50609-01-3

Usage

Uses

Used in Pharmaceutical Development:
4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamine is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs targeting specific biological pathways, potentially leading to innovative treatments for a range of medical conditions.
Used in Medicinal Chemistry Research:
In the realm of medicinal chemistry, 4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamine serves as a valuable compound for research purposes. It can be employed to study the structure-activity relationships of drug molecules, aiding in the design and optimization of more effective and safer pharmaceutical agents.
Used in Drug Discovery:
4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamine is used as a starting material in drug discovery processes. Its chemical properties and structural features make it a promising candidate for the development of novel therapeutic agents, particularly in the areas of central nervous system disorders, cardiovascular diseases, and other conditions that may benefit from its pharmacological profile.
Used in Chemical Synthesis:
Beyond its direct application in drug development, 4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamine is also used as a building block in the synthesis of a variety of organic compounds. Its versatility in chemical reactions allows for the creation of diverse chemical entities, expanding the scope of its applications in various industries.

InChI:InChI=1/C12H18N2O/c13-11-3-5-12(6-4-11)15-10-9-14-7-1-2-8-14/h3-6H,1-2,7-10,13H2

Upstream product

• 7250-67-1 1-(2-chloroethyl)pyrrolidine hydrochloride 
• 123-30-8 4-amino-phenol 
• 100-00-5 4-chlorobenzonitrile 
• 2955-88-6 1-pyrrolidineethanol 
• 350-46-9 4-Fluoronitrobenzene 
• 100-02-7 4-nitro-phenol 
• 3383-72-0 1-(2-chloroethoxy)-4-nitrobenzene 
• 16365-27-8 2-(4-nitrophenoxy)ethanol 
• 13288-06-7 1-(2-bromoethoxy)-4-nitrobenzene 
• 1081-73-8 1-[2-(4-bromophenoxy)ethyl]pyrrolidine 
• 85002-96-6 1-(2-(4-nitrophenoxy)ethyl)pyrrolidine hydrochloride 
• 265654-77-1 1-(2-(4-nitrophenoxy)ethyl)pyrrolidine 

Downstream Products

• 936092-38-5 5-methyl-N₂-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidine-2,4-diamine 
• 936091-26-8 N-tert-butyl-3-{5-methyl-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-pyrimidin-4-ylamino}-benzenesulfonamide 

Relevant academic research and scientific papers

High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates

Commercially available Pd/C can be used as a catalyst for nitro group reductions with only 0.4 mol % Pd loading. The reaction can be performed using either silane as a transfer hydrogenating agent or simply a hydrogen balloon (μ1 atm pressure). With this technology, a series of nitro compounds was reduced to the desired amines in high chemical yields. Both the catalyst and surfactant were recycled several times without loss of reactivity.

Identification of a Novel 2,8-Diazaspiro[4.5]decan-1-one Derivative as a Potent and Selective Dual TYK2/JAK1 Inhibitor for the Treatment of Inflammatory Bowel Disease

In this study, we described a series of 2,8-diazaspiro[4.5]decan-1-one derivatives as selective TYK2/JAK1 inhibitors. Systematic exploration of the structure-activity relationship through the introduction of spirocyclic scaffolds based on the reported selective TYK2 inhibitor 14l led to the discovery of the superior derivative compound 48. Compound 48 showed excellent potency on TYK2/JAK1 kinases with IC50 values of 6 and 37 nM, respectively, and exhibited more than 23-fold selectivity for JAK2. Compound 48 also demonstrated excellent metabolic stability and more potent anti-inflammatory efficacy than tofacitinib in acute ulcerative colitis models. Moreover, the excellent anti-inflammatory effect of compound 48 was mediated by regulating the expression of related TYK2/JAK1-regulated genes, as well as the formation of Th1, Th2, and Th17 cells. Taken together, these findings suggest that compound 48 is a selective dual TYK2/JAK inhibitor, deserving to be developed as a clinical candidate.

PYRAZOLE DERIVATIVES AS MODULATORS OF THE WNT/B-CATENIN SIGNALING PATHWAY

Pyrazole compounds (I) for treating various diseases and pathologies are disclosed. More particularly, the present disclosure concerns the use of a pyrazole compounds, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis Alzheimer's disease, lung disease, inflammation, auto-immune diseases and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as neurological conditions/disorders/diseases linked to overexpression of DYRK1A.

N2-substituted alkoxy aromatic cyclo-2-aminopyrimidine derivative and application thereof

The invention provides an N2-substituted alkoxy aromatic cyclo-2-aminopyrimidine derivative and application thereof. The N2-substituted alkoxy aromatic cyclo-2-aminopyrimidine derivative comprises anoptical isomer and pharmaceutically acceptable salt thereof. Preliminary pharmacodynamic indication shows that the compound disclosed by the invention has FLT3 inhibitory activity, wherein the proliferation inhibition activity is realized on various leukemia cell strains; moreover, the derivative is effective for multiple mutations of AML, such as internal tandem repeat mutation of a near-membranestructural domain and D835 point mutation of an activated ring in a kinase structural domain and almost has no inhibition effect on c-KIT. The derivative can overcome drug resistance brought by clinical point mutation, can reduce toxic and side effects of bone marrow inhibition, and can be applied to preparation of antitumor drugs. The general structural formula of the derivative is shown in thespecification.

Diphenylamino pyrimidine compound for inhibiting kinase activity

The invention provides a diphenylamino pyrimidine compound for inhibiting the kinase activity, and particularly provides a medicinal composition of a substituted diphenylamino pyrimidine compound andapplication thereof. The compound is a compound as shown in a formula (I) in the specification, or pharmaceutically acceptable salt, prodrug, hydrate thereof or solvent compound, crystal form, N-oxideand various diastereomers thereof. The compound can be used for treating diseases which can be treated with JAK2 kinase inhibitors.

5-HETEROARYL SUBSTITUTED INDAZOLE-3-CARBOXAMIDES AND PREPARATION AND USE THEREOF

Indazole compounds for treating various diseases and pathologies are disclosed. More particularly, the present disclosure concerns the use of an indazole compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., tendinopathy, dermatitis, psoriasis, morphea, ichthyosis, Raynaud's syndrome, Darier's disease, scleroderma, cancer, abnormal cellular proliferation, angiogenesis, Alzheimer's disease, lung disease, and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as neurological conditions/disorders/diseases linked to overexpression of DYRK1A.

Discovery of 4-piperazinyl-2-aminopyrimidine derivatives as dual inhibitors of JAK2 and FLT3

Hybridization strategy is an effective strategy to obtain multi-target inhibitors in drug design. In this study, we assembled the pharmacophores of momelotinib and tandutinib to get a series of 4-piperazinyl-2-aminopyrimidine derivatives. All compounds were tested for the inhibition of JAK2 and FLT3 enzymes, of which, compounds with potent enzyme activities were assayed for antiproliferative activities against three cancer cell lines (HEL, MV4-11, and HL60). The structure-activity relationship studies were conducted through variations in two regions, the “A” phenyl ring and “B” phenyl ring. Compound 14j showed the most balanced in vitro inhibitory activity against JAK2 and FLT3 (JAK2 IC50 = 27 nM, FLT3 IC50 = 30 nM), and it also showed potent inhibition against the above tested cell lines. In the cellular context, 14j strongly induced apoptosis by arresting cell cycle in the G1/S phase, and was selected as a promising JAK2/FLT3 dual inhibitor.

MULTI-SUBSTITUTED PYRIMIDINE DERIVATIVES WITH EXCELLENT KINASE INHIBITORY ACTIVITIES

Disclosed are a novel pyrimidine derivative compound, a pharmaceutically acceptable salt thereof, a method for preparing the compound and a pharmaceutical use of the compound as an anticancer agent or a therapeutic agent for degenerative brain diseases. Specifically, the novel pyrimidine derivative compound has excellent inhibitory activities against kinase enzymes such as ARK5/NUAK1, ACK1, FLT3, JAK1, JAK2 and JAK2 (V617F) and thus is useful for treating and preventing leukemia, ovarian cancer, breast cancer, non-small cell carcinoma, colorectal cancer, glioma, and brain protein abnormalities such as Alzheimer's disease, progressive supranuclear palsy and frontotemporal dementia, that is, degenerative diseases caused by Tau deposition.

AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS

In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.

Diaminopyrimidine derivatives for kinase inhibitors

The present invention relates to a novel diaminopyrimidine compound and a pharmaceutically acceptable salt thereof, a method for producing the compound, and a medical use of the compound as an anticancer agent. According to the present invention, the nove