IL94427A - Process for the production of delmopinol and new intermediates used in this process - Google Patents
Process for the production of delmopinol and new intermediates used in this processInfo
- Publication number
- IL94427A IL94427A IL9442790A IL9442790A IL94427A IL 94427 A IL94427 A IL 94427A IL 9442790 A IL9442790 A IL 9442790A IL 9442790 A IL9442790 A IL 9442790A IL 94427 A IL94427 A IL 94427A
- Authority
- IL
- Israel
- Prior art keywords
- propylpentyl
- propyl
- compounds
- mixture
- compound
- Prior art date
Links
- 239000000543 intermediate Substances 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 20
- QSFOWAYMMZCQNF-UHFFFAOYSA-N delmopinol Chemical compound CCCC(CCC)CCCC1COCCN1CCO QSFOWAYMMZCQNF-UHFFFAOYSA-N 0.000 title claims description 17
- 229960003854 delmopinol Drugs 0.000 title claims description 14
- -1 2-propylpentyl Chemical group 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims description 28
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 21
- 230000002829 reductive effect Effects 0.000 claims description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 239000000203 mixture Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 238000001035 drying Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- RLUDGGHEFUDPLJ-UHFFFAOYSA-N 4-propylhept-1-en-4-ol Chemical compound CCCC(O)(CCC)CC=C RLUDGGHEFUDPLJ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 150000002546 isoxazolidines Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000001345 alkine derivatives Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- MCFJLLFFCSTWHV-UHFFFAOYSA-N 2-propylpentyl 4-methylbenzenesulfonate Chemical compound CCCC(CCC)COS(=O)(=O)C1=CC=C(C)C=C1 MCFJLLFFCSTWHV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 150000002547 isoxazolines Chemical class 0.000 description 3
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- PHUWAKFNUBADFE-UHFFFAOYSA-N 3-(4-propylheptyl)morpholine Chemical compound CCCC(CCC)CCCC1COCCN1 PHUWAKFNUBADFE-UHFFFAOYSA-N 0.000 description 2
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- WVLCITYWJRJQJX-UHFFFAOYSA-N 4-propylhept-1-ene Chemical compound CCCC(CCC)CC=C WVLCITYWJRJQJX-UHFFFAOYSA-N 0.000 description 2
- XZAXWRHYIPMZHS-UHFFFAOYSA-N 4-propylhept-1-yne Chemical compound CCCC(CCC)CC#C XZAXWRHYIPMZHS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JYZUFTSYNSOVNI-UHFFFAOYSA-N 1-bromo-4-propylheptane Chemical compound CCCC(CCC)CCCBr JYZUFTSYNSOVNI-UHFFFAOYSA-N 0.000 description 1
- MKHGVMIXRPGHOO-UHFFFAOYSA-N 2-(benzenesulfonyl)-3-phenyloxaziridine Chemical compound C=1C=CC=CC=1S(=O)(=O)N1OC1C1=CC=CC=C1 MKHGVMIXRPGHOO-UHFFFAOYSA-N 0.000 description 1
- LASHFHLFDRTERB-UHFFFAOYSA-N 2-propylpentan-1-ol Chemical compound CCCC(CO)CCC LASHFHLFDRTERB-UHFFFAOYSA-N 0.000 description 1
- OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical compound ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 description 1
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 238000006736 Huisgen cycloaddition reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- WMWSRIHFAVOHSW-UHFFFAOYSA-N lithium;ethane-1,2-diamine;ethyne Chemical compound [Li+].[C-]#C.NCCN WMWSRIHFAVOHSW-UHFFFAOYSA-N 0.000 description 1
- DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Luminescent Compositions (AREA)
- Photoreceptors In Electrophotography (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8901837A SE8901837D0 (sv) | 1989-05-24 | 1989-05-24 | Substituted isoxazolidines and isoxazolines |
| SE8901838A SE8901838D0 (sv) | 1989-05-24 | 1989-05-24 | New process and intermediates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL94427A0 IL94427A0 (en) | 1991-03-10 |
| IL94427A true IL94427A (en) | 1994-07-31 |
Family
ID=26660511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9442790A IL94427A (en) | 1989-05-24 | 1990-05-17 | Process for the production of delmopinol and new intermediates used in this process |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US5155220A (ja) |
| EP (1) | EP0426826B1 (ja) |
| JP (1) | JP3042876B2 (ja) |
| KR (1) | KR0176248B1 (ja) |
| CN (1) | CN1039325C (ja) |
| AT (1) | ATE104968T1 (ja) |
| AU (1) | AU631648B2 (ja) |
| CA (2) | CA2032513C (ja) |
| DD (1) | DD300104A5 (ja) |
| DE (1) | DE69008486T2 (ja) |
| DK (1) | DK0426826T3 (ja) |
| ES (1) | ES2053195T3 (ja) |
| FI (1) | FI97057C (ja) |
| GE (1) | GEP19971047B (ja) |
| GR (1) | GR1001407B (ja) |
| HU (1) | HU205118B (ja) |
| IE (1) | IE65640B1 (ja) |
| IL (1) | IL94427A (ja) |
