WO2001095723A1 - Parasiticidal composition - Google Patents
Parasiticidal composition Download PDFInfo
- Publication number
- WO2001095723A1 WO2001095723A1 PCT/GB2001/002610 GB0102610W WO0195723A1 WO 2001095723 A1 WO2001095723 A1 WO 2001095723A1 GB 0102610 W GB0102610 W GB 0102610W WO 0195723 A1 WO0195723 A1 WO 0195723A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition according
- composition
- imidazole
- triazole
- alcohol
- 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.)
- Ceased
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Definitions
- the invention relates to a parasiticidal composition and in particular to a composition for controlling headlice infestation in humans.
- Lice infestation in man is generally caused by insects from the families Pediculidae and Pthiridae, in particular Pedicuhis humanus species and Pthirus pubis.
- the azole antifungal agents have five-membered organic rings that contain either two or three nitrogen molecules (the imidazoles and the triazoles respectively). Two types of antifungal affect the cell membrane-polyenes and imidazoles.
- the clinically useful imidazoles are clotrimazole, miconazole, and ketoconazole, two important triazoles are itraconazole and fluconazole.
- the azole antifungal agents are thought to inhibit cytochrome P 50 - dependent enzymes involved in the biosynthesis of cell membranes
- kitoconazole was the original model for the orally administered antifungal azoles. It can be administered both orally and topically and has a range of activity including infections. It is also active against mucosal candidiasis and a variety of cutaneous mycoses, including dermatophyte infections, pityriasis versicolor, and cutaneous candidiasis.
- the triazoles (fluconazole, itraconazole) have become the standard for the azoles, and have replaced amphotericin B for managing certain forms of the systemic mycoses.
- the compounds work by binding to sterols in the cell membrane.
- the principal sterol in fungal cell membranes is ergosterol, while the principal sterol in mammalian cell membranes is cholesterol.
- Polyenes have a stronger affinity for ergosterol than cholesterol, so they show greater activity against fungal cells than mammalian cells.
- the binding forms channels of about 0.8nm in diameter, which in turn allows leakage of up to 90% of cellular potassium ions (K+). This is followed by a loss of magnesium ions (Mg++). The loss of K+ ions inhibits a variety of metabolic processes, including glycolysis and respiration.
- Imidazoles bind to the fungal cytochrome P- 45 o. This inhibits production of ergosterol synthesis or its incorporation into the cell membrane. This interferes with the membrane function and permeability. This means many components, including K+, leak out of the cell. Examples include ketoconazole, miconazole, econazole, fluconazole, clotrimazole, and intraconazole. According to the present invention there is provided a parasiticidal composition comprising an imidazole and/or a triazole and a physiologically acceptable carrier.
- the imidazole is selected from one or more of the group consisting of clotrimazole, ketoconazole, and miconazole and that the triazole is selected from fluconazole and itraconazole.
- composition is adapted for topical application to a subject. It is particularly preferred that the composition is adapted for application as a lotion or mousse for the hair.
- composition may further comprise alcohol, such as isopropanol and/or ethanol, and the physiologically acceptable carrier may comprise the alcohol.
- alcohol such as isopropanol and/or ethanol
- physiologically acceptable carrier may comprise the alcohol.
- composition may comprise at least about 0.2% v/v imidazole and/or triazole.
- the composition may further comprise a constituent having ovicidal activity.
- the ovicidal agent may comprise a terpene, preferably one or both of d- limonene and geranyl acetate.
- composition is for use in the treatment and/or prevention of human infestation by parasites from the families Pediculidae and Pthiridae.
- a process for preparing a parasiticidal composition which comprises bringing an imidazole and/or a triazole into association with at least one carrier therefor.
- a process for preparing a parasiticidal composition which comprises bringing an imidazole and/or a triazole into association with at least one carrier therefor.
- an imidazole and/or a triazole in the manufacture of a composition for use in controlling parasite infestations in humans, in particular infestation by parasites from the families Pediculidae and Pthiridae.
