Method for synthesizing Drospirenone

A trospironone and condensation technology is applied in the field of synthesizing the steroid progesterone trospirenone, which can solve the problems of low yield, poor specificity, low yield and the like of the 7-position hydroxyl group, and achieves large-scale industrial production value and low cost. , the effect of simple operation

Inactive Publication Date: 2009-04-22
JIANGSU CHUANGUO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] However, there are some defects in the above-mentioned synthetic method. The yield of route one introducing the 7-position hydroxyl group is low, and the route two introduces the 6 and 7-position cyclopropane. The specificity is poor, so the yield of the two routes is relatively low and the cost is high.

Method used

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  • Method for synthesizing Drospirenone
  • Method for synthesizing Drospirenone
  • Method for synthesizing Drospirenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 3β, 5-dihydroxy-6β, 7β, 15β, 16β-dimethylene-5β-androst-17-epoxy

[0032] Operation: Heat 30ml of DMSO, 20ml of THF, and 5g of potassium tert-butoxide to 60°C for 0.5 hours, cool to below 0°C, quickly add 8g of bromotrimethylsulfide, stir at 0°C for 30 minutes, add S-10, and React at 0°C for one hour, TLC detects that the reaction is complete, analyze with ice water, filter, and dry to obtain 4.95 g of solid, and the plate layer shows that there are basically no impurities. TLC: cyclohexane: ethyl acetate = 1:2

Embodiment 2

[0033] Example 2 3β, 5-dihydroxy-6β, 7β, 15β, 16β-dimethylene-5β-androsta-21,17-carboxylide-21-ethyl carboxylate

[0034] Operation: Dissolve 3.6g of sodium ethoxide in 30ml of absolute ethanol, heat to 30-35 degrees, add 9ml of diethyl malonate, the internal temperature rises to 35-40 degrees, continue stirring for 10 minutes, put in 3g of raw materials, heat After reflux for 3 hours, the layer detection reaction was completed, cooled to room temperature, and water analysis. Filter to obtain a solid, and dry at room temperature 3.45g (do not heat and dry). The plies show slight impurities on top.

[0035] TLC cyclohexane: ethyl acetate = 1:2

Embodiment 3

[0036] Example 3 3β, 5-dihydroxy-6β, 7β, 15β, 16β-dimethylene-5β-androsta-21,17-carboxylate

[0037] Operation: Dissolve 11.2g of the raw material in 67ml of DMF under the protection of argon, add water, heat and reflux for 4 hours, TLC detects that the reaction is complete, cool to room temperature, analyze with saturated saline, filter, place and dry at room temperature to obtain 9.2g, and proceed directly Oxidized, the ply shows slight impurities.

[0038] TLC cyclohexane: ethyl acetate = 1:2

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Abstract

This invention provides a method for synthesizing steroidal progesterone drospirenone. The method comprises: utilizing 3beta, 5-dihydroxyl-6beta, 7beta, 15beta, 16beta-dimethylene-5beta-androstan-17-one (compound I) as the raw material, introducing epoxy at the 17 site, condensing, dehydrogenating, and oxidizing to obtain drospirenone. The method has such advantages as easy operation, high yield and is suitable for industrialization.

Description

Technical field: [0001] The invention belongs to the technical field of medicinal chemistry. In particular it relates to a method for the synthesis of the steroidal progestogen drospirenone. Background technique: [0002] The chemical name of drospirenone is 6β, 7β, 15β, 16β-dimethylene-3-oxo-17α-pregna-4-ene-21,17-carboxylate. A new type of synthetic progesterone with anti-mineralocorticoid and anti-androgenic activity, its pharmacological action spectrum is very similar to natural progesterone, which belongs to steroidal progestogen. It was first developed by ScheringAG in Germany. Yasmin, an oral contraceptive preparation made from this raw material product, consists of 3 mg drospirenone and 30 μg ethinyl estradiol, and has the advantages of better tolerance and less adverse reactions. The synthetic route of reporting drospirenone is as follows at present: [0003] (1) EP51143, DE19633685, see reaction formula (1). [0004] [0005] [0006] Reaction formula (1...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J53/00C07J21/00
Inventor 李金亮赵楠
Owner JIANGSU CHUANGUO PHARMA CO LTD
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