Macrolide and carbostyril heterocomplex and preparation method thereof

A macrolide and quinolone technology, applied in the preparation of macrolide and quinolone hybrids, in the field of macrolide and quinolone hybrids, can solve the problems of low activity of Streptococcus pneumoniae and the like

Active Publication Date: 2019-06-28
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 aga...

Method used

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  • Macrolide and carbostyril heterocomplex and preparation method thereof
  • Macrolide and carbostyril heterocomplex and preparation method thereof
  • Macrolide and carbostyril heterocomplex and preparation method thereof

Examples

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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 invention provides a macrolide and carbostyril heterocomplex. The macrolide and carbostyril heterocomplex is characterized by comprising compounds shown in the formula I and the formula II, or thecompounds shown in the formula I and the formula II and salt formed by inorganic acid or organic acid and accepted by pharmacy, the macrolide and carbostyril heterocomplex can better adapt to industrial production and has good activity of resisting sensitive bacteria and drug-resistance bacteria on clinically common streptococcus pneumoniae, staphylococcus aureus, streptococcus pyogenes, catarrhmoraxella catarrhalis, haemophilus influenza and other pathogenic bacteria which are capable of resisting erythrocin, and clinical bacterial pneumonia or pneumonia caused by other microorganisms (suchas mycoplasma, legionella and the like) and other tissue infections can be effectively treated.

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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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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