477251-77-7

Usage

Functional Group

Ethyl ester derivative of 1,8-naphthyridine-3-carboxylic acid

Structural Feature

Contains a 3-bromophenyl group

Application

Used in research and development, particularly in the pharmaceutical industry

Potential Use

Applications in drug discovery and medicinal chemistry

Role

May be used as a building block for the synthesis of potential pharmaceutical compounds

Utility

Chemical structure and properties make it potentially useful for studying biological processes and developing new drugs

Upstream product

• 591-19-5 m-Bromoaniline 
• 220731-02-2 ethyl 3-(2-chloropyridin-3-yl)-3-oxopropionate 
• 412319-88-1 ethyl-3,3-dimethylaminoacrylate 
• 49609-84-9 2-Chloronicotinoyl chloride 
• 701977-68-6 Ethyl 3-(3-Bromoanilino)-2-(2-Chloronicotinoyl) Acrylate 

Downstream Products

• 477251-78-8 1-(3-Bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylic Acid 
• 500355-37-3 N-isopropyl-1-[(3-phenylethynyl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide 
• 500355-51-1 N-isopropyl-1-[3-(3-hydroxy-3-phenylbut-1-ynyl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide 
• 477251-79-9 N-Isopropyl-1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide 

Relevant academic research and scientific papers

A convenient one-pot synthesis of 1,8-naphthyridones

In this paper, we disclose an efficient one-pot procedure for the preparation of substituted 1,8-naphthyridin-4-one analogues. Previous efforts to effect this type of transformation were complicated by the formation of benzene tricarboxylate. Via the use of excess base, the impurity formation was completely inhibited. This allowed for the clean preparation of the desired intermediate and subsequent formation of naphthyridone analogues in a single flask, which could then be crystallized directly from the reaction mixture in good yield and high purity.

Alternative Forms of the Phosphodiesterase-4 Inhibitor N-Cyclopropyl-1--4-Oxo-1,4-Dihydro-1,8-Naphthyridine-3-Carboxyamide

The present invention is directed to alternative forms of the title phosphodiesterase 4 inhibitor which has the structural formula shown immediately below:

Discovery of MK-0952, a selective PDE4 inhibitor for the treatment of long-term memory loss and mild cognitive impairment

The structure-activity relationship of a novel series of 8-biarylnaphthyridinones acting as type 4 phosphodiesterase (PDE4) inhibitors for the treatment of long-term memory loss and mild cognitive impairment is described herein. The manuscript describes a new paradigm for the development of PDE4 inhibitor targeting CNS indications. This effort led to the discovery of the clinical candidate MK-0952, an intrinsically potent inhibitor (IC 50 = 0.6 nM) displaying limited whole blood activity (IC50 = 555 nM). Supporting in vivo results in two preclinical efficacy tests and one test assessing adverse effects are also reported. The comparative profiles of MK-0952 and two other Merck compounds are described to validate the proposed hypothesis.

Optimization and structure-activity relationship of a series of 1-phenyl-1,8-naphthyridin-4-one-3-carboxamides: Identification of MK-0873, a potent and effective PDE4 inhibitor

A SAR study of a series of 1-phenyl-1,8-naphthyridin-4-one-3-carboxamides is described. Optimization of the series was based on in vitro potency against PDE4, inhibition of the LPS-induced production of TNF-α in human whole blood and minimizing affinity f

ALTERNATIVE FORMS OF THE PHOSPHODIESTERASE-4 INHIBITOR N-CYCLOPROPYL-1-{3-[(1-OXIDOPRYIDIN-3-YL)ETHYNYL]PHENYL}-4-OXO-1,4-DIHYDRO-1,8-NAPHTHYRIDINE-3-CARBOXYAMIDE

The present invention is directed to alternative forms of the title phosphodiesterase 4 inhibitor which has the structural formula shown immediately below: Compound IX

METHOD OF PREPARING INHIBITORS OF PHOSPHODIESTERASE-4

In one aspect, the present invention is directed to a one pot method of preparing intermediates of Formula V, which are useful in making inhibitors of phosphodiesterase-4: The present invention is also directed to a method of preparing phosphodiesterase inhibitors comprising the Formula

4-OXO-1-(3-SUBSTITUTED PHENYL-1,4-DIHYDRO-1,8-NAPHTHYRIDINE-3-CARBOXAMIDE PHOSPHODIESTERASE-4 INHIBITORS

Compounds represented by Formula (I):or a pharmaceutically acceptable salt thereof, are phosphodiesterase 4 inhibitors useful in the treatment of asthma and inflammation and useful for the enhancement of cognition.

1-biaryl-1,8-naphthyridin-4-one phosphodiesterase-4 inhibitors

Compounds represented by Formula (I): or a pharmaceutically acceptable salt thereof, are phosphodiesterrase 4 inhibitors useful in the treatment of asthma and inflammation.

Alkyne-aryl phosphodiesterase-4 inhibitors

Compounds represented by Formula (I): or a pharmaceutically acceptable salt thereof, are phosphodiesterase 4 inhibitors useful in the treatment of asthma and inflammation.