US2498687A - Vasoconstrictor composition - Google Patents

Vasoconstrictor composition Download PDF

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US2498687A
US2498687A US626182A US62618245A US2498687A US 2498687 A US2498687 A US 2498687A US 626182 A US626182 A US 626182A US 62618245 A US62618245 A US 62618245A US 2498687 A US2498687 A US 2498687A
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ephedra
ephedrine
vasoconstrictor
base
exchange
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Delmar H Larsen
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/17—Gnetophyta, e.g. Ephedraceae (Mormon-tea family)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
    • A61K47/585—Ion exchange resins, e.g. polystyrene sulfonic acid resin

Definitions

  • This invention relates to preparations of ephedrine and related compounds, and more particularly to improved compositions for oral administration of such drugs.
  • Ephedrine is, as is well-known, the principal alkaloid of the pharmacologically active species of ephedra, or mahuang, particularly Ephedra equisetina Bunge, E. sz'm'ca Stapf, E. nebrodensis, E. intermedia, E. oulgaris (so-called), and others. In these species the usual content of ephedrine varies between about A;% and 1%% by weight, and occasionally as high as 1.9%. Ephedrine may also be obtained synthetically. Related compounds may also be synthesized, and will be further referred to hereinbelow.
  • ephedrine acts in a similar manner to epinephrine, stimulating the sympathetic nervous system. It is a vasoconstrictor, and is particularly useful in the symptomatic treatment, of allergic manifestations such as asthma, urticaria, angioneurotic edema, and the like, and has the great advantage over epinephrine of being effective when given orally. 7
  • Ephedrine itself is likewise not without disadvantageous secondary reactions, commonly causing anxiety, palpitation, restlessness, sleeplessness, and the like, particularly in the allergic individual, who is often predisposed to such symptoms. It is therefore common to compound ephedrine with sedatives such as the barbiturates in order to overcome the undesired reactions.
  • sedatives such as the barbiturates
  • the use of such sedatives, while accomplishing the immediate purpose, is in turn undesirable, particularly when barbiturates are used, as these may be habit-forming, and may cause such degenerative conditions as agranulocytosis with long-continued use.
  • One of the objects of this invention is to provide a means of administering ephedrine and related compounds while avoiding the undesirable subsidiary reactions therefrom.
  • Another object of the invention is to provide a means of administering ephedra while avoiding the undesirable subsidiary reactions therefrom.
  • Another object of the invention is to provide a'means of prolonging the action of oral vasoconstrictor medication while at the same time reducing the intensity of the initial effects of treatment.
  • Another object is to provide a novel and useful medication for allergic disorders.
  • diuretics and cardiac stimulants such as caffeine, theobromine, theophylline, and aminophylline are sometimes useful as adjuncts, as are antispasmodics such as belladonna, stramonium, and hyoscyamus and their alkaloids, and also alkali metal and alkaline-earth halides such as calcium, sodium, and potassium iodides, and potassium and calcium chlorides.
  • sedatives such as bromides, chloral hydrate, and barbiturates can of course be added, but their use is made large unnecessary by the synergistic action of the ephedra rine.
  • zeolites such as analcite, matrolite, heulandite, stilbite, common greensand zeolites, and even synthetically made zealites of of the alumino-silicate type; or even such of those of the recently introduced organic cation exchangers of, for example, the sulfonated coal or the synthetic resin type, as are non-toxic. These will naturally be'finely divided-:and' may'be present in such.
  • the base exchange reaction may be carried out during manufacture,- asfcr example'by mixing the two reacting substances with water, drying, and comminuting; or they may bef'simply mixed dry, allowing reaction to take place when they are. moistened "by .the gastric juices.
  • .another basebesides the vasoconstrictor is present, such as. for example. caffeine or. theophylline, .a. portionor .all of. this other baselmay likewise. beboundby base. exchange. "Wherethe reaction is not.
  • Ephedrine has been used as the'example ofjthe vasoconstrictor .hereinabove ;'.but it will be understood that thereare otheranalogues and-derivatives having anessentially similar action and likewise-adapted for oral administration which can alsorbe usedinxaccor'dance withthe principles of this invention.
  • Naturallyfluhose which .are volatile..in..the..f-ree state, such as li-phenyland .1-cyclohexyl-2- aminopropane, areibestusedlin the non-volatile salt' form, to avoid loss. by evaporation, Any other bases employed, such as xanthine diuretics, may of course also be in the free base or salt form.
  • ephedra is the well-known crude drug ephedra, or mahuang, of species containing ephedrine in pharmacologically active quantities.
  • the drug consists largely of the green stems of the plant.
  • the amountsof fullers earth is sufficient to adsorb'about half of the ephedrinehydrochloride, assuming a base-exchange capacity of 3 30 --m i1liequivalents per grams.
  • Mixture A a-nd'MixtureB are :packed intoopposite ends ofpa -gelatin-capsule, whichsare then putvtogeth'er.
  • Each alkaloidis provided with approximately half its equivalent weight :in
  • compositionfor medicinal use comprising,
  • ephedrine and vasoconstrictive ephedra in a weight-ratio of ephedrinezephedra between the approximate limits of 1:20 and 1 :2, together with a comminuted solid cation-exchange material in quantity sufiicient to adsorb by base-exchange a substantial proportion of the ephedrine.
  • a composition for medicinal use comprising; an orally effective vasoconstrictor containing the group RCC-N where R is a six membered carbon ring and vasoconstrictive ephedra in a weight-ratio of vasoconstrictor:ephedra between the approximate limits of 1 :20 and 1 :2.
  • a composition for medicinal use comprising, an orally efiective vasoconstrictor containing the group R--CCN- where R is a six membered carbon ring and vasoconstrictive ephedra in a Weight-ratio of vasoconstrictorzephedra between the approximate limits of 1:20 and 1:2, together with a comminuted solid cation-exchange material in quantity suflicient to adsorb by base-exchange a substantial proportion of the vasoconstrictor.
  • a composition for medicinal use comprising, an orally efiective vasoconstrictor containing the group R--CCN- where R is a six membered carbon ring and vasoconstrictive ephedra; a xanthine diuretic chosen from the group consisting of cafieine, theobromine, theophylline, and their double salts with ethylene diamine, sodium acetate, and sodium salicylate; and a base-exchange material; in which the vasoconstrictor: ephedra ratio lies between the limits of 1:20 and 1 :2, and in which the vasoconstrictor and ephedra are mixed with a partial stoichiometric equivalent of the base-exchange material, and in which the 6 xanthine diuretic is separately mixed with a partially stoichiometric equivalent of the base-exchange material, and in which the vasoconstrictor and xanthine diuretic portions are juxtaposed for simultaneous administration.
  • composition according to claim 4 and wherein the comminuted solid cation-exchange material is selected from the group consisting of zeolites, fullers earths, bentonites and illites.

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Description

Patented Feb. 28, 1950 UNITED STATES PATENT OFFICE No Drawing. Application November 1, 1945, Serial No. 626,182
'7 Claims.
This invention relates to preparations of ephedrine and related compounds, and more particularly to improved compositions for oral administration of such drugs.
Ephedrine is, as is well-known, the principal alkaloid of the pharmacologically active species of ephedra, or mahuang, particularly Ephedra equisetina Bunge, E. sz'm'ca Stapf, E. nebrodensis, E. intermedia, E. oulgaris (so-called), and others. In these species the usual content of ephedrine varies between about A;% and 1%% by weight, and occasionally as high as 1.9%. Ephedrine may also be obtained synthetically. Related compounds may also be synthesized, and will be further referred to hereinbelow.
Pharmacologically, ephedrine acts in a similar manner to epinephrine, stimulating the sympathetic nervous system. It is a vasoconstrictor, and is particularly useful in the symptomatic treatment, of allergic manifestations such as asthma, urticaria, angioneurotic edema, and the like, and has the great advantage over epinephrine of being effective when given orally. 7
The crude drug ephedra is seldom given to obtain the therapeutic action of ephedrine (except possibly by Chinese herb doctors) because of undesirable side reactions caused by other constituents of the crude drug. Ephedrine itself, whether obtained naturally or synthetically, is likewise not without disadvantageous secondary reactions, commonly causing anxiety, palpitation, restlessness, sleeplessness, and the like, particularly in the allergic individual, who is often predisposed to such symptoms. It is therefore common to compound ephedrine with sedatives such as the barbiturates in order to overcome the undesired reactions. The use of such sedatives, while accomplishing the immediate purpose, is in turn undesirable, particularly when barbiturates are used, as these may be habit-forming, and may cause such degenerative conditions as agranulocytosis with long-continued use.
One of the objects of this invention is to provide a means of administering ephedrine and related compounds while avoiding the undesirable subsidiary reactions therefrom.
Another object of the invention is to provide a means of administering ephedra while avoiding the undesirable subsidiary reactions therefrom.
Another object of the invention is to provide a'means of prolonging the action of oral vasoconstrictor medication while at the same time reducing the intensity of the initial effects of treatment.
Another object is to provide a novel and useful medication for allergic disorders.
I have discovered that a remarkable synergism between ephedrine and ephedra when taken together in certain ratios. As stated above, neither ephedrine nor ephedra is wholly satisfactory when used alone, but when so combined that the ratio of total ephedrine to ephedra is between about 1:20 and 1:2, and more desirably between about 1:10 and 1:3, the hereinbefore cited undesirable side reactions of ephedrine are greatly reduced. At the ratios given not enough ephedra is taken in to cause in turn the reactions incident upon it, and indeed the ephedrine itself appears to' modify these. It will be appreciated that ratios of this magnitude do not occur in natural mahuang, ephedrine contents of respectively 1% and 2% giving ephedrinezephedra ratios of 1:99 and 1:49.
The pharmacology of ephedra as to all of its minor constituents has not been sufiiciently elucidated that an explanation of the phenomena of this invention can be given; but it seems not unlikely that hitherto unappreciated constituents of ephedra have the property of modifying the pharmacological action of ephedrine so that the purpose of this invention can be realized, but that the ephedrinezephedra ratio in naturally occuring ephedra has such values that the elfect is defeated when enough ephedra is taken to provide a therapeutic quantity of ephedrine. However, it should be understood that I do not wish to be limited to any particular theory of action.
