CA1314552C - Preparation of quinolines - Google Patents
Preparation of quinolinesInfo
- Publication number
- CA1314552C CA1314552C CA000568488A CA568488A CA1314552C CA 1314552 C CA1314552 C CA 1314552C CA 000568488 A CA000568488 A CA 000568488A CA 568488 A CA568488 A CA 568488A CA 1314552 C CA1314552 C CA 1314552C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- hydrogen
- sulfuric acid
- chloro
- quinoline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title claims description 8
- 229940111121 antirheumatic drug quinolines Drugs 0.000 title abstract description 10
- 150000003248 quinolines Chemical class 0.000 title abstract description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 38
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 28
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 10
- 239000011630 iodine Substances 0.000 claims abstract description 10
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 8
- 150000002576 ketones Chemical class 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000003197 catalytic effect Effects 0.000 claims abstract description 6
- 229910052736 halogen Chemical group 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract 4
- 150000002367 halogens Chemical group 0.000 claims abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 235000013350 formula milk Nutrition 0.000 claims description 11
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 230000036647 reaction Effects 0.000 claims description 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 21
- 229940032330 sulfuric acid Drugs 0.000 description 15
- ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 229940039407 aniline Drugs 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 235000009518 sodium iodide Nutrition 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 4
- PZAXENZUGIIHBG-UHFFFAOYSA-N 7-chloro-3,8-dimethylquinoline Chemical compound CC1=C(Cl)C=CC2=CC(C)=CN=C21 PZAXENZUGIIHBG-UHFFFAOYSA-N 0.000 description 3
- NKWDCLXGUJHNHS-UHFFFAOYSA-N 7-chloro-8-methylquinoline Chemical compound C1=CN=C2C(C)=C(Cl)C=CC2=C1 NKWDCLXGUJHNHS-UHFFFAOYSA-N 0.000 description 3
- -1 Z-methylaniline Chemical compound 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- MUDSDYNRBDKLGK-UHFFFAOYSA-N 4-methylquinoline Chemical compound C1=CC=C2C(C)=CC=NC2=C1 MUDSDYNRBDKLGK-UHFFFAOYSA-N 0.000 description 2
- FXDITTUYSNDPFH-UHFFFAOYSA-N 7-chloro-2,8-dimethylquinoline Chemical compound C1=CC(Cl)=C(C)C2=NC(C)=CC=C21 FXDITTUYSNDPFH-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
- COHDHYZHOPQOFD-UHFFFAOYSA-N arsenic pentoxide Chemical compound O=[As](=O)O[As](=O)=O COHDHYZHOPQOFD-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- JTHNLKXLWOXOQK-UHFFFAOYSA-N hex-1-en-3-one Chemical compound CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229940083608 sodium hydroxide Drugs 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000012485 toluene extract Substances 0.000 description 2
- MBDOYVRWFFCFHM-SNAWJCMRSA-N (2E)-hexenal Chemical compound CCC\C=C\C=O MBDOYVRWFFCFHM-SNAWJCMRSA-N 0.000 description 1
- YKOLZVXSPGIIBJ-UHFFFAOYSA-N 2-Isopropylaniline Chemical compound CC(C)C1=CC=CC=C1N YKOLZVXSPGIIBJ-UHFFFAOYSA-N 0.000 description 1
