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Synthesis method of sildenafil analog

A technology of sildenafil and a synthesis method, which is applied in the field of sildenafil analog synthesis, can solve the problems of unsuitability for industrial scale-up production, complicated operation and high production cost, and achieves reduction of total cost, simple operation and total income. high rate effect

Active Publication Date: 2015-05-27
JINAN MEILUWEI BIOTECH CO LTD
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  • Description
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Problems solved by technology

[0007] The synthesis process starts with 5-[2-ethoxy-5-(4-methylpiperazin-1-ylcarbonyl)]phenyl-1-methyl-3-n-propyl-1,6-dihydro- 7H-pyrazolo[4,3-d]pyrimidin-7-one as raw material, and P 2 S 5 Prepared through one-step vulcanization reaction, the production cost is relatively high, and the operation is complicated, so it is not suitable for industrial scale-up production

Method used

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  • Synthesis method of sildenafil analog
  • Synthesis method of sildenafil analog
  • Synthesis method of sildenafil analog

Examples

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Effect test

Embodiment 1

[0034] A kind of synthetic method of sildenafil analogue, comprises the following steps:

[0035] (1) Compound (B): 5-[2-ethoxy-5-(chloromethyl-1-ylcarbonyl)]phenyl-1-methyl-3-n-propyl-1,6-dihydro Preparation of -7H-pyrazolo[4,3-d]pyrimidin-7-one

[0036] Put 180g (1.592mol) of chloroacetyl chloride into a dry 500ml reaction bottle, cool the reaction solution to below 20°C, add 122.4g (0.9175mol) of anhydrous aluminum trichloride in batches below 20°C, and stir for 10min . After the reaction was completed, the reaction solution was cooled with ice water to below 20°C, and 55.68g (0.1784mol) of compound (A) was put into the reaction flask in batches, and the feeding speed was controlled so that the internal temperature did not exceed 20°C. After the casting, the reaction was stirred at 45-50°C for 3h. After the reaction was completed, the reaction solution was added back into the ice-water mixture. After the solid material was completely precipitated, it was filtered, collec...

Embodiment 2

[0044] A kind of synthetic method of sildenafil analogue, comprises the following steps:

[0045] (1) Compound (B): 5-[2-ethoxy-5-(chloromethyl-1-ylcarbonyl)]phenyl-1-methyl-3-n-propyl-1,6-dihydro Preparation of -7H-pyrazolo[4,3-d]pyrimidin-7-one

[0046] Put 180g (1.592mol) of chloroacetyl chloride into a dry 500ml reaction bottle, cool the reaction solution to below 20°C, add 125g (0.9370mol) of anhydrous aluminum trichloride in batches below 20°C, and stir for 10min after the injection is complete. After the reaction was completed, the reaction solution was cooled with ice water to below 20°C, and 55.72g (0.1785mol) of compound (A) was put into the reaction flask in batches, and the feeding speed was controlled so that the internal temperature did not exceed 20°C. After the casting was completed, the reaction was stirred at 45-50°C for 4h. After the reaction was completed, the reaction solution was added back into the ice-water mixture. After the solid material was comple...

Embodiment 3

[0054] A kind of synthetic method of sildenafil analogue, comprises the following steps:

[0055] (1) Compound (B): 5-[2-ethoxy-5-(chloromethyl-1-ylcarbonyl)]phenyl-1-methyl-3-n-propyl-1,6-dihydro Preparation of -7H-pyrazolo[4,3-d]pyrimidin-7-one

[0056] Put 180g (1.592mol) of chloroacetyl chloride into a dry 500ml reaction bottle, cool the reaction solution to below 20°C, add 124.3g (0.9317mol) of anhydrous aluminum trichloride in batches below 20°C, and stir for 10min . After the reaction was completed, the reaction solution was cooled with ice water to below 20°C, and 55.86g (0.1789mol) of compound (A) was put into the reaction flask in batches, and the feeding speed was controlled so that the internal temperature did not exceed 20°C. After the casting, the reaction was stirred at 45-50°C for 2h. After the reaction was completed, the reaction solution was added back into the ice-water mixture. After the solid material was completely precipitated, it was filtered, collec...

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Abstract

The invention provides a synthesis method of a sildenafil analog. The chemical name of the sildenafil analog is 5-[2-ethoxy-5-(4-methylpiperazine-1-yl-thiocarbonyl)]phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazol[4,3d]pyrimidine-7-thioketone; the sildenafil analog is prepared from 5-(2-ethoxy)phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazol[4,3-d]pyrimidine-7-one as a raw material through four steps of chemical reactions. The synthesis method of the sildenafil analog is simple in synthesis step operations, economic and environmentally friendly; the yield of each step is above 75% and the total yield is relatively high; the synthesis method is suitable for industrial production.

Description

technical field [0001] The invention relates to the improvement of the preparation process of organic compounds, in particular to a synthesis method of sildenafil analogues. Background technique [0002] Sildenafil (sidenafil, trade name viagra, Chinese name: Viagra, Viagra) chemical name is 5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)]phenyl- 1-Methyl-3-n-propyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one is a phosphodiesterase inhibitor developed by American Pfizer (Pfizer) Developed and produced by the company, it is the first clinical oral drug specially used for the treatment of male erectile dysfunction (ED), which can significantly improve erectile dysfunction and premature ejaculation. It was launched in China in July 2000. The listing of sildenafil has created a new field for the treatment of male impotence. The currently marketed drugs for the treatment of male erectile dysfunction include vardenafil jointly developed by German Bayer and Glaxo smithkline, and ta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 王靖林刘桂贞于瑞梅曾庆梅李洋王松
Owner JINAN MEILUWEI BIOTECH CO LTD
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