NO845172L - Fremgangsmaate for fremstilling av imidazolinonderivater - Google Patents
Fremgangsmaate for fremstilling av imidazolinonderivaterInfo
- Publication number
- NO845172L NO845172L NO845172A NO845172A NO845172L NO 845172 L NO845172 L NO 845172L NO 845172 A NO845172 A NO 845172A NO 845172 A NO845172 A NO 845172A NO 845172 L NO845172 L NO 845172L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- imidazolin
- pharmaceutically acceptable
- propylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- 150000003839 salts Chemical class 0.000 claims abstract description 41
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 6
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 239000000126 substance Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- VQSXCZMVUMSITD-UHFFFAOYSA-N 3-[3-(piperidin-1-ylmethyl)phenoxy]propan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CCCCC2)=C1 VQSXCZMVUMSITD-UHFFFAOYSA-N 0.000 claims description 9
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 5
- XZAKYJBLDUAUSD-UHFFFAOYSA-N 2-[3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino]-1,4-dihydroimidazol-5-one Chemical compound O=C1CNC(NCCCOC=2C=C(CN3CCCCC3)C=CC=2)=N1 XZAKYJBLDUAUSD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000006308 propyl amino group Chemical group 0.000 claims description 4
- QTPROSYLXAPWHM-UHFFFAOYSA-N 3-benzyl-2-[3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino]-4h-imidazol-5-one Chemical compound C=1C=CC(CN2CCCCC2)=CC=1OCCCNC1=NC(=O)CN1CC1=CC=CC=C1 QTPROSYLXAPWHM-UHFFFAOYSA-N 0.000 claims description 3
- JSHJYBBDHIWCIX-UHFFFAOYSA-N 3-methyl-2-[3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino]-4h-imidazol-5-one Chemical compound CN1CC(=O)N=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 JSHJYBBDHIWCIX-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- XKXZAVLRYZDNHM-UHFFFAOYSA-N 2-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethylamino]-1,4-dihydroimidazol-5-one Chemical compound O1C(CN(C)C)=CC=C1CSCCNC1=NC(=O)CN1 XKXZAVLRYZDNHM-UHFFFAOYSA-N 0.000 claims description 2
- MYSHQAHXATZEFM-UHFFFAOYSA-N 2-[3-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropyl]-1,4-dihydroimidazol-5-one Chemical compound O=C1CNC(CCCOC=2N=CC=C(CN3CCCCC3)C=2)=N1 MYSHQAHXATZEFM-UHFFFAOYSA-N 0.000 claims description 2
- LKSXHDOPFVYBTJ-UHFFFAOYSA-N 3-ethyl-2-[3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino]-4h-imidazol-5-one Chemical compound CCN1CC(=O)N=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 LKSXHDOPFVYBTJ-UHFFFAOYSA-N 0.000 claims description 2
- RKZIJNDMXFLZFP-UHFFFAOYSA-N 3-methyl-2-[3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino]-4h-imidazol-5-one;dihydrochloride Chemical compound Cl.Cl.CN1CC(=O)N=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 RKZIJNDMXFLZFP-UHFFFAOYSA-N 0.000 claims description 2
- ADASGSGBPNAOJS-UHFFFAOYSA-N 3-methyl-2-[3-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropylamino]-4h-imidazol-5-one Chemical compound CN1CC(=O)N=C1NCCCOC1=CC(CN2CCCCC2)=CC=N1 ADASGSGBPNAOJS-UHFFFAOYSA-N 0.000 claims description 2
- PQPFFTPGHQLIAS-UHFFFAOYSA-N 4,4-dimethyl-2-[3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino]-1h-imidazol-5-one Chemical compound O=C1C(C)(C)NC(NCCCOC=2C=C(CN3CCCCC3)C=CC=2)=N1 PQPFFTPGHQLIAS-UHFFFAOYSA-N 0.000 claims description 2
