213672-66-3

Usage

InChI:InChI=1/C15H21NO3/c17-10-13-8-4-5-9-14(13)16-15(18)19-11-12-6-2-1-3-7-12/h1-3,6-7,13-14,17H,4-5,8-11H2,(H,16,18)/t13-,14-/m1/s1

Upstream product

• 89854-92-2 (1R,2R)-(2-Amino-cyclohexyl)-methanol 
• 501-53-1 benzyl chloroformate 
• 5691-37-2 (+/-)-trans-2-hydroxymethyl-1-cyclohexylamine hydrochloride 
• 29586-59-2 trans-2-hydroxymethylcyclohexylamine 
• 109087-15-2 cis-2-hydroxymethylcyclohexylamine 
• 178112-24-8 [(1R,2R)-2-((R)-1-Phenyl-ethylamino)-cyclohexyl]-methanol 
• 163877-12-1 (R,R,R)-2--1-carbethoxycyclohexane 
• 163705-86-0 (1S,2R,αR)-2--1-carbethoxycyclohexane 
• 121506-74-9 ethyl (-)-N-<(R)-1-phenylethyl>-1-aminocyclohexene-2-carboxylate 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 100-51-6 benzyl alcohol 
• 13149-00-3 1,2-cis-cyclohexanedicarboxylic anhydride 
• 17488-76-5 C₁₀H₁₆O₄ 
• 17488-76-5 (1S,2R)-Cyclohexane-1,2-dicarboxylic acid monoethyl ester 

Downstream Products

• 275812-32-3 N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-N'-((1R,2S)-2-{[3(S)-(4-fluorobenzyl)piperidinyl]methyl}cyclohexyl)urea 
• 213672-66-3 ((1S,2R)-2-Hydroxymethyl-cyclohexyl)-carbamic acid benzyl ester 
• 213672-84-5 trans-(1R,2R)-1-(benzyloxycarbonylamino)-2-hydroxymethyl-cyclohexane 
• 852660-37-8 N-((1R,2S)-2-{[tert-butoxycarbonyl[3-(4-fluorophenyl)propyl]amino]methyl}cyclohexyl)-N'-[3-(1-methyl-1H-tetrazol-5-yl)phenyl]urea 
• 852660-52-7 N-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-N'-((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino]methyl}cyclohexyl)urea 
• 852660-57-2 N-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-N'-((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)(methyl)amino]methyl}cyclohexyl)urea 
• 852660-58-3 benzyl ((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)(methyl)amino]methyl}cyclohexyl)carbamate 
• 852660-36-7 (1R,2S)-2-({tert-butoxycarbonyl-[3-(4-fluorophenyl)-propyl]amino}-methyl)-cyclohexylamine 
• 852660-59-4 N-(2RS)-{[(1S,2R)-2-aminocyclohexyl]methyl}-6-fluoro-N-methyl-1,2,3,4-tetrahydronaphthalen-2-amine 
• 852660-56-1 N-{[(1S,2R)-2-aminocyclohexyl]methyl}-(2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-amine 
• 852660-41-4 (1R,2S)-2-({[3-(4-fluorophenyl)-propyl]-methyl-amino}-methyl)-cyclohexylamine 
• 852660-38-9 N-((1R,2S)-2-{[[3-(4-fluorophenyl)propyl](methyl)amino]methyl}cyclohexyl)-N'-[3-(1-methyl-1H-tetrazol-5-yl)phenyl]urea 
• 852660-32-3 N-((1R,2S)-2-{[[3-(4-fluorophenyl)propyl]amino]methyl}cyclohexyl)-N'-[3-(1-methyl-1H-tetrazol-5-yl)phenyl]urea 

Relevant academic research and scientific papers

Novel Compounds

Compounds of Formulae I, or pharmaceutically acceptable salts thereof: wherein X, R1, R2 and R3 are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

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-AMINO COMPOUNDS 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.

Piperidine amides as modulators of chemo kine 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.

Enzymatic resolution of alicyclic 1,3-amino alcohols in organic media

Racemic cis- and trans-2-aminocyclohexane-1-methanol and cis- and trans- 2-amino-4-cyclohexene-1-methanol were resolved via lipase-catalysed O- acylation of their Z derivatives, using vinyl butyrate in different ether solvents. In accordance with the empi