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Nitrate medicament for inhibiting angiogenesis

A technology of drugs and compounds, applied in the field of medicine, can solve problems such as ineffective regression of new blood vessels

Active Publication Date: 2010-01-13
TIANJIN JINYAO GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Steroids alone can somewhat reduce neovascularization, but alone are not effective in regressing neovascularization

Method used

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  • Nitrate medicament for inhibiting angiogenesis
  • Nitrate medicament for inhibiting angiogenesis
  • Nitrate medicament for inhibiting angiogenesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0175] Example 1 4-(pregna-4,9(11)-diene-3,20-diketone-21-hydroxy-21-acetate-17-oxo)-4-oxo-butyric acid-2- [2-(3-Benzenesulfonyl-1,2,5-oxadiazole-2-oxide-4-oxy)ethoxy]ethyl ester

[0176]

[0177] 1) 4-(pregna-4,9(11)-diene-3,20-diketone-21-hydroxy-21-acetate-17-oxo)-4-oxo-butanoic acid (3.1) synthesis

[0178] Dissolve 15mmol pregna-4,9(11)-diene-3,20-diketone-17,21-dihydroxy-21-acetate in 80ml pyridine, add 0.30mmol DMAP, add 30mmol succinic anhydride, heat to reflux After 5 hours, the reaction was stopped. After cooling, it was poured into 200 ml of saturated ice-cold brine, and the pH was adjusted to 5 with hydrochloric acid. A white solid precipitated out after resting, and was filtered and washed with water to obtain 8.1 mmol of the product.

[0179] 2) 4-(pregna-4,9(11)-diene-3,20-diketone-21-hydroxyl-21-acetate-17-oxygen)-4-oxo-butyric acid-2-[ Synthesis of 2-(3-Benzenesulfonyl-1,2,5-oxadiazole-2-oxide-4-oxo-)ethoxy]ethyl ester (9.1)

[0180] Dissolve 8mmol of t...

Embodiment 2

[0185] Example 2 4-(pregna-4,9(11)-diene-3,20-diketone-21-hydroxyl-17-oxo)-4-oxo-butanoic acid-2-[2-(3 -Benzenesulfonyl-1,2,5-oxadiazole-2-oxide-4-oxo)ethoxy]ethyl ester

[0186]

[0187] 4mmol 4-(pregna-4,9(11)-diene-3,20-diketone-21-hydroxy-21-acetate-17-oxo)-4-oxo-butyric acid-2-[ 2-(3-Benzenesulfonyl-1,2,5-oxadiazole-2-oxide-4-oxo-)ethoxy]ethyl ester was dissolved in 10ml of methanol and chloroform (1:1), under nitrogen protection Add dropwise an aqueous solution of sodium carbonate (0.0045mol) saturated at 0°C at 0°C, stir for 10 hours, adjust the pH of the reaction system to neutral with hydrochloric acid, concentrate under pressure, remove chloroform, and dilute the solution in 40ml of ice water , filtered, and dried to obtain the crude product of the title compound. The crude product was subjected to column chromatography, eluting with methanol and chloroform (1:4) as the mobile phase, and the main compound was concentrated under reduced pressure, washed into meth...

Embodiment 3

[0192] Example 3 2-(pregna-4,9(11)-diene-3,20-diketone-17-hydroxyl-21-oxo-)-2-oxo-acetic acid-2-[2-(3 -Benzenesulfonyl-1,2,5-oxadiazole-2-oxide-4-oxo-)ethoxy]ethyl ester

[0193]

[0194] 1) Synthesis of 2-(pregna-4,9(11)-diene-3,20-diketone-17-hydroxyl-21-oxo-)-2-oxo-acetic acid (3.3)

[0195] Dissolve 15mmol of pregna-4,9(11)-diene-3,20-diketone-17,21-dihydroxyl in 80ml of pyridine, add 30mmol of oxalic anhydride, heat and reflux for 5 hours to stop the reaction, after cooling Pour it into 200 ml of saturated ice-cold brine, adjust the pH to 5 with hydrochloric acid, a white solid precipitates out after resting, filter and wash with water to obtain 10.3 mmol of the product.

[0196] 2) 2-(pregna-4,9(11)-diene-3,20-diketone-17-hydroxyl-21-oxo-)-2-oxo-acetic acid-2-[2-(3- Synthesis of Benzenesulfonyl-1,2,5-oxadiazole-2-oxide-4-oxo-)ethoxy]ethyl ester (9.3)

[0197] Dissolve 10mmol of the compound obtained in step 1) in 300ml of anhydrous dichloromethane, add 11mmol of co...

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Abstract

The invention provides a nitrate medicament for inhibiting angiogenesis. The general formula (I) of the medicament is T-(B-M)t1, wherein t1 is 1 or 2, T-Ht1 is a steroidal compound, and T-H means that oxygen atoms of the T are connected with the H to form the hydroxyl connection, namely the O-H typed connection. The compound of the formula (I) can be synthesized by taking the steroidal compound T-Ht1 as a raw material, and can be used for preparing the medicaments of treating angiogenesis diseases of human or mammals, particularly the medicaments of treating the diseases such as tumors, ocular angiogenesis, malignant blood diseases, bronchial asthma, leukoaraiosis and the like.

Description

Technical field: [0001] The invention belongs to the field of medicine, in particular to a compound of formula (I) and a synthesis method thereof. The present invention also relates to the use and pharmaceutical preparation of the compound in medicine, especially for the treatment of tumor and ocular angiogenesis. Background technique: [0002] Angiogenesis includes two concepts: embryonic angiogenesis (vasculogenesis, VG) and postnatal angiogenesis (anglogenesis, AG). VG refers to the differentiation of vascular endothelial progenitor cells (Endothelial progenitor cells, EPCs) or hemangioblasts (angloblasts) into endothelial cells in the absence of a vascular system, and the formation of a vascular network. AG refers to that in adult blood vessels, the existing mature endothelial cells break through the wall matrix to migrate, proliferate and remodel, and continue to elongate the vascular branches in the way of sprouting. Angiogenesis in the present invention refers to po...

Claims

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Application Information

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IPC IPC(8): C07J43/00A61K31/58A61P43/00A61P35/00
Inventor 卢彦昌陈立营孙亮胡筱芸陈松
Owner TIANJIN JINYAO GRP
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