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United States Patent Office OC ...) H 2,697,709 United States Patent Office Patented Dec. 21, 1954 2 lent tautomeric formulas some of which are illustrated 2,697,709 below: MERCAPTO HETEROCYCLES AND METHOD OF MAKHNG SH George H. Hitchings, Tuckahoe, and Gertrude B. Elion, Bronxville, N. Y., assignors to Burroughs Wellcome & Y \, : Y \, Co. (U. S. A.) Inc., Tuckahoe, N. Y., a corporation of N New York O .C. ) No Drawing. Application June 11, 1952, S SE Serial No. 292,974 Claims priority, application Great Britain June 14, 1951 5 7 Claims. (CI. 260-252) P s P The present invention relates to 6-mercaptopurines and to processes for preparing the same. Its main object is The mercaptopurines, in general, melt only with de to provide new compositions of matter which are useful composition and at high temperatures. The melting as inhibitors of microorganisms and in providing tem points, therefore, are not suitable for characterization. porary remission in the treatment of acute leukemia and More characteristic are the ultra-violet absorption spec chronic myelogenous leukemia. A further object is to tra which exhibit absorption maxima in the region 310 provide methods of introduction of a mercapto group 350 mu (other maxima at shorter wave lengths may also into the 6-position of the purine system. Additional ob 25 be. present). ... " jects will become apparent from the description and ap The 6-mercaptopurines form salts with both bases and pended claims. acids. The non-toxic salts are the pharmacological equiv The new group of substances may be formulated as alents of the free purines. follows: 30 EXAMPLE 1. SH 6-mercaptopurine A mixture of 9.5 g. of 4-amino-5-formamido-6-hy droxypyrimidine, 55 g. of finely ground phosphorus xl.OC) N pentasulfide and 300 ml. of tetralin was heated at 190° with mechanical stirring for two hours. After cooling, the insoluble residue was filtered off and washed with where X is selected from the class consisting of hydrogen petroleum ether. The solid was then suspended in 350 and chloro, hydroxyl, mercapio, amino, alkyl, alkyl ml. of water and 2 N sodium hydroxide added gradually amino and alkylmercapto radicals. 40 with stirring until all the phosphorus pentasulfide had The compositions are prepared from intermediates of been decomposed and the pH remained at 8. The mixture the type: was then filtered and acidified to pH 5 with acetic acid. Cl A dark yellow precipitate formed slowly and was, col lected after several hours at room temperature. This 45 precipitate (3.0 g.) by its ultraviolet absorption spectrum was 6-mercaptopurine. Concentration of the mother liquors to 150 ml. and standing for several days pro ...) duced another precipitate (2.6 g.) which was a mixture OCH of 6-mercaptopurine and the starting pyrimidine. wherein X has the values aforementioned, by reaction 50 with reagents of the class consisting of sodium hydro EXAMPLE 2 sulfide and thiourea. They may also be prepared from 6-mercaptopurine intermediates of the type: Two grams of 4-amino-5-formamido-6-hydroxypyrimi dine and 10 g. of finely ground phosphorus pentasulfide 55 were refluxed in 80 ml. of pyridine for three hours. The excess pyridine was then removed under reduced pres sure and the gummy residue boiled with 100 ml. of water for five minutes. The pH was adjusted to 4 by the addi tion of hydrochloric acid and the solution was cooled. ..) 60 A small amount of dark brown precipitate formed in by reaction with phosphorus pentasulfide, as described several hours. This was discarded, since it did not have in our copending application, Serial No. 292,975, filed the characteristic ultraviolet absorption spectrum of 6 June 11, 1952, now Patent No. 2,691,654. In a further mercaptopurine. The precipitation of the 6-mercapto variation, a 4-amino-5-formamido-6-hydroxypyrimidine 65 purine was slow, requiring two weeks before 0.7 g. of may be reacted with phosphorus pentasulfide whereupon this product was collected. sulfurization and cyclization occur in one operation. The examples described below illustrate the methods EXAMPLE 3 which may be used to obtain the desired compositions. 6-mercaptopurine It will be obvious that many variations are possible, 70 especially in the order in which several of the necessary A mixture of 18.5 g. hypoxanthine and 80 g. of phos steps may be performed. The examples, therefore, are phorus pentasulfide in 500 ml. of tetralin was heated illustrative only and not restrictive, the scope of the in at 200 for eight hours. The mixture was cooled and vention being defined in the claims. - filtered. The solid residue, after being washed with The 6-mercaptopurines may be converted to purinyl 75 petroleum ether and dried at room temperature, was 6-disulfides by oxidation. In many biological systems an boiled with 2 liters of water. The hot solution was fil equilibrium between mercapto compounds and disulfides tered and the pH adjusted to 5 with ammonium hydrox is known to be established as a general property of sulfur ide. Dark yellow crystals of 6-mercaptopurine hydrate compounds of this type. The two forms therefore are precipitated on standing (12 g.). Concentration of the pharmacological equivalents. 