NZ197246A - Imidazole derivatives and antifungal pharmaceutical compositions - Google Patents
Imidazole derivatives and antifungal pharmaceutical compositionsInfo
- Publication number
- NZ197246A NZ197246A NZ197246A NZ19724681A NZ197246A NZ 197246 A NZ197246 A NZ 197246A NZ 197246 A NZ197246 A NZ 197246A NZ 19724681 A NZ19724681 A NZ 19724681A NZ 197246 A NZ197246 A NZ 197246A
- Authority
- NZ
- New Zealand
- Prior art keywords
- formula
- imidazole
- pharmaceutically acceptable
- acid addition
- imidazole derivatives
- Prior art date
Links
- 150000002460 imidazoles Chemical class 0.000 title claims description 32
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title claims description 21
- 230000000843 anti-fungal effect Effects 0.000 title description 4
- 229940121375 antifungal agent Drugs 0.000 title description 3
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 17
- -1 3- [ (4 , 6-dichlorobenzofuran-3-yl) -methoxy]phenethyl Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- MRGVUWNMTRFDSW-UHFFFAOYSA-N 2-(2-phenylethyl)-1h-pyrrole Chemical compound C=1C=CNC=1CCC1=CC=CC=C1 MRGVUWNMTRFDSW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 206010017533 Fungal infection Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 208000031888 Mycoses Diseases 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- YAXVJPLTIWGXJV-UHFFFAOYSA-N 2-(bromomethyl)-5-chloro-1-benzofuran Chemical compound ClC1=CC=C2OC(CBr)=CC2=C1 YAXVJPLTIWGXJV-UHFFFAOYSA-N 0.000 claims description 3
- UDTLANWPHSQSCO-UHFFFAOYSA-N 5-chloro-2-methyl-1-benzofuran Chemical compound ClC1=CC=C2OC(C)=CC2=C1 UDTLANWPHSQSCO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
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- 238000011200 topical administration Methods 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
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- 239000000203 mixture Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
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- QSWSKDXFOIOXKW-UHFFFAOYSA-N 1h-imidazole;nitric acid Chemical compound O[N+]([O-])=O.C1=CNC=N1 QSWSKDXFOIOXKW-UHFFFAOYSA-N 0.000 description 4
- NSWRTEAIQBHTDY-UHFFFAOYSA-N 3-(bromomethyl)-4,6-dichloro-1-benzofuran Chemical compound ClC1=CC(Cl)=C2C(CBr)=COC2=C1 NSWRTEAIQBHTDY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- 241000222122 Candida albicans Species 0.000 description 3
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- 229940095731 candida albicans Drugs 0.000 description 3
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- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
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- BLIDJLTVFNGWQF-UHFFFAOYSA-N 3-(bromomethyl)-6-chloro-1-benzofuran Chemical compound ClC1=CC=C2C(CBr)=COC2=C1 BLIDJLTVFNGWQF-UHFFFAOYSA-N 0.000 description 2
- UIXOZFFMGRBBHR-UHFFFAOYSA-N 4,6-dichloro-3-methyl-1-benzofuran Chemical compound ClC1=CC(Cl)=C2C(C)=COC2=C1 UIXOZFFMGRBBHR-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000893980 Microsporum canis Species 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 230000001678 irradiating effect Effects 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- QXHHHPZILQDDPS-UHFFFAOYSA-N 1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound S1C=CC(COC(CN2C=NC=C2)C=2C(=CC(Cl)=CC=2)Cl)=C1Cl QXHHHPZILQDDPS-UHFFFAOYSA-N 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960004214 tioconazole Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000005253 yeast cell Anatomy 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8018691 | 1980-06-06 | ||
| GB8106459 | 1981-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ197246A true NZ197246A (en) | 1984-09-28 |
