89999-90-6

Usage

Chemical Properties

Light yellow crystalline

InChI:InChI=1/C7H4ClNO/c8-6-2-1-3-7(10)5(6)4-9/h1-3,10H

Upstream product

• 6575-07-1 2-chloro-6-nitrobenzonitrile 
• 18362-30-6 2-chloro-6-hydroxybenzaldehyde 
• 1056958-45-2 C₉H₆ClNO₂ 
• 668-45-1 2-chloro-6-fluorobenzonitrile 
• 92161-40-5 2-benzyloxy-6-chlorobenzonitrile 

Downstream Products

• 201467-03-0 6-chloro-2-hydroxy-3-nitrobenzonitrile 
• 198226-53-8 2-chloro-6-([(2R)-2-oxiranylmethyl]oxy)benzonitrile 
• 867040-04-8 (+/-)-2-chloro-6-(3-chloro-2-hydroxypropoxy)benzonitrile 
• 867040-05-9 Acetic acid (S)-2-(3-chloro-2-cyano-phenoxy)-1-chloromethyl-ethyl ester 
• 284035-33-2 NPS 2143 
• 1187330-93-3 2-chloro-6-(2-hydroxy-3-((2-methyl-1-(naphthalen-2-yl)propan-2-yl)amino)propoxy)benzonitrile 
• 198226-62-9 (+/-)-2-chloro-6-(oxiran-2-ylmethoxy)benzonitrile 
• 284035-33-2 2-Chloro-6-[(S)-3-(1,1-dimethyl-2-naphthalen-2-yl-ethylamino)-2-hydroxy-propoxy]-benzonitrile 
• 6575-10-6 2-Chlor-6-methoxybenzoesaeurenitril 
• 1638631-92-1 methyl 4-[(2-cyano-3-methoxyphenyl)amino]-2-(triisopropylsilyloxy)benzoate 
• 1638631-89-6 2-methoxy-6-[3-(triisopropylsilyloxy)phenylamino]benzonitrile 
• 1638631-88-5 7-benzyloxy-2-methoxy-6-methylcarbazole-1-carbaldehyde 

Relevant academic research and scientific papers

Discovery of CNS Penetrant CXCR2 Antagonists for the Potential Treatment of CNS Demyelinating Disorders

Structure-activity relationship exploration of the historical biarylurea series led to the identification of novel CNS penetrant CXCR2 antagonists with nanomolar potency, favorable PK profile, and good developability potentials. More importantly, the key

Chromatography-free entry to substituted salicylonitriles: Mitsunobu-triggered domino reactions of salicylaldoximes

A mild and efficient one-pot procedure is described to transform salicylaldoximes into salicylonitriles using Mitsunobu chemistry. The reactions proceed through the corresponding 1,2-benzisoxazoles that undergo the Kemp elimination in situ to generate the

Synthesis of the calcilytic ligand NPS 2143

(R)-3 (NPS 2143) is a negative allosteric modulator of the human calcium-sensing receptor (CaSR) and as such represents an important pharmacological tool compound for studying the CaSR. Herein, we disclose for the first time a complete experimental description, detailed characterisation and assessment of enantiomeric purity for (R)-3. An efficient, reproducible and scalable synthesis of (R)-3 that requires a minimum of chromatographic purification steps is presented. (R)-3 was obtained in excellent optical purity (er > 99:1) as demonstrated by chiral HPLC and the pharmacological profile for (R)-3 is in full accordance with that reported in the literature.

Antagonists of the calcium receptor I. Amino alcohol-based parathyroid hormone secretagogues

Functional screening of the former SmithKline Beecham compound collection against the human calcium receptor (CaR) resulted in the identification of the amino alcohol-based hit 2 (IC50 = 11 μM). Structure-activity studies of 2 focused on the optimization of the right- and left-hand side aromatic moieties as well as the amino alcohol linker region. Critical to the optimization of this antagonist template was the discovery that the chirality of the C-2 secondary alcohol played a key role in enhancing both CaR potency as well as selectivity over the β-adrenergic receptor subtypes. These SAR studies ultimately led to the identification of 38 (NPS 2143; SB-262470A), a potent and orally active CaR antagonist. Pharmacokinetic characterization of 38 in the rat revealed that this molecule had a large volume of distribution (11 L/kg), which resulted in a prolonged systemic exposure, protracted increases in the plasma levels of PTH, and an overall lack of net bone formation effect in a rodent model of osteoporosis.

Monoaryl-substituted salicylaldoximes as ligands for estrogen receptor β

Salicylaldoximes possess a hydrogen-bonded pseudocyclic A′ ring in place of the typical phenolic A ring that is characteristic of most estrogen receptor (ER) ligands. Monoaryl-substituted salicylaldoximes were obtained by replacing the phenol moiety (ring

Chemoenzymatic synthesis of calcilytic agent NPS-2143 employing a lipase-mediated resolution protocol

The kinetic resolution of chlorohydrin (±)-6 has been successfully carried out via a lipase-mediated transesterification with vinyl acetate in organic as well as ionic liquid media to yield (R)-alcohol 6 and (S)-acetate 7 in high enantioselectivity. An en

Evaluation of Potent and Selective Small-Molecule Antagonists for the CXCR2 Chemokine Receptor

N,N′-Diarylureas were prepared, and the structure-activity relationship relative to the CXCR2 receptor was examined. This led to the identification of a potent and highly selective CXCR2 antagonist, which in addition was shown to be functionally active bo

Discovery of potent and orally bioavailable N,N′-diarylurea antagonists for the CXCR2 chemokine receptor

A series of 3-substituted N,N′-diarylureas was prepared and CXCR2 receptor affinities as well as pharmacokinetic properties were examined. A series of 3-substituted N,N′-diarylureas was prepared and the structure-activity relationship relative to CXCR2 re

IL-8 RECEPTOR ANTAGONISTS

Novel IL-8 receptor antagonists and methods of using them are provided.

Method of using calcilytic compounds

The present invention features calcilytic compounds. "Calcilytic compounds" refer to compounds able to inhibit calcium receptor activity. Also described are the use of calcilytic compounds to inhibit calcium receptor activity and/or achieve a beneficial effect in a patient; and techniques which can be used to obtain additional calcilytic compounds.