1383814-64-9

Usage

Uses

Used in Pharmaceutical Industry:
(1R,2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide is used as an impurity in the production of Avibactam, a novel β-lactamase inhibitor. Its presence in the synthesis process of Avibactam is significant as it can impact the overall efficacy and safety of the final product. The compound is crucial in the development and optimization of Avibactam's production methods to ensure its purity and effectiveness as a potent inhibitor of lactamase from Mycobacterium tuberculosis.
In the context of Avibactam's application, (1R,2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide serves as a critical reference point for researchers and pharmaceutical companies to understand the synthesis process, optimize the production, and minimize the presence of impurities. This, in turn, helps to improve the overall quality and effectiveness of Avibactam as a β-lactamase inhibitor, ultimately contributing to the development of more effective treatments for tuberculosis and other bacterial infections.

Upstream product

• 1416134-49-0 (2S,5R)-5-(benzyloxyamino)-piperidine-2-carboxylic acid amide 
• 1383814-70-7 (2R,5S)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid 
• 1383814-69-4 (2R,5S)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate 
• 1383814-72-9 (2R,5S)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1383814-71-8 (2R,5S)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1] octane-2-carboxylic acid cyclohexylamine salt 
• 32159-21-0 Cbz-L-pGlu-OH 
• 1383814-53-6 (2S,5S)-tert-butyl 5-hydroxy-1-(2,2,2-trifluoroacetyl)piperidine-2-carboxylate 
• 1383814-52-5 (2S,5S)-tert-butyl 5-hydroxypiperidine-2-carboxylate 
• 169825-97-2 N-benzyloxycarbonyl-(2S,5S)-5-hydroxypipecolic acid tert-butyl ester 
• 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 
• 1383814-58-1 (2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid methyl ester 
• 1383814-56-9 (2S,5R)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate 
• 1383814-54-7 (2S,5R)-tert-butyl 5-(benzyloxyamino)-1-(2,2,2-trifluoroacetyl)piperidine-2-carboxylate 
• 147489-30-3 (2S)-5-oxopiperidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 

Downstream Products

• 1192651-80-1 ({[(2S,5R)-2-carbamoyl-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3,2,1]-oct-6-yl]oxy}sulfonyl)tetrabutylammonium salt 

Relevant academic research and scientific papers

2-CYANOPYRROLDINES, -PIPERIDINES OR -DAZEPINES AS HYPERGLYCEMIC AGENTS

Nitrogen containing compounds of Formula (I), pharmaceutical compositions comprising these compounds and their use in treating hypoglycaemia is disclosed.

CRYSTALLINE FORM OF AN AVIBACTAM DERIVATIVE

A crystalline form of an avibactam derivative (1), i.e. crystalline ethyl 3-(((((1R,2S,5R)-2-carbamoyl-7-oxo-l,6-diazabicyclo[3.2.1]octan-6-yl)oxy)sulfonyl)oxy)-2,2-dimethylpropanoate anhydrate (I), pharmaceutical compositions thereof, and the use of the crystalline avibactam derivative for treating bacterial infections are provided.

Avibactam intermediate, and preparation method and application of avibactam intermediate

The invention discloses an avibactam intermediate, and a preparation method of the avibactam intermediate. The preparation method comprises the steps of allowing a compound II to react with a sulfonation reagent in the presence of an alkaline agent and then react with the alkaline agent to form the avibactam intermediate, wherein the alkaline agent is trialkylamine, pyridine, alkylpyridine, N-alkylpiperidine, dialkyl phenylamine or dialkyl benzylamine; alkyl in trialkyl amine is C5-8 alkyl; alkyl in alkyl pyridine in C1-4 alkyl; alkyl in N-alkylpiperidine is C1-4 alkyl; alkyl in dialkyl phenylamine is C1-4 alkyl; and alkyl in dialkyl benzylamine is C1-4 alkyl. Compared with the traditional method, the method adopts the alkaline agent with appropriate alkalinity to substitute the traditional alkaline agent; the alkaline agent can react with the compound II in a step directly with the sulfonation reagent; the post-treatment is simple; and the method is more suitable for industrial mass production.

Orally Absorbed Derivatives of the β-Lactamase Inhibitor Avibactam. Design of Novel Prodrugs of Sulfate Containing Drugs

Only one FDA-approved β-lactamase inhibitor has ever been orally available: clavulanic acid, approved in 1984. Avibactam, approved by FDA in 2015, is the first of a new class of BLIs called diazabicyclooctanes, or "DBOs". This class has much broader coverage than clavulanic acid but can only be administered by intravenous injection. Herein, we describe the synthesis and testing of the first approved BLI to be rendered orally bioavailable since clavulanic acid (1984).

Beta-lactamase inhibitors and uses thereof

β-Lactamase inhibiting compounds, therapeutic methods of using the β-lactamase inhibiting compounds, particularly in combination with β-lactam antibiotics and pharmaceutical compositions thereof are disclosed. The β-lactamase inhibiting compounds are suitable for oral administration.

One-pot method of preparing avey batanBatan sodium (by machine translation)

The invention discloses a method for preparing avey batanBatan sodium pot method. The method to (2S, 5R) - 5 - [(benzyloxy) amino] piperidine - 2 - carboxylic acid ethyl ester oxalate as the starting material first with triphosgene generating compounds II, then after hydrolysis to obtain compound III ammoniation of adding ammonia water, then in hydrogenation reaction using formic acid, ammonium formate or hydrazine hydrate as hydrogen donor hydrogenation after avey batanBatan sodium and get. The method adopts the one-pot preparation avey batanBatan sodium, and the raw material is cheap, mild reaction conditions, the operation is simple, and higher safety, high yield, purity is good, is suitable for the large-scale industrial production. (by machine translation)

Synthetic method for avibactam sodium salt

The invention discloses a synthetic method for avibactam sodium salt. The method comprises the following steps: taking (2S, 5R)-5-[(benzyl oxyl) amino] piperidine-2-formamide as a starting material; constructing a urea ring by carbonyl diimidazole under the effect of dimethyldichlorosilance to obtain (2S, 5R)-6-(benzyl oxyl)-7-oxo-1,6-diazabicyclo [3.2.1] octane-2-formamide; then carrying out hydrogenation to remove benzyl; carrying out sulfonation reaction on the compound and a sulfonated reagent; synthesizing into a quaternary ammonium salt intermediate by using quaternary ammonium salt; and finally carrying out ion exchange to obtain the avibactam sodium salt. The improved process is low in cost, simple and convenient to operate, good in product quality and suitable for industrial production. In a process of synthesizing the intermediate (2S, 5R)-6-(benzyl oxyl)-7-oxo-1,6-diazabicyclo [3.2.1] octane-2-formamide, dimethyldichlorosilance which is low in price is used, and therefore, the production cost is greatly reduced.

Diazabicyclo octanone sulfuric acid monoester synthesis method

The invention relates to a synthesis method of a compound diazabicyclo octanone sulfuric acid monoester for preventing and treating bacterial infection diseases. According to the synthesis method, cheap and available glutamate lactam is taken as a raw material and reacts for twelve steps, and chemical synthesis of diazabicyclo octanone sulfuric acid monoester is completed with higher total yield. According to the novel synthesis method of diazabicyclo octanone sulfuric acid monoester, the preparation method is simple and convenient, an intermediate is stable, environmental protection and economy are achieved, and the reaction is easy to control.

Method for synthesizing beta-lactamase inhibitor Avibactam

The invention relates to a method for synthesizing a beta-lactamase inhibitor Avibactam and belongs to the technical field of preparation of beta-lactamase inhibitors. The method disclosed by the invention comprises the following steps: (1) taking a compound 2 as a raw material, and reacting with RNH2 so as to produce a compound 3; (2) enabling the compound 3 and a biocatalyst to produce a compound 4 in an organic solvent in the presence of glucose or sucrose; (3) enabling the compound 4 to react with trifluoroacetic anhydride so as to obtain a compound 5; (4) enabling the compound 5 to react with RONH2 so as to produce a compound 6; (5) hydrolyzing the compound 6 under alkaline conditions so as to produce a compound 7; (6) enabling the compound 7 to react with triphosgene so as to produce a compound 8; (7) enabling the compound 8 to react with ammonium formate in the presence of a catalyst so as to produce a compound 9 in the organic solvent, wherein the catalyst is a Pd/C system; and (8) enabling the compound 9 to react with a sulfonating agent, thereby obtaining the product 1. The method disclosed by the invention is stable in process, high in yield, simple and safe in operation and low in production cost.

A PROCESS FOR SODIUM SALT OF (2S, 5R)-2-CARBOXAMIDO-7-OXO-6-SULFOOXY -1,6-DIAZA-BICYCLO[3.2.1]OCTANE

A process for preparation of a sodium salt of (2S, 5R)-2- carboxamido-7-oxo-6-sulfooxy-l,6-diaza-bicyclo[3.2.1]octane is disclosed which is comprising the amidation of a compound of Formula (II) to obtain a compound of Formula (III).