- YXFZWWXCNIRWHK-UHFFFAOYSA-N 4-benzyl-2-[3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino]-1,4-dihydroimidazol-5-one Chemical compound N1C(CC=2C=CC=CC=2)C(=O)N=C1NCCCOC(C=1)=CC=CC=1CN1CCCCC1 YXFZWWXCNIRWHK-UHFFFAOYSA-N 0.000 claims description 2
- CIBCDBBVDRYLSY-UHFFFAOYSA-N 4-methyl-2-[3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino]-1,4-dihydroimidazol-5-one Chemical compound O=C1C(C)NC(NCCCOC=2C=C(CN3CCCCC3)C=CC=2)=N1 CIBCDBBVDRYLSY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- AZZPAAYLMUOGNP-UHFFFAOYSA-N 2-methylsulfanyl-1,4-dihydroimidazol-5-one Chemical compound CSC1=NC(=O)CN1 AZZPAAYLMUOGNP-UHFFFAOYSA-N 0.000 claims 1
- XBIZLNNDBBZBAS-UHFFFAOYSA-N 3-methyl-2-methylsulfanyl-4h-imidazol-5-one Chemical compound CSC1=NC(=O)CN1C XBIZLNNDBBZBAS-UHFFFAOYSA-N 0.000 claims 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 3
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
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- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 52
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
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- -1 skin inflammation Chemical compound 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 239000003921 oil Substances 0.000 description 23
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
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- FLDCYXOIVORVJI-UHFFFAOYSA-N 2-[[4-[(dimethylamino)methyl]pyridin-2-yl]methylsulfanyl]ethanamine Chemical compound CN(C)CC1=CC=NC(CSCCN)=C1 FLDCYXOIVORVJI-UHFFFAOYSA-N 0.000 description 2
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- 150000002367 halogens Chemical class 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
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- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
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- VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
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- FEQAUBVIUZJXKN-UHFFFAOYSA-N propan-2-imine;hydrochloride Chemical compound [Cl-].CC(C)=[NH2+] FEQAUBVIUZJXKN-UHFFFAOYSA-N 0.000 description 1
- HHAVHBDPWSUKHZ-UHFFFAOYSA-N propan-2-ol;propan-2-one Chemical compound CC(C)O.CC(C)=O HHAVHBDPWSUKHZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
-
- 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838311443A GB8311443D0 (en) | 1983-04-27 | 1983-04-27 | Chemical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO845172L true NO845172L (no) | 1984-12-21 |
Family
ID=10541762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO845172A NO845172L (no) | 1983-04-27 | 1984-12-21 | Fremgangsmaate for fremstilling av imidazolinonderivater |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4567176A (hu) |
| EP (1) | EP0132914B1 (hu) |
| JP (1) | JPS60501207A (hu) |
| KR (1) | KR840008330A (hu) |
| AT (1) | ATE34978T1 (hu) |
| DE (1) | DE3471929D1 (hu) |
| ES (1) | ES8505668A1 (hu) |
| FI (1) | FI845095A0 (hu) |
| GB (1) | GB8311443D0 (hu) |
| GR (1) | GR81941B (hu) |
| HU (1) | HUT34744A (hu) |
| IL (1) | IL71639A0 (hu) |
| NO (1) | NO845172L (hu) |
| PT (1) | PT78498B (hu) |
| WO (1) | WO1984004304A1 (hu) |
| ZA (1) | ZA843088B (hu) |
| ZW (1) | ZW6784A1 (hu) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8417194D0 (en) * | 1984-07-05 | 1984-08-08 | Boots Co Plc | Therapeutic agents |
| TW221689B (hu) * | 1991-08-27 | 1994-03-11 | Otsuka Pharma Co Ltd | |
| GB9611046D0 (en) * | 1996-05-25 | 1996-07-31 | Wivenhoe Techn Ltd | Pharmacological compounds |
| WO2005097751A2 (en) | 2004-03-31 | 2005-10-20 | Janssen Pharmaceutica, N.V. | Non-imidazole heterocyclic compounds as histamine h3-receptor ligands |
| EA015555B1 (ru) | 2006-05-30 | 2011-08-30 | Янссен Фармацевтика Н.В. | Замещенные пиридиламидные соединения в качестве модуляторов гистаминового h-рецептора |
| CN101868454A (zh) | 2007-11-20 | 2010-10-20 | 詹森药业有限公司 | 作为组胺h3受体调节剂的环烷基氧基吡啶化合物和杂环烷基氧基吡啶化合物 |
| WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3968216A (en) * | 1969-10-29 | 1976-07-06 | Smith Kline & French Laboratories Limited | Method of inhibiting histamine activity with guanidine compounds |
| GB1419994A (en) * | 1973-05-03 | 1976-01-07 | Smith Kline French Lab | Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them |
| IN151188B (hu) * | 1978-02-13 | 1983-03-05 | Smith Kline French Lab | |
| ZA793443B (en) * | 1978-07-26 | 1980-12-31 | Glaxo Group Ltd | Heterocyclic derivatives |
| ZW21281A1 (en) * | 1980-10-01 | 1981-11-18 | Smith Kline French Lab | Amine derivatives |
| GR79384B (hu) * | 1982-08-20 | 1984-10-22 | Hoechst Uk Ltd |
-
1983
- 1983-04-27 GB GB838311443A patent/GB8311443D0/en active Pending
-
1984
- 1984-04-13 HU HU842253A patent/HUT34744A/hu unknown
- 1984-04-13 DE DE8484302550T patent/DE3471929D1/de not_active Expired
- 1984-04-13 EP EP84302550A patent/EP0132914B1/en not_active Expired
- 1984-04-13 WO PCT/GB1984/000127 patent/WO1984004304A1/en active Application Filing
- 1984-04-13 JP JP59501699A patent/JPS60501207A/ja active Pending
- 1984-04-13 AT AT84302550T patent/ATE34978T1/de active
- 1984-04-18 US US06/601,527 patent/US4567176A/en not_active Expired - Fee Related
- 1984-04-24 GR GR74486A patent/GR81941B/el unknown
- 1984-04-25 IL IL71639A patent/IL71639A0/xx unknown
- 1984-04-26 KR KR1019840002229A patent/KR840008330A/ko not_active Application Discontinuation
- 1984-04-26 ZW ZW67/84A patent/ZW6784A1/xx unknown
- 1984-04-26 ES ES531933A patent/ES8505668A1/es not_active Expired
- 1984-04-26 ZA ZA843088A patent/ZA843088B/xx unknown
- 1984-04-26 PT PT78498A patent/PT78498B/pt unknown
- 1984-12-21 NO NO845172A patent/NO845172L/no unknown
- 1984-12-21 FI FI845095A patent/FI845095A0/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US4567176A (en) | 1986-01-28 |
| GR81941B (hu) | 1984-12-12 |
| DE3471929D1 (de) | 1988-07-14 |
| ATE34978T1 (de) | 1988-06-15 |
| ZA843088B (en) | 1985-02-27 |
| ES531933A0 (es) | 1985-06-01 |
| FI845095L (fi) | 1984-12-21 |
| ES8505668A1 (es) | 1985-06-01 |
| HUT34744A (en) | 1985-04-28 |
| EP0132914B1 (en) | 1988-06-08 |
| PT78498B (en) | 1986-06-02 |
| IL71639A0 (en) | 1984-07-31 |
| EP0132914A2 (en) | 1985-02-13 |
| JPS60501207A (ja) | 1985-08-01 |
| ZW6784A1 (en) | 1985-04-17 |
| PT78498A (en) | 1984-05-01 |
| FI845095A0 (fi) | 1984-12-21 |
| WO1984004304A1 (en) | 1984-11-08 |
| GB8311443D0 (en) | 1983-06-02 |
| KR840008330A (ko) | 1984-12-14 |
| EP0132914A3 (en) | 1985-12-27 |
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