Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of moxifloxacin hydrochloride structural analogue and preparation method thereof

A technology similar to moxifloxacin hydrochloride and its structure, which is applied in the field of new moxifloxacin hydrochloride structural analogs and its preparation, can solve the problems of the impact on the safety and effectiveness of the final drug delivery and the increase of impurity content, so as to ensure safety and reliability, The effect of simple operation and mild reaction conditions

Active Publication Date: 2016-03-23
NANJING CHIA TAI TIANQING PHARMA
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, during the stability test of the finished product of moxifloxacin hydrochloride, a new impurity with a new structure was found, and with the progress of the experiment, the content of the impurity increased significantly. The safety and effectiveness of the

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of moxifloxacin hydrochloride structural analogue and preparation method thereof
  • A kind of moxifloxacin hydrochloride structural analogue and preparation method thereof
  • A kind of moxifloxacin hydrochloride structural analogue and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the preparation of compound II

[0036] Add 57.0g of 2-cyclopentenone, 165.0g of N-methoxymethyl-N-trimethylsilylmethyl-benzylamine, and 750ml of DCM into a 1L three-necked flask, stir and cool. Slowly add 180ml of TFA dropwise, and control the internal temperature at -5~0°C. After the dropwise addition is completed, the temperature is raised, and the reaction is monitored by TLC until the end point. Pour the reaction solution into a pre-prepared 2M sodium hydroxide (3750ml) solution, add DCM (300ml*2) for extraction, combine the organic layers, dry over anhydrous magnesium sulfate, filter with suction, and concentrate under reduced pressure to obtain a brown oil (II) .

Embodiment 2

[0037] Embodiment 2: the preparation of compound III

[0038] Add 149.61g 2-benzylhexahydrocyclopenta[C]pyrrol-4-(1H)-one (II), 72.47g hydroxylamine hydrochloride, 144.07g potassium carbonate, 1500ml methanol and 52.5ml water in a 3L three-necked flask, Raise the temperature to reflux, stir, and monitor the reaction to the end point by TLC. After cooling to room temperature, it was filtered with suction, and the filtrate was concentrated under reduced pressure until no liquid dripped out. Add 800ml of water to the concentrated oil, extract with DCM (800ml*2), combine the organic phases, and dry over anhydrous magnesium sulfate. Suction filtration and concentration under reduced pressure gave 153.0 g of a brown oil, which was decolorized to give a white solid, namely compound III.

Embodiment 3

[0039] Embodiment 3: the preparation of compound IV

[0040] Add 17.42g of 2-benzylhexahydrocyclopenta[C]pyrrole-4-(1H)-ketoxime (Ⅲ), 8.71g of sodium hydroxide, 430ml of acetone and 160ml of water into a 1L three-necked flask, and divide Add 20.20 g of p-toluenesulfonyl chloride in batches, after the addition is complete, stir the reaction, and monitor the reaction to the end point by TLC. The reaction solution was extracted with DCM (250ml*2), the organic layers were combined, dried over anhydrous magnesium sulfate, filtered with suction, and concentrated under reduced pressure until there was no liquid drop, and 59.81g of a brown oil was obtained.

[0041] Add 42ml of glacial acetic acid and 42ml of acetic anhydride to the oil obtained above, stir, and monitor the reaction to the end point by TLC. Add 210ml of water, wash with ethyl acetate (50ml*2), adjust the pH of the water phase to 12-14 with 15% sodium hydroxide solution, wash with petroleum ether (50ml*3), and wash th...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a novel moxifloxacin hydrochloride structural analog 1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(4-oxo hexahydro-1H-pyrrolo[3,4-c] pyridine-6(2H)yl)-1,4-dihydroquinoline-3-carboxylic acid (I), a preparation method of the analog, and an application of the compound in quality control research on moxifloxacin hydrochloride.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to a novel moxifloxacin hydrochloride structural analog and a preparation method thereof. Background technique [0002] Moxifloxacin hydrochloride (moxifloxacinhydrochloride, 1-cyclopropyl-7-(S,S-2,8-diazo-bicyclo[4.3.0]nonan-8-yl)-6-fluoro-8-methoxy Base-1,4-dihydro-4-oxo-3-quinoline carboxylic acid hydrochloride) is the fourth-generation quinolone antibacterial drug developed by Bayer in Germany, which was first listed in Germany in September 1999. A widely used broad-spectrum antibacterial drug, which has the characteristics of broad-spectrum, high efficiency, low drug resistance, and low toxicity. The structural formula is as follows: [0003] [0004] The quality standards of this drug have been recorded in British Pharmacopoeia, European Pharmacopoeia and American Pharmacopoeia, which clearly indicate that it may contain 5 kinds of impurities A, B,...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 黄俊郭璇赵超钱修文柴雨柱朱谧徐丹杨治旻田舟山
Owner NANJING CHIA TAI TIANQING PHARMA