959617-87-9

Usage

Uses

Used in Pharmaceutical Industry:
(3R,4R)-benzyl 4-aMino-3-hydroxypiperidine-1-carboxylate is used as a building block for synthesizing pharmaceutical compounds due to its unique structural properties, including an amino group, a hydroxyl group, and a cyclic piperidine ring.
Used in Medicinal Chemistry:
(3R,4R)-benzyl 4-aMino-3-hydroxypiperidine-1-carboxylate is used as a valuable intermediate in organic synthesis and drug discovery, providing versatility in functionalization through its benzyl group, which allows for the modification of the compound's properties for specific applications.

Upstream product

• 167832-25-9 trans(±)benzyl-4-azido-3-hydroxypiperidine-1-carboxylate 

Downstream Products

• 1007596-64-6 benzyl (3R,4R)-4-(benzhydrylideneamino)-3-hydroxy-piperidine-1-carboxylate 
• 1007596-96-4 (3R,4R)-tert-butyl 3-azido-4-[(diphenylmethylene)amino]piperidine-1-carboxylate 
• 1007596-93-1 tert-butyl (3R,4R)-4-[(diphenylmethylene)amino]-3-hydroxypiperidine-1-carboxylate 
• 1007596-95-3 (3R,4R)-tert-butyl 4-amino-3-hydroxypiperidine-1-carboxylate 
• 1007596-66-8 benzyl (3S,4R)-4-amino-3-azidopiperidine-1-carboxylate 
• 1007596-67-9 benzyl (3S,4R)-3-azido-4-[(3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl)amino]piperidine-1-carboxylate 
• 1007596-65-7 benzyl (3S,4R)-3-azido-4-(benzhydrylideneamino)piperidine-1-carboxylate 

Relevant academic research and scientific papers

Optimization of pyrrolamide topoisomerase II inhibitors toward identification of an antibacterial clinical candidate (AZD5099)

AZD5099 (compound 63) is an antibacterial agent that entered phase 1 clinical trials targeting infections caused by Gram-positive and fastidious Gram-negative bacteria. It was derived from previously reported pyrrolamide antibacterials and a fragment-based approach targeting the ATP binding site of bacterial type II topoisomerases. The program described herein varied a 3-piperidine substituent and incorporated 4-thiazole substituents that form a seven-membered ring intramolecular hydrogen bond with a 5-position carboxylic acid. Improved antibacterial activity and lower in vivo clearances were achieved. The lower clearances were attributed, in part, to reduced recognition by the multidrug resistant transporter Mrp2. Compound 63 showed notable efficacy in a mouse neutropenic Staphylococcus aureus infection model. Resistance frequency versus the drug was low, and reports of clinical resistance due to alteration of the target are few. Hence, 63 could offer a novel treatment for serious issues of resistance to currently used antibacterials.

PYRROLE DERIVATIVES WITH ANTIBACTERIAL ACTIVITY

Compounds of formula (I) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.