475504-31-5

Usage

Type

Chemical compound
With pharmacological properties

Use

Medication for treating Parkinson's disease and Parkinsonian tremors
By blocking the action of certain neurotransmitters in the brain

Mechanism of action

Antagonist at muscarinic acetylcholine receptors
Involved in movement and muscle control

Chemical structure

Derivative of the tropane alkaloid
Structurally related to atropine
Includes a benzyl group, a methyl group, and a piperidine ring
Contains a hydroxy and carboxylate group

Duration of action

Relatively long

Forms available

Oral and injectable
For clinical use

Upstream product

• 501-53-1 benzyl chloroformate 
• 211058-81-0 methyl (2R,4S)-4-hydroxy-2-piperidinecarboxylate 
• 475504-29-1 (2R)-4-formylpipecolic acid methyl ester 
• 127474-54-8 (R)-2-(benzyloxycarbonylamino)pent-4-enoic acid 
• 127515-28-0 (R)-methyl 2-[N-(benzyloxycarbonyl)amino]-4-pentenoate 
• 50299-14-4 N-Acetyl-α-allylglycine 

Downstream Products

• 321744-26-7 N-Boc-4-hydroxy-2-piperidine carboxylic acid methyl ester 
• 475504-32-6 (2R,4R)-4-hydroxypipecolic acid methyl ester 
• 211055-76-4 (2R,4S)-4-(2,4-Dichloro-phenoxy)-piperidine-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Use of hydrolases for the synthesis of cyclic amino acids

The synthesis of several cyclic amino acids that have all the necessary structural features to make them ideal scaffolds for use in medicinal chemistry is described. A key step in each synthesis is the use of hydrolase enzymes to define a chiral centre. I

Chemoenzymatic synthesis of the four diastereoisomers of 4-hydroxypipecolic acid from N-acetyl-(R,S)-allylglycine: Chiral scaffolds for drug discovery

All four diastereoisomers of 4-hydroxypipecolic acid were prepared in a form conveniently protected for drug discovery applications with the use of industrially scaleable methodology. Resolution of the racemic starting material using proprietary acylases followed by an acyliminium ion cyclisation gave diastereomeric mixtures of 4-formyloxypipecolic acid, which were differentiated using an enzyme-catalysed hydrolysis. The products were separated by partition, and by following a sequence of straightforward chemical steps, the individual stereoisomers of the protected 4-hydroxypipecolates were crystallized to optical purity in 100 g quantities.

Novel constrained CCK-B dipeptoid antagonists derived from pipecolic acid

A new series of 4-substituted pipecolic acid derivatives was prepared and incorporated into dipeptoids. The resulting products behave as moderately potent CCK-B antagonists but their constrained structure and its comparison with structurally related compounds yield valuable information about the conformational requirements for optimal recognition of the CCK-B receptor by antagonists.