Prepn process of 5-losartan carboxylate

The technology of losartan carboxylate and formic acid is applied in the field of preparation of 5-carboxylate losartan, which can solve the problems of containing many impurities, being difficult to industrialize production, and failing to meet product purity requirements well, and achieving a simple process. Effect

Inactive Publication Date: 2007-03-21
NANJING UNIV OF AERONAUTICS & ASTRONAUTICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In the above two methods, the chromatographic method is used for separation, which shows that the product contains more impurities and cannot meet the purity requirements of the product well.
At the same time, it is difficult to use chromatographic methods for industrial production

Method used

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  • Prepn process of 5-losartan carboxylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Example 1: 500 ml of distilled water and 0.25 mol of potassium permanganate were added to a 2000 ml three-neck flask protected by nitrogen and mechanically stirred. 0.30 mol of tetrabutylamine chloride was divided into four equal portions and added over 20 minutes. After stirring for 30 minutes, 1000 ml of pyridine was added. After stirring for 15 minutes, the insoluble matter was filtered off. The filtrate was put back into the original three-neck flask with nitrogen protection and mechanical stirring. Heat to forty degrees. 0.1 mol of the compound of formula (I) was added in portions within 30 minutes. Keep the reaction temperature below fifty degrees. After stirring for one hour, 30% aqueous formaldehyde (200ml) was added. Stir until the red color of the reaction subsides. The reaction formed a large brown precipitate which was filtered. The solid was washed three times with 100 ml of 1M NaOH solution. The almost colorless filtrate was concentrated to one thi...

Embodiment 2

[0012] Example 2: 250 ml of distilled water and 0.25 mol of potassium permanganate were added to a 2000 ml three-neck flask protected by nitrogen and mechanically stirred. 0.30 mol of tetrabutylamine chloride was divided into four equal portions and added over 20 minutes. After stirring for 30 minutes, 1000 ml of pyridine was added. After stirring for 15 minutes, the insoluble matter was filtered off. The filtrate was put back into the original three-neck flask with nitrogen protection and mechanical stirring. Heat to seventy degrees. 0.1 mol of the potassium salt of the compound of formula (I) was added in portions within 30 minutes. Keep the reaction temperature below eighty degrees. After stirring for one hour, 30% aqueous formaldehyde (200ml) was added. Stir until the red color of the reaction subsides. The reaction formed a large brown precipitate which was filtered. The solid was washed three times with 100 ml of 1M NaOH solution. The almost colorless filtrate wa...

Embodiment 3

[0013] Example 3: 500 ml of distilled water and 0.25 mol of potassium permanganate were added to a 2000 ml three-neck flask protected by nitrogen and mechanically stirred. 0.30 mol of tetrabutylamine chloride was divided into four equal portions and added over 20 minutes. After stirring for 30 minutes, 1000 ml of dimethylformamide were added. After stirring for 15 minutes, the insoluble matter was filtered off. The filtrate was put back into the original three-neck flask with nitrogen protection and mechanical stirring. 0.1 mol of the potassium salt of the compound of formula (I) was added in portions within 30 minutes. Keep the reaction temperature below twenty degrees. After stirring for ten hours, 30% aqueous formaldehyde (200 ml) was added. Stir until the red color of the reaction subsides. The reaction formed a large brown precipitate which was filtered. The solid was washed three times with 100 ml of 1M NaOH solution. The almost colorless filtrate was concentrated...

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Abstract

The present invention discloses preparation process of 5-losartan carboxylate. In polar solvent, such as DMF, pyridine, acetone, the mixed solvent with water, etc, losartan or its ammonium salt, alkali metal salt, hydrochloride, sulfate, formate, etc and the organic salt or inorganic salt of permanganic acid react to produce 5-losartan carboxylate or its ammonium salt, alkali metal salt, hydrochloride, sulfate, formate, etc. The preparation process is direct, economic, efficient and suitable for industrial production.

Description

1. Technical field [0001] The invention relates to a preparation method of an active metabolite of the antihypertensive drug losartan—losartan 5-carboxylate. 2. Background technology [0002] Losartan (formula (I)) can inhibit the activity of angiotensin II (angiotension II), so it can effectively alleviate the hypertension caused by angiotensin. In addition, because losartan can reduce the total cholesterol, it is suitable for treating high blood pressure Cholesterol also has a certain effect. In fact, it has been confirmed that losartan mainly works through its active metabolite in the human body—the 5-carboxylic acid metabolite EXP-3174 (formula (II)). EXP-3174 The activity is 10-40 times that of losartan, and its half-life is longer (6-9 hours, losartan is about 1 hour). It may become a new and more effective antihypertensive drug. Knowing that 5-carboxylate losartan After the importance of sartan, it is very important to explore the synthetic method that can be used to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10C07D233/00C07D257/00
CPCC07D403/10
Inventor 陈礼勤李健
Owner NANJING UNIV OF AERONAUTICS & ASTRONAUTICS
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