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Industrialized synthesis method of medicinal indocyanine green

A technology of indocyanine green and synthetic method, which is applied in the field of pharmacy, can solve the problems of many reaction steps, inconvenient industrial production, and low product yield, and achieve the effects of less synthetic reaction steps, easy production operation, and simple process operation

Inactive Publication Date: 2014-11-05
卫材(辽宁)制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When preparing 2, literature [2] adopts a solvent-free method, which is easy to solidify in the later stage of the reaction, difficult to stir, and difficult to operate
The requirements are harsh, the reaction steps are many, the organic solvent used is relatively harmful to the environment, and the product yield is low, the impurities are difficult to control, the production cost is high, and it is not convenient for industrial production

Method used

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  • Industrialized synthesis method of medicinal indocyanine green
  • Industrialized synthesis method of medicinal indocyanine green
  • Industrialized synthesis method of medicinal indocyanine green

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 1) Synthesis of 2,3,3-trimethyl-1-(4-sulfobutyl)-4,5-benzindole betaine:

[0018]

[0019] Specifically: mix 2,3,3-trimethyl-4,5-benzindolebenzene and 1,4-butyl sultone at a weight ratio of 1:1.6, in the presence of xylene Reflux at 140°C for 3 hours, cool to 50°C and add acetone 6 times the volume of xylene, reflux at 55°C for 0.5 hour, cool to 20°C, filter and dry. That is, light blue solid 2,3,3-trimethyl-1-(4-sulfobutyl)-4,5-benzindole betaine, wherein, according to 2,3,3-trimethyl Base-4,5-benzindolebenzene 1:0.8 weight ratio was added to xylene.

[0020] 2) 2-[6-(N-ethylanilino)-1,3,5-hexatrien-1-yl]-3,3-dimethyl-1-(4-sulfobutyl)-4 , Synthesis of 5-benzindole betaine

[0021]

[0022] Specific process: the above-mentioned obtained 2,3,3-trimethyl-1-(4-sulfobutyl)-4,5-benzindole betaine and 2-pentenedial dianiline hydrochloride Salts were mixed at a weight ratio of 1:0.9, refluxed and condensed at 140°C for 5 minutes in the presence of acetic anhydride, t...

Embodiment 2

[0029] 1) Synthesis of 2,3,3-trimethyl-1-(4-sulfobutyl)-4,5-benzindole betaine:

[0030]

[0031]Specifically: mix 2,3,3-trimethyl-4,5-benzindolebenzene and 1,4-butyl sultone at a weight ratio of 1:1.7, in the presence of xylene Reflux at 142°C for 2 hours, cool to 60°C, add acetone 4 times the volume of xylene, reflux at 52°C for 0.5 hour, cool to 25°C, and filter and dry. That is, light blue solid 2,3,3-trimethyl-1-(4-sulfobutyl)-4,5-benzindole betaine, wherein, according to 2,3,3-trimethyl Base-4,5-benzindolebenzene 1:1.2 weight ratio was added to xylene.

[0032] 2) 2-[6-(N-ethylanilino)-1,3,5-hexatrien-1-yl]-3,3-dimethyl-1-(4-sulfobutyl)-4 , Synthesis of 5-benzindole betaine

[0033]

[0034] Specific process: the above-mentioned obtained 2,3,3-trimethyl-1-(4-sulfobutyl)-4,5-benzindole betaine and 2-pentenedial dianiline hydrochloride The salts were mixed in a weight ratio of 1:1.1, refluxed and condensed at 130°C for 10min in the presence of acetic anhydride, t...

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Abstract

The invention belongs to the pharmaceutical technical field, and in particular relate to an industrialized synthesis method of medicinal indocyanine green. The synthesis method is as follows: 2, 3, 3-trimethyl-4, 5-benzo indole benzene and 1, 4-butyl sultone are mixed in the weight ratio of 1: 1.6 to 1.7 for reflux for 2-3 hours in the presence of xylene to obtain a light blue solid; the light blue solid and 2-glutacondianil hydrochloride are mixed in the weight ratio of 1: 0.9-1.1 weight ratio for reflux in the presence of acetic anhydride to obtain a blue black solid; the obtained light blue solid and the blue black solid are mixed in the weight ratio of 1: 1.3 to 1.7 for mixing and reflux reaction for 15-20min by addition of triethylamine in presence of anhydrous ethanol, after the reaction liquid is cooled, diethyl ether is added for extraction, the extraction liquid is filtered, filtrate is collected, a sodium iodide methanol solution is dripped, after the reaction, methanol is evaporated out, and the medicinal indocyanine green is obtained by drying. The synthesis method is mild in reaction conditions, improves yield, reduces cost, and reduces the product impurity content.

Description

technical field [0001] The invention belongs to the technical field of pharmacy, in particular to an industrial synthesis method of medicinal indocyanine green. Background technique [0002] Indocyanine green is a fully synthetic tricarboxylic cyanine diagnostic reagent, also known as indigo green, which was developed by Kodak Laboratories in the United States in 1955. The preparation of indocyanine green is indocyanine green injection, which is widely used as a diagnostic reagent in hepatobiliary surgery. It is an ideal diagnostic reagent for clinical diagnosis of liver and gallbladder and other related diseases (Zhang Chengfen, Chen Youxin. Carry out research on indocyanine green choroidal angiography to improve the clinical diagnosis, treatment and research level of fundus diseases [J]. Chinese Journal of Fundus Diseases, 1988, 14(2 ):66-67.). [0003] Current literature reports (Heseltine DW, Brooker LGS. Tricarbocyanine infrared absorbing dyes [P]. US: 2895955, 1959-0...

Claims

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Application Information

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IPC IPC(8): C07D209/60
CPCC07D209/60
Inventor 贾天亮郑桂荣刘绍杰
Owner 卫材(辽宁)制药有限公司
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