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Novel oxazolidinone compound and preparation method thereof

A compound and composition technology, applied in the field of new oxazolidinone compounds and their preparation, can solve the problems of linezolid with obvious side effects, increased risk of drug resistance, lack of platelets, etc., and achieve excellent antibacterial activity

Inactive Publication Date: 2016-11-23
BRIGHTGENE BIO MEDICAL TECH (SUZHOU) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Although there are a variety of drugs with good curative effects that provide a variety of clinical options, there are still many problems, such as vancomycin, the first-choice drug for the treatment of skin and skin structure infections, which has the risk of ototoxicity and nephrotoxicity, and drug resistance. Increased risk; and long-term use of linezolid has obvious side effects, such as platelet deficiency, flora disorder, increased mortality, and more drug-resistant strains, etc.

Method used

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  • Novel oxazolidinone compound and preparation method thereof
  • Novel oxazolidinone compound and preparation method thereof
  • Novel oxazolidinone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1 : Preparation of tedizolid phosphate dimeglumine (formula I' compound)

[0052]

[0053]

[0054] Add 10g (0.0222mol) tedizolid phosphate to 100ml water, add 8.67g (0.0444mol) N-methyl-D-glucamine dropwise to the above solution, after the dropwise addition, stir at room temperature for 1~2h , filtered the reaction solution, collected the mother liquor, and freeze-dried the mother liquor to obtain 18.54 g (99.3% yield) of a white solid, namely tedizolid dimethylglumine phosphate.

[0055] 1 H-NMR (DMSO-D 6 +D 2 O): δ8.90(s,1H), 8.22~8.16(m,2H), 7.73~7.66(m,2H), 7.51~7.48 (dd,1H), 4.88~4.84(m,1H), 4.44 ( s,3H), 4.15~4.10(t,1H), 4.00~3.96(dd,1H), 3.88~3.85(m,2H), 3.74~3.73(m,3H), 3.48~3.44(m,3H), 3.40~3.34(m,5H), 2.80~2.68(m,4H), 2.37~2.68(s,6H). Tedizolid Dimeglumine Phosphate 1 Please see Appendix 1 for the H-NMR spectrum.

Embodiment 2

[0056] Example 2 : Preparation of tedizolid phosphate dimeglumine (formula I' compound)

[0057] Add 10g (0.0222mol) tedizolid phosphate to 100ml water, add 13.0g (0.0666mol) N-methyl-D-glucamine dropwise to the above solution, after the dropwise addition, stir at room temperature for 1~2h , filtered the reaction solution, collected the mother liquor, and freeze-dried the mother liquor to obtain 18.57 g of white solid (yield 99.5%), namely tedizolid dimethylglumine phosphate.

[0058] 1 H-NMR (DMSO-D 6 +D 2 O): δ8.90(s,1H), 8.22~8.16(m,2H), 7.73~7.66(m,2H), 7.51~7.48 (dd,1H), 4.88~4.84(m,1H), 4.44 ( s,3H), 4.15~4.10(t,1H), 4.00~3.96(dd,1H), 3.88~3.85(m,2H), 3.74~3.73(m,3H), 3.48~3.44(m,3H), 3.40~3.34(m,5H), 2.80~2.68(m,4H), 2.37~2.68(s,6H).

Embodiment 3

[0059] Example 3 : Preparation of tedizolid monomeglumine phosphate (formula I'' compound)

[0060]

[0061] Add 10g (0.0222mol) tedizolid phosphate to 100ml water, add 4.34g (0.0222mol) N-methyl-D-glucamine dropwise to the above solution, after the dropwise addition, stir at room temperature for 1~2h , filtered the reaction solution, collected the mother liquor, and freeze-dried the mother liquor to obtain 14.2 g of white solid (yield 98.9%), namely tedizolid monomeglumine phosphate.

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PUM

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Abstract

The invention provides a novel oxazolidinone compound, a preparation method thereof and a medicine composition containing the compound and used for antibiotic. It is shown that the novel oxazolidinone compound has antibacterial activity on gram-positive bacteria like staphylococcus and enteric bacteria, and a new medicine choice is provided for clinical treatment of related diseases. Tedizolid phosphate reacts with N-methyl-D-glucosamine to prepare meglumine of tedizolid phosphoric acid, the technological method is simple, and the prepared compound has the advantages of being good in stability and suitable for preparing tablets and injections.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to novel oxazolidinone compounds, their preparation methods and their use as medicines. Background technique [0002] Oxazolidinones as a class of chemical constituents find wide application in drugs for the treatment and prevention of medical diseases such as bacterial infections and atherosclerosis. Various structures of oxazolidinone derivatives are known. For example, US4461773, US4476136, US4250318 and the like disclose mono-substituted or di-substituted derivatives of 3-phenyl-2-oxazolidinone. [0003] Pharmacia & Upjohn developed oxazolidinone derivatives represented by formulas 1 and 2 (WO93 / 23384, WO95 / 14684 and WO95 / 07271). Among them, the oxazolidinone derivative represented by formula 1 named "Zyvox" has successfully obtained the permission of the US Food and Drug Administration (FDA) and entered the market. However, it has been found that these conventional synthet...

Claims

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Application Information

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IPC IPC(8): C07F9/6558C07C213/08C07C215/10A61K31/675A61P31/04A61P31/06
Inventor 袁建栋陈耀杭文明
Owner BRIGHTGENE BIO MEDICAL TECH (SUZHOU) CO LTD
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