US2541103A - Spermicidal composition - Google Patents
Spermicidal composition Download PDFInfo
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- US2541103A US2541103A US23620A US2362048A US2541103A US 2541103 A US2541103 A US 2541103A US 23620 A US23620 A US 23620A US 2362048 A US2362048 A US 2362048A US 2541103 A US2541103 A US 2541103A
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- spermicidal
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- alkylphenoxyethanol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/14—Topical contraceptives and spermacides
Definitions
- This invention relates to novel compositions of matter and more particularly to novel'compositions which are intended for topical use.
- the invention is directed to novel compositions of matter useful chiefly for application to the mucous surfaces of the'vaginal cavity where they act as spermicidal media.
- spermicidal compositions Prior to this invention a number of difierent spermicidal compositions have been proposed. Among them are, the sperniicidal compositions disclosed in the United States patent of Frank V. Sander, No. 2,330,846, issued on October 5, 1943. That patent discloses spermicidal compositions comprising essentially an aqueous vehicle having therein an unsaturated higher fatty acid of ten or more carbon atoms, e. g., ricinoleic,
- spermicidal compositions that are dispersing and wetting agent which is a water soluble alkylphenoxyethanol having the following general formula V g oomom)zon in which R i an alkyl radical, preferably in the position para to the oxygen atom, and may be 1 or greater than 1.
- a mixture of water soluble alkylphenoxyethanols may be used, andin the preferred practice a: has an average value of from 9,25 to 10.25, and the average molecular weight of the said ethers is 595 to 639.
- a: is approximately 9.75, and R is tertiary octyl and is in the para position.
- R is an alkyl radical having 1 to 22' carbon atoms and the value of .r is in the range of 1' to 12, which is the preferred range, although compounds in which the value ofxc is greater thanl2 are also. of i 9 Claims. (CL 167-58) to employ those in which R. has 8 carbon atoms and especially thosein which R is tertiary octyl having the following graphic formula:
- CH3 CH3 CHa-b-CHZ a Ha Dispersing and wetting agents such as those described above enable a fine division of the unsaturated fatty acid to be obtained, and this contributes substantially to the spermicidal power of the formulation.
- the vehicle employed in the combination is preferably an aqueous vehicle, and vegetable gums are preferred as ingredients but synthetic resins and cellulose derivatives may also be used.
- a thickened mass comprising water and locust bean gum, tragacanth, Irish moss, alginates, acacia, or various other equivalent vegetable gums, used either alone or in combination with one or more of said unsaturated fatty acids and one or more of said alkylphenoxyethanols.
- the amounts of said fatty acid and alkylphenoxyethanols present in the aqueous vehicle is small, and it is preferable that the ratio of the quantity by Weight respectively of the fatty acid and the alkylphenoxyethanol to the vehicle be no greater than about 5 to 100 and generally is in the range of .5 to 100 and 1 to 100.
- antiseptic agents such as boric acid, oxyquinoline sulphate, phenols, cresols, thymols, chlorinated phenols, cresols and thymols; an anti-molding compound such as propyl para-hydroxy benzoate; a hygroscopic agent such as glycerine as well as other substances such as perfumes, etc.
- the invention accordingly comprises compositions of matter possessing the characteristics, properties and the relation of constituents which will be exemplified in the composition hereinafter described and the scope of the invention will be indicated in the claims.
- Typical spermicidal compositions in the nature ,of jellies embodying the invention may be prepared by following any of the well-known pro- :cedures and using the components of the folvalue.
- pro- :cedures the components of the folvalue.
- alkylphenoxyethanols I prefer lowing examples, all parts being given by Weight,
- Example II A spermicidal composition having the same formula as Example I but in which the alkylphenoxyethanol is a mixture of the para-alkylphenoxyethanols in which R is di-isobutyl, and x has an approximate value of 9.75.
