GB2167296A - Topical pharmaceutical compositions containing glycyrrhizin - Google Patents

Topical pharmaceutical compositions containing glycyrrhizin Download PDF

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Publication number
GB2167296A
GB2167296A GB08429749A GB8429749A GB2167296A GB 2167296 A GB2167296 A GB 2167296A GB 08429749 A GB08429749 A GB 08429749A GB 8429749 A GB8429749 A GB 8429749A GB 2167296 A GB2167296 A GB 2167296A
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United Kingdom
Prior art keywords
glycyrrhizin
treatment
composition according
herpes simplex
pharmaceutical composition
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Granted
Application number
GB08429749A
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GB8429749D0 (en
GB2167296B (en
Inventor
Ruth Segal
Sara Pisanty
Emma Azaz
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Yissum Research Development Co of Hebrew University of Jerusalem
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Yissum Research Development Co of Hebrew University of Jerusalem
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Publication date
Priority to IL65184A priority Critical patent/IL65184A/en
Priority to IL65184A priority patent/IL65184A0/en
Application filed by Yissum Research Development Co of Hebrew University of Jerusalem filed Critical Yissum Research Development Co of Hebrew University of Jerusalem
Priority to GB08429749A priority patent/GB2167296B/en
Priority to DE19843443242 priority patent/DE3443242A1/en
Priority to CH5651/84A priority patent/CH662510A5/en
Priority to FR848418155A priority patent/FR2573655B1/en
Publication of GB8429749D0 publication Critical patent/GB8429749D0/en
Publication of GB2167296A publication Critical patent/GB2167296A/en
Application granted granted Critical
Publication of GB2167296B publication Critical patent/GB2167296B/en
Expired legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/16—Fluorine compounds
    • 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
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • 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

Abstract

Topical pharmaceutical compositions for treating skin and oral diseases comprise glycyrrhizin and a topically effective medicament (e.g. antimycotics, antibiotics, corticosteroids, anti-caries agents, anti-viral agent or estrogens) in an aqueous medium.

