Patent GB-1032564-A (GB)
Title: Steroid-guanylhydrazones
Inventor: SCHUTZ SIEGISMUND
IPC: C07J41/00
Filed: 1963-10-31
Abstract: The invention comprises 4-chloro-androst-4-en - 3,17 - bis - guanylhydrazone, androstane-3,17 - bis - guanylhydrazone, 5a  - cyanoandrostone - 3,17 - bis - guanylhydrazone, androsta - 1,4 - diene - 3,17 - bis - guanylhydrazone, 6b  - hydroxy - pregna - 4,14 - diene-3,20 - bis - guanylhydrazone, 9a  - fluoropregna - 1,4 - diene - 11b ,16a ,17a ,21-tetrol-3,20 - bis - guanylhydrazone, 9a  - fluoro - 16a -methyl - pregna - 1,4 - diene - 11b ,16a ,17a ,21-tetrol - 3,20 - bis - guanylhydrazone, androst-4 - en - 11 - one - 3,17 - bis - guanylhydrazone, pregn - 5 - en - 3b  - ol - 7,20 - bis - guanylhydrazone, 19 - nor - androst - 4 - en - 3,17bis - guanylhydrazone, pregna - 3,5 - diene-7,20 - bis - guanylhydrazone, pregnane - 3,6,20-tris - guanylhydrazone, pregn - 4 - en - 3 - one-20 - guanylhydrazone, 2,6 - dinitroso - androst-4 - ene - 3,17 - bis - guanylhydrazone, 2,6-dinitroso - preg - 4 - ene - 3,20 - bis - guanylhydrazone, pregn - 4 - en - 21 - ol - 3,20 - bisguanylhydrazone, 17a ,21 - dihydroxy - pregn-4 - en - 3,20 - bis - guanylhydrazone, 16a ,17a -dihydroxy - pregn - 4 - en - 3,20 - bis -guanylhydrazone, b  - nor - pregn - 4 - en - 3,20 - bisguanylhydrazone, 2b (H) - pregn - 4 - eno[3,2 - c] - cyclohex - 21 - en - 11,20 - bis - guanylhydrazone, cholestane - 3,6 - bis - guanylhydrazone, androsta - 3,S - diene - 7,17 - bisguanylhydrazone, 9a  - fluoro - 11b ,16a ,17aa -trihydroxy - 17ab  - hydroxymethyl - D - homoandrosta - 1,4 - diene - 3,17 - bis - guanylhydrazone, A - nor - pregn - 3 - ene - 2,20 - bisguanylhydrazone, pregn - 4 - ene - 3,6,20 - trisguanylhydrazone, 12a  - acetoxy - 5b  - pregnane-3,20 - bis -guanylhydrazone, aldosteroneguanylhydrazone, 2b  - formyl - pregn - 4 - en-20b  - ol - 3 - guanylhydrazone, 3,5 - cycloandrostane - 6,17 - dione - bis - guanylhydrazone, 16b  - formyl - androst - 5 - en - 3b  - ol-17 - one - bis - guanylhydrazone, 2a  - (31-guanylhydrazonebutyl) - pregn - 4 - ene - 3,20-bis - guanylhydrazone, 2a  - (31 - guanylhydrazonebutyl) - androst - 4 - en - 17b  - ol - 3guanylhydrazone, 2#c - (31 - guanylhydrazonebutyl) - androst - 4 - ene - 3,17 - bis - guanylhydrazone, 2b (H) - androst - 4 - eno - [3,2 - c]cyclohex - 21 - en - 11,17 - bis - guanylhydrazone, 2#c - (31 - guanylhydrazonebutyl) - pregn - 4 -en20 20 - ol - 3 - guanylhydrazone, 16#c -(31 - guanylhydrazonebutyl) - androst - 5 - en - 3b  - ol - 17-guanylhydrazone, pregn - 4 - en - 11#c,17#c-diol - 3,20 - bis - guanylhydrazone, 5b  - pregnan-12#c - ol - 3,20 - bis - guanylhydrazone, 16b -(H) - androst - 4 - eno - [17,16 - c] - cyclohex-21 - en - 11,3 - bis - guanylhydrazone, and 17b  - formyl - androst - 4 - en - 3 - one - bis-guanylhydrazone, and their preparation from the corresponding carbonyl-steroids by (a) reaction with aminoguanidine, or an acid addition salt thereof, (b) conversion to a thiosemicarbazone and treatment with ammonia, (c) conversion to a hydrazone and reaction with cyanamide, or (d) hydrolysis of a 3-enamine product to a 3-ketone, the compounds being retained as the hydrochlorides.  2,6 - Dinitroso derivatives of androst - 4 - en-3,17-dione and pregn-4-en-3,20-dione are prepared by nitrosylation with isoamyl nitrite.  2#c - (3 - Ketobutyl) - pregn - 4 - en - 20b  - ol - 3-one and 16#c - (31 - ketabutyl) - androst - 5 - en-3b  - ol - 17 - one are prepared by reaction of the corresponding 2- or 16-hydroxymethylene compounds with methyl vinyl ketone in the presence of triethylamine.  2#c - (31 - Ketobutyl) - androst - 4 - en - 3,17-dione and 2b (H) - androst - 4 - eno - [3,2 - c]-cyclohex - 21 - en - 11,17 - dione are prepared by oxidation of the corresponding 17b -hydroxy compounds with chromium trioxide.