Pleuromutilin compound, preparation method of pleuromutilin compound, polymorphism and preparation method of polymorphism

A technology for pleuromutilin and compounds, applied in the field of drug synthesis, to achieve the effects of high reaction yield, simple synthesis process, and simple treatment method

Inactive Publication Date: 2016-03-16
LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the overuse of antibiotics has led to serious drug resistance in many bacteria

Method used

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  • Pleuromutilin compound, preparation method of pleuromutilin compound, polymorphism and preparation method of polymorphism
  • Pleuromutilin compound, preparation method of pleuromutilin compound, polymorphism and preparation method of polymorphism
  • Pleuromutilin compound, preparation method of pleuromutilin compound, polymorphism and preparation method of polymorphism

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Experimental program
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Embodiment 1

[0045] Embodiment 1: A kind of pleuromutilin compound

[0046] A pleuromutilin compound, which is 14-O-[(4-amino-6-hydroxy-pyrimidin-2-yl) mercaptoacetyl] Mutilin formula (i), and 14-O-[(4 -Amino-6-keto-pyrimidin-2-yl)thioacetyl]Multiline (formula ii), wherein 14-O-[(4-amino-6-keto-pyrimidin-2-yl)thioacetyl] Mutilin (formula ii) is another conformation of 14-O-[(4-amino-6-hydroxy-pyrimidin-2-yl)thioacetyl] Mutilin formula (i).

Embodiment 2

[0048] The preparation method of pleuromutilin compounds described in Example 1: 4.45 g of pleuromutilin (0.01 mol) with a purity of 85%, 2.10 g of p-toluenesulfonyl chloride (0.01 mol) and 40 mL of methyl iso Butanone (methylisobutylketone, MIBK) was added into a 100mL three-necked flask, heated and stirred to dissolve pleuromutilin and p-toluenesulfonyl chloride. When the temperature rose to 60°C, 2.2mL of 10N NaOH aqueous solution was added dropwise, and the reaction 30min; then the pH value of the reaction solution was adjusted to 8-9 with 5N hydrochloric acid, and 1.65g of 4-amino-6-hydroxy-2-mercaptopyrimidine sodium salt (0.01mol) (4-amino-6-hydroxy-2-mercapto The preparation method of the sodium salt of pyrimidine is to dissolve NaOH in methanol, add dropwise 4-amino-6-hydroxy-2-mercaptopyrimidine, and stir for 30 minutes to obtain), continue the reaction at 60°C for 5 hours, and evaporate to dryness under reduced pressure Add 20mL of water and 20mL of tert-butyl methy...

Embodiment 3

[0051] The preparation method of pleuromutilin compounds described in Implementation 1: 4.45 g of pleuromutilin (0.01 mol) with a purity of 85%, 2.10 g of p-toluenesulfonyl chloride (0.01 mol) and 40 mL of methyl isobutyl Add ketone (methylisobutylketone, MIBK) into a 100mL three-necked flask, heat up, and stir to dissolve pleuromutilin and p-toluenesulfonyl chloride. When the temperature rises to 50°C, add 2.2mL of 10N NaOH aqueous solution dropwise, and react for 60min ; Then the reaction solution was adjusted to pH 8-9 with 5N hydrochloric acid, and 1.65 g of 4-amino-6-hydroxyl-2-mercaptopyrimidine sodium salt (0.01mol) was added (4-amino-6-hydroxyl-2-mercaptopyrimidine The preparation method of the sodium salt is to dissolve NaOH in methanol, dropwise add 4-amino-6-hydroxy-2-mercaptopyrimidine, and stir for 30 minutes to obtain), continue to react at 50°C for 6 hours, and evaporate MIBK to dryness under reduced pressure , add 20mL of water and 20mL of tert-butyl methyl eth...

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Abstract

The invention discloses a preparation method of a pleuromutilin compound, a polymorphism and a preparation method of the polymorphism. The pleuromutilin compound comprises a 14-O-[(4-amino-6-hydroxy-pyrimidine-2-yl) thio acetyl] matrix shown in a structural formula (i) and / or a 14-O-[(4-amino-6-one-pyrimidine-2-yl) thio acetyl] matrix shown in a structural formula (ii). The novel pleuromutilin compound disclosed by the invention has obvious inhibiting effects on multiple drug resistant bacteria such as methicillin resistant staphylococcus aureus and staphylococcus epidermidis as well as common pathogenic bacteria such as escherichia coli and streptococcus mastitidis in veterinary clinics, so that the pleuromutilin compound can be applied to preparation of antibacterial drugs and particularly anti-drug resistant bacterium drugs.

Description

technical field [0001] The invention relates to a pleuromutilin compound, a preparation method, a polymorph and a preparation method of the polymorph, and belongs to the field of drug synthesis. Background technique [0002] The discovery of antibiotics has played an important role in human history. However, the overuse of antibiotics has led to serious drug resistance in many bacteria. Drug-resistant bacteria, especially Staphylococcus pneumoniae, Streptococcus pneumoniae, Mycobacterium tuberculosis, etc., cause more than two million deaths every year, seriously threatening human health. Therefore, it is particularly important to develop new anti-drug-resistant fungal drugs. [0003] Pleuromutilin (see formula i for chemical structure) was first obtained from higher fungi in the 1950s Pleurotus multilus (Fr.) Sacc. and Pleurotus Passecke-rianus Pilat A diterpenoid compound with antibacterial activity was isolated from The compound consists of a 5-6-8 three-membered ri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/46A61P31/04
CPCC07D239/46C07B2200/13
Inventor 尚若锋衣云鹏梁剑平刘宇郝宝成郭志廷
Owner LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS
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