- Example III A spermicidal composition having the same formula as that of Example I but in which the alkylphenoxyethanol is para tertiaryamylphen y hanol- E mr o IV"
- Example V A s 'm dal comp it o hav t same formula as that of Example I but in which the alkylphenoxyethanol is para-tertiaryoctylphenoxyethanol.
- Example VI A spermicidal composition having the same formula as that of Example I but in which the alkylphenoxyethanol is para-tertiar-yoctylphenoxydiethoxyethanol.
- Example VIII A spermicidal composition having the same formula as that of Example I; exceptthat the alkylphenoxyethanol is omitted.
- the specific spermicidal compositions of Examples II to VIII inclusive were tested to de termine their spermicidal power. Two grams of a spermicidal composition represented by Examples II to VIII inclusive were placed in a test tube containing 98 grams of a physiological saline solution. The saline solution contained 9 grams of sodium chloride per liter of water. The test tube was shaken vigorously until the jelly was uniformly distributed in the saline solution. One cc. of the jelly in saline solution was added to a second test tube containing 0.2 cc. of fresh human semen; the contents of the second tube were quickly mixed and examined micro.- scopically to determine the activity of the "4 i i spermatozoa.
- the tabulated results also indicate the effectiveness of the alkylphenoxyethanolsin potentiating the spermicidal power of a composition containing an unsaturated fatty acid as a spermicidal agent in that the time required for such a potentiated composition to completely immotilize spermatozoa when tested according to the above procedure is a maximum of sixminutes, whereas the same composition, except. that the alkylphenoxyethanol is omitted, requires a corresponding maximum period of 56 minutes to completely immotilize spermatozoa.
- the novel spermicidalcompositions of the present invention comprising the combination with a vehicle a an; un atur ted fatty a l oi en or r carblonaatomsof. ne r m r of. sa d alkylphenoxyetna-noi are many tim mo e ect v than the ol compositions in. whi h me v hicle included one of; saidzfatty acid b t not on o a mi t r of the said alkxlphenoxyethanols,
- a spermicidal composition comprising in combination with a vehicle, an unsaturated fatty acid containing at least carbon atoms, and an alkylphenoxyethanol of the following general formula in which R is an alkyl radical having a number of carbon atoms within the range of 1 to 22, and cc has a value of at least one.
- a spermicidal composition comprising in combination with a vehicle, an unsaturated fatty acid containing at least 10 carbon atoms, and a para-alkylphenoxyethanol of the following general formula EKG-(0013101391011 in which R, is an alkyl radical and :c has a value of at least one.
- a spermicidal composition comprising in combination with a vehicle, an unsaturated fatty acid containing at least 10 carbon atoms, and a para-alkylphenoxyethanol of the following general formula R- ocrnom).on
- R is an alkyl radical having a number of carbon atoms within the range of 1 to 22, and a: has a value of at least one.
- a spermicidal composition comprising in combination with a vehicle, an unsaturated fatty acid containing at least 10 carbon atoms, and a para-alkylphenoxyethanol of the following general formula in which R is di-isobutyl and a: has a value of at least one.
- a spermicidal composition comprising in combination with an aqueous vehicle, an unsaturated fatty acid containing at least 10 carbon atoms, and a mixture of para-alkylphenoxyethanols of the following general formula R-O-(OCHzCHz):OH
- R is di-isobutyl and the average value of a: in said mixture is approximately 9.25 to 10.25 and the average molecular weight of said ethers is approximately 595 to 639.
- a spermicidal composition comprising in combination with a vehicle, ricinoleic acid, and a para-alkylphenoxyethanol of the following general formula in which R is an alkyl and the value of :c is at least 1.
- a spermicidal composition comprising in combination with a vehicle, ricinoleic acid, and a. para-alkylphenoxyethanol of the following general formula in which R is di-isobutyl and a: has a value of at least one.
