US2970032A - Stable solutions of compounds of tannins with boric acid - Google Patents
Stable solutions of compounds of tannins with boric acid Download PDFInfo
- Publication number
- US2970032A US2970032A US661593A US66159357A US2970032A US 2970032 A US2970032 A US 2970032A US 661593 A US661593 A US 661593A US 66159357 A US66159357 A US 66159357A US 2970032 A US2970032 A US 2970032A
- Authority
- US
- United States
- Prior art keywords
- boric acid
- solution
- tannin
- tannins
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004327 boric acid Substances 0.000 title claims description 15
- 229920001864 tannin Polymers 0.000 title description 11
- 239000001648 tannin Substances 0.000 title description 11
- 235000018553 tannin Nutrition 0.000 title description 10
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 title description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 28
- 235000019441 ethanol Nutrition 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000011877 solvent mixture Substances 0.000 claims description 13
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 3
- -1 BORIC ACID COMPOUND Chemical class 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 29
- 239000000203 mixture Substances 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 4
- 208000031888 Mycoses Diseases 0.000 description 3
- 208000010195 Onychomycosis Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 201000005882 tinea unguium Diseases 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000002474 Tinea Diseases 0.000 description 2
- 241000893966 Trichophyton verrucosum Species 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 230000001364 causal effect Effects 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
- 208000035415 Reinfection Diseases 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000036074 healthy skin Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 238000002803 maceration Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C3/00—Tanning; Compositions for tanning
Definitions
- the present invention relates to new and improved tanning agent solutions and more particularly to stable solutions of boric acid compounds of tannins which are not only suited for tanning animal skins but also and more particularly for topical application to humans and animals in the treatment of disease symptoms caused by fungi and bacteria and known as mycoses.
- solutions of compounds of tannins with boric acid in a solvent mixture of ethyl acetate, ethyl alcohol, acetic acid and water in proportions corresponding to the equilibrium mixture fulfilling the requirements of the law of mass action (Guldberg and Waage, 1879) and containing a maximum of 4% of acetic acid are extraordinarily stable and undergo no or substantially no change even after long periods of standing.
- Such solutions are not only well suited for tanning of animal skins to produce light leathers, but also for topical application in the treatment of mycoses. It was found that in treatment of mycoses in many instances not only leads to rapid healing but also the treated skin areas become resistant to reinfection.
- the equilibrium solvent mixture of ethyl alcohol, acetic acid, ethyl acetate and water employed according to the present invention must at least substantially correspond to the following equation:
- composition of such equilibrium solvent mixture according to the invention can, for example, be calculated as follows when the mixture is to contain 9% of weight of water and 2% by weight of acetic acid employing the following equations:
- the tannin-boric acid compounds employed according to the invention can be prepared according to the procedures described in application S.N. 192,633, filed October 27, 1951. For example, the following procedures can be employed:
- the resulting clear solution of the tannin-boric acid compound produced was stable and could be stored for any desired length of time without decomposition.
- the solution was of the following composition:
- the solution was also clinically tested on 30 cases of onychomycosis (caused by ringworms and germs) of varying degrees of severity, ranging from (1) patients having one or more nails indicating a beginning of an onychomycosis in the form of a discoloration of apart of the nail, (2) patients having nails already partly split or de formed and (3) patients having nails in which the whole nail was swollen and deformed.
- Table I Number patients treated Cured Improved The treatment of the less serious cases required about 4 weeks and the more serious required several months.
- the two patients with incurable onychomycosis were seriously infected cases having suffered lesions involving all nails for 4 and 12 years, respectively.
- the causal organism in these two cases was Candida albicans.
- the preferred concentrations of the tannin-boric acid compound in the solutions according to the invention lie ganismEpiderm0phyton inguinale) and eczema mycotica (causal organismvarious ringworms and germs) were treated with such a 5% solution.
- the patients treated were divided into three groups according to severity of the disease, namely:
- Group 1 Single seat (foci) of disease up to a diameter of 2 cm.
- Group 3 Several larger foci or several foci of long standing andresistant to other therapy. 7
- the treatment consisted of painting the solution on the A diseased areas twice daily for about 2 to 4 weeks in the case of the patients of Group 1, increasing up to 14 weeks for patients in Group 3.
