US2789938A - Method of producing a diuretic effect with p-carboxybenzenesulfonamide - Google Patents

Method of producing a diuretic effect with p-carboxybenzenesulfonamide Download PDF

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US2789938A
US2789938A US322356A US32235652A US2789938A US 2789938 A US2789938 A US 2789938A US 322356 A US322356 A US 322356A US 32235652 A US32235652 A US 32235652A US 2789938 A US2789938 A US 2789938A
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carboxybenzenesulfonamide
sodium
ions
composition
grams
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US322356A
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Paul W Wilcox
Jr Karl H Beyer
Ziegler Carl
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Merck and Co Inc
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings

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  • This invention relates to diuretic compositions, and more particularly to a composition containing an agent which serves to increase the elimination of cations, principally sodium and potassium.
  • the invention also involves the process of increasing the elimination of cations, and more particularly the sodium cation, from the body of man or other animals. This process involves the administration of the active agent and the regulation of the quantity consumed so as to bring about this desired result.
  • compositions which, when consumed, makes it possible for a person to apply the desired amounts of salt to his food.
  • the composition of the invention serves to provide for excretion of a major amount of this salt intake with the result that the patient is allowed a diet to which he will adhere and at the same time the daily salt balance approximates that resulting from moderate to severe salt restriction without the aid of this invention.
  • composition of the invention there are a number of clinical indications for the use of the composition of the invention.
  • various edematous states it is desirable to eliminate cations, and principally the sodium cations, from the body, in order to bring about a reduction of the edematous condition.
  • the composition of the invention By giving such a patient the composition of the invention, this condition will be markedly improved.
  • composition of the invention may be particularly useful in the patient prone to congestive heart failure.
  • the active agent of the composition of the invention is para-carboxybenzenesulfonamide (or 'para-sulfamylbenzoic acid), having the structural formula:
  • This active agent may be combined with either a solid or a liquid carrier or diluent.
  • the resulting compound may be put up in the form of tablets, powder, or capsules, or in any form which can be used for oral consumption.
  • the liquid preparation may be bottled or even put up in encapsulated form for ease of oral administration.
  • the liquid form may as well be for parenteral administration and in this event precautions should of course be taken to produce a sterile composition.
  • the active ingredient may be either in complete solution or may be in suspension.
  • the unit dosage of the composition should contain therapeutic amounts of the active agent.
  • a unit dosage of the ingredient will contain from 10 mg. to 16 gm., a more preferred range being from 100 mg. to 4.0 gm.
  • the total daily oral intake for an adult should be from 0.5 to 16 grams, and most generally from 2 to 8 grams. About one-fourth these amounts would be taken parenterally.
  • a person required to take this composition will ordinarily prefer at one time to take one or a few tablets or capsules, or one or a few tablespoons of a liquid preparation, or a few cc. of an injectable preparation, the frequency of administration is apparent.
  • compositions are provided which are free of any material amounts of sodium or potassium.
  • a primary purpose of the invention is to increase the elimination of these cations, it follows that it would be desirable not to introduce any sodium or potassium into the person with the active agent of the invention.
  • ordinary pharmaceutical compositions contain sodium and potassium compounds, a feature of the invention resides in their elimination (other than as slight contaminants) from the compositions of the invention.
  • compositions in accordance with the invention, are the following, and from them other suitable compositions will be apparent.
  • Example lI.Sterile solution Grams Ammomia water 28.3% NH; 19.54 p-Carboxybenzenesulfonamide 50 Pyrogen-free double distilled Water, q. s.
  • Example III -Dry filled capsules Kg. p-Carboxybenzenesulfonamide 4 Corn starch USP 0.8
  • Yield 8000 capsules each containing 0.5 gram of pcarboxybenzenesulfonamide.
  • Example I V.Sft elastic capsules p-Carboxybenzenesulfonamide "kilo-.. Peanut oil, q. s. (to form soft creamy mixture).
  • Each cc. of the suspension mixture contains 1.0 gram of the p-carboxybenzenesulfonamide.
