US3019226A - Piperazine salt of phytic acid - Google Patents
Piperazine salt of phytic acid Download PDFInfo
- Publication number
- US3019226A US3019226A US805375A US80537559A US3019226A US 3019226 A US3019226 A US 3019226A US 805375 A US805375 A US 805375A US 80537559 A US80537559 A US 80537559A US 3019226 A US3019226 A US 3019226A
- Authority
- US
- United States
- Prior art keywords
- phytic acid
- salt
- solution
- piperazine salt
- sodium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/098—Esters of polyphosphoric acids or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/117—Esters of phosphoric acids with cycloaliphatic alcohols
Definitions
- This invention relates to new urolitholytic agents and more particularly to new compounds which are the salts of phytic acid and non-toxic organic bases.
- sodium phytate is of use in lowering urinary calcium, thereby reducing the incidence of kidney stones in susceptible persons.
- relatively large dosages of the medicament are required, usually in the range of about 5 grams to about 20 grams daily.
- persons who have a history of kidney stones are often afilicted with other physiological conditions, such as hypertension or related cardiac conditions, which counterindicate the ingestion of large quantities of sodium ion.
- sodium phytate suffers the disadvantage of requiring the administration of large quantities of sodium ions to patients from whom sodium (e.g. salt) should be kept.
- the compounds of this invention which comprise the salts of phytic acid and non-toxic organic bases, preferably organic bases which yield watersoluble salts with phytic acid, such as non-toxic organic bases of less than ten carbon atoms, as exemplified by the non-toxic lower alkyl amines, di(lower alkyl) amines, hydroxy(lower alkyl)amines (e.g. p-aminoethanol and 1- amino-Z-propanol), di-hydroxy(lower alkyl)amines, trihydroxy(lower alkyl)amines (e.g.
- amino-lower alkanediols amino-lower alkanepolyols (e.g. N-methyl-glucamine)
- hydroxy-polyalkylene-polyamines [c.g. N-(hydroxyethyl)diethylenetriamine and N-(hydroxyethyl)propylenediamine], ester and ether derivatives of such hydroxy containing amines (e.g. acetylethanolamine and Z-aminoethoxyethanol), polyalkylene-polyamines (e.g.
- phytic acid is reacted with the desired non-toxic organic base to yield the fully or partially neutralized corresponding phytate derivative; or (b) by metathesis, an inorganic salt of phytic acid, such as an alkali metal salt (e.g. sodium phytate) is treated with the desired non-toxic organic base or an inorganic acid-addition salt thereof (e.g. hydrochloride) to yield a phytic acid derivative fully or partially neutralized with the desired non-toxic organic base; or (c) phytic acid is treated with an inorganic acid salt of 3,019,226 Patented Jan. 30, 1962 Q the desired non-toxic organic base.
- an alkali metal salt e.g. sodium phytate
- an inorganic acid-addition salt thereof e.g. hydrochloride
- the compounds of this invention are useful in the treatment and/or prevention of renal calculi, for which purpose they are administered perorally in a daily dose of about 5 grams to about 20 grams.
- the compounds of this invention can be formulated in the usual manner to give peroral compositions, such as tablets, capsules or powders, or may be suspended or dissolved in customary manner to give elixers, syrups, etc.
- EXAMPLE 3 Phytic acid, salt with 6 moles of choline To 100 cc. of 45% aqueous solution of choline bicar bonate is added 64 cc. of a 40% aqueous solution of phytic acid. The pH of the resulting solution is 5.1 and the total volume is cc. The product can be isolated by diluting 80 cc. of the solution to 500 cc. with water (pH 5.3) and freeze-drying to yield a gummy solid.
- EXAMPLE 4 Phytic acid, salt with p-aminoethanol To 100 cc. of a 40% aqueous solution of phytic acid is added 51.2 g. (0.84 M) of p-aminoethanol. The pH of the resulting solution is 6.4 and the total volume is cc. 100 cc. of this solution is diluted to 800 cc. and freezedried to yield the product as a viscous oil.
