1159501-66-2

Basic information

• Product Name: (R)-2-((tert-butoxycarbonyl)aMino)-3-(diethoxyphosphoryl)propanoic acid
• Synonyms: (R)-2-((tert-butoxycarbonyl)aMino)-3-(diethoxyphosphoryl)propanoic acid;N-(tert-Butoxycarbonyl)-3-(diethoxyphosphoryl)-L-alanine
• CAS NO: 1159501-66-2
• Molecular Formula: C12H24NO9P
• Molecular Weight: 357.294021
• EINECS: -0
• Mol File: 1159501-66-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 467.5±40.0 °C(Predicted)
• Appearance: /
• Density: 1.201±0.06 g/cm3(Predicted)
• PKA: 3.48±0.10(Predicted)
• CAS DataBase Reference: (R)-2-((tert-butoxycarbonyl)aMino)-3-(diethoxyphosphoryl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-((tert-butoxycarbonyl)aMino)-3-(diethoxyphosphoryl)propanoic acid(1159501-66-2)
• EPA Substance Registry System: (R)-2-((tert-butoxycarbonyl)aMino)-3-(diethoxyphosphoryl)propanoic acid(1159501-66-2)

Safety Data

• Hazardous Substances Data: 1159501-66-2(Hazardous Substances Data)

Usage

General Description

The chemical compound "(R)-2-((tert-butoxycarbonyl)aMino)-3-(diethoxyphosphoryl)propanoic acid" is a derivative of the amino acid proline. It consists of a proline backbone with an additional amino group protected by a tert-butoxycarbonyl (Boc) group and a diethoxyphosphoryl group attached to the alpha carbon. The Boc group serves as a temporary protection for the amino group, allowing for selective manipulation of the proline during chemical synthesis. The diethoxyphosphoryl group, on the other hand, is commonly used as a phosphonate protecting group in organic synthesis. (R)-2-((tert-butoxycarbonyl)aMino)-3-(diethoxyphosphoryl)propanoic acid likely has applications in peptide synthesis and organic chemistry.

Upstream product

• 170848-34-7 N-t-butoxycarbonyl-3-iodo-D-alanine methyl ester 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 851475-17-7 2-(R)-tert-butoxycarbonylamino-3-(diethoxyphosphoryl)-propionic acid methyl ester 
• 651036-12-3 [2-(R)-chloro-1-(2-trimethylsilanyl-ethoxymethoxymethyl)-ethyl]-carbamic acid tert-butyl ester 
• 651035-90-4 (2-(R)-chloro-1-hydroxymethyl-ethyl)-carbamic acid tert-butyl ester 
• 651035-84-6 2-(R)-tert-butoxycarbonylamino-3-chloro-propionic acid methyl ester 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 851475-14-4 [2-(R)-(tert-butoxycarbonylamino)-3-(2-trimethylsilanyl-ethoxymethoxy)-propyl]-phosphonic acid diethyl ester 
• 851475-15-5 (2-(R)-tert-butoxycarbonylamino-3-hydroxy-propyl)-phosphonic acid diethyl ester 

Relevant articles and documents

4-((R)-2-{[6-((S)-3-Methoxypyrrolidin-1-yl)-2-phenylpyrimidine-4-carbonyl]amino}-3-phosphonopropionyl)piperazine-1-carboxylic Acid Butyl Ester (ACT-246475) and Its Prodrug (ACT-281959), a Novel P2Y12 Receptor Antagonist with a Wider Therapeutic Window in the Rat Than Clopidogrel

Recent post hoc analyses of several clinical trials with P2Y12 antagonists showed the need for new molecules being fully efficacious as antiplatelet agents and having a reduced propensity to cause major bleeding. We have previously reported the discovery of the 2-phenylpyrimidine-4-carboxamide analogs as P2Y12 antagonists with nanomolar potency in the disease-relevant platelet aggregation assay in human plasma. Herein we present the optimization steps that led to the discovery of clinical candidate ACT-246475 (30d). The key step was the replacement of the carboxylic acid functionality by a phosphonic acid group which delivered the most potent molecules of the program. In addition, low in vivo clearance in rat and dog was achieved for the first time. Since the bioavailability of 30d was low in rat and dog, we developed the bis((isopropoxycarbonyl)oxy)methyl ester prodrug (ACT-281959, 45). Compound 30d showed efficacy in the rat ferric chloride thrombosis model when administered intravenously as parent or orally as its prodrug 45. Moreover, 30d displays a wider therapeutic window as compared to clopidogrel in the rat surgical blood loss model.

6-(3-AZA-BICYCLO[3.1.0]HEX-3-YL)-2-PHENYL-PYRIMIDINES

The present invention relates to 6-(3-aza-bicyclo[3.1.0]hex-3-yl)-2-phenyl-pyrimidine derivatives and their use as P2Y12 receptor antagonists in the treatment and/or prevention of peripheral vascular, of visceral-, hepatic- and renal-vascular, of cardiovascular and of cerebrovascular diseases or conditions associated with platelet aggregation, including thrombosis in humans and other mammals.

PHOSPHONIC ACID DERIVATES AND THEIR USE AS P2Y12 RECEPTOR ANTAGONISTS

The invention relates to 2-phenyl-pyrimidine derivatives containing a phosphonic acid motif and their use as P2Y12 receptor antagonists in the treatment and/or prevention of peripheral vascular, of visceral-, hepatic- and renal-vascular, of cardiovascular and of cerebrovascular diseases or conditions associated with platelet aggregation, including thrombosis in humans and other mammals. (I).