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Glucopyranose-substituted pyrazole compound and preparation method thereof

A compound and reaction technology, applied in the field of glucopyranose-substituted pyrazole compounds and its preparation, can solve the problems of low purity of the final compound and unfavorable drug preparation process, so as to ensure controllable drug quality, easy industrial production, The effect of easy separation and purification

Active Publication Date: 2019-07-26
YABAO PHARMA GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The purity of the final compound obtained is not high, which is not conducive to the subsequent drug preparation process

Method used

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  • Glucopyranose-substituted pyrazole compound and preparation method thereof
  • Glucopyranose-substituted pyrazole compound and preparation method thereof
  • Glucopyranose-substituted pyrazole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] 626g of compound (16), 6L of acetonitrile, 840g of cesium carbonate and 1770g of 2,3,4,6-tetra-O-pivaloyl-α-D-glucosyl bromide (compound (17)) were successively added to the reactor, Heat to 40°C-45°C, react for 4-5 hours, then cool down to 20-25°C, filter, rinse the solid with acetonitrile once; dissolve the filter cake with 8L ethyl acetate and 10L water and separate the liquid, and concentrate the organic phase to about 3L , add 10L of acetonitrile, stir for 12h, precipitate out solid, filter, rinse the filter cake with acetonitrile, and dry in vacuum at 60°C for 24h to obtain 652g of off-white solid compound (9c), yield 61%, HPLC purity 98.52%. 1HNMR (400MHz, MeOD) ( figure 1 ): δ7.10(s, 1H), 7.03(d, J=8.0Hz, 1H), 6.86(d, J=8.0Hz, 1H), 6.39(d, J=15.6, 1H), 6.19-6.12( m, 1H), 5.59(d, J=8.4Hz, 1H), 5.40-5.35(t, J=9.6Hz, 1H), 5.17-5.06(m, 2H), 4.18-4.14(dd, J=12.4Hz , 4.4Hz, 1H), 4.10-4.06(dd, J=12.4Hz, 1.6Hz, 1H), 3.92-3.89(dd, J=10Hz, 2.4Hz, 1H), 3.64-3.54(dd, J=20...

Embodiment 2

[0076] With the maleate of 5.00kg compound (16), 40L tetrahydrofuran, 5.47kg potassium phosphate and 11.67kg2,3,4,6-tetra-O-pivaloyl-α-D-glucosyl bromide (compound (17) ) into the reaction kettle in turn, heated to 40-45°C, cooled to 15-25°C after reacting for 4-5 hours, filtered, and rinsed the solid with tetrahydrofuran once. The filter cake was dissolved with 36L of ethyl acetate and 20L of water and separated. The organic phase was concentrated to about 18L, 64L of acetonitrile was added, and stirred for 15h. After filtering, the filter cake was rinsed with acetonitrile, and dried under vacuum at 60°C for 24 hours to obtain 4.50 kg of off-white solid compound (9c), with a yield of 57% and a purity of 99.19% by HPLC.

[0077] 4.45kg of compound (9c) and 45L of butyl acetate were added to the reaction kettle in turn, and the temperature was lowered to 15°C-20°C. Add 4.13kg of methanesulfonic acid in batches and react for 2-3 hours. Add 22L of 9% aqueous potassium hydroxid...

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Abstract

The invention relates to a glucopyranose-substituted pyrazole compound as a drug intermediate, and a preparation method and a use thereof. Specifically, the invention relates to a key intermediate forpreparation of a compound of a novel SGLTs inhibitor for treatment of diabetes, and a preparation method and a use thereof.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a glucopyranose-substituted pyrazole compound used as a drug intermediate, a preparation method and application thereof. Background technique [0002] Diabetes mellitus is a group of lifelong metabolic diseases characterized by chronic hyperglycemia caused by multiple etiologies. Long-term high blood sugar will cause damage to large blood vessels and microvessels and endanger the heart, brain, kidneys, peripheral nerves, eyes, feet, etc. According to the statistics of the World Health Organization, there are more than 100 complications of diabetes, which is the disease with the most known complications at present, and the incidence rate is also on the rise. The kidney plays a very important role in the body's glucose metabolism. Glucose cannot freely pass through the lipid bilayer of the cell membrane in the body, and must rely on the glucose transporter on the cell membrane. S...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/02C07H1/00
CPCC07H17/02C07H1/00A61P3/10
Inventor 张斐王鹏孙丽丽朱琳
Owner YABAO PHARMA GRP CO LTD
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