IL110461A - תהליך להכנת פיראזול ותולדות שלו - Google Patents
תהליך להכנת פיראזול ותולדות שלוInfo
- Publication number
- IL110461A IL110461A IL11046194A IL11046194A IL110461A IL 110461 A IL110461 A IL 110461A IL 11046194 A IL11046194 A IL 11046194A IL 11046194 A IL11046194 A IL 11046194A IL 110461 A IL110461 A IL 110461A
- Authority
- IL
- Israel
- Prior art keywords
- hydrazine
- formula
- iodine
- reaction
- mixture
- Prior art date
Links
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 42
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 30
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000011630 iodine Substances 0.000 claims abstract description 29
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 29
- 239000011541 reaction mixture Substances 0.000 claims abstract description 27
- 150000002429 hydrazines Chemical class 0.000 claims abstract description 20
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 17
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- -1 nitro, carboxyl Chemical group 0.000 claims abstract description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 239000003085 diluting agent Substances 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 17
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 16
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 14
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 11
- 238000004821 distillation Methods 0.000 description 10
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 9
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 9
- 238000010626 work up procedure Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 238000006386 neutralization reaction Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 235000009518 sodium iodide Nutrition 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 238000010908 decantation Methods 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 150000001602 bicycloalkyls Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VQTVFIMEENGCJA-UHFFFAOYSA-N 3,4-dimethyl-1H-pyrazole Chemical compound CC=1C=NNC=1C VQTVFIMEENGCJA-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RIKMMFOAQPJVMX-UHFFFAOYSA-N fomepizole Chemical compound CC=1C=NNC=1 RIKMMFOAQPJVMX-UHFFFAOYSA-N 0.000 description 3
- 229960004285 fomepizole Drugs 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000004677 hydrates Chemical class 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 3
- 150000003217 pyrazoles Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- LSZQMSSIUQNTDX-UHFFFAOYSA-N 1,5-dimethylpyrazole Chemical compound CC1=CC=NN1C LSZQMSSIUQNTDX-UHFFFAOYSA-N 0.000 description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- ACWQBUSCFPJUPN-HWKANZROSA-N trans-2-methyl-2-butenal Chemical compound C\C=C(/C)C=O ACWQBUSCFPJUPN-HWKANZROSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UNMYWSMUMWPJLR-UHFFFAOYSA-L Calcium iodide Chemical compound [Ca+2].[I-].[I-] UNMYWSMUMWPJLR-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001619 alkaline earth metal iodide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- XQPRBTXUXXVTKB-UHFFFAOYSA-M caesium iodide Chemical compound [I-].[Cs+] XQPRBTXUXXVTKB-UHFFFAOYSA-M 0.000 description 1
- 229910001640 calcium iodide Inorganic materials 0.000 description 1
- 229940046413 calcium iodide Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- GEOVEUCEIQCBKH-UHFFFAOYSA-N hypoiodous acid Chemical class IO GEOVEUCEIQCBKH-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- JJXWKXZOHOUFCX-UHFFFAOYSA-N methylhydrazine;hydrate Chemical compound O.CNN JJXWKXZOHOUFCX-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000005527 organic iodine compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000002904 solvent 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
