, 2006), Chinese Patent Application No. 200510123089.1 (filed on December 15, 2005), Chinese Patent Application No. 200510123090.4 (filed on 2005 Submitted on December 15) priority. , we have combined the above 3 patent contents into this patent application. [0002] In this patent application, we refer to and quote numerous documents in order to fully and clearly explain the level of the present invention. technical field [0003] The present invention relates to the preparation and application of a compound, especially the preparation and application of sinomenine derivatives. Background technique [0004] The inflammatory response is a part of the body's defense in order to restore and maintain the structure and function of the tissue after the body is injured. Most of the body's defense substances are in the blood. Inflammation refers specifically to the process ...

Claims

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Application Information

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IPC IPC(8): A61K31/485C07D221/28
Inventor 王捷
Owner NATUREMED GROUP CORP
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