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Method for preparing sarpogrelate hydrochloride

A technology of sarcogrelate hydrochloride and salt formation, which is applied in the field of preparation of sarcogrelate hydrochloride, can solve the problems that it is difficult to obtain high-purity products and difficult to remove, and achieve the effect of simple industrial production, easy operation and low production cost

Inactive Publication Date: 2013-05-22
NANJING KANGRAN PHARMA TECH
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] 2-((3-methoxy)styryl)phenol (III) is prepared by catalytic hydrogenation of intermediate 2-((3-methoxy)styryl)phenol (II), however 2-(( 3-methoxy) styryl) phenol (II) is usually prepared by the Wittig reaction, which will produce a large amount of triphenylphosphine oxide, which is difficult to remove. At present, the existing methods are all purified by chromatographic column:
[0013] Chinese patent CN1824647A mentions the use of acetone-water as the recrystallization solvent, and the inventor found that it is difficult to obtain high-purity products by using this system

Method used

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  • Method for preparing sarpogrelate hydrochloride
  • Method for preparing sarpogrelate hydrochloride

Examples

Experimental program
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Embodiment 1

[0038] 100 kg (containing 55% of triphenylphosphine oxide) of 2-((3-methoxy) styryl) phenol mixture prepared by Wittig reaction (J.Med.Chem.1990, 33:1818-1823) Into a 1000L autoclave, add 450 liters of ethanol, 15 kg of 5% Pd-C, add hydrogen to 0.5Mpa, stir and hydrogenate at a temperature of 50°C for 3 hours, filter and concentrate to obtain a light yellow oil with a yield of 96%, HPLC Detection showed complete hydrogenation. Example 22-((3-methoxy)phenethyl)phenol (mixture)

Embodiment 2

[0039] Add 190 grams of 2-((3-methoxy) styryl) phenol mixture (containing 52% triphenylphosphine oxide) prepared by Wittig reaction into the reaction flask, add methanol 1000 ml, 20 grams of Raney nickel, Introduce hydrogen, stir and hydrogenate at 40°C for 10 hours, filter, and concentrate to obtain a light yellow oil, which is detected by HPLC and shows that the hydrogenation is complete. Example 32-((3-methoxy)phenethyl)phenol (mixture)

Embodiment 3

[0040] As in Example 1, 10% palladium carbon was used instead, the pressure was 1 MPa, and the reaction was carried out at room temperature, with a yield of 95%.

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Abstract

Provided is a preparing method of sarpogrelate hydrochloride, characterized in that 2-((3-methoxyl)styrylcoumarin)phenol mixture containing triphenylphosphine oxide is catalyzed and hydrogenated, and then reacted with epichlorohydrin and dimethylamine to obtain 2-(dimethylamino)-1-(o-(m-methoxyphenylethyl)phenoxymethyl)ethanol, at the same time, triphenylphosphine oxide is separated or not, reacted with succinic anhydride, salt-formed with chlorine hydride, and re-crystallization by a proper solvent, so as to obtain sarpogrelate hydrochloride.

Description

technical field [0001] The present invention relates to a kind of preparation method of sagrester hydrochloride, more specifically, relate to a kind of use 2-((3-methoxy) styryl) phenol containing triphenylphosphine oxide as raw material to prepare sarcogrelor hydrochloride ester method. Background technique [0002] Sarpogrelate Hydrochloride (Sarpogrelate Hydrochloride) chemical name Succinic acid (2-dimethylamino-1-o (m-methoxyphenethyl) phenoxymethyl) ethyl ester hydrochloride (Butanedioic Acid, mono2-(Dimethylamino )-1-[[o-(m-methoxyphenethyl)phenoxy]methyl]ethyl ester hydrochloride, CAS Registry Number: 135159-51-2, the structural formula is as follows: [0003] [0004] This product can selectively antagonize the 5-hydroxytryptamine (5-HT) receptors of platelets and blood vessels, inhibit platelet aggregation, and is clinically used to improve ischemic symptoms such as ulcers, pain and cold sensation caused by chronic arterial occlusive disease. [0005] Journal ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C219/06C07C213/00
Inventor 陆爱华陈华明苏丽花高能王兴国
Owner NANJING KANGRAN PHARMA TECH
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