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Preparation method of progestin-1,4-double bond-11-one-21-acetate compound

A compound, iodide technology, applied in the field of preparation of progesterone compounds, can solve the problems of small progress and the like

Inactive Publication Date: 2017-06-27
TIANJIN JINYAO GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] In recent years, researchers have been working hard to innovate and improve the single-step process, but limited by traditional empirical thinking, the adjustment of the process route is currently being carried out and little progress has been made.

Method used

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  • Preparation method of progestin-1,4-double bond-11-one-21-acetate compound
  • Preparation method of progestin-1,4-double bond-11-one-21-acetate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] General reaction formula:

[0074]

[0075] Reaction process: Arthrobacter Simple ATCC 21032 was subjected to slant culture, primary culture and secondary culture in sequence, the culture temperature was 28-32°C, the micronized substrate compound 2 was put into a 5L fermenter, and the feeding concentration was 3 -4%, the reaction temperature is 28-32°C, when the remaining substrate is less than 4%, the fermentation is considered to be complete. After the reaction was completed, the temperature was raised to 70°C to terminate the reaction, the fermentation broth was extracted with ethyl acetate, the ethyl acetate was concentrated, and the conversion rate of the substrate was measured, and compound 3 was obtained by recrystallization method using methanol.

[0076]

Embodiment 2

[0082] General reaction formula:

[0083]

[0084] Synthesis:

[0085] Put 5g of compound 3 into the reactor, add 50ml of methanol, cool down to 20°C, add 3g of calcium oxide, and add iodine solution dropwise for 1-2 hours (preparation method of iodine solution: put 9g of iodine into a 200ml single-necked bottle, add 2g of anhydrous chlorine Calcium chloride, 30ml methanol, stirring for 2 hours to dissolve) is completed, keep warm until there is no raw material point, add 400ml of ice water, stir to precipitate solid, filter to obtain iodide, no need to dry, then put it directly into another reactor, add 200ml Acetone, 20ml of glacial acetic acid, 10g of potassium acetate, heated to 60°C and reacted to the point of no raw materials, concentrated acetone under reduced pressure, added 400ml of ice water to stir the precipitate, filtered to obtain a solid, and dried at 80°C to obtain compound 4.

[0086]

[0087]

Embodiment 3

[0089] General reaction formula:

[0090]

[0091] Reaction process: add 10g compound 4 (content is 97.4%, maximum impurity <2%), dimethyl sulfoxide 30g, activator to react in 100ml chloroalkane at -15 ℃, detect substrate content by high performance liquid phase< After 1%, add an organic base to adjust the pH to 8.5-10, concentrate under reduced pressure to no chlorinated alkanes, cool down to 0°C, dilute with 100ml of 0°C water under stirring, and filter to obtain compound 1.

[0092]

[0093]

[0094]

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PUM

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Abstract

The invention relates to a preparation method of a progestin-1,4-double bond-11-one-21-acetate compound. By utilizing the preparation method, the compound with the basic structure of progestin-1,4-double bond-11-one-21-acetate can be prepared in a high yield manner according to a following reaction route through regulating biodehydrogenation reaction and a 11-site hydroxyl oxydone radical.

Description

[0001] Technical field: [0002] The invention relates to a preparation method of a pregnane compound, which has a basic structure of pregnane-1,4 double bond-11-one-21-acetate. [0003] Background technique: [0004] In the research on the synthesis of steroid hormones, it was found that the chemical modification of molecular structure, such as the introduction of certain groups, can greatly increase the efficacy of drugs, reduce side effects, and even make drugs produce different types of curative effects. The structure of anti-inflammatory steroids can increase its anti-inflammatory activity exponentially after introducing a double bond at the C1,2 position. The structure of prednisone and cortisone only differs in the 1,2-position double bond, but the difference in anti-inflammatory activity is 4 times . The C-11 oxygen-containing functional group introduced into the anti-inflammatory steroid structure is indispensable for the drug to have anti-inflammatory and glucose met...

Claims

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Application Information

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IPC IPC(8): C12P33/00C12P33/20C07J5/00C07J13/00C07J71/00C12R1/06
CPCC07J5/0053C07J5/0076C07J13/005C07J71/001C12P33/00C12P33/20
Inventor 张杰王福军高占元
Owner TIANJIN JINYAO GRP
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