- IFLLHNMCIXRVEC-UHFFFAOYSA-N 2-butyl-3-chloroaniline Chemical compound CCCCC1=C(N)C=CC=C1Cl IFLLHNMCIXRVEC-UHFFFAOYSA-N 0.000 description 1
- HDVUPIFFKAHPJY-UHFFFAOYSA-N 2-butylaniline Chemical compound CCCCC1=CC=CC=C1N HDVUPIFFKAHPJY-UHFFFAOYSA-N 0.000 description 1
- RWNBRROKBLKJDU-UHFFFAOYSA-N 2-ethyl-3-fluoroaniline Chemical compound CCC1=C(N)C=CC=C1F RWNBRROKBLKJDU-UHFFFAOYSA-N 0.000 description 1
- WKURVXXDGMYSDP-UHFFFAOYSA-N 2-propyl-aniline Chemical compound CCCC1=CC=CC=C1N WKURVXXDGMYSDP-UHFFFAOYSA-N 0.000 description 1
- AEIOZWYBDBVCGW-UHFFFAOYSA-N 2-tert-butylaniline Chemical compound CC(C)(C)C1=CC=CC=C1N AEIOZWYBDBVCGW-UHFFFAOYSA-N 0.000 description 1
- YNFNCYIUPQLIEX-UHFFFAOYSA-N 3-bromo-2-ethylaniline Chemical compound CCC1=C(N)C=CC=C1Br YNFNCYIUPQLIEX-UHFFFAOYSA-N 0.000 description 1
- IILVSKMKMOJHMA-UHFFFAOYSA-N 3-bromo-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Br IILVSKMKMOJHMA-UHFFFAOYSA-N 0.000 description 1
- OMZRDBSLAGVDMI-UHFFFAOYSA-N 3-chloro-2-ethylaniline Chemical compound CCC1=C(N)C=CC=C1Cl OMZRDBSLAGVDMI-UHFFFAOYSA-N 0.000 description 1
- BLLIICMFQDJIES-UHFFFAOYSA-N 3-chloro-2-propan-2-ylaniline Chemical compound CC(C)C1=C(N)C=CC=C1Cl BLLIICMFQDJIES-UHFFFAOYSA-N 0.000 description 1
- WPYGEGUIGYISJW-UHFFFAOYSA-N 3-chloro-2-propylaniline Chemical compound CCCC1=C(N)C=CC=C1Cl WPYGEGUIGYISJW-UHFFFAOYSA-N 0.000 description 1
- SLDLVGFPFFLYBM-UHFFFAOYSA-N 3-fluoro-2-methyl-aniline Chemical compound CC1=C(N)C=CC=C1F SLDLVGFPFFLYBM-UHFFFAOYSA-N 0.000 description 1
- XYYHROWBTBFMBY-UHFFFAOYSA-N 3-fluoro-2-propylaniline Chemical compound CCCC1=C(N)C=CC=C1F XYYHROWBTBFMBY-UHFFFAOYSA-N 0.000 description 1
- FKYHSWFYBFHXKN-UHFFFAOYSA-N 7-chloro-3-methylquinoline Chemical compound C1=C(Cl)C=CC2=CC(C)=CN=C21 FKYHSWFYBFHXKN-UHFFFAOYSA-N 0.000 description 1
- HUSFLDKRAODFGV-UHFFFAOYSA-N 7-chloro-4,8-dimethylquinoline Chemical compound ClC1=CC=C2C(C)=CC=NC2=C1C HUSFLDKRAODFGV-UHFFFAOYSA-N 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 229940046413 calcium iodide Drugs 0.000 description 1
- 229910001640 calcium iodide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LABTWGUMFABVFG-UHFFFAOYSA-N methyl propenyl ketone Chemical compound CC=CC(C)=O LABTWGUMFABVFG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 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
- 238000007086 side reaction Methods 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
- MBDOYVRWFFCFHM-UHFFFAOYSA-N trans-2-hexenal Natural products CCCC=CC=O MBDOYVRWFFCFHM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/18—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3719014.8-44 | 1987-06-06 | ||
| DE19873719014 DE3719014A1 (de) | 1987-06-06 | 1987-06-06 | Verfahren zur herstellung von chinolinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1314552C true CA1314552C (en) | 1993-03-16 |
Family
ID=6329209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000568488A Expired - Lifetime CA1314552C (en) | 1987-06-06 | 1988-06-02 | Preparation of quinolines |
