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Preparation method of gliclazide side chain and preparation method of gliclazide

A technology of gliclazide and side chain, which is applied in the preparation of gliclazide and the new preparation field of side chain of diabetes drug gliclazide, which can solve the problems of difficult industrialization, harsh reaction conditions, and high equipment requirements. Achieve the effects of reduced preparation cost, low hydrogen pressure, and simple post-treatment

Active Publication Date: 2019-08-13
PANJIN GELIN KAIMO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the main disadvantages of this method are harsh reaction conditions, high requirements for equipment, high energy consumption, relatively high production risk, unfavorable for safe production, and relatively difficult industrialization.
In addition, the catalyst in this method cannot be effectively recovered and reused, and the cost of one-time use is too high

Method used

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  • Preparation method of gliclazide side chain and preparation method of gliclazide
  • Preparation method of gliclazide side chain and preparation method of gliclazide
  • Preparation method of gliclazide side chain and preparation method of gliclazide

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preparation example Construction

[0039] The invention provides a preparation method of gliclazide side chain N-amino-3-azabicyclo[3.3.0]octane (I), using N-aminocyclopentane imide (II) as raw material, A highly active ruthenium carbon catalyst modified with a transition metal atom is used for one-step hydrogenation to obtain a gliclazide side chain (I), and the specific preparation method is as follows:

[0040]

[0041] Dissolving N-aminocyclopentane imide (II) in an acidic aqueous solution, adding a highly active ruthenium-carbon catalyst modified by a transition metal atom, under the condition that the hydrogen pressure is 6-9MPa and the temperature is 90-140°C, Reduction for 16 to 20 hours produces N-amino-3-azabicyclo[3.3.0]octane (I). Then cool down to room temperature, release the pressure, and filter. The filter cake ruthenium carbon catalyst can be applied (recycled) to the next reaction. The filtrate is concentrated under reduced pressure. The acid water is usually recovered after distillation an...

Embodiment 1

[0064] (1) Preparation of molybdenum atom modified ruthenium carbon catalyst

[0065] Weigh 47.26kg of activated carbon powder and disperse it in 200L of deionized water; weigh 6.723kg of ruthenium chloride trihydrate and dissolve it in 100L of deionized water; under stirring conditions, mix the two and absorb for 1 hour; weigh 1.911kg of molybdic acid Ammonium solid ((NH 4 ) 6 Mo 7 o 24 4H 2 (2), be dissolved in 50L deionized water, and gradually add in the above-mentioned gac solution under stirring condition; After stirring and absorbing for 1 hour, add sodium borohydride aqueous solution (1.2kg sodium borohydride is dissolved in 100L deionized water) gradually, react 1 at room temperature Hours later, filter with suction, wash 5 times with deionized water to near neutrality, and dry in an oven at 80° C. for 12 hours to obtain a molybdenum atom-modified ruthenium carbon catalyst, wherein the mass percentage of ruthenium is 5 wt%, and the mass percentage of molybdenum T...

Embodiment 2

[0072] In the 500L autoclave, add N-aminocyclopentane imide 100kg, acetic acid 70L, water 250L, stirring and dissolving, add the molybdenum atom modified ruthenium carbon catalyst (ruthenium content: 5wt% of 5wt%) prepared in embodiment 1 (1), Molybdenum content: 2wt%) 15kg. Under the conditions of controlling the hydrogen pressure to 8 MPa and the temperature to 135° C., the reaction was carried out for 20 hours. Cool down to room temperature, release the pressure, and filter. The filter cake ruthenium carbon catalyst sleeve is used for the next reaction. The filtrate was transferred to a concentration kettle to concentrate under reduced pressure, and the acetic acid water jacket was recovered for the next reaction. Concentrate to obtain about 114kg of the crude gliclazide side chain. Add hydrochloric acid to process, then add toluene-ethanol mixed solvent to recrystallize, centrifuge shakes off material, oven dry, obtain N-amino-3-azabicyclo[3.3.0]octane hydrochloride 97....

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Abstract

The invention relates to a preparation method of N-amino-3-azabicyalo [3.3.0] octane serving as a gliclazide side chain. The gliclazide side chain is obtained by carrying out one-step hydrogenation reduction on N-cyclopentyl amine imide through a transition metal atom-modified ruthenium-carbon catalyst. The activity of the modified ruthenium-carbon catalyst used in the method is obviously higher than that of an existing commercial ruthenium-carbon catalyst, so that the imide hydrogenation reaction which is hard to realize in the N-cyclopentyl amine imide can be carried out successfully. The preparation method of the gliclazide side chain is safe, efficient, high in yield and simple for posttreatment; the catalyst can be cyclically used indiscriminately, so that the production cost is substantially reduced, and green synthesis is basically realized; no waste water and no waste slag are produced; and the preparation method is particularly suitable for large-scale industrial production. The invention further relates to a production method of gliclazide, which has the advantages of short synthesis path, high yield, low preparation cost and the like.

Description

technical field [0001] The present invention relates to a new preparation method of the side chain of diabetes drug gliclazide, in particular to a new preparation method of N-amino-3-azabicyclo[3.3.0]octane, an intermediate of gliclazide. The invention relates to a preparation method of gliclazide, which belongs to the technical field of organic synthesis. Background technique [0002] Gliclazide is a second-generation sulfonylurea oral hypoglycemic drug, which can effectively lower blood sugar and improve blood coagulation function, and is especially suitable for patients with various subtypes of non-insulin-dependent diabetes mellitus, and has less side effects. With the improvement of people's living standards in our country, diabetes has attracted much attention as a disease of the rich, and research on hypoglycemic drugs has very important practical significance. [0003] The key to the synthesis of gliclazide is the synthesis of its side chain N-amino-3-azabicyclo[3.3...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/52
CPCC07D209/52
Inventor 宫宁瑞
Owner PANJIN GELIN KAIMO TECH CO LTD
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