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Novel chemical synthesis method for preparing mecobalamine

A kind of methylcobalamin, a new type of technology, applied in the field of chemical synthesis for synthesizing methylcobalamin, can solve the problems of serious environmental pollution, difficult to remove, purchase and the like

Active Publication Date: 2013-05-22
SHANDONG INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The above several synthetic methods have some defects in varying degrees. Methods 1 and 2 all use highly toxic methylating reagents (methyl iodide, methyl p-toluenesulfonate), methods 3, 4, and 5 Some of the methylating reagents used cannot be purchased commercially on a large scale (monomethyl oxalate, dimethyl oxalate, methyl ammonium hexafluorosilicate), and some have serious environmental pollution (methylmercuric iodide). The methylating reagent used in Reaction 6 will produce methyl sulfide which is environmentally polluting during the reaction, and the dimethyl sulfoxide produced at the same time is extremely difficult to get from the reaction due to its high boiling point (189°C) and good compatibility with water. system, and easy to generate by-products in the methylation process
Method 7 has the disadvantages of low temperature crystallization yield loss, etc.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 1) Reductive methylation

[0031] In a 500ml glass reaction bottle, add 20g cyanocobalamin, 1.4g cobalt chloride hexahydrate, 250ml purified water according to the proportion, stir and cool to 10-15°C to dissolve, keep stirring at 10-15°C, start to drop and dissolve NaBH at the same time 4 Purified aqueous solution (6g / 60ml), methanol solution of formaldehyde (37-40% w / w) aqueous solution (40.5ml formaldehyde aqueous solution / 25.5ml methanol), after about 45 minutes, continue to react for 2 hours. After the reaction, use 36 Adjust the pH of the reaction liquid to 6.0 with % acetic acid, stir again for 15 minutes until the pH remains unchanged, then control the vacuum degree to -0.08 MPa, and distill under reduced pressure at a temperature below 40°C.

[0032] 2), elution

[0033] Adsorb the reaction solution with a macroporous resin column (macroporous resin model: Amberlite XAD-2), and wash repeatedly with purified water to remove inorganic salts. Subsequently, 20% a...

Embodiment 2

[0040] 1) Reductive methylation

[0041] In a 500ml glass reaction bottle, add 20g cyanocobalamin, 1.4g cobalt chloride hexahydrate, 250ml purified water according to the proportion, stir and cool to 10-15°C to dissolve, keep stirring at 10-15°C, start to drop and dissolve NaBH at the same time 4 Purified aqueous solution (8g / 80ml), formaldehyde solution (37-40% w / w) in methanol solution (54ml formaldehyde solution / 34ml methanol), drop it in about 1 hour, continue to react for 2 hours, after the reaction, use 36% Adjust the pH of the reaction solution to 6 with acetic acid, stir again for 15 minutes until the pH remains unchanged, then control the vacuum to -0.08 MPa, and distill under reduced pressure at a temperature below 40°C.

[0042] 2), elution

[0043] Adsorb the reaction solution with a macroporous resin column (macroporous resin model: Amberlite XAD-2), and wash repeatedly with purified water to remove inorganic salts. Subsequently, 20% acetone was added for elutio...

Embodiment 3

[0050] 1) Reductive methylation

[0051] In a 500ml glass reaction bottle, add 20g cyanocobalamin, 1.4g cobalt chloride hexahydrate, 250ml purified water according to the proportion, stir and cool to 10-15°C to dissolve, keep stirring at 10-15°C, start to drop and dissolve NaBH at the same time 4 Purified aqueous solution (10g / 100ml), formaldehyde solution (37-40% w / w) in methanol solution (67.5ml formaldehyde solution / 42.5ml methanol), drop it in about 1.5 hours, continue to react for 2 hours, after the reaction, use Adjust the pH of the reaction solution to 6 with 36% acetic acid, stir for 15 minutes and retest until the pH remains unchanged, then control the vacuum degree to -0.08 MPa, and distill under reduced pressure at a temperature below 40°C. .

[0052] 2), elution

[0053] Adsorb the reaction solution with a macroporous resin column (macroporous resin model: Amberlite XAD-2), and wash repeatedly with purified water to remove inorganic salts. Subsequently, 20% acet...

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Abstract

The invention discloses a novel chemical synthesis method for preparing mecobalamine. The novel chemical synthesis method comprises the steps of: dissolving cyanocobalamin and cobalt chloride hexahydrate in deionized water to obtain reaction liquid, simultaneously dropwise adding a sodium borohydride aqueous solution and a methanol / formaldehyde solution to the reaction liquid, and generating mecobalamine in one step through reductive methylation. According to the novel chemical synthesis method, the cyanocobalamin is taken as a raw material, and the mecobalamine is synthesized in one step; and therefore, the novel chemical synthesis method is simple in operation and has low requirements on equipment, little pollution and wide application prospect, and conditions are easy to control.

Description

technical field [0001] The invention relates to a novel chemical synthesis method for synthesizing methylcobalamin. Background technique [0002] Methylcobalamin (Methylcobalamin), chemical name: cobalt-α-[α-5,6-dimethylbenzimidazolyl]-cobalt-β-methylcobalamin amide, molecular formula: C63H91CoN13O14P, molecular weight: 1344.38, is a A dark red crystal or crystalline powder, odorless, tasteless, highly hygroscopic, and easily decomposed when exposed to light. Methylcobalamin is a coenzyme vitamin B developed by Eisai Co., Ltd. 12 , is mainly used in medicine to treat peripheral nerve diseases and vitamin B deficiency 12 caused by megaloblastic anemia, with other coenzyme B vitamins 12 Compared with similar drugs, methylcobalamin has good conductivity to nerve tissue, can smoothly enter nerve cells, promote nucleic acid, protein, and lipid metabolism, and repair damaged nerves by stimulating the regeneration of axons and sheaths. A more effective drug for treating periphe...

Claims

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Application Information

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IPC IPC(8): C07H23/00C07H1/00
Inventor 沈乃涛任业明赵思太冯光玲张雯段崇刚
Owner SHANDONG INST OF PHARMA IND
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