Description

SPECIFICATION Pharmaceutical compositions The present invention relates to pharmaceutical preparations having a synergistic effect, which comprise glycyrrhizin in an aqueous medium in combination with an effective drug. These are of value in the treatment of various oral diseases and especially for aphtous stomatitis. They are of value for the treatment of lesions caused by Herpes simplex. The drug of choice for the treatment of stomatitis is triamcynolone, and for the treatment of Herpex simplex the drug of choice is IDU.
SUMMARY OF THE INVENTION: According to the present invention there are provided novel compositions of matter for the treatment of oral diseases and for the treatment of labial, nasal and genital lesions caused by Herpex simplex. The novel pharmaceutical compositions comprise an active ingredient or a combination of some active ingredients in an aqueous carrier containing glycyrrhizin. Glycyrrhizin is the glucuronide of glycyrrhetic acid and is a constituent of liquorice. The syrup of glycyrrhiza is used as demulcent, as expectorant and as pharmaceutical vehicle. It has now been discovered that at certain concentrations glycyrrhizin possesses excellent dispersing properties and that it forms stable gels which can be used advantageously in oral medicine. The novel preparations have excellent rheological properties for oral application.The substance has a sweet taste, yet tests carried out have shown that glycyrrhizin, in the concentrations tested, inhibits the adherence of streptococcus mutans and of actinomyces viscusus which are amongst the main cariogenic microorganisms to teeth.
BACKGROUND OF THE INVENTION Among the common primary diseases occurring the oral cavity are allergic stomatitis, oral candidiasis, herpetic stomatitis, aphthous ulcerations, etc.
In diseases such as Leukemias, Pemphigus Vulgaris, Erythema Multiforme etc., there are secondary signs which manifest themselves in inflammatory and ulcerative forms in the mouth.
These local conditions cause not only serious discomform to the patient but are a source of infection to the whole body. Medication is often administered systematically, thus exposing the patient to various side-effects. Undoubtedly, the local application of a drug is preferable whenever possible.
Herpes simplex infections causing herpes labialis and nasalis are known by the popular names of fever blisters or cold sores. They cause painful itching and burning and induce great discomfort to those afflicted by them. In recent years a marked increase in genital herpes infections has been observed and herpes simplex has now replaced syphillis as the second most common venereal disease. Most of the existing medications for topical treatment of these afflictions are ointments or creams which are not very effective.
The efficiency of local applications depends, among other factors, on the effectiveness of the contact to the affected area and its duration, and its penetration capabilities. It is customary, therefore, to use a vehicle that facilitates the application and prolongs the contact with the affect site.
Serious problems are encountered in topical medications to be applied to mucousal membranes, i.e., nasal and genital. Because of their high humidity, the medicine must be applied in a water soluble vehicle, since an oily base would prevent the direct contact of the drug with the affected area.
Special difficulties exist in application of oral medications. The mouth is rich with flora, and having a constant temperature of 36.8"C and a high humidity, it provides an ideal medium for the development of micro-organisms.
An efficient vehicle for oral treatment must withstand the constant saliva rinsing, and must resist enzymatic decomposition. Furthermore, the vehicle must have an agreeable taste and smell, and obviously, must be non-toxic. The medicine must be applied in water soluble vehicle since an oily base will prevent the direct contact of the drug with the affected area.
According to the invention, there are provided compositions for the treatment of lesions (oral, nasal and genital) caused by several reasons such as allergies, pathogenic agents, alcerations, etc.
STATE OF THE PRIOR ART: The existing preparations for treating diseases of the oral cavity are either inpalatable, or are intended for dermal application. For example, antiinflammatory ointments are prepared in oily bases, thus, being non effective for oral use. Syrups which are often used for topical oral application in order to disguise the taste of drugs, stimulate the formation of dental caries.
The existing preparations too are mostly in the form of ointments, creams or solutions in dimethylsulfoxide, thus not very effective for application to mucous membranes.
In the course of the preparation of galenic emulsions and suspensions, we realized that there exists a natural product, Glycyrrhizin, which possesses excellent dispersing qualities.
At concentrations ranging between 1-2%, Glycyrrhizin forms stable gels with ideal rheological properties for pharmaceutical preparations. Furthermore Glycyrrhizin is well known for its agreeable sweet taste, which has caused it to be a valuable additive to the food industry.
These qualities make the glycyrrhizin gel a highly appropriate vehicle for medications to be topically applied to the oral cavity and to all other muccous membranes.
Pompei et al. presented results relating to the effect of glycyrrhizin as inhibitor of viruses (see Nature 1979, 281(5733) 688-90. 688-690; Riv. Farmacol. Ter. 1979, 10 (3) 281-4). However these results were confined to cell cultures and no data are presented with regard to the in vivo effects of glycyrrhizin on herpes simplex. Experiments are carried out by us indicated that glycyrrhizin when applied in vivo, lacks almost any effect on herpes simplex infections.
IDU is a well known antiviral agent and has proved effective in the treatment of lesions of herpes (see for example Bauer et al. Chemotherapy of Virus Diseases, Pergamon Press 1973 50-53).
The present invention is a composition of IDU in glycyrrhizin-gel. It has the following considerable advantages over the conventional ointment: On application an immediate relief in the pain is obtained healing is speeded up considerably; the aqueous base is absorbed very quickly and therefore the unaesthetic effect of the ointment base preparations is eliminated; an 0.2% concentration of the active IDU achieves better results than 0.5% concentrations in the ointment.
Results and comparative studies are provided in the experimental section.
Infections caused by Herpes simplex affect mucous membranes of the mouth, nose, eyes and genitalia. According to the present invention there are provided compositions which are effective for the treatment of Herpes nasalis and labialis, and probably also for genital herpes. This composition is advantageously provided in the form of aqueous gel. The efficacy of the novel preparations was compared with compositions based on the use of Idoxuridine (IDU) as active ingredient, which are widely used for the treatment of such afflictions.
When the novel compositions of the present invention are applied, pain disappears almost immediately and the time of healing is drastically reduced. When the medication is used in prodomata stages, the lesions are abortive.
Pharmaceutical compositions based on idoxuridine (IDU) are in use for more than 10 years. In view of the extensive experience with such preparations, and in view of the comparison with the preparations of the present invention, it is assumed that there exists a synergistic effect between the antiviral compound IDU and the anti-inflammatory component glycyrrhizin.