  • Example V I Effervescent granule p-Carboxybenzenesulfonamide kg 4 Dulcin kg 0.025
  • Each 4 gm. of granular material contains 2 gm. of pcarboxybenzenesulfonamide.
  • Example VII Granale p-Carboxybenzenesulfonamide kg 4 Powdered sugar USP kg 1.5 Corn starch USP kg 0.5
  • Distilled water a suflicient quantity, about 1000 cc.
  • Example VIII Efiervescent tablet p-Carboxybenzenesulfonamide kg. 4 Dulcin kg 0.025 Calcium Carbonate USP powder kg 3.325
  • Theoretical yield 2000 tablets, each weighing 4 grams and each containing 2 grams of p-carboxybenzenesulfonamide.
  • Example X Powder p-Carboxybenzenesulfonamide 4 Powdered sugar USP 2 Yield: 2000 doses, each weighing 3 grams and each containing 2 grams of p-carboxybenzeuesulfonamide.
  • composition of the invention having the p-carboxybenzenesulfonamide present in smaller or greater concentration
  • the active agent could be present in as low as 1 or 2% by weight of the composition, especially if a clear aqueous solution of relatively insoluble derivatives (hereinafter mentioned) of the p-carb0xybenzenesulfonamide are to be used.
  • the higher relative proportions, as 10% and more, are to be recommended and this may be even if the patient can tolerate the undiluted p-carboxybenzenesulfonamide.
  • the active material in this latter case can be packaged as the pure compound and be labeled for medicinal use with instructions by the physician as to the quantity and frequency of consumption by the patient.
  • a daily amount of from 2 to 16 grams may be prescribed. In most instances the daily intake will be from 4 to 8 grams.
  • the attending physician can determine the proper daily consumption by physical observation of the patient and by measurement of the patients sodium and potassium balance. Based on this information, the daily administration should be regulated to approximately the minimum to bring about and maintain the desired sodium and potassium elimination.
  • the ammonium salt may be utilized.
  • the sodium or potassium salt may be used, but as has been mentioned, this is counterindicated as it introduces the ions which are intended to be eliminated from the body.
  • Other salts may be utilized by replacing the hydrogen of the carboxyl group.
  • the invention contemplates as well other derivatives of the acid, and this includes the lower alkyl esters, the amide, and either the mono or the disubstituted lower alkyl derivatives of the amide form.
  • Representative compounds which may be substituted in the above examples in amounts to yield an equivalent therapeutic effeet, are the following:
  • a method of increasing the elimination of an ion selected from the group consisting of sodium and potassium ions from the body which comprises administering a composition comprising not less than 1.0% by weight of p-carboxybenzenesulfonarnide to a person suffering from an abnormal retention of these ions.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Description

United States Patent METHOD OF PRODUCING A DIURETIC EFFECT WITH p-CARBOXYBENZENESULFONAMIDE No Drawing. Application November 24, 1952,
Serial No. 322,356
5 Claims. (Cl. 167-55) This invention relates to diuretic compositions, and more particularly to a composition containing an agent which serves to increase the elimination of cations, principally sodium and potassium.
The invention also involves the process of increasing the elimination of cations, and more particularly the sodium cation, from the body of man or other animals. This process involves the administration of the active agent and the regulation of the quantity consumed so as to bring about this desired result.
Many persons suffer from an abnormal retention of sodium, principally as the chloride. This may result in the development of edema, may precipitate an episode of congestive heart failure, or may aggravate a pre-existing hypertension. One way to overcome this is to decrease the amount of sodium chloride intake, but-this is an unsatisfactory solution for the reason that many such foods are unpalatable. That is, people object so much to the bland taste of the food that they refuse to adhere to a regime of an extremely low salt consumption.
In accordance with the present invention a composition is provided which, when consumed, makes it possible for a person to apply the desired amounts of salt to his food. The composition of the invention serves to provide for excretion of a major amount of this salt intake with the result that the patient is allowed a diet to which he will adhere and at the same time the daily salt balance approximates that resulting from moderate to severe salt restriction without the aid of this invention.
Furthermore, there are a number of clinical indications for the use of the composition of the invention. In various edematous states it is desirable to eliminate cations, and principally the sodium cations, from the body, in order to bring about a reduction of the edematous condition. By giving such a patient the composition of the invention, this condition will be markedly improved.
The value of salt restriction as a means of limiting the development of edema is well documented. The composition of the invention may be particularly useful in the patient prone to congestive heart failure.
The active agent of the composition of the invention is para-carboxybenzenesulfonamide (or 'para-sulfamylbenzoic acid), having the structural formula:
no 0 o-Q-s ORNH! This active agent may be combined with either a solid or a liquid carrier or diluent. The resulting compound may be put up in the form of tablets, powder, or capsules, or in any form which can be used for oral consumption. Likewise, the liquid preparation may be bottled or even put up in encapsulated form for ease of oral administration. The liquid form may as well be for parenteral administration and in this event precautions should of course be taken to produce a sterile composition. I
In making the composition, conventional pharmaceutical practices may be carried out andthis applies to com- 2,789,938 Patented Apr. 23, 1957 positions for either oral or parenteral use. Ordinary care should be exercised to make sure that no incompatible condition exists with respect to the diluent which is being employed. In the liquid preparation, the active ingredient may be either in complete solution or may be in suspension.
Irrespective of the particular kind of dosage form which is made, the unit dosage of the composition should contain therapeutic amounts of the active agent. Thus, a unit dosage of the ingredient will contain from 10 mg. to 16 gm., a more preferred range being from 100 mg. to 4.0 gm. The total daily oral intake for an adult should be from 0.5 to 16 grams, and most generally from 2 to 8 grams. About one-fourth these amounts would be taken parenterally. Bearing in mind that a person required to take this composition will ordinarily prefer at one time to take one or a few tablets or capsules, or one or a few tablespoons of a liquid preparation, or a few cc. of an injectable preparation, the frequency of administration is apparent.
As a further feature of the invention, compositions are provided which are free of any material amounts of sodium or potassium. As a primary purpose of the invention is to increase the elimination of these cations, it follows that it would be desirable not to introduce any sodium or potassium into the person with the active agent of the invention. As ordinary pharmaceutical compositions contain sodium and potassium compounds, a feature of the invention resides in their elimination (other than as slight contaminants) from the compositions of the invention.
Representative compositions, in accordance with the invention, are the following, and from them other suitable compositions will be apparent.
Example I.Compressea' tablets p-Carboxybenzenesulfonamide 57 lb. 13 oz. Dextrine white NF V 4 lb. 8 oz. Corn starch paste, 1 part Gelatin solution, 2 parts "i 1 8 Distilled water, q. s.
Starch USP dried-MP 3000 7 lb. 8 oz. Talc USP 3 1b. 8 oz. Magnesium stearate purif. imp. powd 3 oz.
Total weight granulation lb.
Compress into 0.65 gram tablets each containing 0.5 gram of p-carboxybenzenesulfonamide. Theoretical yield: 52,500.
Example lI.Sterile solution Grams Ammomia water 28.3% NH; 19.54 p-Carboxybenzenesulfonamide 50 Pyrogen-free double distilled Water, q. s.
Example III.-Dry filled capsules Kg. p-Carboxybenzenesulfonamide 4 Corn starch USP 0.8
" Yield: 8000 capsules each containing 0.5 gram of pcarboxybenzenesulfonamide.
Example I V.Sft elastic capsules p-Carboxybenzenesulfonamide "kilo-.. Peanut oil, q. s. (to form soft creamy mixture).
Make into soft elastic capsules of a suitable size, each capsule representing 500 mg. p-carboxybenzenesulfonamide.
Example V.-Saspension (oral) Distilled Water, q. s. ad.
Each cc. of the suspension mixture contains 1.0 gram of the p-carboxybenzenesulfonamide.
Example V I .Effervescent granule p-Carboxybenzenesulfonamide kg 4 Dulcin kg 0.025
Calcium carbonate powder USP kg 3.375
Corn starch paste 12.5% 1000 cc. allow kg 0.100
Distilled water, a sufficient quantity about 250 cc.
Citric acid fine USP granules kg 0.5 8.0
Yield: 2000 doses. Each 4 gm. of granular material contains 2 gm. of pcarboxybenzenesulfonamide.
Example VII .Granale p-Carboxybenzenesulfonamide kg 4 Powdered sugar USP kg 1.5 Corn starch USP kg 0.5
Distilled water, a suflicient quantity, about 1000 cc.
6 Yield: 2000 doses. Each 3 gm. dose of granular material contains 2 gm. of p-carboxybenzenesulfonamide.
Example VIII .Efiervescent tablet p-Carboxybenzenesulfonamide kg. 4 Dulcin kg 0.025 Calcium Carbonate USP powder kg 3.325
Corn starch paste 12.5% 1.5 liters allow kg 0.150
Distilled water, a suflicient quantity, about 0.5 liter.
Citric acid USP fine granules kg 0.47
Magnesium stearate .kg 0.03
Theoretical yield: 2000 tablets, each weighing 4 grams and each containing 2 grams of p-carboxybenzenesulfonamide.
Example IX.Efiervescent powder Kg. p-Carboxybenzenesulfonamide 4 Dulcin 0.025 Calcium carbonate USP powder 3.475 Citric acid USP powder 0.5 8.0
Yield: 2000 doses of 4 grams each, each containing 2 grams of p-carboxybenzenesulfonamide.
Example X .Powder p-Carboxybenzenesulfonamide 4 Powdered sugar USP 2 Yield: 2000 doses, each weighing 3 grams and each containing 2 grams of p-carboxybenzeuesulfonamide.
Other examples of the composition of the invention having the p-carboxybenzenesulfonamide present in smaller or greater concentration will be apparent. Thus the active agent could be present in as low as 1 or 2% by weight of the composition, especially if a clear aqueous solution of relatively insoluble derivatives (hereinafter mentioned) of the p-carb0xybenzenesulfonamide are to be used. However, because of the relatively large amount of the active agent which must be taken daily, the higher relative proportions, as 10% and more, are to be recommended and this may be even if the patient can tolerate the undiluted p-carboxybenzenesulfonamide. The active material in this latter case can be packaged as the pure compound and be labeled for medicinal use with instructions by the physician as to the quantity and frequency of consumption by the patient.
As has been mentioned, a daily amount of from 2 to 16 grams may be prescribed. In most instances the daily intake will be from 4 to 8 grams. The attending physician can determine the proper daily consumption by physical observation of the patient and by measurement of the patients sodium and potassium balance. Based on this information, the daily administration should be regulated to approximately the minimum to bring about and maintain the desired sodium and potassium elimination.
Although the invention has been described with particular reference to p-carboxybenzenesulfonamide, numerous derivatives of it may be employed as they presumably yield this acid in the body. For example, as is evident from Example II, the ammonium salt may be utilized. The sodium or potassium salt may be used, but as has been mentioned, this is counterindicated as it introduces the ions which are intended to be eliminated from the body. Other salts may be utilized by replacing the hydrogen of the carboxyl group.
The invention contemplates as well other derivatives of the acid, and this includes the lower alkyl esters, the amide, and either the mono or the disubstituted lower alkyl derivatives of the amide form. Representative compounds which may be substituted in the above examples in amounts to yield an equivalent therapeutic effeet, are the following:
Ethyl p-sulfamylbenzoate p-Sulfamy1benzamide CHaNHOC SOzNHz p-Sulfamyl-N-methylbenzamlde (CHa)2NOC SOgNHs p-Sulfamyl-N,N dlmethylbenzamide 3 1) 2 O C S OzNHz p-Sulfamyl-N,N-di-n-propylbenzamide Ill-04119020 SOzNHQ n-Butyl p-sultamylbenzoate OHOzC Cs sec-Butyl p-sulfamylbenzoate S OgNHt .7 a ll Cyclohexyl p-sulfamylbenzoate tert.-Buty1 p-sulfamylbenzoate 2-diethylaminoethyl p-sulfamylbenzoate hydrochloride 2-diethy1aminoethyl p-sulfamylbenzamide hydrochloride NHzNHO C SOzN H2 p-Sulfamylbenzoyl hydrazine SO.NH.
m-Carboxybenzenesulfonamide S OzNH:
o-Carboxybenzenesulfonamide NHzNH O C I @s 021N112 m-Sulfamylbenzoyl hydrazine S OzN H2 O-Sulfumylbenzoyl hydrazine o-Chloro- -sulfamylbenzoie acid CHsO p-Sulfamyl-o-methoxybenzoic acid sium ions from the body which consists in administering to a living person suffering from an abnormal retention of these ions p-carboxybenzenesulfonamide in an amount suflicient to eliminate the excess sodium and potassium ions and bring about the desired electrolyte balance in the person.
2. The process of increasing the elimination of an ion selected from the group consisting of sodium and potassium ions from the body which consists in orally administering to a living person suffering from an abnormal retention of these ions p-carboxybenzenesulfonamide in an amount sufiicient to eliminate the excess sodium and potassium ions and bring about the desired electrolytic balance in the person.
3. The process of increasing the elimination of an ion selected from the group consisting of sodium and potassium ions from the body which consists in parenterally administering to a living person suifering from an abnormal retention of these ions p-carboxybenzenesulfonamide in an amount sufficient to eliminate the excess sodium and potassium ions and bring about the desired electrolyte balance in the person.
4. The process of increasing the elimination of an ion selected from the group consisting of sodium and potassium ions from the body which consists in administering to a living person suffering from an abnormal retention of these ions from A; to 16 grams daily of p-carboxybenzenesulfonamide in an amount suflicient to eliminate the excess sodium and potassium ions and bring about the desired electrolyte balance in the person.
5. A method of increasing the elimination of an ion selected from the group consisting of sodium and potassium ions from the body Which comprises administering a composition comprising not less than 1.0% by weight of p-carboxybenzenesulfonarnide to a person suffering from an abnormal retention of these ions.
References Cited in the file of this patent UNITED STATES PATENTS Miller Aug. 26, 1952 Fiechtinger Dec. 29, 1953 OTHER REFERENCES

Claims (1)

1. THE PROCESS OF INCREASING THE ELIMINATION OF AN ION SELECTED FROM THE GROUP CONSISTING OF SODIUM AND POTASSIUM IONS FROM THE BODY WHICH CONSISTS IN ADMINISTERING TO A LIVING PERSON SUFFERING FROM AN ABNORMAL RETENTION OF THESE IONS P-CARBOXYBENZENESULFONAMIDE IN AN AMOUNT SUFFICIENT TO ELIMINATE THE EXCESS SODIUM AND POTASSIUM IONS AND BRING ABOUT THE DESIRED ELECTROLYTE BALANCE IN THE PERSON.
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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2967130A (en) * 1957-09-05 1961-01-03 Robert G Sanders p-sulfamyl beta-hydroxyethyl carbanilate diuretic compositions
US2991283A (en) * 1957-01-28 1961-07-04 Bofors Ab Substituted amino alkyl esters of paraalkyl sulfamide benzoic acids
DE1146873B (en) * 1960-02-16 1963-04-11 British Drug House Ltd Process for the preparation of 4-chloro-3-sulfamylbenzoic acid and its alkali metal salts
DE1153745B (en) * 1960-05-09 1963-09-05 Parke Davis & Co Process for the preparation of 4-halo-3-sulfamoylbenzoic acid esters
US3110815A (en) * 1959-09-12 1963-11-12 Quarzlampen Gmbh Remote control apparatus for moving an operating lamp
US3112337A (en) * 1960-05-09 1963-11-26 Parke Davis & Co 4-halo-3-sulfamoylbenzoic acid esters
US3162651A (en) * 1961-05-08 1964-12-22 Fidelity Union Trust Company Thienylalkyl esters of 3-sulphamyl-4-chlorobenzoic acid
US3165512A (en) * 1960-09-23 1965-01-12 Geigy Chem Corp Morpholinones
US3346568A (en) * 1961-09-14 1967-10-10 Ciba Geigy Corp 2-amino-5-sulfamyl-benzoic acid hydrazides
US20080131506A1 (en) * 2005-02-16 2008-06-05 Solvay (Societe Anonyme) Tablets Comprising a Biologically Active Substance and an Excipient Containing Calcium Carbonate
WO2008130332A1 (en) 2007-04-20 2008-10-30 Unimed Pharma, Spol. S R.O. Subsituted sulphonamides, process for their preparation, pharmaceutical composition comprising thereof and their use

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2608507A (en) * 1949-08-20 1952-08-26 Sharp & Dohme Inc Dialkyl sulfamyl benzoic acids
US2664439A (en) * 1951-07-25 1953-12-29 Ruhrchemie Ag Process for the production of benzoic-p-sulfonamide

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2608507A (en) * 1949-08-20 1952-08-26 Sharp & Dohme Inc Dialkyl sulfamyl benzoic acids
US2664439A (en) * 1951-07-25 1953-12-29 Ruhrchemie Ag Process for the production of benzoic-p-sulfonamide

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2991283A (en) * 1957-01-28 1961-07-04 Bofors Ab Substituted amino alkyl esters of paraalkyl sulfamide benzoic acids
US2967130A (en) * 1957-09-05 1961-01-03 Robert G Sanders p-sulfamyl beta-hydroxyethyl carbanilate diuretic compositions
US3110815A (en) * 1959-09-12 1963-11-12 Quarzlampen Gmbh Remote control apparatus for moving an operating lamp
DE1146873B (en) * 1960-02-16 1963-04-11 British Drug House Ltd Process for the preparation of 4-chloro-3-sulfamylbenzoic acid and its alkali metal salts
DE1153745B (en) * 1960-05-09 1963-09-05 Parke Davis & Co Process for the preparation of 4-halo-3-sulfamoylbenzoic acid esters
US3112337A (en) * 1960-05-09 1963-11-26 Parke Davis & Co 4-halo-3-sulfamoylbenzoic acid esters
US3165512A (en) * 1960-09-23 1965-01-12 Geigy Chem Corp Morpholinones
US3162651A (en) * 1961-05-08 1964-12-22 Fidelity Union Trust Company Thienylalkyl esters of 3-sulphamyl-4-chlorobenzoic acid
US3346568A (en) * 1961-09-14 1967-10-10 Ciba Geigy Corp 2-amino-5-sulfamyl-benzoic acid hydrazides
US20080131506A1 (en) * 2005-02-16 2008-06-05 Solvay (Societe Anonyme) Tablets Comprising a Biologically Active Substance and an Excipient Containing Calcium Carbonate
US7892576B2 (en) * 2005-02-16 2011-02-22 Solvay (Societe Anonyme) Tablets comprising a biologically active substance and an excipient containing calcium carbonate
WO2008130332A1 (en) 2007-04-20 2008-10-30 Unimed Pharma, Spol. S R.O. Subsituted sulphonamides, process for their preparation, pharmaceutical composition comprising thereof and their use
AU2008241590B2 (en) * 2007-04-20 2012-06-21 Unimed Pharma, Spol. S R.O. Substituted sulphonamides, process for their preparation, pharmaceutical composition comprising thereof and their use
RU2474574C2 (en) * 2007-04-20 2013-02-10 ЮНИМЕД ФАРМА, спол. с.р.о. Substituted sulphonamides, method for production thereof, medicinal agents containing said sulphonamides and use thereof

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