220347-05-7

Basic information

• Product Name: AR-C 124910XX
• Synonyms: AR-C 124910XX;Deshydroxyethoxy Ticagrelor;(1S,2R,3S,4R)-4-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)cyclopentane-1,2,3-triol;Ticagrelor impurity G (Ticagrelor metabolite)
• CAS NO: 220347-05-7
• Molecular Formula: C₂₁H₂₄F₂N₆O₃S
• Molecular Weight: 478.5154664
• Product Categories: Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 220347-05-7.mol

Chemical Properties

• Boiling Point: 722.7±70.0 °C(Predicted)
• Appearance: /
• Density: 1.75±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.38±0.70(Predicted)
• CAS DataBase Reference: AR-C 124910XX(CAS DataBase Reference)
• NIST Chemistry Reference: AR-C 124910XX(220347-05-7)
• EPA Substance Registry System: AR-C 124910XX(220347-05-7)

Safety Data

• Hazardous Substances Data: 220347-05-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
AR-C 124910XX is used as an active pharmaceutical ingredient for the development of drugs targeting specific medical conditions. Its chemical properties allow it to interact with biological systems, making it a promising candidate for therapeutic applications.
Used in Anticancer Applications:
In the field of oncology, AR-C 124910XX is used as an anticancer agent, potentially effective against various types of cancer. It may modulate oncological signaling pathways and exhibit inhibitory effects on tumor growth and progression.
Used in Drug Delivery Systems:
To enhance the efficacy and bioavailability of AR-C 124910XX, it is used in conjunction with novel drug delivery systems. These systems, which may include organic and metallic nanoparticles, aim to improve the compound's delivery to target cells and tissues, ultimately enhancing its therapeutic outcomes.
Used in Cardiovascular Applications:
AR-C 124910XX is used as a preventative agent in the treatment of heart attacks, myocardial infarction, and other pulmonary diseases. It serves as a deshydroxyethoxy analog of Ticagrelor (T437700), an antiplatelet agent, which helps in reducing the risk of blood clot formation and improving cardiovascular health.

Upstream product

• 345898-95-5 N-(((4S,5R)-2,2-dimethyl-5-vinyl-1 ,3-dioxolan-4-yl)methylene)-1-phenylmethanamine oxide 
• 220352-36-3 trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid 
• 1006614-49-8 (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine 
• 145783-15-9 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine 
• 274693-27-5 ticagrelor 
• 50600-40-3 (3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 155855-51-9 tetrahydro-2,2-dimethyl-6-phenylmethyl-(3aS,4S,7R,7aS)-4,7-methano-4H-1,3-dioxolo[4,5-d][1,2]oxazine 
• 155899-66-4 (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 367-11-3 ortho-difluorobenzene 
• 532-20-7 D-Ribose 
• 1006376-62-0 (1R,2R)-trans-2(3,4-difluorophenyl)cyclopropyl carboxamide 
• 376608-70-7 trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl chloride 
• 1006376-63-1 (S)-2-(3,4-difluorophenyl)ethylene oxide 
• 1006376-60-8 (1S)-2-chloro-1-(3,4-difluorophenyl)-1-ethanol 

Downstream Products

• 274693-49-1 (3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 274693-27-5 ticagrelor 

Relevant articles and documents

Concise synthesis of the major metabolite M8 from ticagrelor and simultaneous determination of ticagrelor and M8 by a novel LC/MS method

Ticagrelor is an oral antiplatelet agent that has been approved for preventing de novo and recurrent acute coronary syndrome. To date, only a few studies have attempted to clarify population differences in the pharmacokinetics and pharmacodynamics of ticagrelor between Caucasians and Asians. Our aim was to develop a simple quantification method for ticagrelor and its pharmacologically active metabolite M8 (AR-C124910XX) in human plasma and urine. First, we concisely synthesized M8 from ticagrelor via a five-step sequence: the hydroxyethyl group of ticagrelor was removed by bromination and subsequent zinc-mediated chemoselective reduction. Then, we developed a simple liquid chromatography–mass spectrometry method using ticlopidine as an internal standard. Ticagrelor, M8, and internal standard were separated with a reverse-phase C18 column, and ticagrelor and M8 were detected at m/z [+] of 523.25 and 479.25, respectively, with good sensitivity and precision in the concentration ranges of 10 to 100 μM and 5 to 50 μM, respectively. This novel liquid chromatography–mass spectrometry system may be attractive to investigators in private laboratories because it is less costly than liquid chromatography/mass spectrometry/mass spectrometry systems. Our method is expected to accelerate further clinical studies on the disposition and pharmacodynamics of ticagrelor.

Synthesis of ticagrelor analogues belonging to 1,2,3-triazolo[4,5-d]pyrimidines and study of their antiplatelet and antibacterial activity

Based on the recent observation that the antiplatelet agent ticagrelor and one of its metabolite exert bactericidal activity against gram-positive bacteria, a series of 1,2,3-triazolo[4,5-d]pyrimidines structurally related to ticagrelor were synthesized and examined as putative antiplatelet and antibacterial agents. The aim was to assess the possibility of dissociating the two biological properties and to find novel 1,2,3-triazolo[4,5-d]pyrimidines expressing antiplatelet activity and devoid of in vitro antibacterial activity. The new compounds synthesized were known metabolites of ticagrelor as well as structurally simplified analogues. Some of them were found to express antiplatelet activity and to lose the antibacterial activity, supporting the view that the two activities were not necessarily linked.

Method of synthesis of Ticagrelor

The invention provides a method of synthesis of Ticagrelor (1). The method comprises the steps that firstly a compound (2) and a compound (3) are subject to a substitution reaction to prepare a compound (4); the compound (4) after being subject to the substitution reaction of sulfur alcohol is prepared into a compound (5); the compound (5) and a compound (6) after being subject to the substitution reaction of palladium catalyst non-symmetric terpene propyl alcohol is prepared into a compound (7); the compound (7) after being subject to non-asymmetric di-hydroxylation reaction is prepared into a compound (8); the compound (8) after being subject to di-hydroxy protective reaction is prepared into a compound (9); the compound (9) after being subject to the substitution reaction of hydroxyl is prepared into a compound (10); finally Ticagrelor (1) is obtained by subjecting the compound (10) to the deprotection reaction of hydroxyl. The method of synthesis of Ticagrelor is simple to operate, low in production cost, high in product quality, and suitable for industrial production. (The picture file is appended to the application.).

Synthesis and biological evaluation of ticagrelor derivatives as novel antiplatelet agents

Ticagrelor (1) is the first reversible P2Y12 receptor antagonist blocking adenine diphosphate (ADP)-induced platelet aggregation with rapid onset and offset of effects. In this study, synthesis of ticagrelor and its derivatives has been accomplished in a convergent way. The compound design was based on modifications of ticagrelor and its major metabolite (33) in order to ameliorate their pharmacokinetic properties and dosing profile. The final compounds (1a-g, 35a-g) were evaluated for their inhibitory effect on ADP-induced platelet aggregation in rats. The assay results showed that some compounds (e.g., 1b, 1d, 33, 35b, 35f) exhibited comparable potency with that of ticagrelor.