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Indole compounds and preparation method and application thereof as drug-resistant bacteria resistant drugs

A compound and indole technology, applied in the field of chemical and compound medicine, can solve problems such as slow progress and inability to treat drug-resistant bacteria

Inactive Publication Date: 2016-06-15
BEIFANG UNIV OF NATITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current slow progress in the development of new drugs and the inability of existing drugs to treat drug-resistant bacteria further exacerbate the above problems

Method used

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  • Indole compounds and preparation method and application thereof as drug-resistant bacteria resistant drugs
  • Indole compounds and preparation method and application thereof as drug-resistant bacteria resistant drugs
  • Indole compounds and preparation method and application thereof as drug-resistant bacteria resistant drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0168] Embodiment 1 general formula III, the preparation of I compound

[0169]

[0170] Preparation of intermediate 1-(3- or 4-substituted benzyl)-3-formyl-5(or 6)-methoxycarbonylindole 3 in general formula V

[0171]

[0172] Preparation of 3-formyl-5(or 6)-methoxycarbonylindole (2)

[0173] 5 (or 6)-methoxycarbonylindole (1) and phosphorus oxychloride (POCl 3 ) Vilsmeier-Hack reaction occurs under the condition of dry N,N-dimethylsulfoxide to generate 3-formyl-5 (or 6)-methoxycarbonylindole (2)

[0174] Preparation of 3-formyl-5 (or 6)-methoxycarbonylindole (2) manipulation example

[0175] Preparation of 3-formyl-5-methoxycarbonylindole

[0176]Under nitrogen protection, 5.00 g (28.57 mmol) of methyl indole-5-carboxylate was added to 20 mL of ultra-dry DMF, cooled to 0°C, and then 3.62 mL (38.86 mol) of phosphorus oxychloride was slowly added dropwise. After reacting at 0°C for 10 min, react at room temperature for 3 h. After cooling the reaction liquid to 0°C, ...

Embodiment 2

[0236] Embodiment two general formula IV, the preparation of II compound

[0237] Preparation of target compound Ⅳ

[0238] Intermediate (3) or (4) or (8) respectively reacts with 4,5-dihydroimidazole-2-hydrazine hydrogen bromide VI in dry methanol to reflux the target compound IV;

[0239] Preparation of 1-p-chlorobenzyl-5-methoxycarbonyl-3-indolecarbaldehyde, (4,5-dihydro-1H-imidazol-2-yl)hydrazonone hydrogen bromide salt (compound 61 in Table 8) manipulation instance

[0240] 0.05 g (0.15 mmol) of 1-p-chlorobenzyl-3-formyl-6-methoxycarbonylindole was added to 2 mL of anhydrous methanol, and then 4,5-dihydroimidazole-2-hydrazine was brominated 0.03 g (0.15 mmol) of hydrogen was added to the reaction solution, and heated to 75°C for reaction. After the reaction, the reaction solution was cooled to room temperature, and diethyl ether was added to stand still to precipitate a solid, which was filtered under reduced pressure, and the filter cake was washed with diethyl ether ...

Embodiment 3

[0250] Embodiment 3 The preparation of compound sterile powder injection of the present invention

[0251] 1. Prescription:

[0252] Prescription 1:

[0253] Any one of compound III or IV 250g (calculated as compound)

[0254] A total of 1000 sticks were prepared

[0255] Prescription 2:

[0256] Any one of compound III or IV 500g (calculated as compound)

[0257] A total of 1000 sticks were prepared

[0258] Prescription 3:

[0259] Any one of compound III or IV 1000g (calculated as compound)

[0260] A total of 1000 sticks were prepared

[0261] Prescription 4:

[0262] Any one of compound III or IV 2000g (calculated as compound)

[0263] A total of 1000 sticks were prepared

[0264] 2. Preparation process:

[0265] (1) Aseptically process the antibiotic glass bottles, rubber stoppers, etc. used for the preparation;

[0266] (2) Weigh the raw materials according to the prescription (feeding after conversion), put the sterile powder in the filling machine for subp...

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Abstract

The invention discloses indole compounds represented by the general formula defined in the specification and salts and preparation method thereof, corresponding medical uses of the compounds and the salts thereof, and drugs and disinfectants containing the compounds and the salts thereof. A lot of experiments prove that the compounds and the salts thereof have good bacteriostatic and bactericidal activity on MRSA (drug-resistant staphylococcus aureus), MDR K.pneumonia (drug-resistant klebsiella pneumonia), and MDR A.baumanii (drug-resistant acinetobacter baumannii). In the formula, X is methylene, carbonyl or sulfonyl; R1 is fluorine, chlorine, bromine, methoxy acyl, nitro or hydrogen; R2 is methoxyl acyl, (p-methoxyl acyl)phenyl, (p-trifluoro oxy)phenyl, (p-trifluoro)phenyl, (m-methoxy acyl)phenyl, (m-trifluoro oxy)phenyl, (p-fluoro m-chloro)phenyl or hydrogen; and HA is inorganic acid or a part of organic acid with strong acidity, preferably hydrochloric acid or hydrobromic acid.

Description

technical field [0001] The invention relates to the field of chemical and medical application of compounds, in particular to an indole compound containing indole, aminoguanidine or hydrazinone and a salt thereof, a preparation method and a medical application as an anti-drug-resistant bacteria drug. Background technique [0002] In recent years, with the continuous development and marketing and clinical application of various antibiotics, especially under the requirements of some medical institutions, medical personnel and patients based on the rapid elimination of infected patients, the abnormal use of large doses and excessive doses of antibiotics has become more and more serious. These phenomena have led to the rapid development and evolution of drug-resistant bacteria against antibacterial agents: the emergence of methicillin-resistant Staphylococcus aureus (MRSA) and methicillin-sensitive Staphylococcus aureus (MSSA) have given clinical antibacterial and anti-infective ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/14C07D403/12A61K31/404A61K31/4178A61P31/04A01N47/44A01N43/50A01P1/00
CPCA01N43/50A01N47/44C07D209/14C07D403/12
Inventor 洪伟王昊常喆李京洋杨延辉王瑜谭晓丽欧阳溢凡杨浩
Owner BEIFANG UNIV OF NATITIES
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