A kind of sinomenine derivative and its preparation method, application and pharmaceutical composition

A derivative, the technology of sinomenine, is applied in the field of biomedicine to achieve the effects of preventing and treating aplastic anemia, easy standardized production, and good pharmacodynamic characteristics

Active Publication Date: 2021-07-02
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The structure and pharmacological activity of this compound have not been reported so far

Method used

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  • A kind of sinomenine derivative and its preparation method, application and pharmaceutical composition
  • A kind of sinomenine derivative and its preparation method, application and pharmaceutical composition
  • A kind of sinomenine derivative and its preparation method, application and pharmaceutical composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the preparation of sino-wcj-43

[0034] Molecular formula: C 38 h 37 NO 7

[0035] Nomenclature: 1-cinnamoyloxymethylene-4-cinnamoyloxy-7,8-didehydro-3,7-dimethoxy-17-methyl-morphinan-6-one, 1-cinnamoyloxymethylene-4-cinnamoyloxy-7, 8 Didehydro-3,7-dimethoxy-17-methyl-morphinan-6-one.

[0036] Compound synthesis route:

[0037]

[0038] Step 1: Weigh 10.0 g of sinomenine hydrochloride, dissolve it in 200 ml of water, add 20.0 g of paraformaldehyde (2-3 times the mass of sinomenine hydrochloride) under stirring, heat and reflux for 4h-12h, and monitor the reaction process by TLC. After the reaction, use CHCl 3 Extraction (100mL × 3 or the number of extractions can be increased), combined organic phase, anhydrous Na 2 SO 4 After drying, filtering, and evaporating off the solvent, a white solid was obtained, and 1-hydroxymethylene sinomenine was obtained.

[0039] Step 2, take about 50 mg of 1-hydroxymethylene sinomenine, dissolve it in dichlorome...

experiment example 1

[0042] Experimental example 1: Inhibitory effect of sino-wcj-43 on LPS-induced production of inflammatory proton NO in primary mouse peritoneal macrophages

[0043] Macrophages perform the body's non-specific immune function. Under the induction of bacterial lipopolysaccharide LPS, they can produce inflammatory factors such as NO, participate in and mediate the inflammatory response, and have high levels in the initial stage of various inflammatory immune processes and in the process of pathological development. Level. By detecting the amount of NO produced by primary cultured mouse peritoneal macrophages, it can be used as a preliminary observation of the anti-inflammatory activity of the compound in vitro.

[0044] experimental method:

[0045] Primary mouse peritoneal macrophages were inoculated in 96-well plates, and compounds of different concentrations were added for pre-protection for 1 h; then, LPS was added to make the final concentration 1 μg / ml, and the cells were ...

experiment example 2

[0050] Experimental example 2: Effect of sino-wcj-43 on otitis induced by croton oil in mice

[0051] experimental method:

[0052] Take 18-20g male Kunming mice, divide them into groups randomly, and apply 0.02ml of croton oil on both sides of the left ear of each group of animals respectively; 30 minutes later, each group of animals is subcutaneously injected with 50mg / kg and 100mg / kg body weight of the test compound respectively , the model control group was given an equal volume of vehicle; 4 hours after the administration, the mice were killed by neck dislocation, and both ears were cut off along the baseline of the auricles, and the ear pieces at the same positions of the left and right ears were removed with a 6 mm diameter punch, and weighed with an analytical balance. Calculate ear swelling degree (ear swelling degree=left ear piece weight-right ear piece weight) and ear swelling inhibition rate [ear swelling inhibition rate (%)=(model group average ear swelling degre...

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PUM

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Abstract

The invention discloses the structure and preparation method of a sinomenine derivative compound sino-wcj-43 as shown in formula (I), and its application in inflammatory diseases and aplastic anemia. The derivative of the present invention relates to the synthesis of a novel structural derivative sino-wcj-43 using sinomenine hydrochloride as a raw material. The invention discloses that the preparation method of sino-wcj-43 or a pharmaceutically acceptable salt thereof is simple, and has obvious anti-inflammatory and therapeutic effects on aplastic anemia, and can be used in the treatment of inflammatory diseases in the form of monomer or pharmaceutical composition. and clinical application of aplastic anemia.

Description

technical field [0001] The present invention relates to the field of biomedicine, in particular to a preparation method of a sinomenine derivative or a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing the derivative or a pharmaceutically acceptable salt thereof and its anti-inflammatory effect Diseases and applications in aplastic anemia. Background technique [0002] Aplastic anemia (referred to as aplastic anemia, AA) is an acquired bone marrow hematopoietic failure disease caused by chemical, physical, biological factors or unknown reasons, manifested as low bone marrow hematopoietic function, pancytopenia and anemia , bleeding, infection syndrome. The cause or mechanism of its pathogenesis is very complicated, and it is currently believed to be related to the inherent defects of hematopoietic stem cells, abnormal hematopoietic microenvironment and immune dysfunction. Although the specific pathogenesis has not been clarified, there has b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/28A61K31/485A61P29/00A61P19/02A61P11/06A61P11/00A61P13/12A61P7/06
CPCC07D221/28
Inventor 林明宝吉腾飞侯琦白金叶杨慧魏灿晶范燕楠
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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