The novel pharmaceutical compositions comprise a quantity of from about 0.5 to 2.5% glycyrrhizin, and preferably from 1 to 2 percent of this substance, in an aqueous medium, in combination with active ingredients such as antibiotics, fungicides, antiinflammatory steroid, antivirals and the like.
According to the invention there are also provided compositions for the treatment of oral, nasal and genital lesions caused by Herpes simplex. These contain an effective antiviral agent such as idoxuridine (IDU), in combination with gycyrrhrizin. The novel compositions are highly effective and it is believed that this is due to a synergistic effect of these two constituents.
As glycyrrhizin is accepted in food industry and also as adjuvant in pharmaceuticals for disguising unpleasant flavors, no toxicological problems arise as to the use of this natural substance as ingredient of the novel compositions of the present invention. The following examples, which are to be construed in a non-limitative manner, illustrate the present invention.
Unless otherwise defined, the following examples refer to aqueous solutions. Percents are by weight.
Example 1: Oral Antimycotic Preparation for Treatment of Oral Candidiasis. An Oral pharmaceutical preparation in gel form was prepared as follows: Nystatin 2% Glycyrrhizin 1 % Methyl Cellulose-4000 2% Propyl Gallate 0.1% Methyl Paraben 0.15% 1% Vanilline Alcoholic Solution 0.5% in Phosphate buffer pH 7.0 Example 2: Antibiotic Gel for Treating Oral Infections (Diseases) 0.5% Neomycine 1% Bacitracine 1.25% Glycyrrhizin in water Example 3: Antiinflammatory Preparation for Treatment of Oral Ulcerations: Triamcynolone 0.1% Glycyrrhizin 1 % Benzoic Acid 0.1 % in water Example 4:Preparation for Treatment Athropic Mucosa: Estradiol 0.1-0.01% Glycyrrhizin 2% Benzoic acid 0.1 % in water Example 5: Mestranol 0.001% Glycyrrhizin 2% Benzoic Acid 0.1 % in water Example 6: Premarin 0.063% Glycyrrhizin 2 % Benzoic acid 1 % in water Example 7: Anticariogenic Gels and Mouth Washes a) NaF 0.2% Glycyrrhizin 1.25% in H3PO4- 0.1 M b) NaF 2% Glycyrrhizin 1.25% in H3PO4 0.1 M c) NaF 0.01% Glycyrrhizin 0.25% in water.
Preparations for the Treatment of Mucosal Lesions, oral, nasal and genital, caused by Herpes simplex Virus.
Example 8: Idoxuridine (IDU) 0.2% glycyrrhizin 2.0% benzoic acid 0.1% in water Example 9: Idoxuridine (IDU 0.2% glycyrrhizin 1.5% benzoic acid 0.1 % in water Example 10: Idoxuridine 0.1 % glycyrrhizin 2% benzoic acid 0. 1 % in water Example 11: IDU 0.1% glycyrrhizin 1.5% benzoic acid 0.1 % in water Example 12: Treatment of Herpes Simplex A study was carried out to evaluate the effectivity of the mode of action of IDU in an aqueous glycyrrhizin base, and to compare it with conventional preparations such as VIRUSAN ointment produced by Ikapharm, Israel, which contains the active IDU in an ointment base at a concentration of 0.5%.
The comparison was made with preparations according to Example 8 of the present application. This was prepared by dissolving 0.2 g IDU and 2.0 g glycyrrhizin in 100 ml of a 0.1% solution of benzoic acid in water at elevated temperture with stirring. After about 5 minutes a homogeneous mixture was obtained, and after cooling there was obtained a transparent gel.
The study group encompassed 120 patients who had been referred to the Oral Medical Clinic of Hadassa University Hospital in Jerusalem by their physicians. The patients ranged from 18 to 60 years: there were 82 females and 38 males. There were divided into 3 groups; the objects and details of the investigation were explained and the consent of the participants was obtained.
The tests were carried out by the double-blind method. The first group was treated with a gel of the vehicle only (glycyrrhizin) alone. The second group was treated with a preparation according to the above (Example 8). The third group was treated with VIRUSAN produced by Ikapharm, which contains 0.5% IDU in an ointment base.
The patients applied the preparation every 2 hours during day time until crusting was achieved. The patients recorded duration of the lesions and degree of pain.
The results inducate that: a. The vehicle by itself gave immediate relief of pain after application. Time of healing which was about 8 to 14 days without any treatment, was reduced to about 8 to 10 days, which is not a significant result.
b. The VIRUSAN ointment did not relieve pain but resulted in a reduction of healing time to about 4 to 8 days.
c. The preparation of Example 8 relieved pain immediately and shortened time of healing to 2-4 days (6 in very severe cases) when used in the prodromal stage, the lesions were abortive, the appearance of the ointment was much superior to that of VIRUSAN. The acceptance of the novel preparation was favorable because of its smooth consistency and transparent appearance.
If healing takes place without treatment, severe ulcerations may result. The preparations according to the present invention reduce pain very markedly, the area of ulceration is substantially reduced and healing time is shortened.
Example 13: Treatment of Aph to us Stomatitis A composition according to Example 3 was used. This was prepared from 32 ml distilled water, 50 ml of 0.2 % benzoic acid in water, and 2 g glycyrrhizin, which were warmed with stirring until a clear solution was obtained, after which 18 ml ethanol were added. While still warm the mixture was poured into a mortar containing a mixture of 100 mg triamcynolone acetonide and a few drops of glycerin Thorough mixing resulted in a homogeneous suspension which gelatinized upon cooling.
Experiments were carried out with compositions of the invention for the treatment of recurrent aphtous stomatitis. The composition used was according to Example 3. The study was carried out with 134 patients ranging from 7 to 62 years, with 56 females and 78 males. Major aphtosis was found in 57 patients and minor aphtosis in 77. The objects of the study were explained to the patients and their consent was obtained. The patients kept full daily ulcer records and visited the clinic weekly for at least 6 months; recurrent aphtous stomatitis (RAS) was present for at least one year. The patients recorded localization, number, size and duration of ulcers and degree of pain on daily record charts. The study was by the double blind method.
The patients were divided into 3 groups, the first received glycyrrhizin alone (49 cases), the second received the vehicle plus triamcynolone, 0.1% (65 cases), and the third received Kenalog in Orabase (Squibb) (20 cases).
The patients applied the drug topically three times a day, continuing administration until the ulcer had healed. They were requested to abstain from eating and drinking for 30 minutes following each application.
The following results were obtained: 1) Patients treated with glycyrrhizin alone major aphtosis: improvement 22.7%; no change 77.3% minor aphtosis: " 68% " " 26%; remission: 1 case.
2) Patients treated with triamcynolone 0. 1% glycyrrhizin: major aphtosis: improvement 60%; no change 40% minor aphtosis: " 46%; remission 46% 3) Patients treated with Kenalog in Orabase showed similar results as those of group(2). The Kenalog preparation caused a certain discomfort during its use and a number of patients discontinued its use due to this. The preparation according to the present invention is much superior in this respect.
It is apparent that the good therapeutic effect is due to a synergistic effect between glycyrrhizin and trimcynolone. Due to its palatable taste and smooth consistency, the novel composition is more readily accepted by the patients than the conventional preparations.

