Patent GB-900572-A (GB)
Title: Funtumia alkaloids
IPC: A61K36/24
Filed: 1958-09-26
Abstract: 900,572. Funtumia alkaloids and steroids. OLETTA S.A. Sept. 26, 1958 [Sept. 27, 1957; Feb. 22, 1958; June 4, 1958], No. 30862/58. Class 2(3). The invention comprises 3α-amino-allopregnan-20-ol (funtumidine) and 3α-aminoallopregnan-20-one (funtumine) and their acidadditions salts; and a process for their isolation from plants of the genus Funtumia which comprises extracting parts of the plants or whole plants with a water-immiscible solvent, acidifying the extract and if necessary removing any crystals which form, rendering the acid solution alkaline to precipitate a solid and/or washing with aqueous alkali any removed crystals, separating the solid from the solution and/or washings and extracting it with an organic solvent, evaporating the extract to dryness, dissolving the residue in benzene and separating funtumine from funtumidine by chromatographic or ion-exchange methods. (It is stated that after removal of these steroids further elution of the chromatographic column yields a sapogenin of m.p. 260‹C. which is recrystallizable from methanol or ethyl acetate, positive to Liebermann's reaction, contains no nitrogen and shows in the infra-red spectrum an OH band at about 3mÁ and a CO band at about 6mÁ). The plants, which are preferably of the species F.latifolia, F.Africana or F.elastica, may first be crushed, washed with pstroleum ether and left for a number of hours in contact with water or alkali before the initial extraction. The invention also comprises (1) the process of oxidizing funtumidine to funtumine with chromic acid in acetic acid; (2) the process of reducing funtumine to funtumidine, advantageously with sodium in alcohol; (3) the process of producing 20-epifuntumidine (3α-amino-20#-hydroxy-allopregnane) by dissolving funtumine in methanol, adding potassium or sodium borohydride, agitating the mixture, diluting the solution, extracting with an immiscible solvent, and washing, drying and evaporating the extract; (4) a process for the production of allopregnane-3,20-dione which comprises reacting funtumine either with nitrous acid in acetic, tartaric or hydrochloric acid to give a secondary alcohol and oxidizing this with chromic acid in acetic acid or pyridine or by the Oppenauer method, or with hypochlorous acid in ether to form the corresponding chloramine, dechlorinating this with sodium ethoxide and hydrolysing the ketimine with sulphuric acid; (5) a process for producing 3α- amino-androstan-17#-ol by treating funtumine with a peracid and hydrolysing the product (which, when peracetic acid is used, is 17#- acetoxy-3α-amino-androstane); and (6) a process for producing. 3α-amino-androstan-17-one by oxidizing the product of (5). Examples describe the processes of (1), (2) and (3), the second process detailed under (4), and the preparation of 20α- or 20#-hydroxy-allopregnan-3-one from funtumidine or 20-epi-funtumidine by this lastnamed process. The hydrochlorides of funtumine and funtumidine, which are stated to have anaesthetic and antipyretic properties, may be dissolved in aqueous propylene glycol or other solvents such as methyl acetamide to give injection solutions, or may be made up into tablets, an example of which is provided.