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Preparation method of fluvastatin sodium dehydrated metabolite

A technology of fluvastatin sodium and metabolites, which is applied in the field of preparation of dehydrated metabolites of fluvastatin sodium, can solve problems such as tissue damage and gene changes, and achieve the effects of reasonable route design, high yield and strong operability

Active Publication Date: 2017-06-30
TLC NANJING PHARMA RANDD CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Genetic alterations may be due to the production of drug metabolites, but may also be due to tissue damage, or interactions between metabolites and other receptors

Method used

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  • Preparation method of fluvastatin sodium dehydrated metabolite
  • Preparation method of fluvastatin sodium dehydrated metabolite
  • Preparation method of fluvastatin sodium dehydrated metabolite

Examples

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Embodiment 1

[0043] Such as figure 1 Shown, a kind of preparation method of fluvastatin sodium dehydration metabolite, it comprises the following steps:

[0044] Step (A): Preparation of intermediate product (1)

[0045] 20g fluvadiol was dissolved in 400mL THF, added 11.1g manganese dioxide, stirred at room temperature after 12 hours, the reaction was complete, and the manganese dioxide was removed by suction filtration, the solid was washed with THF, the filtrate was concentrated, and purified with a chromatographic column to obtain the compound (1 ), yield 85.33%.

[0046] Step (B): Preparation of intermediate product (2)

[0047] Take 12g of compound (1) and dissolve it in 120mL of dichloromethane, add 5.3g of imidazole and 9.7g of tert-butyldimethylsilyl chloride, react at room temperature for 18 hours, TLC shows that the reaction is complete, the reaction solution is followed by water, 0.5N hydrochloric acid and chloride After washing with aqueous sodium solution, drying over anhy...

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Abstract

The invention discloses a preparation method of a fluvastatin sodium dehydrated metabolite. According to the invention, t-Butyl(E)-3,5-dihydroxy-7-[3'-(4''-fluorophenyl)-1'-methylethyl-indol-2'-yl]-6-heptenoate is used as a raw material. By seven steps of reactions including selective oxidation of No.5 hydroxy, protection of No.3 hydroxy with a silyl-ether protective group, reduction of No.5 hydroxy, docking with benzoyl chloride, palladium-catalyzed dehydration into double bond, deprotection of silyl-ether with silyl-ether deprotection reagent and NaOH hydrolysis of tert-butyl ester, etc., the target molecule is synthesized. The whole route design is reasonable, post-treatment is simple, raw materials are cheap and easily available, and purity of the prepared target product can reach 99.9% and above. The product can be used in pharmacokinetic study. The invention provides a test sample for the research on metabolic mechanism of fluvastatin and has important application value.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to a preparation method of fluvastatin sodium dehydrated metabolites. Background technique [0002] Fluvastatin sodium (Fluvastatin sodium), chemical name [3R*,5S*-(E)]-(±)-7-[3-(4-fluorophenyl)-1-isopropyl-1H-ind Sodium indol-2-yl]-3,5-dihydroxy-6-heptenoate is the fourth HMG-CoA reductase inhibitor developed after lovastatin, pravastatin and simvastatin. Its indole ring mimics the coenzyme, and the mevalonate chain mimics the product mevalonate, which can simultaneously block HMG-CoA substrates and products, and play the role of endogenous cholesterol synthesis rate-limiting enzyme, thereby inhibiting Mevalonate generates cholesterol and stimulates the high-affinity low-density lipoprotein (LDL) receptors in the liver to increase, eventually reducing serum low-density lipoprotein cholesterol (LDL-C) levels and total cholesterol (TC) levels. [0003] Fluvastatin is a pair o...

Claims

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Application Information

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IPC IPC(8): C07D209/24
CPCY02P20/55C07D209/24
Inventor 陈强丁亚胡永铸刘春王忠义
Owner TLC NANJING PHARMA RANDD CO LTD
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