KR840008020A - 치환된 디아졸릴알킬-카비놀의 제조방법 - Google Patents
치환된 디아졸릴알킬-카비놀의 제조방법 Download PDFInfo
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- KR840008020A KR840008020A KR1019840001059A KR840001059A KR840008020A KR 840008020 A KR840008020 A KR 840008020A KR 1019840001059 A KR1019840001059 A KR 1019840001059A KR 840001059 A KR840001059 A KR 840001059A KR 840008020 A KR840008020 A KR 840008020A
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- carbon atoms
- alkyl
- phenyl
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- 238000004519 manufacturing process Methods 0.000 title claims 2
- -1 Phenoxy, phenylthio Chemical group 0.000 claims 27
- 125000004432 carbon atom Chemical group C* 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- CQLUAZFJZKLONU-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methyl-1,3-bis(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)(C)N1C=NC=N1 CQLUAZFJZKLONU-UHFFFAOYSA-N 0.000 claims 1
- NBWZGDIPLPDPDC-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-methyl-1,3-bis(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(F)=CC=1)C(C)(C)N1C=NC=N1 NBWZGDIPLPDPDC-UHFFFAOYSA-N 0.000 claims 1
- GOVOSHDWVQNDFU-UHFFFAOYSA-N 2-(oxiran-2-yl)-1h-pyrrole Chemical compound C1OC1C1=CC=CN1 GOVOSHDWVQNDFU-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- HXWDPSKLYFFVIS-UHFFFAOYSA-N 3-methyl-2-phenyl-1,3-bis(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC=CC=1)C(C)(C)N1C=NC=N1 HXWDPSKLYFFVIS-UHFFFAOYSA-N 0.000 claims 1
- NQXBRQZPHIYOKB-UHFFFAOYSA-N [F].[Ag] Chemical compound [F].[Ag] NQXBRQZPHIYOKB-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000002720 diazolyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- 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
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- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (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)
- Luminescent Compositions (AREA)
- Photoreceptors In Electrophotography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Polymerization Catalysts (AREA)
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- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
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Abstract
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Description
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Claims (6)
