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Method for preparing ecabet sodium

A technology of ecabet sodium and sodium salt, which is applied in the field of preparation of ecabet sodium, an anti-digestive ulcer drug, can solve the problems of low selectivity and low yield, and achieve simple and easy-to-obtain raw materials and high yield. High, complete sulfonation conversion effect

Active Publication Date: 2014-10-08
CHONGQING KANGLE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In the preparation method of ecabet sodium disclosed above, due to some insufficient factors such as low yield and low selectivity, qualified samples must be refined many times.

Method used

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  • Method for preparing ecabet sodium
  • Method for preparing ecabet sodium
  • Method for preparing ecabet sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1.1 Preparation of 12-sulfonic acid dehydroabietic acid (II)

[0029] Add compound (III) (100 g, 0.333 mol) into 20% oleum (399.6 g, containing 0.999 mol of sulfur trioxide) pre-cooled to 3°C to 10°C, stir and react for 1.5 to 2 hours, then pour into 1000 g of ice In water, a large amount of off-white precipitates were precipitated, filtered, and the filter cake was dried under reduced pressure to obtain compound (II) off-white solid (HPLC purity>99.0%, yield 91%).

[0030] 1.2 Preparation of ecabet sodium (I)

[0031] Compound (II) (80g, 0.210mol) was added to an aqueous solution of 25% sodium isooctanoate (36.6g, 0.221mol) as a sodium forming agent, stirred and reacted for 0.5-1h, heated up, and filtered after dissolving and clarifying. Cool the filtrate in an ice-water bath to 0°C to 10°C, a large amount of white solids are precipitated, filter, and dry the filter cake under reduced pressure to obtain (I) white solid (specific rotation+72°, moisture 18.06%, HPLC pur...

Embodiment 2

[0033] 2.1 Preparation of 12-sulfonic acid dehydroabietic acid (II)

[0034] Add compound (III) (100 g, 0.333 mol) into 20% oleum (133.2 g, containing 0.333 mol of sulfur trioxide) pre-cooled to 3°C to 10°C, stir and react for 1.5 to 2 hours, then pour into 1000 g of ice In water, a large amount of off-white precipitates were precipitated, filtered, and the filter cake was dried under reduced pressure to obtain compound (II) off-white solid (HPLC purity>99.0%, yield 85%).

[0035] 2.2 Preparation of ecabet sodium (I)

[0036] Compound (II) (80 g, 0.210 mol) was added to an aqueous solution of sodium forming agent 25% sodium isooctanoate (17.55 g, 0.105 mol), stirred for 0.5 to 1 h, heated to raise the temperature, and filtered after being dissolved and clarified. Cool the filtrate in an ice-water bath to 0°C to 10°C, a large amount of white solids are precipitated, filter, and dry the filter cake under reduced pressure to obtain (1) white solid (specific rotation+70°, moistur...

Embodiment 3

[0038] 3.1 Preparation of 12-sulfonic acid dehydroabietic acid (II)

[0039] Add compound (III) (100g, 0.333mol) into 20% oleum (666g, containing 1.665mol of sulfur trioxide) pre-cooled to 3°C-10°C, stir for 1.5-2h, then pour into 1000g of ice water , a large amount of off-white precipitates were precipitated, filtered, and the filter cake was dried under reduced pressure to obtain compound (II) off-white solid (HPLC purity>98.0%, yield 88%).

[0040] 3.2 Preparation of ecabet sodium (I)

[0041]Compound (II) (80 g, 0.210 mol) was added to an aqueous solution of 25% sodium isooctanoate (70.2 g, 0.420 mol) as a sodium forming agent, stirred for 0.5 to 1 h, heated to raise the temperature, and filtered after being dissolved and clarified. Cool the filtrate in an ice-water bath to 0°C to 10°C, a large amount of white solids are precipitated, filter, and dry the filter cake under reduced pressure to obtain (1) white solid (specific rotation+71°, moisture 18.35%, HPLC purity>99.0%...

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Abstract

The invention discloses a method for preparing ecabet sodium. The method disclosed by the invention is characterized by comprising the following steps of carrying out sulfonation reaction on dehydroabietic acid (formula III) as a starting material and fuming sulfuric acid to obtain 12-sulfonic dehydroabietic acid (formula II) and enabling the compound shown as the formula II and a sodium-forming agent to form a sodium salt in a solvent system at least containing water to obtain ecabet sodium. By virtue of the method disclosed by the invention, the deficiencies of the prior art are overcome and the method has the advantage of high sulfonation yield and high selectivity in sodium salt forming, simple operation, safety and environment friendliness and is suitable for industrial production.

Description

Technical field: [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to a preparation method of ecabet sodium, an anti-digestive ulcer medicine. Background technique: [0002] Anti-peptic ulcer drug Ecabet Sodium (Ecabet Sodium, see formula I), chemical name is (+)-(1R, 4aS, 10aR)-1,2,3,4a,9,10,10a-octahydro -1,4a-Dimethyl-7-(1-methylethyl)-6-sulfonic acid-1-phenanthrene carboxylic acid-6-sodium salt pentahydrate, the English name is (+)-(1R,4aS , 10aR)-1, 2, 3, 4a, 9, 10, 10a-octahydro-1, 4a-dimethyl-7-(1-methylethyl)-6-sulfo-1-Phenanthrenecarboxylic acid-6-monosodium salt pentahydrate, which belongs to Antacid drugs with special curative effect can be widely used for gastric ulcer, and have protective effect on gastric mucosal injury between acute gastritis and chronic gastritis. The drug was first reported in the journals of the American Chemical Society in the 1930s. In the 1980s, Japan’s Tanabe Pharmaceutica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/58C07C303/32
Inventor 张运辉查正华刘英超张宇生李锡伦杨继斌蔡中文王亚川
Owner CHONGQING KANGLE PHARMA
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