US2907781A - Monohydroxy magnesium aluminum salt of an amino aliphatic acid and method of preparing same - Google Patents

Monohydroxy magnesium aluminum salt of an amino aliphatic acid and method of preparing same Download PDF

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US2907781A
US2907781A US590299A US59029956A US2907781A US 2907781 A US2907781 A US 2907781A US 590299 A US590299 A US 590299A US 59029956 A US59029956 A US 59029956A US 2907781 A US2907781 A US 2907781A
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aluminum
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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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/06—Aluminium compounds
    • C07F5/069—Aluminium compounds without C-aluminium linkages
    • 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
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages

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  • the primary object of the present invention toprovide a new and unique chemical compound which can be used as a pharmaceutical agent for controlling stomach acidity without producing undesirable side effects, such as constipation, laxation, acid rebound, and the like.
  • FIG. 1 is a graph. containing a number of curves which serve to show the antacid properties of the composition of the present invention in comparison with other conventional antacids;
  • Fig. 2 is a graph which serves to show the acid neutralizing properties of the composition of the present invention in comparison with conventional antacids.
  • the present invention resides in the discovery that amino aliphatic acids, such as glycine, alanine, lysine, and glutamic acid, can be .reacted with basic aluminum and magnesium salts to produce a monohydroxy aluminum magnesium salt of the amino acid. If glycine is reacted with stoichiometric quantities of aluminum and magnesium compounds, it is possible to produce mono-hydroxy mono-magnesium quadri-aluminum amino acetate, which composition has unusual antacid properties.
  • amino aliphatic acids such as glycine, alanine, lysine, and glutamic acid
  • Example I A 25% slurry of aluminum oxide (purified) containing 51 pounds of aluminum salt is heated to to F., and with continued heat and agitation, 37 pounds 8 ounces of glycine is slowly added. The physical conditions are maintained for 30 to 60 minutes after the addition of the glycine is complete to form Compound A.
  • reaction mixture of Compound A is then cooled to room temperature with constant stirring, and 18 pounds 4 ounces of hydrogen chloride, which has been diluted to 4 to 8 Normal with distilledwater, is slowly added.
  • the reaction mixture of Compound A is then cooled to room temperature with constant stirring, and 18 pounds 4 ounces of hydrogen chloride, which has been diluted to 4 to 8 Normal with distilledwater, is slowly added.
  • a 25 slurry containing 51 pounds of aluminum oxide (purified) is stirred vigorously while 18 pounds 4 ounces of hydrogen chloride, diluted to 4 to 8 Normal with distilled water, is added. Agitation is maintained for 30 minutes after the addition of the hydrogen, chloride is completed.
  • the reaction mixture is filtered and Patented Oct. 6, 1959 of the present invention will anhydrous a I 3 dried at 165 F. at 10 millimeters pressure. The resulting 69 pounds 3 ounces of Compound C is then ready for use in subsequent reactions.
  • the resulting hydroxy aluminum magnesium aminoacetate is partially soluble in the dimethylformarnide, so 200 pounds of distilled water is added to the reaction mixture, which results in the precipitation of a white semi-crystalline material.
