Preparation method of Eslicarbazepine

A technology of chiral catalyst and hydrogen source, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalyst, organic chemistry, etc., can solve separation and purification difficulties, reduce solvent recovery utilization rate, and use a large amount of catalyst and other issues, to achieve the effect of high atom economy, atom economy, green environmental protection, and high recycling rate

Active Publication Date: 2011-11-23
浙江瑞博制药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Similarly, the disadvantages are: the hydrogen source used is a mixture of tertiary ammonia compounds and formic acid, which will cause the reaction to produce by-products, making separation and purification difficult; the reaction solvent used is a mixed solvent, thereby reducing the recovery rate of the solvent; the reaction temperature is very high. High, the reaction can only be carried out under the condition of more than 100 ° C, and the amount of catalyst is large, so it is necessary to continue to screen the catalyst

Method used

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  • Preparation method of Eslicarbazepine
  • Preparation method of Eslicarbazepine
  • Preparation method of Eslicarbazepine

Examples

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Effect test

Embodiment 1

[0047] Evacuate the 1L autoclave to 2 ((S)-Xyl-SDP)((R,R)-DPEN)](RuCl 2 (p-cymene) and (R, R-DPEN) are from reagent companies, (S)-Xyl-SDP is from Zhejiang Jiuzhou Pharmaceutical Co., Ltd.) and 500ml of degassed absolute ethanol. Use high-purity nitrogen to change the gas in the kettle three times, and then replace nitrogen with high-purity hydrogen three times. Heating to 55-60°C, and then leading to high-purity hydrogen to 10.0Mpa, keeping for 48 hours. Sampling analysis showed that oxcarbazepine was <0.10%. Drain the hydrogen in the kettle, replace the hydrogen in the kettle with nitrogen three times, transfer the reaction solution to a 1000ml ordinary reaction bottle, concentrate the ethanol, stop the concentration when about 450ml is evaporated, and add 500ml of pure water while it is hot. Raise the temperature to reflux, then slowly cool to 5-10°C, and keep it for 2 hours, filter, wash the filter cake with iced ethanol water (1:10), and dry the product under vacuum at ...

Embodiment 2

[0049] Evacuate the 1L autoclave to 2 ((S)-Tol-SDP)((R,R)-DPEN)](RuCl 2 (p-cymene) and (R, R-DPEN) come from Reagent Company, (S)-Tol-SDP comes from Zhejiang Jiuzhou Pharmaceutical Co., Ltd.) and 400ml of degassed anhydrous isopropanol. things. Use high-purity nitrogen to change the gas in the kettle three times, and then replace nitrogen with high-purity hydrogen three times. Heating to 70-80°C, and then leading to high-purity hydrogen to 5.0Mpa, keeping until oxcarbazepine<0.10% to end the reaction. Drain the hydrogen in the kettle, replace the hydrogen in the kettle with nitrogen three times, transfer the reaction solution to a 1000ml common reaction bottle, concentrate the isopropanol, stop the concentration when about 350ml is evaporated, and add 500ml of pure water while it is hot. Raise the temperature to reflux, then slowly cool to 5-10°C, and keep it for 2 hours, filter, wash the filter cake with icy isopropanol water (1:10), and dry the product under vacuum at 50°C...

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Abstract

The invention relates to the field of chemical substance and medicament preparation, specifically to a preparation method of Eslicarbazepine. The preparation method provided by the invention is to perform a reaction of Oxcarbazepine in the presence of a chiral catalyst [MX2((S)-xyl-SDP)((R,R)-DPEN)] to obtain Eslicarbazepine. [MX2((S)-xyl-SDP)((R,R)-DPEN)] is mainly formed by the coordination combination of a chiral diphosphine ligand (a) compound, a chiral nitrogen ligand (b) compound and a metal salt catalyst (MX2(p-cymene)), wherein R1, R2, R3, R4 and R5 are C1-C6 alkyl group or C6-C10 aryl group or hydrogen or -OR6; R6 is C1-C6 alkyl group or C6-C10 aryl group or hydrogen; R7 is C6-C10 aryl group or C1-C6 alkyl group; R8 is C6-C10 aryl group or C1-C6 alkyl group or hydrogen; M is Ru, Rh, Ir, Fe, Co or Ni; and X is a halogen.

Description

technical field [0001] The invention relates to the field of chemical substances and medicine preparation, in particular to the preparation of a chiral medicine. Background technique [0002] Elixipine, also known as Eslicarbazepine ((S)-Licarbazepine), the English name is: Eslicarbazepine, or S-licarbazepine, the CAS number is 104746-04-5, and the chemical name is S-10-monohydroxy- dihydro-carbamazepin (S-10-monohydroxy-dihydro-carbamazepine), molecular formula: C15H14N2O2, molecular weight: 254.28, structural formula as shown below: [0003] [0004] Elixipine [0005] It is mainly marketed in the form of acetate, that is, Eslicarbazepine acetate, which is a typical chiral drug, mainly for the treatment of epilepsy, central and peripheral nervous system disorders, anxiety, neuropathic pain and neuropathic pain related illnesses. [0006] According to the reported literature, the synthesis method of elixipine acetate is as follows: firstly prepare elixipine, and then ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/22B01J31/24
Inventor 车大庆朱国良
Owner 浙江瑞博制药有限公司
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