252989-87-0

Usage

Uses

Used in Pharmaceutical Industry:
3-((tert-Butoxycarbonyl)aMino)-3-(6-chloropyridin-3-yl)propanoic acid is used as a building block for the synthesis of therapeutic agents. Its Boc protective group allows for selective deprotection under acidic conditions, enabling the synthesis of various pharmaceutical compounds with specific biological activities.
Used in Organic Synthesis:
3-((tert-Butoxycarbonyl)aMino)-3-(6-chloropyridin-3-yl)propanoic acid is used as an important intermediate in organic synthesis. Its unique structure and functional groups make it a versatile compound for the preparation of various organic molecules with potential applications in different fields, such as materials science, agrochemicals, and pharmaceuticals.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 297773-48-9 3-amino-3-(6-chloro-pyridin-3-yl)-propionic acid 
• 23100-12-1 6-chloronicotinylaldehyde 

Relevant academic research and scientific papers

An expedient method for resolution of 3-amino-3-(3′-pyridyl)propionic acid and related compounds

Preparation of methyl (S)-3-amino-3-(3′-pyridyl)propionate dihydrochloride in high enantiomeric purity by selective crystallization of a diastereomeric salt of a carboxylic acid precursor (W-BOC-protected) with (1R,2S)-(-)-ephedrine is described. Further demonstration of the usefulness of this procedure to resolve other 3-amino-3-[(substituted)pyridyl]propionic acids is also described.

Potent, orally active GPIIb/IIIa antagonists containing a nipecotic acid subunit. Structure-activity studies leading to the discovery of RWJ-53308

Although intravenously administered antiplatelet fibrinogen receptor (GPIIb/IIIa) antagonists have become established in the acute-care clinical setting for the prevention of thrombosis, orally administered drugs for chronic use are still under development. Herein, we present details from our exploration of structure-activity surrounding the prototype fibrinogen receptor antagonist RWJ-50042 (racemate of 1), which was derived from a unique approach involving the γ-chain of fibrinogen (Hoekstra et al. J. Med. Chem. 1995, 38, 1582). Our analogue studies culminated in the discovery of RWJ-53308 (2), a potent, orally active GPIIb/IIIa antagonist. To progress from RWJ-50042 to a suitable candidate for clinical development, we conducted a series of optimization cycles that employed solid-phase parallel synthesis for the rapid, efficient preparation of nearly 250 analogues, which were assayed for fibrinogen receptor affinity and inhibition of platelet aggregation induced by four different activators. This strategy produced several promising analogues for advanced study, including 3-(3,4- methylenedioxybenzene)-β-amino acid analogue 3 (significant improved in vivo potency) and 3-(3-pyridyl)-β-amino acid 2 (significantly improved potency, oral absorption, and duration of action). In dogs, 2 displayed significant ex vivo antiplatelet activity on oral administration at 1.0 mg/kg, 16% systemic oral bioavailability, minimal metabolic transformation, and an excellent safety profile. Additionally, 2 was found to be efficacious in three in vivo thrombosis models: canine arteriovenous (AV) shunt (0.01-0.1 mg/kg, iv), guinea pig photoactivation-induced injury (0.3-3 mg/kg, iv), and guinea pig ferric chloride-induced injury (0.3-1 mg/kg, iv). On the basis of its noteworthy preclinical data, RWJ-53308 (2) was selected for clinical evaluation.