Claims (10)

CLAIMS:
1. A preparation of the prevention of and for the treatment of dermal disease including oral diseases, and for the treatment of lessions caused by Herpes simplex, comprising glycyrrhizin in an aqueous medium, combined with a drug.
2. A preparation according to claim 1, for the treatment of oral diseases, containing 0.5 to 2.0 per cent by weight glycyrrhizin in an aqueous medium in combination with a drug selected from antimycotic agents, antibiotics, steroids and anticariogenic agents.
3. A pharmaceutical composition according to claim 2, wherein the antimycotic agent is nystatin.
4. A pharmaceutical composition according to claim 2, wherein the antiinflammatory steroid is triamcynolone.
5. A pharmaceutical composition according to claim 2, wherein the antiathropic agents, promoting keratinization of the oral mucosa, are estradiol or mestranol.
6. A pharmaceutical composition according to claim 2, wherein the anticariogenic agent is sodium fluoride.
7. A composition according to claim 1, for the treatment of Herpes simplex lesions, containing in addition an effective quantity of an antiviral agent.
8. A composition according to claim 7, wherein the antiviral agent is idoxuridine (IDU).
9. A pharmaceutical composition according to claim 7, in ointment form, for the treatment of Herpes simplex lesions containing in combination glycyrrhizin and idoxuridine.
10. A preparation for the prevention of and for the treatment of dermal disease including oral diseases, and for the treatment of lesions caused by Herpes simplex, comprising glycyrrhizin in an aqueous medium, combined with a drug, substantially as hereinbefore described and illustrated by the foregoing Examples.
GB08429749A 1982-03-05 1984-11-24 Pharmaceutical compositions containing glycyrrhizin Expired GB2167296B (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
IL65184A IL65184A (en) 1982-03-05 1982-03-05 Preparation comprising glycyrrhizin for the treatment of dermal,including oral diseases
IL65184A IL65184A0 (en) 1982-03-05 1982-03-05 Preparation for the treatment of oral diseases,comprising glycyrrhizin
GB08429749A GB2167296B (en) 1982-03-05 1984-11-24 Pharmaceutical compositions containing glycyrrhizin
DE19843443242 DE3443242A1 (en) 1982-03-05 1984-11-27 Glycyrrhizin and a medicament containing an active compound
CH5651/84A CH662510A5 (en) 1982-03-05 1984-11-27 GLYCYRRHIZINE AND A MEDICINAL PRODUCT CONTAINING AN ACTIVE SUBSTANCE.
FR848418155A FR2573655B1 (en) 1982-03-05 1984-11-29 PHARMACEUTICAL COMPOSITION BASED ON GLYCYRRHYZINE FOR DERMAL DISEASES

