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Erythromycin A derivative and preparation method thereof

A technology of erythromycin and its derivatives, which is applied in the field of erythromycin A derivatives and its preparation, and can solve the problems of poor activity of drug-resistant bacteria and the like

Inactive Publication Date: 2012-03-21
SHANGHAI INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With the increasingly serious problem of drug-resistant bacteria worldwide, the second-generation macrolide antibiotics show their weakness of poor activity against drug-resistant bacteria

Method used

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  • Erythromycin A derivative and preparation method thereof
  • Erythromycin A derivative and preparation method thereof
  • Erythromycin A derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0110] Example 1 9-hydrazone erythromycin thiocyanate A (intermediate 12)

[0111] Erythromycin thiocyanate A (40g, 0.0504mol) was dissolved in methanol (40ml), and 85% hydrazine hydrate (4.3ml, 0.0757mol) was added, heated to reflux for 18h and then cooled to precipitate a solid, filtered, and the filter cake was washed with water to obtain a white solid Intermediate 12 (27.1 g, 66.6%).

Embodiment 2

[0112] Example 2 9-hydrazone erythromycin A (intermediate 13)

[0113] 9-hydrazone erythromycin thiocyanate A (20g, 0.0248mol) was dissolved in dichloromethane (400ml)-water (400ml), adjusted to pH 9-10 with 3mol / L sodium hydroxide solution, separated the organic phase, After washing with water, drying with anhydrous sodium sulfate, and filtering, the filtrate was evaporated to dryness under reduced pressure to obtain intermediate 13 (14.0 g, 75.7%) as a white foam.

[0114] MS (ESI + , m / e): 748 [M+H] +

Embodiment 3

[0115] Example 3 9-(propane-2-ylidene hydrazono)erythromycin A (intermediate 15)

[0116] 9-Hydrazone erythromycin A (5.00g, 6.69mmol) was dissolved in acetone (15ml), heated to reflux for 2h and then cooled. A solid precipitated and was filtered to give white solid intermediate 15 (4.70g, 89.2%).

[0117] MS (ESI + , m / e): 788 [M+H] +

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Abstract

The invention discloses an erythromycin A derivative and a preparation method thereof. R1 and R2 are independently H, C1-C6 alkyl groups, substituted or unsubstituted C6-C10 aromatic groups, or substituted or unsubstituted C4-C8 heteroaryls; or R1 and R2 are connected to form (CH2)n, wherein n is 2-7; substitutional groups of the aromatic groups or the heteroaryls are one or more of C1-C6 alkoxyl groups, the C1-C6 alkyl groups and the C6-C10 aromatic groups; a hetero atom in the heteroaryls is S, O or N; R is H or groups shown in the description; R3 is the C1-C6 alkyl groups substituted by the substituted or unsubstituted C6-C10 aromatic groups; the substitutional groups of the C6-C10 aromatic groups are nitro groups; and R4 is carbonyl groups or H substituted by the C1-C6 alkyl groups. The compound disclosed by the invention has stronger antibiotic activity, particular for gram positive bacteria.

Description

technical field [0001] The present invention specifically relates to an erythromycin A derivative and a preparation method thereof. Background technique [0002] In the more than 20 years when the antibacterial mechanism of erythromycin A has not been elucidated, the chemical modification of erythromycin A is mainly limited to the preparation of various erythromycin A esters or salts to improve its water solubility or reduce bitterness, enhance antibacterial activity, Improve pharmacokinetic properties and reduce toxic and side effects to obtain better clinical effects. [0003] [0004] Formula 1-1 second generation macrolide antibiotics [0005] By the 1970s, research results on the pharmacological mechanism of erythromycin A, the relationship between acid stability and pharmacokinetic properties, and the causes of gastrointestinal irritation and side effects of erythromycin A were reported successively. The work has entered a new stage. Since the 1980s, aiming at th...

Claims

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Application Information

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IPC IPC(8): C07H17/08C07H1/00A61P31/04
Inventor 沈舜义葛涵张芸徐屹军
Owner SHANGHAI INST OF PHARMA IND
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