139290-69-0

Basic information

• Product Name: (+/-)-ALPHA-(2,3-DIMETHOXY-PHENYL)-1-[2-(4-FLUOROPHENYL)ETHYL]-4-PIPERIDINE-METHANOL
• Synonyms: MDL 100151;4-PIPERIDINEMETHANOL, ALPHA-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUOROPHENYL)ETHYL]-;(+/-)-ALPHA-(2,3-DIMETHOXY-PHENYL)-1-[2-(4-FLUOROPHENYL)ETHYL]-4-PIPERIDINE-METHANOL;(-(-(2,3-Dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidine-methanol;4-Piperidinemethanol, (-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-;rac-MDL100907;4-PiperidineMethanol, a-(2,3-diMethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-;4-Piperidinemethanol, (2,3-dimethoxyphenyl)-1-[2-(4-fluoropenyl)ethyl]
• CAS NO: 139290-69-0
• Molecular Formula: C₂₂H₂₈FNO₃
• Molecular Weight: 373.46
• Mol File: 139290-69-0.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+/-)-ALPHA-(2,3-DIMETHOXY-PHENYL)-1-[2-(4-FLUOROPHENYL)ETHYL]-4-PIPERIDINE-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-ALPHA-(2,3-DIMETHOXY-PHENYL)-1-[2-(4-FLUOROPHENYL)ETHYL]-4-PIPERIDINE-METHANOL(139290-69-0)
• EPA Substance Registry System: (+/-)-ALPHA-(2,3-DIMETHOXY-PHENYL)-1-[2-(4-FLUOROPHENYL)ETHYL]-4-PIPERIDINE-METHANOL(139290-69-0)

Safety Data

• Hazardous Substances Data: 139290-69-0(Hazardous Substances Data)

Usage

Chemical Properties

Colourless to yellowish solid

Upstream product

• 252364-39-9 4-[1-oxo-1-(2,3-dimethoxyphenyl)methyl]-N-2-(4-fluorophenylethyl)piperidine 
• 91-16-7 1,2-dimethoxybenzene 
• 139290-66-7 1-[2-(4-fluorophenyl)-ethyl]-4-piperidinecarboxamide 
• 243640-37-1 4-[1-hydroxy-1-(2,3-dimethoxyphenyl)methyl]-N-2-(4-fluorophen-1-oxo-ethyl)piperidine 
• 869749-06-4 (S)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol, (2S,3S)-(+)-di-(p-anisoyl)-tartaric acid salt 
• 243640-20-2 (R)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol, (2S,3S)-(+)-di-(p-anisoyl)-tartaric acid salt 
• 243640-29-1 4-[1-oxo-1-(2,3-dimethoxyphenyl)methyl]-N-2-(4-fluorophen-1-oxo-ethyl)piperidine 
• 175673-57-1 (-)-MDL 100907 
• 332-42-3 (2-bromoethyl)-4-fluorobenzene 
• 140235-25-2 (+/-)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol 
• 7589-27-7 2-(4-Fluorophenyl)ethanol 
• 175553-32-9 1-[2-(4-fluorophenyl)ethyl]-4-piperidinecarboxylic acid N-methoxy N-methyl amide 
• 175553-31-8 1-[2-(4-fluorophenyl)-ethyl]-piperidine-4-carboxylic acid ethyl ester 
• 1126-09-6 4-carbethoxypiperidine 

Downstream Products

• 243640-20-2 (R)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol, (2S,3S)-(+)-di-(p-anisoyl)-tartaric acid salt 
• 869749-06-4 (S)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol, (2S,3S)-(+)-di-(p-anisoyl)-tartaric acid salt 
• 243640-24-6 (R)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol, butyrate ester 
• 243640-22-4 α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol, butyrate ester 
• 175673-57-1 (-)-MDL 100907 
• 175553-30-7 (S)-(-)-α-(2-hydroxy-3-methoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanone 
• 175553-29-4 (R)-(+)-α-(2-hydroxy-3-methoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanone 
• 139290-65-6 R-(+)-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol 
• 139290-76-9 (S,S)-(+)-α-[(2,3-dimethoxyphenyl)-[1-[2-(4-fluorophenyl)ethyl]-4-piperidinyl]methyl]-α-methoxybenzene acetate 

Relevant articles and documents

Synthesis and in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT2A receptor imaging with PET

Radiolabelled piperidine derivatives such as [11C]MDL 100907 and [18F]altanserin have played an important role in diagnosing malfunction in the serotonergic neurotransmission. A variety of novel piperidine MDL 100907 derivatives, possible to label with 18F-fluorine, were synthesized to improve molecular imaging properties of [11C]MDL 100907. Their in vitro affinities to a broad spectrum of neuroreceptors and their lipophilicities were determined and compared to the clinically used reference compounds MDL 100907 and altanserin. The novel compounds MA-1 (53) and (R)-MH.MZ (56) show Ki-values in the nanomolar range towards the 5-HT2A receptor and insignificant binding to other 5-HT receptor subtypes or receptors. Interestingly, compounds MA-1 (53), MH.MZ (55) and (R)-MH.MZ (56) provide a receptor selectivity profile similar to MDL 100907. These compounds could possibly be preferable antagonistic 18F-tracers for visualization of the 5-HT2A receptor status. Medium affine compounds (VK-1 (32), (51), (52), (54)) were synthesized and have Ki values between 30 and 120 nM. All promising compounds show log P values between 2 and 3, that is, within the range of those for the established radiotracers altanserin and MDL 100907. The novel compounds MA-1 (53) and (R)-MH.MZ (56) thus appear to be promising high affine and selective tracers of 18F-labelled analogues for 5-HT2A imaging with PET.

Processes for the preparation of (R)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol"

The present invention provides various processes for the preparation of (R)-±-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol. These processes may be characterized by the following scheme:

Use of MDL-100,907 for treatment of allergic and eosinophil mediated diseases

Methods of modulating eosinophil migration, chemotaxis or generation, in vitro, ex vivo, and in vivo are provided. Methods include contacting eosinophils with an amount of 5-HT2A receptor agonist or antagonist sufficient to modulate eosinophil migration, chemotaxis or generation.