It is in some cases desirable, but not necessary for the purposes of this invention in its broadest aspects, to include other ingredients in a preparation for allergic relief embodying the principles of the invention. Thus, diuretics and cardiac stimulants such as caffeine, theobromine, theophylline, and aminophylline are sometimes useful as adjuncts, as are antispasmodics such as belladonna, stramonium, and hyoscyamus and their alkaloids, and also alkali metal and alkaline-earth halides such as calcium, sodium, and potassium iodides, and potassium and calcium chlorides. sedatives such as bromides, chloral hydrate, and barbiturates can of course be added, but their use is made large unnecessary by the synergistic action of the ephedra rine.
To prolong the effect of the medication, and at the same time to lessen the impact of the drugs on the system, it is desirable to add a suitable quantity of a substance exhibiting base exchange,
such as clays of moderate or high base exchange with the ephed-,
3 capacity like fullers earth, illite, bentonite, and similar clays; or zeolites such as analcite, matrolite, heulandite, stilbite, common greensand zeolites, and even synthetically made zealites of of the alumino-silicate type; or even such of those of the recently introduced organic cation exchangers of, for example, the sulfonated coal or the synthetic resin type, as are non-toxic. These will naturally be'finely divided-:and' may'be present in such. quantity (as maybe readily calculated from the base exchange capacity for large cations of the exchange substance and the stoichiometric equivalence of the ephedrineior.v other alkaloid or organic base present) asto bind all or only a portion of the organicb'ase,'viz., ephedrine. The base exchange reaction may be carried out during manufacture,- asfcr example'by mixing the two reacting substances with water, drying, and comminuting; or they may bef'simply mixed dry, allowing reaction to take place when they are. moistened "by .the gastric juices.
I prefer to bind up only aportion of the organic base, viz., ephedrine, in this-manner, so thatthe remainder is available for. absorption as soomas it reaches. the stomach, while-the. exchangedlportion is-withheld vfrom availability until the. alkaline regions of the intestines. are reached, whereupon 'the base tends to. be liberated fromthe cation exchanger.asaconsequence of the higher pH. Where .another basebesides the vasoconstrictor is present, such as. for example. caffeine or. theophylline, .a. portionor .all of. this other baselmay likewise. beboundby base. exchange. "Wherethe reaction is not. effected d'uringrmanufacture, it may beldesirable to separate the various organic bases in separate capsules or .pills or. portions thereof, each with itsproperamount of, cation exchanger, so'that the reaction of the stronger base with the cation exchanger to the exclusion of-the weakeris avoided.
"Ephedrine has been used as the'example ofjthe vasoconstrictor .hereinabove ;'.but it will be understood that thereare otheranalogues and-derivatives having anessentially similar action and likewise-adapted for oral administration which can alsorbe usedinxaccor'dance withthe principles of this invention. "Examples of: theseiarei' racemic ephedrine which of course contains half ofrthe ofiicial stereoisomem benzyl ephedrine, ethyl ephedrine, neo-synephrine' (a-hydroxy p=methylaminoethyl-3-hydroxybenzene), .propa'drine (-ahydroxy-p-aminopropylb'enzene), amphetamine (1-phenyl 2-aminopropane) benzedrex (1-03 clohexyl-2-aminopropa'ne) desoxyephedrine;privine (aL-naphthyLZ-methyI imidazoline) and others, which'ior'the most part may be structurally consideredas "derivatives of ethylamine, and more'particulariyas p aryl ethylamine derivatives. All'of" the foregoing compounds contain the group R'C C-'-N where'R is a sixmembered carbon ring. Those skilled in'the art recognize the six-membered carbon ring. ethyl amine structure as contributing vasoconstrictive action,v as described in "fThe Pharmacological Basisof Therapeutics by Goodman and Gilman, page427. It will lee-understood that these vasocon'strictor amines can be employed as the free basaorlin the. salt" form, for example, .as the hydrochloride, sulfate, acetate, and so forth. (Their actionwhere used according to the invention is independent. or whether they are. in the'freelamine or salt form. Naturallyfluhose which .are volatile..in..the..f-ree state, such as li-phenyland .1-cyclohexyl-2- aminopropane, areibestusedlin the non-volatile salt' form, to avoid loss. by evaporation, Any other bases employed, such as xanthine diuretics, may of course also be in the free base or salt form.
