SK286290A3 - Manufacturing process of pyrazoles - Google Patents
Manufacturing process of pyrazoles Download PDFInfo
- Publication number
- SK286290A3 SK286290A3 SK2862-90A SK286290A SK286290A3 SK 286290 A3 SK286290 A3 SK 286290A3 SK 286290 A SK286290 A SK 286290A SK 286290 A3 SK286290 A3 SK 286290A3
- Authority
- SK
- Slovakia
- Prior art keywords
- reaction
- iodine
- iodide
- mol
- hydrazine
- Prior art date
Links
- 150000003217 pyrazoles Chemical class 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 6
- -1 iodite Chemical compound 0.000 claims description 14
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 9
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims description 7
- 150000003219 pyrazolines Chemical class 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 claims description 4
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 150000001351 alkyl iodides Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 229910001511 metal iodide Inorganic materials 0.000 claims description 3
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract description 29
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract description 16
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract description 14
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 9
- 229910052740 iodine Inorganic materials 0.000 abstract description 9
- 239000011630 iodine Substances 0.000 abstract description 9
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 abstract description 7
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract description 7
- 238000011065 in-situ storage Methods 0.000 abstract description 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 239000012429 reaction media Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 150000002497 iodine compounds Chemical class 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 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 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 235000009518 sodium iodide Nutrition 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- JXHKUYQCEJILEI-UHFFFAOYSA-N 3,5-diphenyl-1h-pyrazole Chemical compound C=1C(C=2C=CC=CC=2)=NNC=1C1=CC=CC=C1 JXHKUYQCEJILEI-UHFFFAOYSA-N 0.000 description 2
- LVSQXDHWDCMMRJ-UHFFFAOYSA-N 4-hydroxybutan-2-one Chemical compound CC(=O)CCO LVSQXDHWDCMMRJ-UHFFFAOYSA-N 0.000 description 2
- OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- UNMYWSMUMWPJLR-UHFFFAOYSA-L Calcium iodide Chemical compound [Ca+2].[I-].[I-] UNMYWSMUMWPJLR-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- AXMVYSVVTMKQSL-UHFFFAOYSA-N UNPD142122 Natural products OC1=CC=C(C=CC=O)C=C1O AXMVYSVVTMKQSL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 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 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000005527 organic iodine compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical class CCC(=O)CC FDPIMTJIUBPUKL-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
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010626 work up procedure Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3918979A DE3918979A1 (de) | 1989-06-10 | 1989-06-10 | Verfahren zur herstellung von pyrazol und dessen derivaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK286290A3 true SK286290A3 (en) | 1997-04-09 |
| SK278414B6 SK278414B6 (en) | 1997-04-09 |
Family
ID=6382485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK2862-90A SK278414B6 (en) | 1989-06-10 | 1990-06-08 | Producing method of pyrazoles |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4996327A (cs) |
| EP (1) | EP0402722B1 (cs) |
| JP (1) | JP2868588B2 (cs) |
| KR (2) | KR910000653A (cs) |
| AT (1) | ATE100799T1 (cs) |
| CA (1) | CA2018206C (cs) |
| CZ (1) | CZ279830B6 (cs) |
| DE (2) | DE3918979A1 (cs) |
| DK (1) | DK0402722T3 (cs) |
| ES (1) | ES2062181T3 (cs) |
| HU (1) | HU207299B (cs) |
| IL (1) | IL94559A (cs) |
| SK (1) | SK278414B6 (cs) |
| ZA (1) | ZA904430B (cs) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4028393A1 (de) * | 1990-09-07 | 1992-03-12 | Basf Ag | Verfahren zur herstellung von 3-methylpyrazol |
