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Azithromycin derivative and its use

A technology of azithromycin and derivatives, applied in the field of azithromycin derivatives, can solve the problems of poor activity of macrolide-resistant bacteria

Inactive Publication Date: 2007-11-21
SHANGHAI INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] But these antibiotics are still poorly active against macrolide-resistant bacteria

Method used

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  • Azithromycin derivative and its use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Example 1 4"-(2-benzylidene) carbazate azithromycin (compound 1)

[0062]Synthesize 4"-carbazate azithromycin (F) (0.620mmol), benzaldehyde (1.240mmol) and acetic acid (1.860mmol) according to the general method, then evaporate the solvent, add ethyl acetate to dissolve, wash with water, and anhydrous Dry over sodium sulfate, filter, evaporate the solvent to dryness under reduced pressure, dry column chromatography, successively use ethyl acetate:petroleum ether:diethylamine volume ratio as 3:5:0.5 and 5:5:1 as eluent, 0.476 g of the product was obtained, and the yield was 85.8%.

[0063] MS(ESI+):895[M+H] + . 1 HNMR (400M, CDCl 3 )δ 8.3 (1H, s), 7.9 (1H, s), 7.7 (2H, m), 7.4 (3H, m), 5.2 (1H, d, 11-CH-), 4.7 (1H, d), 4.5 (1H, d), 4.3 (1H, m), 3.35 (3H, s, 3"-OCH 3 ), 2.25(6H, s, 3'-N(CH 3 ) 2 ).

Embodiment 2

[0064] Example 2 4"-[2-(2-phenylvinylmethylene)]carbazate azithromycin (compound 2)

[0065] Synthesize 4"-carbazate azithromycin (F) (0.620mmol), cinnamaldehyde (1.240mmol) and acetic acid (1.860mmol) according to the general method, evaporate the solvent, add ethyl acetate to dissolve, wash with water, anhydrous sulfuric acid Sodium drying, filtration, evaporated to dryness under reduced pressure, dry column chromatography, the volume ratio of ethyl acetate:petroleum ether:diethylamine is 3:4:0.5 as eluent, and the product is 0.098g, yield 17.2% .

[0066] MS(ESI+):921[M+H] + . 1 HNMR (400M, CDCl 3 )δ 8.9 (1H, s), 7.8 (1H, s), 7.3 (5H, m), 6.9 (1H, s), 6.8 (1H, s), 5.2 (1H, d, 11-CH-), 4.7 (1H,d), 4.5(1H,d), 4.3(1H,m), 3.35(3H,s,3"-OCH 3 ), 2.35(6H, s, 3'-N(CH 3 ) 2 ).

[0067] 13 CNMR (400M, CDCl 3 )δ 178.5, 148.0, 138.7, 135.8, 128.8, 128.8, 128.7, 126.8, 125.0, 102.6, 95.0, 83.9, 79.9, 78.5, 77.4, 77.3, 77.0, 76.7, 74.2, 73.5, 73.1, 79.06, 67. 63.2, 62.3, 60.3,...

Embodiment 3

[0068] Example 3 4"-[2-(4-methoxybenzylidene)]carbazate azithromycin (compound 3)

[0069] Synthesize 4"-carbazate azithromycin (F) (0.620mmol), p-methoxybenzaldehyde (1.240mmol) and acetic acid (1.860mmol) according to the general method, evaporate the solvent, add ethyl acetate to dissolve, wash with water , dried over anhydrous sodium sulfate, filtered, evaporated to dryness under reduced pressure, dry column chromatography, ethyl acetate: petroleum ether: diethylamine volume ratio is 3: 5: 0.5 as eluent, to obtain yellowish foam Add ethyl acetate to dissolve, add water to stir, cool in an ice-water bath, adjust the pH of the solution to 3 with 1.0N hydrochloric acid, and separate the water phase. Under the condition of continued cooling in the ice-water bath, adjust the pH to 9 with 3.0N sodium hydroxide solution , extracted with ethyl acetate, combined the organic phases, washed with water, anhydrous Na 2 SO 4 After drying, filtering, and evaporating the solvent under r...

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PUM

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Abstract

An azithromycin derivative, its medicinal acceptable salt and its usage are disclosed. In structural formula of medicinal acceptable salt, IR is -R1 or -A-R1; A is C1-5 alkylene, C2-5 vinylene, C2-5 acetylene, C3-6 naphthelene, 3-6 valence heterocyclene or C6-10 arylene containing 1-2 selected from N, O and S hetero-atom; R1 is 5-15 valence aromatic nucleus containing 0-3 selected from N, O and S hetero-atom, which can be substituted by various substituting group. It can be used to prepare medicines in treatment and prevention of infectious diseases.

Description

technical field [0001] The invention discloses an azithromycin derivative and application thereof. Background technique [0002] Erythromycin is still widely used because of its good antibacterial activity and safety. In the 1980s, the second-generation macrolide antibiotics such as clarithromycin, roxithromycin, dirithromycin, and azithromycin came out successively. Compared with erythromycin, this type of antibiotic has enhanced acid resistance, expanded antibacterial spectrum, and improved pharmacokinetic properties. It has strong antibacterial activity against Gram-positive bacteria, some Gram-negative bacteria, mycoplasma, etc., and has been widely used by these antibiotics. A medicine for treating infections caused by bacteria. Some of them have been used clinically as excellent antibiotics. For example, azithromycin (see U.S. Patents USP 4,474,768 and USP 4,517,359 J.Chem.Research (S) (1988) 152, J.Chem.Research (M) (1988) 1239 ) has the following structure: [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/08A61K31/7052A61K31/04
Inventor 沈舜义王章跃朱传娴葛涵
Owner SHANGHAI INST OF PHARMA IND
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