503437-19-2Relevant academic research and scientific papers
Preparation method and application of N-cyanomethyl bis(trifluoromethyl) nicotinamide
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Paragraph 0021; 0022; 0027, (2017/11/04)
The invention discloses a preparation method of N-cyanomethyl bis(trifluoromethyl) nicotinamide. The preparation method is implemented according to the following steps of: by adopting 2, 6-dichloro-3-cyano-4-tirfluoromethyl pyridine as a material, carrying out nitrile-group hydrolysis, hydrogenolysis and amidation reaction, and finally preparing the N-cyanomethyl bis(trifluoromethyl) nicotinamide, wherein the filtrate generated in the amidation reaction can be used as a reaction solvent for amidation reaction again after heating filtration and cooling filtration to prepare the N-cyanomethyl bis(trifluoromethyl) nicotinamide. The N-cyanomethyl bis(trifluoromethyl) nicotinamide prepared by adopting the preparation method is 71.1-85.7% in yield and 99.1-99.9%, and can be applied as a standard product for detecting the content of flonicamid and calibrating the content of impurities in the preparation process. The preparation method is applicable to preparing the N-cyanomethyl bis(trifluoromethyl) nicotinamide and monitoring flonicamid.
Synthesis and Structure-Activity Relationships of Novel 7-Substituted 1,4-Dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic Acids as Antitumor Agents. Part 2
Tsuzuki, Yasunori,Tomita, Kyoji,Shibamori, Koh-Ichiro,Sato, Yuji,Kashimoto, Shigeki,Chiba, Katsumi
, p. 2097 - 2109 (2007/10/03)
We have previously reported that a series of 7-substituted 6-fluoro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acids possess moderate cytotoxic activity. In a further attempt to find clinically useful antitumor agents, we investigated the structure-activity relationships (SARs) of a new series of compounds obtained by changing the C-6 position of the fluorine atom in addition to the C-5 and C-7 positions and evaluating their cytotoxic activity against several murine and human tumor cell lines. Our results showed that the 6-unsubstituted 1,8-naphthyridine structure had the most potent cytotoxic activity against murine P388 leukemia twice that of the 6-fluoro analogue. In addition, introduction of an amino group at the C-5 position did not have any substantial effect on the cytotoxic activity, while both the 5-chloro and 5-trifluoromethyl groups decreased the cytotoxic activity by 5- to 10-fold. Moreover, aminopyrrolidine derivatives at the C-7 position showed more potent cytotoxic activity than other amines or carbon derivatives. Among the 7-(3-aminopyrrolidinyl) derivatives, the trans-3-methoxy-4-methylaminopyrrolidinyl derivative (271) was determined to have potent cytotoxic activity in both in vitro and in vivo assays and high water solubility. Finally, the (S,S)-isomer (AG-7352, 3) of 271, with a cytotoxic activity against human tumor cell lines more potent than that of etoposide, was selected for further development.
1,6-naphthyridine derivatives and their use to treat diabetes and related disorders
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Page/Page column 48, (2010/02/05)
The invention relates generally to naphthyridine derivatives of the formula wherein one of U, X, Y and Z is nitrogen and the others are C—R, where R is hydrogen or a substituent. More specifically, the invention relates to 1,6-naphthyridine derivatives and pharmaceutical compositions containing such derivatives. Methods of the invention comprise administration of a naphthyridine derivative of the invention for the treatment of diabetes and related disorders.
Antibacterial compounds
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Page 40, (2010/02/03)
Antibacterials having formula (I) and salts, prodrugs, and salts of prodrugs thereof, processes for making the compounds and intermediates used in the processes, compositions containing the compounds, and methods of prophylaxis and treatment of bacterial infections using the compounds are disclosed.
