1958
DOI: 10.1007/bf02327380
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Dihydrobenzothiadiazine dioxides with potent diuretic effect

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Cited by 81 publications
(34 citation statements)
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“…Modifications of drugs such as diuretics can be caused by metabolism [2][3][4][5][6] or by intentional alterations of the molecules prior to administration in order to characterize the influence of functional groups on the efficiency of the particular remedy [7][8][9][10]. For instance, the diuretic effect of chlorothiazide (6-chloro-7-sulfamoyl-1,2,4-benzothiadiazine-1,1-dioxide) was increased by a factor of 10 by the hydration of its N-3¢C-4 double bond to hydrochlorothiazide (6-chloro-7-sulfamoyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide) [11][12][13], and the substitution of a 2,6-dimethylanilide residue by a 2,6-dimethylpiperidyl group and a hydroxyl group by a hydrogen changes the diuretic agent xipamide to clopamide ( Figure 1). The identification of structural deviations can be accomplished by means of different ionization techniques such as electron impact ionization (EI) [14 -16] or electrospray ionization (ESI) [17][18][19], followed by MS-MS experiments with efficient collision-activated dissociation (CAD), generating structure informative fragment ions of the analytes.…”
mentioning
confidence: 99%
“…Modifications of drugs such as diuretics can be caused by metabolism [2][3][4][5][6] or by intentional alterations of the molecules prior to administration in order to characterize the influence of functional groups on the efficiency of the particular remedy [7][8][9][10]. For instance, the diuretic effect of chlorothiazide (6-chloro-7-sulfamoyl-1,2,4-benzothiadiazine-1,1-dioxide) was increased by a factor of 10 by the hydration of its N-3¢C-4 double bond to hydrochlorothiazide (6-chloro-7-sulfamoyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide) [11][12][13], and the substitution of a 2,6-dimethylanilide residue by a 2,6-dimethylpiperidyl group and a hydroxyl group by a hydrogen changes the diuretic agent xipamide to clopamide ( Figure 1). The identification of structural deviations can be accomplished by means of different ionization techniques such as electron impact ionization (EI) [14 -16] or electrospray ionization (ESI) [17][18][19], followed by MS-MS experiments with efficient collision-activated dissociation (CAD), generating structure informative fragment ions of the analytes.…”
mentioning
confidence: 99%
“…It is still today the thiazide diuretic of choice and used in numerous combination drugs. Hydrochlorothiazide is prepared from 4-amino-6-chlorobenzene-1,3-disulfonamide by reaction with formaldehyde [334,335]. Merck & Co. were issued also a patent on this substance, but Ciba had the earlier priority [336,337].…”
Section: Thiazides and Related Diureticsmentioning
confidence: 99%
“…Research on diuretics in the late 1950s at Merck Sharp & Dohme Research Laboratories culminated in the develop ment of chlorothiazide (22), an agent whose lineage can be traced directly to the carbonic anhydrase inhibitors. Additional thiazide diuretics have been developed, most notably hydrochlorothiazide (23). A systematic program of chemical modifica tion eventually led to the development of furosemide (24), the prototype of the high-ceiling or loop diuretics.…”
Section: Sulfonamidesmentioning
confidence: 99%