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Roxadustat key intermediate and synthetic method thereof

A technology of roxadustat and its synthetic method, which is applied in the field of organic synthesis route design and the synthesis of raw materials and intermediates, can solve the problems of unsuitability for industrial production, harsh reaction conditions, and long reaction steps, and achieve low equipment requirements, Mild reaction conditions and low production cost

Active Publication Date: 2019-02-05
HEBEI DONGKANG BIOTECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0023] The object of the present invention is to provide a key intermediate of roxadustat for the problems of long synthesis reaction steps of roxadustat, harsh reaction conditions, high energy consumption, environmental pollution, and unsuitability for industrial production in the prior art. Its synthesis method is expected to shorten the synthesis steps of roxadustat by utilizing the intermediate, and the whole reaction process has mild conditions and is suitable for industrial production

Method used

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  • Roxadustat key intermediate and synthetic method thereof
  • Roxadustat key intermediate and synthetic method thereof
  • Roxadustat key intermediate and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1~5

[0056] Embodiment 1~5 key intermediate of roxadustat

[0057] Examples 1-5 are respectively a key intermediate of roxadustat, methyl-7-phenoxyisoquinoline-3-carboxylate, which have the structure of formula (I),

[0058]

[0059] In the formula (I), the R group is an alkyl group containing 1 to 5 carbon atoms, and the R groups in Examples 1 to 5 are respectively methyl, ethyl, isopropyl, n-butyl or tert-butyl, See the table below for details:

[0060]

Embodiment 1

[0063] Methyl-7-phenoxyisoquinoline-3-carboxylate of Example 1

[0064]

Embodiment 2

[0065] The methyl-7-phenoxyisoquinoline-3-carboxylic acid ethyl ester of embodiment 2

[0066]

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Abstract

The invention discloses a Roxadustat key intermediate and a synthetic method thereof. The Roxadustat key intermediate is 1-methyl-7-phenoxyisoquinoline-3-carboxylate. The synthetic method for the Roxadustat key intermediate comprises the following three steps that firstly, 4-phenoxybenzaldehyde and N-acetylglycine are subjected to Erlenmeyer-Pl-chl condensation reaction in the presence of acetic anhydride and sodium acetate or potassium acetate, then alcoholysis reaction is carried out with alcohol in the presence of alkali, and finally, Bischler-Napieralski cyclization reaction is carried outwith leiws acid in the presence of a solvent so as to obtain the Roxadustat key intermediate. The synthetic method has the advantages that the raw materials are easy to obtain, the reaction conditions are mild, the requirement for equipment is low, the yield is high, the synthesis steps of Roxadustat are shortened, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis route design and synthesis of raw materials and intermediates, and specifically relates to a key intermediate of roxadustat and a synthesis method thereof. Background technique [0002] Roxadustat is the first oral small molecule HIF-PHI developed by Fibrogen, mainly for the treatment of renal anemia. It can inhibit HIF-prolyl hydroxylase under normal oxygen partial pressure, Stabilize HIF-α, promote endogenous erythropoietin, Erythropoietin, EPO production, improve iron absorption and utilization, and comprehensively regulate erythropoiesis. The results of two Phase III clinical trials in China for the treatment of anemia in dialysis-dependent (DD-CKD) and non-dialysis-dependent (NDD-CKD) chronic kidney disease patients met the primary efficacy endpoints. On December 18, 2017, roxadustat was included in the priority review by CDE as "compared with the existing treatment methods and has...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/26
CPCC07D217/26
Inventor 李素方张赓远柳天乐柳昆鹏齐艺冰李若璇常睿博崔玉兰邵艳新徐昊楠原圣璋
Owner HEBEI DONGKANG BIOTECH CO LTD
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