-
- 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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4328228A DE4328228A1 (de) | 1993-08-23 | 1993-08-23 | Verfahren zur Herstellung von Pyrazol und dessen Derivaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL110461A0 IL110461A0 (en) | 1994-10-21 |
| IL110461A true IL110461A (he) | 1998-07-15 |
Family
ID=6495762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11046194A IL110461A (he) | 1993-08-23 | 1994-07-26 | תהליך להכנת פיראזול ותולדות שלו |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5569769A (he) |
| EP (1) | EP0715622B1 (he) |
| JP (1) | JP3717177B2 (he) |
| KR (1) | KR100342146B1 (he) |
| CN (1) | CN1069637C (he) |
| AT (1) | ATE165348T1 (he) |
| AU (1) | AU7536194A (he) |
| CA (1) | CA2169380C (he) |
| CZ (1) | CZ288738B6 (he) |
| DE (2) | DE4328228A1 (he) |
| ES (1) | ES2115968T3 (he) |
| HU (1) | HU216078B (he) |
| IL (1) | IL110461A (he) |
| RU (1) | RU2130930C1 (he) |
| SK (1) | SK280883B6 (he) |
| TW (1) | TW252108B (he) |
| UA (1) | UA47392C2 (he) |
| WO (1) | WO1995006036A1 (he) |
| ZA (1) | ZA946357B (he) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19500838A1 (de) * | 1995-01-13 | 1996-07-18 | Basf Ag | Verfahren zur Herstellung von 3,5-Diarylpyrazolen |
| DE19645313A1 (de) | 1996-11-04 | 1998-05-07 | Basf Ag | Substituierte 3-Benzylpyrazole |
| US6514977B1 (en) | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
| PL336990A1 (en) * | 1997-05-22 | 2000-07-31 | Searle & Co | 3(5)-heteroaryl group substituted pyrazoles as inhibitors of kinase p 38 |
| US6087496A (en) | 1998-05-22 | 2000-07-11 | G. D. Searle & Co. | Substituted pyrazoles suitable as p38 kinase inhibitors |
| JP2002502380A (ja) | 1997-05-22 | 2002-01-22 | ジー．ディー．サール アンド カンパニー | ｐ３８キナーゼ阻害剤としてのピラゾール誘導体 |
| US6979686B1 (en) | 2001-12-07 | 2005-12-27 | Pharmacia Corporation | Substituted pyrazoles as p38 kinase inhibitors |
| WO1998058914A1 (de) * | 1997-06-23 | 1998-12-30 | Basf Aktiengesellschaft | Verfahren zur herstellung substituierter pyrazole |
| KR100697482B1 (ko) | 2001-09-25 | 2007-03-20 | 파마시아 코포레이션 | 치환된 피라졸의 제조 방법 |
| US7057049B2 (en) | 2001-09-25 | 2006-06-06 | Pharmacia Corporation | Process for making substituted pyrazoles |
| US7682601B2 (en) * | 2003-04-15 | 2010-03-23 | Mallinckrodt Inc. | Bifunctional tridentate pyrazolyl containing ligands for re and tc tricarbonyl complexes |
| EP1948613A2 (en) | 2005-04-21 | 2008-07-30 | Orphan Medical Inc. | Process fot the preparation of ultrapure 4-methylpyrazole |
| US20110009463A1 (en) * | 2007-10-17 | 2011-01-13 | Yuri Karl Petersson | Geranylgeranyl transferase inhibitors and methods of making and using the same |
| US8178696B2 (en) | 2008-04-21 | 2012-05-15 | Albemarle Corporation | Processes for producing N-alkylpyrazole |
| DE102009060150B4 (de) * | 2009-12-23 | 2013-06-06 | K+S Aktiengesellschaft | Verfahren zur Herstellung von Säureadditionssalzen von Pyrazolen |
| EP2607358A4 (en) | 2010-08-19 | 2014-01-29 | Univ Tokyo | NEW OMEGA-3 FATTY ACIDS RECOVERY-RESISTANT METABOLITE |
| CN102558057B (zh) * | 2012-01-16 | 2014-04-02 | 兰州大学 | 多取代吡唑制备方法 |
| WO2020093715A1 (en) | 2018-11-07 | 2020-05-14 | Fujian Yongjing Technology Co., Ltd | New process for manufacture of pyrazoles or pyrimidones |