Family
ID=26275759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ197246A NZ197246A (en) | 1980-06-06 | 1981-05-29 | Imidazole derivatives and antifungal pharmaceutical compositions |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4402968A (show.php) |
| EP (1) | EP0041673B1 (show.php) |
| KR (1) | KR840002434B1 (show.php) |
| AR (1) | AR231137A1 (show.php) |
| AU (1) | AU539737B2 (show.php) |
| CA (1) | CA1155853A (show.php) |
| DE (1) | DE3166569D1 (show.php) |
| DK (1) | DK161581A (show.php) |
| ES (1) | ES8203883A1 (show.php) |
| FI (1) | FI69075C (show.php) |
| GR (1) | GR75675B (show.php) |
| HU (1) | HU188098B (show.php) |
| IE (1) | IE52118B1 (show.php) |
| IL (1) | IL63007A (show.php) |
| MC (1) | MC1389A1 (show.php) |
| NO (1) | NO811934L (show.php) |
| NZ (1) | NZ197246A (show.php) |
| PT (1) | PT73150B (show.php) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4517194A (en) * | 1982-06-25 | 1985-05-14 | Ciba-Geigy Corporation | Azolylmandelic acid derivatives and use thereof for controlling microorganisms |
| US5135943A (en) * | 1984-02-02 | 1992-08-04 | Ferrer Internacional S.A. | 1H-imidazole derivative compounds and pharmaceutical compositions containing the same |
| US5714167A (en) | 1992-06-15 | 1998-02-03 | Emisphere Technologies, Inc. | Active agent transport systems |
| US6221367B1 (en) | 1992-06-15 | 2001-04-24 | Emisphere Technologies, Inc. | Active agent transport systems |
| US5578323A (en) | 1992-06-15 | 1996-11-26 | Emisphere Technologies, Inc. | Proteinoid carriers and methods for preparation and use thereof |
| US6099856A (en) * | 1992-06-15 | 2000-08-08 | Emisphere Technologies, Inc. | Active agent transport systems |
| US5693338A (en) * | 1994-09-29 | 1997-12-02 | Emisphere Technologies, Inc. | Diketopiperazine-based delivery systems |
| US5643957A (en) * | 1993-04-22 | 1997-07-01 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6090958A (en) * | 1995-03-31 | 2000-07-18 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5989539A (en) * | 1995-03-31 | 1999-11-23 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6001347A (en) | 1995-03-31 | 1999-12-14 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5965121A (en) * | 1995-03-31 | 1999-10-12 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| BR9604880A (pt) * | 1995-03-31 | 1998-05-19 | Emisphere Tech Inc | Composto composição forma de unidade de dosagem métodos para administração de um agente biologicamente ativo para preparar uma composição para administração de um agente ativo e para preparar um composto e composição farmacológica |
| US5866536A (en) * | 1995-03-31 | 1999-02-02 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5750147A (en) | 1995-06-07 | 1998-05-12 | Emisphere Technologies, Inc. | Method of solubilizing and encapsulating itraconazole |
| GB2320248B (en) * | 1995-09-11 | 1999-04-14 | Emisphere Tech Inc | Method for preparing omega-aminoalkanoic acid derivatives from cycloalkanones |
| IL126318A (en) | 1996-03-29 | 2004-09-27 | Emisphere Tech Inc | Compounds and compositions for delivering active agents and some novel carrier compounds |
| JP2000512671A (ja) | 1996-06-14 | 2000-09-26 | エミスフェアー テクノロジーズ インク | マイクロカプセル化香料及び調製方法 |
| US6060513A (en) * | 1997-02-07 | 2000-05-09 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5876710A (en) * | 1997-02-07 | 1999-03-02 | Emisphere Technologies Inc. | Compounds and compositions for delivering active agents |
| US5879681A (en) * | 1997-02-07 | 1999-03-09 | Emisphere Technolgies Inc. | Compounds and compositions for delivering active agents |
| US6313088B1 (en) | 1997-02-07 | 2001-11-06 | Emisphere Technologies, Inc. | 8-[(2-hydroxy-4-methoxy benzoyl) amino]-octanoic acid compositions for delivering active agents |