  • the reaction mixture is filtered, the solid portion Washed once with water, refiltered, and dried at 110 F.
  • Example II The same procedure as Example I can be followed using glutarnic acid instead of glycine and using 2 mols of the various reactants for each mol of glutamic acid, the latter being a dicarboxy acid.
  • the finished product is. an hydroxy magnesium aluminum di-salt of glutarnic acid and, based on empirical analysis is found to have the following molecular formula:
  • the preparations herem described provide excellent acid neutralization in the stomach over extended periods of'time and maintain an evenly buffered condition within the stomach, thereby maintaining the stomach pH with in the optimum limits of pH 3 to pH 5.
  • the curves designated A, B, Cjand D are, respectively, aluminum hydroxide gel, 21 di-hydroxy-mono-salt of glycine, aluminum hydroxide and magnesium trisilicate, and an unreacted mixture of calcium carbonate and glycine.
  • the curve designated E is mono hydroxy mono magnesium-quadri-aluminum amino acetate.
  • compositions of the present invention possess exceptionally high acid-consuming capacity and unusual effective buffering properties and, therefore, provide an effective and safe antacid which ar'fords prompt relief from any and all discomfort caused by gastric hyperacidity,
  • the buffering capacity is so well controlled mately five .hours, thus efiectively eliminating any possibility of acid rebound or alkalosis.
  • the antacid compositions of the present invention do not have any laxative or constitpating effect, do not provoke allergic reactions, and may be administered in tablet, capsule, or liquid form, depending upon the needs and requirements of the patient.
  • the antacid compositions of the present invention effectively coat ulcerated areas and supply desirable amino nitrogen in a form which aids tissue repair of the ulcerated areas.
  • the method of preparing hydroxy aluminum magnesium salts of amino aliphatic acids of the group consisting of glycine, glutamic acid, lysine, and alanine comprises reacting aluminum oxide with the amino aliphatic acid to form a first reaction product, adding hydrogen chloride to said first reaction product to form a second reaction product, reacting aluminum oxide with hydrogen chloride to form a third reaction product, mixing a solution of magnesium dimethyl with a solution of the third reaction product to form a fourth reaction product, adding to said fourth reaction product the second reaction product, and thereafter precipitating the hydroxy aluminum magnesium salt of the amino aliphatic acid.
  • the method of preparing a mono-hydroxy monomagnesium quadri-aluminum salt of an amino aliphatic acid of the class consisting of glycine, glutamic acid, lysine and alanine comprises adding hydrogen chloride to the reaction product of aluminum oxide and the amino aliphatic acid to form an intermediate compound, adding magnesium dimethyl to the reaction product of the aluminum oxide and hydrogen chloride to form another intermediate compound, and thereafter reacting said intermediate compounds with each other to form said salt.
  • the method of preparing a monohydroxy monomagnesium quadri-aluminum salt of amino aliphatic acids of the class consisting of glycine, glutamic acid, lysine, and alanine comprises reacting a solution of the amino aliphatic acid with stoichiometric quantities of aluminum oxide and magnesium dimethyl at elevated temperature in dimethylformamide.

