175865-59-5

Basic information

• Product Name: Valganciclovir hydrochloride
• Synonyms: Rs 079070-194;Unii-4p3T9qf9nz;Valcyt;Valcyte;Valganciclovir hydrochlorid;Valganciclovir Hydrochloride (500 mg);2-[(2-AMino-1,6-dihydro-6-oxo-9H-purin-9-yl)Methoxy]-3-hydroxypropyl Ester;L-Valine,2-[(2-aMino-1,6-dihydro-6-oxo-9H-purin-9-yl)Methoxy]-3-hydroxypropyl ester,hydrochloride (1:1)
• CAS NO: 175865-59-5
• Molecular Formula: C₁₄H₂₂N₆O₅*ClH
• Molecular Weight: 390.82
• EINECS: 1308068-626-2
• Product Categories: CLEOCIN;API;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals
• Mol File: 175865-59-5.mol

Chemical Properties

• Melting Point: 162-164°C
• Boiling Point: 629.1 °C at 760 mmHg
• Flash Point: 334.3 °C
• Appearance: white to tan/
• Vapor Pressure: 1.08E-16mmHg at 25°C
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: H2O: ≥8mg/mL
• Stability: Hygroscopic
• CAS DataBase Reference: Valganciclovir hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Valganciclovir hydrochloride(175865-59-5)
• EPA Substance Registry System: Valganciclovir hydrochloride(175865-59-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 175865-59-5(Hazardous Substances Data)

Usage

Uses

Used in Antiviral Treatment:
Valganciclovir hydrochloride is used as an antiviral agent for the treatment of HIV associated retinitis and for the prevention of post-transplant cytomegalovirus (CMV) infections. It inhibits viral DNA synthesis by targeting the CMV polymerase.
Used in HIV-related Cell Signaling Studies:
Valganciclovir hydrochloride is used in HIV-related cell signaling studies, providing insights into the mechanisms of the virus and potential therapeutic targets.
Used in the Treatment of Retrovirus:
As a pro-drug of ganciclovir, valganciclovir hydrochloride is used in the treatment of retrovirus, particularly cytomegalovirus (CMV) infections.
Used in Antibacterial Applications:
Valganciclovir hydrochloride is used as an antibacterial agent, inhibiting protein synthesis in certain bacterial pathogens.
Used in Pharmaceutical Quality Control:
Valganciclovir hydrochloride is used as a certified pharmaceutical secondary standard for application in quality control, providing a convenient and cost-effective alternative to pharmacopeia primary standards for pharma laboratories and manufacturers.

Originator

Roche (Switzerland)

Biochem/physiol Actions

Valganciclovir hydrochloride hydrate is an antiviral used to treat cytomegalovirus infection. It is the prodrug of ganciclovir, a synthetic analog of 2′-deoxy-guanosine which is phosphorylated to a dGTP analog that competitively inhibits the incorporation of dGTP by viral DNA polymerase.

InChI:InChI=1/C14H22N6O5.ClH/c1-7(2)9(15)13(23)24-4-8(3-21)25-6-20-5-17-10-11(20)18-14(16)19-12(10)22;/h5,7-9,21H,3-4,6,15H2,1-2H3,(H3,16,18,19,22);1H/t8?,9-;/m0./s1

Upstream product

• 194154-40-0 2-(2-amino-1,6 dihydro-6-oxo-purine-9-yl)-methoxy-3-hydroxy-1-propyl-N-(benzyloxy carbonyl)-L-valinate 
• 72-18-4 L-valine 
• 1219792-46-7 O-mesyl ganciclovir 
• 1219792-38-7 2-[(2-amino-1,6-dihydro-6-oxopurin-9-yl)methyloxy]-3-hydroxypropyl 2'-(S)-azido-3'-methylbutanoate 
• 175865-68-6 valganciclovir acetate 
• 1219792-43-4 N-trytil-2-(2-amino-1,6-dihydro-6-oxopurin-9-yl)methoxy-3-trityloxy-1'-propanyl-2'-(S)-azido-3'-methylbutanoate 
• 82410-32-0 ganciclovir 
• 40224-47-3 azidovaline 
• 109082-85-1 N²-trityl-9-<(3-hydroxy-2-propoxy-1-trityloxy)methyl>guanine 
• 175865-55-1 (2S)-2-((2-amino-6-oxo-1H-purin-9(6H)-yl)methoxy)-3-(benzyloxy)propyl-2-(benzyloxycarbonylamino)-3-methylbutanoate 
• 960495-42-5 L-valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-(acetyloxy)propyl ester hydrochloride 
• 88110-89-8 monoacetoxygancyclovir 
• 38075-43-3 (S)-2-{[1-(5-Chloro-2-hydroxy-phenyl)-1-phenyl-meth-(Z)-ylidene]-amino}-3-methyl-butyric acid 

