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Publication numberUS2467884 A
Publication typeGrant
Publication dateApr 19, 1949
Filing dateFeb 2, 1944
Priority dateFeb 2, 1944
Publication numberUS 2467884 A, US 2467884A, US-A-2467884, US2467884 A, US2467884A
InventorsNathaniel M Elias
Original AssigneeNathaniel M Elias
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Spermicides
US 2467884 A
Abstract  available in
Images(6)
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Claims  available in
Description  (OCR text may contain errors)

Patented Apr. 19, 1949 OFFICE SPERMICIDES Nathaniel M. Elias, New York, N. Y.

No Drawing. Application February 2, 1944, Serial No. 520,774

6 Claims. (Cl. 167-58) This invention relates to compositions useful for topical remedies which will be used chiefly in contact with the mucous membranes in the vaginal cavity. The topical remedies of this invention comprise spermicidal compositions which may range in pl-I value from 1.0 to 7.0, that is, from fairly acid to neutral compositions. One advantage of this invention is the fact that such a range of 'pH values is possible, since I have found a class of spermicide] substances suitable for such compositions which are neutral and relatively harmless. In this way, the spermicidal activity and the acidity are separated one from the other and a pH may be chosen which is best suited for the physiological environment, the pH being established by means of whatever simple organic or inorganic acids and buffer salts may seem desirable. The limitations of pH 1.0 to pH 7.0 are given because it has been found that there is a tendency for the tissues to be irritated by a pH lower than 1.0 or higher than 7.0. Also pH of 7.0 is given as an upper limitation because above this pH an environment is created which may make undesirable infections possible. The invention will now be more particularly described.

I have discovered that a large class of neutral aliphatic hydroxy compounds are definitely spermicidal when suillciently subdivided, and are not at all or negligibly irritating, so that highly spermicidal compositions can be made with them for topical use. The smaller the subdivision in a suitable vehicle the more effectively spermicidal the compound. In the case of insoluble substances of this class. the emulsion particles should be under, 1.5 micronsdown to actual solution in the case of the soluble compounds, where the particles may be considered to be molecular in size. This class includes the following:

(a) Straight chain fatty monohydroxy alcohols having from 8 to 11 carbon atoms in the chain,

(b) Branched chain fatty alcohols from 8 to 18 carbon atoms in the chain.

(c) Glyceryl or ethylene glycol or propyleneglycol monoethers of the alcohols mentioned in (a) and (b).

(d) Polyethylene glycol or polypropylene glycol mono ethers of these alcohols, the poly glycols ranging from the diglycol up to polyglycols of molecular weight of about .4000.

2 glycol monoesters of unsaturated fatty acids having from 10 to 18 carbons in the chain,

(f) The polyethylene glycol and the polypropylene-glycol mono esters of fatty acids, saturated and unsaturated, having from 10 to 18 carbons in the chain, the poly glycols ranging in molecular weightfrom diglycol to poly glycol of molecular weight of about 4000,

(g) Glyceryl monolactate monoesters of unsaturated fatty acids of 10 to 18 carbon atoms.

It will be noted that these compounds comprise higher fatty alcohols, hydroxyethers, hydroxy esters and hydroxy ester ethers. Examples of the fatty alcohols are n-ethyl hexanol (branched chain), n-octanol (straight chain), n-decanol (straight chain), undecanol (branched chain), tetra decanol (branched chain) and heptadecanol (branched chain). These fatty alcohols have the formula ROH where R is the fatty chain.

Examples of the hydroxy ethers are the glyceryl, the propylene glycol-, the diglycol-, the

ethylene glycol, the nonaethylene glycol, the

duodecaethylene glycol, -the polyethylene glycol (molecular weight 1500) -mono ethers of the above alcohols.

The hydroxy ethers of the fatty monohydric alcohols may be made by etherifying one molecule of a poly hydroxy alcohol with one molecule of the fatty monohydroxy alcohol according to the following equation:

The polyhydric alcohols with which the fatty acids are esterifled include ethyleneand propylene-glycol, glycerine and poly alcohols higher than glycerine. For commercial purposes sorbitol and mannitol, which are the highest polyhydric alcohols now available. would constitute the prac- (e) Glyceryl or ethylene glycol or propylene 6 'ticable upper limit. They also include the vari- 3 ous ether and poly ether polyhydric alcohols, such as the poly-ethyleneand polypropyleneglycols. The poly ethylene glycols have the following formula:

OH' CH2 (CHaOCHz) nCHzOH where n may be any integer from 1 to about 90.

