CA1261845A - Method for oxidizing groups to carboxylic acids under basic conditions - Google Patents
Method for oxidizing groups to carboxylic acids under basic conditionsInfo
- Publication number
- CA1261845A CA1261845A CA000452079A CA452079A CA1261845A CA 1261845 A CA1261845 A CA 1261845A CA 000452079 A CA000452079 A CA 000452079A CA 452079 A CA452079 A CA 452079A CA 1261845 A CA1261845 A CA 1261845A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- methyl
- oxidizing
- copper
- cobalt
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 230000001590 oxidative effect Effects 0.000 title claims abstract description 19
- 150000001735 carboxylic acids Chemical class 0.000 title abstract description 14
- 239000010949 copper Substances 0.000 claims abstract description 28
- 229910052802 copper Inorganic materials 0.000 claims abstract description 23
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 22
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 16
- 239000010941 cobalt Substances 0.000 claims abstract description 16
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052709 silver Inorganic materials 0.000 claims abstract description 16
- 239000004332 silver Substances 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 63
- 238000007254 oxidation reaction Methods 0.000 claims description 19
- WXYKQNAKEPRCGF-UHFFFAOYSA-N 2-methylquinoline-3-carboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C)=NC2=C1 WXYKQNAKEPRCGF-UHFFFAOYSA-N 0.000 claims description 18
- JJLJMEJHUUYSSY-UHFFFAOYSA-L copper(II) hydroxide Inorganic materials [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 17
- 230000003647 oxidation Effects 0.000 claims description 17
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- YHUVMHKAHWKQBI-UHFFFAOYSA-N quinoline-2,3-dicarboxylic acid Chemical compound C1=CC=C2N=C(C(O)=O)C(C(=O)O)=CC2=C1 YHUVMHKAHWKQBI-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 4
- ZUGAIMFLQLPTKB-UHFFFAOYSA-N 3-pyridin-3-ylpropan-1-ol Chemical compound OCCCC1=CC=CN=C1 ZUGAIMFLQLPTKB-UHFFFAOYSA-N 0.000 claims description 3
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 3
- AEJIMXVJZFYIHN-UHFFFAOYSA-N copper;dihydrate Chemical compound O.O.[Cu] AEJIMXVJZFYIHN-UHFFFAOYSA-N 0.000 claims description 3
- 229960003512 nicotinic acid Drugs 0.000 claims description 3
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 2
- HNTZKNJGAFJMHQ-UHFFFAOYSA-N 2-methylpyridine-3-carboxylic acid Chemical compound CC1=NC=CC=C1C(O)=O HNTZKNJGAFJMHQ-UHFFFAOYSA-N 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 25
- 235000011121 sodium hydroxide Nutrition 0.000 description 20
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 12
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 229910001868 water Inorganic materials 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 7
- 229940083608 sodium hydroxide Drugs 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 229960004643 cupric oxide Drugs 0.000 description 4
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- ONHGVIQHHDYDHI-UHFFFAOYSA-N 2-methylquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=C2C=C(C(O)=O)C(C)=NC2=C1 ONHGVIQHHDYDHI-UHFFFAOYSA-N 0.000 description 3
- 239000005751 Copper oxide Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229910019093 NaOCl Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 2