- Human lice pediculus humanus, were obtained from the culture colony maintained by the Medical Entomology Centre. Adult female and male lice, in approximately equal numbers, were used for each test. The lice were fed on the morning of the test and allowed a minimum of 4 hours to recover, during which time they were able to excrete excess water imbibed with their blood meal. Lice were counted into batches that were provided with squares of an open meshed nylon gauze (tulle), as a substrate upon which to stand, and each batch allocated to a marked 30 millimetre plastic Petri dish.
- tulle open meshed nylon gauze
- the gauze bearing lice was immersed in the fluid for 10 seconds, during which time the gauze was turned at least twice to ensure removal of air bubbles. After removal from the fluid the gauze and insects were lightly blotted to remove excess fluid and returned to their marked Petri dish. The same procedure was repeated for the other replicate gauze squares in that batch.
- Gauze squares bearing lice were incubated under normal maintenance conditions (30° ⁇ 2° Celsius and 50% ⁇ 15% relative humidity) for the remainder of the test period.
- the insects and gauze were washed using a bland toiletry shampoo (Boots frequent wash shampoo) diluted one part shampoo with fourteen parts water (FWS 1:15) after which they were rinsed three times using 250 millilitres of warm (34° Celsius) tap water poured through and over the gauze squares. They were then blotted dry using medical wipe tissue and incubated under normal maintenance conditions in clean plastic Petri dishes of the appropriate size until the results were recorded.
- Mortality percentages were corrected by Abbott's formula. The percent of mortality in a control was subtracted from the percent mortality in the test and then divided by the percent mortality in the test.
- An insect's exoskeleton serves not only as a protective covering over the body, but also as a surface for muscle attachment, a water-tight barrier against desiccation, and a sensory interface with the environment.
- the typical insect exoskeleton is a multi-layered structure with four functional regions, epicuticle, procuticle, epidermis, and basement membrane.
- the epidermis is a single layer of epithelial cells. It is responsible for producing at least part of the basement membrane as well as all of the overlying layers of cuticle.
- the procuticle lies immediately above the epidermis. It contains microfibers of chitin surrounded by a matrix of protein that varies in composition from insect to insect and even from place to place within the body of a single insect.
- procuticle stratifies into a hard, outer exocuticle and a soft, inner endocuticle.
- exocuticle Differentiation of exocuticle involves a chemical process (called sclerotization) that occurs shortly after each molt.
- sclerotization individual protein molecules are linked together by quinone compounds. These reactions "solidify” the protein matrix, creating rigid "plates” of exoskeleton known as sclerites.
- Quinone cross-linkages do not form in parts of the exoskeleton where resilin (an elastic protein) is present in high concentrations. These areas are membranes and they remain soft and flexible because they never develop a well-differentiated exocuticle.
- the epicuticle is the outermost part of the cuticle. Its function is to reduce water loss and block the invasion of foreign matter.
- the innermost layer of epicuticle is often called the cuticulin layer, a stratum composed of lipoproteins and chains of fatty acids.
- a layer of wax molecules lies just above the cuticulin layer, it serves as a barrier to movement of water into or out of the insect's body. In many insects a cement layer covers the wax and protects it from abrasion.
- imidazoles act as either sclerotisizers or they simply cause a diffusion gradient across the louse resulting in death.
- the results tend to indicate also that this effect may be enhanced by the use of an alcoholic vehicle.
- formulations having parasiticidal activity were prepared as follows:
- formulations which can be prepared in accordance with this invention include lotions and mousses as well as, potentially, other hair treatments.
- additional constituents which are required will vary according to the desired properties of the final product.
- the skilled worker will be familiar with such constituents and their usage, which can include, for example, surfactants, silicone compounds, suspending agents colourings and perfumes.
- compositions according to the invention To enhance the activity of the compositions according to the invention it has been found that further constituents having ovicidal activity can be added without adversely affecting their efficacy.
- further constituents are terpenes and in particular, the te ⁇ enes d-limonene and geranyl acetate can be used, each at a concentration of from 0.2% v/v to 1.0% v/v.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to imidazole selected from one or more of the group consisting of clotrimazole, ketoconazole, and miconazole and that the triazole is selected from fluconazole and itraconazole.
Description
PARASITICIDAL COMPOSITION
The invention relates to a parasiticidal composition and in particular to a composition for controlling headlice infestation in humans.
