CH668772A5 - 1,2,4-triazol-derivat, verfahren zu dessen herstellung und seine verwendung. - Google Patents
1,2,4-triazol-derivat, verfahren zu dessen herstellung und seine verwendung. Download PDFInfo
- Publication number
- CH668772A5 CH668772A5 CH2871/85A CH287185A CH668772A5 CH 668772 A5 CH668772 A5 CH 668772A5 CH 2871/85 A CH2871/85 A CH 2871/85A CH 287185 A CH287185 A CH 287185A CH 668772 A5 CH668772 A5 CH 668772A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- formula
- cyclopropyl
- compound according
- chlorophenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 10
- -1 1-cyclopropyl-l-methyl-ethyl Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 229940121375 antifungal agent Drugs 0.000 claims description 3
- 241000233866 Fungi Species 0.000 claims description 2
- 239000003429 antifungal agent Substances 0.000 claims description 2
- 230000003032 phytopathogenic effect Effects 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000000843 anti-fungal effect Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QQCZXHWLXJBWJN-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(2-cyclopropylpropan-2-yl)oxirane Chemical compound C1OC1(C=1C=CC(Cl)=CC=1)C(C)(C)C1CC1 QQCZXHWLXJBWJN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 241000221577 Uromyces appendiculatus Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 150000003944 halohydrins Chemical class 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
- FEVALTJSQBFLEU-UHFFFAOYSA-N 1-methyl-4-methylsulfinylbenzene Chemical compound CC1=CC=C(S(C)=O)C=C1 FEVALTJSQBFLEU-UHFFFAOYSA-N 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- ZIOLCZCJJJNOEJ-UHFFFAOYSA-N 2-pyrrol-1-ylethanol Chemical class OCCN1C=CC=C1 ZIOLCZCJJJNOEJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 240000001436 Antirrhinum majus Species 0.000 description 1
- 241001480043 Arthrodermataceae Species 0.000 description 1
- 241000895502 Blumeria graminis f. sp. tritici Species 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 241001181537 Hemileia Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 241000498271 Necator Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000208181 Pelargonium Species 0.000 description 1
- 244000045930 Phaseolus coccineus Species 0.000 description 1
- 235000010632 Phaseolus coccineus Nutrition 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- 241000221535 Pucciniales Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010041736 Sporotrichosis Diseases 0.000 description 1
- 206010046914 Vaginal infection Diseases 0.000 description 1
- 201000008100 Vaginitis Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229960004125 ketoconazole Drugs 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3425848 | 1984-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH668772A5 true CH668772A5 (de) | 1989-01-31 |
Family
ID=6240558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH2871/85A CH668772A5 (de) | 1984-07-13 | 1985-07-04 | 1,2,4-triazol-derivat, verfahren zu dessen herstellung und seine verwendung. |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS6144878A (it) |
| AU (1) | AU582761B2 (it) |
| BE (1) | BE902837A (it) |
| CH (1) | CH668772A5 (it) |
| DE (1) | DE3524296C2 (it) |
| DK (1) | DK163058C (it) |
| FR (1) | FR2567515B1 (it) |
| GB (1) | GB2161483B (it) |
| IE (1) | IE58516B1 (it) |
| IL (1) | IL75774A (it) |
| IT (1) | IT1200087B (it) |
| LU (1) | LU86001A1 (it) |
| NL (1) | NL8501962A (it) |
| NZ (1) | NZ212718A (it) |
| PH (1) | PH23287A (it) |
| SE (1) | SE456679B (it) |
| ZA (1) | ZA855286B (it) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH647513A5 (de) * | 1979-11-13 | 1985-01-31 | Sandoz Ag | Triazol-derivate, deren herstellung und verwendung. |
| JPS5697276A (en) * | 1979-11-13 | 1981-08-05 | Sandoz Ag | Alphaaaryll1hh1*2*44triazolee11ethanols |
| ZA817473B (en) * | 1980-11-19 | 1982-10-27 | Ici Plc | Triazole and imidazole compounds |
| CH658654A5 (de) * | 1983-03-04 | 1986-11-28 | Sandoz Ag | Azolderivate, verfahren zu ihrer herstellung und mittel die diese verbindungen enthalten. |
-
1985
- 1985-07-04 CH CH2871/85A patent/CH668772A5/de not_active IP Right Cessation
- 1985-07-06 DE DE3524296A patent/DE3524296C2/de not_active Expired - Lifetime
- 1985-07-08 FR FR8510531A patent/FR2567515B1/fr not_active Expired
- 1985-07-09 BE BE1/011292A patent/BE902837A/fr not_active IP Right Cessation
- 1985-07-09 NL NL8501962A patent/NL8501962A/nl active Search and Examination
- 1985-07-09 IT IT48324/85A patent/IT1200087B/it active
- 1985-07-11 AU AU44779/85A patent/AU582761B2/en not_active Expired
- 1985-07-11 GB GB08517526A patent/GB2161483B/en not_active Expired
- 1985-07-11 DK DK318185A patent/DK163058C/da not_active IP Right Cessation
- 1985-07-11 PH PH32517A patent/PH23287A/en unknown
- 1985-07-11 IL IL75774A patent/IL75774A/xx not_active IP Right Cessation
- 1985-07-11 IE IE174785A patent/IE58516B1/en not_active IP Right Cessation
- 1985-07-11 NZ NZ212718A patent/NZ212718A/xx unknown
- 1985-07-11 SE SE8503443A patent/SE456679B/sv not_active IP Right Cessation
- 1985-07-12 LU LU86001A patent/LU86001A1/fr unknown
- 1985-07-12 ZA ZA855286A patent/ZA855286B/xx unknown
- 1985-07-12 JP JP60155017A patent/JPS6144878A/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IT1200087B (it) | 1989-01-05 |
| IL75774A0 (en) | 1985-11-29 |
| DK318185D0 (da) | 1985-07-11 |
| AU582761B2 (en) | 1989-04-13 |
| ZA855286B (en) | 1987-02-25 |
| JPS6144878A (ja) | 1986-03-04 |
| IT8548324A0 (it) | 1985-07-09 |
| NL8501962A (nl) | 1986-02-03 |
| IE58516B1 (en) | 1993-10-06 |
| GB8517526D0 (en) | 1985-08-14 |
| GB2161483B (en) | 1988-07-13 |
| SE8503443L (sv) | 1986-01-14 |
| PH23287A (en) | 1989-06-30 |
| AU4477985A (en) | 1986-01-16 |
| NZ212718A (en) | 1989-01-27 |
| SE456679B (sv) | 1988-10-24 |
| IE851747L (en) | 1986-01-13 |
| DE3524296A1 (de) | 1986-01-16 |
| DE3524296C2 (de) | 1994-08-25 |
| SE8503443D0 (sv) | 1985-07-11 |
| GB2161483A (en) | 1986-01-15 |
| DK163058C (da) | 1992-06-09 |
| DK163058B (da) | 1992-01-13 |
| IL75774A (en) | 1989-12-15 |
| LU86001A1 (fr) | 1986-02-12 |
| BE902837A (fr) | 1986-01-09 |
| DK318185A (da) | 1986-01-14 |
| FR2567515A1 (fr) | 1986-01-17 |
| FR2567515B1 (fr) | 1988-09-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0011769B1 (de) | Hydroxyethyl-azole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel | |
| DE3406993A1 (de) | Neue azolderivate | |
| EP0011768B1 (de) | Hydroxypropyl-triazole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2350123C2 (de) | 1-Propyl-imidazol-Derivate und deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| EP0218118B1 (de) | Arylmethylazole und deren Salze, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung | |
| DE3430833C2 (de) | Neue Azolverbindungen | |
| EP0008804A1 (de) | Imidazolylvinylether, Verfahren zu deren Herstellung, deren Verwendung und diese Ether enthaltende Arzneimittel und Pflanzenschutzmittel | |
| EP0003796B1 (de) | Substituierte Diphenyl-imidazolyl-methane, Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel | |
| EP0180835A2 (de) | Antimykotische Azolylcyclopropylcarbinolderivate | |
| EP0118070B1 (de) | Substituierte 1,3-Diazolyl-2-propanole, Verfahren zu ihrer Herstellung und ihre Verwendung als antimykotische Mittel | |
| EP0036153A1 (de) | 1,1-Diphenyl-2-(1,2,4-triazol-1-yl)-äthan-1-ole als Antimykotika | |
| DE60318395T2 (de) | R-(-)-1-[2-(7-chlorobenzo-[b]-thiophen-3-yl-methoxy)-2-(2,4-dichlorphenyl)ethyl]-1h-imidazol | |
| EP0085842B1 (de) | Antimykotische Mittel | |
| DD246998A5 (de) | Verfahren zur herstellung von triazol-derivaten | |
| EP0104300B1 (de) | Diazolyl-alkanole, Verfahren zu ihrer Herstellung und ihre Verwendung als antimykotische Mittel | |
| EP0009707A1 (de) | Halogenierte 1-Azolyl-1-fluorphenoxy-butan-Derivate, Verfahren zu ihrer Herstellung, sie enthaltende Fungizide Mittel sowie ihre Verwendung als Fungizide | |
| DD216928A5 (de) | Verfahren zur herstellung neuer triazol-derivate | |
| EP0057863B1 (de) | Antimikrobielle Mittel | |
| DE3524296C2 (de) | Neues Azol, Verfahren zu dessen Herstellung und seine Verwendung | |
| DD246296A5 (de) | Verfahren zur herstellung neuer bis-triazol-derivate | |
| DE69901925T2 (de) | 2-(3-Phenyl-2-propenyl)-1,2,3,4-tetrahydro-isochinolin-derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| EP0149814B1 (de) | Azolylmethylcycloacetale, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel | |
| EP0031883B1 (de) | Antimikrobielle Mittel enthaltend Hydroxybutylimidazol-Derivate | |
| DE69828524T2 (de) | Tetrahydrofuran-phosphat- und hydroxy-ester als prodrugs der entsprechenden antifungiziden mittel | |
| EP0057864A2 (de) | 2-Azolylmethyl-1,3-dioxolan- und -dioxan-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PFA | Name/firm changed |
Owner name: SANDOZ AG TRANSFER- NOVARTIS AG |
|
| PL | Patent ceased |