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Novel nitrogen-containing medicament with anti-inflammatory activity

A compound and composition technology applied in the field of androstane glucocorticoid receptor agonist compounds

Active Publication Date: 2013-03-06
TIANJIN PHARMA GROUP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 1960, Smith et al reported (J Chromatog3 1960, 381) that acetic acid was used instead of acetone without success

Method used

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  • Novel nitrogen-containing medicament with anti-inflammatory activity
  • Novel nitrogen-containing medicament with anti-inflammatory activity
  • Novel nitrogen-containing medicament with anti-inflammatory activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0207] Example 1: 6α,9α-difluoro-11β-hydroxyl-16α,17α-[(22-Rcyclohexylmethine)dioxy]-3-oxoandrost-1,4-diene-17β- Preparation of nitrile methyl carboxylate

[0208]

[0209] Put 10mmol of 6α, 9α-difluoro-16α, 17α, 11β-trihydroxy-3-oxoandrost-1,4-diene-17β-carboxylic acid nitrile methyl ester, 50ml of 70% HF into a plastic bottle, ice Cool the salt bath to about -5°C, stir for 10 to 20 minutes, then slowly add 14 mmol cyclohexylformaldehyde dropwise, and keep stirring at -5°C for 1 hour after the drop is complete. with 10% NH 4 OH / H 2 About 500ml of O was neutralized and diluted to pH = 7, filtered, and dried to obtain 6α, 9α-difluoro-11β-hydroxyl-16α, 17α-[(22-R,S cyclohexylmethine) dioxygen as a white powdery solid ]-3-oxoandrost-1,4-diene-17β-carboxynitrile methyl ester 8.04mmol, use silica gel 254 to carry out column chromatography, wash with acetone / petroleum ether=4 / 3 as the mobile phase, take the main The point substance is 6α, 9α-difluoro-11β-hydroxyl-16α, 17α-[(2...

Embodiment 2

[0214] Example 2: 6α,9α-Difluoro-11β-hydroxy-16α,17α-[(22R,S-Propylmethylene)bisoxy-]-3-oxoandrost-1,4-diene Preparation of -17β-carboxynitrile methyl ester

[0215]

[0216] Dissolve 10mmol of 6α, 9α-difluoro-16α, 17α, 11β-trihydroxy-3-oxoandrost-1,4-diene-17β-carboxynitrile methyl ester in 50ml of dichloromethane under a salt ice bath , 0.7ml 70% HClO 4 , cool down to -5°C, slowly add 14mmol n-butyraldehyde dropwise, keep stirring for 1h, 20%NH 3 / H 2 O was neutralized to neutral, the layers were separated, the organic layer was taken, concentrated under reduced pressure, poured into methanol for recrystallization, and obtained 7.43 mmol of the title compound, 22R:S=84:16.

[0217] Elemental analysis calculated value (%): C26H31F2NO6 C, 63.53; H, 6.36; F, 7.73; N, 2.85; O, 19.53

[0218] Elemental analysis found value (%): C 63.76, H 6.41, N 2.79, O 19.38

[0219] 13 C-NMR: Numerical value of carbon from position 1 to position 23

[0220] ( ), 37.1, 13.9, 14.8 (22...

Embodiment 3

[0221] Example 3: 6α,9α-difluoro-11β-hydroxy-16α,17α-[(22R-propylmethylene)bisoxy-]-3-oxoandrost-1,4-diene-17β- Preparation of nitrile methyl carboxylate

[0222]

[0223] 5 mmol of the compound obtained in Example 2 was subjected to column chromatography using silica gel 254, washed with acetone / petroleum ether=4 / 3 as the mobile phase, and 3.43 mmol of the title compound was obtained as the main point substance.

[0224] Two-dimensional nuclear Overhaus effect spectroscopy (NOESY), from which the stereo configuration of protons and substituents was determined. Among them, the 18-methyl H and the 16-position H have NOE effect, and the 22-position H and the 16-position H have an NOE effect, which proves that R2 is H.

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Abstract

The invention relates to an androstane azotic glucocorticoid receptor stimulant compound and a preparation method thereof. The invention further relates to the pharmaceutical preparations comprising the compound and the therapeutic use of the compound, in particular to inflammatory disease, allergic disease or anaphylactic disease.

Description

field of invention [0001] The invention relates to an androstane glucocorticoid receptor agonist compound and a preparation method thereof. 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 well known to have anti-inflammatory properties and are widely used in the treatment of inflammatory disorders or diseases such as asthma and rhinitis. Abroad in the 1950s and 1960s, a lot of research was done on the 16, 17 dihydroxy acetal (ketone) process, and a variety of 16, 17 dihydroxy acetals (ketones) represented by fluocinolone, triamcinolone acetonide, and halcinonide were synthesized successively. Hydroxyketal drugs, after entering the 1970s, 16, 17 bishydroxyacetal drugs represented by budesonide have achieved great success. In 2004, the sales of drugs related to budeson...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00A61K31/58A61P29/00A61P37/00
Inventor 卢彦昌张乐孙亮
Owner TIANJIN PHARMA GROUP CORP
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