CA1108132A - Procede de fabrication d'oxymorphone - Google Patents
Procede de fabrication d'oxymorphoneInfo
- Publication number
- CA1108132A CA1108132A CA337,908A CA337908A CA1108132A CA 1108132 A CA1108132 A CA 1108132A CA 337908 A CA337908 A CA 337908A CA 1108132 A CA1108132 A CA 1108132A
- Authority
- CA
- Canada
- Prior art keywords
- demethylating
- process according
- boron
- amount
- boron compound
- 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 40
- UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 title claims abstract description 32
- 229960005118 oxymorphone Drugs 0.000 title claims abstract description 32
- 229960002085 oxycodone Drugs 0.000 claims abstract description 36
- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 claims abstract description 35
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 32
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000002879 Lewis base Substances 0.000 claims abstract description 3
- 229910052796 boron Inorganic materials 0.000 claims abstract description 3
- 150000007527 lewis bases Chemical class 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 54
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 35
- 230000001335 demethylating effect Effects 0.000 claims description 34
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 32
- 150000001639 boron compounds Chemical class 0.000 claims description 24
- 239000012429 reaction media Substances 0.000 claims description 21
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
- 230000007062 hydrolysis Effects 0.000 claims description 17
- 238000006460 hydrolysis reaction Methods 0.000 claims description 17
- 239000012649 demethylating agent Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- 238000010520 demethylation reaction Methods 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
- 239000010410 layer Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- -1 e.g. Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910015845 BBr3 Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000017858 demethylation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RSSHKMSIEMOBQX-KFIKYVJASA-N (4r,4as,7ar,12bs)-4a-hydroxy-9-methoxy-3-methyl-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C.O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C RSSHKMSIEMOBQX-KFIKYVJASA-N 0.000 description 1
- UNPLRYRWJLTVAE-UHFFFAOYSA-N Cloperastine hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)OCCN1CCCCC1 UNPLRYRWJLTVAE-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229940023032 activated charcoal Drugs 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/06—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with a hetero atom directly attached in position 14
- C07D489/08—Oxygen atom
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95305678A | 1978-10-19 | 1978-10-19 | |
| US953,056 | 1978-10-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1108132A true CA1108132A (fr) | 1981-09-01 |
Family
ID=25493512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA337,908A Expired CA1108132A (fr) | 1978-10-19 | 1979-10-18 | Procede de fabrication d'oxymorphone |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS55501025A (fr) |
| AU (1) | AU5189779A (fr) |
| BE (1) | BE879494A (fr) |
| CA (1) | CA1108132A (fr) |
| CS (1) | CS211364B2 (fr) |
| DK (1) | DK258280A (fr) |
| ES (1) | ES485154A1 (fr) |
| FI (1) | FI793235A (fr) |
| FR (1) | FR2439201A1 (fr) |
| GB (1) | GB2049680A (fr) |
| IL (1) | IL58489A0 (fr) |
| IT (1) | IT7969032A0 (fr) |
| NL (1) | NL7920126A (fr) |
| NO (1) | NO793297L (fr) |
| SE (1) | SE8004454L (fr) |
| WO (1) | WO1980000841A1 (fr) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4795813A (en) * | 1981-08-17 | 1989-01-03 | The Florida Board Of Regents On Behalf Of The Florida State University | Synthesis of derivatives of codeine and other 3-O-alkylmorphines |
| US5668285A (en) * | 1986-10-31 | 1997-09-16 | The United States Of America As Represented By The Department Of Health And Human Services | Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates |
| FR2636330B1 (fr) * | 1988-09-13 | 1990-11-30 | Sanofi Sa | Procede de preparation de derives de morphinane |
| DK0496830T3 (da) * | 1989-10-16 | 1999-10-11 | Us Health | Total syntese af northebain, normorphin, noroxymorphonenantiomerer og derivater via N-nor-mellemprodukter |
| AU2002320309B2 (en) | 2001-07-06 | 2007-07-12 | Endo Pharmaceuticals, Inc. | Oxymorphone controlled release formulations |
| US8329216B2 (en) | 2001-07-06 | 2012-12-11 | Endo Pharmaceuticals Inc. | Oxymorphone controlled release formulations |
| US7776314B2 (en) | 2002-06-17 | 2010-08-17 | Grunenthal Gmbh | Abuse-proofed dosage system |
| DE10336400A1 (de) | 2003-08-06 | 2005-03-24 | Grünenthal GmbH | Gegen Missbrauch gesicherte Darreichungsform |
| DE10361596A1 (de) | 2003-12-24 | 2005-09-29 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| US20070048228A1 (en) | 2003-08-06 | 2007-03-01 | Elisabeth Arkenau-Maric | Abuse-proofed dosage form |
| DE102005005446A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Bruchfeste Darreichungsformen mit retardierter Freisetzung |
