239074-29-4

Usage

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL TRANS-(4-HYDROXYMETHYL)CYCLOHEXYLCARBAMATE is used as a key intermediate in the synthesis of C-2 hydroxyethyl imidazopyrrolo pyridines, which are JAK1 inhibitors. These inhibitors play a crucial role in the development of treatments for various inflammatory and autoimmune diseases by targeting the JAK/STAT signaling pathway.
Additionally, TERT-BUTYL TRANS-(4-HYDROXYMETHYL)CYCLOHEXYLCARBAMATE is utilized in the preparation of Mer kinase inhibitors. These inhibitors are specifically designed for the treatment of pediatric acute lymphoblastic leukemia, a type of cancer that predominantly affects children and young adults. By targeting the Mer kinase pathway, these inhibitors aim to halt the uncontrolled growth of cancer cells and provide a potential therapeutic option for patients suffering from this aggressive form of leukemia.

InChI:InChI=1/C12H23NO3/c1-12(2,3)16-11(15)13-10-6-4-9(8-14)5-7-10/h9-10,14H,4-8H2,1-3H3,(H,13,15)/t9-,10-

Upstream product

• 130309-46-5 trans-4-(tert-butoxycarbonylamino)cyclohexane carboxylic acid 
• 146307-51-9 methyl (1R,4R)-4-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate 
• 62456-15-9 methyl trans-4-amino-cyclohexanecarboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 50-00-0 formaldehyd 
• 15177-67-0 trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid 
• 1776-53-0 trans-4-aminocyclohexanecarboxylic acid 
• 1467-84-1 ((1R,4R)-4-aminocyclohexyl)methanol 
• 53292-90-3 trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid 
• 128699-69-4 C₉H₁₅NO₄ 
• 27960-59-4 trans-4-aminocyclohexanecarboxylic acid hydrochloric acid 

Downstream Products

• 181308-57-6 trans-(4-formyl-cyclohexyl)-carbamic acid tert-butyl ester 
• 1021919-05-0 C₁₃H₂₅NO₃ 
• 683269-95-6 N-[trans-4-[[(methylsulfonyl)oxy]methyl]cyclohexyl]carbamic acid tert-butyl ester 
• 1207529-80-3 {(1r,4r)-4-[(tert-butoxycarbonyl)amino]cyclohexyl}methyl trifluoromethanesulfonate 
• 1319743-42-4 trans-N-[4-(3,3-dimethyl-2-oxo-2,3-dihydro-indol-1-ylmethyl)-cyclohexyl]-4-fluoro-3-trifluoromethyl-benzamide 
• 1319743-51-5 trans-1-(4-amino-cyclohexylmethyl)-3,3-dimethyl-1,3-dihydro-indol-2-one 
• 1313279-47-8 trans-(4-cyanomethyl-cyclohexyl)-carbamic acid tert-butyl ester 
• 1313279-48-9 2-((1r,4r)-4-aminocyclohexyl)acetonitrile hydrochloride 
• 506427-91-4 trans N-tert-butoxycarbonyl-4-{2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]ethyl}-cyclohexylamine 
• 791778-53-5 trans-4-(2-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethyl)cyclohexane-1-amine 
• 215790-29-7 trans-2-(1-(4-(N-tert-butoxycarbonyl)amino)cyclohexyl)acetaldehyde 
• 1418002-46-6 C₁₉H₂₂N₆O₂S 
• 1418003-25-4 trans-[4-(2-aminomethyl-1,3,5,9-tetraaza-cyclopenta[a]naphthalen-1-yl)-cyclohexyl]-acetonitrile 
• 1418003-24-3 trans-[1-(4-cyanomethyl-cyclohexyl)-1H-1,3,5,9-tetraaza-cyclopenta[a]naphthalen-2-ylmethyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Radical hydroxymethylation of alkyl iodides using formaldehyde as a C1 synthon

Radical hydroxymethylation using formaldehyde as a C1 synthon is challenging due to the reversible and endothermic nature of the addition process. Here we report a strategy that couples alkyl iodide building blocks with formaldehyde through the use of photocatalysis and a phosphine additive. Halogen-atom transfer (XAT) from α-aminoalkyl radicals is leveraged to convert the iodide into the corresponding open-shell species, while its following addition to formaldehyde is rendered irreversible by trapping the transient O-radical with PPh3. This event delivers a phosphoranyl radical that re-generates the alkyl radical and provides the hydroxymethylated product.