- EXAMPLE 5 Phytic acid, salt with triethanol amine To a solution of 92.4 grams of sodium phytate in 100 ml. of water, there is added a solution of 220 grams triethanol amine hydrochloride in 500 ml. of water. The solution is then freeze-dried and the residue suspended in 500 ml. of absolute ethanol. The insoluble sodium chloride is removed by filtration and the filtrate is concentrated to dryness under reduced pressure to give the de' sired product as a viscous oil.
Description
United States Patent Ofifice 3,019,226 PIPERAZINE SALT F PHY TIC ACID Jack Bernstein, New Brunswick, and William A. Lott,
Maplewood, NJ., assignors to Olin Mathieson Chemical Corporation, New York, N.Y., a corporation of Virginia No Drawing. Filed Apr. 10, 1959, Ser. No. 805,375 1 Claim. (Cl. 260-268) This invention relates to new urolitholytic agents and more particularly to new compounds which are the salts of phytic acid and non-toxic organic bases.
Recently it has been found that sodium phytate is of use in lowering urinary calcium, thereby reducing the incidence of kidney stones in susceptible persons. To be effective in the reduction of renal calculi, however, relatively large dosages of the medicament are required, usually in the range of about 5 grams to about 20 grams daily. Unfortunately persons who have a history of kidney stones are often afilicted with other physiological conditions, such as hypertension or related cardiac conditions, which counterindicate the ingestion of large quantities of sodium ion. Hence, sodium phytate suffers the disadvantage of requiring the administration of large quantities of sodium ions to patients from whom sodium (e.g. salt) should be kept.
It is an object of this invention, therefore, to provide a new class of chemical compounds which are useful in the treatment and/or prevention of renal calculi and which are less likely to cause untoward side-eifects.
This object is achieved by the compounds of this invention which comprise the salts of phytic acid and non-toxic organic bases, preferably organic bases which yield watersoluble salts with phytic acid, such as non-toxic organic bases of less than ten carbon atoms, as exemplified by the non-toxic lower alkyl amines, di(lower alkyl) amines, hydroxy(lower alkyl)amines (e.g. p-aminoethanol and 1- amino-Z-propanol), di-hydroxy(lower alkyl)amines, trihydroxy(lower alkyl)amines (e.g. triethanolamine and triisopropanolamine), amino-lower alkanediols, amino-lower alkanepolyols (e.g. N-methyl-glucamine), hydroxy-polyalkylene-polyamines [c.g. N-(hydroxyethyl)diethylenetriamine and N-(hydroxyethyl)propylenediamine], ester and ether derivatives of such hydroxy containing amines (e.g. acetylethanolamine and Z-aminoethoxyethanol), polyalkylene-polyamines (e.g. triethylene-tetramine), monocyclic N-heterocyclic compounds, such as piperazine and 4-(aminopropyl)morpholine, and quaternary ammonium salts such as choline. (By salts of phytic acid and nontoxic organic bases is meant not only salts wherein all twelve acidic hydrogen ions of the phytic acid are combined with organic bases, but also salts wherein the phytic acid is partially neutralized and salts wherein some of the phosphate groups are neutralized with inorganic bases, such as alkali metals.)
To prepare the compounds of this invention: (a) phytic acid is reacted with the desired non-toxic organic base to yield the fully or partially neutralized corresponding phytate derivative; or (b) by metathesis, an inorganic salt of phytic acid, such as an alkali metal salt (e.g. sodium phytate) is treated with the desired non-toxic organic base or an inorganic acid-addition salt thereof (e.g. hydrochloride) to yield a phytic acid derivative fully or partially neutralized with the desired non-toxic organic base; or (c) phytic acid is treated with an inorganic acid salt of 3,019,226 Patented Jan. 30, 1962 Q the desired non-toxic organic base. If sodium phytate is employed as the reactant, then preferably all or substantially all of the sodium ion is replaced thereby minimizing the sodium content of the final phytate product.