- a spermicidal composition comprising in combination with an aqueous vehicle, ricinoleic acid, and a mixture of para-alkylphenoxyethanols of the following general formula RQ-(OCIHCHMOH in which R is di-isobutyl and the average value of a: in said mixture is 9.75 and the average molecular Weight of the said ethers in 635.
Description
Patented Feb. 13, 1951 UNITED SPERMICIDAL COMPOSITION Frank V. Sander, Milwaukee, Wis., assignor to Ortho Pharmaceutical Corporation, a corporation of New Jersey No Drawing. Application April 27, 1948, Serial No. 23,620
This invention relates to novel compositions of matter and more particularly to novel'compositions which are intended for topical use. In one of its more specific aspects the invention is directed to novel compositions of matter useful chiefly for application to the mucous surfaces of the'vaginal cavity where they act as spermicidal media. i
Prior to this invention a number of difierent spermicidal compositions have been proposed. Among them are, the sperniicidal compositions disclosed in the United States patent of Frank V. Sander, No. 2,330,846, issued on October 5, 1943. That patent discloses spermicidal compositions comprising essentially an aqueous vehicle having therein an unsaturated higher fatty acid of ten or more carbon atoms, e. g., ricinoleic,
oleic and linoleic acids, and a surface tension depressant, e. g., sulfonated fatty acids and alcohols and the salts and esters thereof, the unsaturated fatty acid being suspended in the vehicle as finely dispersed particles. While the spermicidal compositions disclosed in said patent have found acceptance in the art, I have provided novel spermicidal compositions that are dispersing and wetting agent which is a water soluble alkylphenoxyethanol having the following general formula V g oomom)zon in which R i an alkyl radical, preferably in the position para to the oxygen atom, and may be 1 or greater than 1. A mixture of water soluble alkylphenoxyethanols may be used, andin the preferred practice a: has an average value of from 9,25 to 10.25, and the average molecular weight of the said ethers is 595 to 639. In the preferred specific embodiment of my invention,
a: is approximately 9.75, and R is tertiary octyl and is in the para position. Generally R, is an alkyl radical having 1 to 22' carbon atoms and the value of .r is in the range of 1' to 12, which is the preferred range, although compounds in which the value ofxc is greater thanl2 are also. of i 9 Claims. (CL 167-58) to employ those in which R. has 8 carbon atoms and especially thosein which R is tertiary octyl having the following graphic formula:
CH3 CH3 CHa-b-CHZ" a Ha Dispersing and wetting agents such as those described above enable a fine division of the unsaturated fatty acid to be obtained, and this contributes substantially to the spermicidal power of the formulation.
The vehicle employed in the combination is preferably an aqueous vehicle, and vegetable gums are preferred as ingredients but synthetic resins and cellulose derivatives may also be used.
In the practice of this invention, there may be employed as a vehicle a thickened mass comprising water and locust bean gum, tragacanth, Irish moss, alginates, acacia, or various other equivalent vegetable gums, used either alone or in combination with one or more of said unsaturated fatty acids and one or more of said alkylphenoxyethanols. The amounts of said fatty acid and alkylphenoxyethanols present in the aqueous vehicle is small, and it is preferable that the ratio of the quantity by Weight respectively of the fatty acid and the alkylphenoxyethanol to the vehicle be no greater than about 5 to 100 and generally is in the range of .5 to 100 and 1 to 100. Also present may be one or more antiseptic agents such as boric acid, oxyquinoline sulphate, phenols, cresols, thymols, chlorinated phenols, cresols and thymols; an anti-molding compound such as propyl para-hydroxy benzoate; a hygroscopic agent such as glycerine as well as other substances such as perfumes, etc.
The invention accordingly comprises compositions of matter possessing the characteristics, properties and the relation of constituents which will be exemplified in the composition hereinafter described and the scope of the invention will be indicated in the claims.
