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New use of rifamycin-nitroimidazole coupling molecule

A technology of nitroimidazolium and rifamycin, which is applied in the field of medicinal chemistry, can solve the problem of no documented antibacterial activity, and achieve the effects of low frequency of drug resistance, strong antibacterial activity, and good application prospects

Inactive Publication Date: 2017-06-13
TENNOR THERAPEUTICS (SUZHOU) LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Compound 4-deoxy-3,4-[2-spirocycle-[2-(2-methyl-5-nitro-imidazol-1-yl)ethyl]-piperidine is disclosed in U.S. Patent No. 7,678,791B2 -4-base]]-(1hydrogen)-imidazo-(2,5-dihydro)rifamycin S, the compound has antimicrobial activity against Gram-positive bacteria and Escherichia coli and other bacteria, but No documented antimicrobial activity against ammonia-producing flora in the gastrointestinal tract

Method used

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  • New use of rifamycin-nitroimidazole coupling molecule
  • New use of rifamycin-nitroimidazole coupling molecule
  • New use of rifamycin-nitroimidazole coupling molecule

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] This example provides the application of the rifamycin-nitroimidazole coupling molecule represented by formula I in inhibiting anaerobic or facultative anaerobic ammonia-producing bacteria in the gastrointestinal tract;

[0020]

[0021] Wherein, the anaerobic or facultative anaerobic ammonia-producing bacteria group in the gastrointestinal tract includes Bifidobacterium infantis subspecies, Bacteroides fragilis, Clostridium perfringens, Eggerthia tarda, Fusobacterium necrosis, A combination of one or more of Eubacterium rectum, Clostridium difficile, Helicobacter pylori, Lactobacillus salivarius and Peptostreptococcus prausinii.

[0022] In this example, compound I rifamycin-nitroimidazole conjugated molecules were tested for drug susceptibility to pathogenic bacteria related to hepatic encephalopathy, and the pathogenic bacteria included the above-mentioned anaerobic ammonia-producing bacteria group. Tests were performed under anaerobic conditions using an agar dil...

Embodiment 2

[0040] This example provides the prescription and preparation method of a fast-release oral preparation of the rifamycin-nitroimidazole conjugate molecule represented by formula I.

[0041]

[0042] Weigh the rifamycin-nitroimidazole coupling molecule and auxiliary materials represented by the formula I according to the above-mentioned prescription amount. Dissolve povidone K30 (PVP K30) and sodium dodecyl sulfate (SDS) in purified water, stir for 1 hour, and use it as an adhesive for later use; couple rifamycin-nitroimidazole shown in formula I Molecule, mannitol and carboxymethyl starch sodium (DST) are passed through a 30-mesh sieve, added to the granulator, pre-mixed, the impeller stirring speed is 700rpm, and the time is about 15 minutes. Then use a peristaltic pump to add an appropriate amount of purified water and binder to the mixture of the granulator at a fixed speed (145-165g / min). The stirring speed of the impeller of the granulator is 400rpm, and the time is ab...

Embodiment 3

[0045] This example provides a method for preparing an injection of the rifamycin-nitroimidazole conjugate molecule represented by formula I.

[0046]

[0047] Add mannitol, acetaldehyde sodium sulfoxylate, and Tween-80 to an appropriate amount of water for injection under nitrogen protection, add the rifamycin-nitroimidazole coupling molecule shown in formula I, and stir at a medium speed for 10-15 minutes. Wet the rifamycin-nitroimidazole coupling molecule shown in formula I, and slowly add 1N NaOH dropwise, which takes about 175 minutes (fast at the beginning and slow at the end), to the rifamycin-nitroimidazole shown in formula I The coupling molecules are completely dissolved, filtered through two microporous membranes of 0.45+0.22 μm, the filtrate is filled into 10mL glass bottles, each bottle contains 3.5mL, the glass bottles are transferred to a lyophilizer for lyophilization, and the formula is obtained after capping The freeze-dried powder injection of the rifamyc...

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Abstract

The invention discloses application of a rifamycin-nitroimidazole coupling molecule represented in a formula I in inhibition of anaerobic or facultative anaerobic ammonia producing floras in gastrointestinal tracts. The rifamycin-nitroimidazole coupling molecule represented in the formula I is similar to an antibacterial spectrum of rifaximin and has relatively strong antibacterial activity to common ammonia producing floras in the gastrointestinal tracts; and meanwhile, the rifamycin-quinolizidone dual-target molecule has the property of low spontaneous drug resistance frequency and has very good application prospects in prevention and treatment of infection of hepatic encephalopathy and relevant anaerobic bacteria. The formula is as shown in the specification.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a new application of a rifamycin-nitroimidazole coupling molecule. Background technique [0002] Hepatic encephalopathy (Hepatic Encephalopathy, HE) is one of the important complications of acute and chronic end-stage liver disease and liver cirrhosis, which seriously affects the prognosis and quality of life of patients. Once HE occurs in patients with chronic liver disease, the 1-year survival rate does not exceed 50%, and the 3-year survival rate does not exceed 25%. Among them, patients with covert hepatic encephalopathy (CHE) often have no significant clinical symptoms and can only be discovered through neuropsychological tests. According to statistics, at least 30% of patients with liver cirrhosis may be accompanied by varying degrees of HE. A recent survey of 16 tertiary hospitals in 13 provinces and cities in China found that the incidence of CHE among inp...

Claims

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Application Information

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IPC IPC(8): A61K31/438A61P1/00A61P31/04A61P1/16A61P25/00
CPCA61K31/438
Inventor 马振坤袁鹰刘宇王晓梅
Owner TENNOR THERAPEUTICS (SUZHOU) LTD
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