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Benzothiazine derivative, a preparation method and uses thereof

A technology of benzothiazine and derivatives, which is applied in the field of benzothiazine derivatives and its preparation, and can solve problems such as inability to guarantee compounds

Active Publication Date: 2018-08-28
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

DprE1 enzyme is a promising anti-mycobacterium tuberculosis target, and none of the inhibitors developed for it has entered the clinical research stage. In addition, the defects in the pharmacokinetic properties of BTZ043 and PBTZ169 cannot guarantee these Compound eventually becomes marketed drug

Method used

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  • Benzothiazine derivative, a preparation method and uses thereof
  • Benzothiazine derivative, a preparation method and uses thereof
  • Benzothiazine derivative, a preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Example 1 Compound 1a 2-(4-(2-fluorophenoxy)piperidin-1-yl)-8-nitro-6-(trifluoromethyl)-4H-benzo[e][1, 3] Preparation of Thiazin-4-one

[0098]

[0099] 1.1. Dissolve N-Boc-4-hydroxypiperidine, 2-fluorophenol, and triphenylphosphine in tetrahydrofuran, add diethyl azodicarboxylate dropwise to the above solution, and stir at room temperature for reaction. The end of the reaction was monitored by TLC, concentrated to dryness, and purified by silica gel column chromatography to obtain intermediate 2. Intermediate 2 was dissolved in dichloromethane, trifluoroacetic acid was added dropwise, and the reaction was stirred at room temperature. TLC monitored the completion of the reaction and concentrated to dryness. Diluted with dichloromethane, washed with saturated sodium bicarbonate solution, washed the organic phase with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain intermediate 3 (4-(2-fluorophenoxy)piperidine).

[0100] 1....

Embodiment 2

[0103] Example 2 Compound 1b 2-(4-(4-fluorophenoxy)piperidin-1-yl)-8-nitro-6-(trifluoromethyl)-4H-benzo[e][1, 3] Preparation of Thiazin-4-one:

[0104]

[0105] 2.1. The preparation method of 4-(4-fluorophenoxy)piperidine is the same as 1.1, and the raw materials are N-Boc-4-hydroxypiperidine and 4-fluorophenol.

[0106] 2.2. Add 20 mL of dichloromethane to 2-chloro-3-nitro-5-trifluoromethylbenzoic acid (12 mmol), slowly add oxalyl chloride (30.5 mmol) and 0.05 mL of DMF dropwise under stirring at room temperature, and react for two hours . After the reaction, the reaction solution was spin-dried, dissolved in 15 mL of dichloromethane, slowly added dropwise to ammonium thiocyanate (36 mmol), then added PEG-400 (0.2 g), stirred at room temperature for 1.5 hours; filtered, and the filtrate was added dropwise to 4- (4-fluorophenoxy)piperidine in dichloromethane solution, stirred at room temperature for 40 minutes. After the reaction was completed, the reaction solution was ...

Embodiment 3

[0109] Example 3 Compound 1c 2-(4-(3-fluorophenoxy)piperidin-1-yl)-8-nitro-6-(trifluoromethyl)-4H-benzo[e][1, 3] Preparation of Thiazin-4-one:

[0110]

[0111] 3.1. The preparation method of 3-(3-fluorophenoxy)piperidine is the same as 1.1, and the raw materials are N-BBoc-4-hydroxypiperidine and 3-fluorophenol;

[0112] 3.2. Add 20 mL of dichloromethane to 2-chloro-3-nitro-5-trifluoromethylbenzoic acid (12 mmol), slowly add oxalyl chloride (30.5 mmol) and 0.05 mL of DMF dropwise under stirring at room temperature, and react for two hours . After the reaction, the reaction solution was spin-dried, dissolved in 15 mL of dichloromethane, slowly added dropwise to ammonium thiocyanate (36 mmol), then added PEG-400 (0.2 g), stirred at room temperature for 1.5 hours; filtered, and the filtrate was added dropwise to 3- (3-fluorophenoxy)piperidine in dichloromethane solution, stirred at room temperature for 40 minutes. After the completion of the reaction, the reaction solution...

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Abstract

The invention belongs to the field of chemical medicine, particularly relates to a benzothiazine derivative, a preparation method and uses thereof, and provides a benzothiazine derivative, a preparation method and uses thereof, wherein the structure is represented by a formula I. The invention further provides a preparation method and uses of the benzothiazine derivative. The formula I is definedin the specification.

Description

technical field [0001] The invention belongs to the field of chemistry and medicine, and specifically relates to benzothiazine derivatives and their preparation methods and applications. Background technique [0002] Tuberculosis is one of the diseases with the highest morbidity and mortality in history. In the 21st century, tuberculosis is still the main cause of death in developing countries, and in recent years, the incidence and mortality of tuberculosis have also increased in developed countries. Global tuberculosis mortality due to poor living conditions due to poverty, prevalence of AIDS (AIDZ), emergence of multidrug-resistant Mycobacterium tuberculosis (MDR-TB) and extensively drug-resistant Mycobacterium tuberculosis (XDR-TB) The number has increased continuously in recent years, and the existing anti-tuberculosis drugs can no longer meet the needs of cure. At present, one-third of the world's population, that is, 2 billion people, carry Mycobacterium tuberculosi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04C07D417/14A61K31/5415A61P31/06
CPCC07D417/04C07D417/14Y02P20/55
Inventor 余洛汀魏于全高超
Owner SICHUAN UNIV
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