IL97582A - Process for the preparation of pyridine carbudioates converted to fluoromethyl - Google Patents
Process for the preparation of pyridine carbudioates converted to fluoromethylInfo
- Publication number
- IL97582A IL97582A IL9758291A IL9758291A IL97582A IL 97582 A IL97582 A IL 97582A IL 9758291 A IL9758291 A IL 9758291A IL 9758291 A IL9758291 A IL 9758291A IL 97582 A IL97582 A IL 97582A
- Authority
- IL
- Israel
- Prior art keywords
- process according
- dabco
- starting material
- trifluoromethyl
- amount
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 74
- -1 fluoromethyl-substituted pyridine Chemical class 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title description 10
- 238000005796 dehydrofluorination reaction Methods 0.000 claims abstract description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 70
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 28
- 239000007858 starting material Substances 0.000 claims description 17
- 230000003197 catalytic effect Effects 0.000 claims description 13
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 11
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000010 aprotic solvent Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 150000003738 xylenes Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 3
- 125000005907 alkyl ester group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 229910001882 dioxygen Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- VDAUQOYNJNOZSQ-UHFFFAOYSA-N 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)pyridine-3,5-dicarbothioic s-acid Chemical group CC(C)CC1=C(C(O)=S)C(C(F)F)=NC(C(F)(F)F)=C1C(O)=S VDAUQOYNJNOZSQ-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 65
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 38
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 239000012973 diazabicyclooctane Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- 238000006297 dehydration reaction Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 230000018044 dehydration Effects 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- IQDUSUMPAWCGJY-UHFFFAOYSA-N pyridine-2,3-dicarbothioic s-acid Chemical class SC(=O)C1=CC=CN=C1C(S)=O IQDUSUMPAWCGJY-UHFFFAOYSA-N 0.000 description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- TUDHHJQPQZFEIH-UHFFFAOYSA-N piperidine-4,4-diol Chemical class OC1(O)CCNCC1 TUDHHJQPQZFEIH-UHFFFAOYSA-N 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000012024 dehydrating agents Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000012035 limiting reagent Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- GVBSRTBYUFJDIW-UHFFFAOYSA-N pyridine-3,5-dicarbothioic s-acid Chemical compound OC(=S)C1=CN=CC(C(O)=S)=C1 GVBSRTBYUFJDIW-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- MXWKCJYCAHVAHK-UHFFFAOYSA-N 2h-pyran-2,3-diol Chemical class OC1OC=CC=C1O MXWKCJYCAHVAHK-UHFFFAOYSA-N 0.000 description 1
- RDOAUPPSCNSYPM-UHFFFAOYSA-N 3,4-dihydropyridine Chemical class C1CC=NC=C1 RDOAUPPSCNSYPM-UHFFFAOYSA-N 0.000 description 1
- BKVFOAJKAAHXEZ-UHFFFAOYSA-N 3-o,5-o-dimethyl 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)pyridine-3,5-dicarbothioate Chemical compound COC(=S)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=S)OC)=C1CC(C)C BKVFOAJKAAHXEZ-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- RDTHWWKRUNOJBW-UHFFFAOYSA-N pyridine-2-carbodithioic acid Chemical compound SC(=S)C1=CC=CC=N1 RDTHWWKRUNOJBW-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/83—Thioacids; Thioesters; Thioamides; Thioimides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrane Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/495,183 US5099023A (en) | 1990-03-19 | 1990-03-19 | Process for preparation of fluoromethyl-substituted pyridine carbodithioates |
