Patent GB-292962-A (GB)
Title: A process for obtaining a hormone from female internal secretory organs
Filed: 1928-06-27
Abstract: 292,962. Soc. of Chemical Industry in Basle, (Assignees of Frankel, S.). June 24, 1927, [Convention date]. Medicines for internal use.-A hormone is obtained in a chemically pure form from extracts of female sexual organs bv first eliminating in known manner the phosphatides, cholesterin, cholesterin esters, and fats, and then treating the extract to remove fatty acids with an agent, such as the acetate of a heavy metal or of an alkaline earth, which will form soaps which are insoluble in the solvent employed. The soap produced and excess of the metal salt are removed, and the hormone so obtained is either crystallized at very low temperature from a suitable organic solvent, or is converted into its dibromide and finally debrominated. According to an example, placenta is dried, extracted with benzene or alcohol, the solvent distilled off and the residue extracted with acetone. The acetone solution is cooled to precipitate impurities and distilled to remove the acetone, and the residue is taken up in methyl alcohol. This solution is treated with a feebly ammoniacal solution of lead acetate in methyl alcohol and the filtrate concentrated and poured into water from which the hormone is extracted with petroleum, ether. The petroleum ether solution is washed with water and then treated with a solution of a salt, such as the sulphate of sodium or potassium or nitrite of silver, to remove any soluble lead soaps. The purified solution so obtained is then evaporated, taken up in absolute ether, and cooled by means of a mixture of carbonic acid snow and ether to crystallize out the chemically pure hormone. Alternatively the solution in petroleum ether is evaporated, the residue taken up in ether or glacial acetic acid, and bromine is added. Excess bromine is removed with sodium carbonate, the solvent is evaporated, and the residue dissolved in alcohol and boiled with zinc dust coated with copper or with amalgamated zinc dust to debrominate the hormone. The solution obtained is filtered, poured into water, extracted with a solvent such as benzene or ether, and the extract is washed with water and finally evaporated in vacuo to obtain the hormone. The hormone is stated to have the formula C16H28O2 and to be the lactone of an open-chain oxy-acid having a double linking between the twelfth and thirteenth carbon atoms of the chain. An oxy-acid may be obtained by splitting up the lactone. The hormone may be treated with thionyl chloride and hydrazine hydrate to obtain a body which is apparently a dimolecular hydrazide having an ether bridge and having the formula C32H66O3N4. Specification 113,311 is referred to. The Specification as open to inspection under Sect. 91 (3) (a) describes also a process wherein in place of treating the petroleum ether solution directly with a precipitant for lead compounds, as in the example above, it is evaporated, the residue taken up in methyl alcohol, treated with a solution of the precipitant, concentrated, and, after addition of water, is again extracted with petroleum ether. The process is then completed as in the example above. This subject-matter does not appear in the Specification as accepted.