Relevant articles and documents

Synthetic method of valganciclovir hydrochloride

The invention discloses a method for synthesizing valganciclovir hydrochloride, which comprises the following steps: with 1,3-dichloro-2-acetoxymethoxypropane as an initial raw material, preparing monochlorinated ganciclovir, and carrying out esterification, hydrolysis and deprotection salification to finally obtain the valganciclovir hydrochloride. The invention provides a synthesis method of siganciclovir hydrochloride, which avoids the problem of separation and conversion of N-7 and N-9 isomers in the diacetyl guanine condensation process. The method directly synthesizes monochlorinated ganciclovir without using ganciclovir, instead of the synthesis of monoacetyl ganciclovir in the prior art, so that the method avoids the problem of diester compound separation caused by ganciclovir residues, has the advantages of short process steps, simple operation, convenient purification and low cost, is beneficial to industrial production, and is suitable for synthesis of valganciclovir hydrochloride.

Preparation method of valganciclovir hydrochloride

The invention provides a preparation method as shown in a formula I, and a preparation method of 2-[(2-amino-1,6-dihydro-6-oxo-9H-purine-9-yl)methoxy]-3-hydroxyl-L-valine propyl ester hydrochloride. The method is high in yield, stable in product quality and beneficial to industrial production.

A method for preparing valganciclovir hydrochloride

The invention discloses a method for preparing valganciclovir hydrochloride I. The method comprises the following steps of: 1, dissolving phosphorus oxychloride into an inert solvent, and performing a reaction of the mixture and the alcoholic liquor to obtain phosphoryl halide II; 2, performing a reaction of ganciclovir and the phosphoryl halide II obtained in the step to obtain ganciclovir monoester III; 3, esterfying the ganciclovir monoester III in the step 2 and N-carbobenzoxy-L-valine to obtain ganciclovir diester IV; 4, acidizing the ganciclovir diester IV in the step 3 for dephosphorylation to obtain N-carbobenzoxy-L-valine ganciclovir monoester V; and 5, performing a hydrogenation reaction on the product in the step 4 to prepare the valganciclovir hydrochloride I. By the method, the ganciclovir monoester with high purity and yield can be produced, the post-processing is easy, and the post-processing difficulty is reduced.

PROCESS FOR THE PREPARATION OF 2-AMINO-9-((2-PHENYL-1,3-DIOXAN-5-YLOXY)METHYL)-1H-PURIN-6(9H)-ONE COMPOUND USEFUL IN THE PREPARATION OF VALGANCICLOVIR

The present invention provides an improved industrially feasible process for the preparation of 2-amino-9-((2-phenyl-1,3-dioxan-5-yloxy)methyl)-1H-purin-6(9H)-one, Formula which is a useful intermediate for the preparation of Valganciclovir and pharmaceutically acceptable salts thereof, and involves the use of said new intermediate compounds in the process to obtain Valganciclovir.

A succinct synthesis of valganciclovir hydrochloride, a cytomegalovirus (CMV) retinitis inhibitor

A concise and efficient synthesis of valganciclovir hydrochloride 1, a CMV retinitis inhibitor, without involving protection-deprotection sequences, is described. The synthetic utility of (2S)-azido-3-methylbutyric acid, which acts as a masked L-valine equivalent, is demonstrated in the synthesis of 1. ARKAT-USA, Inc.

PREPARATION OF VALGANCICLOVIR AND ITS SALTS

The application relates to processes for preparing valganciclovir and pharmaceutically acceptable salts thereof, as well as intermediates for the processes. valganciclovir hydrochloride is represented by Formula II.

PROCESS FOR THE PREPARATION OF VALGANCICLOVIR HYDROCHLORIDE

The present invention provides a novel process for the preparation of pure valganciclovir hydrochloride.

PREPARATION OF VALGANCICLOVIR AND ITS SALTS

Processes for preparing valganciclovir and pharmaceutically acceptable salts thereof, as well as intermediates for the processes.

AMORPHOUS VALGANCICLOVIR HYDROCHLORIDE

The present application relates to amorphous forms of valganciclovir salts such as the hydrochloride and processes for their preparation.

Process for the preparation and purification of valgancyclovir

A process for the preparation of valgancyclovir which comprises: a) reacting a compound of formula 7, in an aprotic solvent, in the presence of a condensing agent, with a compound of formula 8, wherein R1, and R2 may be, each independently, hydrogen, an halogen atom or an hydroxyl group; the double bond may either be in the E or Z configuration or a mixture thereof to yield a compound of formula 9 b) mild hydrolysis of compound obtained in a) to give valgancyclovir.