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Description

Oct. 6,1959 v. M. HERMELIN 2,907,781 uonommaoxy MAGNESIUM ALUMINUM SALT OF AN AMINO ALIPHATIC ACID AND METHOD OF PREPARING SAME Filed June 8, 1956 RETARDED DIGESTION AND ALKALOSIS RANGE FOR NORMAL DIGESTION HYPERACIDITY x I I. Kin. U A
TIME HOURS FIG.
I50 I75 ACID NEUTRALIZATION FACTOR FIG.
INVENTbR. VICTOR M. HERMELIN ATTORNEY MONOHYDROXY MAGNESIUM ALUMINUM SALT OF AN AMINO ALIPHATIC ACID .AND METHOD OF PREPARING SAME Victor M. Hermelin, University City, Mo. Application June 8, 1956, Serial No. 590,299 7 Claims. (Cl. 260-448) This invention relates in general to basic metallic salts instantaneously with the hydrochloric acid of the stomach and create an alkaline condition which retards normal digestion and in extreme cases will produce acute alkalosis. Furthermore, strong alkaline agents, ,when present in excess, are just as irritating, to the ulcerated areas of the stomach lining as excess acid. Consequently, the use of so-called soda tablets, simple carbonates, and the like are no longer" considered as acceptable medicinals in ulcer therapy.
In more recent years, various preparations containing aluminum hydroxide, magnesium trisilicate, calcium compounds, and the like have been developed, but are subject to various objections. For example, aluminum hydroxide has a congestive effect in the intestinal tract and tends to constipate the patient. Calcium compounds are quite similar in action to somewhat stronger alkalis, causing acid rebound and alkalosis. Furthermore, magnesium salts generally have alaxative eflect.
Physiological studies of hyperacidity have indicated that the pathological condition is not merely a simple matter of neutralizing excess quantities of hydrochloric acids of the gastric juice. It is actually a rather complex 1 problem of promoting normal digestion and, at the same time, maintaining a condition within the stomach in which enzymatic action is not elevated to a level at which the tissues of the stomach are attacked. It has been found that the ideal range of acidity which should .be maintained within the stomach extends from pH 3 to pH 5. Within this range, the stomach enzymes do not tend to digest the tissue of the stomach lining and all stomach conditions are ideal for normal digestion. When the pH drops below 3, considerable discomfort ensues and a prolonged continuance of such hyperacidity will irritate the stomach lining and ultimately produce ulcers. On the other hand, when the stomach pH is in excess of 5, a condition of acid deficiency exists under which digestion is materially retarded, and whenthe pH exceeds 7, digestion is virtually stopped. Such conditions of extreme alkalinity ,ordinarilyresult in serious acid rebound within a short space of time, but if such alkaline condition continues over a prolonged period 'of time,
ice
take such preparations repeatedly at short intervals with unsatisfactory results.
It is, therefore, the primary object of the present invention toprovide a new and unique chemical compound which can be used as a pharmaceutical agent for controlling stomach acidity without producing undesirable side effects, such as constipation, laxation, acid rebound, and the like.
It is another object of the present invention to provide a pharmaceutical agent which, When ingested into the stomach of a patient, will neutralize excess gastric acidity and hold the acidity of the stomach within an optimum range for a relatively long period of time.
' Itis also an object of the present invention to provide a pharmaceutical agent adapted for the treatment of gastric hyperacidity and being capable of forming a soft gelatinous protective coating over the stomach lining.
It is a further object of the present invention to provide a pharmaceutical agent of the type ,stated which, in addition to its antacid and protective gel-forming properties, also has the property of promoting the healing of active ulcers through protein reconstitution.
It is an additional object of the present invention to provide a pharmaceutical agent which, when ingested into the stomach, has a continuous and attenuated acid neutralizing and buffering action, so that less frequent dosages are required, thereby contributing materially to the comfort and convenience of the patient.
Other and further objects be apparent from the following description and appended claims. I
In the drawing- Fig. 1 is a graph. containing a number of curves which serve to show the antacid properties of the composition of the present invention in comparison with other conventional antacids; and
