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Usage

Uses

Used in Medicinal Chemistry:
5-Bromo-7-[trans-4-(tert-butyldimethylsilyloxy)cyclohexyl]-2-chloro-7H-pyrrolo[2,3-d]pyrimidine is used as a potential candidate in medicinal chemistry for its unique structure and properties. The presence of the pyrrolo[2,3-d]pyrimidine core and the protecting tert-butyldimethylsilyloxy group suggests that it may have applications in the development of new pharmaceutical drugs.
Used in Organic Synthesis:
In the field of organic synthesis, 5-Bromo-7-[trans-4-(tert-butyldimethylsilyloxy)cyclohexyl]-2-chloro-7H-pyrrolo[2,3-d]pyrimidine is used as a building block for more complex organic molecules. Its specific structure allows for further chemical modifications and reactions, making it a valuable component in the synthesis of advanced organic compounds.
Used in Drug Development:
5-Bromo-7-[trans-4-(tert-butyldimethylsilyloxy)cyclohexyl]-2-chloro-7H-pyrrolo[2,3-d]pyrimidine is utilized in drug development for its potential to contribute to the creation of novel therapeutic agents. Its unique chemical features may offer new avenues for treating various diseases and conditions, pending further research and development.
Used in Chemical Research:
In the realm of chemical research, 5-Bromo-7-[trans-4-(tert-butyldimethylsilyloxy)cyclohexyl]-2-chloro-7H-pyrrolo[2,3-d]pyrimidine serves as a subject of study to explore its chemical properties, reactivity, and potential interactions with other molecules. This research can lead to a better understanding of its applications and limitations in various chemical processes.
Used in Pharmaceutical Industry:
Within the pharmaceutical industry, 5-Bromo-7-[trans-4-(tert-butyldimethylsilyloxy)cyclohexyl]-2-chloro-7H-pyrrolo[2,3-d]pyrimidine is used as a starting material or intermediate in the synthesis of new drugs. Its unique structure and the presence of the protecting group make it a promising candidate for the development of innovative medications.

Upstream product

• 1060816-58-1 5-bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine 
• 1621619-12-2 trans-4-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexan-1-ol 
• 1621619-13-3 7-(trans-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidine 
• 27489-62-9 trans-4-hydroxycyclohexylamine 
• 103202-62-6 cis-4-((tert-butyldimethylsilyl)oxy)cyclohexan-1-ol 
• 1621619-13-3 C₁₈H₂₈ClN₃OSi 
• 1621619-12-2 C₁₂H₁₄ClN₃O 

Downstream Products

• 1429881-91-3 trans-4-(2-(butylamino)-5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexan-1-ol 

Relevant academic research and scientific papers

Near infrared imaging of Mer tyrosine kinase (: MERTK) using MERi-SiR reveals tumor associated macrophage uptake in metastatic disease

The receptor tyrosine kinase Mer (MERTK) is a promising drug target in cancer, where it can influence the metastasis-promoting signaling of both tumor cells and immune cells alike; however, no small molecule probes currently exist to selectively image Mer. In this work, we design and synthesize a selective near-infrared fluorescent molecular probe of Mer (MERi-SiR). Confocal microscopy of metastases in mice reveals predominant probe accumulation in Mer-expressing tumor-associated macrophages.

THE METHODS FOR TREATMENT OF TUMORS

This invention is in the area of improved therapeutic combinations for and methods of treating selected cancers using specific Mer tyrosine kinase (MerTK) inhibitors in combination with immune checkpoint inhibitors. In one aspect, an improved treatment for select cancers is disclosed using specific Mer tyrosine kinase (MerTK) inhibitors, for example UNC2371, in combination with an immune checkpoint inhibitor, for example, a cytotoxic T-lymphocyte-associated protein 4 (CTLA4) inhibitor, a programmed cell death protein 1 (PD1) inhibitor, or a programmed death-ligand 1 (PDL-1) inhibitor.

UNC2025, a potent and orally bioavailable MER/FLT3 dual inhibitor

We previously reported a potent small molecule Mer tyrosine kinase inhibitor UNC1062. However, its poor PK properties prevented further assessment in vivo. We report here the sequential modification of UNC1062 to address DMPK properties and yield a new potent and highly orally bioavailable Mer inhibitor, 11, capable of inhibiting Mer phosphorylation in vivo, following oral dosing as demonstrated by pharmaco-dynamic (PD) studies examining phospho-Mer in leukemic blasts from mouse bone marrow. Kinome profiling versus more than 300 kinases in vitro and cellular selectivity assessments demonstrate that 11 has similar subnanomolar activity against Flt3, an additional important target in acute myelogenous leukemia (AML), with pharmacologically useful selectivity versus other kinases examined.

PYRROLOPYRIMIDINE COMPOUNDS FOR THE TREATMENT OF CANCER

The ectopic expression of Mer receptor tyrosine kinase (Mer) has been identified as a tumor cell survival gene product in Acute Lymphoblastic Leukemia (ALL) cells and a potential cause of ALL chemoresistance. Hence, we investigated whether the development of small molecule Mer inhibitors was possible. A first aspect of the present invention is a compound (sometimes referred to as an active compound herein) of Formula I, IA, or IB.