280773-16-2

Usage

Uses

Used in Pharmaceutical Research:
2-Nitro-N-(5-chloro-pyridin-2-yl)-5-methoxy-benzamide is used as a research compound for exploring its potential biological activities and therapeutic effects. Its structural features, including the nitro group, chlorine atom, and pyridine ring, may contribute to its pharmacological properties, making it a candidate for further investigation in drug development.
Used in Drug Development:
In the pharmaceutical industry, 2-Nitro-N-(5-chloro-pyridin-2-yl)-5-methoxy-benzamide is utilized as a starting material or intermediate in the synthesis of new drugs. Its unique chemical structure may offer novel mechanisms of action or selectivity against specific targets, which could be beneficial in the treatment of various diseases.

InChI:InChI=1/C13H10ClN3O4/c1-21-9-3-4-11(17(19)20)10(6-9)13(18)16-12-5-2-8(14)7-15-12/h2-7H,1H3,(H,15,16,18)

Upstream product

• 1882-69-5 5-methoxy-2-nitro-benzoic acid 
• 1072-98-6 5-chloro-2-pyridylamine 

Downstream Products

• 280773-17-3 2-amino-N-(5-chloro-pyridin-2-yl)-5-methoxy-benzamide 
• 330942-05-7 betrixaban 
• 1416698-97-9 2-(4-(N-(2-chloroacetyl)-S-methylsulfonimidoyl)benzamido)-N-(5-chloropyridin-2-yl)-5-methoxybenzamide 
• 1147095-86-0 S-[4-(N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-methoxyphenyl}carbamoyl)phenyl]-S-methyl-N-(2-diethylamino-acetyl)sulfoximide 
• 1147095-60-0 S-[4-(N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-methoxyphenyl}carbamoyl)phenyl]-S-methyl sulfoximide 
• 1514962-30-1 5-(2-((6-amidohexyl)amino)-2-oxoethyoxy)-2-(4-(N,N-dimethylcarbamimidoyl)benzamido)-N-(pyridine-2-yl)benzamide 
• 1616693-62-9 C₁₂H₈ClN₃O₄ 
• 1616693-63-0 C₁₅H₁₂ClN₃O₆ 
• 1616693-64-1 C₁₄H₁₀ClN₃O₆ 
• 1616693-65-2 C₂₅H₃₂ClN₅O₇ 
• 1639024-44-4 C₃₅H₄₅N₇O₆ 

Relevant academic research and scientific papers

Improved preparation method of beta-caraban

The invention relates to the fields of organic chemistry and pharmacy, and particularly relates to an improved method for preparing betrixaban. Compared with the prior art, the method has the advantages that the defects of use of high-corrosion hydrogen chloride gas, heavy burden for 'three wastes' treatment, difficult refining and purification of products and the like can be overcome. The method is characterized in that a metal organic compound RMR' (M is selected from Mg and Zn, R is selected from Cl, Br, I, alkyl or aryl, and R' is selected from akly or aryl) is used for reacting with dimethylamine or salt thereof in an aprotic solvent; then the obtained reacting liquid reacts with the compound or salt thereof in a formula II to prepare betrixaban. The improved novel method has the advantages of use of easily available raw materials, mild reaction condition, convenience in operation, excellent product quality and low cost and is suitable for industrial large-scale production.

Method for preparing betrixaban intermediate

The invention provides a method for preparing a betrixaban intermediate. The method comprises the following step of using 5-methoxyl-2-nitrobenzoic acid and 2-amino-5-chloropyridine as initiating rawmaterials, so as to prepare N-(5-chloro-2-pyridyl)-5-met

Design, synthesis and biological evaluation of anthranilamide derivatives as potential factor Xa (fXa) inhibitors

Factor Xa (fXa) is a crucial player in various thromboembolic disorders. Inhibition of fXa can provide safe and effective antithrombotic effects. In this study, a series of anthranilamide compounds were designed by utilizing structure-based design strategies. Optimization at P1 and P4 groups led to the discovery of compound 16g: a highly potent, selective fXa inhibitor with pronounced in vitro anticoagulant activity. Moreover, 16g also displayed excellent in vivo antithrombotic activity in the rat venous thrombosis (VT) and arteriovenous shunt (AV-SHUNT) models. The bleeding risk evaluation showed that 16g had a safer profile than that of betrixaban at 1 mg/kg and 5 mg/kg dose. Additionally, 16g also exhibited satisfactory PK profiles. Eventually, 16g was selected to investigate its effect on hypoxia-reoxygenation- induced H9C2 cell viability. MTT results showed that H9C2 cell viability can be remarkably alleviated by 16g.