- 229910000431 copper oxide Inorganic materials 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- UPWOEMHINGJHOB-UHFFFAOYSA-N oxo(oxocobaltiooxy)cobalt Chemical compound O=[Co]O[Co]=O UPWOEMHINGJHOB-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- LYVWMIHLNQLWAC-UHFFFAOYSA-N [Cl].[Cu] Chemical compound [Cl].[Cu] LYVWMIHLNQLWAC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- JFBJUMZWZDHTIF-UHFFFAOYSA-N chlorine chlorite Inorganic materials ClOCl=O JFBJUMZWZDHTIF-UHFFFAOYSA-N 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- NFFYXVOHHLQALV-UHFFFAOYSA-N copper(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Cu].[Cu] NFFYXVOHHLQALV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- -1 hyl nicotinic acid Chemical compound 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B33/00—Oxidation in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/215—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of saturated hydrocarbyl groups
-
- 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
- C07D213/803—Processes of preparation
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Quinoline Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US485,769 | 1983-04-18 | ||
| US06/485,769 US4623726A (en) | 1983-04-18 | 1983-04-18 | Method for oxidizing alkyl groups on pyridine, quinoline and benzene ring compounds to carboxylic acids under basic conditions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1261845A true CA1261845A (en) | 1989-09-26 |
Family
ID=23929381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000452079A Expired CA1261845A (en) | 1983-04-18 | 1984-04-16 | Method for oxidizing groups to carboxylic acids under basic conditions |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US4623726A (https=) |
| EP (1) | EP0126893B1 (https=) |
| JP (1) | JPS59199637A (https=) |
| KR (2) | KR920003836B1 (https=) |
| AR (1) | AR240910A1 (https=) |
| AU (1) | AU566449B2 (https=) |
| BR (1) | BR8401813A (https=) |
| CA (1) | CA1261845A (https=) |
| DE (1) | DE3478742D1 (https=) |
| DK (3) | DK168211B1 (https=) |
| ES (1) | ES531657A0 (https=) |
| HU (1) | HU200980B (https=) |
| IE (1) | IE57308B1 (https=) |
| IL (1) | IL71466A (https=) |
| IN (1) | IN162865B (https=) |
| ZA (1) | ZA842889B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4816588A (en) * | 1986-09-12 | 1989-03-28 | American Cyanamid Company | Method for the preparation of pyridine-2,3-dicarboxylic acids |
| DE3706792A1 (de) * | 1987-03-03 | 1988-09-15 | Basf Ag | Verfahren zur herstellung von 7-chlor-chinolin-8-carbonsaeure |
| JP2743473B2 (ja) * | 1988-07-04 | 1998-04-22 | 日産化学工業株式会社 | ピラゾールカルボン酸類の製造方法 |
| US5202442A (en) * | 1988-07-04 | 1993-04-13 | Nissan Chemical Industries, Ltd. | Process for preparing pyrazolecarboxylic acid compounds |
| DK0388619T3 (da) * | 1989-03-22 | 1994-10-03 | American Cyanamid Co | Fremgangsmåde til fremstilling af substituerede 2,3-pyridindicarboxylsyrer ved sekvensvis oxidation af substituerede quinoliner |
| US5002641A (en) * | 1990-06-28 | 1991-03-26 | Reilly Industries, Inc. | Electrochemical synthesis of niacin and other N-heterocyclic compounds |
| EP0743279A1 (en) * | 1995-05-16 | 1996-11-20 | The Procter & Gamble Company | Process for the manufacture of hypochlorite bleaching compositions |
| US5928559A (en) * | 1995-05-16 | 1999-07-27 | The Procter & Gamble Company | Process for the manufacture of hypochlorite bleaching compositions |
| PL236815B1 (pl) * | 2015-11-09 | 2021-02-22 | Wojciech Bukowski | Zastosowanie preparatu antybakteryjnego i antygrzybicznego |