In the examples and claims which follow, ephedra is the well-known crude drug ephedra, or mahuang, of species containing ephedrine in pharmacologically active quantities. The drug consists largely of the green stems of the plant.
Examples Grains .iEphedrine sulfate .Ephedra 2 The powdered ingredients are encapsulated.
Grains E'phedrine Ephedra 1 /2 Aminophylline 1% The; powdered ingredients are formed into a pill.
. Grains Ephedrine hydrochloride 1 Ephedra 4 Fullers earth 3 The 'powdered ingredients are encapsulated.
The amountsof fullers earth is sufficient to adsorb'about half of the ephedrinehydrochloride, assuming a base-exchange capacity of 3 30 --m i1liequivalents per grams.
Mixture A a-nd'MixtureB are :packed intoopposite ends ofpa -gelatin-capsule, whichsare then putvtogeth'er. Each alkaloidis provided with approximately half its equivalent weight :in
; bentonite, .and 13hBr.ma/nn8r"Of packing insures that eachportion of-bentonite willbe saturated withits properalkaloid.
Grains Amphetamine'sulfate" Benzylephe'drine hydrochloride 4/8 Neosynephrin'e hydrochloride 4A; Ephedra 5 Sodiumiodide 5 The powdered ingredients are encapsulated.
In the examples. above, the quantities given are fora vsingleldose.
What :I olaimis:
i. l. A composition for "medicinal use:comprising, ephedrine and jvasoconstrictive. ephedra in a weight-ratio ref ephedrine :ephedra. between the approximatelimits of 1 :20 and 1.: 2.
2. A compositionfor medicinal use comprising,
ephedrine and vasoconstrictive ephedra in a weight-ratio of ephedrinezephedra between the approximate limits of 1:20 and 1 :2, together with a comminuted solid cation-exchange material in quantity sufiicient to adsorb by base-exchange a substantial proportion of the ephedrine.
3. A composition for medicinal use comprising; an orally effective vasoconstrictor containing the group RCC-N where R is a six membered carbon ring and vasoconstrictive ephedra in a weight-ratio of vasoconstrictor:ephedra between the approximate limits of 1 :20 and 1 :2.
4. A composition for medicinal use comprising, an orally efiective vasoconstrictor containing the group R--CCN- where R is a six membered carbon ring and vasoconstrictive ephedra in a Weight-ratio of vasoconstrictorzephedra between the approximate limits of 1:20 and 1:2, together with a comminuted solid cation-exchange material in quantity suflicient to adsorb by base-exchange a substantial proportion of the vasoconstrictor.
5. A composition for medicinal use comprising, an orally efiective vasoconstrictor containing the group R--CCN- where R is a six membered carbon ring and vasoconstrictive ephedra; a xanthine diuretic chosen from the group consisting of cafieine, theobromine, theophylline, and their double salts with ethylene diamine, sodium acetate, and sodium salicylate; and a base-exchange material; in which the vasoconstrictor: ephedra ratio lies between the limits of 1:20 and 1 :2, and in which the vasoconstrictor and ephedra are mixed with a partial stoichiometric equivalent of the base-exchange material, and in which the 6 xanthine diuretic is separately mixed with a partially stoichiometric equivalent of the base-exchange material, and in which the vasoconstrictor and xanthine diuretic portions are juxtaposed for simultaneous administration.
6. A composition according to claim 3 and wherein the ephedra is comminuted.
7. A composition according to claim 4 and wherein the comminuted solid cation-exchange material is selected from the group consisting of zeolites, fullers earths, bentonites and illites.
DELMAR I-I. LARSEN.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 1,250,331 Lloyd Dec. 18, 1917 2,033,856 Smith Mar. 10, 1936 2,222,952 Mothes Nov, 26, 1940 FOREIGN PATENTS Number Country Date 690,488 Germany Apr. 26, 1940 691,339 Germany May 23, 1940 OTHER REFERENCES Chen and SchmidtEphedrine and Related Substances, pages 82-94, Williams and Wilkins 00., Baltimore, 1930. (Copy in Division 43.)
Chen-The Chemist and Druggist, November 26, 1938, Ephedrine and Ma Huang. (Reprint in Division 43, 4 pages.)

