145574-24-9

Upstream product

• 79-37-8 oxalyl dichloride 
• 67-68-5 dimethyl sulfoxide 
• 145574-13-6 benzyl (1S,4S,5S)-6-(3,4-dimethoxybenzyl)-4-hydroxy-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate 
• 407-25-0 trifluoroacetic anhydride 
• 214837-07-7 (3S,4S)-<1-(3,4-dimethoxybenzyl)-2-oxo-4-<(R)-2-oxo-1,3-dioxololan-3-yl>azetidin-3-yl>carbamic acid benzyl ester 

Downstream Products

• 145574-48-7 benzyl (1S,4R,5S)-6-(3,4-dimethoxybenzyl)-7-oxo-4-<(trifluoromethyl)sulfonyloxy>-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate 
• 145574-49-8 benzyl (1S,4S,5S)-4-fluoro-6-(3,4-dimethoxybenzyl)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate 
• 145574-50-1 benzyl (1S,4S,5S)-4-fluoro-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate 
• 145632-44-6 benzyl (1S,1R,5S)-6-(3,4-dimethoxybenzyl)-4-hydroxy-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate 

Relevant academic research and scientific papers

Structure-based design of β-lactamase inhibitors. 1. Synthesis and evaluation of bridged monobactams

Bridged monobactams are novel, potent, mechanism-based inhibitors of class C β-lactamases, designed using X-ray crystal structures of the enzymes. They stabilize the acyl-enzyme intermediate by blocking access of water to the enzyme-inhibitor ester bond.

BICYCLIC AND TRICYCLIC BETA-LACTAMS

There are described compounds of the formula in which R signifies lower alkoxycarbonyl, lower alkoxycarbonylamino, the acyl residue of an a- or P-amino acid or a residue of the general formula Q-X-Y- wherein Q signifies a 3- to 6-membered ring which optionally contains nitrogen, sulphur and/or oxygen and which is optionally bonded with a fused ring, X signifies a direct bond or a linear "spacer" with up to 6 atoms consisting of carbon, nitrogen, oxygen and/or sulphur, of which up to 2 atoms can be nitrogen atoms and 1 atom can be oxygen or sulphur, and Y represents one of the groups ?CO-, -CS-, -CONH- and (where X contains neither sulphur nor carbonyl as a terminal component) -SO2- and in which R1 signifies hydrogen, halogen, carbamoyloxy, lower alkanoyloxy or a group of the formula ?S-Het, wherein Het represents a 5- or 6-membered heteroaromatic group containing nitrogen, sulphur and/or oxygen, and R2 represents the sulpho group -SO3H or R1 and R2 together signify a group of the formula wherein A represents hydrogen or a residue which is usable in the 3-position of cephalosporin antibiotics, and in which R3 represents hydrogen or R1 and R3 together represent a group of the formula =CH-Ra (c) wherein Ra signifies one of the groups ?CORb (c1) -CH2-OCORc (c2) -CH2-NRdRe (c3) -CH2-S-Het (C4) in which R6 represents lower alkoxy or amino, Rc represents lower alkyl, phenyl or amino, Rd and Re each independently represent hydrogen or lower alkyl or Rd and Re together with the N atom to which they are attached represent a 5- or 6-membered N-heterocycle which optionally contains a further nitrogen, oxygen or sulphur atom and Het represents a 5- or 6-membered heteroaromatic group containing nitrogen, sulphur and/ or oxygen, and pharmaceutically compatible salts of these compounds. The products have P-lactamase inhibiting properties. They are useful in combination with beta-lactam antibiotics in the control of beta-lactamase forming pathogens

β-lactam compounds

Compounds of the formula STR1 where Z, A, and R are as disclosed herein and pharmaceutically compatible, readily hydrolyzable esters and salts of these compounds are disclosed. The compounds have β-lactamase inhibiting properties and are useful in the control of β-lactamase-forming pathogens in combination with β-lactam antibiotics. They also exhibit antibacterial activity of their own and can accordingly be used themselves in the control or treatment of infectious diseases.