91476-82-3

Usage

Uses

Used in Pharmaceutical Synthesis:
5,6,7,8-Tetrahydro-imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the formation of biologically active molecules.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 5,6,7,8-Tetrahydro-imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester serves as a precursor for the synthesis of various heterocyclic compounds, which are essential in creating complex organic structures with potential applications in different industries.
Used in Medicinal Chemistry Research:
5,6,7,8-Tetrahydro-imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester is utilized as a research compound in medicinal chemistry to explore its potential in the development of new drugs, given its unique properties and reactivity.
Used in Drug Development:
In the pharmaceutical industry, 5,6,7,8-Tetrahydro-imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester is used as a starting material for drug development, facilitating the creation of innovative therapeutic agents that address unmet medical needs.

InChI:InChI=1/C9H13N3O2/c1-2-14-9(13)7-6-12-4-3-10-5-8(12)11-7/h6,10H,2-5H2,1H3

Upstream product

• 1053656-22-6 7-(tert-butyl) 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate 
• 92234-23-6 ethyl 3-bromo-2-hydroxy propionate 
• 70-23-5 ethyl Bromopyruvate 
• 77112-52-8 ethyl imidazo[1,2-a]pyrazine-2-carboxylate 

Downstream Products

• 1575607-74-7 (2R,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-(2-(ethoxycarbonyl)-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)butan-2-ol 
• 1608503-32-7 7-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)-N-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxamide 
• 1608503-33-8 7-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)-N-(2-fluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxamide 
• 1608503-34-9 C₂₅H₂₂ClFN₆O 
• 1608503-35-0 7-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)-N-(4-fluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxamide 
• 1608503-36-1 C₂₅H₂₁ClF₂N₆O 
• 1608503-42-9 phenyl 7-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylate 
• 1338562-13-2 C₁₅H₂₂N₄O₃ 
• 1338563-42-0 ethyl 7-(1-methylcyclohexanecarbonyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylate 
• 1338563-43-1 ethyl 7-(o-tolylcarbamoyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylate 
• 723286-62-2 ethyl 7-[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylate 
• 1053656-22-6 7-(tert-butyl) 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate 
• 623564-19-2 7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester 
• 1174069-07-8 ethyl 7-(tert-butoxycarbonyl)-3-chloro-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylate 

Relevant academic research and scientific papers

ROCK INHIBITOR, AND PREPARATION METHOD THEREFOR AND USE THEREOF

The invention relates to a ROCK inhibitor represented by formula (I), its preparation method and its use. The ROCK inhibitor has excellent ROCK inhibition activity, in particular good selective inhibition on ROCK2 kinase, has good safety and metabolic stability, and has high bioavailability. The process of preparing the ROCK inhibitor is simple, and the ROCK inhibitor is easy to purify, and therefore offers good prospects for application.

HETEROCYCLIC COMPOUNDS AS PRMT5 INHIBITORS

The compounds of Formula I, Formula Ia, and Formula Ib are described herein along with their analogs, tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites, and prodrugs thereof. These compounds inhibit PRMT5 and are useful as therpeautic or ameliorating agent for diseases that are involved in cellular growth such as malignant tumors, schizophrenia, Alzheimer's disease, Parkinson's disease and the like.

A Continuous Flow Strategy for the Facile Synthesis and Elaboration of Semi-Saturated Heterobicyclic Fragments

An efficient hydrogenation protocol under continuous flow conditions was developed for the synthesis of underrepresented semi-saturated bicyclic fragments containing highly sp3-rich skeletons for fragment-based drug discovery (FBDD) programs. Excellent yields were generally achieved by using Pd/C (10 % w/w) and RaNi at 25–150 °C under 4–100 bar of hydrogen pressure. The generated fragments, with appropriate physicochemical properties, present diverse hydrogen-bonding pharmacophores and useful vectors for their synthetic elaboration in the optimization stage. Successive, simple functionalizations in continuous flow were accomplished to demonstrate the opportunity to develop multi-step continuous flow synthesis of valuable starting points for FBDD campaigns. A conclusive quality control (QC) was essential to discard those structures which do not fit the typical fragment library parameters.

HETERO-HALO INHIBITORS OF HISTONE DEACETYLASE

This invention provides compounds that are inhibitors of HDAC2. The compounds (e.g., compounds according to Formula I, II or any of Compounds 100-128 or any of those in Tables 2 or 3) accordingly are useful for treating, alleviating, or preventing a condition in a subject such as a neurological disorder, memory or cognitive function disorder or impairment, extinction learning disorder, fungal disease or infection, inflammatory disease, hematological disease, or neoplastic disease, or for improving memory or treating, alleviating, or preventing memory loss or impairment.

HEDGEHOG PATHWAY SIGNALING INHIBITORS AND THERAPEUTIC APPLICATIONS THEREOF

The hedgehog (Hh) signaling pathway is a pathway which regulates patterning, growth and cell migration during embryonic development, but in adulthood is limited to tissue maintenance and repair. Mutational inactivation of the inhibitory pathway components leads to constitutive ligand-independent activation of the Hh signaling pathway, results in cancers such as basal cell carcinoma and medulloblastoma. Ligand-dependent activation of Hh signaling is involved in prostate cancer, pancreatic cancer, breast cancer and blood cancers. Therefore, inhibition of the aberrant Hh signaling represents a promising approach toward novel anticancer therapy. The invention provides novel molecules of formula I that inhibit hedgehog pathway signaling and provides therapeutic applications for the treatment of malignancies (basal cell carcinoma, medulloblastoma, glioblastoma, non-small cell lung cancer, prostate cancer, pancreatic cancer, blood cancers, mesenchymal cancers, etc.), prevention of tumor regrowth, sensitization of radio-chemo therapies, and other diseases (inflammation, fibrosis and immune disorders).

Scaffold hopping approach to a new series of smoothened antagonists

The hedgehog (Hh) signaling pathway is a key regulator during embryonic development, while in adults, it has limited functions such as stem cell maintenance and tissue repair. The aberrant activity of the Hh signaling in adults has been linked to numerous human cancers. Inhibition of Hh signaling therefore represents a promising approach toward novel anticancer therapies. The Smoothened (Smo) receptor mediates Hh signaling. Here we report a new series of Smo antagonists which were obtained by a scaffold hopping strategy. Compounds from this new scaffold demonstrated decent inhibition of Hh pathway signaling. The new scaffold can serve as a starting point for further optimization.

Design, synthesis, and structure-activity relationship studies of novel fused heterocycles-linked triazoles with good activity and water solubility

Triazoles with fused-heterocycle nuclei were designed and evaluated for their in vitro activity on the basis of the binding mode of albaconazole using molecular docking, along with SAR of antifungal triazoles. Tetrahydro-[1,2,4] triazolo[1,5-a]pyrazine and tetrahydro-thiazolo[5,4-c]pyridine nuclei were preferable to the other four fused-heterocycle nuclei investigated. Potent in vitro activity, broad spectrum and better water solubility were attained when triazoles containing nitrogen aromatic heterocycles were attached to these two nuclei. The most potent compounds 27aa and 45x, with low hERG inhibition and hepatocyte toxicity, both exhibited excellent activity against Candida, Cryptococcus, and Aspergillus spp., as well as selected fluconazole-resistant strains. A high water-soluble compound 58 (the disulfate salt of 45x) displayed unsatisfactory in vivo activity because of its poor PK profiles. Mice infected with C.alb. SC5314 and C.alb. 103 (fluconazole-resistant strain) and administered with 27aa displayed significantly improved survival rates. 27aa also showed favorable pharmacokinetic (PK) profiles.

BENZODIOXANE INHIBITORS OF LEUKOTRIENE PRODUCTION FOR COMBINATION THERAPY

The present invention relates to a combination comprising compounds of formula (I): wherein R1 to R3, A, X and n are as defined herein, and an additional active agent. The present invention also relates to pharmaceutical compositions comprising these combinations, and methods of using these combinations to treat various diseases and disorders.

BENZODIOXANES FOR INHIBITING LEUKOTRIENE PRODUCTION

The present invention relates to compounds of formula (I) wherein R1 to R3, A, X and n are as defined herein. The compounds of formula (I) are useful as inhibitors of leukotriene A4 hydrolase (LTA4H) and treating LTA4H related disorder. The present invention also relates to pharmaceutical compositions comprising the compounds of formula (I), methods of using these compounds in the treatment of various diseases and disorders, and processes for preparing these compounds.

3-AMINO-4-PHENYLBUTANOIC ACID DERIVATIVES AS DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES

The present invention is directed to 3-amino-4-phenylbutanoic acid derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme ("DP-IV inhibitors") and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.