479622-22-5

Upstream product

• 100-39-0 benzyl bromide 
• 1359824-26-2 C₂₇H₄₂N₂O₅Si 
• 114214-69-6 tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 85310-69-6 pyrrolidin-3-ylmethanol 
• 479622-21-4 3-[1-(tert-butyl-dimethyl-silanyl)-2-carboxy-4-oxo-azetidin-3-ylmethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 479622-36-1 3-iodomethylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 5731-17-9 1-(Phenylmethyl)-3-pyrrolidinemethanol 

Downstream Products

• 479622-23-6 (2S,3R)-3-(1-{Benzyloxycarbonylamino-[(E)-benzyloxycarbonylimino]-methyl}-pyrrolidin-3-ylmethyl)-4-oxo-azetidine-2-carboxylic acid benzyl ester 
• 727725-99-7 4-[(2S,3R)-2-Benzyloxycarbonyl-3-(1-tert-butoxycarbonyl-pyrrolidin-3-ylmethyl)-4-oxo-azetidine-1-carbonyl]-piperazine-1-carboxylic acid 1-isopropyl-2-methyl-propyl ester 

Relevant academic research and scientific papers

Beta lactam compounds and their use as inhibitors of tryptase

Beta lactam compounds are provided which have the structure wherein B, A, D, R1, R2, R3 and X1 are as defined herein, and which are useful as inhibitors of tryptase, thrombin, trypsin, Factor Xa, Factor VIIa, and urokinase-type plasminogen activator and may be employed in preventing and/or treating asthma and allergic rhinitis.

Synthesis of potent and highly selective nonguanidine azetidinone inhibitors of human tryptase

Azetidinones such as BMS-363131 (2) and BMS-363130 (3), which contain a guanidine group in the C-3 side chain were previously shown to be very potent inhibitors of human tryptase with high selectivity versus other serine proteases, including trypsin. In this letter, we describe the discovery of a number of potent azetidinone tryptase inhibitors in which the guanidine moiety at the ring C-3 position is replaced with primary or secondary amine or aminopyridine functionality. In particular, BMS-354326 (4) is a highly potent tryptase inhibitor (IC50=1.8nM), which has excellent selectivity against trypsin and most other related serine proteases.

Synthesis of potent and highly selective inhibitors of human tryptase

The serine protease tryptase has been implicated in allergic and inflammatory diseases and associated with asthma. The synthesis and SAR of a series of N1-activated-4-carboxy azetidinones are described, resulting in identification of BMS-363131 (2) as a potent inhibitor of human tryptase (IC503000-fold) for tryptase versus related serine proteases including trypsin.