919351-41-0

Basic information

• Product Name: AZD1283
• Synonyms: AZD1283;6-[4-[[(Benzylsulfonyl)amino]carbonyl]piperidin-1-yl]-5-cyano-2-methylnicotinic acid ethyl ester;ethyl 6-(4-((benzylsulfonyl)carbamoyl)piperidin-1-yl)-5-cyano-2-methylnicotinate AZD1283
• CAS NO: 919351-41-0
• Molecular Formula: C23H26N4O5S
• Molecular Weight: 470.54134
• Mol File: 919351-41-0.mol

Chemical Properties

• Appearance: /
• Solubility: insoluble in H2O; insoluble in EtOH; ≥18.15 mg/mL in DMSO
• CAS DataBase Reference: AZD1283(CAS DataBase Reference)
• NIST Chemistry Reference: AZD1283(919351-41-0)
• EPA Substance Registry System: AZD1283(919351-41-0)

Safety Data

• Hazardous Substances Data: 919351-41-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
AZD1283 is used as a therapeutic agent for the treatment of conditions related to platelet activation and thrombus formation. Its ability to antagonize P2Y12R makes it a promising candidate for managing disorders associated with abnormal blood clotting, such as arterial thrombosis, stroke, and myocardial infarction.
Used in Cardiovascular Research:
In the field of cardiovascular research, AZD1283 serves as a valuable tool for studying the role of P2Y12R in platelet function and thrombus formation. By inhibiting the activity of this receptor, researchers can gain insights into the underlying mechanisms of blood clotting and develop new strategies for preventing and treating related diseases.
Used in Drug Development:
AZD1283 is also utilized in the development of new drugs targeting P2Y12R and related pathways. Its reversible antagonistic properties make it a suitable candidate for the creation of innovative pharmaceuticals aimed at improving cardiovascular health and managing blood clotting disorders.

Biological Activity

the central role of the p2y12 receptor in platelet function makes it an attractive target for the development of novel antiplatelet therapies. azd1283 is found to be a potent, selective and reversible antagonist of the p2y12 receptor.

in vitro

it was observed that the benzylic azd1283 and its analogue 13 were both potent in the higher order residual platelet count assay in which the two tested 5-chlorothienyls showed low (ic50 >22 μm) potency [1].

in vivo

in a modified folts model in dog, both azd1283 and its analogue 13 could dose-dependently induce increases in blood flow and inhibition of adp-induced platelet aggregation with antithrombotic ed50 values of 3.0 and 10.0 μg/kg/min, respectively. the dose that induced a larger than 3-fold increase in bleeding time were 33 and 100 μg/kg/min for azd1283 and 13, respectively [2].

IC 50

0.011, 0.025 and 3.2 μm for binding, gtpγs and residual platelet count (rpc), respectively

references

[1] bach p, antonsson t, bylund r, bj?rkman ja, ?sterlund k, giordanetto f, van giezen jj, andersen sm, zachrisson h, zetterberg f. lead optimization of ethyl 6-aminonicotinate acyl sulfonamides as antagonists of the p2y12 receptor. separation of the antithrombotic effect and bleeding for candidate drug azd1283. j med chem. 2013;56(17):7015-24.

Upstream product

• 498-94-2 isonipecotic acid 
• 64119-42-2 ethyl 6-chloro-5-cyano-2-methylnicotinate 
• 919354-22-6 4-[(benzylsulfonyl)carbamoyl]piperidinium hydrochloride 
• 1939-99-7 benzenesulfonyl chloride 
• 919354-24-8 1-[3-cyano-5-(ethoxycarbonyl)-6-methylpyridin-2-yl]-piperidine-4-carboxylic acid 
• 4563-33-1 phenyl-methanesulfonic acid amide 
• 52600-52-9 5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester 
• 141-97-9 ethyl acetoacetate 
• 134653-70-6 ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate 
• 512821-88-4 tert-butyl 4-[(benzylsulfonyl)carbamoyl]-piperidine-1-carboxylate 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 919354-21-5 N-(benzylsulfonyl)piperidine-4-carboxamide 

Relevant articles and documents

Development of a Multi-Kilogram-Scale Synthesis of AZD1283: A Selective and Reversible Antagonist of the P2Y12 Receptor

Ethyl 6-chloro-5-cyano-2-methylnicotinate (4) was coupled with 4-piperidinecarboxylic acid (isonipecotic acid) in 81% yield to pyridine acid 10. An amide coupling between 10 and benzylsulfonamide (6) afforded AZD1283 (1) in 79% yield using CDI as coupling reagent. The synthesis has been developed and scaled up to 20 kg batches of 1, supporting preclinical and clinical studies. Development work towards 2-chloropyridine 4 and benzylsulfonamide (6) is included.

Lead optimization of ethyl 6-aminonicotinate acyl sulfonamides as antagonists of the P2Y12 receptor. Separation of the antithrombotic effect and bleeding for candidate drug AZD1283

Synthesis and structure-activity relationships of ethyl 6-aminonicotinate acyl sulfonamides, which are potent antagonists of the P2Y12 receptor, are presented. Shifting from 5-chlorothienyl to benzyl sulfonamides significantly increased the pot

2-AMINO-6-ALKYL SUBSTITUTED PYRIDINE DERIVATIVES USEFUL AS P2Y12 INHIBITORS 308

The present invention relates to certain new pyridin analogues of Formula ( I ) to processes for preparing such compounds, to their utility as P2Y12 inhibitors and as anti-trombotic agents etc, their use as medicaments in cardiovascular disease

NOVEL CRYSTALLINE FORMS I AND II

The present invention relates to 6-(4-{[(benzylsulfonyl)amino]carbonyl}piperidin-1-yl)-5-cyano-2-methylnicotinic acid ethyl ester, form I and II, to processes for preparing such compounds, to their utility as P2Y12 inhibitors and as anti-thromb

NEW PYRIDINE ANALOGUES VIII 518

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

NEW PYRIDINE ANALOGUES

The present invention relates to certain new pyridin analogues of Formula (I) Chemical formula should be inserted here. Please see paper copy Formula (I) to processes for preparing such compounds, to their utility as P2Y12 inhibitors and as anti-trombotic agents etc, their use as medicaments in cardiovascular diseases as well as pharmaceutical compositions containing them.