145195-63-7

Basic information

• Product Name: CIS-ENTACAPONE
• Synonyms: CIS-ENTACAPONE;(2Z)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide;(Z)-Entacapone;Entacapone Related Compound A (25 mg) ((Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylacrylamide);Entacapone EP IMpurity A;Entacapone Related CoMpound A;Entacapone impurity A;Entacapone impurity A -I
• CAS NO: 145195-63-7
• Molecular Formula: C₁₄H₁₅N₃O₅
• Molecular Weight: 305.29
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 145195-63-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 142-144°C
• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Dichloromethane (Slightly), Methanol (Slightly)
• CAS DataBase Reference: CIS-ENTACAPONE(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-ENTACAPONE(145195-63-7)
• EPA Substance Registry System: CIS-ENTACAPONE(145195-63-7)

Safety Data

• Hazardous Substances Data: 145195-63-7(Hazardous Substances Data)

Usage

Description

cis-Entacapone is a metabolite of the catechol-O-methyltransferase (COMT) inhibitor entacapone . It is also a potential impurity found in commercial preparations of entacapone and a degradant of entacapone formed by UV light exposure.

Chemical Properties

Orange Solid

Uses

Different sources of media describe the Uses of 145195-63-7 differently. You can refer to the following data:
1. cis-Entacapone (Entacapone EP Impurity A) is the (Z)-Isomer of Entacapone polymorphic form B. Antiparkinsonian.
2. (Z)-Isomer of Entacapone polymorphic form B. Antiparkinsonian

Upstream product

• 26391-06-0 2-cyano-N,N-diethylacetamide 
• 116313-85-0 3,4-dihydroxy-5-nitrobenzaldehyde 
• 686349-59-7 entacapone 
• 146698-91-1 2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxy-5-nitrophenyl)prop-2-enamide 

Downstream Products

• 1047659-02-8 entacapone; sodium salt 
• 1047659-01-7 entacapone; piperidine salt 
• 130929-57-6 entacapone 

Relevant articles and documents

DENGUE AND WEST NILE VIRUS PROTEASE INHIBITORS

Compounds and methods of treating or preventing a Flavivirus infection in a subject are provided. The methods comprise administering to the subject a therapeutically effective amount of a compound as described herein. The methods are useful in treating and/or preventing Flavivirus infections such as, for example, West Nile Virus, Dengue Virus, and Japanese Encephalitis Virus. Methods of inhibiting a Flavivirus protease in a cell are also provided.

PROCESS AND PRODUCT

The present invention relates to an improved process for isolation and purification of Entacapone, pharmaceutical compositions and therapeutic uses thereof. The process provides an improved yield and improved isomeric purity of produced Entacapone.

PROCESS FOR MANUFACTURING ENTACAPONE

A new process for manufacturing entacapone comprising reacting 3,4-dihydroxy-5-nitrobenzaldehyde with N,N-diethyl-2-cyanoacetamide in the presence of a catalyst in a C 4 to 8 alcohol at reduced pressure and at a temperature of at least 70 °C, cooling the mixture to a temperature of 30 °C or below, seeding the mixture with N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide comprising at least 10 % of the Z-isomer by weight in the seeding crystals, cooling the mixture to a temperature of 5 °C or below, isolating the crystallized product and converting the obtained mixture of the E- and Z-isomers of N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide to the E-isomer (entacapone).