Compound as well as preparation method and application thereof

A compound and complex technology, applied in the field of compounds and their preparation, can solve the problems of unfavorable drug purity of canagliflozin, unknown impurity structure, control of production process, etc., and achieves easy control of process operation, low cost, and improved quality Effect

Inactive Publication Date: 2018-09-28
湖北华世通生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the prior art, although the structures of some canagliflozin impurities have been analyzed, the structures of some impurities are still unknown, which is not conducive to the control of the purity in the production process of canagliflozin and the optimization of the production process

Method used

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  • Compound as well as preparation method and application thereof
  • Compound as well as preparation method and application thereof
  • Compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065]

[0066] S1. Add 20g of D-gluconolactone into a 100ml dry three-necked flask, add 70g of acetic anhydride, add 30g of cation exchange resin at room temperature, and keep it at 40-50°C for 2-3 hours after the addition is completed. TLC monitors that the reaction solution is basically No gluconolactone. After the reaction was completed, the cation exchange resin was filtered out, and the filtrate was concentrated under reduced pressure at 70-80°C until there was no distillate, and about 41 g of compound 1 was obtained as a brownish-yellow oily viscous liquid, with a yield of about 105%.

[0067] S2. In a 100ml dry three-neck flask, add 30ml of toluene, 13g, cooled down to 0-10°C under the protection of nitrogen, 30ml of tetrahydrofuran solution of sec-butylmagnesium chloride and lithium chloride was added under stirring, and kept at -10-0°C for 1-2 hours to obtain the prepared Grignard reagent.

[0068] S3. Add 20g of compound 1 and 20ml of tetrahydrofuran into anothe...

Embodiment 2

[0072]

[0073] S1. Add 300g of D-gluconolactone into a 1000ml dry three-necked flask, add 800g of acetic anhydride, add 450g of cation exchange resin at room temperature, and keep it at 40-50°C for 6-8 hours after the addition is completed. TLC monitors that the reaction solution is basically No gluconolactone. After the reaction was completed, the cation exchange resin was filtered out, and the filtrate was concentrated under reduced pressure at 70-80°C until there was no distillate, and about 642 g of brown oily viscous liquid Compound 1 was obtained, with a yield of about 110%.

[0074] S2. In a 100ml dry three-neck flask, add 30ml of toluene, 15g, under the protection of nitrogen, lower the temperature to 0-10°C, add 30ml of tetrahydrofuran solution of sec-butylmagnesium chloride and lithium chloride under stirring, and keep it at -10-0°C for 1-2 hours to obtain the prepared Grignard reagent.

[0075] S3~S5 are the same as embodiment 1.

experiment example

[0077] The following is a method for qualitative and quantitative detection of the canagliflozin impurity formula I prepared in Example 2 of the present invention. The present invention finds that the prepared canagliflozin impurity formula I can make the quality detection of the finished product of canagliflozin more accurate and controllable, and in the finished product of canagliflozin produced by the original research process route, the impurity also remains in the finished product If the structure of the impurity formula I of canagliflozin is not determined, the related substances in the canagliflozin bulk drug cannot be effectively controlled.

[0078] The method for detecting the finished product of canagliflozin by adopting the impurity formula I of canagliflozin prepared by the present invention below.

[0079] Related substances: get about 25 mg of canagliflozin, dissolve and quantitatively dilute with acetonitrile-water (80:20) to make the test solution containing a...

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Abstract

The invention relates to the field of chemical synthesis, in particular to a compound as well as a preparation method and application thereof. The compound is an impurity generated in the production process of canagliflozin, and can be applied to quality control of canagliflozin products by serving as a standard substance or a reference substance.

Description

technical field [0001] The present invention relates to the field of chemical synthesis, in particular to a compound and its preparation method and application. Background technique [0002] Canagliflozin is currently a class of drugs clinically used in the treatment of diabetes and is the first SGLT-2 inhibitor approved by the FDA. SGLT-2 is a new target for diabetes treatment. It has a different mechanism of action from traditional diabetes treatment drugs. It can excrete excess glucose from the urine, thereby reducing glycosylated proteins and improving insulin sensitivity in the liver and peripheral tissues. Improve β-cell function, and at the same time further improve hepatic insulin resistance, thereby promoting the return of higher glycogen output to normal. [0003] The original research company of canagliflozin is Takeda. At present, the main methods for the synthesis of canagliflozin in China are as follows: [0004] [0005] During the synthesis process, beca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14G01N30/02G01N30/04
CPCC07D409/14G01N30/02G01N30/04G01N2030/042
Inventor 喻耀梁樱崔健赵阿龙
Owner 湖北华世通生物医药科技有限公司
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