160707-69-7

Basic information

• Product Name: Apricitabine
• Synonyms: APRICITABINE;4-Amino-1-[(2R,4R)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl]-2(1H)-pyrimidinone;(-)-Bch 10652;2(1H)-Pyrimidinone, 4-amino-1-((2R,4R)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl)-;2(1H)-Pyrimidinone, 4-amino-1-(2-(hydroxymethyl)-1,3-oxathiolan-4-yl)-, (2R-cis)-;Avx 754;Avx754;Bch 10618
• CAS NO: 160707-69-7
• Molecular Formula: C8H11N3O3S
• Molecular Weight: 229.26
• Mol File: 160707-69-7.mol

Chemical Properties

• Boiling Point: 475.4±55.0 °C(Predicted)
• Appearance: /
• Density: 1.73
• PKA: 13.83±0.10(Predicted)
• CAS DataBase Reference: Apricitabine(CAS DataBase Reference)
• NIST Chemistry Reference: Apricitabine(160707-69-7)
• EPA Substance Registry System: Apricitabine(160707-69-7)

Safety Data

• Hazardous Substances Data: 160707-69-7(Hazardous Substances Data)

Usage

Uses

Used in HIV Treatment:
Apricitabine is used as an antiviral agent for the treatment of HIV/AIDS. It has been shown to be effective against lamivudine and zidovudine resistant virus strains, providing an alternative treatment option for patients with drug-resistant HIV.
Used in Pharmaceutical Industry:
Apricitabine is used as a research compound in the pharmaceutical industry for the development of new drugs targeting HIV and other viral infections. Its unique structure and potent inhibitory activity against HIV-1 reverse transcriptase make it a valuable asset in the ongoing fight against HIV and the development of new antiviral therapies.

Clinical Use

Apricitabine is an NRTI currently under clinical development that has a good safety profile, including a good mitochondrial toxicity profile. There may be a niche for apricitabine in the treatment of individuals infected with viral strains with reduced susceptibility to other nucleoside analogs, including strains with M184V and TAMs. NRTIs are recommended for clinical use in combination with other classes of antiretrovirals within highly active antiretroviral treatment (HAART) regimens for HIV infection. In light of its activity in vitro against HIV strains resistant to existing NRTIs, apricitabine is likely to be most useful for the treatment of antiretroviral-experienced patients failing therapy containing one of these agents. Investigating the efficacy, tolerability, and resistance selection properties of new antiretrovirals within combination HAART regimens is complicated by the confounding effects of the other prescribed agents. Therefore, developmental NRTIs are commonly evaluated first within short-term (r14 day) trials of monotherapy in antiretroviral naive HIV-infected patients. To date, apricitabine has shown efficacy in two phase II trials, one as monotherapy in antiretroviral-naive patients, and one within HAART for antiretroviral-experienced patients.

InChI:InChI=1/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-14-7(3-12)15-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7-/m1/s1

Upstream product

• 143338-44-7 2-[(phenylcarbonyloxy)methyl]-1,3-oxathiolane 
• 215436-53-6 cis-2-benzoyloxymethyl-4-(N₄'-acetylcytosin-1'-yl)-1,3-oxathiolane 
• 160706-00-3 2S-t-butyldiphenylsilyloxymethyl-4R-(N₄'-acetylcytosin-1'-yl)-1,3-oxathiolane 
• 186707-07-3 Trans and Cis-2S-t-butyldiphenylsilyloxymethyl-4-acetoxy-1,3-oxathiolane 
• 1126897-48-0 C₁₇H₁₇N₃O₅S 
• 1137664-38-0 2-(R)-benzoyloxymethyl-4-(R)-(N-benzoylcytosin-1-yl)-1,3-oxathiolane 
• 338389-72-3 (-)-cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3-oxathiolane p-toluensulfonate 
• 908337-01-9 (-)-cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3-oxathiolane (1R)-(-)-10-camphorsulfonate 
• 160579-78-2 2R-t-butyldiphenylsilyloxymethyl-4R-(N-4'-acetylcytosin-1'-yl)-1,3-oxathiolane 
• 186707-06-2 Trans and Cis-2R-t-butyldiphenylsilyloxymethyl-4-acetoxy-1,3-oxathiolane 
• 1137664-40-4 2-(S)-benzoyloxymethyl-4-(S)-(N-benzoylcytosin-1-yl)-1,3-oxathiolane 
• 160705-99-7 2S-t-butyldiphenylsilyloxymethyl-4S-(N-4'-acetylcytosin-1'-yl)-1,3-oxathiolane 
• 160705-94-2 2R-t-butyldiphenylsilyloxymethyl-4S-(N-4'-acetylcytosin-1'-yl)-1,3-oxathiolane 
• 909904-83-2 (-)-cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3-oxathiolane (1S)-(+)-10-camphorsulfonate 