| US5990166A (en) * | 1997-02-07 | 1999-11-23 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5939381A (en) * | 1997-02-07 | 1999-08-17 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6358504B1 (en) | 1997-02-07 | 2002-03-19 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5804688A (en) * | 1997-02-07 | 1998-09-08 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5863944A (en) * | 1997-04-30 | 1999-01-26 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5962710A (en) * | 1997-05-09 | 1999-10-05 | Emisphere Technologies, Inc. | Method of preparing salicyloylamino acids |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1475271A (en) * | 1975-04-30 | 1977-06-01 | Pfizer Ltd | 1-aryl-2-1-imidazolyl-alkyl ethers and thioethers and their use as antifungal agents |
| MX3866E (es) * | 1975-07-28 | 1981-08-26 | Syntex Inc | Metodo mejorado para preparar derivados de imidazoles n-alquil sustituidos |
| US4045568A (en) * | 1975-07-28 | 1977-08-30 | Syntex (U.S.A.) Inc. | Derivatives of substituted N-alkyl imidazoles |
| GB1511390A (en) * | 1975-12-04 | 1978-05-17 | Pfizer Ltd | Imidazolylalkyl sulphide antifungal agents |
| IT1096361B (it) * | 1978-05-18 | 1985-08-26 | Recordati Chem Pharm | Dibenzileteri sostituiti terapeuticamente attivi |
| US4221803A (en) * | 1979-05-09 | 1980-09-09 | Recordati, S.A. | Substituted dibenzyl ethers and pharmaceutical compositions containing said ethers for the treatment of infections |
| US4248881A (en) * | 1979-12-20 | 1981-02-03 | E. R. Squibb & Sons, Inc. | Imidazolylethoxymethyl derivatives of pyrazole |
-
1981
- 1981-04-03 CA CA000374678A patent/CA1155853A/en not_active Expired
- 1981-04-09 DK DK161581A patent/DK161581A/da not_active IP Right Cessation
- 1981-05-15 AR AR285348A patent/AR231137A1/es active
- 1981-05-28 FI FI811646A patent/FI69075C/fi not_active IP Right Cessation
- 1981-05-29 US US06/268,304 patent/US4402968A/en not_active Expired - Fee Related
- 1981-05-29 KR KR1019810001901A patent/KR840002434B1/ko not_active Expired
- 1981-05-29 NZ NZ197246A patent/NZ197246A/en unknown
- 1981-06-01 AU AU71213/81A patent/AU539737B2/en not_active Ceased
- 1981-06-01 EP EP81104168A patent/EP0041673B1/de not_active Expired
- 1981-06-01 DE DE8181104168T patent/DE3166569D1/de not_active Expired
- 1981-06-01 IL IL63007A patent/IL63007A/xx unknown
- 1981-06-03 HU HU811645A patent/HU188098B/hu unknown
- 1981-06-04 MC MC811519A patent/MC1389A1/fr unknown
- 1981-06-04 GR GR65150A patent/GR75675B/el unknown
- 1981-06-05 ES ES502792A patent/ES8203883A1/es not_active Expired
- 1981-06-05 NO NO811934A patent/NO811934L/no unknown
- 1981-06-05 PT PT73150A patent/PT73150B/pt unknown
- 1981-06-05 IE IE1250/81A patent/IE52118B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES502792A0 (es) | 1982-05-01 |
| DK161581A (da) | 1981-12-07 |
| PT73150B (en) | 1983-05-11 |
| AU539737B2 (en) | 1984-10-11 |
| MC1389A1 (fr) | 1982-04-27 |
| FI69075C (fi) | 1985-12-10 |
| KR840002434B1 (ko) | 1984-12-27 |
| PT73150A (en) | 1981-07-01 |
| IL63007A0 (en) | 1981-09-13 |
| AR231137A1 (es) | 1984-09-28 |
| IE52118B1 (en) | 1987-06-24 |
| GR75675B (show.php) | 1984-08-02 |
| ES8203883A1 (es) | 1982-05-01 |
| EP0041673A1 (de) | 1981-12-16 |
| IE811250L (en) | 1981-12-06 |
| NO811934L (no) | 1981-12-07 |
| CA1155853A (en) | 1983-10-25 |
| KR830006228A (ko) | 1983-09-20 |
| HU188098B (en) | 1986-03-28 |
| IL63007A (en) | 1985-04-30 |
| DE3166569D1 (en) | 1984-11-15 |
| EP0041673B1 (de) | 1984-10-10 |
| US4402968A (en) | 1983-09-06 |
| AU7121381A (en) | 1981-12-10 |
| FI811646L (fi) | 1981-12-07 |
| FI69075B (fi) | 1985-08-30 |
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