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Erythromycylamine preparation method

A technology for erythromycin and a compound, which is applied in the field of preparing erythromycin, can solve the problems of relatively high pH requirements, difficult preparation and use, increased cost, etc., and achieves the effects of high product content, easy procurement, and convenient post-processing.

Inactive Publication Date: 2015-08-26
HEADING NANJING PHARMTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 2. Wildsmith, etc. use aluminum amalgam and zinc amalgam for reduction, which is very polluting and difficult to prepare and use
The production of by-products is reduced, and the stability of the synthesis method is relatively good, but the post-processing is extracted and separated for many times, which increases the cost and requires relatively high pH.

Method used

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  • Erythromycylamine preparation method
  • Erythromycylamine preparation method
  • Erythromycylamine preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045]

[0046] Dissolve 1 (3.99kg, 5.22mol) in methanol (20L), add hydrazine hydrate 80% aqueous solution (1.63kg 26.1mol), calcium oxide (1.31kg 23.37mol), stir at room temperature for 16h, then add Water, precipitated solid 2, suction filtered, and dried solid 2 at 40-50°C to obtain 4kg, yield 95%, purity 94.65%, see figure 1 .

[0047] Dissolve 2 (4kg 4.96mol) in methanol (40L), add sodium nitrite (3.42kg 49.6mol) and water (4kg) in turn, and stir at room temperature for 30 minutes. Control -10°C, add 3N hydrochloric acid (20L) dropwise, and control the pH=2.5~3, adjust the pH=2.5~3 with a small amount of 1N hydrochloric acid after dropping, extract with dichloromethane (12L*2), use 15% hydrogen in the water phase Sodium oxide (8L) was used to adjust the pH to 9.2-9.8, extracted with L dichloromethane (12L*2), and the organic phase was washed once with water (2L) at an external temperature of 35°C, and concentrated until no distillate was produced to obtain 3. Cool do...

Embodiment 2

[0049]

[0050] Dissolve 1 (1kg, 1.31mol) in methanol (5L), add hydrazine hydrate 80% aqueous solution (0.39kg 7.86mol), calcium oxide (0.59kg 10.48mol), stir at room temperature for 16h, add water under rapid stirring, The solid 2 was precipitated, filtered with suction, and the solid 2 was dried at 40-50° C. to obtain 1 kg with a yield of 95% and a purity of 95%.

[0051]Dissolve 2 (1kg 1.24mol) in methanol (10L), add sodium nitrite (0.856kg 12.4mol) and water (1kg) in turn, and stir at room temperature for 30 minutes. Control -10°C, add 3N hydrochloric acid (5L) dropwise, and control the pH=2.5~3, adjust the pH=2.5~3 with a small amount of 1N hydrochloric acid after dropping, extract with dichloromethane (3L*2), use 15% hydrogen in the water phase Sodium oxide (2L) was used to adjust the pH to 9.2-9.8, extracted with dichloromethane (3L*2), the organic phase was washed once with water (2L) at an external temperature of 35°C, and concentrated until no distillate appeared ...

Embodiment 3

[0054]

[0055] Dissolve 1 (10kg, 13.1mol) in methanol (20L), add hydrazine hydrate 80% aqueous solution (4.1kg 65.5mol), calcium oxide (3.3kg 58.6mol), stir at room temperature for 16h, add water under rapid stirring, Solid 2 was precipitated, filtered with suction, and dried at 40-50° C. to obtain 10.02 kg with a yield of 95% and a purity of 95%.

[0056] Dissolve 2 (10.02kg 12.42mol) in methanol (100L), add sodium nitrite (12.8kg 186mol) and water (10kg) in turn, and stir at room temperature for 30 minutes. Control -10°C, add 3N hydrochloric acid (50L) dropwise, and control the pH=2.5~3, adjust the pH=2.5~3 with a small amount of 1N hydrochloric acid after dropping, extract with dichloromethane (30L*2), use 15% hydrogen in the water phase Sodium oxide (20L) was used to adjust the pH to 9.2-9.8, extracted with L dichloromethane (30L*2), the organic phase was washed once with water (5L) at an external temperature of 35°C, and concentrated until no distillate was produced t...

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Abstract

The invention discloses an erythromycylamine preparation method and relates to the field of drug preparation. Erythromycylamine is synthesized through three steps of reduction reaction, diazo reaction and re-reduction reaction. In the first step, hydrazine hydrate is used for reduction, and accordingly, no by-product isomer is produced, and the product yield is high; in the second step, the intermediate imide can be separated effectively by adjusting acid alkali, and reduction can be performed continuously without decomposing out raw materials; in the third step, sodium borohydride is used for reduction, so that the yield is high, aftertreatment can be performed conveniently, and the product content is high. Calcium oxide is used for removing water, moisture generated through the reaction can be removed, and accordingly, the reaction can be performed rightwards constantly, and the productivity is high. The whole process route is simple, the raw materials are easy to purchase, the cost is low, the operation can be performed conveniently, the yield is high, and the purity and the content of the prepared erythromycylamine are high.

Description

Technical field: [0001] The invention relates to the field of medicine preparation, in particular to a method for preparing erythromycin. Background technique: [0002] The purposes and existing market of dirithromycin: erythromycin is an effective intermediate for preparing dirithromycin. Dirithromycin is obtained by docking with side chains from erythromycin. The antibacterial spectrum of dirithromycin is similar to that of erythromycin, and it has better pharmacokinetic properties than erythromycin: (1) stable to acid and less irritating to the stomach; (2) long elimination half-life after oral administration (32.5 ±1.8) hours, 1.2 hours for erythromycin; (3) The tissue concentration is 20-40 times higher than the plasma concentration in the same period (erythromycin is only 1-12 times higher); (4) After non-enzymatic hydrolysis in the body, it rapidly It is converted into erythromycin with the same activity, does not produce inactive metabolites (metabolites with low t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/08C07H1/00
CPCC07H17/08C07H1/00
Inventor 李文森
Owner HEADING NANJING PHARMTECH CO LTD
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