691875-73-7

Upstream product

• 133787-04-9 methyl (RS)-N-phthaloyl-2-amino-4-pentenoate 
• 42365-62-8 [3,5-bis(trifluoromethyl)phenyl]methanamine hydrochloride 
• 182261-52-5 methyl (S)-4-oxo-2-phthalimidobutanoate 
• 101386-28-1 2-(1,3-dioxoisoindolin-2-yl)pent-4-enoic acid 
• 85-44-9 phthalic anhydride 
• 691877-48-2 C₂₆H₂₆N₂O₄ 
• 85068-29-7 3,5-bis-trifluoromethylbenzylamine 

Downstream Products

• 691875-74-8 C₂₆H₂₇F₆N₃O 

Relevant academic research and scientific papers

4-Amino-2-alkyl-butyramides as small molecule CCR2 antagonists with favorable pharmacokinetic properties

A systematic examination of the central aromatic portion of the lead (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-(4-fluorophenyl)-4-(1′H-spiro[indene-1,4′-piperidin]-1′-yl)butanamide (9) led to the discovery of a novel class of CCR2 receptor antagonists, which carry small alicyclic groups such as cyclopropyl, cylobutyl, or cyclopropylmethyl attached at C2 of the carbon backbone. The most potent compound discovered, namely (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-cyclopropyl-4-[(1R,3′R)-3′-methyl-1′H-spiro[indene-1,4′-piperidin]-1′-yl]butanamide (29), showed very high binding affinity (IC50 = 4 nM, human monocyte) and excellent selectivity toward other related chemokine receptors. The excellent pharmacokinetic profile of this new lead compound allows for extensive in vivo evaluation.

GAMMA-AMINOAMIDE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

The present invention is directed to compounds of the formula (I), wherein R1, R2, R3, R4, R5, R6, R7, R8, R11, R12, W, X, and n are defined herein, which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2.