NOUVEAUX STEROIDES, LEUR PROCEDE DE PREPARATION ET LEURS APPLICATIONS

1409240 3α- Hydroxy-19-nov-5α-pregnane- 11,20-dione GLAXO LABORATORIES Ltd 8 Nov 1972 [11 Nov 1971] 52466/71 Heading C2U The novel title compound is prepared by sterospecific reduction of the corresponding 3-one, preferably by the method disclosed in Specification 1,409,239, or by hydrogenating the corresponding #16-steroid. 19 - Nor - 5α- pregnane - 3,11,20 - trione is prepared by converting 11α,17α-dihydroxy-19- norpregn.-4-ene-3,20-dione to a semicarbazide and dehydrating and hydrolysing this to give 11α - hydroxy - 19 - norpregna - 4,16 - diene- 3,20 - dione, reducing this to 3#,11α,29#-trihydroxy - 19 - nor - 5α - pregnane and oxidizing this. 3α - Hydroxy 19 - nor - 5α - pregn. - 16- ene - 11,20 - dione is prepared by hydrogenating the same starting material to give 11α,- 17α - dihydroxy - 19 - nor - 5α - pregnane - 3,20 - diene, dehydrating this via a semicarbazide to 11α-hydroxy - 19-nor - 5α-pregn- 16-ene-3,20-dione, oxidizing this to 19 - nor - 5α - pregn - 16 - ene - 3,11,20 - trione and sterospecifically reducing this. The novel comound may be converted to 2#-substituted-5α-pregnanes via the corresponding 2α,3α-epoxy compound and to the corresponding 17#-carboxy-androstane and its esters by oxidation and, when desired, esterification. The novel steroid is stated to possess anaesthetic, hypnotic and sedative properties and it may be made up into pharmaceutical compositions with suitable carriers. Surface-active agents may be used to prepare aqueous injection solutions.