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Method for producing intermediate useful for synethesis of SGLT inhibitor

A technology of compounds and catalysts, applied in the field of preparation of intermediates, can solve problems such as safety management burden

Pending Publication Date: 2021-03-30
DAEWOONG PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, the method for preparing diphenylmethane derivatives disclosed in Korean Patent Application Publication No. 2017-0142904 imposes a burden on safety management due to the use of heavy metals such as pyridinium chlorochromate (PCC), and requires separate preparation of Grignard reagents process, resulting in a cost burden due to the additional process

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  • Method for producing intermediate useful for synethesis of SGLT inhibitor
  • Method for producing intermediate useful for synethesis of SGLT inhibitor
  • Method for producing intermediate useful for synethesis of SGLT inhibitor

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Embodiment 1

[0315] Now, the present invention will be described in more detail with reference to the following examples. These examples are provided for illustrative purposes only and should not be construed as limiting the scope and spirit of the invention.

[0316] The abbreviations described in the examples below have the following meanings.

[0317] -DMF:N,N-Dimethylformamide

[0318] -EtOH: ethanol

[0319] -Et 3 SiH: Triethylsilane

[0320] -MC: dichloromethane

[0321] -MC / AN: dichloromethane and acetonitrile

[0322] -NaOH: sodium hydroxide

[0323] -RT or rt: room temperature

[0324] Reaction Pattern Diagram

[0325]

[0326] The first step: 4-bromo-7-chloro-2,3-dihydrobenzofuran-6-carboxylic acid (compound 2)

[0327]

[0328]Add 4N sodium hydroxide (51.4 mL, 205.8 mmol) to 4-bromo-7-chloro-2,3-dihydrobenzofuran-6-carboxylic acid methyl ester (Compound 1) (20.0 g, 68.6 mmol) in ethanol (200 mL). The mixture was stirred at room temperature for 2 hours, and after...

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Abstract

The present invention relates to a method for producing an intermediate useful for the synthesis of a diphenylmethane derivative that can be used as a SGLT inhibitor. A method for synthesizing a compound of formula 7 according to the present invention has solved the problem of an existing synthesis process which requires an additional process due to the synthesis of Grignard reagent and the management of a related substance. In addition, the process can be simplified by minimizing the formation of the related substance and eliminating the need for reprocessing of reaction products, thereby becoming capable of maximizing a yield of a diphenylmethane derivative.

Description

technical field [0001] The invention relates to a preparation method of an intermediate used for synthesizing diphenylmethane derivatives which can be used as SGLT inhibitors. Background technique [0002] Sodium-glucose cotransporter (SGLT) causes glucose to be transported against the concentration gradient, and Na + transport along a concentration gradient. Currently, two important SGLT subtypes, SGLT1 and SGLT2, have been cloned. SGLT1 is located in the intestine, kidney, and heart and regulates cardiac glucose transport. Furthermore, SGLT1 is a high-affinity, low-dose transporter responsible for only a small fraction of renal glucose reuptake. In contrast, SGLT2 is a low-affinity, high-dose transporter predominantly localized in the apical region of proximal tubule epithelial cells in the prophase. In healthy individuals, more than 99% of glomerular filtered plasma glucose is reabsorbed and less than 1% of total filtered glucose is excreted in the urine. It is estim...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/82C07D409/04C07H7/06C07H1/00
CPCC07H1/00C07H7/06C07D307/79C07D493/04C07D407/04C07D307/82C07D409/04
Inventor 李庆日尹羲均
Owner DAEWOONG PHARM CO LTD
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