Methods for preparing fluoxymesterone and intermediate thereof

A technique for an intermediate and fluoxymethylene, which is applied in the field of preparation of steroid compounds, can solve the problems of insufficient fluoxymester process route, difficulty in obtaining starting materials, production waste, etc., and achieves reduction of production cost and industrialization conditions, and easy operation. , the effect of the line is reasonable

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

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Problems solved by technology

4. Aplastic anemia Treatment of aplastic anemia and anemia caused by other reasons may improve bone marrow hematopoietic function, especially red blood cell production, but the effect is very slow
[0007] There are deficiencies in the process route for the preparation of fluoxymesterone in the above-mentioned patent, mainly because the starting materials are not easy to obtain, and biological fermentation is required, and the yield is only 6.7%, resulting in waste in production

Method used

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  • Methods for preparing fluoxymesterone and intermediate thereof
  • Methods for preparing fluoxymesterone and intermediate thereof
  • Methods for preparing fluoxymesterone and intermediate thereof

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0031] Preparation of 9,11-double bond-17α-methyltestosterone

[0032]

[0033] (1) 9, 11 dehydration

[0034] Put 10g11αhydroxy-4AD and 45ml tetrahydrofuran into the reaction flask under stirring, cool down to -60°C, then add 9gPCl 5 Add it to the reaction flask, control the temperature to react at -50~-60℃ for 2 hours, monitor with thin layer chromatography until the reaction ends without raw materials, pour the reaction solution into 50 times of ice water to dilute, add 10g of flake alkali to neutralize, and precipitate out crystals. It was left to stand, filtered, the filter cake was washed with water until neutral, and dried to obtain 9.2 g of compound 4,9(11)-androstadiene-3,17-dione (II).

[0035] (2) 3-position keto group protection

[0036] 9.2g of 4,9(11)-androstadiene-3,17-dione (II) and 200ml of benzene obtained in step (1) were put into a reaction flask under stirring, and 12ml of pyrrolidine and 10mg of p-toluenesulfonic acid were added. acid, heated to ref...

Embodiment 2

[0043] Preparation of 9,11-double bond-17α-methyltestosterone II

[0044]

[0045] (1) 9, 11 dehydration

[0046] Put 10g11αhydroxy-4AD and 45ml dioxane into the reaction flask under stirring, cool down to -50℃, then add 9.5gPOCl 3 Add it into the reaction flask, control the temperature to react at -50~-60℃ for 3 hours, monitor with thin layer chromatography until the reaction ends without raw materials, pour the reaction solution into 50 times ice water to dilute, add 10g of flake alkali to neutralize, and precipitate out crystals. Set aside, filter, wash the filter cake with water until neutral, and dry to obtain 9.1 g of compound 4,9(11)-androstadiene-3,17-dione (II).

[0047] (2) 3-position keto group protection

[0048] 9.1g of 4,9(11)-androstadiene-3,17-dione (II) and 200ml of toluene obtained in step (1) were put into a reaction flask under stirring, and 15ml of morpholine and 20mg of p-toluenesulfonic acid were added. acid, heated to reflux for 3h, the reactor wa...

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Abstract

The invention relates to methods for preparing fluoxymesterone and an intermediate (V) thereof. The method for preparing the intermediate of the fluoxymesterone comprises the following processes of: with 11alpha hydroxy-4AD (I) as an initial raw material, 9 and 11 position dehydration, 3 position ketonic group protection, 17 position ketonic group Grignard reaction and 3 position hydrolysis protection to obtain the intermediate of the fluoxymesterone.

Description

technical field [0001] The present invention relates to the preparation method of steroid compound, especially relate to the preparation method of fluoxymester and its intermediate. Background technique [0002] Fluoxymesterone is an androgen, its function and application are similar to methyl testosterone, characterized by slower metabolism in the body, longer duration of action, and more uses, mainly including: 1. Symptoms, cryptorchidism) during the replacement therapy with testosterone, can promote the development of the penis and secondary sexual characteristics. If combined with chorionic gonadotropin to treat cryptorchidism, the testis can descend from the recess. 2. Functional uterine bleeding mainly exerts hemostatic effect through the effect of anti-estrogen to make uterine muscle fibers and uterine vasoconstriction, and endometrial atrophy to play a hemostatic effect, which is especially suitable for menopause. 3. The application of testosterone in metastatic br...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
Inventor 王淑丽金玉鑫郑彤
Owner TIANJIN JINYAO GRP
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