Fig. 2 is a graph which serves to show the acid neutralizing properties of the composition of the present invention in comparison with conventional antacids.
Broadly speaking, the present invention resides in the discovery that amino aliphatic acids, such as glycine, alanine, lysine, and glutamic acid, can be .reacted with basic aluminum and magnesium salts to produce a monohydroxy aluminum magnesium salt of the amino acid. If glycine is reacted with stoichiometric quantities of aluminum and magnesium compounds, it is possible to produce mono-hydroxy mono-magnesium quadri-aluminum amino acetate, which composition has unusual antacid properties.
The more detailed practice of the present invention is illustrated by the following examples:
Example I A 25% slurry of aluminum oxide (purified) containing 51 pounds of aluminum salt is heated to to F., and with continued heat and agitation, 37 pounds 8 ounces of glycine is slowly added. The physical conditions are maintained for 30 to 60 minutes after the addition of the glycine is complete to form Compound A.
The reaction mixture of Compound A is then cooled to room temperature with constant stirring, and 18 pounds 4 ounces of hydrogen chloride, which has been diluted to 4 to 8 Normal with distilledwater, is slowly added. The
- resulting compound is then filtered 01f and dried at the patient will sufier from serious nutritional deficiencies F. and 10 millimeters pressure. The resulting 97 pounds 12 ounces of Compound B is then stored under conditions awaiting further use.
A 25 slurry containing 51 pounds of aluminum oxide (purified) is stirred vigorously while 18 pounds 4 ounces of hydrogen chloride, diluted to 4 to 8 Normal with distilled water, is added. Agitation is maintained for 30 minutes after the addition of the hydrogen, chloride is completed. The reaction mixture is filtered and Patented Oct. 6, 1959 of the present invention will anhydrous a I 3 dried at 165 F. at 10 millimeters pressure. The resulting 69 pounds 3 ounces of Compound C is then ready for use in subsequent reactions.
Eighty pounds of anhydrous 'dimethylformamide is used to make a slurry of 69 pounds 3 ounces of Compound'C. A solution of 27 pounds 3 ounces of magnesium dimethyl is made in additional anhydrous dimethyl-j formamideQand-the two are rapidly mixed and agitated. The temperature is slowly elevated until a constant temperature ofl40 F. is achieved. The reaction continues until 25 pounds 4 ounces of methyl chloride is evolved to produce Compound D. At this point 97 pounds 12 ounces of Compound B is rapidly added to the reaction mixture and the reaction continues with the liberation of another 25 pounds. 4 ounces of methyl chloride. The resulting hydroxy aluminum magnesium aminoacetate is partially soluble in the dimethylformarnide, so 200 pounds of distilled water is added to the reaction mixture, which results in the precipitation of a white semi-crystalline material. The reaction mixture is filtered, the solid portion Washed once with water, refiltered, and dried at 110 F.
The chemical reactions involved in the above procedure' can be schematically written as follows:
m (Compound D) (5) Compound D' Compound B ll i ll A1-OA1-Mg-AlOA1 I CH CIT .111120 O= E-CHzNHz The finished product resulting from this reaction is mono hydroxy-mono-magnesium-quadri-ahuninum amino acetate and has the following molecular formula:
O OH ll This product is a definite chemical compound as demonstrated by the fact that when the above described reaction is carried out in successive batches varying the quantitles but not the proportions of materials used, the product' consistently exhibits the following quantitative analysis: &
Percent Aluminurn' 21.49
"Q -00] Nitrogen 2.89
1 that the pH curve is maintained completely within the idealrange of pH 3'to pH 5 for a period of approxi- These percentages conform very closely to the theoretical percentages of aluminum, magnesium, and nitrogen present in the above designated chemical compound.
Example II The same procedure as Example I can be followed using glutarnic acid instead of glycine and using 2 mols of the various reactants for each mol of glutamic acid, the latter being a dicarboxy acid.
The finished product is. an hydroxy magnesium aluminum di-salt of glutarnic acid and, based on empirical analysis is found to have the following molecular formula:
Example III The same procedure as Example I can be followed I 'using lysine instead of glycine. Since lysine is a mono- =dCHNH -(CHz)2-NH V A similar saltof alanine has been prepared" and by empiricalanalysis has been found to bev m noagma; um-rnono-hydroxy-quadri-aluminum alpha amino propionate. This compound also has been found to have similar therapeutic properties. i
