135159-51-2

Basic information

• Product Name: Sarpogrelate hydrochloride
• Synonyms: (+/-)-2-(dimethylamino)-1-{[o-(m-methoxyphenethyl)phenoxy]methyl}ethyl hydrogen succinate hydrochloride;SARPOGRELATE HCL;SARPOGRELATE HYDROCHLORIDE;Anplag;Butanedioic acid, mono[2-(dimethylamino)-1-[[2-[2-(3-methoxyphenyl)ethyl]phenoxy]methyl]ethyl] ester, hydrochloride (9CI);Butanedioic acid, mono[2-(dimethylamino)-1-[[2-[2-(3-methoxyphenyl)ethyl]phenoxy]methyl]ethyl] ester, hydrochloride, (+-)-;MCI 9042;4-[1-(dimethylamino)-3-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]propan-2-yl]oxy-4-oxobutanoic acid hydrochloride
• CAS NO: 135159-51-2
• Molecular Formula: C₂₄H₃₁NO₆*ClH
• Molecular Weight: 465.96698
• EINECS: 1806241-263-5
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;fang;strong recommend
• Mol File: 135159-51-2.mol

Chemical Properties

• Melting Point: 145-148°C
• Boiling Point: 585.9 °C at 760 mmHg
• Flash Point: 308.1 °C
• Appearance: colorless liquid
• Vapor Pressure: 1.43E-14mmHg at 25°C
• Storage Temp.: Desiccate at RT
• Solubility: deionized water: ≥5mg/mL
• CAS DataBase Reference: Sarpogrelate hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Sarpogrelate hydrochloride(135159-51-2)
• EPA Substance Registry System: Sarpogrelate hydrochloride(135159-51-2)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 135159-51-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Sarpogrelate hydrochloride is used as an antithrombotic agent for its ability to inhibit platelet aggregation and blood vessel constriction, making it particularly useful for patients with Type 2 diabetes mellitus.
Used in Cardiovascular Applications:
Sarpogrelate hydrochloride is used as an antiplatelet agent to reduce the risk of arterial thrombosis and peripheral obstructive disease, as well as to decrease ventricular hypertrophy and infarct size in a rat model of myocardial infarction.
Used in Research and Development:
Sarpogrelate hydrochloride is used as a selective antagonist of the serotonin (5-HT) receptor subtypes 5-HT2A, 5-HT2B, and 5-HT2C for studying the role of these receptors in various biological processes and developing new therapeutic strategies.

Originator

Mitsubishi Kasei (Japan )

Biological Activity

Selective 5-HT 2A receptor antagonist (pK i values are 8.52, 7.43 and 6.57 for 5-HT 2A , 5-HT 2C and 5-HT 2B receptors respectively). Displays selectivity over 5-HT 1 , 5-HT 3 , 5-HT 4 H 1 , H 2 , M 3 , α 1 -adrenergic, α 2 -adrenergic and β -adrenergic receptors. Displays cardioprotective activity in vivo .

in vitro

the major metabolite (r,s)-m-1, and m-1 enantiomers of sarpogrelate specifically blocked 5-ht at 5-ht2a receptors. the stereochemical configuration of the ligands does not obviously play a key role at binding to the 5-ht2a receptor [2].

in vivo

pad patients were divided into two groups. one group treated with 100 mg sarpogrelate in oral 3 times one day for 12 weeks (n = 10), while the other group who remained on conventional therapy as control group (n = 11). forearm blood flow (fbf) and leg blood flow (lbf) responses to reactive hyperemia (rh) and sublingual administration of nitroglycerin (ntg) were measured by strain-gauge plethysmography. after twelve weeks of its administration, fbf and lbf responses during rh exhibited significant increases from 13.2 6 1.7 to 18.1 6 2.2 ml/min every 100 ml tissue (p , 0.01) and from 8.2 6 0.9 to 14.2 6 2.1 ml/min every 100 ml tissue (p , 0.05), respectively. augmentation of fbf and lbf induced by sarpogrelate responses to rh was maintained at 24 weeks. the control group had no change observed in at each follow-up time point. the changes in fbf and lbf after sublingual ntg were similar during follow-up periods in the two groups. these findings suggest that longterm oral administration of sarpogrelate improves vascular function in patients with pad [3].

references

[1] nishio h1, inoue a, nakata y. binding affinity of sarpogrelate, a new antiplatelet agent, and its metabolite for serotonin receptor subtypes. arch int pharmacodyn ther. 1996 mar-apr;331(2):189-202.[2] pertz h1, elz s. in-vitro pharmacology of sarpogrelate and the enantiomers of its major metabolite: 5-ht2a receptor specificity, stereoselectivity and modulation of ritanserin-induced depression of 5-ht contractions in rat tail artery. j pharm pharmacol. 1995 apr;47(4):310-6.[3] miyazaki m1, higashi y, goto c, chayama k, yoshizumi m, sanada h, orihashi k, sueda t. sarpogrelate hydrochloride, a selective 5-ht2a antagonist, improves vascular function in patients with peripheral arterial disease. j cardiovasc pharmacol. 2007 apr;49(4):221-7.

InChI:InChI=1/C24H31NO6.ClH/c1-25(2)16-21(31-24(28)14-13-23(26)27)17-30-22-10-5-4-8-19(22)12-11-18-7-6-9-20(15-18)29-3;/h4-10,15,21H,11-14,16-17H2,1-3H3,(H,26,27);1H

Upstream product

• 108-30-5 succinic acid anhydride 
• 135963-42-7 (R,S)-1-<2-<2-(3-methoxyphenyl)ethyl>phenoxy>-3-(dimethylamino)-2-propanol 
• 167145-13-3 2-[2-(3-methoxyphenyl)ethyl]phenol 
• 135261-74-4 (±)-1-{2-[2-(3-methoxyphenyl)ethyl]-phenoxy}-3-(dimethylamino)-2-propanol hydrochloride 

Downstream Products

• 110-15-6 succinic acid 
• 135963-42-7 (R,S)-1-<2-<2-(3-methoxyphenyl)ethyl>phenoxy>-3-(dimethylamino)-2-propanol 

Relevant articles and documents

METHODS FOR PREPARING SARPOGRELATE HYDROCHLORIDE AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention provides hydrochloride salt hydrochloride. More specifically, the present invention relates to a method for preparing a hydrochloride salt having high purity and less toxicity in the body, and a pharmaceutical formulation comprising the same. The present invention relates to a hydrochloride and a pharmaceutical composition containing the same, and to a pharmaceutical composition containing the same, and a pharmaceutical composition containing the same, and a pharmaceutical composition containing the same. (by machine translation)

Crystallizine Sapogrelate Hydrochloride and a method for forming the same

Disclosed are sarpogrelate hydrochloride crystals used an anticoagulant. A method to produce the sarpogrelate hydrochloride crystals by the present invention includes: a step of making 2-[2-hydroxy-3-dimethylaminopropoxy]-3andprime;-methoxybenzyl hydrochloride represented by chemical formula 3 react with succinic anhydride represented by chemical formula 4 in the presence of an organic base; a step of removing the hydrochloride of the generated organic base after completion of the reaction; and a step of adding aqueous hydrochloric acid solution to filtrate from which the hydrochloride of the organic base is removed. The sarpogrelate hydrochloride crystals include 60-80 wt% of sarpogrelate hydrochloride form I crystals and 20-40 wt% of sarpogrelate hydrochloride form II crystals. The present invention is able to solve the mixing problem of the sarpogrelate hydrochloride form II crystals.COPYRIGHT KIPO 2019

Process for preparing sand Greythe ester is new hydrochloric acid

The present invention discloses a preparation method of sarpogrelate hydrochloride. According to the preparation method, 2-[2-(3-methoxyphenyl)ethyl]phenol is adopted as a starting reactant, benzyl triethylammonium chloride is adopted as a phase transfer catalyst, the starting reactant, the phase transfer catalyst and epichlorohydrin form an ether in toluene and water, dimethylamine is adopted to carry out aminolysis in a pressurization reactor after the ether is formed to obtain 1-dimethylamino-3-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]-2-propanol, the 1-dimethylamino-3-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]-2-propanol and succinic anhydride are subjected to esterification in acetone, hydrogen chloride gas is directly introduced without recovery and replacement of the solvent to form a hydrochloride, and re-crystallization with acetone is performed to obtain the sarpogrelate hydrochloride refined product, wherein the purity is more than 99%.

Syntheses and Platelet Aggregation Inhibitory and Antithrombotic Properties of ethyl>benzenes

A series of ethyl>benzene derivatives were synthesized and evaluated for their ability to inhibit collagen-induced platelet aggregation in vitro and to protect experimantal thrombosis in mice.The results showed that the compounds were in vitro inhibitors of collagen-induced platelet aggregation.Most of them were also effective in the mouse antithrombotic assay.The compounds were found to be potent antagonists to S2 serotonergic receptor, and good correlation (r = 0.85) between their S2 serotonergic receptor antagonism and their potency as platelet antiaggregatory drugs was observed.Among the compounds studied, monophenoxy>methyl>ethyl>succinate hydrochloride (12b, MCI-9042) was selected for further pharmacological and toxicological evaluation.

Pharmaceutically active (3-aminopropoxy)bibenzyl derivatives

(3-Aminopropoxy)bibenzyl derivatives are prepared and found useful as pharmaceutical agents, particularly as inhibitors of platelet aggregation.