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Method for producing 3-(2,2,2-trimethylhydrazinium)propionate dihydrate

A technology of trimethylhydrazine and dihydrate, applied in the field of preparing pharmaceutically active compounds, can solve the problems of high production cost, not being used for drugs, the danger of unstable organic composition decomposition, etc.

Inactive Publication Date: 2009-09-23
GRINDEKS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has many disadvantages: strong base ion exchangers are unstable and undergo decomposition and oxidation when handled; they can only withstand a limited number of regeneration cycles; large amounts of solvents, acids and bases, and deionized water are required to regenerate the resin ; by this method the low ion exchange capacity of compound (1) and the resulting high production costs are typical
Although this method can be used for inorganic salts, it is not used for pharmaceuticals due to the risk of decomposition of unstable organic components

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Suspend 66.8g of KOH (90% of the main substance content) in 450ml of ethanol, and add 120.5g of 3-(2,2,2-trimethylhydrazine) within 5-10 minutes under stirring at 18-20°C Methyl propionate bromide. Stirring was continued at 18-20°C until ester saponification was complete (controlled by TLC). The mixture was then cooled to 2-4 °C and washed with CO 2 Saturated to pH 8.1-8.5. The precipitate thus formed was filtered off, washed with 3 x 20 ml ethanol and the combined filtrates were evaporated. 89 g (92%) of a semi-crystalline solid (3-(2,2,2-trimethylhydrazine)propionate content 94%) are obtained. Crystallization from ethanol or 2-propanol or another suitable solvent affords 3-(2,2,2-trimethylhydrazine)propionate dihydrate (>99.5% pure) with a melting point of 85-87°C .

Embodiment 2

[0023] Suspend 34.0g KOH (90% main substance content) in 450ml ethanol, and add 120.5g of 3-(2,2,2-trimethylhydrazine) within 5-10 minutes under stirring at 18-20°C Methyl propionate bromide. Stirring was continued at 18-20°C until ester saponification was complete (controlled by TLC). The mixture was then cooled to 2-4 °C and washed with CO 2Saturated to pH 8.1-8.5. The precipitate thus formed was filtered off, washed with 3 x 20 ml ethanol and the combined filtrates were evaporated. 90 g (93%) of a semi-crystalline solid (3-(2,2,2-trimethylhydrazine)propionate content 93%) are obtained. Crystallization from ethanol or 2-propanol or another suitable solvent affords 3-(2,2,2-trimethylhydrazine)propionate dihydrate (>99.5% pure) with a melting point of 85-87°C .

Embodiment 3

[0025] Suspend 66g of KOH (90% main substance content) in 450ml of ethanol, and add 136g of 3-(2,2,2-trimethylhydrazine) propionic acid within 5-10 minutes under stirring at 18-20°C Methyl Sulfate. Stirring was continued at 18-20°C until ester saponification was complete (controlled by TLC). The mixture was then cooled to 2-4 °C and washed with CO 2 Saturated to pH 8.1-8.5. The precipitate thus formed was filtered off, washed with 3 x 10 ml ethanol and the combined filtrates were evaporated. 89.5 g (89%) of semi-crystalline solid were obtained. Crystallization from ethanol or 2-propanol or another suitable solvent affords 3-(2,2,2-trimethylhydrazine)propionate dihydrate (>99.5% pure) with a melting point of 85-87°C .

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Abstract

A method for producing 3-(2,2,2-trimethylhydrazinium)propionate dihydrate by saponification of salts of 3-(2,2,2-trimethylhydrazinium)propionate esters with subsequent purification step using saturation with carbon dioxide or sulphur dioxide in alcoholic solution.

Description

technical field [0001] The present invention relates to the preparation of pharmaceutically active compounds, namely the pharmaceutically active substance 3-(2,2,2-trimethylhydrazine) propionate dihydrate, the known drug medolium of formula (1) (Meldonium) (INN) method. [0002] (CH 3 ) 3 N + NHCH 2 CH 2 COO - .2H 2 O(1) Background technique [0003] Medolonium is a cardiovascular drug with an average daily dose of 1.0 g. Since this formulation is used as an over-the-counter drug, there is a need for inexpensive mass production methods. The known methods for preparing medodonium are not convenient for large-scale production. [0004] It was therefore the object of the present invention to improve the hitherto known process for producing medodonium in such a way that it is less expensive to produce and can be applied to large-scale production. [0005] A wide variety of methods are known for the preparation of compounds of formula (1). The usual scheme used so far...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C241/02C07C243/40
CPCC07C2529/40C07C1/26C07C17/10C07C9/00C07C19/075
Inventor 乔治·席尔瓦
Owner GRINDEKS
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