| DE102004032049A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
| DE102005005449A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| US8871779B2 (en) | 2006-03-02 | 2014-10-28 | Mallinckrodt Llc | Process for preparing morphinan-6-one products with low levels of α,β-unsaturated ketone compounds |
| JP5774853B2 (ja) | 2008-01-25 | 2015-09-09 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 医薬投薬形 |
| WO2009135680A1 (fr) | 2008-05-09 | 2009-11-12 | Grünenthal GmbH | Procédé de préparation d'une formulation de poudre intermédiaire et d'une forme galénique solide finale en utilisant une étape de congélation par pulvérisation |
| CA2765971C (fr) | 2009-07-22 | 2017-08-22 | Gruenenthal Gmbh | Forme galenique extrudee a chaud a liberation controlee |
| AU2010275755B2 (en) | 2009-07-22 | 2014-04-24 | Grünenthal GmbH | Oxidation-stabilized tamper-resistant dosage form |
| EP2611426B1 (fr) | 2010-09-02 | 2014-06-25 | Grünenthal GmbH | Forme pharmaceutique inviolable comportant un sel inorganique |
| PL2611425T3 (pl) | 2010-09-02 | 2014-09-30 | Gruenenthal Gmbh | Odporna na ingerencję postać dawki zawierająca polimer anionowy |
| PT2736495T (pt) | 2011-07-29 | 2017-11-30 | Gruenenthal Gmbh | Comprimido resistente à adulteração proporcionando libertação imediata de fármaco |
| HUE034710T2 (hu) | 2011-07-29 | 2018-02-28 | Gruenenthal Gmbh | Visszaéléssel szemben ellenálló, azonnali hatóanyagfelszabadulást biztosító tabletta |
| WO2013127831A1 (fr) | 2012-02-28 | 2013-09-06 | Grünenthal GmbH | Forme pharmaceutique inviolable comprenant un composé pharmacologiquement actif et un polymère anionique |
| MX362357B (es) | 2012-04-18 | 2019-01-14 | Gruenenthal Gmbh | Forma de dosificacion farmaceutica resistente a la adulteracion y resistente a la liberacion inmediata de la dosis. |
| US10064945B2 (en) | 2012-05-11 | 2018-09-04 | Gruenenthal Gmbh | Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc |
| EP3003279A1 (fr) | 2013-05-29 | 2016-04-13 | Grünenthal GmbH | Forme pharmaceutique inviolable contenant une ou plusieurs particules |
| EP3003283A1 (fr) | 2013-05-29 | 2016-04-13 | Grünenthal GmbH | Forme dosifiée inviolable à profil de libération bimodale |
| JP6449871B2 (ja) | 2013-07-12 | 2019-01-09 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | エチレン−酢酸ビニルポリマーを含有する改変防止剤形 |
| WO2015078891A1 (fr) | 2013-11-26 | 2015-06-04 | Farmaceutici Formenti S.P.A. | Préparation de composition pharmaceutique en poudre par cryo-broyage |
| CN106572980A (zh) | 2014-05-12 | 2017-04-19 | 格吕伦塔尔有限公司 | 包含他喷他多的防篡改即释胶囊制剂 |
| EP3148512A1 (fr) | 2014-05-26 | 2017-04-05 | Grünenthal GmbH | Microparticules protégées contre une libération massive dans l'éthanol |
| EP3285745A1 (fr) | 2015-04-24 | 2018-02-28 | Grünenthal GmbH | Forme galénique inviolable avec libération immédiate et résistance à l'extraction par solvant. |
| JP2018526414A (ja) | 2015-09-10 | 2018-09-13 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 乱用抑止性の即放性製剤を用いた経口過剰摂取に対する保護 |
| EP3252055B1 (fr) | 2016-05-31 | 2018-09-19 | Alcaliber Investigacion Desarrollo e Innovacion SLU | Procédé d'obtention de 3,14-diacetyloxymorphone à partir d'oripavine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3249616A (en) * | 1966-05-03 | Ix-dfflydroxy-g-oxo-n-phenethylmor- phinan (cis) and production thereof | ||
| US2806033A (en) * | 1955-08-03 | 1957-09-10 | Lewenstein | Morphine derivative |
| US3775414A (en) * | 1972-05-10 | 1973-11-27 | Bristol Myers Co | Process for the preparation of 14-hydroxymorphinan derivatives |
-
1979
- 1979-10-12 NO NO793297A patent/NO793297L/no unknown
- 1979-10-18 JP JP50190279A patent/JPS55501025A/ja active Pending
- 1979-10-18 IL IL58489A patent/IL58489A0/xx unknown
- 1979-10-18 IT IT7969032A patent/IT7969032A0/it unknown
- 1979-10-18 FR FR7925895A patent/FR2439201A1/fr not_active Withdrawn
- 1979-10-18 ES ES485154A patent/ES485154A1/es not_active Expired
- 1979-10-18 BE BE0/197710A patent/BE879494A/fr unknown
- 1979-10-18 FI FI793235A patent/FI793235A/fi not_active Application Discontinuation
- 1979-10-18 GB GB8014422A patent/GB2049680A/en not_active Withdrawn
- 1979-10-18 CA CA337,908A patent/CA1108132A/fr not_active Expired
- 1979-10-18 NL NL7920126A patent/NL7920126A/nl unknown
- 1979-10-18 AU AU51897/79A patent/AU5189779A/en not_active Abandoned
- 1979-10-18 WO PCT/US1979/000862 patent/WO1980000841A1/fr unknown
- 1979-10-19 CS CS797115A patent/CS211364B2/cs unknown
-
1980
- 1980-06-16 SE SE8004454A patent/SE8004454L/xx not_active Application Discontinuation
- 1980-06-17 DK DK258280A patent/DK258280A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT7969032A0 (it) | 1979-10-18 |
| FI793235A (fi) | 1980-04-20 |
| GB2049680A (en) | 1980-12-31 |
| JPS55501025A (fr) | 1980-11-27 |
| ES485154A1 (es) | 1980-06-16 |
| BE879494A (fr) | 1980-02-15 |
| WO1980000841A1 (fr) | 1980-05-01 |
| NO793297L (no) | 1980-04-22 |
| DK258280A (da) | 1980-06-17 |
| FR2439201A1 (fr) | 1980-05-16 |
| SE8004454L (sv) | 1980-06-16 |
| CS211364B2 (en) | 1982-02-26 |
| AU5189779A (en) | 1980-04-24 |
| IL58489A0 (en) | 1980-01-31 |
| NL7920126A (nl) | 1980-08-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 19980901 |