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A kind of preparation method of glimepiride intermediate

A technology for intermediates and compounds, applied in the field of API preparation, can solve the problems of impurities Ⅴ and Ⅵ exceeding the standard and exceeding the limit, difficult to remove, and low impurity content.

Active Publication Date: 2022-05-31
迪嘉药业集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] Purpose of the invention: To solve the problem that the compound I prepared by the prior art has high impurity content and is difficult to remove, to provide a method for preparing compound I with low impurity content
[0020] Because the purification of 4-(2-aminoethyl)benzenesulfonamide is relatively easy, it is easy to obtain high-purity commercial raw materials, and according to the method of route 2 document (3), the problem of exceeding the standard and exceeding the limit of impurities Ⅴ and Ⅵ is solved question

Method used

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  • A kind of preparation method of glimepiride intermediate
  • A kind of preparation method of glimepiride intermediate
  • A kind of preparation method of glimepiride intermediate

Examples

Experimental program
Comparison scheme
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Embodiment 1（1

[0047] Example 1 (1.0 molar equivalent of acetic acid)

[0048] Compound IX. 5.0g, 4-(2-aminoethyl)benzenesulfonamide 4.08g, acetic acid 1.22g and isopropanol 50g heated reflux for 8h (4-(2-aminoethyl)benzene sulfonamide remaining amount of 0.74%), cooled 25 °C, filtered, 50 °C dryed to compound I.6.67g, HPLC detection purity of 99.86%, impurity VIII. 0.05%, impurities V. and VI. undetected, yield 93.2%

Embodiment 2（1

[0049] Example 2 (1.0 molar equivalent acetic acid amplification effect)

[0050] The compound IX. 40.0g, 4-(2-aminoethyl)benzenesulfonamide 32.64g, acetic acid 9.8g and isopropanol 160g were heated and refluxed for 8h, cooled at 25 °C, filtered, and dried at 50 °C to give Compound I. 53.65g, yield 93.6%, HPLC detection purity of 99.78%, impurity VIII. 0.06%, impurity V. and VI. undetected.

Embodiment 3（2

[0051] Example 3 (2.0 molar equivalent of acetic acid)

[0052]The compound IX. 10.0g, 4-(2-aminoethyl)benzenesulfonamide 8.16g, glacial acetic acid 4.9g and isopropanol 50g heated reflux for 7h, cooled 25 °C, filtered, 50 °C dried to compound I. 13.18g, yield 92.0%, HPLC method detection purity of 99.71%, impurities VIII. 0.04%, impurities V. and VI. undetected.

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Abstract

The invention relates to a preparation method of glimepiride intermediate compound I, which belongs to the technical field of preparation of raw materials. The preparation method of the present invention comprises the following steps: reacting compound II and diphenyl carbonate under the catalysis of a base (refer to Synlett, 28(18), 2495-2498; 2017) to prepare compound IX; then compound IX and 4‑(2‑Aminoethyl)benzenesulfonamide is fed at a ratio of 1:1, a weak acid is added, isopropanol is added, and the reaction is heated under reflux. The technical scheme of the present invention provides a method for preparing a high-purity glimepiride intermediate.

Description

Technical field [0001] The present invention relates to a method for preparing a glimepiride intermediate compound I., belonging to the field of API preparation technology. Background [0002] Glimepiride is a third-generation sulfonylurea long-acting anti-diabetic drug developed by the German company Hoechst in the 1980s and first listed in Sweden under the trade name Amaryl in September 1995. Since glimepiride has a weak effect on the cardiovascular KATP channel, there are fewer cardiovascular adverse reactions. Glimepiride has the advantages of high efficiency, long-term effect, small dosage (2 to 4mg / day), and small side effects. [0003] All current routes for the synthesis of glimepiride require the use of the intermediate 4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl] benzenesulfonamide (i.e., Compound I). [0004] [0005] At present, there are two main routes reported in the synthesis literature on this intermediate: [0006] Route 1 [0007] [0008] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/38
CPCC07D207/38Y02P20/55
Inventor 吴荣贵薛复照徐可岭王常德
Owner 迪嘉药业集团股份有限公司
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