1581275-05-9

Upstream product

• 875-51-4 4-Bromo-2-nitroaniline 
• 364-73-8 4-Bromo-1-fluoro-2-nitrobenzene 
• 1581275-04-8 tert-butyl 4-(4-acetylamino-3-nitrophenyl)piperazine-1-carboxylate 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 881-50-5 N-(4-bromo-2-nitrophenyl)acetamide 

Downstream Products

• 193902-99-7 tert-butyl 4-(3,4-diaminophenyl)piperazine-1-carboxylate 
• 1581275-12-8 5-(4-(biphenyl-4-ylmethyl)piperazin-1-yl)-1H-benzo[d]imidazol-2(3H)-one 
• 1581275-13-9 5-(4-((4'-fluorobiphenyl-4-yl)methyl)piperazin-1-yl)-1H-benzo[d]imidazol-2(3H)-one 
• 1581275-14-0 5-(4-((5-phenylpyridin-3-yl)methyl)piperazin-1-yl)-1H-benzo[d]imidazol-2(3H)-one 
• 1581275-15-1 5-(4-((5-(4-fluorophenyl)pyridin-3-yl)methyl)piperazin-1-yl)-1H-benzo[d]imidazol-2(3H)-one 
• 1581275-16-2 5-(4-(3-(cyclopentenyl)benzyl)piperazin-1-yl)-1H-benzo[d]imidazol-2(3H)-one 

Relevant academic research and scientific papers

Heterocyclic compounds as FGFR4 inhibitors

The present invention provides heterocyclic compounds as selective inhibitors of fibroblast growth factor receptor 4 (FGFR4), pharmaceutical compositions containing the compounds, methods of preparingthe compounds, and methods of treating cell proliferative diseases, such as cancer, using the compounds of the invention.

Fused tricyclic derivative as FGFR4 inhibitor

The present invention provides a fused tricyclic derivative that is the selective inhibitor of fibroblast growth factor receptor 4 (FGFR4), a pharmaceutical composition containing the compound, a method of making the compound and a method of treating cell proliferative diseases, such as cancer, using the compounds of the invention.

PYRIMIDINE FGFR4 INHIBITORS

Provided herein are compounds of Formula I useful as FGFR4 inhibitors, as well as methods of use of the same.

Synthesis and dual D2 and 5-HT1A receptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones

A series of new 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)- ones have been synthesized and evaluated for dual D2 and 5-HT1A receptor binding affinities. The synthesized ligands are structurally related to bifeprunox, a potential atypical antipsychotic, having potent D2 receptor antagonist and 5-HT1A receptor agonist properties. The Suzuki-Miyaura reaction of cyclic vinyl boronate with appropriate aryl halide yielded arylpiperidine, which was eventually transformed to piperidinyl-1H-benzo[d]imidazol-2(3H)-one. The reductive amination of the latter with appropriate biarylaldehdyes rendered the synthesis of 5-piperidinyl-1H-benzo[d]imidazol-2(3H)-ones. Likewise, the Buchwald-Hartwig coupling reactions of 1-boc-piperazine with appropriate aryl halide and subsequent removal of the boc group rendered arylpiperazine. The reductive amination of the latter with appropriate biarylaldehdyes accomplished the synthesis of 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones. The structure-activity relationship studies showed that cyclopentenylpyridine and cyclopentenylbenzyl groups contribute significantly to the dual D2 and 5-HT1A receptor binding affinities of these compounds.

Benzo[D]imidazole derivatives of piperidine and piperazine

The benzo[d]imidazole derivatives of piperidine and piperazine are 5-piperazinyl and 5-piperadinyl-1H-benzo[d]imidazol-2(3H)-ones that exhibit D2 and 5-HT1A receptor binding affinities, making them suitable for use as the active ingredient of pharmaceuticals for the treatment of schizophrenia. The derivatives have the general formula: where X is carbon or nitrogen and R is a selected biaryl group, or a pharmaceutically acceptable salt thereof. The piperidinyl compounds are prepared by removal of the Boc group from tert-Butyl-4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylate. Subsequent reductive amination with a selected biarylaldehyde completes the synthesis of the 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones. The piperazinyl compounds are prepared by preparation of the intermediate tert-Butyl 4-(3,4-diaminophenyl)piperazine-1-carboxylate. Removal of the Boc group and subsequent reductive amination with a selected biarylaldehyde completes the synthesis of the 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones.