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Novel glycopeptide antibiotic derivative and pharmaceutical composition, and preparation method and purpose thereof

A technology of glycopeptide antibiotics and derivatives, applied in the field of medicinal chemical synthesis, can solve problems such as the threat of clinical anti-infective treatment and the decrease of vancomycin sensitivity.

Active Publication Date: 2012-09-26
ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the empirical treatment of MRSA with glycopeptide antibiotics has led to the development of bacterial resistance, for example, the sensitivity of MRSA to vancomycin has decreased, which will pose a serious threat to clinical anti-infective treatment. New glycopeptide antibiotics effective against drug-resistant strains are imminent
[0003] Chinese patent 200910053906.9 reports a new type of glycopeptide compound, the structure of which is shown as compound (II) of the present invention, which has antibacterial activity. Research on structural modification has not been reported in the literature

Method used

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  • Novel glycopeptide antibiotic derivative and pharmaceutical composition, and preparation method and purpose thereof
  • Novel glycopeptide antibiotic derivative and pharmaceutical composition, and preparation method and purpose thereof
  • Novel glycopeptide antibiotic derivative and pharmaceutical composition, and preparation method and purpose thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the synthesis of compound 1

[0039] At room temperature, the compound represented by general formula (II) (500mg, 0.31mmol) was dissolved in 10mlDMF / methanol (1:1), and 4-bromobenzaldehyde (63mg, 0.34mmol) was added, and the reaction solution was heated at 60°C Heat and stir for 2 hours, cool to room temperature, add sodium cyanoborohydride (40mg, 0.62mmol), stir at room temperature for 2 hours, evaporate the methanol from the reaction solution under reduced pressure, pour the residue into 70ml acetone to precipitate precipitate, suction filter, wash with acetone , purified by preparative HPLC to obtain 100 mg of the final product (Compound 1), with a yield of 18.4%.

Embodiment 2

[0040] Embodiment 2: the synthesis of compound 1

[0041]The compound represented by general formula (II) (300mg, 0.19mmol) was dissolved in 6mlDMF / methanol (1:1), 4-bromobenzaldehyde (70mg, 0.38mmol) was added, the reaction solution was stirred at 0°C for 3 hours, and Sodium cyanoborohydride (24 mg, 0.38 mmol), stirred at room temperature for 2 hours, the reaction solution was evaporated under reduced pressure to remove methanol, the residue was poured into 50 ml of acetone to precipitate a precipitate, filtered by suction, washed with acetone, and purified by preparative HPLC to obtain the final product (Compound 1) 50 mg, yield 14.7%.

[0042] 1 H-NMR (400MHz, DMSO-d 6 +D 2 O)δ(ppm): 7.81(2H), 7.59-7.23(8H), 6.79(3H), 6.50(1H), 6.35(2H), 5.86-5.13(7H), 4.95-4.20(10H), 3.55- 2.50(6H), 2.45-2.00(4H), 1.90-0.95(15H), 0.89-0.84(6H).

Embodiment 3

[0043] Embodiment 3: the synthesis of compound 10

[0044] The compound represented by general formula (II) (500mg, 0.31mmol) was dissolved in 10ml of DMF / methanol (1:1), 4'-chloro-biphenylcarbaldehyde (100mg, 0.46mmol) was added, and the reaction solution was heated at 65°C After stirring for 2 hours, cool to room temperature, add sodium cyanoborohydride (40 mg, 0.62 mmol), and stir at room temperature for 2 hours. The reaction solution was evaporated to remove methanol under reduced pressure, and the residue was poured into 70 ml of acetone to precipitate a precipitate. Suction filtration, washing with acetone, Purified by preparative HPLC to obtain 130 mg of the final product (compound 10), with a yield of 23.5%.

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Abstract

The invention discloses a glycopeptide antibiotic derivative shown as a general formula (I) and pharmaceutically accepted salt thereof, and a preparation method thereof. R1 represents C3-9 saturated fatty alkyl, decylamine methyl or an aromatic group, which is unsubstituted or substituted phenyl ring, biphenyl ring or naphthalene ring; and a substituent of the phenyl ring, biphenyl ring or naphthalene ring is one or more selected from the group of halogen, hydroxy, amino, C1-9 alkyloxy, nitro and isopropyl. R2 represents H or CH2-R3. R3 represents C3-9 saturated aliphatic hydrocarbon group. In addition, the invention also provides a pharmaceutical composition containing the glycopeptide antibiotic derivative and pharmaceutically acceptable salt thereof as active components, and application thereof. The compound and pharmaceutical composition provided by the invention have good antibiosis activity and great significance for development of novel antibacterial medicament.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical chemical synthesis, and relates to a novel glycopeptide antibiotic derivative and its pharmaceutically acceptable salt, preparation method and application. Background technique [0002] Glycopeptide antibiotics are the drug of choice for clinical treatment of methicillin-resistant Staphylococcus aureus (MRSA) infection. However, the empirical treatment of MRSA with glycopeptide antibiotics has led to the development of bacterial resistance, such as the decreased sensitivity of MRSA to vancomycin, which will pose a serious threat to clinical anti-infective treatment. New glycopeptide antibiotics effective against drug-resistant strains are imminent. [0003] Chinese patent 200910053906.9 reports a new type of glycopeptide compound, the structure of which is shown as compound (II) of the present invention, which has antibacterial activity. There is no literature report on the research of st...

Claims

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Application Information

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IPC IPC(8): C07K9/00C07K1/107A61K38/14A61P31/04
CPCA61K38/00C07K9/006
Inventor 邵昌周伟澄魏维蒋晓岳张顺利孙新强阮林高沈芳李秋爽周亭戈梅罗敏玉
Owner ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
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