Country Status (9)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3930167A1 (de) * | 1989-09-09 | 1991-03-14 | Basf Ag | Verfahren zur herstellung von 3-methylchinolin-8-carbonsaeure |
| FR2672596B1 (fr) * | 1991-02-07 | 1995-07-13 | Roussel Uclaf | Nouveaux derives bicycliques azotes, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant. |
| US5126456A (en) * | 1991-10-17 | 1992-06-30 | Merck & Co., Inc. | 7-chloroquinaldine synthesis |
| US6103904A (en) * | 1997-07-17 | 2000-08-15 | Basf Corporation | Skraup reaction process for synthesizing quinolones |
| JP4969099B2 (ja) * | 2005-12-21 | 2012-07-04 | エア・ウォーター株式会社 | ６−キノリノールの製造方法 |
| CN101555225B (zh) * | 2009-05-22 | 2011-10-12 | 北京欧凯纳斯科技有限公司 | 一种多取代喹啉化合物的制备方法 |
| CN101851197B (zh) * | 2010-06-07 | 2011-03-23 | 江苏绿利来股份有限公司 | 二氯喹啉酸的合成和精制方法 |
| CN102464613B (zh) * | 2010-11-10 | 2015-07-01 | 中国石油大学(北京) | 一种喹啉衍生物的合成方法 |
| CN102060761B (zh) * | 2011-01-11 | 2012-10-17 | 浙江大学 | 一种制备喹啉衍生物的方法 |
| CN102070521B (zh) * | 2011-01-19 | 2012-10-03 | 北京成宇化工有限公司 | 喹啉衍生物的制备方法 |
| CN107698503A (zh) * | 2017-11-22 | 2018-02-16 | 金凯(辽宁)化工有限公司 | 一种8‑氟喹啉的制备方法和3‑碘‑8‑氟喹啉的制备方法 |
| CN111377859B (zh) * | 2018-12-28 | 2022-12-16 | 北京颖泰嘉和生物科技股份有限公司 | 7-氯-8-甲基喹啉的制备方法 |
| CN109912503B (zh) * | 2019-04-01 | 2022-04-08 | 江南大学 | 一种2,3-二酰基喹啉类化合物的合成方法 |
| CN115894357A (zh) * | 2022-11-18 | 2023-04-04 | 山东兴文工业技术研究院有限公司 | Skraup法合成3,8-二甲基-7-氯喹啉 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2358162A (en) * | 1941-09-01 | 1944-09-12 | Stafford Allen And Sons Ltd | Process for the preparation of compounds containing fused pyridine rings |
| US3787418A (en) * | 1971-02-17 | 1974-01-22 | American Cyanamid Co | 6-alkyl-3-methylquinaldinic acids |
| DE3326255A1 (de) * | 1983-07-21 | 1985-01-31 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von chinolinen |
-
1987
- 1987-06-06 DE DE19873719014 patent/DE3719014A1/de active Granted
-
1988
- 1988-05-31 ES ES88108661T patent/ES2074988T3/es not_active Expired - Lifetime
- 1988-05-31 AT AT88108661T patent/ATE125797T1/de not_active IP Right Cessation
- 1988-05-31 DE DE3854245T patent/DE3854245D1/de not_active Expired - Lifetime
- 1988-05-31 EP EP88108661A patent/EP0294685B1/de not_active Expired - Lifetime
- 1988-06-02 CA CA000568488A patent/CA1314552C/en not_active Expired - Lifetime
- 1988-06-04 KR KR1019880006737A patent/KR950014790B1/ko not_active Expired - Lifetime
- 1988-06-06 CN CN88104315A patent/CN1028170C/zh not_active Expired - Lifetime
- 1988-06-06 JP JP63137611A patent/JP2569126B2/ja not_active Expired - Lifetime
-
1995
- 1995-08-18 GR GR950402266T patent/GR3017158T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE125797T1 (de) | 1995-08-15 |
| KR950014790B1 (ko) | 1995-12-14 |
| CN1030231A (zh) | 1989-01-11 |
| JP2569126B2 (ja) | 1997-01-08 |
| EP0294685A2 (de) | 1988-12-14 |
| CN1028170C (zh) | 1995-04-12 |
| DE3854245D1 (de) | 1995-09-07 |
| KR890000426A (ko) | 1989-03-14 |
| DE3719014C2 (enrdf_load_stackoverflow) | 1989-03-30 |
| JPS63310868A (ja) | 1988-12-19 |
| EP0294685B1 (de) | 1995-08-02 |
| ES2074988T3 (es) | 1995-10-01 |
| DE3719014A1 (de) | 1988-12-15 |
| GR3017158T3 (en) | 1995-11-30 |
| EP0294685A3 (en) | 1990-05-09 |
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