Nucleoside derivative for preventing and treating inflammatory reaction as well as application thereof

A technology of inflammatory response and derivatives, applied in the field of medicine, can solve problems such as unclear rheumatoid arthritis, and achieve the effects of improving inflammatory indicators, simple structure and synthesis process, and reducing production costs.

Active Publication Date: 2019-06-21
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The treatment methods mainly include general treatment, drug treatment, surgery and other treatments, but it is not clear which anti-rheumatic drug should be the first choice for the treatment of rheumatoid arthritis to effectively improve the condition

Method used

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  • Nucleoside derivative for preventing and treating inflammatory reaction as well as application thereof
  • Nucleoside derivative for preventing and treating inflammatory reaction as well as application thereof
  • Nucleoside derivative for preventing and treating inflammatory reaction as well as application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] In this example, compounds 1-19 were synthesized.

[0025] 1. Synthesis of compound 1: 1-ethyl-3-7-dimethylxanthine

[0026] Dissolve 540mg (3mmoL) of theobromine (3mmoL) and 720mg (30mmol) of NaH in 80mL of DMF, add 2mL (24.7mmol) of ethyl iodide dropwise under stirring, add water to quench the reaction after 4 hours of reaction, and spin dry under reduced pressure. :CH 3 CH 2 OCOCH 3 =3:1 (v / v) was used as the mobile phase to pass through a silica gel column to obtain 495mg (2.5mmol) of compound 1 with a yield of 85%.

[0027] Compound 1 was detected by proton NMR spectrum, carbon NMR spectrum and mass spectrometry, and the results were as follows: 1 H NMR (400 MHz, DMSO) δ 8.00 (s, 1H), 3.92–3.85 (m, 5H), 3.40 (s, 3H), 1.11 (t, J=7.0 Hz, 3H).

[0028] 13 C NMR (101MHz, DMSO) δ154.09(s), 150.54(s), 148.08(s), 142.75(s), 106.56(s), 35.44(s), 33.05(s), 29.20(s), 13.02 (s).

[0029] HRMS (TOF MS ES+) for C 9 h 12 N 4 o 2 Na + (M+Na + ) calcd 231.0858, found...

Embodiment 2

[0102] In the examples, the ameliorating effects of compounds 1-19 prepared in Example 1 on pancreatitis were tested.

[0103] 1. Test method

[0104] (1) Animals: adult healthy male Blab / c mice, 25-30 g.

[0105] (2) Grouping

[0106] The Blab / c mice were randomly divided into blank control group, model control group, caffeine treatment group, and compound 1-compound 19 treatment groups, with 10 mice in each group.

[0107] (3) Construct pancreatitis model

[0108] Sodium taurocholate was used to make the model, fasting for 12 hours before the experiment, without water, and performing the operation in a sterile environment. Inject 3.5% sodium pentobarbital intraperitoneally. After anesthesia, disinfect the surgical site with alcohol cotton balls, place sterile gauze on the surgical site, and cut laparotomy at the width of two fingers under the xiphoid process. After seeing the liver, start the incision , put a cotton swab soaked in normal saline into the abdominal cavity,...

Embodiment 3

[0119] In the examples, the improving effect of compounds 1-19 prepared in Example 1 on arthritis was tested.

[0120] 1. Test method

[0121] (1) Animals: four SD rats in one cage, kept under constant temperature (25±2°C) and lighting control (12h day / night cycle), the animals were fed with standard feed, and fed for at least 7 days before the start of the experiment to adapt to the environment.

[0122] (2) Grouping

[0123] SD rats were randomly divided into blank control group, model control group, caffeine treatment group, indomethacin treatment group, and compound 1-compound 19 treatment groups, with 10 rats in each group.

[0124] (3) SD rats were fasted for 12 hours before the operation, and weighed and recorded before the operation. The blank control group received no treatment.

[0125]SD rats in the model control group, caffeine treatment group, indomethacin treatment group, and compound 1-compound 19 treatment groups were intraperitoneally injected with 10% chl...

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PUM

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Abstract

The invention provides a nucleoside derivative for preventing and treating inflammatory reaction as well as application of the derivative to preparation of medicines for preventing and treating inflammatory diseases. The nucleoside derivative for preventing and treating inflammatory reaction, which is provided by the invention, can obviously improve the disease conditions of pancreatitis, hepatitis, arthritis and the like, can improve the damaged and inflammatory indexes of organs and has the effect better than that of a positive control medicine indometacin. Compared with the traditional anti-inflammatory medicines aspirin, ibuprofen, indometacin, butazodine, diclofenac, piroxicam and glucocorticoid, the nucleoside derivative for preventing and treating inflammatory reaction, which is provided by the invention, has the advantage that the side effect is obviously smaller.

Description

technical field [0001] The invention belongs to the field of medicines, and relates to nucleoside derivatives for preventing and treating inflammatory reactions, and the application of the derivatives in preparing medicines for preventing and treating inflammatory diseases. Background technique [0002] Inflammation is a basic biological response of the body against the invasion of pathogenic microorganisms, which can promote the repair of damaged cells and tissues and prevent further damage. However, excessive inflammatory response can lead to damage and necrosis of tissues and organs and even systemic organs. [0003] At present, inflammation is a common and frequently-occurring disease that threatens human health. For the treatment of inflammation, people often use glucocorticoid steroidal anti-inflammatory drugs and traditional non-steroidal anti-inflammatory drugs. Even if the existing anti-inflammatory drugs can effectively control infectious and non-infectious inflam...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/10C07D473/08C07D473/06C07D473/02C07D239/553A61P29/00A61P1/18A61P19/02A61P1/16A61K31/513A61K31/522
CPCA61K31/513A61K31/522A61P1/16A61P1/18A61P19/02A61P29/00C07D239/553C07D473/06C07D473/08C07D473/10
Inventor 黄文
Owner WEST CHINA HOSPITAL SICHUAN UNIV
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