Opicapone

Base Information

• Chemical Name: Opicapone
• CAS No.: 923287-50-7
• Molecular Formula: C₁₅H₁₀Cl₂N₄O₆
• Molecular Weight: 413.174
• Mol file: 923287-50-7.mol

Synonyms:BIA 9-1067;Opicapone;

Chemical Property of Opicapone

Chemical Property:

• Boiling Point: 701.1±70.0 °C (760 mmHg)
• PKA: 4.67±0.38(Predicted)
• PSA: 150.66000
• Density: 1.80±0.1 g/cm3 (20 °C, 760 mmHg)
• LogP: 4.59830

Purity/Quality:

99% ^*data from raw suppliers

Opicapone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Opicapone is a selective and reversible catechol O-methyltransferase (COMT) inhibitor that was developed by the Portuguese pharmaceutical firm Bial and sold to Neurocrine Biosciences. The drug was approved by the USFDA as adjunctive treatment to levodopa (L-Dopa)/ dopa-decarboxylase inhibitor (DDCI) therapy in adults with Parkinson’s disease (PD) and end-of-dose motor fluctuations that cannot be stabilized on those combinations. In 14- to 15- week double-blind multinational trials and in one-year openlabel extension studies in this patient population, opicapone was an effective and generally well-tolerated adjunctive therapy to L-Dopa plus a DDCI and other PD therapies. During the double-blind phase, adjunctive opicapone (50 mg once daily) provided significantly greater improvements in motor fluctuations than placebo, and no new unexpected safety concerns were identified after treatment with opicapone over a 1.4 year period. Furthermore, no serious cases of hepatotoxicity were reported in clinical trials, which represents a significant safety profile improvement over existing standard-of-care COMT inhibitors enticapone, tolcapone, and nebicapone.
• Uses: Opicapone, is used for the synthesis of novel nitrocatechol-substituted heterocycles, having the ability to inhibit catechol-O-methyltransferase (COMT), used for the treatment of Parkinson`s diseases.

Technology Process of Opicapone

There total 22 articles about Opicapone 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: 95.3%

5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-2-hydroxy-3-methoxy-1-nitrobenzene (1402714-41-3) → 2,5-dichloro-3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-4,6-dimethylpyridine 1-oxide (923287-50-7)

Guidance literature:

With pyridine; aluminum (III) chloride; In 1-methyl-pyrrolidin-2-one; at 5 - 62 ℃; for 2.66667h; Concentration; Time; Large scale;

Reference yield: 94.0%

2,5-dichloro-3-[5-(3,4-dimethoxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl]-4,6-dimethylpyridine-1-oxide → 2,5-dichloro-3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-4,6-dimethylpyridine 1-oxide (923287-50-7)

Guidance literature:

With aluminum (III) chloride; In N,N-dimethyl-formamide; at 5 - 85 ℃; for 6h;

Reference yield: 87.0%

3-(5-(3,4-bis(benzyloxy)-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-2,5-dichloro-4,6-dimethylpyridine 1-oxide (1044137-00-9) → 2,5-dichloro-3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-4,6-dimethylpyridine 1-oxide (923287-50-7)

Guidance literature:

With boron trifluoride; In dichloromethane; at -78 - 20 ℃; for 1h; Inert atmosphere;

upstream raw materials:

3-(5-(3,4-bis(benzyloxy)-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-2,5-dichloro-4,6-dimethylpyridine 1-oxide

acetylacetone

3-Cyano-4,6-dimethyl-2(1H)-pyridon

5-chloro-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile