- 5-aminothiazole non-steroidal anti-inflammatory compound as well as preparation method and application thereof
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The invention discloses a 5-aminothiazole non-steroidal anti-inflammatory compound. The compound which is efficient, low in toxicity and small in side effect is prepared from an ester intermediate containing a thiazine ring and a 5-aminothiazole derivative through a transesterification reaction. The preparation method of the compound is simple, the compound has the active groups of the existing non-steroidal anti-inflammatory medicine; meanwhile, the special change of the nitrogen atom position is also designed; compared with the existing non-steroidal anti-inflammatory medicines, the compoundhas better anti-inflammatory and analgesic effects, particularly has good curative effects on arthritis, osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, soft tissue inflammation and thelike, has small toxic and side effects on human bodies, and has a very wide market prospect.
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Paragraph 0105; 0142-0143; 0145
(2020/09/20)
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- Piroxicam hapten and preparation method and application thereof
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The invention aims to provide a piroxicam hapten and a synthesis method and application thereof, belonging to the field of drug safety detection. The preparation method comprises the following steps:1) mixing saccharin and ethyl bromoacetate for reacting to prepare an intermediate product 1; 2) mixing and extracting the intermediate product 1 with DMSO and MeONa to obtain an intermediate product2; 3) mixing the intermediate product 2 and CH3I for reacting to obtain an intermediate product 3; 4) mixing the intermediate product 3 and 6-aminonicotinic acid methyl ester for reacting to obtain anintermediate product 4; 5) after adding of the intermediate product 4 into a reagent for miscibility reaction, purifying to obtain the final product, namely the piroxicam hapten. Immunological detection method has the advantages of high sensitivity, strong specificity, simple sample pretreatment, short detection time, strong stability, no need of special equipment and reagents, intuitive judgmentof results and the like, thus being particularly suitable for rapid detection of illegal addition of piroxicam chemical drugs in vast basic inspection personnel and large quantities of anti-rheumatism Chinese patent medicines.
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- Discovery of cyclicsulfonamide derivatives as 11β-hydroxysteroid dehydrogenase 1 inhibitors
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A new series of cyclic sulfonamide derivatives was synthesized and evaluated for their ability to inhibit 11β-HSD1. Cyclic sulfonamides with phenylacetyl substituents at the 2-position showed nanomolar inhibitory activities. Among them, compound 4e exhibited a good in vitro inhibitory activity and selectivity toward human 11β-HSD2.
- Kim, Se Hoan,Ramu, Ravirala,Kwon, Sung Wook,Lee, Su-Hee,Kim, Chi Hyun,Kang, Seung Kyu,Rhee, Sang Dal,Bae, Myung Ae,Ahn, Sung Hoon,Ha, Duck Chan,Cheon, Hyae Gyeong,Kim, Ki Young,Ahn, Jin Hee
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supporting information; experimental part
p. 1065 - 1069
(2010/06/14)
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- Site-specific acid-base properties of tenoxicam
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The Hammett approach, as a new deductive tool, was introduced to characterize the otherwise inaccessible minor protonation pathway of tenoxicam (1), the non-steroidal anti-inflammatory drug. A total of eight compounds, constituting a systematic series of side chain-substituted analogues of tenoxicam and piroxicam (2), were synthesized and studied in terms of acid-base properties and Hammett constants to identify the ideal replacement of the unprotonated pyridin-2-yl group, a key moiety in both molecules. Hammett constants of the phenyl substituents have been found to be in a linear correlation with the experimental log K values of the enolate sites, the basic moiety of the extended conjugated system in this family of piroxicam derivatives. Then, a similar correlation was observed for the analogous tenoxicam derivatives. After identifying the 2-aza Hammett constant of the pyridin-2-yl group and the corresponding log K value, the site-specific acid-base properties of tenoxicam could be quantitated. This novel method is assessed to be a fine-tuning tool to find the ideal substituent by using analogue-based deductive method to obtain site-specific constants of the minor protonation/deprotonation pathway in drugs and biomolecules. The tenoxicam microconstant values indicate that the enolate moiety is of extremely low basicity (reflected by the log kO = 3.70 and log kO N = 1.09 values), which can, however, be interpreted in terms of the peculiar ring system and the overwhelming electron-withdrawing effects of the adjacent heteroatoms. A diagram depicting the pH-dependent distribution of 1 microspecies is also presented.
- Koczian, Kristof,Voelgyi, Gergely,Koekoesi, Jozsef,Noszal, Bela
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p. 1681 - 1690
(2008/02/13)
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- CONDITIONS OF THE DIECKMANN CONDENSATION OF ALKYL 2-(N-METHYL-N-(ALKOXYCARBONYLMETHYL)SULFAMOYL-BENZOATES
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The Dieckmann condensation of alkyl 2-(N-methyl-N-(alkoxycarbonylmethyl)sulfamoyl)benzoates IIIa-IIIe with various bases affords alkyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxides IVa-IVe which are intermediates in the synthesis of antiinflammatory drug piroxicam.The yields of benzothiazines IVa-IVe depend mostly on the nature of a base, reaction temperature and solvent used for these condensations.Hitherto undescribed esters IIIb-IIIe were sythesized and their structures were confirmed by 1H and 13C NMR, and mass spectra.
- Patek, Marcel,Hampl, Frantisek
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p. 3267 - 3277
(2007/10/02)
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