FR2611202A1 - Procede de synthese de composes alcaloides dimeres - Google Patents
Procede de synthese de composes alcaloides dimeres Download PDFInfo
- Publication number
- FR2611202A1 FR2611202A1 FR8800650A FR8800650A FR2611202A1 FR 2611202 A1 FR2611202 A1 FR 2611202A1 FR 8800650 A FR8800650 A FR 8800650A FR 8800650 A FR8800650 A FR 8800650A FR 2611202 A1 FR2611202 A1 FR 2611202A1
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- alkyl
- alk
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- 238000000034 method Methods 0.000 title claims abstract description 41
- 230000008569 process Effects 0.000 title claims abstract description 28
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 10
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 8
- 229930013930 alkaloid Natural products 0.000 title claims description 10
- -1 ALKALOID COMPOUNDS Chemical class 0.000 title description 16
- 150000002081 enamines Chemical class 0.000 claims abstract description 40
- 150000007975 iminium salts Chemical class 0.000 claims abstract description 35
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- 229960003048 vinblastine Drugs 0.000 claims abstract description 31
- 238000005273 aeration Methods 0.000 claims abstract description 15
- 238000006213 oxygenation reaction Methods 0.000 claims abstract description 15
- 239000005515 coenzyme Substances 0.000 claims abstract description 8
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims abstract description 7
- 229960004528 vincristine Drugs 0.000 claims abstract description 6
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 30
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 19
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 18
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- 239000000047 product Substances 0.000 claims description 16
- 230000009467 reduction Effects 0.000 claims description 16
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical group C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 238000006062 fragmentation reaction Methods 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
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- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910021645 metal ion Inorganic materials 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- KGUMNRYFUFLBGA-UHFFFAOYSA-N 1,4-dihydropyridine-3-carboxamide Chemical class NC(=O)C1=CNC=CC1 KGUMNRYFUFLBGA-UHFFFAOYSA-N 0.000 claims description 3
- 238000006972 Polonovski rearrangement reaction Methods 0.000 claims description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
- 239000012346 acetyl chloride Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 150000002432 hydroperoxides Chemical class 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 241000863480 Vinca Species 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims 4
- 230000008020 evaporation Effects 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 2
- JYUXDXWXTPSAEL-UHFFFAOYSA-N 1,4-dioxane;oxolane Chemical compound C1CCOC1.C1COCCO1 JYUXDXWXTPSAEL-UHFFFAOYSA-N 0.000 claims 1
- QUIJMHDIAFOPRK-UHFFFAOYSA-N 1-cyclooctylazocane Chemical group C1CCCCCCC1N1CCCCCCC1 QUIJMHDIAFOPRK-UHFFFAOYSA-N 0.000 claims 1
- 241001661930 Aspidosperma Species 0.000 claims 1
- 241001246918 Tabernanthe iboga Species 0.000 claims 1
- 229940122803 Vinca alkaloid Drugs 0.000 claims 1
- 150000004075 acetic anhydrides Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000000935 solvent evaporation Methods 0.000 claims 1
- KKAJSJJFBSOMGS-UHFFFAOYSA-N 3,6-diamino-10-methylacridinium chloride Chemical compound [Cl-].C1=C(N)C=C2[N+](C)=C(C=C(N)C=C3)C3=CC2=C1 KKAJSJJFBSOMGS-UHFFFAOYSA-N 0.000 abstract description 4
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- 239000002184 metal Substances 0.000 abstract 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910001448 ferrous ion Inorganic materials 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 229910000462 iron(III) oxide hydroxide Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000005371 permeation separation Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- AQTQHPDCURKLKT-JKDPCDLQSA-N vincristine sulfate Chemical compound OS(O)(=O)=O.C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 AQTQHPDCURKLKT-JKDPCDLQSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000527897A CA1341261C (en) | 1987-01-22 | 1987-01-22 | Process for the synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2611202A1 true FR2611202A1 (fr) | 1988-08-26 |
| FR2611202B1 FR2611202B1 (enrdf_load_stackoverflow) | 1994-08-19 |
Family
ID=4134803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8800650A Granted FR2611202A1 (fr) | 1987-01-22 | 1988-01-21 | Procede de synthese de composes alcaloides dimeres |
