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Method for preparing azo onium diol sodium salt

A technology of azonium glycol sodium salt and sodium methoxide, applied in the field of preparing azonium glycol sodium salt, can solve the problems of high equipment requirements, unfavorable large-scale production, inconvenient operation and the like

Inactive Publication Date: 2008-07-30
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because NO gas has a strong corrosive effect, stainless steel autoclaves and corresponding supporting facilities are required, so the requirements for equipment are relatively high, and the operation is inconvenient, which is not conducive to large-scale production

Method used

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  • Method for preparing azo onium diol sodium salt

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Preparation of Sodium Salt of Diethylaminoazonium Diol

[0029] In a 100mL three-necked flask device, add diethylamine (0.01mol), 50mL of anhydrous ether, 50mg of zeolite, 3.2mL of 25% sodium methoxide methanol solution, and use N 2 Replace the air in the reaction bottle for 3 times, and then replace the N in the reaction bottle with NO gas 2 3 times. Slowly introduce NO gas under stirring, and react at room temperature for 48h. Close the valve of the NO gas cylinder, pump out the remaining NO gas under reduced pressure, filter, wash the filter cake with 50 mL of ether, and dry in vacuo to obtain a crude product, which is dissolved in 10 mL of anhydrous methanol, filtered three times with a 0.22 μm organic filter membrane, and kept at room temperature Methanol was removed under reduced pressure and dried in vacuo to obtain a white solid powder, m.p.196-199°C, yield 34% [reported yield 26%, Bioorg.Med.Chem, 2007, 15: 6796-6801]. 1 H NMR (300MHz, D 2 O) δ: 1.12(t, J=...

Embodiment 2

[0031] Preparation of Sodium Salt of Pyrrolidinium Azonium Diol

[0032]In a 250mL three-necked flask device, add pyrrolidine (0.02mol), anhydrous ether 100mL, TiO 2 100mg, 6.4mL of 25% sodium methoxide in methanol. use N 2 Replace the air in the reaction device for 3 times, and then replace the N in the reaction device with NO gas 2 3 times. Slowly introduce NO gas under stirring, and react at room temperature for 48h. Close the valve of the NO gas cylinder, pump out the remaining NO gas, filter, wash the filter cake with 100mL ether, and dry it in vacuum. Redissolve in 20mL of anhydrous methanol, filter 3 times through a 0.22 μm organic filter, remove methanol under reduced pressure, and dry in vacuo to obtain a white solid powder, m.p.168-171°C, yield 89.5% [reported yield 54%, J . Med. Chem. 1997, 40(13): 1947-1954]. 1 H NMR (D 2 (2, 300 MHz) δ: 2.99 (m, 4H), 1.68 (m, 4H).

Embodiment 3

[0034] Preparation of piperidinium azonium diol sodium salt

[0035] In a 250mL three-necked flask device, add piperidine (0.03mol), anhydrous ether 150mL, TiO 2 150mg, 9.6mL of 25% sodium methoxide in methanol. use N 2 Replace the air in the reaction device for 3 times, and then replace the N in the reaction device with NO gas 2 3 times. Slowly introduce NO gas under stirring, and react at room temperature for 48h. Close the valve of the NO gas cylinder, pump out the unreacted NO gas, filter, wash the filter cake with 150mL ether, and dry it in vacuum. Redissolve in 30 mL of anhydrous methanol, filter 3 times through a 0.22 μm organic filter, remove methanol under reduced pressure, and dry in vacuo to obtain a white solid powder, m.p.277 ° C, yield 89.4% [yield 70%, J.Am.Chem .Soc.1961, 83:1819-1822]. 1 H NMR (D 2 (2, 300 MHz) δ: 3.10 (m, 4H), 1.53-1.59 (m, 6H). ,

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Abstract

The invention relates to the field of the medicinal chemistry and in particular relates to a method for preparing azo onium diol sodium salt. The invention is characterized in that: the primary amine or secondary amine reacts with nitric oxide and sodium methoxide / methanol solution under catalysis of NO gas adsorbent. The preparation method of the invention does not need autoclave and the corresponding equipment. The invention shows simple operation and lower cost with good safety, and is suitable for industrialized production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a method for preparing sodium azonium diol. technical background [0002] Azonium diol sodium salt (see below for the structure, wherein the O connected to the azonium ion is O 1 , the O attached to the nitrogen atom is O 2 ) is a very important nitric oxide (NO) donor, which is particularly prominent in the selective release of NO and its targeting effect. It is known that the anion form (NONOate) of the sodium salt of azonium diol is unstable under physiological conditions (pH 7.4, 37 ° C), and it is easy to release NO, with a half-life ranging from a few minutes to a few hours; but once O 2 When protected, a stable prodrug is formed, and the half-life can be extended to tens of hours. Under the action of a specific enzyme, the prodrug can selectively release NO, thereby exerting a targeting effect. For example, the O 2 with -CH 2 OAc connection, the product can exist s...

Claims

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Application Information

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IPC IPC(8): C07C291/08C07D295/28
Inventor 张奕华黄张建赖宜生丁晔彭司勋
Owner CHINA PHARM UNIV
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