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US3836540A - 1-(dimesitylmethyl)imidazole - Google Patents

1-(dimesitylmethyl)imidazole Download PDF

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Publication number
US3836540A
US3836540A US00330909A US33090973A US3836540A US 3836540 A US3836540 A US 3836540A US 00330909 A US00330909 A US 00330909A US 33090973 A US33090973 A US 33090973A US 3836540 A US3836540 A US 3836540A
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imidazole
compounds
acid
dimesitylmethyl
addition
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US00330909A
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Der Stelt C Van
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Brocades Stheeman and Pharmacia
Koninklijke Pharmaceutische Fabrieken NV
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Koninklijke Pharmaceutische Fabrieken NV
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • N-tritylimidazole derivatives show fungicide activities.
  • South African Pat. 68/ 5,392 discloses antimycotics of the general formula:
  • this invention relates to the acid addition and quaternary ammonium salts, thereof, more specifically, the pharmaceutically acceptable acid addition and quaternary ammonium salts.
  • this invention encompasses pharmaceutical compositions containing said compounds and methods for using said compositions as anti-fungal agents and in the treatment of diseases caused by M ycoplasma gallisepticum.
  • acid addition salt is intended to encompass the salts formed by the addition of most organic and inorganic acids, such as sulfuric acid, phosphoric acid, hydriodic acid, oxalic acid, tartaric acid, etc.
  • quaternary ammonium salt is intended to encompass compounds such as the methyl iodide, ethyl sulfate, benzyl chloride, etc.
  • salts When the preceding terms are prefaced by the term pharmaceutically acceptable, it is intended to limit the salts to those having a relatively low order of toxicity, such as in the case of acid addition salts being limited to the hydrochlorides, sulfates, phosphates, acetates, citrates, maleates, fumaraates, etc., and in the case of the quaternary ammonium salts to the chlorides, sulfates, phosphates, etc.
  • the compounds of this invention have valuable therapeutic properties. They have a strong fungicidal activity against pathogenic fungi such as Candida albicans, Epidermophyton floccosum, Microsporum audouinii, Microsporum canis, T richophyton schoenleinni. This activity makes the compounds useful in the treatment of various fungus diseases in humans and animals.
  • the compounds of this invention are also useful as agricultural fungicides and pre-emergence herbicides. They may, for instance, be used in the control of early blight of tomato and anthracnose disease of cucumber and as eradicants for powdery mildew of bean.
  • the compounds of this invention may be administered orally, parenterally or topically in a pharmacologically acceptable carrier according to accepted pharmaceutical practice.
  • the dosage and mode of administration will depend on the mammalian species and the disease treated. In adult humans the oral dosage will be from 25-250 mg./kg. daily.
  • preparations such as salves, ointments, lotions or powders, containing from 0.1 to 5%, preferably 1 to 2% by weight of the active substance may be used.
  • the preparations may take any of the forms customarily employed for administration of therapeutic substances.
  • Tablets and pills may be formulated in the usual manner with one or more pharmaceutically acceptable diluents or excipients, for example lactose or starch, and include materials of a lubricating nature, for example calcium or magnesium stearate.
  • Capsules made of absorbable material, such as gelatin may contain the active substance alone or in admixture with a solid or liquid diluent.
  • Liquid preparations may be in the form of suspensions, emulsions, syrups or elixirs of the active substance in water or other liquid medium commonly used for making orally acceptable pharmaceutical formulations, such as liquid paraffin, or a syrup or elixir base.
  • the active substance may also be made up in a form suitable for parenteral administration, i.e. as a suspension or emulsion in sterile water or an organic liquid usually employed for injectable preparations, for example, a vegetable oil such as olive oil, or a sterile solution in water or an organic solvent.
  • a form suitable for parenteral administration i.e. as a suspension or emulsion in sterile water or an organic liquid usually employed for injectable preparations, for example, a vegetable oil such as olive oil, or a sterile solution in water or an organic solvent.
  • the active substance can also be used in the form of preparations for local application such as salves, ointments, lotions or powders, containing generally used excipients.
  • Ointments may, for instance, contain semi-solid ointment bases such as Vaseline.