| LV (1) | LV10276B (ja) |
| MD (1) | MD423C2 (ja) |
| NO (2) | NO179870C (ja) |
| NZ (1) | NZ233730A (ja) |
| PH (1) | PH31619A (ja) |
| PT (1) | PT94131B (ja) |
| RU (1) | RU2042670C1 (ja) |
| WO (1) | WO1990014342A1 (ja) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5147632A (en) * | 1990-10-31 | 1992-09-15 | Warner-Lambert Company | Anti-plaque compositions comprising a combination of morpholinoamino alcohol and chelating agent |
| GB9226857D0 (en) * | 1992-12-23 | 1993-02-17 | Boyd Edward A | Pharmaceutical compositions |
| US5552757A (en) * | 1994-05-27 | 1996-09-03 | Littelfuse, Inc. | Surface-mounted fuse device |
| US6878004B2 (en) * | 2002-03-04 | 2005-04-12 | Littelfuse, Inc. | Multi-element fuse array |
| CA2526209A1 (en) | 2003-06-12 | 2004-12-23 | Btg International Limited | Cyclic hydroxylamine as psychoactive compounds |
| CN100408382C (zh) * | 2003-11-26 | 2008-08-06 | 力特保险丝有限公司 | 交通工具电气保护装置及利用该装置的系统 |
| GB0523435D0 (en) | 2005-11-17 | 2005-12-28 | Sinclair Pharmaceuticals Ltd | Process |
| EP3184150B1 (en) | 2005-11-22 | 2019-06-19 | Maelor Laboratories Limited | Treatment of sub-gingival pocket infections |
| GB0602424D0 (en) | 2006-02-07 | 2006-03-22 | Sinclair Pharmaceuticals Ltd | Compounds |
| GB0604018D0 (en) | 2006-02-28 | 2006-04-05 | Sinclair Pharmaceuticals Ltd | Method |
| GB0615814D0 (en) | 2006-08-09 | 2006-09-20 | Sinclair Pharmaceuticals Ltd | Medicament |
| GB201105162D0 (en) | 2011-03-28 | 2011-05-11 | Lane Jonathan | Improved deodorant formulations |
| IT201600130729A1 (it) | 2016-12-23 | 2018-06-23 | Lundbeck Pharmaceuticals Italy S P A | Processo per la produzione degli intermedi del delmopinolo |
| IT201600130642A1 (it) | 2016-12-23 | 2018-06-23 | Lundbeck Pharmaceuticals Italy S P A | Processo per la produzione di 2(3 alchilmorfolino)-etan-1-olo |
| IT201600130538A1 (it) | 2016-12-23 | 2018-06-23 | Lundbeck Pharmaceuticals Italy S P A | Processo per la produzione del delmopinolo |
| IT201700076821A1 (it) | 2017-08-24 | 2019-02-24 | Lundbeck Pharmaceuticals Italy S P A | Nuovo sale del delmopinolo |
| US11780818B2 (en) | 2020-01-31 | 2023-10-10 | You First Services, Inc. | Methods of making delmopinol and salts thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE439011B (sv) * | 1980-03-21 | 1985-05-28 | Ferrosan Ab | Morfolinoforeningar, kompositioner innehallande dessa och anvendning derav |
| JPS59164762A (ja) * | 1983-03-09 | 1984-09-17 | Univ Osaka | 第２アミンからニトロンを合成する方法 |
-
1990
- 1990-05-14 DK DK90908724.9T patent/DK0426826T3/da active
- 1990-05-14 ES ES90908724T patent/ES2053195T3/es not_active Expired - Lifetime
- 1990-05-14 JP JP2508104A patent/JP3042876B2/ja not_active Expired - Lifetime
- 1990-05-14 DE DE69008486T patent/DE69008486T2/de not_active Expired - Lifetime
- 1990-05-14 AT AT9090908724T patent/ATE104968T1/de not_active IP Right Cessation
- 1990-05-14 US US07/634,186 patent/US5155220A/en not_active Expired - Lifetime
- 1990-05-14 HU HU905108A patent/HU205118B/hu unknown
- 1990-05-14 WO PCT/SE1990/000323 patent/WO1990014342A1/en active IP Right Grant
- 1990-05-14 AU AU56758/90A patent/AU631648B2/en not_active Expired
- 1990-05-14 CA CA002032513A patent/CA2032513C/en not_active Expired - Lifetime
- 1990-05-14 CA CA002187114A patent/CA2187114C/en not_active Expired - Lifetime
- 1990-05-14 EP EP90908724A patent/EP0426826B1/en not_active Expired - Lifetime
- 1990-05-15 IE IE174890A patent/IE65640B1/en not_active IP Right Cessation
- 1990-05-17 IL IL9442790A patent/IL94427A/en not_active IP Right Cessation
- 1990-05-18 NZ NZ233730A patent/NZ233730A/xx unknown
- 1990-05-23 GR GR900100397A patent/GR1001407B/el not_active IP Right Cessation
- 1990-05-23 CN CN90103088A patent/CN1039325C/zh not_active Expired - Lifetime
- 1990-05-23 DD DD340953A patent/DD300104A5/de unknown
- 1990-05-23 PT PT94131A patent/PT94131B/pt not_active IP Right Cessation
-
1991
- 1991-01-11 FI FI910148A patent/FI97057C/fi active
- 1991-01-11 NO NO910131A patent/NO179870C/no not_active IP Right Cessation
- 1991-01-23 RU SU914894641A patent/RU2042670C1/ru active
- 1991-01-24 KR KR1019910700084A patent/KR0176248B1/ko not_active IP Right Cessation
- 1991-05-14 NO NO911873A patent/NO180120C/no not_active IP Right Cessation
-
1993
- 1993-06-15 LV LVP-93-582A patent/LV10276B/en unknown
- 1993-07-27 GE GEAP19931228A patent/GEP19971047B/en unknown
- 1993-09-07 PH PH46833A patent/PH31619A/en unknown
-
1994
- 1994-07-14 MD MD95-0039A patent/MD423C2/ro unknown
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