Process for synthesis of lonidamine

A technology of lonidamine and synthetic method, which is applied in the direction of drug combination, organic chemistry, antineoplastic drugs, etc., and can solve the problems of cost and complex production process of lonidamine

Active Publication Date: 2005-03-16
SHANGHAI ZHAOHUI PHARMA +1
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0007] The technical problem to be solved in the present invention is exactly the problem

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  • Process for synthesis of lonidamine
  • Process for synthesis of lonidamine
  • Process for synthesis of lonidamine

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Embodiment Construction

[0029] 1, the synthesis of β-acetylphenylhydrazine (I)

[0030] Add a solution of 265g (2.5mol) of phenylhydrazine, 600ml (10.5mol) of glacial acetic acid and 350ml of water into a 2L three-necked flask. Warm to reflux, stir for 3 hours, then cool to room temperature. The solid was precipitated, filtered, washed with water, and dried to obtain 290 g of off-white crystal I. Yield 78.2%. mp: 127.5-129.5°C

[0031] 2. Synthesis of N-acetylisonitrosoacetanilide (II)

[0032] In the three-necked flask of 3L, add I 76g (0.51mol), water 2300ml, concentrated hydrochloric acid 27ml, hydroxylamine hydrochloride 69 grams (0.9mol), anhydrous sodium sulfate 367 grams, chloral hydrate 157 grams (0.96mol). Raise the temperature to 80--95°C. Keep stirring for 0.4 hours. Rapidly raise the temperature to 110°C, stir for 4 minutes, rapidly cool to 55-65°C, add 5 g of activated carbon for decolorization and stir, quickly filter off the oil, freeze to precipitate a yellow solid, filter, wash...

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Abstract

The invention relates to a process for synthesizing 1-[(2,4-dichlorobenzene) methyl]-1H-indazole-3-carboxyl acid which consists of, using phenylhydrazine as starting raw material, producing beta-acetylphenylhydrazine through reaction with glacial acetic acid, reacting with hydrated chloral and hydroxylamine hydrochloride, obtaining N-acetamido-isonitro-acetanilide, preparing 1H-indazole-3-carboxylic acid under the condition of concentrated sulfuric acid, finally subjecting 1H-indazole-3-carboxylic acid with 2,4-dichlorin benzyl chloride.

Description

technical field [0001] The invention relates to a method for synthesizing 1-[(2,4-dichlorophenyl)methyl]-1H-indazole-3-carboxylic acid, i.e., lonidamine. Background technique [0002] Cancer is currently one of the major diseases that seriously affect human health and threaten human life; together with cardiovascular and cerebrovascular accidents, it constitutes the top three causes of death in all countries in the world today. Therefore, the World Health Organization and the health departments of governments of various countries have listed conquering cancer as a top priority. Lonidamine is a dichlorobenzene derivative of indazole acid, which is used to treat various tumors, including colon cancer, lung cancer, breast cancer, prostate cancer and kidney cancer, chronic lymphocytic leukemia, and as chemotherapy, Sensitizer for hyperthermia and radiotherapy. At present, there is a patent and a number of literature reports on its synthesis, and these literature methods basica...

Claims

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Application Information

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IPC IPC(8): A61P35/00C07D231/56
Inventor 刘彩连董志超张伟唐平高金花
Owner SHANGHAI ZHAOHUI PHARMA
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