Novel nitric acid esters steroidal compounds

A compound and hydrocarbon technology, applied in the directions of steroids, non-active components of polymer compounds, organic chemistry, etc., can solve problems such as loss of ulcers, and achieve the effects of low side effects, high activity and good stability

Inactive Publication Date: 2009-04-01
TIANJIN PHARMA GROUP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the specificity of drugs, the development of these products also has greater risks. Among them, NO-donating non-steroidal anti-inflammatory drugs (NO-NsAIDs) AZD3582 (also known as HCI3012, naproxcinod) has entered phase III clinical research, but Recently its developer Astra has announced that the drug has lost its goal of treating ulcers

Method used

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  • Novel nitric acid esters steroidal compounds
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Embodiment 1. methylprednisolone acetate 17-(3-nitrooxy) propionate

[0098]

[0099] 1 Methylprednisolone acetate 17-(3-chloro)propionate

[0100]

[0101] method 1:

[0102] 40ml of triethylamine, 0.05g of DMAP and 0.015mol of 3-chloropropionyl chloride were stirred in the reaction and cooled to 0°C, slowly added 0.01mol of methylprednisolone acetate and kept at a temperature of 0-5°C, The reaction is an exothermic reaction, so the addition rate and temperature need to be carefully controlled. Keep the temperature of the above reaction solution below 10°C. After the addition is completed, it will slowly rise to 10-15°C within 1 hour. , diluted to 50ml, the pH is 1-2, the temperature is 0 degrees water, slowly add hydrochloric acid to adjust the pH to 3-5, the liquid is extracted three times with 90ml of dichloromethane (30mlX3), and then washed with 90ml of water three times (30mlX3) Adjust the pH value of the dichloromethane layer to neutral, concentrate the ...

Embodiment 2

[0112] Example 2. Methylprednisolone 17-(3-nitrooxy)propionate

[0113]

[0114] 0.002mol of methylprednisolone acetate 17-(3-nitrooxy)propionate prepared as above was dissolved in 20ml of methanol and chloroform (1:1), and added dropwise at 0°C under nitrogen protection. Saturated 0.005 mol aqueous sodium carbonate solution was vigorously stirred for 10 hours, the pH of the reaction system was adjusted to neutral with hydrochloric acid, concentrated under reduced pressure, chloroform was removed, the solution was diluted in 50 ml 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.

[0115] Elemental analysis calculated values: C 61.09%, H 6.77%, N 2.85%, O 29.30%,

[...

Embodiment 3

[0119] Embodiment 3. Betamethasone acetate 17-(5-nitrooxy)valerate

[0120]

[0121] Taking betamethasone acetate as raw material, according to the method of embodiment 1 and 5-bromovaleryl chloride, AgNO 3 The reaction affords the title compound.

[0122] Elemental analysis calculated value (%): C, 60.09; H, 6.61; F, 3.28; N, 2.42; O, 27.60

[0123] Elemental analysis measured value: C29H38FNO10 C 60.00%, H 6.63%, N 2.33%, F 3.34 O 27.70%

[0124] 13 C-NMR (CDCl 3 ): 1 to 29 carbon values:

[0125] 152.0, 128.5, 185.9, 121.4, 166.7, 31.2, 27.1, 34.1, 100.9, 47.9, 70.9, 37.2, 46.8, 44.0, 33.2, 47.2, 94.8, 17.1, 22.1, 212.5, 68.4, 174.1, 34.2, 21. 74.9, 170.1, 20.9, 19.81

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Abstract

The invention relates to novel nitrate-steroidal compounds and the preparation method of the compounds. The invention also relates to the medical preparation containing the compounds and the therapeutic application of the compounds, especially the treatment to inflammatory, allergic and anaphylactic diseases.

Description

field of invention [0001] The present invention relates to a kind of novel nitrate steroid compound and their preparation method. The invention also relates to pharmaceutical preparations containing this compound and to the therapeutic use of this compound, in particular for the treatment of inflammatory, allergic or allergic diseases. Background technique: [0002] Glucocorticoids are necessary to maintain life, and have important effects on protein, sugar, fat, water, electrolyte metabolism and the functions of various tissues and organs. Superphysiological amounts of glucocorticoids have anti-inflammatory, anti-allergic and immune-suppressing effects. Pharmacological action, clinical application is very extensive. Supraphysiological doses of glucocorticoids can treat primary or secondary adrenal insufficiency; treat various types of adrenal hyperplasia (including 21-hydroxylase deficiency, 17- Hydroxylase deficiency, 11-hydroxylase deficiency, etc.); using the anti-infl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J5/00C07J7/00A61K31/573A61K47/48A61P29/00A61P31/00A61P37/00A61K47/40
Inventor 卢彦昌李静孙亮陈立营
Owner TIANJIN PHARMA GROUP CORP
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