CA1097356A - 2,4-dichlorophenyl-imidazolyl-ethan-ones and -ols, a process for their preparation and their use as medicaments - Google Patents

2,4-dichlorophenyl-imidazolyl-ethan-ones and -ols, a process for their preparation and their use as medicaments

Info

Publication number: CA1097356A
Authority: CA; Canada
Prior art keywords: dichlorophenyl; ethan; imidazol; hydrochloride; bromo
Prior art date: 1977-02-11
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

Application number

CA296,581A

Other languages

English (en)

French (fr)

Inventor

Wolfgang Kramer

Karl H. Buchel

Manfred Plempel

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date 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 date listed.)

1977-02-11

Filing date

1978-02-09

Publication date

1981-03-10

1978-02-09 Application filed by Bayer AG filed Critical Bayer AG

1981-03-10 Application granted granted Critical

1981-03-10 Publication of CA1097356A publication Critical patent/CA1097356A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 27
238000002360 preparation method Methods 0.000 title claims description 5
TYKOUAUXOORKDQ-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1h-imidazol-2-yl)ethanone Chemical class ClC1=CC(Cl)=CC=C1CC(=O)C1=NC=CN1 TYKOUAUXOORKDQ-UHFFFAOYSA-N 0.000 title claims 2
239000003814 drug Substances 0.000 title abstract description 14
150000001875 compounds Chemical class 0.000 claims abstract description 29
239000000460 chlorine Substances 0.000 claims abstract description 13
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
125000000468 ketone group Chemical group 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
150000002367 halogens Chemical group 0.000 claims abstract 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
-1 imidazolyl-ethanone compound Chemical class 0.000 claims description 17
239000003085 diluting agent Substances 0.000 claims description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 13
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 9
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239000011230 binding agent Substances 0.000 claims description 5
ZQEQHJYFFWRJLP-UHFFFAOYSA-N 2-bromo-2-(2,4-dichlorophenoxy)-1-(2,4-dichlorophenyl)ethanone Chemical compound ClC1=CC(Cl)=CC=C1OC(Br)C(=O)C1=CC=C(Cl)C=C1Cl ZQEQHJYFFWRJLP-UHFFFAOYSA-N 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
229930194542 Keto Natural products 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
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OSMJIXXVEWORDJ-UHFFFAOYSA-N 1-(1h-imidazol-2-yl)ethanone Chemical compound CC(=O)C1=NC=CN1 OSMJIXXVEWORDJ-UHFFFAOYSA-N 0.000 claims 2
HSWOGPQQOLPLGS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-(2,4-dichlorophenyl)-2-imidazol-1-ylethanone;hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1OC(N1C=NC=C1)C(=O)C1=CC=C(Cl)C=C1Cl HSWOGPQQOLPLGS-UHFFFAOYSA-N 0.000 claims 2
CXBGDIJOKOQYSC-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-(2,4-dichlorophenyl)-2-imidazol-1-ylethanol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)C(N1C=NC=C1)OC1=CC=C(Cl)C=C1 CXBGDIJOKOQYSC-UHFFFAOYSA-N 0.000 claims 1
GAYYCXIPFLQXAF-UHFFFAOYSA-N 2-bromo-1-(2,4-dichlorophenyl)-2-(4-phenylphenoxy)ethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C(Br)OC1=CC=C(C=2C=CC=CC=2)C=C1 GAYYCXIPFLQXAF-UHFFFAOYSA-N 0.000 claims 1
LRKISXWSRYGWSR-UHFFFAOYSA-N 2-bromo-1-(2,4-dichlorophenyl)-2-phenoxyethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C(Br)OC1=CC=CC=C1 LRKISXWSRYGWSR-UHFFFAOYSA-N 0.000 claims 1
CNGBSENIGHFAPJ-UHFFFAOYSA-N 2-bromo-2-(4-chlorophenoxy)-1-(2,4-dichlorophenyl)ethanone Chemical compound C1=CC(Cl)=CC=C1OC(Br)C(=O)C1=CC=C(Cl)C=C1Cl CNGBSENIGHFAPJ-UHFFFAOYSA-N 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
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OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
229940095731 candida albicans Drugs 0.000 description 1
TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000012973 diazabicyclooctane Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000010642 eucalyptus oil Substances 0.000 description 1
229940044949 eucalyptus oil Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229940028332 halog Drugs 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
239000001525 mentha piperita l. herb oil Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000003020 moisturizing effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
235000019477 peppermint oil Nutrition 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000009877 rendering Methods 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
JCMLRUNDSXARRW-UHFFFAOYSA-N trioxouranium Chemical compound O=[U](=O)=O JCMLRUNDSXARRW-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- 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
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA296,581A 1977-02-11 1978-02-09 2,4-dichlorophenyl-imidazolyl-ethan-ones and -ols, a process for their preparation and their use as medicaments Expired CA1097356A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19772705677 DE2705677A1 (de)	1977-02-11	1977-02-11	2,4-dichlorphenyl-imidazolyl-aethanone(ole), verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DEP2705677.5		1977-02-11

