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Quinoline derivatives, preparation method and applications thereof

A technology of derivatives and quinolines, applied in the field of medicinal chemistry, can solve problems such as lack of market opportunities

Inactive Publication Date: 2009-09-09
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the increasing emergence of multi-drug resistant strains and the occurrence of HIV patients with TB, tuberculosis has become the leading cause of infectious death in adults after AIDS in the world
Since the discovery of the anti-TB activity of rifampicin 40 years ago, few new drugs for the treatment of TB have been developed due to lack of market opportunity

Method used

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  • Quinoline derivatives, preparation method and applications thereof
  • Quinoline derivatives, preparation method and applications thereof
  • Quinoline derivatives, preparation method and applications thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0042] Preparation of representative reaction intermediates:

[0043] Synthetic route I

[0044] 1.1N-(4-bromophenyl)-3-phenylpropanamide (N-(4-bromophenyl)-3-phenylpropanamide, number: M-03)

[0045]

[0046] Reagents and reaction conditions: (a).SOCl 2 , CHCl 3 , reflux; (b).Et 3 N, CH 2 Cl 2 , -5~5℃

[0047] Experimental operation: (a) In a 250ml single-necked bottle, add 20.0g (0.13mol) of 3-phenylpropanoic acid (3-phenylpropanoic acid) and 20ml of dichloromethane, stir to dissolve, add 15ml of thionyl chloride dropwise, Heated to reflux for 3h. After the reaction was completed, the remaining thionyl chloride and the solvent were distilled off to obtain 22.0 g of light yellow liquid with a yield of 98.2%, which was directly carried out to the next reaction. (b) In a 500ml single-necked bottle, add 21.0g (0.12mol) of p-bromoaniline (M-02) and 200ml of dichloromethane, stir to dissolve, dropwise add 22ml of triethylamine, and drop 3 -22.0 g (0.13 mol) of phenylpr...

Embodiment I-01

[0085] N-((6-bromo-2-methoxyquinolinyl-3-yl)(phenyl)methyl)-2-dimethylamino-N-(naphthyl-1-yl)acetamide

[0086] (N-((6-bromo-2-methoxyquinolin-3-yl)(phenyl)methyl)-2-(dimethylamino)-N-(naphthalen-1-yl)acetamide

[0087]

[0088] Reagents and reaction conditions: (CH 3 ) 2 NHHCl, KHCO 3 , CH 3 CN, reflow

[0089] Experimental operation: Add 1.0g (0.002mol) N-((6-bromo-2-methoxyquinolinyl-3-yl)(phenyl)methyl)-2-chloro- N-(Naphthyl-1-yl)acetamide (N-((6-bromo-2-methoxyquinolin-3-yl)(phenyl)methyl)-2-chloro-N-(naphthalen-1-yl)acetamide, Code: M-08), 0.3g (0.003mol) dimethylamine hydrochloride, 1.8g (0.018mol) potassium bicarbonate and 30ml acetonitrile, heated to reflux overnight. Evaporate the solvent to dryness, add water, extract with (20ml×3) dichloromethane, combine the organic phases, dry (MgSO 4 ), filtered, and the solvent was evaporated to dryness to obtain a brown solid crude product. Purified by column chromatography, 0.8 g of the target product was obtained ...

Embodiment I-02

[0091]Example 1-02: 2-(benzyl (methyl)amino)-N-((6-bromo-2-methoxyquinolinyl-3-yl)(phenyl)methyl)-N-( Naphthyl-1-yl)acetamide

[0092] 1 H NMR (300MHz, CDCl 3 )δ2.28 (S, 3H; NCH 3 ), 3.27 (S, 2H; CH 2 ), 3.62 (S, 2H; NCH 2 ), 3.96 (S, 3H; OCH 3 ), 6.14 (S, 1H; CH), 6.65-7.56 (m, 7H; naphthalenering), 7.26-7.13 (m, 10H; benzene ring), 7.68-7.94 (m, 4H; quinoline ring); MS (ESI ( +))m / s 630(M+H + ).

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Abstract

The invention relates to new substituted quinoline derivatives presented in general formula (1a), or general formula (1b) or general formula (1c), a medical acid added salt, a stereochemical heterogeneous formula and a tautomeric form thereof. The compound can be used for curing mycobacterium diseases, in particular to diseases caused by pathogenic mycobacteria, such as mycobacterium tuberculosis, mycobacterium bovis, mycobacterium avium and mycobacterium marinum and is particularly defined as following: R1 is mutually independent bromines; p is equal to 1, R2 is an alkoxy, and R3 is a randomly substituted phenyl or naphthyl; q is equal to 1, R4 and R5 are mutually independent hydrogen and a methyl or an ethyl, and R6 is hydrogen; r is equal to 0 or 1 and R7 is hydrogen. The invention also relates to a composition of the compound, applications of the compound of the composition to medicines for curing the mycobacterium diseases, and a method for preparing the compound of the composition, which comprises a medical carrier and is used as activated ingredient of curable effective quantity.

Description

Technical field: [0001] The invention belongs to the technical field of medicinal chemistry, relates to quinoline derivatives and a preparation method thereof, and also relates to the application of the derivatives in the preparation of medicines for treating mycobacterium infection. Background technique: [0002] Mycobacterium tuberculosis is a widespread and potentially fatal infectious agent worldwide, the most common cause of which is tuberculosis. The World Health Organization estimates that more than eight million people worldwide are infected with tuberculosis every year, and two million people die from tuberculosis every year. Since Mycobacterium tuberculosis (TB) was discovered on March 24, 1882, humans have been working hard to explore the way to eliminate Mycobacterium tuberculosis. In the 1950s, due to the chemotherapy method established by Schatz, Bugie and Waksman, the tuberculosis The epidemic has been controlled to a certain extent. However, due to the incr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/227A61K31/47A61P31/06
Inventor 孙铁民蔡志强祝石柳建波
Owner SHENYANG PHARMA UNIVERSITY
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