683241-92-1

Usage

Uses

Used in Medicinal Chemistry:
6-[4-(tert-butoxycarbonyl)piperazin-1-yl]-5-chloronicotinic acid is used as a precursor in the synthesis of pharmaceuticals for its potential pharmacological activities. 6-[4-(tert-butoxycarbonyl)piperazin-1-yl]-5-chloronicotinic acid's structure, incorporating both a piperazine ring and a chloronicotinic acid group, positions it for use in developing new drugs with specific therapeutic targets.
Used in Drug Development:
In the pharmaceutical industry, 6-[4-(tert-butoxycarbonyl)piperazin-1-yl]-5-chloronicotinic acid is utilized as a building block for the creation of novel drug candidates. Its unique chemical structure allows for the design of molecules that can interact with biological targets, potentially leading to the development of treatments for various diseases.
Used in Organic Synthesis:
6-[4-(tert-butoxycarbonyl)piperazin-1-yl]-5-chloronicotinic acid serves as an intermediate in organic synthesis, particularly where the Boc protecting group is strategically employed to prevent unwanted reactions during the synthesis process. This feature makes it valuable in the preparation of complex organic molecules with specific functionalities.

Upstream product

• 683241-93-2 4-(3-chloro-5-methoxycarbonyl-pyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 56055-54-0 methyl 2,3-dichloro-pyridine-5-carboxylate 
• 41667-95-2 5,6-dichloronicotinic acid 

Downstream Products

• 683241-96-5 tert-butyl 4-(3-chloro-5-((perfluorophenoxy)carbonyl)pyridin-2-yl)piperazine-1-carboxylate 

Relevant academic research and scientific papers

Synthesis, structure-property relationships and pharmacokinetic evaluation of ethyl 6-aminonicotinate sulfonylureas as antagonists of the P2Y12 receptor

The present paper describes the development of a new series of P2Y 12 receptor antagonists based on our previously reported piperazinyl urea series 1 (IC50 binding affinity = 0.33 μM, aq solubility 50 binding affinity = 0.042 μM, aq solubility = 90 μM, microsomal CLint (HLM) = 70 μM/min/mg). Further improvements in affinity and metabolic stability were achieved by replacing the central piperazine ring with a 3-aminoazetidine as exemplified by 3 (IC50 binding affinity = 0.0062 μM, aq solubility = 83 μM, microsomal CLint (HLM) = 28 μM/min/mg). The improved affinity observed in the in vitro binding assay also translated to the potency observed in the WPA aggregation assay (47: 19 nM and 3: 9.5 nM) and the observed in vitro ADME properties translates to the in vivo PK properties observed in rat. In addition, we found that the chemical stability of the sulfonylureas during prolonged storage in solution was related to the sulfonyl urea linker and depended on the type of solvent and the substitution pattern of the sulfonyl urea functionality.

II. SAR studies of pyridyl-piperazinyl-piperidine derivatives as CXCR3 chemokine antagonists

The structure-human CXCR3 binding affinity relationship of a series of pyridyl-piperazinyl-piperidine derivatives was explored. The optimization campaign highlighted the pronounced effect of 2'-piperazine substitution on CXCR3 receptor affinity. Analog 18j, harboring a 2'(S)-ethylpiperazine moiety, exhibited a human CXCR3 IC50 of 0.2 nM.

Novel CXCR3 antagonists with a piperazinyl-piperidine core

High-throughput screening of an encoded combinatorial aryl piperazine library led to the identification of a novel series of potent piperazinyl-piperidine based CXCR3 antagonists. Analogs of the initial hit were synthesized via solid and solution phase me

NOVEL PYRIDINE COMPOUNDS

The present invention relates to certain novel pyridin compounds of Formula ( I ) to processes for preparing such compounds, to their utility as P2Y12 inhibitors and as anti-trombotic agents etc, and processes for their preparation, their use as medicaments in cardiovascular diseases as well as pharmaceutical compositions containing them.

Design of potent, orally available antagonists of the transient receptor potential vanilloid 1. Structure-activity relationships of 2-piperazin-1-yl-1H- benzimidazoles

The vanilloid receptor-1 (VR1 or TRPV1) is a membrane-bound, nonselective cation channel that is predominantly expressed by peripheral neurons sensing painful stimuli. TRPV1 antagonists produce antihyperalgesic effects in animal models of inflammatory and neuropathic pain. Herein, we describe the synthesis and the structure-activity relationships of a series of 2-(4-pyridin-2- ylpiperazin-1-yl)-1H-benzo-[d]imidazoles as novel TRPV1 antagonists. Compound 46ad was among the most potent analogues in this series. This compound was orally bioavailable in rats and was efficacious in blocking capsaicin-induced flinch in rats in a dose-dependent manner. Compound 46ad also reversed thermal hyperalgesia in a model of inflammatory pain, which was induced by complete Freund's adjuvant (CFA).

BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS VANILLOID RECEPTOR LIGANDS

Compounds of formula (I) are useful in the treatment of vanilloid-receptor-meditated diseases, such as inflammatory or neuropathic pain and diseases involving sensory nerve function such as asthma, rheumatoid arthritis, osteoarthritis, inflammatory bowel disorders, urinary incontinence, migraine and psoriasis.