The preparations herem described provide excellent acid neutralization in the stomach over extended periods of'time and maintain an evenly buffered condition within the stomach, thereby maintaining the stomach pH with in the optimum limits of pH 3 to pH 5.,
Various comparative tests made with mono-hydroxy mono-rnagnesium-quadri-aluminum amino acetate and a number of the leading ethical preparations now on the market demonstrate that the compositions of the present invention possess unusual and hitherto unattainable .antacid properties. In Fig. 1, the curves designated A, B, Cjand D are, respectively, aluminum hydroxide gel, 21 di-hydroxy-mono-salt of glycine, aluminum hydroxide and magnesium trisilicate, and an unreacted mixture of calcium carbonate and glycine. The curve designated E is mono hydroxy mono magnesium-quadri-aluminum amino acetate. The rapid onset of acid neutralizing action and thelong-duration gently sloping pH curve quite clearly indicate the unusual therapeutic properties of the compounds of the-present invention. This is also corroborated by the comparative study of acid neutraliz ing"cap'acity, asshow'njiri Fig. 2. p
The compositions of the present invention possess exceptionally high acid-consuming capacity and unusual effective buffering properties and, therefore, provide an effective and safe antacid which ar'fords prompt relief from any and all discomfort caused by gastric hyperacidity,
Furthermore, the buffering capacity is so well controlled mately five .hours, thus efiectively eliminating any possibility of acid rebound or alkalosis. :It has also been found that the antacid compositions of the present invention do not have any laxative or constitpating effect, do not provoke allergic reactions, and may be administered in tablet, capsule, or liquid form, depending upon the needs and requirements of the patient. Furthermore, the antacid compositions of the present invention effectively coat ulcerated areas and supply desirable amino nitrogen in a form which aids tissue repair of the ulcerated areas.
The above description and examples are intended to illustrate the invention only and it is to be understood that any modifications or variations which conform to the spirit of the invention are intended to be included within the scope of the claims.
I claim:
1. As a composition of matter, a mono-hydroxy monomagnesium quadri-aluminum salt of an amino aliphatic acid of the class consisting of glycine, glutamic acid, lysine, and alanine.
2. As a composition of matter, mono-hydroxy monomagnesium quadri-aluminum amino acetate.
3. As a composition of matter, monohydroxy mono magnesium quadri-aluminum diamino caproate.
4. The method of preparing hydroxy aluminum magnesium salts of amino aliphatic acids of the group consisting of glycine, glutamic acid, lysine, and alanine, which method comprises reacting aluminum oxide with the amino aliphatic acid to form a first reaction product, adding hydrogen chloride to said first reaction product to form a second reaction product, reacting aluminum oxide with hydrogen chloride to form a third reaction product, mixing a solution of magnesium dimethyl with a solution of the third reaction product to form a fourth reaction product, adding to said fourth reaction product the second reaction product, and thereafter precipitating the hydroxy aluminum magnesium salt of the amino aliphatic acid.
5. The method of preparing a mono-hydroxy monomagnesium quadri-aluminum salt of an amino aliphatic acid of the class consisting of glycine, glutamic acid, lysine and alanine, which method comprises adding hydrogen chloride to the reaction product of aluminum oxide and the amino aliphatic acid to form an intermediate compound, adding magnesium dimethyl to the reaction product of the aluminum oxide and hydrogen chloride to form another intermediate compound, and thereafter reacting said intermediate compounds with each other to form said salt.
6. The method of preparing a monohydroxy monomagnesium quadri-aluminum salt of amino aliphatic acids of the class consisting of glycine, glutamic acid, lysine, and alanine, which method comprises reacting a solution of the amino aliphatic acid with stoichiometric quantities of aluminum oxide and magnesium dimethyl at elevated temperature in dimethylformamide.
7. As a composition of matter the bis-(mono-hydroxy mono-magnesium quadri-aluminum) salt of glutamic acid.
References Cited in the file of this patent UNITED STATES PATENTS 2,480,743 Krantz et *al. Aug. 30, 1949 2,588,090 Delmar Mar. 4, 1952 2,641,604 Maistre et al June 9, 1953 OTHER REFERENCES Brown: Journal Appl. Chem., 1951, 1, suppl. 2, 159.

