US3167475A - Anti-anaphylactic compositions - Google Patents

Anti-anaphylactic compositions Download PDF

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US3167475A
US3167475A US76504A US7650460A US3167475A US 3167475 A US3167475 A US 3167475A US 76504 A US76504 A US 76504A US 7650460 A US7650460 A US 7650460A US 3167475 A US3167475 A US 3167475A
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anaphylactic
compositions
alkanolamines
ethanolamine
ethyl
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US76504A
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Gottfried Siegfried
Baxendale Lily
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Biorex Laboratories Ltd
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Biorex Laboratories Ltd
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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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • A61K31/13—Amines
    • 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
    • A61K31/13—Amines
    • A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline
    • 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
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/225—Polycarboxylic acids
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • 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
    • A61K31/65—Tetracyclines

Definitions

  • alkanolamines and compounds derived therefrom possess valuable anti-anaphylactic activity when administered experimentally to guinea pigs.
  • These alkanolamine compounds can be administered in simple vehicles, such as distilled water, or in more elaborate vehicles, such as tablet bases.
  • These alkanolamine compounds produce a protective action which can be observed as an increase in the time in which sensitized animals can tolerate an antigen without undergoing anaphylactic shock.
  • compositions should be of considerable value in the treatment of allergic conditions, such as asthma, urticaria or conditions in which some allergic mechanism represents a contributory factor.
  • the low molecular weight alkanolamines which are used according to the present invention may be represented by the general formula:
  • R R and R which may be same or different, are hydrogen atoms or methyl or ethyl radicals; and the esters, salts, amides and quaternary ammonium salts thereof.
  • Examples of compounds which may be added to the alkanolamines are ipecacuanha and cocillana (i.e., expectorants), codeine and pholcodine (i.e., anti-tussives), mepyramine maleate and phenindamine tartrate (i.e., anti-histiminics), adrenaline and ephedrine (i.e., antiasthmatics), prednisone and triamcinolone (i.e., corticosteroids and corticosteroid-like compounds), tetracycline and chloramphenicol (i.e., antibiotics), creosote and cetrimide B.P.
  • ipecacuanha and cocillana i.e., expectorants
  • codeine and pholcodine i.e., anti-tussives
  • mepyramine maleate and phenindamine tartrate i.e., anti-histiminics
  • bactericides i.e., bactericides
  • domiphen bromide and benzalkonium chloride i.e., bacteriostatics
  • aspirin cortisone
  • xanthoglabrol i.e., glycyrrhetinic acid and derivatives thereof (i.e., anti-inflammatory agents)
  • xanthines and ephedrine i.e., bronchodilators
  • the compositions according to the present invention may be made up in the form of inhalations, aerosols, tablets, injections, onematas, suppositories, ointments, lotions and suspensions by admixice ture with an appropriate solid or liquid pharmaceutical carrier or diluent.
  • alkanolamines coming within the scope of the above general formula are ethanolamine, N-methylethanolamine, 'N,N-dimethyl-ethanolamine, choline, N- ethyl-ethanolamine, N,N-diethyl-ethanolamine, N,N,N- triethyl-N-ethylol ammonium salts, N-methyl-Z-aminopropanol, N,N-dimethyl-2-amino-propanol, 2-aminopropanol, N,N,N-trimethyl-N-(Z-propylol) ammonium salts, phoshatidyl-ethanolamine and ethanolamine phosphatase.
  • alkanolamines according to the present invention synergism exists between the alkanolamines according to the present invention and blood pressure-reducing drugs, such as pentaerythrityl tetranitrate, diuretic drugs, such as acetazolarnide and chloroth'iazide, and anti-coagulant drugs, such as phenindione.
  • blood pressure-reducing drugs such as pentaerythrityl tetranitrate
  • diuretic drugs such as acetazolarnide and chloroth'iazide
  • anti-coagulant drugs such as phenindione.
  • Such compositions may be used, for example, in the treatment of arteriosclerosis and coronary thromboses.
  • Fiat tabella. Injection 200 mg. diphenylhydramine hydrochloride 1000 mg. ethyanolamine succinate 900 mg. sodium chloride 100 ml. distilled water 900 mg. domiphen bromide
  • the resultant solution is sterilized by heating for 30 minutes at C. 1 cc. of the sterilized solution is injected as required
  • Enema 200 mg. ethanolamine maleate '100 mg. mepyramine maleate mg. sodium chloride 10 mg. prednisolone phosphate ml. distilled water 0.1% w./w. cetrimide (5)
  • Suppository 200 mg. diphenylhydramine hydrochloride 1000 mg. ethyanolamine succinate 900 mg. sodium chloride 100 ml. distilled water 900 mg. domiphen bromide
  • Enema 200 mg. ethanolamine maleate '100 mg. mepyramine maleate mg. sodium chloride 10 mg. prednisolone phosphate ml.
  • a tablet consisting essentially of 1 part by weight of 2 [-(2 dimethylamino ethyl) (p methoxybenzyl) amino1-pyridine maleate and 2 parts by Weight of choline hydrochloride.
  • Anti-anaphylactic composition of matter consisting essentially of 2-5 parts by Weight of a member selected from the group consisting of alkanolamines of the formula and the pharmaceutically acceptable quaternary ammonium salts and pharmaceutically acceptable bases thereof, in which R; is a member selected from the group consisting of hydrogen, methyl and ethyl, R is a member selected from the group consisting of hydrogen, methyl and ethyl, and R is a member selected from the group consisting of hydrogen, methyl and ethyl and one part by Weight of 2-[(2-dimethy1aminoethyl) (p-methoxybenzyl)-amino]-pyridine maleate, in admixture with a pharmaceutical carrier.

