167073-19-0

Basic information

• Product Name: Pitavastatin Ethyl Ester
• Synonyms: Pitavastatin Ethyl Ester;6-Heptenoic acid, 7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-, ethyl ester, (3R,5S)-;[3R,5S(E)]-Ethyl 7-[2-cyclopropyl-4-(p-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-6-heptenoate
• CAS NO: 167073-19-0
• Molecular Formula: C₂₇H₂₈FNO₄
• Molecular Weight: 449.5139232
• Mol File: 167073-19-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 428.7°C at 760 mmHg
• Flash Point: 213.1°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 1.49E-07mmHg at 25°C
• Refractive Index: 1.53
• Storage Temp.: 2-8°C
• PKA: 13.53±0.20(Predicted)
• CAS DataBase Reference: Pitavastatin Ethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: Pitavastatin Ethyl Ester(167073-19-0)
• EPA Substance Registry System: Pitavastatin Ethyl Ester(167073-19-0)

Safety Data

• Hazardous Substances Data: 167073-19-0(Hazardous Substances Data)

Usage

Uses

Pitavastatin Ethyl Ester is used as a reactant in an improved process for preparing quinoline derivatives.

InChI:InChI=1/C11H23Cl2N2O2PS/c1-3-10-19-11-4-9-17-18(16,14(11)2)15(7-5-12)8-6-13/h11H,3-10H2,1-2H3

Upstream product

• 254452-91-0 ethyl 5(S)-(E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-5-hydroxy-3-oxo-6-heptenoate 
• 477950-34-8 ethyl (E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-3,5-dihydroxyhept-6-enoate 
• 64-17-5 ethanol 
• 147526-32-7 pitavastatin 
• 148901-68-2 (E)-3-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-propenal 
• 1403338-19-1 methyl (2E)-3-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]acrylate 
• 1403338-24-8 ethyl (5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-5-(tert-butyldimethylsilyloxy)-3-oxo-6-heptenoate 
• 1403338-27-1 C₂₉H₃₄FNO₃Si 
• 222306-19-6 (3S,4E)-5-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-3-hydroxypentenoic acid 
• 1403338-23-7 C₃₂H₃₆FN₃O₂Si 
• 1403338-21-5 (3S,4E)-5-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-3-hydroxypentenoic acid (R)-α-methylbenzylamine salt 
• 1403338-20-4 (1S)-2-hydroxy-1,2,2-triphenylethyl (4E)-5-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-3-hydroxy-4-pentenoate 
• 121660-37-5 2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline 
• 166803-31-2 (E)-7-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dioxo-hept-6-enoic acid ethyl ester 

Downstream Products

• 574705-92-3 sodium (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoate 
• 147526-32-7 pitavastatin calcium salt 
• 1403338-25-9 ethyl (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-3,5-dihydroxy-6-heptenoate, trifluoroacetate salt 
• 147526-32-7 pitavastatin 

Relevant articles and documents

Virtual screening and experimental validation identify novel modulators of nuclear receptor RXRα from Drugbank database

Retinoid X receptor alpha (RXRα), an important ligand-dependent transcription factor, plays a critical role in the development of various cancers and metabolic and neurodegenerative diseases. Therefore, RXRα represents one of the most important targets in modern drug discovery. In this study, Drugbank 2.0 with 1280 old drugs were virtually screened by Glide according to the crystal structure of ligand-binding domain (LBP) of RXRα. 15 compounds selected were tested for their binding and transcriptional activity toward RXRα by Biacore and reporter gene assay, respectively. The identified new scafford ligand of RXRα, Pitavastatin (1), was chemically optimized. Our results demonstrated that statin compounds Pitavastatin (1) and Fluvastatin (4) could bind to the LBP of RXRα (KD = 13.30 μM and 11.04 μM, respectively) and serve as transcriptional antagonists of RXRα. On the contrary, compound (12) (domperidone) and (13) (rosiglitazone maleate) could bind to the LBP of RXRα (KD = 8.80 μM and 15.01 μM, respectively) but serve as transcriptional agonists of RXRα.

PROCESS FOR PREPARING QUINOLINE DERIVATIVE

The present invention relates to a novel process for preparing Pitavastatin calcium salt of formula (I).

Process for producing (3R,5S)-(E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin- 3-yl]-3, 5-dihydroxyhept-6-enic acid esters

A process for producing a compound represented by the following formula (IV): (wherein R denotes a hydrogen atom, an alkyl group, or an aryl group), comprising reducing a compound selected from the group consisting of: a compound represented by the following formula (I): (wherein R is as defined in the formula); a compound represented by the following formula (II): (wherein R is as defined in the formula); and a compound represented by the following formula (III): (wherein R is as defined in the formula), by reacting the compound with a cell of a microorganism and/or a cell preparation thereof capable of stereo-selectively reducing a keto group.