Olprinone hydrochloride

Base Information

• Chemical Name: Olprinone hydrochloride
• CAS No.: 119615-63-3
• Molecular Formula: C₁₄H₁₀N₄O*ClH
• Molecular Weight: 286.721
• European Community (EC) Number: 634-250-2
• UNII: F18B658J56
• DSSTox Substance ID: DTXSID7045813
• Wikidata: Q27116316
• Metabolomics Workbench ID: 68113
• ChEMBL ID: CHEMBL1436121
• Mol file: 119615-63-3.mol

Synonyms:1,2-dihydro-6-methyl-2-oxo-5-(imidazo(1,2-a)pyridin-6-yl)-3-pyridinecarbonitrile;E 1020;E-1020;loprinone hydrochloride;olprinone

Chemical Property of Olprinone hydrochloride

Chemical Property:

• Melting Point: >3000C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 83.18000
• Density: 1.34g/cm³
• LogP: 2.60738
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≤4 mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 286.0621387
• Heavy Atom Count: 20
• Complexity: 525

Purity/Quality:

99% ^*data from raw suppliers

LoprinoneHydrochloride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C=C(C(=O)N1)C#N)C2=CN3C=CN=C3C=C2.Cl
• Recent NIPH Clinical Trials: Efficacy of Olprinone Hydrochloride During Pulmonary Resection for Lung Cancer
• 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.
• Uses: Inotropic agent which inhibits cAMP phosphodiesterase. Cardiotonic. Inotropic agent which inhibits cAMP phosphodiesterase. Cardiotonic

Technology Process of Olprinone hydrochloride

There total 4 articles about Olprinone hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.6%

olprinone (106730-54-5) → 1,2-dihydro-6-methyl-2-oxo-5-(imidazo[1,2-a]pyridin-6-yl)-3-pyridine carbonitrile hydrochloride (119615-63-3)

Guidance literature:

With hydrogenchloride; In methanol; water; at 70 - 80 ℃; for 0.166667h;

Reference yield:

6-bromoimidazo[1,2-a]pyridine (6188-23-4) → 1,2-dihydro-6-methyl-2-oxo-5-(imidazo[1,2-a]pyridin-6-yl)-3-pyridine carbonitrile hydrochloride (119615-63-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: ethylmagnesium bromide / tetrahydrofuran / 1.5 h / 65 - 70 °C

1.2: 2 h / 65 - 70 °C

2.1: hydrogenchloride; ozone / methanol; water / -10 °C

3.1: isopropyl alcohol / 1 h / 80 - 85 °C

4.1: sodium methylate / ethanol / 1 h / Reflux

5.1: hydrogenchloride / methanol; water / 0.17 h / 70 - 80 °C

With hydrogenchloride; ethylmagnesium bromide; sodium methylate; ozone; In tetrahydrofuran; methanol; ethanol; water; isopropyl alcohol;

Reference yield:

6-(2-methyl-2-propenyl)imidazo<1,2-a>pyridine (116355-20-5) → 1,2-dihydro-6-methyl-2-oxo-5-(imidazo[1,2-a]pyridin-6-yl)-3-pyridine carbonitrile hydrochloride (119615-63-3)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogenchloride; ozone / methanol; water / -10 °C

2: isopropyl alcohol / 1 h / 80 - 85 °C

3: sodium methylate / ethanol / 1 h / Reflux

4: hydrogenchloride / methanol; water / 0.17 h / 70 - 80 °C

With hydrogenchloride; sodium methylate; ozone; In methanol; ethanol; water; isopropyl alcohol;

upstream raw materials:

6-bromoimidazo[1,2-a]pyridine

6-(2-methyl-2-propenyl)imidazo<1,2-a>pyridine

1-imidazo<1,2-a>pyridin-6-yl-2-propanone

olprinone

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