934665-56-2

Usage

Molecular structure

A complex organic compound with a piperidinecarboxylic acid core and various functional groups attached.

Core

1-Piperidinecarboxylic acid

Side chain

2-[1-[3,4-difluoro-2-[(2-fluoro-4-iodophenyl)aMino]benzoyl]-3-hydroxy-3-azetidinyl]

Stereochemistry

The compound has a 2R stereoisomer configuration, indicating the spatial arrangement of its atoms.

Fluorine atoms

Present at the 3rd and 4th positions of the phenyl ring in the side chain.

Iodine atom

Attached to the 4th position of the phenyl ring in the side chain.

Amine group

Part of the (2-fluoro-4-iodophenyl)aMino segment in the side chain.

Hydroxyl group

Located on the 3rd carbon of the azetidinyl side chain.

Ester group

Esterified with 1,1-diMethylethyl.

Potential applications

The compound may have pharmaceutical applications, but further research and testing are required to determine its specific uses and effects.

Upstream product

• 388077-74-5 rac-N-(tert-butoxycarbonyl)piperidine-2-carboxamide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4043-87-2 pipecolic Acid 
• 98303-20-9 1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid 
• 934666-39-4 (R,S) tert-butyl 2-(3-hydroxy-3-azetidinyl)-1-piperidinecarboxylate 
• 391211-97-5 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-benzoic acid 
• 934664-27-4 1,1-dimethylethyl 2-(3-hydroxy-1-{[(phenylmethyl)oxy]carbonyl}azetidin-3-yl)piperidine-1-carboxylate 
• 153749-89-4 2-cyanopiperidine-1-carboxylic acid tert-butyl ester 
• 109-04-6 2-bromo-pyridine 
• 833451-96-0 3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzoyl chloride 
• 1415560-00-7 C₁₀H₉F₃N₂O₂*ClH 
• 26250-84-0 (S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid 
• 934666-39-4 1,1-dimethylethyl (2S)-2-(3-hydroxyazetidin-3-yl)piperidine-1-carboxylate 
• 934665-53-9 1,1-dimethylethyl (2S)-2-(1-{[(phenylmethyl)oxy]carbonyl}-3-{[(2R)-3,3,3-trifluoro-2-(methyloxy)-2-phenylpropanoyl]oxy}azetidin-3-yl)piperidine-1-carboxylate 

Relevant academic research and scientific papers

PROCESS FOR THE PRODUCTION OF COBIMETINIB

The present invention relates to a novel route of synthesis for the production of enantiomerically pure Cobimetinib, new intermediates in the synthesis of Cobimetinib and an amorphous Cobimetinib hemifumarate salt comprising a high salt content.

Strain-Release-Driven Homologation of Boronic Esters: Application to the Modular Synthesis of Azetidines

Azetidines are important motifs in medicinal chemistry, but there are a limited number of methods for their synthesis. Herein, we present a new method for their modular construction by exploiting the high ring strain associated with azabicyclo[1.1.0]butane. Generation of azabicyclo[1.1.0]butyl lithium followed by its trapping with a boronic ester gives an intermediate boronate complex which, upon N-protonation with acetic acid, undergoes 1,2-migration with cleavage of the central C-N bond to relieve ring strain. The methodology is applicable to primary, secondary, tertiary, aryl, and alkenyl boronic esters and occurs with complete stereospecificity. The homologated azetidinyl boronic esters can be further functionalized through reaction of the N-H azetidine, and through transformation of the boronic ester. The methodology was applied to a short, stereoselective synthesis of the azetidine-containing pharmaceutical, cobimetinib.

A 3 - (piperidin - 2 - yl) - azetidine - 3 - ol derivatives of synthetic method and use thereof

The invention discloses a synthesis method of 3-(piperidyl-2-yl)-azetidinyl-3-ol derivatives and a method for synthesizing Cobimetinib from the compounds. The method comprises the following steps: by using compounds F as an initial raw material, carrying

Method for synthesizing S-3-(piperidine-2-yl)-azacyclo-azetidine-3-alcohol

The invention discloses a method for synthesizing S-3-(piperidine-2-yl)-azacyclo-azetidine-3-alcohol. The method comprises the following steps: condensing a compound S-N-Boc-piperidine-2-formic acid of a formula A and CDI so as to obtain a compound of a f

Novel carboxamide-based allosteric MEK inhibitors: Discovery and optimization efforts toward XL518 (GDC-0973)

The ERK/MAP kinase cascade is a key mechanism subject to dysregulation in cancer and is constitutively activated or highly upregulated in many tumor types. Mutations associated with upstream pathway components RAS and Raf occur frequently and contribute to the oncogenic phenotype through activation of MEK and then ERK. Inhibitors of MEK have been shown to effectively block upregulated ERK/MAPK signaling in a range of cancer cell lines and have further demonstrated early evidence of efficacy in the clinic for the treatment of cancer. Guided by structural insight, a strategy aimed at the identification of an optimal diphenylamine-based MEK inhibitor with an improved metabolism and safety profile versus PD-0325901 led to the discovery of development candidate 1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-[(2S) -piperidin-2-yl]azetidin-3-ol (XL518, GDC-0973) (1). XL518 exhibits robust in vitro and in vivo potency and efficacy in preclinical models with sustained duration of action and is currently in early stage clinical trials.

METHODS OF USING MEK INHIBITORS

The present invention provides methods of treating cancer by administering a compound of Formula (I), or a pharmaceutically acceptable salt or solvate thereof, in combination with other cancer treatments.

METHODS OF USING COMBINATIONS OF MEK AND JAK-2 INHIBITORS

A method of treating a disease in a mammal, comprising administering to the mammal a therapeutically effective amount of a MEK compound of Formula I(M), or a pharmaceutical composition comprising a therapeutically effective amount of a MEK compound of Formula I(M) and a pharmaceutically acceptable carrier, in combination with a therapeutically effective amount of a JAK-2 compound of Formula I(J), or a pharmaceutical composition comprising a therapeutically effective amount of a JAK-2 compound of Formula I(J) and a pharmaceutically acceptable carrier, wherein the MEK compound of Formula I(M) and JAK-2 compound of Formula I(J) are as defined in the specification.