Bei quxi class crystal form and its preparation and use

The invention discloses crystal forms of a factor Xa inhibitor betrixaban, a preparing method thereof, pharmaceutical compositions comprising the crystal forms of the betrixaban, and uses of the crystal forms of the betrixaban in preparation of medicines used for preventing or treating mammal diseases characterized by adverse thrombus formation.

Synthesis and structure-activity relationship of potent, selective and orally active anthranilamide-based factor Xa inhibitors: Application of weakly basic sulfoximine group as novel S4 binding element

A novel series of potent and efficacious factor Xa inhibitors which possesses sulfoximine moiety as novel S4 binding element in anthranilamide chemotype has been identified. Lead optimization at this novel P4 group led to many potent factor Xa inhibitors with excellent anticoagulant activity in human plasma. Selected compounds were dosed orally in rats and checked for their ex vivo prothrombin time prolonging activity, which resulted in identification of compound 5-chloro-N-(5-chloropyridin-2-yl)-2-(4-(N-(2-(diethylamino)acetyl)-S- methylsulfonimidoyl)benzamido)benzamide (18f). The detailed pharmacokinetic evaluation and subsequent metabolism study of 18f suggested the presence of an active metabolite. The compound 18f and its active metabolite 18b demonstrated excellent in vivo efficacy in both arterial and venous thrombosis model in rats and were found to be highly selective against related serine proteases. Based on this promising profile, compound 18f was selected for further evaluation.

URETHANES, UREAS, AMIDINES AND RELATED INHIBITORS OF FACTOR XA

The invention relates to a new class of compounds, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions that are effective as selective inhibitors of factor Xa, both in the isolated state and in a complex with other proteins. The compounds of the invention can be used for treating and preventing diseases, such as acute coronary syndrome, myocardial infarction, unstable angina, refractory angina, thromboses caused by post-thrombolytic therapy or coronary angioplasty, acute ischemia mediated cerebrovascular syndrome, embolic stroke, thrombotic stroke, and other diseases in humans and other mammals associated with blood coagulation problems.

METHODS OF SYNTHESIZING FACTOR XA INHIBITORS

Described herein are novel methods of preparing a compound of Formula II or a pharmaceutically acceptable salt thereof. In some embodiments, the method is for preparing betrixaban or a pharmaceutically acceptable salt thereof. Also described are compositions comprising substantially pure betrixaban free base or salt thereof.

Discovery of betrixaban (PRT054021), N-(5-chloropyridin-2-yl)-2-(4-(N,N-dimethylcarbamimidoyl)benzamido)-5-methoxybenzamide, a highly potent, selective, and orally efficacious factor Xa inhibitor

Systematic SAR studies of in vitro factor Xa inhibitory activity around compound 1 were performed by modifying each of the three phenyl rings. A class of highly potent, selective, efficacious and orally bioavailable direct factor Xa inhibitors was discovered. These compounds were screened in hERG binding assays to examine the effects of substitution groups on the hERG channel affinity. From the leading compounds, betrixaban (compound 11, PRT054021) has been selected as the clinical candidate for development.

Unit dose formulations and methods of treating thrombosis with an oral factor Xa inhibitor

Unit doses of factor Xa inhibitor compounds and methods of using these compounds for inhibiting blood coagulation in a human patient are taught herein. The unit dose of the factor Xa inhibitor compounds disclosed herein required to inhibit coagulation in a primate is lower than the unit dose required to obtain similar levels of coagulation inhibition in other animal models, such as rodents. Also taught are in vitro assays useful in predicting in vivo antithrombotic activity in humans.

METHODS OF SYNTHESIZING PHARMACEUTICAL SALTS OF A FACTOR XA INHIBITOR

Novel methods of preparing a compound of Formula I which is an inhibitor of Factor Xa and its maleate salt, are described herein.