| US07/495,184 US5099024A (en) | 1990-03-19 | 1990-03-19 | Process for preparation of fluoromethyl-substituted pyridine carbodithioates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL97582A true IL97582A (en) | 1994-12-29 |
Family
ID=27051674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9758291A IL97582A (en) | 1990-03-19 | 1991-03-18 | Process for the preparation of pyridine carbudioates converted to fluoromethyl |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0448541B1 (de) |
| JP (1) | JP2514283B2 (de) |
| KR (1) | KR930008232B1 (de) |
| AT (1) | ATE130608T1 (de) |
| AU (1) | AU630545B2 (de) |
| CA (1) | CA2038445C (de) |
| DE (1) | DE69114742D1 (de) |
| HU (1) | HU210336B (de) |
| IL (1) | IL97582A (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5051512A (en) * | 1990-03-19 | 1991-09-24 | Monsanto Company | Process for preparation of fluoromethyl-substituted piperidine carbodithioates |
| US5055583A (en) * | 1990-03-19 | 1991-10-08 | Monsanto Company | Process for preparation of fluoromethyl-substituted piperidine carbodithioates |
| HU209737B (en) * | 1990-03-19 | 1994-10-28 | Monsanto Co | Process for preparation of 4-alkyl-2,6 bis (fluoromethyl)-3,4-dihydro-pyridine- dicarboxylic acid-oxyesters and thioesters |
| JP5861763B1 (ja) | 2014-11-12 | 2016-02-16 | 第一精工株式会社 | 電気コネクタおよびその製造方法 |
| JP6239493B2 (ja) | 2014-12-12 | 2017-11-29 | 第一精工株式会社 | 電気コネクタ |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4692184A (en) | 1984-04-24 | 1987-09-08 | Monsanto Company | 2,6-substituted pyridine compounds |
| ES8506627A1 (es) * | 1983-08-11 | 1985-08-01 | Monsanto Co | Un procedimiento para preparar derivados de piridina sustituidos en las posiciones 2 y 6 |
| US4785129A (en) * | 1988-02-16 | 1988-11-15 | Monsanto Company | Methyl 4,4,4-trifluoro-3-oxo-butanethioate |
| US5051512A (en) * | 1990-03-19 | 1991-09-24 | Monsanto Company | Process for preparation of fluoromethyl-substituted piperidine carbodithioates |
| US5055583A (en) * | 1990-03-19 | 1991-10-08 | Monsanto Company | Process for preparation of fluoromethyl-substituted piperidine carbodithioates |
| HU209737B (en) * | 1990-03-19 | 1994-10-28 | Monsanto Co | Process for preparation of 4-alkyl-2,6 bis (fluoromethyl)-3,4-dihydro-pyridine- dicarboxylic acid-oxyesters and thioesters |
-
1991
- 1991-03-18 CA CA002038445A patent/CA2038445C/en not_active Expired - Fee Related
- 1991-03-18 KR KR1019910004255A patent/KR930008232B1/ko not_active Expired - Fee Related
- 1991-03-18 IL IL9758291A patent/IL97582A/en not_active IP Right Cessation
- 1991-03-18 EP EP91870044A patent/EP0448541B1/de not_active Expired - Lifetime
- 1991-03-18 AU AU73504/91A patent/AU630545B2/en not_active Ceased
- 1991-03-18 JP JP3216723A patent/JP2514283B2/ja not_active Expired - Lifetime
- 1991-03-18 AT AT91870044T patent/ATE130608T1/de not_active IP Right Cessation
- 1991-03-18 HU HU91876A patent/HU210336B/hu not_active IP Right Cessation
- 1991-03-18 DE DE69114742T patent/DE69114742D1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2514283B2 (ja) | 1996-07-10 |
| EP0448541A3 (en) | 1992-03-11 |
| ATE130608T1 (de) | 1995-12-15 |
| CA2038445A1 (en) | 1991-09-20 |
| DE69114742D1 (de) | 1996-01-04 |
| HUT56822A (en) | 1991-10-28 |
| AU7350491A (en) | 1991-09-19 |
| EP0448541A2 (de) | 1991-09-25 |
| KR920005715A (ko) | 1992-04-03 |
| JPH0641082A (ja) | 1994-02-15 |
| AU630545B2 (en) | 1992-10-29 |
| KR930008232B1 (ko) | 1993-08-27 |
| EP0448541B1 (de) | 1995-11-22 |
| HU210336B (en) | 1995-03-28 |
| CA2038445C (en) | 1997-09-30 |
| HU910876D0 (en) | 1991-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| HP | Change in proprietorship | ||
| MM9K | Patent not in force due to non-payment of renewal fees |