376608-74-1

Usage

Uses

Used in Pharmaceutical Industry:
Ethanol, 2-[[(3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylthio)-4-pyrimidinyl]amino]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]is used as a reagent in the synthesis of Ticagrelor (T437700) derivatives. Ticagrelor is an antiplatelet agent that helps prevent blood clots and is used to treat patients with acute coronary syndrome or a history of myocardial infarction, stroke, or peripheral arterial disease. The unique structure of this ethanol derivative allows it to participate in the formation of these important therapeutic agents, contributing to their efficacy and safety in treating cardiovascular conditions.

Upstream product

• 145783-15-9 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine 
• 274693-55-9 [3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol 
• 1402150-30-4 2-[[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-yl]oxy]-1-ethanol oxalate 
• 145783-12-6 4,6-dihydroxy-2-(propylsulfanyl)pyrimidine 
• 145783-13-7 4,6-dihydroxy-5-nitro-2-(propylthio)pyrimidine 
• 145783-14-8 4,6-dichloro-5-nitro-2-(propylsulfanyl)pyrimidine 
• 1265919-25-2 2-[((3aR,4S,6R,6aS)-6-{[5-nitro-6-chloro-2-(propylthio)-4-pyrimidinyl]amino}-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]-1-ethanol 
• 345898-95-5 N-(((4S,5R)-2,2-dimethyl-5-vinyl-1 ,3-dioxolan-4-yl)methylene)-1-phenylmethanamine oxide 
• 274693-54-8 benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate 
• 866551-95-3 ethyl 2-(6-(benzyloxycarbonylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy) acetate 
• 274693-53-7 [3aS-(3aα,4α,6α,6aα)]-(tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)carbamic acid phenylmethyl ester 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 376608-72-9 4,6-dihydroxy-5-((E)-2-(4-methylphenyl)diazenyl)-2-(propylsulfanyl)pyrimidine 
• 376608-73-0 4,6-dichloro-5-((E)-2-(4-methylphenyl)diazenyl)-2-(propylsulfanyl)pyrimidine 

Downstream Products

• 376608-75-2 2-({(3aR,4S,6R,6aS)-6-[7-chloro-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-3-yl]-2,2-dimethyltetrahydro-3aH-cyclopentadiene[d][1,3]dioxolene-4-yl}oxy)ethanol 
• 2096989-55-6 ticagrelor 
• 1644461-85-7 C₂₃H₂₈F₂N₆O₅S 
• 376608-75-2 C₁₇H₂₄ClN₅O₄S 
• 1644461-85-7 C₂₃H₂₈F₂N₆O₅S 
• 2096989-55-6 [1S-[1a,2a,3β(1S*,2R*),5B]]-3-[7-[2-(3,4-difluorophenyl)cyclopropylamino]-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol 

Relevant academic research and scientific papers

Synthesis and biological evaluation of: N 6derivatives of 8-azapurine as novel antiplatelet agents

Two series of novel N6 derivatives of 8-azapurine I and II were designed as antiplatelet agents. Series I and II were N6 amino derivatives and N6 hydrazone derivatives of 8-azapurine, respectively. The compounds were synthesized in acceptable yields via conventional procedures, including nucleophilic substitution, diazotization, and amination or hydrazonation with amino alcohol and 4,6-dichloropyrimidine as starting materials. To assess the ability of the synthesized compounds as antiplatelet agents, the ADP-induced platelet aggregation assay of Born was performed both in vitro and in vivo using ticagrelor as a reference control substance. The analysis of the structure-activity relationship and molecular docking were also discussed in detail. The results demonstrated that series I and II compounds exhibited antiplatelet activity in vitro and IIh was the most active compound (IC50 = 0.20 μM) among the target compounds, being almost 4-fold better than ticagrelor (IC50 = 0.74 μM). For a preliminary assessment of the safety profile, a bleeding test (mouse tail) and a single-dose toxicity test were conducted. The use of compound IIh resulted in a shorter bleeding time, less blood loss and lower acute toxicity compared to ticagrelor. In addition, a molecular docking study was performed to investigate the binding capacity and binding mode between IIh and P2Y12. This journal is

NEW USE OF TRIAZOLO[4,5-D]PYRIMIDINE DERIVATIVES

Triazolo[4,5-d]pyrimidine derivatives of formula (I) for use in prognosis and/or diagnosis of bacterial infection in a host mammal and method of imaging thereof. Formula (I) wherein R1 is C3-5 alkyl optionally substituted by one or m

Preparation process of ticagrelor intermediate

The invention discloses a preparation process of a ticagrelor intermediate. The process comprises the following steps of dissolving 4,6-dichloro-2-(propylthio)-5-aminopyrimidine and sodium bicarbonatein water at a temperature of 15-25 DEG C; performing heating, adding an aqueous solution of 2-[[(3aR, 4S, 6R, 6aS)-6-amino-2, 2-dimethyltetrahydro-3aH- cyclopentadiene [d] [1,3]-dioxol-4-yl] oxy]-1-ethanol (III) or a salt thereof, and performing stirring at a constant temperature until a reaction is finished; stopping heating, cooling a reaction mixture, adding ethyl acetate, separating liquid, and washing an organic phase with water; stirring the organic phase, slowly dropwise adding n-hexane at a certain temperature, and separating out a solid to obtain the intermediate. According to the process, the use of excessive organic base such as triethylamine is avoided, the cheap and easily available sodium bicarbonate is used, the production cost is low, the reaction time is short, three wastes are few, and the obtained ticagrelor intermediate is the solid with the high purity, is high in yield and is more suitable for industrial production.