PYRIMIDINYL GROUP-CONTAINING TRICYCLIC COMPOUND SERVING AS C-MET INHIBITOR

Disclosed are a pyrimidinyl group-containing tricyclic compound and applications thereof in preparing a cancer-treating medicament. Specifically disclosed are a compound as represented by formula (I), a pharmaceutically acceptable salt of same, or an isomer thereof.

Discovery of a Gut-Restricted JAK Inhibitor for the Treatment of Inflammatory Bowel Disease

To identify Janus kinase (JAK) inhibitors that selectively target gastrointestinal tissues with limited systemic exposures, a class of imidazopyrrolopyridines with a range of physical properties was prepared and evaluated. We identified compounds with low intrinsic permeability and determined a correlation between permeability and physicochemical properties, clogP and tPSA, for a subset of compounds. This low intrinsic permeability translated into compounds displaying high colonic exposure and low systemic exposure after oral dosing at 25 mg/kg in mouse. In a mouse PK/PD model, oral dosing of lead compound 2 demonstrated dose-dependent inhibition of pSTAT phosphorylation in colonic explants post-oral dose but low systemic exposure and no measurable systemic pharmacodynamic activity. We thus demonstrate the utility of JAK inhibitors with low intrinsic permeability as a feasible approach to develop gut-restricted, pharmacologically active molecules with a potential advantage over systemically available compounds that are limited by systemic on-target adverse events.

Generation of highly potent DYRK1A-dependent inducers of human β-Cell replication via Multi-Dimensional compound optimization

Small molecule stimulation of β-cell regeneration has emerged as a promising therapeutic strategy for diabetes. Although chemical inhibition of dual specificity tyrosine-phosphorylation-regulated kinase 1A (DYRK1A) is sufficient to enhance β-cell replicat

Identification of 2-Imidazopyridine and 2-Aminopyridone Purinones as Potent Pan-Janus Kinase (JAK) Inhibitors for the Inhaled Treatment of Respiratory Diseases

Janus kinases (JAKs) have a key role in regulating the expression and function of relevant inflammatory cytokines involved in asthma and chronic obstructive pulmonary disease. Herein are described the design, synthesis, and pharmacological evaluation of a series of novel purinone JAK inhibitors with profiles suitable for inhaled administration. Replacement of the imidazopyridine hinge binding motif present in the initial compounds of this series with a pyridone ring resulted in the mitigation of cell cytotoxicity. Further systematic structure-activity relationship (SAR) efforts driven by structural biology studies led to the discovery of pyridone 34, a potent pan-JAK inhibitor with good selectivity, long lung retention time, low oral bioavailability, and proven efficacy in the lipopolysaccharide-induced rat model of airway inflammation by the inhaled route.

D2 Dopamine Receptor G Protein-Biased Partial Agonists Based on Cariprazine

Functionally selective G protein-coupled receptor ligands are valuable tools for deciphering the roles of downstream signaling pathways that potentially contribute to therapeutic effects versus side effects. Recently, we discovered both Gi/o-bi

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

NOVEL JAK1 SELECTIVE INHIBITORS AND USES THEREOF

The new 1H-furo[3,2-b]imidazo[4,5-d]pyridine derivatives are selective Jak1 kinase inhibitors useful in treating disorders related to Jak1 activities such as autoimmune diseases or disorders, inflammatory diseases or disorders, and cancer or neoplastic di

Synthesis of Novel Tetrahydroisoquinoline CXCR4 Antagonists with Rigidified Side-Chains

A structure-activity relationship study of potent TIQ15-derived CXCR4 antagonists is reported. In this investigation, the TIQ15 side-chain was constrained to improve its drug properties. The cyclohexylamino congener 15a was found to be a potent CXCR4 inhi

IMIDAZOPYRROLOPYRIDINE AS INHIBITORS OF THE JAK FAMILY OF KINASES

2-((1r,4r)-4-(imidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclohexyl)acetonitrile compounds, pharmaceutical compositions containing them, methods of making them, and methods of using them including methods for treating disease states, disorders, and conditions mediated by JAK, such as inflammatory bowel disease.