Prucalopride succinate

Base Information

• Chemical Name: Prucalopride succinate
• CAS No.: 179474-85-2
• Molecular Formula: C18H26ClN3O3.C4H6O4
• Molecular Weight: 485.96
• European Community (EC) Number: 680-639-5
• UNII: 4V2G75E1CK
• DSSTox Substance ID: DTXSID701027749
• Wikidata: Q27260539
• NCI Thesaurus Code: C152112
• RXCUI: 2107309
• ChEMBL ID: CHEMBL2105748
• Mol file: 179474-85-2.mol

Synonyms:4-amino-5-chloro-N-(1-(3-methoxypropyl)-4-piperidinyl)-2,3-dihydro-1-benzofuran-7-carboxamide;motegrity;prucalopride;R 093877;R093877;Resolor;resotran;resotrans

Chemical Property of Prucalopride succinate

Chemical Property:

• Appearance/Colour: Off-White to Pale Brown Solid
• Melting Point: >196°C (dec.)
• PSA: 154.91000
• LogP: 3.11750
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 485.1928781
• Heavy Atom Count: 33
• Complexity: 538

Purity/Quality:

99.9% ^*data from raw suppliers

PrucaloprideSuccinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCCCN1CCC(CC1)NC(=O)C2=CC(=C(C3=C2OCC3)N)Cl.C(CC(=O)O)C(=O)O
• Recent EU Clinical Trials: Characterization of nerve-modulated macrophage population in the gastrointestinal tract
• Uses: Butanedioic acid 4-amino-5-chloro-2,3-dihydro-N-[1-(3-methoxypropyl)-4-piperidinyl]-7-benzofurancarboxamide is a selective 5-HT4 receptor agonist used effective for chronic constipation, but is not currently approved in the U.S. Prucalopride is approved for the treatment of chronic constipation in Europe. Prucalopride is a selective 5-HT4 receptor agonist used effective for chronic constipation, but is not currently approved in the U.S. Prucalopride is approved for the treatment of chronic constipation in Europe.
• Clinical Use: Prucalopride succinate, a first-in-class dihydrobenzofurancarboxamide, is a selective serotonin (5- HT4) receptor agonist. The drug, marketed under the brand name Resolor?, possesses enterokinetic activity and was developed by the Belgian-based pharmaceutical firm Movetis. Prucalopride alters colonic motility patterns via serotonin 5-HT4 receptor stimulation, triggering the central propulsive force for defecation.

Technology Process of Prucalopride succinate

There total 14 articles about Prucalopride succinate 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: 94.0%

4-amino-1-(3-methoxypropyl)piperidine (179474-79-4) + succinic acid (110-15-6) + 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid (123654-26-2) → prucalopride succinate (179474-85-2)

Guidance literature:

4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; for 1.5h;

4-amino-1-(3-methoxypropyl)piperidine; In tetrahydrofuran; at 45 ℃; for 4h;

succinic acid; In ethanol; at 20 ℃; for 2h; Solvent; Reagent/catalyst; Temperature;

Reference yield: 93.0%

succinic acid (110-15-6) + prucalopride (179474-81-8) → prucalopride succinate (179474-85-2)

Guidance literature:

In ethanol; at 40 ℃; for 3h;

Reference yield:

methyl 4-acetylamino-2,3-dihydrobenzo[b]furan-7-carboxylate (149466-67-1) → prucalopride succinate (179474-85-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 2.17 h / 25 - 75 °C

2.1: water; sodium hydroxide / methanol / 2.17 h / 25 - 55 °C

3.1: sulfuric acid / 8 h / 10 °C / Reflux

4.1: water; sodium hydroxide / methanol / 2 h / Reflux

5.1: chloroformic acid ethyl ester; triethylamine / chloroform / 0 - 30 °C

5.2: 25 - 30 °C

6.1: sulfuric acid / water / 10 - 95 °C

7.1: triethylamine; potassium iodide / N,N-dimethyl-formamide / 90 - 95 °C

8.1: methanol; isopropyl alcohol / 0.25 h / 60 - 65 °C

With N-chloro-succinimide; sulfuric acid; water; chloroformic acid ethyl ester; triethylamine; potassium iodide; sodium hydroxide; In methanol; chloroform; water; N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

ethyl 1-(3-methoxy-propyl)-piperidin-4-carboxylate

1-[3-(methyloxy)propyl]-4-piperidinecarboxamide

4-amino-1-(3-methoxypropyl)piperidine

succinic acid

Refernces

• 1、 -. "PROCESSES FOR THE PREPARATION OF HIGHLY PURE PRUCALOPRIDE SUCCINATE AND ITS INTERMEDIATES". Page/Page column 29. . Retrieved 2017/09/05.