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Novel technology for synthesizing pregnene 11-site beta-hydroxy

A compound and reaction technology, applied in the field of production technology for preparing prednisolone and derivatives thereof, can solve the problems of incomplete hydrolysis, great difficulty in deprotection, easy generation of impurities, etc., so as to reduce labor costs and reduce solvent consumption. , the effect of simplifying the operation steps

Active Publication Date: 2012-03-14
TIANJIN JINYAO GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, due to the protection of the 17-hydroxyl group, such as the formation of a 17-ester, the deprotection is more difficult, the hydrolysis will be incomplete, and impurities are likely to be produced, which will cause greater troubles to the later stage of refining.

Method used

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  • Novel technology for synthesizing pregnene 11-site beta-hydroxy
  • Novel technology for synthesizing pregnene 11-site beta-hydroxy
  • Novel technology for synthesizing pregnene 11-site beta-hydroxy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] step a

[0037] Add 10mmol of compound 1.1 into 50ml of ethanol, reflux and add 45mmol of tetrahydropyrrole and 0.6ml of triethyl orthoformate under nitrogen protection, react until there is no raw material, concentrate under reduced pressure and cool to 0°C, dilute in 100ml of ice water, filter , to obtain 2.19.4 mmol of solid.

[0038] step b

[0039] Add 2.19mmol of the solid to 50ml of methanol and 2ml of pyridine, stir and heat to 40-45°C, add KBH within 15 minutes 4 12mmol, react until there is no raw material, control the temperature below 40°C and add acetic acid dropwise until the pH is 7, concentrate under reduced pressure and cool down to 0°C, dilute in 100ml ice water, filter to obtain 3.18.2mmol of solid.

[0040] step c

[0041] Add 3.15mmol of the solid to 50ml of 10% acetic acid aqueous solution, stir at room temperature, and react until no raw material is found. After extracting three times with 30ml of chloroform, check the concentration...

Embodiment 2

[0043]

[0044] step a

[0045] Add 10mmol of compound 1.2 into 50ml of cyclohexane, reflux and separate water, add 50mmol of 2-methyltetrahydropyrrole dropwise under nitrogen protection, react until no raw materials are left, concentrate under reduced pressure and cool to 0°C, precipitate solid 2.2, filter , to obtain 2.29.0 mmol of solid.

[0046] step b

[0047] Add 2.28mmol of the solid into 50ml of methanol, stir and heat to 40-45°C, add NaBH within 15 minutes 4 12mmol, react until there is no raw material, control the temperature below 40°C and gradually add acetic acid until the pH is 7, concentrate under reduced pressure and cool down to 0°C, dilute in 100ml ice water, filter to obtain 3.27.1mmol of solid.

[0048] step c

[0049] Add 3.25mmol of the solid to 50ml of 10% aqueous acetic acid solution, stir at room temperature, and react until there is no raw material. After extracting three times with 30ml of chloroform, check the concentration, recrystallize with...

Embodiment 3

[0051]

[0052] step a

[0053] Add 10mmol of compound 1.3 into 50ml of absolute ethanol, reflux and add 50mmol of tetrahydropyrrole and 0.6ml of triethyl orthoformate under nitrogen protection, react until there is no raw material, concentrate under reduced pressure and cool to 0°C, dilute in 100ml of ice water , filtered to obtain 2.18.9 mmol of solid.

[0054] steps b and c

[0055]Add 2.18mmol of the solid to 50ml of methanol and 2ml of pyridine, stir and heat to 40-45°C, then add 0.03g of CdCl 2 (2 / 5)H 2 O, join KBH in 15 minutes 4 12mmol, react until there is no raw material, control the temperature below 40°C and add 50% acetic acid aqueous solution dropwise to pH 3, concentrate under reduced pressure and cool to 0°C, dilute in 100ml ice water, filter to obtain 4.37.1mmol of solid.

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Abstract

The invention discloses a novel technology for synthesizing pregnene 11-site beta-hydroxy. According to the invention, nafoxidine or a derivative thereof is used for forming a protecting group for pregnene 3, 20 ketone; borohydride is used for reducing pregnene 11 ketone; and nafoxidine is dissociated by using an acid. According to the invention, the three steps of reactions can be completed in a same reaction system; or the last two steps can be completed in a same reaction system. In the step c, the protecting group can be removed without the application of an organic solvent.

Description

Technical field: [0001] The invention relates to a new process for synthesizing the 11-position β-hydroxyl of pregnane, in particular, the process can be used as a production process for preparing prednisolone and its derivatives. Background technique: [0002] The presence of oxygen-containing functional groups at C-11 in the steroidal structure is more important, and it is indispensable for anti-inflammatory effects and glucose metabolism. Xu Lu et al. reported (Applied Chemistry 1995, 1, 59) to analyze the conformation of steroidal anti-inflammatory drugs by means of molecular mechanics, and studied the correlation between the conformation and activity of such compounds. The results showed that not only in specific positions The substitution of the oxygen atom, and the steric position and steric energy of the oxygen atom are important factors affecting the activity of this type of compound. [0003] Some steroidal compounds with 11-hydroxyl, especially 11β-hydroxyl, have...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J75/00C07J7/00C07J13/00C07J71/00C07J43/00
CPCY02P20/55
Inventor 孙亮陈松赵琳
Owner TIANJIN JINYAO GRP
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