Lice infestation in man is generally caused by insects from the families Pediculidae and Pthiridae, in particular Pedicuhis humanus species and Pthirus pubis.
The control of parasite infestations such as headlice has recently been managed by mosaic policies, with insecticides from the groups consisting DDT, cyclodienes, organophosphates, carbamates and pyrethroids.
To ensure the availability of a diversity of insecticidal treatments there is a continuing requirement for novel insecticides to ensure suitable mosaic policies are maintained.
It is an object of the present invention to seek to provide an alternative novel insecticide for the treatment of headlice.
The azole antifungal agents have five-membered organic rings that contain either two or three nitrogen molecules (the imidazoles and the triazoles respectively). Two types of antifungal affect the cell membrane-polyenes and imidazoles.
The clinically useful imidazoles are clotrimazole, miconazole, and ketoconazole, two important triazoles are itraconazole and fluconazole.
In general, the azole antifungal agents are thought to inhibit cytochrome P 50- dependent enzymes involved in the biosynthesis of cell membranes, kitoconazole was the original model for the orally administered antifungal azoles. It can be administered both orally and topically and has a range of activity including infections. It is also active against mucosal candidiasis and a variety of cutaneous mycoses, including dermatophyte infections, pityriasis versicolor, and cutaneous candidiasis.
The triazoles (fluconazole, itraconazole) have become the standard for the azoles, and have replaced amphotericin B for managing certain forms of the systemic mycoses.
The compounds work by binding to sterols in the cell membrane. The principal sterol in fungal cell membranes is ergosterol, while the principal sterol in mammalian cell membranes is cholesterol. Polyenes have a stronger affinity for ergosterol than cholesterol, so they show greater activity against fungal cells than mammalian cells. The binding forms channels of about 0.8nm in diameter, which in turn allows leakage of up to 90% of cellular potassium ions (K+). This is followed by a loss of magnesium ions (Mg++). The loss of K+ ions inhibits a variety of metabolic processes, including glycolysis and respiration.
Imidazoles bind to the fungal cytochrome P-45o. This inhibits production of ergosterol synthesis or its incorporation into the cell membrane. This interferes with the membrane function and permeability. This means many components, including K+, leak out of the cell. Examples include ketoconazole, miconazole, econazole, fluconazole, clotrimazole, and intraconazole.
According to the present invention there is provided a parasiticidal composition comprising an imidazole and/or a triazole and a physiologically acceptable carrier.
It is preferred that the imidazole is selected from one or more of the group consisting of clotrimazole, ketoconazole, and miconazole and that the triazole is selected from fluconazole and itraconazole.
It is preferred that the composition is adapted for topical application to a subject. It is particularly preferred that the composition is adapted for application as a lotion or mousse for the hair.
The composition may further comprise alcohol, such as isopropanol and/or ethanol, and the physiologically acceptable carrier may comprise the alcohol.
The composition may comprise at least about 0.2% v/v imidazole and/or triazole.
The composition may further comprise a constituent having ovicidal activity. The ovicidal agent may comprise a terpene, preferably one or both of d- limonene and geranyl acetate.
It is preferred that the composition is for use in the treatment and/or prevention of human infestation by parasites from the families Pediculidae and Pthiridae.
According to a further aspect of the invention there is provided a process for preparing a parasiticidal composition, which comprises bringing an imidazole and/or a triazole into association with at least one carrier therefor.
According to a yet further aspect of the invention there is provided the use of an imidazole and/or a triazole in the manufacture of a composition for use in controlling parasite infestations in humans, in particular infestation by parasites from the families Pediculidae and Pthiridae.
The invention will further be described by way of illustration by reference to the following experiments.
Method of Testing the Pediculicidal Activity of a Composition.
Samples of clotrimazole, miconazole and ketocanazole were used. In preparation for use the stock chemicals were diluted to the appropriate level using 60% propan-2-ol (isopropyl alcohol, isopropanol) diluted with 40% distilled water.
Solutions of the clotrimazole, miconazole and ketoconazole were made on a weight for weight basis (w/w) in the alcohol vehicle.
Measurement of Pediculicidal Activity by Immersion.