| CN110386900A (zh) * | 2019-08-21 | 2019-10-29 | 温州市华润医药化工有限公司 | 一种3-甲基吡唑的制备方法 |
| CN112321507A (zh) * | 2020-09-18 | 2021-02-05 | 武威金仓生物科技有限公司 | 一种3,4-二甲基吡唑及其磷酸盐的制备方法 |
| CN115028582B (zh) * | 2022-06-23 | 2024-04-12 | 曲靖师范学院 | 一种n-芳基吡唑类药物e-52862的制备方法及其产品 |
| CN120157619A (zh) * | 2025-03-17 | 2025-06-17 | 湖北荆洪生物科技股份有限公司 | 一种4-甲基吡唑的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH615384A5 (he) * | 1978-12-07 | 1980-01-31 | Buss Ag | |
| DE2922591A1 (de) * | 1979-06-02 | 1980-12-04 | Basf Ag | Verfahren zur herstellung von pyrazolen |
| DE3423930A1 (de) * | 1984-06-29 | 1986-01-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von pyrazolinen |
| GB8824400D0 (en) * | 1988-10-18 | 1988-11-23 | Glaxo Group Ltd | Chemical compounds |
| JP2861103B2 (ja) * | 1988-10-26 | 1999-02-24 | 日産化学工業株式会社 | ４―メチルピラゾール類の製造方法 |
| DE3918979A1 (de) * | 1989-06-10 | 1990-12-13 | Basf Ag | Verfahren zur herstellung von pyrazol und dessen derivaten |
| DE4028393A1 (de) * | 1990-09-07 | 1992-03-12 | Basf Ag | Verfahren zur herstellung von 3-methylpyrazol |
-
1993
- 1993-08-23 DE DE4328228A patent/DE4328228A1/de not_active Withdrawn
-
1994
- 1994-07-26 IL IL11046194A patent/IL110461A/he not_active IP Right Cessation
- 1994-07-27 TW TW083106844A patent/TW252108B/zh not_active IP Right Cessation
- 1994-08-13 DE DE59405805T patent/DE59405805D1/de not_active Expired - Lifetime
- 1994-08-13 JP JP50732195A patent/JP3717177B2/ja not_active Expired - Lifetime
- 1994-08-13 CN CN94193526A patent/CN1069637C/zh not_active Expired - Lifetime
- 1994-08-13 RU RU96105941A patent/RU2130930C1/ru active
- 1994-08-13 SK SK235-96A patent/SK280883B6/sk not_active IP Right Cessation
- 1994-08-13 KR KR1019960700868A patent/KR100342146B1/ko not_active Expired - Lifetime
- 1994-08-13 EP EP94925456A patent/EP0715622B1/de not_active Expired - Lifetime
- 1994-08-13 CZ CZ1996520A patent/CZ288738B6/cs not_active IP Right Cessation
- 1994-08-13 US US08/596,376 patent/US5569769A/en not_active Expired - Lifetime
- 1994-08-13 HU HUP9600419A patent/HU216078B/hu unknown
- 1994-08-13 ES ES94925456T patent/ES2115968T3/es not_active Expired - Lifetime
- 1994-08-13 UA UA96031027A patent/UA47392C2/uk unknown
- 1994-08-13 CA CA002169380A patent/CA2169380C/en not_active Expired - Lifetime
- 1994-08-13 WO PCT/EP1994/002708 patent/WO1995006036A1/de not_active Ceased
- 1994-08-13 AT AT94925456T patent/ATE165348T1/de active
- 1994-08-13 AU AU75361/94A patent/AU7536194A/en not_active Abandoned
- 1994-08-22 ZA ZA946357A patent/ZA946357B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5569769A (en) | 1996-10-29 |
| ZA946357B (en) | 1996-02-22 |
| HU216078B (hu) | 1999-04-28 |
| CZ52096A3 (en) | 1996-05-15 |
| CN1069637C (zh) | 2001-08-15 |
| JPH09501686A (ja) | 1997-02-18 |
| TW252108B (he) | 1995-07-21 |
| ATE165348T1 (de) | 1998-05-15 |
| CA2169380C (en) | 2004-10-19 |
| ES2115968T3 (es) | 1998-07-01 |
| IL110461A0 (en) | 1994-10-21 |
| DE4328228A1 (de) | 1995-03-02 |
| UA47392C2 (uk) | 2002-07-15 |
| HU9600419D0 (en) | 1996-04-29 |
| CA2169380A1 (en) | 1995-03-02 |
| DE59405805D1 (de) | 1998-05-28 |
| HUT74479A (en) | 1997-01-28 |
| SK23596A3 (en) | 1996-10-02 |
| RU2130930C1 (ru) | 1999-05-27 |
| AU7536194A (en) | 1995-03-21 |
| CN1131943A (zh) | 1996-09-25 |
| CZ288738B6 (cs) | 2001-08-15 |
| KR960703866A (ko) | 1996-08-31 |
| WO1995006036A1 (de) | 1995-03-02 |
| JP3717177B2 (ja) | 2005-11-16 |
| EP0715622A1 (de) | 1996-06-12 |
| SK280883B6 (sk) | 2000-09-12 |
| EP0715622B1 (de) | 1998-04-22 |
| KR100342146B1 (ko) | 2002-11-22 |
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