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1-(beta-d-pyranoglucosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene and l-phenylalanine eutectic compound and preparation method thereof

A kind of co-crystal and crystallization technology, applied in 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl Base] benzene and L-phenylalanine co-crystal and the preparation field thereof, can solve the problem of renal diabetes without showing adverse clinical consequences and the like, and achieve the effect of being beneficial to finished medicine and good stability

Inactive Publication Date: 2014-08-06
JIANGSU HANSOH PHARMA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, familial renal diabetes has shown no significant adverse clinical consequences and the disease has a benign course

Method used

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  • 1-(beta-d-pyranoglucosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene and l-phenylalanine eutectic compound and preparation method thereof
  • 1-(beta-d-pyranoglucosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene and l-phenylalanine eutectic compound and preparation method thereof
  • 1-(beta-d-pyranoglucosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene and l-phenylalanine eutectic compound and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0022] Heat and dissolve L-phenylalanine (4g, 24.3mmol) in 60ml of water, filter, and add the resulting solution to the ethanol solution containing the compound of formula (I) (10g, 22.5mmol). The resulting solution was heated to 80°C, slowly cooled to 30°C, filtered, and the filter cake was recrystallized with 100ml of 50% water / ethanol to obtain 11.2g of a white solid, which was 1 HNMR and attached figure 1 The XRD shown was identified as the co-crystal of formula (Ia).

[0023] 1 HNMR (400MHz, DMSO-d6), δ2.27(s,3H), 2.87(d,0.5H), 3.16-3.31(m,6H), 3.41-3.48(m,3H), 3.69(d,1H) , 3.96(d,1H), 4.11(dd,2H), 4.6-5.2(m,2.5H), 6.77(d,1H), 7.11-7.19(m,4.5H), 7.23(m,2H), 7.27 (d,2H), 7.56(dd,2H)

Embodiment 2

[0025] L-phenylalanine (2g, 12.2mmol) was heated and dissolved in 30ml of water, filtered, and the resulting solution was added to a solution of isopropanol (50ml) containing the compound of formula (I) (5g, 11.3mmol). The resulting solution was heated to 81°C, slowly cooled to 40°C, filtered, and the filter cake was recrystallized with 80ml of 50% water / isopropanol to obtain 5.8g of a white solid.

Embodiment 3

[0027] L-phenylalanine (2g, 12.2mmol) was heated and dissolved in 30ml of water, filtered, and the resulting solution was added to a solution of isopropanol (40ml) containing the compound of formula (I) (5g, 11.3mmol). The resulting solution was heated to 70°C, slowly cooled to 40°C, filtered, and the filter cake was recrystallized with 60ml of 50% water / isopropanol to obtain 5.2g of a white solid.

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Abstract

The invention discloses an eutectic compound of 1-(beta-D-pyranoglucosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene and L-phenylalanine and a preparation method thereof. Specifically speaking, the invention discloses the eutectic compound shown in a formula (Ia) and formed by L-phenylalanine and a sodium-glucose co-transporter 2 (SGLT-2) inhibitor shown in a formula (I), i.e., 1-(beta-D-pyranoglucosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene. The XRD characteristic peaks of the eutectic compound are shown in a figure 1. The preparation method comprises the following steps: mixing an aqueous solution of L-phenylalanine with an ethanol solution of the compound I; carrying out heating for dissolving of the two substances; then carrying out stirring, cooling and crystallization; and subjecting a filtrate to ethanol water recrystallization so as to obtain the eutectic compound. The formula (I) and the formula (Ia) are described in the specification.

Description

technical field [0001] The present invention relates to SGLT2 inhibitors 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene and L-benzene Structure of alanine co-crystal and its preparation method. Background technique [0002] As people's living standards and lifestyles change, the prevalence of diabetes is increasing. It is estimated that since 2007, there have been about 246 million diabetic patients in the world, accounting for 5.9% of the world's total population. It is estimated that by 2025, the number of patients will It will increase to 380 million, or 7.9% of the total adult population, seriously endangering human health. The diabetes drug market has become a large market with rapid growth. The research and development of new hypoglycemic drugs has long been a hot topic in the international pharmaceutical community. [0003] Diabetes is mainly divided into type 1 diabetes and type 2 diabetes. The former is caused by the inability of panc...

Claims

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Application Information

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IPC IPC(8): C07H7/04C07H1/06C07C229/36C07C227/42
Inventor 赵军军潘必高田辉
Owner JIANGSU HANSOH PHARMA CO LTD
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