Human lice, pediculus humanus, were obtained from the culture colony maintained by the Medical Entomology Centre. Adult female and male lice, in approximately equal numbers, were used for each test. The lice were fed on the morning of the test and allowed a minimum of 4 hours to recover, during which time they were able to excrete excess water imbibed with their blood meal. Lice were counted into batches that were provided with squares of an
open meshed nylon gauze (tulle), as a substrate upon which to stand, and each batch allocated to a marked 30 millimetre plastic Petri dish.
For the test procedure an aliquot of approximately 5 millilitres of the imidazole solution was poured into the base of a clean 30 millimetre plastic Petri dish.
The gauze bearing lice was immersed in the fluid for 10 seconds, during which time the gauze was turned at least twice to ensure removal of air bubbles. After removal from the fluid the gauze and insects were lightly blotted to remove excess fluid and returned to their marked Petri dish. The same procedure was repeated for the other replicate gauze squares in that batch.
Gauze squares bearing lice were incubated under normal maintenance conditions (30° ± 2° Celsius and 50% ± 15% relative humidity) for the remainder of the test period. At the end of exposure period the insects and gauze were washed using a bland toiletry shampoo (Boots frequent wash shampoo) diluted one part shampoo with fourteen parts water (FWS 1:15) after which they were rinsed three times using 250 millilitres of warm (34° Celsius) tap water poured through and over the gauze squares. They were then blotted dry using medical wipe tissue and incubated under normal maintenance conditions in clean plastic Petri dishes of the appropriate size until the results were recorded.
For these tests lice were exposed for 2 hours.
A control comparison test was performed using the 60% propan-2-ol (isopropanol) solvent, which is routinely used in our laboratory and causes
minimum mortality to lice, in place of the imidazole solution. All other procedures for this comparator were the same as for the test groups.
The results of tests against lice were recorded after 24 hours.
Results
Activity of each imidazole against lice was effectively complete with 2.5% solutions. Dead lice showed signs of dehydration and most had burst guts so that they took on a dark red colour throughout the tissues.
Treatment Replicate Number of lice Mortality %
Total Killed Moribund
Clotrimazole 1 21 19 2 100 in lPA
Miconazole 1 20 17 3 100
Ketoconazole 1 21 4 4 60
Control 1 20 2 0 10.0
Mortality percentages were corrected by Abbott's formula. The percent of mortality in a control was subtracted from the percent mortality in the test and then divided by the percent mortality in the test.
The results indicate that imidazoles are very effective pediculicides.
The mode of action of the present invention is not fully understood, however, it is hypothesised that these actives work on the exoskeleton of the lice.
An insect's exoskeleton (integument) serves not only as a protective covering over the body, but also as a surface for muscle attachment, a water-tight barrier against desiccation, and a sensory interface with the environment.
The typical insect exoskeleton is a multi-layered structure with four functional regions, epicuticle, procuticle, epidermis, and basement membrane.
The epidermis is a single layer of epithelial cells. It is responsible for producing at least part of the basement membrane as well as all of the overlying layers of cuticle.
The procuticle lies immediately above the epidermis. It contains microfibers of chitin surrounded by a matrix of protein that varies in composition from insect to insect and even from place to place within the body of a single insect.
In some parts of the body, procuticle stratifies into a hard, outer exocuticle and a soft, inner endocuticle.
Differentiation of exocuticle involves a chemical process (called sclerotization) that occurs shortly after each molt. During sclerotization, individual protein molecules are linked together by quinone compounds. These reactions "solidify" the protein matrix, creating rigid "plates" of exoskeleton known as sclerites.
Quinone cross-linkages do not form in parts of the exoskeleton where resilin (an elastic protein) is present in high concentrations. These areas are membranes and they remain soft and flexible because they never develop a well-differentiated exocuticle.
The epicuticle is the outermost part of the cuticle. Its function is to reduce water loss and block the invasion of foreign matter. The innermost layer of epicuticle is often called the cuticulin layer, a stratum composed of lipoproteins and chains of fatty acids. A layer of wax molecules lies just above the cuticulin layer, it serves as a barrier to movement of water into or out of the insect's body. In many insects a cement layer covers the wax and protects it from abrasion.
