Preparation method for progestin

A technology of progesterone and androstenedione, which is applied in the field of preparation of the progesterone drug progesterone, can solve the problems of not obvious cost advantages, difficult purification, poor quality, etc., and achieve low cost, wide source of raw materials, and good quality effects

Active Publication Date: 2015-01-07
HUNAN KEREY BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the obtained impurities are many, the quality is poor, and the purification is difficult
If refined repeatedly until the quality is qualified, the total weight yield is only 60-65%, and the cost advantage is not obvious

Method used

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  • Preparation method for progestin
  • Preparation method for progestin
  • Preparation method for progestin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A. Preparation of ether compounds

[0028] In a 1000ml three-necked flask, add 100g 4AD, 200ml ethanol, 80ml triethyl orthoformate, 2g p-toluenesulfonic acid, keep warm at 20-25°C and stir for 12-16 hours. TLC detects the end point of the reaction. After the reaction, add 3ml Pyridine, stir for 20-25 minutes to neutralize the acid, then cool the system to -5-0°C, stir and crystallize for 2-3 hours, filter with suction, wash with a small amount of ethanol, combine the lotion and filtrate, recover the solvent and use the crude product mechanically; filter cake Drying below 70°C gave 101.6g of ether compound with HPLC content of 99.2% and weight yield of 101.6%.

[0029] B. Preparation of nitro compounds

[0030]In a 1000ml three-necked flask, add 100g of ether compound, 400ml of nitroethane, and 5ml of ethylenediamine, keep warm at 85-90°C and stir for 6-8 hours. TLC detects the end point of the reaction. After the reaction, concentrate under reduced pressure and recover...

Embodiment 2

[0034] A. Preparation of ether compounds

[0035] In a 1000ml three-neck flask, add 100g4AD, 600ml dichloromethane, 80ml triethyl orthoformate, 2g p-toluenesulfonic acid, keep warm at 20-25°C and stir for 12-16 hours. TLC detects the end point of the reaction. After the reaction, Add 3ml of pyridine, stir for 20-25 minutes to neutralize the acid, concentrate under reduced pressure, recover dichloromethane, lower the temperature, add 100ml of ethanol, then cool the system to -5-0°C, stir and crystallize for 2-3 hours, suction filter, a small amount Wash with ethanol, combine the lotion and filtrate, recover the solvent and reuse the crude product; dry the filter cake below 70° C. to obtain 100.2 g of ether compound, the HPLC content is 99.4%, and the weight yield is 100.2%.

[0036] B. Preparation of nitro compounds

[0037] In a 1000ml three-necked flask, add 100g of ether compound, 60ml of nitroethane, 600ml of toluene, and 5ml of ethylenediamine, keep warm at 85-90°C and st...

Embodiment 3

[0041] A. Preparation of ether compounds

[0042] In a 1000ml three-neck flask, add 100g 4AD, 200ml ethanol, 80ml triethyl orthoformate, add 2g of HCl gas, seal it, keep it warm at 2025°C and stir for 12-16 hours. TLC detects the reaction end point. After the reaction, add 3ml Pyridine, stir for 20-25 minutes to neutralize the acid, then cool the system to -5-0°C, stir and crystallize for 2-3 hours, filter with suction, wash with a small amount of ethanol, combine the lotion and filtrate, recover the solvent and apply the crude product; filter cake After drying below 70°C, 103.2 g of the ether compound was obtained, the HPLC content was 99.1%, and the weight yield was 103.2%.

[0043] B. Preparation of nitro compounds

[0044] In a 1000ml three-neck flask, add 100g of ether compound, 400ml of nitroethane, and 5ml of N,N-tetramethylethylenediamine, keep warm at 85-90°C and stir for 6-8 hours. TLC detects the end point of the reaction. , concentrated under reduced pressure, an...

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Abstract

The invention relates to a preparation method for progestin. 4-androstenedione is used as a raw material. The preparation method comprises the following steps: A, etherate is synthetized, wherein the 4-androstenedione and triethyl orthoformate perform an acid catalyzed reaction in organic solvents of dichloromethane, low-carbon alcohol and the like to obtain the etherate 3-ethoxy-androstane-3, 5-diolefin-17-ketone; B, a nitro substance is synthetized, wherein the etherate in the organic solvents and nitroethane perform 17-bit addition under the catalysis of ethylenediamine to obtain the nitro substance 3-ethoxy-20-nitro-pregnane-3, 5, 17 (20)-triene; and C, the progestin is synthetized, wherein the nitro substance is reduced by zinc powder in organic solvents of acetic acids, low-carbon alcohol and the like, acid hydrolysis is performed, so that semi-finished products of the progestin are obtained, the semi-finished products of the progestin are decolored and refined by alcohol and activated carbon to obtain the progestin, the content of HPLC is more than 99.5%, the melting point is 128-131 DEG C, and the total yield of synthetized weight is 83-87%. When the method disclosed by the invention is used for producing the progestin, the yield is high, the degree of purity is good, the quality is stable, the solvent recovering rate is high, and the method is economic and environment-friendly.

Description

technical field [0001] The invention belongs to the preparation technology of steroid hormone medicine, and in particular relates to a preparation method of progesterone medicine progesterone. Background technique [0002] Progesterone is an endogenous progesterone that plays an important role in human fertility. Clinically, it is widely used in functional uterine bleeding, threatened abortion and habitual abortion, menorrhagia, dysmenorrhea, amenorrhea, endometriosis and advanced breast cancer, and it is also used in family planning. progesterone drugs. [0003] The traditional production method of progesterone is to extract diosgenin from the yam plant, through protection, oxidative cracking, and elimination, the obtained key intermediate acetic acid gestational dienolone (diene for short) is used as raw material, through catalytic hydrogenation, hydrolysis , Austenitic oxidation three-step reaction, its synthetic route is shown in the appendix figure 1 . The productio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
CPCC07J7/002
Inventor 胡爱国谢来宾吴来喜谢勇
Owner HUNAN KEREY BIOTECH
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