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Method for preparing fosaprepitant intermediate

An intermediate and temperature control technology, applied in the field of preparation of fosaprepitant intermediates, can solve the problems of death, malnutrition, affecting treatment effect and the like

Active Publication Date: 2013-04-03
JIANGSU HANSOH PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Because platinum, doxorubicin and other anti-tumor drugs will cause severe vomiting during the use, acute and severe nausea and vomiting may lead to dehydration, electrolyte imbalance, and malnutrition in patients, and severe cases may be caused by damage to the digestive tract mucosa. Bleeding, infection, and even death make patients fearful of chemotherapy and significantly reduce their compliance, resulting in reduced chemotherapy or suspension of treatment, which seriously affects the therapeutic effect. Therefore, antiemetic drugs are important adjuvant drugs for antitumor therapy, especially The use of drugs for the treatment of moderate and severe vomiting is also mainly concentrated in the field of adjuvant therapy for tumors

Method used

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  • Method for preparing fosaprepitant intermediate
  • Method for preparing fosaprepitant intermediate

Examples

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Effect test

Embodiment 1

[0021] Synthesis of step 1 formula III compound

[0022] Add 50% glyoxylic acid (67ml, 0.61mol) and tetrahydrofuran (130ml) to a 250ml reaction flask, heat to reflux, add dropwise a solution of N-benzylethanolamine (41.5g, 0.27mol) in tetrahydrofuran (20ml), dropwise Reflux overnight until the reaction is complete, evaporate tetrahydrofuran under reduced pressure, add water (170ml), stir and cool, and a solid precipitates, stir in an ice-water bath for 30 minutes, filter and wash with ice water to obtain 60.7g of wet product, and dry to obtain a light yellow solid, namely formula III Compound (51.8g, 91%), mp 132-136°C.

[0023]

[0024] The synthesis of step 2 formula I compound

[0025] The compound of formula III (51.8g, 0.250mol) was dissolved in dry acetonitrile (90ml), cooled to 5°C in an ice-water bath, trifluoroacetic anhydride (52.6g, 0.250mol) was added dropwise, and the inner temperature was raised to 30°C and stirred for 1 hour Then add dropwise (R)-1-[3,5-bis...

Embodiment 2

[0029] The method of Example 1 was adopted, except that in step 2, the n-hexane in the purification reagent was replaced by n-heptane, and finally the compound of formula I (62.6 g, 89.0%) was obtained.

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Abstract

The invention relates to a method for preparing a fosaprepitant intermediate which is a compound shown in a formula (I). The method includes the steps of reacting a compound in a formula (II) and glyoxylic acid to generate a compound in a formula (III), reacting the compound in the formula (III) and (R)-1-(3,5-bi(trifluoromethyl) phenyl) ethanol, and then separating and purifying. According to the method, preparation steps are simple, the reaction yield is high, and the fosaprepitant intermediate is suitable for large-scale production of medical industry.

Description

technical field [0001] The invention relates to a preparation method of a compound intermediate for treating chemotherapy-induced nausea and vomiting and postoperative nausea and vomiting, especially a preparation method of a fosaprepitant intermediate. Background technique [0002] Because platinum, doxorubicin and other anti-tumor drugs will cause severe vomiting during the use, acute and severe nausea and vomiting may lead to dehydration, electrolyte imbalance, and malnutrition in patients, and severe cases may be caused by damage to the digestive tract mucosa. Bleeding, infection, and even death make patients fearful of chemotherapy and significantly reduce their compliance, resulting in reduced chemotherapy or suspension of treatment, which seriously affects the therapeutic effect. Therefore, antiemetic drugs are important adjuvant drugs for antitumor therapy, especially The use of drugs for the treatment of moderate and severe vomiting is also mainly concentrated in th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/32
Inventor 徐士伟袁阜平
Owner JIANGSU HANSOH PHARMA CO LTD
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