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Usage

Uses

Used in Medicinal Chemistry:
5-Bromo-1,2-dihydro-2-oxo-spiro[3H-indole-3,4'-piperidine]-1'-carboxylic acid 1,1-dimethylethyl ester is used as a potential pharmaceutical agent for its unique molecular structure that may interact with biological targets, offering new avenues for drug discovery and development.
Used in Organic Synthesis:
In the field of organic synthesis, 5-Bromo-1,2-dihydro-2-oxo-spiro[3H-indole-3,4'-piperidine]-1'-carboxylic acid 1,1-dimethylethyl ester serves as a valuable building block. Its functional groups and spiro ring system can be utilized in the creation of novel compounds with specific properties for various applications, including the development of new materials and pharmaceuticals.
Used in Research and Development:
5-Bromo-1,2-dihydro-2-oxo-spiro[3H-indole-3,4'-piperidine]-1'-carboxylic acid 1,1-dimethylethyl ester is employed in research settings to explore its chemical properties, reactivity, and potential interactions with biological systems. This research can lead to a better understanding of its role in chemical and biological processes, potentially uncovering new uses and applications.
Used in Chemical Libraries:
For high-throughput screening in drug discovery, 5-Bromo-1,2-dihydro-2-oxo-spiro[3H-indole-3,4'-piperidine]-1'-carboxylic acid 1,1-dimethylethyl ester is used as a component of chemical libraries. Its inclusion allows researchers to test a wide range of compounds against various diseases and conditions, facilitating the identification of new lead compounds for medicinal development.
Used in Advanced Material Development:
5-Bromo-1,2-dihydro-2-oxo-spiro[3H-indole-3,4'-piperidine]-1'-carboxylic acid 1,1-dimethylethyl ester may also be used in the development of advanced materials, such as sensors, due to its unique chemical and physical properties. Its potential to interact with specific molecules or change its properties under certain conditions makes it a candidate for innovative material applications.

Upstream product

• 118753-70-1 N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine 
• 59-48-3 2-oxoindole 
• 20870-78-4 5-bromo-2-indolin-2-one 
• 252882-60-3 tert-butyl 2-oxo-1,2-dihydro-1'H-spiro[indole-3,4-piperidine]-1'-carboxylate 

Downstream Products

• 1086280-87-6 C₂HF₃O₂*C₃₁H₂₈BrN₃O 

Relevant academic research and scientific papers

1,3,8-triazaspiro[4.5]decane-2,4-diones as efficacious pan-inhibitors of hypoxia-inducible factor prolyl hydroxylase 1-3 (HIF PHD1-3) for the treatment of anemia

The discovery of 1,3,8-triazaspiro[4.5]decane-2,4-diones (spirohydantoins) as a structural class of pan-inhibitors of the prolyl hydroxylase (PHD) family of enzymes for the treatment of anemia is described. The initial hit class, spirooxindoles, was identified through affinity selection mass spectrometry (AS-MS) and optimized for PHD2 inhibition and optimal PK/PD profile (short-acting PHDi inhibitors). 1,3,8-Triazaspiro[4.5]decane-2,4-diones (spirohydantoins) were optimized as an advanced lead class derived from the original spiroindole hit. A new set of general conditions for C-N coupling, developed using a high-throughput experimentation (HTE) technique, enabled a full SAR analysis of the spirohydantoins. This rapid and directed SAR exploration has resulted in the first reported examples of hydantoin derivatives with good PK in preclinical species. Potassium channel off-target activity (hERG) was successfully eliminated through the systematic introduction of acidic functionality to the molecular structure. Undesired upregulation of alanine aminotransferese (ALT) liver enzymes was mitigated and a robust on-/off-target margin was achieved. Spirohydantoins represent a class of highly efficacious, short-acting PHD1-3 inhibitors causing a robust erythropoietin (EPO) upregulation in vivo in multiple preclinical species. This profile deems spirohydantoins as attractive short-acting PHDi inhibitors with the potential for treatment of anemia.

SPIROINDALONES

The present invention relates to spiroindalone compounds useful as HIF prolyl hydroxylase inhibitors to treat anemia and like conditions.