- EXAMPLE 2 An equilibrium solvent mixture was prepared by mixing 23.60 kg. of ethyl acetate, 1.80 kg. of water, 61.93 kg. of 96% ethyl alcohol and 0.99 kg. of acetic acid. 11.68 kg. of the tannin-boric acid compound prepared as described above under (a) were then dissolved therein.
- Limed kip skins which were still moist were repeatedly immersed in alcohol of increasing concentration (starting concentration 50%) to remove the moisture contained therein and dried at a temperature below 40 C. to drive off the alcohol retained. The thus dried skins were then tanned in the tanning solution for six hours.
- the solvent mixture employed in Example 1 for the production of the tannin-boric acid compound solution can be distilled off from such solution to leave the tanninboric acid compound.
- the recovered distilled solvent mixture has the same concentration as the original mixture, namely, acetic acid 2% by wt., water 9% by wt., ethyl alcohol 59% by wt. and ethyl acetate 30% by wt., and can be reused for the production of further quantities of tannin-boric acid compounds.
- a tanning solution comprising a substantially stable clear solution of a tannin-boric acid compound in an equilibrium solvent mixture of ethyl acetate, ethyl alcohol, acetic acid and water in such proportions as to satisfy the equation (Molar concentration of acid) X (molar concentration of alcohol) y 4 (Molar concentration of ester) X (molar concentration of water) the quantity of acetic acid in said equilibrium solvent mixture not exceeding 4%.
- a tanning solution according to claim 1 which contains 5 to 15% of the tannin-boric acid compound.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
Description
STABLE SOLUTIONS OF COMPOUNDS OF TANNINS WITH BORIC ACID Otto C. Jekel, 1 Freihammerstrasse, Salzburg-Obergnigl, Austria =No Drawing. Filed May 27, 1957, $61. No. 661,593 2 Claims (c1. s 94.33
The present invention relates to new and improved tanning agent solutions and more particularly to stable solutions of boric acid compounds of tannins which are not only suited for tanning animal skins but also and more particularly for topical application to humans and animals in the treatment of disease symptoms caused by fungi and bacteria and known as mycoses.
Solutions of tannins have in the past had the disadvantage of decomposition, changing color and forming solid precipitates after standing a shorter or longer period of time. These phenomena occurred even in the absence of air and light and consequently are independent of the access of air or light. For example, an acetic acid solu tion of tannic acid in n-propanol already becomes cloudy after standing only a few days and assumes a dark color after standing a longer time. The decomposition of such tannin solutions is not readily prevented by chemical means.
According to the invention it was unexpectedly found that solutions of compounds of tannins with boric acid in a solvent mixture of ethyl acetate, ethyl alcohol, acetic acid and water in proportions corresponding to the equilibrium mixture fulfilling the requirements of the law of mass action (Guldberg and Waage, 1879) and containing a maximum of 4% of acetic acid are extraordinarily stable and undergo no or substantially no change even after long periods of standing. Such solutions are not only well suited for tanning of animal skins to produce light leathers, but also for topical application in the treatment of mycoses. It was found that in treatment of mycoses in many instances not only leads to rapid healing but also the treated skin areas become resistant to reinfection.
The equilibrium solvent mixture of ethyl alcohol, acetic acid, ethyl acetate and water employed according to the present invention must at least substantially correspond to the following equation:
(Molar concentration of the ethyl alcohol) X (molar concentration of the acetic acid) :1 (Molar concentration of the ethyl acetate) M (molar concentration of the water) The composition of such equilibrium solvent mixture according to the invention can, for example, be calculated as follows when the mixture is to contain 9% of weight of water and 2% by weight of acetic acid employing the following equations:
X (A) (I) (E) X .11 88.(E)+9+46.(A) +2=1oo United States Etent G 2,970,032 Patented Jan. 31, 1961 the solvent mixture corresponding to a stationary equilibrium is as follows:
, Percent Acetic acid 2 Water 9 It is not absolutely necessary that the concentrations of the solvent mixture be maintained with the greatest exactitude in accordance with calculated quantities for the equilibrium mixture, but the best results are obtained with the exact quantities. The further the quantities deviate from those theoretically required for the equilibrium mixture, the less stable the solutions of tanninboric acid compounds prepared therewith are.