For a fuller understanding of the invention, reference should be had to the following examples which are given as specific illustrations. It should be understood, however, that the in- .vention is not limited to the specific details se forth in the illustrations; i
Typical spermicidal compositions in the nature ,of jellies embodying the invention may be prepared by following any of the well-known pro- :cedures and using the components of the folvalue. Of these alkylphenoxyethanols, I prefer lowing examples, all parts being given by Weight,
3 The procedure in my U. S. Patent 2,330,846 for the preparation of a spermicidal composition is particularly satisfactory for preparing the compositions of the instant invention.
Water (q. 5. ad. 100) pH adjusted to 4. 5 with acetic acid 87. 65 Example II A spermicidal composition having the same formula as Example I but in which the alkylphenoxyethanol is a mixture of the para-alkylphenoxyethanols in which R is di-isobutyl, and x has an approximate value of 9.75.
Example III A spermicidal composition having the same formula as that of Example I but in which the alkylphenoxyethanol is para tertiaryamylphen y hanol- E mr o IV" A spermicidal composition having the same formula as that of Example I but in which the l lp o xy th s ra to ar amylphenoxydiethoxyethanol.
Example V A s 'm dal comp it o hav t same formula as that of Example I but in which the alkylphenoxyethanol is para-tertiaryoctylphenoxyethanol.
Example VI A spermicidal composition having the same formula as that of Example I but in which the alkylphenoxyethanol is para-tertiar-yoctylphenoxydiethoxyethanol.
Ex e I A spermicidal composition having the same formula as that of Example I but in which the alkylphenoxyethanol is paraetertiaryoctylphenoxytetraethoxyethanol.
Example VIII A spermicidal composition having the same formula as that of Example I; exceptthat the alkylphenoxyethanol is omitted.
The specific spermicidal compositions of Examples II to VIII inclusive were tested to de termine their spermicidal power. Two grams of a spermicidal composition represented by Examples II to VIII inclusive were placed in a test tube containing 98 grams of a physiological saline solution. The saline solution contained 9 grams of sodium chloride per liter of water. The test tube was shaken vigorously until the jelly was uniformly distributed in the saline solution. One cc. of the jelly in saline solution was added to a second test tube containing 0.2 cc. of fresh human semen; the contents of the second tube were quickly mixed and examined micro.- scopically to determine the activity of the "4 i i spermatozoa. The time required for the mixing of the contents of the second test tube, the placing of a sample on a suitable slide, and its subcording to the above procedure. Three series of tests were made of the seven formulations at intervals of a few days so that each formulation was tested three times. Each series of tests was made on a sampl of human sem n obtained by pooling individual S ecimens from, three donors. The semen specimens, were collected, cooled, Poole/(ll an used within a few hours to insure that. the spermat a ad full m t l ty l the, time the test. were made.
Composition of- Test #1 Test #2 Test #3 Example IT. -20 sec. =40 sec. -.-20 sec. Example III 1 min. 1 min. 50 sec. Example 6 min. 5 min. 4 min.
' l min. 15 sec. 1 min. 25sec. 1v min. 15 sec.
45 sec. sec. l'inin. 50 sec. 1 min.
56 min. 52 min.
The tabulated results further show that all of the spermicidal compositions of Examples 11 and VII inclusive, are capable of immotiliz-ing spermatozoa in at least six minutes even when so greatly diluted as in the heretofore described tests wherein the composition tested contained only 2 per cent of a spermicidal composition. At this dilution one grain of the novel spermicidal composition in saline solution contains only 0.00015 gram of one of the said unsaturated fatty acids and 0.0002 gram ofone of the said paraalkylphenoxyethanols;
The tabulated results also indicate the effectiveness of the alkylphenoxyethanolsin potentiating the spermicidal power of a composition containing an unsaturated fatty acid as a spermicidal agent in that the time required for such a potentiated composition to completely immotilize spermatozoa when tested according to the above procedure is a maximum of sixminutes, whereas the same composition, except. that the alkylphenoxyethanol is omitted, requires a corresponding maximum period of 56 minutes to completely immotilize spermatozoa.
