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Process for connecting side chain to androstane compound at 17th position

A compound, the technology of androsteroid, which is applied in the field of steroid chemical synthesis, can solve the problem of high cost and achieve the effect of good safety and price

Inactive Publication Date: 2005-03-16
TIANJIN PHARMA GROUP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, they used highly toxic substances such as potassium cyanide and other high-cost reagents, which will cause certain problems in terms of production costs and waste liquid treatment after production.

Method used

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  • Process for connecting side chain to androstane compound at 17th position

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 1. Preparation of androst-3,5[6]-dien-17-one-3-ethoxyl (2)

[0021] After mixing 40 g of androst 4-ene-3,17-dione and 640 g of ethanol, 71.76 g of triethyl orthoformate and 4 g of PTS (p-toluenesulfonic acid) were added. The reaction medium was kept stirring at 45° C. in an oil bath for 4 hours, cooled to 20° C., poured into 1000 g of water, separated, washed with water, and dried to obtain 43.2 g of substance (2), with a yield of 98.4%.

[0022] 2. Preparation of androst-3,5[6]-diene-3-ethoxy-17-(2-diethylmalonate)ene (3)

[0023] After mixing 30 g of substance (2) with 263.61 g of anhydrous benzene, 48.65 g of diethyl 1,3-malonate and 3 g of potassium tert-butoxide were added, and the reaction medium was refluxed at 90° C. under oil bath conditions. And take the water device to remove the water generated by its reaction. After 4 hours of reflux, the mixture stopped heating and was lowered to 20 ° C. After mixing the organic phase with 300 g of water, the layers were...

Embodiment 2

[0035] 1. Preparation of androst-3,5[6]-dien-17-one-3-ethoxy-6α-methyl (2)

[0036] After mixing 40 g of androst 4-ene-3,17-diketone-6α-methyl and 400 g of ethanol, 107.64 g of triethyl orthoformate and 5 g of pyridine hydrobromide were added. The reaction medium was kept stirring at 80° C. in an oil bath for 5 hours, cooled to 15° C., poured into 850 g of water, separated, washed with water, and dried to obtain 40.9 g of substance (2), with a yield of 93.5%.

[0037] 2. Preparation of androst-3,5[6]-diene-3-ethoxy-17-(2-diethyl malonate)-6α-methyl (3)

[0038] After mixing 30 g of substance (2) with 263.6 g of anhydrous toluene and adding 38 g of diethyl 1,3-malonate and 3 g of potassium tert-butoxide, the reaction medium was refluxed at 85° C. in an oil bath, and Take the water separator to remove the water generated by its reaction. After refluxing for 3 hours, the mixture stopped heating and was lowered to 20 ° C. After mixing the organic phase with 400 g of water, the l...

Embodiment 3

[0049] 1. Preparation of androst-3,5[6],9[11]-triene-17-one-3-ethoxyl (2)

[0050] After mixing 40 g of androster 4,9(11)-diene-3,17-diketone (1) and 552.7 g of ethanol, 67.28 g of triethyl orthoformate and 3.4 g of PTS (p-toluenesulfonic acid) were added. The reaction medium was kept stirring at 48°C in an oil bath for 8 hours, cooled to 10°C and poured into 800g of water, then separated, washed with water and dried to obtain 42.6g of substance (2), yield 96.9%.

[0051] 2. Preparation of androst-3,5[6],9[11]-triene-3-ethoxy-17-(2-diethyl malonate)ene (3)

[0052] After mixing 30g of substance (2) with 237.25g of anhydrous benzene and adding 44.38g of dimethyl 1,3-malonate and 1.8g of potassium tert-butoxide, the reaction medium was refluxed at 90°C in an oil bath , and take the water separation device to remove the water generated by its reaction. After 4 hours of reflux, the mixture stopped heating and was lowered to 10°C. After mixing the organic phase with 270 g of wate...

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Abstract

Process for connecting side chain to androstane compound at 17th position by using androstene 4-alkene-3,17 bisketone or androstene 1,4-bisketone contained in the raw material as main block and its 9[11] as double bonds, steroid compounds including oxygen atom on position 11, halogen or methyl on position 6, to substance containing 3,5[6]-diene-3-ethyoxyl, to substance containing 17-(2-diethyl malonate) alkene, to substance containing 17(20) alkene-21-carboxylic ethyl ester, to substance containing 4.17(20) diene-21-hydroxide, to substance containing 21-acetic ester, to substance containing 17.20-bishydroxyl, and the 17 hydroxyl and 20 ketone are produced through selective oxidation process.

Description

technical field [0001] The invention belongs to steroid chemical synthesis technology, in particular to a preparation method for androsteroid compound by connecting side chains at the 17-position to generate pregnant steroid compound. Background technique [0002] Pregn-4-ene-3,20-diketone-21-acetate and its derivatives are key intermediates in the synthesis of pregnansteroids, used in the manufacture of steroids such as dexamethasone, betamethasone, methylprednisolone, etc. Body drugs, with high economic value. The method commonly used now is Schwarz in 1973, and the technology published by V et al. in Cesk Farm magazine (Czech Republic) 22, No. 5, page 231--233. It is prepared by using pregna-5,16-diene-20-one-3-hydroxyl-3-acetate (referred to as diene). Some improvements have been made to this method in the future, but basically the raw materials have not changed. However, as pregna-5,16-diene-20-one-3-hydroxy-3-acetate is produced by di...

Claims

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Application Information

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IPC IPC(8): C07J1/00C07J3/00
Inventor 卢彦昌
Owner TIANJIN PHARMA GROUP CORP