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A kind of hybrid compound of macrolide and quinolone and preparation method thereof

A technology of macrolide and quinolone, which is applied in chemical synthesis and pharmaceutical fields, and can solve the problem of low activity of Streptococcus pneumoniae

Active Publication Date: 2021-06-11
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, it is necessary to find a new structure, which is different from telithromycin, which has hepatotoxicity, and overcomes the defect that the current 9-oximone lactone has very low activity against constitutive Streptococcus pneumoniae. Staphylococcus, etc. also have antibacterial activity, which is clinically used for pneumonia caused by pathogenic microorganisms including Streptococcus pneumoniae

Method used

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  • A kind of hybrid compound of macrolide and quinolone and preparation method thereof
  • A kind of hybrid compound of macrolide and quinolone and preparation method thereof
  • A kind of hybrid compound of macrolide and quinolone and preparation method thereof

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Embodiment 1

[0024] The present invention provides a hybrid of macrolide and quinolone, the hybrid of macrolide and quinolone is a compound with general formula I and formula II, or, the hybrid of macrolide and quinolone Compounds include pharmaceutically acceptable salts formed by compounds of the general formula I and II and inorganic acids or organic acids, which are metabolized or converted into the general structure as prodrugs under physiological conditions in vivo. Shown compound, and plays a pharmacological role as an active ingredient. In the embodiments of the present invention, various pharmaceutically acceptable acids can form salts on the nitrogen of 5-O-desosamine dimethylamino in general formula I and general formula II, and the prodrug is esterified on the 2'-OH , similar as erythromycin ethyl succinate as a prodrug, the ester group can be hydrolyzed in vivo to release 2'-OH again. Conventional methods for the preparation of prodrugs can be found in Design of Prodrugs (H. ...

Embodiment 2

[0081] The reaction scheme of a kind of macrolide and quinolone hybrid in the embodiment of the present invention is as follows, and described macrolide and quinolone hybrid are the compound with general formula II, prepare as shown in general formula II The method of described macrolide and quinolone hybrid specifically can comprise the following steps:

[0082]

[0083] The reaction conditions are: (a) acetic anhydride, methylene chloride; (b) potassium tert-butoxide, 80% propargyl bromide, dimethyl sulfoxide / tetrahydrofuran (1:1); (c) pyridine, triphosgene, Dichloromethane, -10℃-room temperature; (d) N-chlorosuccinimide (NCS), dimethyl sulfide (DMS), triethylamine, dichloromethane, -15--5℃; (e ) N-fluorobenzenesulfonimide (NFSI), NaH, N, N-dimethylformamide, -5-0°C; (f) ArBr or ArI, CuI, bis(triphenylphosphine) dichloride Palladium chloride, triethylamine, 80°C, acetonitrile; (g) 65°C, methanol.

[0084] In order to enable those skilled in the art to better understand ...

Embodiment 3

[0140] The reaction scheme of a kind of macrolide and quinolone hybrid in the embodiment of the present invention is as follows, and described macrolide and quinolone hybrid are the compound with general formula I, prepare as shown in general formula I The method of described macrolide and quinolone hybrid specifically can comprise the following steps:

[0141]

[0142] The reaction conditions are: (a) potassium tert-butoxide, allyl bromide, dimethyl sulfoxide / tetrahydrofuran (1:1); (b) pyridine, triphosgene, dichloromethane, -10°C-room temperature; (c ) N-chlorosuccinimide (NCS), dimethyl sulfide (DMS), triethylamine, dichloromethane, -15--5 ° C; (d) N-fluorobenzenesulfonimide (NFSI ), NaH, N, N-dimethylformamide, -5-0°C; (e) ArBr or ArI, palladium acetate, tris(o-methylphenyl)phosphorus, triethylamine, 60-90°C, acetonitrile ; (f) 65°C, methanol.

[0143] In order to enable those skilled in the art to better understand the present invention, the preparation method of the...

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Abstract

The present invention provides a macrocyclic lactone and quinolone hybrid, characterized in that the macrocyclic lactone and quinolone hybrid include compounds with general formula I and general formula II, or, the macrocyclic lactone and quinolone hybrids include pharmaceutically acceptable salts formed by compounds of the general formula I and II and inorganic acids or organic acids, and the macrolide and quinolone hybrids can be better adapted to industrial production , and has good anti-susceptible and anti-drug resistance against common clinical erythromycin-resistant Streptococcus pneumoniae, Staphylococcus aureus, Streptococcus pyogenes, Mora catarrhalis and Haemophilus influenzae Bacterial activity, can effectively treat clinical bacterial pneumonia or pneumonia caused by other microorganisms (such as mycoplasma, Legionella, etc.), and other tissue infections;

Description

technical field [0001] The invention relates to the fields of chemical synthesis and pharmacy, in particular to a macrolide and quinolone hybrid and a method for preparing the macrolide and quinolone hybrid. Background technique [0002] Fourteen-membered macrolide antibiotics-erythromycin (erythromycin) is a very important drug for the treatment of respiratory tract infections. It has provided humans with an efficient and safe way to use drugs for half a century. play an irreplaceable role. At present, more and more strains of respiratory pathogens isolated clinically show drug resistance, such as Streptococcus pneumoniae (S.pneumoniae), Staphylococcus aureus (S.aureus) and Streptococcus pyogenes (S.pyogenes). In particular, there are more and more isolated strains of multi-drug resistance clinically, and some strains of Staphylococcus aureus are even resistant to various antibacterial drugs with different antibacterial mechanisms such as macrolides, β-lactams, and quinolo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/08C07H1/00A61P31/04A61P11/00A61K31/7048
CPCY02A50/30
Inventor 梁建华马聪璇
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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