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7-(4,4-dimethyl 3-aminomethylpentazane-1-radicle) substituted, quinoline carboxylic acid derivative and its preparation

A dimethyl, carboxylic acid technology, applied in the direction of organic chemistry, antibacterial drugs, etc., can solve the problem of low activity of gram-positive bacteria

Inactive Publication Date: 2005-02-23
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Early quinolones have stronger antibacterial activity to Gram-negative bacteria, but lower activity to Gram-positive bacteria, although newly listed quinolones such as gatifloxacin (Drug, 1999,58 (4) : 683) and other antibacterial activities have been improved, but in general, the activity against Gram-positive bacteria needs to be further enhanced, and the antibacterial activity against some specific bacteria such as Streptococcus pneumoniae, Enterococcus, etc. needs to be enhanced

Method used

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  • 7-(4,4-dimethyl 3-aminomethylpentazane-1-radicle) substituted, quinoline carboxylic acid derivative and its preparation
  • 7-(4,4-dimethyl 3-aminomethylpentazane-1-radicle) substituted, quinoline carboxylic acid derivative and its preparation
  • 7-(4,4-dimethyl 3-aminomethylpentazane-1-radicle) substituted, quinoline carboxylic acid derivative and its preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Example 1 1-benzyl-3,3-dimethyl-2,4-dioxopyrrolidine

[0063] In a 1000ml three-neck flask equipped with a drying tube and a mechanical stirrer, add dry DMF (300ml), ethyl acetoacetate (130g, 1mol), add anhydrous potassium carbonate (286g, 2.2mol) under stirring, and drop Add iodomethane (390 g, 2.8 mol). After completion, the reaction was stirred at room temperature for 7 days. Filter off the solid, and wash the solid with dichloromethane (about 100ml), add water (500ml) to the filtrate, extract with dichloromethane (about 100ml×3), combine the organic layers, wash three times with water, dry over anhydrous magnesium sulfate, filter, and evaporate The solvent was dried to obtain light yellow oil (125 g, yield 79.0%).

[0064] In a 500ml three-necked flask, add the above compound oil (77g, 0.487mol), absolute ethanol (180ml), add bromine (77g, 0.481mol) dropwise under ice bath, complete, stir at room temperature for 2hr, evaporate under reduced pressure Add about hal...

Embodiment 2

[0070] Example 2 1-benzyl-3,3-dimethyl-2-oxo-4-ethoxycarbonylmethylenepyrrolidine

[0071] Add 60% sodium hydride (6.5g) to dry tetrahydrofuran (150ml), stir and cool down to 0°C ~ -5°C, add triethyl phosphonate dropwise, complete, stir at room temperature for 1.5hr, the reaction liquid is jelly-like , compound Example 1 (28.0 g, 0.129 mol) was added dropwise at room temperature. After completion, react at room temperature for 2 hr, dilute with ethyl acetate (300 ml), wash with saturated brine until neutral, dry over anhydrous magnesium sulfate, and evaporate the solvent to The oily product C-7 was obtained by drying (30.95 g, 83.6%).

[0072] 1 HNMR (CDCl 3 )δppm: 1.163~1.276 (3H, t, ethyl ester CH 3 ), 1.316 (6H, s, 3-2×CH 3 ), 4.066~4.135 (2H, q, ethyl ester CH 2 ), 4.342, 4.351 (2H, d, benzyl-CH 2 ), 4.524 (2H, s, 5-CH 2 ), 5.813~5.829 (1H, t, alkene=CH), 7.219~7.346 (5H, m, ArH)

[0073] EIMS: 287(M + ), 258 (M + -CO-H), 91(C 6 h 5 CH 2 + )

Embodiment 3

[0074] Example 3 1-benzyl-3,3-dimethyl-2-oxo-4-ethoxycarbonylmethylpyrrolidine

[0075] Add absolute ethanol (700ml), active nickel and the compound of Compound Example 2 (30.95g, 0.108mol), and react at room temperature under 40-50psi hydrogen pressure for 12hr. TLC shows that the reaction is complete, and the nickel powder is filtered off, and the solvent is evaporated to After drying, a pale yellow oil (29.3 g, 94.0%) was obtained.

[0076] 1 HNMR (CDCl 3 )δppm: 0.970 (3H, s, 3-CH 3 ), 1.187 (3H, s, 3-CH 3 ), 1.187~1.244 (3H, t, ethyl ester CH 3 , J=7.8Hz), 2.197~2.253 (1H, m, 4-CH), 2.403~2.478 (2H, m, side chain CH 2 ), 2.789~2.850, 3.330~3.387 (2H, tt, 5-CH 2 , coupled with hydrocarbons, J=9Hz), 4.060~4.131 (2H, q, ethyl ester CH 2 , J=7.2Hz), 4.297~4.575 (2H, dd, benzyl-CH 2 ), 7.180~7.314 (5H, m, ArH)

[0077] EIMS: 289(M + ), 244 (M + -OEt), 114(C 6 h 5 N=CH 2 ), 91(C 6 h 5 CH 2 + )

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Abstract

A 7-(4,4-dimethyl-3-aminomethyl pyrrolidine-1-yl) substituted neoquinoline carbonic acid derivative, which can be used as antibacterial agent or feed additive, and its preparing process are disclosed.

Description

Technical field: [0001] The present invention relates to new fluoroquinolones and naphthyridone formic acid derivatives with excellent antibacterial activity and their preparation methods; and to antibacterial agents and feed additives containing them. Background technique: [0002] Quinolones have developed from nalidixic acid (J.Med.Chem.1962, 5, 1063) in 1962 to now a class of broad-spectrum, high-efficiency, low-toxic synthetic drugs. Early quinolones have stronger antibacterial activity to Gram-negative bacteria, but lower activity to Gram-positive bacteria, although newly listed quinolones such as gatifloxacin (Drug, 1999,58 (4) : 683) etc. have improved antibacterial activity, but generally speaking, the activity against Gram-positive bacteria needs to be further enhanced, and it is necessary to enhance the antibacterial activity to some specific bacteria such as Streptococcus pneumoniae, Enterococcus etc. simultaneously. [0003] It has been reported (JP05,345,777; ...

Claims

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Application Information

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IPC IPC(8): A61P31/04C07D215/56C07D471/04
Inventor 郭慧元王玉成刘九雨王秀云
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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