Relevant articles and documents

ENANTIOMERIC RESOLUTION OF 2,4-DISUBSTITUTED 1,3-OXATHIOLANE NUCLEOSIDES

Single enantionmers of compounds of formula (B), in either the cis or trans configuration, wherein R1 and R2 are as defined herein, can be separated from enantiomeric mixtures thereof by reacting the compound with an acid to produce

Enantiomeric resolution of 2-substituted 4-substituted 1,3-oxathiolanes nucleosides

Single enantionmers of compounds of formula (B), in either the cis or trans configuration, wherein R1 and R2 are as defined herein, can be separated from enantiomeric mixtures thereof by reacting the compound with an acid to produce a conglomerate salt that has the following characteristics: the IR spectrum of the salt of the racemic compound, a 1:1 mixture of (?) and (+) crystals, is identical to that of the each of the single enantiomer, andthe salt of the racemic compound has a melting point lower that that of either single enantiomer. The conglomerate salt is then separated by preferential crystallization.

A PROCESS FOR CHIRAL RESOLUTION OF 2-SUBSTITUTED 4-SUBSTITUTED 1,3-OXATHIOLANES

The present invention relates to a novel process for the chiral resolution of 2-substituted 4-substituted 1,3-oxathiolanes and derivatives thereof. The present invention also relates to novel 2-substituted 4-substituted 1,3-oxathiolanes derivatives.

PROCESS AND METHODS FOR THE PREPARATION OF OPTICALLY ACTIVE CIS-2-HYDROXYMETHYL-4-(CYTOSIN-1′-YL)-1,3-OXATHIOLANE OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

There is provided a method for resolving a compound of formula (III), in the cis configuration: There is also provided a process for producing optically active compound of formula (I) or (II): wherein: R1, R2, R3 are as de

Process and methods for the preparation of optically active cis-2-hydroxymethyl-4- (cytosin-1'-yl) -1,3-oxathiolane or pharmaceutically acceptable salts thereof

There is provided a method for resolving a compound of formula III, in the cis configuration: There is also provided a process for producing optically active compound of formula I or II: wherein: R1, R2, R3 are as defined

Substituted 1,3-oxathiolanes with antiviral properties

This invention relates to single enantiomers of novel cis-substituted 1,3-oxathiolanes, of the formula (I): wherein; R1is hydrogen, and R2is cytosine or 5-fluorocytosine; and pharmaceutically acceptable salts and esters thereof. This invention also relates to pharmaceutical compositions containing them and to the use of these compounds as antiviral agents, particularly in combination therapy.

Substituted 1,3-oxathiolanes with antiviral properties

This invention relates to single enantiomers of novel cis-substituted 1,3-oxathiolanes, of the formula (I): wherein; R1is hydrogen, and R2is cytosine or 5-fluorocytosine, and pharmaceutically acceptable salts and esters thereof. This

A new strategy for the asymmetric synthesis of 1,3-oxathiolane-based nucleoside analogues

A ready asymmetric synthesis of 3'-oxathionucleosides has been accomplished in three main steps from benzoyloxyethanal. The synthesis is characterized by high overall yield and considerable enantiomeric excesses. It represents a general synthetic path to prepare a wide range of heterosubstituted sulfur-containing nucleoside analogues.

Short synthesis of 2,4-disubstituted 1,3-oxathiolane and 1,3-dithiolane cytosine nucleosides: Facile introduction of a 4-benzoate group using benzoyl peroxide

Introduction of a benzoate group at position 4 in 2-substituted 1,3- oxathiolane and 1,3-dithiolane using benzoyl peroxide is described. The coupling reaction between 1,3-oxathiolane derivatives 3 and pyrimidine bases in the presence of TMSI produced cis