Polypropylene glycols have a similar structure except that there is a methyl group added for every two carbons in the chain.

The mono ethers of the glycols and the poly glycols may also be formed by reacting ethylene oxide or propylene oxide with the monohydroxy alcohol itself as follows: (n+ l) C2H4O +ROH ROCH2 (CHnOCHz) nCHflOH Here C2H4O is ethylene oxide, ROH is the fatty alcohol, and 11. may be zero, in which case the group (CH2OCH2) disappears, or may be any integer above zero.

The mono esters of the glycols and poly glycols may be formed similarly as follows:

(11+ 1) C2H4O +RCOOH RCOOCH2 (CHzOCHz) "CH-20H By taking a mono glyceride of a fatty acid and esterifying it further with one molecule of lactic acid and by the elimination of one molecule of water by means of heat alone or by the use of a catalyst, there is obtained a monolactate of the monofatty ester of glycerine. This has one resid-' ual hydroxyl group left free on the glycerine molecule and has an additional hydroxyl group left on the lactate portion of the molecule. Such compounds come within the scope of this invention. This class of compound has the following general formula:

O C OCzHaOH CzHt.- C OR where R is the hydrocarbon residue of the higher fatty acid.

In general, I have found that a greater num ber of hydroxyl or ether radicals in the hydrophilic group are necessary to produce spermicidal products in compounds where the fatty portion of the molecule is saturated than where the fatty portion of the molecule is unsaturated or hydroxylated. In such saturated compounds I have found that the longer the molecular chain of the fatty portion the greater the number of hydroxyl radicals or hydroxyl and ether radicals needed in the hydrophilic group to produce a spermicidal compound.

In using any of the compounds for spermicidal work it is necessary to have them thoroughly emulsified and suitable emulsifying agents are generally desirable. This emulsification is essential since if the particles are small the spermicidal value is improved. When the compounds becomewater soluble as in the case of the higher polyglycol esters and ethers, the presence of an emulsifier is not essential. However. here also it may be desirable to assist in the wetting action of the product in use.

Examples of the esters of the higher saturated fatty acids suitable for this invention are the following:

The mono stearates, the monohydroxy stearates, the monopalmitates, the mono myristates, the mono laurates and monocaprates of nona ethylene glycol, hexaethylene glycol, diethylene glycol, polyethylene glycol (molecular weight 1500), poly propylene glycol (molecular weight 1000), duo deco-ethylene glycol, etc.

In the case of esters containing unsaturated higher fatty radicals the same comments apply as in the case of the saturated compounds. These compounds have much lower melting points than the esters made with saturated fatty radicals, and so emulsify more readily. The glyceryl mono esters of the various eighteen carbon unsaturated fatty acids are quite effective, as are the ethylene and propylene glycol mono esters.

Similarly, the polyethylene and polypropylene glycol esters show strong spermicidal values. In this case also, the effectiveness o f'ithel products are enhanced by the use or emulsifying agents which reduce the surface tension and by thorough emulsification. especially with those compounds which are insoluble in water and not self-dispersible. Here also it is desirable to use them in neutral or acid solution.

Examples of the unsaturated compounds which are found to be spermicidal are the following:

The mono-oleates, -ricinoleates, -1inoleates, -linolenates, ricinolenates and undecylenates of the following poly hydroxy compounds: Glycerine, ethylene glycol, propylene glycol, diethylene glycol, tripropylene glycol, tetraethylene glycol, hexaethylene glycol, nonaethylene glycol, duodecaethylene glycol, polyethylene glycol (molecular weight 1500), polypropylene glycol (molecular weight 1000), polyethylene glycol (molecular weight 4000), sorbitol, mannitol, sorbitan and glyceryl monolactate.

