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17alpha-hydroxy-19-norpregn-4,9-diene-3,20-dione preparation process

A preparation process, a pregnant-method, which is applied in the field of pharmaceutical preparation, can solve the problems of low cost and achieve the effects of easy operation, easy amplification and high yield

Inactive Publication Date: 2015-07-15
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to solve the problem of the industrial preparation of 17α-hydroxy-19-norpregna-4,9-diene-3,20-dione (1) in the prior art, according to the structural characteristics of compound 1, it was invented A novel preparation of 17α-hydroxy-19-norpregna-4,9-diene-3,20-dione with mild conditions, easy operation, high yield, low cost, and easy scale-up, suitable for industrial production process, the reaction formula is:

Method used

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  • 17alpha-hydroxy-19-norpregn-4,9-diene-3,20-dione preparation process

Examples

Experimental program
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Effect test

Embodiment 1

[0022] In a 500ml four-necked round-bottomed flask, add 20g of compound 2, 150ml of a THF / toluene 1:1 mixed solution, and 64.6ml of a 3mol / L THF solution of methylmagnesium bromide. Stir continuously with a mechanical stirrer. The reaction solution was raised to 70°C, and after 96 hours of reaction, the TLC plate monitored the reaction raw materials to basically react completely, put the reaction solution into an ice-water bath to cool it to 0°C and slowly add 100ml of saturated aqueous ammonium chloride solution dropwise, After the dropwise addition, it was stirred at room temperature for 2 hours, then poured into a separating funnel, extracted with toluene, the organic layer was collected, and 100 ml of trifluoroacetic acid and water were added to the organic layer to stir at room temperature for 2 hours. After 1 hour, the reaction solution was cooled to 0°C, slowly added dropwise with ammonia water to neutralize the pH value to 7, then the organic layer was collected by liqu...

Embodiment 2

[0025] In a 500ml four-necked round-bottomed flask, add 20g of compound 2, 150ml of a THF / toluene 1:1 mixed solution, and 64.6ml of a 3mol / L THF solution of methylmagnesium bromide. Stir continuously with a mechanical stirrer. The reaction solution was raised to 80°C, and after 57 hours of reaction, the TLC plate monitored the reaction raw materials to basically react completely, put the reaction solution into an ice-water bath to cool it to 0°C and slowly add 100ml of saturated aqueous ammonium chloride solution dropwise, After the dropwise addition, it was stirred at room temperature for 2 hours, then poured into a separating funnel, extracted with toluene, the organic layer was collected, and 100 ml of trifluoroacetic acid and water were added to the organic layer to stir at room temperature for 2 hours. After 1 hour, the reaction solution was cooled to 0°C, slowly added dropwise with ammonia water to neutralize the pH value to 7, then the organic layer was collected by liqu...

Embodiment 3

[0027] In a 500ml four-necked round-bottomed flask, add 20g of compound 2, 150m of a mixed solution of THF:toluene=1:1, and 96.9ml of a 3mol / L THF solution of methylmagnesium bromide, and use a mechanical stirrer to keep stirring. , the reaction solution was raised to 70°C, and after 20 hours of reaction, the TLC plate monitored the reaction raw materials to basically react completely, put the reaction solution into an ice-water bath to cool it to 0°C and slowly add 100ml of saturated ammonium chloride aqueous solution dropwise , after the dropwise addition, it was stirred at room temperature for 2 hours, then poured into a separatory funnel, extracted with toluene, the organic layer was collected, and then 100 ml of trifluoroacetic acid and water were added to the organic layer to stir at room temperature After 2 hours, the reaction solution was cooled to 0°C, slowly added dropwise with ammonia water to neutralize the pH value to 7, then the organic layer was collected by liqu...

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Abstract

The present invention provides a 17alpha-hydroxy-19-norpregn-4,9-diene-3,20-dione preparation process, which comprises: adding a reaction substrate 2 to an anhydrous mixing solvent, adding a methyl Grignard reagent, reacting for a certain time at a suitable temperature, carrying out a complete hydrolysis reaction on the obtained intermediate product under an acid condition after the reaction substrate completely reacts, and treating the reaction mixture to obtain the 17alpha-hydroxy-19-norpregn-4,9-diene-3,20-dione, wherein the reaction formula is defined in the instruction. The process of the present invention has advantages of avoidance of harsh reaction condition, high yield up to 88.5%, mild conditions, easy operation, and easy scale-up, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of pharmaceutical preparation, and in particular relates to a preparation process of 17α-hydroxy-19-norpregna-4,9-diene-3,20-dione. By adopting the new process, the product has high yield and low cost, and is very suitable for industrial production. Background technique [0002] Ulipristal Acetate is a new type of emergency contraceptive developed by HRA Pharma in France. It was launched in France in 2009 under the trade name Ella One. It is an oral tablet for use within 120 hours (5 days). Emergency contraception for unprotected intercourse or contraceptive failure. The chemical name of ulipristal acetate is 17α-acetoxy-11β-[4-(N,N-dimethylamino)phenyl]-19-norpregna-4,9-diene-3, 20‐diketone. [0003] [0004] 17α-Hydroxy-19-Norpregna-4,9-diene-3,20-dione (17α-Hydroxy-19-Norpregna-4,9-dien-3,20-dione) is a synthetic uridine acetate A key intermediate of hestatin, Pemmaraju N.Rao et al. describe 17α-hydroxy-19-n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
CPCC07J7/0045
Inventor 袁森林单晓燕陈旭东
Owner SHANGHAI INST OF PHARMA IND CO LTD
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