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Novel glycopeptide antibiotic derivatives and pharmaceutical composition, as well as its preparation method and use
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A technology of glycopeptide antibiotics and derivatives is applied in the field of preparation of glycopeptide antibiotic derivatives and pharmaceutically acceptable salts thereof, and can solve the problems of the threat of clinical anti-infective treatment and the decrease of vancomycin sensitivity.
Active Publication Date: 2017-06-27
ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY +1
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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
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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%.
[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 present invention discloses a class of glycopeptide antibiotic derivatives represented by the general formula (I), pharmaceutically acceptable salts thereof and a preparation method thereof, wherein R1 is a C3-C9 saturated aliphatic hydrocarbon group, decylaminomethyl group, or Aromatic group, the aromatic group is an unsubstituted or substituted benzene ring, biphenyl ring, or naphthalene ring, and the substituent of the benzene ring, biphenyl ring, or naphthalene ring is one or more halogen, hydroxyl, Amino, C1-C9 alkoxy, nitro, or isopropyl; R2 is H or CH2-R3, R3 is C3-C9 saturated aliphatic hydrocarbon group. In addition, the present invention also provides pharmaceutical compositions containing the glycopeptide antibiotic derivatives and pharmaceutically acceptable salts thereof as active ingredients and applications thereof. The compounds and pharmaceutical compositions provided by the invention have good antibacterial activity and are of great significance for the development of new antibacterial drugs.
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] Glycopeptideantibiotics 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...
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Patent Type & Authority Patents(China)
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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