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Beta-lactam compound and application and preparation method thereof

A compound and technology of general formula, applied in the field of beta-lactam compounds and their preparation, to achieve the effects of low drug resistance and excellent antibacterial activity

Active Publication Date: 2021-12-07
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

However, there is still a lot of room for improvement in drug resistance of aztreonam derivatives currently available

Method used

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  • Beta-lactam compound and application and preparation method thereof
  • Beta-lactam compound and application and preparation method thereof
  • Beta-lactam compound and application and preparation method thereof

Examples

Experimental program
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preparation example Construction

[0093] In another aspect of the present invention, the preparation method of the compound represented by the following general formula (I) is provided, which comprises:

[0094] Step a:

[0095] By reacting the compound shown in the following formula (1) and the compound shown in the formula (2), the compound shown in the formula (3) is generated;

[0096]

[0097] In the above formulas, PG represents a protecting group;

[0098] R 1 , R 2 Each independently represents a hydrogen atom, a C1-10 straight-chain or branched alkyl group optionally with substituents, or both form a cycloalkyl group with a ring carbon number of 3 to 8; R 3 , R 4 Each independently represents a hydrogen atom, a C1-10 linear or branched alkyl group optionally having a substituent, a C6-12 aryl group optionally having a substituent, or both together form a ring with 3 to 3 carbon atoms. 8 cycloalkyl group; X represents C or N; Y represents a straight-chain or branched alkenyl or alkynyl group or...

Embodiment

[0192] Hereinafter, the present invention will be described in more detail using production examples, test examples, and the like, but the present invention is not limited to these examples.

[0193] The specific synthetic route of compound (A-1)~(A-7) is as follows:

[0194]

manufacture example 1

[0196] Production Example 1: Synthesis of Compound (A-1)

[0197]

[0198] Step 1a (Step 1a): Compound 7a (1.0mmol) was dissolved in DMF (10.0v / g), triethylamine (2.0mmol) was added, triphenylchloromethane (1.2mmol) was added in batches, and the reaction was stirred at room temperature After 6 hours, TLC monitoring, after the reaction is complete, add water / ethyl acetate for extraction, combine the organic phases, dry and concentrate, and separate by column chromatography to obtain the target compound 7b.

[0199] Step 1b (Step 1b): Dissolve compound 7b (1.0mmol) in 1,4-dioxane (5v / g) / water (5v / g), stir at room temperature, add sodium hydroxide (5.0mmol), Continue to stir the reaction, TLC monitors, the raw material disappears, distill out 1,4-dioxane under reduced pressure, adjust the pH to 2-3, stir for 10 minutes, filter, wash the filter cake with water until the filtrate is neutral, collect and dry the filter cake to obtain compound 7c.

[0200] Step 1 (Step 1): compo...

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PUM

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Abstract

The invention relates to a beta-lactam compound and application and a preparation method thereof, and relates to a compound as shown in the following general formula (I), which has good antibacterial property on bacteria, especially gram-negative bacteria, low drug resistance and good prospect of effectively treating various diseases (in the formula (I), R1 and R2 each independently represent a hydrogen atom, a C1-10 linear or branched alkyl group optionally having a substituent, or both together form a cycloalkyl group having 3 to 8 ring carbon atoms; R3 and R4 each independently represent a hydrogen atom, a C1-10 linear or branched alkyl group optionally having a substituent, and a C6-C12 aryl group optionally having a substituent, or both together form a cycloalkyl group having 3 to 8 ring carbon atoms; X represents C or N; and Y represents a linear or branched alkenyl or alkynyl group having 2-6 carbon atoms, which may have a substituent, or a carboxyl group. ).

Description

technical field [0001] The invention relates to a novel β-lactam compound and a preparation method thereof. The β-lactam compound has good antibacterial properties against bacteria, especially Gram-negative bacteria, and has extremely low drug resistance, and is suitable for preparing antibacterial agents with excellent performance. Background technique [0002] So far, a variety of antibacterial agents have been developed, such as β-lactams, aminoglycosides, tetracyclines, fluoroquinolones, glycopeptides, macrolides, etc. Among them, β-lactams, such as aztreonam shown in the following formula, have become the most important for the treatment of severe bacterial infections because of their broad antibacterial spectrum, strong antibacterial activity, stability to β-lactamase, etc., and low toxicity. one of the antibacterial drugs. However, the antibacterial activity of aztreonam against some bacteria, especially Gram-negative bacteria, is not ideal. In view of this, the syn...

Claims

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Application Information

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IPC IPC(8): C07D417/12A61K31/427A61K31/433A61P31/04
CPCC07D417/12A61P31/04Y02A50/30Y02P20/55
Inventor 宋丹青唐胜游雪甫李志文汪燕翔卢曦李迎红胡辛欣郭志浩王秀坤
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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