1083057-12-8

Basic information

• Product Name: tert-butyl 3-(3-methylpyridin-2-yl)benzoate
• Synonyms: tert-butyl 3-(3-methylpyridin-2-yl)benzoate;Benzoic acid, 3-(3-Methyl-2-pyridinyl)-, 1,1-diMethylethyl ester;3-(3-Methyl-2-pyridinyl)benzoic acid 1,1-dimethylethyl ester
• CAS NO: 1083057-12-8
• Molecular Formula: C17H19NO2
• Molecular Weight: 269
• Mol File: 1083057-12-8.mol

Chemical Properties

• Boiling Point: 386.8±30.0 °C(Predicted)
• Appearance: /
• Density: 1.070±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 4.34±0.22(Predicted)
• CAS DataBase Reference: tert-butyl 3-(3-methylpyridin-2-yl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 3-(3-methylpyridin-2-yl)benzoate(1083057-12-8)
• EPA Substance Registry System: tert-butyl 3-(3-methylpyridin-2-yl)benzoate(1083057-12-8)

Safety Data

• Hazardous Substances Data: 1083057-12-8(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
Tert-butyl 3-(3-methylpyridin-2-yl)benzoate is used as a fragrance ingredient for its characteristic sweet or fruit-like odor, adding pleasant scents to various products.
Used in Flavor Industry:
In the flavor industry, tert-butyl 3-(3-methylpyridin-2-yl)benzoate is utilized as a flavoring agent, contributing to the taste profiles of food and beverages.
Used in Chemical Synthesis:
This aromatic ester serves as an intermediate in the synthesis of various organic compounds, particularly in the pharmaceutical and agrochemical sectors, due to its unique structural features.
Used in Stabilizer Formulations:
Due to the resistance to oxidation and degradation of the tertiary butyl group, tert-butyl 3-(3-methylpyridin-2-yl)benzoate can be used as a component in stabilizer formulations to protect materials from oxidative degradation.

Upstream product

• 3430-17-9 2-bromo-3-picoline 
• 75-75-2 methanesulfonic acid 
• 220210-56-0 3-(tert-butoxycarbonyl)phenylboronic acid 

Downstream Products

• 1083057-13-9 tert-butyl 3-(3-methyl-1-oxo-1λ-pyridin-2-yl)benzoate 
• 1083057-14-0 tert-butyl 3-(6-amino-3-methylpyridin-2-yl)benzoate 
• 1160221-25-9 tert-butyl 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamido)-3-methylpyridin-2-yl)benzoate 
• 1160221-26-0 Lumacaftor hydrochloride 
• 936727-05-8 Lumacaftor 

Relevant articles and documents

METHODS OF TREATMENT FOR CYSTIC FIBROSIS

This application describes methods of treating cystic fibrosis or a CFTR mediated disease comprising administering Compound I or a pharmaceutically acceptable salt thereof. (I) The application also describes pharmaceutical compositions comprising Compound I or a pharmaceutically acceptable salt thereof and optionally comprising one or more additional CFTR modulating agents.

Evaluation of 1,2,3-Triazoles as Amide Bioisosteres In Cystic Fibrosis Transmembrane Conductance Regulator Modulators VX-770 and VX-809

The 1,2,3-triazole has been successfully utilized as an amide bioisostere in multiple therapeutic contexts. Based on this precedent, triazole analogues derived from VX-809 and VX-770, prominent amide-containing modulators of the cystic fibrosis transmembrane conductance regulator (CFTR), were synthesized and evaluated for CFTR modulation. Triazole 11, derived from VX-809, displayed markedly reduced efficacy in F508del-CFTR correction in cellular TECC assays in comparison to VX-809. Surprisingly, triazole analogues derived from potentiator VX-770 displayed no potentiation of F508del, G551D, or WT-CFTR in cellular Ussing chamber assays. However, patch clamp analysis revealed that triazole 60 potentiates WT-CFTR similarly to VX-770. The efficacy of 60 in the cell-free patch clamp experiment suggests that the loss of activity in the cellular assay could be due to the inability of VX-770 triazole derivatives to reach the CFTR binding site. Moreover, in addition to the negative impact on biological activity, triazoles in both structural classes displayed decreased metabolic stability in human microsomes relative to the analogous amides. In contrast to the many studies that demonstrate the advantages of using the 1,2,3-triazole, these findings highlight the negative impacts that can arise from replacement of the amide with the triazole and suggest that caution is warranted when considering use of the 1,2,3-triazole as an amide bioisostere.

