CH634058A5 - 2,4-Dichlorophenylimidazolyl ethanones or ethanols, a process for their preparation and drugs containing them - Google Patents

2,4-Dichlorophenylimidazolyl ethanones or ethanols, a process for their preparation and drugs containing them Download PDF

Info

Publication number: CH634058A5
Authority: CH; Switzerland
Prior art keywords: dichlorophenyl; ethane; formula; bromo; ethanols
Prior art date: 1977-02-11

Application number

CH117278A

Other languages

German (de)

English (en)

Inventor

Wolfgang Kraemer

Karl Heinz Buechel

Manfred Plempel

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

1978-02-02

Publication date

1983-01-14

1978-02-02 Application filed by Bayer Ag filed Critical Bayer Ag

1983-01-14 Publication of CH634058A5 publication Critical patent/CH634058A5/de

Links

LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims description 19
235000019441 ethanol Nutrition 0.000 title claims description 15
238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 8
239000003814 drug Substances 0.000 title claims description 7
229940079593 drug Drugs 0.000 title description 2
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 1
150000001875 compounds Chemical class 0.000 claims description 16
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
239000003085 diluting agent Substances 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
239000011230 binding agent Substances 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
BYWILFCUFLEVDA-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-1-(1h-imidazol-2-yl)ethanol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(C)C1=NC=CN1 BYWILFCUFLEVDA-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
125000000468 ketone group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
BDZXLIZMDQHWNE-UHFFFAOYSA-N 2-[1-(2,4-dichlorophenyl)ethyl]-1h-imidazole Chemical class C=1C=C(Cl)C=C(Cl)C=1C(C)C1=NC=CN1 BDZXLIZMDQHWNE-UHFFFAOYSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
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-1 phenoxyimidazolyl Chemical class 0.000 description 13
239000000126 substance Substances 0.000 description 11
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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150000003973 alkyl amines Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
230000001857 anti-mycotic effect Effects 0.000 description 1
150000003974 aralkylamines Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
229940091771 aspergillus fumigatus Drugs 0.000 description 1
239000002585 base Substances 0.000 description 1
229960002903 benzyl benzoate Drugs 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
235000019437 butane-1,3-diol Nutrition 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000000378 calcium silicate Substances 0.000 description 1
229910052918 calcium silicate Inorganic materials 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
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
229910052799 carbon Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
239000012973 diazabicyclooctane Substances 0.000 description 1
QVQGTNFYPJQJNM-UHFFFAOYSA-N dicyclohexylmethanamine Chemical compound C1CCCCC1C(N)C1CCCCC1 QVQGTNFYPJQJNM-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
229940093499 ethyl acetate Drugs 0.000 description 1
239000010642 eucalyptus oil Substances 0.000 description 1
229940044949 eucalyptus oil Drugs 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
WHWDWIHXSPCOKZ-UHFFFAOYSA-N hexahydrofarnesyl acetone Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)=O WHWDWIHXSPCOKZ-UHFFFAOYSA-N 0.000 description 1
239000003906 humectant Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000000314 lubricant 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
238000004519 manufacturing process Methods 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
239000001525 mentha piperita l. herb oil Substances 0.000 description 1
244000005700 microbiome Species 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical class [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 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
239000000312 peanut oil Substances 0.000 description 1
235000019477 peppermint oil Nutrition 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
239000003495 polar organic solvent Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011787 zinc oxide Substances 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)

CH117278A 1977-02-11 1978-02-02 2,4-Dichlorophenylimidazolyl ethanones or ethanols, a process for their preparation and drugs containing them CH634058A5 (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
CH634058A5 true CH634058A5 (en)	1983-01-14

Family

ID=6000864

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH117278A CH634058A5 (en)	1977-02-11	1978-02-02	2,4-Dichlorophenylimidazolyl ethanones or ethanols, a process for their preparation and drugs containing them

Country Status (17)

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

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/fr 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/fr 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
CA1097356A (fr)	1981-03-10
JPS53101375A (en)	1978-09-04
NO780315L (no)	1978-08-14
AU516580B2 (en)	1981-06-11
FR2380263B1 (fr)	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
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
1987-10-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0011769B1 (fr)	1982-04-14	Hydroxyéthyl azoles, procédé pour leur préparation ainsi que leur utilisation dans des médicaments
EP0043419B1 (fr)	1984-03-14	Composition antimycotique
EP0011768B1 (fr)	1981-10-21	Hydroxypropyl triazoles, procédé pour leur préparation et médicaments contenant ces composés
EP0005250B1 (fr)	1981-08-12	Hydroxypropyl-imidazoles, procédé pour leur préparation et médicaments les contenant
EP0120276A1 (fr)	1984-10-03	Diazolylalkyl ou triazolylalkyl carbinols substitués, leur procédé de préparation et leur application comme agents antimycosiques
EP0003796B1 (fr)	1980-10-15	Diphényl-imidazolyl-méthanes substitués, leur procédé de préparation et médicaments les contenant
EP0180850A2 (fr)	1986-05-14	Dérivés d'azolylméthyl-cyclopropyl-carbinols antimycotiques
EP0180835A2 (fr)	1986-05-14	Dérivés d'azolylcyclopropylcarbinals à activité antimycotique
EP0118070B1 (fr)	1986-10-08	1,3-Diazolyl-2-propanols substitués, leur procédé de préparation et leur application comme antimycosiques
DE3204795A1 (de)	1983-08-18	Azolyl-phenoxy-tetrahydrofuran-2-yliden-methane, verfahren zu ihrer herstellung sowie antimikrobielle mittel, die diese stoffe enthalten
DE2242454A1 (de)	1974-03-07	1-aethyl-imidazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
EP0104300B1 (fr)	1986-03-26	Diazolyl-alcanoles, procédé pour leur préparation et leur utilisation comme agents antimycotiques
EP0011770B1 (fr)	1981-10-14	Fluorényl-azolylméthyl-carbinols, procédé pour leur préparation médicaments contenant ces composés et procédé pour la préparation de ces médicaments
EP0057863B1 (fr)	1984-06-13	Agent antimicrobien
CH634058A5 (en)	1983-01-14	2,4-Dichlorophenylimidazolyl ethanones or ethanols, a process for their preparation and drugs containing them
EP0022969B1 (fr)	1983-05-25	Compositions antimycotiques contenant des azolylalcénols et leur préparation
EP0037049A1 (fr)	1981-10-07	Dérivés de biphénylyl-imidazolyléthane, procédé pour leur préparation et médicaments les contenant
EP0031883B1 (fr)	1983-03-02	Agent antimicrobien contenant des dérivés hydroxybutyl imidazoliques
DE2832677A1 (de)	1980-02-07	Hydroxypropyl-imidazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
EP0041615B1 (fr)	1984-02-22	Application d'alcools et de cétones d'imidazolyl vinyle comme agents antimicrobiens
CH620683A5 (fr)	1980-12-15
DE2824690A1 (de)	1979-12-13	Substituierte imidazolyl-thiazolyl- methane, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
EP0308781A2 (fr)	1989-03-29	Préparations antimycosiques
DE2820489A1 (de)	1979-11-15	Hydroxypropyl-imidazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE3019028A1 (de)	1981-11-26	Antimikrobielle mittel