Method for preparing sarpogrelate hydrochloride

A technology for sarpogrelate hydrochloride and salt formation, which is applied in the field of preparation of sarpogrelate hydrochloride, can solve the problems of being difficult to remove, difficult to obtain high-purity products, and the like, and achieves the effects of easy operation, easy industrial production and low production cost.

Inactive Publication Date: 2008-08-13
NANJING KANGRAN PHARMA TECH
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  • Summary
  • Abstract
  • 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 prepared by Wittg reaction usually, can produce a large amount of triphenylphosphine oxides, is difficult to remove, and existing method is all by crossing chromatographic column purification at present:
[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
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 2-((3-methoxy)phenethyl)phenol (mixture)

[0039] 100 kg (containing 55% of triphenylphosphine oxide) of 2-((3-methoxy) styryl) phenol mixture prepared by Wittg 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.

Embodiment 2

[0040] Example 2 2-((3-methoxy)phenethyl)phenol (mixture)

[0041] Add 190 grams of 2-((3-methoxy) styryl) phenol mixture (containing 52% triphenylphosphine oxide) prepared by Wittg reaction into the reaction flask, add 1000 ml of methanol, 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.

Embodiment 3

[0042] Example 3 2-((3-methoxy)phenethyl)phenol (mixture)

[0043] 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, mono 2-( Dimethylamino)-1-[[o-(m-methoxyphenethyl)phenoxy]methyl]ethyl ester hydrochloride, CAS RegistryNumber: 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 Applications(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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