ADRENAL HORMONES AND RELATED COMPOUNDS. IV. 6-METHYL STEROIDS¹

Highly β‐Selective Epoxidation of Δ 5 ‐Unsaturated Steroids Catalyzed by Ketones

“…Compounds 8 a and 8 b (as a mixture in a ratio of 1: Epoxides 6 a and 6 b [26] (as a mixture in a ratio of 1:15.1), 7 a and 7 b [27] (as a mixture in a ratio of 1:10.4), 9 a and 9 b [28] (as a mixture in a ratio of 1:8.8), 10 a and 10 b [27] (as a mixture in a ratio of 1:11.6), 12 a, [29] 12 b, [30] 13 b, [30] 14 b, [31] 15 b, [32] 16 b, [33] 17 b, [18] 18 b, [34] 19 b, [18] 20 b, [35] and 21 b [36] have spectroscopic data which are identical with those reported in literature.…”

Hormones

“…Insertion of a 6α-methyl group into the corticosteroid nucleus by scientists at Upjohn [256] and British Drug Houses [257] gave rise to derivatives with enhanced glucocorticoid activity and low mineralocorticoid activity. The most potent orally, parenterally, and topically active compounds are 6α-methylprednisolone (131), which has approximately 10 times the anti-inflammatory activity of cortisol in animal experiments, and 6α-methyl-9α-fluoroprednisolone (132), which has relatively low mineralocorticoid activity and almost 100 times the glucocorticoid potency of cortisol in animal experiments.…”

The Pharmacology of Cortisone, Cortisol (Hydrocortisone) and their New Analogues

“…Using this compound the metabolic end-products are small enough rot to disguise the falls in I7ketosteroid and 17-hydroxysteroid excretion which follow the steroid-induced suppression of endogenous corticotrophin in patients with adrenal hyperplasia. Some More Recent Cortisol Derivatives By the addition of a 6-methyl group to cortisol or prednisolone or a i6-OH group to FHC or 9-alpha fluoroprednisolone compounds can be obtained with even greater glucocorticoid potency than prednisolone, and without excessive mineralocorticoid activity (Spero et al, 1956;Bernstein et al, I956). These compounds, which have not yet been subjected to full clinical trial, are unlikely to offer advantages over prednisolone as they seem to have no important qualitative differences in their glucocorticoid actions.…”