Country Status (11)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1341262C (en) * | 1987-08-06 | 2001-06-26 | Camille A. Boulet | A new process of the synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine |
| US5047528A (en) * | 1987-01-22 | 1991-09-10 | University Of Bristish Columbia | Process of synthesis of vinblastine and vincristine |
| USRE37449E1 (en) | 1987-02-06 | 2001-11-13 | University Of British Columbia | Process of synthesis of 3′,4′-anhydrovinblastine, vinblastine and vincristine |
| US5037977A (en) * | 1988-08-11 | 1991-08-06 | Mitsui Petrochemical Industries Ltd. | Method for production of dimeric alkaloids |
| US5432279A (en) * | 1989-03-04 | 1995-07-11 | Mitsui Petrochemical Industries, Inc. | Process for the preparation of binary indole alkaloids |
| CA2011389A1 (en) * | 1989-03-04 | 1990-09-04 | Naoya Sakamoto | Process for the preparation of binary indole alkaloids |
| FR2779146B1 (fr) * | 1998-06-02 | 2002-01-18 | Roowin | Nouveaux derives de vinca-alcaloides et procedes de preparation |
| CN103936769B (zh) * | 2014-04-30 | 2016-10-05 | 淮海工学院 | 一种制备高光学纯脱水长春碱的方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2358412A1 (fr) * | 1976-07-13 | 1978-02-10 | Parcor | Procede de preparation de la vincamine et d'alcaloides apparentes |
| GB1536407A (en) * | 1974-12-30 | 1978-12-20 | Anvar | Process for the preparation of bis-indolic compounds |
| GB1551054A (en) * | 1976-03-04 | 1979-08-22 | Atta Ur Rahman | Syntheses of vinblastine vincristine and vinrosidine |
| US4279817A (en) * | 1975-05-30 | 1981-07-21 | The United States Of America As Represented By The Department Of Health & Human Services | Method for producing dimer alkaloids |
-
1987
- 1987-01-22 CA CA000527897A patent/CA1341261C/en not_active Expired - Fee Related
-
1988
- 1988-01-20 SE SE8800170A patent/SE467874B/sv not_active IP Right Cessation
- 1988-01-20 DE DE3801450A patent/DE3801450C2/de not_active Expired - Fee Related
- 1988-01-21 GB GB8801296A patent/GB2204036B/en not_active Expired - Lifetime
- 1988-01-21 ZA ZA88408A patent/ZA88408B/xx unknown
- 1988-01-21 IL IL85154A patent/IL85154A/xx not_active IP Right Cessation
- 1988-01-21 NL NL8800134A patent/NL8800134A/nl not_active Application Discontinuation
- 1988-01-21 CH CH206/88A patent/CH675724A5/de not_active IP Right Cessation
- 1988-01-21 IT IT8819156A patent/IT1215751B/it active
- 1988-01-21 FR FR8800650A patent/FR2611202A1/fr active Granted
- 1988-01-22 JP JP63013473A patent/JPH0613531B2/ja not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1536407A (en) * | 1974-12-30 | 1978-12-20 | Anvar | Process for the preparation of bis-indolic compounds |
| US4279817A (en) * | 1975-05-30 | 1981-07-21 | The United States Of America As Represented By The Department Of Health & Human Services | Method for producing dimer alkaloids |
| GB1551054A (en) * | 1976-03-04 | 1979-08-22 | Atta Ur Rahman | Syntheses of vinblastine vincristine and vinrosidine |
| FR2358412A1 (fr) * | 1976-07-13 | 1978-02-10 | Parcor | Procede de preparation de la vincamine et d'alcaloides apparentes |
Non-Patent Citations (4)
| Title |
|---|
| ANGEWANDTE CHEMIE, vol. 94, no. 6, 1982, pages 465-466; N. BABA et al.: "Abh{ngigkeit der Enantioselektivit{t von der relativen Konzentration des Substrats bei einer NADH-Modellreaktion" * |
| CHEMICAL ABSTRACTS, vol. 100, 1984, page 650, résumé no. 103314t, Columbus, Ohio, US; N. BABA et al.: "Addition effect of some macrocyclic polyethers on the asymmetric reduction with chiral NADH model compounds", & BULL. INST. CHEM. RES. KYOTO UNIV. 1983, 61(2), 113-16 * |
| CHEMICAL REVIEWS, vol. 82, 1982, pages 223-243, Columbus, Ohio, US; D.M. STOUT et al.: "Recent advances in the chemistry of dihydropyridines" * |
| JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, 1979, pages 582-584, Cambridge, GB; N. LANGLOIS et al.: "Antitumour alkaloids of the vinblastine-type: Air oxidation of anhydrovinblastine" * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3801450C2 (de) | 1999-02-25 |
| IL85154A0 (en) | 1988-06-30 |
| ZA88408B (en) | 1989-04-26 |
| IL85154A (en) | 1992-08-18 |
| GB8801296D0 (en) | 1988-02-17 |
| DE3801450A1 (de) | 1988-08-18 |
| SE8800170D0 (sv) | 1988-01-20 |
| IT8819156A0 (it) | 1988-01-21 |
| CA1341261C (en) | 2001-06-26 |
| SE467874B (sv) | 1992-09-28 |
| SE8800170L (sv) | 1988-07-23 |
| JPH01131187A (ja) | 1989-05-24 |
| CH675724A5 (enrdf_load_stackoverflow) | 1990-10-31 |
| IT1215751B (it) | 1990-02-22 |
| GB2204036B (en) | 1991-03-27 |
| JPH0613531B2 (ja) | 1994-02-23 |
| GB2204036A (en) | 1988-11-02 |
| NL8800134A (nl) | 1988-08-16 |
| FR2611202B1 (enrdf_load_stackoverflow) | 1994-08-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ER | Errata listed in the french official journal (bopi) |
Free format text: 34/88 |
|
| ST | Notification of lapse |