  • the active substance may be mixed with finely divided solid substances such as talc or boric acid;
  • the compounds of this invention are advantageously used in formulations containing 0.1-l0 percent by weight of the active substance. Suitable amounts of the active substance to be applied range from 1-l5 kg. per hectare.
  • the compounds of this invention show a high degree of activity against Mycoplasma gallise pticum in poultry, especially chickens and turkeys.
  • these compounds when administered orally to poultry in a daily dose range of from about 100 mg. to about 500 mg. per kg. of body weight, preferably 200 mg. to 500 mg. per kg. of body weight, find additional utility in treating or preventing chronic respiratory infections in poultry caused by Mycoplasma gallisepticum.
  • the compounds may be mixed with a nontoxic, edible carrier to form a feed supplement which is then incorporated in the animal feed in the desired concentration, or they may be administered in unit dosage forms, or in the form of a liquid drench.
  • a feed supplement which is then incorporated in the animal feed in the desired concentration
  • they may be administered in unit dosage forms, or in the form of a liquid drench.
  • water-soluble salts or a dispersible, wettable powder containing the active ingredient may be added to the drinking water of the animals.
  • the means employed for administering these imidazoles to animals are not critical, and any of the methods now used or available for treating animals infected with or susceptible to infection from Mycoplasma gallisepticum are satisfactory.
  • the compounds are mixed with a suspending agent such as bentonite and the solid product added to water just prior to administration.
  • a suspending agent such as bentonite
  • the preferred drenches in accordance with this invention contain from about 50% by weight of active compound.
  • novel feed and feed supplement compositions are provided in which the compounds of this invention are present as the active ingredient.
  • Such compositions comprise the i-midazole intimately dispersed in or admixed 'with an inert carrier or diluent, i.e. one that is nonreactive with respect to the imidazole and that may be administered with safety to the animals.
  • the carrier or diluent is preferably one that is or may be an ingredient of the animal ration.
  • the active ingredient is present in relatively large amounts.
  • These supplements are suitable for addition to the feed either directly or after an intermediate dilution or blending step.
  • carriers or diluents suitable for such compositions are solid orally ingestible carriers such as distillers dried grains, corn meal, citrus meal, fermentation residues, ground oyster shells, Attapulgus clay, wheat shorts, molasses solubles, corn cob meal, edible vegetable substances, toasted dehulled soya flour, soybean mill feed, antibiotic mycelia, soya grits, crushed limestone and the like.
  • the compounds are intimately dispersed or admixed throughout the solid inert carrier by methods such as grinding, stirring, milling, or tumbling.
  • compositions of any desired concentration may be prepared.
  • Formulations containing from about 5%? to about 50% by weight, and preferably from about -30% by weight, of active ingredient are particularly suitable for addition to feeds.
  • the active compound is normally dispersed or mixed uniformly in the diluent but in some instances may be sorbed on the carrier.
  • Feed supplements are prepared by uniformly mixing the appropropriate imidazole with the carrier or carriers. Such supplements are added to the finished animal feed in an amount adequate to give the final concentration desired for controlling or treating chronic respiratory disease by way of the animal ration.
  • the 1-(dimesityl)imidazole is prepared by reacting a compound of the general formula:
  • V preferably a halogen atom or the toluene-p-sulphonate radical.
  • the reaction is preferably carried out by heating the reactants in an inert organic solvent such as benzene, toluene, xylene or dioxan. Improved yields can sometimes be obtained by using a solvent with a high dielectric constant, such as acetonitrile, dimethylsulphoxide or dimethylformamide.
  • imidazole (X represents a hydrogen atom)
  • the reaction is preferably carried out in the presence of a base, which may suitably be an excess of the imidazole compound.
  • bases such as potassium carbonate or tertiary amines (e.g. triethylamine) may also be used.
  • Alkali metal salts of imidazole compound may be prepared by reacting the imidazole with a solution or suspension of the alkali metal or a hydride thereof in an inert organic solvent such as benzene or toluene, or with the appropriate alkoxide (e.g. methoxide) dissolved in an alcohol (e.g. methanol).
