Salicylamide acetyl

Synthesis of the prototype begins with Friedel Crafts acetylation of salicylamide ( ). Bromination of the ketone (25) followed by displacement with amine gives the corresponding ami noketone ( ). Catalytic hydrogenation to the ami noalcohol completes the synthesis of labetolol (24). The presence of two chiral centers at remote positions leads to the two diastereomers being obtained in essentially equal amounts. 

Via (N—C—C—C—O—C—C) intermediates (type c). Salicylamide (351 R = H) can be converted to 1,4-benzoxazepine derivatives, e.g. its reaction with 2-chloropheny-lacetic acid gives (351 R = CH(Ph)C02H) which on treatment with acetyl chloride cyclizes to the 3,5-dione (352). Similarly reaction of (351 R = H) with phenacyl bromide gives (351 R = CH2COPh) which undergoes acid-catalyzed cyclization to give (353). 

Salicylamide with 2-chlorophenylacetic acid followed by acetyl chloride gives the 3,5-dione (369). Similarly phenacyl bromide gives (370). 

Nieminen (58) described a gas chromatographic method for simultaneous separation and quantitation of some antipyretics including salicylamide containing phenobarbital, caffeine and codeine phosphate. Codeine phosphate was first separated from the samples as the base. Although the separation was excellent for all components, yet acetyl-salicylic acid interferes with the separation of salicylamide. 

An example of two ion exchange separations are shown in Figure 5-32. The first separation is of phthalic acid, terephthalic acid and isophthalic acid using a 10-mM boric acid mobile phase adjusted to pH 9.2 using sodium hydroxide. The other separation in Figure 5-32 is of caffeine, w-acetyl-p-aminophenyl, aspirin, and salicylamide. In order for all of these compounds to be eluted in a reasonable time, the 10-mM boric acid solution also contains 20 mM sodium nitrate for ionic strength adjustment. 

Lurie, I.S. McGuiness, K. The quantitation of heroin and selected basic impurities via reversed phase HPLC. II. The analysis of adulterated samples. J.Liq.Chromatogr., 1987,10, 2189-2204 [UV detection electrochemical detection simultaneous acetaminophen, acetylcodeine, acetylmorphine, acetyl-procaine, aminopyrene, amitriptyline, antipyrene, barbital, benztropine, caffeine, cocaine, codeine, diamorphine, diazepam, diphenhydramine, dipyrone, ephedrine, ethylmorphine, lidocaine, meconin, methamphetamine, methap3rrilene, methaqualone, monoacetylmorphine, morphine, nalorphine (IS), niacinamide, noscapine, papaverine, phenacetin, phenmetrazine, phenobarbital, phenolphthsdein, procaine, propanophenone, propoxyphene, pyrilamine, quinidine, quinine, salicylamide, salicylic acid, secobarbital, strychnine, tartaric acid, tetracaine, thebaine, tripelennamine, tropacocaine, vitamin Bj, vitamin B3]... 

About 10% of asthmatics are hypersensitive to aspirin, and in some individuals life-threatening bronchoconstriction can occur. This is not a drug-drug interaction but an adverse response of asthmatic patients to aspirin, whether taking an anti-asthmatic drug or not. The reasons are not fully understood. Those known to be sensitive to aspirin may also possibly react to other NSAIDs, in particular the acetylated salicylates, the indole and indene acetic acids, and the propionic acid derivatives (see Table 6.1 , (p.l34)). The fenamates, oxicams, pyrazolones and pyrazolidinediones are better tolerated. The nonacetylated salicylates (sodium salicylate, salicylamide, choline magnesium trisalicylate) are normally well tolerated. Aspirin-sensitive individuals are also less likely to react to nimesulide. ... 

Sequential spectrophotometric measurements of two drugs (ascorbic acid-thiamine, acetyl salicylic acid-thiamine, or paracetamol-salicylamide) and fluorimetric measurements (warfarin-thiabendazole) have been performed using two sohd-phase reactors first, a precolumn retains one of the analytes and the nonretained one is monitored in a flow cell containing a solid-phase reactor anionic exchange for the spectrophotometric measured couples or CIS bonded silica for the fluorimetric measurements. The next step is to elute the formerly retained analyte to be monitored. 

Simultaneous Determination of Acetyl-salicylic Acid, Salicylic Acid, and Salicylamide in Plasma by Gas-Liquid Chromatography J. Pharm. Pharmacol. 27(6) 425-429 (1975) CA 83 172321k... 

Plienyl-S-acetyl-A -pyra olm-dioarhon aOare-(3.5).dimethylester 26. 269. Verbindnng aus Salicylamid... 

Sabinol, 75 Saccharic acid, 33 Salicylaldehyde, 52 Salicylamide, 49 Salicylic acid, 40, 48, 51, 52 acetyl-, 13 Salicyluric acid, 49 Saligenin, 15 Santenone, 79 Scurvy, 18 Sodium alginate, 20 Sodium benzoate, 31 Sodium n-butyrate, 29 Sodium feri-butyl acetate, 29 Stilbestrol, 81, 84 Streptomycin, 70 Synovial fluid, 15, 16 Syringaldehyde, 53 Sulfadiazine, 14, 62 Sulfamerazine, 62 Sulfamezathine, 62 Sulfanilamide, 61, 63 Sulfapyridine, 61, 62 Sulfathiazole, 61... 

---