529508-57-4

Usage

Uses

Used in Pharmaceutical Industry:
5-(Bromomethyl)-4-chloropyrrolo[2,1-f][1,2,4]triazine is used as an adaptor associated kinase 1 (AAK1) inhibitor for its potential therapeutic effects in treating various diseases. AAK1 is a non-receptor protein kinase that has been implicated in the regulation of intracellular trafficking, cytoskeletal dynamics, and cell signaling. Inhibition of AAK1 may help in the development of novel therapeutic strategies for conditions such as cancer, neurodegenerative diseases, and other disorders where AAK1 plays a role in their pathogenesis.

Upstream product

• 529508-56-3 4-chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine 
• 310435-15-5 C₈H₇N₃O₃ 
• 427878-70-4 ethyl 4-hydroxy-5-methylpyrrolo[2,1-f ][1,2,4]-triazine-6-carboxylate 
• 427878-69-1 1-amino-3-methyl-1H-pyrrole-2,4-dicarboxylic acid diethyl ester 
• 5448-16-8 3-methyl-1H-pyrrole-2,4-dicarboxylic acid diethyl ester 

Downstream Products

• 942416-44-6 C₁₃H₁₀ClN₃S 
• 529508-59-6 [1-(3-fluoro-benzyl)-1H-indazol-5-yl]-(5-phenylsulfanylmethyl-pyrrolo[2,1-f][1,2,4]triazin-4-yl)-amine 
• 529509-71-5 4-{4-[1-(3-fluoro-benzyl)-1H-indazol-5-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethoxy}-piperidine-1-carboxylic acid tert-butyl ester 
• 1265683-88-2 Br^(1-)*C₂₀H₂₈N₅⁽¹⁺⁾ 
• 1265683-89-3 Br^(1-)*C₂₀H₂₈N₅⁽¹⁺⁾ 
• 1265683-90-6 Br^(1-)*C₂₀H₂₈N₅⁽¹⁺⁾ 
• 1265683-91-7 Br^(1-)*C₁₉H₂₅FN₅⁽¹⁺⁾ 
• 1265683-92-8 Br^(1-)*C₁₉H₂₅ClN₅⁽¹⁺⁾ 
• 1265683-93-9 Br^(1-)*C₁₉H₂₅BrN₅⁽¹⁺⁾ 
• 1265683-94-0 Br^(1-)*C₁₉H₂₄Cl₂N₅⁽¹⁺⁾ 
• 1265683-95-1 Br^(1-)*C₁₉H₂₄ClFN₅⁽¹⁺⁾ 
• 1265683-96-2 Br^(1-)*C₂₀H₂₇ClN₅O⁽¹⁺⁾ 
• 529509-61-3 {4-[1-(3-fluoro-benzyl)-1H-indazol-5-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-yl}-methanol 

Relevant academic research and scientific papers

Development of a practical synthesis of a functionalized pyrrolo[2,1-f][1,2,4]triazine nucleus

Functionalized pyrrolotriazine 1b is a key heterocyclic building block in the synthesis of BMS-690514, a potent anticancer agent. Described herein are our development activities that led to the efficient preparation of 1b on a large scale. The key transformations include a selective C-alkylation of an oxalacetate salt with a hydrazonyl bromide to form a 2-hydrazonoethyl-3- oxosuccinate, followed by cyclodehydration to an aminopyrrole. Subsequent deprotection and condensation with formamidine afforded the pyrrolotriazine scaffold. Further elaboration of this core provided the desired pyrrolotriazinyl amine.

Novel pyrrolo[2,1-f][1,2,4]triazin-4-amines: Dual inhibitors of EGFR and HER2 protein tyrosine kinases

A novel series of 5-((4-aminopiperidin-1-yl)methyl)-pyrrolo[2,1-f][1,2,4] triazin-4-amines with small aniline substituents at the C4 position were optimized for dual EGFR and HER2 protein tyrosine kinase inhibition. Compound 8l exhibited promising oral efficacy in both EGFR and HER2-driven human tumor xenograft models.

New C-5 substituted pyrrolotriazine dual inhibitors of EGFR and HER2 protein tyrosine kinases

Novel C-5 substituted pyrrolotriazines were optimized for dual EGFR and HER2 protein tyrosine kinase inhibition. The lead compound exhibited promising oral efficacy in both EGFR and HER2 driven human tumor xenograft models. It is hypothesized that its C-5

5-((4-Aminopiperidin-1-yl)methyl)pyrrolotriazine dual inhibitors of EGFR and HER2 protein tyrosine kinases

Pyrrolotriazine dual EGFR/HER2 kinase inhibitors with a 5-((4-aminopiperidin-1-yl)methyl) solubilizing group were found to be superior to analogs with previously reported C-5 solubilizing groups. New synthetic methodology was developed for the parallel sy

SYNTHETIC PROCESS

The present invention provides a process for preparing compounds of formula (IV), or a pharmaceutically acceptable salt thereof. The compounds prepared by the process of the invention inhibit tyrosine kinase activity of growth factor receptors such as HER

Di-substituted pyrrolotrizine compounds

The present invention provides compounds of formula I and pharmaceutically acceptable salts thereof. The compounds of the invention inhibit tyrosine kinase activity of growth factor receptors such as HER1, HER2 and HER4 thereby making them useful as antiproliferative agents for the treatment of cancer and other diseases.

PYRROLOTRIAZINE COMPOUNDS AS KINASE INHIBITORS

The present invention provides compounds of formula (I); and pharmaceutically acceptable salts thereof. The formula (I) compounds inhibit tyrosine kinase activity of growth factor receptors such as HER1, HER2 and HER4 thereby making them useful as antiproliferative agents. The formula (I) compounds are also useful for the treatment of other diseases associated with signal transduction pathways operating through growth factor receptors.

C-5 Modified indazolylpyrrolotriazines

The present invention provides compounds of formula I and pharmaceutically acceptable salts thereof. The formula I compounds inhibit tyrosine kinase activity of growth factor receptors such as HER1, HER2 and HER4 thereby making them useful as antiproliferative agents. The formula I compounds are also useful for the treatment of other diseases associated with signal transduction pathways operating through growth factor receptors.