Claims (2)

1. AS A COMPOSITION OF MATTER, A MONO-HYDROXY MONOMAGNESIUM QUADRI-ALUMINUM SALT OF AN AMINO ALIPHATIC ACID OF THE CLASS CONSISTING OF GLYCINE, GLUTAMIC ACID, LYSINE, AND ALANINE.
4. THE METHOD OF PREPARING HYDROXY ALUMINUM MAGNESIUM SALTS OF AMINO ALIPHATIC ACIDS OF THE GROUP CONSISTING OF GLYCINE, GLUTAMIC ACID, LYSINE, AND ALANINE, WHICH METHOD COMPRISE REACTING ALUMINUM OXIDE WITH THE AMINO ALIPHATIC ACID TO FORM A FIRST REACTION PRODUCT, ADDING HYDROGEN CHLORIDE TO SAID FIRST REACTION PRODUCT TO FORM A SECOND REACTION PRODUCT, REACTING ALUMINUYM OXIDE WITH HYDROGEN CHLORIDE TO FORM A THIRD REACTION PRODUCT, MIXING A SOLUTION OF MAGNESIUM DIMETHYL WITH A SOLUTION OF THE THIRD REACTION PRODUCT TO FORM A FOURTH REACTION PRODUCT, ADDING TO SAID FOURTH REACTION PRODUCT THE SECOND REACTION PRODUCT, AND THEREAFTER PRECIPITATING THE HYDROXY ALUMINUM MAGNESIUM SALT OF THE AMINO ALIPHATIC ACID.
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3208986A (en) * 1958-11-28 1965-09-28 Montedison Spa Polymerization catalysts and their use in the polymerization of unsaturated hydrocarbons
US3342814A (en) * 1962-01-15 1967-09-19 Union Carbide Corp Adducts of metal borohydrides and organic polynitrogen compounds
US3347893A (en) * 1961-12-27 1967-10-17 Union Carbide Corp Adducts
FR2051516A1 (en) * 1969-05-12 1971-04-09 Spezialchemie Gmbh Et Co
US3920792A (en) * 1972-05-08 1975-11-18 Stewart M Beekman Stable antacid compositions based on aluminum hydroxide and containing hydroxy magnesium aminoacetate and process for preparing the same
US4013699A (en) * 1973-08-09 1977-03-22 Rhone-Poulenc S.A. Aluminium and/or magnesium salts of amino-acids
US4385068A (en) * 1980-03-10 1983-05-24 Davinci Laboratories, A Division Of Food Science Corporation N,N-Dimethylglycine and use in immune response
US4631189A (en) * 1980-03-10 1986-12-23 Da Vinci Laboratories, a division of FoodScience Corporation N,N-dimethylglycine and use in immune response

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2480743A (en) * 1946-05-03 1949-08-30 Krantz Basic aluminum salt of an aliphatic amino acid and method of preparing the same
US2588090A (en) * 1950-04-14 1952-03-04 Geza S Delmar Process for the preparation of basic aluminum salts of alpha amino acids
US2641604A (en) * 1949-05-28 1953-06-09 Chattanooga Medicine Co Aluminum salts of dibasic amino acids

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2480743A (en) * 1946-05-03 1949-08-30 Krantz Basic aluminum salt of an aliphatic amino acid and method of preparing the same
US2641604A (en) * 1949-05-28 1953-06-09 Chattanooga Medicine Co Aluminum salts of dibasic amino acids
US2588090A (en) * 1950-04-14 1952-03-04 Geza S Delmar Process for the preparation of basic aluminum salts of alpha amino acids

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3208986A (en) * 1958-11-28 1965-09-28 Montedison Spa Polymerization catalysts and their use in the polymerization of unsaturated hydrocarbons
US3347893A (en) * 1961-12-27 1967-10-17 Union Carbide Corp Adducts
US3342814A (en) * 1962-01-15 1967-09-19 Union Carbide Corp Adducts of metal borohydrides and organic polynitrogen compounds
FR2051516A1 (en) * 1969-05-12 1971-04-09 Spezialchemie Gmbh Et Co
US3920792A (en) * 1972-05-08 1975-11-18 Stewart M Beekman Stable antacid compositions based on aluminum hydroxide and containing hydroxy magnesium aminoacetate and process for preparing the same
US4013699A (en) * 1973-08-09 1977-03-22 Rhone-Poulenc S.A. Aluminium and/or magnesium salts of amino-acids
US4385068A (en) * 1980-03-10 1983-05-24 Davinci Laboratories, A Division Of Food Science Corporation N,N-Dimethylglycine and use in immune response
US4631189A (en) * 1980-03-10 1986-12-23 Da Vinci Laboratories, a division of FoodScience Corporation N,N-dimethylglycine and use in immune response

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