Quaternary furyl-, thienyl-, and pyrrolylpyridinium salts. Oral hypoglycemic agents

Quaternary Pyridinium Compounds

“…Hypoglycemic activity (as measured in mice, and in one case also chicks, 580) was found with pyrazolyl (572), thiazolyl (573), oxazolyl (5741, isoxazolyl (575)(576)(577), and 1,2,4-oxa-dimly1 (578) derivatives, as well as those containing a furan, thiophene, pyrrole (579), and 3-indolyl(580) ring. Hypoglycemic activity (as measured in mice, and in one case also chicks, 580) was found with pyrazolyl (572), thiazolyl (573), oxazolyl (5741, isoxazolyl (575)(576)(577), and 1,2,4-oxa-dimly1 (578) derivatives, as well as those containing a furan, thiophene, pyrrole (579), and 3-indolyl(580) ring.…”

Synthesis of some cis and trans 2-(substituted amino)cyclohexyl phenyl ketones

“…Anal. (CgH10IN¡O7H, I, N;C: caled, 35.7; found, 35.2. Addition of Et20 to the mother liquors gave 0.4 g of orange solid which was recrystallized (MeOH) several times to give 68 mg of orange crystals of 6a: § mp 166-167°dec; nmr 5 4.75 (s, 3, 3), 7.33 (s, 1, =CH), 9.55 (d, 1, /H H = 6 cps, Ha), 9.80 (broad m, 1, Hb).…”

“…A solution of 0.4 g (2.25 mmol) of 7b and 1 ml of Mel in 15 ml of MeOH was stirred at room temperature for 48 hr, cooled, and filtered to give 0.28 g of red solid. Recrystallization (MeOH) gave 0.22 g of 5b as deep red crystals: mp 220-222°dec; nmr 4.67 (s, 3, 3), 7.79 (d, l,/ = 1 cps, =CH), 9.63 Addition of Et20 to the mother liquors gave 0.4 g of orange solid which was recrystallized (twice MeOH, twice Me2CO) to give 0.172 g of orange crystals of 6b: § mp 171°dec; nmr 5 4.75 (s, 3, N+CH3), 7.69 (d, 1, / = 1 cps, =CH), 9.50 (d, 1,/H H = 6 cps, Ha), 9.87 (d,l,/HbHc=l cp*. Hb).…”

“…Anal. (C8H9IN4O)t, , I, N. Addition of Et20 to the mother liquors gave 0.5 g of brown solid which was recrystallized (EtOH-Et20) to 0.35 g of very hygroscopic crystals of 6c: § mp 126-127°dec; nmr 5 4.83 (s, 3, N*CH3), 9.60 (d, 1,7h hc = 6 cps, Ha), 10.3 (broad m, 1, Hb). Anal.…”