The tannin-boric acid compounds employed according to the invention can be prepared according to the procedures described in application S.N. 192,633, filed October 27, 1951. For example, the following procedures can be employed:
(a) 25.5 parts by weight of pure tannin and 4.5 parts by weight of boric acid are dissolved in 70 parts by weight of ethyl alcohol (96 vol. percent). After the solution has been allowed to stand at v room temperature (about 20 C.) for one hour the ethyl alcohol is removed by distillation and the residue remaining is a compound of boric acid and tannin. Other inert solvents, such as, for example, acetone, can be employed instead of the ethyl alcohol indicated.
The equilibrium solvent mixture of acetic acid, ethyl alcohol, ethyl acetate and water according to the inven- EXAMPLE l 7 parts by weight of tannin and 3 parts by weight of boric acid were dissolved in a mixture of 1.8 parts by Weight of acetic acid, 8.1 parts of water, 53.1 parts of ethyl alcohol and 27.0 parts of ethyl acetate and the resulting solution was boiled under reflux for 1 hour. The resulting clear solution of the tannin-boric acid compound produced was stable and could be stored for any desired length of time without decomposition. The solution was of the following composition:
Percent by wt. Tannin-boric acid compound 10 Acetic acid 1.8
Water e 8.1 Ethyl alcohol 53.1 Ethyl acetate 27.0
Patch tests on human patients (50) on healthy skin revealed no sign of non-compatability with the patients tested.
The solution was also clinically tested on 30 cases of onychomycosis (caused by ringworms and germs) of varying degrees of severity, ranging from (1) patients having one or more nails indicating a beginning of an onychomycosis in the form of a discoloration of apart of the nail, (2) patients having nails already partly split or de formed and (3) patients having nails in which the whole nail was swollen and deformed.
When the lesions on the nails of the patients were slight the nails were given no pretreatment before application of the solution according to the invention. When the lesions were more severe, the nails were pretreated with a 5% alcoholic caustic potash solution until slight maceration occurred (about minutes) and then rinsed with water and painted with the solution according to the invention. The number of applications of the solution according to the invention was twice daily except in instances where the patients work required them to come into contact with water repeatedly, the patients were requested to make several additional applications daily. The following table gives the results attained:
Table I Number patients treated Cured Improved The treatment of the less serious cases required about 4 weeks and the more serious required several months. The two patients with incurable onychomycosis were seriously infected cases having suffered lesions involving all nails for 4 and 12 years, respectively. -The causal organism in these two cases was Candida albicans.
The preferred concentrations of the tannin-boric acid compound in the solutions according to the invention lie ganismEpiderm0phyton inguinale) and eczema mycotica (causal organismvarious ringworms and germs) were treated with such a 5% solution. The patients treated were divided into three groups according to severity of the disease, namely:
Group 1: Single seat (foci) of disease up to a diameter of 2 cm.
Group 2: Single larger foci.
Group 3: Several larger foci or several foci of long standing andresistant to other therapy. 7
The treatment consisted of painting the solution on the A diseased areas twice daily for about 2 to 4 weeks in the case of the patients of Group 1, increasing up to 14 weeks for patients in Group 3.
The following table gives the results attained:
Table II Number No impa-tients Cured Improved provetreated ment 31 24 7 21 12 8 1 Group 3 13 7 3 3 The patients in which no improvement occurred were for tanning animal skins, especially for the production 4 of light fine leathers. The following example illustrates the preparation of a leather tanning solution suitable for tanning leather:
EXAMPLE 2 An equilibrium solvent mixture was prepared by mixing 23.60 kg. of ethyl acetate, 1.80 kg. of water, 61.93 kg. of 96% ethyl alcohol and 0.99 kg. of acetic acid. 11.68 kg. of the tannin-boric acid compound prepared as described above under (a) were then dissolved therein.
The following procedure was employed to employ such solution in tanning kip skins:
Limed kip skins which were still moist were repeatedly immersed in alcohol of increasing concentration (starting concentration 50%) to remove the moisture contained therein and dried at a temperature below 40 C. to drive off the alcohol retained. The thus dried skins were then tanned in the tanning solution for six hours.