- 일반식(Ⅱ)의 아졸릴-옥시란을 희석제 및 경우에 따라서는 염기 존재하에 일반식(Ⅲ)의 아졸과 반응시킴을 특징으로 하여 일반식(I)의 치환된 디아졸릴 알킬-카비놀 및 그의 생리학적으로 허용되는 산부가염을 제조하는 방법.상기식에서, A는 질소 또는 CH그룹을 나타내고, B는 질소 또는 CH그룹을 나타내며, X는 수소 또는 알킬을 나타내고, Y는 알킬, 또는 X가 수소일 경우, 알케닐, 알키닐 또는 임의 치환된 벤질을 나타내며, R는 임의 치환된 페닐 또는 하기 일반식의 그룹을 나타낸다.(여기에서, Alk1은 알킬을 나타내고, Alk2는 알킬을 나타내거나, Alk1및 Alk2는 함께 지환족을 나타내며, R1은 알킬, 알케닐, 또는 각 경우에 임의 치환된 페닐, 페닐알킬, 페녹시, 페닐티오, 페녹시알킬, 페닐티오알킬, 벤질옥시 또는 벤질티오를 나타낸다)
- 제1항에 있어서, A는 질소 또는 CH그룹을 나타내고; B는 질소 또는 CH그룹을 나타내며; X는 수소 또는 탄소수 1 내지 6인 직쇄 또는 측쇄알킬을 나타내고 Y는 탄소수 1 내지 6인 직쇄 또는 측쇄알킬, 또는 X가 수소일 경우 탄소수 3내지 6인 직쇄 또는 측쇄알케닐 또는 알키닐 또는 할로겐, 탄소수 1내지 4인 알킬, 탄소수 1내지 4인 알콕시 및 알킬티오, 또는 탄소수 1 또는 2이며 동일 또는 상이한 할로겐원자, 바람직하게는 불소 및 염소를 1내지 5개 함유하는 할로게노알킬, 하롤게노알콕시 및 할로게노알킬티오, 니트로- 및 시아노중에서 선택된 같거나 다른 치환체에 의해 페닐부분이 임의로 일-, 이-, 또는 삼-치환된 벤질을 나타내며; R은 동일 또는 상이한 치환체에 의해 임의로 일-, 이- 또는 삼-치환된 페닐을 나타내고, 여기에서 바람직한 치환체로는 할로겐, 탄소수 1내지 4인 알킬, 탄소수 1내지 4인 알콕시 및 알킬티오, 탄소수 1또는 2이며 동일 또는 상이한 할로겐원자, 바람직하게느 불소 및 염소원자를 1내지 5개 함유하는 할로게노알킬, 할로게노알콕시 및 할로게노알킬티오, 니트로, 시아노, 하이드록실, 하이드록시카보닐, 알킬부분이 탄소수 1내지 4인 알콕시카보닐, 탄소수 1내지 4인 하이드록스 이미노알킬, 각 알킬부분이 탄소수 1내지 4인 알콕스아미노알킬 및 할로겐 및/또는 탄소수 1 또는 2인 알킬에 의해 임의로 치환된 페닐, 페녹시, 벤질 및 벤질옥시가 있으며, 또는 바람직하게는 R이 하기 일반식의 그룹을 나타내는 일반식(I)의 화합물을 제조하는 방법.상기식에서 Alk1은 탄소수 1내지 4인 직쇄 또는 측쇄알킬을 나타내고, Alk2는 탄소수 1내지 4인 직쇄 또는 측쇄 알킬을 나타내거나; Alk1및 Alk2가 이들이 결합된 탄소원자와 함께는 3원 내지 7원 지환족환을 나타내고; R1은 탄소수 1내지 6인 직쇄 또는 측쇄알킬; 탄소수 2내지 4인 알케닐; 또는 각 경우에 동일 또는 상이한 치환체, 바람직하게는 상기한 R에서 언급한 페닐에 대한 치환체에 의해 페닐부분이 임의로 일-, 이-또는 삼 치환된 페닐, 알킬부분이 탄소수 1내지 4인 페닐알킬, 페녹시, 페닐티오, 알킬부분이 탄소수 1내지 4인 페녹시알킬, 알킬부분이 탄소수 1내지 4인 페닐티오알킬, 벤질옥시 또는 벤질티오를 나타낸다.
- 제1항에 있어서, A는 질소 또는 CH그룹을 나타내고; B는 질소 또는 CH그룹을 나타내며; X는 수소 또는 탄소수 1내지 4인 직쇄 또는 측쇄알킬을 나타내고; Y는 탄소수 1내지 4인 직쇄 또는 측쇄알킬, 또는 X가 수소일 경우, 알릴, 메탈릴, 프로파길, 메틸프로파길, 또는 불소, 염소, 브롬, 메틸, 이소프로필, 3급-부틸, 메톡시, 메틸티오, 트리플루오로메틸, 트리플루오로메톡시, 트리-풀루오로메틸티오, 니트로 및 시아노중에서 선택된 동일 또는 상이한 치환체에 의해 페닐부분에서 임의로 일-또는 이-치환된 벤질을 나타내며, R은 불소, 염소, 브롬, 메틸, 이소프로필, 3급-부틸, 메톡시, 메틸티오, 트리플루 오로메틸, 트리플루오로메톡시, 트리플루오로메틸티오, 니트로, 시아노, 하이드록실, 하이드록시카보닐, 메톡시카보닐, 에톡시카보닐, 하이드록스이미노메틸, 1-하이드록스이미노에틸, 메톡스-이미노메틸, 1-메톡스이미노에틸 및 각각 불소, 염소 또는 메틸로 임의로 치환된 페닐, 페녹시, 벤질 및 벤질옥시중에서 선택된 동일 또는 상이한 치환체에 의해 임의로 일 또는 이-치환된 페닐, 또는 하기 일반식의 그룹을 나타내는 일반식(I)의 화합물을 제조하는 방법.상기식에서, Alk1은 메틸 또는 에틸을 나타내고; Alk2는 메틸 또는 에틸을 나타내며; Alk1및 Alk2가 이들이 결합한 탄소원자와 함께는 사이클로부틸, 사이클로펜틸 또는 사이클로헥실을 나타내고; R1은 메틸, 에틸, n-프로필, l-프로필, n-부틸, 네오펜틸, 또는 각 경우에 동일 또는 상이한 치환체, 바람직하게는 상기한 R에서 엔급한 페닐에 대한 치환체에 의해 페닐부분이 임의로 일-또는 이-치환된 페닐, 벤질, 페네틸, 페녹시, 페닐티오, 페녹시메틸, 페녹시에틸, 페닐티오메틸, 페닐티오에틸, 벤질옥시 또는 벤질티오를 나타낸다.
- 제1항에 있어서, 제조된 화합물이 2-(4-클로로페닐)-1,3-디-(1,2,4-트리아졸-1-일)-3-메틸-2-부탄올인 방법.
