NO813122L - Fremgangsmaate for fremstilling av dihydro-1h-pyrrolizin-3,5(2h,6h)-dion. - Google Patents
Fremgangsmaate for fremstilling av dihydro-1h-pyrrolizin-3,5(2h,6h)-dion.Info
- Publication number
- NO813122L NO813122L NO813122A NO813122A NO813122L NO 813122 L NO813122 L NO 813122L NO 813122 A NO813122 A NO 813122A NO 813122 A NO813122 A NO 813122A NO 813122 L NO813122 L NO 813122L
- Authority
- NO
- Norway
- Prior art keywords
- preparation
- dihydro
- animal
- dione
- liquid
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 7
- 229920004518 DION® Polymers 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 17
- IEZDOKQWPWZVQF-UHFFFAOYSA-N rolziracetam Chemical compound C1CC(=O)N2C(=O)CCC21 IEZDOKQWPWZVQF-UHFFFAOYSA-N 0.000 claims description 9
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- RXQWTAFAOOIGTO-UHFFFAOYSA-N 2,2-dimethyl-4-nitroheptanedioic acid Chemical compound OC(=O)C(C)(C)CC([N+]([O-])=O)CCC(O)=O RXQWTAFAOOIGTO-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003814 drug Substances 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 239000008188 pellet Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 230000006872 improvement Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 208000000044 Amnesia Diseases 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000003255 drug test Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- -1 flavorings Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012549 training Methods 0.000 description 3
- 208000031091 Amnestic disease Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 208000026139 Memory disease Diseases 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- 244000299461 Theobroma cacao Species 0.000 description 2
- 235000009470 Theobroma cacao Nutrition 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 230000006986 amnesia Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000015654 memory Effects 0.000 description 2
- 230000006984 memory degeneration Effects 0.000 description 2
- 230000006993 memory improvement Effects 0.000 description 2
- 208000023060 memory loss Diseases 0.000 description 2
- ZWKJBVNSPMQOLX-UHFFFAOYSA-N methyl 3-(5-oxopyrrolidin-2-yl)propanoate Chemical compound COC(=O)CCC1CCC(=O)N1 ZWKJBVNSPMQOLX-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000006403 short-term memory Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- CSBJIXVKDCZBPF-UHFFFAOYSA-N 3-(5-oxopyrrolidin-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCC(=O)N1 CSBJIXVKDCZBPF-UHFFFAOYSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- JWWGSSBSDDOWPP-UHFFFAOYSA-N dimethyl 4-nitroheptanedioate Chemical compound COC(=O)CCC([N+]([O-])=O)CCC(=O)OC JWWGSSBSDDOWPP-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18694580A | 1980-09-15 | 1980-09-15 | |
| US06/290,114 US4372966A (en) | 1980-09-15 | 1981-08-07 | Use of dihydro-1H-pyrrolizine-3,5(2H,6H)-dione as a cognition activator |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO813122L true NO813122L (no) | 1982-03-16 |
Family
ID=26882585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO813122A NO813122L (no) | 1980-09-15 | 1981-09-14 | Fremgangsmaate for fremstilling av dihydro-1h-pyrrolizin-3,5(2h,6h)-dion. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4372966A (es) |
| EP (1) | EP0048132B1 (es) |
| AU (1) | AU545556B2 (es) |
| CA (1) | CA1154679A (es) |
| DD (1) | DD201797A5 (es) |
| DE (1) | DE3165563D1 (es) |
| ES (1) | ES505456A0 (es) |
| FI (1) | FI812853L (es) |
| GR (1) | GR75026B (es) |
