10394-38-4

Usage

Uses

Used in Pharmaceutical Industry:
1-METHYL-1H-BENZOIMIDAZOL-5-YLAMINE TRIHYDROCHLORIDE is used as a synthetic intermediate for the production of usnic acid derivatives, which are known for their potential as tau-aggregation and neuroinflammation inhibitors. These derivatives have potential applications in the treatment of neurodegenerative diseases such as Alzheimer's disease, where they can help reduce the formation of tau protein aggregates and alleviate neuroinflammation.

InChI:InChI=1/C8H9N3/c1-11-5-10-7-4-6(9)2-3-8(7)11/h2-5H,9H2,1H3

Upstream product

• 5381-79-3 1-methyl-6-nitro-1H-benzoimidazole 
• 5381-78-2 1-methyl-5-nitro-1H-benzo[d]imidazole 
• 51-17-2 benzoimidazole 
• 74-88-4 methyl iodide 
• 94-52-0 6-nitro-1H-benzo[d]imidazole 
• 53484-15-4 5-bromo-1-methyl-1H-benzo[d]imidazole 
• 95-54-5 1,2-diamino-benzene 
• 1632-83-3 1-Methylbenzimidazole 
• 41939-61-1 N₁-methyl-4-nitrobenzene-1,2-diamine 

Downstream Products

• 1610766-88-5 C₂₃H₂₆N₆O₃ 
• 1574357-72-4 1-(3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)-3-(4-((2-((1-methyl-1H-benzo[d]imidazol-5-yl)amino)pyrimidin-4-yl)oxy)naphthalen-1-yl)urea 
• 332886-13-2 2-{[(1-methyl-benzimidazol-5-yl)imino]methyl}phenol 
• 920978-70-7 N-(1-methyl-1H-benzimidazol-5-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide 
• 920978-57-0 N-(1-methyl-1H-benzimidazol-5-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-c]pyridine-2-carboxamide 
• 128056-54-2 2-(4-Chloro-phenyl)-8-methyl-5,8-dihydro-2H-1,2,5,8,10-pentaaza-dicyclopenta[a,h]naphthalen-3-one 
• 73857-49-5 3,8-Dimethyl-7-phenyl-3,6-dihydro-imidazo[4,5-e]indole 

Relevant academic research and scientific papers

13C and 15N NMR spectra of aminobenzimidazoles in solution and in the solid state

The 13C [hexadeutero-dimethylsulfoxide (DMSO-d6), hexamethyl-phosphoramide (HMPA)-d18 and solid-state] and 15N (solid-state) NMR spectra of six C-aminobenzimidazoles have been recorded. The tautomerism of 4(7)-aminobenzimidazoles and 5(6)- aminobenzimidazoles has been determined and compared with B3LYP/6-311++G(d,p) calculations confirming the clear predominance of the 4-amino tautomer and the slight preference for the 6-amino tautomer. GIAO-calculated absolute shieldings compare well with experimental chemical shifts. Copyright

Fusion of 2-(furan-2-yl)thiazole to 1-methyl-1H-benzimidazole

Methylation of 5(6)-nitro-1H-benzimidazole with methyl iodide in the presence of potassium hydroxide and N-methylpyrrolidin-2-one gave a mixture of isomeric 1-methyl-5-nitro- and 1-methyl-6-nitro-1H-benzimidazoles which were reduced with tin in concentrated aqueous HCl on heating. The resulting amines reacted with furan-2-carbonyl chloride in N-methylpyrrolidin-2-one to give furan-2-carboxamides which were treated with excess P2S5 in pyridine. Oxidation of isomeric furan-2-carbothioamides with K3[Fe(CN)6] in alkaline medium afforded a mixture of intramolecular cyclization products, 2-(furan-2-yl)-6-methyl-6H-imidazo[4,5-g][1,3]benzothiazole and 2-(furan-2-yl)-8-methyl-8H-imidazo[4,5-g][1,3]benzothiazole which were separated by column chromatography and identified.

SUBSTITUTED HETEROARYL COMPOUNDS AND METHODS OF USE

The present invention provides novel heteroaryl compounds, pharmaceutical acceptable salts and formulations thereof. They are useful in preventing, managing, treating or lessening the severity of a protein kinase-mediated disease. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of protein kinase-mediated disease.

Substituted heteroaryl compounds and compositions and uses thereof (by machine translation)

The invention discloses substituted heteroaryl compounds and compositions thereof and their use. The compounds of formula (I) compound or type shown in (I) a compound represented by stereo isomers, tautomers, nitrogen oxide, solvate, metabolite, pharmaceutically acceptable salt or its prodrug. The invention also provides a pharmaceutical composition, the compounds and pharmaceutical compositions can be regulated protein kinase, particularly Aurora kinase and JAK kinase activity, for the prevention, treatment, treatment and reduce protein kinase, in particular JAK kinase activity mediated diseases or disorders. (by machine translation)

5-SULFAMOYL-2-HYDROXYBENZAMIDE DERIVATIVES

The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R, R1 and R2 are as defined herein, or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

HEPARAN SULFATE BIOSYNTHESIS INHIBITORS FOR THE TREATMENT OF DISEASES

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions in need of inhibition of heparan sulfate biosynthesis.

New antibacterial diazotized derivatives of 5-amino azaheterocycles

Six new diazotized derivatives of pharmacologically important azaheterocycles (2a-d, 4a-b) were prepared from their corresponding 5-amino benzimidazoles (1a-d) and benzimidazolones (3a-b). All new compounds have been characterized on the basis of their IR, NMR and Mass spectral data. Antibacterial activity of these compounds is also been reported.

METHODS AND COMPOSITIONS FOR THE TREATMENT OF MYELOPROLIFERATIVE DISEASES AND OTHER PROLIFERATIVE DISEASES

Compounds of the present invention find utility in the treatment of hyperproliferative diseases, mammalian cancers and especially human cancers including but not limited to malignant, melanomas, glioblastomas, ovarian cancer, pancreatic cancer, prostate cancer, lung cancers, breast cancers, kidney cancers, cervical carcinomas, metastasis of primary tumor sites secondary sites, myeloproliferative diseases, chronic myelogenous leukemia, acute lymphocytic leukemia, papillary thyroid carcinoma, non small cell lung cancer, mesothelioma, hypereosinophilic syndrome, gastrointestinal stromal tumors, colonic cancers, thyroid cancer, ocular diseases characterized by hyperproliferation leading to blindness including various retinopathies, i.e. diabetic retinopathy and age-related macular degeneration, rheumatoid arthritis, asthma, chronic obstructive pulmonary disease, human inflammation, rheumatoid spondylitis, ostero-arthritis, asthma, gouty arthritis, sepsis, septic shock, endotoxic shock, Gram-negative sepsis, toxic shock syndrome, adult respiratory distress syndrome, stroke, reperfusion injury, neural trauma, neural ischemia, psoriasis, restenosis, chronic obstructive pulmonary disease, bone resorptive diseases, graft-versus-host reaction, Crohn's disease, ulcerative colitis, inflammatory bowel disease, pyresis, and combinations thereof, a disease caused by c-ABL kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, c-KIT kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, VEGFR kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, PDGFR kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, FLT-3 kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, TIE-2 kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, TRK kinases, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, c-MET kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, or a disease caused by a HER kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof.

Structure-activity relationship of human glutaminyl cyclase inhibitors having an N-(5-methyl-1H-imidazol-1-yl)propyl thiourea template

In an effort to design inhibitors of human glutaminyl cyclase (QC), we have synthesized a library of N-aryl N-(5-methyl-1H-imidazol-1-yl)propyl thioureas and investigated the contribution of the aryl region of these compounds to their structure-activity relationships as cyclase inhibitors. Our design was guided by the proposed binding mode of the preferred substrate for the cyclase. In this series, compound 52 was identified as the most potent QC inhibitor with an IC50 value of 58 nM, which was two-fold more potent than the previously reported lead 2. Compound 52 is a most promising candidate for future evaluation to monitor its ability to reduce the formation of pGlu-Aβ and Aβ plaques in cells and transgenic animals.

KINASE INHIBITORS USEFUL FOR THE TREATMENT OF MYLEOPROLIFERATIVE DISEASES AND OTHER PROLIFERATIVE DISEASES

The present invention is concerned with novel compounds useful in the treatment of hyperproliferative diseases and mammalian cancers, especially human cancers. The invention also pertains to methods of modulating kinase activities, pharmaceutical compositions, and methods of treating individuals, incorporating or using the compounds. The preferred compounds are active small molecules set forth in formulae Ia-Iww.