- 제1항에 있어서, 제조된 화합물이 2-(4-플루오로페닐)-1,3-디-(1,2,4-트리아졸-1-일)-3-메틸-2-부탄올인 방법.
- 제1항에 있어서, 제조된 화합물이 2-페닐-1,3-디-(1,2,4-트리아졸-1-일)-3-메틸-2-부탄올인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3304218.3 | 1983-03-02 | ||
| DE19833307218 DE3307218A1 (de) | 1983-03-02 | 1983-03-02 | Substituierte diazolylalkyl-carbinole, verfahren zu ihrer herstellung und ihre verwendung als antimykotische mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840008020A true KR840008020A (ko) | 1984-12-12 |
Family
ID=6192203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840001059A KR840008020A (ko) | 1983-03-02 | 1984-03-02 | 치환된 디아졸릴알킬-카비놀의 제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5011850A (ko) |
| EP (1) | EP0120276B1 (ko) |
| JP (1) | JPS59164778A (ko) |
| KR (1) | KR840008020A (ko) |
| AT (1) | ATE22887T1 (ko) |
| AU (2) | AU561701B2 (ko) |
| CA (3) | CA1245666A (ko) |
| DE (2) | DE3307218A1 (ko) |
| DK (1) | DK83684A (ko) |
| ES (1) | ES530114A0 (ko) |
| GR (1) | GR79549B (ko) |
| HU (2) | HU191254B (ko) |
| IL (2) | IL71098A (ko) |
| ZA (1) | ZA841552B (ko) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8306351D0 (en) * | 1983-03-08 | 1983-04-13 | Ici Plc | Azole fungicides |
| DK159205C (da) * | 1983-03-16 | 1991-03-04 | Pfizer | Bis(triazol)alkanol-forbindelser, anvendelse af disse, farmaceutiske praeparater og landbrugsfungicider indeholdende disse og fremgangsmaade til behandling af planter eller froe, som har en svampeinfektion |
| US4992454A (en) * | 1983-03-16 | 1991-02-12 | Pfizer Inc. | Antifungal 1,3-bis (1H-1,2,4-triazol-1-yl)-2-aryl butan-2-ols and derivatives thereof |
| DE3325313A1 (de) * | 1983-07-13 | 1985-01-31 | Bayer Ag, 5090 Leverkusen | Fungizide mittel, deren herstellung und verwendung |
| DE3440117A1 (de) * | 1984-11-02 | 1986-05-15 | Bayer Ag, 5090 Leverkusen | Substituierte azolylcyclopropyl-azolylmethyl-carbinol-derivate |
| DE3501370A1 (de) * | 1985-01-17 | 1986-07-17 | Bayer Ag, 5090 Leverkusen | 1-aryl-2,2-dialkyl-2-(1,2,4-triazol-1-yl)-ethanole |
| US4851423A (en) * | 1986-12-10 | 1989-07-25 | Schering Corporation | Pharmaceutically active compounds |
| DE3720756A1 (de) * | 1987-06-24 | 1989-01-05 | Bayer Ag | Azolylmethyl-cyclopropyl-carbinol-derivate |
| GB8716651D0 (en) * | 1987-07-15 | 1987-08-19 | Ici Plc | 2-propanol derivatives |
| DE3725396A1 (de) * | 1987-07-31 | 1989-02-09 | Bayer Ag | Hydroxyethyl-azolyl-oximether |
| DE3732384A1 (de) * | 1987-09-25 | 1989-04-06 | Bayer Ag | Bisazolyl-hydroxyalkyl-derivate enthaltende antimykotische mittel |
| DE3803833A1 (de) * | 1988-02-09 | 1989-08-17 | Bayer Ag | Substituierte azolylmethyloxirane |
| NO171272C (no) * | 1988-03-04 | 1993-02-17 | Sankyo Co | Analogifremgangsmaate til fremstilling av terapeutisk aktive 1,2,4-triazolforbindelser |
| GB8819308D0 (en) * | 1988-08-13 | 1988-09-14 | Pfizer Ltd | Triazole antifungal agents |
| GB9002375D0 (en) * | 1990-02-02 | 1990-04-04 | Pfizer Ltd | Triazole antifungal agents |
| EP0548553A1 (en) * | 1991-11-25 | 1993-06-30 | Takeda Chemical Industries, Ltd. | Optically active azole compounds, their production and use |
| ES2062941B1 (es) * | 1993-03-15 | 1995-10-01 | Uriach & Cia Sa J | Nuevos derivados de azol activos por via oral. |
| NZ270418A (en) * | 1994-02-07 | 1997-09-22 | Eisai Co Ltd | Polycyclic triazole & imidazole derivatives, antifungal compositions |
