232275-49-9

Basic information

• Product Name: Methyl 2,6-dichloro-4-aminobenzoate
• Synonyms: Methyl 2,6-dichloro-4-aminobenzoate;4-AMino-2,6-dichlorobenzoic acid Methyl este;4-Amino-2,6-dichlorobenzoic acid methyl ester;Methyl 4-amino-2,6-dichlorobenzoate;methyl4-amino-2,6-dichlorobenzoate(WX192023)
• CAS NO: 232275-49-9
• Molecular Formula: C₈H₇Cl₂NO₂
• Molecular Weight: 220.05268
• Mol File: 232275-49-9.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 367.9±37.0 °C(Predicted)
• Appearance: /
• Density: 1.433
• Storage Temp.: 2-8°C(protect from light)
• PKA: 0.35±0.10(Predicted)
• CAS DataBase Reference: Methyl 2,6-dichloro-4-aminobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,6-dichloro-4-aminobenzoate(232275-49-9)
• EPA Substance Registry System: Methyl 2,6-dichloro-4-aminobenzoate(232275-49-9)

Safety Data

• Hazardous Substances Data: 232275-49-9(Hazardous Substances Data)

Upstream product

• 232275-50-2 methyl 2,6-dichloro-4-nitrobenzoate 
• 86569-78-0 methyl 2,4,6-trichlorobenzoate 
• 67-56-1 methanol 
• 22509-50-8 2,6-dichloro-4-nitrobenzoic acid 
• 50-43-1 2,4,6-trichlorobenzoic acid 
• 99-99-0 1-methyl-4-nitrobenzene 
• 7149-69-1 1,3-dichloro-2-methyl-5-nitrobenzene 
• 1098619-84-1 trifluoro-methanesulfonic acid 4-tert-butoxycarbonylamino-2,6-dichloro-phenyl ester 
• 5930-28-9 4-amino-2,6-dichlorophenol 
• 155891-93-3 (3,5-Dichloro-4-hydroxy-phenyl)-carbamic acid tert-butyl ester 
• 409127-35-1 4-tert-butoxycarbonylamino-2,6-dichloro-benzoic acid methyl ester 
• 88135-16-4 2,6-dichloro-4-nitrobenzoyl chloride 

Downstream Products

• 1613730-11-2 methyl 4-amino-2,6-dichloro-3-iodobenzoate 
• 1613730-12-3 methyl 4-amino-2,6-dichloro-3-((trimethylsilyl)ethynyl)benzoate 

Relevant articles and documents

Definitive Metabolite Identification Coupled with Automated Ligand Identification System (ALIS) Technology: A Novel Approach to Uncover Structure-Activity Relationships and Guide Drug Design in a Factor IXa Inhibitor Program

A potent and selective Factor IXa (FIXa) inhibitor was subjected to a series of liver microsomal incubations, which generated a number of metabolites. Using automated ligand identification system-affinity selection (ALIS-AS) methodology, metabolites in the incubation mixture were prioritized by their binding affinities to the FIXa protein. Microgram quantities of the metabolites of interest were then isolated through microisolation analytical capabilities, and structurally characterized using MicroCryoProbe heteronuclear 2D NMR techniques. The isolated metabolites recovered from the NMR experiments were then submitted directly to an in vitro FIXa enzymatic assay. The order of the metabolites' binding affinity to the Factor IXa protein from the ALIS assay was completely consistent with the enzymatic assay results. This work showcases an innovative and efficient approach to uncover structure-activity relationships (SARs) and guide drug design via microisolation-structural characterization and ALIS capabilities.

A convenient synthesis of a lymphocyte function-associated antigen-1 (LFA-1) antagonist of 'Compound 4'

The lymphocyte function-associated antigen-1 (LFA-1) antagonist of 'Compound 4' was synthesised by a convenient route using cheap, commercially available starting materials and catalysts under mild reaction conditions and by easily handled reactions. The total yield in the preparation of 'Compound 4' was more than 38% via Sonogashira coupling of an iodide and an alkyne, reduction of the alkyne catalysed by Raney nickel and later steps involving hydrolysis of an ester, condensation of an acid and an amine and a final hydrolysis of an ester.

