OA10847A - Azole compounds endowed with antimycotic activity for human and veterinary use - Google Patents
Azole compounds endowed with antimycotic activity for human and veterinary use Download PDFInfo
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- OA10847A OA10847A OA9800152A OA9800152A OA10847A OA 10847 A OA10847 A OA 10847A OA 9800152 A OA9800152 A OA 9800152A OA 9800152 A OA9800152 A OA 9800152A OA 10847 A OA10847 A OA 10847A
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- chloro
- hydrogen
- formula
- fluoro
- compounds
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- 230000001857 anti-mycotic effect Effects 0.000 title abstract description 30
- 150000003851 azoles Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 100
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 27
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 13
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- -1 1,1,2,2-tetrafluoroethyl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 5
- 230000010933 acylation Effects 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000002255 enzymatic effect Effects 0.000 claims description 4
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- 230000000707 stereoselective effect Effects 0.000 claims description 4
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- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 241000058882 Rhinolophus pusillus Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 241000223230 Trichosporon Species 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
- 238000002815 broth microdilution Methods 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 102220059961 rs786201335 Human genes 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000002653 sulfanylmethyl group Chemical group [H]SC([H])([H])[*] 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 206010052366 systemic mycosis Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- 238000011200 topical administration Methods 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
- 150000003852 triazoles Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07D233/60—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 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- 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
-
- 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
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Devices For Medical Bathing And Washing (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT96MI000371A IT1283038B1 (it) | 1996-02-28 | 1996-02-28 | Composti azolici ad attivita' antimicotica per uso umano e veterinario |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA10847A true OA10847A (en) | 2003-02-05 |
Family
ID=11373418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA9800152A OA10847A (en) | 1996-02-28 | 1998-08-28 | Azole compounds endowed with antimycotic activity for human and veterinary use |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US5869512A (en:Method) |
| EP (1) | EP0877739B1 (en:Method) |
| JP (1) | JP2000505466A (en:Method) |
| KR (1) | KR19990087363A (en:Method) |
| CN (1) | CN1082050C (en:Method) |
| AP (1) | AP9801328A0 (en:Method) |
| AT (1) | ATE219066T1 (en:Method) |
| AU (1) | AU713049B2 (en:Method) |
| BG (1) | BG102711A (en:Method) |
| BR (1) | BR9707773A (en:Method) |
| CA (1) | CA2247390A1 (en:Method) |
| CZ (1) | CZ291790B6 (en:Method) |
| DE (1) | DE69713276T2 (en:Method) |
| DK (1) | DK0877739T3 (en:Method) |
| EA (1) | EA003189B1 (en:Method) |
| EE (1) | EE03684B1 (en:Method) |
| ES (1) | ES2176689T3 (en:Method) |
| GE (1) | GEP20002091B (en:Method) |
| HU (1) | HUP9900569A3 (en:Method) |
| IL (1) | IL125701A (en:Method) |
| IT (1) | IT1283038B1 (en:Method) |
| NO (1) | NO983953L (en:Method) |
| NZ (1) | NZ331919A (en:Method) |
| OA (1) | OA10847A (en:Method) |
| PL (1) | PL328582A1 (en:Method) |
| PT (1) | PT877739E (en:Method) |
| SI (1) | SI0877739T1 (en:Method) |
| SK (1) | SK283391B6 (en:Method) |
| TR (1) | TR199801688T2 (en:Method) |
| UA (1) | UA55405C2 (en:Method) |
| WO (1) | WO1997031903A1 (en:Method) |
| ZA (1) | ZA971665B (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1296925B1 (it) * | 1997-12-05 | 1999-08-03 | Zambon Spa | Procedimento per la preparazione di composti ad attivita' antimicotica |
| US6297115B1 (en) * | 1998-11-06 | 2001-10-02 | Advanced Micro Devices, Inc. | Cmos processs with low thermal budget |