| CN109535091B (zh) * | 2018-12-04 | 2022-05-13 | 淮安国瑞化工有限公司 | 以1-(4-氯苯基)-2-(1h-1,2,4-三唑-1-基)乙酮合成环唑醇的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU557755A3 (ru) * | 1968-08-19 | 1977-05-05 | Янссен Фармасьютика Н.В. (Фирма) | Способ получени производных имидазола |
| IE44186B1 (en) * | 1975-12-03 | 1981-09-09 | Ici Ltd | 1,2,4-triazolyl alkanols and their use as pesticides |
| IT1097314B (it) * | 1978-07-26 | 1985-08-31 | Recordati Chem Pharm | Derivati dell'imidazolo ad attivita' anticonvulsivante |
| GB2078719B (en) * | 1980-06-02 | 1984-04-26 | Ici Ltd | Heterocyclic compounds |
| GB2104065B (en) * | 1981-06-04 | 1985-11-06 | Ciba Geigy Ag | Heterocyclyl-substituted mandelic acid compounds and mandelonitriles and their use for combating microorganisms |
| DE3262386D1 (en) * | 1981-06-06 | 1985-03-28 | Pfizer Ltd | Antifungal agents, processes for their preparation, and pharmaceutical compositions containing them |
-
1983
- 1983-03-02 DE DE19833307218 patent/DE3307218A1/de not_active Withdrawn
-
1984
- 1984-02-20 DE DE8484101710T patent/DE3460971D1/de not_active Expired
- 1984-02-20 AT AT84101710T patent/ATE22887T1/de not_active IP Right Cessation
- 1984-02-20 EP EP84101710A patent/EP0120276B1/de not_active Expired
- 1984-02-21 DK DK83684A patent/DK83684A/da not_active Application Discontinuation
- 1984-02-27 AU AU25063/84A patent/AU561701B2/en not_active Ceased
- 1984-02-28 ES ES530114A patent/ES530114A0/es active Granted
- 1984-02-28 JP JP59035451A patent/JPS59164778A/ja active Granted
- 1984-02-28 IL IL71098A patent/IL71098A/xx unknown
- 1984-02-29 CA CA000448581A patent/CA1245666A/en not_active Expired
- 1984-03-01 ZA ZA841552A patent/ZA841552B/xx unknown
- 1984-03-01 GR GR73973A patent/GR79549B/el unknown
- 1984-03-02 KR KR1019840001059A patent/KR840008020A/ko not_active Application Discontinuation
- 1984-03-02 HU HU84856A patent/HU191254B/hu not_active IP Right Cessation
- 1984-03-02 HU HU843946A patent/HU194189B/hu not_active IP Right Cessation
-
1986
- 1986-10-06 US US06/915,435 patent/US5011850A/en not_active Expired - Fee Related
- 1986-11-21 IL IL80726A patent/IL80726A0/xx not_active IP Right Cessation
-
1987
- 1987-02-11 AU AU69164/87A patent/AU6916487A/en not_active Abandoned
- 1987-07-07 CA CA000541541A patent/CA1239409A/en not_active Expired
- 1987-07-07 CA CA000541542A patent/CA1249592A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3460971D1 (en) | 1986-11-20 |
| ES8503672A1 (es) | 1985-04-01 |
| HU191254B (en) | 1987-01-28 |
| HU194189B (en) | 1988-01-28 |
| US5011850A (en) | 1991-04-30 |
| JPH0437829B2 (ko) | 1992-06-22 |
| ATE22887T1 (de) | 1986-11-15 |
| CA1239409A (en) | 1988-07-19 |
| DE3307218A1 (de) | 1984-09-06 |
| AU561701B2 (en) | 1987-05-14 |
| ZA841552B (en) | 1984-10-31 |
| IL71098A (en) | 1988-05-31 |
| IL80726A0 (en) | 1987-02-27 |
| AU6916487A (en) | 1987-05-28 |
| EP0120276B1 (de) | 1986-10-15 |
| CA1245666A (en) | 1988-11-29 |
| AU2506384A (en) | 1984-09-06 |
| DK83684D0 (da) | 1984-02-21 |
| CA1249592A (en) | 1989-01-31 |
| JPS59164778A (ja) | 1984-09-17 |
| ES530114A0 (es) | 1985-04-01 |
| DK83684A (da) | 1984-09-03 |
| GR79549B (ko) | 1984-10-30 |
| EP0120276A1 (de) | 1984-10-03 |
| IL71098A0 (en) | 1984-05-31 |
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