119615-63-3

Basic information

• Product Name: OLPRINONE HYDROCHLORIDE
• Synonyms: 3-pyridinecarbonitrile,1,2-dihydro-5-(imidazo(1,2-a)pyridin-6-yl)-6-methyl-2-o;e1020;xo-,monohydrochloride,monohydrate;OLPRINONE HCL;1,2-Dihydro-5-imidazo[1,2-α]pyridin-6-yl-6-methyl-2-oxo-3-pyridinecarbonitrile Hydrochloride;Coretec;Loprinone hydrochloride, 1,2-Dihydro-5-(imidazo[1,2-a]pyridin-6-yl)-6-methyl-2-oxo-3-pyridinecarbonitrile hydrochloride;3-Pyridinecarbonitrile,1,2-dihydro-5-imidazo[1,2-a]pyridin-6-yl-6-methyl-2-oxo-,monohydrochloride
• CAS NO: 119615-63-3
• Molecular Formula: C14H10N4O.ClH.H2O
• Molecular Weight: 304.736
• Product Categories: Heterocyclic Compounds;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 119615-63-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: >3000C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: beige/solid
• Density: 1.34g/cm³
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≤4 mg/mL
• CAS DataBase Reference: OLPRINONE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: OLPRINONE HYDROCHLORIDE(119615-63-3)
• EPA Substance Registry System: OLPRINONE HYDROCHLORIDE(119615-63-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: US4201450
• Hazardous Substances Data: 119615-63-3(Hazardous Substances Data)

Usage

Description

Coatec was launched in Japan for acute cardiac insufficiency in cases resistant to other treatments. There are three related synthetic routes, 5-6 steps each, to loprinone all converging on 1-(imidazo[1,2a]pyridyl-6-yl)-Zpropanone as an advanced intermediate. It is a potent and selective inhibitor of PDE Ⅲ and a long lasting, orally active, positive inotropic agent. The PDE Ⅲ inhibition caused increased levels of CAMP which leads to the positive inotropic effect that was not altered by β or H2-preceptor antagonists. It was 100 times less potent at PDE I and PDE Ⅱ with no Na-K-ATPase activity. Improved hemodynamic parameters with slight changes in heart rate and blood pressure were seen in vivo. It is not mutagenic and its primary metabolite was less active.

Chemical Properties

Off-White Crystalline Powder

Originator

Eisai (Japan)

Uses

Different sources of media describe the Uses of 119615-63-3 differently. You can refer to the following data:
1. Inotropic agent which inhibits cAMP phosphodiesterase. Cardiotonic.
2. Inotropic agent which inhibits cAMP phosphodiesterase. Cardiotonic

Brand name

Coatec

InChI:InChI=1/C14H10N4O.ClH/c1-9-12(6-11(7-15)14(19)17-9)10-2-3-13-16-4-5-18(13)8-10;/h2-6,8H,1H3,(H,17,19);1H

Upstream product

• 6188-23-4 6-bromoimidazo[1,2-a]pyridine 
• 116355-20-5 6-(2-methyl-2-propenyl)imidazo<1,2-a>pyridine 
• 116355-08-9 1-imidazo<1,2-a>pyridin-6-yl-2-propanone 
• 106730-54-5 olprinone 

Relevant articles and documents

Olprinone hydrochloride compound preparation method

The invention discloses an olprinone hydrochloride compound preparation method. 6-bromoimidazo[1,2-a]pyridine is used as a starting material to prepare an olprinone hydrochloride compound through Grignard reaction, ozone oxidation, additive reaction, closed-loop reaction, salification and refining. The preparation process is mild in reaction condition, technically stable, high in repeatability andproduct yield, less in impurity and suitable for industrial production.