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A kind of preparation method of ecabet sodium

A technology of icabet sodium and sodium salt is applied in the field of preparation of anti-peptic ulcer drug icabet sodium, which can solve the problems of low selectivity, low yield and the like, and achieves simple and easy-to-obtain raw materials and high yield. High and complete sulfonation conversion rate

Active Publication Date: 2016-08-17
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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  • A kind of preparation method of ecabet sodium
  • A kind of preparation method of ecabet sodium
  • A kind of preparation method of ecabet sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1.1 Preparation of 12-sulfonic acid dehydroabietic acid (II)

[0030] 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%).

[0031] 1.2 Preparation of ecabet sodium (I)

[0032] 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

[0034] 2.1 Preparation of 12-sulfonic acid dehydroabietic acid (II)

[0035] 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%).

[0036] 2.2 Preparation of ecabet sodium (I)

[0037] 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

[0039] 3.1 Preparation of 12-sulfonic acid dehydroabietic acid (II)

[0040] 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%).

[0041] 3.2 Preparation of ecabet sodium (I)

[0042]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 preparation method of ecabet sodium, which is characterized in that: the method of the invention uses dehydroabietic acid (formula III) as a starting material, and carries out sulfonation reaction with oleum to obtain 12-sulfonic acid Base dehydroabietic acid (formula II), the compound of formula II and a sodium forming agent form a sodium salt in at least an aqueous solvent system to obtain ecabet sodium. The method of the invention overcomes the disadvantages of the prior art, and has the advantages of high sulfonation yield, high selectivity for sodium salt formation, simple operation, safety and environmental protection, 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 drug. 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-monosodiumsalt 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 Pharmaceuticals noti...

Claims

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Application Information

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Patent Type & Authority Patents(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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