HU194189B - Process for production of triasolile- methil-ketons - Google Patents
Process for production of triasolile- methil-ketons Download PDFInfo
- Publication number
- HU194189B HU194189B HU843946A HU394686A HU194189B HU 194189 B HU194189 B HU 194189B HU 843946 A HU843946 A HU 843946A HU 394686 A HU394686 A HU 394686A HU 194189 B HU194189 B HU 194189B
- Authority
- HU
- Hungary
- Prior art keywords
- carbon atoms
- alkyl
- phenyl
- straight
- chain
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 238000000034 method Methods 0.000 title description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- -1 cyano, hydroxyl Chemical group 0.000 abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 abstract 18
- 125000000217 alkyl group Chemical group 0.000 abstract 13
- 125000001424 substituent group Chemical group 0.000 abstract 6
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- ZVOJDNBIWZSDOP-UHFFFAOYSA-N 1,3-bis(1h-pyrrol-2-yl)propan-2-one Chemical class C=1C=CNC=1CC(=O)CC1=CC=CN1 ZVOJDNBIWZSDOP-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
- LAUCRHAKXNKEGF-UHFFFAOYSA-N 1,3-bis(1H-pyrrol-2-yl)propane-1,2,3-trione Chemical class N1C(=CC=C1)C(=O)C(=O)C(=O)C=1NC=CC=1 LAUCRHAKXNKEGF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- IGJQUJNPMOYEJY-UHFFFAOYSA-N 2-acetylpyrrole Chemical class CC(=O)C1=CC=CN1 IGJQUJNPMOYEJY-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 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
- GNHQSAUHXKRQMC-UHFFFAOYSA-N benzene;chlorine Chemical compound [Cl].C1=CC=CC=C1 GNHQSAUHXKRQMC-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Luminescent Compositions (AREA)
- Photoreceptors In Electrophotography (AREA)
- Polymerization Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| HU194189B true HU194189B (en) | 1988-01-28 |
Family
ID=6192203
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU843946A HU194189B (en) | 1983-03-02 | 1984-03-02 | Process for production of triasolile- methil-ketons |
| HU84856A HU191254B (en) | 1983-03-02 | 1984-03-02 | Process for production of derivatives of di- and triasol-alkyl-carbonile and containing thereof medical preparatives with antimycotical effect |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU84856A HU191254B (en) | 1983-03-02 | 1984-03-02 | Process for production of derivatives of di- and triasol-alkyl-carbonile and containing thereof medical preparatives with antimycotical effect |
Country Status (14)
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/ES8503672A1/es not_active Expired
- 1984-02-28 IL IL71098A patent/IL71098A/xx unknown
- 1984-02-28 JP JP59035451A patent/JPS59164778A/ja active Granted
- 1984-02-29 CA CA000448581A patent/CA1245666A/en not_active Expired
- 1984-03-01 GR GR73973A patent/GR79549B/el unknown
- 1984-03-01 ZA ZA841552A patent/ZA841552B/xx unknown
- 1984-03-02 KR KR1019840001059A patent/KR840008020A/ko not_active Ceased
- 1984-03-02 HU HU843946A patent/HU194189B/hu not_active IP Right Cessation
- 1984-03-02 HU HU84856A patent/HU191254B/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 |
| DK83684D0 (da) | 1984-02-21 |
| IL71098A0 (en) | 1984-05-31 |
| AU561701B2 (en) | 1987-05-14 |
| GR79549B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-10-30 |
| AU2506384A (en) | 1984-09-06 |
| IL80726A0 (en) | 1987-02-27 |
| ES530114A0 (es) | 1985-04-01 |
| CA1239409A (en) | 1988-07-19 |
| JPH0437829B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-06-22 |
| HU191254B (en) | 1987-01-28 |
| KR840008020A (ko) | 1984-12-12 |
| EP0120276B1 (de) | 1986-10-15 |
| ZA841552B (en) | 1984-10-31 |
| US5011850A (en) | 1991-04-30 |
| JPS59164778A (ja) | 1984-09-17 |
| ES8503672A1 (es) | 1985-04-01 |
| ATE22887T1 (de) | 1986-11-15 |
| DK83684A (da) | 1984-09-03 |
| CA1249592A (en) | 1989-01-31 |
| AU6916487A (en) | 1987-05-28 |
| CA1245666A (en) | 1988-11-29 |
| IL71098A (en) | 1988-05-31 |
| EP0120276A1 (de) | 1984-10-03 |
| DE3307218A1 (de) | 1984-09-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |