Sarpogrelate hydrochloride

Base Information

• Chemical Name: Sarpogrelate hydrochloride
• CAS No.: 135159-51-2
• Deprecated CAS: 86819-20-7
• Molecular Formula: C24H32ClNO6
• Molecular Weight: 465.974
• European Community (EC) Number: 663-199-9
• UNII: FQN8N8QP1B
• DSSTox Substance ID: DTXSID8046662
• Wikidata: Q27278133
• NCI Thesaurus Code: C132071
• ChEMBL ID: CHEMBL541829
• Mol file: 135159-51-2.mol

Synonyms:2-(dimethylamino)-1-((2-(3-methoxyphenyl)phenoxy)methyl)ethyl hydrogensuccinate hydrochloride;MCI 9042;MCI-9042;mono-(2-(dimethylamino)-1-((2-(2-(3-methoxyphenyl)ethyl)phenoxy)methyl)ethyl)succinate hydrochloride;sarpogrelate

Chemical Property of Sarpogrelate hydrochloride

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 1.43E-14mmHg at 25°C
• Melting Point: 145-148°C
• Boiling Point: 585.9 °C at 760 mmHg
• Flash Point: 308.1 °C
• PSA: 85.30000
• LogP: 3.99940
• Storage Temp.: Desiccate at RT
• Solubility.: deionized water: ≥5mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 14
• Exact Mass: 465.1918154
• Heavy Atom Count: 32
• Complexity: 540

Purity/Quality:

98% ^*data from raw suppliers

Sarpogrelate hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CC(COC1=CC=CC=C1CCC2=CC(=CC=C2)OC)OC(=O)CCC(=O)O.Cl
• Recent ClinicalTrials: Bioequivalence Study of Anplag? 90mg (Ticagrelor) Tablet & Brilinta? 90 mg (Ticagrelor) Tablet in Healthy Adult Male Pakistani Subjects Under Fasting Condition
• Recent NIPH Clinical Trials: A prospective, randomized, open-label clinical trial evaluating the effect of sarpogrelate hydrochloride on skin perfusion pressure in hemodialysis patients with arteriosclerosis obliterans
• Description: Sarpogrelate hydrochloride, a potent and selective serotonin 5-HT2 receptor antagonist, was launched in Japan as an antithrombotic. It exhibits inhibition of ex vivo platelet aggregation stimulated by serotonin in combination with collagen and suppression of blood vessel constriction mediated by 5-HT2 in vitro. Its antithrombotic effects have been demonstrated in several in vivo experimental models including reduction of the mortality rate in acute pulmonary thromboembolic disease, arterial thrombosis, and peripheral obstructive disease. Sarpogrelate has been shown to be especially useful as an antiplatelet agent for patients with Type 2 diabetes mellitus, in whom 5-HT2mediated amplification of collageninduced platelet aggregation is significantly increased. Sarpogrelate is a selective antagonist of the serotonin (5-HT) receptor subtypes 5-HT2A, 5-HT2B, and 5-HT2C (Kis = 3.02, 269, and 37.2 nM, respectively, for human recombinant receptors expressed in CHO-K1 cells). It is selective for 5-HT2 (Ki = 70.8 nM) over 5-HT1 (Ki = >26,000 nM), α1-, α2-, and β-adrenergic (Kis = 640-123,800 nM), and muscarinic receptors (Ki = >40,000 nM). In vitro, it inhibits aggregation of rat whole blood induced by collagen, 5-HT with collagen, and 5-HT with ADP (; IC50s = 57.7, 0.56, and 22.7 μM, respectively). In vivo, it inhibits leukocyte-endothelial interactions in the femoral artery induced by a high-fat high-fructose diet (HFFD) in mice when administered at a dose of 5 mg/kg per day. Sarpogrelate (5 mg/kg per day) decreases ventricular hypertrophy and infarct size in a rat model of myocardial infarction.
• Uses: Sarpogrelate hydrochloride is a potent and selective 5-HT2A receptor antagonist ress-induced hemolysis.

Technology Process of Sarpogrelate hydrochloride

There total 4 articles about Sarpogrelate hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.4%

succinic acid anhydride (108-30-5) + (±)-1-{2-[2-(3-methoxyphenyl)ethyl]-phenoxy}-3-(dimethylamino)-2-propanol hydrochloride (135261-74-4) → sarpogrelate hydrochloride (135159-51-2,86819-20-7)

Guidance literature:

(±)-1-{2-[2-(3-methoxyphenyl)ethyl]-phenoxy}-3-(dimethylamino)-2-propanol hydrochloride; With sodium hydroxide; In dichloromethane; water;

succinic acid anhydride; In tetrahydrofuran; at 35 - 40 ℃;

With hydrogenchloride; In water; for 1h; pH=3;

Reference yield: 92.5%

succinic acid anhydride (108-30-5) + (R,S)-1-<2-<2-(3-methoxyphenyl)ethyl>phenoxy>-3-(dimethylamino)-2-propanol (135963-42-7,127003-40-1) → sarpogrelate hydrochloride (135159-51-2,86819-20-7)

Guidance literature:

succinic acid anhydride; (R,S)-1-<2-<2-(3-methoxyphenyl)ethyl>phenoxy>-3-(dimethylamino)-2-propanol; In acetone; for 6h; Reflux;

With hydrogenchloride; In acetone; at 0 - 20 ℃; for 8h; pH=1 - 2; Concentration;

Reference yield:

2-[2-(3-methoxyphenyl)ethyl]phenol (167145-13-3) → sarpogrelate hydrochloride (135159-51-2,86819-20-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / toluene; water / 8 h / Reflux

2.1: water; tetrahydrofuran / 3 h / 750.08 Torr / Inert atmosphere; Autoclave

3.1: acetone / 6 h / Reflux

3.2: 8 h / 0 - 20 °C / pH 1 - 2

With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In tetrahydrofuran; water; acetone; toluene;

upstream raw materials:

succinic acid anhydride

(±)-1-{2-[2-(3-methoxyphenyl)ethyl]-phenoxy}-3-(dimethylamino)-2-propanol hydrochloride

2-[2-(3-methoxyphenyl)ethyl]phenol

(R,S)-1-<2-<2-(3-methoxyphenyl)ethyl>phenoxy>-3-(dimethylamino)-2-propanol

Downstream raw materials:

succinic acid

(R,S)-1-<2-<2-(3-methoxyphenyl)ethyl>phenoxy>-3-(dimethylamino)-2-propanol

Refernces

• 1、 -. "Crystallizine Sapogrelate Hydrochloride and a method for forming the same". Paragraph 0057; 0058. . Retrieved 2019/10/08.
• 2、 Kikumoto, Ryoji,Hara, Hiroto,Ninomiya, Kunihiro,Osakabe, Masanori,Sugano, Mamoru,et al.. "Syntheses and Platelet Aggregation Inhibitory and Antithrombotic Properties of ethyl>benzenes". . p. 1818 - 1823. Retrieved 2007/10/02.