86718-70-9

Basic information

• Product Name: (+)-Cisapride
• Synonyms: (+)-cis-Apride;(+)-(R)-Cisapride
• CAS NO: 86718-70-9
• Molecular Formula: C₂₃H₂₉ClFN₃O₄
• Molecular Weight: 0
• Mol File: 86718-70-9.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-Cisapride(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Cisapride(86718-70-9)
• EPA Substance Registry System: (+)-Cisapride(86718-70-9)

Safety Data

• Hazardous Substances Data: 86718-70-9(Hazardous Substances Data)

Usage

Description

(+)-Cisapride is a prokinetic agent that stimulates the muscles in the gastrointestinal tract, enhancing their movements and accelerating stomach emptying. It is commonly used to treat conditions like gastroesophageal reflux disease (GERD) and gastroparesis. Despite its efficacy, it has been linked to serious side effects, such as irregular heartbeats and heart rhythm disturbances, leading to its withdrawal from the market in several countries. Nevertheless, (+)-cisapride remains significant for research and development of new gastrointestinal drugs.

Uses

Used in Pharmaceutical Industry:
(+)-Cisapride is used as a prokinetic agent for treating conditions such as gastroesophageal reflux disease (GERD) and gastroparesis, due to its ability to stimulate gastrointestinal muscles and speed up stomach emptying.
Used in Research and Development:
(+)-Cisapride is utilized as a key molecule in the research and development of new drugs targeting the gastrointestinal system, despite its withdrawal from the market due to serious side effects.

Upstream product

• 7206-70-4 4-amino-5-chloro-2-methoxybenzoic acid 
• 503433-37-2 C₁₅H₂₃FN₂O₂ 
• 150007-96-8 C₁₁H₁₂ClNO₅ 
• 1129-78-8 1-(3-bromopropoxy)-4-fluorobenzene 
• 401502-00-9 N-(3-(4-fluorophenoxy)propyl)prop-2-en-1-amine 
• 1345718-98-0 (3S,4R,αR)-N(1)-(3'-(4''-fluorophenoxy)propyl)-3-methoxy-4-[N-benzyl-N-(α-methylbenzyl)amino]piperidine 
• 1345718-97-9 (R,R,R)-N(1)-[3'-(4''-fluorophenoxy)propyl]-3-methoxy-4-[N-benzyl-N-(α-methylbenzyl)amino]piperidin-2-one 
• 1345718-96-8 (R,R,R)-N(1)-[3'-(4''-fluorophenoxy)propyl]-3-hydroxy-4-[N-benzyl-N-(α-methylbenzyl)amino]-piperidin-2-one 
• 1345718-95-7 tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-5-[N'-allyl-N'-3'-(4''-fluorophenoxy)propylamino]pentanoate 
• 1345718-94-6 tert-butyl (E)-5-[N-allyl-N-3'-(4''-fluorophenoxy)propylamino]pent-2-enoate 

Downstream Products

• 125557-41-7 4-Amino-5-chloro-N-{(3S,4R)-1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-(2-methanesulfinyl-ethoxy)-benzamide 
• 102671-13-6 4-Amino-5-chloro-N-{(3S,4R)-1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-(2-methylsulfanyl-ethoxy)-benzamide 
• 102671-04-5 4-Amino-5-chloro-N-{(3S,4R)-1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-hydroxy-benzamide 

Relevant articles and documents

Asymmetric syntheses of 3,4-syn- and 3,4-anti-3-substituted-4- aminopiperidin-2-ones: Application to the asymmetric synthesis of (+)-(3S,4R)-cisapride

The conjugate addition of lithium (R)-N-benzyl-N-(α-methylbenzyl) amide to δ-(N-allylamino)-α,β-unsaturated esters, followed by N-deallylation and cyclisation of the resultant β,δ-diamino esters, gives the corresponding 4-aminopiperidin-2-ones as single diastereoisomers (>99:1 dr). Subsequent deprotonation with LiHMDS and functionalisation of the resultant lithium enolate gives 3,4-anti-3-substituted-4-aminopiperidin-2-ones in >99:1 dr. Alternatively, in situ oxidation of the intermediate lithium (Z)-β-amino enolates formed upon conjugate addition gives α-hydroxy-β,δ-diamino esters, which after N-deallylation and cyclisation gives the corresponding 3,4-syn-3-hydroxy-4-aminopiperidin-2-ones in >99:1 dr. The utility of this methodology was successfully demonstrated in a concise asymmetric synthesis of the gastroprokinetic agent (+)-(3S,4R)- cisapride {(+)-(3S,4R)-N(1)-[3′-(4″-fluorophenoxy)propyl]-3-methoxy- 4-(2?-methoxy-4?-amino-5?-chlorobenzamido)piperidine} in nine steps from commercially available starting materials with an overall yield of 19%.