Dimethylamino sphaelactone fumarate and use thereof

A technology of fumarate and dimethylamine, which is applied in the preparation of carboxylates, medical preparations containing active ingredients, and organic active ingredients, etc., can solve the problems of restricting drug research and development, serious hygroscopicity, and instability.

Inactive Publication Date: 2015-09-02
ACCENDATECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the literature (J. Med. Chem. 2012, 55, 8757? 8769), it was reported that the compound of formula (Ⅱ) was used to treat leukemia, but further resear

Method used

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  • Dimethylamino sphaelactone fumarate and use thereof
  • Dimethylamino sphaelactone fumarate and use thereof
  • Dimethylamino sphaelactone fumarate and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Embodiment 1 The preparation of dimethylamine containing smilide fumarate

[0012] To a 250 mL round-bottomed flask equipped with mechanical stirring, a thermometer and a reflux condenser, add fumaric acid (1.98 g, 17 mmol), ethyl acetate (2.5 mL), stir, and heat to 77 ° C; Lactone (5.0 g, 17 mmol) and ethyl acetate (15 mL) were mixed uniformly, added dropwise to the reaction, vigorously stirred; after the dropwise addition, the reaction solution was kept at 77 ° C for 3 hours; heating was stopped, and under stirring, Naturally cooled to room temperature, filtered, washed with ethyl acetate, and dried in vacuo for 24 hours to obtain the compound of formula (I), a white solid of 6.3 g, a yield of 90%.

[0013] Prepare the data of the compound of formula (I):

[0014] Molecular formula: C 21 H 31 NO 7

[0015] Molecular weight: 409

[0016] Appearance: white solid powder

[0017] Elemental analysis data:

[0018] element Calculated / % test value / % ...

Embodiment 2

[0023] Example 2 Pharmacological action of dimethylamine containing smilide fumarate

[0024] Form various cancer cells into 2×10 5 / mL cell suspension, added to a 24-well round-bottom cell culture plate, added test compounds, 5 wells for each tested concentration, incubated at 37 degrees, 5% carbon dioxide saturated humidity for 18 hours, using MTT method in enzyme-linked The absorbance measured by the detector at a wavelength of 570 nm refers to the calculation of the inhibitory effect of the compounds of the present invention on the test cancer cells.

[0025]

[0026] Table 1 Inhibitory effects of compounds of formula (I) on various cancer cells

[0027] cell line Compounds of formula (I) HL-60 31.5 K562 22.3 MCF-7 19.5 CNE-1 26.3 CNE-2 26.5 SW620 33.4 A549 28.3 HepG-2 17.7 Ec9706 23.2 SGC7901 14.7 SW1116 37.1 A498 24.1 ASPC-1 31.5 HT-29 19.2 HeLa 29.4 GL15 45.2 ...

Embodiment 3

[0029] Example 3 Stability comparison of compound of formula (I) and compound of formula (II)

[0030] 1. High temperature test

[0031] Take the compound of formula (I) and compound of formula (II) and put them in an open container, put them in a constant temperature box at 60°C for 10 days, take samples at 0 days, 5 days and 10 days, observe the properties, and determine the content.

[0032]

[0033] Table 2 High temperature test results (60℃)

[0034]

[0035] 2. High humidity test

[0036] Take the compound of formula (I) and compound of formula (II) and put them in an open container, place them in a closed container with a relative humidity of 90±5% (saturated potassium nitrate solution), and place them for 10 days. Sampling, observe the properties, and determine the content.

[0037] Table 3 High humidity test results (90±5%)

[0038]

[0039] The results show that the compound of formula (I) is more stable than the compound of formula (II) no matter un...

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Abstract

The invention relates to a compound represented by formula (I), that is, dimethylamino sphaelactone fumarate, and a use thereof. The compound of formula (I) has the advantages of high stability and low hygroscopicity.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to dimethylamine mimilactone fumarate and its application. [0002] Background technique [0003] It was reported in the literature (J. Med. Chem. 2012, 55, 8757?8769) that the compound of formula (II) was used to treat leukemia, but further studies found that the compound of formula (II) had defects such as instability and serious hygroscopicity, which limited its use. Further drug development. [0004] (Ⅱ) [0005] The compound provided by the invention overcomes the defects of the compound of formula (II) such as instability and severe hygroscopicity, and has the advantages of high stability and low hygroscopicity. Contents of the invention [0006] The present invention provides the compound of formula (I), dimethylaminomildolactone fumarate and its application. [0007] [0008] (Ⅰ) [0009] Use of the compound of formula (I) for treating cancer. Wher...

Claims

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Application Information

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IPC IPC(8): C07D307/93C07C57/15C07C51/41A61K31/365A61P35/00A61P35/02
Inventor 邱传将齐杰王桂燕
Owner ACCENDATECH
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