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Preparation method of aprepitant III crystal form substance

A technology for aprepitant and crystal forms, applied in organic chemistry and other fields

Inactive Publication Date: 2014-05-14
TIANJIN CHEMPHARMATECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Wherein the reagent DIBALH used is both expensive and difficult to operate. Others use highly toxic sodium cyanide, and precious metal rhodium, azide compound of potential safety hazard and expensive tri(sec-butyl)lithium borohydride. The production process is neither safe nor expensive. tall

Method used

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  • Preparation method of aprepitant III crystal form substance
  • Preparation method of aprepitant III crystal form substance
  • Preparation method of aprepitant III crystal form substance

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Step 1: Synthesis of compound 3

[0020]

[0021] Add 80 g of acetonitrile into a 100 ml reaction flask, stir, and then add 10 g of 4-benzyl-2-hydroxy-morpholin-3-one. After cooling to 20°C, 9.2 g of trifluoroacetic anhydride was added. Add 10.5g of (R)-1-(3,5-bistrifluoromethylphenyl)ethanol in acetonitrile (20g) solution at 20-35°C, add 3.5g of boron trifluoride ether, and stir at 20-40°C for 2 hours . When the HPLC conversion rate is greater than 90%, slowly add 40 ml of 5M aqueous sodium hydroxide solution prepared in advance, and the temperature is less than 25°C. 8 g of tetrahydrolinalool was added, concentrated under reduced pressure, and acetonitrile was concentrated to dryness. Add 45 g of n-heptane and 20 g of water to the concentrated solution, filter, separate the liquid and discard the water phase. The organic phase was distilled under atmospheric pressure, and when it was collected to 1 / 10 of the original volume, it was cooled to 0-10°C and crystall...

Embodiment 2

[0032] Stability Comparison of Crystals of the Invention and Compounds of the Prior Art

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Abstract

The invention discloses a preparation method of an aprepitant (CAS NO.170729-80-3) III crystal form substance.

Description

Background technique [0001] Compound 5-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)- 4-morpholinyl] methyl]-1,2-dihydro-3H-1,2,4-triazol-3-ketone's general formula (I) is: [0002] [0003] Aprepitant is the only substance P / neurokinin 1 (NK1) receptor antagonist developed by Merck in the United States that has been approved for clinical use. In March 2003, it was approved by the US FDA to go on the market with the trade name Emend. It has a better preventive effect on acute and delayed nausea and vomiting reactions caused by highly emetogenic anti-tumor chemotherapy drugs (including high-dose cisplatin therapy). It will become the focus of clinical application of chemotherapy antiemetic drugs in the future. [0004] Examples of known routes: [0005] [0006] Prior Art (1) Brands, K.M.J.; Payack.J.F.; Rosen.J.D.; Todd D.Nelson, T.D.; Candelario, A.; Z.J.; Tschaen, M.D.; Hansen, K.; Devine, P.N.; Pye, P.J.; Rossen, K.; P.J.; J.Am.C...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/06
CPCC07D413/06
Inventor 王鑫
Owner TIANJIN CHEMPHARMATECH CO LTD
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