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Mulin acetate containing substituted squaric acid and application thereof

A technology of substituents and representatives, which is used in medical preparations containing active ingredients, organic chemistry, pharmaceutical formulations, etc.

Active Publication Date: 2013-08-14
BEIJING ABLEPHARMTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

One of the proven strategies is to reevaluate previously discovered antimicrobial agents that have good activity against resistant strains but have not been used in humans

Method used

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  • Mulin acetate containing substituted squaric acid and application thereof
  • Mulin acetate containing substituted squaric acid and application thereof
  • Mulin acetate containing substituted squaric acid and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0102]The above-mentioned content of the present invention will be further described in detail through specific implementation in the form of examples below. However, it should not be construed that the scope of the above-mentioned subject matter of the present invention is limited to the following examples. All technologies realized based on the above contents of the present invention belong to the scope of the present invention. Example 1: 2-(1-(2-amino-3,4-dioxocyclobuten-1-yl)amino-2-methylpropyl)thioglycolic acid (3aS, 4R, 5S, 6s, 8R , 9R, 9aR, 10R)-octahydro-5,8-dihydroxy-4,6,9,10-tetramethyl-6-vinyl-3a,9-propane-3aH-cyclopentacyclooctene-1 (4H)-Keto-8-ester is Table Compound 1

[0103] Step 1: Preparation of N-tert-butoxycarbonyl-2-hydroxy-2-methylpropylamine

[0104] 1-Amino-2-methylpropanol (8.9g, 0.1mol) was dissolved in 200ml of dichloromethane, triethylamine (15.2g, 0.15mol) was added, Boc anhydride (26.2g, 0.12mol) was added under stirring at room temperature...

Embodiment 2

[0115] Example 2: 2-(1-(2-(piperazin-1-yl)-3,4-dioxocyclobuten-1-yl)amino-2-methylpropyl)thioglycolic acid (3aS, 4R, 5S, 6S, 8R, 9R, 9aR, 10R)-octahydro-5,8-dihydroxy-4,6,9,10-tetramethyl-6-vinyl-3a,9-propane-3aH- Cyclopentane-1(4H)-one-8-ester is Table Compound 07

[0116] Step 1: Preparation of 3-(piperazin-1-yl)-4-ethoxy-3-cyclobutene-1,2-dione

[0117] Dissolve the diethyl squarylate (1.7 g, 0.01 mol) obtained in Example 1 in 30 ml of absolute ethanol, add piperazine (0.86 g, 0.01 mol), heat to reflux for 12 hours, and concentrate under reduced pressure Add 50 milliliters of ether, stir, precipitate white solid, filter under reduced pressure, obtain 3-(piperazin-1-yl)-4-ethoxyl-3-cyclobutene-1,2-dione (1.49g , 71%). 1 H NMR (400MHz, CDCl 3 )δ4.06(q, 2H), 2.32(t, 4H), 2.18(t, 4H), 1.96(br.s, 1H), 1.21(t, 3H); LC-MS m / z=211[M +H] + .

[0118] Step 2: 2-(1-(2-(piperazin-1-yl)-3,4-dioxocyclobuten-1-yl)amino-2-methylpropan-2-yl)thioglycolic acid (3aS, 4R, 5S, 6S, 8...

Embodiment 3

[0120] Example 3: 2-(1-(2-Amino-3,4-dioxocyclobuten-1-yl)piperidin-3-yl)thioglycolic acid (3aS, 4R, 5S, 6S, 8R, 9R ,9aR,10R)-octahydro-5,8-dihydroxy-4,6,9,10-tetramethyl-6-vinyl-3a,9-propane-3aH-cyclopentacyclooctene-1(4H )-keto-8-ester is the form compound 13

[0121] Step 1: Preparation of N-tert-butoxycarbonyl-3-hydroxypiperidine mesylate

[0122] Dissolve N-tert-butoxycarbonyl-3-hydroxypiperidine (2.01 g, 0.01 mol) in 50 ml of dichloromethane, add 0.02 mol of triethylamine, cool to 0° C. in an ice-water bath, slowly add methanesulfonyl chloride ( 1.37g, 0.012mol), after the dropwise addition, keep stirring at 0°C for 2 hours until the raw material disappears, then add 10ml of saturated ammonium chloride aqueous solution dropwise at 0°C to quench the reaction. The dichloromethane layer was separated by a separating funnel, the aqueous layer was extracted twice with 10 ml of dichloromethane, and the organic layers were combined. The organic phase was washed with 10 ml o...

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Abstract

The invention relates to Mulin acetate containing substituted squaric acid and an application thereof which belong to the technical field of medicines, specifically to substituted squaric acid containing Mulin acetate as shown in a general formula (I), pharmaceutically acceptable salt, a hydrate and an isomer thereof, wherein R1, R2, R3, R4, R5 and B are defined in the specification. The invention also relates to a preparation method of these compounds, a pharmaceutical composition containing these compounds and an application of these compounds in the preparation of drugs for treating or preventing bacteria and virus. As for staphylococcus aureus and Streptococcus equin MIC value, the compounds have an antibacterial effect 15-20 times higher than a control commercially-available antibiotic tiamulin in the test. And the compounds provided by the invention are effective antimicrobial agents. And the compounds provided by the invention are effective antimicrobial agents.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a substituted squarylium acetate, its pharmaceutically acceptable salt, its hydrate, and its isomer; the invention also relates to a preparation method of these compounds, and a pharmaceutical combination containing these compounds compounds, and the application of these compounds in the preparation of therapeutic / or preventive antibacterial and antiviral drugs. Background technique [0002] Since the discovery of penicillin, human beings have been studying antibiotics for nearly a hundred years. During this period, research on new antibacterial drugs mainly focused on drugs such as β-lactams, macrolides and quinolones. The discovery of antibacterial drugs has greatly improved the healthy living standards of human beings, but the ensuing abuse of antibiotics has led to the emergence of drug resistance. It was not until the 1990s that the development and expansion of drug resista...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/52C07C323/58C07C319/20C07D295/135C07D211/54C07D207/08C07D241/04C07D279/12A61K31/22A61K31/495A61K31/54A61K31/451A61K31/496A61K31/541A61K31/40A61P31/04A61P31/12
Inventor 陈剑
Owner BEIJING ABLEPHARMTECH CO LTD
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