Ethionamides

A thioamide of isonicotinic acid has also shown tuberculostatic activity in the clinic. The additional substitution on the pyridine ring precludes its preparation from simple starting materials. Reaction of ethyl methyl ketone with ethyl oxalate leads to the ester-diketone, 12 (shown as its enol). Condensation of this with cyanoacetamide gives the substituted pyridone, 13, which contains both the ethyl and carboxyl groups in the desired position. The nitrile group is then excised by means of decarboxylative hydrolysis. Treatment of the pyridone (14) with phosphorus oxychloride converts that compound (after exposure to ethanol to take the acid chloride to the ester) to the chloro-pyridine, 15. The halogen is then removed by catalytic reduction (16). The ester at the 4 position is converted to the desired functionality by successive conversion to the amide (17), dehydration to the nitrile (18), and finally addition of hydrogen sulfide. There is thus obtained ethionamide (19)... [Pg.255]

Dimethyl tubocurarine Iodide Cyanacetamid Ethionamide Protionamide Cyanamide Albendazole Butalamine HCl Cimetide Cyanoacetamide Allopurinol Cyanoacetic acid Aminometradine Amisometradine Cyclopentamine HCl Sulindac... [Pg.1625]

Tear-Efrin - Phenylephrine HCI Tebacin acid - Aminosalicylic acid Tebertin - Inosine Teberus Ethionamide Tebesium - Isoniazid Tebilon - Isoniazid Tebloc - Loperamide HCI Tebrezid - Pyrazinamide Techlon - Pentoxifylline Teclinazets - Tetracycline T-E Cypionate - Estradiol cypionate Tedarol - Triamcinolone Tedarol - Triamcinolone acetonide Tedarol - Triamcinolone diacetate Teejel - Choline salicylate Tefsiel - Tegafur... [Pg.1746]

C4HJO 78-93-3) see Beclobrate Bemegride Clinofibrate Clobetasone butyrate Ethionamide Ethosuximide Methylpentynol Paramethadione 1-butene... [Pg.2316]

CJH4N2O 107-91-5) see Alloputinol Amrinone Ethionamide Milrinone Nevirapine Olprinone hydrochloride Protionamide cyanoacetic acid... [Pg.2338]

Ethionamide Ethoheptazine Ethyl biscoumacetate Etiroxate Fenoxazoline Flurbiprofen Indobufen Indoramin Isocarboxazid Lofexidine Methotrexate Methyidopate Methylphenobarbital Nadoxolol Naphazoline Petindopril Phcnobarbital Propiverine Protionamide Proxazole Pyridoxine Retinol Thiamphenicol Tolazoline Tribenoside ethanolamine... [Pg.2372]

Fig. 5.17 Antitubercular compounds (see text also for details of antibiotics) A, PAS B, isoniazid C, ethionamide D, pyrazinamide E, prothionamide F, thiaeetazone G, ethambutol.

Ethionamide monooxygenase EtaA Physiological substrates unidentified Mycobacterium tuberculosis 200447... [Pg.111]

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