1578153-81-7

Basic information

• Product Name: (S)-4-(((R)-6-(2-chloro-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-?4-yl)methyl)morpholine-3-carboxylic acid
• Synonyms: (S)-4-(((R)-6-(2-chloro-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-?4-yl)methyl)morpholine-3-carboxylic acid
• CAS NO: 1578153-81-7
• Molecular Weight: 508.958
• Mol File: 1578153-81-7.mol

Chemical Properties

• CAS DataBase Reference: (S)-4-(((R)-6-(2-chloro-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-?4-yl)methyl)morpholine-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-(((R)-6-(2-chloro-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-?4-yl)methyl)morpholine-3-carboxylic acid(1578153-81-7)
• EPA Substance Registry System: (S)-4-(((R)-6-(2-chloro-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-?4-yl)methyl)morpholine-3-carboxylic acid(1578153-81-7)

Safety Data

• Hazardous Substances Data: 1578153-81-7(Hazardous Substances Data)

Upstream product

• 84194-36-5 2-chloro-4-fluorobenzaldehyde 
• 141-97-9 ethyl acetoacetate 
• 1187929-04-9 (3S)-morpholine-3-carboxylic acid hydrochloride salt 
• 247037-78-1 ethyl 4-(2-chloro-4-fluorophenyl)-6-methyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate 
• 64-17-5 ethanol 
• 143444-49-9 (R)-1-ethoxy-1-oxopropan-2-yl 3-oxobutanoate 
• 106825-79-0 (S)-morpholine-3-carboxylic acid 
• 247037-81-6 ethyl 4-(R)-(2-chloro-4-fluorophenyl)-2-(thiazol-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate 

Relevant articles and documents

A New Approach of Mitigating CYP3A4 Induction Led to the Discovery of Potent Hepatitis B Virus (HBV) Capsid Inhibitor with Optimal ADMET Profiles

Described herein is a new approach to mitigate CYP3A4 induction. In this unconventional approach, a fine-tuning of the dihedral angle between the C4 phenyl and the dihydropyrimidine core of the heteroaryldihydropyrimidine (HAP) class of capsid inhibitors

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Discovery and Pre-Clinical Characterization of Third-Generation 4-H Heteroaryldihydropyrimidine (HAP) Analogues as Hepatitis B Virus (HBV) Capsid Inhibitors

Described herein are the discovery and structure-activity relationship (SAR) studies of the third-generation 4-H heteroaryldihydropyrimidines (4-H HAPs) featuring the introduction of a C6 carboxyl group as novel HBV capsid inhibitors. This new series of 4-H HAPs showed improved anti-HBV activity and better drug-like properties compared to the first- and second-generation 4-H HAPs. X-ray crystallographic study of analogue 12 (HAP_R01) with Cp149 Y132A mutant hexamer clearly elucidated the role of C6 carboxyl group played for the increased binding affinity, which formed strong hydrogen bonding interactions with capsid protein and coordinated waters. The representative analogue 10 (HAP_R10) was extensively characterized in vitro (ADMET) and in vivo (mouse PK and PD) and subsequently selected for further development as oral anti-HBV infection agent.

PROCESSES FOR PREPARING DIHYDROPYRIMIDINE DERIVATIVES AND INTERMEDIATES THEREOF

The present invention relates to processes for preparing a dihydropyrimidine derivative having Formula (I) or a tautomer thereof having Formula (Ia), as well as a intermediate thereof. The processes of the invention have simple operation, high optical purity of product, high yield and convenient work-up, which is suitable for industrial production.

PROCESSES FOR PREPARING DIHYDROPYRIMIDINE DERIVATIVES AND INTERMEDIATES THEREOF

The present invention refers to processes for preparing a dihydropyrimidine compound having Formula (I), or a tautomer thereof having Formula (la), as well as a intermediate thereof. The process of the invention has simple operation, high optical purity of product, high yield and convenient work-up, which is suitable for industrial production.

6-AMINO ACID HETEROARYLDIHYDROPYRIMIDINES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION

The invention provides novel compounds having the general formula:, wherein R1, R2, R3, R4 and A are as described herein, compositions including the compounds and methods of using the compounds.