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Synthesis process for preparing steride 6-fluorine with triazine alizarin complexone

A technology of fluorine reagents and steroids, which is applied in the field of synthesis technology for the preparation of six-position fluorine groups of steroids, and can solve problems such as limitations, high prices, and high manufacturing costs

Inactive Publication Date: 2011-05-04
TIANJIN JINYAO GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, due to the special structure of Selectfluor, its manufacturing cost is relatively high, and the price is expensive, which is greatly restricted in the process of industrialization

Method used

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  • Synthesis process for preparing steride 6-fluorine with triazine alizarin complexone
  • Synthesis process for preparing steride 6-fluorine with triazine alizarin complexone
  • Synthesis process for preparing steride 6-fluorine with triazine alizarin complexone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090]

[0091] Add 0.2mol of raw materials into the reaction flask, add 400ml of N,N-dimethylformamide, pass nitrogen gas under stirring, cool down to -10 degrees, add 0.24mol of fluorinating agent of formula (III-1), and react for 5 hours , use triethylamine to adjust the pH to be neutral, dilute the solution in ice water, filter and dry to obtain 0.189mol of the product.

Embodiment 2

[0093]

[0094] Add 0.2mol of raw materials into the reaction flask, add 450ml of chloroform and methanol mixture (chloroform / methanol=2 / 8, v / v), pass nitrogen gas under stirring, cool down to 10 degrees, add the fluorinating agent of formula (III-2) 0.22mol, after reacting for 2 hours, dilute the solution in ice water, use ammonia water to adjust the pH to be neutral, stir for 10 minutes, then extract twice with 200ml chloroform, combine the chloroform layers and concentrate under reduced pressure, recrystallize with methanol, and dry by freeze filtration , 0.170mol 6αF was obtained.

Embodiment 3

[0096]

[0097] Add 0.2 mol of raw materials into the reaction flask, add 250 ml of acetonitrile, pass argon gas under stirring, control the temperature to 0 degrees, add 0.25 mol of the fluorinating agent of formula (III-3), react for 2 hours, and dilute the solution in ice water , using ammonia water to adjust the pH to be neutral, stirring for 10 minutes, and then extracting twice with 250ml chloroform, combining the chloroform layers and concentrating under reduced pressure, recrystallizing with methanol, freeze-filtering and drying to obtain 0.168mol 6αF product.

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Abstract

The invention relates to a synthesis process for preparing steride 6-fluorine with triazine alizarin complexone. In the process, a compound in a formula (II) and alizarin complexone react in an organic solvent to get a compound (I), wherien R1=H, halogen or OH; R2=H, alpha-OH, or acyloxy of alpha-C1-5; R3=H, OH, or alpha, beta C1-3 alkyl; R2, R3=alpha epoxy and double bonds; 15, 16 are 15-position C and 16-position C in a steroidring; M and Q are respectively H or alkyl 1 to 6 C, such as methyl and cyclohexyl; the M and the Q can also be five-membered or six-membered heterocyclic rings with one O or N heteroatom, such as furan, pyridine, piperidine and the like; R4=H, or alpha and beta hydroxyl; R5=H or alpha halogen; R4 and R5=beta epoxy and double bonds; R6= H or alkyl of 1 to 4 C, and a serpentine curve in a molecular formula is represented as substituent alpha or beta; and a full line and a dotted line between position 1 and position 2 are single bond or double bonds.

Description

Technical field: [0001] The invention relates to a synthesis process for preparing the six-position fluorine group of steroids, especially the process has less requirements on the molecular structure of steroids. Background technique: [0002] Introducing 6αF into the structure of corticosteroids can significantly increase the anti-inflammatory effect. Many commonly used corticosteroids have the structure of 6αF, such as fluocinolone, diflumetasone, fluticasone, etc., but because they are optical isomers, their synthesis has relatively low Great difficulty. [0003] Historically, many scientists have conducted multiple researches in this area and achieved certain results. Since the 1960s, scientists have obtained steroidal 6αF substances through various synthetic methods. [0004] For the synthesis process of 6αF with epicortisol as the starting material, Li Yuhua et al. The reaction temperature, solution pH, solvent polarity and other factors were optimized to increase t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J75/00C07J71/00C07J7/00C07J5/00
Inventor 孙亮陈松赵琳
Owner TIANJIN JINYAO GRP