METHODS OF TREATMENT FOR CYSTIC FIBROSIS

Compound I of the formula (I) and/or pharmaceutically acceptable salt(s) of Compound I comprised in a pharmaceutical composition and methods of using the same to treat cystic fibrosis.

PHARMACEUTICAL COMPOSITIONS OF 3-(6-(1-(2,2-DIFLUOROBENZO[D][1,3]DIOXOL-5-YL)CYCLOPROPANECARBOXAMIDO)-3-METHYLPYRIDIN-2-YL)BENZOIC ACID AND ADMINISTRATION THEREOF

A pharmaceutical composition comprising Compound 1,(3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid), and at least one excipient selected from: a filler, a diluent, a disintegrant, a surfactant, a binder, a glidant and a lubricant, the composition being suitable for oral administration to a patient in need thereof to treat a CFTR mediated disease such as Cystic Fibrosis. Methods for treating a patient in need thereof include administering an oral pharmaceutical formulation of Compound 1 to the patient.

MODULATOR OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR, PHARMACEUTICAL COMPOSITIONS, METHODS OF TREATMENT, AND PROCESS FOR MAKING THE MODULATOR

Compounds of Formula (I) pharmaceutically acceptable salts thereof, deuterated derivatives of any of the foregoing, and metabolites of any of the foregoing are disclosed. Pharmaceutical compositions comprising the same, methods of treating cystic fibrosis using the same, and methods for making the same are also disclosed. Also disclosed are solid state forms of Compound 1 and salts and solvates thereof.

PROCESS FOR THE PREPARATION OF LUMACAFTOR

The present disclosure relates to processes for the preparation of lumacaftor useful for treating a cystic fibrosis transmembrane conductance regulator (CFTR)-mediated disease such as cystic fibrosis. The present disclosure also provides intermediates useful in the preparation of lumacaftor

Pharmaceutical compositions of 3-(6-(1-(2,2-difluorobenzo[D][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid and administration thereof

A pharmaceutical composition comprising Compound 1, (3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid), and at least one excipient selected from: a filler, a diluent, a disintegrant, a surfactant, a binder, a glidant and a lubricant, the composition being suitable for oral administration to a patient in need thereof to treat a CFTR mediated disease such as Cystic Fibrosis. Methods for treating a patient in need thereof include administering an oral pharmaceutical formulation of Compound 1 to the patient.

FORMULATIONS OF 3-(6-(1-(2,2-DIFLUOROBENZO[D][1,3]DIOXOL-5-YL) CYCLOPROPANECARBOXAMIDO)-3-METHYLPYRIDIN-2-YL)BENZOIC ACID

A pharmaceutical composition comprising Compound 1, (3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid), and at least one excipient selected from: a filler, a disintegrant, a surfactant, a binder, and a lubricant, the composition being suitable for oral administration to a patient in need thereof to treat a CFTR mediated disease such as Cystic Fibrosis. Processes of preparing pharmaceutical compositions comprising Compound 1 are also disclosed.

PROCESS OF PREPARING PHARMACEUTICAL COMPOSITIONS FOR THE TREATMENT OF CFTR MEDIATED DISEASES

Processes of preparing pharmaceutical compositions comprising 3-(6-(1-(2,2- difluorobenzo[d][1,3] dioxol-5 -yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid (Compound 1) in Form I and a solid dispersion comprising substantially amorphous N-(5- hydroxy-2,4-ditert-butyl-phenyl)-4-oxo-lH-quinoline-3-carboxamide (Compound 2), methods of treating, lessening the severity of, or symptomatically treating CFTR mediated diseases, such as cystic fibrosis, methods of administering, and kits thereof are disclosed.

Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases

The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.