179474-81-8

Basic information

• Product Name: Prucalopride
• Synonyms: Prucalopride;4-Amino-5-chloro-2,3-dihydro-N-[1-(3-methoxypropyl)-4-piperidinyl]-7-benzofurancarboxamide;4-Amino-5-chloro-2,3-dihydro-N-(1-(3-methoxypropyl)-4-piperidyl)-7-benzofurancarboxamide;R 093877;R093877;Resolor;Unii-0A09iuw5tp;Prucalopride(R-93877)
• CAS NO: 179474-81-8
• Molecular Formula: C₁₈H₂₆ClN₃O₃
• Molecular Weight: 367.874
• EINECS: 1312995-182-4
• Product Categories: API;Inhibitors
• Mol File: 179474-81-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 90.7°
• Boiling Point: 481.369 °C at 760 mmHg
• Flash Point: 244.923 °C
• Appearance: /
• Density: 1.28
• Vapor Pressure: 2E-09mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: 2-8°C
• PKA: 13.65±0.20(Predicted)
• CAS DataBase Reference: Prucalopride(CAS DataBase Reference)
• NIST Chemistry Reference: Prucalopride(179474-81-8)
• EPA Substance Registry System: Prucalopride(179474-81-8)

Safety Data

• RIDADR: UN 3077 9 / PGIII
• Hazardous Substances Data: 179474-81-8(Hazardous Substances Data)

Usage

Description

Prucalopride is a potent and selective agonist of the serotonin (5-HT) receptor subtype 5-HT4, with high specificity for this receptor over a panel of 53 other receptors. It is known to induce contractions in the guinea pig colon and increase colonic motility in dogs, as well as enhance acetylcholine and histamine levels in the rat prefrontal cortex and power of hippocampal theta oscillations.

Uses

Used in Pharmaceutical Industry:
Prucalopride is used as a treatment for chronic idiopathic constipation, due to its ability to increase colonic motility and facilitate non-cholinergic contractions induced by electrical stimulation. It is also used to increase acetylcholine and histamine levels in the rat prefrontal cortex, which may have potential applications in the treatment of various neurological disorders.
Used in Research Applications:
Prucalopride is used as a research tool for studying the role of the 5-HT4 receptor in various physiological processes, including gastrointestinal motility, neurotransmitter release, and cognitive function. Its high selectivity for the 5-HT4 receptor makes it a valuable compound for investigating the specific functions and mechanisms of this receptor subtype.

Biochem/physiol Actions

In healthy male individuals, prucalopride decreases the display of esophageal acid and promotes gastric emptying. It is effective, safe and shows good tolerance for the treatment of men with chronic constipation.

Enzyme inhibitor

This novel enterokinetic drug (FW = 367.87 g/mol; CAS 179474-81-8), also known by the tradename Resolor? and its systematic name, 4-amino-5- chloro-N-[1-(3-methoxypropyl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-7- carboxamide, is a selective, high affinity serotonin 5-HT4 receptor agonist with that stimulates colonic mass movements, which provide the main propulsive force for defecation. It exhibits high affinity to both 5-HT4 receptor isoforms, with respective pKi values of 8.60 and 8.10 for the human 5-HT4A and 5-HT4B receptors. Based on 50 other binding assays,tonly the human D4 receptor (pKi = 5.63), the mouse 5-HT3 receptor (pKi = 5.41) and the human s1 (pKi = 5.43) shown measurable affinity, resulting in >290x selectivity for 5-HT4 receptors. Prucalopride also differs from other 5-HT4 agonists, such as tegaserod and cisapride, that interact with other receptors (5-HT1B/D and cardiac human ether-a-go-go K+ or hERG channel, respectively).

InChI:InChI=1/C18H26ClN3O3/c1-24-9-2-6-22-7-3-12(4-8-22)21-18(23)14-11-15(19)16(20)13-5-10-25-17(13)14/h11-12H,2-10,20H2,1H3,(H,21,23)

Upstream product

• 1249604-45-2 ethyl 1-(3-methoxy-propyl)-piperidin-4-carboxylate 
• 179474-79-4 4-amino-1-(3-methoxypropyl)piperidine 
• 123654-26-2 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid 
• 143878-29-9 4-acetamido-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid methyl ester 
• 182808-04-4 methyl 4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylate 
• 137211-63-3 ethyl 4-[[(4-amino-5-chloro-2,3-dihydrobenzofuran-7-yl)carbonyl]amino]-1-piperidinecarboxylate 
• 137211-64-4 4-amino-5-chloro-2,3-dihydro-N-(4-piperidinyl)benzofuran-7-carboxamide 
• 36215-07-3 1-Chloro-3-methoxypropane 
• 149466-67-1 methyl 4-acetylamino-2,3-dihydrobenzo[b]furan-7-carboxylate 
• 202664-85-5 methyl 4-acetylamino-2-hydroxy-3-(2-hydroxyethyl)benzoate 
• 555-16-8 4-nitrobenzaldehdye 
• 2403-53-4 2-(4-nitrophenyl)-1,3-dioxolane 
• 19073-14-4 4-(1,3-dioxolan-2-yl)aniline 
• 52161-21-4 N-[4-(1,3-dioxolan-2-yl)phenyl]acetamide 

Downstream Products

• 179474-85-2 prucalopride succinate 

Relevant articles and documents

Method for preparing prucalopride

The invention provides a method for preparing prucalopride. The method comprises the following steps: taking 3-chloro-4-methylaniline as an initial raw material, performing amino protection, nucleophilic substitution, hydroxy protection, aromatic hydrocarbon chlorination, free radical bromination, hydrolysis, molecular Friedel-Crafts alkylation reaction ring closure, amino deprotection and oxidative amidation, thereby obtaining the prucalopride. According to the scheme, a dangerous process is not adopted, any highly toxic reagent is not used, the method is safe, green and environmental-friendly, the amount of by-products produced in the reaction is small, and the yield is improved.

PROCESSES FOR THE PREPARATION OF HIGHLY PURE PRUCALOPRIDE SUCCINATE AND ITS INTERMEDIATES

Provided herein are purification processes for the preparation of highly pure prucalopride succinate salt. Provided also herein are improved, commercially viable and industrially advantageous processes for the preparation of Prucalopride and its intermediate compounds, for example, methyl 4-acetylamino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylate and alkyl 4-[[(4-amino-5-chloro-2,3-dihydro-7-benzofuranyl)carbonyl]-amino]-1-piperidinecarboxylate.