376608-75-2

Usage

Uses

Used in Pharmaceutical Industry:
2-[[(3aR,4S,6R,6aS)-6-[7-Chloro-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol is used as a reagent in the synthesis of Ticagrelor (T437700), an orally active reversible P2Y12 receptor antagonist. Ticagrelor is prescribed for the prevention of thrombosis, a condition characterized by the formation of blood clots within the circulatory system. 2-[[(3aR,4S,6R,6aS)-6-[7-Chloro-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol helps in the development of Ticagrelor by facilitating its synthesis, making it an essential component in the production process.

Upstream product

• 376608-74-1 2-[((3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylsulfanyl)-4-pyrimidinyl]amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]-1-ethanol 
• 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 
• 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 
• 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

• 274693-26-4 [3aR-[3aα,4α,6α,(1R,2S),6aα]]-2-[6-[[[7-(2-(3,4-difluorophenyl)cyclopropyl)]amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenteno-1,3-dioxolan-4-yl]oxy]ethanol 
• 1644461-85-7 C₂₃H₂₈F₂N₆O₅S 
• 1644461-85-7 C₂₃H₂₈F₂N₆O₅S 

Relevant academic research and scientific papers

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

Method for preparing ticagrelor advanced intermediate by applying continuous flow reaction technology

The invention discloses a method for preparing a ticagrelor advanced intermediate by using a continuous flow reaction technology. The method comprises the following steps: reacting TGM-1 with sodium nitrite in a first microchannel reactor, carrying out diazotization reaction, cyclizing to synthesize triazole, and carrying out butt coupling on TGM-2 and an intermediate TGC under the action of an alkali reagent in a second microchannel reactor to obtain the target product isopropylidene ticagrelor TGI. According to the scheme, the whole preparation process is simple, operation is convenient, itis possible to prepare the macromolecular compound isopropylidene ticagrelor through the continuous flow reaction technology by reasonably designing reaction parameters, and the preparation yield of the method is high; and compared with a traditional reaction kettle batch-type chemical synthesis method, the method of the invention has the advantages of high-speed mixing, narrow reactant retentiontime, good repeatability, almost no amplification effect, convenience in real-time monitoring of the reaction process, high safety performance and the like, and is beneficial to large-scale productionand application of the substance.

PROCESS FOR THE PREPARATION OF TICAGRELOR

The present invention relates to a process for the preparation of ticagrelor, which provides a product of high purity, in particular, with no detectable levels of Nnitrosmine impurities. The process comprises a first step of treating 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]ethanol starting material with sodium nitrite, followed by acidic washing; in a second step, the 2-[[(3aR,4S,6R,6aS)-6-[7-chloro-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H- cyclopenta-1,3-dioxol-4-yl]oxy]ethanol obtained in the previous step is coupled with trans-(1 fl,2S)-2-(3,4-difluorophenyl)cyclopropylamine, and the reaction is followed by a first washing at basic pH a second washing at acidic pH; and in an third step, the compound obtained in the previous step is deprotected by treatment with mineral acid, followed by acidic washing.

S-type chiral sulfoxide compound preparation method

The invention belongs to the field of chemical synthesis, and particularly relates to an S-type chiral sulfoxide compound preparation method, which mainly comprises four steps of cyclization, substitution, catalytic oxidation and hydrolysis removal of isopropylidene, wherein a catalytic oxidation reaction is carried out by adopting a certain catalyst and a certain catalytic system (a metal organiccatalyst, a chiral reagent and water) according to a certain ratio and according to a certain sequence to obtain the high-purity S-type chiral sulfoxide compound. According to the invention, the reaction conditions are mild, the high-purity S-type chiral sulfoxide compound can be obtained with high yield under the optimal conditions, and the subsequent research on the biological activity of the S-type chiral sulfoxide compound is facilitated.

Preparation method of R-type chiral sulfoxide compound

The invention belongs to the field of chemical synthesis, and particularly relates to a preparation method of an R-type chiral sulfoxide compound. The preparation method mainly comprises the four steps of ring formation, substitution, catalytic oxidation

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.

Ticagrelor condensation impurity preparation method

The invention belongs to the field of chemical synthesis, and particularly relates to a ticagrelor condensation impurity preparation method, which mainly comprises three steps of cyclization, couplingand isopropylidene removal. According to the present invention, a coupling reaction is performed by combining an alkaline non-metal catalyst and a certain reaction temperature, and an isopropylideneremoval reaction is performed by using trace 2, 3-dichloro-5, 6-dicyano-p-benzoquinone, such that the yield of the target product can be significantly improved, the purity can achieve 97.80% without column chromatography purification, and the method is environmentally-friendly, safe, simple and easy to perform; and the method can adopt the one-pot boiling synthesis method to prepare the target product, so that the tedious experiment steps are reduced, the conditions are mild, and the method is suitable for large-scale industrial production of ticagrelor condensation impurities.

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.

Preparation method of ticagrelor medicinal crystal form II

The invention relates to a preparation method of ticagrelor, in particular to a preparation method of a ticagrelor medicinal crystal form II. The invention provides a new method of preparing the ticagrelor medicinal crystal form II from 2-(3AR, 4S, 6R, 6AS)-6-(5-amino-6-chloro-2-propylthio-4-pyrimidinyl)amino tetrahydro-2, 2-dimethyl-4H-cyclopenteno-1, 3-dioxolane-4-yl]oxo]-ethanol. The method hasthe characteristics of stable process, high crystal form purity, small and uniform particle size, and is easy for large-scale production.

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.