Claims (1)

  1. 3. A COMPOSITION FOR MEDICINAL USE COMPRISING; AN ORALLY EFFECTIVE VASOCONSTRICTOR CONTAINING THE GROUP R-C-C-N WHERE R IS A SIX MEMBERED CARBON RING AND VASOCONSTRICTIVE EPHEDRA IN A WEIGHT-RADIO OF VASCONSTRICTOR:EPHEDRA BETWEEN THE APPROXIMATE LIMITS OF 1:20 AND 1:2.
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2990332A (en) * 1958-04-02 1961-06-27 Wallace & Tiernan Inc Pharmaceutical preparations comprising cation exchange resin adsorption compounds and treatment therewith
US3007847A (en) * 1956-05-08 1961-11-07 Warner Lambert Pharmaceutical Antispasmodic composition
US3027303A (en) * 1958-06-04 1962-03-27 Bristol Myers Co Hematinic compositions
US3035979A (en) * 1959-04-15 1962-05-22 Wallace & Tiernan Inc Pharmaceutical composition containing a resin-narcotic compound and a resinantihistamine compound
US3084099A (en) * 1958-08-04 1963-04-02 Wallace & Tiernan Inc Therapeutic amine-resin complex composition and method of using same
US3100738A (en) * 1961-08-09 1963-08-13 Neisler Lab Inc Uniform release process
US3108044A (en) * 1957-10-03 1963-10-22 Clinical Products Ltd Medicament of polystyrene anion exchange resin having a barbiturate adsorbed thereon
US3342685A (en) * 1957-10-03 1967-09-19 Clinical Products Ltd Vitamin-cation exchange resin therapy and method of eliminating drug odor
US3699219A (en) * 1969-07-15 1972-10-17 Haver Lockland Lab Method of administering amino acids to convalescing livestock and composition therefor

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1250331A (en) * 1915-07-06 1917-12-18 John Uri Lloyd Alkaloidal compound.
US2033856A (en) * 1934-07-05 1936-03-10 Claude R Smith Compounds of bentonite with organic bases and process of producing same
DE690488C (en) * 1939-02-24 1940-04-26 Chemisch Pharmazeutische A G B Process for the production of concentrated aqueous caffeine solutions
DE691339C (en) * 1939-02-24 1940-05-23 Chemisch Pharmazeutische A G B Process for the preparation of concentrated aqueous theophylline solutions
US2222952A (en) * 1938-01-15 1940-11-26 Bilhuber Inc E Theophylline and caffeine solution

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1250331A (en) * 1915-07-06 1917-12-18 John Uri Lloyd Alkaloidal compound.
US2033856A (en) * 1934-07-05 1936-03-10 Claude R Smith Compounds of bentonite with organic bases and process of producing same
US2222952A (en) * 1938-01-15 1940-11-26 Bilhuber Inc E Theophylline and caffeine solution
DE690488C (en) * 1939-02-24 1940-04-26 Chemisch Pharmazeutische A G B Process for the production of concentrated aqueous caffeine solutions
DE691339C (en) * 1939-02-24 1940-05-23 Chemisch Pharmazeutische A G B Process for the preparation of concentrated aqueous theophylline solutions

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3007847A (en) * 1956-05-08 1961-11-07 Warner Lambert Pharmaceutical Antispasmodic composition
US3108044A (en) * 1957-10-03 1963-10-22 Clinical Products Ltd Medicament of polystyrene anion exchange resin having a barbiturate adsorbed thereon
US3342685A (en) * 1957-10-03 1967-09-19 Clinical Products Ltd Vitamin-cation exchange resin therapy and method of eliminating drug odor
US2990332A (en) * 1958-04-02 1961-06-27 Wallace & Tiernan Inc Pharmaceutical preparations comprising cation exchange resin adsorption compounds and treatment therewith
US3027303A (en) * 1958-06-04 1962-03-27 Bristol Myers Co Hematinic compositions
US3084099A (en) * 1958-08-04 1963-04-02 Wallace & Tiernan Inc Therapeutic amine-resin complex composition and method of using same
US3035979A (en) * 1959-04-15 1962-05-22 Wallace & Tiernan Inc Pharmaceutical composition containing a resin-narcotic compound and a resinantihistamine compound
US3100738A (en) * 1961-08-09 1963-08-13 Neisler Lab Inc Uniform release process
US3699219A (en) * 1969-07-15 1972-10-17 Haver Lockland Lab Method of administering amino acids to convalescing livestock and composition therefor

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