Production process of ticagrelor fine product

The present invention discloses a production process of a ticagrelor fine product. The process comprises the steps of adopting 4,6-dichloro-5-amino-2-propylthiopyrimidine (IIa) and a compound (IIb) asstarting raw materials, and carrying out five processes including a substitution process I, a cyclization process, a substitution process II, a hydrolysis process and a refining process to finally obtain the ticagrelor fine product. The method provides a ticagrelor production process, uses cheap and easily available raw materials, has the advantages of low production cost, simple reaction conditions, convenient post-treatment, high yield and high product purity, and is more suitable for industrial production.

Improved preparation method of ticagrelor intermediate (by machine translation)

Step, Step: Reaction 1: Reaction of Compound 1 and Compound 2 with ethylene glycol, triethylamine under nitrogen protection, to obtain ticagrelor intermediate product, wherein the mixed solvent is an alcohol solvent, weak alkaline agent, in which the purity of intermediate product, is not less than, and the content of impurities, is not more than, in step (II) of inert gas protection descent temperature; to obtain ticagrelor intermediate. 2: The mixed solvent is obtained by filtering, organic layers under reduced pressure . The product obtained in Step 1, is obtained by adding an inert solvent (II), (II) and purifying/water, to, obtain a (II) ticagrelor intermediate product, obtained 99.2%, by stirring and dissolving, 3 into 0.05%; an active carbon decolorizing, filtrate .] 99.2%, filtering method of an 3 intermediate product thereof, 0.05%. is carried out in an inert gas protection falling temperature. (by machine translation)

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.

Preparation method of ticagrelor

The invention provides a preparation method of ticagrelor. According to the preparation method, a compound shown in a formula (i) is used as a raw material, and the ticagrelor is prepared by means ofcondensation, ring formation, condensation and deprotection; the preparation method is simple and convenient in technological process and easy to operate, thus being suitable for large-scale production; furthermore, the preparation method provided by the invention is mild in synthesis conditions, high in product yield and good in product purity, can effectively control the preparation cost, and reduces the medication burden of patients.

Preparation method of ticagrelor

The invention relates to synthesis of a pharmaceutical compound and in particular relates to a preparation method of ticagrelor. The method disclosed by the invention comprises the steps as follows: step 1, synthesizing an intermediate Im-1; step 2, synthesizing an intermediate Im-2; step 3, synthesizing an intermediate Im-3; step 4, synthesizing a crude product Im-4; and step 5, carrying out refining, namely recrystallizing the crude product of ticagrelor by using 10-15 times of mixed solution of dichloromethane and tertiary butanol, and carrying out washing, filtering and drying to obtain arefined product of ticagrelor, wherein the volume ratio of dichloromethane to tertiary butanol in the mixed solution of dichloromethane and tertiary butanol is 1:(2-3).

Synthesizing method of ticagrelor

The invention relates to synthesis of a medicine compound, in particular to a synthesizing method of ticagrelor. The synthesizing method comprises the following steps of S1, synthesizing an intermediate Im-1; S2, synthesizing an intermediate Im-2; S3, synthesizing an intermediate Im-3; S4, synthesizing a crude product Im-4; S5, refining: recrystallizing a crude product of the ticagrelor by a mixedsolution of dichloromethane and tertiary butanol, washing, filtering, and drying, so as to obtain a refined product of the ticagrelor.

Preparation method of high-purity ticagrelor

The invention discloses a preparation method of high-purity ticagrelor. The preparation method comprises the following steps: preparing intermediates TG-1, TG-2, TG-3 and TG-4; and refining the ticagrelor. According to the preparation method, matching of reactants is adjusted, the reaction time and temperature are optimized, and a post-processing manner is adopted; a specific catalyst and a specific devitrification solvent are selected, so that the reaction efficiency of the intermediates is improved, the reaction time is shortened and the purity of the intermediates is improved; after a crudeproduct of the ticagrelor is obtained, different devitrification solvents and a staged crystallization process are adopted to obtain the ticagrelor with high purity, so that the production cost is reduced, the advantages of being high efficiency and clean in production are achieved, and the operability is strong; and the purity of the obtained ticagrelor product is not lower than 99.8%, and no single impurity exceeds 0.06%.