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Folyhydrophenanthrene-3-Monosulfates

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Folyhydrophenanthrene-3-Monosulfates Patented June 16, 1953 2,642,427 ,642,427 soF CYCLOPENTANo foLYHYDROPHENANTHRENE-3-MoNoSULFATEs . Richard B. Hasbrouck, Waukegan, III, assignor - . corporationto Abbott Laboratories, of Illinois. : North Chicago, III, a . Application August 1, 1951, Serial No. 239,857 . s: laims. (CI. 260-239.5) This invention relates to therapeutic prepara ring, to about 95-100° C., and the heating is con tions having hormone activity, and includes tinued for about one and one-quarter hours. At among its objects and advantages, compounds of the end of the heating period the reaction massis increased stability, and methods for producing cooled to about room temperature and about 70 the same. Specifically, the invention relates to parts of anhydrous ether is added. The dense, piperazine salts of the half acid sulfate esters of pink, granular solid which forms is filtered and cyclopentanopolyhydrophenanthrenes. Washed With anhydrous ether. The Solid, which The compounds of the present invention are is a mixture of ammonium estrone-3-imonosulfate. derived from hormone type steroids, known as and pyridine. Sulfamate, is dried. the cyclopentanopolyhydrophenanthrene. Series; 10 About 24 parts of piperazine hexahydrate (or which includes restrogenic steroids, such as es: an equivalent amount of anhydrous piperazine) trone, estradiol, equilin; and equilenin; androster dissolved in a solution of about 125 parts of meth ones; pregnenolones; stereo-isomerides and de anol and 40 parts of water, is added to the crude rivatives thereof, etc. According to the invention, stable organic salts adjustedamnonium to 8-8.5estrone-3-monosulfate. with more of the piperazine, The pH and is of the cyclopentanopolyhydrophenanthrenes are the mixture is gently heated until solution is ef produced, which are particularly suitable for oral fected. The Solution is evaporated to dryness, administration. The salts are odorless, or practi to remove the last traces of water. The dried cally so, and inoffensive to the user. The Saits residue is extracted with about 200 parts of meth are soluble in aqueous media and are stable anol, by slurrying the solid in the methanol and therein. filtering. ... The methanol extract is clarified with Butenandt, Z. Physiol. Chem. 259,222-34 (1939), decolorizing charcoal, and partially concentrated. during an investigation of estrone, prepared sev About 400 parts of anhydrous ether are added eral alkaloid salts of estrone sulfate. The Salts With stirring to the concentrated methanol Sou are quite insoluble in aqueous solutions and are 25 tion, precipitating the piperazine estrone-3-mono not, therefore, particularly adapted for human Sulfate as light tan crystals. The crystals are consumption. A further disadvantage of these dried in vacuum. When recrystallized from meth estrone salts if used for medication, is the fact anol the product melts at 193-195°C. that if any dissociation takes place in the Solu In the example the Sulfamic acid is used in a tion, the alkaloids thus liberated from the con 30 3-molar excess to the estrone, to insure a high pounds produce the general alkaloid effects, which yield of the ammonium estrone sulfate. The ex are undesirable. Some of the alkaloids used to ceSS Sulfamic acid is converted to pyridine, Sul produce the salts are extremely toxic or poisonous famate. and therefore, impractical for use. The ammonium estrone sulfate is a very desir Generally, the compounds of my invention may able intermediate in the process, as the ammoni be prepared from the known naturally occurring 35 um group may be replaced by the piperazine sodium steroid 3-monosulfates or from the ster group. It is important that the basic group of oids per se. The steroids may be sulfonated ac cording to known procedures with Such sulfonat the intermediate salt of the estrone sulfate be less ing agents as sulfur trioxide, chlorosulfonic acid, basic than the piperazine, otherwise no reaction sulfamic acid, etc., and recovered as water-soluble 40 will occur between the two compounds. salts, such as, sodium, annonium, or other alkali Eacample II or alkali metal salts. The salt is then reacted with piperazine (or a piperazine salt) to produce the desired piperazine cyclopentanopolyhydro To a solution of 0.650 gm. of piperazine