| EP3782985A1 (en) | 2019-08-19 | 2021-02-24 | BASF Agrochemical Products B.V. | Process for manufacturing 5-methoxymethylpyridine-2,3-dicarboxylic acid derivatives |
| CN117143012A (zh) * | 2023-07-21 | 2023-12-01 | 江西帝劢药业有限公司 | 一种喹啉酸的合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2515593A (en) | 1947-02-03 | 1950-07-18 | Shell Dev | Production of pyridine-carboxylic acids |
| US2513099A (en) | 1947-09-09 | 1950-06-27 | Allied Chem & Dye Corp | Oxidation of heterocyclic aromatic nitrogen compounds |
| US2793213A (en) | 1954-07-23 | 1957-05-21 | Allied Chem & Dye Corp | Process for preparing pyridine carboxylic acids |
| US4450055A (en) * | 1983-03-30 | 1984-05-22 | Celanese Corporation | Electrogenerative partial oxidation of organic compounds |
| US4496440A (en) * | 1984-06-04 | 1985-01-29 | The Dow Chemical Company | Oxidation of hydrophobic --CH2 OH compounds at oxidized nickel anodes |
-
1983
- 1983-04-18 US US06/485,769 patent/US4623726A/en not_active Expired - Lifetime
-
1984
- 1984-03-28 DE DE8484103414T patent/DE3478742D1/de not_active Expired
- 1984-03-28 EP EP84103414A patent/EP0126893B1/en not_active Expired
- 1984-03-30 IN IN211/CAL/84A patent/IN162865B/en unknown
- 1984-04-08 IL IL71466A patent/IL71466A/xx not_active IP Right Cessation
- 1984-04-16 ES ES531657A patent/ES531657A0/es active Granted
- 1984-04-16 CA CA000452079A patent/CA1261845A/en not_active Expired
- 1984-04-17 AR AR296332A patent/AR240910A1/es active
- 1984-04-17 JP JP59075903A patent/JPS59199637A/ja active Granted
- 1984-04-17 BR BR8401813A patent/BR8401813A/pt not_active IP Right Cessation
- 1984-04-17 IE IE946/84A patent/IE57308B1/en not_active IP Right Cessation
- 1984-04-17 ZA ZA842889A patent/ZA842889B/xx unknown
- 1984-04-17 AU AU26897/84A patent/AU566449B2/en not_active Expired
- 1984-04-17 KR KR1019840002011A patent/KR920003836B1/ko not_active Expired
- 1984-04-17 DK DK198084A patent/DK168211B1/da not_active IP Right Cessation
- 1984-04-18 HU HU841499A patent/HU200980B/hu unknown
-
1986
- 1986-08-25 US US06/900,462 patent/US4750978A/en not_active Expired - Lifetime
-
1991
- 1991-10-11 KR KR1019910017899A patent/KR920000693B1/ko not_active Expired
-
1993
- 1993-06-22 DK DK074193A patent/DK170154B1/da not_active IP Right Cessation
- 1993-06-22 DK DK074093A patent/DK168623B1/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AR240910A1 (es) | 1991-03-27 |
| US4623726A (en) | 1986-11-18 |
| JPH0582372B2 (https=) | 1993-11-18 |
| IE840946L (en) | 1984-10-18 |
| AU566449B2 (en) | 1987-10-22 |
| DK74193D0 (da) | 1993-06-22 |
| DK168211B1 (da) | 1994-02-28 |
| BR8401813A (pt) | 1984-11-27 |
| AU2689784A (en) | 1984-10-25 |
| US4750978A (en) | 1988-06-14 |
| EP0126893A1 (en) | 1984-12-05 |
| EP0126893B1 (en) | 1989-06-21 |
| DK74193A (da) | 1993-06-22 |
| DK74093D0 (da) | 1993-06-22 |
| HUT36771A (en) | 1985-10-28 |
| IL71466A (en) | 1989-12-15 |
| DK198084A (da) | 1984-10-19 |
| IL71466A0 (en) | 1984-07-31 |
| IN162865B (https=) | 1988-07-16 |
| HU200980B (en) | 1990-09-28 |
| DK74093A (da) | 1993-06-22 |
| DE3478742D1 (en) | 1989-07-27 |
| DK198084D0 (da) | 1984-04-17 |
| DK170154B1 (da) | 1995-06-06 |
| ZA842889B (en) | 1984-11-28 |
| DK168623B1 (da) | 1994-05-09 |
| KR920000693B1 (ko) | 1992-01-20 |
| IE57308B1 (en) | 1992-07-15 |
| KR840008460A (ko) | 1984-12-15 |
| ES8506573A1 (es) | 1985-08-01 |
| JPS59199637A (ja) | 1984-11-12 |
| AR240910A2 (es) | 1991-03-27 |
| ES531657A0 (es) | 1985-08-01 |
| KR920003836B1 (ko) | 1992-05-15 |
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