ChemicalBook--->CAS DataBase List--->163706-36-3

163706-36-3

163706-36-3 Structure

163706-36-3 Structure
IdentificationBack Directory
[Name]

cangrelor tetrasodium
[CAS]

163706-36-3
[Synonyms]

CS-1027
angrelor tetrasodium
cangrelor tetrasodium
Cangrelor Tetrasodium Salt
AR-C 69931 Tetrasodium Salt
Cangrelor tetrasodium salt >=98% (HPLC)
tetrasodium 5'-O-[({[dichloro(phosphonato)methyl]phosphinato...
N-[2-(Methylthio)ethyl]-2-[(3,3,3-trifluoropropyl)thio]adenosine-5'-O-(β,γ-dichloromethylene)triphosphate tetrasodium salt
tetrasodium 5'-O-[({[dichloro(phosphonato)methyl]phosphinato}oxy)phosphinato]-N-[2-(methylsulfanyl)ethyl]-2-[(3,3,3-trifluoropropyl)sulfanyl]adenosine
(Dichloro((((((2R,3S,4R,5R)-3,4-dihydroxy-5-(6-((2-(methylthio)ethyl)amino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)methyl)phosphonic acid tetrasodium salt
[EINECS(EC#)]

813-784-1
[Molecular Formula]

C17H21Cl2F3N5Na4O12P3S2
[MDL Number]

MFCD14635359
[MOL File]

163706-36-3.mol
[Molecular Weight]

864.287
Chemical PropertiesBack Directory
[storage temp. ]

4°C, away from moisture and light
[solubility ]

DMSO:100.0(Max Conc. mg/mL);115.7(Max Conc. mM)
[form ]

A solid
[color ]

White to off-white
[Water Solubility ]

Soluble to 100 mM in water
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P280-P305+P351+P338
Hazard InformationBack Directory
[Description]

Cangrelor tetrasodium is a direct purinergic platelet receptor (P2Y12) inhibitor that blocks ADP-induced platelet activation and aggregation. The drug, which was developed by The Medicine Company, binds reversibly to the P2Y12 receptor, preventing further signaling and platelet activation. Cangrelor, which was approved in June 2015 by the FDA, is indicated as an adjunct to percutaneous coronary intervention for reducing the risk of periprocedural myocardial infarction, repeat coronary revascularization, and stent thrombosis in patients who have not been treated with a P2Y12 platelet inhibitor and are not being given a glycoprotein IIb/IIIa inhibitor. The most common side effect observed with the drug was bleeding.
[Uses]

Antiplatelet agent.
[Definition]

ChEBI: An organic sodium salt that is the tetrasodium salt of cangrelor. Used as an intravenous antiplatelet drug that prevents formation of harmful blood clots in the coronary arteries.
[Synthesis]

While several discovery-scale routes to cangrelor tetrasodium were previously reported,14 an improved procedure developed with the goal of providing a manufacturing scale route to cangrelor tetrasodium has recently been reported by Jinan Bestcomm Pharmaceutical R&D. Starting from commercially available 2-thiobarbituric acid (36), S-alkylation with 3,3,3-trifluoropropyl iodide proceeded in high yield (94%) under basic conditions. Nitration of this intermediate with HNO3/AcOH generated a nitro-pyrimidine diol in 80% yield. Bis-chlorination via treatment with POCl3 provided the corresponding dichloro pyrimidine (92%), and subsequent nitro reduction with AcOH/Fe under aqueous conditions yielded intermediate 37 (quantitative yield), which readily provided the bis-aniline analogue by reaction with ammonia in EtOH/H2O at 80 ??C. Condensation with triethyl orthoformate/ HCl at room temperature provided access to the desired purine in high yield (97%). A one-pot alkylation/amination strategy was then employed, first relying on S-alkylation of 2- aminoethanethiol hydrochloride with MeI/NaOH and reaction of the resulting amine with the purine chloride generated 38 in 88% across the sequence. Alkylation of 38 with commercial furanose 39 proceeded in a regioselective manner favoring N-9 functionalization, employing conditions similar to those previously described by Almond and co-workers. Toward this end, silylation of 38 with N,O-bis-(trimethylsilyl)acetamide (BSA) followed by subjection to TMSOTf and 39, resulted in the desired N-9 alkylated product, which was carried crude to global deacetylation with NaOH/EtOH at room temperature, making way for smooth conversion to alcohol 40 (87% from 38). Although phosphorylation of 40 has been performed using a variety of related methods,14 the largest scale conditions reported to date consist of initial 5?? alcohol activation with POCl3 and PO(OEt)3 in the presence of 1,8-diaminonaphthalene, furnishing the 5?? monophosphonate intermediate. This intermediate was not isolated but further treated with a solution of dichloromethylenebis(phosphonic acid) tributylammonium salt and tributylamine in DMF at 0 ??C, yielding cangrelor as a crude ammonium salt following quench with NH4HCO3.15 Purification via ion exchange chromatography provided cangrelor as its ammonium salt in 68% yield over the threestep sequence, which was subjected to aqueous NaHCO3 solution and lyophilization and provided cangrelor tetrasodium salt (IV). This synthesis was performed starting on >100 g scale of 36 and required only one chromatography step which involved ion exchange chromatography of the cangrelor ammonium salt. More recently, while beyond the scope of this article, additional reports have been disclosed describing the development of specific pharmaceutical formulations for delivery of cangrelor in high purity.