It is proposed that imidazoles act as either sclerotisizers or they simply cause a diffusion gradient across the louse resulting in death. The results tend to indicate also that this effect may be enhanced by the use of an alcoholic vehicle.
Formulation
Using the results of these tests, formulations having parasiticidal activity were prepared as follows:
Lotion Formulation
Imidazole 1.0%
Water 30.0%
Isopropyl Alcohol to 100%
Mousse Formulation
Imidazole 1.0%
Polawax 4.0%
Crodamol DA 2.0%
Propylene Glycol 2.0%
Polysorbate 60 1.0%
Sodium Lauryl Sulphate 0.5%
Isopropyl Alcohol 5.0%
Water 79.5%
Butane 5.0%
Thus, formulations which can be prepared in accordance with this invention include lotions and mousses as well as, potentially, other hair treatments. The precise nature and qualities of additional constituents which are required will vary according to the desired properties of the final product. The skilled worker will be familiar with such constituents and their usage, which can include, for example, surfactants, silicone compounds, suspending agents colourings and perfumes.
To enhance the activity of the compositions according to the invention it has been found that further constituents having ovicidal activity can be added without adversely affecting their efficacy. These further constituents are terpenes and in particular, the teφenes d-limonene and geranyl acetate can be used, each at a concentration of from 0.2% v/v to 1.0% v/v.
Claims
1. A parasiticidal composition, comprising an imidazole and/or a triazole in a physiologically acceptable carrier.
2. A composition according to claim 1, wherein the imidazole, is selected from the group consisting of clotrimazole, ketoconazole and micronazole, and the triazole is selected from the group consisting of fluconazole and itraconazole.
3. A composition according to claim 1 or claim 2, adapted for topical application to a subject.
4. A composition according to claim 3, adapted for application as a lotion or a mousse.
5. A composition according to any preceding claim, further comprising alcohol.
6. A composition according to claim 5, wherein the physiologically acceptable carrier comprises the alcohol.
7. A composition according to claim 5 or claim 6, the alcohol comprising isopropanol and/or ethanol.
8. A composition according to any preceding claim, comprising at least about 0.2%) v/v imidazole and/or triazole.
9. A composition according to any preceding claim, further comprising a constituent having ovicidal activity.
10. A composition according to claim 9, the further constituent comprising a terpene or terpenes.
11. A composition according to claim 10, the terpene comprising one or both of d-limonene and geranyl acetate.
12. A composition according to any preceding claim, for use in the treatment and/or prevention of human infestation by parasites from the families Pediculidae and Pthiridae.
13. A composition according to any preceding claim, comprising an imidazole and/or triazole, water and isopropyl alcohol in the form of a lotion.
14. A composition according to any of claims 1 to 12, comprising an imidazole and/or triazole, polawax, crodamol DA, propylene glycol, polysorbate 60, sodium lauryl sulphate, isopropyl alcohol, water and butane in the form of a mousse.
15. A process for preparing the parasiticidal composition claimed in any of claims 1 to 14, which comprises bringing an imidazole and/or a triazole into association with at least one physiologically acceptable carrier therefor.
16. A process according to claim 15, wherein the composition comprises a lotion or mousse.
17. A process according to claim 15 or claim 16, further including the step of bringing the imidazole and/or triazole into contact with alcohol.
18. A process according to any of claims 15 to 17, which is a process for preparing a composition for use in the treatment of human infestation by parasites from the families Pediculidae and Pthiridae.
19. The use of an imidazole and/or triazole in the manufacture of a composition for use in the treatment of parasite infestation.
