382637-99-2

Upstream product

• 102-09-0 bis(phenyl) carbonate 
• 30748-47-1 5-acetyl-4-methylthiazole-2-amine 
• 1885-14-9 phenyl chloroformate 
• 1694-29-7 3-chloropentane-2,4-dione 

Downstream Products

• 275812-32-3 1-(5-Acetyl-4-methyl-thiazol-2-yl)-3-{(1R,2S)-2-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-cyclohexyl}-urea 
• 388109-48-6 (3S,4S)-3-amino-4-[(S)-3-(4-fluorobenzyl)-piperidin-1-ylmethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 388097-48-1 (3R,4R)-4-[3-(5-acetyl-4-methyl-thiazol-2-yl)-ureido]-3-[(S)-3-(4-fluoro-benzyl)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid t-butyl ester 
• 388101-50-6 C₃₀H₄₂FN₅O₄S 
• 388105-01-9 C₂₉H₄₀FN₅O₄S 
• 676621-35-5 1-(5-acetyl-4-methylthiazol-2-yl)-3-{1-[2-(4-fluorophenyl)ethyl]-piperidin-3-ylmethyl}urea 
• 503186-98-9 N-(5-Acetyl-4-methyl-thiazol-2-yl)-N'-{(1R,2S)-2-[(5S)-5-(4-fluoro-benzyl)-3-oxo-piperazin-1-yl-methyl]-cyclohexyl}-urea 
• 935853-15-9 1-(5-acetyl-4-methylthiazol-2-yl)-3-{4-[(4-fluorobenzyl)methylamino]butyl}urea 
• 852660-68-5 N-(5-acetyl-4-methyl-thiazol-2-yl)-N'-[(1R,2S,5R)-5-(N-methyl)acetamido-2-[N-methyl-3-(4-fluorophenyl)propylamino]methyl-cyclohexyl]urea 
• 852660-69-6 N-(5-acetyl-4-methyl-thiazol-2-yl)-N'-[(1R,2S,5S)-5-(N-methyl)acetamido-2-[N-methyl-3-(4-fluorophenyl)propylamino]methyl-cyclohexyl]urea 
• 852660-83-4 N-((1R,3R,4S)-3-({[(5-acetyl-4-methyl-1,3-thiazol-2-yl)amino]carbonyl}amino)-4{[3-(4-fluorophenyl)propyl(propyl)amino]methyl}cyclohexyl)-N-methylacetamide 
• 852660-84-5 N-((1S,3R,4S)-3-({[(5-acetyl-4-methyl-1,3-thiazol-2-yl)amino]carbonyl}amino)-4{[3-(4-fluorophenyl)propyl(propyl)amino]methyl}cyclohexyl)-N-methylacetamide 
• 852661-21-3 N-((1R,3S,4R)-4-({[(5-acetyl-4-methyl-1,3-thiazol-2-yl)amino]carbonyl}amino)-3-{[[3-(4-fluorophenyl)propyl](methyl)amino]methyl}cyclohexyl)-N-methylacetamide 
• 852661-22-4 N-((1S,3S,4R)-4-({[(5-acetyl-4-methyl-1,3-thiazol-2-yl)amino]carbonyl}amino)-3-{[[3-(4-fluorophenyl)propyl](methyl)amino]methyl}cyclohexyl)-N-methylacetamide 

Relevant academic research and scientific papers

Discovery of Multitarget Agents Active as Broad-Spectrum Antivirals and Correctors of Cystic Fibrosis Transmembrane Conductance Regulator for Associated Pulmonary Diseases

Enteroviruses (EVs) are among the most frequent infectious agents in humans worldwide and represent the leading cause of upper respiratory tract infections. No drugs for the treatment of EV infections are currently available. Recent studies have also linked EV infection with pulmonary exacerbations, especially in cystic fibrosis (CF) patients, and the importance of this link is probably underestimated. The aim of this work was to develop a new class of multitarget agents active both as broad-spectrum antivirals and as correctors of the F508del-cystic fibrosis transmembrane conductance regulator (CFTR) folding defect responsible for >90% of CF cases. We report herein the discovery of the first small molecules able to simultaneously act as correctors of the F508del-CFTR folding defect and as broad-spectrum antivirals against a panel of EVs representative of all major species.

ARYLUREA DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

A compound of formula (I), wherein substituents are as given above, useful in the treatment of a disease mediated by the action of CCR3, in particular inflammatory or obstructive airway diseases.

Stereoselective process for a CCR3 antagonist

A convergent, multikilogram, stereoselective synthesis of 1 is described. A key fragment, (S)-3-(4-fluorobenzyl)piperidine (2) was synthesized from valerolactam in three steps using our recently discovered Ir-BDPP-catalyzed asymmetric hydrogenation. Anoth

Discovery of CC chemokine receptor-3 (CCR3) antagonists with picomolar potency

Starting with our previously described20 class of CC chemokine receptor-3 (CCR3) antagonist, we improved the potency by replacing the phenyl linker of 1 with a cyclohexyl linker and by replacing the 4-benzylpiperidine with a 3-benzylpiperidine. The resulting compound, 32, is a potent and selective antagonist of CCR3. SAR studies showed that the 3-acetylphenyl urea of 32 could be replaced with heterocyclic ureas or heterocyclic-substituted phenyl ureas and still maintain the potency (inhibition of eotaxin-induced chemotaxis) of this class of compounds in the low-picomolar range (IC50 = 10-60 pM), representing some of the most potent CCR3 antagonists reported to date. The potency of 32 for mouse CCR3 (chemotaxis IC50 = 41 nM) and its oral bioavailability in mice (20% F) were adequate to assess the efficacy in animal models of allergic airway inflammation. Oral administration of 32 reduced eosinophil recruitment into the lungs in a dose-dependent manner in these animal models. On the basis of its overall potency, selectivity, efficacy, and safety profile, the benzenesulfonate salt of 32, designated DPC168, entered phase I clinical trials.

N-ureidoalkyl-piperidines as modulators of chemokine receptor activity

The present application describes modulators of chemokine receptor activity of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases, as well as autoimmune pathologies such as rheum

N-substituted heterocyclic amines as modulators of chemokine receptor activity

The present application describes modulators of chemokine receptors of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.

Piperizinones as modulators of chemokine receptor activity

The present application describes modulators of CCR3 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.

N-ureidoheterocycloalkyl-piperidines as modulators of chemokine receptor activity

The present application describes modulators of CCR3 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.