hexa 45 hydrate in 5 cc. of methanol is added 0.275 gm. phenanthrene-3-monosulfate. of ammonium estradiol-3-monosulfate. The mix The following examples illustrate in detail the ture is warmed gently to dissolve the solids. It present invention. is then concentrated to dryness in vacuum. The Eacample I residue is stirred With about 10 cc. of methanol at 50 40-50 for about one hour. The solution is fil About 10 parts (by weight) of estrone and about tered and the residue Washed with a small amount 10.8 parts of sulfamic acid are placed in a suitable of methanol. About 30 cc. of anhydrous ether reaction vessel such as an ordinary round is added gradually to the methanol solution. The bottomed glass flask, with about 40 parts of py product, piperazine estradiol-3-monosulfate, pre ridine. Dimethylaniline may be substituted for 55 cipitates as light tan crystals, melting point is the pyridine. The mixture is heated, With stir 188° C. - -- 2,642,427 3 4. Eacample III This application is a continuation-in-part of my copending application Serial No. 103,968, filed Piperazine estradiol-3-monosulfate may also be July 9, 1949, now abandoned, entitled “Thera prepared by the hydrogenation of piperazine peutic Compounds.' estrone. Sulfate as follows: A solution of 0.9 gm. of piperazine estrone-3- Others may readily adapt the invention for use monosulfate and 0.750 gm. of piperazine hexa under various conditions of service, by employing hydrate dissolved in 70 cc. of methanol is hydro one or more of the novel features disclosed or genated at 20 lbs. hydrogen pressure in the pres equivalents thereof. As at present advised with ence of 0.15gm. of prehydrogenated-platinum ox respect to the apparent scope of my invention, ide catalyst. After the hydrogen adsorption is 0. I desire to claim the following subject matter. complete, the catalyst is removed by filtration, I claim: . and the filtrate is concentrated under reduced 1. A therapeutic compound selected from the pressure until crystallization starts. ... About 10 group consisting of piperazine estrone-3-mono “volunes of anhydrous ether is then slowly added sulfate, piperazine estradiol-3-monosulfate, pi 15 perazine. equilin-3-monosulfate and piperazine to complete the crystallization. The resulting equilenin-3-monosulfate. piperazine estradiol-3-monosulfate is recovered 2. Piperazine estrone-3-monosulfate. by filtration, washed with ether and dried. 3. Piperazine estradiol-3-monosulfate. Eacample IV 4. Piperazine equilin-3-monosulfate. To a Solution of 0.500 gm. of piperazine hexa 20 5. Piperazine equilenin-3-monosulfate. hydrate in 5 cc. of methanol is added 0.200 gm. 6. The process which comprises reacting a salt of ammonium equilin-3-monosulfate. The mix of a member of the group consisting of estrone ture is warmed gently to effect solution and then 3-monosulfate, estradiol-3-monosulfate, equilin concentrated to dryness in vacuum. The residue 3-monosulfate and equilenin-3-monosulfate with is extracted with 10 cc. of methanol at 40-50 23 piperazine. for about one hour, and then filtered. The fil 7. The process which comprises, reacting am trate is treated with about 30 cc. of ether, added monium estrone-3-monosulfate with piperazine gradually. The product, piperazine equilin-3- to produce piperazine estrone-3-monosulfate. monosulfate, precipitates as a light tan powder. 8. The process which comprises, reacting am 30 monium estradiol-3-monosulfate with piperazine Eacample V to produce piperazine estradiol-3-monosulfate. To a solution of 0.600 gm. piperazine hexa 9. The process which comprises, reacting am hydrate in 5 cc. of methanol is added 0.225 gm. monium equilin-3-monosulfate with piperazine to Of ammonium equilenin-3 - monosulfate. The produce piperazine equilin-3-monosulfate. mixture is warmed gently to cause solution to 35 10. The process which comprises, reacting am take place. It is then concentrated to dryness in monium equilenin-3-monosulfate with piperazine vacuum. The residue is stirred With about 10 to produce piperazine equilenin-3-monosulfate. CC. of methanol for about an hour and then fil RICHARD B. HASBROUCK. tered. To the filtrate is added gradually about 30 cc. of ether. The product, piperazine equilenin 40 References Cited in the file of this patent 3-monosulfate, precipitates as nearly white, small Butenandt, Zeit. Physiol. Chem. 259, pp. 222 Crystals. 234 (1939). .
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