20. The use according to claim 19, wherein the composition is for use in the treatment of infestation in humans by parasites from the families Pediculidae a d Pthiridae.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2001264110A AU2001264110A1 (en) | 2000-06-15 | 2001-06-15 | Parasiticidal composition |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0014667A GB0014667D0 (en) | 2000-06-15 | 2000-06-15 | Parasiticidal composition |
| GB0014667.0 | 2000-06-15 | ||
| GB0019255.9 | 2000-08-04 | ||
| GB0019255A GB0019255D0 (en) | 2000-08-04 | 2000-08-04 | Parasiticidal composition |
| GB0027435A GB0027435D0 (en) | 2000-11-09 | 2000-11-09 | Parasiticidal composition |
| GB0027435.7 | 2000-11-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2001095723A1 true WO2001095723A1 (en) | 2001-12-20 |
Family
ID=27255766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB2001/002610 Ceased WO2001095723A1 (en) | 2000-06-15 | 2001-06-15 | Parasiticidal composition |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU2001264110A1 (en) |
| WO (1) | WO2001095723A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005070421A1 (en) * | 2004-01-22 | 2005-08-04 | Alparis S.A. De C.V. | Fluconazole-tinidazole combination for the treatment of vaginal infections, composition thereof and preparation and use of same |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3565992A (en) * | 1968-03-08 | 1971-02-23 | Dow Chemical Co | Halogenated imidazole and imidazole salts used for controlling insect and helminth parasites |
| GB2092582A (en) * | 1981-02-09 | 1982-08-18 | Ciba Geigy Ag | Substituted 2-(anilinomethyl)- 2-imidazoline derivatives and pesticidal compositions containing them |
| EP0113945A1 (en) * | 1983-01-19 | 1984-07-25 | Eli Lilly And Company | Amine salts |
| EP0496316A1 (en) * | 1991-01-19 | 1992-07-29 | Hoechst Aktiengesellschaft | Pour-on formulation for application of anthelminthics |
| US5174475A (en) * | 1991-03-26 | 1992-12-29 | Glaxo Inc. | Sequential dosing of antifungal and antiinflammatory compositions |
| WO1993018010A1 (en) * | 1992-03-12 | 1993-09-16 | Pfizer Limited | Benzimidazole anthelmintic agents |
| EP0712847A1 (en) * | 1993-08-11 | 1996-05-22 | Nippon Soda Co., Ltd. | Imidazole derivative, process for producing the same, and pest control drug |
| WO1997036486A1 (en) * | 1996-03-29 | 1997-10-09 | Merial | Solution for direct application on the skin for controlling cattle and sheep parasites |
| EP0957094A1 (en) * | 1998-05-14 | 1999-11-17 | Pfizer Inc. | 1-(2-Halogenaryl)azoles as antiparasitic agents |
-
2001
- 2001-06-15 AU AU2001264110A patent/AU2001264110A1/en not_active Abandoned
- 2001-06-15 WO PCT/GB2001/002610 patent/WO2001095723A1/en not_active Ceased
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3565992A (en) * | 1968-03-08 | 1971-02-23 | Dow Chemical Co | Halogenated imidazole and imidazole salts used for controlling insect and helminth parasites |
| GB2092582A (en) * | 1981-02-09 | 1982-08-18 | Ciba Geigy Ag | Substituted 2-(anilinomethyl)- 2-imidazoline derivatives and pesticidal compositions containing them |
| EP0113945A1 (en) * | 1983-01-19 | 1984-07-25 | Eli Lilly And Company | Amine salts |
| EP0496316A1 (en) * | 1991-01-19 | 1992-07-29 | Hoechst Aktiengesellschaft | Pour-on formulation for application of anthelminthics |
| US5174475A (en) * | 1991-03-26 | 1992-12-29 | Glaxo Inc. | Sequential dosing of antifungal and antiinflammatory compositions |
| WO1993018010A1 (en) * | 1992-03-12 | 1993-09-16 | Pfizer Limited | Benzimidazole anthelmintic agents |
| EP0712847A1 (en) * | 1993-08-11 | 1996-05-22 | Nippon Soda Co., Ltd. | Imidazole derivative, process for producing the same, and pest control drug |
| WO1997036486A1 (en) * | 1996-03-29 | 1997-10-09 | Merial | Solution for direct application on the skin for controlling cattle and sheep parasites |
| EP0957094A1 (en) * | 1998-05-14 | 1999-11-17 | Pfizer Inc. | 1-(2-Halogenaryl)azoles as antiparasitic agents |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005070421A1 (en) * | 2004-01-22 | 2005-08-04 | Alparis S.A. De C.V. | Fluconazole-tinidazole combination for the treatment of vaginal infections, composition thereof and preparation and use of same |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2001264110A1 (en) | 2001-12-24 |
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