934666-39-4

Usage

Uses

Used in Pharmaceutical Industry:
1,1-DiMethylethyl (2S)-2-(3-hydroxyazetidin-3-yl)piperidine-1-carboxylate serves as a potential drug candidate due to its structural complexity and the presence of the hydroxyazetidin group, which is known for its pharmacological properties. It may be developed into a therapeutic agent targeting specific biological pathways or used as a precursor in the synthesis of other medicinal compounds.
Used in Medicinal Chemistry Research:
As a derivative of piperidine with a unique hydroxyazetidin group, 1,1-DiMethylethyl (2S)-2-(3-hydroxyazetidin-3-yl)piperidine-1-carboxylate is utilized in medicinal chemistry for the exploration of new chemical entities. Researchers may investigate its interactions with biological targets, its potential therapeutic effects, and its role as a building block for the creation of novel pharmaceuticals.
Used in Drug Synthesis:
1,1-DiMethylethyl (2S)-2-(3-hydroxyazetidin-3-yl)piperidine-1-carboxylate may also be employed as an intermediate in the synthesis of other pharmaceutical compounds. Its unique structure can be further modified or used to create new molecules with specific therapeutic properties, contributing to the development of innovative treatments for various medical conditions.

Upstream product

• 1415560-00-7 C₁₀H₉F₃N₂O₂*ClH 
• 109-04-6 2-bromo-pyridine 
• 934664-27-4 1,1-dimethylethyl 2-(3-hydroxy-1-{[(phenylmethyl)oxy]carbonyl}azetidin-3-yl)piperidine-1-carboxylate 
• 934665-52-8 1,1-dimethylethyl (2R)-2-(1-{[(phenylmethyl)oxy]carbonyl}-3-{[(2R)-3,3,3-trifluoro-2-(methyloxy)-2-phenylpropanoyl]oxy}azetidin-3-yl)piperidine-1-carboxylate 
• 934665-54-0 1,1-dimethylethyl (2R)-2-(3-hydroxy-1-{[(phenylmethyl)oxy]carbonyl}azetidin-3-yl)piperidine-1-carboxylate 
• 26250-84-0 (S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid 
• 28697-17-8 N-BOC-D-pipecolic acid 
• 3105-95-1 pipecolinic acid 
• 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 
• 934665-55-1 1,1-dimethylethyl (2S)-2-(3-hydroxy-1-{[(phenylmethyl)oxy]carbonyl}azetidin-3-yl)piperidine-1-carboxylate 
• 388077-74-5 rac-N-(tert-butoxycarbonyl)piperidine-2-carboxamide 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 934662-91-6 cobimetinib 
• 934665-56-2 tert-butyl (S)-2-{1-[3,4-difluoro-2-(2-fluoro-4-iodophenylamino)benzoyl]-3-hydroxy-3-azetidinyl}perhydropyridine-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.

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

Synthesis method of cobimetinib

The invention discloses a synthesis method of cobimetinib. The method comprises the following steps: respectively carrying out salt forming reaction and bromination reaction on (R)-N-Boc-2-piperidinecarboxylic acid, silver nitrate (or mercuric oxide) and

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

Preparation method of cobimetinib

The invention discloses a preparation method of cobimetinib (Cobimetinib, XL518, GDC-0973) (I). The method includes the preparation steps of preparing an intermediate [2-oxo-2-((2S)-1-t-butyloxycarboryl-2-based]acetate through acyl cyanide formation, hydrolysis, esterification and Boc prortection with (2S)-2-pipecolic acid as the raw material, preparing an intermediate (2S)-1-t-butyloxycarboryl-2-(3-azetidinol-3-based)piperidine by conducting the addition reaction, the reduction action and the cyclization reaction on the intermediate body, and making the intermediate (2S)-1-t-butyloxycarboryl-2-(3-azetidinol-3-based)piperidine and a side chain subjected to a condensation reaction to obtain the cobimetinib (I). According to the preparation method, raw materials can be easily obtained, the process is simple, and the method is economical, environmentally friendly and suitable for industrialized production.

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.

NOVEL 6-ARYLAMINO PYRIDONE CARBOXAMIDE AS MEK INHIBITORS

The invention provides novel substituted 6-arylamino pyridone carboxamides represented by Formula I, or a pharmaceutically acceptable salt, solvate, poly- morph, ester, tautomer or prodrug thereof, and a composition comprising these compounds. The compounds provided can be used as inhibitors of MEK and are useful in the treatment of inflammatory diseases, cancer and other hyperproliferative diseases. The invention further provides a method of treatment for inflammatory diseases, cancer and other hyperproliferative diseases in mammals, especially humans.

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.