In any of the formulae herein given, where water soluble fatty hydroxy esters or fatty hydroxy ethers are used, there is an approximate molecular equivalence in spermicidal power so that substitutions of one for another of the esters or ethers may be made in proportion to their molecular weights. There appears to be a slight advantage in the water soluble compounds in favor of the unsaturated esters and ethers as compared to the saturated esters, but as a rough guide molecular equivalence is helpful. Accordingly, in Formula 1 below, 3 lbs. of nona ethylene glycol monolaurate has been used. If now polyethylene glycol laurate is used having a molecular weight of 1682 (made from polyethylene glycol of molecular weight 1500), then, since the molecular weight of nona ethylene glycol monolaurate is 596, it would be necessary to. use 2.82 times as much or 8.46 lbs. toobtain a roughly equivalent spermicidal jelly. If a-poly glycol stearate of molecular weight 1086 (made from a polyethylene glycol of molecular weight 820) be used, 1.8 times as much or 5.4 lbs.- would be desirable. If a nona ethylene glycol undecylenate were used, having a molecular weight of 578, somewhat less than 2.9 lbs. would be approximately equivalent.

Molecular equivalence while' applying fairly well to the water soluble compounds applies to a much smaller degree only to'the water insoluble compounds. Here the degree of dispersion is an important factor. However, in general, the greater the dispersion and the more finely divided the particles the more spermicidal is the finished composition.

Having thus described the range of spermicidal substances coming within the scope of the present invention, I shall now give examples of how they may be used in finished spermicidal compositions. In accordance with the present invention, the said substances are uniformly distributed in vehicles to form various spermicidal compositions, these compositions being generally classified as foam powders.- suppositories and tampons. The

particle size of the said substances in said vehicles varies from molecular, i. e.. a solution, to"

approximately 1.5 microns.

JELLIEB In generalit should be noted that in any of the following Jelly formulae glycerine is added to prevent dehydration of the jelly and also to prevent freezing of the composition. The various vegetable gums, such as gum tragacanth, gum karaya and gum arabic may be substituted by other gums such as .Irish moss, Indian gum,

alginates, synthetic cellulose derivativessuch as cqlloresin, locust bean gum, etc. The butyl para /h'ydroxy benzoate may be substituted by other mol'd preventive material such as the methyl,

ethyl or propyl para hydroxy benzoates. The oxyquinoline sulphate may be substituted by other bacteriostatic materials such as the phenols, the alkali alkyl sulphates, etc. The emulsifying agent, sodium lauryl sulphate may be substituted by any or the known alkali, ammonium or substituted ammonium alkyl sulphates or other sulfonated substancessuch as suitonated oils, suifonated hydrocarbons, suifonated castor oil and similar products.

The water soluble acids which may be substituted for lactic'or boric acids as shown in the formulae may include acetic acid, tartaric acid and similar acids. shown in the formula is a butter and may be substituted by sodium acetate or by alkali borates. tartrates, phosphates, lactates, etc.

It is understood that where the water soluble organic acids are used they exert a certain known spermicidal power, but this spermicidal power alone is insufiicient toachieve the effectiveness now possible with these new compositions. I

In the case of boric acid, this product has very slight spermicidal emcacy and is used simply for regulating the, pH of the composition. The fact that compositions of extremely high spermic'idal value, even though neutral, are made possible by this invention, establishes the utility of these compositions regardless of the presence or absence of added acid.

The proportion of the gums used indicates the viscosity range chiefly preferred, but such viscosities may range either lower or higher than indicated in the compositions described without seriously afiecting the utility of the product.

NEUTRAL Jrznnms Usmc War-rm SoLunLn Mono The potassium acetate as AcmJmumUsnra Warn Sonora: Mono Ferry i Earns m 5 mm Bowen Oaamc Acmm No mum!!! 7 Formula 2 Pounds Nona ethylene'lllycol mono laurate.-. 3.0- Oxyquinoline sulphate 0.05 Giycerine i 10.0 Lactic acid-% 2.35 Gum tragacanth 2.0 Gum arabic 0.5 Gum karaya 1.0 Butyl parahydroxy benzoate 0.05 Potassium acetate, sumcient for pH of 3.0 About 0.05 Perfume 0.05

Add suflicient water to make 100.00

In this type of formula, using water soluble esters, the approximate equivalence rule given previously applies.

Less of thespermicidal ester is used here than in Formula 1, since part of the spermicidal action is provided by the lactic acid.

However, more of the ester may be used if a still more spermicidal composition is desired.