| JPH05156545A (ja) * | 1991-12-10 | 1993-06-22 | Takata Kk | ノンコート織布及びその製造方法 |
| WO1994002461A1 (en) * | 1992-07-28 | 1994-02-03 | Merck Sharp & Dohme Limited | Azacyclic compounds |
| DE4328228A1 (de) * | 1993-08-23 | 1995-03-02 | Basf Ag | Verfahren zur Herstellung von Pyrazol und dessen Derivaten |
| DE4415484A1 (de) * | 1994-05-03 | 1995-11-09 | Basf Ag | Verfahren zur Herstellung von 1-(Het)aryl-3-hydroxy-pyrazolen |
| US5510361A (en) * | 1994-10-20 | 1996-04-23 | The Procter & Gamble Company | Di-tert-butylphenol compounds with heterocyclic moiety, useful as anti-inflammatory agents |
| 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 |
| UA59402C2 (uk) * | 1997-06-23 | 2003-09-15 | Басф Акцієнгезелльшафт | Спосіб одержання похідних піразолу |
| MX2007013118A (es) | 2005-04-21 | 2008-01-11 | Orphan Medical Inc | Proceso para la preparacion de 4-metilpirazol ultrapuro. |
| US8410135B2 (en) * | 2007-06-15 | 2013-04-02 | Solvay Pharmaceuticals B.V. | 4,5 dihydro-(1H)-pyrazole derivatives as cannabinoid CB1 receptor modulators |
| EP2282998B1 (en) | 2008-04-21 | 2014-09-10 | Albemarle Corporation | Processes for producing n-alkylpyrazole |
| KR101005834B1 (ko) * | 2008-08-04 | 2011-01-05 | 이화여자대학교 산학협력단 | 피라졸의 제조방법 |
| CN102311388B (zh) * | 2011-07-07 | 2013-05-22 | 林文斌 | 一种工业化生产3,4-二甲基吡唑及其磷酸盐的方法 |
| CN102399189B (zh) * | 2011-11-29 | 2014-12-31 | 上虞盛晖化工股份有限公司 | 一种3,4-二甲基吡唑磷酸盐的合成方法 |
| CN102558057B (zh) * | 2012-01-16 | 2014-04-02 | 兰州大学 | 多取代吡唑制备方法 |
| CN102911119B (zh) * | 2012-09-30 | 2015-06-17 | 浙江工业大学 | 3,4-二甲基吡唑和3,4-二甲基吡唑磷酸盐的制备方法 |
| CN106316956A (zh) * | 2015-07-02 | 2017-01-11 | 胡梓国 | 吡唑的工业生产方法 |
| CN105153036A (zh) * | 2015-09-28 | 2015-12-16 | 乐平市康鑫医药化工有限公司 | 丙烯醛固定床反应制备吡唑的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3029160A1 (de) * | 1980-08-01 | 1982-03-04 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von pyrazolen |
| DE3035395A1 (de) * | 1980-09-19 | 1982-05-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von pyrazol |
| DE3603376A1 (de) * | 1986-02-05 | 1987-08-06 | Basf Ag | Verfahren zur herstellung von pyrazolen |
| DE3716293A1 (de) * | 1987-05-15 | 1988-11-24 | Basf Ag | Verfahren zur herstellung von pyrazolen |
-
1989
- 1989-06-10 DE DE3918979A patent/DE3918979A1/de not_active Withdrawn
-
1990
- 1990-05-29 IL IL9455990A patent/IL94559A/en unknown
- 1990-06-02 DK DK90110517.1T patent/DK0402722T3/da active
- 1990-06-02 ES ES90110517T patent/ES2062181T3/es not_active Expired - Lifetime
- 1990-06-02 DE DE90110517T patent/DE59004384D1/de not_active Expired - Lifetime
- 1990-06-02 AT AT90110517T patent/ATE100799T1/de not_active IP Right Cessation
- 1990-06-02 EP EP90110517A patent/EP0402722B1/de not_active Expired - Lifetime
- 1990-06-04 CA CA002018206A patent/CA2018206C/en not_active Expired - Lifetime
- 1990-06-07 US US07/534,270 patent/US4996327A/en not_active Expired - Lifetime
- 1990-06-08 ZA ZA904430A patent/ZA904430B/xx unknown
- 1990-06-08 KR KR1019900008384A patent/KR910000653A/ko not_active IP Right Cessation
- 1990-06-08 CZ CS902862A patent/CZ279830B6/cs unknown
- 1990-06-08 SK SK2862-90A patent/SK278414B6/sk not_active IP Right Cessation
- 1990-06-08 KR KR1019900008384A patent/KR0140875B1/ko active
- 1990-06-08 HU HU903775A patent/HU207299B/hu unknown
- 1990-06-08 JP JP2148891A patent/JP2868588B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HU903775D0 (en) | 1990-11-28 |
| KR0140875B1 (ko) | 1998-06-01 |
| DK0402722T3 (da) | 1994-02-28 |
| CZ286290A3 (en) | 1995-03-15 |
| JP2868588B2 (ja) | 1999-03-10 |
| HUT54349A (en) | 1991-02-28 |
| KR910000653A (ko) | 1991-01-29 |
| CA2018206C (en) | 2000-02-29 |
| ZA904430B (en) | 1992-02-26 |
| ATE100799T1 (de) | 1994-02-15 |
| EP0402722B1 (de) | 1994-01-26 |
| JPH03115265A (ja) | 1991-05-16 |
| SK278414B6 (en) | 1997-04-09 |
| ES2062181T3 (es) | 1994-12-16 |
| IL94559A0 (en) | 1991-03-10 |
| CA2018206A1 (en) | 1990-12-10 |
| DE3918979A1 (de) | 1990-12-13 |
| HU207299B (en) | 1993-03-29 |
| US4996327A (en) | 1991-02-26 |
| EP0402722A1 (de) | 1990-12-19 |
| CZ279830B6 (cs) | 1995-07-12 |
| IL94559A (en) | 1994-02-27 |
| DE59004384D1 (de) | 1994-03-10 |
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