80 mother liquors led to the recovery of 5 g. of unreacted The compounds may be written in a variety of equiva hypoxanthine. 2,697,709 4 3 2-methyl-6-chloropurine, was neutralized with sodium EXAMPLE 4 hydroxide and 50 ml. of 17 N sodium hydroxide then 6-mercaptopurine added slowly, with chilling. The alkaline solution was saturated with hydrogen sulfide at 0° and then heated A mixture of 5 g. of hypoxanthine, 5 g. of "liver of 5 at 120 in a sealed vessel for 6 hours. After cooling, the sulfur' and 20 g. of phosphorus pentasulfide in 150 ml. reaction mixture was concentrated under reduced pressure of tetralin was heated at 200 for 12 hours. The mix and acidified with hydrochloric acid. The 2-methyl-6- ture was cooled and the insoluble residue collected and mercaptopurine was collected and purified by solution in washed with benzene. The residue was boiled with 600 aqueous alkali and precipitation with hydrochloric acid. ml. of water and filtered hot. On cooling, 6-mercapto O purine precipitated as yellow crystals. EXAMPLE 11 EXAMPLE 5 2-methylmercapto-6-mercaptopurine 6-mercaptopurine Sixteen grams of 2-methylmercapto-6-hydroxypurine 5 and 8 ml. of dimethylaniline were refluxed in 280 ml. of A mixture of 4.5 g. of hypoxanthine and 26 g. of phosphoryl chloride for two hours. The excess phos phosphorus pentasulfide in 100 ml. of pyridine was re phoryl chloride was removed in vacuo and the remaining fluxed for 8 hours. The excess pyridine was then re Syrup poured on 300 g. of crushed ice. The crude 2 moved in vacuo, and the residue boiled with 150 ml. of methylmercapto-6-chloropurine which precipitated was water. This solution was acidified with hydrochloric acid 20 collected, washed with water and dried at 120°. and 6-mercaptopurine precipitated slowly on standing. Five grams of 2-methylmercapto-6-chloropurine was heated with 55 ml. of 2 N sodium hydrosulfide at 140 EXAMPLE 6 for six hours in a sealed tube. The reaction mixture was acidified with acetic acid and 2-methylmercapto-6-mer Purinyl-6-disulfide 25 captopurine precipitated. The compound was purified by A solution of 8.65 g. of 6-mercaptopurine hydrate and sellion dilute sodium hydroxide and reprecipitation 14 g. of potassium carbonate in 250 ml. of hot water was with acid. cooled to 20. To this was added slowly with shaking EXAMPLE 12 50 ml. of 1 N aqueous iodine-potassium iodide solution. 30 The end-point of the reaction was determined by the 2-methylamino-6-mercaptopurine use of starch solution as an indicator for the excess Five grams of 2-methylmercapto-6-hydroxypurine and iodine. After chilling for ten minutes the precipitate of 20 ml. of 14% methanolic methylamine were heated in a purinyl-disulfide was filtered off, washed with water, Sealed vessel at 140 for 19 hours. The reaction mixture methanol and ether and dried at room temperature. 35 was taken to dryness in vacuo and the residue dissolved in 10 ml. of concentrated hydrochloric acid and 50 ml. EXAMPLE 7 of water. The solution was filtered and neutralized with ammonium hydroxide, whereupon 2-methylamino-6-hy. 2-amino-6-mercaptopurine droxypurine (2.7 g.) precipitated. A mixture of 2.7 g of finely divided guanine, 10 g. of 40 A mixture of 2.7 g of 2-methylamino-6-hydroxypurine, pulverized phosphorus pentasulfide, 10 ml. of pyridine 4 g. of pulverized "liver of sulfur" and 15 g. of phosphorus and 100 ml. of tetralin was heated at 200 with me pentasulfide was heated at 200 for 10 hours with me chanical stirring for 5 hours. After cooling, the mix chanical stirring. After cooling, the insoluble material ture was filtered and the insoluble residue treated with was filtered off, washed with benzene and dried. It was 150 ml. of water and 50 ml. of concentrated ammonium then treated with 250 ml. of water and 15 ml. of concen hydroxide. The ammoniacal solution was filtered, heated trated ammonium hydroxide and heated to boiling. The to boiling and acidified with acetic acid. Upon cooling, ammoniacal solution was filtered and acidified with glacial 2-amino-6-mercaptopurine precipitated as a dark yellow acetic acid. After cooling, the precipitate of 2-methyl powder. amino-6-mercaptopurine was collected, washed with water and dried at 100°. Its ultraviolet absorption spectrum EXAMPLE 8 closely resembles that of 2-amino-6-mercaptopurine. 2-amino-6-mercaptopurine One gram of crude 2-amino-6-chloropurine was heated EXAMPLE 13 with 20 ml.
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