Publications (1)

Publication Number	Publication Date
CA1097356A true CA1097356A (en)	1981-03-10

Family

ID=6000864

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA296,581A Expired CA1097356A (en)	1977-02-11	1978-02-09	2,4-dichlorophenyl-imidazolyl-ethan-ones and -ols, a process for their preparation and their use as medicaments

Country Status (17)

Country	Link
JP (1)	JPS53101375A (de)
AT (1)	AT361910B (de)
AU (1)	AU516580B2 (de)
BE (1)	BE863851A (de)
CA (1)	CA1097356A (de)
CH (1)	CH634058A5 (de)
DE (1)	DE2705677A1 (de)
DK (1)	DK61378A (de)
ES (1)	ES466867A1 (de)
FI (1)	FI66851C (de)
FR (1)	FR2380263A1 (de)
GB (1)	GB1554841A (de)
IL (1)	IL54001A (de)
IT (1)	IT1093702B (de)
NL (1)	NL177214C (de)
NO (1)	NO147448C (de)
SE (1)	SE442401B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2713777C3 (de) *	1977-03-29	1979-10-31	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von l-Azolyl-33-dimethyl-l-phenoxy-butan-2-onen
AT394800B (de) *	1979-09-06	1992-06-25	Bristol Myers Squibb Co	Mittel zur wachstumshemmung von pilzen und bakterien
AT382147B (de) *	1979-09-06	1987-01-12	Bristol Myers Co	Verfahren zur herstellung von neuen 1-phenaethylimidazol-derivaten
GB2086885A (en) *	1980-09-13	1982-05-19	Beecham Group Ltd	Imidazoles

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2105490C3 (de) *	1971-02-05	1979-06-13	Bayer Ag, 5090 Leverkusen	1 -Imidazolylketonderivate

1977
- 1977-02-11 DE DE19772705677 patent/DE2705677A1/de not_active Withdrawn
1978
- 1978-01-27 NO NO780315A patent/NO147448C/no unknown
- 1978-02-02 CH CH117278A patent/CH634058A5/de not_active IP Right Cessation
- 1978-02-07 GB GB4884/78A patent/GB1554841A/en not_active Expired
- 1978-02-09 SE SE7801526A patent/SE442401B/sv unknown
- 1978-02-09 JP JP1305978A patent/JPS53101375A/ja active Pending
- 1978-02-09 FI FI780431A patent/FI66851C/fi not_active IP Right Cessation
- 1978-02-09 IL IL54001A patent/IL54001A/xx unknown
- 1978-02-09 IT IT20129/78A patent/IT1093702B/it active
- 1978-02-09 CA CA296,581A patent/CA1097356A/en not_active Expired
- 1978-02-10 ES ES466867A patent/ES466867A1/es not_active Expired
- 1978-02-10 AT AT94378A patent/AT361910B/de not_active IP Right Cessation
- 1978-02-10 FR FR7803833A patent/FR2380263A1/fr active Granted
- 1978-02-10 NL NLAANVRAGE7801579,A patent/NL177214C/xx not_active IP Right Cessation
- 1978-02-10 BE BE185068A patent/BE863851A/xx not_active IP Right Cessation
- 1978-02-10 DK DK61378A patent/DK61378A/da not_active Application Discontinuation
1979
- 1979-02-13 AU AU33243/78A patent/AU516580B2/en not_active Expired