A kind of the second aryl amine derivative and its preparation method, pharmaceutical composition and use thereof

The invention provides diarylamide type derivatives having a structure shown as a formula (I) as follows, or pharmaceutically acceptable salts thereof, a preparing method of the derivatives, compositions containing the derivatives and the pharmaceutically acceptable salts, and medicine uses of the derivatives and the pharmaceutically acceptable salts. The diarylamide type derivatives having the structure shown as the formula (I) or the pharmaceutically acceptable salts thereof have antagonistic effects on FXR. Integral animal experiments show that the compounds have effects of decreasing blood sugar and reducing blood fat. The compounds can be used for treating hyperlipidemia and type 2 diabetes mellitus.

Identification of an imidazopyridine scaffold to generate potent and selective TYK2 inhibitors that demonstrate activity in an in vivo psoriasis model

Herein we report identification of an imidazopyridine class of potent and selective TYK2 inhibitors, exemplified by prototype 6, through constraint of the rotatable amide bond connecting the pyridine and aryl rings of compound 1. Further optimization led to generation of compound 30 that potently inhibits the TYK2 enzyme and the IL-23 pathway in cells, exhibits selectivity against cellular JAK2 activity, and has good pharmacokinetic properties. In mice, compound 30 demonstrated dose-dependent reduction of IL-17 production in a PK/PD model as well as in an imiquimod-induced psoriasis model. In this efficacy model, the IL-17 decrease was accompanied by a reduction of ear thickness indicating the potential of TYK2 inhibition as a therapeutic approach for psoriasis patients.

Preparation of fluorous Yamaguchi reagents and evaluation of their reactivity in esterification

Fluorous Yamaguchi (FY) reagents bearing a perfluoroalkyl chain were prepared and employed in esterification reactions; the yields were similar to those obtained with the traditional Yamaguchi (TY) reagent. Fluorous benzoic acids derived from the FY reagents were separated easily after the reaction. GC analysis revealed that the initial rates of reaction with the FY reagents were higher than those with the TY reagent. The acidities of benzoic acids produced from the FY and TY reagents were predicted by DFT to be similar (1.20 and 0.96, respectively).

FACTOR IXA INHIBITORS

In its many embodiments, the present invention provides a novel class of benzamide compounds represented by Formula (I) or pharmaceutically acceptable salts or solvates thereof, or pharmaceutical compositions comprising one or more said compounds or pharmaceutically acceptable salts or solvates thereof, and methods for using said compounds or pharmaceutically acceptable salts or solvates thereof for treating or preventing a thromboses, embolisms, hypercoagulability or fibrotic changes.

INDOLE CARBOXAMIDE DERIVATIVES AS P2X7 RECEPTOR ANTAGONISTS

The invention relates to indole carboxamide derivatives of formula (I), wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10 and n are as defined in the description, their preparation and their use as pharmaceutically active compounds.

Lead optimization of a 4-aminopyridine benzamide scaffold to identify potent, selective, and orally bioavailable TYK2 inhibitors

Herein we report our lead optimization effort to identify potent, selective, and orally bioavailable TYK2 inhibitors, starting with lead molecule 3. We used structure-based design to discover 2,6-dichloro-4-cyanophenyl and (1R,2R)-2-fluorocyclopropylamide modifications, each of which exhibited improved TYK2 potency and JAK1 and JAK2 selectivity relative to 3. Further optimization eventually led to compound 37 that showed good TYK2 enzyme and interleukin-12 (IL-12) cell potency, as well as acceptable cellular JAK1 and JAK2 selectivity and excellent oral exposure in mice. When tested in a mouse IL-12 PK/PD model, compound 37 showed statistically significant knockdown of cytokine interferon-γ (IFNγ), suggesting that selective inhibition of TYK2 kinase activity might be sufficient to block the IL-12 pathway in vivo.

IMIDAZOPYRIDINE COMPOUNDS, COMPOSITIONS AND METHODS OF USE

The invention provides compounds of Formulas Ia-Ib, stereoisomers or pharmaceutically acceptable salts thereof, wherein A, X, R1, R2, R4, R5 and R16 are defined herein, a pharmaceutical composition that includes a compound of Formulas Ia-Ib and a pharmaceutically acceptable carrier, adjuvant or vehicle, and methods of using the compound or composition in therapy.

JANUS KINASE INHIBITOR COMPOUNDS AND METHODS

The invention provides compounds of Formula I, stereoisomers or pharmaceutically acceptable salts thereof, wherein A, B, D, R1, R2, R4 and R5 are defined herein, a pharmaceutical composition that includes a compound of Formula I and methods of use thereof