Process for the conversion of 3-enol ethers of 3-keto-delta**4-steroids unsubstituted at c4 and c6 to the corresponding 3 - keto - delta**4-6beta - (n-disubstituted)aminomethyl compounds

Abstract

Abstract THIS INVENTION RELATES TO A NOVEL AND GENERAL PROCESS FOR THE CONVERSION OF THE 3-ENOL ETHERS (1) OF 3-KETO-$4STEROIDS, UNSUBSTITUTED AT THE 4 AND 6 POSITIONS, OF THE ANDROSTANE, 19-NORADROSTANE, PREGNANE, 19-NORPREGNANE, STIGMASTANE AND SPIROSTANE SERIES INTO THE CORRESPONDING 3-KETO-$4-6B-(N-DISUBSTITUTED) AMINOMETHYL DERIVATIVES (III). THE COMPOUNDS OF FORMULA III HAVE ANABOLIC, ANDROGENIC, ANTI-FERTILITY, ANTI-FLAMMATORY AND ESTROGENIC ACTIVITIES, AND ARE CONSEQUENTLY USEFUL IN TREATING MAMMALS, INCLUDING HUMANS, BIRDS AND OTHER ANIMALS IN THOSE CONDITIONS AND/OR AILMENTS WHERE SUCH ACTIVITIES ARESIRED. FOR EXAMPLE, IN PREVENTING PREGNANCY, INCREASING PELT SIZE IN FEMALE MINK, TREATING ARTHRITIS, OSTEOPOROSIS, ETC. THE COMPOUNDS OF FORMULA III ARE ADDITIONALLY USEFUL AS INTERMEDIATES IN THE PREPARATION, BY KNOWN METHODS, OF THE PHYSIOLOGICALLY ACTIVE AND THERAPEUTICALLY USEFUL 6METHYL STEROIDS, SUCH AS MEDROXYPROGESTERONE ACETATE (6A-METHYL-17A-HYDROXY-4-PREGNENE-3,20-DIONE-17ACETATE), DIMETHISTERONE (6A-METHYL-17B-HYDROXY-17A-(1PROPYNYL)-4-ANDROSTEN-3-ONE), METHYLPRENISOLONE (6AMETHYL-11B,17A,21-TRIHYDROXY-1,4-PREGNADIENE-3,20DIONE), FLUOROMETHYLONE (6A-METHYL-9A-FLUORO-11B,17A-DIHYDROXY-1,4-PREGNADIENE-3,20-DIONE), ETC.

Inventors

• 👤 Verlan H Van Rheenen

Bibliographic Details