| HU (1) | HU184883B (es) |
| IE (1) | IE51514B1 (es) |
| IL (1) | IL63663A (es) |
| NO (1) | NO813122L (es) |
| NZ (1) | NZ198342A (es) |
| PH (1) | PH18690A (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4547519A (en) * | 1982-05-24 | 1985-10-15 | Warner-Lambert Company | Tetrahydro-3,5-dioxo-1H-pyrrolizine-7a(5H)-carboxylic acid and benzyl esters and amides thereof and their use in reversing amnesia |
| US4559358A (en) * | 1982-05-24 | 1985-12-17 | Warner-Lambert Company | 5-Oxo-2-pyrrolidinepropanoic acid and derivatives for reversing electroshock amnesia |
| US4525476A (en) * | 1983-05-26 | 1985-06-25 | Warner-Lambert Company | N-[1-oxo-3-(5-oxo-2-pyrrolidinyl)propyl]-alpha-aminoacids and derivatives as cognition activators |
| US4551470A (en) * | 1983-08-29 | 1985-11-05 | Warner-Lambert Company | Hexahydro-3,5-dioxo-1H-pyrrolizine-2-carboxylic acid and derivatives, and use for reversing electroconvulsive shock amnesia |
| US4562195A (en) * | 1984-02-02 | 1985-12-31 | Warner-Lambert Company | Reversing amnesia with saturated tricyclic nitrogen-containing diones |
| US4530929A (en) * | 1984-02-02 | 1985-07-23 | Warner-Lambert Company | Benzotricyclic nitrogen-containing diones and their use in reversing electroconvulsive shock-induced amnesia |
| US4548947A (en) * | 1984-05-07 | 1985-10-22 | Warner-Lambert Company | 1-(Substituted-aryl)-dihydro-1H-pyrrolizine-3,5-[2H,6H-]diones and use for reversing amnesia |
| US4677098A (en) * | 1985-11-22 | 1987-06-30 | Warner-Lambert Company | Substituted dihydro-1H-pyrolizine-3,5(2H,6H)-diones |
| US4663464A (en) * | 1986-03-21 | 1987-05-05 | Warner-Lambert Company | Process for the preparation of dihydro-1H-pyrrolizine-3,5-(2H,6H)-dione |
| IT1233860B (it) * | 1988-02-08 | 1992-04-21 | Isf Spa | Derivati del peridroazacicloalca (1,2-a) imidazolo ad attivita' nootropa |
-
1981
- 1981-08-07 US US06/290,114 patent/US4372966A/en not_active Expired - Fee Related
- 1981-08-26 IL IL63663A patent/IL63663A/xx unknown
- 1981-09-01 AU AU74799/81A patent/AU545556B2/en not_active Ceased
- 1981-09-08 GR GR65982A patent/GR75026B/el unknown
- 1981-09-10 EP EP81304140A patent/EP0048132B1/en not_active Expired
- 1981-09-10 DE DE8181304140T patent/DE3165563D1/de not_active Expired
- 1981-09-11 PH PH26190A patent/PH18690A/en unknown
- 1981-09-14 ES ES505456A patent/ES505456A0/es active Granted
- 1981-09-14 FI FI812853A patent/FI812853L/fi not_active Application Discontinuation
- 1981-09-14 IE IE2133/81A patent/IE51514B1/en unknown
- 1981-09-14 NZ NZ198342A patent/NZ198342A/en unknown
- 1981-09-14 NO NO813122A patent/NO813122L/no unknown
- 1981-09-15 CA CA000385964A patent/CA1154679A/en not_active Expired
- 1981-09-15 HU HU812668A patent/HU184883B/hu unknown
- 1981-09-15 DD DD81233310A patent/DD201797A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1154679A (en) | 1983-10-04 |
| ES8206526A1 (es) | 1982-08-16 |
| AU7479981A (en) | 1982-03-25 |
| FI812853L (fi) | 1982-03-16 |
| IE812133L (en) | 1982-03-15 |
| NZ198342A (en) | 1984-11-09 |
| AU545556B2 (en) | 1985-07-18 |
| DD201797A5 (de) | 1983-08-10 |
| EP0048132A2 (en) | 1982-03-24 |
| HU184883B (en) | 1984-10-29 |
| US4372966A (en) | 1983-02-08 |
| DE3165563D1 (en) | 1984-09-20 |
| ES505456A0 (es) | 1982-08-16 |
| GR75026B (es) | 1984-07-12 |
| IL63663A (en) | 1984-12-31 |
| IE51514B1 (en) | 1987-01-07 |
| PH18690A (en) | 1985-09-05 |
| IL63663A0 (en) | 1981-11-30 |
| EP0048132A3 (en) | 1982-05-12 |
| EP0048132B1 (en) | 1984-08-15 |
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