Patent GB-419607-A (GB)
Title: The manufacture of neutral, water-soluble organo-metallic compounds
IPC: C07F9/92
Filed: 1933-05-15
Abstract: Neutral, water-soluble derivatives of enhanced therapeutic utility are prepared by treating an aminoarylarseno-arsenic, -antimony or -bismuth compound with an alkylene oxide or derivative thereof in the presence of a solvent.  The starting materials, in which the arsenic atoms of the arylarseno radicles are directly connected with inorganically - bound arsenic, antimony or bismuth atoms, may be prepared by reacting upon aminoarylarsines with inorganic trivalent arsenic, antimony or bismuth compounds in solution, or in the case of the arsenic and antimony compounds, by reducing a mixture of an aminoaryl-arsonic acid or -arsenoxide with an inorganic arsenic or antimony compound.  A second method for the preparation of the derivatives consists in reacting with an alkylene oxide upon an aminoarylarsine and treating the product with an inorganic arsenic, antimony or bismuth compound in the presence of a solvent.  The same derivatives, except those containing bismuth, may also be prepared by treating an aminoaryl-arsonic acid or -arsenoxide with an alkylene oxide and reducing the product in the presence of an inorganic arsenic or antimony compound.  In each of the three methods minimum contact with the air is essential.  The products, which contain hydroxyalkylamino groups, may be treated simultaneously or subsequently with formaldehyde-bisulphite or -sulphoxylate, and in the case of the compounds obtained by the second and third methods, may be reacted with further amounts of alkylene oxide.  According to the examples, (1) 4-hydroxy - 3 - aminophenylarsine acetate is treated with glycide in methyl alcohol, then with antimony trichloride, and finally with formaldehyde and sodium bisulphite; the probable formula of the product is given; (2) 4 - hydroxy - 3 - aminophenylarsine acetate is reacted with glycide and antimony trichloride or bismuth chloride in methyl alcohol; (3) 4 - hydroxy - 3 - aminophenylarseno - antimony, prepared from 4-hydroxy-3-aminophenylarsine acetate and tartar emetic (see German Specification 558,567), is treated with formaldehyde-sodium bisulphite and glycide; (4) 4-hydroxy-3-aminophenylarsine acetate is converted into the arseno-arsenic compound by the process of Specification 388,054 and treated with formaldehyde-sodium sulphoxylate and glycide in the presence of water; similarly 4-aminophenylarseno-arsenic is treated with formaldehyde-sulphoxylate or -bisulphite and glycide; (5) 4 - hydroxy - 3 - aminophenylarseno - arsenic (see Specification 388,054) is treated in water with glycide and formaldehyde-sodium bisulphite; (6) 4 - hydroxy - 3 - aminophenylarsine acetate is reacted with propylene oxide in methyl alcohol solution and then with antimony trichloride and sodium formaldehyde-bisulphite.  The samples are prepared from (1) 4-hydroxy-3-aminophenylarsine acetate, a  - diethylamino - epihydrin and bismuth chloride, and (2) 4 - hydroxy - 3 - aminophenylarsine acetate, a -diethylaminoepihydrin and antimony trichloride. Specifications 326,537, [Class 2 (iii)], 405,260 and 405,618 also are referred to.  The Specification as open to inspection under Sect. 91 also describes the preparation of compounds from (1) 4-hydroxy-3-aminophenylarsine acetate, glucosane, antimony or bismuth trichloride and sodium formaldehyde-bisulphite, and (2) 4-hydroxy-3-aminophenylarsine acetate, a -diethylaminoepihydrin and arsenic trichloride.  This subject-matter does not appear in the Specification as accepted.