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A kind of preparation method of balsalazide sodium

A technology of balsalazide sodium and balsalazide, which is applied in the field of medicine, can solve the problems of reducing operational risk, high adsorption capacity of activated carbon, and increasing production costs, and achieves reduced production costs and environmental pollution, mild reaction conditions, and improved production efficiency. safety effect

Inactive Publication Date: 2017-11-14
辽宁省药物研究院
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Problems solved by technology

[0009] Although the reduction reaction step in this method replaces the high temperature and high pressure hydrogenation reaction method, which reduces the risk of operation, the method uses FeCl 3 ·6H 2 O / activated carbon is the catalyst, and the active ingredient of the catalyst is FeCl 3 ·6H 2 O, the role of activated carbon is as FeCl 3 ·6H 2 The carrier of O, however, the adsorption of activated carbon is very large, and the reaction product will also be adsorbed on the activated carbon, which is difficult to separate, resulting in a decrease in yield, and adding activated carbon also increases the production cost; the method is carried out at the reflux temperature of ethanol, and the reaction The time is 4 hours, the reaction temperature is higher, and the reaction time is also longer

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  • A kind of preparation method of balsalazide sodium
  • A kind of preparation method of balsalazide sodium
  • A kind of preparation method of balsalazide sodium

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Embodiment 1

[0046] The preparation of embodiment 1, balsalazide sodium

[0047] (1) Dissolve 50g of β-alanine in 500ml of sodium hydroxide aqueous solution, then add 100g of p-nitrobenzoyl chloride, and react for 2 hours under stirring, then filter, wash with water, and vacuum dry the dried product with acetone Recrystallized to obtain p-nitrobenzoyl-β-alanine with a yield of 84.3%, mp: 163-164°C;

[0048] (2) Add 40g of the p-nitrobenzoyl-β-alanine obtained in step 1) and 100ml of solvent water to the reactor, dissolve and add the catalyst FeCl at room temperature 3 ·6H 2 O reacted with reducing agent hydrazine hydrate for 2 hours, in which the catalyst FeCl 3 ·6H 2 The amount of O is 2.5% of the mass of p-nitrobenzoyl-β-alanine, and the molar ratio of p-nitrobenzoyl-β-alanine to hydrazine hydrate is 1:2.5; then adjust the pH value with hydrochloric acid to 1-2, filtered, washed with water, and dried to obtain p-aminobenzoyl-β-alanine with a yield of 90.4%, mp: 154-156°C, and a purit...

Embodiment 2

[0054] The preparation of embodiment 2, balsalazide sodium

[0055] (1) Dissolve 90g of β-alanine in 500ml of sodium hydroxide aqueous solution, then add 150g of p-nitrobenzoyl chloride; react for 4 hours under stirring, then filter, wash with water, and dry in vacuum. The dried product is washed with acetone Recrystallized to obtain p-nitrobenzoyl-β-alanine with a yield of 82.5%, mp: 163-164°C;

[0056] (2) Add 40g of the p-nitrobenzoyl-β-alanine obtained in step 1) and 100ml of solvent water to the reactor, dissolve and add the catalyst FeCl at room temperature 3 ·6H 2 O reacted with reducing agent hydrazine hydrate for 1 hour, in which the catalyst FeCl 3 ·6H 2 The amount of O is 2.0% of the mass of p-nitrobenzoyl-β-alanine, and the molar ratio of p-nitrobenzoyl-β-alanine to hydrazine hydrate is 1:1.5; then adjust the pH value with hydrochloric acid to 1-2, filtered, washed with water, and dried to obtain p-aminobenzoyl-β-alanine with a yield of 89.9%, mp: 154-156°C, an...

Embodiment 3

[0060] Embodiment 3, the preparation of balsalazide sodium

[0061] (1) Dissolve 60g of β-alanine in 500ml of sodium hydroxide aqueous solution, then add 120g of p-nitrobenzoyl chloride; stir for 3 hours, then filter, wash with water, and vacuum dry the dried product with acetone Recrystallized to obtain p-nitrobenzoyl-β-alanine with a yield of 80.1%;

[0062] (2) Add 40g of the p-nitrobenzoyl-β-alanine obtained in step 1) and 100ml of solvent water to the reactor, dissolve and add the catalyst FeCl at room temperature 3 ·6H 2 O reacted with reducing agent hydrazine hydrate for 2.5 hours, wherein the catalyst FeCl 3 ·6H 2 The amount of O is 3.0% of the mass of p-nitrobenzoyl-β-alanine, and the molar ratio of p-nitrobenzoyl-β-alanine to hydrazine hydrate is 1:3; then adjust the pH value with hydrochloric acid to 1-2, filtered, washed with water, and dried to obtain p-aminobenzoyl-β-alanine with a yield of 89.9%, mp: 154-156°C, and a purity (HPLC) greater than 98.0%;

[006...

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Abstract

The invention relates to a preparation method of balsalazide disodium, which includes following steps: (1) with paranitrobenzoyl chloride as a raw material, performing a reaction with [beta]-alanine in a NaOH water solution to obtain paranitrobenzoyl-[beta]-alanine; (2) with hydrazine hydrate as a reduction agent, FeCl3.6H2O as a catalyst and water as a solvent, performing a reduction to the paranitrobenzoyl-[beta]-alanine to obtain paraminobenzoyl-[beta]-alanine; (3) performing a diazo-reaction and a coupling reaction to the paraminobenzoyl-[beta]-alanine to obtain balsalazide acid; and (4) performing a salt forming reaction to the balsalazide acid to obtain balsalazide disodium. In the invention, the reduction reaction is carried out with hydrazine hydrate as the reduction agent, FeCl3.6H2O as the catalyst and water as the solvent, so that an expensive Pd-C catalyst is replaced and usage of hydrogen is canceled, so that the preparation method is greatly improved in operation safety and reduced in synthetic cost.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a preparation method of balsalazide sodium. Background technique [0002] Balsalazide disodium, alias: balsalazide disodium; scientific name: 5-[4-[[(2-carboxyethyl)carbamoyl]phenylazo]salicylic acid disodium salt dihydrate substance, molecular formula C 17 h 13 N 3 Na 2 o 6 2H 2 O, molecular weight: 437.31, CAS number: 150399-21-6, the structural formula is as follows: [0003] [0004] Balsalazide sodium was first successfully developed by Astra Company in Sweden. It was first launched in the UK in 1997 and is currently widely used in countries such as the UK, Italy, Austria, Belgium, Denmark and Luxembourg. Compared with similar drugs, it has the characteristics of quick onset, good curative effect and few side effects. [0005] Balsalazide sodium is a 5-aminosalicylic acid compound, which belongs to the prodrug preparation of 5-aminosalicylic acid. After oral administration...

Claims

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Application Information

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IPC IPC(8): C07C245/08C07C237/36C07C231/12
Inventor 贾卫茹赵鑫张勇吴云飞周阳
Owner 辽宁省药物研究院
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