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Nitric acid ester 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: 2009-04-22
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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  • Nitric acid ester medicament for inhibiting angiogenesis
  • Nitric acid ester medicament for inhibiting angiogenesis
  • Nitric acid ester medicament for inhibiting angiogenesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0130] Example 1 Pregna-4,9(11)-diene-3,20-diketone-17,21-dihydroxy-17-(3-nitrooxy)propionate-21-acetate

[0131]

[0132] 1. Pregna-4,9(11)-diene-3,20-diketone-17,21-dihydroxy-17-(3-chloro)propionate-21-acetate

[0133] method 1:

[0134] 40ml of triethylamine, 0.05g of DMAP and 0.015mol of 3-chloropropionyl chloride were stirred in the reaction and cooled to 0 degrees, slowly added 0.01mol of pregna-4,9(11)-diene-3, 20-diketone-17, 21-dihydroxy-21-acetate and keep the temperature at 0-5 degrees. This reaction is an exothermic reaction, so the addition speed and temperature need to be carefully controlled. Keep the temperature of the above reaction solution at 10°C Below, slowly rise to 10-15 degree in 1 hour after adding, and after 15 hours of this temperature insulation, dilute to 50mlPH and be 1-2 the water that temperature is 0 degree, slowly add hydrochloric acid and adjust pH to be 3-5, this The liquid was extracted three times with 90ml of dichloromethane (30mlX3)...

Embodiment 2

[0145] Example 2 Pregna-4,9(11)-diene-3,20-diketone-17,21-dihydroxy-17-(3-nitrooxy)propionate

[0146]

[0147] Dissolve 0.002mol of pregna-4,9(11)-diene-3,20-diketone-17,21-dihydroxy-17-(3-nitrooxy)propionate-21-acetate in methanol and 10ml of chloroform (1:1), under the protection of nitrogen, add dropwise 0.0025mol aqueous sodium carbonate solution saturated at 0°C at 0°C, after stirring for 10 hours, adjust the pH of the reaction system to be neutral with hydrochloric acid, then pressurize and concentrate to remove Chloroform, the solution was diluted 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 and eluted with methanol and chloroform (1:4) as the mobile phase. The main compound was concentrated under reduced pressure, washed into methanol for recrystallization, and 0.001 mol of the title compound was obtained.

[0148] Elemental analysis calculated value (%): C, 62...

Embodiment 3

[0153] Example 3 Pregna-4,9(11)-diene-3,20-diketone-17,21-dihydroxy-21-(3-methyl-4-nitrooxy)-2-thiophenecarboxylic acid ester

[0154]

[0155] With pregna-4,9(11)-diene-3,20-diketone-17,21-dihydroxyl as raw material, according to the method of Example 1 and 4-bromo-3-methyl-2-thienyl Acid chloride, AgNO 3 The reaction affords the title compound.

[0156] 1. Pregna-4,9(11)-diene-3,20-diketone-17,21-dihydroxy-21-(3-methyl-4-bromo)-2-thiophenecarboxylate

[0157] method 1:

[0158] Stir 40ml of triethylamine and 0.015mol of 4-bromo-3-methyl-2-thiophenoyl chloride in the reaction chamber and cool down to 0 degrees, slowly add 0.01mol of pregna-4,9(11)-bis En-3,20-diketone-17,21-dihydroxy and keep the temperature at 0-5 degrees. This reaction is an exothermic reaction, so the addition speed and temperature need to be carefully controlled. Keep the temperature of the above reaction solution below 10°C After the addition, slowly rise to 10-15 degrees within 1 hour, and after...

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PUM

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Abstract

The invention relates to a nitric acid ester drug for inhibiting the regeneration of blood vessels. The drug is the compound 1, ester or salt of the compound with the following general formula: T-(B-O-NO2)t1, wherein t1 is 1 or 2; T-H is a steroids compound; T is a residual steroids radial of the compound 1 after removing H, and T and H are connected in the form of O-H, namely connecting an oxygen atom on T and H, to form a hydroxide radical The compound is used for preparing the drug for treating tumor and ocular neovascularization disease.

Description

Technical field: [0001] The invention belongs to the field of medicine, in particular to a compound of formula (1) 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 (vasculogenesls, VG) and postnatal angiogenesis (anglogenesls, AG). VG refers to the differentiation of vascular endothelial progenitor cells (endothellalprogenltor, cells, EPCs) or hemangioblasts (angloblasts) into endothelial cells in the absence of a vascular system, and form 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 postnatal angi...

Claims

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Application Information

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IPC IPC(8): C07J7/00C07J5/00A61K31/56A61K47/48A61P35/00A61K47/54
Inventor 郝于田卢彦昌李静胡筱芸孙亮
Owner TIANJIN JINYAO GRP
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