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IL65184A IL65184A0 (en) 1982-03-05 1982-03-05 Preparation for the treatment of oral diseases,comprising glycyrrhizin
GB08429749A GB2167296B (en) 1982-03-05 1984-11-24 Pharmaceutical compositions containing glycyrrhizin

Publications (3)

Publication Number Publication Date
GB8429749D0 GB8429749D0 (en) 1985-01-03
GB2167296A true GB2167296A (en) 1986-05-29
GB2167296B GB2167296B (en) 1988-11-16

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GB08429749A Expired GB2167296B (en) 1982-03-05 1984-11-24 Pharmaceutical compositions containing glycyrrhizin

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CH (1) CH662510A5 (en)
DE (1) DE3443242A1 (en)
FR (1) FR2573655B1 (en)
GB (1) GB2167296B (en)
IL (2) IL65184A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4795740A (en) * 1986-05-20 1989-01-03 Cohen Eric A Antiviral peptides and means for treating herpes infections
US5002932A (en) * 1987-11-24 1991-03-26 Yves Langelier Antiviral pharmaceutical compositions and method of treating herpes
US5122376A (en) * 1989-05-12 1992-06-16 Isf Societa Per Azioni Calcitonin gene related peptide
US5183802A (en) * 1987-11-13 1993-02-02 Isf Societa Per Azioni Pharmaceutical compositions for intranasal administration of calcitonin
WO1993025209A1 (en) * 1992-06-18 1993-12-23 Fabulon Rg Kozmetikai Kft. Compositions for the treatment and prophylaxis of inflammations and dermatoses induced by viruses and process for the preparation thereof
US6696433B2 (en) 1996-07-22 2004-02-24 Renovo Limited Use of sex steroids function modulators to treat wounds and fibrotic disorders
EP1446167A2 (en) * 2001-11-05 2004-08-18 Orahealth Corporation Treating canker sores with patches to speed healing and relieve pain

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8824835D0 (en) * 1988-10-24 1988-11-30 Univ Court Of The University O Administrations of corticosteroids
CA2044663A1 (en) * 1990-07-12 1992-01-13 Makoto Tanaka Water-dispersible polyene antifungal complexes
FR2685205A1 (en) * 1991-12-23 1993-06-25 Ardeval Laboratoires SOLID - BASED PLANT COMPOSITION, PREPARATION METHOD AND APPLICATIONS THEREOF.

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1567307A (en) * 1976-12-01 1980-05-14 Unilever Ltd Salts of glycyrrhizinic acid

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2071494B (en) * 1980-03-08 1984-05-31 Maruzen Kasei Co Ltd Cosmetics containing 18-glycyrrhizins
JPS61151115A (en) * 1984-12-24 1986-07-09 Sanyo Scott Kk Cleansing foam

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1567307A (en) * 1976-12-01 1980-05-14 Unilever Ltd Salts of glycyrrhizinic acid

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4795740A (en) * 1986-05-20 1989-01-03 Cohen Eric A Antiviral peptides and means for treating herpes infections
US5183802A (en) * 1987-11-13 1993-02-02 Isf Societa Per Azioni Pharmaceutical compositions for intranasal administration of calcitonin
US5002932A (en) * 1987-11-24 1991-03-26 Yves Langelier Antiviral pharmaceutical compositions and method of treating herpes
US5122376A (en) * 1989-05-12 1992-06-16 Isf Societa Per Azioni Calcitonin gene related peptide
WO1993025209A1 (en) * 1992-06-18 1993-12-23 Fabulon Rg Kozmetikai Kft. Compositions for the treatment and prophylaxis of inflammations and dermatoses induced by viruses and process for the preparation thereof
US6696433B2 (en) 1996-07-22 2004-02-24 Renovo Limited Use of sex steroids function modulators to treat wounds and fibrotic disorders
EP1446167A2 (en) * 2001-11-05 2004-08-18 Orahealth Corporation Treating canker sores with patches to speed healing and relieve pain
EP1446167A4 (en) * 2001-11-05 2010-09-29 Orahealth Corp Treating canker sores with patches to speed healing and relieve pain

Also Published As

Publication number Publication date
FR2573655B1 (en) 1990-07-20
FR2573655A1 (en) 1986-05-30
GB8429749D0 (en) 1985-01-03
DE3443242A1 (en) 1986-05-28
CH662510A5 (en) 1987-10-15
GB2167296B (en) 1988-11-16
IL65184A (en) 1985-08-30
IL65184A0 (en) 1982-05-31

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Effective date: 19921124