1426573-07-0

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1171080-45-7 (2S,5R)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt 
• 81470-51-1 tert-butyl N-benzyloxycarbonyl-L-pyroglutamate 
• 53100-44-0 L-N-t-butoxycarbonylpyroglutamic acid 
• 1416134-47-8 (2S,5R)?5?[(benzyloxy)amino]piperidine?2?carboxylate 
• 1171080-44-6 (2S,5R)-5-(benzyloxyamino)-piperidine-2-carboxylic acid benzyl ester 
• 1416134-73-0 (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate methyl ester 
• 1463501-46-3 (2S,5R)-5-(benzyloxyamino)piperidin-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 695183-75-6 (2S,5S)-5-hydroxypiperidin-2-carboxylic acid methyl ester 
• 63088-78-8 (2S,5R)-5-hydroxypiperidine-2-carboxylic acid 

Downstream Products

• 1452458-86-4 RG₆₀₈₀ 
• 1383814-60-5 (2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid 2,5-dioxopyrrolidin-1-yl ester 

Relevant academic research and scientific papers

Diastereoselective FeCl3·6H2O/NaBH4 Reduction of Oxime Ether for the Synthesis of β-Lactamase Inhibitor Relebactam

Relebactam, a potent β-lactamase inhibitor, in combination with Primaxin is an FDA-approved (Recarbrio) treatment for serious and antibiotic-resistant bacterial infections. An efficient synthesis of key chiral piperidine intermediate 1 suitable for large-scale preparation of relebactam is described. The key steps include a unique highly diastereoselective FeCl3·6H2O/NaBH4 reduction of a chiral oxime ether and chemoselective amidation of the resulting unprotected pipecolic acid. Nuclear magnetic resonance studies and density functional theory calculations were carried out on the substrate-Fe(III) complexes, which shed light on diastereoselective reduction.

Preparation method of Avibactam intermediate

The invention relates to a preparation method of an Avibactam intermediate. The intermediate is (1R, 2S, 5R)-6-benzyloxy-7-oxo-1,6-diazacyclo[3.2.1]octane-2-methanamide. The method is easy to implement; total yield is high; purity of the product obtained is high; and the product is easy to purify.

Synthesis of bicyclic β-lactamase inhibitor relabactam derivatives from a relabactam intermediate

We have developed highly efficient chemistry to prepare two key intermediates from a Relabactam intermediate available from the process chemistry. The new intermediates enabled us to quickly synthesize other Ralebactam derivatives such as compound 1.

Production method for diazabicyclooctane derivative and intermediary body thereof

The present invention provides a production method for a diazabicyclooctane derivative expressed by formula (IV), and an intermediary body thereof (in the formula: P is an acid-removable NH protective group; R1 represents a 2, 5-dioxopyrrolidine-1-yl, a 1, 3-dioxo-3a, a 4, 7, 7a-tetrahydro-1H-isoindole-2(3H)-yl, a 1, 3-dioxohexahydro-1H-isoindole-2(3H)-yl, or a 3, 5-dioxo-4-azatricyclo[5.2.1.02, 6]deca-8-en-4-yl; R2 represents hydrogen, C1CO-, or C13COCO-, R3 represents a C1-6 alkyl or a heterocyclyl, or joins with a bonded -O-NH- to form a 3-7 member heterocyclyl ring; and OBn represents a benzyloxy).

CRYSTALLINE FORMS OF DIAZABICYCLOOCTANE DERIVATIVE AND PRODUCTION PROCESS THEREOF

A crystalline form of a diazabicyclooctane derivative represented by the following Formula (VII), and processes for producing the same:

CRYSTAL OF DIAZABICYCLEOCTANE DERIVATE AND METHOD FOR PRODUCING THE SAME

The present invention provides a crystal of diazabicycleoctane derivate represented by the following formula (VII), especially formula (VII-1), and a method for producing the same.

A PROCESS FOR PREPARATION OF SODIUM (2S, 5R)-6-(BENZYLOXY)-7-OXO-1,6-DIAZABICYCLO[3.2.1]OCTANE-2-CARBOXYLATE

A process for preparation of a compound of Formula (I) is disclosed.

NOVEL -LACTAMASE INHIBITOR AND METHOD FOR PRODUCING SAME

The currently available β-lactamase inhibitors are insufficient to inhibit the incessantly increasing β-lactamase, and novel β-lactamase inhibitors has been required today for the difficult treatment for bacterial infectious diseases caused by resistant bacteria which produce class C β-lactamase, extended-spectrum β-lactamase (ESBL) belonging to class A and D, or class A KPC-2 decomposing even carbapenem as a last resort for β-lactam antibiotic. A compound represented by the the formula (I), preparation process of the same, β-lactamase inhibitors and method for treating bacterial infectious diseases are provided.

NITROGEN CONTAINING COMPOUNDS AND THEIR USE

Compounds of Formula (I), their preparation and use in preventing or treating bacterial infections are disclosed.