Acrn Jnnnus Usma Warns SOLUBLE Mono Esrnas m Bonrc Acrn Formula 3 Pounds Nonaethylene glycol mono laurate -2.0 Sodium lauryl sulfate I. 0.5 Gum tragacanth 3.0 Glycerine 10.0 Gum arabic 0.5 Butyl para hydroxy benzoate 0.05 Boric acid-adjust pH to 4.3 About 0.5 Perfume 0.05

Water suflicient to make atotal of 100.00

Here boric acid is used, and since this contri-- butes little to the spermicidal value, 3 lbs. of the ester are used. In addition, sodium lauryl sulphate is used whichhas a bacteriostatic action as well as a wetting action so the ox-yquinoline sulphate may be omitted. The function of the boric acid is simply to bring the composition to a pH value of 4.3.

Nmnar. Jum s Usmc Warm Insonunnr: Mono v Fury Esrnas' Wrm Annnn Emsrrmn Add suflicient water to make total of 100.00

The sodium laurly sulfate here assists in the dispersal of the glyceryl mono-undecylenate as well as exerting a bacteriostatic action.

Acm Jznms Usma Warns INsoLUnLn Mono FATTY Esrzns Arm AN Acm Formula 5 This formula is identical with Formula 3 except that the 2 lbs. of nonaethylene glycol laurate is replaced eate.

Acro Jzuazs Usmc WATER Insomnia: Bram FATTY ALcoHoLs Wrrn Anon by 2 lbs. of glyceryl monoricinol Formula 6 Pounds n-Decyl Alcohol 1.0 Sodium lauryl sulfate 0.8 Glycerine 10.0 Gum tragacanth 3.2 Gum arable 0.7

Butyl para hydroxy benzoate 0.05

Perfume 0.05 Boric acidadjust pH to 4.3 About 0.5

Water suflicient to make total 100.0

Acrn JELuEs Usmc WATER INSOLUBLI Mono FAm ETHER AND Bonrc Acm Formula 7 This formula is identical with Formula 3 except that 2 lbs. of the glyceryl mono ether of octyl alcohol are used instead of 3 lbs. of nonaethylene glycol monolaurate.

J ELLIES IN WHICH BOTH A WATER SOLUBLE AND WATER INSOLUBLE ESTER ARE UsEn Here the nonaethylene glycol monolaurate assists in emulsifying the glyceryl monoricinoleate and they both exert spermicidal action. which is additive.

JELLIES m Wmcrr A WATER SOLUBLE Mono FATTY ETHER 1s USED Formula 8A 2.5 lbs. nona ethylene glycol mono ether of octanol is substituted for the 3 lbs. of none. ethylene glycol laurate in Formula 2.

CREAMS In forming spermicidal creams, I have found it essential to provide a suitable cream base to carry the spermicidal material. Such a base is made up of a high molecular alcohol such as stearyl alcohol or cetyl alcohol or saturated mono-higher fatty esters of glycerine or sorbitan or glyceryl mono lactate with an emulsifier such as one of the alkyl sulfates and water. I have found it convenient to reduce the cost of such a base by diluting it with stearic acid in which case the more costly high molecular alcohols such as cetyl and stearyl or the saturated mono fatty esters of glycerine or of sorbitan or of glyceryl monolactate are required in less quantity.

Because of the necessity for emulsifying the base forming constituents of the creams, it is essential always to have in the composition an emulsifying agent. It must be present in amount suillcient to emulsify the base. and in case a water insoluble non-self-dlspersible spermicidal material is used, there must besuflicient in addition for emulsifying this also. Of course, where the spermicidal agent is self emulsifying somewhat less of the emulsifier will be required than is otherwise the case. This is also true where the sperimicidai agent is water soluble.

NmnAr. Cm! Usmc WArn sown: Ann WATER IIISOLUBLI Mono FATTY Es'rzxs Formula 9 Pounds Glyceryi mono stearate 18.0 Giyceryl mono laurate 2.0 Glycerine 8.5 Nona ethylene glycol undecylenate 2.0 Sodium lauryl sulfate 0.7 Perfume 0.05

Adjust to pH of 7.0 with either boric acid or 179011.

Water sumcient to total 100.0

Acrn CREAM Usnm WATER SOLUBLI Aim wAm Insowsu: Mono FATTY Earns FormulaIO Pounds Glyceryl mono stearate 5.5 Stearic acid 10.0 sorbitan stearate 4.5 Nona ethylene glycol mono laurate 3.0 Glycerine 8.5 Sodium lauryl sulfate 0.6 Lactic acid 85% 1.2 Potassium acetate to adjust pH to 3.3 About 0.2

Water suflicient to make total 100.0

Acrn CREAM Usmo MIXTURE or WATER INsoLuBLE Mono FATTY ESTERS Formula 11 Pounds Stearic acid 18.0 Sorbitan stearate 4.5 Glyceryl monoricinoleate 2.0 Glycerine 8.5 Sodium lauryl sulfate 0.6 Boric acid-adjust to pH of 4.3 Perfume .05

Water sufllcient to make total 100.0

Acm CREAM Usmc ONLY WATER SOLUBLE Mono FATTY ESTERS Formula 12 Pounds Stearic acid 4.0 Stearylalcohol 8.0 Nona ethylene glycol mono laurate 3.0 Glycerine 8.5 Sodium lauryl sulfate 0.5 Lactic acid 85% 2.0 Potassium acetate to adjust pH to 3.0 About 0.3 Perfume .05

Water sufficient to make total 100.0

OTHER CREAM FoRmULAE Srrowme VARIATIONS IN THE INGREDIENTS FOR THE BASE Formula 14 i a Pounds Glyceryl monostearate 18.0 Nonaethylene. glycol laurate 3.0 Sodium lauryl sulfate 0.0 Boric acid 2.0 Glycerine v 8.0

Water sufllcient to make total of 100.0

Formula 15 Pounds Glyceryl monostearate 10.0 Stearic acid 10.0 Nonaethylene glycol laurate 2.0 Sodium lauryl sulfate 0.7 Boric acid 2.0 Glycerine 8.0

Water sufllcient to make total of 100.0

Formula 16 Pounds Stearic acid 18.0 Glyceryl monostearate 2.0 Sodium lauryl sulfate 0.8 Glyceryl monoricinoleate 1.3 Boric acid v 1.0 Glycerine 8.0

Water sufflcient to make total of 100.0

' CONCENTRATED FOAM JELLIES For concentrated foam producing jellies. pow ders or similar mixtures to be used with moist sponges or moist tampons, it is desirable to have very high concentrations of spermicidal materials, since a small amount only is used on the sponge or tampon. The sodium alkyl sulfate assists the polyglycol mono ester in foam formation.

The following formulae are examples of my new compositions for this purpose.

Comm-marsh Foam Janus-s roa Us]: Wrm Morsr SPONGE on Tmon Usmows'rnn SOLUBLI Mono FATTY Es'rnn Formula 18 This is identical with Formula 17 except that the nonaethylene glycol laurate is replaced with 20 lbs. of glyceryl monorlcinoleate, which is insoluble. I CONCENTRATED Foam Pnonucmo Mfxrrms Wrncn MAY BE Ussn Wrrn Morsr Tmon on Morsr SPONGE Usmo Warns Somsn: Mono FATTY Es'rss Formula 19 Pounds Nonaethylene glycol laurate 20.0 Borlc acid 4.0 Gum arabic 2.0 Sodium lauryl sulfate 5.0 Perfume 0.1 Glycerine 10.0

Water to make total of --100.0

' The vehicle in the caseof the foam powders consists of kaolin and sucrose and lauryl sulfate. The spermicide] material is uniformly mixed throughout the powder.

- Couclnum Pom Pownrn ion Us: Wrra Morsr Sronon on Tarpon Formula 21 Same as previous formula except that lbs. of nonaethylene glycol mono laurate is substituted for the 15 lbs. of glyceryl monoricinoleate.

BUPPOSITORIES weight polyglycols themselves in which the spermicidal factor is uniformly mixed. Examples are as follows: Formula 22 I To 96 parts polyethylene glycol of molecular weight 1500 is added 4 parts of nonaethylene glycol mono undecylenate and both are melted together.

This mixture is then adjusted to a melting point of 36.5 by the addition of poly ethylene glycol of molecular weight 4000.

The resulting product is melted and cast in suppository molds.

Formula 23 Formula 24 To 96 lbs. of a poly ethylene glycol of melting point of C. is added 2 lbs. of boric acid and 4 lbs. of a poly ethylene glycol mono laurate having a molecular weight of 800. The mixture is melted together and then cast in suppository molds.

Snnmcnm. Tam ons TO BE Ussn WITH Ammo Momma Here cotton. lambs wool. or other fibre and the added water constitutes the vehicle through which the spermicidal factor is distributed.

Formula 25 Cotton. lambs wool, natural or artificial silk or nylon flufl are impregnated with a water solution containing 50 parts of nonaethylene glycol mono laurate and 3 parts boric acid in a total of 100.

The material is pressed until. there remains in it only 10% of the solution. It is then cut up into tampons weighing approximately grams each, provided with strings, packaged and sterilized.

Formula 26 Identical with formula 25 except that the monoethylene glycol laurate solution is replaced by molten poly ethylene glycol mono laurate of molecular weight of about 1700.

Formula 27 Identical with formula 25 except that the mono ethylene glycol laurate solution is replaced by molten polyethylene glycol mono undecylenate of molecular weight of about 1680.

I have described what I believe to be the best embodiments of my invention. I do not wish, however, to be confined to the embodiments set forth, but what I desire to cover by Letters Patent is set forth in the appended claims.

Iclaim:

1. A harmless spermicide comprising 9, nonalkaline vehicle and a neutral aliphatic hydroxy material of sufllcient spermicidal power and in sufficient proportions to constitute the major spermicidal ingredient in total spermicidal eflect distributed therein, the size of the particles of the material distributed ranging from molecular to approximately 1.5 microns, said material being selected from the class consisting of (a) straight chain fatty monohydroxy alcohols havlngfrom 8 to 11 carbon atoms in the chain, (b) branched chain fatty alcohols from 8 to 18 carbon atoms in the chain, (c) glyceryl, ethylene glycol and propylene-glycol monoethers of the alcohols mentioned in (a) and (b), (d) polyethylene glycol and polypropylene glycol mono ethers of these alcohols, the poly glycols ranging from the diglycol up to polyglycols of molecular weight of about 4000, (e) glyceryl, ethylene glycol and propylene glycol monoesters of unsaturated fatty acids having from to 18 carbons in the chain, (f) the polyethylene glycol and the polypropylene-glycol monoesters of fatty acids, saturated and unsaturated, having from 10 to 18 carbons in the chain, the polyglycols ranging in molecular weight from diglycol to polyglycol of molecular weight of about 4000, (g) glyceryl monolactate monoesters of unsaturated fatty acids of 10 to 18 carbon atoms, and mixtures thereof, the consistency of the vehicle being such that when the material is 12 distributed throughout it, the resulting composition may be positioned for effective action in a body cavity.

2. The spermicide as defined in claim 1, in 5 which the vehicle is an aqueous vehicle.

.3. The spermicide as defined in claim 1 and containing a water soluble acid for bringing the pH of the resulting composition within the range of 7.0 to approximately 1.0.

.4. The spermicide of claim 1 in which the vehicle consists of water and an aliphatic compound in emulsified form, selected from the group consisting of glyceryl-, anhydrohexitolether and glyceryl monolactate-monoesters of the saturated fatty acids ranging from 10 to 18 carbon atoms in the fatty chain, cetyl alcohol, stearyl alcohol and stearic acid.

5. The spermicide as defined in claim 1 and containing a. substance for reducing the surface tension of the composition.

6. The spermicide as defined in claim 1 and containing a buffer.

NATHANIEL M. ELIAS.

REFERENCES CITED UNITED STATES PATENTS 90 Number Name Date 2,052,025 Harris Aug. 25, 1936 2,055,063 Bird Sept. 22, 1936 2,149,240 Crossley Feb. 28, 1939 2,173,203 Harris Sept. 19, 1939 85 2,192,907 Harris Mai. 12, 1940 2,269,529 Goldsmith Jan. 13, 1942 2,302,121 Harris Nov. 1'7, 1942 FOREIGN PATENTS (0 Number Country Date 110,600 Australia May 23, 1940 OTHER REFERENCES Journal of Contraception, Sept. 1938, pages 149 5 to 153, article by Climenko.

Human Fertility, Feb. 1941, pages 1-7, article by Brown and Gamble.

Drug and Cosmetic 1nd., Oct. 1943, pages 388, 389 and 395 by Glickman. Garrell, Clin. Med., July 1941, pages 163-166.

spans and Tweens pamphlet, Atlas Powder 00., Nov. 1942, 20 pages.

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Classifications
U.S. Classification514/558, 514/843, 604/286, 514/560, 554/223, 514/738, 514/723, 514/722, 554/224, 514/724, 554/227, 514/841, 424/DIG.140
Cooperative ClassificationY10S514/841, Y10S514/843, Y10S424/14, A61K31/20