Preparation method for frovatripan succinate
A technology for furotriptan and succinic acid, which is applied in the fields of drug synthesis and organic compound synthesis and preparation, can solve the problems of low purity, high equipment requirements, infeasible methods, etc., and achieves overcoming the problems of the prior art, reasonable method selection, and technological progress. The effect of simple and easy route
Inactive Publication Date: 2015-04-22
CP PHARMA QINGDAO CO LTD
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Problems solved by technology
[0009] Patent CN103421855 mentions a synthetic method of furatriptan succinate intermediate, but the reaction steps are complex and the cycle is long; CN1034072 uses high-performance liquid phase chiral chromatographic column separation to obtain furotriptan in a single configuration, but the The chiral separation method can only prepare a small amount of scientific research supplies in the laboratory, which cannot be realized in industrial production; the final product prepared in CN1039491 is the racemate of furovatriptan, and the medicinal raw material is furotriptan in a single configuration. Triptan; CN1200931 utilizes the method of chiral resolution to obtain the compound of single configuration, and chiral resolution is widely used in industry, and operation is simple, and cost is lower, but needs catalytic pressurized hydrogenation in this route, requires to equipment Higher; Zhang Lijun, Synthesis of Furotriptan and Benzimidazole Derivatives, Master Thesis of Jilin University, the method mentioned in it was verified by the inventor, and the results proved that this method could not obtain furovatriptan in a single configuration, and its method is not feasible
[0010] In summary, there are certain limitations in the existing methods, such as low yield, low purity, long cycle, etc.
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[0025] The main process involved in this embodiment is the same as in the summary of the invention, wherein the specific process of compound 4 and compound 5 is as follows:
[0026] 1. Preparation of compound 4:
[0027]
[0028] Put L-pyroglutamic acid and MeOH into a 50L reaction kettle, stir and raise the temperature to 50°C, and set aside; put the intermediate compound 3 and MeOH into another 50L reaction kettle, stir and raise the temperature to 50-55°C, keep it warm for 1h, while The insoluble matter was removed by hot filtration, and the filtrate was poured into the above-mentioned L-pyroglutamic acid methanol solution for heat preservation, and the temperature was raised to reflux for 1 h. Naturally cool down to 20°C, add acetic acid dropwise, slowly cool down to 0°C after the dropwise addition, stir and crystallize for 3 hours, filter with suction, wash the filter cake with a small amount of methanol at 5°C, and dry the solid under vacuum at 40°C for 10 hours to ob...
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The invention discloses a preparation method for frovatripan succinate, belonging to technical field of medicine synthesis and organic compound synthesis and preparation. The preparation method comprises the following steps: by taking 4-cyanophenylhydrazine hydrochloride as a starting raw material, performing cyclization with N-methyl-1,4-dioxaspiro[4.5] decane-8-amine hydrochloride in hydrochloric acid, splitting with L-pyroglutamic acid and then catalytically hydrolyzing by using a boron trifluoride-acetic acid complex, and then salifying by using succinic acid to form frovatripan succinate. The preparation method can be used for making up for the defects in the prior art, is simple in synthesis process, stable in yield, high in product purity and suitable for industrial production.
Description
technical field [0001] The invention relates to a preparation method of furatriptan succinate, which belongs to the technical field of medicine synthesis and organic compound synthesis and preparation. Background technique [0002] Furotriptan succinate, Chinese chemical name: R-(+)3-methylamino-6-carbonamide-1,2,3,4-tetrahydrocarbazole monosuccinate monohydrate, the structural formula is as follows: [0003] [0004] Molecular formula: C 14 h 17 N 3 O·C 4 h 6 o 4 ·H 2 o [0005] Molecular weight: 379.4 [0006] Furotriptan was developed by Ireland's Elan Pharm acutieallne, and was approved by the US FDA in November 2001 in the form of its succinate (1:1) for the acute treatment of migraine with or without aura. Frova. At present, this product is not registered for sale in China. [0007] Furotriptan is a new type of anti-migraine drug that belongs to selective 5-HT1B / 1D receptor agonists. It overcomes the disadvantages of low oral bioavailability, short h...
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Login to View More IPC IPC(8): C07D209/88
CPCC07D209/88
Inventor 王明刚任莉陈阳生孙桂玉臧云龙
Owner CP PHARMA QINGDAO CO LTD