The compounds of this invention are useful in the treatment and/or prevention of renal calculi, for which purpose they are administered perorally in a daily dose of about 5 grams to about 20 grams. The compounds of this invention can be formulated in the usual manner to give peroral compositions, such as tablets, capsules or powders, or may be suspended or dissolved in customary manner to give elixers, syrups, etc.
The following examples illustrate the invention (all temperatures being centigrade):
EXAMPLE 1 Phytic acid, salt with 3 moles of piperazine hexahydrate To 200 cc. of a 40% aqueous solution of phytic acid is added 97 g. (0.5 M) of piperazine hexahydrate. The resulting solution has a pH of 3.7 and a total volume of 275 cc. 100 cc. of this solution is diluted to 800 cc. (pH 4.2) and freeze-dried to yield about 39 g. of product melting at about 90100.
EXAMPLE 2 Phytic acid, salt with 6 moles of piperazine decahydrate To 200 cc. of 40% aqueous solution of phytic acid is added 194 g. (1.0 M) of piperazine hexahydrate. The solution has a pH of 7.4 and a total volume of 360 cc. After standing a few minutes crystallization occurs. Then 500 cc. of methanol is added and the mixture allowed to stand. The solid is filtered and washed with methanol to yield about 159 g. of product melting at about with decomposition.
EXAMPLE 3 Phytic acid, salt with 6 moles of choline To 100 cc. of 45% aqueous solution of choline bicar bonate is added 64 cc. of a 40% aqueous solution of phytic acid. The pH of the resulting solution is 5.1 and the total volume is cc. The product can be isolated by diluting 80 cc. of the solution to 500 cc. with water (pH 5.3) and freeze-drying to yield a gummy solid.
EXAMPLE 4 Phytic acid, salt with p-aminoethanol To 100 cc. of a 40% aqueous solution of phytic acid is added 51.2 g. (0.84 M) of p-aminoethanol. The pH of the resulting solution is 6.4 and the total volume is cc. 100 cc. of this solution is diluted to 800 cc. and freezedried to yield the product as a viscous oil.
EXAMPLE 5 Phytic acid, salt with triethanol amine To a solution of 92.4 grams of sodium phytate in 100 ml. of water, there is added a solution of 220 grams triethanol amine hydrochloride in 500 ml. of water. The solution is then freeze-dried and the residue suspended in 500 ml. of absolute ethanol. The insoluble sodium chloride is removed by filtration and the filtrate is concentrated to dryness under reduced pressure to give the de' sired product as a viscous oil.
3 EXAMPLE 6 Phytic acid, salt with N-methylglucamine References Cited in the file of this patent UNITED STATES PATENTS Stoehr July 17, 1894 Connstein Jan. 15, 1901 Adams et a1 Jan. 6, 1942 Karrer Mar. 18, 1952 Blackett et al. Dec. 18, 1956 Petrow et al Apr. 29, 1958 Bond Dec. 29, 1959
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US805375A US3019226A (en) | 1959-04-10 | 1959-04-10 | Piperazine salt of phytic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US805375A US3019226A (en) | 1959-04-10 | 1959-04-10 | Piperazine salt of phytic acid |
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US3019226A true US3019226A (en) | 1962-01-30 |
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US805375A Expired - Lifetime US3019226A (en) | 1959-04-10 | 1959-04-10 | Piperazine salt of phytic acid |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3216949A (en) * | 1962-07-05 | 1965-11-09 | Universal Oil Prod Co | Water-soluble corrosion inhibitors |
