478833-52-2

Upstream product

• 364066-92-2 (2S,5R)-1-(4-fluorobenzyl)-2,5-dimethylpiperazine 
• 217645-80-2 5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde 
• 217648-11-8 2-chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 478833-49-7 1-((2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl)-2-(4-chloro-2-(hydroxymethyl)phenoxy)ethanone 

Downstream Products

• 713114-94-4 (5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyl)-phosphonic acid 
• 813446-39-8 (2-(2-((2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl)-2-oxoethoxy)-5-chlorophenyl)methanesulfonic acid L-arginine cocrystal 
• 478833-57-7 (5-chloro-2-{2-[4-(4-fluorobenzyl)-2R,5S-dimethylpiperazin-1-yl]-2-oxoethoxy}-phenyl)-methanesulfonic acid sodium salt 
• 478833-25-9 (2-(2-((2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl)-2-oxoethoxy)-5-chlorophenyl)methanesulfonic acid 

Relevant academic research and scientific papers

Route development and bulk synthesis of CP-865,569

The synthesis of zwitterionic CP-865,569 by three different synthetic routes is described. The first two routes differ in the method of introducing the sulfonic acid at the penultimate step: by sulfite displacement of a benzylic chloride and by oxidation of a benzylic thioacetate. The third route is a convergent route to the drug candidate. The synthesis strategy was primarily driven by the need to introduce the sulfonic acid functionality at the final stage of the synthesis due to the high water solubility and low organic solubility of the desired product.

Novel phosphorus-containing derivatives

A compound of the Formula I a prodrug thereof, or the pharmaceutically acceptable salt of the compound or prodrug; wherein X, Y, a, b, c, d, R1, R2, R3, R4, R5, R6 and R7 are as defined above and are useful to treat inflammation and other immune disorders. The present invention also relates to pharmaceutical compositions that include compounds of Formula I and a pharmaceutically acceptable carrier. Moreover, the present invention relates to methods of using the above-described compounds and compositions to treat and prevent diseases and conditions.