211364-69-1

Basic information

• Product Name: Mono-POC Tenofovir
• Synonyms: Mono-POC Tenofovir;Mono-POC Tenofovir (Mixture of DiastereoMers);((((R)-1-(6-aMino-9H-purin-9-yl)propan-2-yloxy)Methyl)(hydroxy)phosphoryloxy)Methyl isopropyl carbonate;Mono-POC PMPA;tenofovirMonoester;Tenofovir Disoproxil Related CoMpound E;(8R)-9-(6-Amino-9H-purin-9-yl)-5-hydroxy-8-methyl-2,4,7-trioxa-5-phosphanonanoic acid 1-methylethyl ester 5-oxide;Tenofovir monoisoproxil
• CAS NO: 211364-69-1
• Molecular Formula: C14H22N5O7P
• Molecular Weight: 403.327541
• Product Categories: Amines;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Phosphorylating and Phosphitylating Agents
• Mol File: 211364-69-1.mol

Chemical Properties

• Melting Point: 303-305°C (dec.)
• Boiling Point: 599.297°C at 760 mmHg
• Flash Point: 316.244°C
• Appearance: /
• Density: 1.562g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Dichloromethane (Slightly), Methanol (Slightly, Heated), Water (Slightly)
• PKA: 1.88±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Mono-POC Tenofovir(CAS DataBase Reference)
• NIST Chemistry Reference: Mono-POC Tenofovir(211364-69-1)
• EPA Substance Registry System: Mono-POC Tenofovir(211364-69-1)

Safety Data

• Hazardous Substances Data: 211364-69-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Mono-POC Tenofovir is used as an anti-HIV agent for its ability to inhibit the replication of the human immunodeficiency virus (HIV). It plays a crucial role in the treatment and management of HIV/AIDS by suppressing the viral load and helping to prevent the progression of the disease.
Used as an Antiviral:
In the field of antiviral research and treatment, Mono-POC Tenofovir is utilized as a potent antiviral agent. Its reverse transcriptase inhibitory properties make it effective against various viral infections, including HIV. It works by blocking the activity of reverse transcriptase, an enzyme essential for the replication of certain viruses, thus limiting their ability to multiply and spread within the host.
Used in Research and Development:
Mono-POC Tenofovir is also used in the research and development of new antiviral drugs and therapies. Its unique chemical properties and potent antiviral activity make it a valuable compound for studying the mechanisms of viral replication and the development of novel treatments for viral infections.

InChI:InChI=1/C14H22N5O7P/c1-9(2)26-14(20)23-7-25-27(21,22)8-24-10(3)4-19-6-18-11-12(15)16-5-17-13(11)19/h5-6,9-10H,4,7-8H2,1-3H3,(H,21,22)(H2,15,16,17)

Upstream product

• 180587-75-1 (R)-diethyl (((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate 
• 14047-28-0 (R)-9-(2-hydroxypropyl)adenine 
• 66224-66-6 adenine 
• 35180-01-9 chloromethyl isopropyl carbonate 
• 147127-20-6 tenofovir 
• 201341-05-1 tenofovir disoproxil 
• 201341-05-1 bis-isopropyloxycarbonylmethyl 9-((R)-2-(phosphonomethoxy)propyl)adenine 

Downstream Products

• 1246812-40-7 propan-2-yl {[(propan-2-yloxy)carbonyl]oxy}methyl {[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methanephosphonate 

Relevant articles and documents

NUCLEOSIDE AND NUCLEOTIDE CONJUGATE COMPOUNDS AND USES THEREOF

This disclosure provides nucleoside and nucleotide conjugate compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases,

Tenofovir phenyl propionate phosphoramidate compound as well as pharmaceutical composition and application thereof

The invention discloses a tenofovir phenyl propionate phosphoramidate compound as well as a pharmaceutical composition and an application of the tenofovir phenyl propionate phosphoramidate compound. The tests prove that the compound has the activity of inhibiting HBV virus replication, and has the advantages of higher activity, lower toxicity and the like than the existing drug tenofovir disoproxil fumarate (TDF) for treating AIDS. The experiments also prove that the compound also has the activity of inhibiting HIV-1 virus replication, and can be used for developing medicines for treating AIDSor medicines for treating hepatitis B.

Tenofovir disoproxil fumarate analog preparation method

The present invention discloses a tenofovir disoproxil fumarate analog preparation method, which comprises: carrying out a substitution reaction on adenine as a raw material and (R)-propylene carbonate in the presence of an alkali, carrying out a substitution reaction with (diethoxyphosphoryl)methyl-4-methylbenzenesulfonate, hydrolyzing with a concentrated hydrochloric acid solution, crystallizingto obtain anhydrous tenofovir, carrying out a reaction on the anhydrous tenofovir and chloromethyl isopropyl carbonate to obtain tenofovir monoester, and carrying out a reaction with 2-bromopropane to obtain the target compound. According to the present invention, the selected starting raw materials are inexpensive and easy to obtain, the process is simple, and the material utilization rate and total yield are improved; and the intermediate of the method is purified by re-crystallization, such that the yield is high, and the purity is high.

Preparation method and application of tenofovir monoester

The invention belongs to the field of medicines, and in particular relates to a preparation method and application of tenofovir monoester. The method comprises the following steps: preparing tenofovirand chloromethyl isopropyl carbonate; dissolving the tenofovir into an organic solvent, adding an organic alkali and a catalyst, adding the chloromethyl isopropyl carbonate, and performing a reactionto obtain a solid tenofovir disoproxil; and performing hydrolysis on the solid tenofovir disoproxil in an alkali aqueous solution to obtain the tenofovir monoester. The preparation method of the tenofovir monoester provided by the invention has easily-available raw materials, is simple and convenient to operate, and has low requirements on equipment, and important significance for effectively controlling quality of tenofovir disoproxil fumarate.

Preparation method of tenofovir disoproxil

The invention belongs to the field of pharmaceutical chemistry, and specifically relates to a preparation method of tenofovir disoproxil. The preparation method comprises the following steps: (1) mixing tenofovir, an organic alkali, a catalyst, and a reaction solvent to obtain a mixed solution, wherein the catalyst is 4-dimethylaminopyridine; (2) adding chloroformic acid isopropyl carbonate into the mixed solution to carry out reactions; and (3) carrying out separation to obtain tenofovir disoproxil. The preparation method has the advantages that 4-dimethylaminopyridine (DMAP) is taken as the catalyst, the monoester impurity can be controlled to be less than 4% without using recrystallization; under same technological conditions, the monoester impurity content of a product prepared by using other catalysts is 9 to 14%, and the monoester impurity content is 15 to 20% if no catalyst is used.

Acyclic nucleoside phosphamide D-amino-acid ester derivative, preparation method of derivative salt and application of derivative to antiviral effect

The invention belongs to the field of medical chemical antiviral effects, and relates to an acyclic nucleoside phosphamide D-amino-acid ester derivative, a preparation method of derivative salt and an application of the derivative to the antiviral effects. The invention further provides a compound comprising the derivative, a stereoisomer of the derivative, pharmaceutically acceptable salt, a hydrate, a solvate or crystal and drug combination and an application of the compound or combination to treatment and/or prevention of Aids and hepatitis B virus infection. The in vivo activity of the compound is remarkably superior to that of a pro-drug of acyclic nucleoside phosphamide L-amino-acid ester, and the compound has obvious clinical application values.

Process improvements for the manufacture of tenofovir disoproxil fumarate at commercial scale

The three-step manufacturing process used in the synthesis of tenofovir disoproxil fumarate (1) was studied and optimized, leading to a more productive and robust process. The yield was improved from about 13% overall to 24%. Key process improvements identified included implementation of a telescoped process for the second stage that obviated the need for an extraction and solvent exchange, and significant optimization of the final reaction, including the beneficial effect of adding a quaternary ammonium salt to the alkylation reaction and development of a nonaqueous process for removal of NMP and triethylamine from the product mixture to decrease the level of decomposition of product during the isolation.