While several illustrations of equilibrium solvent mixtures have been given by way of example, the proportions of the components of such equilibrium mixture can be varied as long as they at least substantially conform with the quantities required for a stationary equilibrium at the prevailing temperature and as long as the quantity of acetic acid in such equilibrium mixture does not exceed 4%.
The solvent mixture employed in Example 1 for the production of the tannin-boric acid compound solution can be distilled off from such solution to leave the tanninboric acid compound. The recovered distilled solvent mixture has the same concentration as the original mixture, namely, acetic acid 2% by wt., water 9% by wt., ethyl alcohol 59% by wt. and ethyl acetate 30% by wt., and can be reused for the production of further quantities of tannin-boric acid compounds.
This application is a continuation-in-part of my eopending application Serial No. 256,375, filed November 14, 1951, now abandoned.
Instead of pure tannin there also can be used commercial tannins of various kinds as starting material. It is also possible to employ the boric acid excess but in this case the surplus remains unchanged.
I claim:
1. A tanning solution comprising a substantially stable clear solution of a tannin-boric acid compound in an equilibrium solvent mixture of ethyl acetate, ethyl alcohol, acetic acid and water in such proportions as to satisfy the equation (Molar concentration of acid) X (molar concentration of alcohol) y 4 (Molar concentration of ester) X (molar concentration of water) the quantity of acetic acid in said equilibrium solvent mixture not exceeding 4%.
2. A tanning solution according to claim 1 which contains 5 to 15% of the tannin-boric acid compound.
References Cited in the file of this patent UNITED STATES PATENTS 9,125 Keil July 7, 1942 OTHER REFERENCES Brewster: Organic Chemistry, 1948, Prentice-Hall
Claims (1)
1. A TANNING SOLUTION COMPRISING A SUBSTANTIALLY STABLE CLEAR SOLUTION OF A TANNIN>BORIC ACID COMPOUND IN AN EQUILIBRIUM SOLVENT MIXTURE OF ETHYL ACETATE, ETHYL ALCOHOL, ACETIC ACID AND WATER IN SUCH PROPORTIONS AS TO SATISFY THE EQUATION
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US661593A US2970032A (en) | 1957-05-27 | 1957-05-27 | Stable solutions of compounds of tannins with boric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US661593A US2970032A (en) | 1957-05-27 | 1957-05-27 | Stable solutions of compounds of tannins with boric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2970032A true US2970032A (en) | 1961-01-31 |
Family
ID=24654259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US661593A Expired - Lifetime US2970032A (en) | 1957-05-27 | 1957-05-27 | Stable solutions of compounds of tannins with boric acid |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2970032A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5268174A (en) * | 1988-09-29 | 1993-12-07 | Kabushiki Kaisha Sangi | Antimicrobial hydroxyapatite powders containing hinokitiol, protamine or sorbic acid |
| WO2002098402A1 (en) * | 2001-06-04 | 2002-12-12 | Bogart Mark H | Methods for the treatment of nail fungus and other microbial and mycotic conditions and compositions useful therefor |
| EP1416799A4 (en) * | 2001-07-23 | 2004-11-10 | Univ Ramot | METHODS AND COMPOSITIONS FOR TREATING FUNGAL INFECTIONS |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2289125A (en) * | 1938-04-18 | 1942-07-07 | Wilfred B Kell | Therapeutic agent for the treatment of fungus infection |
-
1957
- 1957-05-27 US US661593A patent/US2970032A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2289125A (en) * | 1938-04-18 | 1942-07-07 | Wilfred B Kell | Therapeutic agent for the treatment of fungus infection |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5268174A (en) * | 1988-09-29 | 1993-12-07 | Kabushiki Kaisha Sangi | Antimicrobial hydroxyapatite powders containing hinokitiol, protamine or sorbic acid |
| WO2002098402A1 (en) * | 2001-06-04 | 2002-12-12 | Bogart Mark H | Methods for the treatment of nail fungus and other microbial and mycotic conditions and compositions useful therefor |
| US6664292B2 (en) * | 2001-06-04 | 2003-12-16 | Mark H. Bogart | Methods for the treatment of nail fungus and other microbial and mycotic conditions and compositions useful therefor |
| EP1416799A4 (en) * | 2001-07-23 | 2004-11-10 | Univ Ramot | METHODS AND COMPOSITIONS FOR TREATING FUNGAL INFECTIONS |
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