US3255190A (en) * | 1961-05-31 | 1966-06-07 | Lab For Pharmaceutical Dev Inc | Amine salts of pyrrolidone carboxylic acid |
US3522258A (en) * | 1966-05-20 | 1970-07-28 | Farmaceutici Italia | Piperazine di-(n-acetyl-glycinate) |
US3528983A (en) * | 1967-05-04 | 1970-09-15 | Edward Henderson | Piperazinium bis(acetylsalicylate) |
WO2007004244A1 (en) * | 2005-06-30 | 2007-01-11 | Maria De Luca | Salts or complexes of methyl donors with phytic acid or its derivatives and method for the synthesis thereof |
JP2007238532A (en) * | 2006-03-10 | 2007-09-20 | National Institute Of Advanced Industrial & Technology | Fat-soluble metal phosphate and flame retardant or metal extracting agent comprising the same as active ingredient |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US523018A (en) * | 1894-07-17 | bayer | ||
US665879A (en) * | 1899-06-26 | 1901-01-15 | Firm Of Benno Jaffe | Piperazin quinate and process of making same. |
US2268556A (en) * | 1939-01-06 | 1942-01-06 | Du Pont | Fire retardant textile |
US2589707A (en) * | 1950-06-06 | 1952-03-18 | Korner John | Choline gallate and its preparation |
US2774759A (en) * | 1955-01-06 | 1956-12-18 | American Cyanamid Co | Preparation of choline base and choline salts |
US2832783A (en) * | 1954-05-28 | 1958-04-29 | British Drug Houses Ltd | Preparation of piperazine adipate |
US2919275A (en) * | 1957-07-30 | 1959-12-29 | Houdry Process Corp | Purification of piperazine |
-
1959
- 1959-04-10 US US805375A patent/US3019226A/en not_active Expired - Lifetime
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US523018A (en) * | 1894-07-17 | bayer | ||
US665879A (en) * | 1899-06-26 | 1901-01-15 | Firm Of Benno Jaffe | Piperazin quinate and process of making same. |
US2268556A (en) * | 1939-01-06 | 1942-01-06 | Du Pont | Fire retardant textile |
US2589707A (en) * | 1950-06-06 | 1952-03-18 | Korner John | Choline gallate and its preparation |
US2832783A (en) * | 1954-05-28 | 1958-04-29 | British Drug Houses Ltd | Preparation of piperazine adipate |
US2774759A (en) * | 1955-01-06 | 1956-12-18 | American Cyanamid Co | Preparation of choline base and choline salts |
US2919275A (en) * | 1957-07-30 | 1959-12-29 | Houdry Process Corp | Purification of piperazine |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3255190A (en) * | 1961-05-31 | 1966-06-07 | Lab For Pharmaceutical Dev Inc | Amine salts of pyrrolidone carboxylic acid |
US3216949A (en) * | 1962-07-05 | 1965-11-09 | Universal Oil Prod Co | Water-soluble corrosion inhibitors |
US3522258A (en) * | 1966-05-20 | 1970-07-28 | Farmaceutici Italia | Piperazine di-(n-acetyl-glycinate) |
US3528983A (en) * | 1967-05-04 | 1970-09-15 | Edward Henderson | Piperazinium bis(acetylsalicylate) |
WO2007004244A1 (en) * | 2005-06-30 | 2007-01-11 | Maria De Luca | Salts or complexes of methyl donors with phytic acid or its derivatives and method for the synthesis thereof |
JP2010235616A (en) * | 2005-06-30 | 2010-10-21 | Luca Maria De | Salt or complex of methyl donor with phytic acid or its derivative, and method for synthesis thereof |
KR101346974B1 (en) * | 2005-06-30 | 2014-01-02 | 마리아 드 루카 | Salts or complexes of methyl donors with phytic acid or its derivatives and method for the synthesis thereof |
JP2007238532A (en) * | 2006-03-10 | 2007-09-20 | National Institute Of Advanced Industrial & Technology | Fat-soluble metal phosphate and flame retardant or metal extracting agent comprising the same as active ingredient |
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