Also Published As

Publication number	Publication date
SE442401B (sv)	1985-12-23
FI780431A7 (fi)	1978-08-12
JPS53101375A (en)	1978-09-04
NO780315L (no)	1978-08-14
AU516580B2 (en)	1981-06-11
FR2380263B1 (de)	1982-11-19
ES466867A1 (es)	1978-10-01
IT1093702B (it)	1985-07-26
NO147448C (no)	1983-04-13
NL177214B (nl)	1985-03-18
NL7801579A (nl)	1978-08-15
DK61378A (da)	1978-08-12
AT361910B (de)	1981-04-10
ATA94378A (de)	1980-09-15
FR2380263A1 (fr)	1978-09-08
FI66851B (fi)	1984-08-31
IL54001A (en)	1981-09-13
IT7820129A0 (it)	1978-02-09
CH634058A5 (en)	1983-01-14
FI66851C (fi)	1984-12-10
IL54001A0 (en)	1978-04-30
NO147448B (no)	1983-01-03
BE863851A (fr)	1978-08-10
SE7801526L (sv)	1978-08-12
NL177214C (nl)	1985-08-16
GB1554841A (en)	1979-10-31
AU3324378A (en)	1979-08-23
DE2705677A1 (de)	1978-08-17

Legal Events

Date	Code	Title	Description
1998-03-10	MKEX	Expiry

Publication	Publication Date	Title
US3812142A (en)	1974-05-21	Imidazolyl ketones
US4358458A (en)	1982-11-09	Tertiary imidazolyl alcohols and method for the treatment of generalized and local infections caused by fungi and yeasts
JPH0222731B2 (de)	1990-05-21
IE48881B1 (en)	1985-06-12	New hydroxyethyl-azole compounds,their production and their medicinal use
IE48880B1 (en)	1985-06-12	New hydroxypropyl-triazole compounds,their production and their medicinal use
US4233311A (en)	1980-11-11	Antimicrobial agents and their use
US4246274A (en)	1981-01-20	Antimycotic hydroxypropyl-imidazoles
US4238498A (en)	1980-12-09	Antimycotic substituted diphenyl-imidazolyl-methanes
US4215131A (en)	1980-07-29	Antimicrobial agents
CA1097356A (en)	1981-03-10	2,4-dichlorophenyl-imidazolyl-ethan-ones and -ols, a process for their preparation and their use as medicaments
US4894382A (en)	1990-01-16	Substituted 1,3-diazolyl-2-propanols and their use as antimycotic agents
IE51146B1 (en)	1986-10-15	1,1-diphenyl-2-.(1,2,4-triazol-1-yl)-ethan-1-ols,their preparation and therapeutic agents containing these compounds
IL44794A (en)	1977-08-31	Antimicrobial compositions containing certain 1,2,4-or 1,2,3-triazolyl o,n-acetal derivatives
US4489085A (en)	1984-12-18	Antimicrobial agents and their use employing imidazolyl-enal ethers
GB1564371A (en)	1980-04-10	Antimicrobial agents containing imidazole derivatives
US5126359A (en)	1992-06-30	Substituted bisazoles and their use as medicaments
US4239765A (en)	1980-12-16	Fluorenyl-azolylmethyl-carbinol compounds and their medicinal use
CA1160237A (en)	1984-01-10	Biphenylyl-azolylethane compounds, their production and their medicinal use
IL45771A (en)	1977-11-30	Pharmaceutical compositions containing 1-(2-phenoxy-3-hydroxy-alkyl)-1,2,4-triazole derivatives
IE52055B1 (en)	1987-05-27	New ethenylimidazole derivatives,processes for their preparation and pharmaceutical compositions containing them:intermediates,useful in their preparation and a process for the preparation thereof
JPH0456035B2 (de)	1992-09-07
JPH03870B2 (de)	1991-01-09
CA1232909A (en)	1988-02-16	1,2,4-triazolylpropanols, and their production and use
CA1060026A (en)	1979-08-07	Diaryloxy-imidazolyl-o,n-acetals, process for their preparation and their use as medicaments
CA1146950A (en)	1983-05-24	Hydroxybutyl-imidazole derivatives