IE52387B1 - Aroylimidazolones and analogues thereof - Google Patents
Aroylimidazolones and analogues thereofInfo
- Publication number
- IE52387B1 IE52387B1 IE491/82A IE49182A IE52387B1 IE 52387 B1 IE52387 B1 IE 52387B1 IE 491/82 A IE491/82 A IE 491/82A IE 49182 A IE49182 A IE 49182A IE 52387 B1 IE52387 B1 IE 52387B1
- Authority
- IE
- Ireland
- Prior art keywords
- dihydro
- compound
- chloride
- imidazole
- formula
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 56
- -1 pyrryl Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- QPMMUGRPEYWUNZ-UHFFFAOYSA-N 4-(pyridine-4-carbonyl)-1,3-dihydroimidazol-2-one Chemical compound C=1C=NC=CC=1C(=O)C1=CNC(=O)N1 QPMMUGRPEYWUNZ-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 abstract description 9
- 230000003177 cardiotonic effect Effects 0.000 abstract description 4
- 239000000496 cardiotonic agent Substances 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 description 29
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- 238000006243 chemical reaction Methods 0.000 description 18
- 238000000034 method Methods 0.000 description 17
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- 239000002585 base Substances 0.000 description 11
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- 239000000243 solution Substances 0.000 description 9
- WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical class O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 description 8
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- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- 230000000747 cardiac effect Effects 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- 125000004414 alkyl thio group Chemical group 0.000 description 4
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- 229940100198 alkylating agent Drugs 0.000 description 4
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- 238000004587 chromatography analysis Methods 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
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- 239000000376 reactant Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 3
- 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 3
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 150000001266 acyl halides Chemical class 0.000 description 3
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- 239000007943 implant Substances 0.000 description 3
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
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- 238000007911 parenteral administration Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- PSAYJRPASWETSH-UHFFFAOYSA-N pyridine-2-carbonyl chloride Chemical class ClC(=O)C1=CC=CC=N1 PSAYJRPASWETSH-UHFFFAOYSA-N 0.000 description 3
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- 230000009885 systemic effect Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
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- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
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- 230000002378 acidificating effect Effects 0.000 description 2
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- 125000003435 aroyl group Chemical group 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- YCDOKVYDOXHREN-UHFFFAOYSA-N 4-bromopyridine-3-carbonyl chloride Chemical group ClC(=O)C1=CN=CC=C1Br YCDOKVYDOXHREN-UHFFFAOYSA-N 0.000 description 1
- YNKXUNTWNWDIED-UHFFFAOYSA-N 4-ethyl-1,3-dihydroimidazol-2-one Chemical compound CCC1=CNC(=O)N1 YNKXUNTWNWDIED-UHFFFAOYSA-N 0.000 description 1
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- OPNYNEOPPFFHFV-UHFFFAOYSA-N 4-propan-2-yloxypyridine-2-carbonyl chloride Chemical compound CC(C)OC1=CC=NC(C(Cl)=O)=C1 OPNYNEOPPFFHFV-UHFFFAOYSA-N 0.000 description 1
- OSFVFNVXUQRYIX-UHFFFAOYSA-N 5-methylpyridine-3-carbonyl chloride Chemical compound CC1=CN=CC(C(Cl)=O)=C1 OSFVFNVXUQRYIX-UHFFFAOYSA-N 0.000 description 1
- AVYDMRAXLHLEJG-UHFFFAOYSA-N 6-fluoropyridine-2-carbonyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=N1 AVYDMRAXLHLEJG-UHFFFAOYSA-N 0.000 description 1
- IFGABUQRWWPAIC-UHFFFAOYSA-N 6-methoxypyridine-3-carbonyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=N1 IFGABUQRWWPAIC-UHFFFAOYSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
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Classifications
-
- 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
- C07D233/66—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 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
- C07D233/84—Sulfur 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
- C07D233/66—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 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
- C07D233/70—One oxygen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Luminescent Compositions (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24088981A | 1981-03-05 | 1981-03-05 | |
| US06/314,312 US4405628A (en) | 1981-03-05 | 1981-10-23 | 4-Pyridylimidazolones and method of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE820491L IE820491L (en) | 1982-09-05 |
| IE52387B1 true IE52387B1 (en) | 1987-10-14 |
Family
ID=26933806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE491/82A IE52387B1 (en) | 1981-03-05 | 1982-03-04 | Aroylimidazolones and analogues thereof |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4405628A (enExample) |
| EP (1) | EP0059948B1 (enExample) |
| KR (1) | KR890000765B1 (enExample) |
| AT (1) | ATE16489T1 (enExample) |
| AU (1) | AU557590B2 (enExample) |
| CA (1) | CA1190550A (enExample) |
| DE (1) | DE3267352D1 (enExample) |
| DK (1) | DK168627B1 (enExample) |
| ES (2) | ES510087A0 (enExample) |
| GB (1) | GB2096600B (enExample) |
| GR (1) | GR76518B (enExample) |
| HK (1) | HK61686A (enExample) |
| IE (1) | IE52387B1 (enExample) |
| IL (1) | IL65137A (enExample) |
| MY (1) | MY8600700A (enExample) |
| NO (1) | NO157175C (enExample) |
| NZ (1) | NZ199885A (enExample) |
| PH (1) | PH18345A (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4367236A (en) * | 1981-11-04 | 1983-01-04 | Merrell Dow Pharmaceuticals Inc. | Method for the treatment of cardiac failure with alkanoylimidazol-2-one derivatives |
| US4552880A (en) * | 1983-02-15 | 1985-11-12 | Merrell Dow Pharmaceuticals Inc. | Aroylimidazolones |
| US4532250A (en) * | 1983-11-23 | 1985-07-30 | American Hospital Supply Corporation | 5-Heteroarylimidazol-2-ones having cardiotonic activity |
| US4556665A (en) * | 1984-07-09 | 1985-12-03 | Schering A.G. | Cardiotonic 1,3-dihydro-4-[[(imidazol-1-yl)aryl]carbonyl]imidazol-2-ones |
| ZA855592B (en) * | 1984-07-30 | 1986-03-26 | Merrell Dow Pharma | The preparation of 1,3-dihydro-4-pyridoyl-2h-imidazol-2-ones |
| US4803278A (en) * | 1984-07-30 | 1989-02-07 | Merrell Dow Pharmaceuticals, Inc. | Preparation of 1,3-dihydro-4-pyridoyl-2H-imidazol-2-ones |
| US4999365A (en) * | 1987-03-20 | 1991-03-12 | Merrell Dow Pharmaceuticals Inc. | Method of reducing reperfusion injury with imidazol-2-thiones |
| ZA881807B (en) * | 1987-03-20 | 1988-09-05 | Merrell Dow Pharmaceuticals Inc. | Method for reducing reperfusion injury with imidazol-2-thiones |
| ZA887662B (en) * | 1987-10-19 | 1989-06-28 | Merrell Dow Pharma | Method for reducing reperfusion injury with imidazol-2-thione-carboxamides |
| EP0536279A1 (en) * | 1990-06-29 | 1993-04-14 | The Upjohn Company | Substituted 1-(alkoxyphenyl)piperazines with cns and antihypertensive activity |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| DK2170930T3 (da) | 2007-06-04 | 2012-11-05 | Synergy Pharmaceuticals Inc | Agonister af guanylatcyclase, anvendelige til behandlingen af gastrointestinale sygdomme, inflammation, cancer og andre sygdomme |
| US20100120694A1 (en) | 2008-06-04 | 2010-05-13 | Synergy Pharmaceuticals, Inc. | Agonists of Guanylate Cyclase Useful for the Treatment of Gastrointestinal Disorders, Inflammation, Cancer and Other Disorders |
| CA2730603C (en) | 2008-07-16 | 2019-09-24 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| US9580471B2 (en) | 2011-03-01 | 2017-02-28 | Synergy Pharmaceuticals, Inc. | Process of preparing guanylate cyclase C agonists |
| WO2014131024A2 (en) | 2013-02-25 | 2014-08-28 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| US9486494B2 (en) | 2013-03-15 | 2016-11-08 | Synergy Pharmaceuticals, Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| US9708367B2 (en) | 2013-03-15 | 2017-07-18 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| AU2014274812B2 (en) | 2013-06-05 | 2018-09-27 | Bausch Health Ireland Limited | Ultra-pure agonists of guanylate cyclase C, method of making and using same |
| MX375926B (es) | 2013-08-09 | 2025-03-07 | Ardelyx Inc | Compuestos y metodos para inhibir el transporte de fosfato. |
| JP2022533251A (ja) | 2019-05-21 | 2022-07-21 | アルデリックス， インコーポレイテッド | 患者において血清リン酸塩を低下させるための組み合わせ |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2441933A (en) * | 1945-07-30 | 1948-05-18 | Hoffmann La Roche | Substituted imidazolones and process of making them |
| US3538104A (en) * | 1969-02-28 | 1970-11-03 | Geigy Chem Corp | Pyridyl-2-imidazolones |
| ZA803332B (en) * | 1979-06-18 | 1981-01-28 | Richardson Merrell Inc | Novel 4-aroylimidazol-2-ones |
| NZ193935A (en) * | 1979-06-18 | 1985-05-31 | Richardson Merrell Inc | 4-aroyl-imidazol-2-one derivatives;pharmaceutical compositions |
| PH18106A (en) * | 1981-02-18 | 1985-03-21 | Merrell Dow Pharma | Novel-4-aroylimidazol-2-ones |
-
1981
- 1981-10-23 US US06/314,312 patent/US4405628A/en not_active Expired - Lifetime
-
1982
- 1982-03-01 IL IL65137A patent/IL65137A/xx not_active IP Right Cessation
- 1982-03-01 PH PH26929A patent/PH18345A/en unknown
- 1982-03-01 CA CA000397351A patent/CA1190550A/en not_active Expired
- 1982-03-02 NZ NZ199885A patent/NZ199885A/en unknown
- 1982-03-02 AU AU81037/82A patent/AU557590B2/en not_active Ceased
- 1982-03-02 GR GR67455A patent/GR76518B/el unknown
- 1982-03-03 ES ES510087A patent/ES510087A0/es active Granted
- 1982-03-04 DE DE8282101706T patent/DE3267352D1/de not_active Expired
- 1982-03-04 IE IE491/82A patent/IE52387B1/en not_active IP Right Cessation
- 1982-03-04 GB GB8206412A patent/GB2096600B/en not_active Expired
- 1982-03-04 KR KR8200933A patent/KR890000765B1/ko not_active Expired
- 1982-03-04 DK DK095482A patent/DK168627B1/da not_active IP Right Cessation
- 1982-03-04 EP EP82101706A patent/EP0059948B1/en not_active Expired
- 1982-03-04 NO NO820686A patent/NO157175C/no unknown
- 1982-03-04 AT AT82101706T patent/ATE16489T1/de active
-
1983
- 1983-01-25 ES ES519254A patent/ES8402827A1/es not_active Expired
-
1986
- 1986-08-21 HK HK616/86A patent/HK61686A/xx not_active IP Right Cessation
- 1986-12-30 MY MY700/86A patent/MY8600700A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK95482A (da) | 1982-09-06 |
| GB2096600A (en) | 1982-10-20 |
| IL65137A (en) | 1987-02-27 |
| ES8305352A1 (es) | 1983-04-16 |
| HK61686A (en) | 1986-08-29 |
| AU8103782A (en) | 1982-09-09 |
| DK168627B1 (da) | 1994-05-09 |
| IE820491L (en) | 1982-09-05 |
| ES519254A0 (es) | 1984-03-01 |
| ATE16489T1 (de) | 1985-11-15 |
| NO157175B (no) | 1987-10-26 |
| ES8402827A1 (es) | 1984-03-01 |
| NO157175C (no) | 1988-02-03 |
| US4405628A (en) | 1983-09-20 |
| PH18345A (en) | 1985-06-05 |
| GB2096600B (en) | 1985-06-05 |
| EP0059948A1 (en) | 1982-09-15 |
| MY8600700A (en) | 1986-12-31 |
| KR890000765B1 (ko) | 1989-04-05 |
| NZ199885A (en) | 1985-04-30 |
| EP0059948B1 (en) | 1985-11-13 |
| IL65137A0 (en) | 1982-05-31 |
| CA1190550A (en) | 1985-07-16 |
| GR76518B (enExample) | 1984-08-10 |
| AU557590B2 (en) | 1986-12-24 |
| NO820686L (no) | 1982-09-06 |
| KR830009046A (ko) | 1983-12-17 |
| ES510087A0 (es) | 1983-04-16 |
| DE3267352D1 (en) | 1985-12-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |