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A kind of preparation method of terbinafine hydrochloride z type isomer

A technology of terbinafine hydrochloride and isomers, which is applied in the field of medicine, can solve the problems of unrecorded impurity analysis and detection, and achieve the effects of stable product quality, mild conditions, and simple synthesis steps

Active Publication Date: 2017-05-24
吉林修正药业新药开发有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] There are many patent documents about the preparation of terbinafine hydrochloride, all of which describe the preparation process of terbinafine hydrochloride in detail, but there is no record about the analysis and detection of impurities, so as to realize the control of drug quality

Method used

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  • A kind of preparation method of terbinafine hydrochloride z type isomer
  • A kind of preparation method of terbinafine hydrochloride z type isomer
  • A kind of preparation method of terbinafine hydrochloride z type isomer

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Embodiment Construction

[0023] Weigh 50.0 g of the terbinafine hydrochloride EZ mixture and place it in a 500 ml three-neck flask, add 200 ml of isopropanol thereinto, raise the temperature to 70° C., and keep the temperature for 2 hours. Slowly cool down to 20°C and keep warm for 2 hours, then cool down to 0°C and keep warm for 2 hours. After filtration, the filtrate was concentrated under reduced pressure to obtain an oil.

[0024] Put 10 g of the oily substance in a 100 ml three-necked flask, add 50 ml of 4-chlorophenyl tert-butyl ether, raise the temperature to 120°C, and keep the temperature for 1 hour. Then lower the temperature to 10° C., keep the temperature for 3 hours, and filter to obtain the off-white compound, terbinafine hydrochloride Z-isomer. 1 H-NMR (400MHz, CDCl 3 )δ1.25(s, 9H), 2.27(d, 2H), 3.03(d, 2H), 4.06(d, 2H), 5.62(t, 1H), 6.21(t, 1H), 7.10(m, 1H ), 7.19(m, 1H), 7.29(m, 1H), 7.31(m, 1H), 7.51(m, 1H), 7.64(m, 1H), 7.77(m, 1H)

[0025] Use octadecylsilane bonded silica gel ...

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Abstract

The invention discloses a method for preparing a terbinafine hydrochloride Z-shaped isomer serving as a high-purity isomer impurity compound for allylamine medicament terbinafine hydrochloride impurity analysis. The preparation method comprises the following steps: 1, adding a terbinafine EZ mixture to isopropanol, heating to 40-86 DEG C for dissolving, preserving the heat for 0.5-4 hours, slowly cooling to 10-20 DEG C, preserving the heat for 1-3 hours, cooling to -10-0 DEG C, preserving the heat for 1-5 hours, filtering, and concentrating the filtrate under reduced pressure to obtain an oily matter; and 2, adding 4-chlorphenyl-tert-butyl ether into the oily matter obtained in step 1, heating to 100-150 DEG C, preserving the heat for 1-5 hours, cooling to 0-40 DEG C, preserving the heat for 1-10 hours, and filtering to obtain an off-white compound. The method has the positive effect of obtaining the terbinafine hydrochloride isomer with relatively high purity. The isomer serving as a known impurity is used in quality analysis of terbinafine hydrochloride to determine the position of an impurity in a sample and survey the resolution between the impurity and the sample, so that the analysis method is more accurate. The preparation conditions are mild, the synthesis steps are simple, and the quality of the product is stable.

Description

[0001] Technical field: [0002] The invention belongs to the field of medicine, and in particular relates to an allylamine drug terbinafine hydrochloride isomer impurity with broad-spectrum antifungal activity, (Z)-N-(6,6-dimethylhept-2-ene-4- The preparation method of alkynyl)-N-methyl-1-naphthylmethylamine. [0003] Background technique: [0004] Terbinafine hydrochloride is an allylamine drug with broad-spectrum antifungal activity. This product can specifically interfere with the early biosynthesis of fungal ergosterol, highly selectively inhibit fungal squalene epoxidase, and hinder the epoxidation reaction of squalene in the process of fungal cell membrane formation, thereby achieving the goal of killing or Inhibits the action of fungi. [0005] At present, the main route of administration is still oral preparations, so it is very important to highlight the control of drug purity. The structure of terbinafine hydrochloride is E configuration, and its Z configuration i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/30C07C209/88
Inventor 阎君林子琦白冰王化录曹翠
Owner 吉林修正药业新药开发有限公司
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