Description

United States Patent 3,167,475 ANTl-ANAPHYLACTEC QOMPUSITEUNS Siegfried Gottfried, llford, and Lily Banendale, London,
England, assignors to lfiiorex Laboratories Limited, London, England, a corporation of the United Kingdom No Drawing. Filed Bee. 19, 1960, Ser. No. 76,504 Claims priority, application Great Britain, Dec. 31, 1959, 44,460/59 2 Claims. (Cl. 167-65) The present invention is concerned with new antianaphylactic compositions.
Using the test procedure outlined by Herxheimer, J. Physiol., 117, 251 (1952), we have found that the lower alkanolamines and compounds derived therefrom possess valuable anti-anaphylactic activity when administered experimentally to guinea pigs. These alkanolamine compounds can be administered in simple vehicles, such as distilled water, or in more elaborate vehicles, such as tablet bases. These alkanolamine compounds produce a protective action which can be observed as an increase in the time in which sensitized animals can tolerate an antigen without undergoing anaphylactic shock.
We have found that the protective action obtained by the use of these alkanolamine compounds is not very great when they are administered on their own but when administered in conjunction with known anti-histaminics which themselves only have a slight protective action, a considerable potentiation of activity is obtained. We have also found that a potentiation of the activity of these alkanolamine compounds is achieved when they are combined with expectorants, anti-tussives, anti-histaminics, anti-asthmatics, bronchodilators, corticosteroids, anti-biotics, bactericidals, tbacteriostatics and/or anti-inflammatory agents.
This discovery has obvious valuable clinical applications since the compositions should be of considerable value in the treatment of allergic conditions, such as asthma, urticaria or conditions in which some allergic mechanism represents a contributory factor.
The low molecular weight alkanolamines which are used according to the present invention may be represented by the general formula:
N-OHCH2O1I R3 R1 wherein R R and R which may be same or different, are hydrogen atoms or methyl or ethyl radicals; and the esters, salts, amides and quaternary ammonium salts thereof.
Examples of compounds which may be added to the alkanolamines are ipecacuanha and cocillana (i.e., expectorants), codeine and pholcodine (i.e., anti-tussives), mepyramine maleate and phenindamine tartrate (i.e., anti-histiminics), adrenaline and ephedrine (i.e., antiasthmatics), prednisone and triamcinolone (i.e., corticosteroids and corticosteroid-like compounds), tetracycline and chloramphenicol (i.e., antibiotics), creosote and cetrimide B.P. (i.e., bactericides), domiphen bromide and benzalkonium chloride (i.e., bacteriostatics), aspirin, cortisone), xanthoglabrol, glycyrrhetinic acid and derivatives thereof (i.e., anti-inflammatory agents), and xanthines and ephedrine (i.e., bronchodilators). Mepyramine is 2-[ (Z-dimethylamino-ethyl) (p-methoxybenzyl) amino]-pyridine; domiphen is dodecyldim=ethyl-(2-phenoxy-ethyl)ammonium bromide; and cetrimide is cetyltrimethylammonium bromide. The compositions according to the present invention, which have been shown to exhibit true synergism, may be made up in the form of inhalations, aerosols, tablets, injections, onematas, suppositories, ointments, lotions and suspensions by admixice ture with an appropriate solid or liquid pharmaceutical carrier or diluent.
Examples of alkanolamines coming within the scope of the above general formula are ethanolamine, N-methylethanolamine, 'N,N-dimethyl-ethanolamine, choline, N- ethyl-ethanolamine, N,N-diethyl-ethanolamine, N,N,N- triethyl-N-ethylol ammonium salts, N-methyl-Z-aminopropanol, N,N-dimethyl-2-amino-propanol, 2-aminopropanol, N,N,N-trimethyl-N-(Z-propylol) ammonium salts, phoshatidyl-ethanolamine and ethanolamine phosphatase.
It is thought that the mechanism of the synergism of the alkanolamines of the above general formula and, for example, anti-histamines, can be outlined as follows: in 1956 Brocklehurst described at the Ciba foundation symposium on histamine, the liberation from sensitized guinea pig lung of two active principles which can be described as chemical mediators of anaphylaxis. He described these chemical mediators as histamine and the slow reacting substances of anaphylaxis (SRS/A). We have shown experimentally that alkanolamines and derivatives thereof of the above given general formula are capable of preventing the release of SRS/A in anaphylaxis. They have a negligible effect on the release of histamine in the same condition and it is, therefore, concluded that the histamine which is released in anaphylaxis is eifectively controlled by the anti-histamine contained in the composition and that the alkanolamine derivatives potentiate this action by preventing the release of SRS/A, which is, for example, normally responsible for bronchospasm, even in the presence of anti-histamine molecules which are incapable of antagonising the pharmacological action of SRS/A.
We have also found that synergism exists between the alkanolamines according to the present invention and blood pressure-reducing drugs, such as pentaerythrityl tetranitrate, diuretic drugs, such as acetazolarnide and chloroth'iazide, and anti-coagulant drugs, such as phenindione. Such compositions may be used, for example, in the treatment of arteriosclerosis and coronary thromboses.
The following examples are given for the purpose of illustrating the present invention.
(1) Inhalation:
500 mg. antazolidine sulphate 1000 mg. ethanolamine hydrochloride 900 mg. sodium chloride 9000 mg. friars balsam ml. water 1 tablespoonful is added to about /2 pint hot water and the vapours given oil are inhaled. Tablet: 25 mg, mepyramine maleate 5 mg. choline hydrochloride incipient, q.s.
Fiat tabella. Injection: 200 mg. diphenylhydramine hydrochloride 1000 mg. ethyanolamine succinate 900 mg. sodium chloride 100 ml. distilled water 900 mg. domiphen bromide The resultant solution is sterilized by heating for 30 minutes at C. 1 cc. of the sterilized solution is injected as required, Enema: 200 mg. ethanolamine maleate '100 mg. mepyramine maleate mg. sodium chloride 10 mg. prednisolone phosphate ml. distilled water 0.1% w./w. cetrimide (5) Suppository:
3 g. chloramphenicol 6 g. choline hydrochloride 3 Q.s. cocoa butter Fiatto mould -30 suppositories. Ointment: 2 g. .benzalkonium chloride 1 g. glycyrrhetinic acid 5 g. ethanolamine hydrochloride Ad 100 g. water-miscib1e ointment base Lotion: 200mg. glycyrrhetinic acid hemisuccinate, disodium salt 1000 mg. ethanolami'ne maleate 900 mg. sodium chloride 900 mg. domiphen bromide 100 ml. distilled Water What we claim is:
1. A tablet consisting essentially of 1 part by weight of 2 [-(2 dimethylamino ethyl) (p methoxybenzyl) amino1-pyridine maleate and 2 parts by Weight of choline hydrochloride.
2. Anti-anaphylactic composition of matter consisting essentially of 2-5 parts by Weight of a member selected from the group consisting of alkanolamines of the formula and the pharmaceutically acceptable quaternary ammonium salts and pharmaceutically acceptable bases thereof, in which R; is a member selected from the group consisting of hydrogen, methyl and ethyl, R is a member selected from the group consisting of hydrogen, methyl and ethyl, and R is a member selected from the group consisting of hydrogen, methyl and ethyl and one part by Weight of 2-[(2-dimethy1aminoethyl) (p-methoxybenzyl)-amino]-pyridine maleate, in admixture with a pharmaceutical carrier.
References Cited by the Examiner Remington, Practice of Pharmacy, 1956, page 1011.
Merck Index, 7th Ed, 1960, pages 84, 253, 390, 794, 84-8, 1056.
J. of Am. Med. Assoc., February 28, 1959, 169:9, 124/ 956.
Swineford, J. of Allergy, 27:2, pp. 137-142, March 1956.
Kile: Antibiotic Medicine and Clinical Therapy, vol. 9 No. 4, September 1958, pp. 578-581.
American Drug Index, 1959, pp. 514518, p. 160.
LEWIS GOTTS, Primary Examiner.
W. B. KNIGHT, FRANK CACCIAPAGLIA, 111.,
Examiners.

Claims (1)

  1. 2. ANTI-ANAPHYLACTIC COMPOSITION OF MATTER CONSISTING ESSENTIALLY OF 2-5 PARTS BY WEIGHT OF A MEMBER SELECTED FROM THE GROUP CONSISTING OF ALKANOLAMINES OF THE FORMULA
US76504A 1959-12-31 1960-12-19 Anti-anaphylactic compositions Expired - Lifetime US3167475A (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2081516A1 (en) * 1970-02-16 1971-12-03 Bristol Myers Co
US4140798A (en) * 1976-11-24 1979-02-20 Kewanee Industries, Inc. Method of inhibiting microorganisms
US4683243A (en) * 1984-02-08 1987-07-28 Richardson-Vicks, Inc. Analgesic and anti-inflammatory compositions comprising diphenhydramine and methods of using same
US4755532A (en) * 1984-02-08 1988-07-05 Richardson-Vicks, Inc. Analgesic and anti-inflammatory compositions comprising diphenhydramine and methods of using same
US4906625A (en) * 1984-02-08 1990-03-06 Richardson-Vicks, Inc. Analgesic and anti-inflammatory compositions comprising diphenhydramine and metyhods of using same
AT390878B (en) * 1984-02-08 1990-07-10 Richardson Vicks Inc METHOD FOR PRODUCING A PHARMACEUTICAL PREPARATION USING AN ANALGETIC AND ANTI-INFLAMMATORY NON-STEROID ACTIVE SUBSTANCE
US4985459A (en) * 1984-02-08 1991-01-15 Richardson-Vicks, Inc. Analgesic and anti-inflammatory compositions comprising diphenhydramine and methods of using same
WO2020021483A1 (en) * 2018-07-27 2020-01-30 Grzegorz Kalbarczyk Arkona Laboratorium Farmakologii Composition for the treatment of oral cavity inflammations

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2469923A1 (en) * 1979-11-26 1981-05-29 Ile De France NEW MEDICINAL PRODUCT BASED ON ASPIRIN AND HEPTAMINOL
US6013273A (en) * 1997-01-27 2000-01-11 Novartis Nutrition Ag Treatment of endotoxic shock

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2081516A1 (en) * 1970-02-16 1971-12-03 Bristol Myers Co
US4140798A (en) * 1976-11-24 1979-02-20 Kewanee Industries, Inc. Method of inhibiting microorganisms
US4683243A (en) * 1984-02-08 1987-07-28 Richardson-Vicks, Inc. Analgesic and anti-inflammatory compositions comprising diphenhydramine and methods of using same
US4755532A (en) * 1984-02-08 1988-07-05 Richardson-Vicks, Inc. Analgesic and anti-inflammatory compositions comprising diphenhydramine and methods of using same
US4906625A (en) * 1984-02-08 1990-03-06 Richardson-Vicks, Inc. Analgesic and anti-inflammatory compositions comprising diphenhydramine and metyhods of using same
AT390878B (en) * 1984-02-08 1990-07-10 Richardson Vicks Inc METHOD FOR PRODUCING A PHARMACEUTICAL PREPARATION USING AN ANALGETIC AND ANTI-INFLAMMATORY NON-STEROID ACTIVE SUBSTANCE
US4985459A (en) * 1984-02-08 1991-01-15 Richardson-Vicks, Inc. Analgesic and anti-inflammatory compositions comprising diphenhydramine and methods of using same
WO2020021483A1 (en) * 2018-07-27 2020-01-30 Grzegorz Kalbarczyk Arkona Laboratorium Farmakologii Composition for the treatment of oral cavity inflammations

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FR874M (en) 1961-10-16

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