Synthesis_163706-36-3

[storage]

Store at -20°C
Spectrum DetailBack Directory
[Spectrum Detail]

cangrelor tetrasodium(163706-36-3)1HNMR
163706-36-3 suppliers list
Company Name: Apeloa production Co.,Limited
Tel: +8619933239880 , +8619933239880
Website: www.apcl.com.cn/
Company Name: Shanghai Daken Advanced Materials Co.,Ltd
Tel: +86-371-66670886
Website: https://www.dakenchem.com/
Company Name: Shanghai Yingrui Biopharma Co., Ltd.
Tel: +86-21-33585366 - 03@
Website: www.shyrchem.com
Company Name: ATK CHEMICAL COMPANY LIMITED
Tel: +undefined-21-51877795
Website: www.atkchemical.com
Company Name: career henan chemical co
Tel: +86-0371-86658258 +8613203830695 , +8613203830695
Website: www.coreychem.com/
Company Name: Shenzhen Nexconn Pharmatechs Ltd
Tel: +86-755-89396905 +86-15013857715 , +86-15013857715
Website: https://www.chemicalbook.com/ShowSupplierProductsList31188/0.htm
Company Name: Wuhan Chemwonders Technology Inc.
Tel: 027-85778276
Website: www.chemwonders.com
Company Name: BOC Sciences
Tel: +1-631-485-4226
Website: www.bocsci.com/
Company Name: Chongqing Chemdad Co., Ltd
Tel: +86-023-6139-8061 +86-86-13650506873 , +86-86-13650506873
Website: http://www.chemdad.com/
Company Name: Shanghai Yingrui Biopharma Co.,Ltd
Tel: 21-33585366
Website: www.shyrchem.com
Company Name: Shanghai Rochi Pharmaceutical Co.,Ltd.
Tel: 21-38751876 +8615000076078 , +8615000076078
Website: http://www.rochipharma.com/en/index.aspx
Company Name: AFINE CHEMICALS LIMITED
Tel: +86-0571-85134551
Website: www.afinechem.com/index.html
Company Name: Shenzhen Shengda Pharma Limited
Tel: 755-85269922 +8613424394241 , +8613424394241
Website: www.shengdapharm.com
Company Name: Hefei Hirisun Pharmatech Co., Ltd
Tel: +8615056975894 , +8615056975894
Website: www.hirisunpharm.com
Company Name: changzhou huayang technology co., ltd
Tel: +8615250961469 , +8615250961469
Website: http://www.huayangchem.com/template/eabout.html
Company Name: Alfa Chemistry
Tel:
Website: www.alfa-chemistry.com/
Company Name: InvivoChem
Tel: +1-708-310-1919 +1-13798911105 , +1-13798911105
Website: https://www.invivochem.com/
Company Name: Hefei TNJ Chemical Industry Co.,Ltd.
Tel: +86-0551-65418684 +8618949823763 , +8618949823763
Website: www.tnjchem.com
Tags:163706-36-3 Related Product Information
62-33-9 10378-23-1 15708-41-5 6610-25-9 14402-88-1 27360-85-6 6381-92-6