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Niraparib synthesis method

A synthetic method and synthetic route technology, applied in the field of synthesis of Niraparib, can solve problems such as difficult to realize large-scale industrial production, limit industrial safety production, long synthetic route, etc., achieve large-scale production, easy large-scale production, The effect of easy control of operating conditions

Inactive Publication Date: 2017-03-01
SHAANXI UNIV OF SCI & TECH
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Problems solved by technology

The synthetic route is relatively long, and Niraparib obtained by using Chiralpak AS-H normal phase chiral chromatographic column is not easy to achieve large-scale industrial production, and unstable and difficult post-processing raw materials such as sodium azide are used in the reaction, which limits industrialization Safe Production

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Embodiment 1

[0037] Niraparib intermediate 1 Synthesis

[0038]The synthesis of Niraparib intermediate 1 is carried out in two steps, the first step (esterification): 3-methyl-2-nitrobenzoic acid and methyl alcohol are pressed by n (3-methyl-2-nitrobenzoic acid): The ratio of n (methanol) = 1:5, that is, take 182g of 3-methyl-2-nitrobenzoic acid, place 160.2g of methanol in a conical flask with a reflux device, heat slowly, and wait for 3-methyl-2- After the nitrobenzoic acid was completely dissolved in methanol, 6 mL of concentrated sulfuric acid was added, and the temperature was raised to 58°C for the reaction. The product was methyl 3-methyl-2-nitrocarboxylate (Niraparib intermediate 1) and water. The generated Niraparib intermediate 1 is subjected to the second step (refinement and extraction): after the esterification reaction is completed, after the temperature of the reaction solution drops to room temperature, adjust the pH of the solution to neutral with sodium bicarbonate, and...

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Abstract

The invention discloses a Niraparib synthesis method. The method comprises that through esterification, 3-methyl hydroformylation, 3-schiff base reaction, cyclization, amidation, BOC removal and chiral resolution, optically pure Niraparib with purity of 91% or more is prepared from 3-methyl-2-nitrobenzoic acid. The method has the advantages of simple process, high efficiency, easy operation and less equipment requirement, and is a method suitable for industrial production.

Description

technical field [0001] The invention relates to the synthesis of anticancer drugs, in particular to a synthesis method for preparing Niraparib. Background technique [0002] The chemical name of Niraparib is 2-[4-((3S)-3-piperidinyl)phenyl]-2H-indazole-7-carboxamide, which is an oral poly ADP ribose polymerase (PARP) inhibitor, Inhibits cellular repair of DNA damage. For cancer cells with BRCA gene mutations, if PARP activity is further inhibited, these cells will generate a lot of DNA damage when they divide, leading to the death of cancer cells. However, normal cells can still repair DNA without PARP because of the presence of BRCA, but the effect is worse, but they can survive. This is why PARP inhibitors act as targeted drugs to selectively kill BRCA mutant cancer cells. Niraparib is suitable for cancers with BRCA1 / 2 gene mutations, such as ovarian cancer and breast cancer, and was developed by Tesaro, an American biotechnology company. A phase III clinical trial cal...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/10
CPCC07D401/10C07B2200/13
Inventor 梁承远贾敏一田丹妮
Owner SHAANXI UNIV OF SCI & TECH
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