| EP1475370B1 (en) | 2002-02-15 | 2009-08-05 | Mitsui Chemicals, Inc. | Optically active azole derivative and process for producing the same |
| GB0222964D0 (en) | 2002-10-03 | 2002-11-13 | Unilever Plc | Polymeric film for water soluble package |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU187399B (en) * | 1980-12-24 | 1985-12-28 | Sumitomo Chemical Co | Process for preparing imidazolyl-propanol derivatives |
| EP0061835B1 (en) * | 1981-03-18 | 1989-02-01 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
| DE3271901D1 (en) * | 1982-02-03 | 1986-08-07 | Ici Plc | Heterocyclic compounds useful as pesticides and processes for making them |
| US4505919A (en) * | 1982-10-09 | 1985-03-19 | Pfizer Inc. | Antifungal S-arylmethyl- and S-heterocyclylmethyl ethers of 2-aryl-3-mercapto-1-(1H-1,2,4-triazol-1-yl) propan-2-ols |
| AU572889B2 (en) * | 1983-09-26 | 1988-05-19 | Sumitomo Chemical Company, Limited | 1,2,4 - triazolyl propanols |
| KR930004193B1 (ko) * | 1984-10-02 | 1993-05-21 | 스미또모 세이야꾸 가부시끼가이샤 | N-치환된 트리아졸 유도체의 제조방법 |
| US5081138A (en) * | 1986-12-17 | 1992-01-14 | Merck Frosst Canada, Inc. | 3-hetero-substituted-n-benzyl-indoles and prevention of leucotriene synthesis therewith |
| IT1198240B (it) * | 1986-12-23 | 1988-12-21 | Agrimont Spa | Azolilderivati fungicidi |
| IT1232943B (it) * | 1987-11-09 | 1992-03-10 | Mini Ricerca Scient Tecnolog | Azolilderivati fungicidi. |
| US5134152A (en) * | 1989-12-07 | 1992-07-28 | Sankyo Company, Limited | Oxetane derivatives and their use as anti-fungal or fungicidal agents |
| CA2031892C (en) * | 1989-12-25 | 2000-08-01 | Minoru Tokizawa | Triazole derivatives |
| FI913983L (fi) * | 1990-08-26 | 1992-02-29 | Sankyo Co | Svampmotverkande triazolderivat, deras framstaellning och anvaendningar. |
| GB9307924D0 (en) * | 1993-04-16 | 1993-06-02 | Zeneca Ltd | Chrial synthesis |
| CA2145458A1 (en) * | 1994-03-28 | 1995-09-29 | Hiroki Kodama | Triazole compound and production process and use thereof |
| IT1273509B (it) * | 1995-04-07 | 1997-07-08 | Zambon Spa | Composti azolici ad attivita' antimicotica per uso umano e veterinario |
-
1996
- 1996-02-28 IT IT96MI000371A patent/IT1283038B1/it active IP Right Grant
-
1997
- 1997-02-25 NZ NZ331919A patent/NZ331919A/en unknown
- 1997-02-25 DE DE69713276T patent/DE69713276T2/de not_active Expired - Fee Related
- 1997-02-25 US US08/806,149 patent/US5869512A/en not_active Expired - Fee Related
- 1997-02-25 KR KR1019980706773A patent/KR19990087363A/ko not_active Ceased
- 1997-02-25 CZ CZ19982748A patent/CZ291790B6/cs not_active IP Right Cessation
- 1997-02-25 CA CA002247390A patent/CA2247390A1/en not_active Abandoned
- 1997-02-25 EA EA199800693A patent/EA003189B1/ru not_active IP Right Cessation
- 1997-02-25 HU HU9900569A patent/HUP9900569A3/hu unknown
- 1997-02-25 PL PL97328582A patent/PL328582A1/xx unknown
- 1997-02-25 CN CN97192673A patent/CN1082050C/zh not_active Expired - Fee Related
- 1997-02-25 SK SK1161-98A patent/SK283391B6/sk unknown
- 1997-02-25 ES ES97906121T patent/ES2176689T3/es not_active Expired - Lifetime
- 1997-02-25 WO PCT/EP1997/000886 patent/WO1997031903A1/en not_active Application Discontinuation
- 1997-02-25 IL IL12570197A patent/IL125701A/xx not_active IP Right Cessation
- 1997-02-25 AP APAP/P/1998/001328A patent/AP9801328A0/en unknown
- 1997-02-25 PT PT97906121T patent/PT877739E/pt unknown
- 1997-02-25 BR BR9707773-9A patent/BR9707773A/pt not_active Application Discontinuation
- 1997-02-25 JP JP9530577A patent/JP2000505466A/ja active Pending
- 1997-02-25 UA UA98084619A patent/UA55405C2/uk unknown
- 1997-02-25 AT AT97906121T patent/ATE219066T1/de not_active IP Right Cessation
- 1997-02-25 AU AU20929/97A patent/AU713049B2/en not_active Ceased
- 1997-02-25 SI SI9730373T patent/SI0877739T1/xx unknown
- 1997-02-25 EE EE9800261A patent/EE03684B1/xx not_active IP Right Cessation
- 1997-02-25 TR TR1998/01688T patent/TR199801688T2/xx unknown
- 1997-02-25 EP EP97906121A patent/EP0877739B1/en not_active Expired - Lifetime
- 1997-02-25 GE GEAP19974471A patent/GEP20002091B/en unknown
- 1997-02-25 DK DK97906121T patent/DK0877739T3/da active
- 1997-02-26 ZA ZA9701665A patent/ZA971665B/xx unknown
-
1998
- 1998-08-21 BG BG102711A patent/BG102711A/bg unknown
- 1998-08-24 US US09/138,904 patent/US6103909A/en not_active Expired - Fee Related
- 1998-08-27 NO NO983953A patent/NO983953L/no not_active Application Discontinuation
- 1998-08-28 OA OA9800152A patent/OA10847A/en unknown
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