  • an inert organic solvent such as benzene or toluene
  • an alcohol e.g. methanol
  • the dimesitylrnethyl esters can generally be obtained by reacting the corresponding diphenylmethanol compound with the appropriate acid in manner known per se.
  • the chlorides may be prepared by reacting the alcohol with thionyl chloride in manner known per se. From the halides the toluene-p-sulphonates may be prepared by reaction with the silver salt of toluenep-sulphonic acid.
  • Acid addition and quaternary ammonium salts of ldimesitylmethyl)imidazole may be prepared by methods known per se.
  • the base may be treated with the equivalent amount of the acid in an inert solvent to obtain the corresponding acid addition salt, or the base may be treated with the equivalent amount of an appropriate alkyl halide or dialkyl sulphate in a solvent having high dielectric properties, for example acetonitrile, to obtain the quaternary ammonium salt.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

THIS INVENTION RELATES TO 1-(DIMESITYLMETHYL) IMIDAZOLE AND ITS ACID ADDITION AND QUATERNARY AMMONIUM SALTS AND TO A PROCESS FOR ITS PREPARATION. IN ADDITION, TO PHARMACEUTICAL COMPOSITIONS CONSISTING SAID COMPOUNDS AND METHODS FOR USING SAID COMPOSITIONS AS ANTI-FUNGAL AGENTS AND IN THE TREATMENT OF INFECTIONS CAUSED BY MYCOPLASMA GALLISEPTICUM.

Description

United States Patent once 3,836,540 Patented Sept. 17, 1974 3,836,540 1-(DHVIESITYLMETHYL)IMIDAZOLE Cornelis van der Stelt, Haarlem, Netherlands, assignor to N.V. Koninklijke Pharmaceutische Fabrieken v/h Brocades-Stheeman & Pharmacia, Meppel, Netherlands No Drawing. Continuation-impart of abandoned application Ser. No. 151,551, June 9, 1971. This application Feb. 9, 1973, Ser. No. 330,909 Claims priority, application Great Britain, June 22, 1970, 30,247/70; Dec. 4, 1970, 57,788/70 Int. Cl. C07d 49/36 US. Cl. 260-309 2 Claims ABSTRACT OF THE DISCLOSURE This invention relates to l-(dimesitylmethyl)imidazole and its acid addition and quaternary ammonium salts and to a process for its preparation. In addition, to pharmaceutical compositions containing said compounds and methods for using said compositions as anti-fungal agents and in the treatment of infections caused by Mycoplasma galliseptz'cum.
This is a continuation-in-part of Ser. No. 151,551, filed June 9, 1971, now abandoned.
BACKGROUND OF THE INVENTION It is known that N-tritylimidazole derivatives show fungicide activities. For instance, South African Pat. 68/ 5,392 discloses antimycotics of the general formula:
CH3 CH3 CII34/\ CH3 WNW CH3 I CH3 In addition to l-(dimesityl)imidazole, this invention relates to the acid addition and quaternary ammonium salts, thereof, more specifically, the pharmaceutically acceptable acid addition and quaternary ammonium salts.
Lastly, this invention encompasses pharmaceutical compositions containing said compounds and methods for using said compositions as anti-fungal agents and in the treatment of diseases caused by M ycoplasma gallisepticum.
In the present invention the term acid addition salt is intended to encompass the salts formed by the addition of most organic and inorganic acids, such as sulfuric acid, phosphoric acid, hydriodic acid, oxalic acid, tartaric acid, etc.
The term quaternary ammonium salt is intended to encompass compounds such as the methyl iodide, ethyl sulfate, benzyl chloride, etc.
When the preceding terms are prefaced by the term pharmaceutically acceptable, it is intended to limit the salts to those having a relatively low order of toxicity, such as in the case of acid addition salts being limited to the hydrochlorides, sulfates, phosphates, acetates, citrates, maleates, fumaraates, etc., and in the case of the quaternary ammonium salts to the chlorides, sulfates, phosphates, etc.
The compounds of this invention have valuable therapeutic properties. They have a strong fungicidal activity against pathogenic fungi such as Candida albicans, Epidermophyton floccosum, Microsporum audouinii, Microsporum canis, T richophyton schoenleinni. This activity makes the compounds useful in the treatment of various fungus diseases in humans and animals.
The compounds of this invention are also useful as agricultural fungicides and pre-emergence herbicides. They may, for instance, be used in the control of early blight of tomato and anthracnose disease of cucumber and as eradicants for powdery mildew of bean.
For use as therapeutics the compounds of this invention may be administered orally, parenterally or topically in a pharmacologically acceptable carrier according to accepted pharmaceutical practice. The dosage and mode of administration will depend on the mammalian species and the disease treated. In adult humans the oral dosage will be from 25-250 mg./kg. daily. For topical application, e.g. in the treatment of skin diseases, preparations such as salves, ointments, lotions or powders, containing from 0.1 to 5%, preferably 1 to 2% by weight of the active substance may be used.
The preparations may take any of the forms customarily employed for administration of therapeutic substances. Tablets and pills may be formulated in the usual manner with one or more pharmaceutically acceptable diluents or excipients, for example lactose or starch, and include materials of a lubricating nature, for example calcium or magnesium stearate. Capsules made of absorbable material, such as gelatin may contain the active substance alone or in admixture with a solid or liquid diluent. Liquid preparations may be in the form of suspensions, emulsions, syrups or elixirs of the active substance in water or other liquid medium commonly used for making orally acceptable pharmaceutical formulations, such as liquid paraffin, or a syrup or elixir base. The active substance may also be made up in a form suitable for parenteral administration, i.e. as a suspension or emulsion in sterile water or an organic liquid usually employed for injectable preparations, for example, a vegetable oil such as olive oil, or a sterile solution in water or an organic solvent.
The active substance can also be used in the form of preparations for local application such as salves, ointments, lotions or powders, containing generally used excipients. Ointments may, for instance, contain semi-solid ointment bases such as Vaseline. In powders the active substance may be mixed with finely divided solid substances such as talc or boric acid;
When used for agricultural purposes the compounds of this invention are advantageously used in formulations containing 0.1-l0 percent by weight of the active substance. Suitable amounts of the active substance to be applied range from 1-l5 kg. per hectare.
In addition, the compounds of this invention show a high degree of activity against Mycoplasma gallise pticum in poultry, especially chickens and turkeys. Thus, these compounds, when administered orally to poultry in a daily dose range of from about 100 mg. to about 500 mg. per kg. of body weight, preferably 200 mg. to 500 mg. per kg. of body weight, find additional utility in treating or preventing chronic respiratory infections in poultry caused by Mycoplasma gallisepticum.
In treating poultry, especially chickens and turkeys, the compounds may be mixed with a nontoxic, edible carrier to form a feed supplement which is then incorporated in the animal feed in the desired concentration, or they may be administered in unit dosage forms, or in the form of a liquid drench. Alternatively, water-soluble salts or a dispersible, wettable powder containing the active ingredient may be added to the drinking water of the animals.
The means employed for administering these imidazoles to animals are not critical, and any of the methods now used or available for treating animals infected with or susceptible to infection from Mycoplasma gallisepticum are satisfactory.
In order to treat infected animals by means of a drench, the compounds are mixed with a suspending agent such as bentonite and the solid product added to water just prior to administration. The preferred drenches in accordance with this invention contain from about 50% by weight of active compound.
The compounds described herein may also be administered as a component of the feed of the animals or dissolved or suspended in the drinking water. According to the invention, novel feed and feed supplement compositions are provided in which the compounds of this invention are present as the active ingredient. Such compositions comprise the i-midazole intimately dispersed in or admixed 'with an inert carrier or diluent, i.e. one that is nonreactive with respect to the imidazole and that may be administered with safety to the animals. The carrier or diluent is preferably one that is or may be an ingredient of the animal ration.