Ba ed upon, the results at the tests, the novel spermicidalcompositions of the present invention comprising the combination with a vehicle a an; un atur ted fatty a l oi en or r carblonaatomsof. ne r m r of. sa d alkylphenoxyetna-noi are many tim mo e ect v than the ol compositions in. whi h me v hicle included one of; saidzfatty acid b t not on o a mi t r of the said alkxlphenoxyethanols,
Since certain changes. may be made in the 7 above compositions. of matter and different: em-
bodiments of the invention could be made without: departing from its scope, it is intended that all matter contained; in theabove description shall In instances where in which R is an alkyl radical and a: has a value of at least one.
2. A spermicidal composition comprising in combination with a vehicle, an unsaturated fatty acid containing at least carbon atoms, and an alkylphenoxyethanol of the following general formula in which R is an alkyl radical having a number of carbon atoms within the range of 1 to 22, and cc has a value of at least one.
3. A spermicidal composition comprising in combination with a vehicle, an unsaturated fatty acid containing at least 10 carbon atoms, and a para-alkylphenoxyethanol of the following general formula EKG-(0013101391011 in which R, is an alkyl radical and :c has a value of at least one.
4. A spermicidal composition comprising in combination with a vehicle, an unsaturated fatty acid containing at least 10 carbon atoms, and a para-alkylphenoxyethanol of the following general formula R- ocrnom).on
in which R is an alkyl radical having a number of carbon atoms within the range of 1 to 22, and a: has a value of at least one.
5. A spermicidal composition comprising in combination with a vehicle, an unsaturated fatty acid containing at least 10 carbon atoms, and a para-alkylphenoxyethanol of the following general formula in which R is di-isobutyl and a: has a value of at least one.
6. A spermicidal composition comprising in combination with an aqueous vehicle, an unsaturated fatty acid containing at least 10 carbon atoms, and a mixture of para-alkylphenoxyethanols of the following general formula R-O-(OCHzCHz):OH
in which R is di-isobutyl and the average value of a: in said mixture is approximately 9.25 to 10.25 and the average molecular weight of said ethers is approximately 595 to 639.
7. A spermicidal composition comprising in combination with a vehicle, ricinoleic acid, and a para-alkylphenoxyethanol of the following general formula in which R is an alkyl and the value of :c is at least 1.
8. A spermicidal composition comprising in combination with a vehicle, ricinoleic acid, and a. para-alkylphenoxyethanol of the following general formula in which R is di-isobutyl and a: has a value of at least one.
9. A spermicidal composition comprising in combination with an aqueous vehicle, ricinoleic acid, and a mixture of para-alkylphenoxyethanols of the following general formula RQ-(OCIHCHMOH in which R is di-isobutyl and the average value of a: in said mixture is 9.75 and the average molecular Weight of the said ethers in 635.
FRANK V. SANDER.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,149,240 Crossley -ili'eb. :28, 1939 2,330,846 Sander Oct. 5, 1943 2,436,184 Stillman et a1 Feb. 17, 1948 OTHER REFERENCES Dickinson: Control of Conception, 2nd ed., 1938, Williams and Wilkins 00., Baltimore, Md., pages 71-73.
J. A. P. A., Prac. Phar. Ed, Mar. 1946, page 138.
Claims (1)
1. A SPERMICIDAL COMPOSITION COMPRISING IN COMBINATION WITH A VEHICLE, AN UNSATURATED FATTY ACID CONTAINING AT LEAST 10 CARBON ATOMS, AND AN ALKYLPHENOXYETHANOL OF THE FOLLOWING GENERAL FORMULA
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US23620A US2541103A (en) | 1948-04-27 | 1948-04-27 | Spermicidal composition |
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Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2752284A (en) * | 1952-09-27 | 1956-06-26 | Ortho Pharma Corp | Spermicidal composition |
US2777796A (en) * | 1951-11-30 | 1957-01-15 | Nathaniel M Elias | Spermicidal composition |
US2943979A (en) * | 1959-06-23 | 1960-07-05 | Nathaniel M Elias | Concentrated foam-producing spermicides |
US3514517A (en) * | 1964-09-19 | 1970-05-26 | Eisai Co Ltd | Intravaginal contraceptive compositions employing terpenylphenyl polyoxyethylene ethers |
US4193813A (en) * | 1976-09-07 | 1980-03-18 | Medi-Coll, Inc. | Method for making collagen sponge |
WO1983000086A1 (en) * | 1981-07-06 | 1983-01-20 | Univ Georgia Res Found | Use of calmodulin binding drugs in uterus to prevent pregnancy |
US4443446A (en) * | 1980-05-30 | 1984-04-17 | University Of Georgia Research Foundation, Inc. | Use of psychoactive drugs as vaginal contraceptives |
US4551148A (en) * | 1982-09-07 | 1985-11-05 | Kv Pharmaceutical Company | Vaginal delivery systems and their methods of preparation and use |
US4564362A (en) * | 1983-07-07 | 1986-01-14 | Burnhill Michael S | Vaginal device |
US4601714A (en) * | 1983-07-07 | 1986-07-22 | Burnhill Michael S | Vaginal device |
US4602042A (en) * | 1983-10-14 | 1986-07-22 | Imperial Chemical Industries Plc | Contraceptive methods |
WO1987002576A1 (en) * | 1985-10-31 | 1987-05-07 | Kv Pharmaceutical Company | Vaginal delivery systems |
US4722936A (en) * | 1983-05-05 | 1988-02-02 | Joseph Jacob | Deodorization vaginal products and catamenials |
US4777171A (en) * | 1984-06-11 | 1988-10-11 | Bar-Ilan University | Method and composition for the therapeutic and prophylactic treatment of trauma to the skin |
US5266329A (en) * | 1985-10-31 | 1993-11-30 | Kv Pharmaceutical Company | Vaginal delivery system |
US5335373A (en) * | 1991-11-29 | 1994-08-09 | Dresdner Jr Karl P | Protective medical gloves and methods for their use |
US5357636A (en) * | 1992-06-30 | 1994-10-25 | Dresdner Jr Karl P | Flexible protective medical gloves and methods for their use |
US5700679A (en) * | 1996-06-07 | 1997-12-23 | Novavax, Inc. | Lipid vesicles having a bilayer containing a surfactant with anti-viral and spermicidal activity |
US20050025847A1 (en) * | 2003-02-26 | 2005-02-03 | Program For Appropriate Technology In Health | Microbicidal compositions and method of use |
US20050037033A1 (en) * | 2003-05-23 | 2005-02-17 | Program For Appropriate Technology In Health | Microbicidal compositions and methods and use |
US20050271643A1 (en) * | 2003-08-14 | 2005-12-08 | Iryna Sorokulova | Bacterial strains, compositions including same and probiotic use thereof |
US20060058265A1 (en) * | 2004-07-09 | 2006-03-16 | Gilead Sciences, Inc. | Topical antiviral formulations |
WO2011067302A1 (en) | 2009-12-01 | 2011-06-09 | Seprox Biotech, S.L. | Topical use of hydroxytyrosol and derivatives for the prevention of hiv infection |
EP2546358A1 (en) | 2011-07-15 | 2013-01-16 | Laboratorios Del. Dr. Esteve, S.A. | Methods and reagents for efficient control of HIV progression |
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US2149240A (en) * | 1938-05-19 | 1939-02-28 | Calco Chemical Co Inc | Vaginal preparation |
US2330846A (en) * | 1939-05-01 | 1943-10-05 | Ortho Products Inc | Spermicide |
US2436184A (en) * | 1945-11-08 | 1948-02-17 | Eaton Lab Inc | Pharmaceutical jelly |
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US2149240A (en) * | 1938-05-19 | 1939-02-28 | Calco Chemical Co Inc | Vaginal preparation |
US2330846A (en) * | 1939-05-01 | 1943-10-05 | Ortho Products Inc | Spermicide |
US2436184A (en) * | 1945-11-08 | 1948-02-17 | Eaton Lab Inc | Pharmaceutical jelly |
Cited By (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2777796A (en) * | 1951-11-30 | 1957-01-15 | Nathaniel M Elias | Spermicidal composition |
US2752284A (en) * | 1952-09-27 | 1956-06-26 | Ortho Pharma Corp | Spermicidal composition |
US2943979A (en) * | 1959-06-23 | 1960-07-05 | Nathaniel M Elias | Concentrated foam-producing spermicides |
US3514517A (en) * | 1964-09-19 | 1970-05-26 | Eisai Co Ltd | Intravaginal contraceptive compositions employing terpenylphenyl polyoxyethylene ethers |
US4193813A (en) * | 1976-09-07 | 1980-03-18 | Medi-Coll, Inc. | Method for making collagen sponge |
US4377577A (en) * | 1980-05-30 | 1983-03-22 | University Of Georgia Research Foundation, Inc. | Use of psychoactive drugs in uterus to prevent pregnancy |
US4443446A (en) * | 1980-05-30 | 1984-04-17 | University Of Georgia Research Foundation, Inc. | Use of psychoactive drugs as vaginal contraceptives |
WO1983000086A1 (en) * | 1981-07-06 | 1983-01-20 | Univ Georgia Res Found | Use of calmodulin binding drugs in uterus to prevent pregnancy |
US4551148A (en) * | 1982-09-07 | 1985-11-05 | Kv Pharmaceutical Company | Vaginal delivery systems and their methods of preparation and use |
US4722936A (en) * | 1983-05-05 | 1988-02-02 | Joseph Jacob | Deodorization vaginal products and catamenials |
US4564362A (en) * | 1983-07-07 | 1986-01-14 | Burnhill Michael S | Vaginal device |
US4601714A (en) * | 1983-07-07 | 1986-07-22 | Burnhill Michael S | Vaginal device |
US4602042A (en) * | 1983-10-14 | 1986-07-22 | Imperial Chemical Industries Plc | Contraceptive methods |
US4777171A (en) * | 1984-06-11 | 1988-10-11 | Bar-Ilan University | Method and composition for the therapeutic and prophylactic treatment of trauma to the skin |
WO1987002576A1 (en) * | 1985-10-31 | 1987-05-07 | Kv Pharmaceutical Company | Vaginal delivery systems |
US5266329A (en) * | 1985-10-31 | 1993-11-30 | Kv Pharmaceutical Company | Vaginal delivery system |
US5335373A (en) * | 1991-11-29 | 1994-08-09 | Dresdner Jr Karl P | Protective medical gloves and methods for their use |
US5357636A (en) * | 1992-06-30 | 1994-10-25 | Dresdner Jr Karl P | Flexible protective medical gloves and methods for their use |
US5700679A (en) * | 1996-06-07 | 1997-12-23 | Novavax, Inc. | Lipid vesicles having a bilayer containing a surfactant with anti-viral and spermicidal activity |
US20050025847A1 (en) * | 2003-02-26 | 2005-02-03 | Program For Appropriate Technology In Health | Microbicidal compositions and method of use |
US20050037033A1 (en) * | 2003-05-23 | 2005-02-17 | Program For Appropriate Technology In Health | Microbicidal compositions and methods and use |
US20050271643A1 (en) * | 2003-08-14 | 2005-12-08 | Iryna Sorokulova | Bacterial strains, compositions including same and probiotic use thereof |
US20060058265A1 (en) * | 2004-07-09 | 2006-03-16 | Gilead Sciences, Inc. | Topical antiviral formulations |
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