In the feed supplement compositions the active ingredient is present in relatively large amounts. These supplements are suitable for addition to the feed either directly or after an intermediate dilution or blending step. Examples of carriers or diluents suitable for such compositions are solid orally ingestible carriers such as distillers dried grains, corn meal, citrus meal, fermentation residues, ground oyster shells, Attapulgus clay, wheat shorts, molasses solubles, corn cob meal, edible vegetable substances, toasted dehulled soya flour, soybean mill feed, antibiotic mycelia, soya grits, crushed limestone and the like. The compounds are intimately dispersed or admixed throughout the solid inert carrier by methods such as grinding, stirring, milling, or tumbling. By selecting proper diluents and by altering the ratio of carrier to active ingredient, compositions of any desired concentration may be prepared. Formulations containing from about 5%? to about 50% by weight, and preferably from about -30% by weight, of active ingredient are particularly suitable for addition to feeds. The active compound is normally dispersed or mixed uniformly in the diluent but in some instances may be sorbed on the carrier.
Feed supplements are prepared by uniformly mixing the appropropriate imidazole with the carrier or carriers. Such supplements are added to the finished animal feed in an amount adequate to give the final concentration desired for controlling or treating chronic respiratory disease by way of the animal ration.
The 1-(dimesityl)imidazole is prepared by reacting a compound of the general formula:
CH3 CH CH CH3 CH3 CH wherein Y represents the acid residue of a reactive ester,
V preferably a halogen atom or the toluene-p-sulphonate radical. The reaction is preferably carried out by heating the reactants in an inert organic solvent such as benzene, toluene, xylene or dioxan. Improved yields can sometimes be obtained by using a solvent with a high dielectric constant, such as acetonitrile, dimethylsulphoxide or dimethylformamide.
When imidazole (X represents a hydrogen atom) is employed, the reaction is preferably carried out in the presence of a base, which may suitably be an excess of the imidazole compound. However, other bases such as potassium carbonate or tertiary amines (e.g. triethylamine) may also be used.
Alkali metal salts of imidazole compound may be prepared by reacting the imidazole with a solution or suspension of the alkali metal or a hydride thereof in an inert organic solvent such as benzene or toluene, or with the appropriate alkoxide (e.g. methoxide) dissolved in an alcohol (e.g. methanol).
Compounds wherein X represents a silver atom may be prepared from those in which X is hydrogen by the method described by G. Wyss, Ber. Dtsch. Chem. Ges., 10, 1373 (1877).
The dimesitylrnethyl esters can generally be obtained by reacting the corresponding diphenylmethanol compound with the appropriate acid in manner known per se. The chlorides may be prepared by reacting the alcohol with thionyl chloride in manner known per se. From the halides the toluene-p-sulphonates may be prepared by reaction with the silver salt of toluenep-sulphonic acid.
Acid addition and quaternary ammonium salts of ldimesitylmethyl)imidazole may be prepared by methods known per se. For example, the base may be treated with the equivalent amount of the acid in an inert solvent to obtain the corresponding acid addition salt, or the base may be treated with the equivalent amount of an appropriate alkyl halide or dialkyl sulphate in a solvent having high dielectric properties, for example acetonitrile, to obtain the quaternary ammonium salt.
By the term methods known per se as used in the specification is meant methods heretofore used or describe in the literature.
The following Example, in which the yields expressed are in terms of the theoretical yield, illustrates the preparation of the compounds of the present invention.
EXAMPLE 1 A solution of 27.7 g. (0.1 mole) 2,2',4,4',6,6'-hexamethyl-diphenylmethyl chloride in ml. of anhydrous toluene is added drop-Wise to a refluxing sollution of 13.6 g. (0.2 mole) of imidazole in 75 ml. of anhydrous toluene. The solution is refluxed for 6 hours, cooled and extracted with water. The organic layer is dried over sodium sulphate and the solvent is distilled off. To the oily residue 9.0 g. of oxalic acid in diethyl ether are added, which gives a precipitate consisting of the oxalate of 1- dimesityl-methyl) imidazole. After repeated recrystallizations from a mixture of methanol and diethyl ether, the base is liberated by addition of 2N sodium hydroxide and extracted with diethyl ether. The ether is distilled off and the oily residue is dried in vacuo over phosphorous pentoxide. After 24 hours the substance solidifies. Its melting point is 122123 C.
Analysis.Calculated for C H N 82.97% C; 8.23% FOREIGN PATENTS H; 0% N- F l IldI 82.8% C; 8-1% H; 8.7% N. 1 4 7 32 5 19 7 France 2 What is claimed is:
1. 1-(dimesitylmethyl)imidazole or a pharmaceutically OTHER REFERENCES acceptable acid addition or quarternary ammonium salt 5 urnari et aL: Bul. Soc. Chim., France, 1968, pp. thereof.
2. The compound of claim 1, (1-dimesitylmethyl)imid- US$ et Chem Abst" columns 12194'5 Draber et al.: Chem. Abst., vol. 73, No. 98949w 1970 References Cited 10 UNITED STATES PATENTS NATALIE TROUSOF, Primary Examiner 3,321,366 5/1967 Mussell et a1 260--309 Us CL 3,660,577 5/1972 Buchel et a1. 260309 424 273
US00330909A 1970-06-22 1973-02-09 1-(dimesitylmethyl)imidazole Expired - Lifetime US3836540A (en)

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GB3024770 1970-06-22
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BE (1) BE768808A (en)
CA (1) CA955940A (en)
CH (1) CH561185A5 (en)
DE (1) DE2130673A1 (en)
ES (1) ES392480A1 (en)
FR (1) FR2100809B1 (en)
IT (1) IT1048388B (en)
LU (1) LU63391A1 (en)
NL (1) NL7108387A (en)
SE (1) SE373367B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4238498A (en) * 1978-02-24 1980-12-09 Bayer Aktiengesellschaft Antimycotic substituted diphenyl-imidazolyl-methanes
US4243670A (en) * 1976-09-28 1981-01-06 Bayer Aktiengesellschaft α-(4-Biphenylyl)-benzyl-azolium salts and their use for combating micro-organisms
US4251540A (en) * 1977-03-31 1981-02-17 Bayer Aktiengesellschaft Combating crop damaging fungi with α-(4-biphenylyl)-benzyl-azolium salts
US4602025A (en) * 1984-06-18 1986-07-22 Eli Lilly And Company Aromatase inhibitors
US4755526A (en) * 1984-06-18 1988-07-05 Eli Lilly And Company Method of inhibiting aromatase
US6103733A (en) * 1998-09-09 2000-08-15 Bachmann; Kenneth A. Method for increasing HDL cholesterol levels using heteroaromatic phenylmethanes
US20060211632A1 (en) * 2005-03-17 2006-09-21 Bachmann Kenneth A PXR agonists for cardiovascular disease

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE40911B1 (en) * 1974-04-11 1979-09-12 Schering Ag Imidazole derivatives and process for their manufacture
DE69615184T2 (en) * 1995-06-07 2002-06-13 Taisho Pharmaceutical Co., Ltd. FUNGICIDE

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4243670A (en) * 1976-09-28 1981-01-06 Bayer Aktiengesellschaft α-(4-Biphenylyl)-benzyl-azolium salts and their use for combating micro-organisms
US4251540A (en) * 1977-03-31 1981-02-17 Bayer Aktiengesellschaft Combating crop damaging fungi with α-(4-biphenylyl)-benzyl-azolium salts
US4238498A (en) * 1978-02-24 1980-12-09 Bayer Aktiengesellschaft Antimycotic substituted diphenyl-imidazolyl-methanes
US4602025A (en) * 1984-06-18 1986-07-22 Eli Lilly And Company Aromatase inhibitors
US4755526A (en) * 1984-06-18 1988-07-05 Eli Lilly And Company Method of inhibiting aromatase
US6103733A (en) * 1998-09-09 2000-08-15 Bachmann; Kenneth A. Method for increasing HDL cholesterol levels using heteroaromatic phenylmethanes
US20060211632A1 (en) * 2005-03-17 2006-09-21 Bachmann Kenneth A PXR agonists for cardiovascular disease

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IT1048388B (en) 1980-11-20
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LU63391A1 (en) 1971-09-22
CA955940A (en) 1974-10-08
NL7108387A (en) 1971-12-24
FR2100809A1 (en) 1972-03-24
FR2100809B1 (en) 1974-08-30
DE2130673A1 (en) 1971-12-23
CH561185A5 (en) 1975-04-30
BE768808A (en) 1971-12-21
AT303721B (en) 1972-12-11

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